Polycyclic compound and organic light-emitting device containing the same

Abstract

The present invention relates to a polycyclic compound having a characteristic fused ring structure and an organic light-emitting device using the compound as a dopant in an emitting layer. The compound according to the present invention can realize an organic light-emitting device with improved efficiency and long life, and can be industrially usefully used in various display devices such as flat, flexible, and wearable displays as well as lighting devices.

Description

[Technical Field]

[0001] The present invention relates to a polycyclic compound employed in an organic layer such as a light-emitting layer in an organic light-emitting device, and an organic light-emitting device containing the same. [Background technology]

[0002] An organic light-emitting device is a self-luminous device in which electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in the light-emitting layer to form excitons, which then emit energy and emit light. Such organic light-emitting devices have the advantages of low driving voltage, high brightness, wide viewing angle, and fast response speed, and are applicable to full-color flat panel light-emitting displays, making them attracting attention as next-generation light sources.

[0003] In order for such an organic light emitting device to exhibit the above-mentioned characteristics, it is necessary to optimize the structure of the organic layers in the device and ensure that the materials constituting each organic layer, such as a hole injection material, a hole transport material, a hole blocking material, a light emitting material, an electron transport material, an electron injection material, and an electron blocking material, are supported by stable and efficient materials. However, there is still a need to continue developing stable and efficient organic layer structures and materials for organic light emitting devices.

[0004] In particular, to achieve maximum efficiency in the light-emitting layer, the energy bandgaps of the host and dopant must be appropriately matched so that holes and electrons can transfer to the dopant via stable electrochemical pathways, respectively, to form excitons. Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, the present invention aims to provide a polycyclic compound having a characteristic fused ring structure and employing the compound as a dopant material in the light-emitting layer to provide a highly efficient, long-life organic light-emitting device having significantly improved long life and light-emitting efficiency. [Means for solving the problem]

[0006] In order to solve the above problems, the present invention provides a polycyclic compound represented by Chemical Formula 1 or Chemical Formula 2 having a characteristic fused ring structure as shown below, and an organic light-emitting device including the same as a dopant in an emitting layer. [Chemical formula 1] [Chemical formula 2] JPEG2025540511000001.jpg44117[Structural formula 1] JPEG2025540511000002.jpg3335

[0007] In Chemical Formula 1 and Chemical Formula 2, at least one pair of adjacent two of Z1 to Z7, Z1 and Z2, Z2 and Z3, Z4 and Z5, Z5 and Z6, or Z6 and Z7, is a carbon atom, and is simultaneously connected to the two * in Structural Formula 1 to form a ring.

[0008] The specific structures of Chemical Formula 1 and Chemical Formula 2, the specific compounds according to the present invention realized thereby, and the definitions of each substituent will be described later. [Effects of the Invention]

[0009] The present invention relates to a polycyclic compound having a characteristic fused ring structure and an organic light-emitting device using the compound as a dopant in the light-emitting layer. The present invention can realize an organic light-emitting device with improved efficiency and long life, and can be usefully used in various display elements such as flat, flexible, and wearable displays as well as lighting elements. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will now be described in more detail. One aspect of the present invention relates to a compound represented by the following Chemical Formula 1 or Chemical Formula 2. [Chemical formula 1] [Chemical formula 2] JPEG2025540511000003.jpg44117[Structural formula 1] JPEG2025540511000004.jpg3335

[0011] In the above Chemical Formula 1 and Chemical Formula 2, X is B, P=O, P=S or Al; Y1 is NR1, O, S, CR2R3, SiR4R5 or GeR6R7; and Y2 is NR8, O or S.

[0012] A is selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic heterocycle having 2 to 50 carbon atoms, and a fused ring of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms.

[0013] In Chemical Formula 1 and Chemical Formula 2, at least one pair of adjacent two of Z1 to Z7, Z1 and Z2, Z2 and Z3, Z4 and Z5, Z5 and Z6, or Z6 and Z7, is a carbon atom, and is simultaneously connected to the two * in Structural Formula 1 to form a ring. In this case, the remaining Z1 to Z7 that do not form a ring and Z8 to Z 14 are the same or different from each other and are each independently CR9 or N.

[0014] In addition, the above Z1 to Z 14 When comprises multiple CR9s, each CR9 may be the same or different. Z, Q and W are the same or different and each independently represent NR 10 , C.R. 11 R 12 , SiR 13 R 14 , GeR 15 R 16 , O or S.

[0015] The R1 to R 16are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted The alkyl group is selected from a fused ring group of a substituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0016] m is 0 or 1, and when m is 0, the carbon atom between Z and Z1 and the carbon atom between Z and Z4 are linked by a single bond. o is 0 or 1, and if o is 0, Z 11 and Q are connected to the carbon atom connected to * by a single bond, and n is 0 or 1. When n is 0, Z 14 and W and the carbon atom connected to * are connected by a single bond (with the proviso that o+n≧1).

[0017] In addition, the R2 to R 16 can be linked to adjacent substituents to form additional alicyclic or aromatic monocyclic or polycyclic rings. Furthermore, adjacent R9s may be linked together to form an additional alicyclic or aromatic monocyclic or polycyclic ring.

[0018] Furthermore, the R2 and R3, R4 and R5, R6 and R7, and R 11 and R 12 , R 13 and R 14and R 15 and R 16 can be linked to each other to form additional alicyclic or aromatic monocyclic or polycyclic rings.

[0019] According to one embodiment of the present invention, Z1 to Z7 and Z in Chemical Formula 1 and Chemical Formula 2 11 ~Z 14 At least one of the R9's is CR9, and at least one of the R9's is a bulky substituent that is not hydrogen or deuterium.

[0020] According to an embodiment of the present invention, the formula 1 may be represented by any one selected from the following formulas 1-1 to 1-5. [Chemical formula 1-1] [Chemical formula 1-2] JPEG2025540511000005.jpg54124[Chemical formula 1-3] [Chemical formula 1-4] JPEG2025540511000006.jpg58123[Chemical formula 1-5] JPEG2025540511000007.jpg4075

[0021] In the above Chemical Formula 1-1 to Chemical Formula 1-5, Z, Q, W, Z1 to Z 14 , Y1, Y2, m, n, o and A are the same as defined in Chemical Formula 1 above.

[0022] According to an embodiment of the present invention, the formula 2 may be represented by any one selected from the following formulas 2-1 to 2-5. [Chemical formula 2-1] [Chemical formula 2-2] JPEG2025540511000008.jpg63123[Chemical formula 2-3] [Chemical formula 2-4] JPEG2025540511000009.jpg62119[Chemical formula 2-5] JPEG2025540511000010.jpg4671

[0023] In the above Chemical Formulas 2-1 to 2-5, Z, Q, W, Z1 to Z14 , Y1, Y2, m, n, o and A are the same as defined in Chemical Formula 2 above.

[0024] Furthermore, the term "substituted or unsubstituted" in Chemical Formula 1, Chemical Formula 1-1 to Chemical Formula 1-5, Chemical Formula 2, Chemical Formula 2-1 to Chemical Formula 2-5 and Structural Formula 1 means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkylheteroaryl group having 3 to 30 carbon atoms, a carbon or a fused ring group of an aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, an amine group having 1 to 40 carbon atoms, a silyl group having 1 to 40 carbon atoms, a germanium group having 1 to 40 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or a group in which two or more of the above-mentioned substituents are linked together, wherein hydrogen in the substituent can be substituted with one or more deuterium, and two or more adjacent substituents can be linked together to form an additional alicyclic or aromatic monocyclic or polycyclic ring.

[0025] On the other hand, the range of the carbon number of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms," "substituted or unsubstituted aryl group having 6 to 50 carbon atoms," etc. means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when viewed as unsubstituted without taking into account the portion substituted with the substituent. For example, a phenyl group substituted with a butyl group at the para position corresponds to an aryl group having 6 carbon atoms and substituted with a butyl group having 4 carbon atoms.

[0026] In the present invention, "being linked to each other or to adjacent groups to form an additional ring" means that adjacent substituents among the specified substituents can be bonded to each other, or that a specified substituent can be bonded to another adjacent group to form a substituted or unsubstituted alicyclic or aromatic ring, and the term "adjacent group" can mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted on the ortho position of a benzene ring and two substituents substituted on the same carbon atom of an aliphatic ring can be interpreted as "adjacent groups" to each other. A pair of linked substituents can form an additional ring by removing one hydrogen radical from each of them and connecting them. Carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring can be replaced by heteroatoms such as N, NR, O, S, Si, or Ge. The R can be any of R1 to R in Chemical Formula 1 or Chemical Formula 2. 16 is the same as the definition of

[0027] In the present invention, the alkyl group may be a straight chain or a branched chain, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethyl Examples of alkyl groups include, but are not limited to, butyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0028] In the present invention, specific examples of arylalkyl groups include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and the like.

[0029] In the present invention, specific examples of alkylaryl groups include, but are not limited to, tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl.

[0030] In the present invention, alkenyl groups include straight-chain or branched-chain alkenyl groups, and may be additionally substituted with other substituents. 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 groups.

[0031] In the present invention, alkynyl groups also include straight or branched chains and may be additionally substituted with other substituents, including, but not limited to, ethynyl, 2-propynyl, and the like.

[0032] In the present invention, a cycloalkenyl group refers to a cyclic unsaturated hydrocarbon group that has one or more carbon-carbon double bonds and is not an aromatic ring, and examples thereof include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, 2,4-cycloheptadienyl, and 1,5-cyclooctadienyl.

[0033] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group directly linked to or fused with another ring group, and the other ring group may be an aromatic hydrocarbon ring, or may be another type of ring group, for example, an aliphatic heterocycle, an aliphatic hydrocarbon ring, an aromatic heterocycle, etc. Examples of monocyclic aryl groups include a phenyl group, a biphenyl group, and a terphenyl group, and examples of polycyclic aryl groups include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, a chrysenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluoranthene group, but the scope of the present invention is not limited to these examples.

[0034] In the present invention, an aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyridine ... Examples of such alkyl groups include, but are not limited to, an indyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, an indolocarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a phenothiazinyl group.

[0035] In the present invention, an aliphatic hydrocarbon ring or a cycloalkyl group means a ring consisting of carbon and hydrogen atoms as a non-aromatic ring, and examples thereof include a monocycle or a polycycle, which may be additionally substituted with other substituents. A polycycle means a group directly linked to or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, or may be another type of ring group, such as an aliphatic heterocycle, an aromatic hydrocarbon ring, or an aromatic heterocycle. Specific examples include, but are not limited to, cycloalkyls such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; cycloalkanes such as cyclohexane and cyclopentane; and cyclocycloalkenes such as cyclohexene and cyclobutene.

[0036] In the present invention, the aliphatic heterocycle or heterocycloalkyl group refers to an aliphatic ring containing one or more heteroatoms, such as O, S, Se, N, or Si, and may also include a monocycle or polycycle, which may be additionally substituted with other substituents. The polycycle refers to a group in which a heterocycloalkyl, heterocycloalkane, or the like is directly linked or fused with another ring group, and the other ring group may be an aliphatic heterocycle, or may be another type of ring group, such as an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, or an aromatic heterocycle.

[0037] In the present invention, a fused ring (group) of an aliphatic ring and an aromatic ring refers to an aliphatic-aromatic mixed ring (group), in which two or more rings are linked and fused to each other, and in which the aliphatic ring and the aromatic ring are fused to give a ring that has non-aromaticity overall, and more specifically, refers to an aromatic hydrocarbon ring (group) fused with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring (group) fused with an aliphatic heterocycle, an aromatic heterocycle (group) fused with an aliphatic hydrocarbon ring, an aromatic heterocycle (group) fused with an aliphatic heterocycle, an aromatic hydrocarbon ring fused with an aromatic hydrocarbon ring, The ring (group) may be an aliphatic hydrocarbon ring (group), an aliphatic hydrocarbon ring (group) fused with an aromatic heterocycle, an aliphatic heterocycle (group) fused with an aromatic hydrocarbon ring, or an aliphatic heterocycle (group) fused with an aromatic heterocycle. Specific examples include a tetrahydronaphthyl group, a tetrahydrobenzocycloheptene group, a tetrahydrophenanthrene group, a tetrahydroanthracenyl group, an octahydrotriphenylene group, a tetrahydrobenzothiophene group, a tetrahydrobenzofuranyl group, a tetrahydrocarbazole group, and a tetrahydroquinoline group. In addition, in addition to carbon atoms in the fused ring (group) of the aliphatic ring and the aromatic ring, heteroatoms such as N, NR, O, S, Si, and Ge can be substituted, and the R can be any of R1 to R in Chemical Formula 1 or Chemical Formula 2. 16 is the same as the definition of

[0038] In the present invention, the alkoxy group may specifically be methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited to these.

[0039] In the present invention, the silyl group may include -SiH3, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, etc., and the arylsilyl group refers to a silyl group in which one, two, or three hydrogen atoms in -SiH3 are substituted with an aryl group. The alkylsilyl group refers to a silyl group in which one, two, or three hydrogen atoms in SiH3 are substituted with an alkyl group. The alkylarylsilyl group refers to a silyl group in -SiH3 in which at least one hydrogen atom is substituted with an alkyl group and an aryl group, and which contains one or two alkyl groups and two or one corresponding aryl group. The arylheteroarylsilyl group refers to a silyl group in which at least one hydrogen atom in —SiH3 is replaced by an aryl group and a heteroaryl group, thereby containing one or two aryl groups and two or one corresponding heteroaryl group. The heteroarylsilyl group refers to a silyl group in —SiH3 in which one, two, or three hydrogen atoms are replaced by heteroaryl groups. Examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, and a substituted or unsubstituted triarylsilyl group. The same applies to the alkylsilyl group and heteroarylsilyl group.

[0040] Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0041] Specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutyrosilyl, and dimethylfurylsilyl, and one or more hydrogen atoms in the silyl group can be substituted with the same substituents as in the aryl group.

[0042] In the present invention, the amine group may include -NH, an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, etc., where the arylamine group refers to an amine in which one or two hydrogen atoms in -NH are substituted with an aryl group, the alkylamine group refers to an amine in which one or two hydrogen atoms in -NH are substituted with an alkyl group, the alkylarylamine group refers to an amine in which one hydrogen atom in -NH is substituted with an alkyl group and the remaining hydrogen atom in -NH is substituted with an aryl group, the arylheteroarylamine group refers to an amine in which one hydrogen atom in -NH is substituted with an aryl group and the remaining hydrogen atom in -NH is substituted with a heteroaryl group, and the heteroarylamine group refers to an amine in which one or two hydrogen atoms in -NH are substituted with a heteroaryl group. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, and a substituted or unsubstituted triarylamine group, as well as the alkylamine group and heteroarylamine group.

[0043] Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, or may be a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0044] In the present invention, the germanium group (or germane group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc., and although the definitions of these are the same as those explained for the silyl group, they are substituents obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group, and are applicable to each substituent.

[0045] Specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, and dimethylfurylgermane, and one or more hydrogen atoms in the germanium group can be substituted with the same substituents as in the aryl group.

[0046] In the present invention, the cycloaryl group, aryl group, and heteroaryl group in the cycloalkyloxy group, aryloxy group, heteroaryloxy group, cycloalkylthio group, arylthio group, and heteroarylthio group are the same as the above-mentioned examples of the cycloaryl group, aryl group, and heteroaryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenoxy group, and a 2,4,6-trimethylphenoxy group. Examples of arylthioxy groups include, but are not limited to, a phenylthioxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group. Examples of arylthioxy groups include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

[0047] In the present invention, examples of halogen groups include fluorine, chlorine, bromine or iodine. According to one embodiment of the present invention, the polycyclic compound represented by Chemical Formula 1 or Chemical Formula 2 may be any one selected from compounds represented by the following chemical formulas, but the scope thereof is not limited thereto.

[0048] JPEG2025540511000011.jpg166149 JPEG2025540511000012.jpg174149 JPEG2025540511000013.jpg184149 JPEG2025540511000014.jpg196149

[0049] Another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer, preferably the light-emitting layer, contains a compound represented by Chemical Formula 1 or Chemical Formula 2 as a dopant.

[0050] The light-emitting layer has a structure consisting of a host and a dopant, and may further include a host material. In this case, the content of the dopant including the polycyclic compound according to the present invention may be selected from the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0051] In addition, the light-emitting layer may further contain various dopants and various host materials in addition to the dopant compound and host compound according to the present invention. Thus, not only the host but also the dopant materials in the light-emitting layer may be a mixture or stack of one or more different compounds.

[0052] According to one embodiment of the present invention, the host compound employed in the light-emitting layer may be an anthracene compound represented by the following Chemical Formula 3: [Chemical formula 3] JPEG2025540511000015.jpg5264

[0053] In the above Chemical Formula 3, R 21 ~R 28are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted The alkyl group is selected from a fused ring group of a substituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0054] Ar1 and Ar3 are the same or different and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

[0055] Ar2 and Ar4 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms.

[0056] D n means the number of hydrogen atoms in chemical formula 3 that have been replaced with deuterium atoms, and n is an integer of 0 to 50. According to one embodiment of the present invention, the anthracene compound represented by Chemical Formula 3 may be any one selected from the compounds represented by the following chemical formulas, but the scope thereof is not limited thereto.

[0057] JPEG2025540511000016.jpg185147 JPEG2025540511000017.jpg198147 JPEG2025540511000018.jpg182147 JPEG2025540511000019.jpg188147 JPEG2025540511000020.jpg165147 JPEG2025540511000021.jpg202147 JPEG2025540511000022.jpg189147 JPEG2025540511000023.jpg199147 JPEG2025540511000024.jpg163147 JPEG2025540511000025.jpg179147 JPEG2025540511000026.jpg195147 JPEG2025540511000027.jpg172147 JPEG2025540511000028.jpg176147 JPEG2025540511000029.jpg202147 JPEG2025540511000030.jpg173147 JPEG2025540511000031.jpg173147 JPEG2025540511000032.jpg201147 JPEG2025540511000033.jpg191147 JPEG2025540511000034.jpg200147 JPEG2025540511000035.jpg169147 JPEG2025540511000036.jpg173147 JPEG2025540511000037.jpg138147

[0058] The organic layer of the organic light emitting device according to the present invention may have a single layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, an emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, it is not limited thereto and may include fewer or more organic layers. The organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in the examples below.

[0059] An embodiment of the organic light emitting device according to the present invention will now be described in more detail. The organic light emitting device according to the present invention includes an anode, a hole transport layer, an emitting layer, an electron transport layer, and a cathode. If necessary, the organic light emitting device may further include a hole injection layer between the anode and the hole transport layer, and may further include an electron injection layer between the electron transport layer and the cathode. In addition, one or two intermediate layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed. As described above, the organic light emitting device may further include organic layers having various functions, such as a capping layer, depending on the characteristics of the device.

[0060] Meanwhile, a specific structure of an organic light emitting device according to an embodiment of the present invention, a manufacturing method thereof, and materials for each organic layer will be described below. First, an anode is formed by coating the substrate with an anode material. The substrate can be a substrate commonly used in organic light-emitting devices, but an organic substrate or transparent plastic substrate is preferred due to its transparency, surface smoothness, ease of handling, and water resistance. The anode material is typically indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO), zinc oxide (ZnO), or other transparent and conductive materials.

[0061] A hole injection layer is formed on the anode electrode by vacuum thermal deposition or spin coating of a hole injection layer material, and then a hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating of a hole transport layer material.

[0062] The hole injection layer material is not particularly limited as long as it is commonly used in the art. Specific examples include 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], and DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine].

[0063] The material for the hole transport layer is not particularly limited as long as it is a material commonly used in the art. For example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) can be used.

[0064] Next, a hole-assisting layer and an emitting layer are sequentially stacked on the hole-transporting layer, and a hole-blocking layer can be optionally formed on the emitting layer by vacuum deposition or spin coating. The hole-blocking layer prevents the device's lifetime and efficiency from decreasing if holes pass through the organic emitting layer to the cathode. The hole-blocking layer uses a material with a very low HOMO (Highest Occupied Molecular Orbital) level to prevent this problem. The hole-blocking material used is not particularly limited, but should have electron transport capability and a higher ionization potential than the emitting compound. Typical examples include BAlq, BCP, and TPBI.

[0065] The hole blocking layer may be made of, but is not limited to, BAlq, BCP, Bphen, TPBI, TAZ, BeBq2, OXD-7, Liq, and the like. An electron transport layer is deposited on the hole blocking layer by vacuum deposition or spin coating, followed by forming an electron injection layer. A cathode electrode is formed on the electron injection layer by vacuum thermal deposition of a metal for forming a cathode, thereby completing an organic light emitting device according to one embodiment of the present invention.

[0066] Here, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used as the metal for forming the cathode, and a transmission type cathode using ITO or IZO can be used to obtain a front light emitting element.

[0067] The electron transport layer material has a function of stably transporting electrons injected from the cathode, and known electron transport materials can be used. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), and oxadiazole derivatives (PBD, BMD, BND, etc.).

[0068] In addition, each of the organic layers may be formed by a monomolecular deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used to form each of the layers by heating under vacuum or low pressure conditions, and the solution process refers to a method of mixing a material used to form each of the layers with a solvent and forming a thin film by methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.

[0069] In addition, the organic light emitting device according to the present invention may be used in a device selected from a flat display device, a flexible display device, a monochrome or white flat lighting device, a monochrome or white flexible lighting device, a vehicle display device, a virtual or augmented reality display device, etc. [Example]

[0070] To aid in understanding the present invention, the following examples of synthesis of preferred compounds and device examples are presented. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[0071] Synthesis Example 1: Synthesis of [Compound 1] Synthesis Example 1-1: Synthesis of A-1 JPEG2025540511000038.jpg22137 <a-1a> <a-1b> <a-1>

[0072] Into the reactor, <a-1a> 45g、 <a-1b>32g, tris(dibenzylideneacetone)dibaladium(0) 3.94g, sodium tert-butoxide 41.3g, bis(diphenylphosphino)-1,1'-binaphthyl 2.68g, and toluene 450mL were added and refluxed with stirring for 5 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. The product was purified by silica gel chromatography. <a-1>(38.5g, 64.5%)

[0073] Synthesis Example 1-2: Synthesis of A-2 JPEG2025540511000039.jpg27140 <a-1> <a-2a> <a-2>

[0074] Into the reactor, <a-1> 38g、 <a-2a>After adding 36.8g of bis(tri-tert-butylphosphine)palladium(0), 1.4g of bis(tri-tert-butylphosphine)palladium(0), 26.3g of sodium tert-butoxide, and 400mL of toluene, the mixture was refluxed and stirred for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. The mixture was purified by silica gel chromatography. <a-2>(36.7g, 57.6%)

[0075] Synthesis Example 1-3: Synthesis of A-3 JPEG2025540511000040.jpg34145 <a-2> <a-3a> <a-3>

[0076] Into the reactor, <a-2> 35g、 <a-3a>After adding 18.4g of ethanol, 76.7g of cesium carbonate, and 350mL of dimethylformamide, the mixture was refluxed and stirred for 8 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. The product was purified by silica gel chromatography. <a-3>(38g, 73.1%)

[0077] Synthesis Example 1-4: Synthesis of [Compound 1] JPEG2025540511000041.jpg36109 <a-3>[Compound 1]

[0078] Into the reactor, <a-3>After adding 38g of toluene and 400mL of toluene, 79mL of 2M tertiary-butyllithium pentane solution was added dropwise at -78°C. The mixture was heated to 60°C and stirred for 2 hours, after which nitrogen was blown in at 60°C to completely remove the pentane. After cooling to -78°C, 5.1mL of boron tribromide was added dropwise. The mixture was heated to room temperature and stirred for 2 hours, then cooled to 0°C and 9.4mL of N,N-diisopropylethylamine was added dropwise. The mixture was heated to 120°C and stirred for 16 hours. After cooling to room temperature, 10% aqueous sodium acetate solution and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. Purification by silica gel chromatography gave [Compound 1] (5.4g, 14.7%). MS (MALDI-TOF): m / z 676.27 [M + ]

[0079] Synthesis Example 2: Synthesis of [Compound 5] Synthesis Example 2-1: Synthesis of B-1 JPEG2025540511000042.jpg24120 <b-1a> <b-1b> <b-1>

[0080] Into the reactor, <b-1a> 45g、 <b-1b>After adding 23.5g of tetrakispalladium(0), 5.1g of potassium carbonate, 41.3g of potassium carbonate, 500mL of toluene, 300mL of ethanol, and 200mL of water, the mixture was refluxed and stirred for 8 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and then 12.5g of triphenylphosphine and 400mL of methylpyrrolidone were added, and the mixture was refluxed and stirred for 8 hours. The resulting product was purified by silica gel chromatography. <b-1>(41.7g, 90.6%)

[0081] Synthesis Example 2-2: Synthesis of B-2 JPEG2025540511000043.jpg39138 <a-2> <b-1> <b-2> The compound used in Synthesis Example 1-3 <a-3a>instead of <b-1>It was synthesized in a similar manner except that <b-2>(Yield 79.6%)

[0082] Synthesis Example 2-3: Synthesis of [Compound 5] JPEG2025540511000044.jpg39141 <b-2>[Compound 5] The compound used in Synthesis Example 1-4 <a-3>instead of <b-2>Compound 5 was synthesized in the same manner except for using the compound (15.4% yield). MS (MALDI-TOF): m / z 732.33 [M + ]

[0083] Synthesis Example 3: Synthesis of [Compound 7] Synthesis Example 3-1: Synthesis of C-1 JPEG2025540511000045.jpg25131 <c-1a> <b-1b> <c-1> The compound used in Synthesis Example 2-1 <b-1a>instead of <c-1a>It was synthesized in a similar manner except that <c-1>(yield 81.4%)

[0084] Synthesis Example 3-2: Synthesis of C-2 JPEG2025540511000046.jpg42137 <a-2> <c-1> <c-2> The compound used in Synthesis Example 1-3 <a-3a>instead of <c-1>It was synthesized in a similar manner except that <c-2>(Yield 74.5%)

[0085] Synthesis Example 3-3: Synthesis of [Compound 7] JPEG2025540511000047.jpg42137 <c-2>[Compound 7] The compound used in Synthesis Example 1-4 <a-3>instead of <c-2>Compound 7 was synthesized in the same manner except for using the compound (16% yield). MS (MALDI-TOF): m / z 768.28 [M + ]

[0086] Synthesis Example 4: Synthesis of [Compound 9] Synthesis Example 4-1: Synthesis of D-1 JPEG2025540511000048.jpg24132 <d-1a> <d-1b> <d-1> The compound used in Synthesis Example 2-1 <b-1a>instead of <d-1a>Using <b-1b>instead of <d-1b>It was synthesized in a similar manner except that <d-1>(Yield 74.2%)

[0087] Synthesis Example 4-2: Synthesis of D-2 JPEG2025540511000049.jpg37143 <a-2> <d-1> <d-2> The compound used in Synthesis Example 1-3 <a-3a>instead of <d-1>It was synthesized in a similar manner except that <d-2>(yield 65.7%)

[0088] Synthesis Example 4-3: Synthesis of [Compound 9] JPEG2025540511000050.jpg37143 <d-2>[Compound 9] The compound used in Synthesis Example 1-4 <a-3>instead of <d-2>Compound 9 was synthesized in the same manner except for using the compound (10.1% yield). MS (MALDI-TOF): m / z 804.37 [M + ]

[0089] Synthesis Example 5: Synthesis of [Compound 33] Synthesis Example 5-1: Synthesis of E-1 JPEG2025540511000051.jpg36136 <e-1a> <e-1b> <e-1> The compound used in Synthesis Example 2-1 <b-1a>instead of <e-1a>Using <b-1b>instead of <e-1b>It was synthesized in a similar manner except that <e-1>(yield 88.7%)

[0090] Synthesis Example 5-2: Synthesis of E-2 JPEG2025540511000052.jpg33141 <e-2a> <e-2b> <e-2> The compound used in Synthesis Example 1-1 <a-1a>instead of <e-2a>Using <a-1b>instead of <e-2b>It was synthesized in a similar manner except that <e-2>(yield 81.6%)

[0091] Synthesis Example 5-3: Synthesis of E-3 JPEG2025540511000053.jpg36130 <e-2> <a-2a> <e-3> The compound used in Synthesis Example 1-2 <a-1>instead of <e-2>It was synthesized in a similar manner except that <e-3>(Yield 74.1%)

[0092] Synthesis Example 5-4: Synthesis of E-4 JPEG2025540511000054.jpg39148 <e-3> <e-1> <e-4> The compound used in Synthesis Example 1-3 <a-2>instead of <e-3>Using <a-3a>instead of <e-1>It was synthesized in a similar manner except that <e-4>(yield 65.4%)

[0093] Synthesis Example 5-5: Synthesis of [Compound 33] JPEG2025540511000055.jpg44151 <e-4>[Compound 33] The compound used in Synthesis Example 1-4 <a-3>instead of <e-4>Compound 33 was synthesized in the same manner except for using the compound 33. (Yield: 8.4%) MS (MALDI-TOF): m / z 1044.34 [M + ]

[0094] Synthesis Example 6: Synthesis of [Compound 20] Synthesis Example 6-1: Synthesis of F-1 JPEG2025540511000056.jpg31133 <a-1> <f-1a> <f-1> The compound used in Synthesis Example 1-2 <a-2a>instead of <f-1a>It was synthesized in a similar manner except that <f-1>(yield 88.4%)

[0095] Synthesis Example 6-2: Synthesis of F-2 JPEG2025540511000057.jpg34125 <f-1> <f-2a> <f-2> The compound used in Synthesis Example 1-3 <a-2>instead of <f-1>Using <a-3a>instead of <f-2a>It was synthesized in a similar manner except that <f-2>(Yield 71.5%)

[0096] Synthesis Example 6-3: Synthesis of [Compound 20] JPEG2025540511000058.jpg37142 <f-2>[Compound 20] The compound used in Synthesis Example 1-4 <a-3>instead of <f-2>Compound 20 was obtained by the same synthesis method except for using the compound (10.5% yield). MS (MALDI-TOF): m / z 695.26 [M + ]

[0097] Synthesis Example 7: Synthesis of [Compound 34] Synthesis Example 7-1: Synthesis of G-1 JPEG2025540511000059.jpg28131 <g-1a> <b-1b> <g-1> The compound used in Synthesis Example 2-1 <b-1a>instead of <g-1a>It was synthesized in a similar manner except that <g-1>(Yield 74.7%)

[0098] Synthesis Example 7-2: Synthesis of G-2 JPEG2025540511000060.jpg24131 <a-1a> <g-2a> <g-2> The compound used in Synthesis Example 1-1 <a-1b>instead of <g-2a>It was synthesized in a similar manner except that <g-2>(yield 88.6%)

[0099] Synthesis Example 7-3: Synthesis of G-3 JPEG2025540511000061.jpg30129 <g-2> <g-3a> <g-3> The compound used in Synthesis Example 1-2 <a-1>instead of <g-2>Using <a-2a>instead of <g-3a>It was synthesized in a similar manner except that <g-3>(yield 68.7%)

[0100] Synthesis Example 7-4: Synthesis of G-4 JPEG2025540511000062.jpg32138 <g-3> <g-1> <g-4> The compound used in Synthesis Example 1-3 <a-2>instead of <g-3>Using <a-3a>instead of <g-1>It was synthesized in a similar manner except that <g-4>(Yield 74.3%)

[0101] Synthesis Example 7-5: Synthesis of [Compound 34] JPEG2025540511000063.jpg33120 <g-4>[Compound 34] The compound used in Synthesis Example 1-4 <a-3>instead of <g-4>Compound 34 was synthesized in the same manner except for using the compound 34. (Yield 12.7%) MS (MALDI-TOF): m / z 790.37 [M]

[0102] Examples 1 to 7: Fabrication of organic light-emitting devices The ITO glass was patterned so that the light-emitting area was 2 mm × 2 mm, and then washed. The ITO glass was placed in a vacuum chamber, and the base pressure was 1 × 10 -7 After adjusting the pressure to torr, a hole-injection layer (100 Å) was formed on the ITO using an electron acceptor of the following structural formula [Acceptor-1] and [Chemical Formula F] at a vapor deposition ratio of [Acceptor-1]:[Chemical Formula F] = 2:98. A hole-transport layer (550 Å) of [Chemical Formula F] was then formed, followed by an electron-blocking layer (50 Å) of [Chemical Formula G]. The light-emitting layer was formed by mixing the host [BH-1] described below with a compound of the present invention (2 wt%) and then depositing a hole-blocking layer (50 Å) of [Chemical Formula H]. An electron-transport layer (250 Å) of [Chemical Formula E-1] and [Chemical Formula E-2] in a 1:1 ratio was then deposited. Finally, an organic light-emitting device was fabricated by depositing [Chemical Formula E-2] (10 Å) and Al (1000 Å) in that order. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0103] [Chemical formula F] [Chemical formula G] [Chemical formula H] JPEG2025540511000064.jpg45140[Chemical formula E-1] [Chemical formula E-2] [Acceptor-1] JPEG2025540511000065.jpg39134[BH-1] JPEG2025540511000066.jpg4128

[0104] Comparative Examples 1 to 3 Organic light-emitting devices were fabricated in the same manner as in the previous examples, except that [RD-1] to [RD-3] were used instead of the compounds used in the previous examples, and the light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA. The structures of [RD-1] to [RD-3] are as follows. [RD-1] [RD-2] [RD-3] JPEG2025540511000067.jpg26115

[0105] The external quantum efficiency and lifetime of the organic light emitting devices manufactured in Examples 1 to 7 and Comparative Examples 1 to 3 were measured, and the results are shown in Table 1 below.

[0106] [Table 1]

[0107] As shown in Table 1, a device employing the compound according to the present invention as a dopant compound in the light-emitting layer of an organic light-emitting device can realize a highly efficient, long-life organic light-emitting device with excellent quantum efficiency and life characteristics, compared to devices (Comparative Examples 1 to 3) employing compounds that have a characteristic structure comparable to that of the compound according to the present invention. [Industrial Applicability]

[0108] The present invention relates to a polycyclic compound having a characteristic fused ring structure and an organic light-emitting device using the compound as a dopant in an emitting layer. The compound according to the present invention can realize an organic light-emitting device with improved efficiency and long life, and can be industrially usefully used in various display devices such as flat, flexible, and wearable displays as well as lighting devices. < / g-1> < / g-3> < / g-3a> < / g-2> < / g-2a> < / a-1a> < / b-1b> < / g-1a> < / f-2a> < / f-1> < / f-1a> < / a-1> < / e-1> < / e-3> < / a-2a> < / e-2> < / e-2b> < / e-2a> < / e-1b> < / e-1a> < / d-1> < / a-2> < / d-1b> < / d-1a> < / c-1> < / a-2> < / b-1b> < / c-1a> < / b-1> < / a-2> < / b-1a> < / b-1b> < / b-1a> < / a-2> < / a-3a> < / a-2> < / a-1> < / a-2a> < / a-1> < / a-1a> < / a-1b> < / a-1a>

Claims

1. A polycyclic compound represented by the following chemical formula 1 or 2: [Chemical formula 1] [Chemical formula 2] In the above Chemical Formula 1 and Chemical Formula 2, X is B, P=O, P=S or Al; Y １ is NR １ ,O.S.,CR. ２ R ３ , SiR ４ R ５ or GeR ６ R ７ and Y ２ is NR ８ , O or S; A is any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic heterocycle having 2 to 50 carbon atoms, and a fused ring of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms; Z １ ~Z ７ Two adjacent Zs １ and Z ２ , Z ２ and Z ３ , Z ４ and Z ５ , Z ５ and Z ６ , Z ６ and Z ７ At least one pair of is a carbon atom, and is simultaneously connected to two * in the following structural formula 1 to form a ring, [Structural formula 1] Said Z １ ~Z ７ The remainder of the group that does not form a ring and Z ８ ~Z １４ are the same or different from each other, and each independently represents CR ９ or N, Said Z １ ~Z １４ There are multiple CRs ９ If it contains, each CR ９ are the same or different, Z, Q and W are the same or different and each independently represent NR １０ , C.R. １１ R １２ , SiR １３ R １４ , GeR １５ R １６ , O or S; The R １ ~R １６ are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted carbon any one selected from a fused ring group of an aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group; m is 0 or 1, and when m is 0, Z and Z １ and the carbon atom between Z and Z ４ The carbon atoms between are connected by a single bond, o is 0 or 1, and when o is 0, Z １１ and Q are connected to the carbon atom connected to * by a single bond, n is 0 or 1, and when n is 0, Z １４ and W are connected to the carbon atom connected to * by a single bond, However, o+n≧1, The R ２ ~R １６ can be linked to adjacent substituents to form additional alicyclic or aromatic monocyclic or polycyclic rings; The adjacent plurality of R ９ can be linked together to form additional alicyclic or aromatic monocyclic or polycyclic rings, The R ２ and R ３ , R ４ and R ５ , R ６ and R ７ , R １１ and R １２ , R １３ and R １４ and R １５ and R １６ may be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring; The term "substituted" in "substituted or unsubstituted" in Chemical Formula 1, Chemical Formula 2, and Structural Formula 1 refers to deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, a heterocycloalkyl group having 2 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkylheteroaryl group having 3 to 30 carbon atoms, an aliphatic ring and a carbon atom having 3 to 24 carbon atoms, or an alkylheteroaryl group having 3 to 24 carbon atoms. The term "substituted" means that the substituted group is substituted with one or more substituents selected from the group consisting of a fused ring group with an aromatic ring having 3 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, an amine group having 1 to 40 carbon atoms, a silyl group having 1 to 40 carbon atoms, a germanium group having 1 to 40 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or two or more of the above substituents are substituted with a linked substituent, wherein hydrogen in the substituent can be substituted with one or more deuterium, and two or more adjacent substituents can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring.

2. Z in the above Chemical Formula 1 and Chemical Formula 2 １ ~Z ７ and Z １１ ~Z １４ At least one of the following is CR ９ and the plurality of R ９ The polycyclic compound according to claim 1 , wherein at least one of is not hydrogen or deuterium.

3. The polycyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one selected from the following chemical formulas 1-1 to 1-5: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] In the chemical formulas 1-1 to 1-5, Z, Q, W, Z １ ~Z １４ , Y １ , Y ２ , m, n, o and A are the same as defined in Chemical Formula 1 of claim 1.

4. The polycyclic compound according to claim 1, wherein the chemical formula 2 is represented by any one selected from the following chemical formulas 2-1 to 2-5: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] In the chemical formulas 2-1 to 2-5, Z, Q, W, Z １ ~Z １４ , Y １ , Y ２ , m, n, o and A are the same as defined in Chemical Formula 2 of claim 1.

5. The polycyclic compound according to claim 1, wherein the formula 1 or 2 is any one selected from compounds represented by the following formulas:

6. a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode; The organic light-emitting device according to claim 1 , wherein the organic layer comprises at least one polycyclic compound represented by Chemical Formula 1 or Chemical Formula 2.

7. the organic layer includes one or more layers selected from the group consisting of an electron injection layer, a hole injection layer, a hole transport layer, an electron blocking layer, a functional layer having both a hole injection function and a hole transport function, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a functional layer having both an electron injection function and an electron transport function, The organic light-emitting device according to claim 6 , wherein one or more of the layers contains at least one polycyclic compound represented by Chemical Formula 1 or Chemical Formula 2.

8. The organic light-emitting device according to claim 7 , wherein the light-emitting layer comprises a host and a dopant, and at least one of the polycyclic compounds represented by Chemical Formula 1 or Chemical Formula 2 is a dopant in the light-emitting layer.

9. The organic light-emitting device according to claim 8, wherein the host is an anthracene compound represented by the following Chemical Formula 3: [Chemical formula 3] In the above Chemical Formula 3, R ２１ ~R ２８ are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted carbon any one selected from a fused ring group of an aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group; Ar １ and Ar ３ are the same or different and each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms; Ar ２ and Ar ４ are the same or different and each independently represent one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms; D ｎ means the number of hydrogen atoms in formula 3 that are replaced with deuterium atoms, and n is an integer of 0 to 50.

10. The organic light-emitting device according to claim 9, wherein the compound represented by Chemical Formula 3 is any one selected from the compounds represented by the following chemical formulas:

11. The organic light emitting device according to claim 7 , wherein at least one of the layers is formed by a vapor deposition process or a solution process.

12. The organic light emitting device according to claim 8, wherein the host in the light emitting layer is a mixture or laminate of one or more compounds other than the compound represented by Chemical Formula 3.

13. The organic light emitting device according to claim 8, wherein the dopant in the light emitting layer is a mixture or laminate of one or more compounds other than the compound represented by Chemical Formula 1 or Chemical Formula 2.

14. 10. The organic light-emitting device according to claim 6, wherein the organic light-emitting device is used in any one device selected from the group consisting of a flat display device; a flexible display device; a monochrome or white flat lighting device; a monochrome or white flexible lighting device; a vehicle display device; and a virtual or augmented reality display device.

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