JP2019069976A - Condensed ring compound and organic light emitting element containing the same - Google Patents

Abstract

An object of the present invention is to provide a fused ring compound and an organic light emitting device including the same. A fused ring compound represented by the following formula: (X11: S, O. X21: S, O, etc. L1 to L3: substituted / unsubstituted benzene, etc. a1 to a3: 0, 1, 2, R1 to R7: H, D, halogen, etc. b1 to b3: (Integer of 1 to 5. c1, c2: integer of 1 to 4)

Description

  The present invention relates to a fused ring compound and an organic light emitting device comprising the same.

  Organic light emitting devices are self-luminous devices that have a wide viewing angle, excellent contrast, quick response time, and excellent luminance, drive voltage, and response speed characteristics. And it has the advantage that multi-coloring is possible.

  According to one example, the organic light emitting device includes an anode, a cathode, and an organic layer including a light emitting layer interposed between the anode and the cathode. A hole transport region is provided between the anode and the light emitting layer, and an electron transport region is provided between the light emitting layer and the cathode. Holes injected from the anode move to the light emitting layer through the hole transporting region, and electrons injected from the cathode move to the light emitting layer through the electron transporting region. Carriers such as holes and electrons recombine in the light emitting layer region to form excitons. Light is generated as the excitons change from the excited state to the ground state.

  The present invention has been made in view of the above prior art, and an object of the present invention is to provide a novel fused ring compound and an organic light emitting device employing the same.

前記化学式１Ａ−２で、
Ｘ_１１は、Ｓ又はＯであり、
Ｘ_２１は、Ｎ−［（Ｌ_２１）_ａ２１−（Ｒ_２１）_ｂ２１］、Ｓ、又はＯであり、
Ｌ_１〜Ｌ_３、及びＬ_２１は、それぞれ独立して、下記化学式２−１〜２−３４で表される基のうちから選択され、
ａ１〜ａ３、及びａ２１は、それぞれ独立して、０、１、又は２であり、
Ｒ_１〜Ｒ_７、及びＲ_２１は、それぞれ独立して、水素、重水素、−Ｆ、−Ｃｌ、−Ｂｒ、−Ｉ、シアノ基、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、下記化学式４−１〜４−３１で表される基、及び−Ｓｉ（Ｑ_３）（Ｑ_４）（Ｑ_５）のうちから選択され、
前記Ｑ_３〜Ｑ_５は、それぞれ独立して、水素、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、フェニル基、ナフチル基、アントラセニル基、ピレニル基、フェナントレニル基、フルオレニル基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ピリジニル基、ピリミジニル基、トリアジニル基、キノリニル基、イソキノリニル基、キナゾリニル基、及びキノキサリニル基のうちから選択され、
ｂ１〜ｂ３、及びｂ２１は、それぞれ独立して、１〜５の整数のうちから選択され、
ｃ１及びｃ２は、互いに独立して、１〜４の整数のうちから選択される。

前記化学式２−１〜２−３４で、
Ｙ_１は、Ｏ、Ｓ、Ｓ（＝Ｏ）、Ｓ（＝Ｏ）_２、Ｃ（Ｚ_３）（Ｚ_４）、Ｎ（Ｚ_５）、又はＳｉ（Ｚ_６）（Ｚ_７）であり、
Ｚ_１〜Ｚ_７は、それぞれ独立して、水素、重水素、−Ｆ、−Ｃｌ、−Ｂｒ、−Ｉ、ヒドロキシル基、シアノ基、ニトロ基、アミノ基、アミジノ基、ヒドラジン基、ヒドラゾン基、カルボン酸基又はその塩、スルホン酸基又はその塩、リン酸基又はその塩、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、フェニル基、ナフチル基、アントラセニル基、トリフェニレニル基、ピレニル基、フェナントレニル基、フルオレニル基、クリセニル基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ピリジニル基、ピリミジニル基、トリアジニル基、キノリニル基、イソキノリニル基、キナゾリニル基、キノキサリニル基、ビフェニル基、及び−Ｓｉ（Ｑ_３３）（Ｑ_３４）（Ｑ_３５）のうちから選択され、
前記Ｑ_３３〜Ｑ_３５は、それぞれ独立して、水素、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、フェニル基、ナフチル基、アントラセニル基、ピレニル基、フェナントレニル基、フルオレニル基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ピリジニル基、ピリミジニル基、ピラジニル基、ピリダジニル基、トリアジニル基、キノリニル基、イソキノリニル基、フタラジニル基、キノキサリニル基、シンノリニル基、及びキナゾリニル基のうちから選択され、
ｄ１は、１〜４の整数であり、ｄ２は、１〜３の整数であり、ｄ３は、１〜６の整数であり、ｄ４は、１〜８の整数であり、ｄ５は、１又は２であり、ｄ６は、１〜５の整数であり、
＊及び＊’は、それぞれ隣接する原子との結合サイトである。

前記化学式４−１〜４−３１で、
Ｙ_３１は、Ｏ、Ｓ、Ｃ（Ｚ_３３）（Ｚ_３４）、Ｎ（Ｚ_３５）、又はＳｉ（Ｚ_３６）（Ｚ_３７）であり、
Ｚ_３１〜Ｚ_３７は、それぞれ独立して、水素、重水素、−Ｆ、−Ｃｌ、−Ｂｒ、−Ｉ、ヒドロキシル基、シアノ基、ニトロ基、アミノ基、アミジノ基、ヒドラジン基、ヒドラゾン基、カルボン酸基又はその塩、スルホン酸基又はその塩、リン酸基又はその塩、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、フェニル基、ナフチル基、アントラセニル基、ピレニル基、フェナントレニル基、フルオレニル基、クリセニル基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ピリジニル基、ピリミジニル基、トリアジニル基、キノリニル基、イソキノリニル基、キナゾリニル基、キノキサリニル基、及び−Ｓｉ（Ｑ_３３）（Ｑ_３４）（Ｑ_３５）のうちから選択され、
前記Ｑ_３３〜Ｑ_３５は、それぞれ独立して、水素、Ｃ_１−Ｃ_２０アルキル基、Ｃ_１−Ｃ_２０アルコキシ基、フェニル基、ナフチル基、アントラセニル基、ピレニル基、フェナントレニル基、フルオレニル基、クリセニル基、カルバゾリル基、ベンゾカルバゾリル基、ジベンゾカルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、ピリジニル基、ピリミジニル基、トリアジニル基、キノリニル基、イソキノリニル基、キナゾリニル基、及びキノキサリニル基のうちから選択され、
ｅ１は、１〜５の整数であり、ｅ２は、１〜７の整数であり、ｅ３は、１〜３の整数であり、ｅ４は、１〜４の整数であり、ｅ５は、１又は２であり、ｅ６は、１〜６の整数であり、＊は、隣接する原子との結合サイトである。 The fused ring compound according to one aspect of the present invention made to achieve the above object is represented by the following chemical formula 1A-2.

In Formula 1A-2,
X ₁₁ is S or O,
X _{21 is, N - [(L 21)} a21 - (R 21) b21], an S, or O,
L _{1 to} L ₃ and L ₂₁ are each independently selected from the groups represented by the following chemical formulas 2-1 to 2-34,
a1 to a3 and a21 are each independently 0, 1 or 2;
R _{1 to} R ₇ and R ₂₁ each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group A group, a group represented by the following chemical formulas 4-1 to 4-31, and -Si (Q ₃ ) (Q ₄ ) (Q ₅ );
The Q _{3 to} Q ₅ are each independently hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl Group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, and quinoxalinyl group ,
b1 to b3 and b21 are each independently selected from the integers of 1 to 5, and
c1 and c2 are independently selected from among integers of 1 to 4.

In the above-mentioned chemical formulas 2-1 to 2-34,
Y ₁ is O, S, S (= O), S (= O) ₂ , C (Z ₃ ) (Z ₄ ), N (Z ₅ ), or Si (Z ₆ ) (Z ₇ ),
Z _{1 to} Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group Group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , quinazolinyl group, quinoxalinyl group, a biphenyl group, and -Si _(Q 33) _{(Q 4)} is selected from among the _{(Q 35),}
Each of Q _{33 to} Q ₃₅ independently represents hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl Groups, benzocarbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl and quinazolinyl Is selected
d1 is an integer of 1 to 4, d2 is an integer of 1 to 3, d3 is an integer of 1 to 6, d4 is an integer of 1 to 8, and d5 is 1 or 2 And d6 is an integer of 1 to 5;
Each of * and * 'is a bonding site to an adjacent atom.

In the chemical formulas 4-1 to 4-31,
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ), or Si (Z ₃₆ ) (Z ₃₇ ),
Z _{31 to} Z ₃₇ each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl Group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group , quinoxalinyl group, and _{-Si (Q 33) (Q 34} ) selected from among the _{(Q 35)} It is,
Each of Q _{33 to} Q ₃₅ independently represents hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group Is selected from
e1 is an integer of 1 to 5, e2 is an integer of 1 to 7, e3 is an integer of 1 to 3, e4 is an integer of 1 to 4, and e5 is 1 or 2 And e6 is an integer of 1 to 6, and * is a bonding site to an adjacent atom.

An organic light emitting device according to one aspect of the present invention made to achieve the above object includes a first electrode, a second electrode, and a light emitting layer interposed between the first electrode and the second electrode. And an organic layer containing at least one or more condensed ring compounds represented by Chemical Formula 1A-2.
The fused ring compound may be included in the light emitting layer, the light emitting layer may further include a dopant, and the fused ring compound included in the light emitting layer may play a role of a host.

  According to the present invention, the fused ring compound has excellent electrical properties and thermal stability, and the organic light emitting device employing the fused ring compound has low driving voltage, high efficiency, high brightness, and long life characteristics. You can have

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment of the present invention.

  Hereinafter, specific examples of modes for carrying out the present invention will be described in detail.

The fused ring compound according to the present invention is represented by the following chemical formula 1.

In chemical formula 1,
X ₁₁ represents N-[(L ₁₁ ) a _11- (R ₁₁ ) _{b 11} ], S, O, S (= O), S (= O) ₂ , C (= O), C (R ₁₂ ) (R ₁₃ ) Si (R ₁₂ ) (R ₁₃ ), P (R ₁₂ ), or P (= O) (R ₁₂ ), and f 1 and f 2 are each independently 0 or 1 and f 1 + f 2 is 1 and
X _{21 is, N - [(L 21)} a21 - (R 21) b21], S, O, S (= O), S (= O) 2, C (= O), C (R 22) (R ₂₃ ) Si (R ₂₂ ) (R ₂₃ ), P (R ₂₂ ), or P (= O) (R ₂₂ ), and f3 and f4 are each independently 0 or 1, and f3 + f4 is 1 and
X _{31 to} X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ],
g1 and g2 are each independently 0, 1 or 2, and g1 + g2 is 2,
i) In Formula 1, f1 = 1, f2 = 0, f3 = 1, f4 = 0, g1 = 1, and a g2 = _1, when _{X 11} is _{C (R 12) (R 13} ), X _{21, N - [(L 21)} a21 - (R 21) b21] a not, ii) by the chemical formula 1, f1 = 1, f2 = 0, f3 = 1, f4 = 0, g1 = 1, and g2 = is _{1, X 11} the _N - if _{- [(L 11) a11 (} R 11) b11] _{a, X 21 is,} N _- not _{- [(L 21) a21 (} R 21) b 21] and C (R ₂₂ ) (R ₂₃ ), and iii) in the chemical formula 1, f1 = 1, f2 = 0, f3 = 0, f4 = 1, g1 = 0, and g2 = 2, and X ₁₁ is C (R _{12) (if R 13), X 21 is, N - [(L 21)} a21 - (R 21) b21] a rather, iv) chemical In 1, f1 = 0, f2 = 1, f3 = 1, f4 = 0, g1 = 1, and a g2 = _1, when _{X 11} is _{C (R 12) (R 13} ), X 21 is N-[(L ₂₁ ) a _21- (R ₂₁ ) b ₂₁ ] and not C (R ₂₂ ) (R ₂₃ ) but v) Chemical Formula 1, f1 = 0, f2 = 1, f3 = 1, f4 = 0, g1 = 1, and a g2 = _{1, X 11} the _N - when it is _{- [(L 11) a11 (} R 11) b11], X 21 _is a _{C (R 22) (R 23} ) If vi) in Formula 1 and f1 = 0, f2 = 1, f3 = 1, f4 = 0, g1 = 1, and g2 = 1, and X ₁₁ is S, then X ₂₁ is N- [N] _{(L 21) a21 - (R} 21) b21] a rather, vii) by the chemical formula 1, f1 = 0, f2 = 1, f3 = 1, f4 = 0, g1 = 1, And a g2 = _1, when _{X 11} is _{Si (R 12) (R 13} ), X 21 _{is, N - [(L 21)} a 21 - (R 21) b 21] a rather, viii) chemical formula 1, f 1 = 0, f 2 = 1, f 3 = 0, f 4 = 1, g 1 = 1 and g 2 = 1 and X ₁₁ is N-[(L ₁₁ ) _a11 − (R ₁₁ ) _b11 ] If X ₂₁ is not C (R ₂₂ ) (R ₂₃ ), then
L _{1 to} L ₃ , L ₁₁ and L ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted Unsubstituted C ₃ -C ₁₀ cycloalkenylene, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene, substituted or unsubstituted C ₆ -C ₆₀ arylene, substituted or unsubstituted C ₁ -C ₆₀ A heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero fused polycyclic group,
a1 to a3, a11 and a21 are independently selected from among integers of 0 to 5;
R _{1 to} R ₇ , R _{11 to} R ₁₃ and R _{21 to} R ₂₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group , Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or non-substituted group Substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted _C 1 _{-C 10} heterocycloalkyl group, a substituted or unsubstituted _C 3 _{-C 10} cycloalkenyl group, a substituted or unsubstituted _C 1 _{-C 10} Heteroshi Roarukeniru group, a substituted or unsubstituted _C 6 _{-C 60} aryl group, a substituted or unsubstituted _C 6 _{-C 60} aryloxy group, a substituted or unsubstituted _C 6 _{-C 60} arylthio group, a substituted or unsubstituted _{C 1} -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero fused polycyclic group, -N (Q ₁ ) (Q ₂ ),- It is selected from Si (Q ₃ ) (Q ₄ ) (Q ₅ ), and —B (Q ₆ ) (Q ₇ ),
b1 to b3, b11 and b21 are independently selected from among integers of 1 to 5;
c1 is selected from the integers of 1 to 4;
Substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, Substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted bivalent non-aromatic fused polycyclic group, substituted bivalent non-aromatic hetero fused polycyclic group, Substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C _3- C ₁₀ cycloalkyl group, substituted _C 1 _{-C 10} heterocycloalkyl group, a substituted _C 3 _{-C 10} cycloalkenyl group, _C 1 _{-C 10} Heteroshiku substituted Alkenyl group, a substituted _C 6 _{-C 60} aryl group, a substituted _C 6 _{-C 60} aryloxy group, a substituted _C 6 _{-C 60} arylthio group, a substituted _C 1 _{-C 60} heteroaryl group, a substituted At least one of the substituted monovalent non-aromatic fused polycyclic group and the substituent of the substituted monovalent non-aromatic hetero fused polycyclic group is
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ An aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero fused polycyclic group, _{-N (Q 11) (Q 12} ), - Si (Q 13) (Q 14) (Q 1 5), and _-B (Q 16) substituted with at least one of the _{(Q 17),} C ₁ -C ₆₀ alkyl _Group, C 2 _{-C 60} alkenyl _group, C 2 _{-C 60} alkynyl group, and _C 1 _{-C 60} alkoxy group;
C ₃ -C ₁₀ cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic hetero fused polycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, a monovalent non-aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 21) (Q} 22), - Si (Q 23) ( _{24) (Q 25),} and _{-B (Q} 26) (at least one in _substituted, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl group of _{Q 27), C 3} -C ₁₀ cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group , monovalent nonaromatic condensed Hajime Tamaki, and monovalent non-aromatic heterocyclic condensed Hajime Tamaki; and _{-N (Q 31) (Q 32} ), - Si (Q 33) (Q 34) (Q 35), And -B (Q ₃₆ ) (Q ₃₇ );
_{Q 1 ~Q 7, Q 11 ~Q} 17, Q 21 ~Q 27, and _Q 31 _{to Q 37} independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy groups , Cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl _group, C 2 _{-C 60} alkynyl _group, C 1 _{-C 60} alkoxy _group, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} Ariruoshi _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non Aromatic condensed Hajime Tamaki, and is selected from among the monovalent non-aromatic hetero fused polycyclic group.

  In Chemical Formula 1, the description regarding each substituent refers to the part described in the present specification.

  The fused ring compound is represented by any one of the following chemical formulas 1-1 to 1-12.

In the chemical formulas 1 and 1-1 to 1-12, X ₁₁ represents N-[(L ₁₁ ) a _11- (R ₁₁ ) _{b 11} ], S, O, S (= O), S (= O) ₂ , C (= O), C (R ₁₂ ) (R ₁₃ ), Si (R ₁₂ ) (R ₁₃ ), P (R ₁₂ ), or P (= O) (R ₁₂ ), and X ₂₁ is N _{- [(L 21) a21 -} (R 21) b21], S, O, S (= O), S (= O) 2, C (= O), C (R 22) (R 23), Si ( R ₂₂ ) (R ₂₃ ), P (R ₂₂ ), or P (= O) (R ₂₂ ).

According to an embodiment, in Formula 1 and 1-1 to 1-12, X ₁₁ represents N-[(L ₁₁ ) _a11- (R ₁₁ ) _b11 ], S, O, C (R ₁₂ ) ( R _13), or _Si (R 12) a _{(R 13), X 21 is, N - [(L 21)} a21 - (R 21) b21], S, O, C (R 22) (R 23) Or Si (R ₂₂ ) (R ₂₃ ), but is not limited thereto.

In Chemical Formula 1 and 1-1 to 1-12, X _{31 to} X ₃₄ are each independently N or C-[(L ₂ ) _a2- (R ₂ ) _b2 ].

In Chemical Formula 1, and 1-1 to _1-12, 2 or more _C of _{X 31 ~X 34 - [(L} 2) a2 - (R 2) b 2] when it, or they are different from each other Or the same.

According to an embodiment, in Formula 1, and 1-1 to _1-12, X 31 _{to X 34} are both _C - a _{- [(R 2) b2 (} L 2) a2].

  Accordingly, the fused ring compound is represented by any one of the following chemical formulas 1A-1 to 1A-12.

In the chemical formulas 1A-1 to 1A-12, the descriptions of X ₁₁ , X ₂₁ , L _{1 to} L ₃ , a _{1 to a 3} , R _{1 to} R ₇ and c ₁ refer to the portions described in this specification, c2 is selected from an integer of 1 to 4;

The fused ring compound is
i) In the chemical formula 1-2, when X ₁₁ is C (R ₁₂ ) (R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 − (R ₂₁ ) _b21 ],
ii) In the chemical formula 1-2, when X ₁₁ is N-[(L ₁₁ ) a _11- (R ₁₁ ) b ₁₁ ], X ₂₁ is N-[(L ₂₁ ) a _21- (R ₂₁ ) b ₂₁ And not C (R ₂₂ ) (R ₂₃ ),
In iii) Formula _1-4, when _{X 11} is _{C (R 12) (R 13} ), X 21 _{is, N - [(L 21)} a21 - (R 21) b21] is not,
In iv) Formula _1-8, when _{X 11} is _{C (R 12) (R 13} ), X 21 _{is, N - [(L 21)} a21 - (R 21) b21] a rather and C _{(R 22} Not) (R ₂₃ ),
v) When X ₁₁ is N-[(L ₁₁ ) a _11- (R ₁₁ ) _{b 11} ] in the chemical formula 1-8, X ₂₁ is not C (R ₂₂ ) (R ₂₃ ),
In vi) Formula _1-8, when _{X 11} is _{S, X 21 is, N - [(L 21)} a21 - (R 21) b21] is not,
vii) When X ₁₁ is Si (R ₁₂ ) (R ₁₃ ) in the chemical formula 1-8, X ₂₁ is not N-[(L ₂₁ ) _a21- (R ₂₁ ) b ₂₁ ],
In viii) Chemical Formula 1-11, X11 the _N - if _{- [(L 11) a11 (} R 11) b11] _{a, X 21 is} not _{C (R 22) (R 23} ).

  Therefore, when the fused ring compound is represented by the chemical formula 1-2, it is represented by any one of the following chemical formulas 1A-2-1 to 1A-2-22, and the fused ring compound is represented by the chemical formula 1-4. When it is shown, it is shown by any one of the following chemical formulas 1A-4-1 to 1A-4-24, and when the fused ring compound is shown by the chemical formula 1-8, the following chemical formula 1A-8-1 is shown When it is shown by any one of 1A-8-20 and the fused ring compound is shown by the chemical formula 1-11, any one of the following chemical formulas 1A-11-1 to 1A-11-24 But not limited thereto.

For example, Formula 1A-2-10 has a backbone of Formula 1A-2, but X11 is O, X21 is O, and Formula 1A-2-14 is Formula 1A-2. has a backbone, X11 is S, X21 _is N _- is a chemical formula is _{- [(L 21) a21 (} R 21) b21].

  Chemical formulas 1A-2-1 to 1A-2-22, chemical formulas 1A-4-1 to 1A-4-24, chemical formulas 1A-8-1 to 1A-8-20, and chemical formulas 1A-11-1 to 1A-11 The structure of -24 is understood with reference to the above.

According to one embodiment, the fused ring compound is
The compound is represented by any one of chemical formulas 1-1 to 1-7, and chemical formulas 1-9 to 1-12,
Chemical formulas 1-1 to 1-7, and chemical formulas 1-9 to 1-12,
X ₁₁ and X ₂₁ are each independently O or S, or
X ₁₁ is O or _{S, X 21 is, N - [(L 21)} a21 - (R 21) b21] or a _{C (R 22) (R 23} ),
X ₁₁ is N-[(L ₁₁ ) a _11- (R ₁₁ ) _{b 11} ] or C (R ₁₂ ) (R ₁₃ ), X ₂₁ is O or S, or X ₁₁ is C R ₁₂ ) (R ₁₃ ), and X ₂₁ is C (R ₂₂ ) (R ₂₃ ).

According to another embodiment, the fused ring compound is
It is represented by any one of chemical formulas 1A-1 to 1A-7, and chemical formulas 1A-9 to 1A-12,
In chemical formulas 1A-1 to 1A-7, and chemical formulas 1A-9 to 1A-12,
X ₁₁ and X ₂₁ are each independently O or S, or
X ₁₁ is O or _{S, X 21 is, N - [(L 21)} a21 - (R 21) b21] or a _{C (R 22) (R 23} ),
X11 _is N _- a _{- [(L 11) a11 (} R 11) b11] or _{C (R 12) (R 13} ), or _{X 21} is O or S, or X ₁₁ is C (R ₁₂ ) (R ₁₃ ), and X ₂₁ is C (R ₂₂ ) (R ₂₃ ).

According to still another embodiment, the fused ring compound is represented by any one of Formulas 1-1, 1-3 to 1-7, and Formulas 1-9 to 1-11, and a compound represented by Formula 1- 1,1-3～1-7, and a chemical formula _{1-9~1-11, X 11 is,} N _- a _{- [(L 11) a11 (} R 11) b11], X 21 is, N-[ _{(L 21)} a21 _- a (R _{21) b21].}

According to yet another embodiment, the fused ring compound is represented by any one of chemical formulas 1A-1, 1A-3 to 1A-7, and chemical formulas 1A-9 to 1A-11, and the chemical formula 1A- in 1,1A-3~1A-7 and formula _{1A-9~1A-11,, X} 11 _is, N _- a _{- [(L 11) a11 (} R 11) b11], X 21 is, N-[ _{(L 21)} a21 _- a (R _{21) b21].}

According to yet another embodiment, the fused ring compound is represented by Formula 1-2, and in Formula 1-2, X ₁₁ is O or S, and X ₂₁ is O, S, or N- [ _{(L 21)} a21 _- a (R _{21) b21].}

According to yet another embodiment, the fused ring compound is represented by Formula 1A-2, wherein X ₁₁ is O or S, and X ₂₁ is O, S, or N- [. (L ₂₁ ) a ₂ 1- (R ₂₁ ) _{b 21} ].

According to one embodiment, the fused ring compound is represented by any one of Chemical Formulas 1-1 to 1-7, and Chemical Formulas 1-9 to 1-12, and Chemical Formulas 1-1 to 1-7. And in the chemical formulas 1-9 to 1-12, X ₁₁ is O or S. The fused ring compounds in which X ₁₁ is O or S have improved planarity and have excellent charge mobility due to the O and S lone pair electron pairs.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formulas of Table 1, L _{1 to} L ₃ , L ₁₁ and L ₂₁ are each independently substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ hetero cycloalkenylene groups, substituted or unsubstituted _C 6 _{-C 60} arylene group, a substituted or unsubstituted _C 1 _{-C 60} heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed Hajime Tamaki (substituted or unsubstituted divalent non-aromatic condensed cyclic group) and substitution Properly it is selected from among unsubstituted divalent non-aromatic hetero condensed Hajime Tamaki (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group).

According to an embodiment, L _{1 to} L ₃ , L ₁₁ and L ₂₁ may be independent of each other in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1 do it,
Phenylene group, pentalenylene group, pentenylene group, indenylene group, indylene group, naphthylene group, naphthylene group, azulenylene group, heptalenylene group, heptalenylene group, indacenylene group, acenaphthylene group, acenaphthylene group (Fluorenylene), spiro-fluorenylene group (spiro-fluorenylene), phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrylene), anthracenylene group (anthracenylene), fluoranthenylene group (fluorantheny) ene), triphenylenylene group (triphenylene group), pyrenylene group (pyrenylene group), chrysenylene group (chrysenylene group), naphthacenylene group (naphthacenylene group), picenylene group (picenylene), peryrenylene group (perylenylene), pentaphenylene group (pentaphenylene), hexasenyl group (Hexacenylene), pyrrolylene group (pyrrolylene), imidazolylene group (imidazolylene), pyrazolylene group (pyrazolylene), pyridinylene group (pyridinylene), pyrazinylene group (pyrazinylene), pyrimidinylene group (pyrimidinylene), pyridazinylene Group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene), isoquinolinylene group (isoquinolinylene), benzoquinolinylene group (benzozolinylene) ), Phthalazinylene group (phthalazinylene), naphthyridinylene group (naphthyridinylene), quinoxalinylene group (quinoxalinylene), quinazolinylene group (quinazolinylene), cinnolinylene group (cinnolinylene), carbazolylene group (carbaylene group) zolylene), phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoxazolylene, benzoimidazolylene, benzoimidazolene Furanylene group (furanylene), benzofuranylene group (benzofuranylene), thiophenylene group (thiophenylene), benzothiophenylene group (benzothiophenylene), thiazolylene group (thiazolylene), isothiazolylene group (isothiazolylene) Benzothiazolylene group (benzothiazolylene), isoxazolylene group (isoxazolylene), oxazolylene group (oxazolylene), triazolylene group (triazolylene), tetrazolylene group (tetrazolylene), oxadiazolylene group (oxadiazolylene), triazinylene group (triazinylene) Group (dibenzofuranylene), dibenzothiophenylene group, benzocarbazolylene group (benzocarbazolylene), dibenzocarbazolylene group (dibenzocarbazolylene), imidazopyrimidinylene group (imidazopyrimi group) deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, inylene), and imidazopyridinylene group; Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, C ₁ -C ₂₀ At least one of heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic hetero fused ring group, and —Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, indacenylene group, acenaphthylene group, fluo Nylene group, spiro-fluorenylene group, phenarenylene group, phenanthrenyl group, anthracenylene group, fluorantrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene Group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindoliylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group Group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthro Linylene group, phenazinylene group, benzoxazolylene group, benzimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, Triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, imidazopyrimidinylene, and imidazopyridinylene; Selected from
Q ₃₃ to Q ₃₅ independently of one another, _hydrogen, C 1 _{-C 20} alkyl _group, C 1 _{-C 20} alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, a fluorenyl group, a carbazolyl group , Benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, triazinyl group, isoquinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinnolinyl group, and quinazolinyl group Be done.

According to other embodiments, L _{1 to} L ₃ , L ₁₁ , and L ₂₁ may be phenylene in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formula in Table 1. Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or The salt, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group And a phenylene group, a naphthylene group, and a triphenylene group substituted with at least one of a chrysenyl group, and selected from, but not limited to It is not something that

According to still another embodiment, L _{1 to} L ₃ , L ₁₁ , and L ₂₁ in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Table 1 Each of them is any one of chemical formulas 2-1 to 2-34 independently of each other.

In chemical formulas 2-1 to 2-34,
Y ₁ is O, S, S (= O), S (= O) ₂ , C (Z ₃ ) (Z ₄ ), N (Z ₅ ), or Si (Z ₆ ) (Z ₇ ),
Z _{1 to} Z ₇ are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group Group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , quinazolinyl group, quinoxalinyl group, a biphenyl group, and _{-Si (Q} 33) _{(Q 3} ) Is selected from the group consisting of _{(Q 45),}
Q33 to Q35 are, independently of one another, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzo Carbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinnolinyl group, and selected from quinazolinyl groups;
d1 is an integer of 1 to 4, d2 is an integer of 1 to 3, d3 is an integer of 1 to 6, d4 is an integer of 1 to 8, and d5 is 1 or 2 And d6 is an integer of 1 to 5;
Each of * and * 'is a bonding site to an adjacent atom.

According to still another embodiment, L _{1 to} L ₃ , L ₁₁ , and L ₂₁ in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Table 1 Each of the groups is selected from, but not limited to, the groups represented by Chemical Formulas 3-1 to 3-21.

  Each of * and * 'is a bonding site to an adjacent atom.

According to still another embodiment, L _{1 to} L ₃ , L ₁₁ , and L ₂₁ in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Table 1 Independently of each other
Phenylene, naphthylene, pyridinylene, pyrimidinylene, and triazinylene;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phenylene substituted with at least one of phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, and triazinyl group It is selected from, but not limited to, group, naphthylene group, pyridinylene group, pyrimidinylene group, and triazinylene group.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, a1 represents the number of L ₁ and is 0, 1, 2, 3, 4 Or 5, for example, 0, 1 or 2, and another example is 0 or 1. When a1 is 0, *-(L ₁ ) _a1- * 'is a single bond. When a1 is 2 or more, 2 or more L ₁ are the same as or different from each other. The description according to a2, a3, a11, and a21 is understood with reference to the description according to a1, and the chemical formulas in chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Table 1 Ru.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1, R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R _{21 to} R ₂₃ are mutually independent. Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group Or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkynyl groups, substituted or unsubstituted _C 1 _{-C 60} alkoxy group, a substituted or unsubstituted _C 3 _{-C 10} cycloalkyl group, a substituted or unsubstituted _C 1 _{-C 10} heterocycloalkyl group, a substituted or unsubstituted ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted _C 1 _{-C 10} heterocycloalkenyl groups, substituted or unsubstituted _C 6 _{-C 60} aryl group, a substituted or unsubstituted _C 6 _{-C 60} aryloxy group, Substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-substituted Aromatic hetero fused polycyclic group, -N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ), and -B (Q ₆ ) (Q ₇ ); Ru.

According to an embodiment, R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R ₂₁ to R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R ₂₁ to R ₂₃ is, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group Or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₂₀ alkyl groups, substituted or unsubstituted C ₁ -C ₂₀ alkoxy groups, substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed Hajime Tamaki, a substituted or unsubstituted monovalent non-aromatic hetero fused polycyclic And -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) is selected.

According to still further embodiments, the chemical formula 1,1-1～1-12, and 1A-1~1A-12, as well as by the chemical formula of Table 1, _{i) X 11} is _{N - [(L 11) a11} - If _{(R 11) b} 11] is at least one of _{R 3} and _{R 11, ii) X 21} is _{N - [(L 21) a11} - If a _{(R 21) b11], R} 3 and at least one of R _21, and _{iii) X 11} the _N - a _{- [(L 11) a11 (} R 11) b11], X 21 is _{N - [(L 21) a11} - (R 21) b11 And at least one of R ₃ , R ₁₁ and R ₂₁ is, independently of one another, a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a substituted or unsubstituted C ₂ -C ₂₀ Heteroaryl group, substituted or unsubstituted monovalent non-aromatic Condensed Hajime Tamaki, and is selected from substituted or unsubstituted monovalent non-aromatic hetero fused polycyclic group.

According to yet another embodiment, in the chemical formulas of Formulas 1-1, 1-1-12, and 1A-1 to 1A-12, and Table 1, R ₃ represents at least one nitrogen atom as a ring-constituting atom. Selected from among substituted or unsubstituted C ₁ -C ₃₀ heteroaryl groups, and substituted or unsubstituted monovalent non-aromatic hetero-fused polycyclic groups, including, but not limited to.

According to still another embodiment, R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1 _{21 to} R ₂₃ independently of each other
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its group A salt, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, And a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a phosphoric acid group or a salt thereof;
Phenyl group (phenyl), pentalenyl group (pentalenyl), indenyl group (indenyl), naphthyl group (naphthyl), azulenyl group (azulenyl), heptalenyl group (heptalenyl), indasenyl group (indacenyl), acenaphthyl group (acenaphthyl), fluorenyl group (Fluorenyl), spiro-fluorenyl group (spiro-fluorenyl), benzofluorenyl group (benzofluorenyl), dibenzofluorenyl group (dibenzofluorenyl), phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), Fluorantenyl group (fluorant enyl), triphenylenyl group (triphenylyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacylyl), picenyl group (picenyl), perylenyl group (perylenyl), pentaphenyl group (pentaphenyl), hexacenyl group (hexacenyl group) ), Pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group (thiophenyl), furanyl group (furanyl), imidazolyl group (imidazolyl), Pyrazolyl group (pyrazolyl), thiazolyl group (thi zolyl), isothiazolyl group (isothiazolyl), oxazolyl group (oxazolyl), isoxazolyl group (isooxazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl group) , Indolyl group, indazolyl group (indazolyl), purinyl group (purinyl), quinolinyl group (quinolinyl), isoquinolinyl group (isoquinolinyl), benzoquinolinyl group (benzoquinolinyl), phthalazinyl group (phthalazinyl), naphthyridinyl group (naphthyridin) yl), quinoxalinyl group (quinoxalinyl), quinazolinyl group (quinazolinyl), cinnolinyl group (cinnolinyl), carbazolyl group (carbazolyl), phenanthridinyl group (phenanthridinyl), acridinyl group (acridinyl), phenanthrolinyl group (phenanthrolinyl) , Phenazinyl group, benzoimidazolyl group (benzoimidazolyl), benzofuranyl group (benzofuranyl), benzothiophenyl group, benzothiothiazolyl group, benzobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group Group ( sobenzoxazolyl), triazolyl group (triazolyl), tetrazolyl group (tetrazolyl), oxadiazolyl group (oxadiazolyl), triazinyl group (triazolyl), dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group (benzocarbazolyl) ), Dibenzocarbazolyl group (dibenzocarbazolyl), imidazopyridinyl group (imidazopyridinyl), and imidazopyrimidinyl group (imidazopyrimidinyl);
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubiceni Group, colonenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, Indryl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrizinyl group, acridinyl group, phenanthrolinyl group , Phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl , Tetrazolyl group, oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, benzo carbazolyl group, dibenzofuranyl carbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, a biphenyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro- Fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , Hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinazolinyl group, carbazolyl group, phenanthridinyl group Group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group Isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl And -Si (Q ₃ ) (Q ₄ ) (Q ₅ );
Q ₃ to Q _5, and _Q 33 _{to Q 35} are each independently, _hydrogen, C 1 _{-C 20} alkyl _group, C 1 _{-C 20} alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl Group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group And quinoxalinyl groups selected from, but not limited to.

According to still another embodiment, R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1 _{21 to} R ₂₃ independently of each other
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its group A salt, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a group represented by the following chemical formulas 4-1 to 4-31, and -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) selected from
Q _{3 to} Q ₅ are, independently of one another, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, and quinoxalinyl group Although selected, it is not limited to them.

In chemical formulas 4-1 to 4-31,
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ), or Si (Z ₃₆ ) (Z ₃₇ ),
Z _{31 to} Z ₃₇ are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl Group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group , selected from among a quinoxalinyl group, and _{-Si (Q 33) (Q 34} ) (Q 35) It is,
Q ₃₃ to Q ₃₅ independently of one another, _hydrogen, C 1 _{-C 20} alkyl _group, C 1 _{-C 20} alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, a fluorenyl group, a chrysenyl group , Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, and quinoxalinyl group Is selected
e1 is an integer of 1 to 5, e2 is an integer of 1 to 7, e3 is an integer of 1 to 3, e4 is an integer of 1 to 4, and e5 is 1 or 2 And e6 is an integer of 1 to 6, and * is a bonding site to an adjacent atom.

According to still another embodiment, R _{1 to} R ₇ , R _{11 to} R ₁₃ , and R in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1 _{21 to} R ₂₃ independently of each other
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its group A salt, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a group represented by the following chemical formulas 5-1 to 5-55, or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) selected from
Q _{3 to} Q ₅ are, independently of one another, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, and quinoxalinyl group Although selected, it is not limited to them.

上記化学式５−１〜５−５５の中の＊は、隣接する原子との結合サイトである。

In the chemical formulas 5-1 to 5-55, * is a bonding site to an adjacent atom.

According to yet another embodiment, R ₁ , R ₂ , and R _{4 to} R ₇ in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and the chemical formulas in Table 1 are Although it is hydrogen, it is not limited to it.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, b1 represents the number of R ₁ and is selected from the integers of 1 to 5 Be done. For example, b1 is 1 or 2. As another example, b1 is 1. When b1 is 2 or more, two or more R _{1 s} are the same as or different from each other. The description of b2, b3, b11 and b12 is understood with reference to the description of b1 and the chemical formulas of 1-1, 1-2-1 and 1A-1 to 1A-12 and Table 1 .

Formula 1,1-1～1-12, and 1A-1~1A-12, as well as by the chemical formula of Table 1, c1 _is - shows the number of _{- [(L 1) a1 (} R 1) b1] And is selected from the integers of 1 to 4. For example, c1 is 1 or 2. When c1 is 2 or more, two or more of-[(L ₁ ) _a1- (R ₁ ) _b1 ] are the same as or different from each other.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, X ₁₁ is C (R ₁₂ ) (R ₁₃ ) or Si (R ₁₂ ) (R ₁₃ ) In certain instances, R ₁₂ and R ₁₃ are the same as or different from one another. For example, when X ₁₁ is C (R ₁₂ ) (R ₁₃ ), various modifications are possible, such as R ₁₂ is a methyl group and R ₁₃ is a phenyl group.

In chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, X ₂₁ is C (R ₂₂ ) (R ₂₃ ) or Si (R ₂₂ ) (R ₂₃ ) In certain instances, R ₂₂ and R ₂₃ are the same as or different from one another. For _example, if _{X 21} is _{C (R 22) (R 2} 3), R 22 is a methyl _{group, R 23} may be such as a phenyl group, various modifications can.

In the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and Table 1, L ₃ is a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted R ₃ is selected from bivalent non-aromatic fused polycyclic groups, and R ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and substituted or non-substituted monovalent non-aromatic fused polycyclic groups It is selected.

For example, in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, L ₃ is a phenylene group, a naphthylene group, and a triphenylene group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof Phenylene substituted with at least one of C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, and chrysenyl group It is selected from among a group, a naphthylene group, and a triphenylene group; and R ₃ is selected from among the chemical formulas 4-1 to 4-5.

According to yet another embodiment, L ₃ is selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and R ₃ is And the fused ring compound represented by Chemical Formula 1 selected from a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic fused polycyclic group is, for example, an organic compound described below It is included in the hole transport region of the light emitting element.

According to yet further embodiments, the chemical formula 1,1-1～1-12, and 1A-1~1A-12, as well as by the chemical formula of Table 1, _{R 3} is an electron-transport component. For example, in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or substituted or unsubstituted It is an unsubstituted monovalent non-aromatic hetero-fused polycyclic group.

For example, in the chemical formulas 1, 1-1 to 1-12, and 1A-1 to 1A-12, and in the chemical formula of Table 1, R ₃ is selected from the group represented by chemical formulas 4-6 to 4-25 But not limited to.

According to yet another embodiment, the condensation represented by Formula 1 wherein R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic hetero fused polycyclic group The ring compound is, for example, included in the light emitting layer of the organic light emitting device described later.

  The fused ring compound is any one of the following compounds 1 to 167, but is not limited thereto.

Fused ring compound represented by Formula 1, as in Formula 1 has a core of rigid structure which many rings are fused to each other, relatively high T _{g (e.g.,} 130 ° C. or more T _g), And relatively low _T.sub.ev (e.g., _T.sub.ev below 350.degree. C.). Thus, the fused ring compound represented by Chemical Formula 1 has excellent process heat resistance.

In addition, the fused ring compound represented by Chemical Formula 1 has various groups in Chemical Formula 1 to X ₁₁ and X ₂₁ (In Chemical Formula 1, the list of X ₁₁ and X ₂₁ refers to the place described in the present specification). There is a bipolar structure in which the electron transport component and the hole transport component are uniformly distributed in the molecule. Thus, the fused ring compound represented by the chemical formula 1 is a HOMO (highest occupied molecular orbital) suitable for use as an electric device, for example, a material for an organic light emitting device (for example, a host or a hole transporting layer material for an organic light emitting device). , LUMO (lowest unoccupied molecular orbital), and T ₁ energy levels.

For example, the results of simulation evaluation of the levels of HOMO, LUMO, and T ₁ energy of compounds 50, 59 to 63, 153, 154, and 158 to 166 using Gaussian are as shown in Table 2 below.

From Table 2, the fused ring compound represented by the chemical formula 1 is suitable for use as a material for an electric device, for example, a material for an organic light emitting device (for example, a host or hole transporting layer material of an organic light emitting device). And T ₁ energy levels are identified.

  According to one embodiment, the fused ring compound represented by Formula 1 is used as a green phosphorescent host or a hole transport layer material for an organic light emitting device, but is not limited thereto.

  Those skilled in the art can easily recognize the synthesis method of the fused ring compound represented by Chemical Formula 1 with reference to the synthesis examples described later.

  The fused ring compound represented by Chemical Formula 1 is suitable for use as a host of the organic layer of the organic light emitting device, for example, the light emitting layer of the organic layer, but according to another aspect, the first electrode, the second electrode And an organic layer containing at least one condensed ring compound represented by Chemical Formula 1 including a light emitting layer interposed between the first electrode and the second electrode.

  The organic light emitting device can have a low driving voltage, high efficiency, high luminance, and a long lifetime by providing the organic layer containing the fused ring compound represented by Chemical Formula 1 as described above.

  The fused ring compound represented by Chemical Formula 1 is used between a pair of electrodes of the organic light emitting device. For example, the fused ring compound includes a light emitting layer, a hole transport region between the first electrode and the light emitting layer (eg, includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer) And at least one of an electron transport region (for example, including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer) between the light emitting layer and the second electrode. For example, the fused ring compound represented by Chemical Formula 1 is included in at least one of the light emitting layer and the hole transporting region. At this time, when the fused ring compound is present in the light emitting layer, the light emitting layer further includes a dopant, and the fused ring compound contained in the light emitting layer plays the role of a host. The light emitting layer is a green light emitting layer that emits green light, and the dopant is a phosphorescent dopant.

  In the present specification, “(organic layer) contains one or more kinds of fused ring compounds” means “(one or more organic ring) fused ring compounds belonging to the category of chemical formula 1 or the category of chemical formula 1 It is interpreted that “contains two or more different fused ring compounds”.

  For example, the organic layer contains only Compound 1 as a fused ring compound. At this time, the compound 1 is present in the light emitting layer of the organic light emitting device. Alternatively, the organic layer contains Compound 1 and Compound 2 as a fused ring compound. At this time, Compound 1 and Compound 2 exist in the same layer (for example, both Compound 1 and Compound 2 exist in the light emitting layer) or exist in different layers (for example, Compound 1 is in the light emitting layer) Compound 2 is present in the hole transport layer).

  For example, the first electrode is an anode, the second electrode is a cathode, and the organic layer is i) interposed between the first electrode and the light emitting layer, a hole injection layer, a hole transport layer, and an electron A hole transport region including at least one of the blocking layers, ii) at least one of the hole blocking layer, the electron transport layer, and the electron injection layer interposed between the light emitting layer and the second electrode And an electron transport region including a layer.

  In the present specification, the term "organic layer" is a term indicating an organic light emitting element including a single layer and / or a plurality of layers interposed between the first electrode and the second electrode. The "organic layer" includes not only organic compounds but also metal-containing organometallic complexes and the like.

  According to still another embodiment, the organic layer of the organic light emitting device includes a first compound represented by the following Chemical Formula 41, and a first compound represented by the following Chemical Formula 61, in addition to the fused ring compound represented by the Chemical Formula 1 as described above. It further comprises at least one of the two compounds.

In chemical formulas 41, 61, 61A, 61B,
X ₄₁ represents N-[(L ₄₂ ) a _42- (R ₄₂ ) b ₄₂ ], S, O, S (= O), S (= O) ₂ , C (= O), C (R ₄₃ ) ( R ₄₄ ), Si (R ₄₃ ) (R ₄₄ ), P (R ₄₃ ), P (= O) (R ₄₃ ), or C = N (R ₄₃ ),
In Formula 61, ring A ₆₁ is represented by Formula 61A:
In Formula 61, ring A ₆₂ is represented by Formula 61B:
X _{61 is, N - [(L 62)} a62 - (R 62) b62], S, O, S (= O), S (= O) 2, C (= O), C (R 63) (R ₆₄ ), Si (R ₆₃ ) (R ₆₄ ), P (R ₆₃ ), P (= O) (R ₆₃ ), or C = N (R ₆₃ ),
X ₇₁ is C (R ₇₁ ) or N, X ₇₂ is C (R ₇₂ ) or N, X ₇₃ is C (R ₇₃ ) or N, and X ₇₄ is C (R ₇₄ ) Or N, X ₇₅ is C (R ₇₅ ) or N, X ₇₆ is C (R ₇₆ ) or N, and X ₇₇ is C (R ₇₇ ) or N, X ₇₈ Is C (R ₇₈ ) or N,
Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ —C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero fused polycyclic group, selected from
n1 and n2 are independently selected from among integers of 0 to 3;
a41, a42, a61, and a62 are independently selected from among integers of 0 to 5;
R _{41 to} R ₄₄ , R _{51 to} R ₅₄ , R _{61 to} R ₆₄ , and R _{71 to} R ₇₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphorus Acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed Hajime Tamaki, a substituted or unsubstituted monovalent nonaromatic family hetero fused Hajime _{Tamaki, -N (Q 1) (Q} 2), - Si (Q 3) (Q 4) (Q5), and is selected from among the _{-B (Q 6) (Q 7} ),
b41, b42, b51 to b54, b61, b62 and b79 are each independently selected from the integers of 1 to 3, and
Substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, Substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted bivalent non-aromatic fused polycyclic group, substituted bivalent non-aromatic hetero fused polycyclic group, Substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C _3- C ₁₀ cycloalkyl group, substituted _C 1 _{-C 10} heterocycloalkyl group, a substituted _C 3 _{-C 10} cycloalkenyl group, _C 1 _{-C 10} Heteroshiku substituted Alkenyl group, a substituted _C 6 _{-C 60} aryl group, a substituted _C 6 _{-C 60} aryloxy group, a substituted _C 6 _{-C 60} arylthio group, a substituted _C 1 _{-C 60} heteroaryl group, a substituted At least one of the substituted monovalent non-aromatic fused polycyclic group and the substituent of the substituted monovalent non-aromatic hetero fused polycyclic group is
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ An aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero fused polycyclic group, C ₁ substituted with at least one of —N (Q ₁₁ ) (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) -C ₆₀ alkyl _Group, C 2 _{-C 60} alkenyl _group, C 2 _{-C 60} alkynyl group, and _C 1 _{-C 60} alkoxy group;
C ₃ -C ₁₀ cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic hetero fused polycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, a monovalent non-aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 21) (Q} 22), - Si (Q 23) ( _{24) (Q 25),} and _{-B (Q} 26) (at least one in _substituted, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl group of _{Q 27), C 3} -C ₁₀ cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group , monovalent nonaromatic condensed Hajime Tamaki, and monovalent non-aromatic heterocyclic condensed Hajime Tamaki; and _{-N (Q 31) (Q 32} ), - Si (Q 33) (Q 34) (Q 35), And -B (Q ₃₆ ) (Q ₃₇ );
Q _{1 to} Q ₇ , Q _{11 to} Q ₁₇ , Q _{21 to} Q ₂₇ and Q _{31 to} Q ₃₇ are each independently hydrogen, a C _{1 to} C ₆₀ alkyl group, a C _{2 to} C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl _group, C 1 _{-C 60} alkoxy _group, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, and monovalent It is selected from non-aromatic hetero-fused polycyclic groups.

  For example, in an organic light emitting device, at least one of i) a fused ring compound represented by the chemical formula 1, ii) a first compound represented by the chemical formula 41, and a second compound represented by the chemical formula 61 include.

  As another example, the light emitting layer includes a first host, a second host, and a dopant, but the first host includes a fused ring compound represented by Chemical Formula 1, and the second host includes a second compound represented by Chemical Formula 41. And at least one of a compound and a second compound represented by Chemical Formula 61.

  The weight ratio of the first host to the second host is selected in the range of 1:99 to 99: 1, for example 10:90 to 90:10. When the weight ratio range is satisfied, the electron transport properties by the first host and the hole transport properties by the second host are balanced, and the luminous efficiency and the lifetime of the organic light emitting device are improved.

Ring A ₆₁ is fused to each of the adjacent 5-membered ring and ring A ₆₂ in Chemical Formula 61 while sharing carbon. Ring A ₆₂ is fused while sharing carbon with each of adjacent ring A ₆₁ and the 6-membered ring in the following chemical formula 61.

According to one embodiment, X ₄₁ is N-[(L ₄₂ ) a _42- (R ₄₂ ) _{b 42} ], S or O, but is not limited thereto.

According to another embodiment, X ₆₁ is N-[(L ₆₂ ) a _62- (R ₆₂ ) b ₆₂ ], S or O, but is not limited thereto.

According to yet further embodiments, the chemical formula _{61, X 71} is C _{(R 71), X 72} is C _{(R 72), X 73} is C _{(R 73),} X ₇₄ is C (R ₇₄ ), X ₇₅ is C (R ₇₅ ), X ₇₆ is C (R ₇₆ ), X ₇₇ is C (R ₇₇ ), and X ₇₈ is , C (R ₇₈ ), but is not limited thereto.

In Chemical Formula 61, at least two of R _{71 to} R ₇₄ are optionally linked to each other to form a saturated or unsaturated ring (eg, benzene, naphthalene, etc.).

On the other hand, in Formula 61, at least two of R ₇ 5~R ₇₈ is optionally linked together to form a saturated or unsaturated ring (e.g., benzene, naphthalene, etc.).

Embodiments of Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ , and L ₆₂ in Chemical Formulas 41, 61, 61A, 61B are mutually independently selected from the embodiments of L ₁ in the present specification. Ru.

According to one embodiment, Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ , and L ₆₂ are each independently of each other:
Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluorantrenylene group, toriphene group Nylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexaphenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group Group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphtyl Nylene group, quinoxalinylene group, quinazolinylene group, cinazolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzimidazolylene group, furanylene group, benzofuranylene group, Thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzo A thiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and deuterium, -F, -Cl, -Br, -I, hydro Sill group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused hetero ring group, -Si (Q ₃₃ Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, substituted with at least one of (Q ₃₄ ) (Q ₃₅ ) Group, phenarenylene group, phenanthrenyl group, anthracenylene group, fluorant lenylene group, triphenylenylene , Pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene Group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthronitrile Nylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothio Phenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarba A zolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group;
Q ₃₃ to Q ₃₅ independently of one another, _hydrogen, C 1 _{-C 20} alkyl _group, C 1 _{-C 20} alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, a fluorenyl group, a carbazolyl group A benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group; It is selected.

According to another embodiment, Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ independently of one another are substituted or unsubstituted C ₃ -C _{10 in} Formulas ₄₁ , 61, 61A, 61B. Selected from a cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted divalent non-aromatic fused polycyclic group Be done.

According to still another embodiment, Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ , and L ₆₂ are each independently of each other in Formulas ₄₁ , 61, 61A, 61B.
A phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenarenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group; -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group substituted with phenyl group (biphenyl group), naphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, Anthracenyl group, fluoranthrenyl group, triphenylenyl A phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenarenylene group, a phenanthrenylene group, an anthracenylene group, a fluorantrenylene group, substituted with at least one of a group, pyrenyl group and chrysenyl group It is selected from, but not limited to, triphenylenylene group, pyrenylene group, and chrysenylene group.

In the chemical formula 41, a41 represents the number of L ₄₁ and is an integer of 0 to 5. For example, a41 is 0, 1 or 2. If a41 is 0, in Formula _{41, * - (L 41)} a41 - * ' becomes a single bond. When a41 is 2 or more, 2 or more of L ₄₁ are the same as or different from each other. a42, a61, and a62 are those showing the number of _{L 42, L 61,} and _{L 62,} respectively, refer to the explanation on the a41.

n1, in the chemical formula 41, which shows the number of _{Ar 41,} selected from among integers from 0 to 3. According to one embodiment, n1 is 0 or 1. For example, n1 is 0, but is not limited thereto.

  For example, in Formulas 41, 61, 61A, and 61B, a41, a42, a61, and a62 are each independently 0 or 1, but are not limited thereto.

The embodiments of R _{41 to} R ₄₄ , R _{51 to} R ₅₄ , R _{61 to} R ₆₄ , and R _{71 to} R _{79 in} the chemical formulas 41, 61, 61A, 61B are each independently selected from the group consisting of R in the present specification. It is selected from among the ₁ embodiment.

According to one embodiment, R _{41 to} R ₄₄ , R _{51 to} R ₅₄ , R _{61 to} R ₆₄ , and R _{71 to} R ₇₉ are each independently of each other
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its group A salt, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group;
Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group Group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, and dibenzocarbazolyl group; -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or a salt _thereof, C 1 _{-C 20} alkyl group, _{C 1} C ₂₀ alkoxy group, a phenyl group, pentalenyl group, a naphthyl group, a fluorenyl group, a spiro - fluorenyl group, benzofluorenyl group, dibenzo fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, a fluoranthenyl group, a triphenylenyl group , Pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, and dibenzocarbazolyl group Group substituted with at least one of: phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracene Group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba It is selected from, but not limited to, Zoryl group, and Dibenzocarbazolyl group.

According to yet another embodiment, R ₅₁ , R ₅₃ , and R ₅₄ in Formula 41, and R _{71 to} R _{79 in} Formula 61, independently of one another, are hydrogen, deuterium, -F, -Cl. , -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl _group, C 2 _{-C 20} alkenyl groups _are selected from C 2 _{-C 20} alkynyl group, and _C 1 _{-C 20} of alkoxy groups.

According to yet another embodiment, R ₅₁ , R ₅₃ and R ₅₄ in Formula 41, and R _{71 to} R _{79 in} Formula 61 are hydrogen.

According to still another embodiment, R ₄₁ , R ₄₂ , and R ₅₂ in Formula 41, and R ₆₁ and R _{62 in} Formula 61 are independently of each other among Formulas 4-1 to 4-31. One of the

According to yet another embodiment, R ₄₁ , R ₄₂ , and R ₅₂ in Formula 41, and R ₆₁ and R _{62 in} Formula 61, independently of each other, have Formulas 4-1 to 4-5, and It is represented by one of the chemical formulas 4-26 to 4-31.

According to still another embodiment, R ₄₁ , R ₄₂ , and R ₅₂ in Formula 41, and R ₆₁ and R _{62 in} Formula 61, independently of each other, are Formulas 5-1 to 5-26, and Although it shows with one of Chemical formula 5-56-5-85, it is not limited to them.

  The first compound is represented by one of the following chemical formulas 41-1 to 41-12, and the second compound is represented by one of the following chemical formulas 61-1 to 61-6, but is limited thereto It is not something to be done.

Chemical formula 41-1 to 41-12 and Chemical formula 61-1 to 61-6, X ₄₁ , X ₆₁ , L ₄₁ , L ₄₂ , a ₄₁ , a ₄₂ , L ₆₁ , L ₆₂ , a ₆₁ , a ₆₂ , R ₄ 1 to according to _{R 44, b41, b42, R} 61 ~R 64, b61, b62, R 71 ~R 79, and b79 description refers to the position described herein.

  According to an embodiment, the first compound represented by the chemical formula 41 includes one of the following compounds A1 to A83, and the second compound represented by the chemical formula 61 is one of the following compounds B1 to B20: Including, but not limited to.

  The light emitting layer of the organic light emitting device, for example, the organic light emitting device further includes at least one of a first compound represented by Chemical Formula 41 and a second compound represented by Chemical Formula 61, in addition to the fused ring compound represented by Chemical Formula 1. When it is included, in the organic light emitting device, the balance between the hole transport and the electron transport is more effectively achieved, and the efficiency, the luminance and the lifetime characteristic of the organic light emitting device are improved.

  The synthesis method of the fused ring compound represented by Chemical Formula 1, the first compound represented by Chemical Formula 41, and the second compound represented by Chemical Formula 61 will be readily recognized by those skilled in the art with reference to the synthesis examples described later. be able to.

  FIG. 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a method of manufacturing an organic light emitting device according to an embodiment of the present invention will be described with reference to FIG. The organic light emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

  A substrate is further disposed below the first electrode 11 or above the second electrode 19. Although a substrate used in a general organic light emitting device can be used as a substrate, a glass substrate or a glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, easy handling, and waterproofness It is desirable to use a transparent plastic substrate.

The first electrode 11 is formed, for example, by providing the material for the first electrode on the substrate using a vapor deposition method, a sputtering method, or the like. The first electrode 11 is an anode. The first electrode material is selected from among materials having a high work function so as to facilitate hole injection. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) or the like can be used as the first electrode material. Alternatively, use metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) be able to.

  The first electrode 11 has a single layer or a multilayer structure including two or more layers.

  An organic layer 15 is disposed on the first electrode 11.

  The organic layer 15 includes a hole transport region, an emission layer, and an electron transport region.

  The hole transport region is disposed between the first electrode 11 and the light emitting layer.

  The hole transport region includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

  The hole transport region includes only the hole injection layer or includes only the hole transport layer. Alternatively, the hole transport region has a structure of hole injection layer / hole transport layer or hole injection layer / hole transport layer / electron blocking layer stacked in order from the first electrode 11.

  When the hole transport region includes the hole injection layer, the hole injection layer (HIL) may be formed on the top of the first electrode 11 as in vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) It is formed using various methods.

When the hole injection layer is formed by vacuum evaporation, the evaporation conditions differ depending on the compound used as the hole injection layer material, the structure of the desired hole injection layer, the thermal characteristics, etc. It is selected in a range of about 100 to about 500 ° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 Å / sec, but is not limited thereto.

  When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure of the desired hole injection layer, and the thermal characteristics, and it is about 2,000 rpm A coating speed of about 5,000 rpm and a heat treatment temperature for solvent removal after coating are selected in a temperature range of about 80 ° C. to about 200 ° C., but are not limited thereto.

  The conditions for forming the hole transport layer and the electron blocking layer refer to the conditions for forming the hole injection layer.

  The hole transport region comprises one or more of the fused ring compounds as described above. For example, in the hole transport region, the hole transport layer comprises one or more of the fused ring compounds as described above.

According to an embodiment, the hole transport region (e.g., the hole transport layer hole transport region), including fused ring compounds represented by Formula 1, in Formula 1, L ₃ is a substituted or non R ₃ is selected from substituted C ₆ -C ₆₀ arylene groups and substituted or unsubstituted divalent non-aromatic fused polycyclic groups, R ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and substituted Or an unsubstituted monovalent non-aromatic fused polycyclic group is selected.

According to another embodiment, the hole transport region (eg, a hole transport layer in the hole transport region) comprises a fused ring compound as shown in Formula 1, but in Formula 1, L ₃ is
A phenylene group, a naphthylene group, and a triphenylene group; and deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group Or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, triphenylenyl groups, pyrenyl groups, phenanthrenyl A phenylene group, a naphthylene group, and a triphenylene group substituted with at least one of a group and a chrysenyl group;
R ₃ is selected from the chemical formulas 4-1 to 4-5.

  Alternatively, the hole transport region may be, for example, 4,4 ′, 4 ′ ′-tris (3-methylphenylphenylamino) triphenylamine (m-MTDATA), 4,4 ′, 4 ′ ′-tris {N, N diphenyl Amino} triphenylamine (TDATA), 4,4 ′, 4 ′ ′-tris (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), N, N′-di (1-naphthyl)- N, N'-diphenylbenzidine (NPB), β-NPB, N, N'-diphenyl-N, N'-di (m-tolyl) benzidine (TPD), Spiro-TPD, Spiro-NPB, methylated NPB, 1,1-Bis [4- [N, N-di (p-tolyl) amino] phenyl] cyclohexane (TAPC), 4-4'-bis [N, N '-(3-tolyl) amino] -3- 3 -Dimethylbiphenyl (HMTPD), 4,4 ′, 4 ′ ′-tris (N-carbazolyl) triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly (3,4-ethylenedioxythiophene) ) / Poly (4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly (4-styrenesulfonate) (PANI / PSS), a compound represented by the following chemical formula 201, and It contains at least one of the compounds represented by the following chemical formula 202.

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ independently from each other
Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group Group, naphthacenylene group, picenylene group, perylenylene group, and pentacenylene group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone Group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C _1- C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl Groups, C ₃ -C ₁₀ cycloalkenyl groups, C ₁ -C ₁₀ heterocycloalkyl groups, C ₁ -C ₁₀ heterocycloalkenyl groups, C ₆ -C ₆₀ aryl groups, C ₆ -C ₆₀ aryloxy groups, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, and substituted by at least one of a monovalent non-aromatic heterocyclic condensed polycyclic group, a phenylene group , Pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluorantenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, Naphthacenylene group, picenylene group, perylenylene group, and pentacenylene group; The inner shell is selected.

  In Chemical Formula 201, xa and xb are each independently an integer of 0 to 5, or 0, 1, or 2. For example, although xa is 1 and xb is 0, it is not limited to them.

In Chemical Formulas 201 and 202, R _{101 to} R ₁₀₈ , R _{111 to} R ₁₁₉ , and R _{121 to} R ₁₂₄ are each independently of each other
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or its group Salts, phosphoric acid groups or salts thereof, C ₁ -C ₁₀ alkyl groups (eg, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group etc.), and C ₁ -C ₁₀ alkoxy groups (eg, Methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group etc.);
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, And a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with any one or more of a phosphoric acid group or a salt thereof;
Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, and pyrenyl group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, Substitution with any one or more of a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group Selected from, but not limited to, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, and pyrenyl group;

In Formula 201, R ₁₀₉ is
Phenyl group, naphthyl group, anthracenyl group, and pyridinyl group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, A carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group; A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group;

  According to one embodiment, the compound represented by Formula 201 is represented by Formula 201A, but is not limited thereto.

For a detailed description of R ₁₀₁ , R ₁₁₁ , R ₁₁₂ , and R ₁₀₉ in Formula 201A, refer to the above.

  For example, the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 include, but are not limited to, the following compounds HT1 to HT20.

  The thickness of the hole transport region is about 100 Å to about 10,000 Å, such as about 100 Å to about 1,000 Å. When the hole transport region includes both the hole injection layer and the hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and the hole transport The thickness of the layer is about 50 Å to about 2,000 Å, such as about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the ranges described above, it is possible to obtain satisfactory hole transport characteristics without a substantial increase in drive voltage. .

  The hole transport region further includes a charge generating material to improve conductivity, in addition to the materials described above. The charge generating material is uniformly or nonuniformly dispersed in the hole transport region.

  The charge generating material is, for example, p-dopant. The p-dopant is any one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ) Examples thereof include, but are not limited to, quinone derivatives; metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1.

  The hole transport region further comprises a buffer layer.

  The buffer layer serves to compensate the optical resonance distance according to the wavelength of light emitted from the light emitting layer and to increase the efficiency.

  A light emitting layer (EML) is formed on the hole transport region using a method such as vacuum evaporation, spin coating, casting, or LB method. When the light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions and the coating conditions vary depending on the compound to be used, but generally selected from conditions substantially the same as the formation of the hole injection layer Be done.

  The light emitting layer contains a host and a dopant. The host includes one or more of the fused ring compounds shown in Chemical Formula 1.

For example, the host includes a fused ring compound represented by Chemical Formula 1, but in Chemical Formula 1, R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent nonaromatic hetero; It is a condensed polycyclic group.

According to one embodiment, the host includes a fused ring compound represented by Formula 1, but in Formula 1, R ₃ is selected from the group represented by Formulas 4-6 to 4-25.

  When the organic light emitting device is a full color organic light emitting device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, various modifications are possible, such as emitting white light by having a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked. In the red light emitting layer, the green light emitting layer, and the blue light emitting layer, the host includes one or more of the fused ring compounds represented by Chemical Formula 1. According to one embodiment, the host of the green light emitting layer includes one or more of the fused ring compounds represented by Formula 1.

  On the other hand, in the light emitting layer, the host includes a first host and a second host, but the first host includes one or more of the fused ring compounds represented by Chemical Formula 1, and the second host has Chemical Formula 41 And at least one of the first compound shown and the second compound shown in Chemical Formula 61.

  In the light emitting layer, the dopant includes a fluorescent dopant which emits light by a fluorescent emission mechanism or a phosphorescent dopant which emits light by a phosphorescent emission mechanism.

  According to one embodiment, the light emitting layer comprises a host and a phosphorescent dopant comprising one or more of the fused ring compounds shown in Formula 1.

  The phosphorescent dopant includes an organometallic compound represented by the following chemical formula 81.

In chemical formula 81,
M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) ,
Y _{1 to} Y ₄ are each independently carbon (C) or nitrogen (N),
Y ₁ and Y ₂ are linked via a single bond or a double bond, and Y ₃ and Y ₄ are linked via a single bond or a double bond,
CY ₁ and CY ₂ are, independently of one another, benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, Pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzooxazole, isobenzoxazole, triazole, tetrazole, oxadiazole Triazine, dibenzofuran, or dibenzothiophene, and CY ₁ and CY ₂ are optionally bonded to each other via a single bond or an organic linking group,
R ₈₁ and R ₈₂ are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF _5, a substituted or unsubstituted _C 1 _{-C 60} alkyl group, a substituted or unsubstituted _C 2 _{-C 60} alkenyl group , Substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted Ku is unsubstituted _C 6 _{-C 60} aryl group, a substituted or unsubstituted _C 6 _{-C 60} aryloxy group, a substituted or unsubstituted _C 6 _{-C 60} arylthio group, a substituted or unsubstituted _C 1 _{-C 60} heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed Hajime Tamaki, a substituted or unsubstituted monovalent non-aromatic hetero fused Hajime _{Tamaki, -N (Q 1) (Q} 2), - Si (Q ₃ ) (Q ₄ ) (Q ₅ ) or -B (Q ₆ ) (Q ₇ ),
a81 and a82 are each independently selected from the integers of 1 to 5;
n81 is selected from the integers of 0 to 4;
n82 is 1, 2 or 3;
L ₈₁ is a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand.
The description of R ₈₁ and R ₈₂ refers to the description of R ₁₁ in the present specification.

  The phosphorescent dopant includes at least one of the following compounds PD1 to PD74, but is not limited thereto (the compound PD1 is Ir (ppy) 3).

  Alternatively, the phosphorescent dopant includes the following PtOEP or compound PhGD.

  The fluorescent dopants include the following 4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl (DPVBi), DPAVBi, TBPe, 4-dicyanomethylene-2- (p-dimethylaminostyryl)- 6-Methyl-4H-pyran (DCM), dichloromethane (DCM) or 4- (dicyanomethylene) -2-tert-butyl-6- (1,1,7,7-tetramethyldurolidin-4-yl-vinyl 4) 4H-Pyran (DCJTB), Coumarin 6 and 10- (2-benzothiazolyl) -2,3,6,7-tetrahydro-1,2,7,7-tetramethyl-1H, 5H, 11H- [1 At least one of benzopyrano [6,7,8-ij] quinolizine-11-one (C545T).

  When the light emitting layer contains a host and a dopant, the content of the dopant is generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is limited thereto It is not a thing.

  The thickness of the light emitting layer is about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light emitting layer satisfies the above range, the light emitting layer exhibits excellent light emitting characteristics without a substantial increase in driving voltage.

  Next, an electron transport region is disposed on the top of the light emitting layer.

  The electron transport region includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

  For example, the electron transport region has a structure of an electron transport layer, a hole blocking layer / electron transport layer / electron injection layer, or an electron transport layer / electron injection layer, but is not limited thereto. The electron transport layer has a single layer or a multilayer structure including two or more different substances.

  The conditions for forming the hole blocking layer, the electron transporting layer, and the electron injection layer in the electron transport region refer to the conditions for forming the hole injection layer.

  When the electron transport region includes a hole blocking layer, the hole blocking layer may be, for example, at least one of the following 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and Bphen: Including, but not limited to.

  The thickness of the hole blocking layer is about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

  The electron transport layer is formed of BCP, Bphen, tris (8-quinolinolato) aluminum (Alq3), aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenolate (BAlq), 1, 2 , 4-triazole derivative (TAZ), and at least one of NTAZ.

  Alternatively, the electron transport layer contains at least one of the following compounds ET1 and ET2, but is not limited thereto.

  The thickness of the electron transport layer is about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, satisfactory electron transport characteristics can be obtained without a substantial increase in drive voltage.

  The electron transport layer further includes a metal-containing substance in addition to the substance as described above.

  The metal-containing material comprises a Li complex. The Li complex includes, for example, the following compound ET-D1 (lithium quinolate (LiQ)) or ET-D2.

  The electron transport region also includes an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

The electron injection layer contains at least one selected from LiF, NaCl, CsF, Li ₂ O, and BaO.

  The thickness of the electron injection layer is about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in drive voltage.

  A second electrode 19 is provided on the organic layer 15. The second electrode 19 is a cathode. As a material for forming the second electrode 19, metals, alloys, electrically conductive compounds, and combinations thereof having a relatively low work function can be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg) -Ag) or the like is used as a material for forming the second electrode 19. Alternatively, various modifications can be made such as forming the transmissive second electrode 19 using ITO or IZO to obtain a front surface light emitting device.

  As mentioned above, although the organic light emitting element was demonstrated with reference to FIG. 1, it is not limited to them.

In the present specification, a C ₁ -C ₆₀ alkyl group means a C ₁ -C ₆₀ linear or branched aliphatic hydrocarbon monovalent group, and specific examples thereof include a methyl group and an ethyl group. Groups, propyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as a C ₁ -C ₆₀ alkyl group.

In the present specification, a C ₁ -C ₆₀ alkoxy group means a monovalent group having a chemical formula of —OA ₁₀₁ (wherein A ₁₀₁ is a C ₁ -C ₆₀ alkyl group), and as a specific example thereof And include methoxy, ethoxy, isopropyloxy and the like.

In the present specification, a C ₂ -C ₆₀ alkenyl group has a structure containing one or more carbon double bonds in the middle or at the end of a C ₂ -C ₆₀ alkyl group, and as a specific example thereof, Ethenyl group, prophenyl group, butenyl group and the like are included. In the present specification, a C ₂ -C ₆₀ alkenylene group means a divalent group having the same structure as a C ₂ -C ₆₀ alkenyl group.

In the present specification, a C ₂ -C ₆₀ alkynyl group has a structure containing one or more carbon triple bonds in the middle or at the end of a C ₂ -C ₆₀ alkyl group, and a specific example thereof is ethynyl Groups (ethynyl), propynyl groups (propynyl) and the like are included. In the present specification, a C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as a C ₂ -C ₆₀ alkynyl group.

In the present specification, a C ₃ -C ₁₀ cycloalkyl group means a C ₃ -C ₁₀ monovalent saturated hydrocarbon monocyclic group, and as a specific example thereof, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group , Cycloheptyl and the like. In the present specification, a C ₃ -C ₁₀ cycloalkylene group means a divalent group having the same structure as a C ₃ -C ₁₀ cycloalkyl group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkyl group is a C ₁ -C ₁₀ univalent single ring containing at least one hetero atom selected from N, O, P and S as a ring-forming atom A group is meant, and specific examples thereof include tetrahydrofuranyl, tetrahydrothiophenyl and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as a C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, a C ₃ -C ₁₀ cycloalkenyl group is a C ₃ -C ₁₀ monovalent monocyclic group and has at least one double bond in the ring but has aromaticity. And the specific examples thereof include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group and the like. In the present specification, a C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as a C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkenyl group is a C ₁ -C ₁₀ monovalent monovalent ring containing as a ring-forming atom at least one hetero atom selected from N, O, P, and S. A group having at least one double bond in the ring. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 2,3-hydrofuranyl group, 2,3-hydrothiophenyl group and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

As used herein, a C ₆ -C ₆₀ aryl group means a monovalent group having a C ₆ -C ₆₀ carbocyclic aromatic system, and a C ₆ -C ₆₀ arylene group is a C ₆ -C ₆₀ carbocyclic aromatic It means a divalent group having a family system. Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group and the like. When C ₆ -C ₆₀ aryl and _C 6 _{-C 60} arylene group include two or more rings, two or more rings are fused together.

In the present specification, a C ₁ -C ₆₀ heteroaryl group contains at least one heteroatom selected from N, O, P and S as a ring-forming atom, and a C ₁ -C ₆₀ carbocyclic aromatic ring C ₁ -C ₆₀ heteroarylene group contains at least one hetero atom selected from among N, O, P, and S as a ring-forming atom, and C _1- It means a C ₆₀ divalent group having a carbocyclic aromatic system. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group comprise two or more rings, the two or more rings are fused to one another.

In the present specification, a C ₆ -C ₆₀ aryloxy group represents -OA ₁₀₂ (wherein A ₁₀₂ represents a C ₆ -C ₆₀ aryl group), and a C ₆ -C ₆₀ arylthio group (arylthio) represents- SA ₁₀₃ (wherein A ₁₀₃ is a C ₆ -C ₆₀ aryl group).

  In the present specification, a monovalent non-aromatic fused polycyclic group is a molecule in which two or more rings are fused to one another and contains only carbon as a ring-forming atom (for example, the carbon number is 8 to 60), It means a monovalent group having non-aromacity as a whole. Specific examples of the non-aromatic fused polycyclic group include a fluorenyl group and the like. In the present specification, a divalent non-aromatic fused polycyclic group means a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

  In the present specification, the monovalent non-aromatic hetero-fused polycyclic group is N, in which two or more rings are fused to each other and carbon is a ring-forming atom (for example, carbon number is 1 to 60). , O, P, and S, each of which is a monovalent group having a non-aromatic character as a whole including a hetero atom selected from the group consisting of The monovalent non-aromatic hetero-fused polycyclic group includes a carbazolyl group and the like. In the present specification, a divalent non-aromatic hetero-fused polycyclic group means a divalent group having the same structure as a monovalent non-aromatic hetero-fused polycyclic group.

As used herein, a substituted C ₁ -C ₆₀ alkylene group, a substituted C ₂ -C ₆₀ alkenylene group, a substituted C ₂ -C ₆₀ alkynylene group, a substituted C ₃ -C ₁₀ cycloalkylene group, Substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic hetero fused polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted has been _C 2 _{-C 60} alkenyl group, a substituted _C 2 _{-C 60} alkynyl group, a substituted _C 3 _{-C 10} cycloalkyl group, _C 1 _{-C 10} Haitai substituted Cycloalkyl group, a substituted _C 3 _{-C 10} cycloalkenyl group, a substituted _C 1 _{-C 10} heterocycloalkenyl group, substituted _C 6 _{-C 60} aryl group, a substituted _C 6 _{-C 60} aryloxy A substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic fused polycyclic group, and a substituted monovalent non-aromatic heterofused poly At least one substituent of the ring group is
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ An aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero fused polycyclic group, C ₁ substituted with at least one of —N (Q ₁₁ ) (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) -C ₆₀ alkyl _Group, C 2 _{-C 60} alkenyl _group, C 2 _{-C 60} alkynyl group, and _C 1 _{-C 60} alkoxy group;
C ₃ -C ₁₀ cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic hetero fused polycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, a monovalent non-aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 21) (Q} 22), - Si (Q 23) ( _{24) (Q 25),} and _{-B (Q} 26) (at least one in _substituted, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl group of _{Q 27), C 3} -C ₁₀ cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group , monovalent nonaromatic condensed Hajime Tamaki, and monovalent non-aromatic heterocyclic condensed Hajime Tamaki; and _{-N (Q 31) (Q 32} ), - Si (Q 33) (Q 34) (Q 35), and _{-B (Q 36) (Q 37} ); chosen among.

Furthermore, in the present specification, Q _{1 to} Q ₇ , Q _{11 to} Q ₁₇ and Q _{31 to} Q ₃₇ are each independently hydrogen, a C _{1 to} C ₆₀ alkyl group, a C _{2 to} C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl _group, C 1 _{-C 60} alkoxy _group, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, and is selected from among the monovalent non-aromatic hetero fused polycyclic group.

For example, substituted _C 1 _{-C 60} alkylene group, substituted _C 2 _{-C 60} alkenylene group, substituted _C 2 _{-C 60} alkynylene group, a substituted _C 3 _{-C 10} cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, disubstituted divalent nonaromatic condensed Hajime Tamaki, a substituted divalent non-aromatic heterocyclic condensed Hajime Tamaki, a substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, a substituted _C 2 _{-C 60} alkynyl group, a substituted _C 3 _{-C 10} cycloalkyl group, _C 1 _{-C 10} Heteroshikuroa substituted Kill, substituted _C 3 _{-C 10} cycloalkenyl group, a substituted _C 1 _{-C 10} heterocycloalkenyl group, substituted _C 6 _{-C 60} aryl group, a substituted _C 6 _{-C 60} aryloxy group A substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic fused multiple ring group, and a substituted monovalent non-aromatic fused heteropolycycle At least one substituent of the group is
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ An aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero fused polycyclic group, C ₁ substituted with at least one of —N (Q ₁₁ ) (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) -C ₆₀ alkyl _Group, C 2 _{-C 60} alkenyl _group, C 2 _{-C 60} alkynyl group, and _C 1 _{-C 60} alkoxy group;
Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group Group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group , Prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnorinyl group, carbazolyl group Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, Isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group ;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, a monovalent non-aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 21) (Q} 22), - Si (Q 23) ( _{24) (Q 25),} and _{-B (Q} 26) (substituted by at least one of _{Q 27),} a phenyl group, an indenyl group, a naphthyl group, azulenyl group, heptalenyl group, indacenyl group, Acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, Pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group , Thiophenyl group, benzothiophenyl group, thiazolyl group, benzothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo carbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; and _{-N (Q 31) (Q 32} ), - Si (Q 33) (Q 34) (Q 35), and -B ( Q ₃₆ ) (Q ₃₇ ); selected from
Q _{1 to} Q ₇ , Q _{11 to} Q ₁₇ , Q _{21 to} Q ₂₇ and Q _{31 to} Q ₃₇ are each independently hydrogen, a C _{1 to} C ₆₀ alkyl group, a C _{2 to} C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl _group, C 1 _{-C 60} alkoxy group, a cyclopentyl group, a cyclohexyl group, cycloheptyl group, cyclooctyl group, a cyclopentenyl group, Shikurohepuseniru group, cycloheptenyl group, a phenyl group, a naphthyl group, anthracenyl group, pyrenyl group , Phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinnolinyl group And quinazolinyl , Phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indasenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, phenalenyl, phenanthrenyl, anthracenyl substituted with at least one of the following: Group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazoli Group, cinnolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, Thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazo It is selected from among pyrimidinyl and imidazopyridinyl groups, but is not limited thereto.

  As used herein, "biphenyl group" means "phenyl group substituted with phenyl group".

  Hereinafter, the compound and the organic light emitting device according to an embodiment of the present invention will be more specifically described by referring to synthesis examples and examples, but the present invention is not limited to the following synthesis examples and examples. . In the following synthesis example, in the expression “in place of“ A ”,“ B ”is used”, the use amount of “B” and the use amount of “A” are the same on a molar equivalent basis.

〔Example〕
Synthesis Example 1: Synthesis of Compound 153

Synthesis of Intermediate A-3
2-bromo-benzo [1,2-b: 5,4-b '] bisbenzofuran 114 g, 4,4,4', 4 ', 5,5,5', 5'-octamethyl-2,2'- 11.3 g of bi (1,3,2-dioxaborolane), 0.5 g of PdCl ₂ (dppf), and 8.8 g of KOAc are placed in a flask and a vacuum environment is established, and then a nitrogen atmosphere is created, and dimethylformamide is formed there. 150 ml of (DMF) was added, and the mixture was heated and stirred at 100 ° C. for 8 hours. The reaction product obtained therefrom was poured into 1,000 ml of MeOH for crystallization, and the solid obtained by stirring and filtering was dissolved by heating in 500 ml of toluene. The reaction product obtained therefrom is filtered through silica, the solvent is removed to 100 ml of a residual solution, and the mixture is crystallized by adding to 1 L of MeOH and dried, and the intermediate A-3 (79. 4g).

Synthesis of Intermediate A-2
Intermediate A-3 1 g, 1-iodo-2-nitrobenzene 0.8 g, Pd (PPh ₃ ) ₄ 0.3 g, and K ₂ CO ₃ 1 g in 20 ml of tetrahydrofuran (THF) / H ₂ O (1: 1) Then, the mixture was heated and stirred at 90 ° C. for 8 hours. The reaction product obtained therefrom is extracted twice using 20 ml of methylene chloride, and to the extract obtained, 2 g of MgSO ₄ is added to remove water, and then the product is purified by silica gel column chromatography, intermediate Body A-2 (0.85 g) was obtained.

Synthesis of Intermediate A-1
1 g of Intermediate A-2 and 2.1 g of PPh ₃ are added to 15 ml of 1,2-dichlorobenzene, heated and stirred for 22 hours, the solvent is distilled off and the residue thus obtained is purified by silica gel column chromatography, and intermediate Body A-1 (0.59 g) was obtained.

<< Synthesis of Compound 153 >>
Intermediate A-1 1 g, 2-chloro-4,6-diphenylpyrimidine 0.95 g, Pd ₂ (dba) ₃ 0.1 g, NaOtBu 0.6 g were put in a flask and a nitrogen atmosphere was established after setting up a vacuum environment. Thereto, 0.1 g of tri (tert-butyl) phosphine and 15 ml of toluene were added, and the mixture was heated and stirred at 110 ° C. for 8 hours. The reaction product obtained therefrom was freed of solvent under vacuum and purified by silica gel column chromatography to obtain Compound 153 (1.41 g). The compound produced was confirmed by LC-MS (chromatography-mass spectroscopy).
C ₄₀ H ₂₃ N ₃ O ₂ : M + 577. 19
¹ H NMR (500 MHz, CDCl 3): δ, ppm 8.59 (d, 1 H), 8.25 to 8.22 (m, 2 H), 8.17 (d, 1 H), 8.04 to 8.02 (M, 4 H), 7.74 to 7.73 (m, 2 H), 7.53 to 7. 50 (m, 1 H), 7.45 to 7. 35 (m, 9 H), 7.32 to 7 .28 (m, 1 H), 7.16 to 7.13 (m, 1 H), 7.00 (s, 1 H)

Synthesis Example 2: Synthesis of Compound 154

<< Synthesis of Intermediate B-4 >>
1.0 g of 2,8-dibromodibenzo [b, d] thiophene, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2 -Dioxaborolane) 2.2 g of PdCl ₂ (dppf) and 0.2 g of KOAc are put in a flask and a vacuum environment is provided, and then a nitrogen atmosphere is created, and then 15.0 ml of DMF is put there and 80 The mixture was heated and stirred at ° C for 18 hours. After adding 10.0 ml of H ₂ O to the reaction product obtained therefrom, the solid obtained by stirring and filtering is washed with 50 ml of MeOH, and the remaining solid is purified by silica gel column chromatography to obtain an intermediate. B-4 (1.1 g) was obtained.

<< Synthesis of Intermediate B-3 >>
Intermediate B-4 1 g, 1-iodo-2-nitrobenzene 1.2 g, Pd (PPh ₃ ) ₄ 0.3 g and K ₂ CO ₃ 1.9 g were placed in 30 ml THF / H ₂ O (1: 1) The mixture was heated and stirred at 80 ° C. for 10 hours. The reaction product obtained therefrom is extracted using methylene chloride, MgSO ₄ is added to the obtained extract, water is removed, and the concentrate obtained is purified by silica gel column chromatography to obtain an intermediate. B-3 (0.81 g) was obtained.

Synthesis of Intermediate B-2
1 g of Intermediate B-3 and 3.1 g of PPh ₃ were added to 12 ml of 1,2-dichlorobenzene and stirred under heating for 24 hours, then the solvent was distilled off and the resulting residue was purified by silica gel column chromatography to obtain an intermediate 0.31 g of body B-2 was obtained.

<< Synthesis of Intermediate B-1 >>
1 g of Intermediate B-2, 0.6 g of iodobenzene, 0.2 g of Pd ₂ (dba) ₃ and 0.6 g of NaOtBu were placed in a flask and a nitrogen atmosphere was created after a vacuum environment was established. Thereto, 0.1 g of tri (tert-butyl) phosphine and 15 ml of toluene were added, and the reaction product obtained by heating and stirring at 110 ° C. for 8 hours was subjected to silica gel column chromatography by removing the solvent under vacuum. Purification gave Intermediate B-1 (0.8 g).

<< Synthesis of Compound 154 >>
Intermediate B-1 1 g, 2-chloro-4,6-diphenyl pyrimidine 1.1 g, Pd ₂ (dba) ₃ 0.2 g, NaO t Bu 0.5 g are put into a flask, and after establishing a vacuum environment, a nitrogen atmosphere is Had made. Thereto, 0.1 g of tri (tert-butyl) phosphine and 15 ml of toluene were added, and the reaction product obtained by heating and stirring at 110 ° C. for 8 hours was subjected to silica gel column chromatography by removing the solvent under vacuum. Purification gave compound 154 (0.95 g). The compound produced was confirmed by LC-MS.
C ₄₆ H ₂ 8 N ₄ S: M + 668. 31
¹ H NMR (300 MHz, CDCl 3): δ, ppm 8.90 (d, 1 H), 8.04 (d, 1 H), 7.93 (d, 1 H), 7.85 (d, 1 H), 7. 74 (d, 1 H), 7. 60 (s, 2 H), 7. 47 (td, 2 H), 7.35 to 7. 11 (m, 15 H), 7.0 6 to 7.00 (m, 1 H) , 6.80 (t, 2H), 6.58 (t, 1H)

Synthesis Example 3: Synthesis of Compound 155

After adding 1 g of Intermediate B-1 to 11 ml of DMF, 0.2 g of NaH is added, and after stirring for 30 minutes at normal temperature, 0.9 g of 2-chloro-4,6-diphenyl-1,3,5-triazine The mixture was stirred for 8 hours at normal temperature. Methylene chloride was added to the reaction product obtained therefrom to dissolve the solid powder, and it was washed using H ₂ O, and then water was removed and concentrated using MgSO ₄ . The concentrate obtained therefrom was purified by silica gel column chromatography to obtain compound 155 (1.38 g). The compound produced was confirmed by LC-MS.
C ₄₅ H ₂₇ N ₅ S: M + 669.24
¹ H NMR (300 MHz, CDCl 3): δ, ppm 8.93 (d, 1 H), 8.03 (d, 1 H), 7.92 (d, 2 H), 7.69 (q, 4 H), 7. 51 (td, 2H), 7.40 to 7.08 (m, 13H), 7.06 to 7.00 (m, 1H), 6.83 (t, 2H), 6.58 (t, 1H)

Synthesis Example 4 Synthesis of Compound 156

Intermediate A-1 1 g, 3-bromo-1,1'-biphenyl 0.81 g, Pd ₂ (dba) ₃ 0.1 g, and NaOtBu 0.6 g are put in a flask, and after a vacuum environment is provided, a nitrogen atmosphere is provided. made. Thereto, 0.1 g of tri (tert-butyl) phosphine and 15 ml of toluene were added, and the reaction product obtained by heating and stirring at 110 ° C. for 12 hours was subjected to silica gel column chromatography by removing the solvent under vacuum. Purification gave compound 156 (1.18 g). The compound produced was confirmed by LC-MS.
C ₃₆ H ₂₁ NO ₂ : M + 499.18
¹ H NMR (500 MHz, DMSO): δ, ppm 9.33 (s, 1 H), 8.30 (d, 1 H), 8.23 (d, 1 H) 8.17 to 8.15 (m, 2 H) 7.78 (d, 1 H), 7.72 (d, 1 H), 7.64 to 7.36 (m, 13 H), 7.29 to 7.26 (m, 1 H)

Synthesis Example 5 Synthesis of Compound 157

1 g of Intermediate B-2, 1.6 g of iodobenzene, 0.2 g of Pd ₂ (dba) ₃ , and 1.01 g of NaOtBu were placed in a flask and a nitrogen atmosphere was created after a vacuum environment was established. Thereto, 0.1 g of tri (tert-butyl) phosphine and 15 ml of toluene were added, and the reaction product obtained by stirring while heating at 110 ° C. for 8 hours was subjected to removal of the solvent under vacuum and silica gel column chromatography To give compound 157 (0.4 g). The compound produced was confirmed by LC-MS.
C ₃₆ H ₂₂ N ₂ S: M + 514.54
¹ H NMR (300 MHz, CDCl 3): δ, ppm 8.20 to 8.15 (m, 2 H), 8.01 (d, 1 H), 7.96 to 7.92 (m, 2 H), 7.87 (D, 1 H), 7.63 (d, 1 H), 7.5 1 to 7. 28 (m, 10 H), 7.20 to 7.14 (m, 2 H), 7.10 to 7.04 (m) , 2H), 6.82 to 6.76 (m, 1H)

Example 1
As an anode, cut ITO / Ag / ITO 70 / 1,000 / 70 Å deposited glass substrate into 50 mm × 50 mm × 0.5 mm size, and use isopropyl alcohol and pure water for over 5 minutes each After sonic cleaning, it was irradiated with ultraviolet light for 30 minutes, exposed to ozone, cleaned, and provided in a vacuum evaporation apparatus.

  After vacuum depositing 2-TNATA on the anode (ITO / Ag / ITO) on the glass substrate to form a 600 Å thick hole injection layer, 4,4′-bis [N] is formed on the hole injection layer. -(1-Naphthyl) -N-phenylamino] biphenyl (NPB) was vacuum deposited to form a 1,000 Å thick hole transport layer.

Compound 153 (host) and Ir (ppy) ₃ (dopant) were co-evaporated at a weight ratio of 90:10 on the hole transport layer to form a 250 Å thick light emitting layer.

  After vacuum evaporation of BCP on the light emitting layer to form a 50 Å thick hole blocking layer, Alq3 is vacuum deposited on the hole blocking layer to form a 350 Å thick electron transport layer, and an electron transport layer LiV is vacuum deposited on top to form a 10 Å thick electron injection layer, then Mg and Ag are vacuum deposited on the electron injection layer at a weight ratio of 90:10 to form a 120 Å thick cathode An organic light emitting device was manufactured.

<< Example 2, Example 3 and Comparative Example 1 >>
An organic light-emitting device was fabricated using the same method as in Example 1, except that a compound as described in Table 3 below was used instead of Compound 153 as a host when forming the light-emitting layer. I made it.

«Evaluation example 1»
The driving voltage, current density, efficiency, and luminance of the organic light emitting devices of Examples 1 to 3 and Comparative Example 1 are supplied with power from a current voltmeter (Keithley SMU 236), and a luminance meter PR650 Spectoscan Source Measurement Unit (PhotoResearch) And the results are shown in Table 3 below.

  From Table 3, it is confirmed that the organic light emitting devices of Examples 1 to 3 have low driving voltage, high efficiency, and high luminance as compared with the organic light emitting device of Comparative Example 1.

Example 4
Compound compound 156 was used instead of NPB when forming the hole transport layer, and CBP was used instead of compound 153 as the host when forming the light emitting layer, as in Example 1 An organic light emitting device was manufactured using the same method.

Example 5
An organic light-emitting device was manufactured using the same method as Example 4, except that Compound 157 was used instead of Compound 156 to form the hole transport layer.

«Evaluation example 2»
The driving voltages of the organic light emitting devices of Examples 4 and 5 and Comparative Example 1 were evaluated by supplying power from a current voltmeter (Keithley SMU 236), and the results are shown in Table 4 below.

  From Table 4, it is confirmed that the organic light emitting devices of Examples 4 and 5 have lower driving voltage than the organic light emitting device of Comparative Example 1.

Example 6
Using the same method as in Example 1, except that compound 155 (host) and Ir (ppy) 3 (dopant) were co-deposited at a weight ratio of 85:15 when forming the light emitting layer An organic light emitting device was manufactured.

<< Example 7 >>
In forming the light emitting layer, except that compound 155 (first host), compound A2 (second host), and Ir (ppy) 3 (dopant) were co-deposited at a weight ratio of 45:45:10. The organic light emitting device was manufactured using the same method as Example 1.

«Evaluation example 3»
The driving voltage, current density, efficiency, and luminance of the organic light emitting devices of Examples 6 and 7 are supplied with power from a current voltmeter (Keithley SMU 236), and a luminance meter PR650 Spectoscan Source Measurement Unit (manufactured by PhotoResearch) is used. The evaluation is shown in Table 5. Table 5 also shows the data of Comparative Example 1 for comparison.

  From Table 5, it is confirmed that the organic light emitting devices of Examples 6 and 7 have lower driving voltage, higher luminance, and higher efficiency than the organic light emitting device of Comparative Example 1.

  As mentioned above, although the embodiment of the present invention was described in detail, the present invention is not limited to the above-mentioned embodiment, and can be variously changed and carried out within the technical scope of the present invention. It is.

  The fused ring compound of the present invention and the organic light emitting device including the same are effectively applicable to, for example, the technical fields related to light emission.

10 organic light emitting element 11 first electrode 15 organic layer 19 second electrode

Claims (10)

It is shown by following Chemical formula 1 A-2 The condensed ring compound characterized by the above-mentioned.

In Formula 1A-2,
X ₁₁ is S or O,
X _{21 is, N - [(L 21)} a21 - (R 21) b21], an S, or O,
L _{1 to} L ₃ and L ₂₁ are each independently selected from the groups represented by the following chemical formulas 2-1 to 2-34,
a1 to a3 and a21 are each independently 0, 1 or 2;
R _{1 to} R ₇ and R ₂₁ each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group A group, a group represented by the following chemical formulas 4-1 to 4-31, and -Si (Q ₃ ) (Q ₄ ) (Q ₅ );
The Q _{3 to} Q ₅ are each independently hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl Group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, and quinoxalinyl group ,
b1 to b3 and b21 are each independently selected from the integers of 1 to 5, and
c1 and c2 are independently selected from among integers of 1 to 4.

In the above-mentioned chemical formulas 2-1 to 2-34,
Y ₁ is O, S, S (= O), S (= O) ₂ , C (Z ₃ ) (Z ₄ ), N (Z ₅ ), or Si (Z ₆ ) (Z ₇ ),
Z _{1 to} Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group Group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , quinazolinyl group, quinoxalinyl group, a biphenyl group, and -Si _(Q 33) _{(Q 4)} is selected from among the _{(Q 35),}
Each of Q _{33 to} Q ₃₅ independently represents hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl Groups, benzocarbazolyl, dibenzocarbazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, triazinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl and quinazolinyl Is selected
d1 is an integer of 1 to 4, d2 is an integer of 1 to 3, d3 is an integer of 1 to 6, d4 is an integer of 1 to 8, and d5 is 1 or 2 And d6 is an integer of 1 to 5;
Each of * and * 'is a bonding site to an adjacent atom.

In the chemical formulas 4-1 to 4-31,
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ), or Si (Z ₃₆ ) (Z ₃₇ ),
Z _{31 to} Z ₃₇ each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, Carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl Group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group , quinoxalinyl group, and _{-Si (Q 33) (Q 34} ) selected from among the _{(Q 35)} It is,
Each of Q _{33 to} Q ₃₅ independently represents hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group Is selected from
e1 is an integer of 1 to 5, e2 is an integer of 1 to 7, e3 is an integer of 1 to 3, e4 is an integer of 1 to 4, and e5 is 1 or 2 And e6 is an integer of 1 to 6, and * is a bonding site to an adjacent atom. The fused ring compound is represented by any one of the following chemical formulas 1A-2-9 to 1A-2-11, and 1A-2-14 to 1A-2-16. The fused ring compound described in 4.

The fused ring according to claim 1 or 2, wherein L _{1 to} L ₃ and L ₂₁ are each independently any one of the following chemical formulas 3-1 to 3-21. Compound.

Each of * and * 'is a bonding site to an adjacent atom. When X ₂₁ is N-[(L ₂₁ ) a _11- (R ₂₁ ) _{b 11} ], at least one of R ₃ and R ₂₁ independently of each other may be represented by the chemical formulas 4-1 to 4-31. The fused ring compound according to claim 1, which is selected from the groups represented. The fused ring compound according to claim 1, wherein R ₃ is selected from among the groups represented by the chemical formulas 4-6 to 4-31. R _{1 to} R ₇ and R ₂₁ are each independently
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano _group, C 1 _{-C 20} alkyl _group, C 1 _{-C 20} alkoxy group, a group represented by the following chemical formula 5-1～5-55, And -Si (Q ₃ ) (Q ₄ ) (Q ₅ ), and
The Q _{3 to} Q ₅ are each independently hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group The fused ring compound according to claim 1, wherein the fused ring compound is selected from

In the chemical formulas 5-1 to 5-55, * is a bonding site to an adjacent atom. The fused ring compound according to claim 1, which is any one of the following compounds.

  The light emitting layer which intervenes between the 1st electrode, the 2nd electrode, and the 1st electrode and the 2nd electrode contains one or more sorts of condensation ring compounds according to any one of claims 1 to 7. And an organic layer.   The first electrode is an anode, the second electrode is a cathode, and the organic layer is i) interposed between the first electrode and the light emitting layer, a hole injection layer, a hole transport layer, And a hole transport region including at least one of the electron blocking layers, and ii) a hole blocking layer, an electron transport layer, and an electron injection layer interposed between the light emitting layer and the second electrode. And an electron transport region including at least one layer of the organic light emitting diode according to claim 8. The fused ring compound is included in the light emitting layer, and the light emitting layer further includes at least one of a first compound represented by the following chemical formula 41 and a second compound represented by the following chemical formula 61. The organic light emitting device according to claim 8.

In Formulas 41, 61, 61A, and 61B,
X ₄₁ represents N-[(L ₄₂ ) a _42- (R ₄₂ ) b ₄₂ ], S, O, S (= O), S (= O) ₂ , C (= O), C (R ₄₃ ) ( R ₄₄ ), Si (R ₄₃ ) (R ₄₄ ), P (R ₄₃ ), P (= O) (R ₄₃ ), or C = N (R ₄₃ ),
In Formula 61, ring A ₆₁ is represented by Formula 61A.
In the above Formula 61, ring A ₆₂ is represented by the above Formula 61B:
X _{61 is, N - [(L 62)} a62 - (R 62) b62], S, O, S (= O), S (= O) 2, C (= O), C (R 63) (R ₆₄ ), Si (R ₆₃ ) (R ₆₄ ), P (R ₆₃ ), P (= O) (R ₆₃ ), or C = N (R ₆₃ ),
X ₇₁ is C (R ₇₁ ) or N, X ₇₂ is C (R ₇₂ ) or N, X ₇₃ is C (R ₇₃ ) or N, and X ₇₄ is C (R ₇₄ ) Or N, X ₇₅ is C (R ₇₅ ) or N, X ₇₆ is C (R ₇₆ ) or N, and X ₇₇ is C (R ₇₇ ) or N, X ₇₈ Is C (R ₇₈ ) or N,
Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ —C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero fused polycyclic group, selected from
n1 and n2 are independently selected from among integers of 0 to 3;
a41, a42, a61, and a62 are each independently selected from the integers of 0 to 5;
R _{41 to} R ₄₄ , R _{51 to} R ₅₄ , R _{61 to} R ₆₄ , and R _{71 to} R ₇₉ each independently represent hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphorus Acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted _C 1 _{-C 10} heterocycloalkenyl groups, substituted or unsubstituted _C 6 _{-C 60} aryl group, a substituted or unsubstituted _C 6 _{-C 60} aryloxy group, Substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-substituted aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 1) (Q} 2), - Si (Q 3) (Q 4) (Q5), and is selected from among the _{-B (Q 6) (Q 7} ),
b41, b42, b51 to b54, b61, b62 and b79 are each independently selected from the integers of 1 to 3, and
Wherein substituted _C 3 _{-C 10} cycloalkylene group, substituted _C 1 _{-C 10} heterocycloalkylene, substituted _C 3 _{-C 10} cycloalkenylene, substituted _C 1 _{-C 10} heterocycloalkyl cycloalkenylene A substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted divalent non-aromatic fused polycyclic group, a substituted divalent non-aromatic hetero fused polycyclic group , A substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, substituted _C 1 _{-C 10} heterocycloalkyl group, a substituted _C 3 _{-C 10} cycloalkenyl group, _C 1 _{-C 10} heteroaryl which is substituted Kuroarukeniru group, a substituted _C 6 _{-C 60} aryl group, a substituted _C 6 _{-C 60} aryloxy group, a substituted _C 6 _{-C 60} arylthio group, a substituted _C 1 _{-C 60} heteroaryl group, At least one of the substituted monovalent non-aromatic fused polycyclic group and the substituent of the substituted monovalent non-aromatic hetero fused polycyclic group is
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ An aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero fused polycyclic group, C ₁ substituted with at least one of —N (Q ₁₁ ) (Q ₁₂ ), —Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), and —B (Q ₁₆ ) (Q ₁₇ ) -C ₆₀ alkyl _Group, C 2 _{-C 60} alkenyl _group, C 2 _{-C 60} alkynyl group, and _C 1 _{-C 60} alkoxy group;
C ₃ -C ₁₀ cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic hetero fused polycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, Phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed Hajime Tamaki, a monovalent non-aromatic heterocyclic condensed Hajime _{Tamaki, -N (Q 21) (Q} 22), - Si (Q 23) ( _{24) (Q 25),} and _{-B (Q} 26) (at least one in _substituted, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl group of _{Q 27), C 3} -C ₁₀ cycloalkenyl _group, C 1 _{-C 10} heterocycloalkenyl _radical, C 6 _{-C 60} aryl _group, C 6 _{-C 60} aryloxy _group, C 6 _{-C 60} arylthio _group, C 1 _{-C 60} heteroaryl group , monovalent nonaromatic condensed Hajime Tamaki, and monovalent non-aromatic heterocyclic condensed Hajime Tamaki; and _{-N (Q 31) (Q 32} ), - Si (Q 33) (Q 34) (Q 35), And -B (Q ₃₆ ) (Q ₃₇ );
The Q _{1 to} Q ₇ , Q _{11 to} Q ₁₇ , Q _{21 to} Q ₂₇ , and Q _{31 to} Q ₃₇ are each independently hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl _group, C 1 _{-C 60} alkoxy _group, C 3 _{-C 10} cycloalkyl _group, C 1 _{-C 10} heterocycloalkyl _group, C 3 _{-C 10} cycloalkenyl _group, C 1 _{-C 10} heteroaryl A cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic fused polycyclic group, and It is selected from among nonvalent heteroaromatic fused polycyclic groups.

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