Heterocyclic compound and organic light-emitting element including same

Abstract

The present invention relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light emitting element including the same.

Description

Technical Field

[0001] This application claims priority to and the benefits of Korean Patent Application No. 10-2022-0054354 filed in the Korean Intellectual Property Office on May 2, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present disclosure relates to a heterocyclic compound and an organic light-emitting device comprising the heterocyclic compound. Background Art

[0003] An organic light emitting device (OLED) is a self-luminous display device, and has the advantages of a wide viewing angle, a high response speed, and an excellent contrast ratio.

[0004] The organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined into pairs in the organic thin film, and then light is emitted when the electrons and holes are annihilated. The organic thin film can be formed in a single layer or multiple layers as required.

[0005] 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 form a light-emitting layer by itself can be used, or a compound that can play the role of a host or a dopant of a light-emitting layer based on a host-dopant can be used. In addition, a compound that can play the role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection and the like can also be used as the material of the organic film.

[0006] In order to enhance the performance, lifetime or efficiency of organic light emitting devices, there is a continuous need to develop organic thin film materials.

[0007] [Prior Art Documents]

[0008] [Patent document]

[0009] U.S. Patent No. 4,356,429 Summary of the invention

[0010] Technical issues

[0011] The present disclosure aims to provide a heterocyclic compound and an organic light-emitting device comprising the same.

[0012] Technical Solutions

[0013] To achieve the above object, one embodiment of the present disclosure provides a heterocyclic compound represented by the following Chemical Formula 1.

[0014] [Chemical formula 1]

[0015]

[0016] In Chemical Formula 1,

[0017] R1 to R7 are the same as or different from each other and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkynyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, -P(=O)R1 R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0018] At least one of R1 to R5 is a group represented by the following Chemical Formula 2,

[0019] a is an integer of 0 to 4, and when a is 2 or more, R6 are the same as or different from each other, and

[0020] Ar1 is a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0021] [Chemical formula 2]

[0022]

[0023] L1 to L3 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,

[0024] b is an integer of 0 to 5, when b is 2 or more, L1 are the same as or different from each other,

[0025] c is an integer of 0 to 5, and when c is 2 or more, L2 are the same as or different from each other,

[0026] d is an integer of 0 to 5, and when d is 2 or more, L3 are the same as or different from each other, and

[0027] Ar2 and Ar3 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.

[0028] In addition, the present disclosure provides an organic light-emitting component, the organic light-emitting component comprising:

[0029] a first electrode;

[0030] a second electrode disposed opposite to the first electrode; and

[0031] One or more organic material layers are disposed between the first electrode and the second electrode,

[0032] At least one of the one or more organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0033] In addition, the present disclosure provides an organic light-emitting component, wherein the organic material layer includes a hole transport layer, and the hole transport layer contains the heterocyclic compound.

[0034] In addition, the present disclosure provides an organic light-emitting component, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer contains the heterocyclic compound.

[0035] Beneficial effects

[0036] The compounds described in this specification can be used as organic material layer materials of organic light-emitting components. The compounds can play the role of hole injection layer materials, electron blocking layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, hole blocking layer materials, electron injection layer materials and similar materials in organic light-emitting components. In particular, the compounds can be used as hole transport layer materials, electron blocking layer materials or light-emitting layer materials of organic light-emitting components.

[0037] Specifically, the heterocyclic compound represented by Chemical Formula 1 has high hole mobility, and has an appropriate highest occupied molecular orbital (HOMO) energy level and a high lowest unoccupied molecular orbital (LUMO) energy level, thereby reducing the driving voltage and enhancing the luminous efficiency and lifetime properties. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figures 1 to 3are diagrams each schematically showing a lamination structure of an organic light emitting device according to an embodiment of the present disclosure. DETAILED DESCRIPTION

[0039] Hereinafter, the present disclosure will be described in more detail.

[0040] In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is substituted (that is, a position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0041] In the present specification, “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, C1 to C60 straight or branched alkyl, C2 to C60 straight or branched alkenyl, C2 to C60 straight or branched alkynyl, C3 to C60 monocyclic or polycyclic cycloalkyl, C2 to C60 monocyclic or polycyclic heterocycloalkyl, C6 to C60 monocyclic or polycyclic aryl, C2 to C60 monocyclic or polycyclic heteroaryl, -SiRR'R", -P(=O)RR', C1 to C20 alkylamino, C6 to C60 monocyclic or polycyclic arylamino and C2 to C60 monocyclic or polycyclic heteroarylamino, or substituted or unsubstituted with a substituent in which two or more substituents selected from the above-exemplified substituents are linked.

[0042] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0043] 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 of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0044] In the present specification, alkenyl 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 of the alkenyl may be 2 to 60, specifically 2 to 40 and more specifically 2 to 20. Specific examples 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 group, styryl and the like, but are not limited thereto.

[0045] 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 of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0046] In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic alkoxy group. 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 may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

[0047] In this specification, cycloalkyl includes monocyclic or polycyclic groups with 3 to 60 carbon atoms, and can be further substituted by other substituents. In this article, polycyclic groups mean groups in which cycloalkyl is directly linked or fused to other cyclic groups. In this article, the other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The number of carbon atoms of cycloalkyl may be 3 to 60, specifically 3 to 40 and more specifically 5 to 20. Specific examples of cycloalkyl may 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 and similar groups, but are not limited thereto.

[0048] In this specification, heterocycloalkyl includes O, S, 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 mean groups in which heterocycloalkyl and other cyclic groups are directly linked or fused. In this article, the other cyclic groups can be heterocycloalkyl, but can also be different types of cyclic groups, such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms of heterocycloalkyl can be 2 to 60, specifically 2 to 40 and more specifically 3 to 20.

[0049] In this specification, aryl includes monocyclic or polycyclic groups having 6 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic groups mean groups in which aryl is directly linked or fused to other cyclic groups. In this article, the other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. The aryl may include a spirocyclic group. The number of carbon atoms of the aryl may be 6 to 60, specifically 6 to 40 and more specifically 6 to 25. Specific examples of aryl may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, The invention also includes, but is not limited to, 1,2-dihydro-1H-indenyl, 2,3-dihydro-1H-indenyl, 2,4 ...

[0050] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different from each other, and each may be independently a substituent formed by at least one of the following: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group. Specifically, the phosphine oxide group may be substituted by an aryl group, and as the aryl group, the above examples may be applied. Examples of the phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but are not limited thereto.

[0051] In the present specification, a silyl group is a substituent group containing Si and having a Si atom directly linked as a free radical, and is represented by -SiR101R102R103. R101 to R103 are the same as or different from each other, and may each independently be a substituent group formed by at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0052] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0053] When the fluorenyl group is substituted, it may include and the like, however, the structure is not limited thereto.

[0054] In the present specification, a spirocyclic group is a group including a spirocyclic structure and may have 15 to 60 carbon atoms. For example, a spirocyclic group may include a structure in which a 2,3-dihydro-1H-indenyl or a cyclohexane spirocyclic ring is bonded to a fluorenyl group. Specifically, a spirocyclic group may include any one of the groups of the following structural formulas.

[0055]

[0056] 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 may be further substituted with other substituents. In this article, polycyclic groups mean groups in which heteroaryl is directly linked or fused to other cyclic groups. In this article, other cyclic groups may be heteroaryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40 and more specifically 3 to 25. Specific examples of the heteroaryl group may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl group, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl group, isoquinazolinyl, quinozolinyl group, naphthyridinyl, acridinyl, phenanthridinyl group ... group), imidazopyridyl, naphthazinyl, triazaindenyl, 2-indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridyl, dibenzosilole group, spirobis(dibenzosilole) group, dihydrophenanthridyl, ... group), thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindolinyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenanthiazinyl, phthalazinyl, naphthyridinyl, phenanthroline, benzo[c][1,2,5]thiadiazolyl, 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]dihydroindolinyl, 5,11-dihydroindeno[1,2-b]carbazolyl and the like, but are not limited thereto.

[0057] In the present specification, the amino group may be selected from the group consisting of a monoalkylamino group, a monoarylamino group, a monoheteroarylamino group, -NH2, a dialkylamino group, a diarylamino group, a diheteroarylamino group, an alkylarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, and the number of carbon atoms is not particularly limited thereto, but is preferably 1 to 30. Specific examples of the amino group may include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, a diphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, a triphenylamino group, a biphenylnaphthylamino group, a phenylbiphenylamino group, a biphenylfluorenylamino group, a phenyltriphenyleneamino group, a biphenyltriphenyleneamino group, and the like, but are not limited thereto.

[0058] In the present specification, an arylene group means an aryl group having two bonding sites, i.e., a divalent group. Except for each arylene group being a divalent group, the above-provided description about an aryl group can be applied to an arylene group. In addition, a heteroarylene group means a heteroaryl group having two bonding sites, i.e., a divalent group. Except for each heteroarylene group being a divalent group, the above-provided description about a heteroaryl group can be applied to a heteroarylene group.

[0059] In the present specification, an "adjacent" group may mean a substituent that replaces an atom directly linked to an atom substituted by a corresponding substituent, a substituent that is spatially closest to a corresponding substituent, or another substituent that replaces an atom substituted by a corresponding substituent. For example, two substituents that replace at ortho positions in a benzene ring and two substituents that replace at the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.

[0060] In the present disclosure, "where no substituent is specified in a chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to the presence of deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0061] In one embodiment of the present disclosure, "the situation where no substituent is specified in the chemical formula or compound structure" may mean that all positions that can be substituents 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 article, the content of deuterium may be 0% to 100%.

[0062] In one embodiment of the present disclosure, in the case where no substituents are specified in the chemical formula or compound structure, when deuterium is not explicitly excluded (for example, "the deuterium content is 0%", "the hydrogen content is 100%", or "the substituents are all hydrogen"), hydrogen and deuterium can be used interchangeably in the compound.

[0063] In one embodiment of the present disclosure, deuterium is one of the isotopes of hydrogen, is an element having a deuteron formed by one proton and one neutron as a nucleus, and can be expressed as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0064] In one embodiment of the present disclosure, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0065] In one embodiment of the present disclosure, when the total number of substituents that the base compound may have 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%.

[0066] In other words, in one example, The phenyl group having a deuterium content of 20% may mean that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium among the substituents is 1 (T2 in the formula). In other words, the phenyl group having a deuterium content of 20% may be represented by the following structural formula.

[0067]

[0068] In addition, in one embodiment of the present disclosure, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not include a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0069] In the present disclosure, the C6 to C60 aromatic hydrocarbon ring refers to a compound including an aromatic ring formed by C6 to C60 carbon and hydrogen. Examples of the C6 to C60 aromatic hydrocarbon ring may include phenyl, biphenyl, terphenyl, terphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene, Perylene, azulene and similar compounds, but are not limited thereto, and include all aromatic hydrocarbon ring compounds known in the art and satisfying the above-mentioned number of carbon atoms.

[0070] One embodiment of the present disclosure provides a heterocyclic compound represented by the following Chemical Formula 1.

[0071] [Chemical formula 1]

[0072]

[0073] In Chemical Formula 1,

[0074] R1 to R7 are the same as or different from each other and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkynyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, -P(=O)R1 R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0075] At least one of R1 to R5 is a group represented by the following Chemical Formula 2,

[0076] a is an integer of 0 to 4, and when a is 2 or more, R6 are the same as or different from each other, and

[0077] Ar1 is a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0078] [Chemical formula 2]

[0079]

[0080] L1 to L3 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,

[0081] b is an integer of 0 to 5, and when b is 2 or more, L1 are the same as or different from each other,

[0082] c is an integer of 0 to 5, and when c is 2 or more, L2 are the same as or different from each other,

[0083] d is an integer of 0 to 5, and when d is 2 or more, L3 are the same as or different from each other, and

[0084] Ar2 and Ar3 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.

[0085] In one embodiment of the present disclosure, R1 to R7 are the same as or different from each other, and are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C2 to C30 alkynyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, -P(=O)R101R102, -SiR101R102R103, or a group represented by Chemical Formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other and may each independently be 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.

[0086] In another embodiment of the present disclosure, R1 to R7 are the same as or different from each other, and are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 heterocycloalkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl, -P(=O)R101R102, -SiR101R102R103, or a group represented by Chemical Formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other and may each independently be 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.

[0087] In another embodiment of the present disclosure, R1 to R7 are the same as or different from each other, and may be each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 heterocycloalkyl, substituted or unsubstituted a substituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, -P(=O)R101R102, -SiR101R102R103, or a group represented by Chemical Formula 2, and R101, R102 and R103 are the same as or different from each other and may each independently be 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.

[0088] In another embodiment of the present disclosure, R1 to R7 are the same as or different from each other, and may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl, or a group represented by Chemical Formula 2.

[0089] In another embodiment of the present disclosure, R1 to R7 are the same as or different from each other, and may each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, or a group represented by Chemical Formula 2.

[0090] In another embodiment of the present disclosure, R6 and R7 are the same as or different from each other, and can be independently hydrogen or deuterium.

[0091] In another embodiment of the present disclosure, at least one of R1 to R4 may be a group represented by Chemical Formula 2, and R5 may be a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0092] In another embodiment of the present disclosure, at least one of R1 to R4 may be a group represented by Chemical Formula 2, and R5 may be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0093] In another embodiment of the present disclosure, at least one of R1 to R4 may be a group represented by Chemical Formula 2, and R5 may be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0094] In another embodiment of the present disclosure, at least one of R1 to R4 may be a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, and R5 may be a group represented by Chemical Formula 2.

[0095] In another embodiment of the present disclosure, at least one of R1 to R4 may be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and R5 may be a group represented by Chemical Formula 2.

[0096] In another embodiment of the present disclosure, at least one of R1 to R4 may be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group, and R5 may be a group represented by Chemical Formula 2.

[0097] In one embodiment of the present disclosure, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0098] In another embodiment of the present disclosure, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0099] In another embodiment of the present disclosure, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group.

[0100] In another embodiment of the present disclosure, Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.

[0101] In one embodiment of the present disclosure, L1 to L3 are the same as or different from each other, and may each independently be a direct bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0102] In another embodiment of the present disclosure, L1 to L3 are the same as or different from each other, and may each independently be a direct bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0103] In another embodiment of the present disclosure, L1 to L3 are the same as or different from each other, and may each independently be a direct bond or a substituted or unsubstituted C6 to C20 arylene group.

[0104] In another embodiment of the present disclosure, L1 to L3 are the same as or different from each other, and may each independently be a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted fluorenyl group.

[0105] In one embodiment of the present disclosure, Ar2 and Ar3 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0106] In another embodiment of the present disclosure, Ar2 and Ar3 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0107] In another embodiment of the present disclosure, Ar2 and Ar3 are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0108] In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of, for example, greater than 0%, 1% or greater, 10% or greater, 20% or greater, 30% or greater, 40% or greater, or 50% or greater, and 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less, relative to the total number of hydrogen atoms and deuterium atoms.

[0109] In another embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

[0110] In another embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 20% to 90% with respect to the total number of hydrogen atoms and deuterium atoms.

[0111] In another embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 30% to 80% with respect to the total number of hydrogen atoms and deuterium atoms.

[0112] In another embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 50% to 70% with respect to the total number of hydrogen atoms and deuterium atoms.

[0113] In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may be a heterocyclic compound represented by any one of the following Chemical Formulas 1-1 and 1-2.

[0114] [Chemical formula 1-1]

[0115]

[0116] [Chemical formula 1-2]

[0117]

[0118] In Chemical Formula 1-1 and Chemical Formula 1-2,

[0119] R8 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, -P(=O)R101 R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0120] e is an integer of 0 to 3, and when e is 2 or more, R8 are the same as or different from each other,

[0121] Ar4 and Ar5 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,

[0122] R6, R7, a and Ar1 have the same definitions as in Chemical Formula 1, and

[0123] L1 to L3, Ar2 to Ar3, and b to d have the same definitions as in Chemical Formula 2.

[0124] In one embodiment of the present disclosure, R8 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, -P( =O)R101R102, or -SiR101R102R103, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, and R101, R102 and R103 are the same as or different from each other and may each independently be 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.

[0125] In another embodiment of the present disclosure, R8 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, -P( =O)R101R102, or -SiR101R102R103, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle, and R101, R102 and R103 are the same as or different from each other and may each independently be 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.

[0126] In another embodiment of the present disclosure, R8 may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, -P(=O)R101R102, or -SiR101R102R103, and R101, R102 and R103 are the same as or different from each other and may each independently be substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C2-C20 heteroaryl.

[0127] In another embodiment of the present disclosure, R8 may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heteroaryl.

[0128] In another embodiment of the present disclosure, R8 may be hydrogen or deuterium.

[0129] In one embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0130] In another embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0131] In another embodiment of the present disclosure, Ar4 and Ar5 are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0132] In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may be represented by any one of the following compounds.

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] In addition, by introducing various substituents into the structure of Chemical Formula 1, a compound having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used for hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used for manufacturing organic light emitting devices into the core structure, a material that meets the conditions required for each organic material layer can be synthesized.

[0162] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap may be finely controlled, and at the same time, the properties at the interface between organic materials may be enhanced, and material applications may become diversified.

[0163] Meanwhile, the heterocyclic compound represented by Chemical Formula 1 has a high glass transition temperature (Tg) and thus has excellent thermal stability. Such improvement in thermal stability becomes an important factor in providing driving stability to the device.

[0164] The heterocyclic compound according to one embodiment of the present disclosure can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and from the intermediate compounds, a heterocyclic compound represented by Chemical Formula 1 can be prepared. More specifically, the heterocyclic compound according to one embodiment of the present disclosure can be prepared based on the preparation examples to be described later.

[0165] Another embodiment of the present disclosure provides an organic light-emitting device including a heterocyclic compound represented by Chemical Formula 1. "Organic light-emitting device" may be expressed by terms such as "organic light-emitting diode", "OLED", "OLED device" and "organic electroluminescent (EL) device".

[0166] In addition, an embodiment of the present disclosure provides an organic light-emitting component, the organic light-emitting component comprising:

[0167] a first electrode;

[0168] a second electrode disposed opposite to the first electrode; and

[0169] One or more organic material layers are disposed between the first electrode and the second electrode,

[0170] At least one of the one or more organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0171] In one embodiment of the present disclosure, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0172] In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0173] In one embodiment of the present disclosure, the organic material layer may include one or more types selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer and a hole injection layer, and one or more types of layers selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer and a hole injection layer may include a heterocyclic compound represented by Chemical Formula 1.

[0174] In another embodiment of the present disclosure, the organic material layer may include a hole transport layer, and the hole transport layer may include a heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the hole transport layer, the heterocyclic compound has high hole mobility and has an appropriate HOMO energy level, and therefore, the use of the heterocyclic compound in the hole transport layer is beneficial for hole transport to the light-emitting layer, thereby reducing the driving voltage of the organic light-emitting device and enhancing the driving efficiency and lifespan.

[0175] In another embodiment of the present disclosure, the organic material layer may include an electron blocking layer, and the electron blocking layer may include a heterocyclic compound represented by Chemical Formula 1. The heterocyclic compound has a high LUMO energy level, and therefore, the use of the heterocyclic compound in the electron blocking layer can increase the probability of holes and electrons forming excitons, and can increase the possibility of emitting as light in the light-emitting layer. Therefore, the electron blocking ability is enhanced, and holes and electrons form a charge balance, which can enable the organic light-emitting device to achieve excellent driving efficiency and lifespan.

[0176] In another embodiment of the present disclosure, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0177] In another embodiment of the present disclosure, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0178] In another embodiment of the present disclosure, the organic material layer may include an electron transport layer, an emission layer, or a hole blocking layer, and the electron transport layer, the emission layer, or the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0179] In another embodiment of the present disclosure, the organic material layer may include a hole transport layer, an electron blocking layer, or a light-emitting auxiliary layer, and the hole transport layer, the electron blocking layer, or the light-emitting auxiliary layer may include the heterocyclic compound represented by Chemical Formula 1.

[0180] In another embodiment of the present disclosure, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound represented by Chemical Formula 1.

[0181] In another embodiment of the present disclosure, the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Chemical Formula 1.

[0182] In one embodiment of the present disclosure, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light emitting device.

[0183] In another embodiment of the present disclosure, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light emitting device.

[0184] In another embodiment of the present disclosure, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light emitting device.

[0185] In one embodiment of the present disclosure, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the red organic light emitting device.

[0186] In another embodiment of the present disclosure, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

[0187] In another embodiment of the present disclosure, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0188] In one embodiment of the present disclosure, the organic light-emitting device may further include one, two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0189] The specific description of the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

[0190] Figures 1 to 3 The stacking sequence of electrodes and organic material layers of an organic light-emitting device according to one embodiment of the present disclosure is shown. However, this is not intended to limit the scope of the present application to these drawings, and the structure of an organic light-emitting device known in the art can also be applied to the present application.

[0191] Figure 1The organic light emitting device is shown 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 structure is not limited to this structure, and as Figure 2 As shown in , an organic light-emitting component can also be obtained in which a negative electrode (400), an organic material layer (300) and a positive electrode (200) are sequentially stacked on a substrate.

[0192] Figure 3 The case where the organic material layer is multi-layered is shown. 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). However, the scope of the present application is not limited to such a stacked structure, and as required, layers other than the light-emitting layer may not be included, and other necessary functional layers may be further added. For example, a light-emitting auxiliary layer ( Figure 3 not shown).

[0193] In addition to using the heterocyclic compound represented by Chemical Formula 1 to form one or more organic material layers, conventional organic light-emitting device manufacturing methods and materials may be used to manufacture the organic light-emitting device of the present disclosure.

[0194] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer using a solution coating method and a vacuum deposition method. In this article, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

[0195] The organic material layer of the organic light-emitting device disclosed herein may be formed in a single-layer structure, but may also be formed in a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device disclosed herein may have a structure including an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

[0196] In addition, one embodiment of the present disclosure provides a composition for an organic material layer, the composition including a heterocyclic compound represented by Chemical Formula 1.

[0197] The specific description of the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

[0198] The composition for an organic material layer may be used when forming an organic material layer of an organic light emitting device, and in particular, may be more preferably used when forming a hole transport layer, an electron blocking layer or a light emitting auxiliary layer.

[0199] In one embodiment of the present disclosure, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1, and a phosphorescent dopant may be used together with the heterocyclic compound.

[0200] As the phosphorescent dopant material, materials known in the art may be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M may be used, however, the scope of the present disclosure is not limited to these examples.

[0201] M may be iridium, platinum, osmium or a similar material.

[0202] L is through sp 2 Carbon and heteroatoms are anionic bidentate ligands coordinated to M, and X can play the role of trapping electrons or holes. Non-limiting examples of L may include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and the like. Non-limiting examples of X' and X" may include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate and the like.

[0203] Specific examples of the phosphorescent dopant are shown below, however, the phosphorescent dopant is not limited to these examples.

[0204]

[0205] In one embodiment of the present disclosure, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1, and an iridium-based dopant may be used together with the heterocyclic compound.

[0206] In one embodiment of the present disclosure, as an iridium-based dopant, (piq)2(Ir)(acac) may be used as a red phosphorescent dopant, or Ir(ppy)3 may be used as a green phosphorescent dopant.

[0207] In one embodiment of the present disclosure, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7%, based on the total weight of the light-emitting layer.

[0208] One embodiment of the present disclosure provides a method for manufacturing an organic light-emitting component, the method comprising:

[0209] preparing a substrate;

[0210] forming a first electrode on a substrate;

[0211] forming one or more organic material layers on the first electrode; and

[0212] forming a second electrode on the one or more organic material layers,

[0213] The forming of one or more organic material layers includes forming the one or more organic material layers using the composition for organic material layers of an organic light-emitting device according to an embodiment of the present disclosure.

[0214] In one embodiment of the present disclosure, the forming of the organic material layer may be forming the heterocyclic compound represented by Chemical Formula 1 using a thermal vacuum deposition method.

[0215] The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

[0216] In an organic light-emitting device according to an embodiment of the present disclosure, materials other than the heterocyclic compound represented by Chemical Formula 1 are shown below, however, these materials are only for illustrative purposes and are not intended to limit the scope of the present application, and these materials may be replaced by materials known in the art.

[0217] As the positive electrode material, materials each having a relatively large work function may be used, and transparent conductive oxides, metals, conductive polymers, or the like may 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

[0218] As the negative electrode material, materials each having a relatively small work function can be used, and metals, metal oxides, conductive polymers, or the like can be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and similar materials, but are not limited thereto.

[0219] As the hole injection layer material, a known hole injection layer material can be used, and for example, a phthalocyanine compound, such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a star-shaped sudden-action amine derivative described in the document [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (4,4',4"-tris[ph 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene, m-MTDAPB); soluble conductive polymers such as polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate); and similar materials.

[0220] As the hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low molecular weight materials or high molecular weight materials can also be used.

[0221] As materials for the electron transport layer, 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, 8-hydroxyquinoline and its derivatives, and metal complexes of similar materials can be used, and polymer materials and low molecular weight materials can also be used.

[0222] As an example of the electron injection layer material, LiF is generally used in the art, however, the present application is not limited thereto.

[0223] As the light-emitting layer material, a red, green or blue light-emitting material can be used, and two or more light-emitting materials can be mixed and used as needed. In this article, when used, the two or more light-emitting materials can be deposited in the form of separate supply sources, or can be pre-mixed and deposited in the form of one supply source. In addition, a fluorescent material can also be used as the light-emitting layer material, however, a phosphorescent material can also be used. As the light-emitting layer material, a material that emits light alone by combining holes and electrons injected from the positive electrode and the negative electrode, respectively, can be used, however, a material having a host material and a dopant material that participate in light emission together can also be used.

[0224] When the host of the light-emitting layer material is mixed and used, the hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials among n-type host materials and p-type host materials may be selected and used as the host material of the light-emitting layer.

[0225] Depending on the materials used, the organic light emitting device according to one embodiment of the present disclosure may be a top-emission type, a bottom-emission type, or a dual-emission type.

[0226] The heterocyclic compound according to one embodiment of the present disclosure may also be used in organic electronic devices including organic solar cells, organic photo conductors, organic transistors and the like based on principles similar to those used in organic light emitting devices.

[0227] Hereinafter, preferred examples are provided to help understand the present disclosure. However, the following examples are provided only to make it easier to understand the present disclosure, and the present disclosure is not limited thereto.

[0228] <Preparation Example>

[0229] Preparation Example 1. Preparation of Compound 005

[0230]

[0231] Preparation Example 1-1. Preparation of Compound 005-P5

[0232] After dissolving 1-iododibenzo[b,d]furan-2-ol (50 g, 161.24 mmol) and phenylboronic acid (21.63 g, 177.37 mmol) in 1,4-dioxane (500 ml) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (5.59 g, 4.84 mmol) and potassium carbonate (K2CO3) (55.71 g, 403.11 mmol) were introduced thereto, and the mixture was stirred under reflux for 12 hours.

[0233] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. Thereafter, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005-P5 (35 g, yield 83%).

[0234] Preparation Example 1-2. Preparation of Compound 005-P4

[0235] After compound 005-P5 (35 g, 134.47 mmol) was dissolved in dichloromethane (500 mL), triethylamine (16.33 g, 161.36 mmol) was added thereto, and after trifluoromethanesulfonic anhydride (45.53 g, 161.36 mmol) was slowly added thereto at 0°C, the mixture was stirred for 1 hour.

[0236] After the reaction was completed, distilled water was slowly added to the reaction solution to terminate the reaction, and then the obtained product was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005-P4 (47 g, yield 89%).

[0237] Preparation Example 1-3. Preparation of Compound 005-P3

[0238] After compound 005-P4 (47 g, 119.79 mmol) and (3-chloro-2-nitrophenyl)boric acid (26.53 g, 131.77 mmol) were dissolved in 1,4-dioxane (500 ml) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (6.92 g, 5.99 mmol) and potassium carbonate (K2CO3) (41.39 g, 299.48 mmol) were introduced thereto, and the mixture was stirred under reflux for 12 hours.

[0239] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005-P3 (37 g, yield 77%).

[0240] Preparation Example 1-4. Preparation of Compound 005-P2

[0241] Compound 005-P3 (37 g, 92.54 mmol) and triphenylphosphine (60.68 g, 231.35 mmol) were introduced into 1,2-dichlorobenzene (500 mL), and the mixture was stirred under reflux for 7 hours.

[0242] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005-P2 (30 g, yield 88%).

[0243] Preparation Example 1-5. Preparation of Compound 005-P1

[0244] After compound 005-P2 (30 g, 81.56 mmol) and bromobenzene (15.37 g, 97.87 mmol) were dissolved in toluene (300 ml), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (3.73 g, 4.08 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (3.89 g, 8.16 mmol) and sodium tert-butoxide (NaOtBu) (15.68 g, 163.12 mmol) were introduced thereto, and the mixture was stirred under reflux for 3 hours.

[0245] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005-P1 (26 g, yield 72%).

[0246] Preparation Example 1-6. Preparation of Compound 005

[0247] After compound 005-P1 (10 g, 22.53 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-3-amine (7.6 g, 23.65 mmol) were dissolved in toluene (100 ml), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (1.03 g, 1.13 mmol), Xphos (1.07 g, 2.25 mmol) and sodium tert-butoxide (NaOtBu) (4.33 g, 45.05 mmol) were introduced thereto, and the mixture was stirred under reflux for 2 hours.

[0248] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 005 (13 g, yield 79%).

[0249] Each target compound was prepared as in Table 1 below and in the same manner as in Preparation Example 1, except that Compound A in Table 1 below was used instead of phenylboronic acid, Compound B in Table 1 below was used instead of (3-chloro-2-nitrophenyl)boric acid, Compound C in Table 1 below was used instead of bromobenzene, and Compound D in Table 1 below was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-3-amine when preparing Compound 005.

[0250] [Table 1]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] Preparation Example 2. Preparation of Compound 483

[0259]

[0260] Preparation Example 2-1. Preparation of Compound 483-P5

[0261] After dissolving 1-iododibenzo[b,d]furan-2-ol (30 g, 96.75 mmol) and di([1,1'-biphenyl]-4-yl)amine (32.65 g, 101.58 mmol) in toluene (500 ml), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (4.43 g, 4.84 mmol), Xphos (4.61 g, 9.67 mmol) and sodium tert-butoxide (NaOtBu) (18.59 g, 193.49 mmol) were introduced thereto, and the mixture was stirred under reflux for 2 hours.

[0262] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483-P5 (36 g, yield 74%).

[0263] Preparation Example 2-2. Preparation of Compound 483-P4

[0264] After compound 483-P5 (36 g, 71.49 mmol) was dissolved in dichloromethane (500 mL), triethylamine (8.68 g, 85.78 mmol) was added thereto, and after trifluoromethanesulfonic anhydride (24.2 g, 85.78 mmol) was slowly added thereto at 0°C, the mixture was stirred for 1 hour.

[0265] After the reaction was completed, distilled water was slowly added to the reaction solution to terminate the reaction, and then the obtained product was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483-P4 (40 g, yield 88%).

[0266] Preparation Example 2-3. Preparation of Compound 483-P3

[0267] After compound 483-P4 (40 g, 62.93 mmol) and (3-chloro-2-nitrophenyl)boric acid (13.94 g, 69.22 mmol) were dissolved in 1,4-dioxane (500 ml) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (3.64 g, 3.15 mmol) and potassium carbonate (K2CO3) (21.74 g, 157.32 mmol) were introduced thereto, and the mixture was stirred under reflux for 12 hours.

[0268] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483-P3 (32 g, yield 79%).

[0269] Preparation Example 2-4. Preparation of Compound 483-P2

[0270] Compound 483-P3 (32 g, 49.76 mmol) and triphenylphosphine (32.63 g, 124.39 mmol) were introduced into 1,2-dichlorobenzene (500 mL), and the mixture was then stirred under reflux for 7 hours.

[0271] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483-P2 (25 g, yield 82%).

[0272] Preparation Example 2-5. Preparation of Compound 483-P1

[0273] After compound 483-P2 (25 g, 40.91 mmol) and bromobenzene (7.71 g, 49.09 mmol) were dissolved in toluene (300 ml), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (1.87 g, 2.05 mmol), Xphos (1.95 g, 4.09 mmol) and sodium tert-butoxide (NaOtBu) (7.86 g, 81.82 mmol) were introduced thereto, and the mixture was stirred under reflux for 3 hours.

[0274] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483-P1 (20 g, yield 71%).

[0275] Preparation Example 2-6. Preparation of Compound 483

[0276] After compound 483-P1 (10 g, 14.55 mmol) and phenylboronic acid (1.86 g, 15.28 mmol) were dissolved in 1,4-dioxane (100 ml) and distilled water (20 ml), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.17 g, 0.29 mmol), Xphos (0.35 g, 0.73 mmol) and potassium carbonate (K2CO3) (5.03 g, 36.38 mmol) were introduced thereto, and the mixture was stirred under reflux for 12 hours.

[0277] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 483 (7 g, 66% yield).

[0278] Each target compound was prepared as in Table 2 below and in the same manner as in Preparation Example 2, except that compound E in Table 2 below was used instead of di([1,1'-biphenyl]-4-yl)amine, compound F in Table 2 below was used instead of (3-chloro-2-nitrophenyl)boric acid, compound G in Table 2 below was used instead of bromobenzene, and compound H in Table 2 below was used instead of phenylboric acid when preparing compound 483.

[0279] [Table 2]

[0280]

[0281] Preparation Example 3. Preparation of Compound 059

[0282] After compound 044-P1 (10 g, 22.53 mmol) and ((4-diphenylamino)phenyl)boronic acid (6.84 g, 23.65 mmol) were dissolved in 1,4-dioxane (100 ml) and distilled water (20 ml), tri(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.26 g, 0.45 mmol), Xphos (0.54 g, 1.13 mmol) and potassium carbonate (K2CO3) (7.78 g, 56.32 mmol) were introduced thereto, and the mixture was stirred under reflux for 12 hours.

[0283] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 059 (11 g, yield 75%).

[0284] Each target compound was prepared as in Table 3 below and in the same manner as in Preparation Example 3, except that Compound I in Table 3 below was used instead of Compound 044-P1 and Compound J in Table 3 below was used instead of ((4-diphenylamino)phenyl)boronic acid in the preparation of Compound 059.

[0285] [Table 3]

[0286]

[0287]

[0288] Preparation Example 4. Preparation of Compound 531

[0289]

[0290] Compound 108 (10 g, 13.28 mmol), trifluoromethanesulfonic acid (2.99 g, 19.92 mmol) and D6-benzene (100 mL) were introduced into a reaction flask, and the mixture was then stirred under reflux for 5 hours.

[0291] After the reaction was completed, distilled water was slowly added to the reaction solution to terminate the reaction, and then the obtained product was extracted with dichloromethane and distilled water. The organic layer was dried with anhydrous MgSO4, and then the solvent was removed with a rotary evaporator. After that, the obtained product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 531 (9 g, yield 86%).

[0292] The synthesis results of the compounds described in Preparation Examples 1 to 4 and Tables 1 to 3 are shown in Tables 4 and 5 below.

[0293] Table 4 below shows 1 The measured values ​​of H nuclear magnetic resonance (NMR) (CDCl 3 , 300 MHz), and the measured values ​​of field desorption (FD)-mass spectrometry (MS) (FD-MS: field desorption mass spectrometry) are shown in Table 5 below.

[0294] [Table 4]

[0295]

[0296]

[0297]

[0298] [Table 5]

[0299] Compound FD-MS Compound FD-MS 005 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 279 <![CDATA[m / z=702.84(C 52 H 34 N2O=702.27)]]> 006 <![CDATA[m / z=692.84(C 51 H 36 N2O=692.28)]]> 292 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 023 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 293 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 033 <![CDATA[m / z=682.83(C 48 H 30 N2OS=682.21)]]> 296 <![CDATA[m / z=867.04(C 65 H 42 N2O=866.33)]]> 036 <![CDATA[m / z=816.98(C 61 H 40 N2O=816.31)]]> 310 <![CDATA[m / z=802.96(C 60 H 38 N2O=802.30)]]> 044 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 314 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 051 <![CDATA[m / z=752.90(C 56 H 36 N2O=752.28)]]> 316 <![CDATA[m / z=867.04(C 65 H 42 N2O=866.33)]]> 059 <![CDATA[m / z=652.78(C 48 H 32 N2O=652.25)]]> 323 <![CDATA[m / z=778.94(C 58 H 38 N2O=778.30)]]> 079 <![CDATA[m / z=702.84(C 52 H 34 N2O=702.27)]]> 329 <![CDATA[m / z=776.92(C 58 H 36 N2O=776.28)]]> 083 <![CDATA[m / z=778.94(C 58 H 38 N2O=778.30)]]> 331 <![CDATA[m / z=802.96(C 60 H 38 N2O=802.30)]]> 086 <![CDATA[m / z=742.90(C 55 H 38 N2O=742.30)]]> 341 <![CDATA[m / z=676.80(C 50 H 32 N2O=676.25)]]> 094 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 350 <![CDATA[m / z=853.02(C 64 H 40 N2O=852.31)]]> 108 <![CDATA[m / z=752.90(C 56 H 36 N2O=752.28)]]> 352 <![CDATA[m / z=782.95(C 56 H 34 N2OS=782.24)]]> 114 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 373 <![CDATA[m / z=788.97(C 54 H 32 N2OS2=788.20)]]> 120 <![CDATA[m / z=819.00(C 61 H 42 N2O=818.33)]]> 380 <![CDATA[m / z=875.09(C 63 H 42 N2OS=874.30)]]> 123 <![CDATA[m / z=702.84(C 52 H 34 N2O=702.27)]]> 381 <![CDATA[m / z=682.83(C 48 H 30 N2OS=682.21)]]> 141 <![CDATA[m / z=626.74(C 46 H 30 N2O=626.24)]]> 402 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=742.86(C <h2 style=";text-align:left;direction:ltr"> 54 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> N2O2 = 742.26<h2 style=";text-align:left;direction:ltr"> 156 <![CDATA[m / z=867.04(C 65 H 42 N2O=866.33)]]> 419 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=742.86(C <h2 style=";text-align:left;direction:ltr"> 54 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> N2O2 = 742.26<h2 style=";text-align:left;direction:ltr"> 157 <![CDATA[m / z=865.03(C 65 H 40 N2O=864.31)]]> 433 <![CDATA[m / z=798.99(C 57 H 38 N2OS=798.27)]]> 162 <![CDATA[m / z=702.84(C 52 H 34 N2O=702.27)]]> 434 <![CDATA[m / z=798.99(C 57 H 38 N2OS=798.27)]]> 172 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 442 <![CDATA[m / z=768.94(C 57 H 40 N2O=768.31)]]> 199 <![CDATA[m / z=752.90(C 56 H 36 N2O=752.28)]]> 461 <![CDATA[m / z=726.86(C 54 H 34 N2O=726.27)]]> 202 <![CDATA[m / z=752.90(C 56 H 36 N2O=752.28)]]> 472 <![CDATA[m / z=833.01(C 60 H 36 N2OS=832.25)]]> 206 <![CDATA[m / z=792.96(C 59 H 40 N2O=792.31)]]> 483 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 222 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 487 <![CDATA[m / z=768.94(C 57 H 40 N2O=768.31)]]> 226 <![CDATA[m / z=768.94(C 57 H 40 N2O=768.31)]]> 489 <![CDATA[m / z=726.86(C 54 H 34 N2O=726.27)]]> 237 <![CDATA[m / z=891.06(C 67 H 42 N2O=890.33)]]> 491 <![CDATA[m / z=752.90(C 56 H 36 N2O=752.28)]]> 251 <![CDATA[m / z=828.99(C 62 H 40 N2O=828.31)]]> 505 <![CDATA[m / z=845.04(C 63 H 44 N2O=844.35)]]> 252 <![CDATA[m / z=758.93(C 54 H 34 N2OS=758.24)]]> 513 <![CDATA[m / z=788.97(C 54 H 32 N2OS2=788.20)]]> 255 <h2 style=";text-align:left;direction:ltr"><![CDATA[m / z=742.86(C <h2 style=";text-align:left;direction:ltr"> 54 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> N2O2 = 742.26<h2 style=";text-align:left;direction:ltr"> 525 <![CDATA[m / z=778.94(C 58 H 38 N2O=778.30)]]> 260 <![CDATA[m / z=845.04(C 63 H 44 N2O=844.35)]]> 531 <![CDATA[m / z=789.12(C 56 D 36 N2O (788.51)]]> 262 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]> 539 <![CDATA[m / z=783.03(C 57 H 26 D 14 N2O=782.40)]]> 269 <![CDATA[m / z=802.96(C 60 H 38 N2O=802.30)]]> 544 <![CDATA[m / z=728.88(C 54 H 36 N2O=728.28)]]>

[0300] <Experimental example>

[0301] Experimental example 1.

[0302] Experimental Example 1-1. Fabrication of an organic light-emitting device

[0303] A glass substrate coated with an ITO film having a thickness of 1,500 angstroms was cleaned ultrasonically with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with a solvent (e.g., acetone, methanol, and isopropanol), then dried, and then subjected to ultraviolet ozone (UVO) treatment for 5 minutes using UV in an ultraviolet (UV) cleaner. After this, the substrate was transferred to a plasma cleaner (PT), and after subjecting it to plasma treatment under vacuum to increase the ITO work function and remove residual film, the substrate was transferred to a thermal deposition device for organic deposition.

[0304] 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into a cell in a vacuum deposition apparatus.

[0305]

[0306] The chamber was then evacuated until the vacuum level reached 10 -6 Toler, and then 2-TNATA was evaporated by applying an electric current to the cell to deposit a hole injection layer having a thickness of 600 angstroms on the ITO substrate. The compound represented by Chemical Formula 1 or the comparative compound set forth in Table 6 below was introduced into another cell in the vacuum deposition apparatus, and the compound represented by Chemical Formula 1 or the comparative compound set forth in Table 6 below was evaporated by applying an electric current to the cell to deposit a hole transport layer having a thickness of 1000 angstroms on the hole injection layer.

[0307] After forming the hole injection layer and the hole transport layer as above, the light-emitting layer was thermally vacuum deposited on the hole injection layer and the hole transport layer as follows. As the light-emitting layer, 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-3,3'-di-9H-carbazole was deposited to a thickness of 400 angstroms as a main body, and Ir(ppy)3 as a green phosphorescent dopant was doped and deposited to the main body in an amount of 7%. Thereafter, 60 angstroms of bathocuproine (BCP) was deposited as a hole blocking layer, and 300 angstroms of E1 was deposited on the hole blocking layer as an electron transport layer.

[0308]

[0309] Thereafter, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms as an electron injection layer, and a negative electrode was formed by depositing Al to a thickness of 1200 angstroms, and as a result, an organic light emitting device was manufactured.

[0310] At the same time, for each material to be used in the manufacture of organic light-emitting components, -8 Support up to 10 -6 All organic compounds required for the manufacture of organic light-emitting components were purified by vacuum sublimation under the support.

[0311] Herein, comparative compounds used as a hole transport layer are as follows.

[0312]

[0313] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light Emitting Device

[0314] For each of the organic electroluminescent components manufactured as above, electroluminescence (EL) properties were measured using M7000 manufactured by McScience Inc., and the lifetime measurement system (M6000) manufactured by McScience Inc. was used to measure the lifetime of the organic electroluminescent components when the standard brightness was 20,000 candelas / square meter (cd / m 2 ) at the time of life T 95 , which is the time it takes for the brightness to become 95% relative to the initial brightness.

[0315] The driving voltage, luminous efficiency and lifespan (T 95 ) are shown in Table 6.

[0316] [Table 6]

[0317]

[0318]

[0319] As can be seen from the results shown in Table 6, compared with Comparative Examples 1 to Comparative Examples 4 (organic light-emitting components that do not use the heterocyclic compound represented by Chemical Formula 1 disclosed herein as a hole transport layer material), Examples 1 to Example 65 (organic light-emitting components that use the heterocyclic compound represented by Chemical Formula 1 disclosed herein as a hole transport layer material) show that the driving voltage is reduced and the luminous efficiency and life are significantly improved.

[0320] The compounds M1 to M3 used in Comparative Examples 2 to 4 are similar to the compounds disclosed herein in having a benzofurocarbazole-type five-ring skeleton, but are different from the compounds disclosed herein in terms of the introduced substituents. The heterocyclic compounds disclosed herein have the property of high hole mobility by introducing an arylamine group as a substituent, and have the property of having an appropriate HOMO energy level. Therefore, it can be seen that, compared to the situation when M1 to M3 of Comparative Examples 2 to 4 are used, when the heterocyclic compounds disclosed herein are used as hole transport layers, holes are more easily transported to the light-emitting layer, thereby reducing the driving voltage, and improving the luminous efficiency and lifespan.

[0321] Experimental example 2.

[0322] Experimental Example 2-1. Fabrication of an organic light-emitting device

[0323] A transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung-Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each in sequence, and then stored in isopropyl alcohol before use.

[0324] 4,4',4"-tri(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into a cell in a vacuum deposition apparatus.

[0325]

[0326] The chamber was then evacuated until the vacuum level reached 10 -6The vacuum deposition apparatus was used to deposit a hole transport layer having a thickness of 1000 angstroms on the hole injection layer.

[0327]

[0328] Subsequently, the compound represented by Chemical Formula 1 or the comparative compound set forth in Table 7 was deposited to a thickness of 1000 angstroms as an electron blocking layer.

[0329] A blue light-emitting material having the following structure was deposited on the electron blocking layer as a light-emitting layer. Specifically, H1 (blue light-emitting host material) was vacuum deposited to a thickness of 300 angstroms on a unit cell in a vacuum deposition device, and D1 (blue light-emitting dopant material) was vacuum deposited on H1 in an amount of 5% relative to the host material.

[0330]

[0331] Thereafter, a compound having the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0332]

[0333] Thereafter, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms as an electron injection layer, and a negative electrode was formed by depositing Al to a thickness of 1000 angstroms, and as a result, an organic light emitting device was manufactured.

[0334] At the same time, for each material to be used in the manufacture of organic light-emitting components, -8 Support up to 10 -6 All organic compounds required for the manufacture of organic light-emitting components were purified by vacuum sublimation under the support.

[0335] Herein, comparative compounds used as an electron blocking layer are as follows.

[0336]

[0337] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Device

[0338] For each of the organic electroluminescent components manufactured as above, electroluminescence (EL) properties were measured using M7000 manufactured by Micro Scientific, and the lifetime T when the standard brightness was 20,000 candelas / m2 was measured using the measurement results by a lifetime measurement system (M6000) manufactured by Micro Scientific. 95 , which is the time it takes for the brightness to become 95% relative to the initial brightness.

[0339] The driving voltage, luminous efficiency and lifespan (T 95 ) are shown in Table 7.

[0340] [Table 7]

[0341]

[0342] As can be seen from the results shown in Table 7, compared with Comparative Examples 5 to 8 (organic light-emitting components that do not use the heterocyclic compound represented by Chemical Formula 1 disclosed in the present invention as an electron blocking layer material), Examples 66 to 90 (organic light-emitting components that use the heterocyclic compound represented by Chemical Formula 1 disclosed in the present invention as an electron blocking layer material) show that the driving voltage is reduced and the luminous efficiency and life are significantly improved.

[0343] In general, when electrons migrate to the positive electrode after passing through the hole transport layer without being combined in the light-emitting layer, the efficiency and life of the organic light-emitting device will be reduced. In this article, when a compound with a high LUMO (lowest unoccupied molecular orbital) energy level is used as an electron blocking layer, the electrons that migrate to the positive electrode after passing through the light-emitting layer are blocked by the energy barrier of the electron blocking layer, which can prevent the efficiency and life of the organic light-emitting device from being reduced. In other words, when a compound with a high LUMO (lowest unoccupied molecular orbital) energy level is used as an electron blocking layer, the probability of holes and electrons forming excitons increases, and the probability of being emitted as light in the light-emitting layer increases.

[0344] Therefore, it can be seen that the heterocyclic compounds disclosed herein have a higher LUMO energy level than the compounds of Comparative Examples 5 to 8. When the heterocyclic compounds disclosed herein are used as electron blocking layers of organic light-emitting components, the driving voltage properties, luminous efficiency properties and lifespan properties are all excellent due to the superior electron blocking ability and the charge balance formed by holes and electrons.

[0345]

Explanation of symbols

[0346] 100:Substrate

[0347] 200: Positive electrode

[0348] 300: organic material layer

[0349] 301: hole injection layer

[0350] 302: hole transport layer

[0351] 303: Luminous layer

[0352] 304: Hole blocking layer

[0353] 305: electron transport layer

[0354] 306: electron injection layer

[0355] 400: Negative electrode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, R1 to R7 are the same as or different from each other and are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkynyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, -P(=O)R1 01R102, -SiR101R102R103, and a group consisting of a group represented by the following Chemical Formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group; At least one of R1 to R5 is a group represented by the following Chemical Formula 2; a is an integer of 0 to 4, and when a is 2 or more, R6 are the same as or different from each other; and Ar1 is a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, [Chemical formula 2] L1 to L3 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; b is an integer of 0 to 5, and when b is 2 or more, L1 are the same as or different from each other; c is an integer from 0 to 5, and when c is 2 or more, L2 are the same as or different from each other; d is an integer of 0 to 5, and when d is 2 or more, L3 are the same as or different from each other; and Ar2 and Ar3 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.

2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 and 1-2: [Chemical formula 1-1] [Chemical formula 1-2] In Chemical Formula 1-1 and Chemical Formula 1-2, R8 is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, -P(=O)R101 R102, and a group consisting of -SiR101R102R103, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, and R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group; e is an integer from 0 to 3, and when e is 2 or greater, R8 are the same as or different from each other; Ar4 and Ar5 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; R6, R7, a and Ar1 have the same definitions as in Chemical Formula 1; and L1 to L3, Ar2 to Ar3, and b to d have the same definitions as in Chemical Formula 2.

3. The heterocyclic compound according to claim 1, wherein Ar1 to Ar3 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.

4. The heterocyclic compound according to claim 2, wherein Ar4 and Ar5 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. 5 . The heterocyclic compound according to claim 1 , wherein the heterocyclic compound represented by Chemical Formula 1 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

6. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following compounds:

7. An organic light-emitting component, comprising: a first electrode; a second electrode, arranged to be opposite to the first electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode, One or more layers of the one or more organic material layers comprises the heterocyclic compound as claimed in any one of claims 1 to 6. 8 . The organic light-emitting device according to claim 7 , wherein the one or more organic material layers include a hole transport layer, and the hole transport layer contains the heterocyclic compound. 9 . The organic light-emitting device according to claim 7 , wherein the one or more organic material layers comprises an electron blocking layer, and the electron blocking layer comprises the heterocyclic compound. 10 . The organic light-emitting device according to claim 7 , wherein the one or more organic material layers include a light-emitting layer, and the light-emitting layer contains the heterocyclic compound. 11 . The organic light-emitting device according to claim 7 , wherein the one or more organic material layers include a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound.

12. The organic light-emitting component according to claim 7, further comprising one, two or more layers selected from the group consisting of a light-emitting layer, a light-assisting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

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