Organic light-emitting device organic material layer composition and organic light-emitting device including same

By using the combination of heterocyclic compounds of chemical formula A and chemical formula B as the material of the organic material layer, the problem of insufficient performance and lifetime of existing organic luminescent components is solved, and higher luminescent efficiency and thermal stability are achieved.

CN119968090APending Publication Date: 2025-05-09LT MATERIALS CO LTD
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Patent Information

Application Number
CN202411543631.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2023-11-07
Filing Date
2024-10-31
Publication Date
2025-05-09

AI Technical Summary

Technical Problem

The performance, lifetime or efficiency of existing organic luminescent components is insufficient and new organic film materials need to be developed to improve their performance.

Method used

A combination of heterocyclic compounds represented by chemical formula A and chemical formula B is used as the material of the organic material layer, wherein the heterocyclic compounds of chemical formula A are used as the P-type host material and the heterocyclic compounds of chemical formula B are used as the N-type host material, and the material layer of the organic light emitting component is formed by mixing in an appropriate proportion.

Benefits of technology

The combined material can reduce the drive voltage of the assembly, improve luminescence efficiency, improve the thermal stability of the compound, and extend the life of the assembly.

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Abstract

The present specification relates to a composition for an organic material layer of an organic light-emitting device and an organic light-emitting device including the same.
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Description

Technical Field

[0001] The invention relates to an organic material layer composition of an organic light-emitting component and an organic light-emitting component comprising the same. Background Art

[0002] Organic light-emitting components are self-luminous display devices with advantages such as wide viewing angle, excellent contrast, and fast response speed.

[0003] The organic light-emitting component has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light-emitting component having such a structure, the electrons and holes injected from the two electrodes are combined and paired in the organic thin film, and then light is emitted as they are annihilated. The organic thin film can be formed into a single layer or multiple layers as needed.

[0004] The material of the organic film may have a light-emitting function as required. For example, as the material of the organic film, a compound that can constitute a light-emitting layer by itself can be used, or a compound that can serve as a host or dopant of a host-dopant type light-emitting layer can be used. In addition, a compound that can perform hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection can also be used as a material for the organic film.

[0005] In order to improve the performance, lifespan or efficiency of organic light-emitting components, there is a constant need to develop organic thin film materials.

[0006] [Prior art literature]

[0007] [Patent Document]

[0008] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the invention

[0009] [Technical issues]

[0010] The present specification is directed to providing a composition for an organic material layer of an organic light-emitting component and an organic light-emitting component including the composition.

[0011] [Technical solution]

[0012] Exemplary embodiments of the present specification provide a composition for an organic material layer of an organic light-emitting component, the composition including: a heterocyclic compound represented by the following chemical formula A; and a heterocyclic compound represented by the following chemical formula B.

[0013] [Chemical formula A]

[0014]

[0015] [Chemical formula B]

[0016]

[0017] Among them, in chemical formula A and chemical formula B,

[0018] L1 to L4 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0019] Ar1, Ar2 and Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0020] R1 to R4 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0021] R5 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent R5 are bonded to each other to form a ring,

[0022] l1 to l4 are the same as or different from each other and are each independently an integer of 1 to 3, and when l1 to l4 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other,

[0023] r1 and r4 are the same or different from each other and are each independently an integer from 0 to 3,

[0024] r2 is an integer from 0 to 2,

[0025] r3 and r5 are the same or different from each other and are each independently an integer from 0 to 4,

[0026] When r1 to r5 are each an integer of 2 or more, the substituents in brackets are the same as or different from each other,

[0027] ar1 and ar2 are the same or different from each other and are each independently an integer from 1 to 4, and when ar1 and ar2 are each an integer of 2 or more, the substituents in the brackets are the same or different from each other,

[0028] Ar3 is represented by the following chemical formula K,

[0029] [Chemical formula K]

[0030]

[0031] In the chemical formula K,

[0032] Indicates the part connected to L2,

[0033] Xk is O; S; CRk1Rk2; or NRk3,

[0034] Rk and Rk1 to Rk3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0035] rk is an integer from 0 to 7,

[0036] N-Het1 is represented by the following structural formula N,

[0037] [Structural Formula N]

[0038]

[0039] In structural formula N,

[0040] represents the part connected to L3, and

[0041] Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

[0042] Another exemplary embodiment of the present specification provides an organic light-emitting component, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and an organic material layer having one or more layers arranged between the first electrode and the second electrode, wherein the one or more layers of the organic material layer include the above-mentioned composition of the organic material layer for the organic light-emitting component.

[0043] [Beneficial Effects]

[0044] According to an exemplary embodiment of the present application, the composition for the organic material layer can be used as a material of the organic material layer of the organic light-emitting component. In particular, the composition for the organic material layer is characterized by including a combination of a heterocyclic compound represented by Chemical Formula A and a heterocyclic compound represented by Chemical Formula B. More specifically, the composition for the organic material layer is characterized by including a heterocyclic compound represented by Chemical Formula A as a P-type host material and a heterocyclic compound represented by Chemical Formula B as an N-type host material.

[0045] It was confirmed that when the heterocyclic compound represented by Chemical Formula A, which can be used as a unipolar P-type host material with excellent hole mobility, and the compound represented by Chemical Formula B, which can be used as a unipolar N-type host material with excellent electron mobility, are mixed in an appropriate ratio and the resulting mixture is used as a material of a device, the efficiency and life of the device are improved. Compared with the combination of other compositions (e.g., existing single materials and premixed compositions of two or more materials), this combination has the effect of improving device characteristics.

[0046] Therefore, when the composition for an organic material layer is used in an organic light-emitting device, the driving voltage of the device can be reduced, the light-emitting efficiency of the device can be improved, the thermal stability of the compound can be improved, and the lifespan characteristics of the device can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figures 1 to 3 Each of the diagrams schematically illustrates a stacked structure of an organic light emitting component according to an exemplary embodiment of the present specification. DETAILED DESCRIPTION

[0048] Hereinafter, the contents of this specification will be described in more detail.

[0049] In the present specification, when a portion “includes” a constituent element, unless particularly stated otherwise, this does not mean that another constituent element is excluded but means that another constituent element may be further included.

[0050] In this specification, in the chemical formula Indicates the location to be bonded.

[0051] In this specification, the term "substitution" refers to changing a hydrogen atom bonded to a carbon atom of a compound to another substituent. The position of substitution is not limited, as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can replace. In the case of substitution by two or more substituents, the two or more substituents may be the same as or different from each other.

[0052] In the present specification, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C3-C60 cycloalkyl group; a C2-C60 heterocycloalkyl group; a C6-C60 aryl group; a C2-C60 heteroaryl group; a silyl group; a phosphine oxide group; and an amine group, or substituted by a substituent connected to two or more substituents selected from the substituents exemplified above.

[0053] In this specification, "when no substituent is specified in a chemical formula or a structure of a compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2H) or tritium corresponds to an isotope of hydrogen and, unless expressly excluded, can be interpreted as a concept included in hydrogen.

[0054] That is, in this application, according to Chem. Commun., 2014, 50, 14870, deuterium exhibits an effect equivalent to hydrogen in terms of driving voltage, luminous efficiency and lifetime, or an improved effect in certain evaluation criteria, and since this effect is within the range that a person of ordinary skill in the art can predict may have an equivalent effect without conducting specific experiments, therefore, unless explicitly excluded, the deuterium isotope of hydrogen is interpreted as a concept included in hydrogen.

[0055] According to an exemplary embodiment of the present specification, "when no substituent is indicated in a chemical formula or a structure of a compound", it may mean that all positions where a substituent may appear are hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and in this case, the content of deuterium may be from 0% to 100%.

[0056] According to an exemplary embodiment of the present specification, in the case where “no substituent is indicated in the chemical formula or the structure of the compound”, when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents do not explicitly exclude deuterium like hydrogen, and hydrogen and deuterium can be mixed and used in the compound.

[0057] According to an exemplary embodiment of the present specification, deuterium is one of the isotopes of hydrogen, and is an element formed by 1 proton and 1 neutron as a nucleus, which can be expressed as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0058] According to an exemplary embodiment of the present specification, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and may also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0059] According to an exemplary embodiment of the present specification, when the total number of substituents possessed by the base compound is defined as T1 and the number of specific substituents among the substituents is defined as T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0060] In other words, in one example, The deuterium content of phenyl represented as 20% may mean that the total number of substituents that the phenyl may have is 5 (T1 in the formula), and the number of deuterium atoms in these substituents is 1 (T2 in the formula). In other words, a deuterium content of 20% in a phenyl group may be represented by the following structural formula.

[0061]

[0062] In addition, according to an exemplary embodiment of the present specification, “a phenyl group having a deuterium content of 0%” may mean a phenyl group not including a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0063] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0064] In the present specification, the alkyl group includes a linear or branched form having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0065] In the present specification, alkenyl includes a straight chain or branched form with 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of alkenyl can be 2 to 60, particularly 2 to 40, more particularly 2 to 20. The specific example of alkenyl may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styrenyl, etc., but are not limited thereto.

[0066] In the present specification, the alkynyl group includes a straight chain or branched form having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0067] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0068] In this specification, cycloalkyl includes monocyclic or polycyclic groups with carbon atoms of 3 to 60, and may also be further substituted by other substituents. In this article, polycyclic groups refer to groups in which cycloalkyl is directly connected or fused to another cyclic group. In this article, other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups such as heterocycloalkyl, aryl and heteroaryl. The carbon number of cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0069] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, including monocyclic or polycyclic groups with carbon number of 2 to 60, and can also be further substituted by other substituents. In this article, polycyclic groups refer to the groups that heterocycloalkyl is directly connected or fused with another cyclic group. In this article, other cyclic groups can be heterocycloalkyl, but can also be different types of cyclic groups such as cycloalkyl, aryl and heteroaryl. The carbon number of heterocycloalkyl can be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0070] In this specification, aryl includes monocyclic or polycyclic groups with 6 to 60 carbon atoms, which may be further substituted by other substituents. In this article, polycyclic groups refer to groups in which aryl is directly connected or fused to another cyclic group. In this article, other cyclic groups may also be aryl, but may also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl includes spiro. The carbon number of aryl can be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and condensed ring groups thereof, but are not limited thereto.

[0071] In the present specification, the terphenyl group can be selected from the following structures.

[0072]

[0073] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0074] When the fluorenyl group is substituted, the substituent may be selected from the following structures, but is not limited thereto.

[0075]

[0076] In this specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, including monocyclic or polycyclic groups with 2 to 60 carbon atoms, and can be further substituted by other substituents. In this article, polycyclic groups refer to groups in which heteroaryl is directly connected or fused to another cyclic group. In this article, other cyclic groups can also be heteroaryl, but can also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl and aryl. The number of carbon atoms of heteroaryl can be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of heteroaryl include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene group), imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, oxazinyl, thiazinyl, dioxynyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinozolinyl, naphthyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazonaphthyl naphthalenyl), triazaindene group, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophene group, benzofuran group, dibenzothiophene groupgroup), dibenzofuran group, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilole, spirobi(dibenzosilole), dihydrophenazinyl, phenoxazinyl, phenanthridyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindole[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl), 10,11-dihydro-dibenzo[b,f]azepingroup, 9,10-dihydroacridinyl, phenanthrazinyl, phenothiathiazinyl, phthalazinyl, naphththylidinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 2,3-dihydrobenzo[b]thiophene group), 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, 5,11-dihydroindeno[1,2-b]carbazolyl, etc., but are not limited thereto.

[0077] In the present specification, when the substituent is a carbazolyl group, it means a group bonded to nitrogen or carbon of carbazole.

[0078] In the present specification, when a carbazole group is substituted, another substituent may be substituted with nitrogen or carbon of carbazole.

[0079] In the present specification, the benzocarbazolyl group may be any of the following structures.

[0080]

[0081] In the present specification, the dibenzocarbazolyl group may be any of the following structures.

[0082]

[0083] In the present specification, the naphthobenzofuranyl group may be any of the following structures.

[0084]

[0085] In the present specification, the naphthobenzothienyl group may be any of the following structures.

[0086]

[0087] In the present specification, a silyl group includes Si, is a substituent to which the Si atom is directly attached as a free radical, and is represented by -Si(R101)(R102)(R103), wherein R101 to R103 are the same as or different from each other, and may each independently be a substituent consisting of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0088] Specific examples of the silyl group include (trimethylsilyl), (triethylsilyl), (tert-butyldimethylsilyl), (vinyldimethylsilyl), (propyldimethylsilyl), (triphenylsilyl), (diphenylsilyl), phenylsilyl) and the like, but are not limited thereto.

[0089] In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), wherein R104 and R105 are the same or different from each other, and may be each independently a substituent consisting of at least one of hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specifically, the phosphine oxide group may be substituted by an alkyl group or an aryl group, and the above examples may be applied to the alkyl group and the aryl group. Examples of the phosphine oxide group include dimethyl phosphine oxide group, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, etc., but are not limited thereto.

[0090] In the present specification, an amine group is represented by -N(R106)(R107), R106 and R107 are the same or different from each other, and can be each independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amine group can be selected from -NH 2 The amino group is a group consisting of an amine group, a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group and an arylheteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amino 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, a 9-methyl-anthrylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group and the like, but are not limited thereto.

[0091] In the present specification, the above-mentioned examples of the aryl group can be applied to the aralkenyl group except for the divalent aralkenyl group.

[0092] In the present specification, the above-mentioned examples of the heteroaryl group can be applied to the heteroaralkenyl group, except for the divalent heteroaralkenyl group.

[0093] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is closest in space to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0094] The hydrocarbon ring and heterocyclic ring that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocyclic rings and aromatic heterocyclic rings, and the structures exemplified for the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group and heteroaryl group can be applied to these rings respectively, except for those that are not monovalent groups.

[0095] <Organic material layer composition for organic light-emitting device>

[0096] The organic material layer composition of the organic light emitting device according to the present specification will be described below.

[0097] The organic material layer composition of the organic light emitting device according to the exemplary embodiment of the present specification includes a heterocyclic compound represented by the following Chemical Formula A.

[0098] [Chemical formula A]

[0099]

[0100] In Chemical Formula A, each substituent is as described above.

[0101] The heterocyclic compound represented by chemical formula A is a disubstituted naphthobenzofuran, wherein the first substituent Enhanced electron and hole transport properties, second substituent The hole transport properties are enhanced, so that the overall performance can be excellent in terms of electron and hole transport properties.

[0102] When a heterocyclic compound represented by Chemical Formula A having excellent hole transport properties is used together with a heterocyclic compound represented by Chemical Formula B having fast electron transport properties, the heterocyclic compound can act as a P-type host material to induce charge balance in an organic layer (particularly, an emission layer (EML)) and prevent degradation caused by accumulation of electrons and holes, thereby exhibiting high efficiency and long life.

[0103] The organic material layer composition of the organic light emitting device according to the exemplary embodiment of the present specification includes a heterocyclic compound represented by the following Chemical Formula B.

[0104] [Chemical formula B]

[0105]

[0106] In Chemical Formula B, each substituent is as described above.

[0107] The compound represented by chemical formula B is di-substituted as a tricyclic or more oxygen-containing fused heterocyclic ring, and N-Het1 (represented by structural formula N and corresponding to triazine) is used as a first substituent to enhance the electron transport properties, and Ar4 is used as a second substituent to enhance the hole transport properties. Overall, the compound has excellent electron and hole transport properties, and thus can exhibit high efficiency.

[0108] When the heterocyclic compound represented by Chemical Formula B having fast electron transport properties is used together with the heterocyclic compound represented by Chemical Formula A having excellent hole transport properties, the heterocyclic compound can act as an N-type host material to induce charge balance in an organic layer (particularly, an emission layer (EML)) and prevent degradation caused by accumulation of electrons and holes, thereby exhibiting high efficiency and long life.

[0109] The compound according to the exemplary embodiment may have low driving voltage, high light emitting efficiency and / or long life characteristics when used in an organic light emitting device.

[0110] According to an exemplary embodiment of the present specification, Chemical Formula A may be represented by any one of the following Chemical Formulas A-1 to A-3.

[0111] [Chemical formula A-1]

[0112]

[0113] [Chemical formula A-2]

[0114]

[0115] [Chemical formula A-3]

[0116]

[0117] In Chemical Formulas A-1 to A-3,

[0118] Ar1 to Ar3, L1, L2, R1 to R3, ar1, ar2, l1, l2 and r1 to r3 are each as defined in Formula A,

[0119] R1' is as defined in R1 in formula A,

[0120] R2' is as defined in R2 in formula A,

[0121] r1' is an integer from 0 to 2, when r1' is 2, R1' are the same or different from each other, and

[0122] r2' is 0 or 1.

[0123] According to an exemplary embodiment of the present specification, Chemical Formula A may be represented by any one of the following Chemical Formulas A-101 to A-104.

[0124] [Chemical formula A-101]

[0125]

[0126] [Chemical formula A-102]

[0127]

[0128] [Chemical formula A-103]

[0129]

[0130] [Chemical formula A-104]

[0131]

[0132] In chemical formulas A-101 to A-104,

[0133] L1, L2, Ar1 to Ar3, R1 to R3, l1, l2, ar1, ar2, r1, and r3 are each as defined in Chemical Formula A. According to an exemplary embodiment of the present specification, Chemical Formula B may be represented by any one of the following Chemical Formulas B-1 to B-11.

[0134] [Chemical formula B-1]

[0135]

[0136] [Chemical formula B-2]

[0137]

[0138] [Chemical formula B-3]

[0139]

[0140] [Chemical formula B-4]

[0141]

[0142] [Chemical formula B-5]

[0143]

[0144] [Chemical formula B-6]

[0145]

[0146] [Chemical formula B-7]

[0147]

[0148] [Chemical formula B-8]

[0149]

[0150] [Chemical formula B-9]

[0151]

[0152] [Chemical formula B-10]

[0153]

[0154] [Chemical formula B-11]

[0155]

[0156] In Chemical Formulas B-1 to B-11,

[0157] N-Het1, Ar4, L3, L4, R5, l3, l4 and r5 are each as defined in Formula B,

[0158] R4' and R4" are each as defined for R4 in Formula B,

[0159] R5', R5" and R5"' are each as defined for R5 in Formula B,

[0160] R6 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; or substituted or unsubstituted C2 to C60 heterocycloalkyl,

[0161] r4' and r5' are the same or different from each other and are each independently an integer from 0 to 3,

[0162] r4" and r5" are the same or different from each other and are each independently an integer from 0 to 2,

[0163] r5"' is 0 or 1,

[0164] r6 is an integer from 0 to 4, and

[0165] When R4′, R4″, R5′, R5″ and R6 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other.

[0166] According to an exemplary embodiment of the present specification, Chemical Formula B may be represented by any one of the following Chemical Formulas B-101 to B-132.

[0167] [Chemical formula B-101]

[0168]

[0169] [Chemical formula B-102]

[0170]

[0171] [Chemical formula B-103]

[0172]

[0173] [Chemical formula B-104]

[0174]

[0175] [Chemical formula B-105]

[0176]

[0177] [Chemical formula B-106]

[0178]

[0179] [Chemical formula B-107]

[0180]

[0181] [Chemical formula B-108]

[0182]

[0183] [Chemical formula B-109]

[0184]

[0185] [Chemical formula B-110]

[0186]

[0187] [Chemical formula B-111]

[0188]

[0189] [Chemical formula B-112]

[0190]

[0191] [Chemical formula B-113]

[0192]

[0193] [Chemical formula B-114]

[0194]

[0195] [Chemical formula B-115]

[0196]

[0197] [Chemical formula B-116]

[0198]

[0199] [Chemical formula B-117]

[0200]

[0201] [Chemical formula B-118]

[0202]

[0203] [Chemical formula B-119]

[0204]

[0205] [Chemical formula B-120]

[0206]

[0207] [Chemical formula B-121]

[0208]

[0209] [Chemical formula B-122]

[0210]

[0211] [Chemical formula B-123]

[0212]

[0213] [Chemical formula B-124]

[0214]

[0215] [Chemical formula B-125]

[0216]

[0217] [Chemical formula B-126]

[0218]

[0219] [Chemical formula B-127]

[0220]

[0221] [Chemical formula B-128]

[0222]

[0223] [Chemical formula B-129]

[0224]

[0225] [Chemical formula B-130]

[0226]

[0227] [Chemical formula B-131]

[0228]

[0229] [Chemical formula B-132]

[0230]

[0231] In chemical formulas B-101 to B-132,

[0232] N-Het1, Ar4, L3, L4, R5, l3, l4 and r5 are each as defined in Formula B,

[0233] R4' and R4" are each as defined for R4 in Formula B,

[0234] R5', R5" and R5"' are each as defined for R5 in Formula B,

[0235] R6 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; or substituted or unsubstituted C2 to C60 heterocycloalkyl,

[0236] r4' and r5' are the same or different from each other, and are each independently an integer from 0 to 3,

[0237] r4" and r5" are the same or different from each other, and are each independently an integer from 0 to 2,

[0238] r5"' is 0 or 1,

[0239] r6 is an integer from 0 to 4, and

[0240] When R4′, R4″, R5′, R5″ and R6 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other.

[0241] According to an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0242] According to an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0243] According to an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and may each independently be a direct bond; or a C6 to C30 arylene group that is unsubstituted or substituted with deuterium.

[0244] According to an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and may be each independently a direct bond; an unsubstituted or deuterium-substituted phenylene group; an unsubstituted or deuterium-substituted biphenylene group; or an unsubstituted or deuterium-substituted naphthyl group.

[0245] According to an exemplary embodiment of the present specification, Ar1, Ar2 and Ar4 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0246] According to an exemplary embodiment of the present specification, Ar1, Ar2 and Ar4 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0247] According to an exemplary embodiment of the present specification, Ar1, Ar2 and Ar4 are the same as or different from each other, and may each independently be a C6 to C30 aryl group which is unsubstituted or substituted with a substituent selected from the group consisting of deuterium, an alkyl group and an aryl group; or a C2 to C30 heteroaryl group which is unsubstituted or substituted with a substituent selected from the group consisting of deuterium, an alkyl group and an aryl group.

[0248] According to an exemplary embodiment of the present specification, Ar1, Ar2 and Ar4 are the same as or different from each other, and can each independently be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; a dibenzofuranyl group; a dibenzothienyl group; or a carbazolyl group, which can each independently be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, an alkyl group and an aryl group.

[0249] According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0250] According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0251] According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0252] According to an exemplary embodiment of the present specification, R5 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent R5 groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocyclic ring.

[0253] According to an exemplary embodiment of the present specification, R5 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent R5 groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring.

[0254] According to an exemplary embodiment of the present specification, R5 is hydrogen; or deuterium, or two or more adjacent R5 may be bonded to each other to form a substituted or unsubstituted benzene ring.

[0255] According to an exemplary embodiment of the present specification, R5 is hydrogen; or deuterium, or two or more adjacent R5 may be bonded to each other to form a benzene ring that is unsubstituted or substituted with deuterium.

[0256] According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other and are each independently hydrogen or deuterium, R5 is hydrogen or deuterium, or two or more adjacent R5s may be bonded to each other to form a benzene ring that is unsubstituted or substituted with deuterium.

[0257] According to an exemplary embodiment of the present specification, Rk and Rk1 to Rk3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0258] According to an exemplary embodiment of the present specification, Rk and Rk1 to Rk3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0259] According to an exemplary embodiment of the present specification, Rk and Rk1 to Rk3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0260] According to an exemplary embodiment of the present specification, Rk and Rk1 to Rk3 are the same as or different from each other and may each independently be hydrogen; deuterium; C1 to C20 alkyl groups which are unsubstituted or substituted with deuterium; C6 to C20 aryl groups which are unsubstituted or substituted with deuterium; or C2 to C20 heteroaryl groups which are unsubstituted or substituted with deuterium.

[0261] According to an exemplary embodiment of the present specification, Rk and Rk1 to Rk3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a methyl group that is unsubstituted or substituted with deuterium; an ethyl group that is unsubstituted or substituted with deuterium; or a phenyl group that is unsubstituted or substituted with deuterium.

[0262] According to an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0263] According to an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and may be each independently a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0264] According to an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and may be each independently a C6 to C30 aryl group which is unsubstituted or substituted with deuterium, an alkyl group or an alkenyl group; a C2 to C30 heteroaryl group which is unsubstituted or substituted with deuterium, an alkyl group or an alkenyl group; or a combination thereof.

[0265] According to exemplary embodiments of the present specification, Ra and Rb are the same as or different from each other, and may be each independently phenyl; biphenyl; terphenyl; naphthyl; fluorenyl; phenanthrenyl; dibenzofuranyl; dibenzothienyl; or carbazolyl, which may be each independently unsubstituted or substituted with a substituent selected from the group consisting of deuterium, alkyl, alkenyl and aryl.

[0266] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 1% to 100%.

[0267] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 10% to 100%.

[0268] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 20% to 100%.

[0269] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 30% to 100%.

[0270] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 60% to 100%.

[0271] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 80% to 100%.

[0272] According to an exemplary embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B may be the same as or different from each other, and may each independently be 0% or 90% to 100%.

[0273] According to exemplary embodiments of the present specification, Chemical Formula A may be represented by any one of the following heterocyclic compounds.

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] According to exemplary embodiments of the present specification, Chemical Formula B may be represented by any one of the following heterocyclic compounds.

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] Compounds having the inherent properties of the introduced substituents can be synthesized by introducing various substituents into the structure represented by Chemical Formula A and / or Chemical Formula B. For example, materials satisfying the required conditions of each organic material layer can be synthesized by introducing substituents of hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light emitting layer materials, electron transport layer materials, electron transport auxiliary layer materials, and charge generation layer materials commonly used in the manufacture of organic light emitting components into the core structure.

[0368] Furthermore, the energy band gap can be finely tuned by introducing various substituents into the structure of Chemical Formula A and / or Chemical Formula B, and at the same time, the characteristics at the interface between organic materials can be improved and the use of materials can be diversified.

[0369] According to an exemplary embodiment of the present specification, a molar ratio of the heterocyclic compound represented by Chemical Formula A to the heterocyclic compound represented by Chemical Formula B may be 0.1 to 3:0.1 to 2.

[0370] According to an exemplary embodiment of the present specification, a molar ratio of the heterocyclic compound represented by Chemical Formula A to the heterocyclic compound represented by Chemical Formula B may be 1 to 3:1 to 2.

[0371] In addition, the organic layer composition including the heterocyclic compound of Chemical Formula A and the heterocyclic compound of Chemical Formula B provides excellent thermal stability when used in an organic light-emitting device, which can provide driving stability for future organic light-emitting devices and improve lifespan characteristics.

[0372] <Organic light-emitting components>

[0373] The organic light emitting device according to the present specification will be described below.

[0374] Another exemplary embodiment of the present specification provides an organic light-emitting component, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and an organic material layer having one or more layers arranged between the first electrode and the second electrode, wherein the one or more layers of the organic material layer include the above-mentioned composition of the organic material layer for the organic light-emitting component.

[0375] According to an exemplary embodiment of the present specification, the organic material layer further includes a light emitting layer (emission layer), and the light emitting layer may include a composition for an organic light emitting device.

[0376] In another exemplary embodiment of the present specification, the light emitting layer may include a composition for an organic light emitting device as a host.

[0377] According to an exemplary embodiment of the present specification, the light emitting layer may include a composition for an organic light emitting device as a red host.

[0378] According to an exemplary embodiment of the present specification, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0379] According to an exemplary embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be a cathode.

[0380] According to an exemplary embodiment of the present specification, the organic light emitting component may be a blue organic light emitting component, and the composition of the organic material layer for the organic light emitting component may be used as a material for the blue organic light emitting component.

[0381] According to an exemplary embodiment of the present specification, the organic light emitting component may be a green organic light emitting component, and the composition of the organic material layer for the organic light emitting component may be used as a material for the green organic light emitting component.

[0382] According to an exemplary embodiment of the present specification, the organic light emitting component may be a red organic light emitting component, and the composition of the organic material layer for the organic light emitting component may be used as a material for the red organic light emitting component.

[0383] The organic material layer of the organic light-emitting component of the present specification may have a single-layer structure, but may also have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting component of the present specification 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 organic material layers. However, the structure of the organic light-emitting component is not limited thereto, and may include fewer or more organic material layers.

[0384] According to an exemplary embodiment of the present description, the organic material layer may include an iridium-based dopant.

[0385] According to an exemplary embodiment of the present specification, Ir(ppy) may be used. 3 As the iridium-based dopant, it is a green phosphorescent dopant, but the iridium-based dopant is not limited thereto.

[0386] According to an exemplary embodiment of the present specification, (piq) may be used 2(Ir)(acac) is an iridium-based dopant, which is a red phosphorescent dopant, but the iridium-based dopant is not limited thereto.

[0387] In the organic light-emitting device of the present specification, a material having a relatively high work function can be used as the positive electrode material, and a transparent conductive oxide, a metal or a conductive polymer can be used. Specific examples of the positive electrode material include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); and combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methyl methacrylate), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; but not limited thereto.

[0388] In the organic light-emitting device of the present specification, a material with a relatively low work function can be used as the negative electrode material, and metals, metal oxides or conductive polymers can be used. Specific examples of negative electrode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials, such as LiF / Al or LiO 2 / Al, etc.; but not limited to these.

[0389] In the organic light-emitting component of the present specification, known hole injection materials can also be used as hole injection materials, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the document [Advanced Material, 6, page 677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tris[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) (which is a soluble conductive polymer), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate), etc.

[0390] In the organic light-emitting device of the present specification, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or polymer materials can also be used.

[0391] In the organic light-emitting components of the present specification, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. can be used as electron transport materials, and low molecular weight materials and polymer materials can also be used.

[0392] In the organic light-emitting device of the present specification, for example, a person skilled in the art typically uses LiF as an electron injection material, but the present application is not limited thereto.

[0393] In the organic light-emitting component of the present specification, as the light-emitting material, a red light, green light or blue light-emitting material can be further used, and if necessary, two or more light-emitting materials can be mixed and used. In this case, two or more light-emitting materials can be deposited as separate supply sources, or mixed in advance and deposited as one supply source. In addition, fluorescent materials can also be used as light-emitting materials, but phosphorescent materials can also be used. Materials that emit light by combining holes and electrons injected by the positive electrode and the negative electrode can also be used alone as light-emitting materials, but materials that jointly participate in light emission of the main material and the doping material can also be used.

[0394] When the host of the light-emitting material is mixed, the host of the same series can be mixed, or the host of different series can be mixed. For example, two or more types of materials selected from N-type host materials or P-type host materials can be used as the host material of the light-emitting layer.

[0395] According to exemplary embodiments of the present specification, the organic light emitting component may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0396] According to exemplary embodiments of the present specification, the heterocyclic compound may even function in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like based on a principle similar to that applied to organic light emitting components.

[0397] The organic light-emitting device of the present specification may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0398] Figures 1 to 3 The stacking sequence of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated. However, the scope of the present application is not limited by these drawings, and organic light-emitting device structures known to those skilled in the art can also be applied to the present application.

[0399] according to Figure 1 , showing an organic light-emitting device in which a positive electrode 200, an organic material layer 300 and a negative electrode 400 are sequentially stacked on a substrate 100. However, the organic light-emitting device is not limited to this structure. Figure 2 As shown, an organic light emitting device in which a cathode, an organic material layer and an anode are sequentially stacked on a substrate may also be implemented. The composition for the organic light emitting device may be included in an organic material layer 300, and the organic material layer 300 may be one layer or more layers.

[0400] Figure 3 The case where the organic material layer is multi-layered is exemplified. Figure 3 The organic light-emitting component 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. The composition for the organic light-emitting component may be included in the light-emitting layer 303. However, the scope of the present application is not limited to the above stack structure, and if necessary, other layers except the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0401] According to an exemplary embodiment of the present specification, an organic light-emitting component includes a first electrode; a first stack disposed on the first electrode and including a first light-emitting layer; a charge generation layer disposed on the first stack; a second stack disposed on the charge generation layer and including a second light-emitting layer; and a second electrode disposed on the second stack.

[0402] When the organic light-emitting component according to the exemplary embodiment of the present specification has a dual stack structure as described above, one or more layers of the first light-emitting layer (first stack light-emitting layer) and the second light-emitting layer (second stack light-emitting layer) may include a composition for an organic light-emitting component.

[0403] In addition, the first stack and the second stack may each independently further include one or more layers of the above-mentioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0404] The composition for an organic material layer of an organic light-emitting device can be used when forming an organic material layer of an organic light-emitting device, and can be preferably used as a material for a light-emitting layer.

[0405] The composition for the organic material layer may be a premixed form of the heterocyclic compound of Chemical Formula A and the heterocyclic compound of Chemical Formula B, may be mixed with a powdered material before forming the organic material layer of the organic light-emitting device, and may be mixed with a liquid compound at an appropriate temperature or higher. The composition is solid at a temperature equal to or lower than the melting point of each material, and may remain in a liquid phase when the temperature is adjusted.

[0406] The composition for the organic material layer may further include materials known to those skilled in the art, such as solvents and additives.

[0407] <Method of Manufacturing Organic Light Emitting Component>

[0408] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting component is provided, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises using an organic material layer composition of an organic light-emitting component according to an exemplary embodiment of the present specification to form an organic material layer having one or more layers.

[0409] According to an exemplary embodiment of the present specification, when the organic material layer is formed, the heterocyclic compound represented by Chemical Formula A and the heterocyclic compound represented by Chemical Formula B may be formed using a thermal vacuum deposition method.

[0410] The organic light emitting device according to the exemplary embodiment of the present specification can be manufactured by using a typical manufacturing method and material of the organic light emitting device, except that the organic material layer is formed using the organic material layer composition of the organic light emitting device.

[0411] Specifically, in the method of forming an organic material layer, when manufacturing an organic light-emitting component, the organic material layer can be formed using a heterocyclic compound of chemical formula A and a heterocyclic compound of chemical formula B, not only by a vacuum deposition method, but also by a solution coating method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.

[0412] Hereinafter, the present specification will be described in more detail through examples, but these examples are only used to illustrate the present application and are not intended to limit the scope of the present application.

[0413] Preparation Example

[0414] [Preparation Example 1] Preparation of Compound A006, etc.

[0415]

[0416] 1) Preparation of intermediate A006-1

[0417] In a 1-liter two-necked flask, 10.0 g (30.16 mmol) of 6-bromo-7-chloronaphtho[1,2-b]benzofuran (A), 9.09 g (31.67 mmol) of (9-phenyl-9H-carbazol-1-yl)boronic acid (B), 1.74 g (1.51 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4) and 12.5 g (90.47 mmol) K 2 CO 3 Dissolved in 1,4-dioxane / H 2 O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by methanol recrystallization to obtain 14.15 g (yield 95%) of intermediate A006-1.

[0418] 2) Preparation of Compound A006

[0419] 14.15 g (28.5 mmol) of intermediate A006-1, 9.9 g (28.5 mmol) of 4-(phenanthren-9-yl)-N-phenylaniline (C), 1.3 g (1.4 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ), 1.37 g (2.86 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) and 8.26 g (85.95 mmol) of sodium tert-butoxide (NaOtBu) were placed in a 5000 ml two-necked flask and dissolved in toluene (150 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by methanol recrystallization to obtain 20.06 g (yield 87.2%, 83% calculated based on the starting material) of the target compound A006.

[0420] The synthesis method of the following target compound is the same as the method for preparing compound A006, except that (A), (B) and (C) in the following Table 1 are used instead of (A), (B) and (C) in Preparation Example 1.

[0421] [Table 1]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428] [Preparation Example 2] Preparation of Compound A161, etc.

[0429]

[0430] 1) Preparation of intermediate A161-1

[0431] In a 1-liter two-necked flask, 10.0 g (30.16 mmol) of 6-bromo-7-chloronaphtho[1,2-b]benzofuran (D), 9.69 g (30.16 mmol) of N-phenyl-[1,1':4',1"-terphenyl]-4-amine (E), 1.38 g (1.51 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ), 1.44 g (3.02 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) and 8.69 g (90.47 mmol) of sodium tert-butoxide (NaOtBu) were dissolved in toluene (100 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization with methanol to obtain 15.36 g (yield 89%) of intermediate A161-1.

[0432] 2) Preparation of Compound A161

[0433] 15.36 g (26.84 mmol) of intermediate A161-1, 8.09 g (28.18 mmol) of (9-phenyl-9H-carbazol-1-yl)boronic acid (F), 1.23 g (1.34 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ), 1.28 g (2.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) and 3.2 g (80.52 mmol) of NaOH were placed in a 500 ml two-necked flask and dissolved in 1,4-dioxane / H 2 O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization through methanol to obtain 17.26 g (yield 82.5%, 73% based on the starting material) of the target compound A161.

[0434] The synthesis method of the following compounds is the same as the method for preparing compound A161, except that (D), (E) and (F) in the following Table 2 are used instead of (D), (E) and (F) in Preparation Example 2.

[0435] [Table 2]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441] [Preparation Example 3] Preparation of Compound A226, etc.

[0442]

[0443] 1) Preparation of intermediate A226-1

[0444] In a 1-liter two-necked flask, 10.0 g (30.16 mmol) of 6-bromo-7-chloronaphtho[1,2-b]benzofuran (G), 16.58 g (31.67 mmol) of N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (H), 1.74 g (1.51 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) and 12.5 g (90.47 mmol) K 2 CO 3 Dissolved in 1,4-dioxane / H 2 O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization through methanol to obtain 17.87 g (yield 91.4%) of intermediate A226-1.

[0445] 2) Preparation of Compound A226

[0446] 17.87 g (27.56 mmol) of intermediate A226-1, 7.9 g (27.56 mmol) of (9-phenyl-9H-carbazol-1-yl)boronic acid (I), 1.26 g (1.38 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ), 1.31 g (2.76 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) and 3.31 g (28.69 mmol) of NaOH were placed in a 500 ml two-necked flask and dissolved in 1,4-dioxane / H 2 O (150 ml / 30 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by methanol recrystallization to obtain 19.92 g (yield 84.5%, 74% based on the starting material) of the target compound A226.

[0447] The synthesis method of the following target compound is the same as the method for preparing compound A226, except that (G), (H) and (I) in the following Table 3 are used instead of (G), (H) and (I) in Preparation Example 3.

[0448] [Table 3]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454] [Preparation Example 4] Preparation of Compound B5, etc.

[0455]

[0456] 1) Preparation of intermediate B5-2

[0457] In a 1-liter two-necked flask, 10.0 g (35.52 mmol) of 1-bromo-3-chlorodibenzo[bd]furan (J), 9.47 g (37.30 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.3 g (1.78 mmol) of Pd(dppf)Cl 2 10.46 g (106.56 mmol) of KOAc were dissolved in 1,4-dioxane (100 ml), and the resulting solution was refluxed for 2 hours. The reaction product was filtered and then purified to obtain 10.32 g (yield 88.4%) of intermediate B5-2.

[0458] 2) Preparation of intermediate B5-1

[0459] In a 500 ml two-necked flask, 10.32 g (31.40 mmol) of intermediate B5-2, 8.41 g (31.40 mmol) of (2-chloro-4,6-diphenyl-1,3,5-triazine (K), 1.81 g (1.57 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) and 13.02 g (94.20 mmol) K 2 CO 3 Dissolved in 1,4-dioxane / H 2O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by methanol recrystallization to obtain 11.63 g (yield 85.4%) of the target compound B5-1.

[0460] 3) Preparation of Compound B5

[0461] 11.63 g (26.82 mmol) of intermediate B5-1, 7.35 g (26.82 mmol) of [1,1':4',1"-terphenyl]-4-ylboronic acid (L), 1.23 g (1.34 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ), 1.28 g (2.68 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) and 3.22 g (80.45 mmol) of NaOH were placed in a 500 ml two-necked flask and dissolved in 1,4-dioxane / H 2 O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by methanol recrystallization to obtain 15.32 g (yield 91%, 69% based on the starting material) of the target compound B5.

[0462] The following compounds were synthesized in the same manner as compound A161, except that (J), (K) and (L) in the following Table 4 were used instead of (J), (K) and (L) in Preparation Example 4.

[0463] [Table 4]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474] [Preparation Example 5] Preparation of Compound B422, etc.

[0475]

[0476] 1) Preparation of intermediate B422-2

[0477] 10 g (30.31 mmol) of 5-bromo-7-chloronaphtho[1,2-b]benzofuran (M), 3.88 g (31.82 mmol) of phenylboronic acid (n), 1.75 g (1.52 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) and 12.57 g (90.96 mmol) K 2 CO 3 Place in a 500 ml two-necked flask and dissolve in 1,4-dioxane / H 2 O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization through methanol to obtain 9.15 g (92%) of the target compound B422-2.

[0478] 2) Preparation of intermediate B422-1

[0479] In a 1 L two-necked flask, 9.15 g (27.88 mmol) of intermediate B422-2, 10.62 g (41.83 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 1.28 g (1.39 mmol) of Pd 2 (dba) 3 , 1.33 g (2.79 mmol) of Xphos and 12.31 g (125.48 mmol) of KOAc were dissolved in 1,4-dioxane (100 ml), and the resulting solution was refluxed for 2 hours. The reaction product was filtered and then purified to obtain 10.08 g (yield 86%) of intermediate B442-1.

[0480] 3) Preparation of compound B422

[0481] In a 500 ml two-necked flask, 10.08 g (23.98 mmol) of intermediate B5-1, 7.6 g (23.98 mmol) of 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (0), 1.39 g (1.99 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) and 9.94 g (71.94 mmol) K 2 CO 3 Dissolved in 1,4-dioxane / H 2O (100 ml / 20 ml), and the resulting solution was refluxed for 1 hour. The reaction product was purified by recrystallization through methanol to obtain 12.55 g (yield 91%, 72% based on the starting material) of the target compound B422.

[0482] The following compounds were synthesized in the same manner as compound B422, except that (M), (N) and (O) in the following Table 5 were used instead of (M), (N) and (O) in Preparation Example 5.

[0483] [Table 5]

[0484]

[0485]

[0486]

[0487]

[0488] The following Tables 6 and 7 show the 1H NMR and FD-MS data of the compounds. The following data confirm that the target compound has been synthesized.

[0489] [Table 6]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502] [Table 7]

[0503]

[0504]

[0505]

[0506] Experimental example

[0507] <Experimental Example 1> Fabrication of an Organic Light Emitting Component

[0508] Use distilled water to apply a thin layer of indium tin oxide (ITO) to The glass substrate of thickness was ultrasonically cleaned. After the distilled water cleaning was completed, the glass substrate was ultrasonically cleaned with solvents such as acetone, methanol and isopropanol, and then dried, and then UVO treated with UV in a UV cleaning machine for 5 minutes. Thereafter, the substrate was transferred to a plasma cleaning machine (PT), and then plasma treated under vacuum to obtain the ITO work function and remove the residual film, and transferred to a thermal deposition device for organic deposition.

[0509] On the ITO transparent electrode (positive electrode), a hole injection layer of 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer of N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) were formed as a common layer.

[0510] The light-emitting layer was thermally vacuum deposited thereon in the following manner. The compounds shown in Table 8 below (preliminary mixing when two or more compounds are used) were used as the red host and (piq) 2 (Ir)(acac) was used as a red phosphorescent dopant and (piq) was added at 3% 2 (Ir)(acac) is doped into the main body to deposit a thickness of the luminous layer.

[0511] After that, the deposition thickness The BCP is used as a hole blocking layer with a deposition thickness of Alq 3 Finally, a layer with a thickness of 100 nm is deposited on the electron transport layer. The electron injection layer is formed by depositing lithium fluoride (LiF) with a thickness of An aluminum (Al) negative electrode is formed to form a negative electrode, thereby manufacturing an organic light-emitting component.

[0512] At the same time, all the organic compounds needed to make OLED components are -8 Up to 10 -6 Each material was purified by sublimation under a vacuum of 1000 torr and used to manufacture OLEDs.

[0513] For the organic light-emitting component manufactured as described above, the electroluminescence (EL) characteristics were measured using M7000 manufactured by McScience, and the reference brightness was measured as 6,000 cd / m by a lifetime measurement device (M6000) manufactured by McScience based on the measurement results. 2 T 90 . T 90 It means lifespan (unit: hours), that is, the time required for the brightness to become 90% relative to the initial brightness.

[0514] The properties of the organic light emitting device of the present invention are shown in the following Table 8. The comparative compounds shown in the following Table 8 are as follows.

[0515]

[0516] [Table 8]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534]

[0535]

[0536]

[0537] It can be seen from the results of Table 8 above that when two heterocyclic compounds (specifically a heterocyclic compound of chemical formula A and a heterocyclic compound of chemical formula B) are mixed to deposit the organic material layer of an organic light-emitting component according to the present application, the efficiency or lifespan of the organic light-emitting component is improved.

[0538] Specifically, according to Comparative Examples 1 to 92, when the heterocyclic compound of Chemical Formula A was used alone, a low efficiency of about 7 cd / A and a lifetime of 11 hours or less were exhibited, and according to Comparative Examples 101 to 192, when the heterocyclic compound of Chemical Formula B was used alone, an efficiency of about 59 cd / A and a lifetime of 81 hours or less were exhibited.

[0539] With reference to Examples 1 to 206 in which the heterocyclic compound of Formula A was used in combination with the heterocyclic compound of Formula B, it was confirmed that charge balance was achieved and the device exhibited high efficiency and long life characteristics, particularly, the life was increased by about 10 times compared to Comparative Examples 1 to 92. These results indicate that the heterocyclic compound of Formula A has a fast electron supply and, when combined with the heterocyclic compound of Formula B, also balances the hole supply, thereby balancing the charge in the device and improving the life and efficiency.

[0540] Meanwhile, in the case of compounds K to N in Comparative Examples 93 to 96, only one aromatic amine group was substituted with a monosubstituted dibenzofuran or naphthobenzofuran, and this structure had smaller electronic properties than the heterocyclic compound of Chemical Formula A of the present application, so when these compounds were combined with the heterocyclic compound of Chemical Formula B, as shown in Comparative Examples 201 to 219, low efficiency and short life were observed, indicating that the device characteristics were degraded due to charge imbalance.

[0541] In the case of compounds O to R in Comparative Examples 97 to 100, only one aryl or heteroaryl group is substituted with a monosubstituted naphthobenzofuran, and this structure has weaker hole characteristics than the heterocyclic compound of Chemical Formula A, so when these compounds are combined with the heterocyclic compound of Chemical Formula B, as shown in Comparative Examples 220 to 238, low efficiency and short life are exhibited, indicating that the device characteristics are degraded due to charge imbalance.

[0542] In addition, in the case of compounds S to V in Comparative Examples 193 to 196, only the triazine is substituted with a monosubstituted dibenzofuran or naphthobenzofuran, and this structure has very high electron transport properties compared to the heterocyclic compound of Chemical Formula B, so when these compounds are combined with the compound of Chemical Formula A, as shown in Comparative Examples 239 to 254, low efficiency and short life are exhibited, indicating that the charge imbalance caused by the excessively high electron mobility relative to the hole mobility leads to deterioration of device characteristics.

[0543] In addition, in the case of compounds W to Z in Comparative Examples 197 to 200, only one aryl or heteroaryl group is substituted with a monosubstituted dibenzofuran or naphthobenzofuran, and this structure has significantly lower electron transport properties compared to the heterocyclic compound of Chemical Formula B. Therefore, when these compounds are combined with the heterocyclic compound of Chemical Formula A, as shown in Comparative Examples 255 to 269, low efficiency and short life are exhibited, indicating that the charge imbalance caused by the low electron mobility relative to the hole mobility leads to deterioration of device characteristics.

[0544] In addition, since compound B has high electronic properties, when the ratio of the heterocyclic compound of chemical formula B is higher than that of the heterocyclic compound of chemical formula A, the charge balance is further improved, so the efficiency and life characteristics can be further improved. According to the experimental results, it can be confirmed that when the molar ratio of the heterocyclic compound of chemical formula A to the heterocyclic compound of chemical formula B is 3:1, 2:1 or 1.5:1, excellent efficiency and life are obtained.

[0545] The present invention is not limited to the examples, but can be prepared in various forms, and those skilled in the art will understand that the present invention can be implemented in other specific forms without changing the technical spirit or basic features of the present invention. Therefore, it should be understood that the above examples are illustrative and not restrictive in all aspects.

Claims

1. An organic material layer composition of an organic light-emitting component, characterized in that: The composition includes a heterocyclic compound represented by the following chemical formula A and a heterocyclic compound represented by the following chemical formula B: [Chemical formula A] [Chemical formula B] Among them, in chemical formula A and chemical formula B, L1 to L4 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1, Ar2 and Ar4 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R1 to R4 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, R5 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent R5 are bonded to each other to form a ring, l1 to l4 are the same as or different from each other and are each independently an integer of 1 to 3, and when l1 to l4 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other, r1 and r4 are the same or different from each other and are each independently an integer from 0 to 3, r2 is an integer from 0 to 2, r3 and r5 are the same or different from each other and are each independently an integer from 0 to 4, When r1 to r5 are each an integer of 2 or more, the substituents in brackets are the same as or different from each other, ar1 and ar2 are the same or different from each other and are each independently an integer from 1 to 4, and when ar1 and ar2 are each an integer of 2 or more, the substituents in the brackets are the same or different from each other, Ar3 is represented by the following chemical formula K, [Chemical formula K] In the chemical formula K, Indicates the part connected to L2, Xk is O; S; CRk1Rk2; or NRk3, Rk and Rk1 to Rk3 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, rk is an integer from 0 to 7, N-Het1 is represented by the following structural formula N, [Structural Formula N] In structural formula N, represents the part connected to L3, and Ra and Rb are the same as or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or a combination thereof.

2. The composition according to claim 1, characterized in that Chemical formula A is represented by any one of the following chemical formulas A-1 to A-3: [Chemical formula A-1] [Chemical formula A-2] [Chemical formula A-3] In Chemical Formulas A-1 to A-3, Ar1 to Ar3, L1, L2, R1 to R3, ar1, ar2, l1, l2 and r1 to r3 are each as defined in Formula A, R1' is as defined in R1 in formula A, R2' is as defined in R2 in formula A, r1' is an integer from 0 to 2, and when r1' is 2, R1' are the same as or different from each other, and r2' is 0 or 1.

3. The composition according to claim 1, characterized in that Chemical formula B is represented by any one of the following chemical formulas B-1 to B-11: [Chemical formula B-1] [Chemical formula B-2] [Chemical formula B-3] [Chemical formula B-4] [Chemical formula B-5] [Chemical formula B-6] [Chemical formula B-7] [Chemical formula B-8] [Chemical formula B-9] [Chemical formula B-10] [Chemical formula B-11] In Chemical Formulas B-1 to B-11, N-Het1, Ar4, L3, L4, R5, l3, l4 and r5 are each as defined in Formula B, R4' and R4" are each as defined for R4 in Formula B, R5', R5" and R5"' are each as defined for R5 in Formula B, R6 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; or substituted or unsubstituted C2 to C60 heterocycloalkyl, r4' and r5' are the same or different from each other and are each independently an integer from 0 to 3, r4" and r5" are the same or different from each other and are each independently an integer from 0 to 2, r5"' is 0 or 1, r6 is an integer from 0 to 4, and When R4′, R4″, R5′, R5″ and R6 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other.

4. The composition according to claim 1, characterized in that Chemical formula A is represented by any one of the following chemical formulas A-101 to A-104: [Chemical formula A-101] [Chemical formula A-102] [Chemical formula A-103] [Chemical formula A-104] In chemical formulas A-101 to A-104, L1, L2, Ar1 to Ar3, R1 to R3, l1, l2, ar1, ar2, r1 and r3 are each as defined in Formula A.

5. The composition according to claim 1, characterized in that Chemical formula B is represented by any one of the following chemical formulas B-101 to B-132: [Chemical formula B-101] [Chemical formula B-102] [Chemical formula B-103] [Chemical formula B-104] [Chemical formula B-105] [Chemical formula B-106] [Chemical formula B-107] [Chemical formula B-108] [Chemical formula B-109] [Chemical formula B-110] [Chemical formula B-111] [Chemical formula B-112] [Chemical formula B-113] [Chemical formula B-114] [Chemical formula B-115] [Chemical formula B-116] [Chemical formula B-117] [Chemical formula B-118] [Chemical formula B-119] [Chemical formula B-120] [Chemical formula B-121] [Chemical formula B-122] [Chemical formula B-123] [Chemical formula B-124] [Chemical formula B-125] [Chemical formula B-126] [Chemical formula B-127] [Chemical formula B-128] [Chemical formula B-129] [Chemical formula B-130] [Chemical formula B-131] [Chemical formula B-132] In chemical formulas B-101 to B-132, N-Het1, Ar4, L3, L4, R5, l3, l4 and r5 are each as defined in Formula B, R4' and R4" are each as defined for R4 in Formula B, R5', R5" and R5"' are each as defined for R5 in Formula B, R6 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; or substituted or unsubstituted C2 to C60 heterocycloalkyl, r4' and r5' are the same or different from each other and are each independently an integer from 0 to 3, r4" and r5" are the same or different from each other and are each independently an integer from 0 to 2, r5"' is 0 or 1, r6 is an integer from 0 to 4, and When R4′, R4″, R5′, R5″ and R6 are each an integer of 2 or more, the substituents in the brackets are the same as or different from each other.

6. The composition according to claim 1, characterized in that L1 to L4 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

7. The composition according to claim 1, characterized in that Ar1, Ar2 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

8. The composition according to claim 1, characterized in that R1 to R4 are the same as or different from each other and are each independently hydrogen; or deuterium, and R5 is hydrogen; or deuterium, or two or more adjacent R5 are bonded to each other to form a benzene ring which is unsubstituted or substituted with deuterium.

9. The composition according to claim 1, characterized in that Rk and Rk1 to Rk3 are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

10. The composition according to claim 1, characterized in that Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

11. The composition according to claim 1, characterized in that The deuterium content of the heterocyclic compound represented by Chemical Formula A and the deuterium content of the heterocyclic compound represented by Chemical Formula B are the same as or different from each other, and are each independently 0% or 1% to 100%.

12. The composition according to claim 1, characterized in that Chemical formula A is represented by any one of the following heterocyclic compounds:

13. The composition according to claim 1, characterized in that Chemical formula B is represented by any one of the following heterocyclic compounds:

14. The composition according to claim 1, characterized in that The molar ratio of the heterocyclic compound represented by Chemical Formula A to the heterocyclic compound represented by Chemical Formula B is 0.1-3:0.1-2.

15. An organic light-emitting component, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic material layer having one or more layers disposed between the first electrode and the second electrode, The one or more layers of the organic material layer include the composition according to any one of claims 1 to 14.

16. The organic light emitting component according to claim 15, characterized in that: The organic material layer includes a light-emitting layer, and the light-emitting layer includes the organic material layer composition of the organic light-emitting device.

17. The organic light emitting component according to claim 15, characterized in that: The organic light-emitting component further includes one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

Citation Information

Patent Citations

  • Organic electroluminescent cell

    US4356429A