KR102111829B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

Description

A heterocyclic compound and an organic light emitting device comprising the same {HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a heterocyclic compound and an organic light emitting device including the same.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

The development of new materials for such organic light emitting devices continues to be required.

Korea Patent Publication No. 2000-0051826

A heterocyclic compound and an organic light emitting device including the same are described herein.

An exemplary embodiment of the present specification provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

X is O or S,

R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,

At least one of R4 and R5 is represented by the following formula (2),

[Formula 2]

L1 is a direct bond; Substituted or unsubstituted alkylene; Substituted or unsubstituted alkenylene; Substituted or unsubstituted alkynylene; Substituted or unsubstituted cycloalkylene; Substituted or unsubstituted arylene; Or a substituted or unsubstituted heteroarylene,

Ar1 and Ar2 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,

a is an integer from 0 to 4,

b is an integer from 0 to 2,

p is an integer from 0 to 10,

When a, b, and p are each 2 or more, the structures in parentheses are the same or different from each other.

In addition, an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.

The compounds described herein can be used as a material for the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifespan characteristics in an organic light emitting device.

In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, luminescence, electron transport, or electron injection materials. In addition, the compounds described herein can be preferably used as a light emitting layer, electron transport or electron injection material. Further, more preferably, according to an exemplary embodiment of the present specification, the compound may be used as a material for a hole injection layer, a hole transport layer or an electron blocking layer. In particular, according to an exemplary embodiment of the present specification, the hole transport ability of the compound is excellent.

FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 Did.

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides the compound represented by Chemical Formula 1.

Examples of the substituents are described below, but are not limited thereto.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; And substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups, or substituted or unsubstituted with two or more substituents among the exemplified substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

According to an exemplary embodiment of the present specification, the expression "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Alkyl groups; Aryl group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present specification, the expression "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 50 carbon atoms; And one or more substituents selected from the group consisting of a heterocyclic group having 2 to 50 carbon atoms, which may be substituted or unsubstituted.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRR'R '', wherein R, R 'and R' 'are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the boron group may be represented by the formula of -BRR ', wherein R and R' are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, phenyl boron group, and the like.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, styrenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the aryl amine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, and 9-methyl-anthra Senilamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including the two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group simultaneously.

In the present specification, the aryl heteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.

,

,

, 및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

, And

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heteroatom as a heterocyclic group containing one or more of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group And dibenzofuranyl groups, but are not limited to these.

In the present specification, the description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, and arylheteroarylamine group is described above. A description of one aryl group can be applied.

In the present specification, the alkyl group of the alkylthio group, the alkyl sulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group, and the alkylamine group, the description of the aforementioned alkyl group may be applied.

In the present specification, the heteroaryl group among the heteroaryl group, heteroarylamine group, and arylheteroarylamine group may be applied to the description of the aforementioned heterocyclic group.

In the present specification, the alkenyl group among the alkenyl groups may be applied to the alkenyl group described above.

In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group.

In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups to form a ring is a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming these condensed rings.

In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms as a ring that is not aromatic.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, anthracenyl group, and the like, but are not limited thereto.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.

According to one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3 to 5.

[Formula 3]

[Formula 4]

[Formula 5]

In the formula 3 to 5,

X. R1 to R6, a and b are defined as in Formula 1.

According to an exemplary embodiment of the present specification, at least one of the R4 and R5 may be represented by the formula (2).

According to an exemplary embodiment of the present specification, R4 may be represented by the formula (2).

According to an exemplary embodiment of the present specification, R5 may be represented by the formula (2).

According to an exemplary embodiment of the present specification, L1 is a direct bond; Substituted or unsubstituted alkylene having 1 to 60 carbon atoms; Substituted or unsubstituted alkenylene having 2 to 60 carbon atoms; A substituted or unsubstituted alkynylene having 2 to 60 carbon atoms; A substituted or unsubstituted cycloalkylene having 3 to 60 carbon atoms; Substituted or unsubstituted arylene having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroarylene having 2 to 50 carbon atoms, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Arylene having 6 to 50 carbon atoms; Or heteroarylene having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Or arylene having 6 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Or arylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 50 carbon atoms and heteroaryl group having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Phenylene substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 50 carbon atoms and heteroaryl group having 2 to 50 carbon atoms; Naphthylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 50 carbon atoms and heteroaryl group having 2 to 50 carbon atoms; A phenanthrene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, nitrile, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms; Or fluorenylene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 50 carbon atoms, and heteroaryl group having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Phenylene; Naphthylene; Phenanthryl group; Or fluorenylene substituted with an alkyl group.

According to the exemplary embodiment of the present specification, L1 may be a direct bond or any one selected from the following structures.

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Or phenylene.

According to an exemplary embodiment of the present specification, L1 is a direct bond; Or phenylene substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, nitrile, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is one or more substituents selected from the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 50 carbon atoms and heteroaryl group having 2 to 50 carbon atoms. It is phenylene unsubstituted or substituted with.

According to an exemplary embodiment of the present specification, L1 is phenylene.

According to an exemplary embodiment of the present specification, L1 is a direct bond.

According to an exemplary embodiment of the present specification, X is O.

According to an exemplary embodiment of the present specification, X is S.

According to an exemplary embodiment of the present specification, R3 and R6 are hydrogen.

According to an exemplary embodiment of the present specification, a group other than the group represented by Formula 2 in R4 and R5 is hydrogen, halogen, hydroxy group, nitrile group, amino group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted It is a substituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aryl group, or combines with adjacent groups to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, a group other than the group represented by Formula 2 in R4 and R5 is hydrogen, halogen, hydroxy group, nitrile group, amino group, alkyl group, alkoxy group, aryloxy group, arylthio group, aryl group, or adjacent And a group to form a ring.

According to one embodiment of the present specification, a group other than the group represented by Chemical Formula 2 in R4 and R5 is hydrogen.

According to an exemplary embodiment of the present specification, the R1 To R3 And R6 Is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Alkyl groups; Aryl group; Or a heterocyclic group.

According to an exemplary embodiment of the present specification, the R1 To R3 And R6 Is hydrogen; heavy hydrogen; Halogen group; Nitrile group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 50 carbon atoms; Or a heterocyclic group having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, the R1 To R3 And R6 Is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Or it is a C1-C5 alkyl group.

According to an exemplary embodiment of the present specification, the R1 To R3 And R6 Is hydrogen; Or deuterium.

According to one embodiment of the present specification, R1 to R3 and R6 are hydrogen.

According to an exemplary embodiment of the present specification, the p is 0 or 1.

According to an exemplary embodiment of the present specification, p is 0.

According to an exemplary embodiment of the present specification, the p is 1.

According to one embodiment of the present specification, R1 to R3 and R6 are hydrogen, and a group other than the group represented by Formula 2 in R4 and R5 is hydrogen, and L1 is a direct bond; Or phenylene.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 50 carbon atoms containing at least one of O, N, S and P, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group, a heterocyclic group, or a phenyl group unsubstituted or substituted; A biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; Terphenyl group; Quarterphenyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with an alkyl group or a phenyl group; Spirobifluorenyl group; Naphthyl group; Pyrenyl group; Triphenylene group; Dibenzofuranyl group; Benzo ring condensed dibenzofuranyl group; Polybenzothiophene group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group, or combine with each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, arylamine group, heteroarylamine group, aryl heteroaryl A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an amine group, an aryl group having 6 to 50 carbon atoms, and a heteroaryl group having 2 to 50 carbon atoms; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A biphenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A terphenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A quaterphenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A phenanthryl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A fluorenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A spirobifluorenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A naphthyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A pyrenyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A dibenzofuranyl group unsubstituted or substituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A benzene ring condensed dibenzofuranyl group substituted or unsubstituted with one or more substituents; Selected from the group consisting of deuterium, halogen groups, nitrile groups, alkyl groups having 1 to 10 carbon atoms, arylamine groups, heteroarylamine groups, arylheteroarylamine groups, aryl groups having 6 to 50 carbon atoms, and heteroaryl groups having 2 to 50 carbon atoms. A polybenzothiophene group unsubstituted or substituted with one or more substituents; Or in the group consisting of deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, arylamine group, heteroarylamine group, arylheteroarylamine group, aryl group having 6 to 50 carbon atoms and heteroaryl group having 2 to 50 carbon atoms. It is a carbazole group substituted or unsubstituted with one or more selected substituents, or combined with each other, deuterium, halogen group, nitrile group, alkyl group having 1 to 10 carbon atoms, arylamine group, heteroarylamine group, arylheteroarylamine group, or 6 to 6 carbon atoms. A substituted or unsubstituted ring is formed by one or more substituents selected from the group consisting of 50 aryl groups and heteroaryl groups having 2 to 50 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an phenyl group unsubstituted or substituted with an aryl group or an arylamine group; Biphenyl group; Terphenyl group; Quarterphenyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with an alkyl group or a phenyl group; Spirobifluorenyl group; Naphthyl group; Pyrenyl group; Dibenzofuranyl group; Benzo ring condensed dibenzofuranyl group; Polybenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, at least one of the Ar1 and Ar2 may be any one selected from the following structures.

In the above structures,

A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present specification, at least one of the Ar1 and Ar2 may be any one selected from the following structures.

In the above structures,

A1 and A2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present specification, at least one of the Ar1 and Ar2 may be any one selected from the following structures.

A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present specification, the formula 2 may be any one selected from the following structures.

In the above structures,

The definition of L1 and p is the same as Formula 2,

A3, A4 and Ar11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, Formula 2 may be any one selected from structures represented by the following substituents.

According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.

In addition, the present specification provides an organic light emitting device including the compound represented by Chemical Formula 1.

In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.

The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic layers.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport is Includes the compound of Formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 above.

In one embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes a compound of Formula 1 above.

In one embodiment of the present specification, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection includes the compound of Formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes a compound of Formula 1 above.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

 In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 Did. In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of Formula 1 above.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers contains the heterocyclic compound. In one exemplary embodiment, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.

In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers contains the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be included in one layer of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present specification, when the heterocyclic compound is included in each of the two or more electron transport layers, other materials except the heterocyclic compound may be the same or different from each other.

 The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing metal or conductive metal oxides or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, followed by deposition of a material that can be used as a cathode. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to this method, an organic light emitting device may also be formed by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, 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 : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in a light emitting layer A compound that prevents migration of the excited excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. , Organic anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As the hole transport material, the hole is transported from the anode or the hole injection layer to the hole and is transported to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons This is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The organic light emitting device according to the present specification may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

In one embodiment of the present specification, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited by them.

Manufacturing example

< Manufacturing example  1> Preparation of the following compounds 1-A-1 to 1-A-2

Compound 1-A- 1 of  Compound synthesis

                   [Compound 1-A-1]

1-Bromonaphthalene-2,7-diol (7g, 29,4mmol) and (2-fluorophenyl) boronic acid (4.5g, 32.1mmol) were added to THF (300ml), and then 2M potassium carbonate aqueous solution (100 ml) was added, tetrakistriphenyl-phosphino palladium (210 mg, 0.18 mmol) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium phosphate solution was removed to separate the layers. The filtered white solid was recrystallized with tetrahydrofuran and ethanol to prepare the compound 1-A-1 (4.4 g, yield 60%).

MS [M + H] ⁺ = 255.07

Compound 1-A- 2 of  Compound synthesis

                                             [Compound 1-A-2]

The compound 1-A-1 (5 g, 20 mmol) and potassium phosphate (10.4 g, 49.0 mmol) were added to Xylene (100 ml), and then 12 ml of DMAC was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and terminating the reaction, the mixture was separated using ethyl acetate and a 2N HCl aqueous solution. After removal of the solvent, chloroform and hexane were recrystallized to prepare Compound 1-A-2 (2.8 g, yield 60%).

MS [M + H] ⁺ = 235.07

< Preparation Example 2 > Preparation of the following compounds 1-B-1 to 1-B-2

Synthesis of Compound 1-B-1

                                                [Compound 1-B-1]

Compound 1-B was synthesized in the same manner as in Example 1-A-1, except that 1-bromonaphthalene-2,6-diol was used instead of compound 1-bromonaphthalene-2,7-diol. -1 was prepared.

MS [M + H] ⁺ = 255.07

Compound 1-B-2 compound synthesis

                                            [Compound 1-B-2]

Compound 1-B-2 was synthesized in the same manner as in Synthesis Example 1-A-2, except that 1-B-1 was used instead of Compound 1-A-1.

MS [M + H] ⁺ = 235.07

< Preparation Example 3 > Preparation of the following compounds 1-C-1 to 1-C-2

Synthesis of Compound 1-C-1

                                        [Compound 1-C-1]

The compound 1-A-2 (4.7 g, 20 mmol) and potassium carbonate (4.1 g, 30 mmol) were added to 30 mL of AN and 30 mL of H ₂ O, followed by stirring, and then NNF (8.5 g, 28 mmol) was added. Compound 1-C-1 (8 g, yield 90%) was prepared by extraction with ethyl acetate and water and removal of the solvent.

MS [M + H] ⁺ = 501.3

Compound 1-C-2 compound synthesis

                                    [Compound 1-C-2]

Compound 1-C-2 was synthesized in the same manner as in Synthesis Example 1-C-1, except that 1-B-2 was used instead of Compound 1-A-2.

MS [M + H] ⁺ = 501.3

< Preparation Example 4 > Preparation of the following compounds 1-D-1 to 1-D-12

The compound 1-C-1 or 1-C-2 (1eq) and N (Ar1) (Ar2) (1.03eq) (the definitions of Ar1 and Ar2 are as in Formula 1), sodium-t-butoxide ( 1.4eq) was added to xylene, followed by heating and stirring, followed by adding 2 mmol of [bis (tri-t-butylphosphine)] palladium at 80 ° C. After lowering the temperature to room temperature and terminating the reaction, it was recrystallized using chloroform and ethyl acetate to prepare compounds 1-D-1 to 1-D-12, which are shown in Table 1 below.

< Manufacturing example  5> The following compounds 1-E-1 to 1-E- 5 of  Produce

The compound 1-C-1 or 1-C-2 (1eq) and 4-chlorophenylboronic acid, 3-chlorophenylboronic acid, or 2-chlorophenyl After adding boronic acid (2-chlorophenylboronic acid) and butoxide (1.4eq) to THF (300ml), 2M potassium carbonate aqueous solution (100ml) was added, and tetrakistriphenyl-phosphino palladium was added, followed by 10 It was stirred with heating for an hour. After lowering the temperature to room temperature and terminating the reaction, the potassium phosphate solution was removed to separate the layers. After removing the solvent, recrystallization with ethyl acetate and dried.

After that, N (Ar1) (Ar2) (1.03eq) (the definitions of Ar1 and Ar2 are the same as in Chemical Formula 1), after adding sodium-t-butoxide (1.4eq) to xylene and stirring with heating. 2 mmol% of [bis (tri-t-butylphosphine)] palladium was added at 80 ° C. After lowering the temperature to room temperature and terminating the reaction, recrystallization using chloroform and ethyl acetate to prepare compounds 1-E-1 to 1-E-5, which are shown in Table 2 below.

<Example>

<Example 1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and distilled water was used for Millipore Co. As the product filter, distilled water filtered secondarily was used. After washing the ITO for 30 minutes, the ultrasonic cleaning was repeated 10 times with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, hexanitrile hexaazatriphenylene was thermally vacuum-deposited to a thickness of 500 Pa to form a hole injection layer. On top of that, the compound 1-D-1 (400Å) synthesized in Preparation Example 4 above, which is a material for transporting holes, was vacuum-deposited, and then a host H1 and a dopant D1 compound were vacuum-deposited to a thickness of 300Å as a light emitting layer. Subsequently, the E1 compound (300 kPa) was sequentially vacuum vacuum deposited with an electron injection and transport layer. An organic light emitting device was manufactured by sequentially depositing 12 µm thick lithium fluoride (LiF) and 2,000 µm aluminum on the electron transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, lithium fluoride was maintained at 0.2 Å / sec, and aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.

[Hexanitrile hexaazatriphenylgiren] [HT1]

[H1] [D1]

[E1]

<Example 2>

The same experiment was performed except that Formula 1-D-2 instead of Formula 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1.

<Example 3>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-D-3 was used.

<Example 4>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-D-4 was used.

<Example 5>

The same experiment was performed except that 1-D-5 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Formula 1-D-5 was used.

<Example 6>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-D-6 was used.

<Example 7>

The same experiment was conducted except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Chemical Formula 1-D-7 was used.

<Example 8>

The same experiment was conducted except that 1-D-8 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Formula 1-D-8 was used.

<Example 9>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-D-9 was used.

<Example 10>

The same experiment was performed except that 1-D-10 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Formula 1-D-10 was used.

<Example 11>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Chemical Formula 1-D-11 was used.

. <Example 12>

The same experiment was conducted except that 1-D-1 instead of 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1.

<Example 13>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Formula 1-E-1 was used.

<Example 14>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-E-2 was used.

<Example 15>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-E-3 was used.

<Example 16>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, and Chemical Formula 1-E-4 was used.

<Example 17>

The same experiment was performed except that 1-D-1 synthesized in Preparation Example 4 was used as the hole transport layer in Example 1, except that Formula 1-E-5 was used.

<Comparative Example 1>

The same experiment was performed except that HT1 was used instead of Chemical Formula 1-D-1 synthesized in Preparation Example 4 as the hole transport layer in Example 1.

Table 3 shows the results of experiments of the organic light emitting device manufactured by using each compound as a hole transport layer material, as in Examples 1 to 17 and Comparative Example 1.

Experimental Example
50 mA / ㎠ HTL substances Voltage (V) Current efficiency (cd / A) Comparative Example 1 HT1 6.14 5.87 Example 1 Formula 1-D-1 6.25 6.46 Example 2 Formula 1-D-2 6.14 6.75 Example 3 Formula 1-D-3 6.28 6.62 Example 4 Formula 1-D-4 6.16 6.91 Example 5 Formula 1-D-5 6.23 7.12 Example 6 Formula 1-D-6 6.23 7.20 Example 7 Formula 1-D-7 6.15 7.02 Example 8 Formula 1-D-8 6.18 6.23 Example 9 Formula 1-D-9 6.20 6.77 Example 10 Formula 1-D-10 6.13 5.98 Example 11 Formula 1-D-11 6.22 7.11 Example 12 Formula 1-D-12 6.09 7.01 Example 13 Formula 1-E-1 6.11 6.88 Example 14 Formula 1-E-2 6.23 6.78 Example 15 Formula 1-E-3 6.34 6.89 Example 16 Formula 1-E-4 6.15 6.99 Example 17 Formula 1-E-5 6.27 7.00

The compound derivative of the formula according to the present invention may play a role of hole injection and hole transport in an organic electronic device including an organic light emitting device, and having a substituent at the R4 or R5 position, thereby having higher hole transport properties than the previous substitution position ( hole transporting property), and can improve device performance and life.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron transport layer

Claims (12)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X is O,
R1 to R3 and R6 are hydrogen,
One of R4 and R5 is represented by the following Chemical Formula 2, and a group other than the group represented by the following Chemical Formula 2 of R4 and R5 is hydrogen,
[Formula 2]

L1 is a direct bond; Substituted or unsubstituted alkylene; Substituted or unsubstituted alkenylene; Substituted or unsubstituted alkynylene; Substituted or unsubstituted cycloalkylene; Substituted or unsubstituted arylene; Or a substituted or unsubstituted heteroarylene,
Ar1 and Ar2 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,
a is an integer from 0 to 4,
b is an integer from 0 to 2,
p is an integer from 0 to 10,
When a, b, and p are each 2 or more, structures in parentheses are the same or different from each other. delete The method according to claim 1, wherein at least one of Ar1 and Ar2 is any one selected from the following structures:

A1 to A3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthioxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkyl sulfoxy group; A substituted or unsubstituted aryl sulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring,
The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups.
The method according to claim 1, wherein L1 is a direct bond; Phenylene; Naphthylene; Phenanthrene; Or a fluorenylene substituted with an alkyl group. The method according to claim 1, wherein L1 is a direct bond or a compound selected from any one of the following structures:

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amine group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Aryl heteroarylamine group; Arylphosphine group; And one or more substituents selected from the group consisting of heterocyclic groups. The method according to claim 1, wherein R1 to R3 and R6 are hydrogen, and a group other than the group represented by Formula 2 among R4 and R5 is hydrogen, and L1 is a direct bond; Or phenylene. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group, a heterocyclic group, or a phenyl group unsubstituted or substituted; A biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; Terphenyl group; Quarterphenyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with an alkyl group or a phenyl group; Spirobifluorenyl group; Naphthyl group; Pyrenyl group; Triphenylene group; Dibenzofuranyl group; Benzo ring condensed dibenzofuranyl group; Polybenzothiophene group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group, or combine with each other to form a substituted or unsubstituted ring. The method according to claim 1, wherein the compound of Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound according to any one of claims 1 and 3 to 8 Organic light emitting device. The organic light emitting device of claim 9, wherein the organic material layer containing the compound is a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and hole transport. The organic light emitting device of claim 9, wherein the organic material layer containing the compound is an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport. The organic light emitting device of claim 9, wherein the organic material layer containing the compound is a light emitting layer.

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