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 the same as a dopant of a light-emitting layer, and since an improved organic light-emitting device with high efficiency and long lifespan can be achieved using the compound according to the present invention, the device can be industrially used not only for a lighting element, but also for a light-emitting element. And can be used in various display devices such as flat panel displays, flexible displays, and wearable displays.

Description

Technical Field

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

[0002] Organic light-emitting devices (OLEDs) are self-luminescent devices in which electrons injected from an electron-injecting electrode (cathode) combine with holes injected from a hole-injecting electrode (anode) in a light-emitting layer to form excitons, which emit light while releasing energy. These devices offer the advantages of low driving voltage, high brightness, wide viewing angles, and short response times, and can be applied to full-color flat-panel displays. Due to these advantages, OLEDs are attracting attention as next-generation light sources.

[0003] The above characteristics of organic light-emitting devices are achieved by optimizing the structure of the organic layers of the devices and are supported by stable and efficient materials for the organic layers (e.g., hole injection materials, hole transport materials, hole blocking materials, luminescent materials, electron transport materials, electron injection materials, and electron blocking materials). However, more research is still needed to develop structurally optimized structures for the organic layers of organic light-emitting devices and stable and efficient materials for the organic layers of organic light-emitting devices.

[0004] In particular, to obtain maximum efficiency in the light-emitting layer, an appropriate combination of energy band gaps of the host and dopant is required so that holes and electrons each migrate to the dopant through a stable electrochemical pathway to form excitons. Summary of the Invention

[0005] Technical issues

[0006] Therefore, the present invention aims to provide a polycyclic compound having a characteristic condensed ring structure, and a high-efficiency, long-life organic light-emitting device having significantly improved long life and luminous efficiency by using the same as a dopant material in a light-emitting layer.

[0007] Technical Solution

[0008] One aspect of the present invention provides a polycyclic compound represented by [Chemical Formula 1] or [Chemical Formula 2] having the following characteristic condensed ring structure, and an organic light-emitting device including the same as a dopant in a light-emitting layer.

[0009]

[0010] [Structural Formula 1]

[0011]

[0012] In [Chemical Formula 1] and [Chemical Formula 2], at least one pair of adjacent two of Z1 and Z2, Z2 and Z3, Z4 and Z5, Z5 and Z6, and Z6 and Z7 among Z1 to Z7 is a carbon atom and is simultaneously connected to two * in [Structural Formula 1] to form a ring.

[0013] The specific structures of [Chemical Formula 1] and [Chemical Formula 2], the specific compounds according to the present invention obtained therefrom, and the definitions of each substituent will be described later.

[0014] Beneficial effects

[0015] The present invention relates to a polycyclic compound having a characteristic condensed ring structure and an organic light-emitting device using the same as a dopant for a light-emitting layer, and since an improved organic light-emitting device with high efficiency and long life can be achieved, the device can be effectively used not only for lighting elements but also for various display devices such as flat panel displays, flexible displays and wearable displays. DETAILED DESCRIPTION

[0016] Hereinafter, the present invention will be described in more detail.

[0017] One aspect of the present invention relates to a compound represented by the following [Chemical Formula 1] or [Chemical Formula 2].

[0018]

[0019] [Structural Formula 1]

[0020]

[0021] In [Chemical Formula 1] and [Chemical Formula 2],

[0022] X is B, P=O, P=S or Al, Y1 is NR1, O, S, CR2R3, SiR4R5 or GeR6R7,

[0023] and Y2 is NR8, O or S.

[0024] A is selected from substituted or unsubstituted C6-C 50 Aromatic hydrocarbon ring, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon ring, substituted or unsubstituted C2-C 50 Aromatic heterocyclic, substituted or unsubstituted C2-C 50 Aliphatic heterocycle, and substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 A fused aromatic ring.

[0025] In [Chemical Formula 1] and [Chemical Formula 2], at least one pair of adjacent two of Z1 and Z2, Z2 and Z3, Z4 and Z5, Z5 and Z6, and Z6 and Z7 among Z1 to Z7 is a carbon atom and is simultaneously connected to two * in [Structural Formula 1] to form a ring.

[0026] In this article, the rest of Z1 to Z7 that do not form a ring and Z8 to Z 14 are the same as or different from each other, and are each independently CR9 or N.

[0027] In addition, when Z1 to Z 14 When a plurality of CR9s are included, CR9s may be the same as or different from each other.

[0028] Z, Q and W are the same or different from each other and are each independently NR 10 , CR 11 R 12 、SiR 13 R 14 ,GeR 15 R 16 , O or S.

[0029] R1 to R 16 are the same as or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkynyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 Aromatic ring fused cyclic group, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C1-C 30 Alkylthio, substituted or unsubstituted C5-C 30 an arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0030] m is 0 or 1, and when m is 0, the carbon atoms between Z and Z1 and the carbon atoms between Z and Z4 are connected by a single bond.

[0031] o is 0 or 1, and when o is 0, Z 11 The carbon atom between Q and the carbon atom connected to * is connected by a single bond. n is 0 or 1, and when n is 0, Z 14 The carbon atom between W and the carbon atom connected to * is connected by a single bond (however, o+n≥1).

[0032] In addition, R2 to R 16 It may be linked to adjacent substituents to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0033] Furthermore, adjacent plural R9 groups may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0034] In addition, R2 and R3, R4 and R5, R6 and R7, R 11 and R 12 、R 13 and R 14 , and R 15 and R 16 Each may be linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0035] According to one embodiment of the present invention, Z1 to Z7 and Z in [Chemical Formula 1] and [Chemical Formula 2] 11 to Z 14 At least one of the plurality of R9 is CR9, and at least one of the plurality of R9 is a bulky substituent other than hydrogen or deuterium.

[0036] According to one embodiment of the present invention, [Chemical Formula 1] may be represented by any one selected from the following [Chemical Formula 1-1] to [Chemical Formula 1-5].

[0037]

[0038]

[0039] [Chemical Formula 1-5]

[0040]

[0041] In [Chemical Formula 1-1] to [Chemical Formula 1-5], Z, Q, W, Z1 to Z 14 , Y1, Y2, m, n, o and A have the same definitions as in [Chemical Formula 1].

[0042] According to one embodiment of the present invention, [Chemical Formula 2] may be represented by any one selected from the following [Chemical Formula 2-1] to [Chemical Formula 2-5].

[0043]

[0044]

[0045] [Chemical Formula 2-5]

[0046]

[0047] In [Chemical Formula 2-1] to [Chemical Formula 2-5], Z, Q, W, Z1 to Z 14 , Y1, Y2, m, n, o and A have the same definitions as in [Chemical Formula 2].

[0048] In addition, "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 substituted with one or two or more substituents selected from the group consisting of deuterium, C1-C 24 Alkyl, C1-C 24 Halogenated alkyl, C3-C 24 Cycloalkyl, C2-C 24 Alkenyl, C2-C 24 Alkynyl, C1-C 24 Heteroalkyl, C2-C 24 Heterocycloalkyl, C6-C 30 Aryl, C7-C 30 Arylalkyl, C7-C 30 Alkyl aryl, C 2- C 30 Heteroaryl, C3-C 30 Heteroarylalkyl, C3-C 30 Alkyl heteroaryl, C3-C 24 Aliphatic ring and C 3- C 24 Aromatic ring fused cyclic group, C1-C 24 Alkoxy, C6-C 24 Aryloxy, C6-C 24 Arylsulfinyl, C1-C 40 Amine, C1-C 40 Silyl, C1-C 40 Germanium, cyano, halogen, hydroxyl and nitro, or substituted by two or more of the above substituents connected to each other, and the hydrogen in the substituent may be replaced by one or more deuterium, and two or more adjacent substituents may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0049] At the same time, "substituted or unsubstituted C1-C 30 Alkyl", "substituted or unsubstituted C6-C 50The range of the number of carbon atoms in the alkyl or aryl groups in "aryl" and the like refers to the total number of carbon atoms forming the alkyl or aryl portion when unsubstituted, without taking into account the substitution of that portion with substituents. For example, this means that a phenyl group substituted with a butyl group at the para position corresponds to a C6 aryl group substituted with a C4 butyl group.

[0050] In addition, in the present invention, being connected to each other or to an adjacent group to further form a ring may mean that adjacent substituents in a specific substituent may be bonded to each other or that a specific substituent and another adjacent group may be bonded to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and "adjacent group" may refer to a substituent that replaces an atom directly connected to an atom substituted with a corresponding substituent, a substituent that is positioned closest to a corresponding substituent in space, or another substituent that replaces an atom substituted with a corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent groups" to each other, and the connected pair of substituents each loses a hydrogen group and then is connected to each other to further form a ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be replaced by heteroatoms such as N, NR, O, S, Si and Ge. R has the same R1 to R2 as in [Chemical Formula 1] or [Chemical Formula 2]. 16 Same limitations.

[0051] In the present invention, the alkyl group may be linear or branched. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0052] In the present invention, specific examples of the arylalkyl group may include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and the like, but are not limited thereto.

[0053] In the present invention, specific examples of the alkylaryl group may include tolyl, xylyl, dimethylnaphthyl, tert-butylphenyl, tert-butylnaphthyl, tert-butylphenanthrenyl, and the like, but are not limited thereto.

[0054] In the present invention, alkenyl includes linear or branched forms, and can also be substituted with another substituent. Its specific examples can include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-base, 2-phenylvinyl-1-base, 2,2-diphenylvinyl-1-base, 2-phenyl-2-(naphthyl-1-base)vinyl-1-base, 2,2-bis(diphenyl-1-base)vinyl-1-base, stilbene, styryl etc., but are not limited thereto.

[0055] In the present invention, the alkynyl group also includes linear or branched forms, and may be substituted with another substituent. Examples thereof may include ethynyl, 2-propynyl, etc., but are not limited thereto.

[0056] In the present invention, a cycloalkenyl group is a non-aromatic cyclic unsaturated hydrocarbon group having one or more carbon double bonds. 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.

[0057] In the present invention, the aromatic hydrocarbon ring or aromatic group can be monocyclic or polycyclic. The term "polycyclic group" refers to a group that is directly connected or condensed with other cyclic groups, and other cyclic groups can be aromatic hydrocarbon rings, but can also be other types of cyclic groups such as aliphatic heterocycles, aliphatic hydrocarbon rings and aromatic heterocycles. Examples of monocyclic aromatic groups can include phenyl, biphenyl, terphenyl, etc., and examples of polycyclic aromatic groups can include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylene, tetraphenylene, Examples include phenylene, fluorenyl, acenaphthenyl, triphenylene, fluoranthenyl, and the like; however, the scope of the present invention is not limited to these examples.

[0058] In the present invention, an aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms. Examples thereof may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, indolocarbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline, thiazolyl, isothiophene Azolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl and the like, but not limited thereto.

[0059] In the present invention, an aliphatic hydrocarbon ring or a cycloalkyl group refers to a non-aromatic ring formed only by carbon atoms and hydrogen atoms. Examples thereof may include monocyclic or polycyclic groups, and the aliphatic hydrocarbon ring or cycloalkyl group may also be substituted with other substituents. The term "polycyclic group" refers to a group directly connected or fused to other cyclic groups, and other cyclic groups may be aliphatic hydrocarbon rings, but may also be other types of cyclic groups such as aliphatic heterocycles, aromatic hydrocarbon rings, and aromatic heterocycles. Specific examples thereof may include: cycloalkyl groups 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; cycloalkane groups such as cyclohexyl and cyclopentyl; and cycloalkene groups such as cyclohexenyl and cyclobutenyl, but are not limited thereto.

[0060] In the present invention, aliphatic heterocycle or heterocycloalkyl refers to an aliphatic ring containing one or more heteroatoms such as O, S, Se, N or Si, and also includes monocyclic or polycyclic groups, and may also be substituted with other substituents. The term "polycyclic group" refers to a group in which heterocycloalkyl, heterocycloalkane, etc. are directly connected or fused to other cyclic groups, and the other cyclic groups may be aliphatic heterocycles, but may also be other types of cyclic groups such as aliphatic hydrocarbon rings, aromatic hydrocarbon rings and aromatic heterocycles.

[0061] In the present invention, the condensed ring (cyclic group) of an aliphatic ring and an aromatic ring is an aliphatic-aromatic mixed ring (cyclic group) and refers to a ring in which two or more rings are connected and condensed to each other, and the aliphatic ring and the aromatic ring are condensed to have non-aromatic property as a whole. More specifically, the condensed ring (cyclic group) of an aliphatic ring and an aromatic ring may include an aromatic hydrocarbon ring (cyclic group) condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring (cyclic group) condensed with an aliphatic heterocycle, an aromatic heterocycle (cyclic group) condensed with an aliphatic hydrocarbon ring, an aromatic heterocycle (cyclic group) condensed with an aliphatic heterocycle, an aliphatic hydrocarbon ring (cyclic group) condensed with an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring (cyclic group) condensed with an aromatic heterocycle, an aliphatic heterocycle (cyclic group) condensed with an aromatic hydrocarbon ring, an aliphatic heterocycle (cyclic group) condensed with an aromatic hydrocarbon ring, an aliphatic heterocycle (cyclic group) condensed with an aromatic hydrocarbon ring, and the like, and specific examples thereof may include tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthrenyl, tetrahydroanthracenyl, octahydrotriphenylene, tetrahydrobenzothiophenyl, tetrahydrobenzofuranyl, tetrahydrocarbazolyl, tetrahydroquinolinyl, and the like. In addition, in the condensed ring (cyclic group) of the aliphatic ring and the aromatic ring, a heteroatom such as N, NR, O, S, Si or Ge may be substituted in addition to carbon, and R has the same structure as R1 to R2 in [Chemical Formula 1] or [Chemical Formula 2]. 16 Same limitations.

[0062] In the present invention, the alkoxy group may specifically be methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, etc., but is not limited thereto.

[0063] 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, and the like. 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 containing one or two alkyl groups and two or one aryl groups corresponding thereto by replacing at least one hydrogen atom in -SiH3 with an alkyl group and an aryl group, the arylheteroarylsilyl group refers to a silyl group containing one or two aryl groups and two or one heteroaryl groups corresponding thereto by replacing at least one hydrogen atom in -SiH3 with an aryl group and a heteroaryl group, and the heteroarylsilyl group refers to a silyl group in which one, two or three hydrogen atoms in -SiH3 are substituted with a heteroaryl group. Examples of the arylsilyl group may include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the same applies to the alkylsilyl group and the heteroarylsilyl group.

[0064] Herein, the aryl group in each of the arylsilyl group, heteroarylsilyl group and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and the heteroaryl group in each of the arylsilyl group, heteroarylsilyl group and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0065] Furthermore, specific examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a trimethoxysilyl group, a dimethoxyphenylsilyl group, a diphenylmethylsilyl group, a diphenylvinylsilyl group, a methylcyclobutylsilyl group, a dimethylfurylsilyl group, and the like, and one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

[0066] In the present invention, the amino group may include -NH2, alkylamino, arylamino, alkylarylamino, arylheteroarylamino, heteroarylamino, etc. Arylamino refers to an amino group in which one or two hydrogen atoms in -NH2 are replaced by aryl groups, alkylamino refers to an amino group in which one or two hydrogen atoms in -NH2 are replaced by alkyl groups, and alkylarylamino refers to an amino group in which one hydrogen atom in -NH2 is replaced by alkyl groups and the other hydrogen atom is replaced by aryl groups. Arylheteroarylamino refers to an amino group in which one hydrogen atom in -NH2 is replaced by aryl groups and the other hydrogen atom is replaced by heteroaryl groups, and heteroarylamino refers to an amino group in which one or two hydrogen atoms in -NH2 are replaced by heteroaryl groups. Examples of arylamino may include substituted or unsubstituted monoarylamino, substituted or unsubstituted diarylamino, or substituted or unsubstituted triarylamino, and the same applies to alkylamino and heteroarylamino.

[0067] Herein, the aryl group in each of the arylamine group, the heteroarylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and the heteroaryl group in each of the arylamine group, the heteroarylamine group and the arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0068] In the present invention, the germanium group (or germanyl group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc. The definition thereof follows the description provided for the silyl group and can be applied to each substituent obtained by replacing the silicon (Si) atom in the silyl group with a germanium (Ge) atom.

[0069] In addition, specific examples of the germanium group may include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, and the like, and one or more hydrogen atoms in the germanium group may be substituted with the same substituents as in the case of the aryl group.

[0070] The cycloalkyl, aryl and heteroaryl in cycloalkyloxy, aryloxy, heteroaryloxy, cycloalkylthio, arylthio and heteroarylthio are identical with the examples of cycloalkyl, aryl and heteroaryl provided above.The specific example of aryloxy can include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy etc., and the specific example of arylthio can include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio etc. However, aryloxy and arylthio are not limited thereto.

[0071] In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0072] 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 the compounds represented by the following chemical formulae, however, the scope of the present invention is not limited thereby.

[0073]

[0074]

[0075]

[0076]

[0077] In addition, another aspect of the present invention relates to an organic light-emitting device, which is formed by a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, and the organic layer (preferably the light-emitting layer) contains a compound represented by [Chemical Formula 1] or [Chemical Formula 2] as a dopant.

[0078] The light-emitting layer has a structure formed of a host and a dopant, and may further include a host material. In this article, the content of the dopant comprising the polycyclic compound according to the present invention can generally be selected in the range of about 0.01 parts by weight to about 20 parts by weight based on about 100 parts by weight of the host, however, the content is not limited thereto.

[0079] In addition, the light-emitting layer may also contain various dopants and host materials in addition to the dopant compound and host compound according to the present invention, and therefore, one or more types of compounds different from each other may be mixed or layered to serve not only as a host material but also as a dopant material in the light-emitting layer.

[0080] The host compound used in the light emitting layer according to one embodiment of the present invention may be an anthracene compound represented by the following [Chemical Formula 3].

[0081] [Chemical Formula 3]

[0082]

[0083] In [Chemical Formula 3],

[0084] R 21 to R 28 are the same as or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkynyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 Aromatic ring fused cyclic group, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C1-C 30 Alkylthio, substituted or unsubstituted C5-C 30 an arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0085] Ar1 and Ar3 are the same or different from each other and are each independently a single bond, or a substituted or unsubstituted C6-C 30 Arylene, or substituted or unsubstituted C5-C 30 Heteroarylene.

[0086] Ar2 and Ar4 are the same as or different from each other and are each independently selected from substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C3-C 30 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, and substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30A cyclic group of fused aromatic rings.

[0087] D n It refers to the number of hydrogen atoms replaced by deuterium atoms in [Chemical Formula 3], and n is an integer from 0 to 50.

[0088] 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 formulae, however, the scope of the present invention is not limited thereby.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] In addition, the organic layer of the organic light-emitting device according to the present invention may be formed in a single-layer structure, but may also be formed in a multilayer structure in which two or more organic layers are laminated. For example, the organic layer 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, the structure is not limited thereto and may include fewer or more organic layers. The preferred organic material layer structure of the organic light-emitting device according to the present invention will be described in more detail in the examples described later.

[0112] Hereinafter, one embodiment of the organic light emitting device according to the present invention will be described in more detail.

[0113] The organic light-emitting device of the present invention comprises an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. Optionally, the organic light-emitting device of the present invention may further comprise a hole injection layer between the anode and the hole transport layer, and an electron injection layer between the electron transport layer and the cathode. In addition, one or two intermediate layers may be formed, and a hole blocking layer or an electron blocking layer may also be formed. As described above, organic layers having various functions, such as a capping layer, may also be included depending on the device characteristics.

[0114] Meanwhile, a specific structure of an organic light emitting device according to one embodiment of the present invention, a manufacturing method thereof, and materials of each organic layer may be studied as follows.

[0115] First, the material for the anode electrode is coated on a substrate to form an anode. In this article, a substrate used for a common organic light-emitting device can be used as the substrate, and an organic substrate or a transparent plastic substrate with excellent transparency, surface flatness, ease of handling, and water resistance is preferred. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

[0116] A hole injection layer material is coated on the anode electrode by vacuum thermal deposition or spin coating to form a hole injection layer. Then, a hole transport layer material is coated on the hole injection layer by vacuum thermal deposition or spin coating to form a hole transport layer.

[0117] The hole injection layer material is not particularly limited as long as it is commonly used in the art. Examples thereof may include 4,4',4"-tris(2-naphthylphenyl-phenylamino)triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-bis(4-(phenyl-m-tolylamino)phenyl)biphenyl-4,4'-diamine (DNTPD), and the like.

[0118] The hole transport layer material is also not particularly limited, as long as it is commonly used in the art. Examples thereof may include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-(1,1-biphenyl)-4,4'-diamine (TPD), N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD), and the like.

[0119] Subsequently, a hole auxiliary layer and a light-emitting layer are sequentially laminated on the hole transport layer, and a hole blocking layer can be optionally formed as a thin film on the light-emitting layer using a method of vacuum deposition or spin coating. When the hole passes through the organic light-emitting layer and flows into the cathode, the life and efficiency of the device are reduced, and the hole blocking layer plays a role in preventing this problem by using a material with a very low highest occupied molecular orbital (HOMO) level. The hole blocking material used herein is not particularly limited, but needs to have an ionization potential higher than the light-emitting compound and has electron transport capability. Its representative examples can include BAlq, BCP, TPBI, etc.

[0120] As a material for the hole blocking layer, BAlq, BCP, Bphen, TPBI, TAZ, BeBq2, OXD-7, Liq, etc. may be used, however, the material is not limited thereto.

[0121] After depositing an electron transport layer on the hole blocking layer using a vacuum deposition or spin coating method, an electron injection layer is formed thereon, and a metal for forming a cathode is vacuum thermally deposited on the electron injection layer to form a cathode, and thus, an organic light-emitting device according to one embodiment of the present invention is completed.

[0122] Herein, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used, and in order to obtain a top-emitting light-emitting device, a transmissive cathode using ITO or IZO can be used.

[0123] As a material for the electron transport layer, a known electron transport material that plays a role in stably transporting electrons injected from the cathode can be used. Examples of known electron transport materials may include the following materials: quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, BAlq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), and Oxadiazole derivatives (PBD, BMD, BND, etc.).

[0124] In addition, each organic layer can be formed using a monomolecular deposition method or a solution method. Herein, the monomolecular deposition method refers to a method of forming a thin film by evaporating the material for forming each layer by heating or the like under vacuum or reduced pressure, and the solution method refers to a method of forming a thin film by mixing the material for forming each layer with a solvent and then applying a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, or spin coating to the mixture.

[0125] In addition, the organic light-emitting device of the present invention can be used in devices selected from the following: flat panel display devices, flexible display devices, monochrome or white flat panel lighting devices, monochrome or white flexible lighting devices, display devices for vehicles, display devices for virtual or augmented reality, etc.

[0126] Embodiments of the invention

[0127] Hereinafter, preferred synthesis examples of compounds and device examples are provided to help understand the present invention. However, the following examples are for illustrative purposes only, and the scope of the present invention is not limited thereby.

[0128] Synthesis Example 1: Synthesis of [Compound 1]

[0129] Synthesis Example 1-1: Synthesis of A-1

[0130]

[0131] Will <a-1a> (45g)、 <a-1b>(32 g), tris (dibenzylideneacetone) dipalladium (0) (3.94 g), sodium tert-butoxide (41.3 g), bis (diphenylphosphine) -1,1 '- binaphthyl (2.68 g) and toluene (450 mL) were introduced into a reactor, and the mixture was stirred under reflux for 5 hours. After the mixture was cooled to room temperature, ethyl acetate and water were introduced thereto, and the organic layer was separated. The resultant was purified by silica gel chromatography to obtain <a-1>(38.5 g, 64.5%).

[0132] Synthesis Example 1-2: Synthesis of A-2

[0133]

[0134] Will <a-1> (38g)、 <a-2a>(36.8 g), bis(tri-tert-butylphosphine) palladium (0) (1.4 g), sodium tert-butoxide (26.3 g) and toluene (400 mL) were introduced into a reactor, and the mixture was stirred under reflux for 16 hours. After the mixture was cooled to room temperature, ethyl acetate and water were introduced thereto, and the organic layer was separated. The resultant was purified by silica gel chromatography to obtain <a-2>(36.7 g, 57.6%).

[0135] Synthesis Example 1-3: Synthesis of A-3

[0136]

[0137] Will <a-2> (35g)、 <a-3a>(18.4 g), cesium carbonate (76.7 g) and dimethylformamide (350 mL) were introduced into a reactor, and the mixture was then stirred under reflux for 8 hours. After the mixture was cooled to room temperature, ethyl acetate and water were introduced thereto, and the organic layer was separated. The resultant was purified by silica gel chromatography to obtain <a-3>(38 g, 73.1%).

[0138] Synthesis Example 1-4: Synthesis of [Compound 1]

[0139]

[0140] Will <a-3>(38g) and toluene (400mL) are introduced into the reactor, and 2M tert-butyl lithium pentane solution (79mL) is then added dropwise thereto at -78 ℃. After the temperature is raised to 60 ℃, the mixture is stirred for 2 hours, and then pentane is completely removed by blowing nitrogen therein at 60 ℃. After the temperature is reduced to -78 ℃, boron tribromide (5.1mL) is added dropwise thereto. After the temperature is raised to room temperature, the mixture is stirred for 2 hours, and after the temperature is reduced to 0 ℃, N, N-diisopropylethylamine (9.4mL) is added dropwise thereto. After the temperature is raised to 120 ℃, the mixture is stirred for 16 hours. After the mixture is cooled to room temperature, 10% sodium acetate aqueous solution and ethyl acetate are introduced thereto. The organic layer is separated and concentrated under reduced pressure. The gained is purified by silica gel chromatography to obtain [compound 1] (5.4g, 14.7%).

[0141] MS (MALDI-TOF): m / z 676.27 [M + ]

[0142] Synthesis Example 2: Synthesis of [Compound 5]

[0143] Synthesis Example 2-1: Synthesis of B-1

[0144]

[0145] Will <b-1a> (45g)、 <b-1b>(23.5g), tetrapalladium (0) (5.1g), potassium carbonate (41.3g), toluene (500mL), ethanol (300mL) and water (200mL) were introduced into a reactor, and the mixture was then stirred under reflux for 8 hours. After the mixture was cooled to room temperature, ethyl acetate and water were introduced thereto, and the organic layer was separated. The organic layer was concentrated under reduced pressure, and triphenylphosphine (12.5g) and methyl pyrrolidone (400mL) were then introduced thereto, and the mixture was then stirred under reflux for 8 hours. The resulting product was purified by silica gel chromatography to obtain <b-1>(41.7 g, 90.6%).

[0146] Synthesis Example 2-2: Synthesis of B-2

[0147]

[0148] The same synthesis as in Synthesis Example 1-3 was performed to obtain <b-2>, the difference is that using <b-1>replace <a-3a>(Yield 79.6%)

[0149] Synthesis Example 2-3: Synthesis of [Compound 5]

[0150]

[0151] [Compound 5] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <b-2>replace <a-3>(Yield 15.4%)

[0152] MS (MALDI-TOF): m / z 732.33 [M + ]

[0153] Synthesis Example 3: Synthesis of [Compound 7]

[0154] Synthesis Example 3-1: Synthesis of C-1

[0155]

[0156]

[0157] The same synthesis as in Synthesis Example 2-1 was performed to obtain <c-1>, the difference is that using <c-1a>replace <b-1a>(Yield 81.4%)

[0158] Synthesis Example 3-2: Synthesis of C-2

[0159]

[0160] The same synthesis as in Synthesis Example 1-3 was performed to obtain <c-2>, the difference is that using <c-1>replace <a-3a>(Yield 74.5%)

[0161] Synthesis Example 3-3: Synthesis of [Compound 7]

[0162]

[0163] [Compound 7] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <c-2>replace <a-3>(Yield 16%)

[0164] MS (MALDI-TOF): m / z 768.28 [M + ]

[0165] Synthesis Example 4: Synthesis of [Compound 9]

[0166] Synthesis Example 4-1: Synthesis of D-1

[0167]

[0168] The same synthesis as in Synthesis Example 2-1 was performed to obtain <d-1>, the difference is that using <d-1a>replace <b-1a>, and use <d-1b>replace <b-1b>(Yield 74.2%)

[0169] Synthesis Example 4-2: Synthesis of D-2

[0170]

[0171] The same synthesis as in Synthesis Example 1-3 was performed to obtain <d-2>, the difference is that using <d-1>replace <a-3a>(Yield 65.7%)

[0172] Synthesis Example 4-3: Synthesis of [Compound 9]

[0173]

[0174] [Compound 9] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <d-2>replace <a-3>(Yield 10.1%)

[0175] MS (MALDI-TOF): m / z 804.37 [M + ]

[0176] Synthesis Example 5: Synthesis of [Compound 33]

[0177] Synthesis Example 5-1: Synthesis of E-1

[0178]

[0179] The same synthesis as in Synthesis Example 2-1 was performed to obtain <e-1>, the difference is that using <e-1a>replace <b-1a>, and use <e-1b>replace <b-1b>(Yield 88.7%)

[0180] Synthesis Example 5-2: Synthesis of E-2

[0181]

[0182] By synthesizing in the same manner as in Synthesis Example 1-1, <e-2>, the difference is that using <e-2a>replace <a-1a>, and use <e-2b>replace <a-1b>(Yield 81.6%)

[0183] Synthesis Example 5-3: Synthesis of E-3

[0184]

[0185] The same synthesis as in Synthesis Example 1-2 was performed to obtain <e-3>, the difference is that using <e-2>replace <a-1>(Yield 74.1%)

[0186] Synthesis Example 5-4: Synthesis of E-4

[0187]

[0188] The same synthesis as in Synthesis Example 1-3 was performed to obtain <e-4>, the difference is that using <e-3>replace <a-2>, and use <e-1>replace <a-3a>(Yield 65.4%)

[0189] Synthesis Example 5-5: Synthesis of [Compound 33]

[0190]

[0191] [Compound 33] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <e-4>replace <a-3>(Yield 8.4%)

[0192] MS (MALDI-TOF): m / z 1044.34 [M + ]

[0193] Synthesis Example 6: Synthesis of [Compound 20]

[0194] Synthesis Example 6-1: Synthesis of F-1

[0195]

[0196] The same synthesis as in Synthesis Example 1-2 was performed to obtain <f-1>, the difference is that using <f-1a>replace <a-2a>(Yield 88.4%)

[0197] Synthesis Example 6-2: Synthesis of F-2

[0198]

[0199] The same synthesis as in Synthesis Example 1-3 was performed to obtain <f-2>, the difference is that using <f-1>replace <a-2>, and use <f-2a>replace <a-3a>(Yield 71.5%)

[0200] Synthesis Example 6-3: Synthesis of [Compound 20]

[0201]

[0202] [Compound 20] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <f-2>replace <a-3>(Yield 10.5%)

[0203] MS (MALDI-TOF): m / z 695.26 [M + ]

[0204] Synthesis Example 7: Synthesis of [Compound 34]

[0205] Synthesis Example 7-1: Synthesis of G-1

[0206]

[0207] The same synthesis as in Synthesis Example 2-1 was performed to obtain <g-1>, the difference is that using <g-1a>replace <b-1a>(Yield 74.7%)

[0208] Synthesis Example 7-2: Synthesis of G-2

[0209]

[0210] By synthesizing in the same manner as in Synthesis Example 1-1, <g-2>, the difference is that using <g-2a>replace <a-1b>(Yield 88.6%)

[0211] Synthesis Example 7-3: Synthesis of G-3

[0212]

[0213] The same synthesis as in Synthesis Example 1-2 was performed to obtain <g-3>, the difference is that using <g-2>replace <a-1>, and use <g-3a>replace <a-2a>(Yield 68.7%)

[0214] Synthesis Example 7-4: Synthesis of G-4

[0215]

[0216] The same synthesis as in Synthesis Example 1-3 was performed to obtain <g-4>, the difference is that using <g-3>replace <a-2>, and use <g-1>replace <a-3a>(Yield 74.3%)

[0217] Synthesis Example 7-5: Synthesis of [Compound 34]

[0218]

[0219] [Compound 34] was obtained by performing synthesis in the same manner as in Synthesis Example 1-4, except that <g-4>replace <a-3>(Yield 12.7%)

[0220] MS (MALDI-TOF): m / z 790.37 [M]

[0221] Examples 1 to 7: Fabrication of organic light-emitting devices

[0222] The ITO glass was patterned to have a light-emitting area of 2 mm × 2 mm and then cleaned. The ITO glass was mounted in a vacuum chamber and the base pressure was set at 1 × 10 -7 After support, the electron acceptor of the following structural formula [Acceptor-1] and [Chemical Formula F] were deposited on the ITO As the hole injection layer, the deposition ratio of [Acceptor-1] and [Chemical Formula F] was 2:98. [Chemical Formula F] was deposited As a hole transport layer, [Chemical Formula G] was then deposited As the light-emitting layer, the following host [BH-1] and the compound of the present invention (2 wt%) were mixed and deposited. Afterwards, [chemical formula H] is deposited As a hole blocking layer, [Chemical Formula E-1] and [Chemical Formula E-2] were deposited at a ratio of 1:1. As an electron transport layer, [Chemical Formula E-2] was deposited As the electron injection layer, and deposit Al in this order An organic light-emitting device was manufactured and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0223]

[0224] [BH-1]

[0225]

[0226] Comparative Examples 1 to 3

[0227] Organic light-emitting devices were manufactured in the same manner as in Example, except that [RD-1] to [RD-3] were used instead of the compounds used in Example, and the light emission characteristics of the organic light-emitting devices were measured at 0.4 mA. The structures of [RD-1] to [RD-3] are as follows.

[0228]

[0229]

[0230] For each of the organic light emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 3, the external quantum efficiency and the lifetime were measured, and the results are shown in the following [Table 1].

[0231] [Table 1]

[0232]

[0233] As shown in [Table 1], devices using the compounds according to the present invention as dopant compounds of the light-emitting layer in organic light-emitting devices can realize high-efficiency, long-life organic light-emitting devices with excellent quantum efficiency and lifetime characteristics, compared with devices using compounds having a structure contrasting with the characteristic structure of the compounds according to the present invention (Comparative Examples 1 to 3).

[0234] [Industrial Applicability]

[0235] The present invention relates to a polycyclic compound having a characteristic condensed ring structure and an organic light-emitting device using the same as a dopant for a light-emitting layer. Since an improved organic light-emitting device with high efficiency and long life can be realized using the compound according to the present invention, the device can be industrially used not only for lighting elements but also for various display devices such as flat panel displays, flexible displays and wearable displays. < / b-1a> < / a-2> < / a-1> < / a-1a>

Claims

1. A polycyclic compound represented by the following [Chemical Formula 1] or [Chemical Formula 2]: in, In [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; Y2 is NR8, O or S; A is any one selected from the following: substituted or unsubstituted C6-C 50 Aromatic hydrocarbon ring, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon ring, substituted or unsubstituted C2-C 50 Aromatic heterocyclic, substituted or unsubstituted C2-C 50 Aliphatic heterocycle, and substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 fused aromatic rings; and At least one pair of adjacent two of Z1 and Z2, Z2 and Z3, Z4 and Z5, Z5 and Z6, and Z6 and Z7 among Z1 to Z7 is a carbon atom and is simultaneously connected to two * in [Structural Formula 1] to form a ring, [Structural Formula 1] The rest of Z1 to Z7 that do not form the ring and Z8 to Z 14 are the same as or different from each other, and are each independently CR9 or N; When Z1 to Z 14 When a plurality of CR9s are included, the CR9s may be the same or different from each other; Z, Q and W are the same or different from each other and are each independently NR 10 , CR 11 R 12 、SiR 13 R 14 ,GeR 15 R 16 , O or S; R1 to R 16 are the same as or different from each other and are each independently selected from any one of the following: hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkynyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 Aromatic ring fused cyclic group, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C1-C 30 Alkylthio, substituted or unsubstituted C5-C 30 arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen groups; m is 0 or 1, and when m is 0, the carbon atoms between Z and Z1 and the carbon atoms between Z and Z4 are connected by a single bond; o is 0 or 1, and when o is 0, Z 11 The carbon atom between Q and the carbon atom connected to * are connected by a single bond; n is 0 or 1, and when n is 0, Z 14 The carbon atom between W and the carbon atom connected to * are connected by a single bond; However, o+n≥1; R2 to R 16 optionally linked to adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic rings; Adjacent multiple R9 are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; R2 and R3, R4 and R5, R6 and R7, R 11 and R 12 、R 13 and R 14 , and R 15 and R 16 Each is optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring; as well as The "substituted" in the "substituted or unsubstituted" in [Chemical Formula 1], [Chemical Formula 2] and [Structural Formula 1] means substituted with one or two or more substituents selected from the following: deuterium, C1-C 24 Alkyl, C1-C 24 Halogenated alkyl, C3-C 24 Cycloalkyl, C2-C 24 Alkenyl, C2-C 24 Alkynyl, C1-C 24 Heteroalkyl, C2-C 24 Heterocycloalkyl, C6-C 30 Aryl, C7-C 30 Arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 Heteroaryl, C3-C 30 Heteroarylalkyl, C3-C 30 Alkyl heteroaryl, C3-C 24 Aliphatic ring and C3-C 24 Aromatic ring fused cyclic group, C1-C 24 Alkoxy, C6-C 24 Aryloxy, C6-C 24 Arylsulfinyl, C1-C 40 Amine, C1-C 40 Silyl, C1-C 40 a germanium group, a cyano group, a halogen group, a hydroxyl group and a nitro group, or substituted by two or more of the above substituents which are linked together, and the hydrogen in the substituent is optionally substituted by one or more deuteriums, and two or more adjacent substituents are optionally linked to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

2. The polycyclic compound according to claim 1, wherein Z1 to Z7 and Z in [Chemical Formula 1] and [Chemical Formula 2] 11 to Z 14 At least one of the plurality of R9 is CR9, and at least one of the plurality of R9 is not hydrogen or deuterium.

3. The polycyclic compound according to claim 1, wherein [Chemical Formula 1] is represented by any one selected from the following [Chemical Formula 1-1] to [Chemical Formula 1-5]: In [Chemical Formula 1-1] to [Chemical Formula 1-5], Z, Q, W, Z1 to Z 14 , Y1, Y2, m, n, o and A have the same definitions as in [Chemical Formula 1] of claim 1.

4. The polycyclic compound according to claim 1, wherein [Chemical Formula 2] is represented by any one selected from the following [Chemical Formula 2-1] to [Chemical Formula 2-5]: In [Chemical Formula 2-1] to [Chemical Formula 2-5], Z, Q, W, Z1 to Z 14 , Y1, Y2, m, n, o and A have the same definitions as in [Chemical Formula 2] of claim 1.

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

6. An organic light-emitting device, comprising: a first electrode; a second electrode opposite to the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer contains at least one type of the polycyclic compound represented by [Chemical Formula 1] or [Chemical Formula 2] according to claim 1 .

7. The organic light-emitting device according to claim 6, wherein the organic layer comprises at least one of the following: 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; and At least one of the above layers contains at least one type of the 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 is formed of a host and a dopant, and at least one type of the polycyclic compound represented by [Chemical Formula 1] or [Chemical Formula 2] is the 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 [Chemical Formula 3], R 21 to R 28 are the same as or different from each other and are each independently selected from any one of the following: hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkynyl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 50 Cycloalkyl, substituted or unsubstituted C2-C 50 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 Aromatic ring fused cyclic group, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 Aryloxy, substituted or unsubstituted C1-C 30 Alkylthio, substituted or unsubstituted C5-C 30 arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanium, nitro, cyano and halogen groups; Ar1 and Ar3 are the same or different from each other and are each independently a single bond, or a substituted or unsubstituted C6-C 30 Arylene, or substituted or unsubstituted C5-C 30 heteroarylene; Ar2 and Ar4 are the same as or different from each other and are each independently selected from any one of the following: substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C3-C 30 Heterocycloalkyl, substituted or unsubstituted C2-C 50 Heteroaryl, and substituted or unsubstituted C3-C 30 Aliphatic ring and C3-C 30 Aromatic ring-fused cyclic groups; and D n It refers to the number of hydrogen atoms replaced by deuterium atoms in [Chemical Formula 3], and n is an integer from 0 to 50.

10. The organic light-emitting device according to claim 9, wherein [Chemical Formula 3] is any one selected from the compounds represented by the following chemical formulas: The organic light emitting device according to claim 7 , wherein at least one selected from the layers is formed using a deposition method or a solution method. 12 . The organic light-emitting device according to claim 8 , wherein one or more types of compounds other than one type of the compound represented by [Chemical Formula 3] are mixed or layered to serve as the host in the light-emitting layer. 13 . The organic light-emitting device according to claim 8 , wherein one or more types of compounds other than one type of compound represented by [Chemical Formula 1] or [Chemical Formula 2] are mixed or layered to serve as the dopant in the light-emitting layer.

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

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