KR101390523B1 - Novel compounds and organic electro luminescence device using the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device using the same. More specifically, the present invention relates to a compound in which various substituents are bonded to a basic skeleton in which an indene compound and a condensed heterocyclic moiety are connected to each other, will be. The present invention can provide an organic electroluminescent device with improved efficiency, lifetime, and stability.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound, and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

TECHNICAL FIELD The present invention relates to a novel compound and an organic electroluminescent device including the same and more particularly to a compound used in an organic material layer of an organic electroluminescent device.

A study on the electroluminescent (EL) devices that led to the blue electroluminescence using the anthracene single crystal in 1965 based on the observation of the organic thin film emission of the Bernanose in the 1950s was carried out by Tang in 1987, An organic electroluminescent device having a laminated structure divided by functional layers has been proposed. In order to improve the efficiency and lifetime of the organic electroluminescent device, the organic electroluminescent device has been developed to introduce characteristic organic layers in the device.

In the organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic layer, and the injected holes and electrons meet to form an exciton. When the exciton formed drops to a ground state The light comes out. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, so that the phosphorescent dopant as well as the phosphorescent host have been studied.

Up to now, the hole transport layer. NPB, BCP, Alq ₃ and the like are widely known as materials used as a hole blocking layer and an electron transporting layer, and an anthracene derivative is used as a luminescent material. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having great advantages in terms of efficiency improvement of light emitting materials are blue, green, red phosphorescent dopant materials, CBP is used as a phosphorescent host material.

However, since conventional luminescent materials have good luminescence characteristics, they have low glass transition temperature and are not very satisfactory in terms of the lifetime of the organic electroluminescent devices because of their poor thermal stability, development of luminescent materials having excellent performance is required .

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

X and Y are the same or different and are selected from the group consisting of CR ₃ R ₄ , O, S, NR ₅ , and SiR ₆ R ₇ except when X and Y are both CR ₃ R ₄ ;

R ₁ to R ₇ are the same or different from each other and represent hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl Group, a C ₅ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group , A C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ arylsilyl group, and a C ₃ to C ₄₀ heterocycloalkyl group;

Ar ₁ to Ar ₃ are the same or different from each other, hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ of C ₆ to C ₄₀ aryloxy groups, C ₆ to C ₄₀ arylsilyl groups and C ₆ to C ₄₀ aryl groups, C ₅ to C ₆₀ heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ aryloxy groups, ₄₀ < / RTI > arylamine groups;

a, b and c are an integer of 0 to 4;

Wherein R ₁ to R ₇ are independently selected from the group consisting of hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, A C ₆ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C Which may be unsubstituted or substituted with a substituent selected from the group consisting of an aryl group, a C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ arylsilyl group, and a C ₃ to C ₄₀ heterocycloalkyl group have.

The C ₁ to C ₄₀ alkyl groups and C ₁ to C ₄₀ alkyloxy groups represented by Ar ₁ to Ar ₃ may be linear or branched, and include C ₆ to C ₄₀ aryl groups, C ₅ to C ₄₀ heteroaryl Group, a C ₆ to C ₄₀ aryloxy group and a C ₆ to C ₄₀ arylamine group may be fused or unfused.

In addition, Ar ₁ to Ar ₃ may be fused with adjacent groups to form a ring.

The present invention also provides compounds selected from the group consisting of compounds represented by the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,

X, Y, R ₁ to R ₇ , Ar ₁ to Ar ₃ And a, b and c are the same as defined in the compound represented by the formula (1)

X 'and Y' are the same or different from each other, and CR ₃ "R ₄ '. O, S, NR ₅ 'and SiR ₆ ' R ₇ ', with the proviso that X' and Y 'are not CR ₃ ' R ₄ ';

R ₁ ' To R ₇ 'are the same or different from each other and represent hydrogen, deuterium, halogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A C ₅ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, A C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ arylsilyl group, and a C ₃ to C ₄₀ heterocycloalkyl group;

Ar ₁ 'to Ar ₃ ' are the same or different from each other and represent hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, C ₃ to C ₄₀ heterocycloalkyl, C an aryl group of ₆ ~ C _40, C ₅ ~ heteroaryl group of C _60, C ₁ ~ C ₄₀ alkyloxy group of, C aryloxy of _{6 ~ C 40, C 6 ~} C 40 aryl silyl group, and a C ₆ of ~ C ₄₀ is selected from the group consisting of an aryl amine;

a ', b' and c 'are an integer of 0 to 4;

Here, R ₁ 'to R ₇ ' may also be substituted with the substituents described above as R ₁ to R ₇ .

In the above Ar ₁ 'to Ar ₃ ', the C ₁ to C ₄₀ alkyl group and the C ₁ to C ₄₀ alkyloxy group may be linear or branched, and include C ₆ to C ₄₀ aryl groups, C ₅ to C ₄₀ a heteroaryl group, C ₆ ~ C ₄₀ aryloxy and C ₆ ~ C ₄₀ arylamine groups may be fused or non-fused.

In addition, Ar ₁ 'to Ar ₃ ' may be fused with adjacent groups to form a ring.

On the other hand, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the organic layers is represented by the general formulas And the organic compound layer is an organic compound layer containing any one of the compounds.

Here, the organic material layer may be a light emitting layer, a hole transporting layer, or an electron transporting layer.

When one of the compounds represented by the general formulas (1) to (4) of the present invention is used as a light emitting material of an organic electroluminescent device, the efficiency (luminous efficiency and messenger efficiency), lifetime, The driving voltage and the like can be improved. Therefore, the present invention can improve the performance and lifetime of the full color organic EL panel.

Hereinafter, the present invention will be described in detail.

1, a novel compound

The novel compound according to the present invention is a compound in which an indene compound and a fused heterocyclic moiety are linked to form a basic skeleton and various substituents are bonded thereto, and is represented by the formula 1 (hereinafter referred to as a 'formula I') . The compound I of the present invention can be prepared by mixing various substituents (R ₁ , R ₂ and Ar ₁ to Ar ₃ in the above formula (1)) to control the energy level so that a conventional organic light emitting device material (for example, CBP , 4-dicarbazolybiphenyl), and exhibits a wide energy bandgap.

Specifically, in the compound I of the present invention, the heterocyclic moiety is phenothiazine (a compound in which one of X and Y is NH and the other is S), phenoxazine (X in Formula 1) Or a compound wherein Y is NH and the other is O, arridine (a compound wherein one of X and Y is NH and the other is CH ₂ ), phenazasiline (compound of formula 1) When one of X and Y is NH and the other is SiH ₂ ), various substituents can be easily introduced, and the triplet energy state can be stably formed by the introduced substituent to control the energy level have.

In addition, the compound I of the present invention in which various substituents have been introduced has a significantly increased molecular weight, thereby improving the glass transition temperature and thus having higher thermal stability than conventional materials.

Therefore, when Compound I of the present invention is used as a material for an organic electroluminescent device, not only the phosphorescence characteristics of the device, but also the electron and / or hole transporting ability, luminous efficiency, driving voltage and lifetime characteristics can be improved. At this time, the compound I of the present invention can be used as a material of an organic material layer of an organic electroluminescent device, preferably a material of a light emitting layer, a hole transporting layer or an electron transporting layer, more preferably a host material of a light emitting layer.

Examples of such substituents R ₁ to R ₇ and Ar ₁ to Ar ₃ of the compound I of the present invention include, but are not limited to, the following examples (S1 to S138).

The compound I of the present invention is preferably selected from the group consisting of compounds represented by the following formulas C-1 to C-11, but is not limited thereto.

In the above formulas C-1 to C-11,

The definitions of R ₁ to R ₇ , Ar ₁ to Ar _3, and a, b, and c are the same as those defined in the above-mentioned compound I.

Meanwhile, considering the efficiency and lifetime characteristics of the organic electroluminescent device, R ₁ and R ₂ in the formulas (C-1) to (C-11) are preferably the same and are preferably a methyl group or a phenyl group. In the above formulas C-1 to C-11, R ₃ and R ₄ are also the same and preferably a methyl group or a phenyl group. In the above formulas C-1 to C-11, it is preferable that R ₅ is a C ₆ to C ₄₀ aryl group or a C ₅ to C ₄₀ heteroaryl group.

The compounds represented by the above Formulas C-1 to C-11 can be synthesized as follows.

A. Examples of the compound represented by the formula C-1 include compounds A-1 to A-4

A-1) Synthesis of Compound A-1

(0.128 mol) of 2-bromo-9,9-dimethyl-9,10-dihydroacridine and 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 , 5.25 g (5 mol%) of Pd (dppf) Cl ₂ , 37.55 g (0.383 mol) of KOAc and 500 ml of DMF were placed and stirred at 130 ° C for 12 hours The reaction is terminated, extracted with ethyl acetate and the water is removed with MgSO ₄ . The solvent was removed and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 9,9-dimethyl- 2- (4,4,5,5-tetramethyl- dioxaborolan-2-yl) -9,10-dihydroacridine (0.051 mol) (yield 40%).

8.72 g (0.040 mol) of methyl 2-bromobenzoate, 9,9-dimethyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 18.53 g (0.051 mol) of dihydroacridine, 4.75 g (118.8 mmol) of NaOH and 200 ml / 100 ml of THF / H ₂ O are added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 2.29g (5 mol%) and stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture is extracted with methylene chloride, and the mixture is filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, methyl 2- (9,9-dimethyl-9,10-dihydroacridin-2-yl) benzoate 13.21 (3H) was obtained by column chromatography (Hexane: EA = 3: 1 g (35.7 mmol) (yield 70%).

13.21 g (35.7 mmol) of methyl 2- (9,9-dimethyl-9,10-dihydroacridin-2-yl) benzoate was charged with argon in a vacuum atmosphere, followed by the addition of 1 L of tetrahydrofuran and stirring at -75 ° C for 10 minutes. 100 mL (0.16 mmol) MeLi (1.6 M in hexane) was added, and the mixture was stirred at -75 째 C for 10 minutes and then at room temperature for 3 hours. When the reaction is complete, extract with distilled water and ethyl acetate. The organic layer was dried over MgSO ₄ and then the solvent was removed. The organic layer was separated by column using hexane and ethyl acetate to give 2- (9,9-dimethyl-9,10-dihydroacridin-2-yl) phenylpropan- g (30.3 mmol) (yield 85%).

11.23 g (30.3 mmol) of 2- (9,9-dimethyl-9,10-dihydroacridin-2-yl) phenylpropan-2-ol was placed in a flask, 300 mL of AcOH was added, Lt; / RTI > After adding 400 mL of H ₃ PO ₄ and stirring at room temperature for 1 hour, the reaction is neutralized with NaOH and extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO ₄ and the solvent was removed. The solvent was removed by column separation using hexane and ethyl acetate to obtain 7,7,13,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b ] acridine (yield: 74%).

^{1 H-NMR: δ 1.72 (} s, 12H), 4.00 (s, 1H), 6.67 (s, 1H), 6.73-6.75 (d, 2H), 7.02-7.05 (t, 2H), 7.28-7.38 (t , 2H), 7.46 (s, 1 H) 7.55 - 7.60 (d, 2 H)

Elemental Analysis: C, 88.57; H, 7.12; N, 4.30 [M < + >]: 324

A-2) Synthesis of Compound A-2

Except that 2,7-dibromo-9,9-dimethyl-9,10-dihydroacridine was used instead of 2-bromo-9,9-dimethyl-9,10-dihydroacridine in the synthesis of the compound A-1. Synthesized.

A-3) Synthesis of Compound A-3

The synthesis was carried out in the same manner except that methyl 2-bromo-5-chlorobenzoate was used instead of methyl 2-bromobenzoate in the synthesis of the compound A-1.

A-4) Synthesis of Compound A-4

In the synthesis of A-1 above, 2,7-dibromo-9,9-dimethyl-9,10-dihydroacridine was used instead of 2-bromo-9,9-dimethyl-9,10-dihydroacridine, and methyl 2-bromobenzoate 2-bromo-5-chlorobenzoate.

B. Examples of the compound represented by the formula C-2 include compounds B-1 to B-4

B-1) Synthesis of Compound B-1

Except that 3-bromo-9,9-dimethyl-9,10-dihydroacridine was used in place of 2-bromo-9,9-dimethyl-9,10-dihydroacridine in the synthesis of Compound A-1 .

B-2) Synthesis of Compound B-2

Except that 3,6-dibromo-9,9-dimethyl-9,10-dihydroacridine was used instead of 2,7-dibromo-9,9-dimethyl-9,10-dihydroacridine in the synthesis of Compound A- .

B-3) Synthesis of Compound B-3

Except that 3-bromo-9,9-dimethyl-9,10-dihydroacridine was used instead of 2-bromo-9,9-dimethyl-9,10-dihydroacridine in the synthesis of Compound A-3 .

B-4) Synthesis of Compound B-4

3,6-dibromo-9,9-dimethyl-9,10-dihydroacridine was used instead of 2,7-dibromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene in the synthesis of Compound A- , methyl 2-bromo-5-chlorobenzoate instead of methyl 2-bromobenzoate.

C. Synthesis of Compound Represented by Formulas C-3 to C-11

C-3 to C-11 were obtained by the same method except that 2-bromo-9,9-dimethyl-9,10-dihydroacridine was used in the synthesis of the compound A-1, ≪ / RTI >

C-3 2-bromo-5,10-dihydrophenazine C-4 3-bromo-10H-phenoxazine C-5 3-bromo-10H-phenothiazine C-6 2-bromo-5,10-dihydrodibenzo [b, e] [1,4] azacilline C-7 2-bromo-9,9-dimethyl-9H-thioxanthene C-8 2-bromothianthrene C-9 2-bromo-9,9-dimethyl-9H-xanthene C-10 2-bromo-9,9-dimethyl-9H-thioxanthene C-11 2-bromo-10,10-dimethyl-5,10-dihydrodibenzo [b, e] silane

In addition to the compounds shown above, the present invention can synthesize various compounds represented by the formulas C-1 to C-11 with reference to the above synthesis method. Examples of the compounds represented by formulas C-1 to C-11 of the present invention (specifically, examples of formula C-1) include, but are not limited to, the following compounds (C1 to C112).

On the other hand, the novel compound according to the present invention may be a compound in which the compound I is bonded symmetrically or asymmetrically. That is, the novel compounds according to the present invention can be selected from the group consisting of compounds represented by the following formulas (2) to (4). Specifically, a compound represented by the formula (2) (hereinafter referred to as a 'compound II') is a compound in which the heterocyclic moieties of the compound I are bonded together, and the compound represented by the formula (3) (Hereinafter referred to as "compound IV") is a compound bonded to the indene compound side of Compound I, and the compound represented by Formula 4 (hereinafter referred to as Compound IV) is bonded to the indene compound side.

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,

X, Y, R ₁ to R ₇ , Ar ₁ to Ar ₃ And a, b and c are the same as defined in the compound represented by the formula (1)

X 'and Y' are the same or different from each other, and CR ₃ 'R ₄ '. O, S, NR ₅ 'and SiR ₆ ' R ₇ ', with the proviso that X' and Y 'are not CR ₃ ' R ₄ ';

R ₁ ' To R ₇ 'are the same or different from each other and represent hydrogen, deuterium, halogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group , A C ₅ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, A C ₆ to C ₄₀ arylalkyl group, a C ₃ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ arylsilyl group, and a C ₃ to C ₄₀ heterocycloalkyl group;

Ar ₁ 'to Ar ₃ ' are the same or different from each other and represent hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, C ₃ to C ₄₀ heterocycloalkyl, C an aryl group of ₆ ~ C _40, C ₅ ~ heteroaryl group of C _60, C ₁ ~ C ₄₀ alkyloxy group of, C aryloxy of _{6 ~ C 40, C 6 ~} C 40 aryl silyl group, and a C ₆ of ~ C ₄₀ is selected from the group consisting of an aryl amine;

a ', b' and c 'are an integer of 0 to 4;

Since the compounds II to IV of the present invention contain the compound I as a basic unit, even when any one of the compounds II to IV is used as the material of the organic electroluminescence device, the phosphorescence property of the device, as well as the electron and / Transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. At this time, the compounds II to IV of the present invention can also be used as a material of an organic material layer of an organic electroluminescent device, preferably a material of a light emitting layer, a hole transporting layer or an electron transporting layer, more preferably a host material of a light emitting layer.

Considering the efficiency and lifetime characteristics of the organic electroluminescent device, R ₁ and R ₂ in the compounds II to IV are the same as each other and are a methyl group or a phenyl group, and R ₁ 'and R ₂ ' are also the same and are a methyl group or a phenyl group . R ₃ and R ₄ in the compounds II to IV are the same as each other and are a methyl group or a phenyl group, and R ₃ 'and R ₄ ' are also the same and are preferably a methyl group or a phenyl group. Here, R ₁ and R ₂ may be the same as or different from R ₁ 'and R ₂ ', and R ₃ and R ₄ may also be the same as or different from R ₃ 'and R ₄ '. In addition, in the compounds II to IV, R ₅ and R ₅ 'are preferably a C ₆ to C ₄₀ aryl group or a C ₅ to C ₄₀ heteroaryl group, and they may be the same or different.

The compounds II to IV of the present invention can be synthesized with reference to the synthesis process of the compound I (the process of synthesizing the compounds represented by the formulas C-1 to C-11), and the following compounds (C113 to C118 ), But the present invention is not limited thereto.

2. Organic Field  Light emitting element

The present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers is a compound represented by any one of formulas Is an organic material layer containing any one of the compounds represented by the following formulas.

The organic material layer containing any one of the compounds represented by the general formulas (1) to (4) of the present invention may be any one or more of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer. Specifically, the organic material layer is preferably a hole transporting layer, a light emitting layer, or an electron transporting layer, more preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device according to the present invention may contain a host material. In this case, any one of the compounds represented by the above formulas 1 to 4 may be used as a host material. When the light emitting layer contains any one of the compounds represented by Chemical Formulas 1 to 4 as described above, the hole transporting ability is increased, and the bonding force between holes and electrons in the light emitting layer is increased. Therefore, efficiency (luminous efficiency and power efficiency), lifetime, It is possible to provide an organic electroluminescent device excellent in voltage and the like.

In addition, when the hole transport layer of the organic electroluminescent device according to the present invention includes any one of the compounds represented by the general formulas (1) to (4), the hole transporting ability is improved and the characteristics of the organic electroluminescent device can be improved. When any one of the compounds represented by Chemical Formulas 1 to 4 is included in the hole transporting layer, Ar ₁ , Ar ₁ ', and Ar ₃ in Chemical Formulas 1 to 4 Or Ar ₃ 'is preferably a C ₆ to C ₄₀ arylamine group.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. Here, the electron injection layer may be further stacked on the electron transporting layer. The organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic layers and an anode are sequentially stacked, and an insulating layer or an adhesive layer is interposed between the electrodes and the organic layer.

Examples of the material usable as the anode included in the organic electroluminescent device according to the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black.

Examples of materials usable as a cathode included in the organic electroluminescent device according to the present invention include, but are not limited to, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, Tin, or lead, or alloys thereof; And a multilayer structure material such as LiF / Al or LiO ₂ / Al.

The organic material layer included in the organic electroluminescent device according to the present invention may be a material known in the art except for using any one of the compounds represented by Chemical Formulas 1 to 4 in the light emitting layer, the hole transporting layer, or the electron transporting layer. ≪ / RTI >

Materials that can be used as the substrate included in the organic electroluminescent device according to the present invention are not particularly limited, but examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

The organic electroluminescent device of the present invention may be manufactured by a method known in the art, and the luminescent layer included in the organic material layer may be prepared by a vacuum evaporation method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, and thermal transfer.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[ Synthetic example  1] Synthesis of Compound 1

1-phenyl-1H-benzo [d] thiophene was obtained under nitrogen atmosphere by the same procedure as in Example 1 except that 8.125 g (25.0 mmol) of 7,7,13,13-tetramethyl-7,13-dihydro- 1.25 ml (2.50 mmol) of imidazole, 0.69 g (0.75 mmol) of Pd ₂ (dba) ₃ , 1.22 ml (2.52 mmol) of P (t-bu) ₃ and 6.05 g (63.01 mmol) of NaO And the mixture was stirred under reflux for 24 hours. After completion of the reaction, the mixture was extracted with dichloromethane and the organic layer was dried over MgSO ₄ . After silica gel filtration, the column was subjected to column chromatography with Hexane: Mc 3: 2 (v / v) to obtain Compound 1, 7,7,13,13-tetramethyl- 5- (1-phenyl-1H- benzo [d] imidazol- (11.2 mmol) (yield 45%) of 7,13-dihydro-5H-indeno [1,2-b] acridine.

Elemental Analysis: C, 85.85; H, 6.04; N, 8.12 [M < + >]: 516

[ Synthetic example  2] Synthesis of Compound 2

Except that 3-bromoquinoline was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 87.57; H, 6.24; N, 6.19 [M < + >]: 451

[ Synthetic example  3] Synthesis of Compound 3

Synthesis Example 1 was repeated except that 2-bromo-4,6-diphenylpyridine was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole.

Elemental Analysis: C, 88.77; H, 6.18; N, 5.05 [M < + >]: 553

[ Synthetic example  4] Synthesis of Compound 4

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1 .

Elemental Analysis: C, 84.14; H, 5.79; N, 10.06 [M < + >]: 555

[ Synthetic example  5] Synthesis of Compound 5

Except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 89.01; H, 6.05; N, 4.94 [M < + >]: 565

[ Synthetic example  6] Synthesis of Compound 6

Except that 4-bromo-N, N-diphenylaniline was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 88.69; H, 6.38; N, 4.93 [M < + >]: 567

[ Synthetic example  7] Synthesis of Compound 7

Except that 2-bromo-5-phenylpyridine was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 87.83; H, 6.32; N, 5.85 [M < + >]: 477

[ Synthetic example  8] Synthesis of Compound 8

Except that 2'-bromo-3,4'-bipyridine was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 85.14; H, 6.09; N, 8.76 [M < + >]: 478

[ Synthetic example  9] Synthesis of Compound 9

Except that 9- (4-bromophenyl) -9H-carbazole was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole in Synthesis Example 1.

Elemental Analysis: C, 89.01; H, 6.05; N, 4.94 [M < + >]: 565

[ Synthetic example  10] Synthesis of Compound 10

In Synthesis Example 1, 2-bromo-7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2- except that 2-bromo-4,6-diphenylpyridine was used instead of 2-bromo-1-phenyl-1H-benzo [d] imidazole 2-yl) -7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine Were synthesized.

A solution of the synthesized 2-bromo-5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-7,13-dihydro- 6.3 g (1 eq.) Of tetrakis (triphenylphosphine) palladium (1 eq.), 9.2 g (5 mol%) and 5 g (3 eq.) Of potassium carbonate were placed in a 250 ml round-bottomed flask together with 61 ml of 1,4-dioxane and 18 ml of H ₂ O and refluxed under nitrogen for 3 hours. After completion of the reaction, the reaction solution was filtered through Celite, and then 7.76 g (9.76 mmol) (yield: 80%) of Compound 10 was synthesized by column chromatography.

Elemental Analysis: C, 89.02; H, 5.70; N, 5.28 [M] ^< ⁺ >: 794

[ Synthetic example  11] Synthesis of Compound 11

To a solution of 8.09 g of 2-bromo-5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-7,13- dihydro-5H- indeno [ (12.8 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane), Pd (dppf) Cl ₂ , 3.75 g (38.3 mmol) of KOAc and 50 ml of DMF were added. The mixture was stirred at 130 ° C for 12 hours, and the reaction was terminated. The reaction mixture was extracted with ethyl acetate and the water was removed with MgSO ₄ . The solvent was removed and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to give 5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl- - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7,13-dihydro-5H- indeno [1,2- b] acridine 40%).

Synthesis of 5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ), 7,13-dihydro-5H-indeno [1,2-b] acridine, 3.48 g (5.12 mol), 2-bromo-5- (4,6-diphenylpyridin- 3.24 g (1 equivalent) of tetrakis (triphenylphosphine) palladium (0), 0.35 g (5 mol%) of potassium carbonate, 2.5 g (3 mol) of 13-tetramethyl-7,13-dihydro- Equivalent) were placed in a 250 ml round-bottomed flask together with 35 ml of 1,4-dioxane and 9 ml of H ₂ O, and the mixture was stirred under reflux for 3 hours under a nitrogen atmosphere. After completion of the reaction, the reaction solution was filtered through Celite, and then 4.54 g (4.10 mmol) (yield: 80%) of Compound 11 was synthesized by column chromatography.

Elemental Analysis: C, 88.93; H, 6.01; N, 5.06 [M < + >]: 1105

[ Synthetic example  12] Synthesis of Compound 12

9-chloro-7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine was used in place of 7,7,13,13- dihydro-5H-indeno [1,2-b] acridine was used as the starting material.

9- (4- (pyridin-2-yl) -9H-carbazole was used in place of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -2-yl) phenyl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole. Were synthesized.

Elemental Analysis: C, 85.10; H, 5.30; N, 9.60 [M < + >]: 873

[ Synthetic example  13] Synthesis of Compound 13

Synthesis instead of 9- (4- (pyridin-2-yl) phenyl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -7,13-dihydro-5H-indeno [1,2-b] acridine was used as the starting material.

Elemental Analysis: C, 86.61; H, 5.81; N, 7.58 [M < + >]: 1107

[ Synthetic example  14] Synthesis of Compound 14

Instead of 2-bromo-5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2- b] acridine in Synthesis Example 11 9-chloro-5- (4,6-diphenyl-1,3,5-triazin-2-yl) -7,7,13,13-tetramethyl-7,13- dihydro-5H- indeno [ b] acridine was used as the starting material.

Elemental Analysis: C, 84.29; H, 5.62; N, 10.08 [M < + >]: 1109

[ Synthetic example  15] Synthesis of compound 15

Bromo-10-chloro-7,7,13,13-dihydro-5H-indeno [1,2-b] acridine was used in place of 2-bromo-7,7,13,13-tetramethyl- 5-chloro-5- (4,6-diphenylpyridin-2-yl) - 1, 3-dicarboxylic acid dihydrochloride was prepared using the same procedure except that 13-tetramethyl-7,13-dihydro- Synthesis of 7,7,13,13-tetramethyl-2- (9-phenyl-9H-carbazol-3-yl) -7,13-dihydro-5H-indeno [1,2-b] acridine.

0.47 g (19.6 mmol) of NaH was added to 25 ml of DMF under nitrogen and the mixture was stirred. 1.32 g (7.85 mmol) of 9H-carbazole dissolved in 100 ml of DMF was slowly added thereto, followed by stirring for about 1 hour. Then, 10-chloro-5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-2- (9- , 13-dihydro-5H-indeno [1,2-b] acridine (13.0 g, 15.7 mmol) was slowly added thereto and stirred for 12 hours.

After completion of the reaction, the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed to obtain 3.39 g (3.53 mmol) (yield 45%) of Compound 15.

Elemental Analysis: C, 88.72; H, 5.45; N, 5.83 [M < + >]: 959

[ Synthetic example  16] Synthesis of Compound 16

Synthesis Example 15 was synthesized using bromobenzene instead of 2-bromo-4,6-diphenylpyridine and diphenylamine instead of 9H-carbazole.

Elemental Analysis: C, 88.74; H, 6.08; N, 5.17 [M < + >]: 810

[ Synthetic example  17] Synthesis of Compound 17

Synthesis Example 16 was synthesized in the same manner except that triphenyl (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) silane was used instead of diphenylamine.

Elemental Analysis: C, 88.30; H, 5.97; N, 2.86; Si, 2.87 [M < + >]: 977

[ Synthetic example  18] Synthesis of compound 18

Except that Compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1 .

Elemental Analysis: C, 85.85; H, 6.04; N, 8.12 [M < + >]: 516

[ Synthetic example  19] Synthesis of Compound 19

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 3-bromoquinoline.

Elemental Analysis: C, 87.57; H, 6.24; N, 6.19 [M < + >]: 451

[ Synthetic example  20] Synthesis of Compound 20

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1 and 2-bromo- benzo [d] imidazole was used instead of 2-bromo-4,6-diphenylpyridine.

Elemental Analysis: C, 88.77; H, 6.18; N, 5.05 [M < + >]: 553

[ Synthetic example  21] Synthesis of Compound 21

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

Elemental Analysis: C, 84.14; H, 5.79; N, 10.06 [M < + >]: 555

[ Synthetic example  22] Synthesis of Compound 22

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 3-bromo-9-phenyl-9H-carbazole.

Elemental Analysis: C, 89.01; H, 6.05; N, 4.94 [M < + >]: 565

[ Synthetic example  23] Synthesis of Compound 23

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 4-bromo-N, N-diphenylaniline.

Elemental Analysis: C, 88.69; H, 6.38; N, 4.93 [M < + >]: 567

[ Synthetic example  24] Synthesis of Compound 24

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 2-bromo-5-phenylpyridine.

Elemental Analysis: C, 87.83; H, 6.32; N, 5.85 [M < + >]: 477

[ Synthetic example  25] Synthesis of Compound 25

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 2'-bromo-3,4'-bipyridine.

Elemental Analysis: C, 85.14; H, 6.09; N, 8.76 [M < + >]: 478

[ Synthetic example  26] Synthesis of Compound 26

The compound B-1 was used instead of 7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine in Synthesis Example 1, and 2-bromo- -benzo [d] imidazole was used instead of 9- (4-bromophenyl) -9H-carbazole.

Elemental Analysis: C, 89.01; H, 6.05; N, 4.94 [M < + >]: 565

[ Synthetic example  27] Synthesis of Compound 27

Synthesis Example 10 was synthesized in the same manner except that Compound B-2 was used instead of Compound A-2.

Elemental Analysis: C, 89.02; H, 5.70; N, 5.28 [M] ^< ⁺ >: 794

[ Synthetic example  28] Synthesis of compound 28

Instead of 2-bromo-5- (4,6-diphenylpyridin-2-yl) -7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2- b] acridine in Synthesis Example 11 Except that 2-bromo-5- (4,6-diphenylpyridin-2-yl) -11,11,13,13-tetramethyl-11,13-dihydro-5H-indeno [2,1- Were synthesized in the same manner.

Elemental Analysis: C, 88.93; H, 6.01; N, 5.06 [M < + >]: 1105

[ Synthetic example  29] Synthesis of Compound 29

Synthesis Example 12 was synthesized in the same manner except that Compound B-3 was used instead of Compound A-3.

Elemental Analysis: C, 85.10; H, 5.30; N, 9.60 [M < + >]: 873

[ Synthetic example  30] Synthesis of Compound 30

Synthesis Example 13 was synthesized in the same manner except that Compound B-3 was used instead of Compound A-3.

Elemental Analysis: C, 86.61; H, 5.81; N, 7.58 [M < + >]: 1107

[ Synthetic example  31] Synthesis of Compound 31

Synthesis Example 14 was synthesized in the same manner except that Compound B-3 was used instead of Compound A-3.

Elemental Analysis: C, 84.29; H, 5.62; N, 10.08 [M < + >]: 1109

[ Synthetic example  32] Synthesis of Compound 32

Synthesis Example 15 was synthesized in the same manner except that Compound B-4 was used instead of Compound A-4.

Elemental Analysis: C, 88.72; H, 5.45; N, 5.83 [M < + >]: 959

[ Synthetic example  33] Synthesis of Compound 33

Synthesis Example 16 was synthesized in the same manner except that Compound B-4 was used instead of Compound A-4.

Elemental Analysis: C, 88.74; H, 6.08; N, 5.17 [M < + >]: 810

[ Synthetic example  34] Synthesis of Compound 34

Synthesis Example 17 was synthesized in the same manner except that Compound B-4 was used instead of Compound A-4.

Elemental Analysis: C, 88.30; H, 5.97; N, 2.86; Si, 2.87 [M < + >]: 977

[ Synthetic example  35] Synthesis of Compound 35

The same procedure was followed except that 3-bromo-8-chloro-11,11-dimethyl-11,13-dihydro-5H-indeno [1,2-b] phenazine was used instead of the compound B-4 in Synthesis Example 34 Respectively.

Elemental Analysis: C, 87.87; H, 5.62; N, 6.51 [M < + >]: 859

[ Synthetic example  36] Synthesis of Compound 36

Bromo-11,11-dimethyl-11,13-dihydro-5H-indeno [1,2-b] acridine was used in place of 2-bromo-7,7,13,13-tetramethyl- dihydro-5H-indeno [1,2-b] phenazine and 2-bromo-4,6-diphenylpyridine instead of 2-bromonaphthalene.

Elemental Analysis: C, 89.48; H, 5.22; N, 5.31 [M < + >]: 790

[ Synthetic example  37] Synthesis of Compound 37

Bromo-11,11-dimethyl-11,13-dihydro-5H-indeno [1,2-b] acridine was used in place of 2-bromo-7,7,13,13-tetramethyl- (3-bromophenyl) pyridine was used instead of 2-bromo-4,6-diphenylpyridine and 9-phenyl-3- (4,4,5,5- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (4,4,5-tetramethyl-1,3,2-dioxaborolan- 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole.

Elemental Analysis: C, 83.47; H, 4.75; N, 9.90; O, 1.88 [M < + >]: 847

[ Synthetic example  38] Synthesis of Compound 38

3-bromo-11,11-dimethyl-11,13-dihydroindeno [2,1-b] pyridine was used instead of 3-bromo-11,11-dimethyl-11,13-dihydroindeno [ phenothiazine was used and 2,2 '- (5-bromo-1,3-phenylene) dipyridine was used instead of 2- (3-bromophenyl) pyridine.

Elemental Analysis: C, 81.59; H, 4.60; N, 10.41; S, 3.40 [M < + >]: 940

[ Synthetic example  39] Synthesis of Compound 39

9-chloro-7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1,2-b] acridine was used in place of 9-chloro-7,7,13,13- 7,13-dihydro-5H-benzo [b] fluoreno [3,2-e] [1,4] azasiline.

Elemental Analysis: C, 84.53; H, 5.32; N, 7.25; Si, 2.91 [M < + >]: 964

[ Example  1 to 39] Organic Field  Manufacturing of light emitting device

The compounds synthesized in Synthesis Examples 1 to 39 were subjected to high-purity sublimation purification and each of these compounds was used to prepare a green organic electroluminescent device according to the following procedure.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500A was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech). Then, the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

+ 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) were respectively applied to the ITO transparent electrode prepared above, m-MTDATA (60 nm) / TCTA / LiF (1 nm) / Al (200 nm).

At this time, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP are as follows.

[ Comparative Example ] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Examples 1 to 39 except that CBP having the following structure was used as a light emitting host material in place of the compound synthesized in Synthesis Examples 1 to 39 in the formation of a light emitting layer.

[ Evaluation example ]

The driving voltage, current efficiency and emission peak were measured for the organic electroluminescent devices manufactured in Examples 1 to 39 and Comparative Examples, and the results are shown in Table 2 below.

device host Driving
Voltage (V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Compound 1 6.91 520 40.4 Example 2 Compound 2 6.89 516 41.1 Example 3 Compound 3 6.87 517 41.7 Example 4 Compound 4 6.71 519 41.0 Example 5 Compound 5 6.64 521 41.4 Example 6 Compound 6 6.77 522 42.1 Example 7 Compound 7 6.79 518 41.5 Example 8 Compound 8 6.70 516 41.2 Example 9 Compound 9 6.75 517 42.3 Example 10 Compound 10 6.71 523 42.6 Example 11 Compound 11 6.77 515 42.0 Example 12 Compound 12 6.69 518 41.6 Example 13 Compound 13 6.62 517 40.3 Example 14 Compound 14 6.63 521 40.9 Example 15 Compound 15 6.71 520 41.2 Example 16 Compound 16 6.69 519 41.1 Example 17 Compound 17 6.67 517 41.3 Example 18 Compound 18 6.66 521 40.6 Example 19 Compound 19 6.79 518 41.3 Example 20 Compound 20 6.75 520 41.8 Example 21 Compound 21 6.66 518 40.2 Example 22 Compound 22 6.72 518 40.5 Example 23 Compound 23 6.82 524 41.2 Example 24 Compound 24 6.63 520 41.1 Example 25 Compound 25 6.89 517 40.9 Example 26 Compound 26 6.71 522 40.1 Example 27 Compound 27 6.78 517 40.5 Example 28 Compound 28 6.62 518 40.9 Example 29 Compound 29 6.75 517 41.1 Example 30 Compound 30 6.76 516 41.2 Example 31 Compound 31 6.86 518 41.2 Example 32 Compound 32 6.62 520 40.5 Example 33 Compound 33 6.72 519 40.2 Example 34 Compound 34 6.73 520 39.1 Example 35 Compound 35 6.59 525 39.9 Example 36 Compound 36 6.71 527 39.1 Example 37 Compound 37 6.68 529 39.5 Example 38 Compound 38 6.82 530 38.9 Example 39 Compound 39 6.85 528 38.7 Comparative Example CBP 6.93 516 38.2

As can be seen from the results shown in Table 2, when the compound according to the present invention was used as a light emitting layer of a green organic electroluminescent device (Examples 1 to 39), a green organic electroluminescent device using a conventional CBP (Comparative Example) It can be seen that it shows superior performance in terms of efficiency and driving voltage.

Claims (12)

A compound selected from the group consisting of compounds represented by the following formulas C-1 to C-11:

In the above formulas C-1 to C-6,
R ₁ to R ₄ , R ₆ and R ₇ are the same or different and each represents hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl group, C ₆ ~ of C ₄₀ of the diarylamino group, is selected from the group consisting of a heterocycloalkyl group of C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₄₀ aryl silyl group and C ₃ ~ C ₄₀ of ,
R ₅ is a C ₆ to C ₄₀ aryl group,
Ar ₁ to Ar ₃ are the same or different from each other, hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ of C ₆ to C ₄₀ aryloxy groups, C ₆ to C ₄₀ arylsilyl groups and C ₆ to C ₄₀ aryl groups, C ₅ to C ₆₀ heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ aryloxy groups, An arylamine group having 1 to ₄₀ carbon atoms, and may be fused with adjacent groups to form a ring,
a, b and c are integers of 0 to 4,
In the above formulas C-7 to C-11,
R ₁ to R ₄ , R ₆ and R ₇ are the same or different and each represents hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl group, C ₆ ~ of C ₄₀ of the diarylamino group, is selected from the group consisting of a heterocycloalkyl group of C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₄₀ aryl silyl group and C ₃ ~ C ₄₀ of ,
Ar ₁ to Ar ₃ are the same or different from each other, hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ of C ₆ to C ₄₀ aryloxy groups, C ₆ to C ₄₀ arylsilyl groups and C ₆ to C ₄₀ aryl groups, C ₅ to C ₆₀ heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ aryloxy groups, An arylamine group having 1 to ₄₀ carbon atoms, and may be fused with an adjacent group to form a ring,
a, b and c are an integer of 0 to 4; delete The method according to claim 1,
Wherein R ₁ and R ₂ are the same as each other and are a methyl group or a phenyl group. The method according to claim 1,
Wherein R ₃ and R ₄ are the same as each other and are a methyl group or a phenyl group. delete A compound selected from the group consisting of compounds represented by the following formulas (2) to (4):
(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 2 to 4,
X and Y are the same or different and are selected from the group consisting of CR ₃ R ₄ , O, S, NR ₅ and SiR ₆ R ₇ except that when X and Y are both CR ₃ R ₄ ,
R ₁ to R ₄ , R ₆ and R ₇ are the same or different and each represents hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl group, C ₆ ~ of C ₄₀ of the diarylamino group, is selected from the group consisting of a heterocycloalkyl group of C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₄₀ aryl silyl group and C ₃ ~ C ₄₀ of ,
R ₅ is a C ₆ to C ₄₀ aryl group,
Ar ₁ to Ar ₃ are the same or different from each other, hydrogen, deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ of C ₆ to C ₄₀ aryloxy groups, C ₆ to C ₄₀ arylsilyl groups and C ₆ to C ₄₀ aryl groups, C ₅ to C ₆₀ heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ aryloxy groups, An arylamine group having 1 to ₄₀ carbon atoms, and may be fused with adjacent groups to form a ring,
a, b and c are integers of 0 to 4,
X 'and Y' are the same or different from each other, and CR ₃ 'R ₄ '. O, S, NR ₅ 'and SiR ₆ ' R ₇ ', with the exception that when X' and Y 'are both CR ₃ ' R ₄ '
R ₁ 'to R ₄ ', R ₆ 'and R ₇ ' are the same or different and represent hydrogen, deuterium, halogen, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a C ₅ to C ₄₀ heteroaryl group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group , consisting of a heterocycloalkyl group of C ₆ ~ C ₄₀ of the diarylamino group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group, C ₆ ~ C ₄₀ aryl silyl group and C ₃ ~ C ₄₀ of ≪ / RTI >
R ₅ 'is a C ₆ to C ₄₀ aryl group,
Ar ₁ 'to Ar ₃ ' are the same or different from each other and represent hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, C ₃ to C ₄₀ heterocycloalkyl, C an aryl group of ₆ ~ C _40, C ₅ ~ heteroaryl group of C _60, C ₁ ~ C ₄₀ alkyloxy group of, C aryloxy of _{6 ~ C 40, C 6 ~} C 40 aryl silyl group, and a C ₆ of To C ₄₀ arylamine groups, and may be fused with adjacent groups to form a ring,
a ', b' and c 'are an integer of 0 to 4; The method according to claim 6,
The R ₁ And R < ₂ > are the same as each other,
Wherein R ₁ 'and R ₂ ' are the same as each other,
Wherein R ₁ , R ₂ , R ₁ 'and R ₂ ' are a methyl group or a phenyl group. The method according to claim 6,
The R ₃ And R < ₄ > are the same as each other,
R ₃ 'and R ₄ ' are the same as each other,
Wherein R ₃ , R ₄ , R ₃ 'and R ₄ ' are a methyl group or a phenyl group. delete 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the organic material layers is an organic material layer including a compound according to any one of claims 1, 3, 4, 6 to 8. 11. The method of claim 10,
Wherein the organic compound layer containing the compound is a light emitting layer. 11. The method of claim 10,
Wherein the organic compound layer containing the compound is a hole transport layer.