Polycyclic compound, and organic light-emitting device using same

Abstract

The present invention relates to: a polycyclic compound having a characteristic fused ring structure; and an organic light-emitting device using same. The polycyclic compound according to the present invention can be used in a light-emitting layer in the organic light-emitting device to achieve a highly efficient long-lasting organic light-emitting device having a remarkably improved life span and excellent luminous efficiency, and thus can be effectively used commercially for lighting devices as well as various display devices such as flat panel, flexible, wearable, and virtual or augmented reality displays.

Description

Polycyclic ring compound and organic light-emitting device containing the same

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

[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 a light-emitting layer to form excitons, and the excitons emit energy, thereby emitting light. Such an organic light-emitting device is attracting attention as a next-generation light source due to its advantages of low operating voltage, high brightness, wide viewing angle, and fast response speed, and its applicability to full-color flat panel light-emitting displays.

[0003] In order for these organic light-emitting devices to exhibit the above-described characteristics, the structure of the organic layers within the device must be optimized, and the materials that make up each organic layer, such as hole injection materials, hole transport materials, hole blocking materials, luminescent materials, electron transport materials, electron injection materials, and electron blocking materials, must first be supported by stable and efficient materials. However, the development of the structure of the organic layers and each material for stable and efficient organic light-emitting devices is still continuously necessary.

[0004] In particular, to obtain maximum efficiency in the light-emitting layer, the energy band gaps of the host and dopant must be appropriately combined so that holes and electrons can move to the dopant through stable electrochemical pathways to form excitons.

[0005] Accordingly, the present invention aims to provide a high-efficiency, long-life organic light-emitting device having significantly improved lifespan and luminous efficiency by employing a polycyclic ring compound having a characteristic condensed ring structure and employing the same as a dopant material in a light-emitting layer.

[0006] In order to solve the above problem, the present invention provides a polycyclic ring compound represented by [chemical formula 1] having a characteristic condensed ring structure as follows, and an organic light-emitting device including the polycyclic ring compound as a dopant in a light-emitting layer.

[0007] [Chemical Formula 1]

[0008]

[0009] The specific structure of the above [chemical formula 1] and the specific compound and definition of each substituent according to the present invention implemented accordingly will be described later.

[0010] The present invention relates to a polycyclic ring compound having a characteristic condensed ring structure and an organic light-emitting device employing the same as a dopant in a light-emitting layer, and since it can realize a high-efficiency, long-life organic light-emitting device, it can be usefully utilized in various display devices such as lighting devices, flat panel, flexible, wearable, virtual or augmented reality displays, etc.

[0011] Hereinafter, the present invention will be described in more detail.

[0012] One aspect of the present invention relates to a polycyclic ring compound represented by the following [chemical formula 1].

[0013] [Chemical Formula 1]

[0014]

[0015] In the above [chemical formula 1],

[0016] X, Y1 and Y2 are each independently B or N.

[0017] Z1 and Z2 are the same or different, and are each independently selected from O, S, NR1, CR2R3, SiR4R5, and GeR6R7.

[0018] A1 ring to A4 ring are the same or different from each other, and are each independently 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.

[0019] At this time, at least one of the A1 to A4 rings is characterized by being 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.

[0020] R is 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 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, 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 carbon It is selected from among arylthioxy groups having 5 to 30 carbon atoms, substituted or unsubstituted amine groups, substituted or unsubstituted silyl groups, substituted or unsubstituted germanium groups, nitro groups, cyano groups, and halogen groups.

[0021] R1 to R7 are the same or different, and each independently represents 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 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, 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 It is selected from an alkylthioxy group, 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.

[0022] The above A1 ring is connected to X and Y1 to form a ring, the A2 ring is connected to X and Y2 to form a ring, the A3 ring is connected to Y1 and Z1 to form a ring, and the A4 ring is connected to Y2 and Z2 to form a ring.

[0023] The above R may be linked to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0024] The above R2 and R3, R4 and R5, and R6 and R7 may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0025] The above R1 to R7 may be connected to an adjacent A3 ring or A4 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0026] The above adjacent A1 to A4 rings can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0027]

[0028] In the above [Chemical Formula 1], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 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 2 to 30 carbon atoms, 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, It means that it is substituted with one or two or more substituents selected from the group consisting of an amine group, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or that two or more of the above substituents are substituted with a substituent that is connected, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0029]

[0030] According to one embodiment of the present invention, the compound of [chemical formula 1] according to the present invention is characterized in that when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

[0031] According to one embodiment of the present invention, Z1 and Z2 in the above [chemical formula 1] are the same as or different from each other, and can each be independently selected from O, S, and NR1.

[0032] In addition, according to one embodiment of the present invention, at least one of Z1 and Z2 in the above [chemical formula 1] may be O or S.

[0033]

[0034] In addition, the compound according to the present invention may have at least one deuterium in the above [chemical formula 1] substituted.

[0035]

[0036] According to one embodiment of the present invention, the A1 ring in the above [chemical formula 1] is characterized by being a fused ring of a substituted or unsubstituted aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 3 to 24 carbon atoms, and accordingly, the above [chemical formula 1] can be represented by the following [chemical formula 1-1] to [chemical formula 1-3].

[0037] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0038]

[0039] [Chemical Formula 1-3]

[0040]

[0041] In the above [Chemical Formula 1-1] to [Chemical Formula 1-3],

[0042] X, Y1 and Y2 are each independently B or N.

[0043] Z1 and Z2 are the same or different, and are each independently selected from O, S, and NR1.

[0044] A2 ring to A4 ring are the same or different from each other, and are each independently 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.

[0045] R and R 19 are the same or different from each other, and each independently represents 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 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, 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 aryl group having 1 to 30 carbon atoms It is selected from an alkylthioxy group, 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.

[0046] R1 and R 11 Inland R 14are the same or different from each other, and are each independently selected from 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, 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.

[0047] R 15 Inland R 18 are identical or different from each other, and each is independently hydrogen or deuterium.

[0048] m is an integer of 2.

[0049] The above A2 ring is connected to X and Y2 to form a ring, the above A3 ring is connected to Y1 and Z1 to form a ring, and the above A4 ring is connected to Y2 and Z2 to form a ring.

[0050] The above R may be linked to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0051] The above adjacent R 11 Inland R 14 can be linked to each other to form additional alicyclic or aromatic monocyclic or polycyclic rings.

[0052] The above R1 may be connected to an adjacent A3 ring or A4 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0053] The above adjacent A2 ring and A4 ring can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0054]

[0055] In the above [Chemical Formula 1-1] to [Chemical Formula 1-3], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 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 2 to 30 carbon atoms, 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, It means that it is substituted with one or two or more substituents selected from the group consisting of an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group and a nitro group, or is substituted with a substituent in which two or more of the above substituents are connected, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0056]

[0057] According to one embodiment of the present invention, the compounds of [Chemical Formula 1-1] to [Chemical Formula 1-3] according to the present invention are characterized in that when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

[0058]

[0059] Meanwhile, in the present invention, the term 'substituted or unsubstituted' means that each of the substituents defined above is selected from the group consisting of deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 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 2 to 30 carbon atoms, 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 alkyl group having 1 to It means that it is substituted with one or two or more substituents selected from the group consisting of an amine group having 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group and a nitro group, or is substituted with a substituent in which two or more substituents among the above substituents are connected, and hydrogen in the above substituents can be replaced with one or more deuteriums, and two or more adjacent substituents are connected to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring, for example, an amine group having 1 to 30 carbon atoms is substituted in the A ring, or an amine group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 24 carbon atoms is substituted, or an aryl group having 6 to 30 carbon atoms and an alkyl group having 1 to 24 carbon atoms are substituted with a 6 to 10 carbon atoms It means that 30 aryl groups are substituted simultaneously.

[0060]

[0061] In addition, in the present invention, the carbon number range 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 portion or aryl portion when the substituent is viewed as unsubstituted without considering the substituted portion. For example, a phenyl group substituted with a butyl group at the para-position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0062]

[0063] In addition, in the present invention, the meaning of forming an additional ring by being connected to each other or to adjacent groups means that adjacent substituents among the specified substituents can be connected to each other, or a specified substituent and another adjacent group can be connected to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and the 'adjacent group' can mean a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent located sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as 'adjacent groups', and a pair of connected substituents additionally form a ring by removing one hydrogen radical from each and connecting them, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring can be replaced with heteroatoms such as N, NR, O, S, Si, Ge, etc. (R has the same definition as R1 to R7 in [Chemical Formula 1]).

[0064]

[0065] In the present invention, the alkyl group may be straight-chain or branched, 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-methyl-butyl group, a 1-ethyl-butyl 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-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohectylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, Examples thereof include, but are not limited to, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0066] In the present invention, specific examples of the arylalkyl group include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc.

[0067] In the present invention, specific examples of the alkylaryl group include, but are not limited to, tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, t-butylphenanthryl, etc.

[0068] In the present invention, the alkenyl group includes a straight chain or a branched chain, and may be further substituted by another substituent, and specifically, includes a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, a styrenyl group, etc., but is not limited thereto.

[0069] In the present invention, the alkynyl group also includes a straight chain or branched chain, and may be further substituted by another substituent, and examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0070] In the present invention, a cycloalkenyl group is a cyclic unsaturated hydrocarbon group having one or more carbon double bonds and not an aromatic ring, and may include, but is not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, 2,4-cycloheptadienyl, and 1,5-cyclooctadienyl groups.

[0071] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group directly connected to or condensed with another ring group, and the other ring group may be an aromatic hydrocarbon ring, but may also 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, a terphenyl group, etc., and examples of polycyclic aryl groups include a naphthyl group, 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, a fluoranthene group, etc., but the scope of the present invention is not limited to these examples.

[0072] In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one heteroatom, 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 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 pyrido pyrimidinyl group, a pyrido pyrazinyl group, a pyrazino pyrazinyl 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, Examples thereof include, but are not limited to, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, and phenothiazinyl group.

[0073] In the present invention, an aliphatic hydrocarbon ring or cycloalkyl group means a ring that is not aromatic and is composed only of carbon and hydrogen atoms, and includes, for example, a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent. A polycyclic ring means a group that is directly connected to or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, but may also be another type of ring group, such as an aliphatic heterocycle, an aromatic hydrocarbon ring, an aromatic heterocycle, etc. Specifically, it includes, but is not limited to, cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an adamantyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group, and cycloalkanes such as cyclohexane and cyclopentane, and cyclocycloalkenes such as cyclohexene and cyclobutene.

[0074] In the present invention, an aliphatic heterocycle or heterocycloalkyl group means an aliphatic ring containing at least one heteroatom, and includes a heteroatom such as O, S, Se, N or Si, and also includes a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent, and a polycyclic ring means a group in which a heterocycloalkyl or a heterocycloalkane is directly connected to or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, but may also be another type of ring group, such as an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aromatic heterocycle, etc.

[0075] In the present invention, the fused ring (group) of an aliphatic ring and an aromatic ring is an aliphatic aromatic mixed ring (group), which means a ring in which two or more rings are connected and condensed with each other, and in which an aliphatic ring and an aromatic ring are condensed to have non-aromaticity as a whole, and more specifically, it means an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic heterocycle, an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic heterocycle condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic It can be a heterocyclic group, and 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, a tetrahydroquinoline group, etc. In addition, in the fused ring group of an aliphatic ring and an aromatic ring, it can be replaced with a heteroatom such as N, NR, O, S, Si, Ge, etc. other than carbon (R has the same definition as R1 to R7 in [Chemical Formula 1]).

[0076] In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited thereto.

[0077] 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 means a silyl group in which one, two, or three hydrogens are substituted with an aryl group in -SiH3, and the alkylsilyl group means an amine in which one, two, or three hydrogens are substituted with alkyl in -SiH3, and the alkylarylsilyl group means a silyl group in which at least one hydrogen is substituted with an alkyl group and an aryl group, and includes one or two alkyl groups and two or one corresponding aryl groups, and the arylheteroarylsilyl group means a silyl group in which at least one hydrogen is substituted with an aryl group and a heteroaryl group, and includes one or two aryl groups and two or one corresponding heteroaryl groups, in -SiH3. It means, and the heteroarylsilyl group means a silyl group in which one, two, or three hydrogens in -SiH3 are substituted with a heteroaryl group, and examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the alkylsilyl group and the heteroarylsilyl group are also the same.

[0078] 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.

[0079] In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and at least one hydrogen atom of the silyl group can be substituted with a substituent similar to that of the aryl group.

[0080] In the present invention, the amine group may include -NH2, an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, etc., and the arylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an aryl group, the alkylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an alkyl group, the alkylarylamine group means an amine in which one hydrogen in -NH2 is substituted with an alkyl group and the other hydrogen in -NH2 is substituted with an aryl group, the arylheteroarylamine group means an amine in which one hydrogen in -NH2 is substituted with an aryl group and the other hydrogen in -NH2 is substituted with a heteroaryl group, and the heteroarylamine group means an amine in which one or two hydrogens in -NH2 are substituted with a heteroaryl group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a diarylamine group, or a substituted or unsubstituted triarylamine group, and the same applies to the alkylamine group and heteroarylamine group.

[0081] 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, it 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.

[0082] 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 the definitions of these are as described for the silyl group, but may be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group.

[0083] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc., and one or more hydrogen atoms of the germanium group can be substituted with a substituent similar to that of the aryl group.

[0084] In the present invention, the cycloaryl group, aryl group, and heteroaryl group among the cycloalkyloxy group, aryloxy group, heteroaryloxy group, cycloalkylthio group, arylthio group, and heteroarylthio group are the same as the examples of the cycloaryl group, aryl group, and heteroaryl group described above, and specifically, as an example of the aryloxy group, a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy 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, Examples of arylthioxy groups include, but are not limited to, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, etc., and phenylthioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group, etc.

[0085] In the present invention, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0086]

[0087] According to one embodiment of the present invention, the polycyclic ring compound represented by the above-described [chemical formula 1] may be any one selected from compounds represented by the following chemical formulas, but the scope thereof is not limited thereby.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] In addition, another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer, preferably the light-emitting layer, includes a compound represented by the above-described [chemical formula 1] as a dopant.

[0097] The above light-emitting layer is a structure composed of a host and a dopant, and the light-emitting layer may further include other host or dopant materials in addition to the compound according to the present invention. In this case, the content of the dopant may be typically selected in 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.

[0098] In addition, the light-emitting layer may additionally include various dopants and various host materials in addition to the compound according to the present invention, and accordingly, in the light-emitting layer, not only the host but also the dopant material may be used by mixing or laminating one or more different compounds.

[0099]

[0100] Accordingly, when a compound represented by [chemical formula 1] is used as a fluorescent or delayed fluorescent dopant in the light-emitting layer of the organic light-emitting device according to the present invention, an anthracene compound represented by [chemical formula 2] below may be included as a host material.

[0101] [Chemical Formula 2]

[0102]

[0103] In the above [chemical formula 2],

[0104] R 21 Inland R 28 are the same or different from each other, and each independently represents 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 ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms are fused, 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 aryl group having 1 to 30 carbon atoms Any one selected from an alkylthioxy group, 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.

[0105] Ar1 and Ar3 are the same or different, and each independently represents a single bond or one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a ring group in which a divalent substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms are fused.

[0106] Ar2 and Ar4 are the same or different, and are each independently any 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 ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms are fused.

[0107] D n refers to the number of hydrogens in [chemical formula 2] replaced with deuterium, and n is an integer from 0 to 60.

[0108]

[0109] According to one embodiment of the present invention, the anthracene compound represented by the above-described [chemical formula 2] may be any one selected from compounds represented by the following chemical formulas, but the scope thereof is not limited thereby.

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] The organic layer of the organic light-emitting device according to 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, it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, it is not limited thereto, and a smaller or larger number of organic layers may be included, and the organic layer structure of a preferred organic light-emitting device according to the present invention will be described in more detail in the following examples.

[0134]

[0135] In addition, the organic light-emitting device according to the present invention may, in one embodiment, additionally include various hosts and various dopant materials in the light-emitting layer in addition to the compound according to the present invention, and accordingly, in the light-emitting layer, not only the host but also the dopant material may be used by mixing or laminating one or more different compounds.

[0136] In addition, according to one embodiment of the present invention, the dopant may further include at least one organometallic compound in addition to the compound according to the present invention, and may be used in a mixed or laminated manner.

[0137] Accordingly, in an organic light-emitting device according to one embodiment of the present invention, the light-emitting layer may be configured to include a first host, a second host, an organometallic compound, and a boron thermally activated delayed fluorescent light-emitting material.

[0138] In this case, the organometallic compound functions as a sensitizer, and the boron thermally activated delayed fluorescence emitter material functions as a luminescent dopant, so that the sensitizer compound can receive excitons from the first host and the second host and transfer them to the luminescent dopant.

[0139] Accordingly, excitons from the sensitizer are transferred to the light-emitting dopant compound through the Dexter energy transfer (DET) or Forster resonance transfer (FRET) mechanism, and the exciton energy transferred to the light-emitting dopant compound can emit light while being transferred to the ground state. At this time, the excitons of the sensitizer can be transferred from the first host and the second host through the FRET mechanism, or can be formed by the transfer of excitons generated from the host through the DET mechanism.

[0140] Accordingly, energy transfer through FRET and DET mechanisms between the sensor and the light-emitting dopant is facilitated, and triplet-triplet annihilation is suppressed, enabling the production of a high-efficiency organic light-emitting device.

[0141]

[0142] When the compound of [chemical formula 1] according to the present invention is used as a boron thermally activated delayed fluorescent emitter, it enables Förster energy transfer from the triplet of the phosphorescence sensitizer to the singlet of the boron thermally activated delayed fluorescent emitter, thereby reducing the number of long-lived triplet excitons involved in the deterioration of the device and improving the lifespan.

[0143] In addition, because it has a high molar extinction coefficient, the efficiency and lifespan can be improved due to effects such as an increase in the rate of fluorescence resonance energy transfer from the phosphorescence sensitizer to the emitter and a narrowing of the emission spectrum due to the multiple resonance effect, thereby increasing color purity.

[0144]

[0145] Hereinafter, one embodiment of an organic light-emitting device according to the present invention will be described in more detail.

[0146] The organic light-emitting device according to the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. If necessary, a hole injection layer may be further included between the anode and the hole transport layer. In addition, an electron injection layer may be further included between the electron transport layer and the cathode. In addition, one or two intermediate layers may be further formed, a hole blocking layer or an electron blocking layer may be further formed, and as described above, an organic layer having various functions depending on the characteristics of the device, such as a capping layer, may be further included.

[0147]

[0148] Meanwhile, the specific structure of the organic light-emitting device according to one embodiment of the present invention, the manufacturing method thereof, and each organic layer material are as follows.

[0149] First, an anode is formed by coating an anode material on the upper surface of the substrate. Here, the substrate used is a substrate commonly used in organic light-emitting devices, but an organic substrate or transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and water resistance is preferred. In addition, the anode material used is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity.

[0150] A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on top of the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on top of the hole injection layer.

[0151] The above hole injection layer material can be used without particular limitation as long as it is commonly used in the art, and as specific examples, 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], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], etc. can be used.

[0152] In addition, the hole transport layer material is not particularly limited as long as it is one commonly used in the art, and 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.

[0153] Next, a hole-assisting layer and a light-emitting layer are successively stacked on top of the hole transport layer, and a hole-blocking layer can be selectively formed as a thin film on top of the light-emitting layer by a vacuum deposition method or a spin coating method. The hole-blocking layer prevents the lifespan and efficiency of the device from decreasing when holes pass through the organic light-emitting layer and flow into the cathode by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level. The hole-blocking material used at this time is not particularly limited, but must have an electron transport ability and a higher ionization potential than the light-emitting compound, and representative examples thereof include BAlq, BCP, and TPBI.

[0154] As a material used in the above hole-blocking layer, BAlq, BCP, Bphen, TPBI, TAZ, BeBq2, OXD-7, Liq, etc. can be used, but are not limited thereto.

[0155] An electron transport layer is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, and then an electron injection layer is formed. A cathode electrode is formed by vacuum thermally depositing a metal for forming a cathode on top of the electron injection layer, thereby completing an organic light-emitting device according to one embodiment of the present invention.

[0156] 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 transparent cathode using ITO or IZO can be used to obtain a front-emitting element.

[0157] The above electron transport layer material has the function of stably transporting electrons injected from the cathode, and a known electron transport material can be used. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), and oxadiazole derivatives (PBD, BMD, BND, etc.).

[0158] In addition, each of the above organic layers can be formed by a single molecule deposition method or a solution process, wherein the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process refers to a method of forming a thin film by mixing a material used as a material for forming each layer with a solvent and using a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, or spin coating.

[0159] In addition, the organic light-emitting device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a flat panel lighting device of a single color or white color, a flexible lighting device of a single color or white color, a vehicle display device, a virtual or augmented reality display device, etc.

[0160] Hereinafter, to aid in understanding the present invention, synthetic examples of preferred compounds and device examples are presented. However, the following examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[0161]

[0162] Synthesis Example 1: Synthesis of [Compound 2]

[0163] Synthesis Example 1-1: Synthesis of A-1

[0164]

[0165] <a-1a> <a-1b> <a-1>

[0166] In the reactor <a-1a> 20 g, <a-1b>12.3 g, Pd(dba)31.4 g, P(t-Bu)3HBF41.3 g, t-BuONa 10.8 g, and toluene 250 mL were added and stirred under reflux for 6 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and purified by column chromatography. <a-1>(21 g, 83.6%) was obtained.

[0167]

[0168] Synthesis Example 1-2: Synthesis of A-2

[0169]

[0170] <a-2a> <a-1> <a-2>

[0171] Used in the above synthesis example 1-1 <a-1a>instead <a-2a>Use , <a-1b>instead <a-1>Synthesized in the same way except that <a-2>was obtained. (Yield 79%)

[0172]

[0173] Synthesis Example 1-3: Synthesis of [Compound 2]

[0174]

[0175] <a-2>[Compound 2]

[0176] In the reactor <a-2>Add 3 g, BI39.86 g, BPh32.44 g, and 120 mL of 1,2,4-trichlorobenzene and stir at 180°C for 6 hours. After lowering the temperature to 120°C, add 13.1 mL of N,N-diisopropylethylamine and stir for 1 hour. After completion of the reaction, the organic layer was concentrated under reduced pressure and purified by column chromatography to obtain [Compound 2]. (0.6 g, 19.5%)

[0177] MS (MALDI-TOF): m / z 611.32 [M + ]

[0178]

[0179] Synthesis Example 2: Synthesis of [Compound 7] and [Compound 8]

[0180] Synthesis Example 2-1: Synthesis of B-1

[0181]

[0182] <b-1a> <b-1b> <b-1>

[0183] Used in the above synthesis example 1-1 <a-1a>instead <b-1a>Use , <a-1b>instead <b-1b>Synthesized in the same way except that <b-1>was obtained. (Yield 77%)

[0184]

[0185] Synthesis Example 2-2: Synthesis of B-2

[0186]

[0187] <b-1> <a-1> <b-2>

[0188] Used in the above synthesis example 1-1 <a-1a>instead <b-1>Use , <a-1b>instead <a-1>Synthesized in the same way except that <b-2>was obtained. (Yield 80%)

[0189]

[0190] Synthesis Example 2-3: Synthesis of B-3

[0191]

[0192] <b-2> <b-3>

[0193] In the reactor <b-2>15 g, 200 mL of dichloromethane were added, and then 10.4 g of BBr3 was added dropwise in small amounts while refluxing and stirring at -78°C. After lowering the temperature to room temperature, stirring was performed for 24 hours, and after the reaction was completed, the organic layer was concentrated under reduced pressure and purified by column chromatography. <b-3>(7.3 g, 49.6%) was obtained.

[0194]

[0195] Synthesis Example 2-4: Synthesis of B-4

[0196]

[0197] <b-3> <b-4a> <b-4>

[0198] In the reactor <b-3> 10 g, <b-4a>11 g, 7.8 g of potassium carbonate, 0.04 g of CuI, 0.15 g of Fe(III)(acac), and 400 mL of NMP were added, and the mixture was refluxed and stirred at 180°C for 10 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and purified by column chromatography. <b-4>(2.7 g, 22.8%) was obtained.

[0199]

[0200] Synthesis Example 2-5: Synthesis of [Compound 7] and [Compound 8]

[0201]

[0202] <b-4>[Compound 7] [Compound 8]

[0203] Used in the above synthesis example 1-3 <a-2>instead <b-4>[Compound 7] and [Compound 8] were obtained by the same method except that [compound 7] was used. (Yields: 11% and 6%, respectively)

[0204] MS (MALDI-TOF): m / z 854.55 [M + ]

[0205]

[0206] Synthesis Example 3: Synthesis of [Compound 9] and [Compound 10]

[0207] Synthesis Example 3-1: Synthesis of C-1

[0208]

[0209] <a-1a> <c-1a> <c-1>

[0210] Used in the above synthesis example 1-1 <a-1b>instead <c-1a>Synthesized in the same way except that <c-1>was obtained. (Yield 72%)

[0211]

[0212] Synthesis Example 3-2: Synthesis of C-2

[0213]

[0214] <b-1> <c-1> <c-2>

[0215] Used in the above synthesis example 1-1 <a-1a>instead <b-1>Use , <a-1b>instead <c-1>Synthesized in the same way except that <c-2>was obtained. (Yield 64%)

[0216]

[0217] Synthesis Example 3-3: Synthesis of C-3

[0218]

[0219] <c-2> <c-3>

[0220] Used in the above synthesis example 2-3 <b-2>instead <c-2>Synthesized in the same way except that <c-3>was obtained. (Yield 51%)

[0221]

[0222] Synthesis Example 3-4: Synthesis of C-4

[0223]

[0224] <c-3> <b-4a> <c-4>

[0225] Used in the above synthesis example 2-4 <b-3>instead <c-3>Synthesized in the same way except that <c-4>was obtained. (Yield 23%)

[0226]

[0227] Synthesis Example 3-5: Synthesis of [Compound 9] and [Compound 10]

[0228]

[0229] <c-4>[Compound 9] [Compound 10]

[0230] Used in the above synthesis example 1-3 <a-2>instead <c-4>[Compound 9] and [Compound 10] were obtained by the same method except that [compound 9] was used. (Yields 8% and 5%, respectively)

[0231] MS (MALDI-TOF): m / z 965.56 [M + ]

[0232]

[0233] Synthesis Example 4: Synthesis of [Compound 13]

[0234] Synthesis Example 4-1: Synthesis of D-1

[0235]

[0236] <d-1a> <d-1b> <d-1>

[0237] Used in the above synthesis example 1-1 <a-1a>instead <d-1a>Use , <a-1b>instead <d-1b>Synthesized in the same way except that <d-1>was obtained. (Yield 67%)

[0238]

[0239] Synthesis Example 4-2: Synthesis of D-2

[0240]

[0241] <a-2a> <d-1> <d-2>

[0242] Used in the above synthesis example 1-1 <a-1a>instead <a-2a>Use , <a-1b>instead <d-1>Synthesized in the same way except that <d-2>was obtained. (Yield 73%)

[0243]

[0244] Synthesis Example 4-3: Synthesis of [Compound 13]

[0245]

[0246] <d-2>[Compound 13]

[0247] Used in the above synthesis example 1-3 <a-2>instead <d-2>[Compound 13] was obtained by the same method except that [compound 13] was used. (Yield 18%)

[0248] MS (MALDI-TOF): m / z 667.29 [M + ]

[0249]

[0250] Synthesis Example 5: Synthesis of [Compound 39]

[0251] Synthesis Example 5-1: Synthesis of E-1

[0252]

[0253] <e-1a> <e-1b> <e-1>

[0254] In a reactor under a nitrogen atmosphere <e-1b>26.4 g, cesium carbonate Add 50.6 g, 120 mL of NMP and stir. <e-1a>After adding 10 g, stir at 120℃ for 24 hours. After lowering to 0℃, add 55 mL of 6N HCl and extract with toluene. After completion of the reaction, wash the organic layer with water, concentrate under reduced pressure, and purify by column chromatography. <e-1>was obtained (25.3 g, 87%)

[0255]

[0256] Synthesis Example 5-2: Synthesis of E-2

[0257]

[0258] <d-1a> <a-1b> <e-2>

[0259] Used in the above synthesis example 1-1 <a-1a>instead <d-1a>Synthesized in the same way except that <e-2>was obtained. (Yield 75%)

[0260]

[0261] Synthesis Example 5-3: Synthesis of E-3

[0262]

[0263] <e-1> <e-2> <e-3>

[0264] Used in the above synthesis example 1-1 <a-1a>instead <e-1>Use , <a-1b>instead <e-2>Synthesized in the same way except that <e-3>was obtained. (Yield 75%)

[0265]

[0266] Synthesis Example 5-4: Synthesis of [Compound 39]

[0267]

[0268] <e-3>[Compound 39]

[0269] Used in the above synthesis example 1-3 <a-2>instead <e-3>Compound 39 was obtained by the same method except that it was synthesized using (yield 19.3%).

[0270] MS (MALDI-TOF): m / z 833.46 [M + ]

[0271]

[0272] Examples 1 to 7: Manufacturing of organic light-emitting devices

[0273] After patterning the ITO glass to have a light-emitting area of ​​2 mm × 2 mm, it was cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 × 10 -7 After the thickness was set to torr, a hole injection layer was formed on the ITO with an electron acceptor of the structural formula [Acceptor-1] and [chemical formula F] at a deposition ratio of [Acceptor-1] : [chemical formula F] = 2 : 98 (100 Å). [Chemical formula F] was formed as a hole transport layer (550 Å), and then [chemical formula G] was formed as an electron blocking layer (50 Å). An organic light-emitting device was manufactured by mixing the host [BH-1] described below and the compound of the present invention (2 wt%) to form a film (200 Å), then forming a film of [chemical formula H] (50 Å) as a hole-blocking layer, forming a film of [chemical formula E-1] and [chemical formula E-2] in a ratio of 1:1 to form a film of 250 Å as an electron transport layer, forming a film of [chemical formula E-2] in a thickness of 10 Å, and forming a film of Al (1000 Å) in that order. The luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0274] [Chemical Formula F] [Chemical Formula G] [Chemical Formula H]

[0275]

[0276] [Chemical Formula E-1] [Chemical Formula E-2] [Acceptor-1]

[0277]

[0278] [BH-1]

[0279]

[0280]

[0281] Comparative Examples 1 to 3

[0282] Organic light-emitting devices were manufactured in the same manner as in the above examples, except that [RD-1] to [RD-3] were used instead of the compounds used in the above examples, and the luminescence characteristics of the organic light-emitting devices were measured at 0.4 mA. The structures of [RD-1] to [RD-3] are as follows.

[0283] [RD-1] [RD-2] [RD-3]

[0284]

[0285] For the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 3, external quantum efficiency and lifespan were measured, and the results are shown in [Table 1] below.

[0286] Classification Dopant Efficiency (EQE, %) Lifetime (T97, hr) Example 1 Compound 28.7140 Example 2 Compound 79.5168 Example 3 Compound 89.2154 Example 4 Compound 910.3167 Example 5 Compound 1010.9184 Example 6 Compound 138.9160 Example 7 Compound 398.9135 Comparative Example 1RD-15.662 Comparative Example 2RD-27.598 Comparative Example 3RD-37.385

[0287] As shown in the above [Table 1], a device employing the compound according to the present invention as a dopant compound of a light-emitting layer in an organic light-emitting device can realize a high-efficiency, long-life organic light-emitting device with superior quantum efficiency and lifespan characteristics compared to a device employing a compound having a structure contrasting with the characteristic structure of the compound according to the present invention (Comparative Examples 1 to 3).

[0288] The present invention relates to a polycyclic ring compound having a characteristic condensed ring structure, which can be used as a dopant material for a light-emitting layer in an organic light-emitting device to realize a high-efficiency and long-life organic light-emitting device with excellent device characteristics such as light-emitting efficiency and lifespan, and thus can be industrially usefully utilized in various display devices such as lighting devices, flat panel displays, flexible displays, wearable displays, virtual or augmented reality displays, etc. < / e-2> < / e-1> < / a-1b> < / d-1a> < / e-1b> < / e-1a> < / d-1> < / a-2a> < / d-1b> < / d-1a> < / b-4a> < / c-3> < / c-2> < / c-1> < / b-1> < / c-1a> < / a-1a> < / b-3> < / b-4a> < / b-3> < / b-2> < / a-1> < / b-1> < / b-1b> < / b-1a> < / a-1> < / a-2a> < / a-1a> < / a-1b> < / a-1a>

Claims

1. A polycyclic ring compound represented by the following [chemical formula 1]: [Chemical Formula 1] In the above [chemical formula 1], X, Y1 and Y2 are each independently B or N, Z1 and Z2 are the same or different from each other, and are each independently selected from O, S, NR1, CR2R3, SiR4R5, and GeR6R7, A1 ring to A4 ring are the same or different from each other, and are each independently 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, but at least one is 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, R is 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 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, 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 carbon Any one selected from among an arylthioxy group having a number of 5 to 30, 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, R1 to R7 are the same or different, and each independently represents 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 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, 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 Any one selected from an alkylthioxy group, 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, The above A1 ring is connected to X and Y1 to form a ring, the A2 ring is connected to X and Y2 to form a ring, the A3 ring is connected to Y1 and Z1 to form a ring, and the A4 ring is connected to Y2 and Z2 to form a ring. The above R may be linked to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring, The above R2 and R3, R4 and R5, and R6 and R7 may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above R1 to R7 may be connected to an adjacent A3 ring or A4 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above adjacent A1 to A4 rings may be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, In the above [Chemical Formula 1], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 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 2 to 30 carbon atoms, 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, It means that the compound is substituted with one or more substituents selected from the group consisting of an amine group, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or is substituted with a substituent in which two or more of the above substituents are connected, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

2. In paragraph 1, A polycyclic ring compound characterized in that the A1 ring in the above [chemical formula 1] is a fused ring of a substituted or unsubstituted aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 3 to 24 carbon atoms.

3. In paragraph 1, A polycyclic ring compound characterized in that when X in the above [chemical formula 1] is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

4. In paragraph 1, A polycyclic ring compound, characterized in that Z1 and Z2 in the above [chemical formula 1] are the same or different, and each is independently selected from O, S, and NR1.

5. In paragraph 4, A polycyclic ring compound characterized in that at least one of Z1 and Z2 in the above [chemical formula 1] is O or S.

6. In paragraph 2, The above [chemical formula 1] is a polycyclic ring compound characterized by being represented by the following [chemical formula 1-1] to [chemical formula 1-3]: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above [Chemical Formula 1-1] to [Chemical Formula 1-3], X, Y1 and Y2 are each independently B or N, Z1 and Z2 are the same or different from each other, and are each independently selected from O, S, and NR1, A2 ring to A4 ring are the same or different from each other, and are each independently 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. R and R 19 are the same as or different from each other, and each independently represents 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 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, 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 aryl group having 1 to 30 carbon atoms Any one selected from an alkylthioxy group, 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, R1 and R 11 Inland R 14 are the same as or different from each other, and each independently represents 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 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, R 15 Inland R 18 are identical or different from each other, and each is independently hydrogen or deuterium, m is an integer of 2, The above A2 ring is connected to X and Y2 to form a ring, the A3 ring is connected to Y1 and Z1 to form a ring, and the A4 ring is connected to Y2 and Z2 to form a ring. The above R may be linked to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring, The above adjacent R 11 Inland R 14 can be linked to each other to form additional alicyclic or aromatic monocyclic or polycyclic rings, The above R1 may be linked to an adjacent A3 ring or A4 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above adjacent A2 ring and A4 ring can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, In the above [Chemical Formula 1-1] to [Chemical Formula 1-3], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 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 2 to 30 carbon atoms, 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, It means that the compound is substituted with one or two or more substituents selected from the group consisting of an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or is substituted with a substituent in which two or more of the above substituents are connected, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

7. In paragraph 6, A polycyclic ring compound characterized in that when X in the above [Chemical Formula 1-1] to [Chemical Formula 1-3] is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

8. In paragraph 1, A polycyclic ring compound characterized in that at least one deuterium atom in the above [chemical formula 1] is substituted.

9. In paragraph 1, The above [chemical formula 1] is a polycyclic ring compound characterized by being one selected from the following compounds:

10. Comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, The above organic layer includes at least one layer among 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. An organic light-emitting device, wherein the organic layer comprises at least one polycyclic ring compound represented by [chemical formula 1] according to claim 1.

11. In paragraph 10, An organic light-emitting device in which the light-emitting layer is composed of a host and a dopant, and at least one of the polycyclic ring compounds represented by the above-described [chemical formula 1] is a dopant in the light-emitting layer.

12. In paragraph 11, An organic light-emitting device characterized in that the above dopant is used by mixing or layering at least one other compound in addition to one polycyclic ring compound represented by [chemical formula 1].

13. In paragraph 11, An organic light-emitting device characterized in that at least one anthracene compound represented by the following [chemical formula 2] is mixed or laminated as a host in the light-emitting layer: [Chemical formula 2] In the above [chemical formula 2], R 21 Inland R 28 are the same as or different from each other, and each independently represents 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 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, 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 Any one selected from an alkylthioxy group, 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, Ar1 and Ar3 are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a fused ring group of a divalent substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 3 to 30 carbon atoms. 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. D n Silver refers to the number of hydrogens in [chemical formula 2] replaced by deuterium. n is an integer from 0 to 60.

14. In paragraph 13, An organic light-emitting device characterized in that the compound represented by the above [chemical formula 2] is one selected from the following compounds:

15. In paragraph 10, The organic light-emitting device is an organic light-emitting device used in any one device selected from a flat panel display device; a flexible display device; a flat panel lighting device of a single color or white color; and a flexible lighting device of a single color or white color; a vehicle display device; and a virtual or augmented reality display device.

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