KR20220128102A - Heterocyclic compound, organic light emitting device including same, and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1, an organic light emitting device including the heterocyclic compound, and a composition for an organic material layer. The heterocyclic compound described in the present specification can be used as a material for the organic material layer of the organic light emitting device. The compound can serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, or a charge generating material in the organic light emitting device.

Description

Heterocyclic compound, an organic light emitting device comprising the same, and a composition for an organic material layer {HETEROCYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE INCLUDING SAME, AND COMPOSITION FOR ORGANIC LAYER OF ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer.

The electroluminescent device is a kind of self-emission type display device, and has a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of a material for the organic thin film is continuously required.

U.S. Patent No. 4,356,429

An object of the present specification is to provide a composition for a heterocyclic compound, an organic light emitting device including the same, and an organic material layer

In an exemplary embodiment of the present specification, a heterocyclic compound of Formula 1 is provided.

[Formula 1]

In Formula 1,

L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,

m is an integer of 1 to 5, and when 2 or more, L is the same as or different from each other,

R1 to R10 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Any one of R3, R4 and R6 is represented by the following formula 1-A,

[Formula 1-A]

In Formula 1-A,

R11 to R20 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Adjacent groups of R11 to R20 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or it may form a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle,

는 화학식 1과 결합되는 위치를 의미한다.

denotes a position combined with Chemical Formula 1.

In another embodiment, the 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 organic material layer includes the heterocyclic compound of Formula 1 above.

In another exemplary embodiment, there is provided a composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound of Formula 1 above.

In another embodiment, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer provides a method of manufacturing an organic light emitting device comprising forming one or more organic material layers using the composition for an organic material layer. .

The heterocyclic compound described herein may be used as an organic material layer material of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a charge generating material, and the like in an organic light emitting device. In particular, the compound can be used as a light emitting material of an organic light emitting device.

When the heterocyclic compound of Formula 1 is included in the light emitting material of the organic light emitting device, that is, the light emitting layer, it is possible to provide an organic light emitting device excellent in terms of driving voltage and lifespan.

Specifically, the heterocyclic compound of Formula 1 has a structure in which triazine and carbazole are directly bonded or bonded through a linker, and one arylamine group is substituted at a specific position of the carbazole. When this is done, the hole injection ability of the light emitting layer is strengthened, the driving voltage of the device is lowered, the light efficiency is improved, and the lifespan of the device is increased by the thermal stability of the compound.

1 to 3 are diagrams exemplarily showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present specification.

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

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

In the present specification, "substituted or unsubstituted" means deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; And substituted with one or more substituents selected from the group consisting of an amine group, or substituted with a substituent selected from the above exemplified substituents two or more substituents connected, or means unsubstituted.

In the present specification, "when a substituent is not indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ² H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In an exemplary embodiment of the present application, "when a substituent is not indicated in the chemical formula or compound structure" may mean that all positions that can come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in "when a substituent is not indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.

In the exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, and as an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, hydrogen- It can be expressed as ² , and the element symbol can also be written as D or 2H.

In an exemplary embodiment of the present application, isotopes have the same number of protons (protons), but isotopes that have the same atomic number (Z), but different mass numbers (A) have the same number of protons It can also be interpreted as elements with different numbers of (neutrons).

In the exemplary embodiment of the present application, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents is defined as T2. It can be defined as /T1×100 = T%.

로 표시되는 페닐기에 있어 중수소의 함량 20%라는 것은 페닐기가 가질 수 있는 치환기의 총 개수는 5(식 중 T1)개이고, 그 중 중수소의 개수가 1(식 중 T2)인 경우 20%로 표시될 수 있다. 즉, 페닐기에 있어 중수소의 함량이 20%인 것은 하기 구조식으로 표시될 수 있다.That is, in one example,

20% of the content of deuterium in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, when the number of deuterium is 1 (T2 in the formula), it will be expressed as 20% can That is, the 20% content of deuterium in the phenyl group may be represented by the following structural formula.

In addition, in the exemplary embodiment of the present application, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.

In the present specification, the alkyl group includes a straight or branched chain, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, the alkynyl group includes a straight or branched chain, and may be further substituted by other substituents. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 ,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a hetero atom, includes monocyclic or polycyclic, and may be further substituted by other substituents. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, or the like. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

In the present specification, the aryl group includes a monocyclic or polycyclic ring, and may be further substituted by other substituents. Here, polycyclic means a group in which an aryl group is directly connected to another ring group or condensed. Here, the other ring group may be an aryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. When the aryl group is two or more rings, the carbon number may be 8 to 60, 8 to 40, or 8 to 30. Specific examples of the aryl group include a phenyl group, a biphenyl group, a ter-phenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenyl group Nalenyl group, pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof, and the like, but are not limited thereto.

In the present specification, the terphenyl group may be linear or branched, and may be selected from the following structures.

In the present specification, the branched terphenyl group may be selected from the following structures.

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

,

,

,

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

,

,

,

and the like, but is not limited thereto.

In the present specification, the heteroaryl group includes O, S, SO ₂ , Se, N or Si as a hetero atom, includes monocyclic or polycyclic, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. When the heteroaryl group is two or more rings, the number of carbon atoms may be 4 to 60, 4 to 40, or 4 to 25. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinazolylyl group, naphthyridyl group, acridinyl group, phenanthridyl group Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, benzofuro[2,3-d]pyrimidyl group; benzothieno[2,3-d] pyrimidyl group; Benzofuro[2,3-a]carbazolyl group, benzothieno[2,3-a]carbazolyl group, 1,3-dihydroindolo[2,3-a]carbazolyl group, benzofuro [3,2-a] carbazolyl group, benzothieno [3,2-a] carbazolyl group, 1,3-dihydroindolo [3,2-a] carbazolyl group, benzofuro [2, 3-b] carbazolyl group, benzothieno [2,3-b] carbazolyl group, 1,3-dihydroindolo [2,3-b] carbazolyl group, benzofuro [3,2-b ]carbazolyl group, benzothieno[3,2-b]carbazolyl group, 1,3-dihydroindolo[3,2-b]carbazolyl group, benzofuro[2,3-c]carbazolyl group Group, benzothieno[2,3-c]carbazolyl group, 1,3-dihydroindolo[2,3-c]carbazolyl group, benzofuro[3,2-c]carbazolyl group, benzo Thieno [3,2-c] carbazolyl group, 1,3-dihydroindolo [3,2-c] carbazolyl group, 1,3-dihydroindeno [2,1-b] carbazolyl group , 5,11-dihydroindeno [1,2-b] carbazolyl group, 5,12-dihydroindeno [1,2-c] carbazolyl group, 5,8-dihydroindeno [2, 1-c] carbazolyl group, 7,12-dihydroindeno[1,2-a]carbazolyl group, 11,12-dihydroindeno[2,1-a]carbazolyl group, and the like. , but is not limited thereto.

), 트리에틸실릴기(

), t-부틸디메틸실릴기(

), 비닐디메틸실릴기(

), 프로필디메틸실릴기(

), 트리페닐실릴기(

), 디페닐실릴기(

), 페닐실릴기(

) 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group is a substituent including Si and the Si atoms are directly connected as a radical, and is represented by -Si(R101)(R102)(R103), R101 to R103 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specific examples of the silyl group include a trimethylsilyl group (

), triethylsilyl group (

), t-butyldimethylsilyl group (

), a vinyl dimethylsilyl group (

), propyldimethylsilyl group (

), a triphenylsilyl group (

), a diphenylsilyl group (

), a phenylsilyl group (

), but is not limited thereto.

In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), R104 and R105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the above-described examples may be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethyl phosphine oxide group, a diphenyl phosphine oxide group, and a dinaphthyl phosphine oxide group.

In the present specification, the amine group is represented by -N(R106)(R107), R106 and R107 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. The amine group is -NH ₂ ; monoalkylamine group; monoarylamine group; monoheteroarylamine group; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene group There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

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

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

Rings that adjacent groups may form include hydrocarbon rings and heterocycles, and specifically include aliphatic or aromatic hydrocarbon rings, aliphatic or aromatic heterocycles.

The aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be the structures exemplified by the above-described cycloalkyl group, aryl group, heterocycloalkyl group and heteroaryl group, respectively, except that they are not monovalent groups.

In an exemplary embodiment of the present specification, L in Formula 1 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

In an exemplary embodiment of the present specification, L is a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

In an exemplary embodiment of the present specification, L is a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

In an exemplary embodiment of the present specification, L is a direct bond; or a C6 to C20 arylene group.

In an exemplary embodiment of the present specification, L is a direct bond; phenylene group; or a biphenylene group.

In an exemplary embodiment of the present specification, R1 and R2 of Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group including O or S.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with an alkyl group; a dibenzofuran group unsubstituted or substituted with deuterium; Or it may be a dibenzothiophene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; 9,9-dimethyl-9H-fluorenyl group; dibenzofuran group; or a dibenzothiophene group, which may be further substituted with deuterium.

In an exemplary embodiment of the present specification, R3 to R10 of Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R3 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R3 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R3 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C15 aryl group; Or it may be a substituted or unsubstituted C2 to C15 heteroaryl group.

In an exemplary embodiment of the present specification, R3 to R10 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R5 and R7 to R10 of Formula 1 are each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, any one of R3, R4 and R6 of Formula 1 is represented by Formula 1-A, and the remainder is hydrogen; or deuterium.

[Formula 1-A]

In Formula 1-A,

R11 to R20 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Adjacent groups of R11 to R20 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or it may form a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle,

는 화학식 1과 결합되는 위치를 의미한다.

denotes a position combined with Chemical Formula 1.

In an exemplary embodiment of the present specification, R11 to R20 of Formula 1-A are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6 to C60 aryl group, and adjacent groups of R11 to R20 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle may be formed.

In an exemplary embodiment of the present specification, R11 to R20 are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6 to C30 aryl group, and adjacent groups among R11 to R20 are bonded to each other to form a substituted or unsubstituted C6 to C30 aliphatic or aromatic hydrocarbon ring; Or a substituted or unsubstituted C2 to C30 aliphatic or aromatic heterocycle may be formed.

In an exemplary embodiment of the present specification, R11 to R20 are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6 to C30 aryl group, and adjacent groups among R11 to R20 may be bonded to each other to form a substituted or unsubstituted C2 to C30 aliphatic or aromatic heterocycle.

In an exemplary embodiment of the present specification, R11 to R20 are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6 to C15 aryl group, and adjacent groups among R11 to R20 may be bonded to each other to form a substituted or unsubstituted C2 to C15 aliphatic or aromatic heterocycle.

In an exemplary embodiment of the present specification, R11 to R20 are each independently hydrogen; heavy hydrogen; or a C6 to C15 aryl group unsubstituted or substituted with deuterium, and adjacent groups of R11 to R20 are bonded to each other to form a substituted or unsubstituted benzothiophene ring; Or it may form a substituted or unsubstituted benzofuran ring.

In an exemplary embodiment of the present specification, R11 to R20 are each independently hydrogen; heavy hydrogen; or a phenyl group unsubstituted or substituted with deuterium, and adjacent groups of R11 to R20 are bonded to each other to form a benzothiophene ring substituted or unsubstituted with deuterium; Or it may form a benzofuran ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-3 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

R33, R44 and R66 are each independently hydrogen; or deuterium,

Definitions of the remaining substituents are the same as in Formula 1.

In an exemplary embodiment of the present specification, the content of deuterium in the heterocyclic compound of Formula 1 may be 0% to 100%.

In an exemplary embodiment of the present specification, the content of deuterium in the heterocyclic compound of Formula 1 may be 0%, or 20% to 100%.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied. substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

In one embodiment of the present specification, the first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound of Formula 1 above.

In the exemplary embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

In another exemplary embodiment of the present specification, the first electrode may be a negative electrode, and the second electrode may be an anode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the blue organic light emitting device. For example, the heterocyclic compound of Formula 1 may be included in the emission layer of the blue organic light emitting device.

In the exemplary embodiment of the present specification, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the green organic light emitting device. For example, the heterocyclic compound of Formula 1 may be included in the emission layer of the green organic light emitting device.

In the exemplary embodiment of the present specification, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the red organic light emitting device. For example, the heterocyclic compound of Formula 1 may be included in the emission layer of the red organic light emitting device.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the aforementioned heterocyclic compound.

The heterocyclic compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

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, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

In the organic light emitting device of the present specification, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound of Formula 1 above.

In the organic light emitting device of the present specification, the organic material layer may include a light emitting layer, the light emitting layer may include a host, and the host may include the heterocyclic compound of Formula 1 above.

In the organic light emitting device of the present specification, the organic material layer including the heterocyclic compound of Formula 1 may further include a compound of Formula 2 below.

[Formula 2]

In Formula 2,

R21 and R22 are the same as or different from each other, and are each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r31 is an integer of 0 to 7, and when 2 or more, R31 are the same as or different from each other,

r32 is an integer from 0 to 7, and in the case of 2 or more, R32 is the same as or different from each other.

In an exemplary embodiment of the present specification, the organic material layer including the heterocyclic compound is a light emitting layer, and the light emitting layer may include the heterocyclic compound and the compound of Formula 2 at the same time.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C6 to C30 aryl group; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; Or it may be a substituted or unsubstituted triphenylenyl group.

In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; a phenyl group unsubstituted or substituted with a cyano group or a silyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; 9,9'-spirobi[fluorene]; Or it may be a triphenylenyl group.

)로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 나프틸기; 메틸기 또는 페닐기로 치환 또는 비치환된 플루오레닐기; 9,9'-스피로비[플루오렌]; 또는 트리페닐레닐기일 수 있다.In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently deuterium; halogen group; cyano group; A cyano group or a triphenylsilyl group (

) a substituted or unsubstituted phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; 9,9'-spirobi[fluorene]; Or it may be a triphenylenyl group.

In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto.

In an exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 and the compound of Formula 2 may be included in a weight ratio of 1:10 to 10:1.

In an exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 and the compound of Formula 2 may be included in a weight ratio of 1:5 to 5:1.

In an exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 and the compound of Formula 2 may be included in a weight ratio of 1:2 to 2:1.

The organic light emitting device of the present invention may further include one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

1 to 3 illustrate the stacking order of the electrode and the organic material layer of the organic light emitting device according to an exemplary embodiment of the present specification. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of an organic light emitting device known in the art may also be applied to the present application.

Referring to FIG. 1 , an organic light emitting device in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially stacked on a substrate 100 is illustrated. However, it is not limited to such a structure, and as shown in FIG. 2 , an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case in which the organic material layer is multi-layered. The organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic layer including the heterocyclic compound of Formula 1 may further include other materials if necessary.

In an exemplary embodiment of the present specification, there is provided a composition for an organic material layer of an organic light emitting device including the heterocyclic compound of Formula 1 described above.

In an exemplary embodiment of the present specification, the composition for an organic material layer may further include the compound of Formula 2 above.

In an exemplary embodiment of the present specification, the composition for an organic material layer may include the heterocyclic compound of Formula 1 and the compound of Formula 2 in a weight ratio of 1:10 to 10:1.

In an exemplary embodiment of the present specification, the composition for an organic material layer may include the heterocyclic compound of Formula 1 and the compound of Formula 2 in a weight ratio of 1:5 to 5:1.

In an exemplary embodiment of the present specification, the composition for an organic material layer may include the heterocyclic compound of Formula 1 and the compound of Formula 2 in a weight ratio of 1:2 to 2:1.

In one embodiment of the present specification, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer including the heterocyclic compound of Formula 1 above It provides a method of manufacturing an organic light emitting device.

A method of manufacturing an organic light emitting device according to another exemplary embodiment includes preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer is one or more organic material layers using a composition for an organic material layer including the heterocyclic compound of Formula 1 and the compound of Formula 2 Including the step of forming, the step of forming the organic material layer is a heterocyclic compound of Formula 1; And the compound of Formula 2 may be pre-mixed and formed using a thermal vacuum deposition method.

The pre-mixed refers to mixing the materials in one park before depositing the heterocyclic compound of Formula 1 and the compound of Formula 2 on the organic layer.

The pre-mixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present specification.

In the organic light emitting device according to an exemplary embodiment of the present specification, materials other than the compounds of Formulas 1 and 2 are exemplified below, but these are only for illustration and not for limiting the scope of the present application, may be substituted with known materials.

Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used. Specific examples of the anode material 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); combinations of metals and oxides such as ZnO:Al or SnO ₂ :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.

Materials having a relatively low work function may be used as the cathode material, and a metal, metal oxide, conductive polymer, or the like may be used. 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), 4,4',4''-tris[2-naphthyl(phenyl)amino]tri Phenylamine (2-TNATA), soluble conductive polymer polyaniline/Dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly( 3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid (Polyaniline/Camphor sulfonic acid), or polyaniline/poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrenesulfonate)) can

A pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low molecular weight or high molecular material may be used. For example, N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) may be used.

As the hole blocking material, BCP (Bathocuproine) may be used, but is not limited thereto.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used. For example, tris(8-hydroxyquinolinato)aluminum (Alq ₃ ) may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

A red, green, or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In this case, two or more light emitting materials may be deposited and used as individual sources, or may be premixed and deposited as a single source for use. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material together participate in light emission may be used.

In the exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be used alone as the host material.

In one embodiment of the present specification, as the host material, a mixture of the heterocyclic compound of Formula 1 and the compound of Formula 2 may be used, and additional materials may be further included.

In the exemplary embodiment of the present specification, a green phosphorescent dopant may be used as the dopant material.

In the exemplary embodiment of the present specification, Ir(ppy) ₃ may be used as the dopant material, but is not limited thereto.

When mixing and using a host of a light emitting material, a host of the same series may be mixed and used, or a host of different series may be mixed and used. For example, any two or more types of N-type host material or P-type host material may be selected and used as the host material of the light emitting layer.

The organic light emitting device according to an exemplary embodiment of the present specification may be a top emission type, a back emission type, or a double side emission type depending on a material used.

The compound according to an exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

[Preparation Example 1] Preparation of compound 1-1

1) Preparation of compound 1-1-1

2-chloro-4,6-diphenyl-1,3,5-triazine in a one neck round bottom flask ) [A] (10 g, 0.037 mol), 1-bromo-9H-carbazole [B] (10.02 g, 0.041 mol), NaH (1.33 g, 0.056 mol) and dimethyl A mixture of formamide (Dimethylformamide, DMF) (100 mL) was added and refluxed at 185 °C. After the reaction was completed, quenching was performed, the precipitated solid was filtered, and the solid was dissolved in 1,2-dichlorobenzene, followed by a silica gel filter. After concentration, it was treated with methanol to obtain compound 1-1-1. (16.60g, yield 94%)

2) Preparation of compound 1-1

Compound 1-1-1 (16.60 g, 0.035 mol), diphenylamine [C] (6.51 g, 0.039 mol), Pd ₂ (dba) ₃ (tris(dibenzylideneacetone) in a 1-neck round bottom flask ) Dipalladium (0)) (3.21 g, 0.0035 mol), Tri-tert-butylphosphine (t-Bu ₃ P) (7.08 g, 0.035 mol), Sodium Tert-Butoxide (Sodium) A mixture of tert-butoxide, t-BuONa) (6.87 g, 0.07 mol) and toluene (160 mL) was added and refluxed at 100 °C. After concentration by extraction with dichloromethane (DCM), a silica gel filter was applied, and after concentration, the target compound 1-1 was obtained by treatment with methanol. (16.33 g, yield 65%)

In Preparation Example 1, 2-chloro-4,6-diphenyl-1,3,5-triazine [A] instead of the compound A of Table 1, 1-bromo-9H-carbazole [B] instead of the following table The target compound D of Table 1 was synthesized in the same manner as in Preparation Example 1 except that Compound C of Table 1 was used instead of Compound B of 1, diphenylamine [C] .

[Table 1]

[Preparation Example 2] Preparation of compound 1-200

Compound 1-1 (16.33 g, 0.029 mol), triflic acid (CF ₃ SO ₃ H) (43.52 g, 0.29 mol) and D ₆ -benzene prepared in Preparation Example 1 in a one-necked round-bottom flask (D ₆ -Benzene) (150 mL) The mixture was refluxed at 70 °C. After quenching and extraction with DCM and H ₂ O, the resultant was concentrated and filtered through silica gel. After concentration, it was treated with methanol to obtain compound 1-200. (13.41 g, 78%)

In Preparation Example 1, 2-chloro-4,6-diphenyl-1,3,5-triazine [A] instead of the compound A of Table 2 below, 1-bromo-9H-carbazole [B] instead of the following table After synthesizing in the same manner as in Preparation Example 1 except that Compound C of Table 2 was used instead of Compound B and diphenylamine [C] of 2, the target compound E of Table 2 was prepared in the same manner as in Preparation Example 2 synthesized.

[Table 2]

[Preparation Example 3] Preparation of compound 2-6

9-phenyl-9H,9'H-3,3'-bicarbazole (9-phenyl-9H,9'H-3,3'-bicarbazole) [F] (10g, 0.024mol ), 4-bromo-1,1':4',1''-terphenyl (4-bromo-1,1':4',1''-terphenyl) [G] (8.16 g, 0.026 mol) , CuI (4.57 g, 0.024 mol), trans-1,2-diaminocyclohexane (2.74 g, 0.024 mol), K ₃ PO ₄ (10.19 g, 0.048 mol) 1 ,4-Dioxane was dissolved in 100mL and refluxed at 125°C for 8 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain compound 2-6. (14.06 g, 92%)

In Preparation Example 3, 9-phenyl-9H,9'H-3,3'-bicarbazole [F] instead of the compound F of Table 3 below, 4-bromo-1,1':4',1'' The target compound H of Table 3 was synthesized in the same manner as in Preparation Example 3, except that compound G of Table 3 was used instead of -terphenyl [G] .

[Table 3]

The synthesis confirmation results of the compounds prepared above are shown in Tables 4 and 5 below. Table 4 is a measurement value of the FD-mass spectrometer (FD-Mass: Field desorption mass spectrometry), Table 5 is a measurement value of ¹ H NMR (DMSO, 300Mz).

compound FD-Mass compound FD-Mass 1-1 m/z= 565.68 (C ₃₉ H ₂₇ N ₅ =565.23) 1-2 m/z= 565.68 (C ₃₉ H ₂₇ N ₅ =565.23) 1-3 m/z= 565.68 (C ₃₉ H ₂₇ N ₅ =565.23) 1-8 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-9 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-11 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-12 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-18 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-20 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-26 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-28 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-33 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-35 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-38 m/z= 655.76 (C ₄₅ H ₂₉ N ₅ O=655.24) 1-41 m/z= 655.76 (C ₄₅ H ₂₉ N ₅ O=655.24) 1-42 m/z= 655.76 (C ₄₅ H ₂₉ N ₅ O=655.24) 1-44 m/z= 671.82 (C ₄₅ H ₂₉ N ₅ S=671.21) 1-45 m/z= 655.76 (C ₄₅ H ₂₉ N ₅ O=655.24) 1-47 m/z= 655.76 (C ₄₅ H ₂₉ N ₅ O=655.24) 1-48 m/z= 731.86 (C ₅₁ H ₃₃ N ₅ O=731.27) 1-51 m/z= 747.92 (C ₅₁ H ₃₃ N ₅ S=747.25) 1-53 m/z= 745.84 (C ₅₁ H ₃₁ N ₅ O ₂ =745.25) 1-56 m/z= 745.84 (C ₅₁ H ₃₁ N ₅ O ₂ =745.25) 1-61 m/z= 777.96 (C ₅₁ H ₃₁ N ₅ S ₂ =777.20) 1-64 m/z= 777.96 (C ₅₁ H ₃₁ N ₅ S ₂ =777.20) 1-72 m/z= 777.96 (C ₅₁ H ₃₁ N ₅ S ₂ =777.20) 1-81 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-86 m/z= 641.78 (C ₄₅ H ₃₁ N ₅ =641.26) 1-87 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-90 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-96 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-97 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-104 m/z= 793.97 (C ₅₇ H ₃₉ N ₅ =793.32) 1-105 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-109 m/z= 793.97 (C ₅₇ H ₃₉ N ₅ =793.32) 1-112 m/z= 870.07 (C ₆₃ H ₄₃ N ₅ =869.35) 1-121 m/z= 870.07 (C ₆₃ H ₄₃ N ₅ =869.35) 1-123 m/z= 870.07 (C ₆₃ H ₄₃ N ₅ =869.35) 1-130 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-132 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-136 m/z= 717.88 (C ₅₁ H ₃₅ N ₅ =717.29) 1-146 m/z= 793.97 (C ₅₇ H ₃₉ N ₅ =793.32) 1-152 m/z= 870.07 (C ₆₃ H ₄₃ N ₅ =869.35) 1-161 m/z= 747.92 (C ₅₁ H ₃₃ N ₅ S=747.25) 1-164 m/z= 807.96 (C ₅₇ H ₃₇ N ₅ O=807.30) 1-168 m/z= 807.96 (C ₅₇ H ₃₇ N ₅ O=807.30) 1-169 m/z= 824.02 (C ₅₇ H ₃₇ N ₅ S=823.28) 1-172 m/z= 884.06 (C ₆₃ H ₄₁ N ₅ O=883.33) 1-176 m/z= 884.06 (C ₆₃ H ₄₁ N ₅ O=883.33) 1-177 m/z= 821.94 (C ₅₇ H ₃₅ N ₅ O ₂ =821.28) 1-180 m/z= 821.94 (C ₅₇ H ₃₅ N ₅ O ₂ =821.28) 1-181 m/z= 854.06 (C ₅₇ H ₃₅ N ₅ S ₂ =853.23) 1-195 m/z= 757.94 (C ₅₄ H ₃₉ N ₅ =757.32) 1-196 m/z= 757.94 (C ₅₄ H ₃₉ N ₅ =757.32) 1-200 m/z= 592.40 (C ₃₉ D ₂₇ N ₅ =592.84) 1-204 m/z= 592.40 (C ₃₉ D ₂₇ N ₅ =592.84) 1-225 m/z= 655.24 (C ₄₅ H ₂₉ N ₅ O=655.76) 1-226 m/z= 655.24 (C ₄₅ H ₂₉ N ₅ O=655.76) 1-228 m/z= 655.24 (C ₄₅ H ₂₉ N ₅ O=655.76) 1-236 m/z= 655.24 (C ₄₅ H ₂₉ N ₅ O=655.76) 1-246 m/z= 671.21 (C ₄₅ H ₂₉ N ₅ S=672.82) 1-248 m/z= 671.21 (C ₄₅ H ₂₉ N ₅ S=672.82) 1-260 m/z= 745.25 (C ₅₁ H ₃₁ N ₅ O ₂ =745.84) 1-263 m/z= 745.25 (C ₅₁ H ₃₁ N ₅ O ₂ =745.84) 1-265 m/z= 684.42 (C ₄₅ D ₂₉ N ₅ O=684.94) 1-266 m/z= 700.40 (C ₄₅ D ₂₉ N ₅ S=701.00) 2-6 m/z= 636.80 (C ₄₈ H ₃₂ N ₂ =636.26) 2-8 m/z= 534.66 (C ₄₀ H ₂₆ N ₂ =534.21) 2-16 m/z= 634.78 (C ₄₈ H ₃₀ N ₂ =634.24) 2-34 m/z= 712.90 (C ₅₄ H ₃₆ N ₂ =712.29) 2-44 m/z= 712.90 (C ₅₄ H ₃₆ N ₂ =712.29) 2-52 m/z= 788.99 (C ₆₀ H ₄₀ N ₂ =788.32) 2-61 m/z= 788.99 (C ₆₀ H ₄₀ N ₂ =788.32) 2-73 m/z= 786.98 (C ₆₀ H ₃₈ N ₂ =786.30)

compound ¹ H NMR (DMSO, 300 Mz) 1-1 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 (1H, d), 7.85 (1H, d), 7.50 (6H, m), 7.35 (2H, m), 7.00 to 7.25 (12H, m) 1-2 δ = 8.55 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.94 (1H, d), 7.50 (6H, m), 7.00 to 7.35 (14H, m) 1-3 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 (1H, d), 7.50 (6H, m), 7.00~7.33 (15H, m) 1-8 δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 8.24 (1H, d), 7.94 (2H, m), 7.73 to 7.75 (3H, m), 7.61 (1H, d), 7.00 to 7.50 (20H, m) 1-9 δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 7.94 (2H, m), 7.73 to 7.75 (3H, m), 7.61 (1H, d), 7.00 to 7.50 (21H, m) 1-11 δ = 8.55 (1H, d), 8.24 (1H, d), 7.94 to 7.96 (5H, m), 7.75 (4H, d), 7.00 to 7.49 (24H, m) 1-12 δ = 8.55 (1H, d), 7.94 to 7.96 (5H, m), 7.75 (4H, d), 7.00 to 7.49 (25H, m) 1-18 δ = 8.55 (1H, d), 8.38 (2H, d), 7.94 (3H, m), 7.73 to 7.75 (6H, m), 7.61 (2H, d), 7.00 to 7.49 (25H, m) 1-20 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.94 to 7.96 (4H, m), 7.73 to 7.75 (3H, m), 7.61 (2H, d), 7.00 to 7.50 (22H, m) 1-26 δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (2H, m), 7.94 (1H, d), 7.85 (1H, d), 7.60 to 7.68 (2H, m), 7.50 ( 6H, m), 7.35 (2H, m), 7.00~7.25 (12H, m) 1-28 δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (3H, m), 7.94 (1H, d), 7.60 to 7.68 (2H, m), 7.50 (6H, m), 7.00 to 7.35 (14H, m) 1-33 δ = 8.55 (1H, d), 8.36 to 8.38 (5H, m), 8.21 (1H, s), 7.94 (2H, m), 7.60 to 7.73 (4H, m), 7.47 to 7.50 (7H, m), 7.00~7.35 (15H, m) 1-35 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 (2H, m), 7.60 to 7.75 (6H, m), 7.00 to 7.50 (20H, m) 1-38 δ = 8.55 (1H, d), 8.36 (2H, m), 7.94~8.03 (3H, m), 7.76~7.85 (3H, m), 7.50~7.54 (4H, m), 7.00~7.39 (16H, m) ) 1-41 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.94 to 8.03 (3H, m), 7.76 to 7.82 (2H, m), 7.50 to 7.54 (4H, m), 7.00~7.39 (16H, m) 1-42 δ = 8.55 (1H, d), 8.36 (2H, m), 7.79 to 7.98 (5H, m), 7.50 to 7.54 (4H, m), 7.00 to 7.39 (17H, m) 1-44 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.20 to 8.24 (3H, m), 7.94 (2H, d), 7.49 to 7.56 (5H, m), 7.00 to 7.35 (14H, m) 1-45 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.20 to 8.24 (2H, m), 7.93 to 7.94 (3H, d), 7.49 to 7.56 (5H, m), 7.00~7.35 (15H, m) 1-47 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.03 (1H, d), 7.93 to 7.94 (3H, d), 7.68 (1H, t), 7.49 to 7.56 ( 5H, m), 7.00~7.35 (15H, m) 1-48 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 to 8.03 (3H, m), 7.76 to 7.82 (2H, m), 7.50 to 7.68 (6H, m) ), 7.00~7.39 (16H, m) 1-51 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.91 to 7.94 (7H, m), 7.70 (1H, t), 7.49 to 7.56 ( 5H, m), 7.00~7.35 (14H, m) 1-53 δ = 8.55 (1H, d), 8.24 (1H, d), 7.94 to 8.03 (5H, m), 7.76 to 7.82 (4H, m), 7.54 (2H, d), 7.00 to 7.39 (18H, m) 1-56 δ = 8.55 (1H, d), 7.94~8.03 (4H, m), 7.76~7.82 (3H, m), 7.69 (1H, d), 7.54~7.57 (3H, m), 7.00~7.39 (19H, m) ) 1-61 δ = 8.55 (2H, d), 8.45 (2H, d), 8.24 (1H, d), 7.92 to 7.94 (5H, m), 7.70 (2H, t), 7.49 to 7.56 (4H, m), 7.00 to 7.35 (14H, m) 1-64 δ = 8.55 (2H, d), 8.45 (2H, d), 8.24 (1H, d), 8.03 (1H, d), 7.93 to 7.94 (5H, m), 7.68 to 7.70 (2H, m), 7.35 to 7.56 (4H, m), 7.00~7.35 (14H, m) 1-72 δ = 8.55 (1H, d), 8.45 (2H, d), 8.20 to 8.24 (2H, m), 7.92 to 7.94 (5H, m), 7.70 (1H, t), 7.49 to 7.56 (4H, m), 7.00~7.35 (20H, m) 1-81 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 (1H, d), 7.85 (1H, d), 7.75 (2H, d), 7.35 to 7.55 (15H, m), 7.00 to 7.24 ( 7H, m) 1-86 δ = 8.55 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.94 (1H, d), 7.75 (2H, d), 7.00 to 7.55 (22H, m) 1-87 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 (1H, d), 7.75 (2H, d), 7.00 to 7.55 (23H, m) 1-90 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 (1H, d), 7.75 (4H, d), 7.16 to 7.55 (25H, m) 1-96 δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 8.24 (1H, d), 7.94 (2H, m), 7.73 to 7.75 (5H, m), 7.00 to 7.55 (23H, m) 1-97 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.94 to 7.96 (3H, m), 7.75 (4H, d), 7.00 to 7.55 (24H, m) 1-104 δ = 8.55 (1H, d), 7.94 to 7.96 (5H, m), 7.75 (6H, d), 7.00 to 7.55 (17H, m) 1-105 δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 7.94 (2H, m), 7.73 to 7.75 (5H, m), 7.00 to 7.55 (24H, m) 1-109 δ = 8.55 (1H, d), 8.36 to 8.38 (3H, m), 7.94 (2H, m), 7.73 to 7.75 (7H, m), 7.16 to 7.55 (26H, m) 1-112 δ = 8.55 (1H, d), 7.94 to 7.96 (5H, m), 7.75 (8H, d), 7.16 to 7.55 (29H, m) 1-121 δ = 8.55 (1H, d), 8.36 (2H, m), 7.94 to 7.96 (4H, m), 7.83 to 7.75 (5H, m), 7.00 to 7.61 (27H, m) 1-123 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.94 to 7.96 (3H, m), 7.75 (4H, d), 7.00 to 7.55 (23H, m) 1-130 δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (2H, m), 7.94 (1H, d), 7.85 (1H, d), 7.35 to 7.68 (19H, m), 7.00 to 7.25 (7H, m) 1-132 δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (3H, m), 7.94 (1H, d), 7.68 to 7.75 (3H, m), 7.00 to 7.60 (23H, m) 1-136 δ = 8.55 (1H, d), 8.36 (4H, m), 8.21 to 8.24 (3H, m), 7.94 (1H, d), 7.68 to 7.75 (3H, m), 7.00 to 7.60 (23H, m) 1-146 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.91 to 7.96 (7H, m), 7.75 (4H, d), 7.00 to 7.55 (24H, m) 1-152 δ = 8.55 (1H, d), 8.36 (2H, m), 8.24 (1H, d), 7.91 to 7.96 (8H, m), 7.73 to 7.75 (5H, m), 7.00 to 7.61 (26H, m) 1-161 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.20 to 8.24 (2H, m), 7.93 to 7.94 (3H, d), 7.75 (2H, d), 7.00 to 7.56 (21H, m) 1-164 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 to 8.03 (3H, m), 7.00 to 7.82 (28H, m) 1-168 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 to 8.03 (3H, m), 7.00 to 7.82 (23H, m) 1-169 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.20 to 8.24 (2H, m), 7.93 to 7.94 (3H, d), 7.75 (4H, d), 7.17 to 7.55 (24H, m) 1-172 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 to 8.03 (3H, m), 7.17 to 7.75 (32H, m) 1-176 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (3H, m), 7.94 to 8.03 (3H, m), 7.31 to 7.82 (31H, m), 7.16 (1H, t) 1-177 δ = 8.55 (1H, d), 8.24 (1H, d), 7.94 to 8.03 (5H, m), 7.75 to 7.82 (6H, m), 7.00 to 7.55 (22H, m) 1-180 δ = 8.55 (1H, d), 7.94~8.03 (4H, m), 7.69~7.82 (6H, m), 7.00~7.57 (25H, m) 1-181 δ = 8.55 (1H, d), 8.45 (2H, d), 8.24 (1H, d), 8.12 (1H, s), 7.93 to 8.03 (7H, m), 7.68 to 7.75 (3H, m), 7.00 to 7.56 (20H, m) 1-184 δ = 8.55 (2H, d), 8.45 (2H, d), 8.20~8.24 (2H, m), 7.92~7.94 (5H, m), 7.70~7.75 (3H, m), 7.00~7.56 (21H, m) ) 1-195 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (2H, m), 7.90 to 7.94 (2H, m), 7.78 (1H, d), 7.00 to 7.68 (25H, m), 1.69 (6H, s) 1-196 δ = 8.55 (1H, d), 8.36 (2H, m), 8.21 to 8.24 (2H, m), 7.78 to 7.94 (4H, m), 7.00 to 7.68 (24H, m), 1.69 (6H, s) 1-200 δ = no ¹ H NMR peak with 100% deuterium content 1-204 δ = no ¹ H NMR peak with 100% deuterium content 1-225 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (2H, m), 7.85 (1H, d), 7.64 (1H, d), 7.50 to 7.54 (7H, m), 6.97 to 7.39 (13H, m) 1-226 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94~8.03 (3H, m), 7.80~7.85 (2H, m), 7.50~7.54 (7H, m), 7.00~7.39 (11H, m) ), 6.91 (1H, d) 1-228 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (2H, m), 7.85 (1H, d), 7.50 to 7.54 (7H, m), 7.00 to 7.98 (13H, m), 6.91 (1H, d) 1-236 δ = 8.55 (1H, d), 8.36 (4H, m), 7.94 to 7.98 (2H, m), 7.50 to 7.54 (7H, m), 7.00 to 7.39 (14H, m), 6.91 (1H, d) 1-246 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.93 to 8.01 (3H, m), 7.64 (1H, s), 7.00 to 7.56 ( 18H, m) 1-248 δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.93 to 7.94 (2H, d), 7.00 to 7.59 (20H, m) 1-260 δ = 8.55 (1H, d), 8.36 (4H, m), 8.24 (1H, d), 7.94 to 8.03 (5H, m), 7.80 (2H, d), 7.50 to 7.54 (8H, m), 7.25 to 7.39 (7H, m), 7.16 (1H, t), 6.91 (2H, d) 1-263 δ = 8.55 (1H, d), 8.36 (2H, m), 8.22 (1H, s), 7.94 to 8.03 (4H, m), 7.76 to 7.85 (3H, m), 6.97 to 7.56 (20H, m) 1-265 δ = no ¹ H NMR peak with 100% deuterium content 1-266 δ = no ¹ H NMR peak with 100% deuterium content 2-6 δ = 8.55 (1H, d), 8.30 (1H, d), 8.13 to 8.19 (2H, m), 7.89 to 7.99 (8H, m), 7.75 to 7.77 (3H, m), 7.35 to 7.62 (11H, m) ), 7.16~7.25 (6H, m) 2-8 δ = 8.55 (1H, d), 8.30 (1H, d), 8.11 to 8.19 (5H, m), 7.89 to 7.99 (4H, m), 7.77 to 7.79 (2H, m), 7.50 to 7.62 (10H, m) ), 7.35 (1H, t), 7.16~7.20 (2H, m) 2-16 δ = 9.05 (1H, s), 8.55 (1H, d), 8.13 to 8.33 (7H, m), 7.89 to 7.99 (5H, m), 7.50 to 7.77 (13H, m), 7.35 (1H, t), 7.16~7.20 (2H, m) 2-34 δ = 8.55 (1H, d), 8.30 (1H, d), 8.13 to 8.21 (3H, m), 7.89 to 7.99 (8H, m), 7.35 to 7.77 (17H, m), 7.16 to 7.25 (6H, m) ) 2-44 δ = 8.55 (1H, d), 8.30 (1H, d), 8.13 to 8.19 (2H, m), 7.89 to 7.99 (12H, m), 7.75 to 7.77 (5H, m), 7.58 (1H, d), 7.35~7.50 (8H, m), 7.16~7.25 (6H, m) 2-52 δ = 8.55 (1H, d), 8.30 (1H, d), 8.13 to 8.21 (4H, m), 7.89 to 7.99 (4H, m), 7.35 to 7.77 (20H, m), 7.16 to 7.52 (10H, m) ) 2-61 δ = 8.55 (1H, d), 8.30 (1H, d), 8.13 to 8.19 (2H, m), 7.89 to 7.99 (12H, m), 7.75 to 7.77 (5H, m), 7.58 (1H, d), 7.35~7.50 (8H, m), 7.16~7.25 (10H, m) 2-73 δ = 9.05 (1H, s), 8.55 (1H, d), 8.19 to 8.33 (9H, m), 7.89 to 7.99 (6H, m), 7.35 to 7.77 (19H, m), 7.16 to 7.20 (2H, m) )

<Experimental Example 1>

1) Fabrication of an organic light emitting device

Comparative Examples 1 to 8 and Examples 1 to 67

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and the substrate was transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N,N'-Di) (1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The light emitting layer was deposited by doping the host with 7% Ir(ppy) ₃ using the compounds shown in Table 4 below as a host and Ir(ppy) ₃ (tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, followed by deposition of 400 Å. Thereafter, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1200 Å on the electron injection layer to form a negative electrode, thereby forming an organic electric field. A light emitting device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 ^-8 to 10 ^-6 torr for each material, respectively, and used for OLED manufacturing.

2) Driving voltage and luminous efficiency of organic electroluminescent device

For the organic electroluminescent device manufactured as described above, electroluminescence (EL) characteristics were measured with M7000 of McScience, and the reference luminance was 6,000 cd through the life measuring device (M6000) manufactured by McScience with the measurement result. At /m ² , T ₉₀ was measured. Table 6 shows the characteristics of the organic electroluminescent device of the present invention.

[Comparative example]

compound drive voltage
(V) luminous efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 A 5.83 42.7 (0.275, 0.674) 64 Comparative Example 2 B 6.12 41.8 (0.286, 0.670) 60 Comparative Example 3 C 5.69 44.5 (0.281, 0.675) 77 Comparative Example 4 D 5.66 43.2 (0.283, 0.674) 83 Comparative Example 5 E 5.73 45.5 (0.285, 0.666) 94 Comparative Example 6 F 5.50 46.9 (0.280, 0.672) 100 Comparative Example 7 G 5.57 45.8 (0.265, 0.669) 97 Comparative Example 8 H 5.77 44.7 (0.287, 0.672) 92 Example 1 1-1 3.13 85.9 (0.273, 0.680) 181 Example 2 1-2 3.67 84.7 (0.270, 0.673) 173 Example 3 1-3 3.55 83.6 (0.268, 0.675) 167 Example 4 1-8 3.28 86.2 (0.274, 0.677) 165 Example 5 1-9 3.15 87.6 (0.250, 0.662) 170 Example 6 1-11 3.11 88.0 (0.281, 0.673) 175 Example 7 1-12 3.62 87.9 (0.263, 0.675) 188 Example 8 1-18 3.58 84.6 (0.280, 0.662) 169 Example 9 1-20 3.47 85.7 (0.275, 0.672) 173 Example 10 1-26 3.65 90.2 (0.269, 0.673) 177 Example 11 1-28 3.68 89.3 (0.262, 0.663) 187 Example 12 1-33 3.55 88.5 (0.287, 0.652) 190 Example 13 1-35 3.72 82.7 (0.278, 0.663) 183 Example 14 1-38 3.88 74.6 (0.276, 0.675) 159 Example 15 1-41 3.82 72.8 (0.249, 0.675) 155 Example 16 1-42 3.74 70.3 (0.276, 0.658) 160 Example 17 1-44 4.13 68.9 (0.260, 0.675) 144 Example 18 1-45 4.21 67.7 (0.283, 0.662) 150 Example 19 1-47 4.29 70.3 (0.275, 0.672) 148 Example 20 1-48 4.27 69.2 (0.275, 0.665) 153 Example 21 1-51 4.30 67.9 (0.258, 0.673) 142 Example 22 1-53 4.42 66.1 (0.262, 0.668) 143 Example 23 1-56 4.33 65.3 (0.268, 0.667) 147 Example 24 1-61 4.77 63.3 (0.275, 0.672) 130 Example 25 1-64 4.81 61.5 (0.257, 0.662) 135 Example 26 1-72 4.79 60.7 (0.265, 0.658) 132 Example 27 1-81 3.39 72.9 (0.266, 0.675) 159 Example 28 1-86 3.17 80.3 (0.275, 0.675) 183 Example 29 1-87 3.22 82.1 (0.265, 0.657) 172 Example 30 1-90 3.25 77.9 (0.266, 0.665) 165 Example 31 1-96 3.63 76.2 (0.267, 0.673) 166 Example 32 1-97 3.58 74.3 (0.283, 0.656) 159 Example 33 1-104 3.66 75.9 (0.269, 0.667) 167 Example 34 1-105 3.70 76.3 (0.283, 0.675) 153 Example 35 1-109 3.28 82.0 (0.263, 0.672) 162 Example 36 1-112 3.17 80.7 (0.267, 0.664) 173 Example 37 1-121 3.42 77.6 (0.256, 0.662) 175 Example 38 1-123 3.52 78.9 (0.250, 0.665) 169 Example 39 1-130 3.49 80.7 (0.267, 0.662) 157 Example 40 1-132 3.44 75.5 (0.259, 0.669) 166 Example 41 1-136 3.12 72.9 (0.266, 0.687) 170 Example 42 1-146 3.53 81.6 (0.269, 0.659) 177 Example 43 1-152 3.02 82.7 (0.263, 0.674) 183 Example 44 1-161 4.08 67.5 (0.265, 0.682) 152 Example 45 1-164 4.47 69.2 (0.257, 0.658) 146 Example 46 1-168 4.39 66.8 (0.257, 0.660) 132 Example 47 1-169 4.28 64.9 (0.264, 0.657) 133 Example 48 1-172 4.14 70.3 (0.262, 0.670) 149 Example 49 1-176 4.53 68.7 (0.250, 0.672) 150 Example 50 1-177 4.83 60.7 (0.263, 0.675) 132 Example 51 1-180 4.77 62.4 (0.262, 0.658) 139 Example 52 1-181 5.07 58.8 (0.268, 0.667) 125 Example 53 1-184 5.13 55.9 (0.270, 0.665) 112 Example 54 1-195 5.28 53.8 (0.265, 0.679) 103 Example 55 1-196 5.13 52.7 (0.273, 0.680) 109 Example 56 1-200 2.87 91.3 (0.265, 0.676) 192 Example 57 1-204 2.93 91.7 (0.283, 0.653) 195 Example 58 1-225 2.88 90.2 (0.271, 0.667) 190 Example 59 1-226 2.76 89.7 (0.283, 0.670) 187 Example 60 1-228 2.79 89.5 (0.273, 0.652) 175 Example 61 1-236 2.63 87.6 (0.267, 0.662) 183 Example 62 1-246 3.02 91.0 (0.253, 0.662) 177 Example 63 1-248 3.07 90.7 (0.255, 0.660) 172 Example 64 1-260 2.99 86.5 (0.264, 0.653) 180 Example 65 1-263 3.10 88.3 (0.262, 0.671) 188 Example 66 1-265 2.77 91.3 (0.252, 0.672) 192 Example 67 1-266 2.79 90.5 (0.266, 0.672) 193

Looking at the results of Table 6, the heterocyclic compound of the present invention used in Examples is a carbazole having a property of transferring a hole to a triazine having a property of transferring an electron, and an arylamine group is combined with an electron faster than a hole. It is possible to lower the migration rate and adjust the hole mobility and charge balance by attaching an arylamine substituent to a specific site of the carbazole. Accordingly, the material of the present invention is easy to control the recombination zone of the device.

Positions 1 and 3 of carbazole are relatively electron-rich due to their resonance structure. Of these, the 1st position of carbazole lacks electrons than the 3rd position due to an adjacent nitrogen atom, so when an arylamine substituent is bonded to the 1st position of the carbazole, the electrons lacking the lone pair of P orbitals are filled to balance the charge. and the stability of the molecular structure is also increased. In the same principle, when an arylamine substituent is bonded to the 2nd and 4th positions of the carbazole, which is relatively lacking in electrons due to the resonance structure, the charge balance is higher than when bonding to the 3rd position of the carbazole (Comparative Examples 5 and 6). is appropriate, so that the driving and luminous efficiency are better.

In addition, Comparative Examples 1, 2, and 4 using compounds A, B, and D that do not include an arylamine group, respectively, have a strong electron injection ability compared to the hole injection ability, and thus the charge balance is not met, resulting in a high driving voltage, It has low luminous efficiency and short lifespan.

In the case of Comparative Examples 6 and 7, compounds F and G in which two arylamine groups are substituted in carbazole were used, which is because more holes are injected than in the compound in which one arylamine group is substituted in carbazole, resulting in a hole trap. In terms of driving voltage, luminous efficiency, and lifespan, the effect is not as good as in the embodiment using the compound of the present invention.

<Experimental Example 2>

1) Fabrication of an organic light emitting device

Examples 68-187

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and the substrate was transferred to a thermal deposition equipment for organic deposition.

A hole injection layer 2-TNATA (4,4,4′′-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and a hole transport layer NPB (N,N′-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The light emitting layer was pre _- mixed with one heterocyclic compound of Formula 1 and one compound of Formula 2 described in Table 5 below as a host, and was deposited at 400 Å in one park after preliminary mixing. Deposited by doping 7% of the deposition thickness. After that, 60Å of BCP was deposited as a hole blocking layer, and 200Å of Alq ₃ was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum sublimated and purified under 10 ^-8 to 10 ^-6 torr for each material, respectively, and used for OLED manufacturing.

2) Driving voltage and luminous efficiency of organic electroluminescent device

For the organic electroluminescent device manufactured as described above, electroluminescence (EL) characteristics were measured with M7000 of McScience, and the reference luminance was 6,000 cd through the life measuring device (M6000) manufactured by McScience with the measurement result. At /m ² , T ₉₀ was measured.

The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light emitting device manufactured according to the present invention are shown in Table 7 below.

light emitting layer
compound ratio
(weight ratio) drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Example 68 1-1 : 2-8 1:1 2.31 148.6 (0.263, 0.660) 329 Example 69 1-1 : 2-8 1: 2 2.29 148.2 (0.259, 0.645) 333 Example 70 1-1 : 2-8 1: 3 2.23 146.7 (0.266, 0.659) 348 Example 71 1-2: 2-34 1:1 2.38 155.9 (0.257, 0.660) 358 Example 72 1-2: 2-34 1: 2 2.33 155.7 (0.259, 0.652) 362 Example 73 1-2: 2-34 1: 3 2.32 153.3 (0.273, 0.652) 369 Example 74 1-3 : 2-16 1:1 2.60 155.7 (0.258, 0.704) 349 Example 75 1-3 : 2-16 1: 2 2.55 154.3 (0.260, 0.625) 352 Example 76 1-3 : 2-16 1: 3 2.53 154.0 (0.263, 0.619) 355 Example 77 1-11: 2-61 1:1 2.47 157.3 (0.260, 0.704) 350 Example 78 1-11: 2-61 1: 2 2.46 155.9 (0.255, 0.657) 356 Example 79 1-11: 2-61 1: 3 2.43 154.0 (0.269, 0.635) 363 Example 80 1-20: 2-16 1:1 2.39 157.6 (0.259, 0.680) 359 Example 81 1-20: 2-16 1: 2 2.35 155.3 (0.251, 0.643) 362 Example 82 1-20: 2-16 1: 3 2.34 153.2 (0.245, 0.707) 369 Example 83 1-35: 2-34 1:1 2.19 160.2 (0.261, 0.622) 385 Example 84 1-35: 2-34 1: 2 2.15 158.7 (0.251, 0.625) 389 Example 85 1-35: 2-34 1: 3 2.13 155.3 (0.258, 0.710) 400 Example 86 1-38: 2-52 1:1 2.87 143.7 (0.263, 0.662) 268 Example 87 1-38: 2-52 1: 2 2.86 143.2 (0.260, 0.732) 273 Example 88 1-38: 2-52 1: 3 2.80 142.3 (0.660, 0.658) 279 Example 89 1-41: 2-44 1:1 2.99 145.0 (0.263, 0.637) 264 Example 90 1-41: 2-44 1: 2 2.94 144.5 (0.249, 0.659) 265 Example 91 1-41: 2-44 1: 3 2.91 144.2 (0.265, 0.673) 269 Example 92 1-42: 2-34 1:1 2.93 136.7 (0.252, 0.657) 275 Example 93 1-42: 2-34 1: 2 2.88 136.3 (0.248, 0.632) 277 Example 94 1-42: 2-34 1: 3 2.83 135.2 (0.265, 0.663) 280 Example 95 1-44: 2-16 1:1 3.11 143.8 (0.262, 0.652) 268 Example 96 1-44: 2-16 1: 2 3.07 142.1 (0.245, 0.710) 272 Example 97 1-44: 2-16 1: 3 2.93 141.8 (0.268, 0.628) 279 Example 98 1-48: 2-52 1:1 3.21 145.2 (0.265, 0.667) 262 Example 99 1-48: 2-52 1: 2 3.18 145.0 (0.267, 0.657) 264 Example 100 1-48: 2-52 1: 3 3.16 144.3 (0.257, 0.730) 266 Example 101 1-51: 2-34 1:1 3.10 144.7 (0.250, 0.619) 251 Example 102 1-51: 2-34 1: 2 2.93 143.5 (0.246, 0.622) 253 Example 103 1-51: 2-34 1: 3 2.89 143.2 (0.252, 0.653) 255 Example 104 1-56 : 2-61 1:1 3.78 125.2 (0.265, 0.663) 185 Example 105 1-56 : 2-61 1: 2 3.66 123.7 (0.267, 0.650) 193 Example 106 1-56 : 2-61 1: 3 3.62 120.7 (0.273, 0.663) 197 Example 107 1-64: 2-34 1:1 3.65 123.3 (0.272, 0.662) 187 Example 108 1-64: 2-34 1: 2 3.63 120.8 (0.265, 0.678) 189 Example 109 1-64: 2-34 1: 3 3.57 119.6 (0.268, 0.674) 200 Example 110 1-81: 2-16 1:1 2.70 152.7 (0.273, 0.655) 293 Example 111 1-81: 2-16 1: 2 2.63 150.9 (0.275, 0.668) 313 Example 112 1-81: 2-16 1: 3 2.61 148.7 (0.253, 0.652) 320 Example 113 1-86: 2-52 1:1 2.73 157.3 (0.261, 0.665) 283 Example 114 1-86: 2-52 1: 2 2.66 155.2 (0.274, 0.663) 291 Example 115 1-86: 2-52 1: 3 2.58 152.4 (0.263, 0.675) 305 Example 116 1-96: 2-34 1:1 2.47 157.5 (0.266, 0.662) 307 Example 117 1-96: 2-34 1: 2 2.45 153.2 (0.263, 0.652) 312 Example 118 1-96: 2-34 1: 3 3.36 149.7 (0.263, 0.650) 325 Example 119 1-104: 2-52 1:1 2.23 159.9 (0.268, 0.657) 302 Example 120 1-104: 2-52 1: 2 2.11 156.3 (0.267, 0.665) 313 Example 121 1-104: 2-52 1: 3 2.03 155.7 (0.275, 0.663) 319 Example 122 1-105: 2-52 1:1 2.38 157.6 (0.266, 0.675) 300 Example 123 1-105: 2-52 1: 2 2.32 155.8 (0.264, 0.673) 307 Example 124 1-105: 2-52 1: 3 2.31 154.7 (0.273, 0.663) 312 Example 125 1-121: 2-34 1:1 2.25 160.7 (0.270, 0.681) 307 Example 126 1-121: 2-34 1: 2 2.13 158.3 (0.275, 0.652) 318 Example 127 1-121: 2-34 1: 3 2.07 157.7 (0.273, 0.673) 320 Example 128 1-130: 2-34 1:1 2.71 149.5 (0.263, 0.655) 281 Example 129 1-130: 2-34 1: 2 2.68 148.3 (0.261, 0.660) 293 Example 130 1-130: 2-34 1: 3 2.63 145.2 (0.259, 0.673) 299 Example 131 1-146: 2-52 1:1 2.53 155.3 (0.275, 0.653) 287 Example 132 1-146: 2-52 1: 2 2.50 154.7 (0.265, 0.675) 290 Example 133 1-146: 2-52 1: 3 2.47 150.3 (0.268, 0.654) 294 Example 134 1-152: 2-44 1:1 2.49 153.2 (0.254, 0.662) 291 Example 135 1-152: 2-44 1: 2 2.42 150.1 (0.250, 0.668) 295 Example 136 1-152: 2-44 1: 3 2.34 148.7 (0.267, 0.662) 300 Example 137 1-161: 2-16 1:1 3.38 140.2 (0.259, 0.659) 251 Example 138 1-161: 2-16 1: 2 3.35 139.3 (0.269, 0.687) 255 Example 139 1-161: 2-16 1: 3 3.31 138.2 (0.269, 0.659) 260 Example 140 1-168: 2-34 1:1 3.40 139.2 (0.263, 0.654) 243 Example 141 1-168: 2-34 1: 2 3.37 138.8 (0.265, 0.682) 247 Example 142 1-168: 2-34 1: 3 3.35 136.5 (0.255, 0.657) 253 Example 143 1-176: 2-16 1:1 3.28 137.2 (0.287, 0.672) 238 Example 144 1-176: 2-16 1: 2 3.22 137.0 (0.273, 0.685) 244 Example 145 1-176: 2-16 1: 3 3.12 135.7 (0.270, 0.673) 253 Example 146 1-180: 2-34 1:1 4.33 180.6 (0.258, 0.672) 173 Example 147 1-180: 2-34 1: 2 4.28 177.2 (0.274, 0.657) 175 Example 148 1-180: 2-34 1: 3 4.13 173.5 (0.253, 0.661) 180 Example 149 1-184: 2-8 1:1 4.49 178.2 (0.281, 0.673) 167 Example 150 1-184: 2-8 1: 2 4.32 177.4 (0.263, 0.675) 169 Example 151 1-184: 2-8 1: 3 4.11 173.2 (0.270, 0.668) 173 Example 152 1-200 : 2-8 1:1 2.21 155.7 (0.275, 0.685) 349 Example 153 1-200 : 2-8 1: 2 2.19 153.5 (0.271, 0.675) 351 Example 154 1-200 : 2-8 1: 3 2.15 152.2 (0.268, 0.673) 355 Example 155 1-204: 2-34 1:1 2.29 155.9 (0.275, 0.656) 358 Example 156 1-204: 2-34 1: 2 2.11 158.3 (0.254, 0.661) 365 Example 157 1-204: 2-34 1: 3 2.08 159.7 (0.281, 0.653) 367 Example 158 1-225 : 2-52 1:1 2.61 162.3 (0.273, 0.675) 333 Example 159 1-225 : 2-52 1: 2 2.59 161.8 (0.263, 0.662) 337 Example 160 1-225 : 2-52 1: 3 2.55 160.2 (0.254, 0.670) 342 Example 161 1-226 : 2-73 1:1 3.65 160.7 (0.274, 0.653) 321 Example 162 1-226 : 2-73 1: 2 3.62 159.3 (0.265, 0.672) 335 Example 163 1-226 : 2-73 1: 3 3.60 158.7 (0.273, 0.662) 339 Example 164 1-228 : 2-52 1:1 2.66 161.3 (0.266, 0.678) 338 Example 165 1-228 : 2-52 1: 2 2.63 159.7 (0.265, 0.671) 342 Example 166 1-228 : 2-52 1: 3 2.57 158.2 (0.273, 0.658) 344 Example 167 1-236 : 2-44 1:1 2.59 157.6 (0.267, 0.650) 328 Example 168 1-236 : 2-44 1: 2 2.54 156.3 (0.256, 0.643) 336 Example 169 1-236 : 2-44 1: 3 2.50 155.3 (0.267, 0.655) 341 Example 170 1-246: 2-34 1:1 2.48 158.9 (0.252, 0.661) 358 Example 171 1-246: 2-34 1: 2 2.44 157.7 (0.258, 0.653) 360 Example 172 1-246: 2-34 1: 3 2.37 152.4 (0.274, 0.652) 366 Example 173 1-248 : 2-16 1:1 2.52 157.9 (0.265, 0.665) 372 Example 174 1-248 : 2-16 1: 2 2.47 155.3 (0.275, 0.662) 378 Example 175 1-248 : 2-16 1: 3 2.43 152.7 (0.265, 0.665) 388 Example 176 1-260 : 2-52 1:1 2.38 155.7 (0.264, 0.653) 375 Example 177 1-260 : 2-52 1: 2 2.35 154.6 (0.263, 0.663) 377 Example 178 1-260 : 2-52 1: 3 2.33 152.4 (0.271, 0.673) 382 Example 179 1-263 : 2-52 1:1 2.46 160.3 (0.283, 0.675) 369 Example 180 1-263 : 2-52 1: 2 2.44 159.7 (0.263, 0.665) 372 Example 181 1-263 : 2-52 1: 3 2.41 158.2 (0.277, 0.663) 379 Example 182 1-265: 2-16 1:1 2.20 165.3 (0.274, 0.685) 387 Example 183 1-265: 2-16 1: 2 2.18 163.7 (0.268, 0.675) 395 Example 184 1-265: 2-16 1: 3 2.16 160.5 (0.273, 0.651) 401 Example 185 1-266 : 2-61 1:1 2.15 162.3 (0.255, 0.667) 397 Example 186 1-266 : 2-61 1: 2 2.11 161.7 (0.282, 0.673) 400 Example 187 1-266 : 2-61 1: 3 2.01 161.5 (0.264, 0.676) 403

Comparing the results of Examples 1 to 67 of Table 6 and Examples 68 to 187 of Table 7, when the heterocyclic compound of the present invention and the compound of Formula 2 are mixed and used as a host of the light emitting layer, Comparative Examples 1 to Compared to 8, the driving voltage is lower, the luminous efficiency is improved, and the lifespan is significantly improved. This result can be expected to occur when the two compounds are included at the same time exciplex (exciplex) phenomenon. The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan. In the present invention, it was confirmed that excellent device characteristics were exhibited when the compound of Formula 2 was used as a donor role of the light emitting layer host and the heterocyclic compound of Formula 1 was used as an acceptor role.

100: substrate
200: positive electrode
300: organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (17)

Heterocyclic compound of formula (1):
[Formula 1]

In Formula 1,
L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group,
m is an integer of 1 to 5, and when 2 or more, L is the same as or different from each other,
R1 to R10 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Any one of R3, R4 and R6 is represented by the following formula 1-A,
[Formula 1-A]

In Formula 1-A,
R11 to R20 are each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Adjacent groups of R11 to R20 are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring; Or it may form a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle,

denotes a position combined with Chemical Formula 1. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C20 aryl group; Or a substituted or unsubstituted C2 to C20 heteroaryl group is a heterocyclic compound. The method according to claim 1, wherein R5 and R7 to R10 are each independently hydrogen; Or a heterocyclic compound that is deuterium. The method according to claim 1, wherein R11 to R20 are each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6 to C30 aryl group, and adjacent groups of R11 to R20 combine with each other to form a substituted or unsubstituted C2 to C30 aliphatic or aromatic heterocyclic compound. The method according to claim 1, wherein L is a direct bond; phenylene group; Or a heterocyclic compound that is a biphenylene group. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light-emitting device comprising the heterocyclic compound according to any one of claims 1 to 6. The method according to claim 7, wherein the organic material layer comprises a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound. The method according to claim 7, wherein the organic material layer comprises a light emitting layer,
The light emitting layer includes a host,
The host is an organic light emitting device comprising the heterocyclic compound. The organic light-emitting device according to claim 7, wherein the organic material layer including the heterocyclic compound further comprises a compound of Formula 2 below:
[Formula 2]

In Formula 2,
R21 and R22 are the same as or different from each other, and are each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r31 is an integer of 0 to 7, and when 2 or more, R31 are the same as or different from each other,
r32 is an integer from 0 to 7, and in the case of 2 or more, R32 is the same as or different from each other. 11. The method of claim 10,
The organic material layer containing the heterocyclic compound is a light emitting layer,
The light emitting layer is an organic light emitting device comprising the heterocyclic compound and the compound of Formula 2 at the same time. The organic light-emitting device according to claim 10, wherein Chemical Formula 2 is represented by any one of the following compounds:

. The organic light emitting diode of claim 10, wherein the heterocyclic compound and the compound of Formula 2 are included in a weight ratio of 1:10 to 10:1. The method according to claim 7, wherein the organic light emitting device further comprises one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. phosphorus organic light emitting device. A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound according to any one of claims 1 to 6. The composition for an organic material layer of an organic light emitting device according to claim 15, further comprising a compound of Formula 2 below:
[Formula 2]

In Formula 2,
R21 and R22 are the same as or different from each other, and are each independently deuterium; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r31 is an integer of 0 to 7, and when 2 or more, R31 is the same as or different from each other,
r32 is an integer from 0 to 7, and in the case of 2 or more, R32 is the same as or different from each other. The composition for an organic material layer of an organic light emitting device according to claim 16, wherein the weight ratio of the heterocyclic compound and the compound of Formula 2 in the composition is 1:10 to 10:1.

Images