WO2024014716A1

WO2024014716A1 - Heterocyclic compound, organic light-emitting device comprising same, and composition for organic layer

Info

Publication number: WO2024014716A1
Application number: PCT/KR2023/008044
Authority: WO
Inventors: 허유진; 모준태; 김동준; 최대혁
Original assignee: 엘티소재주식회사
Priority date: 2022-07-13
Filing date: 2023-06-12
Publication date: 2024-01-18
Also published as: KR20240009224A; TW202404956A

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, an organic light-emitting device comprising same, and a composition for an organic layer.

Description

Heterocyclic compounds, compositions for organic light-emitting devices and organic material layers containing the same

This application claims the benefit of priority based on Republic of Korea Patent Application No. 10-2022-0086421, dated July 13, 2022, and includes all contents disclosed in the document of the Korean Patent Application as part of this specification.

The present invention relates to heterocyclic compounds, organic light-emitting devices containing the same, and compositions for organic material layers.

Organic light emitting devices are a type of self-emitting display devices and have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

[Prior art literature]

[Patent Document]

(Patent Document 1) U.S. Patent No. 4,356,429

The present invention seeks to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic material layer.

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

X1 to X3 are the same or different from each other and are each independently O or S,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle. Forming a, R101, R102 and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

a to e are the same or different from each other and are each independently an integer of 0 to 3,

f is an integer from 0 to 4,

m1 and m2 are the same or different from each other and are each independently an integer from 0 to 4,

n1 and n2 are the same as or different from each other, and are each independently an integer of 1 to 5.

Additionally, in an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Formula 1. to provide.

In addition, an exemplary embodiment of the present application provides an organic light-emitting device in which the organic material layer containing the heterocyclic compound of Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula A.

[Formula A]

In Formula A,

X ₁₁ to X ₁₃ are the same as or different from each other and are each independently N or CR',

At least one of X ₁₁ to X ₁₃ is N,

R _a1 to R _a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

In addition, another embodiment of the present application provides a composition for an organic layer comprising a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula A.

The heterocyclic compound according to one embodiment can be used as an organic layer material of an organic light-emitting device. The compound may serve as a hole injection layer material, an electron blocking layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, a hole blocking layer material, an electron injection layer material, etc. in an organic light emitting device. In particular, the compound can be used as a light-emitting layer material for an organic light-emitting device.

The heterocyclic compound may be used alone or in combination with a P-type host as a light-emitting material, and may be used as a host material or dopant material in the light-emitting layer.

In particular, the heterocyclic compound represented by Formula 1 includes a heteroaryl-based substituent in the dibenzofuran or dibenzothiophene structure, which is the core structure, so that the dibenzofuran or dibenzothiophene structure, which is the core structure, has electrons. The properties can be strengthened and the compound's band-gap and triplet excited state energy level (T ₁ ) value can be adjusted. Therefore, when the compound represented by Formula 1 is used in the organic material layer, the driving voltage of the organic light-emitting device can be lowered, the luminous efficiency can be improved, and the lifespan characteristics of the organic light-emitting device can be improved due to the thermal stability of the compound.

Specifically, when the compound represented by Formula 1 is used as a host material for the light-emitting layer, the heteroatom of the amine group improves the hole injection ability of the hole transport group, thereby increasing efficiency and lifespan. In particular, by fixing the position of the arylamine group corresponding to the hole transporting group of Formula 1 to a specific position as shown in Formula 1, it has a steric configuration and has HOMO (Highest Occupied Molecular Orbital) and LUMO. Because it enables strong charge transfer by spatially separating the Lowest Unoccupied Molecular Orbital, it is suitable as a red host material, and when used as an organic material in an organic light-emitting device, high efficiency can be expected.

1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present invention.

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

In this specification, the term "substitution" means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted. , when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, “substituted or unsubstituted” means deuterium; halogen; Cyano group; C1 to C60 straight or branched alkyl group; C2 to C60 straight or branched alkenyl group; C2 to C60 straight or branched alkynyl group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heteroaryl group; -SiRR'R"; -P(=O)RR'; a group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group. It means being substituted or unsubstituted with one or more substituents selected from, or substituted or unsubstituted with a substituent where two or more substituents selected from the above-exemplified substituents are connected.

In the present specification, R, R', and R" are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted It may be a ringed C2 to C60 heteroaryl group.

In this specification, “proton number” refers to the number of substituents that a specific compound can have, and specifically, the proton number may refer to the number of hydrogens. For example, unsubstituted benzene can be expressed as a proton number of 5, an unsubstituted naphthyl group can be expressed as a proton number of 7, and a naphthyl group substituted with a phenyl group can be expressed as a proton number of 6. , in the case of an unsubstituted biphenyl group, it can be expressed as 9 protons.

In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and 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-dimethyl heptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.

In the present specification, the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include 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 is not limited thereto. .

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

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, Isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p -methylbenzyloxy group, etc., but is not limited thereto.

In the present specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted by another substituent. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and 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, etc., but is not limited thereto.

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

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the aryl group include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, and pyrethyl group. Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, and condensed rings thereof etc., but is not limited to this.

In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specifically, it may be substituted with an aryl group, and the examples described above may be applied to the aryl group. For example, the phosphine oxide group includes diphenylphosphine oxide group, dinaphthylphosphine oxide, etc., but is not limited thereto.

In the present specification, the silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -SiR101R102R103, and R101 to R103 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of silyl groups include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited.

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

When the fluorenyl group is substituted,

It may be, but is not limited to this.

In the present specification, a spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group. Specifically, the spiro group below may include any one of the groups of the structural formula below.

In the present specification, the heteroaryl group contains S, O, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl 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, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridinyl group , imidazopyridinyl group, diazanaphthalenyl group, triazindenyl group, 2-indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophenyl group, benzofura Nyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol) group, dihydrophenazinyl group , phenoxazinyl group, phenanthridyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro- Dibenzo[b,f]azepinyl 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]azacylinyl group, pyrazolo[1,5-c]quinazolinyl group, pyrido[1 ,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, 5,11-dihydroindeno[1,2-b]carbazolyl group, etc. Examples include, but are not limited to.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH ₂ ; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and 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 methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited thereto.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group. In addition, a heteroarylene group means that a heteroaryl group has two bonding positions, that is, a bivalent group. The description of the heteroaryl group described above can be applied, except that each of these is a divalent group.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

In the present invention, “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 ( ^2H , Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In one embodiment of the present invention, “when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%.

In one embodiment of the present invention, in “cases where substituents are not indicated in the chemical formula or compound structure,” “content of deuterium is 0%,” “content of hydrogen is 100%,” “substituents are all hydrogen,” etc. If deuterium is not explicitly excluded, hydrogen and deuterium can be used together in a compound.

In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. Hydrogen- It can be expressed as 2, and the element symbol can also be written as D or ² H.

In one embodiment of the present invention, isotopes are atoms with the same atomic number (Z) but different mass numbers (A), and isotopes have the same number of protons but do not contain neutrons. It can also be interpreted as an element with a different number of neutrons.

In one embodiment of the present invention, the meaning of the content T% of a specific substituent means that the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2. It can be defined as /T1×100 = T%.

That is, in one example,

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

Additionally, in one embodiment of the present invention, “a phenyl group with a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.

In the present invention, the C6 to C60 aromatic hydrocarbon ring refers to a compound containing an aromatic ring consisting of C6 to C60 carbons and hydrogen, for example, benzene, biphenyl, triphenyl, triphenylene, naphthalene, Anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. may be mentioned, but are not limited to these, and aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number may be used. Includes all.

[Formula 1]

In Formula 1,

f is an integer from 0 to 4,

In an exemplary embodiment of the present application, Formula 1 may be represented by any of the following Formulas 1-1 to 1-8.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8, the definition of each substituent is the same as that in Formula 1.

In an exemplary embodiment of the present application, X1 to X3 may be O.

In an exemplary embodiment of the present application, X1 to X3 may be S.

In an exemplary embodiment of the present application, X1 and X2 may be O, and X3 may be S.

In an exemplary embodiment of the present application, X1 and X3 may be O, and X2 may be S.

In an exemplary embodiment of the present application, X2 and X3 may be O, and X1 may be S.

In an exemplary embodiment of the present application, X1 and X2 may be S, and X3 may be O.

In an exemplary embodiment of the present application, X1 and X3 may be S, and X2 may be O.

In an exemplary embodiment of the present application, X2 and X3 may be S, and X1 may be O.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle. Forming a, R101, R102 and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl 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 application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle. forming, wherein R101, R102 and R103 are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl 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 application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; A substituted or unsubstituted C6 to C20 aromatic hydrocarbon selected from the group consisting of a substituted or unsubstituted C6 to C20 aryl group and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon It may form a ring or a substituted or unsubstituted C2 to C20 heterocycle.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C60 alkyl 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 application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C30 alkyl group; 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 application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C20 alkyl group; 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 application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Or it may be a substituted or unsubstituted C6 to C20 aryl group.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; A substituted or unsubstituted monocyclic C6 to C10 aryl group; Or it may be a substituted or unsubstituted polycyclic C10 to C20 aryl group.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted phenyl group; Or it may be a substituted or unsubstituted biphenyl group.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it may be halogen.

In an exemplary embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it may be fluorine.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and are each independently 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 application, Ar1 and Ar2 are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic C6 to C10 aryl group; Alternatively, it may be a substituted or unsubstituted polycyclic C10 to C20 aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted chrysenyl group; Or it may be a substituted or unsubstituted phenanthrenyl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium, fluorine, butyl group, or naphthyl group; Biphenyl group substituted or unsubstituted with deuterium or fluorine; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium or fluorine; A phenanthrenyl group substituted or unsubstituted with deuterium; Alternatively, it may be a pyrenyl group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium based on the total number of hydrogen atoms and deuterium atoms in the heterocyclic compound represented by Formula 1 For example, this could be 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more. and may be 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 40% to 70% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, the heterocyclic compound represented by Formula 1 may not contain deuterium, or the content of deuterium may be 50% to 60% based on the total number of hydrogen atoms and deuterium atoms.

In an exemplary embodiment of the present application, L1, L2, Ar1, Ar2, and R1 to R6 may all include non-deuterated H.

In an exemplary embodiment of the present application, at least one of L1, L2, Ar1, Ar2 and R1 to R6 includes D, and at least one of L1, L2, Ar1, Ar2 and R1 to R6 includes non-deuterated H. It can contain at least one.

In an exemplary embodiment of the present application, L1, L2, Ar1, Ar2, and R1 to R6 may all include D.

In an exemplary embodiment of the present application, Formula 1 provides a heterocyclic compound represented by any one of the following compounds. Additionally, in an exemplary embodiment of the present application, the following compound is an example, and is not limited thereto, and may include other compounds included in Formula 1 containing additional substituents.

Additionally, by introducing various substituents into the structure of Formula 1, a compound having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, the conditions required for each organic material layer are met. You can synthesize the desired substances.

In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved and the uses of the material can be diversified.

Another embodiment of the present invention provides an organic light-emitting device containing the heterocyclic compound represented by Formula 1 above. The “organic light emitting device” may be expressed by terms such as “organic light emitting diode”, “OLED (Organic Light Emitting Diodes)”, “OLED device”, “organic electroluminescent device”, etc.

In an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers includes a heterocyclic compound represented by Formula 1. do.

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

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

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the green organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the red organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

Specific details about the heterocyclic compound represented by Formula 1 are the same as described above.

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that one or more organic layers are formed using the heterocyclic compound described above.

The heterocyclic compound may be formed into 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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 to this and may include a smaller number of organic material layers.

In the organic light-emitting device of the present invention, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1 above. When the heterocyclic compound is used in the light-emitting layer, strong charge transfer is possible by spatially separating HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital), thereby driving the organic light-emitting device. Efficiency and lifespan can be improved. More specifically, the heterocyclic compound represented by Formula 1 includes a heteroaryl-based substituent in the dibenzofuran or dibenzothiophene structure as the core structure, thereby providing electrons ( electron characteristics can be strengthened, and the band-gap and triplet excited state energy level (T ₁ ) value of the compound can be adjusted. Therefore, when the compound represented by Formula 1 is used in the organic material layer, the driving voltage of the organic light-emitting device can be lowered, the luminous efficiency can be improved, and the lifespan characteristics of the organic light-emitting device can be improved due to the thermal stability of the compound.

In the organic light-emitting device of the present invention, the organic material layer includes 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 invention, the organic material layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound of Formula 1 as a light-emitting layer host.

In another embodiment of the present invention, the organic light emitting device has one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. Alternatively, it may further include two or more floors.

In one embodiment of the present invention, the organic light-emitting device may include one or more organic material layers, the organic material layer may include a hole transport layer, and the hole transport layer includes a heterocyclic compound represented by Formula 1. can do.

In one embodiment of the present invention, the organic light-emitting device may include one or more organic material layers, the organic material layer may include a hole transport auxiliary layer, and the hole transport auxiliary layer may be a heterogeneous material represented by Formula 1. It may contain a ring compound.

In one embodiment of the present invention, the organic material layer includes a heterocyclic compound represented by Formula 1, and can be used together with a phosphorescent dopant.

As the phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L ₂ MX' and L ₃ M can be used, but the scope of the present invention is not limited by these examples. .

The M may be iridium, platinum, osmium, etc.

L is an anionic bidentate ligand coordinated to M by an sp ² carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L, L' and L" include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiazole Thiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Non-limiting examples of X' and These include silidene, picolinate, and 8-hydroxyquinolinate.

Specific examples of the phosphorescent dopant are shown below, but are not limited to these examples:

In one embodiment of the present invention, the organic material layer includes a heterocyclic compound represented by Formula 1, and can be used with an iridium-based dopant.

In one embodiment of the present invention, (piq) ₂ (Ir) (acac), a red phosphorescent dopant, may be used as the iridium-based dopant.

In one embodiment of the present invention, Ir(ppy) ₃ , a green phosphorescent dopant, may be used as the iridium-based dopant.

In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light emitting layer. .

In the organic light-emitting device according to an embodiment of the present invention, the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include a heterocyclic compound represented by Formula 1 above. .

In an organic light-emitting device according to another embodiment of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by Formula 1.

In an organic light emitting device according to another embodiment of the present invention, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by Formula 1. .

In an organic light-emitting device according to another embodiment of the present invention, the organic material layer includes an electron transport layer, a light-emitting layer, or a hole blocking layer, and the electron transport layer, the light-emitting layer, or the hole blocking layer may include a heterocyclic compound represented by Formula 1. You can.

In an organic light-emitting device according to another embodiment of the present invention, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1 above.

In an organic light-emitting device according to another embodiment of the present invention, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Formula 1.

In an organic light emitting device according to another embodiment, the light emitting layer may include two or more host materials, and at least one of the host materials may include a heterocyclic compound represented by Formula 1.

In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials is a heterogeneous compound represented by Formula 1. It may contain a ring compound.

The pre-mixed means that the light emitting layer first mixes two or more host materials in one source before depositing them on the organic layer.

In the organic light-emitting device according to an exemplary embodiment of the present application, the organic material layer containing the heterocyclic compound represented by the formula (1) further includes a heterocyclic compound represented by the following formula (A): .

[Formula A]

In Formula A,

At least one of X ₁₁ to X ₁₃ is N,

In an exemplary embodiment of the present application, X ₁₁ to X ₁₃ are N; Or CR', and at least one of X ₁₁ to X ₁₃ may be N.

In an exemplary embodiment of the present application, X ₁₁ to X ₁₃ may be N.

In an exemplary embodiment of the present application, X ₁₁ and X ₁₂ may be N, and X ₁₃ may be CR'.

In an exemplary embodiment of the present application, X ₁₁ and X ₁₃ may be N, and X ₁₂ may be CR'.

In an exemplary embodiment of the present application, R _a1 to R _a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C60 heteroaryl group.

In an exemplary embodiment of the present application, R _a1 to R _a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C30 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present application, R _a1 to R _a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group.

In an exemplary embodiment of the present application, R _a1 to R _a3 and R' are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C20 aryl group; Or it may be selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group.

When the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A are included in the organic material layer of an organic light-emitting device, better efficiency and lifespan effects are achieved. This result can be expected to indicate that an exciplex phenomenon occurs when two compounds are included at the same time.

The exciplex phenomenon is a phenomenon in which energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts for the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, thereby helping to improve lifespan.

In an exemplary embodiment of the present application, the formula A may be represented by any one of the following formulas A-1 to A-3.

[Formula A-1]

[Formula A-2]

[Formula A-3]

[Formula A-4]

In Formula A-1 to Formula A-4,

X ₁₁ to X ₁₃ , R _a2 and R _a3 are the same as defined in Formula A,

X4 is O, S or CR _aa R _bb ,

R _aa and R _bb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group,

R _a11 to R _a15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 group. Forms a heterocycle,

L _a1 and L _a2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

Ar _a1 is hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

m11 and m21 are integers from 0 to 2, and when m11 and m21 are 2, the substituents in the parentheses are the same or different from each other,

m3 is an integer from 0 to 8, and when m3 is 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present application, R _a2 and R _a3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a C6 to C40 aryl group substituted or unsubstituted with a C6 to C40 aryl group or a C2 to C40 heteroaryl group; and a C2 to C40 heteroaryl group.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a C6 to C20 aryl group substituted or unsubstituted with a C6 to C20 aryl group or a C2 to C20 heteroaryl group; and a C2 to C20 heteroaryl group.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzothiophene group; Alternatively, it may be a group represented by the following formula (B).

[Formula B-1]

In Formula B-1,

X4 is the same as defined in Formula A-1 to Formula A-3,

R _a16 is hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group,

m4 is an integer from 0 to 3,

* is a connection point bonded to the carbon between X ₁₁ and X ₁₃ in Formulas A-1 to A-3,

Ring A is represented by the following formula B-2.

[Formula B-2]

In Formula B-2,

X4 and R _a16 are the same as defined in Formula B-1,

m5 is an integer from 0 to 4,

** is the connection point with Chemical Formula B-1.

In another embodiment, R _a2 and R _a3 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted by a phenyl group, a naphthyl group, or a carbazole group; naphthyl group; Biphenyl group; Terphenyl group; phenanthrenyl group; Dibenzofuran group; Spirobifluorenyl group; Dibenzothiophene group; Dimethylbenzoindenothiophene group; Or it may be a dimethylbenzoindenofuran group.

In an exemplary embodiment of the present application, R' is hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present application, R _a11 to R _a15 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; -CN; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Alternatively, it may form a substituted or unsubstituted C2 to C60 hetero ring.

In another embodiment, R _a11 to R _a15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another embodiment, R _a11 to R _a15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

In another embodiment, R _a11 to R _a15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

In another embodiment, R _a11 to R _a15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; and substituted or unsubstituted dibenzothiophene groups, or two or more groups adjacent to each other may be combined with each other to form a benzene ring.

In an exemplary embodiment of the present application, L _a1 and L _a2 are the same or different from each other, and are each independently directly bonded; Substituted or unsubstituted C6 to C60 arylene group; Or it may be a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L _a1 and L _a2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C40 arylene group; Or it may be a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L _a1 and L _a2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C20 arylene group; Or it may be a substituted or unsubstituted C2 to C20 heteroarylene group.

In another embodiment, L _a1 and L _a2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or it may be a substituted or unsubstituted naphthalene group.

In an exemplary embodiment of the present application, Ar _a1 is 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 another exemplary embodiment, Ar _a1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ar _a1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

In another exemplary embodiment, Ar _a1 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted phenanthrenyl group.

In an exemplary embodiment of the present application, the heterocyclic compound of Formula A may be represented by any one of the following compounds.

Specific details about the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula A are the same as described above.

The weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula A in the composition may be 1:10 to 10:1, 1:8 to 8:1, and 1:5. It may be from 5:1 to 1:1, and from 1:2 to 2:1, but is not limited thereto.

The composition can be used when forming an organic material of an organic light-emitting device, and can be particularly preferably used when forming a host for a light-emitting layer.

The composition is a simple mixture of two or more compounds, and powdered materials may be mixed before forming the organic material layer of the organic light-emitting device, or compounds in a liquid state at an appropriate temperature or higher may be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

The composition may additionally contain materials known in the art, such as solvents and additives.

The organic light emitting device according to an exemplary embodiment of the present application is a conventional organic material layer, except that one or more organic layers are formed using the heterocyclic compound represented by the above-described formula 1 and the heterocyclic compound represented by formula A. It can be manufactured using light emitting device manufacturing methods and materials.

The compound represented by Formula 1 and the heterocyclic compound represented by Formula A may be formed into 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 and the heterocyclic compound according to Formula A may be used as a material for the blue organic light-emitting device. .

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the compound represented by Formula 1 and the heterocyclic compound represented by Formula A may be used as a material for the green organic light-emitting device. .

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the compound represented by Formula 1 and the heterocyclic compound represented by Formula A may be used as a material for the red organic light-emitting device. .

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

In an exemplary embodiment of the present application, the organic material layer includes at least one layer of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one layer of the hole blocking layer, an electron injection layer, and an electron transport layer is represented by Formula 1. It provides an organic light-emitting device comprising a heterocyclic compound represented by the formula A and a heterocyclic compound represented by the above formula (A).

In an exemplary embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a heterocyclic compound represented by Formula 1, and a heterocyclic compound represented by Formula A. An organic light-emitting device is provided. do.

In an exemplary embodiment of the present application, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes a heterocyclic compound represented by Formula 1, and a heterocyclic compound represented by Formula A. It provides an organic light emitting device comprising a.

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

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

Figure 3 illustrates the case where the organic material layer is multi-layered. The organic light emitting device 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 this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

In one embodiment of the present invention, preparing a substrate; forming a first electrode on the substrate; Forming one or more organic layers on the first electrode; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer includes forming one or more organic material layers using a composition for an organic material layer according to an embodiment of the present invention. It provides a method for manufacturing an organic light-emitting device comprising the step of:

In one embodiment of the present invention, the step of forming the organic layer may include pre-mixing the heterocyclic compound represented by Formula 1 and forming it using a thermal vacuum deposition method.

The pre-mixed means mixing the materials in one source before depositing the heterocyclic compound represented by Formula 1 on the organic layer.

The premixed material may be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.

The organic material layer containing the heterocyclic compound represented by Formula 1 may further include other materials as needed.

In the organic light-emitting device according to an embodiment of the present invention, materials other than the heterocyclic compound represented by Formula 1 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application. It can be replaced by materials known in the art.

As the anode material, materials with a relatively large work function can be used, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO2:Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

As the hole injection layer material, known hole injection layer materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or those described in Advanced Material, 6, p.677 (1994). Described starburst-type amine derivatives, such as tris(4-carbazoyl-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), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid, or Polyaniline/Poly(4-styrenesulfonate), etc. can be used.

As the hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport layer materials 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 its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection layer material in the industry, but the present application is not limited thereto.

Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material may be used as the light-emitting layer material, but it may also be used as a phosphorescent material. The light emitting layer material may be a material that emits light by combining holes and electrons injected from the anode and the cathode respectively, but may also be used as a host material and a dopant material that participates in light emission together.

When using a mixture of hosts of the light emitting layer material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials, such as an n-type host material or a p-type host material, can 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 invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

The heterocyclic compound according to an exemplary embodiment of the present invention may function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

Hereinafter, preferred examples are presented to aid understanding of the present invention, but the following examples are provided to facilitate understanding of the present invention and do not limit the present invention thereto.

<제조예><Manufacturing example>

<제조예 1> 화합물 1-1의 제조<Preparation Example 1> Preparation of compound 1-1

1) 화합물 C1의 제조1) Preparation of Compound C1

Compound A1 10.0g (35.5mmol), Compound B1 6.01 g (35.5mmol), Pd(OAc) ₂ 0.40g (1.78mmol), Xantphos 2.05g (3.55 mmol), NaO t Bu 6.82g (71.0mmol), Toluene 100mL was placed in a 250mL round bottom flask and refluxed for 2 hours. After the reaction was completed, the temperature was lowered to room temperature, and a Celite filter was performed using MC (methylene chloride). After concentration, it was separated using a column with MC:Hexane = 1:2 conditions to obtain 8.15 g (22.0 mmol, yield: 62%) of compound C1.

2) 화합물 E1의 제조2) Preparation of compound E1

20.0 g (71.0 mmol) of Compound A1, 16.6 g (78.1 mmol) of Compound D1, 4.10 g (3.55 mmol) of Pd(PPh ₃ ) ₄ , 19.6 g (142 mmol) of K ₂ CO ₃ , 60 mL of distilled water and 200 mL of dioxane. was added to a 500 mL round bottom flask and refluxed for 2 hours. After the reaction is complete, the temperature is lowered to room temperature and the mixture is washed with distilled water and methanol. After removing the solvent using a rotary evaporator, it was recrystallized with toluene to obtain 22.0 g (59.7 mmol, yield: 84%) of compound E1.

3) 화합물 F1의 제조3) Preparation of compound F1

The compound E1 22.0g (59.7mmol), B ₂ pin ₂ 22.7g (89.5mmol), Pd ₂ dba ₃ 2.73g (2.99mmol), Sphos 2.45g (5.97mmol), KOAc 11.7g (119mmol), dioxane ) 220mL was added to a 1L round bottom flask and refluxed for 4 hours. After the reaction was completed, the salt was removed by filtering under reduced pressure with MC (methylene chloride) while hot. After concentration, it was separated using a column with MC:Hexane = 1:3 conditions to obtain 14.3g (31.0mmol, yield: 52%) of Compound F1.

4) 화합물 1-1의 제조4) Preparation of compound 1-1

The compound C1 8.15g (22.0mmol), compound F1 10.7g (23.1mmol), Pd2dba3 1.01g (1.10mmol), Xphos 1.05g (2.20mmol), NaOH 1.76g (44.0mmol), H2O 24mL, dioxane 82 mL was added to a 250 mL round bottom flask and refluxed for 4 hours. After the reaction was completed, extraction was performed with MC (methylene chloride). After concentrating this, it was separated using a column under the condition MC:Hexane = 1:3 to obtain 11.9g (17.8mmol, yield: 81%) of compound 1-1.

<제조예 2> 화합물 1-2, 1-12, 1-13, 1-15, 1-30, 1-32, 1-33, 1-49, 1-57, 1-65, 1-66, 1-76, 1-80, 1-99, 1-109, 1-112, 1-127, 1-139, 1-145, 1-167, 1-169, 1-178, 1-202, 1-226, 1-230, 1-249, 1-265, 1-268, 1-287, 1-327, 1-336, 1-340 및 G1의 제조<Preparation Example 2> Compound 1-2, 1-12, 1-13, 1-15, 1-30, 1-32, 1-33, 1-49, 1-57, 1-65, 1-66, 1-76, 1-80, 1-99, 1-109, 1-112, 1-127, 1-139, 1-145, 1-167, 1-169, 1-178, 1-202, 1- Preparation of 226, 1-230, 1-249, 1-265, 1-268, 1-287, 1-327, 1-336, 1-340 and G1

Compounds 1-2, 1-12, and 1-13 were prepared in the same manner as the preparation of Compound 1-1, except that Compounds A to F of Table 1 below were used instead of Compounds A1 to F1 in the preparation of Compound 1. , 1-15, 1-30, 1-32, 1-33, 1-49, 1-57, 1-65, 1-66, 1-76, 1-80, 1-99, 1-109, 1 -112, 1-127, 1-139, 1-145, 1-167, 1-169, 1-178, 1-202, 1-226, 1-230, 1-249, 1-265, 1-268 , 1-287, 1-327, 1-336, 1-340 and G1 were synthesized.

<제조예 3> 화합물 1-86의 제조<Preparation Example 3> Preparation of compound 1-86

10.0 g (15.0 mmol) of compound G1 and 100 mL of benzene-d6 were added to a 1L round bottom flask, and 9 mL of TfOH (Triflic acid) was slowly added dropwise. It was stirred at 80°C for 1 hour (h). After the reaction was completed, it was cooled to room temperature and filtered through Celite filter with methylene chloride (MC). After concentration, 8.68 g (12.5 mmol, 83%) of compound 1-86 was obtained by separation using a column with MC:Hexane=1:3 conditions.

<제조예 4> 화합물 1-192 및 1-271의 제조<Preparation Example 4> Preparation of compounds 1-192 and 1-271

Compounds 1-192 and 1-271 were synthesized in the same manner as the preparation of compound 1-86, except that compound G of Table 2 below was used instead of compound G.

<제조예 5> 화합물 2-1의 제조<Preparation Example 5> Preparation of compound 2-1

1) 중간체 2-1-2의 제조1) Preparation of intermediate 2-1-2

1-bromo-3-chlorodibenzo[b,d]furan (10.0 g, 35.5 mmol) B ₂ pin ₂ (13.5 g, 53.3 mmol), Pd(dppf)Cl ₂ (1.30 g, 1.78 mmol), KOAc (10.2 g , 107 mmol) was added to Dioxane (100 mL) and stirred at 100°C for 2 hours. It was filtered while hot and washed several times with DCM. The filtrate was concentrated under reduced pressure and then filtered through silica gel. Concentrated under reduced pressure to obtain intermediate 2-1-2 (10.1 g, 87%).

2) 중간체 2-1-1의 제조2) Preparation of intermediate 2-1-1

Intermediate 2-1-2 (10.1 g, 30.7 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (11.3 g, 30.7 mmol), Pd(PPh ₃ ) ₄ (1.77 g, 1.54 mmol) and K ₂ CO ₃ (12.7 g, 92.1 mmol) were added to Dioxane/H ₂ O (100/30 mL) and stirred at 100°C for 2 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered to obtain intermediate 2-1-1 (12.8 g, 80%).

3) 화합물 2-1 제조3) Preparation of compound 2-1

Intermediate 2-1-1 (14.8 g, 27.7 mmol), phenylboronic acid (3.72 g, 30.5 mmol), Pd ₂ dba ₃ (1.27 g, 0.05 mmol), Xphos (1.32 g, 2.77 mmol), NaOH (2.22 g, 55.4 mmol) was added to Dioxane/H ₂ O and stirred at 130°C for 3 hours. After cooling to room temperature, the resulting solid was filtered. Compound 2-1 (7.36 g, 74%) was obtained through silica gel filter.

<제조예 6> 화합물 2-3, 2-5, 2-8, 2-21 및 2-30의 제조<Preparation Example 6> Preparation of compounds 2-3, 2-5, 2-8, 2-21 and 2-30

The following compounds were synthesized in the same manner as the preparation of compound 2-1 in Preparation Example 5, except that A, B, and C of Table 3 below were used as intermediates in Preparation Example 5.

The remaining compounds other than those described in Preparation Examples 1 to 5 and Tables 1 to 3 were also prepared in the same manner as in the above Preparation Examples, and the synthesis results are shown in Tables 4 and 5 below. Table 4 below shows the measured values of ¹ H NMR (CDCl ₃ , 400 MHz), and Table 5 below shows the measured values of Field desorption mass spectrometry (FD-MS). Compounds 1-86, 1-192, and 1-271 did not contain ¹ H, so the measurement of ¹ H NMR (CDCl ₃ , 400 MHz) was omitted.

화합물compound	¹H NMR (CDCl₃, 400MHz) ^1H NMR (CDCl ₃ , 400MHz)
1-11-1	δ=8.22~8.20(d, 1H), 8.09~8.07(d, 1H), 7.77~7.68(m, 6H), 7.66~7.58(m, 4H), 7.54~7.44(m, 9H), 7.42~7.36(m, 3H), 7.29~7.26(m, 3H), 7.24~7.22(d, 1H), 7.17~7.15(d, 1H)δ=8.22~8.20(d, 1H), 8.09~8.07(d, 1H), 7.77~7.68(m, 6H), 7.66~7.58(m, 4H), 7.54~7.44(m, 9H), 7.42~7.36 (m, 3H), 7.29~7.26(m, 3H), 7.24~7.22(d, 1H), 7.17~7.15(d, 1H)
1-21-2	δ=8.56(s, 1H), 8.25~8.23(d, 1H), 8.11~8.09(d, 1H), 8.05~8.03(d, 1H), 8.01~7.99(d, 1H), 7.86~7.81(m, 3H), 7.75~7.71(m, 5H), 7.67~7.63(m, 7H), 7.54~7.50(m, 7H), 7.45~7.38(m, 2H)δ=8.56(s, 1H), 8.25~8.23(d, 1H), 8.11~8.09(d, 1H), 8.05~8.03(d, 1H), 8.01~7.99(d, 1H), 7.86~7.81(m) , 3H), 7.75~7.71(m, 5H), 7.67~7.63(m, 7H), 7.54~7.50(m, 7H), 7.45~7.38(m, 2H)
1-121-12	δ=8.55(d, 1H), 8.32(d, 1H), 8.08~7.98(m, 6H), 7.88~7.79(m, 3H), 7.70(t, 1H), 7.64(s, 1H), 7.54~7.24(m, 10H), 7.08~7.00(m, 6H)δ=8.55(d, 1H), 8.32(d, 1H), 8.08~7.98(m, 6H), 7.88~7.79(m, 3H), 7.70(t, 1H), 7.64(s, 1H), 7.54~ 7.24(m, 10H), 7.08~7.00(m, 6H)
1-131-13	δ=8.55(d, 1H), 8.45(d, 1H), 8.32(d, 1H), 8.08~7.93(m, 7H), 7.70~7.68(m, 3H), 7.56~7.49(m, 3H), 7.34(t, 1H), 7.25~7.24(m, 5H), 7.08~6.91(m, 7H)δ=8.55(d, 1H), 8.45(d, 1H), 8.32(d, 1H), 8.08~7.93(m, 7H), 7.70~7.68(m, 3H), 7.56~7.49(m, 3H), 7.34(t, 1H), 7.25~7.24(m, 5H), 7.08~6.91(m, 7H)
1-151-15	δ=8.08~7.98(m, 7H), 7.82~7.76(m, 4H), 7.57~7.51(m, 4H), 7.39~7.24(m, 6H), 7.08~7.00(m, 3H), 6.91~6.85(m, 2H), 6.76(t, 1H)δ=8.08~7.98(m, 7H), 7.82~7.76(m, 4H), 7.57~7.51(m, 4H), 7.39~7.24(m, 6H), 7.08~7.00(m, 3H), 6.91~6.85 (m, 2H), 6.76(t, 1H)
1-181-18	δ=8.55(d, 1H), 8.32~8.17(m, 5H), 7.98~7.95(m, 2H), 7.88~7.70(m,5H), 7.54(d, 1H), 7.41~7.24(m, 7H), 7.08~7.00(m, 6H)δ=8.55(d, 1H), 8.32~8.17(m, 5H), 7.98~7.95(m, 2H), 7.88~7.70(m,5H), 7.54(d, 1H), 7.41~7.24(m, 7H) ), 7.08~7.00(m, 6H)
1-301-30	δ=8.08~7.98(m, 3H), 7.88~7.76(m, 6H), 7.69(d, 1H), 7.57~7.51(m, 3H), 7.39~7.24(m, 6H), 7.10~7.00(m, 7H), 6.91(d, 1H), 1.33(s, 9H)δ=8.08~7.98(m, 3H), 7.88~7.76(m, 6H), 7.69(d, 1H), 7.57~7.51(m, 3H), 7.39~7.24(m, 6H), 7.10~7.00(m) , 7H), 6.91(d, 1H), 1.33(s, 9H)
1-321-32	δ = 8.17~8.15 (d, 1H), 8.12~8.10 (d, 2H), 8.06~8.04 (d, 1H), 7.79~7.75 (m, 3H), 7.73~7.52 (m, 13H), 7.43~7.40 (m, 7H), 7.21~7.19 (d, 2H)δ = 8.17~8.15 (d, 1H), 8.12~8.10 (d, 2H), 8.06~8.04 (d, 1H), 7.79~7.75 (m, 3H), 7.73~7.52 (m, 13H), 7.43~7.40 (m, 7H), 7.21~7.19 (d, 2H)
1-331-33	δ=8.12~8.10(d, 1H), 8.08~8.03(m, 2H), 7.94~7.85(m, 3H), 7.78~7.55(m, 7H), 7.52~7.47(m, 5H), 7.34~7.22(m, 7H), 7.19~7.17(d, 1H), 7.12~6.90(m, 3H)δ=8.12~8.10(d, 1H), 8.08~8.03(m, 2H), 7.94~7.85(m, 3H), 7.78~7.55(m, 7H), 7.52~7.47(m, 5H), 7.34~7.22 (m, 7H), 7.19~7.17(d, 1H), 7.12~6.90(m, 3H)
1-491-49	δ=8.09~8.01(m, 3H), 7.83~7.78(m, 4H), 7.72~7.67(m, 4H), 7.58~7.56(d, 1H), 7.51~7.48(m, 6H), 7.33~7.26(m, 6H), 7.23~6.92(m, 5H)δ=8.09~8.01(m, 3H), 7.83~7.78(m, 4H), 7.72~7.67(m, 4H), 7.58~7.56(d, 1H), 7.51~7.48(m, 6H), 7.33~7.26 (m, 6H), 7.23~6.92(m, 5H)
1-571-57	δ=8.28(s, 1H), 8.14~8.12(d, 1H), 7.85~7.81(m, 5H), 7.70~7.59(m, 12H), 7.57~7.40(m, 5H), 7.27~7.25(m, 4H), 7.13~7.11(t, 1H)δ=8.28(s, 1H), 8.14~8.12(d, 1H), 7.85~7.81(m, 5H), 7.70~7.59(m, 12H), 7.57~7.40(m, 5H), 7.27~7.25(m) , 4H), 7.13~7.11(t, 1H)
1-651-65	δ=8.15~8.13(d, 1H), 8.09~8.07(d, 1H), 7.82~7.80(d, 1H), 7.78~7.76(d, 1H), 7.74~7.72(m, 4H), 7.70~7.55(m, 11H), 7.49~7.41(m, 6H), 7.16~7.12(m, 4H)δ=8.15~8.13(d, 1H), 8.09~8.07(d, 1H), 7.82~7.80(d, 1H), 7.78~7.76(d, 1H), 7.74~7.72(m, 4H), 7.70~7.55 (m, 11H), 7.49~7.41(m, 6H), 7.16~7.12(m, 4H)
1-661-66	δ=8.55(d, 2H), 8.32(d, 2H), 8.22(s, 1H), 8.03~7.98(m, 2H), 7.88~7.70(m, 7H), 7.56~7.54(m, 2H), 7.39~7.24(m, 6H), 7.08~6.97(m, 7H)δ=8.55(d, 2H), 8.32(d, 2H), 8.22(s, 1H), 8.03~7.98(m, 2H), 7.88~7.70(m, 7H), 7.56~7.54(m, 2H), 7.39~7.24(m, 6H), 7.08~6.97(m, 7H)
1-761-76	δ=8.22(s, 1H), 8.08~7.98(m, 6H), 7.88~7.76(m, 5H), 7.56~7.51(m, 4H), 7.39(t, 1H), 7.31(t, 1H), 6.97(d, 1H)δ=8.22(s, 1H), 8.08~7.98(m, 6H), 7.88~7.76(m, 5H), 7.56~7.51(m, 4H), 7.39(t, 1H), 7.31(t, 1H), 6.97(d, 1H)
1-801-80	δ=8.16~8.14(d, 1H), 8.10~8.08(d, 1H), 7.85~7.82(d, 2H), 7.77~7.70(m, 7H), 7.69~7.60(m, 3H), 7.58~7.51(m, 8H), 7.45~7.43(m, 6H), 7.21~7.19(d, 1H)δ=8.16~8.14(d, 1H), 8.10~8.08(d, 1H), 7.85~7.82(d, 2H), 7.77~7.70(m, 7H), 7.69~7.60(m, 3H), 7.58~7.51 (m, 8H), 7.45~7.43(m, 6H), 7.21~7.19(d, 1H)
1-991-99	δ=8.78(s, 1H), 8.18~8.16(d, 1H), 8.13~8.11(d, 1H), 8.06~8.02(m, 4H), 7.82~7.77(m, 3H), 7.73~7.71(d, 1H), 7.67~7.62(m, 8H), 7.55~7.49(m, 6H), 7.45~7.34(m, 4H)δ=8.78(s, 1H), 8.18~8.16(d, 1H), 8.13~8.11(d, 1H), 8.06~8.02(m, 4H), 7.82~7.77(m, 3H), 7.73~7.71(d) , 1H), 7.67~7.62(m, 8H), 7.55~7.49(m, 6H), 7.45~7.34(m, 4H)
1-1091-109	δ=7.80~7.47(m, 3H), 7.67~7.55(m, 10H), 7.50~7.47(d, 2H), 7.36~7.32(m, 2H), 7.25~7.13(m, 9H), 7.02~7.00(d, 1H), 6.97~6.95(m, 2H)δ=7.80~7.47(m, 3H), 7.67~7.55(m, 10H), 7.50~7.47(d, 2H), 7.36~7.32(m, 2H), 7.25~7.13(m, 9H), 7.02~7.00 (d, 1H), 6.97~6.95(m, 2H)
1-1121-112	δ=8.52~8.50(d, 1H), 8.17~8.15(m, 3H), 8.10~8.09(d, 1H), 8.02~8.00(d, 1H), 7.77~7.66(m, 6H), 7.62~7.51(m, 9H), 7.49~7.39(m, 6H), 7.19~7.17(m, 2H)δ=8.52~8.50(d, 1H), 8.17~8.15(m, 3H), 8.10~8.09(d, 1H), 8.02~8.00(d, 1H), 7.77~7.66(m, 6H), 7.62~7.51 (m, 9H), 7.49~7.39(m, 6H), 7.19~7.17(m, 2H)
1-1271-127	δ=8.15~8.13(d, 2H), 7.96(s, 1H), 7.90~7.81(m, 3H), 7.70~7.58(m, 10H), 7.56~7.50(m, 5H), 7.47~7.26(m, 8H)δ=8.15~8.13(d, 2H), 7.96(s, 1H), 7.90~7.81(m, 3H), 7.70~7.58(m, 10H), 7.56~7.50(m, 5H), 7.47~7.26(m) , 8H)
1-1391-139	δ=8.16~8.14(d, 1H), 8.09~8.07(d, 1H), 7.88(s, 1H), 7.82~7.80(d, 1H), 7.73~7.54(m, 14H), 7.52~7.40(m, 3H), 7.38~7.24(m, 8H)δ=8.16~8.14(d, 1H), 8.09~8.07(d, 1H), 7.88(s, 1H), 7.82~7.80(d, 1H), 7.73~7.54(m, 14H), 7.52~7.40(m) , 3H), 7.38~7.24(m, 8H)
1-1451-145	δ=8.39(s, 1H), 8.22~8.20(d, 1H), 7.91~7.89(m, 5H), 7.78~7.75(m, 5H), 7.65~7.53(m, 13H), 7.46~7.44(m, 2H), 7.19~7.17(m, 2H)δ=8.39(s, 1H), 8.22~8.20(d, 1H), 7.91~7.89(m, 5H), 7.78~7.75(m, 5H), 7.65~7.53(m, 13H), 7.46~7.44(m) , 2H), 7.19~7.17(m, 2H)
1-1671-167	δ=8.03~7.98(m, 4H), 7.82~7.54(m, 11H), 7.39~7.28(m, 3H), 6.97(d, 1H)δ=8.03~7.98(m, 4H), 7.82~7.54(m, 11H), 7.39~7.28(m, 3H), 6.97(d, 1H)
1-1691-169	δ=8.40 ~8.38(d, 1H), 8.26(s, 1H), 8.01~7.99(d, 1H), 7.83~7.81(m, 2H), 7.77(s, 2H), 7.69~7.48(m, 14H), 7.42~7.38(m, 6H), 7.23~7.19(m, 2H)δ=8.40 ~8.38(d, 1H), 8.26(s, 1H), 8.01~7.99(d, 1H), 7.83~7.81(m, 2H), 7.77(s, 2H), 7.69~7.48(m, 14H) ), 7.42~7.38(m, 6H), 7.23~7.19(m, 2H)
1-1781-178	δ=7.24(t, 4H), 7.08(d, 4H), 7.00(t, 2H)δ=7.24(t, 4H), 7.08(d, 4H), 7.00(t, 2H)
1-2021-202	δ=8.55(s, 1H), 8.24~8.22(d, 1H), 8.10~8.08(d, 1H), 8.06~8.04(d, 1H), 8.01~7.99(d, 1H), 7.87~7.82(m, 3H), 7.76~7.70(m, 5H), 7.66~7.60(m, 8H), 7.55~7.49(m, 8H), 7.44~7.38(m, 2H)δ=8.55(s, 1H), 8.24~8.22(d, 1H), 8.10~8.08(d, 1H), 8.06~8.04(d, 1H), 8.01~7.99(d, 1H), 7.87~7.82(m) , 3H), 7.76~7.70(m, 5H), 7.66~7.60(m, 8H), 7.55~7.49(m, 8H), 7.44~7.38(m, 2H)
1-2261-226	δ=8.65~8.63(d, 1H), 8.44~8.42(d, 1H), 8.21(s, 1H), 8.20~8.18(m, 2H), 8.00~7.98(m, 4H), 7.84~7.82(d, 1H), 7.74~7.72(d, 1H), 7.70~7.62(m, 9H), 7.56~7.49(m, 5H), 7.42~7.39(m, 3H), 7.27~7.25(d, 1H)δ=8.65~8.63(d, 1H), 8.44~8.42(d, 1H), 8.21(s, 1H), 8.20~8.18(m, 2H), 8.00~7.98(m, 4H), 7.84~7.82(d) , 1H), 7.74~7.72(d, 1H), 7.70~7.62(m, 9H), 7.56~7.49(m, 5H), 7.42~7.39(m, 3H), 7.27~7.25(d, 1H)
1-2301-230	δ=8.08~7.98(m, 4H), 7.82~7.69(m, 11H), 7.57~7.25(m, 15H), 7.11(s, 2H), 6.91(d, 1H)δ=8.08~7.98(m, 4H), 7.82~7.69(m, 11H), 7.57~7.25(m, 15H), 7.11(s, 2H), 6.91(d, 1H)
1-2491-249	δ=8.07~8.00(m, 3H), 7.82~7.77(m, 4H), 7.73~7.68(m, 4H), 7.59~7.57(d, 1H), 7.52~7.49(m, 7H), 7.40~7.30(m, 7H), 7.25~7.16(m, 5H)δ=8.07~8.00(m, 3H), 7.82~7.77(m, 4H), 7.73~7.68(m, 4H), 7.59~7.57(d, 1H), 7.52~7.49(m, 7H), 7.40~7.30 (m, 7H), 7.25~7.16(m, 5H)
1-2651-265	δ=8.98(d, 1H), 8.84(d, 1H), 8.08~7.54(m, 21H), 7.39~7.24(m, 6H), 7.08~6.91(m, 4H)δ=8.98(d, 1H), 8.84(d, 1H), 8.08~7.54(m, 21H), 7.39~7.24(m, 6H), 7.08~6.91(m, 4H)
1-2681-268	δ=8.31(d, 2H), 8.08~7.98(m, 8H), 7.82(d, 1H), 7.76(s, 1H), 7.64(d, 1H), 7.54~7.49(m, 5H), 7.39~7.24(m, 6H), 7.08~6.97(m, 4H)δ=8.31(d, 2H), 8.08~7.98(m, 8H), 7.82(d, 1H), 7.76(s, 1H), 7.64(d, 1H), 7.54~7.49(m, 5H), 7.39~ 7.24(m, 6H), 7.08~6.97(m, 4H)
1-2871-287	δ=8.24~7.99(m, 10H), 7.82~7.70(m, 5H), 7.54~7.40(m, 8H), 7.24~7.21(m, 3H), 7.11~7.00(m, 4H)δ=8.24~7.99(m, 10H), 7.82~7.70(m, 5H), 7.54~7.40(m, 8H), 7.24~7.21(m, 3H), 7.11~7.00(m, 4H)
1-3271-327	δ=8.14~8.12(d, 2H), 7.95(s, 1H), 7.89~7.80(m, 4H), 7.71~7.59(m, 11H), 7.57~7.51(m, 6H), 7.48~7.29(m, 9H)δ=8.14~8.12(d, 2H), 7.95(s, 1H), 7.89~7.80(m, 4H), 7.71~7.59(m, 11H), 7.57~7.51(m, 6H), 7.48~7.29(m) , 9H)
1-3361-336	δ=8.55(d, 1H), 8.45(d, 1H), 8.37~8.17(m, 7H), 8.03(d, 1H), 7.94~7.93(m, 2H), 7.78~7.40(m, 22H), 7.11(s, 1H)δ=8.55(d, 1H), 8.45(d, 1H), 8.37~8.17(m, 7H), 8.03(d, 1H), 7.94~7.93(m, 2H), 7.78~7.40(m, 22H), 7.11(s, 1H)
1-3401-340	δ=8.22(s, 1H), 8.03~7.98(m, 4H), 7.88~7.69(m, 9H), 7.57~7.24(m, 17H), 7.08~6.97(m, 4H)δ=8.22(s, 1H), 8.03~7.98(m, 4H), 7.88~7.69(m, 9H), 7.57~7.24(m, 17H), 7.08~6.97(m, 4H)
2-12-1	δ=9.10~9.08(d, 2H), 8.52~8.50(d, 2H), 8.18~7.99(m, 7H), 7.88~7.73(m, 4H), 7.60~7.30(m, 10H)δ=9.10~9.08(d, 2H), 8.52~8.50(d, 2H), 8.18~7.99(m, 7H), 7.88~7.73(m, 4H), 7.60~7.30(m, 10H)
2-32-3	δ=8.34~8.32(d, 4H), 7.97~7.95(d, 1H), 7.87~7.73(m, 4H), 7.54~7.26(m, 16H)δ=8.34~8.32(d, 4H), 7.97~7.95(d, 1H), 7.87~7.73(m, 4H), 7.54~7.26(m, 16H)
2-52-5	δ=8.37~8.29(m, 5H), 7.86~7.73(m, 4H), 7.53~7.39(m, 14H)δ=8.37~8.29(m, 5H), 7.86~7.73(m, 4H), 7.53~7.39(m, 14H)
2-82-8	δ=8.37~8.23(m, 5H), 7.86~7.74(m, 8H), 7.50~7.39(m, 12H), 7.26~7.22(m, 6H)δ=8.37~8.23(m, 5H), 7.86~7.74(m, 8H), 7.50~7.39(m, 12H), 7.26~7.22(m, 6H)
2-212-21	δ=8.98~8.96(d, 2H), 8.40~8.38(d, 4H), 7.79~7.73(m, 4H), 7.58~7.40(m, 12H), 7.26~7.24(m, 5H)δ=8.98~8.96(d, 2H), 8.40~8.38(d, 4H), 7.79~7.73(m, 4H), 7.58~7.40(m, 12H), 7.26~7.24(m, 5H)
2-302-30	δ=8.99~8.97(d, 2H), 8.35~8.33(d, 2H), 8.25~8.23(d, 2H), 7.84~7.66(m, 7H), 7.51~7.40(m, 11H), 7.33~7.24(m, 3H)δ=8.99~8.97(d, 2H), 8.35~8.33(d, 2H), 8.25~8.23(d, 2H), 7.84~7.66(m, 7H), 7.51~7.40(m, 11H), 7.33~7.24 (m, 3H)

화합물compound	FD-MassFD-Mass	화합물compound	FD-MassFD-Mass
1-11-1	m/z= 667.19(C48H29NO3, 667.21)m/z=667.19(C48H29NO3, 667.21)	1-1671-167	m/z= 677.28(C48H19D10NO3, 677.83)m/z=677.28(C48H19D10NO3, 677.83)
1-21-2	m/z= 683.12(C48H29NO2S, 683.19)m/z=683.12(C48H29NO2S, 683.19)	1-1691-169	m/z= 667.23(C48H29NO3, 667.21)m/z=667.23(C48H29NO3, 667.21)
1-121-12	m/z= 683.19(C48H29NO2S, 683.83)m/z=683.19(C48H29NO2S, 683.83)	1-1781-178	m/z= 686.33(C48H10D19NO3, 686.88)m/z=686.33(C48H10D19NO3, 686.88)
1-131-13	m/z= 699.17(C48H29NOS2, 699.89)m/z=699.17(C48H29NOS2, 699.89)	1-1921-192	m/z= 744.33(C48D29NS3, 745.12)m/z=744.33(C48D29NS3, 745.12)
1-151-15	m/z= 685.21(C48H28FNO3, 685.75)m/z=685.21(C48H28FNO3, 685.75)	1-2021-202	m/z= 733.20(C52H31NO2S, 733.20)m/z=733.20(C52H31NO2S, 733.20)
1-181-18	m/z= 699.17(C48H29NOS2, 699.89)m/z=699.17(C48H29NOS2, 699.89)	1-2261-226	m/z= 717.28(C52H31NO3, 717.23)m/z=717.28(C52H31NO3, 717.23)
1-301-30	m/z= 723.28(C52H37NO3, 723.87)m/z=723.28(C52H37NO3, 723.87)	1-2301-230	m/z= 767.25(C56H33NO3, 767.88)m/z=767.25(C56H33NO3, 767.88)
1-321-32	m/z= 667.19(C48H29NO3, 667.21)m/z=667.19(C48H29NO3, 667.21)	1-2491-249	m/z= 717.24(C52H31NO3, 717.23)m/z=717.24(C52H31NO3, 717.23)
1-331-33	m/z= 667.23(C48H29NO3, 667.21)m/z=667.23(C48H29NO3, 667.21)	1-2651-265	m/z= 767.25(C56H33NO3, 767.88)m/z=767.25(C56H33NO3, 767.88)
1-491-49	m/z= 667.24(C48H29NO3, 667.21)m/z=667.24(C48H29NO3, 667.21)	1-2681-268	m/z= 791.25(C58H33NO3, 791.91)m/z=791.25(C58H33NO3, 791.91)
1-571-57	m/z= 667.24(C48H29NO3, 667.21)m/z=667.24(C48H29NO3, 667.21)	1-2711-271	m/z= 764.40(C52D31NO2S, 765.07)m/z=764.40(C52D31NO2S, 765.07)
1-651-65	m/z= 667.21(C48H29NO3, 667.21)m/z=667.21(C48H29NO3, 667.21)	1-2871-287	m/z= 767.18(C52H30FNOS2, 767.94)m/z=767.18(C52H30FNOS2, 767.94)
1-661-66	m/z= 683.19(C48H29NO2S, 683.83)m/z=683.19(C48H29NO2S, 683.83)	1-3271-327	m/z= 743.29(C54H33NO3, 743.24)m/z=743.29(C54H33NO3, 743.24)
1-761-76	m/z= 677.28(C48H19D10NO3, 677.83)m/z=677.28(C48H19D10NO3, 677.83)	1-3361-336	m/z= 841.19(C58H35NS3, 842.10)m/z=841.19(C58H35NS3, 842.10)
1-801-80	m/z= 667.21(C48H29NO3, 667.21)m/z=667.21(C48H29NO3, 667.21)	1-3401-340	m/z= 819.28(C60H37NO3, 819.96)m/z=819.28(C60H37NO3, 819.96)
1-861-86	m/z= 687.42(C48D29NO3, 696.39)m/z=687.42(C48D29NO3, 696.39)	2-12-1	m/z= 575.20(C41H25N3O, 575.67)m/z=575.20(C41H25N3O, 575.67)
1-991-99	m/z= 667.21(C48H29NO3, 667.21)m/z=667.21(C48H29NO3, 667.21)	2-32-3	m/z= 551.20(C39H25N3O, 551.19)m/z=551.20(C39H25N3O, 551.19)
1-1091-109	m/z= 667.24(C48H29NO3, 667.21)m/z=667.24(C48H29NO3, 667.21)	2-52-5	m/z= 525.18(C37H23N3O, 525.18)m/z=525.18(C37H23N3O, 525.18)
1-1121-112	m/z= 667.23(C48H29NO3, 667.21)m/z=667.23(C48H29NO3, 667.21)	2-82-8	m/z= 677.25(C49H31N3O, 677.24)m/z=677.25(C49H31N3O, 677.24)
1-1271-127	m/z= 667.24(C48H29NO3, 667.21)m/z=667.24(C48H29NO3, 667.21)	2-212-21	m/z= 601.22(C43H27N3O, 601.21)m/z=601.22(C43H27N3O, 601.21)
1-1391-139	m/z= 667.18(C48H29NO3, 667.21)m/z=667.18(C48H29NO3, 667.21)	2-302-30	m/z= 601.22(C43H27N3O, 601.21)m/z=601.22(C43H27N3O, 601.21)
1-1451-145	m/z= 667.19(C48H29NO3, 667.21)m/z=667.19(C48H29NO3, 667.21)

<실험예 1><Experimental Example 1>

(1) 유기 발광 소자의 제조(적색 호스트)(1) Manufacturing of organic light emitting device (red host)

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with UV (Ultraviolet ozone) for 5 minutes using UV light in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to increase the work function of ITO and remove the remaining film, and then transferred to a thermal evaporation equipment for organic deposition.

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

A light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited as a host with a compound listed in Table 5 to a thickness of 500 Å, and a red phosphorescent dopant [(piq) ₂ (Ir) (acac)] was doped at 3% by weight based on the weight of the host. Afterwards, BCP (bathocuproine) was deposited to a thickness of 60 Å as a hole blocking layer, and Alq ₃ was deposited to a thickness of 200 Å as an electron transport layer on top of it. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form the cathode. By doing this, an organic light emitting device was manufactured.

Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 -8 to 10 ^-6 torr for each material and used for OLED production.

(2) 유기 발광 소자의 구동 전압 및 발광 효율(2) Driving voltage and luminous efficiency of organic light-emitting devices

The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using the M7000 from McScience, and the standard luminance was measured to be 6,000 cd using the lifespan measurement equipment (M6000) manufactured by McScience based on the measurement results. When /m ² , T ₉₀ was measured. The characteristics of the organic electroluminescent device of the present invention are shown in Table 6 below. Above, T ₉₀ refers to the lifespan (unit: h, time), which is the time for the initial luminance to reach 90%.

	화합물compound	비율 (P:N)ratio (P:N)	구동전압 (V)driving voltage (V)	효율 (cd/A)efficiency (cd/A)	색좌표 (x, y)Color coordinates (x, y)	수명 (T₉₀)life span (T ₉₀ )
비교예 1Comparative Example 1	AA		4.814.81	11.711.7	(0.685, 0.315)(0.685, 0.315)	88
비교예 2Comparative Example 2	BB		4.524.52	10.610.6	(0.685, 0.315)(0.685, 0.315)	99
비교예 3Comparative Example 3	CC		4.694.69	11.811.8	(0.685, 0.315)(0.685, 0.315)	88
비교예 4Comparative Example 4	DD		4.964.96	10.110.1	(0.685, 0.315)(0.685, 0.315)	77
비교예 5Comparative Example 5	A:2-1A:2-1	1:11:1	3.653.65	31.731.7	(0.685, 0.315)(0.685, 0.315)	4949
비교예 6Comparative Example 6	D:2-21D:2-21	1:11:1	3.273.27	40.340.3	(0.685, 0.315)(0.685, 0.315)	105105
실시예 1Example 1	1-11-1		4.264.26	17.917.9	(0.685, 0.315)(0.685, 0.315)	1010
실시예 2Example 2	1-21-2		4.174.17	21.521.5	(0.685, 0.315)(0.685, 0.315)	1010
실시예 3Example 3	1-121-12		4.224.22	19.819.8	(0.684, 0.315)(0.684, 0.315)	1212
실시예 4Example 4	1-131-13		4.284.28	23.123.1	(0.683, 0.316)(0.683, 0.316)	1111
실시예 5Example 5	1-151-15		4.264.26	17.617.6	(0.685, 0.315)(0.685, 0.315)	3030
실시예 6Example 6	1-181-18		4.194.19	22.422.4	(0.685, 0.315)(0.685, 0.315)	1313
실시예 7Example 7	1-301-30		4.214.21	24.124.1	(0.684, 0.315)(0.684, 0.315)	1212
실시예 8Example 8	1-321-32		4.304.30	23.523.5	(0.685, 0.315)(0.685, 0.315)	2121
실시예 9Example 9	1-331-33		4.284.28	14.914.9	(0.685, 0.315)(0.685, 0.315)	2020
실시예 10Example 10	1-491-49		4.214.21	14.214.2	(0.685, 0.315)(0.685, 0.315)	1515
실시예 11Example 11	1-571-57		4.324.32	22.822.8	(0.685, 0.315)(0.685, 0.315)	2323
실시예 12Example 12	1-651-65		4.334.33	23.223.2	(0.685, 0.315)(0.685, 0.315)	1010
실시예 13Example 13	1-661-66		4.194.19	20.720.7	(0.683, 0.315)(0.683, 0.315)	1313
실시예 14Example 14	1-761-76		4.294.29	22.722.7	(0.685, 0.315)(0.685, 0.315)	2222
실시예 15Example 15	1-801-80		4.264.26	29.829.8	(0.685, 0.315)(0.685, 0.315)	1010
실시예 16Example 16	1-861-86		4.184.18	22.622.6	(0.685, 0.315)(0.685, 0.315)	2727
실시예 17Example 17	1-991-99		3.713.71	23.523.5	(0.685, 0.315)(0.685, 0.315)	1111
실시예 18Example 18	1-1091-109		4.124.12	24.724.7	(0.685, 0.315)(0.685, 0.315)	1010
실시예 19Example 19	1-1121-112		3.893.89	15.115.1	(0.685, 0.315)(0.685, 0.315)	1111
실시예 20Example 20	1-1271-127		4.054.05	16.416.4	(0.685, 0.315)(0.685, 0.315)	1010
실시예 21Example 21	1-1391-139		3.983.98	16.516.5	(0.685, 0.315)(0.685, 0.315)	1111
실시예 22Example 22	1-1451-145		4.164.16	25.625.6	(0.685, 0.315)(0.685, 0.315)	1111
실시예 23Example 23	1-1671-167		4.034.03	15.915.9	(0.685, 0.315)(0.685, 0.315)	2424
실시예 24Example 24	1-1691-169		4.024.02	18.018.0	(0.685, 0.315)(0.685, 0.315)	1010
실시예 25Example 25	1-1781-178		4.184.18	22.622.6	(0.685, 0.315)(0.685, 0.315)	1717
실시예 26Example 26	1-1921-192		4.284.28	23.323.3	(0.684, 0.315)(0.684, 0.315)	2828
실시예 27Example 27	1-2021-202		3.933.93	19.819.8	(0.685, 0.315)(0.685, 0.315)	1313
실시예 28Example 28	1-2261-226		4.184.18	17.917.9	(0.685, 0.315)(0.685, 0.315)	1010
실시예 29Example 29	1-2301-230		4.124.12	24.524.5	(0.685, 0.314)(0.685, 0.314)	1313
실시예 30Example 30	1-2491-249		3.863.86	21.321.3	(0.685, 0.315)(0.685, 0.315)	1111
실시예 31Example 31	1-2651-265		4.124.12	25.525.5	(0.684, 0.315)(0.684, 0.315)	1212
실시예 32Example 32	1-2681-268		4.224.22	19.719.7	(0.685, 0.317)(0.685, 0.317)	1414
실시예 33Example 33	1-2711-271		4.144.14	21.221.2	(0.685, 0.317)(0.685, 0.317)	2727
실시예 34Example 34	1-2871-287		4.234.23	20.920.9	(0.685, 0.314)(0.685, 0.314)	2323
실시예 35Example 35	1-3271-327		3.943.94	25.525.5	(0.685, 0.315)(0.685, 0.315)	1212
실시예 36Example 36	1-3361-336		4.304.30	23.123.1	(0.684, 0.315)(0.684, 0.315)	1010
실시예 37Example 37	1-3401-340		3.983.98	23.823.8	(0.685, 0.316)(0.685, 0.316)	1616
실시예 38Example 38	1-1:2-11-1:2-1	1:21:2	2.552.55	63.763.7	(0.685, 0.315)(0.685, 0.315)	177177
실시예 39Example 39		1:11:1	2.402.40	62.162.1	(0.685, 0.315)(0.685, 0.315)	178178
실시예 40Example 40		2:12:1	2.452.45	61.561.5	(0.685, 0.315)(0.685, 0.315)	180180
실시예 41Example 41	1-32:2-31-32:2-3	1:11:1	2.992.99	58.558.5	(0.685, 0.315)(0.685, 0.315)	231231
실시예 42Example 42	1-57:2-31-57:2-3	1:21:2	2.552.55	60.860.8	(0.685, 0.315)(0.685, 0.315)	229229
실시예 43Example 43		1:11:1	2.582.58	59.359.3	(0.685, 0.315)(0.685, 0.315)	235235
실시예 44Example 44		2:12:1	2.752.75	54.154.1	(0.685, 0.315)(0.685, 0.315)	228228
실시예 45Example 45	1-65:2-51-65:2-5	1:11:1	2.452.45	63.063.0	(0.685, 0.315)(0.685, 0.315)	198198
실시예 46Example 46	1-86:2-51-86:2-5	1:11:1	2.802.80	64.164.1	(0.685, 0.315)(0.685, 0.315)	229229
실시예 47Example 47	1-109:2-81-109:2-8	1:11:1	2.432.43	61.161.1	(0.685, 0.315)(0.685, 0.315)	354354
실시예 48Example 48	1-127:2-81-127:2-8	1:11:1	2.402.40	58.358.3	(0.685, 0.315)(0.685, 0.315)	383383
실시예 49Example 49	1-139:2-81-139:2-8	1:21:2	2.402.40	54.154.1	(0.685, 0.315)(0.685, 0.315)	251251
실시예 50Example 50		1:11:1	2.352.35	59.559.5	(0.685, 0.315)(0.685, 0.315)	270270
실시예 51Example 51		2:12:1	2.362.36	60.260.2	(0.685, 0.315)(0.685, 0.315)	298298
실시예 52Example 52	1-169:2-211-169:2-21	1:11:1	2.382.38	61.061.0	(0.685, 0.315)(0.685, 0.315)	243243
실시예 53Example 53	1-202:2-211-202:2-21	1:11:1	2.402.40	59.659.6	(0.685, 0.315)(0.685, 0.315)	234234
실시예 54Example 54	1-226:2-301-226:2-30	1:11:1	2.512.51	57.757.7	(0.685, 0.315)(0.685, 0.315)	243243
실시예 55Example 55	1-249:2-301-249:2-30	1:21:2	2.412.41	56.056.0	(0.685, 0.315)(0.685, 0.315)	185185
실시예 56Example 56		1:11:1	2.602.60	55.455.4	(0.685, 0.315)(0.685, 0.315)	234234
실시예 57Example 57		2:12:1	2.452.45	53.953.9	(0.685, 0.315)(0.685, 0.315)	194194

Compounds A to D used in Table 5 are as follows.

As can be seen from the results in Table 6, in the case of Examples 1 to 53 in which the heterocyclic compound represented by Formula 1 of the present application was used as a host for the organic material layer of the organic light-emitting device, especially the light-emitting layer, the organic compounds of Comparative Examples 1 to 6 It was confirmed that driving voltage and efficiency could be improved compared to light emitting devices.

That is, compared to compounds A to D used in Comparative Examples 1 to 6, the arylamine compound represented by Formula 1 of the present invention used in Examples 1 to 40 has an aryl substituted at a specific position compared to the carbazole compound. It was confirmed that the strong hole transfer (HT) characteristics of the amine group eliminate the hole trap phenomenon occurring in the dopant.

In addition, the compound of the present invention, unlike compounds A to D, does not have a linear structure, but has a steric configuration as shown in Chemical Formula 1, and thus has high thermal stability. In addition, it is used as a red host material because it enables strong charge transfer by spatially separating HOMO (Highest Occupied Molecular Orbital) and LUMO (HOMO, Lowest Unoccupied Molecular Orbital). It was confirmed that it is suitable and that high efficiency can be expected when used as an organic material in an organic light-emitting device.

[Explanation of symbols]

100: substrate

200: anode

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

Heterocyclic compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X1 to X3 are the same or different from each other and are each independently O or S,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring where two or more adjacent groups are bonded to each other; or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

a to e are the same or different from each other and are each independently an integer of 0 to 3,

f is an integer from 0 to 4,

m1 and m2 are the same or different from each other and are each independently an integer from 0 to 4,

n1 and n2 are the same as or different from each other, and are each independently an integer of 1 to 5.
According to paragraph 1,

A heterocyclic compound where Formula 1 is represented by the following Formulas 1-1 to 1-8:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8,

The definitions of X1 to
According to paragraph 1,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Or a substituted or unsubstituted C2 to C30 heteroaryl group, a heterocyclic compound.
According to paragraph 1,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring in which two or more adjacent groups are bonded to each other; or forms a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group, a heterocyclic compound.
According to paragraph 1,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; A substituted or unsubstituted C6 to C20 aromatic hydrocarbon selected from the group consisting of a substituted or unsubstituted C6 to C20 aryl group and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; Or a heterocyclic compound that forms a substituted or unsubstituted C2 to C20 heterocycle.
According to paragraph 1,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; And a heterocyclic compound selected from the group consisting of halogen.
According to paragraph 1,

A heterocyclic compound represented by Formula 1 does not contain deuterium as a substituent, or the content of deuterium is 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.
According to paragraph 1,

The heterocyclic compound represented by Formula 1 is a heterocyclic compound represented by any one of the following compounds:

.
first electrode;

a second electrode provided opposite to the first electrode; and

One or more organic layers provided between the first electrode and the second electrode;

An organic light-emitting device comprising,

An organic light-emitting device, wherein at least one of the organic layers includes the heterocyclic compound according to any one of claims 1 to 8.
According to clause 9,

The organic layer includes a light-emitting layer,

An organic light-emitting device wherein the light-emitting layer includes a heterocyclic compound represented by Formula 1.
According to clause 9,

The organic layer includes a light-emitting layer,

The light emitting layer includes a host material,

An organic light-emitting device wherein the host material includes a heterocyclic compound represented by Formula 1.
According to clause 9,

The organic material layer further includes a heterocyclic compound represented by the following formula (A):

[Formula A]

In Formula A,

X 11 to X 13 are the same as or different from each other and are each independently N or CR',

At least one of X 11 to X 13 is N,

R a1 to R a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; Substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.
According to clause 12,

The heterocyclic compound represented by Formula A is an organic light-emitting device represented by any one of the following compounds:

.
According to clause 9,

The organic light emitting device further includes one or two layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer. Phosphorus, organic light emitting device.
A composition for an organic material layer comprising a heterocyclic compound according to any one of claims 1 to 8 and a heterocyclic compound represented by the following formula (A):

[Formula A]

In Formula A,

X 11 to X 13 are the same as or different from each other and are each independently N or CR',

At least one of X 11 to X 13 is N,

R a1 to R a3 and R' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; A substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.
According to clause 15,

A composition for an organic material layer, wherein the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula A in the composition is 1:10 to 10:1.