Novel compound and organic light emitting device using same

Abstract

The present invention provides a novel compound and an organic light emitting device using same.

Description

Novel compounds and organic light-emitting devices using the same

[0001] Cross-citation with related application(s)

[0002] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0166618, filed November 27, 2023, and Korean Patent Application No. 10-2023-0188163, filed December 21, 2023, the entire contents of which are incorporated herein by reference.

[0003]

[0004] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0005]

[0006] Organic light-emitting diodes (OLEDs) generally refer to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices utilizing this phenomenon boast a wide viewing angle, excellent contrast, and fast response times, and are actively researched due to their superior brightness, operating voltage, and response speed characteristics.

[0007]

[0008] Organic light-emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0009]

[0010] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices such as the above.

[0011]

[0012] [Prior Art Literature]

[0013] [Patent Document]

[0014] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

[0015]

[0016] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0017]

[0018] The present invention provides a compound represented by the following chemical formula 1:

[0019] [Chemical Formula 1]

[0020]

[0021] In the above chemical formula 1,

[0022] X is independently N or CH, provided that at least one of X is N,

[0023] L is deuterium substituted or unsubstituted C 6-60 It's arylene,

[0024] Ar1 is substituted or unsubstituted C 6-60 It's Aryl,

[0025] Ar2 is substituted or unsubstituted C comprising at least one selected from the group consisting of O and S. 2-60 It is heteroaryl,

[0026] R1 is each independently hydrogen, deuterium, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from the group consisting of N, O, and S 2-60 is heteroaryl, and

[0027] n is an integer from 1 to 8,

[0028] However, at least one of L, Ar1, Ar2, and R1 is deuterium or substituted with deuterium.

[0029]

[0030] In addition, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer includes a compound represented by the chemical formula 1.

[0031]

[0032] The compound represented by the above-described chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can significantly improve the lifespan characteristics along with improved efficiency while maintaining a low operating voltage in the organic light-emitting device. In particular, the compound represented by the above-described chemical formula 1 can be used as a hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection material.

[0033]

[0034] Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4).

[0035]

[0036] Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (3), a hole blocking layer (8), an electron injection and transport layer (9), and a cathode (4).

[0037]

[0038] Hereinafter, the present invention will be described in more detail to help understand it.

[0039]

[0040] In this specification, , or or "D" represents a bond connecting to another substituent, and "D" represents deuterium.

[0041]

[0042] The term "unsubstituted or substituted" as used herein means a group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylphosphine group; or a heterocyclic group containing at least one of N, O, and S atoms, or a substituted or unsubstituted group in which two or more of the above-mentioned substituents are linked. For example, the "substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group can be an aryl group or can be interpreted as a substituent in which two phenyl groups are connected.

[0043]

[0044] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0045]

[0046] In the present specification, the ester group may have the oxygen of the ester group replaced by a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.

[0047]

[0048] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0049]

[0050] In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc.

[0051]

[0052] In this specification, the boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, etc.

[0053]

[0054] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0055]

[0056] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexetylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0057]

[0058] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, 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, and styrenyl.

[0059]

[0060] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, 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 the like.

[0061]

[0062] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0063]

[0064] In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, It can be, but is not limited to, the following.

[0065]

[0066] In the present specification, a heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group, There are, but are not limited to, phenothiazinyl groups and dibenzofuranyl groups.

[0067]

[0068] In this specification, the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the examples of the aryl group described above. In this specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine may be applied to the description of the heterocyclic group described above. In this specification, the alkenyl group among the aralkenyl group is the same as the examples of the alkenyl group described above. In this specification, the description of the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description of the heterocyclic group described above may be applied to the heteroarylene except that it is a divalent group. In this specification, the description of the aryl group or the cycloalkyl group described above may be applied to the hydrocarbon ring except that it is not a monovalent group but is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above may be applied, except that the heterocyclic group is not monovalent and is formed by combining two substituents.

[0069]

[0070] As used herein, the term "deuterated or substituted with deuterium" means that at least one of the substitutable hydrogens in the compound, divalent linking group or monovalent substituent is replaced with deuterium.

[0071]

[0072] Additionally, the term "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with one to a maximum of nine hydrogen atoms." For example, the term "unsubstituted or substituted with deuterium phenanthryl" can be understood to mean "unsubstituted or substituted with nine deuterium atoms," considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the phenanthryl structure is nine.

[0073]

[0074] Additionally, the term "deuterated structure" encompasses compounds of all structures in which at least one hydrogen is replaced by a deuterium, divalent linking group, or monovalent substituent. For example, the deuterated structure of phenyl can be understood to refer to monovalent substituents of all structures in which at least one substitutable hydrogen in the phenyl group is replaced by a deuterium, as follows.

[0075]

[0076] Additionally, the "deuterium substitution rate" or "deuteration degree" of a compound means the ratio of the number of substituted deuteriums to the total number of hydrogens that can exist in the compound (the sum of the number of hydrogens replaceable with deuterium in the compound and the number of substituted deuteriums) calculated as a percentage. Therefore, when the "deuterium substitution rate" or "deuteration degree" of a compound is "K%," it means that K% of the hydrogens replaceable with deuterium in the compound have been replaced with deuterium.

[0077]

[0078] At this time, the above "deuterium substitution rate" or "deuteration degree" is determined by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry) can be used to measure the concentration of deuterium in a compound, and more specifically, when MALDI-TOF MS is used, the "deuterium substitution rate" or "degree of deuteration" can be obtained by calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound as a percentage after obtaining the number of substituted deuterium atoms in the compound through MALDI-TOF MS analysis.

[0079]

[0080] (compound)

[0081] The present invention provides a compound represented by the above chemical formula 1.

[0082]

[0083] Specifically, the compound represented by the above chemical formula 1 is a compound in which a carbazole ring and a heterocyclic ring containing one or more Ns are bonded to the ortho position of a benzene ring in a parent nucleus structure, and an aryl and a heteroaryl containing O or S are substituted at specific positions of the heterocyclic ring, and is characterized in that at least one or more of the substituents excluding the benzene ring in the compound is deuterium or substituted with deuterium.

[0084]

[0085] More specifically, in the above chemical formula 1,

[0086] X is independently N or CH, provided that at least one of X is N,

[0087] L is deuterium substituted or unsubstituted C 6-60 It's arylene,

[0088] Ar1 is substituted or unsubstituted C 6-60 It's Aryl,

[0089] Ar2 is substituted or unsubstituted C comprising at least one selected from the group consisting of O and S. 2-60 It is heteroaryl,

[0090] R1 is each independently hydrogen, deuterium, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from the group consisting of N, O, and S 2-60 is heteroaryl, and

[0091] n is an integer from 1 to 8,

[0092] However, at least one of L, Ar1, Ar2, and R1 is deuterium or substituted with deuterium.

[0093]

[0094] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 is characterized in that it introduces a specific substituted / unsubstituted heteroaryl group through an arylene linker L and a substituted / unsubstituted aryl group at a specific position in the heterocyclic portion including N among the parent structure in which a heterocyclic portion including one or more Ns is connected to a carbazole ring through a benzene ring at the center, thereby causing steric hindrance, so that the heterocyclic portion including N and the carbazole portion become a distorted structure. In this case, the electron donating property of the carbazole substituent acts to increase the stability of the overall molecule, while the electron distribution is separated, thereby providing additional CT (charge transfer) characteristics, thereby improving the voltage / efficiency characteristics.

[0095]

[0096] In particular, in the compound represented by the above chemical formula 1, by performing deuterium substitution on the carbazole portion of the above-described parent structure, or by introducing a specific substituted / unsubstituted aryl group at a specific position of the heterocycle containing one or more Ns as described above, i.e., Ar1, and introducing a specific substituted / unsubstituted heteroaryl group at Ar2 via an arylene linker L, deuterium substitution on this substituent portion is performed, thereby controlling electron distribution and balance, and significantly increasing the lifespan improvement effect along with high efficiency of the device.

[0097]

[0098] Specifically, in the above chemical formula 1, L is a deuterium substituted or unsubstituted C 6-30 Arylene, or C 6-20 Arylene, or C 6-12 It's arylene.

[0099]

[0100] For example, L may be substituted with at least one deuterium atom, or substituted with at least two deuterium atom(s), or substituted with at least three deuterium atom(s), or substituted with at least four deuterium atom(s).

[0101]

[0102] More specifically, L may be phenylene substituted or unsubstituted with deuterium, or biphenylene substituted or unsubstituted with deuterium.

[0103]

[0104] For example, L may be any one selected from the group consisting of:

[0105]

[0106] In the above formula,

[0107] D is deuterium,

[0108] n1 is an integer from 1 to 4,

[0109] n2 is an integer from 1 to 3,

[0110] n3 is an integer from 1 to 5.

[0111]

[0112] Among the L-related equations described above, represents a linking group that binds to the triazinyl ring and Ar2 of chemical formula 1, respectively.

[0113]

[0114] In addition, in the above chemical formula 1, Ar1 is substituted or unsubstituted C 6-30 Aryl, or substituted or unsubstituted C 6-20 Aryl, substituted or unsubstituted C 6-12 It's Aryl.

[0115]

[0116] For example, Ar1 may be substituted with at least one deuterium atom, or substituted with at least two deuterium atom(s), or substituted with at least three deuterium atom(s), or substituted with at least five deuterium atom(s).

[0117]

[0118] More specifically, Ar1 may be a phenyl substituted or unsubstituted with deuterium, a biphenyl substituted or unsubstituted with deuterium, or a terphenyl substituted or unsubstituted with deuterium.

[0119]

[0120] For example, Ar1 may be any one selected from the group consisting of:

[0121]

[0122] In the above formula,

[0123] D is deuterium,

[0124] n4 are each independently an integer from 1 to 5,

[0125] n5 are each independently an integer from 1 to 4,

[0126] n6 is an integer from 1 to 3.

[0127]

[0128] Among the Ar1 related formulas mentioned above, represents a linking group bonded to the triazinyl ring of chemical formula 1.

[0129]

[0130] In addition, in the above chemical formula 1, Ar2 is a heteroaryl including at least one selected from the group consisting of O and S, and is substituted or unsubstituted C 2-30 Heteroaryl, or substituted or unsubstituted C 2-20 Heteroaryl, or substituted or unsubstituted C 2-12 It is heteroaryl.

[0131]

[0132] For example, Ar2 may be substituted with at least one deuterium atom, or substituted with at least two deuterium atom(s), or substituted with at least three deuterium atom(s), or substituted with at least five deuterium atom(s).

[0133]

[0134] More specifically, Ar2 may be a deuterium-substituted or unsubstituted dibenzofuranyl, or a deuterium-substituted or unsubstituted dibenzothiophenyl.

[0135]

[0136] For example, Ar2 may be any one selected from the group consisting of:

[0137]

[0138] In the above formula,

[0139] D is deuterium,

[0140] n7 are each independently an integer from 1 to 3,

[0141] n8 is an integer from 1 to 4, each independently.

[0142]

[0143] Among the Ar2 related formulas mentioned above, represents a linking group bonded to the triazinyl ring or L of chemical formula 1.

[0144]

[0145] Meanwhile, the compound represented by the above chemical formula 1 can prevent the problem of lowering molecular stability that may occur due to electron deficiency by carrying out deuterium substitution on the carbazole ring in a parent core structure in which a heterocycle containing one or more Ns connects a carbazole ring through a benzene ring at the center, and can significantly increase the lifespan increase effect.

[0146]

[0147] In the above chemical formula 1, at least one of R1 is deuterium; C substituted with deuterium 6-60 Aryl; or C containing one or more heteroatoms of N, O, and S substituted with deuterium 2-60 It may be heteroaryl.

[0148]

[0149] Specifically, each R1 can independently be hydrogen or deuterium.

[0150]

[0151] More specifically, at least one of R1 may be deuterium, or at least two may be deuterium, or at least three may be deuterium, or at least five may be deuterium.

[0152]

[0153] Meanwhile, in the above chemical formula 1, at least three of L, Ar1, Ar2, and R1 may be deuterium, or at least one of L, Ar1, Ar2, and R1 may be substituted with three or more deuterium.

[0154]

[0155] Preferably, at least five of L, Ar1, Ar2, and R1 are deuterium, or at least one of L, Ar1, Ar2, and R1 may be substituted with five or more deuterium.

[0156]

[0157] Meanwhile, all hydrogens included in the above chemical formula 1 can be replaced with deuterium.

[0158]

[0159] For example, the compound represented by the above chemical formula 1 is substituted with 1 to 60 deuterium atoms.

[0160]

[0161] Preferably, the compound represented by the above chemical formula 1 may be substituted with 1 to 50 deuterium atoms.

[0162]

[0163] More preferably, the compound represented by the above chemical formula 1 may be substituted with 2 or more, or 3 or more, or 4 or more, or 5 or more deuterium atoms, and 45 or less, or 40 or less, or 38 or less, or 36 or less, or 34 or less, or 32 or less, or 30 or less, or 28 or less, or 26 or less, or 24 or less, or 22 or less, or 20 or less, or 18 or less, or 16 or less, or 14 or less, or 12 or less, or 10 or less deuterium atoms.

[0164]

[0165] Meanwhile, representative examples of compounds represented by the chemical formula 1 are as follows.

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355] .

[0356]

[0357] The above compounds may contain at least one or more deuterium atoms.

[0358]

[0359] When the compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound may be 5% or more, 10% or more, 20% or more, 25% or more, 30% or more, 40% or more, or 50% or more, and 100% or less, 90% or less, 80% or less, or 70% or less.

[0360]

[0361] For example, the compound may contain 2 to 30 deuterium atoms. Specifically, when the compound contains deuterium, the compound may contain 2 or more, 3 or more, 5 or more, 6 or more, 7 or more, 8 or more, 10 or more, 11 or more, 12 or more, 15 or more, or 18 or more, but not more than 30, not more than 28, not more than 26, not more than 24, not more than 22, or not more than 20 deuterium atoms.

[0362]

[0363] Meanwhile, the compound represented by the above chemical formula 1 can be used together with the compound represented by the following chemical formula 2 when used in an organic light-emitting device.

[0364] [Chemical Formula 2]

[0365]

[0366] In the above chemical formula 2,

[0367] Ar4 and Ar5 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S 5-60 It is heteroaryl,

[0368] R2 and R3 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S 5-60 It is heteroaryl,

[0369] p and q are each independently an integer from 0 to 7.

[0370]

[0371] In particular, when the compound represented by the above chemical formula 2 is used in an organic light-emitting device together with the compound represented by the above chemical formula 1, it is advantageous even in the case of forming an exciplex, so that the characteristic effects of low voltage, high efficiency, and long life can be more significantly exhibited.

[0372]

[0373] Specifically, in the above chemical formula 2, Ar4 and Ar5 can each independently be phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.

[0374]

[0375] Additionally, R2 and R3 may each be hydrogen or phenyl.

[0376]

[0377] Also, p and q can be 0 or 1, respectively.

[0378]

[0379] Representative examples of compounds represented by the above chemical formula 2 are as follows.

[0380]

[0381]

[0382]

[0383]

[0384] .

[0385]

[0386] In addition, when the compound represented by the above chemical formula 2 is used together with the compound represented by the above chemical formula 1 in one or more organic layers of an organic light-emitting device, the weight ratio of the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be 20:80 to 50:50, or 35:65 to 45:55, and preferably 40:60.

[0387]

[0388] Meanwhile, the compound represented by the above chemical formula 1 can be manufactured by a manufacturing method as shown in the following reaction scheme 1.

[0389]

[0390] [Reaction Formula 1]

[0391]

[0392] In the above reaction formula 1, L, Ar1, Ar2, R1, and n are as defined in the above chemical formula 1, and Q1 and Q are each independently halogen.

[0393]

[0394] For example, Q1 and Q are each independently F, Cl, Br, or I, preferably F, Cl, or Br, more preferably Cl, or Br, and even more preferably Cl.

[0395]

[0396] The above reaction scheme 1 is a Suzuki coupling reaction and an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base. The reactor and reaction conditions for each reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples described below.

[0397]

[0398] For example, in the above reaction scheme 1, the reaction of introducing an L substituent into the parent structure including a carbazole ring and a triazine ring and the reaction of introducing an Ar2 substituent can each be carried out by reacting with a palladium catalyst (Pd catalyst) in the presence of a base.

[0399]

[0400] Examples of such base components include potassium carbonate (K2CO3), sodium bicarbonate (NaHCO3), cesium carbonate (Cs2CO3), sodium acetate (NaOAc), potassium acetate (KOAc), sodium ethoxide (NaOEt), sodium tert-butoxide (NaOtBu), or triethylamine (Et3N), N,N-diisopropylethylamine (EtN(iPr)2). Preferably, the base component may be potassium carbonate (K2CO3).

[0401]

[0402] In addition, as the palladium catalyst, bis(tri-(tert-butyl)phosphine)palladium(0) (bis(tri-(tert-butyl)phosphine)palladium(0), Pd(t-Bu3P)2), tetrakis(triphenylphosphine)palladium(0) (tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4), tris(dibenzylideneacetone)dipalladium(0) (tris(dibenzylideneacetone)-dipalladium(0), bis(dibenzylideneacetone)palladium(0) (bis(dibenzylideneacetone)palladium(0), Pd(dba)2) or palladium(II) acetate (palladium(II) acetate, Pd(OAc)2) can be used. Preferably, the palladium catalyst is tetrakis(triphenylphosphine)palladium(0). (tetrakis(triphenylphosphine)palladium (0), Pd(PPh3)4).

[0403]

[0404] (organic light emitting device)

[0405] Meanwhile, the present invention provides an organic light-emitting device comprising a compound represented by the above chemical formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by the above chemical formula 1.

[0406]

[0407] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0408]

[0409] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes a compound represented by the chemical formula 1.

[0410]

[0411] In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes a compound represented by the chemical formula 1.

[0412]

[0413] Additionally, the organic layer may include an electron blocking layer, and the electron blocking layer includes a compound represented by the chemical formula 1.

[0414]

[0415] Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1.

[0416]

[0417] Additionally, the light-emitting layer further includes a dopant compound.

[0418]

[0419] Additionally, the light-emitting layer includes a compound of chemical formula 1 and a dopant.

[0420]

[0421] For example, the light-emitting layer includes a compound of chemical formula 1 and a dopant, and includes the compound of chemical formula 1 and the dopant in a weight ratio of 100:1 to 1:1.

[0422]

[0423] In addition, the light-emitting layer includes a compound of chemical formula 1 and a dopant, and includes the compound of chemical formula 1 and the dopant in a content ratio of 100:1 to 2:1.

[0424]

[0425] In addition, the light-emitting layer comprises a compound of chemical formula 1 and a dopant, and comprises the compound of chemical formula 1 and the dopant in a weight ratio of 100:1 to 5:1, or 100:1 to 10:1, or 100:1 to 20:1, or 100:1 to 30:1.

[0426]

[0427] For example, the dopant is a metal complex.

[0428]

[0429] Specifically, the dopant is an iridium-based metal complex.

[0430]

[0431] In addition, the organic layer includes a light-emitting layer, the light-emitting layer includes a dopant, and the dopant material is selected from the following structural formulas.

[0432]

[0433]

[0434]

[0435]

[0436] .

[0437]

[0438] The structure specified above is not limited to the dopant compound.

[0439]

[0440] Additionally, the organic layer may include a hole-blocking layer, and the hole-blocking layer includes a compound represented by the chemical formula 1.

[0441]

[0442] In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, the electron injection layer, or the layer that simultaneously injects and transports electrons includes a compound represented by the chemical formula 1.

[0443]

[0444] In addition, the organic layer includes a light-emitting layer and an electron-blocking layer, and the light-emitting layer or the electron-blocking layer may include a compound represented by the chemical formula 1.

[0445]

[0446] Meanwhile, the organic light-emitting device according to the present invention may further include a compound represented by the chemical formula 2 together with the compound represented by the chemical formula 1. For example, the organic light-emitting device according to the present invention includes a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more layers of the organic layers may further include a compound represented by the chemical formula 2 together with the compound represented by the chemical formula 1.

[0447]

[0448] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0449]

[0450] Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, the compound represented by the chemical formula 1 may be included in the light-emitting layer.

[0451]

[0452] FIG. 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (3), a hole blocking layer (8), an electron injection and transport layer (9), and a cathode (4). In this structure, the compound represented by the chemical formula 1 may be included in at least one layer of the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, and the electron injection and transport layer. Specifically, the compound represented by the chemical formula 1 may be included in the light-emitting layer, and for example, may be included as a host material of the light-emitting layer.

[0453]

[0454] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by the chemical formula 1 or a compound represented by the chemical formula 2 together with the compound represented by the chemical formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same material or different materials.

[0455]

[0456] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on the substrate.

[0457]

[0458] In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. In particular, the compound represented by the above chemical formula 1 has excellent solubility in a solvent used in the solution coating method, making it easy to apply the solution coating method. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0459]

[0460] Accordingly, the present invention provides a coating composition comprising a compound represented by the above chemical formula 1 and a solvent.

[0461]

[0462] The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and examples thereof include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc.; ether solvents such as tetrahydrofuran, dioxane, etc.; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, mesitylene, etc.; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, etc.; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, etc. Examples thereof include polyhydric alcohols and their derivatives, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents, such as dimethyl sulfoxide; and amide solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents, such as butyl benzoate and methyl-2-methoxybenzoate; tetralin; and solvents, such as 3-phenoxy-toluene. In addition, the above-mentioned solvents may be used alone or in combination of two or more solvents.

[0463]

[0464] In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

[0465]

[0466] The present invention also provides a method for forming a functional layer using the coating composition described above. Specifically, the method comprises the steps of coating the coating composition according to the present invention described above using a solution process; and heat-treating the coated coating composition.

[0467]

[0468] In the above heat treatment step, the heat treatment temperature is preferably 150°C to 230°C. In addition, the heat treatment time is preferably 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

[0469]

[0470] For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0471]

[0472] As the anode material, a material having a high work function is generally preferred so that hole injection into the organic layer can be facilitated. Specific examples of the anode material include, but are not limited to, 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0473]

[0474] The cathode material is preferably a material having a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0475]

[0476] The above-mentioned hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and has excellent thin film forming ability. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers such as polyaniline and polythiophene.

[0477]

[0478] The above hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. A material having high hole mobility is suitable as the hole transport material, which can transport holes from the anode or the hole injection layer and move them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. In addition, the hole transport layer may use one or more hole transport materials, and may be composed of one or more layers for each hole transport material. For example, the hole transport layer may be composed of a first hole transport layer including an arylamine-based organic material in the form of a polynuclear condensed ring as the hole transport material, and a second hole transport layer including an arylamine-based organic material in the form of a triarylamine as the hole transport material.

[0479]

[0480] The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from recombinating in the light emitting layer and passing to the hole transport layer. It is also called an electron suppression layer. A material having a lower electron affinity than the electron transport layer is preferred for the electron blocking layer. Preferably, the compound represented by the above chemical formula 1 may be included as the material of the electron blocking layer.

[0481]

[0482] The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0483]

[0484] The above-described light-emitting layer may include a host material and a dopant material. The host material may include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound may include, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. Preferably, a compound according to the present invention is used as the host material.

[0485]

[0486] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, examples of aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group. Examples of styrylamine compounds include compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and wherein one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, examples of styrylamine, styryldiamine, styryltriamine, and styryltetraamine include, but are not limited to, styrylamine. In addition, examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes. Preferably, an iridium-based metal complex is used as the dopant material.

[0487]

[0488] The above-mentioned light-emitting layer may be a green light-emitting layer, and when the compound according to the present invention is used as a host material, the stability for electrons and holes is increased, and energy transfer from the host to the green dopant is performed well, thereby improving the driving voltage, light-emitting efficiency, and lifespan characteristics of the organic light-emitting device.

[0489]

[0490] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer is suitable. A material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are used, and in each case, followed by an aluminum layer or a silver layer.

[0491]

[0492] The above electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound having excellent thin-film forming ability. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0493]

[0494] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0495]

[0496] Meanwhile, in the present invention, the "electron injection and transport layer" is a layer that performs the functions of both the electron injection layer and the electron transport layer, and materials that perform the functions of each layer may be used singly or in combination, but are not limited thereto. Preferably, the compound represented by the above chemical formula 1 may be included as the material of the electron injection and transport layer.

[0497]

[0498] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.

[0499]

[0500] In addition, the compound according to the present invention can be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.

[0501]

[0502] The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0503]

[0504] [Example]

[0505] Synthesis Example 1: Preparation of Compound GH1

[0506]

[0507]

[0508] (1-1) Preparation of compound GH1 P-1

[0509] In a nitrogen atmosphere, 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (30 g, 69.3 mmol) and (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid (16.1 g, 69.3 mmol) were added to 600 mL of tetrahydrofuran (THF), stirred, and refluxed. Then, potassium carbonate (K2CO3, 19.2 g, 138.6 mmol) dissolved in 28 mL of water was added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (Pd(PPh3)4, 2.4 g, 2.1 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1660 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound GH1 P-1 (31.7 g, 78%, MS: [M+H] + = 585.2) was manufactured.

[0510]

[0511] (1-2) Preparation of compound GH1

[0512] In a nitrogen atmosphere, the compound GH1 P-1 (30 g, 51.3 mmol) prepared above and dibenzo[b,d]furan-4-yl-d7)boronic acid (11.2 g, 51.3 mmol) were added to 600 mL of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (K2CO3, 14.2 g, 102.6 mmol) dissolved in 28 mL of water was added, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (Pd(PPh3)4, 1.8 g, 1.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 2213 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound GH1 (29.1 g, 78%, MS: [M+H] + = 724.9) was manufactured.

[0513]

[0514] Synthesis Example 2: Preparation of Compound GH2

[0515]

[0516]

[0517] (2-1) Preparation of compound GH2 P-1

[0518] In (1-1) of Synthesis Example 1, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (3-chlorophenyl)boronic acid was used instead of (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid, and the same method as Synthesis Example 1-1 was used to obtain a white solid compound GH2 P-1 (28.7 g, 82%, MS: [M+H] + = 514.2) was manufactured.

[0519]

[0520] (2-2) Preparation of compound GH2

[0521] In (1-2) of Synthesis Example 1, the compound GH2 P-1 prepared above was used instead of the compound GH1 P-1, and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-yl-d7)boronic acid, and the same method as Synthesis Example 1-2 was used to obtain a white solid compound GH2 (26.8 g, 71%, MS: [M+H] + = 646.3) was manufactured.

[0522]

[0523] Synthesis Example 3: Preparation of Compound GH3

[0524]

[0525]

[0526] (3-1) Preparation of compound GH3 P-1

[0527] Except that 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole in (1-1) of Synthesis Example 1, a white solid compound GH3 P-1 (29.8 g, 74%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 1-1. + = 590.2) was manufactured.

[0528]

[0529] (3-2) Preparation of compound GH3

[0530] In Synthesis Example 1 (1-2), except that the compound GH3 P-1 prepared above was used instead of the compound GH1 P-1, a white solid compound GH3 (26.8 g, 71%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 1-2. + = 646.3) was manufactured.

[0531]

[0532] Synthesis Example 4: Preparation of Compound GH4

[0533]

[0534]

[0535] (4-1) Preparation of compound GH4 P-1

[0536] Except that 9-(2-(4-([1,1'-biphessnyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole in (2-1) of Synthetic Example 2, a white solid compound GH4 P-1 (27.6 g, 80%, MS: [M+H]) was obtained in the same manner as in Synthetic Example 2-1. + = 600.3) was manufactured.

[0537]

[0538] (4-2) Preparation of compound GH4

[0539] In Synthesis Example 2 (2-2), except that the compound GH4 P-1 prepared above was used instead of the compound GH2 P-1, a white solid compound GH4 (29.2 g, 80%, MS: [M+H]) was prepared in the same manner as in Synthesis Example 2-2. + = 732.4) was manufactured.

[0540]

[0541] Synthesis Example 5: Preparation of Compound GH5

[0542]

[0543]

[0544] (5-1) Preparation of compound GH5 P-1

[0545] In Synthesis Example 2 (2-1), except that (3'-chloro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (3-chlorophenyl)boronic acid, a white solid compound GH5 P-1 (31 g, 77%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-1. + = 590.2) was manufactured.

[0546]

[0547] (5-2) Preparation of compound GH5

[0548] In (2-2) of Synthesis Example 2, the compound GH5 P-1 prepared above was used instead of the compound GH2 P-1, and dibenzo[b,d]thiophen-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH5 (32 g, 85%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 738.3) was manufactured.

[0549]

[0550] Synthesis Example 6: Preparation of Compound GH6

[0551]

[0552]

[0553] (6-1) Preparation of compound GH6 P-1

[0554] In (2-1) of Synthesis Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of (3-chlorophenyl)boronic acid, and the same method as Synthesis Example 2-1 was used to obtain a white solid compound GH6 P-1 (33 g, 79%, MS: [M+H] + = 596.3) was manufactured.

[0555]

[0556] (6-2) Preparation of compound GH6

[0557] In (2-2) of Synthesis Example 2, the compound GH6 P-1 prepared above was used instead of the compound GH2 P-1, and (dibenzo[b,d]thiophen-4-yl-2,6,8-d3)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH6 (31 g, 82%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 747.3) was manufactured.

[0558]

[0559] Synthesis Example 7: Preparation of Compound GH7

[0560]

[0561]

[0562] (7-1) Preparation of compound GH7 P-1

[0563] In (2-1) of Synthesis Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (3-chlorophenyl-2,4,5,6-d4)boronic acid was used instead of (3-chlorophenyl)boronic acid. In the same manner as in Synthesis Example 2-1, a white solid compound GH7 P-1 (26.7 g, 76%, MS: [M+H]) was obtained. + = 526.3) was manufactured.

[0564]

[0565] (7-2) Preparation of compound GH7

[0566] In (2-2) of Synthesis Example 2, the compound GH7 P-1 prepared above was used instead of the compound GH2 P-1, and (dibenzo[b,d]thiophen-4-yl-d7)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH7 (31 g, 80%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 681.4) was manufactured.

[0567]

[0568] Synthesis Example 8: Preparation of Compound GH8

[0569]

[0570]

[0571] (8-1) Preparation of compound GH8 P-1

[0572] In (2-1) of Synthesis Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)boronic acid was used instead of (3-chlorophenyl)boronic acid, and the same method as Synthesis Example 2-1 was used to obtain a white solid compound GH8 P-1 (34 g, 84%, MS: [M+H] + = 603.3) was manufactured.

[0573]

[0574] (8-2) Preparation of compound GH8

[0575] In (2-2) of Synthesis Example 2, the compound GH8 P-1 prepared above was used instead of the compound GH2 P-1, and (dibenzo[b,d]thiophen-4-yl-d7)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH8 (31 g, 84%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 742.4) was manufactured.

[0576]

[0577] Synthesis Example 9: Preparation of Compound GH9

[0578]

[0579]

[0580] (9-1) Preparation of compound GH9 P-1

[0581] Except that 9-(2-(4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole in (2-1) of Synthesis Example 2, a white solid compound GH9 P-1 (28 g, 82%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-1. + = 594.2) was manufactured.

[0582]

[0583] (9-2) Preparation of compound GH9

[0584] In (2-2) of Synthesis Example 2, the compound GH9 P-1 prepared above was used instead of the compound GH2 P-1, and dibenzo[b,d]thiophen-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH9 (32 g, 85%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 742.3) was manufactured.

[0585]

[0586] Synthesis Example 10: Preparation of Compound GH10

[0587]

[0588]

[0589] (10-1) Preparation of compound GH10 P-1

[0590] In (2-1) of Synthesis Example 2, 9-(2-(4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)boronic acid was used instead of (3-chlorophenyl)boronic acid, and the same method as Synthesis Example 2-1 was followed to obtain a white solid compound GH10 P-1 (29 g, 77%, MS: [M+H] + = 743.3) was manufactured.

[0591]

[0592] (10-2) Preparation of compound GH10

[0593] In (2-2) of Synthesis Example 2, the compound GH10 P-1 prepared above was used instead of the compound GH2 P-1, and (dibenzo[b,d]furan-4-yl-2,6,8-d3)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH10 (28 g, 79%, MS: [M+H]) was obtained in the same manner as in Synthesis Example 2-2, except that + = 878.4) was manufactured.

[0594]

[0595] Synthesis Example 11: Preparation of Compound GH11

[0596]

[0597]

[0598] (11-1) Preparation of compound GH11 P-1

[0599] In (2-1) of Synthesis Example 2, 9-(2-(4-chloro-6-(phenyl)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and the same method as Synthesis Example 2-1 was used to obtain a white solid compound GH11 P-1 (26.7 g, 76%, MS: [M+H] + = 515.2) was manufactured.

[0600]

[0601] (11-2) Preparation of compound GH11

[0602] In (2-2) of Synthesis Example 2, the compound GH11 P-1 prepared above was used instead of the compound GH2 P-1, and dibenzo[b,d] thiophen-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and a white solid compound GH11 (31 g, 80%, MS: [M+H]) was prepared in the same manner as in Synthesis Example 2-2, except that + = 663.2) was manufactured.

[0603]

[0604] Example 1

[0605] A glass substrate coated with a 100 nm thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0606]

[0607] On the ITO transparent electrode thus prepared, the compound HI-A below was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer. On the hole injection layer, the compound HAT below was vacuum deposited to form a first hole transport layer to a thickness of 5 nm, and on the first hole transport layer, the compound HT-A below was vacuum deposited to form a second hole transport layer to a thickness of 50 nm. Subsequently, on the hole transport layer, the compound HT-B below was thermally vacuum deposited to a thickness of 45 nm to form an electron blocking layer. Then, on the electron blocking layer, the compound GH1 below prepared above was mixed with the compound GH-H below at a weight ratio of 1:1, and then vacuum deposited with the compound GD below at a weight ratio of 90:10 to a thickness of 40 nm to form a light emitting layer. Subsequently, on the light emitting layer, the compound ET-A below was vacuum deposited to a thickness of 5 nm to form a hole blocking layer. On the above hole-blocking layer, the following compound ET-B and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 35 nm.

[0608]

[0609] After depositing lithium fluoride (LiF) with a thickness of 1 nm on the electron injection and transport layer, aluminum was then deposited with a thickness of 100 nm to form a cathode, thereby manufacturing an organic light-emitting device.

[0610]

[0611] .

[0612]

[0613] In the above process, the deposition rate of organic materials was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The vacuum during deposition was 1 X 10 -7 torr or 5 X 10 -5 torr was maintained.

[0614]

[0615] Examples 2 to 11

[0616] An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds GH2 to GH11 described in Table 1 below were used instead of compound GH1 when forming the light-emitting layer in the organic light-emitting device of Example 1. In Table 1 below, the structures of compounds GH1 to GH11 are as follows, respectively.

[0617]

[0618] .

[0619]

[0620] Comparative Examples 1 to 9

[0621] An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds GH-C1 to GH-C9 described in Table 1 below were used instead of compound GH1 when forming the light-emitting layer in the organic light-emitting device of Example 1. In Table 1 below, the structures of compounds GH-C1 to GH-C9 are respectively as follows.

[0622]

[0623] .

[0624]

[0625] [Experimental Example]

[0626] Current was applied to the organic light-emitting devices manufactured in Examples 1 to 11 and Comparative Examples 1 to 9, and the voltage, efficiency, luminous color, and lifespan (T95) were measured, and the results are shown in Table 1 below. At this time, the voltage and efficiency were 10 mA / cm 2 The current density was applied and measured, and T95 was measured at a current density of 20 mA / cm. 2 It means the time (hr) until the initial luminance decreases to 95%.

[0627]

[0628] Distinctive luminescent layer compound voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A) (@10mA / cm) 2 ) Fluorescent color T 95 (hr)(@20mA / cm 2) Example 1 Compound GH1 3.59 84.7 Green 150 Example 2 Compound GH2 3.55 82.4 Green 139 Example 3 Compound GH3 3.66 84.5 Green 172 Example 4 Compound GH4 3.69 88.2 Green 159 Example 5 Compound GH5 3.67 86.3 Green 145 Example 6 Compound GH6 3.66 86.1 Green 175 Example 7 Compound GH7 3.58 89.6 Green 192 Example 8 Compound GH8 3.69 82.8 Green 195 Example 9 Compound GH9 3.60 87.7 Green 168 Example 10 Compound GH10 3.61 83.7 Green 164 Example 11 Compound GH113.6286.7Green156Comparative Example 1 Compound GH-C13.8873.0Green92Comparative Example 2 Compound GH-C23.7578.2Green104Comparative Example 3 Compound GH-C33.6388.4Green96Comparative Example 4 Compound GH-C43.7777.4Green102Comparative Example 5 Compound GH-C53.6172.7Green105Comparative Example 6 Compound GH-C63.9880.5Green51Comparative Example 7 Compound GH-C73.6484.5Green133Comparative Example 8 Compound GH-C83.7280.1Green128Comparative Example 9 Compound GH-C93.6979.8Green112

[0629]

[0630] When current was applied to the organic light-emitting devices manufactured by Examples 1 to 11 and Comparative Examples 1 to 9, the results shown in Table 1 were obtained. The green organic light-emitting device of Example 1 used a material that has been widely used in the past, and has a structure in which compound GH1 and compound GH-H are mixed and used as a light-emitting layer, and compound GD is used as a dopant for the green light-emitting layer. Examples 2 to 11 manufactured organic light-emitting devices using compounds GH2 to GH11 instead of compound 1, and Comparative Examples 1 to 9 manufactured organic light-emitting devices using comparative compounds GH-C1 to GH-C9 instead of compound GH1.

[0631]

[0632] From the results in Table 1 above, it was confirmed that when compounds having the structure of Chemical Formula 1 were applied to the light-emitting layer of an organic electroluminescent device, a device having long-life characteristics while maintaining high efficiency with a low driving voltage could be obtained.

[0633]

[0634] Specifically, according to the present invention, the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1 of the present invention is a molecule designed to have a structure in which a substituted / unsubstituted aryl group and a specific substituted / unsubstituted heteroaryl group are introduced at specific positions in the heterocyclic portion including N described above among the parent structure in which a heterocyclic portion including one or more Ns is connected to a carbazole ring through a benzene ring at the center and a benzene ring, thereby inducing steric hindrance, so that the heterocyclic portion including N and the carbazole portion become a distorted structure. In this case, the electron donating property of the carbazole substituent acts to increase the stability of the overall molecule, while the electron distribution is separated, thereby having additional CT (charge transfer) properties, and thereby inducing an improvement in high efficiency characteristics together with a low operating voltage.

[0635]

[0636] However, in this case, there is a high possibility that a problem will arise in molecular stability due to the electron deficiency of the carbazole substituent. To solve this, by performing deuterium substitution on the carbazole portion, or by performing deuterium substitution on a specific position of the heterocyclic portion containing the above-mentioned N, where a specific substituted / unsubstituted heteroaryl group is introduced through an aryl group and an arylene linker L, respectively, the electron distribution and balance can be adjusted, thereby significantly improving the characteristics of high efficiency and long life.

[0637]

[0638] Comparative Example 1 does not have a structure in which a specific substituted / unsubstituted heteroaryl group is introduced through a substituted / unsubstituted aryl group and an arylene linker L at a specific position of the heterocyclic portion containing N in Chemical Formula 1, and thus the overall molecular structure becomes flat, and it was confirmed that the effect mentioned above was not exhibited. In the case of Comparative Examples 2 to 4, the positions at which the phenyl group is introduced are different, and in this case, sufficient steric hindrance did not occur, and therefore, a sufficient improvement effect was not observed. In the case of Comparative Example 5, it was confirmed that since an additional carbazole group was substituted on the carbazole group, the electron donor role of the carbazole substituent was not fully expressed, leading to a decrease in efficiency and lifespan. In this way, when a heterocyclic ring such as a carbazole group is additionally substituted on carbazole, it can be seen that it directly affects the electronic properties of the original carbazole substituent, and thus, when applied to organic light-emitting devices, it exhibits inferior physical properties. Comparative Example 6 introduced a fluorene substituent, but it was confirmed that not only did it not induce sufficient steric hindrance to the carbazole group, but also the stability of the fluorene substituent was reduced, causing a rapid decrease in the lifespan. Comparative Examples 7 to 9 introduced a carbazole thione group, benzofuran, or benzothiophene substituent to the triazine ring, but it was confirmed that the overall molecular stability was reduced, the operating voltage increased, and the efficiency and lifespan were reduced.

[0639]

[0640] As described above, it was confirmed that the compounds of the present invention exhibit superior properties in terms of efficiency and lifespan compared to the comparative compounds depending on the position and type of the substituent.

[0641]

[0642] [Explanation of symbols]

[0643] 1: Substrate 2: Anode

[0644] 3: Emitting layer 4: Cathode

[0645] 5: Hole injection layer 6: Hole transport layer

[0646] 7: Electron blocking layer 8: Hole blocking layer

[0647] 9: Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is independently N or CH, provided that at least one of X is N, L is C substituted or unsubstituted with deuterium. 6-60 It's arylene, Ar 1 Silver substituted or unsubstituted C 6-60 It's Aryl, Ar 2 is a substituted or unsubstituted C comprising at least one selected from the group consisting of O and S; 2-60 It is heteroaryl, R 1 are each independently hydrogen, deuterium, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from the group consisting of N, O, and S 2-60 is heteroaryl, and n is an integer from 1 to 8, But, L, Ar 1 , Ar 2 , and R 1 At least one of them is deuterium or is substituted with deuterium.

2. In paragraph 1, L is phenylene substituted or unsubstituted with deuterium, or biphenylene substituted or unsubstituted with deuterium, compound.

3. In paragraph 1, L is one selected from the group consisting of: compound: Among the above formulas, D is deuterium, n1 is an integer from 1 to 4, n2 is an integer from 1 to 3, n3 is an integer from 1 to 5.

4. In paragraph 1, Ar 1 is a substituted or unsubstituted phenyl with deuterium, a substituted or unsubstituted biphenyl with deuterium, or a substituted or unsubstituted terphenyl with deuterium, compound.

5. In paragraph 1, Ar 1 is one selected from the group consisting of: compound: Among the above formulas, D is deuterium, n4 are each independently an integer from 1 to 5, n5 is an integer from 1 to 4, n6 is an integer from 1 to 3.

6. In paragraph 1, Ar 2 is a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, compound.

7. In paragraph 1, Ar 2 is one selected from the group consisting of: compound: Among the above formulas, D is deuterium, n7 is an integer from 1 to 3, n8 is an integer from 1 to 4, each independently.

8. In paragraph 1, R 1 At least one of them is deuterium; C substituted with deuterium 6-60 Aryl; or C containing one or more heteroatoms of N, O, and S substituted with deuterium 2-60 Heteroaryl, compound.

9. In paragraph 1, L, Ar 1 , Ar 2 , and R 1 At least three of them are deuterium, or L, Ar 1 , Ar 2 , and R 1 At least one of which is substituted with three or more deuterium atoms, compound.

10. In paragraph 1, The compound represented by the above chemical formula 1 is substituted with 1 to 60 deuterium atoms. compound.

11. In paragraph 1, The compound represented by the above chemical formula 1 is one selected from the group consisting of: compound: .

12. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 11.

13. In paragraph 12, The organic layer containing the above compound is a light-emitting layer. Organic light emitting diode.

14. In paragraph 11, The above light-emitting layer further comprises a compound represented by the following chemical formula 2: Organic light emitting diodes: [Chemical formula 2] In the above chemical formula 2, Ar 4 and Ar 5 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S 5-60 It is heteroaryl, R 2 and R 3 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing at least one heteroatom selected from the group consisting of N, O and S 5-60 It is heteroaryl, p and q are each independently an integer from 0 to 7.

15. In paragraph 14, Ar 4 and Ar 5 are each phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl, Organic light emitting diode.

16. In paragraph 14, The compound represented by the above chemical formula 2 is one selected from the group consisting of: Organic light emitting diodes: .

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