KR20220056274A - Heterocyclic compound, organic light emitting device comprising same, manufacturing method of same and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, an organic light emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer. The compound described in the present specification can be used as a material for an organic material layer of the organic light emitting device. In particular, the compound can be used as a hole transport material, a light emitting material, or an electron blocking material for the organic light emitting device.

Description

Heterocyclic compound, organic light emitting device including same, manufacturing method thereof, and composition for organic material layer

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

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

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

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

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

A compound having a chemical structure that can satisfy conditions required for materials usable in an organic light-emitting device, such as an appropriate energy level, electrochemical stability, and thermal stability, and can play various roles required in an organic light-emitting device according to a substituent Research on organic light emitting devices including

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

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

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided.

[Formula 1]

In Formula 1,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; -P(=O)RR'; And -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero form a ring,

Y is O; or S;

L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a C2 to C60 heteroarylene group comprising at least one bond of -N= in a substituted or unsubstituted substituent;

Ar1 and Ar2 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,

N-Het is a C2 to C60 heteroaryl group that is substituted or unsubstituted, and includes at least one bond of -N= in the substituent;

a is an integer from 0 to 3,

m is an integer from 0 to 4,

Wherein R, R' and R" are the same as or different from each other, and 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 is a heteroaryl group of

In addition, according to an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the heterocyclic compound represented by Formula 1 above. provides

In addition, in an exemplary embodiment of the present application, the organic material layer including the heterocyclic compound represented by Formula 1 further comprises a compound represented by Formula A or a compound represented by Formula B below. to provide.

[Formula A]

[Formula B]

In Formula A and Formula B,

Rc, Rd, and Ra1 to Ra3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR101R102R103; -P(=O)R101R102; And -NR101R102 or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

R101, R102, and R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; 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,

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r and s are integers from 0 to 7.

In addition, another exemplary embodiment of the present application is a heterocyclic compound represented by Formula 1; and a compound represented by Formula A or a compound represented by Formula B. It provides a composition for an organic material layer of an organic light emitting device comprising a.

Finally, an exemplary embodiment of the present application includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application. A method of manufacturing an organic light emitting device is provided.

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

In particular, the heterocyclic compound according to the present application has a substituent of a C2 to C60 heteroaryl group including at least one bond of -N= in the substituent to benzene of the indene condensed ring in the core structure, and the core structure itself By strengthening the hole characteristics, it is possible to control a wide band gap and a high T1 value, which shows excellent efficiency when the compound is used as a hole transport material, a light emitting material, or an electron blocking material of an organic light emitting device characterized in that

In addition, the heterocyclic compound represented by Formula 1 and the compound represented by Formula A or Formula B may be simultaneously used as a material of the light emitting layer of the organic light emitting device. In this case, it is possible to lower the driving voltage of the device, improve the light efficiency, and particularly improve the lifespan characteristics of the device due to the thermal stability of the compound.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

Hereinafter, the present application will be described in detail.

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

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

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

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

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

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

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group a nyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, a condensed cyclic group thereof, and the like, but is not limited thereto.

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

,

,

,

,

,

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

,

,

,

,

,

and the like, but is not limited thereto.

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

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. In addition, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR104R105R106, R104 to R106 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

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

The structures exemplified by the above-described cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group may be applied, except that the aliphatic or aromatic hydrocarbon ring or heterocycle that adjacent groups may form is not a monovalent group.

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

In the present specification, "substituted or unsubstituted" means C1 to C60 straight-chain or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR' substituted or unsubstituted with one or more substituents selected from the group consisting of, or substituted or unsubstituted with a substituent to which two or more substituents selected from the above-exemplified substituents are connected means that it has been returned,

Wherein R, R' and R" are the same as or different from each other, and 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 is a heteroaryl group of

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

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

In the exemplary embodiment of the present application, in the case of "when no substituents are indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, etc. If deuterium is not explicitly excluded, hydrogen and deuterium may be mixed and used in the compound. That is, when it is expressed that "substituent X is hydrogen", deuterium is not excluded, such as 100% hydrogen content and 0% deuterium content, and may mean a state in which hydrogen and deuterium are mixed.

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

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

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

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

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

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

In an exemplary embodiment of the present application, a compound represented by Formula 1 is provided.

In an exemplary embodiment of the present application, the C2 to C60 heteroarylene group including at least one bond of -N= in the substituent is a single bond and a double bond in the substituent having a C2 to C60 heteroarylene group. It means that it includes at least one nitrogen (N) having all of them, and a heteroarylene group consisting of only a single bond is not included in the above definition. That is, examples of the C2 to C60 heteroarylene group including at least one -N= bond in the substituent include a pyridine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinol group, a benzimidazole group , a pyridazine group, a tetrazine group, etc., and is not particularly limited as long as at least one bond of -N= is included.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

Definitions of R1 to R5, L1, N-Het, Ar1, Ar2, Y, a, and m are the same as those in Formula 1 above.

In an exemplary embodiment of the present application, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; -P(=O)RR'; And -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero rings can be formed.

In another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; -P(=O)RR'; And -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero rings can be formed.

In another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; -P(=O)RR'; And -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C40 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aliphatic or aromatic hetero rings can be formed.

In another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by Chemical Formula 6 or Chemical Formula 7 below.

[Formula 6]

[Formula 7]

In Formulas 6 and 7,

Definitions of R1 to R5, L1, N-Het, Ar1, Ar2, a, and m are the same as in Formula 1 above.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other and 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 another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C40 alkyl group; Or it may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C30 alkyl group; Or it may be a substituted or unsubstituted C6 to C30 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C20 alkyl group; Or it may be a substituted or unsubstituted C6 to C20 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a C1 to C20 alkyl group; Or it may be a C6 to C20 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a linear C1 to C20 alkyl group; Or it may be a monocyclic C6 to C20 aryl group.

In another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other and each independently a methyl group; or a phenyl group.

In the exemplary embodiment of the present application, Ar1 and Ar2 may have the same substituents as each other.

In the exemplary embodiment of the present application, Ar1 and Ar2 may have different substituents from each other.

In an exemplary embodiment of the present application, L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or it may be a C2 to C60 heteroarylene group including at least one bond of -N= in a substituted or unsubstituted substituent.

In another embodiment, L1 is a direct bond; a substituted or unsubstituted C6 to C40 arylene group; Or it may be a C2 to C40 heteroarylene group including at least one bond of -N= in a substituted or unsubstituted substituent.

In another embodiment, L1 is a direct bond; a substituted or unsubstituted C6 to C40 arylene group; Or it may be a C2 to C40 heteroarylene group including at least 1 or more and 3 or less bonds of -N= in a substituted or unsubstituted substituent.

In another embodiment, L1 is a direct bond; C6 to C20 arylene group; Or it may be a C2 to C20 heteroarylene group including at least 1 or more and 3 or less bonds of -N= in the substituent.

In another embodiment, L1 is a direct bond; phenylene group; biphenylene group; naphthylene group; Or it may be a divalent pyridine group.

In an exemplary embodiment of the present application, N-Het may be a C2 to C60 heteroaryl group that is substituted or unsubstituted and includes at least one bond of -N= in the substituent.

In another exemplary embodiment, N-Het may be a C2 to C60 heteroaryl group that is substituted or unsubstituted and includes at least 1 or more and 3 or less bonds of -N= in the substituent.

In another exemplary embodiment, N-Het may be a C2 to C40 heteroaryl group that is substituted or unsubstituted and includes at least 1 or more and 3 or less bonds of -N= in the substituent.

In another exemplary embodiment, N-Het may be a C2 to C20 heteroaryl group that is substituted or unsubstituted and includes at least 1 or more and 3 or less bonds of -N= in the substituent.

In another exemplary embodiment, N-Het is unsubstituted or substituted with deuterium, a C1 to C60 alkyl group, a C6 to C60 aryl group, or a C2 to C60 heteroaryl group, and the -N= bond in the substituent is at least 1 It may be a C2 to C20 heteroaryl group including 3 or less.

In an exemplary embodiment of the present application, the N-Het may be represented by any one of the following Chemical Formulas 1-1 to 1-5.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,

X1 is N; or CR21, X2 is N; or CR22, X3 is N; or CR23, X4 is N; or CR24, X5 is N; or CR25, X6 is N; or CR26, X7 is N; or CR27, X8 is N; or CR28, X9 is N; or CR29, X10 is N; or CR30;

At least one of X1 to X5 is N,

At least one of X6 to X8 is N,

At least one of X9 and X10 is N;

Y1 is O; or S;

R11 to R14 and R21 to R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; And -SiRR'R" is selected from the group consisting of,

Wherein R, R' and R" are the same as or different from each other, and 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 is a heteroaryl group of

In an exemplary embodiment of the present application, R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R".

In another exemplary embodiment, R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a 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, R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group; Or it may be a C2 to C40 heteroaryl group.

In another exemplary embodiment, R21 to R25 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a carbazole group and a naphthyl group; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; dibenzofuran group; a carbazole group; pyridine group; Or it may be a pyrimidine group.

In the exemplary embodiment of the present application, R11 to R14 may be hydrogen.

In an exemplary embodiment of the present application, R26 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R26 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group; Or it may be a C2 to C40 heteroaryl group.

In another exemplary embodiment, R26 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with a naphthyl group; biphenyl group; naphthyl group; or a benzofuro[3,2-c]pyridine group.

In an exemplary embodiment of the present application, R29 and R30 may be hydrogen.

In an exemplary embodiment of the present application, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R".

In another exemplary embodiment, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C6 to C40 aryl group unsubstituted or substituted with a C6 to C40 aryl group; Or it may be a C2 to C60 heteroaryl group.

In another exemplary embodiment, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with a naphthyl group; naphthyl group; biphenyl group; Or it may be a pyridine group.

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

In another exemplary embodiment, R, R′ and R″ may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

In another exemplary embodiment, R, R' and R" may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 monocyclic aryl group.

In another exemplary embodiment, R, R' and R" are the same as or different from each other, and each independently may be a C6 to C20 monocyclic aryl group.

In another exemplary embodiment, R, R' and R" may be a phenyl group.

According to an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

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

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

On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

In addition, in an exemplary embodiment of the present application, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the heterocyclic compound represented by Formula 1 above. provides

In the 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 the 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 of the blue organic light emitting device.

In the 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 of the green organic light emitting device.

In the 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 of the red organic light emitting device.

In the 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 Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

In the 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 light emitting layer of the green organic light emitting device.

In the 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 light emitting layer of the red organic light emitting device.

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

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

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

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

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

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

In the organic light emitting device according to an exemplary embodiment of the present application, the organic material layer including the heterocyclic compound represented by Formula 1 further comprises a compound represented by Formula A or a compound represented by Formula B below. An organic light emitting device is provided.

[Formula A]

[Formula B]

In Formula A and Formula B,

Rc and Rd, Ra1 to Ra3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR101R102R103; -P(=O)R101R102; And -NR101R102 or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,

R101, R102, and R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; 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,

Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

r and s are integers from 0 to 7.

a heterocyclic compound of Formula 1; and Formula A; Or, when the compound of Formula B is included in the organic material layer of the organic light emitting device, better efficiency and lifespan effect are exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, thereby increasing 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 the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan.

In an exemplary embodiment of the present application, Ra1 to Ra3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR101R102R103; -P(=O)R101R102; and -NR101R102 or two or more groups adjacent to each other may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

In another exemplary embodiment, Ra1 to Ra3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ra1 to Ra3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra1 to Ra3 are the same as or different from each other, and each independently C6 to C40 unsubstituted or substituted with a C1 to C40 alkyl group, a C6 to C40 aryl group, or a C2 to C40 heteroaryl group aryl group; Or it may be a C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra1 to Ra3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group, a carbazole group, a dibenzofuran group, a benzocarbazole group, or a dimethylbenzofluorene group; naphthyl group; a biphenyl group unsubstituted or substituted with a phenyl group; triphenylenyl group; dimethyl fluorenyl group; spirobifluorenyl group; dimethylbenzofluorene group; dibenzothiophene group; dibenzofuran group; naphthodibenzofuran group; Or it may be a terphenyl group.

In an exemplary embodiment of the present application, Rc and Rd of Formula B are the same as or different from each other and each independently hydrogen; Or it may be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Rc and Rd of Formula B are the same as or different from each other and each independently hydrogen; Or it may be a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Rc and Rd of Formula B are the same as or different from each other and each independently hydrogen; Or it may be a C6 to C40 aryl group.

In another exemplary embodiment, Rc and Rd of Formula B are the same as or different from each other and each independently hydrogen; or a phenyl group.

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

In another exemplary embodiment, Ra and Rb of Formula B may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Ra and Rb of Formula B may be the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Ra and Rb of Formula B may be the same as or different from each other, and each independently a C6 to C40 aryl group.

In another exemplary embodiment, Ra and Rb of Formula B are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of -CN and SiRa'Rb'Rc' ; a biphenyl group unsubstituted or substituted with a phenyl group; terphenyl group; naphthyl group; triphenylenyl group; Or a dimethyl fluorenyl group; may be.

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

In another exemplary embodiment, Ra', Rb', and Rc' are the same as or different from each other and each independently a substituted or unsubstituted C6 to C40 aryl group; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra', Rb', and Rc' may be the same as or different from each other and each independently a C6 to C40 aryl group.

In another exemplary embodiment, Ra', Rb', and Rc' may be the same as or different from each other and each independently a C6 to C20 aryl group.

In another exemplary embodiment, Ra', Rb', and Rc' may be a phenyl group.

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

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

In addition, another exemplary embodiment of the present application is a heterocyclic compound represented by Formula 1; and a compound represented by Formula A or a compound represented by Formula B. It provides a composition for an organic material layer of an organic light emitting device comprising a.

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

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

The composition may be used when forming an organic material of an organic light emitting device, and in particular, it may be more preferably used when forming a host of a light emitting layer.

In an exemplary embodiment of the present application, the organic material layer is a heterocyclic compound represented by Formula 1; and a compound represented by Formula A or Formula B, and may be used together with a phosphorescent dopant.

In an exemplary embodiment of the present application, the organic material layer is a heterocyclic compound represented by Formula 1; and a compound represented by Formula A or Formula B, and may be used together with an iridium-based dopant.

As the phosphorescent dopant material, those known in the art may be used.

For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M may be used, but the scope of the present invention is not limited by these examples.

Here, L, L', L", X' and X" are different bidentate ligands, and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, or the like.

L is an anionic bidentate ligand coordinated to M with the iridium-based dopant by sp2 carbon and a hetero atom, and X may function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -benzoquinoline), (thiophenepyrizine), phenylpyridine, benzothiophenepyrizine, 3-methoxy-2-phenylpyridine, thiophenepyrizine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

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

In the exemplary embodiment of the present application, the content of the dopant may have a content of 1% to 15%, preferably 3% to 10%, more preferably 5% to 10% based on the entire emission layer.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer may include 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 the heterocyclic compound.

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 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.

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

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

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

In an exemplary embodiment of the present application, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to an exemplary embodiment of the present application. A method of manufacturing an organic light emitting device is provided.

In the exemplary embodiment of the present application, the step of forming the organic material layer is a heterocyclic compound of Formula 1; And it provides a method of manufacturing an organic light emitting device which is formed by using a thermal vacuum deposition method by pre-mixing the compound of Formula A or the compound of Formula B.

That is, the pre-mixed refers to mixing the materials in one park before depositing the heterocyclic compound of Formula 1 and the compound of Formula A on the organic layer.

In addition, the pre-mixed refers to mixing the materials in one park before depositing the heterocyclic compound of Formula 1 and the compound of Formula B 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 including Formula 1 may further include other materials as needed.

The organic material layer including Formula 1 and Formula A at the same time may further include other materials as needed.

The organic material layer including Formula 1 and Formula B at the same time may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the compounds of Chemical Formula 1, Chemical Formula A, and Chemical Formula B are exemplified below, but these are for illustration only and to limit the scope of the present application is not, and may be substituted with materials known in the art.

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

Materials having a relatively low work function may be used as the anode material, and a metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used, and a low molecular weight or high molecular material may be used.

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

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

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

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

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

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

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

< production example 1> Preparation of compound 1

1) Preparation of compound 1-2

2-chloro-10,10-dimethyl-10H-indeno[1,2-b]benzofuran (2-chloro-10,10-dimethyl-10H-indeno[1) in a one-necked round bottom flask (One neck r.b.f) ,2-b]benzofuran) (10g, 37.2mmol), bis(pinacolato)diboron) (14g, 56mmol) tris(dibenzylideneacetone)dipalladium(0) (3.4g, 3.7 mmol), expos tetrakis (triphenylphosphine) palladium (0) (3.4 g, 7.4 mmol), potassium acetate (7.3 g, 74 mmol), a mixture of 1,4-dioxane (100 ml) was refluxed at 120 ° C. stirred. After the solution was passed through Celite as it was, it was concentrated and subjected to silica gel column chromatography. Compound 1-2, 13g (yield 98%) in a liquid state was obtained.

2) Preparation of compound 1

Compound 1-2 (13g, 36.3mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- diphenyl-1,3,5-triazine) (9.7 g, 36.3 mmol), tetrakis (triphenylphosphine) palladium (0) (4.1 g, 3.6 mmol), potassium carbonate (10 g, 72.6 mmol), 1,4 - A mixture of dioxane/water (130ml/40ml) was stirred under reflux at 120°C. After extraction with dichloromethane, and drying over MgSO ₄ , Compound 1 was obtained using silica gel column chromatography purification. (13.8g, yield: 82%)

In Preparation Example 1, using Compound A of Table 1 instead of Compound 1-1, 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- The following target compound was synthesized in the same manner as in Preparation of Compound 1 of Preparation Example 1, except that compound B of Table 1 was used instead of diphenyl-1,3,5-triazine).

In Preparation Example 1, various starting materials of Compound 2-1, 3-1, or 4-1 of Table 2 below may be used instead of Compound 1-1.

In addition, compound A of Table 3 was used instead of compound 1-1 of Preparation Example 1 by diversifying the halide sites of compounds 2-1, 3-1, and 4-1, and 2-chloro-4,6-diphenyl -1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) was used instead of the compound B of Table 3 to synthesize the following target compound.

Heterocyclic compounds corresponding to Chemical Formula 1 other than the compounds described in Preparation Example 1 and Tables 1 to 3 were also prepared in the same manner as described in Preparation Examples.

Synthesis confirmation data of the compounds prepared above are shown in Tables 4 and 5 below. Table 4 is a measurement value of ¹ H NMR (CDCl ₃ , 200Mz), Table 5 is a measurement value of the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

NO ¹ H NMR (CDCl ₃ , 300 Mz) One 8.28(m, 3H), 7.92(m, 2H), 7.77(d, 1H), 7.67(m, 2H), 7.51~7.32(m, 8H), 1.72(s, 6) 3 8.49 (d, 1H), 8.28 (d, 2H), 8.00 to 7.89 (m, 5H), 7.77 (d, 1H), 7.67 to 7.51 (m, 6H), 7.41 to 7.38 (m, 2H), 1.72 ( s, 6) 7 8.55~8.52(m, 2H), 8.28(d, 2H), 8.12(d, 1H), 7.94~7.89(m, 2H), 7.79(d, 2H), 7.68~7.62(m, 5H), 7.51~ 7.25 (m, 10H). 1.72(s, 6) 8 8.52 (d, 1H), 8.28 (d, 2H), 8.00 to 7.85 (m, 6H), 7.73 to 7.51 (m, 8H), 7.42 to 7.25 (m, 6H), 1.72 (s, 6) 9 8.16 (d, 1H), 7.98 to 7.52 (m, 15H), 7.38 to 7.32 (m, 2H), 1.72 (s, 6) 15 9.09 (s, 1H), 8.52 to 8.49 (m, 3H), 8.00 to 7.92 (m, 7H). 7.73 (d, 1H), 7.59 to 7.42 (m, 8H), 1.72 (s, 6) 17 8.28 (m, 4H), 7.89 (d, 1H), 7.67 to 7.66 (m, 3H), 7.51 to 7.32 (m, 9H), 1.72 (s, 6H) 18 8.05 to 7.98 (m, 2H), 7.89 (d, 1H), 7.79 (m, 2H), 7.67 to 7.66 (m, 2H), 7.52 to 7.32 (m, 8H), 1.72 (2, 6H) 20 8.23(s, 1H), 7.89(d, 1H), 7.79(m, 4H), 7.67~7.66(m, 3H), 7.51(m, 4H), 7.41~7.32(m, 5H), 1.72(s, 6H) 23 8.55(m, 2H), 8.08~8.04(m, 4H), 7.95~7.89(m, 3H), 7.66~8.55(m, 8H), 7.39~7.32(m, 4H), 1.72(s, 6H) 26 8.30(m, 2H), 8.16(d, 1H), 7.98(d, 1H), 7.86~7.83(m, 4H), 7.73~7.67(m, 3H), 7.58~7.39(m, 9H), 1.72( s, 6H) 31 8.45 (d, 1H), 8.34 (s, 1H), 8.00 to 7.87 (m, 6H), 7.73 to 7.50 (m, 9H), 7.39 (t, 1H), 1.72 (s, 6H) 33 8.23(s, 1H), 7.92~7.77(m, 9H), 7.66(d, 1H), 7.51(m, 4H), 7.66~7.25(m, 6H), 7.07(d, 1H), 1.72(s, 6H) 36 8.30 (m, 2H), 8.23 (s, 1H), 8.00 to 7.51 (m, 19H), 7.38 to 7.25 (m, 5H), 7.07 (d, 1H), 1.72 (s, 6H) 38 8.56 (d, 1H), 8.00 (m, 3H), 7.89 to 7.83 (m, 4H), 7.66 to 7.59 (m, 5H), 7.38 to 7.22 (m, 9H), 1.72 (s, 6H) 42 8.34 (m, 1H), 8.23 (s, 1H), 8.00 to 7.87 (m, 12H), 7.77 to 7.73 (m, 2H), 7.59 to 7.50 (m, 6H), 7.25 (d, 1H), 7.07 ( d, 1H), 1.72 (s, 6H) 44 8.30~8.28(m, 4H), 8.16(d, 1H), 7.98~7.92(m, 2H), 7.85~7.73(m, 6H), 7.58~7.41(m, 6H), 7.07(d, 1H), 1.72(s, 6H) 48 9.09(s, 1H), 8.49(d, 1H), 8.28(m, 2H), 8.00~7.85(m, 6H), 7.73(m, 1H), 7.62~7.33(m, 10H), 7.25(d, 2H), 1.72(s, 6H) 50 8.16 (d, 1H), 7.89 to 7.79 (m, 7H), 7.67 to 7.51 (m, 5H), 7.41 to 7.25 (m, 7H), 1.72 (s, 6H) 52 8.55 (d, 2H), 8.08 to 8.04 (m, 4H), 7.95 to 7.85 (m, 5H), 7.67 to 7.55 (m, 8H), 7.39 to 7.25 (m, 6H), 1.72 (s, 6H) 54 8.30 (m, 2H), 8.23 (s, 1H), 7.89 to 7.79 (m, 7H), 7.67 to 7.66 (m, 3H), 7.52 to 7.32 (m, 13H), 1.72 (s, 6H) 57 8.23 (s, 1H), 7.98 (d, 1H), 7.85 to 7.67 (m, 8H), 7.52 to 7.39 (m, 12H), 1.72 (s, 6H) 61 8.28 (m, 2H), 7.98 to 7.85 (m, 5H), 7.75 to 7.64 (m, 6H), 7.52 to 7.32 (m, 10H), 1.72 (s, 6H) 63 9.09(s, 2H), 8.49(d, 2H), 8.30(d, 2H), 8.00~7.92(m, 4H), 7.73~7.50(m, 9H), 7.39~7.25(m, 5H), 1.72( s, 6H) 65 8.23(s, 1H), 7.11(m, 1H), 7.79(m, 4H), 7.66~7.63(m, 3H), 7.51~7.32(m, 15H), 7.11(m, 4H) 66 8.28 (m, 4H), 7.89 to 7.85 (m, 3H), 7.66 to 7.63 (m, 3H), 7.51 to 7.26 (m, 17H), 7.11 (m, 4H) 71 8.16 (d, 1H), 7.83 to 7.79 (m, 5H), 7.66 to 7.51 (m, 5H), 7.41 to 7.26 (m, 11H), 7.11 (m, 4H) 72 9.09 (s, 1H), 8.49 (m, 1H), 8.00 to 7.89 (m, 6H), 7.66 to 7.52 (m, 6H), 7.38 to 7.26 (m, 10H), 7.11 (m, 4H) 73 8.48(m, 1H), 8.28(m, 4H), 7.89(m, 1H), 7.66(m, 1H), 7.51~7.26(m, 16H), 7.11(m, 4H) 76 8.48 (d, 1H), 8.28 (m, 2H), 7.89 to 7.85 (m, 3H), 7.66 (m, 1H), 7.51 to 7.25 (m, 20H), 7.11 (m, 4H) 88 8.48 (m, 1H), 8.28 (m, 2H), 8.00 to 7.85 (m, 6H), 7.73 (d, 1H), 7.85 to 7.25 (m, 18H), 7.11 (m, 4H) 89 8.23 (s, 1H), 7.98 (d, 1H), 7.79 to 7.66 (m, 8H), 7.51 to 7.26 (m, 14H), 7.11 (m, 4H) 91 8.34 (m, 1H), 8.23 (s, 1H), 8.00 to 7.26 (m, 23H), 7.11 (m, 4H) 92 8.28 (m, 4H), 7.98 (d, 1H), 7.85 (m, 3H), 7.73 (m, 2H), 7.52 to 7.25 (m, 16H), 7.11 to 7.06 (m, 5H) 93 8.23(s, 1H), 7.98(d, 1H), 7.79(m, 4H), 7.63(d, 2H), 7.52~7.33(m, 15H), 7.11(m, 4H) 96 9.09(s, 1H), 8.49(d, 1H), 8.28(m, 2H), 8.00~7.92(m, 4H), 7.11(d, 1H), 7.63~7.33(m, 16H), 7.11(m, 4H) 105 8.28 (d, 2H), 7.92 to 7.85 (m, 4H), 7.77 (d, 1H), 7.52 to 7.25 (m, 12H), 1.72 (s, 6H) 107 8.28 to 8.24 (m, 3H), 7.92 to 7.89 (m, 2H), 7.77 (d, 1H), 7.70 to 7.66 (m, 3H), 7.58 to 7.32 (m, 12H), 1.72 (s, 6H) 111 7.55 (d, 1H), 8.42 (d, 1H), 8.28 (d, 2H), 8.08 to 8.04 (m, 2H), 7.89 to 7.85 (m, 4H), 7.77 (d, 1H), 7.67 to 7.41 ( m, 7H), 7.41 to 7.25 (m, 5H), 1.72 (s, 6H) 113 8.34 (s, 1H), 8.00 to 7.82 (m, 6H), 7.77 (d, 1H), 7.70 to 7.59 (m, 6H), 7.38 to 7.32 (m, 4H), 1.72 (s, 6H) 117 8.52 (d, 1H), 8.28 (d, 4H), 7.89 (d, 1H), 7.66 to 7.62 (m, 2H), 7.51 to 7.32 (m, 9H), 1.72 (s, 6H) 119 8.52 to 8.49 (m, 2H), 8.28 (d, 2H), 8.00 to 7.92 (m, 4H), 7.66 to 7.32 (m, 10H), 1.72 (s, 6H) 122 9.09(s, 2H), 8.52~8.49(m, 3H), 8.00~7.89(m, 7H), 7.66~7.59(m, 6H), 7.42~7.32(m, 3H), 1.72(s, 6H) 129 8.28 (d, 4H), 7.92 to 7.85 (m, 4H), 7.77 (d, 2H), 7.66 (d, 1H), 7.51 to 7.32 (m, 10H), 7.07 (m, 1H), 1.72 (s, 6H) 134 8.28 (d, 2H), 8.00 to 7.51 (m, 17H), 7.41 to 7.25 (m, 7H), 7.07 (d, 1H), 1.72 (s, 6H) 142 8.05~7.98(m, 2H), 7.89~7.79(m, 4H), 7.66~7.62(m, 2H), 7.52~7.32(m, 11H), 1.72(s, 6H) 148 9.09 (d, 2H), 8.49 (m, 2H), 8.00 to 7.85 (m, 9H), 7.66 to 7.59 (m, 6H), 7.42 to 7.25 (m, 10H), 1.72 (s, 6H) 150 9.09 (s, 2H), 8.49 (m, 2H), 8.00 to 7.89 (m, 7H), 7.67 to 7.59 (m, 6H), 7.39 to 7.32 (m, 4H), 1.72 (s, 6H) 160 8.28 (m, 2H), 8.00 to 7.85 (m, 6H), 7.73 to 7.51 (m, 9H), 7.41 to 7.25 (m, 6H) , 1.72 (s, 6H) 161 8.28(d, 4H), 7.89~7.85(m, 3H), 7.67~7.66(m, 3H), 7.51~7.25(m, 11H) , 1.72(s, 6H) 162 9.09(s, 1H), 8.49(d, 1H), 8.28(t, 4H), 7.92~7.89(m, 3H), 7.73~7.66(m, 4H), 7.51~7.32(m, 10H) , 1.72( s, 6H) 165 8.55(m, 3H), 8.08~7.95(m, 6H), 7.70~7.55(m, 9H), 7.39~7.32(m, 6H) , 1.72(s, 6H) 169 8.28(t, 4H), 7.98~7.92(m, 2H), 7.77~7.63(m, 3H), 7.52~7.41(m, 8H) , 1.72(s, 6H) 174 8.23(s, 1H), 7.98~7.92(m, 2H), 7.79~7.67(m, 7H), 7.52~7.41(m, 8H) , 1.72(s, 6H) 183 8.52(d, 1H), 8.28(d, 2H), 8.00~7.85(m, 6H), 7.73(d, 2H), 7.62~7.41(m, 10H), 7.25(d, 2H) , 1.72(s, 6H) 189 8.28 (t, 4H), 7.98 (d, 1H), 7.73 to 7.63 (m, 3H), 7.52 to 7.41 (m, 9H) , 1.72 (s, 6H) 197 8.28(m, 2H), 8.23(s, 1H), 7.98(d, 1H), 7.79~7.67(m, 4H), 7.52~7.32(m, 10H) , 1.72(s, 6H) 205 8.28 (t, 4H), 7.98 (d, 1H), 7.85 (d, 2H), 7.73 (d, 1H), 7.62 (s, 1H), 7.52 to 7.33 (m, 10H), 7.25 (d, 2H) , 1.72(s, 6H) 207 8.28(d, 2H), 8.00~7.85(m, 8H), 7.73(d, 2H), 7.62~7.25(m, 15H) , 1.72(s, 6H) 218 8.55 (m, 1H), 8.28 (t. 2H), 8.08 to 7.95 (m, 4H), 7.85 (d, 2H), 7.73 to 7.41 (m, 14H) , 1.72 (s, 6H) 220 8.23(s, 1H), 7.98(d, 1H), 7.79~7.67(m, 8H), 7.57~7.25(m, 16H) , 1.72(s, 6H)

compound FD-MS compound FD-MS One m/z = 465.54 (C32H23N3O=465.18) 113 m/z = 528.60 (C37H24N2O2=528.18) 3 m/z= 515.60 (C36H25N3O=515.20) 115 m/z = 488.58 (C35H24N2O=488.19) 5 m/z=555.62 (C38H25N3O2=555.19) 117 m/z = 465.54 (C32H23N3O = 465.18) 7 m/z= 630.74 (C44H30N4O = 630.24) 119 m/z= 515.60 (C36H25N3O=515.20) 9 m/z = 544.66 (C37H24N2OS =544.16) 121 m/z = 541.64 (C38H27N3O=541.22) 11 m/z = 504.64 (C35H24N2S = 504.17) 123 m/z=541.64 (C38H27N3O=541.22) 13 m/z= 442.57 ( C30H22N2S =442.15 ) 125 m/z=528.60 (C37H24N2O2=528.18) 15 m/z = 581.73 (C40H27N3S = 581.19) 127 m/z = 488.58 (C35H24N2O=488.19) 17 m/z= 465.54 (C32H23N3O=465.18) 129 m/z=541.64 (C38H27N3O=541.22) 19 m/z= 465.54 (C32H23N3O=465.18) 131 m/z=540.65 (C39H28N2O=540.22) 21 m/z= 502.60 (C36H26N2O=502.20) 133 m/z=540.65 (C39H28N2O=540.22) 23 m/z= 565.66 (C40H27N3O=565.22) 135 m/z=514.62 (C37H26N2O=514.20) 25 m/z= 571.69 (C38H25N3OS=571.17) 137 m/z=541.64 (C38H27N3O=541.22) 27 m/z= 555.72 (C39H28N2S= 556.20) 139 m/z=540.65 (C39H28N2O=540.22) 29 m/z= 607.76 (C42H29N3S= 607.21) 141 m/z=654.75 (C47H30N2O2=654.23) 31 m/z= 560.73 ( C37H24N2S2= 560.14) 143 m/z=641.76 (C46H31N3O=641.25) 33 m/z= 540.65 (C39H28N2O=540.22) 145 m/z=631.72 (C44H29N3O2=631.23) 35 m/z = 541.64 (C38H27N3O=541.22) 147 m/z=630.74 (C44H30N4O=630.24) 37 m/z= 541.64 (C38H27N3O=541.22) 149 m/z=541.64 (C38H27N3O=541.22) 39 m/z= 590.71 (C43H30N2O=590.24) 151 m/z=541.64 (C38H27N3O=541.22) 41 m/z=557.71 (C38H27N3S=557.19) 153 m/z=541.64 (C38H27N3O=541.22) 43 m/z=556.72 (C39H28N2S=556.20) 155 m/z=544.66 (C37H24N2OS=544.16) 45 m/z=586.77 (C39H26N2S2=586.15) 157 m/z=515.60 (C36H25N3O=515.20) 47 m/z=557.71 (C38H27N3S=557.19) 159 m/z=514.62 (C37H26N2O=514.20) 49 m/z = 541.64 (C38H27N3O=541.22) 161 m/z=541.64 (C38H27N3O=541.22) 51 m/z=540.65 (C39H28N2O=540.22) 163 m/z = 540.65 (C39H28N2O=540.22) 53 m/z=502.60 (C36H26N2O=502.20) 165 m/z=654.75 (C47H30N2O2=654.23) 55 m/z=494.61 (C33H22N2OS=494.15) 167 m/z=630.74 (C44H30N4O=630.24) 57 m/z=556.72 (C39H28N2S=556.20) 169 m/z=481.61 (C32H23N3S=481.16) 59 m/z=557.71 (C38H27N3S=557.19) 171 m/z=581.73 (C40H27N3S=581.19) 61 m/z=647.79 (C44H29N3OS=647.20) 173 m/z=580.74 (C41H28N2S=580.20) 63 m/z=620.76 (C43H28N2OS=620.19) 175 m/z=560.73 (C37H24N2S2=560.14) 65 m/z=588.70 (C43H28N2O=588.22) 177 m/z=454.58 (C31H22N2S=454.15) 67 m/z = 715.84 (C52H33N3O=715.26) 179 m/z=530.68 (C37H26N2S=530.18) 69 m/z = 665.78 (C48H31N3O=665.25) 181 m/z=557.71 (C38H27N3S=557.19) 71 m/z=562.66 (C41H26N2O=562.20) 183 m/z=607.76 (C42H29N3S=607.21) 73 m/z=589.68 (C42H27N3O=589.22) 185 m/z=560.73 (C37H24N2S2=560.14) 75 m/z = 638.75 (C47H30N2O=638.24) 187 m/z=504.64 (C35H24N2S=504.17) 77 m/z = 664.79 (C49H32N2O=664.25) 189 m/z=481.61 (C32H23N3S=481.16) 79 m/z=652.74 (C47H28N2O2=652.22) 191 m/z=556.72 (C39H28N2S=556.20) 81 m/z=695.83 (C48H29N3OS=695.20) 193 m/z=480.62 (C33H24N2S=480.17) 83 m/z= 680.86 (C49H32N2S=680.23) 195 m/z=560.73 (C37H24N2S2=560.14) 85 m/z= 654.82 (C47H30N2S=654.21) 197 m/z=480.62 (C33H24N2S=480.17) 87 m/z = 694.84 (C48H30N4S=694.22) 199 m/z=581.73 (C40H27N3S=581.19) 89 m/z=604.76 (C43H28N2S=604.20) 201 m/z= 555.73 (C40H29NS=555.20) 91 m/z=654.82 (C47H30N2S=654.21) 203 m/z=556.72 (C39H28N2S=556.20) 93 m/z=604.76 (C43H28N2S=604.20) 205 m/z= 557.71 (C38H27N3S= 557.19) 95 m/z= 654.82 (C47H30N2S=654.21) 207 m/z= 683.86 (C48H33N3S= 683.24) 97 m/z= 479.63 (C34H25NS=479.63) 209 m/z= 636.83 (C43H28N2S2=636.17) 99 m/z= 479.63 (C34H25NS=479.17) 211 m/z= 633.80 (C44H31N3S= 633.22) 101 m/z=587.71 (C44H29NO=587.22) 213 m/z = 555.72 (C39H28N2S = 556.20) 103 m/z= 563.69 (C42H29NO=563.22) 215 m/z= 607.76 (C42H29N3S= 607.21) 105 m/z=541.64 (C38H27N3O=541.22) 217 m/z= 632.81 (C45H32N2S= 632.23) 107 m/z=541.64 (C38H27N3O=541.22) 219 m/z= 707.88 (C50H33N3S= 707.24) 109 m/z = 617.74 (C44H31N3O=617.25) 221 m/z = 555.72 (C39H28N2S = 556.20) 111 m/z = 591.70 (C42H29N3O=591.23) 223 m/z= 633.80 (C44H31N3S= 633.22)

< Experimental example 1>- Fabrication of organic light emitting device

1) Fabrication of an organic light emitting device

A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and then UVO (Ultraviolet Ozone) treatment was performed for 5 minutes using UV in a UV (Ultraviolet) washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition 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'-diphenyl- (1,1'-biphenyl)-4,4'-diamine) was formed.

The light emitting layer was thermally vacuum-deposited thereon as follows. Specifically, the compounds shown in Table 6 were used as the red host of the light emitting layer, and 3wt% of the red phosphorescent dopant (piq) ₂ (Ir) (acac) was doped into the red host to deposit a light emitting layer having a thickness of 500 Å. Thereafter, 60 Å of basocuproine (hereinafter, BCP) was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transport layer.

Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. A light emitting device was manufactured.

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

2) Driving voltage and luminous efficiency of organic light emitting device

For the organic light emitting devices of Examples 1 to 12 and Comparative Examples 1 to 7 prepared as described above, electroluminescence (EL) characteristics were measured with M7000 manufactured by McScience, and the lifespan equipment manufactured by McScience based on the measurement results When the reference luminance was 6,000 cd/m ² through a measuring device (M6000), T ₉₀ was measured. The T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The measured characteristics of the organic light emitting device are shown in Table 6 below.

compound drive voltage
(V _op ) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 A 6.32 2.5 (0.677, 0.323) 21 Comparative Example 2 B 6.01 3.9 (0.690, 0.310) N/D Comparative Example 3 C 6.21 1.7 (0.673, 0.319) 5 Comparative Example 4 D 7.82 1.1 (0.689, 0.311) N/D Comparative Example 5 E 5.83 2.2 (0.671, 0.329) N/D Comparative Example 6 F 5.92 1.8 (0.675, 0.325) 7 Comparative Example 7 G 5.21 4.8 (0.676, 0.324) 11 Example 1 One 4.31 15.1 (0.677, 0.323) 48 Example 2 8 4.20 12.5 (0.685, 0.315) 38 Example 3 15 3.90 16.7 (0.679, 0.321) 40 Example 4 24 3.75 14.5 (0.680, 0.320) 29 Example 5 25 3.66 12.5 (0.683, 0.617) 31 Example 6 36 4.10 11.0 (0.677, 0.323) 27 Example 7 41 3.86 10.9 (0.679, 0.321) 40 Example 8 47 4.54 12.5 (0.676, 0.324) 38 Example 9 73 4.32 13.5 (0.681, 0.319) 29 Example 10 82 4.42 14.1 (0.683, 0.317) 30 Example 11 92 3.89 16.1 (0.679, 0.321) 41 Example 12 93 3.78 15.9 (0.678, 0.322) 31

As can be seen in Table 6, the heterocyclic compound of the present invention was excellent in driving, and it was confirmed that the efficiency and lifespan characteristics were superior to those of the compounds of Comparative Examples 1 to 7.

Specifically, the heterocyclic compound of the present invention has a core structure in which a benzofuran ring/benzothiophene ring having a hetero group and an indole ring are fused, and N-Het of electron properties is substituted on the side of the indole ring having strong hole properties. As a result, the HOMO/LUMO electron distribution cloud overlap is small, which reduces the difference between the S1 and T1 energy gaps, and it can be confirmed from Table 6 that the exciton has an efficiency increase effect by ISC. In addition, it was confirmed that the heterocyclic compound of the present invention has a low molecular weight, low Ts and Td, excellent thermal stability, and thus excellent lifespan characteristics.

In the case of Compound A of Table 6, it was confirmed that LUMO, which should be distributed in triazine, spread to O and invaded even the indole ring of the core structure, resulting in poor lifespan and efficiency.

In the case of compound B of Table 6, compared to the compound of the present invention, it does not have a substituent of N-Het, and has shallow LUMO due to lack of ET characteristics (electron transport character), and thus suitable as a light emitting layer host of an organic light emitting device It was confirmed that the band gap was not present.

In the case of the compound C of Table 6, compared to the compound of the present invention, when the fluorenyl group is condensed on the indole ring, it can be confirmed that the efficiency is not good due to the clogging phenomenon, and the deposition temperature is increased due to the increase of the molecular weight It was confirmed that there was an increasing problem.

In the case of compounds D and G of Table 6, instead of N-Het, which is a substituent showing ET characteristics (electron transport character) of Formula 1 of the present invention, a substituent showing HT characteristics (Hole transport character) is substituted (carbazole-based), It was confirmed that the core of the present invention should perform the role of the ET property, and in the case of the compounds D and G, the ability to accept electrons is relatively low, making it difficult to perform the role as ET.

In the case of compounds E and F of Table 6, the core structure of the present invention is in the form of a compound to act as a linker (Linker). That is, the compound E is a material that strongly exhibits an ET characteristic (electron transport character) by triazine, and the compound F exhibits a strong HT characteristic (hole transport character) by an aryl amine. In the case of the above compounds, it was confirmed that one of the electron or hole properties was insufficient and could not perform its role as a single host, and as can be seen in Table 6, it was not suitable for an organic light emitting device.

< Experimental example 2>

1) Manufacture of organic light emitting device

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

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

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. Specifically, the heterocyclic compound represented by Formula 1 of the present application described in Table 7 below was used as a first host, and the compound described in Table 7 below was mixed in the following ratio as a second host, and red phosphorescence was used. A dopant (piq) ₂ (Ir)(acac) was doped in 2 wt% based on the total weight of the light emitting layer in the red host to deposit a light emitting layer having a thickness of 400 Å.

After that, Alq ₃ was deposited as an electron transport layer at 120 Å, and Bphen was deposited as 120 Å as an N-type charge generation layer thereon, and MoO ₃ was deposited at 100 Å as a P-type charge generation layer thereon. In addition, a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed on the P-type charge generating layer.

Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of 20 Å to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. An electroluminescent device was manufactured.

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

2) Driving voltage and luminous efficiency of organic light emitting device

The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured with M7000 of McScience, and the reference luminance was 6,000 cd through the life instrumentation measuring device (M6000) manufactured by McScience with 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 7 below.

compound
(first host: second host) ratio
(N:P) drive voltage
(V _op ) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 A: A-1 1:1 6.50 3.8 (0.692, 0.308) 7 Comparative Example 2 B: B-2 1:1 6.86 4.5 (0.689, 0.311) 6 Comparative Example 3 C: A-12 1:1 5.86 8.8 (0.672, 0.328) N/D Example 1 1: A-2 1:1 3.89 25.8 (0.682, 0.318) 148 Example 2 8: A-5 1:1 3.79 31.2 (0.679, 0.321) 150 Example 3 9: B-7 1:1 4.01 30.8 (0.677, 0.323) 138 Example 4 15 : B-3 1:1 4.23 21.8 (0.683, 0.317) 141 Example 5 24 : B-4 1:1 3.86 20.9 (0.680, 0.320) 158 Example 6 25: B-11 1:1 3.76 30.8 (0.675, 0.325) 145 Example 7 33 : A-8 1:1 4.31 28.7 (0.676, 0.324) 151 Example 8 36 : A-9 1:1 4.18 30.8 (0.681, 0.319) 132 Example 9 41 : B-10 1:1 3.88 38.1 (0.674, 0.326) 135 Example 10 44 : B-8 1:1 3.68 35.1 (0.677, 0.327) 129 Example 11 47: A-12 1:1 3.56 25.6 (0.678, 0.322) 141 Example 12 48 : A-2 1:1 4.09 29.7 (0.683, 0.317) 149 Example 13 73 : A-6 1:1 4.21 24.6 (0.685, 0.315) 152 Example 14 82 : B-6 1:1 3.90 30.9 (0.683, 0.317) 158 Example 15 92 : B-5 1:1 3.48 31.8 (0.679, 0.321) 146 Example 16 93 : B-8 1:1 3.68 24.5 (0.675, 0.325) 153 Example 17 225 : B-20 1:1 3.81 26.5 (0.673, 3.327) 168

[Group A]

[Group B]

In the case of the compound of the present invention, as a unipolar host that does not contain a moiety of strong HT characteristics (Hole transport character), when mixed with a host of P-type (the second host in Table 7), A more improved performance may be exhibited, which could be confirmed from Experimental Example 2 and Table 7.

In particular, looking at the results of Table 7, it was confirmed that when the compound of Formula 1 and the compound of Formula A or Formula B were included at the same time, better efficiency and lifespan effects were exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon.

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, thereby increasing 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 the host of the emission layer, the driving voltage is because holes are injected into the p-host and electrons are injected into the n-host. can be lowered, thereby helping to improve lifespan. In the present invention, it was confirmed that when the donor role was the compound of Formula A or B, and the acceptor role was the heterocyclic compound of Formula 1 used as the light emitting layer host, excellent device properties were exhibited.

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

Claims (17)

A heterocyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; -P(=O)RR'; And -SiRR'R", or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic hetero form a ring,
Y is O; or S;
L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; Or a C2 to C60 heteroarylene group comprising at least one bond of -N= in a substituted or unsubstituted substituent;
Ar1 and Ar2 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,
N-Het is a C2 to C60 heteroaryl group that is substituted or unsubstituted and includes at least one bond of -N= in the substituent;
a is an integer from 0 to 3,
m is an integer from 0 to 4,
Wherein R, R' and R" are the same as or different from each other, and 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 is a heteroaryl group of The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
Definitions of R1 to R5, L1, N-Het, Ar1, Ar2, Y, a, and m are the same as those in Formula 1 above. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 6 or Chemical Formula 7:
[Formula 6]

[Formula 7]

In Formulas 6 and 7,
Definitions of R1 to R5, L1, N-Het, Ar1, Ar2, a, and m are the same as in Formula 1 above. The heterocyclic compound according to claim 1, wherein N-Het is represented by any one of the following Chemical Formulas 1-1 to 1-5:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,
X1 is N; or CR21, X2 is N; or CR22, X3 is N; or CR23, X4 is N; or CR24, X5 is N; or CR25, X6 is N; or CR26, X7 is N; or CR27, X8 is N; or CR28, X9 is N; or CR29, X10 is N; or CR30;
At least one of X1 to X5 is N,
At least one of X6 to X8 is N,
At least one of X9 and X10 is N;
Y1 is O; or S;
R11 to R14 and R21 to R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; And -SiRR'R" is selected from the group consisting of,
Wherein R, R' and R" are the same as or different from each other, and 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 is a heteroaryl group of The method according to claim 1, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a heterocyclic compound that is deuterium. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

a first electrode; a second electrode provided to face the first electrode; and 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 comprises the heterocyclic compound according to any one of claims 1 to 6 Phosphorus organic light emitting device. The organic light-emitting device according to claim 7, wherein the organic material layer comprising the heterocyclic compound of Formula 1 further comprises a compound represented by Formula A or a compound represented by Formula B:
[Formula A]

[Formula B]

In Formula A and Formula B,
Rc, Rd, and Ra1 to Ra3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR101R102R103; -P(=O)R101R102; And -NR101R102 or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,
R101, R102, and R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; 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,
Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r and s are integers from 0 to 7. The organic light emitting diode of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound of Formula 1 above. The organic light-emitting device of claim 7 , wherein the organic material layer includes an emission layer, the emission layer includes a host material, and the host material includes the heterocyclic compound of Formula 1 above. The method according to claim 7, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. An organic light-emitting device further comprising one 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. The organic light-emitting device according to claim 8, wherein the compound represented by Formula A is represented by any one of the following compounds:

The organic light-emitting device according to claim 8, wherein the compound represented by Formula B is represented by any one of the following compounds:

A heterocyclic compound according to any one of claims 1 to 6; And a compound represented by the following formula (A) or a compound represented by the following formula (B); a composition for an organic material layer of an organic light emitting device comprising:
[Formula A]

[Formula B]

In Formula A and Formula B,
Rc and Rd, Ra1 to Ra3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiR101R102R103; -P(=O)R101R102; And -NR101R102 or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle,
R101, R102, and R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; -CN; 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,
Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
r and s are integers from 0 to 7. The composition for an organic material layer of an organic light emitting device according to claim 14, wherein the weight ratio of the heterocyclic compound represented by Formula 1 in the composition to the compound represented by Formula A or Formula B is 1: 10 to 10: 1. preparing a substrate;
forming a first electrode on the substrate;
forming one or more organic material layers on the first electrode; and
forming a second electrode on the organic material layer;
The method of manufacturing an organic light emitting device, wherein the forming of the organic material layer includes forming one or more organic material layers using the composition for an organic material layer according to claim 14 . The method according to claim 16, wherein the step of forming the organic material layer is a heterocyclic compound represented by Formula 1; and a compound represented by Formula A or Formula B; and pre-mixed to form an organic light emitting device using a thermal vacuum deposition method.

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