Polycyclic compounds and organic light emitting devices using the same

Abstract

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

Description

Technical Field

[0001] The present invention relates to polycyclic compounds for use as organic layers, such as light-emitting layers, in organic light-emitting devices, and organic light-emitting devices comprising the same. Background Technology

[0002] Organic light-emitting devices (OLEDs) are self-emissive devices in which electrons injected from an electron injection electrode (cathode) combine with holes injected from a hole injection electrode (anode) in the light-emitting layer to form excitons, which emit light while releasing energy. Such OLEDs offer advantages such as low driving voltage, high brightness, wide viewing angle, and short response time, and can be applied to full-color flat panel displays. Due to these advantages, OLEDs have attracted attention as a next-generation light source.

[0003] The aforementioned characteristics of organic light-emitting devices (OLEDs) are achieved through structural optimization of the organic layers, supported by stable and effective materials used in these 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, further research is needed to develop structurally optimized structures for the organic layers of OLEDs and to develop stable and effective materials for these layers.

[0004] In particular, to achieve maximum efficiency in the luminescent layer, an appropriate combination of the band gaps of the host and dopant is required so that holes and electrons migrate to the dopant via stable electrochemical pathways to form excitons. Summary of the Invention

[0005] Technical issues

[0006] Therefore, the present invention aims to provide polycyclic compounds with characteristic fused ring structures, and high-efficiency long-lifetime organic light-emitting devices with significantly improved lifetime and luminous efficiency by using them as dopant materials in the light-emitting layer.

[0007] Technical solution

[0008] To address the aforementioned problems, one aspect of the present invention provides a polycyclic compound represented by [Chemical Formula 1] having a fused ring structure and an organic light-emitting device comprising the compound as a dopant in a light-emitting layer.

[0009] [Chemical Formula 1]

[0010]

[0011] The specific structure of [Chemical Formula 1], the specific compounds obtained therefrom according to the invention, and the limitations of each substituent will be described below.

[0012] Beneficial effects

[0013] This invention relates to polycyclic compounds having a characteristic fused ring structure and organic light-emitting devices using them as dopants as light-emitting layers. Since high-efficiency, long-lifetime organic light-emitting devices can be realized, organic light-emitting devices can be effectively used not only for lighting devices, but also for various display devices such as flat panel displays, flexible displays and wearable displays, as well as displays for virtual reality or augmented reality. Detailed Implementation

[0014] The invention will be described in more detail below.

[0015] One aspect of the present invention relates to polycyclic compounds represented by the following [Chemical Formula 1].

[0016] [Chemical Formula 1]

[0017]

[0018] In [Chemical Formula 1],

[0019] X, Y1, and Y2 are each independently B or N.

[0020] Z1 and Z2 may be the same as or different from each other, and each is independently selected from O, S, NR1, CR2R3, SiR4R5 and GeR6R7.

[0021] Rings A1 to A4 may be identical or different from each other, and each is independently selected from substituted or unsubstituted C6-C. 50 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Aromatic heterocycles, substituted or unsubstituted C2-C 50 Aliphatic heterocycles, and C3-C of substituted or unsubstituted heterocycles. 30 Aliphatic rings and C3-C 30 A ring of fused aromatic rings.

[0022] In this paper, at least one of rings A1 to A4 is either substituted or unsubstituted C3-C. 30 Aliphatic rings and C3-C 30 A ring of fused aromatic rings.

[0023] R is selected from hydrogen, deuterium, or substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 50cycloalkyl, substituted or unsubstituted C2-C 50 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups.

[0024] R1 to R7 may be the same as or different from each other, and each is independently selected from substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups.

[0025] Ring A1 is connected to X and Y1 to form a ring, ring A2 is connected to X and Y2 to form a ring, ring A3 is connected to Y1 and Z1 to form a ring, and ring A4 is connected to Y2 and Z2 to form a ring.

[0026] R can be linked to adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0027] R2 and R3, R4 and R5, and R6 and R7 can each connect to each other to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0028] R1 to R7 can be connected to adjacent rings A3 or A4 to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0029] Adjacent rings A1 to A4 can connect with each other to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0030] In [Chemical Formula 1], "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium, C1-C... 24 Alkyl, C1-C 24 Haloalkyl, C2-C 24 alkenyl, C2-C 24 alkynyl group, C3-C 30 cycloalkyl, C1-C 24 Heteroalkyl, C6-C 30 Aryl, C7-C 30 arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 heteroaryl, C2-C 30 Heteroarylalkyl, wherein C3-C 24 Aliphatic rings and C3-C 24 Aromatic ring fused cyclic groups, C1-C 24 Alkoxy, C1-C 30 Amine group, C1-C 30 Silyl, C1-C 30 Germanium-based, C6-C 24 Aryloxy group, C6-C 24 The substituents may be arylthionyl, cyano, halogen, hydroxyl, or nitro, or may be substituted by two or more of the above substituents linked together. One or more hydrogen atoms of the substituents may be replaced by deuterium atoms, and two or more adjacent substituents may be linked together to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0031] According to one embodiment of the invention, in the compound of the invention [Chemical Formula 1], when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

[0032] According to one embodiment of the invention, Z1 and Z2 in [Chemical Formula 1] may be the same as or different from each other, and may each be independently selected from any of O, S and NR1.

[0033] Furthermore, according to one embodiment of the present invention, at least one of Z1 and Z2 in [Chemical Formula 1] may be O or S.

[0034] Furthermore, in the compounds according to the invention, at least one hydrogen atom in [Chemical Formula 1] can be replaced by deuterium.

[0035] According to one embodiment of the present invention, ring A1 in [Chemical Formula 1] is substituted or unsubstituted, wherein C3-C 24 Aliphatic rings and C3-C 24 Aromatic rings fused together, therefore, [Chemical Formula 1] can be represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-3].

[0036]

[0037]

[0038] In [Chemical Formula 1-1] to [Chemical Formula 1-3],

[0039] X, Y1, and Y2 are each independently B or N.

[0040] Z1 and Z2 may be the same as or different from each other, and each is independently selected from O, S and NR1.

[0041] Rings A2 through A4 may be identical or different from each other, and each is independently selected from substituted or unsubstituted C6-C. 50 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Aromatic heterocycles, substituted or unsubstituted C2-C 50 Aliphatic heterocycles, and C3-C of substituted or unsubstituted heterocycles. 30 Aliphatic rings and C3-C 30 A ring of fused aromatic rings.

[0042] R and R 19 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups.

[0043] R1 and R 11 To R 14 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups.

[0044] R 15 To R 18 They may be the same or different from each other, and each is independently hydrogen or deuterium.

[0045] m is an integer 2.

[0046] Ring A2 is connected to X and Y2 to form a ring, ring A3 is connected to Y1 and Z1 to form a ring, and ring A4 is connected to Y2 and Z2 to form a ring.

[0047] R can be linked to adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0048] Adjacent R 11 To R 14 They can connect with each other to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0049] R1 can connect with adjacent rings A3 or A4 to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0050] Adjacent rings A2 and A4 can connect with each other to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0051] In [Chemical Formula 1-1] to [Chemical Formula 1-3], "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium, C1-C 24 Alkyl, C1-C 24 Haloalkyl, C2-C 24 alkenyl, C2-C 24 alkynyl group, C3-C 30 cycloalkyl, C1-C 24 Heteroalkyl, C6-C 30 Aryl, C7-C 30 arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 heteroaryl, C2-C 30 Heteroarylalkyl, wherein C3-C 24 Aliphatic rings and C3-C 24 Aromatic ring fused cyclic groups, C1-C 24 Alkoxy, C1-C 30 Amine group, C1-C 30 Silyl, C1-C 30 Germanium-based, C6-C 24 Aryloxy group, C6-C 24 The substituents may be arylthionyl, cyano, halogen, hydroxyl, or nitro, or may be substituted by two or more of the above substituents linked together. One or more hydrogen atoms of the substituents may be replaced by deuterium atoms, and two or more adjacent substituents may be linked together to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0052] According to one embodiment of the present invention, in the compounds of [Chemical Formula 1-1] to [Chemical Formula 1-3] according to the present invention, when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

[0053] Furthermore, in this invention, the term "substituted or unsubstituted" means that each of the substituents defined above is substituted by one or more substituents selected from the following: deuterium, C1-C 24 Alkyl, C1-C 24 Haloalkyl, C2-C 24 alkenyl, C2-C 24 alkynyl group, C3-C 30 cycloalkyl, C1-C 24 Heteroalkyl, C6-C 30 Aryl, C7-C 30 arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 heteroaryl, C2-C 30 Heteroarylalkyl, wherein C3-C24 Aliphatic rings and C3-C 24 Aromatic ring fused cyclic groups, C1-C 24 Alkoxy, C1-C 30 Amine group, C1-C 30 Silyl, C1-C 30 Germanium-based, C6-C 24 Aryloxy group, C6-C 24 The substituents may be arylthionyl, cyano, halogen, hydroxyl, or nitro, or may be substituted by two or more of the above-mentioned substituents linked together. One or more hydrogen atoms in the substituents may be replaced by deuterium atoms, and two or more adjacent substituents may be linked together to further form alicyclic or aromatic monocyclic or polycyclic rings. For example, this means that ring A is substituted by C1-C2. 30 Amine group, via C1-C 24 Alkyl-substituted C1-C 30 Amino group, or C6-C 30 Aryl and hydroxyl C1-C 24 Alkyl-substituted C6-C 30 Both aryl groups are substituted.

[0054] Furthermore, in this invention, "substituted or unsubstituted C1-C" 30 Alkyl group, substituted or unsubstituted C6-C 50 The range of carbon atoms in alkyl or aryl groups, such as "aryl", refers to the total number of carbon atoms forming the alkyl or aryl moiety when unsubstituted, regardless of whether the moiety is substituted by a substituent. For example, it 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.

[0055] Furthermore, in this invention, the connection between substituents or with adjacent groups to further form a ring can mean that adjacent substituents in a particular substituent can bond to each other or that a particular substituent and another adjacent group can bond to each other to form a substituted or unsubstituted alicyclic or aromatic ring. "Adjacent group" can refer to a substituent that substitutes an atom directly bonded to the atom substituted with the corresponding substituent, a substituent positioned spatially closest to the corresponding substituent, or another substituent that substitutes an atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring and two substituents substituted on the same carbon atom in an alicyclic ring can be interpreted as "adjacent groups," and the connected substituent pairs further form a ring by connecting the substituents to each other after removing a hydrogen group from each of the substituents. The carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring can be replaced by a heteroatom such as N, NR, O, S, Si, or Ge (R has the same limitations as R1 to R7 in [Chemical Formula 1]).

[0056] In this invention, the alkyl group can be linear or branched. Specific examples 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.

[0057] In this invention, specific examples of arylalkyl groups may include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc.

[0058] In this invention, specific examples of alkylaryl groups may include, but are not limited to, tolyl, xylyl, dimethylnaphthyl, tert-butylphenyl, tert-butylnaphthyl, tert-butylphenanthryl, etc.

[0059] In this invention, the alkenyl group includes linear or branched forms and may also be substituted with other substituents. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, etc. It includes, but is not limited to, styrene, etc.

[0060] In this invention, the alkynyl group includes both linear and branched forms, and may also be substituted with other substituents. Examples include ethynyl, 2-propynyl, etc., but are not limited thereto.

[0061] In this invention, the cycloalkenyl group is a non-aromatic cyclic unsaturated hydrocarbon group having one or more carbon double bonds. Examples may include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, 2,4-cycloheptadienyl, and 1,5-cyclooctadienyl.

[0062] In this invention, the aromatic hydrocarbon ring or aryl group can be monocyclic or polycyclic. The term "polycyclic group" refers to a group directly connected or fused with other cyclic groups, and these 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 aryl groups can include phenyl, biphenyl, terphenyl, etc., and examples of polycyclic aryl groups can include naphthyl, anthraceneyl, phenanthryl, pyrene, etc. alkyl, tetraphenyl, Examples of methyl, fluorenyl, acenaphthenic, triphenylene, fluoranyl, etc., are used; however, the scope of this invention is not limited to these examples.

[0063] In this invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms. Examples include thiophene, furanyl, pyrrole, imidazole, and thiazolyl groups. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Triazolyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Indole-Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolinel, thiazolyl, iso azole group, Diazole group, thiadiazole group, benzothiazolium group, phenthiazolium group, etc., but not limited to these.

[0064] In this invention, an aliphatic ring or cycloalkyl group refers to a non-aromatic ring formed solely of carbon and hydrogen atoms. Examples may include monocyclic or polycyclic groups, and the aliphatic ring or cycloalkyl group may be substituted with other substituents. The term "polycyclic group" refers to a group directly attached to or fused with other cyclic groups, and these other cyclic groups may be aliphatic rings, but may also be other types of cyclic groups such as aliphatic heterocycles, aromatic rings, and aromatic heterocycles. Specific examples 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 groups and cyclopentyl groups; and cycloolefin groups such as cyclohexene groups and cyclobutene groups, but are not limited thereto.

[0065] In this invention, aliphatic heterocycles or heterocyclic alkyl groups refer to aliphatic rings containing one or more heteroatoms such as O, S, Se, N, or Si, and also include monocyclic or polycyclic groups, which may be substituted with other substituents. The term "polycyclic group" refers to a group in which heterocyclic alkyl groups, heterocyclic alkanes, etc., are directly connected or fused with other cyclic groups, and the other cyclic groups can be aliphatic heterocycles, but can also be other types of cyclic groups such as aliphatic hydrocarbon rings, aromatic hydrocarbon rings, and aromatic heterocycles.

[0066] In this invention, the ring (cyclic group) in which the aliphatic ring and the aromatic ring are fused is an aliphatic-aromatic mixed ring (cyclic group), and refers to a ring in which two or more rings are connected and fused together, and the aliphatic ring and the aromatic ring are fused together to exhibit non-aromatic properties as a whole. More specifically, the ring (cyclic group) fused with an aliphatic ring and an aromatic ring can include an aromatic hydrocarbon ring (cyclic group) fused with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring (cyclic group) fused with an aliphatic heterocycle, an aromatic heterocycle (cyclic group) fused with an aliphatic hydrocarbon ring, an aromatic heterocycle (cyclic group) fused with an aliphatic heterocycle, an aliphatic hydrocarbon ring (cyclic group) fused with an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring (cyclic group) fused with an aromatic heterocycle, an aliphatic heterocycle (cyclic group) fused with an aromatic hydrocarbon ring, an aliphatic heterocycle (cyclic group) fused with an aromatic heterocycle, etc., and specific examples can include tetrahydronaphthyl, tetrahydrobenzocycloheptenyl, tetrahydrophenanthryl, tetrahydroanthreneyl, octahydrotriphenylene, tetrahydrobenzothiophene, tetrahydrobenzofuranyl, tetrahydrocarbazoleyl, tetrahydroquinolinyl, etc. Furthermore, the carbon in the ring (cyclic group) in which the aliphatic ring and the aromatic ring are fused can be replaced by heteroatoms such as N, NR, O, S, Si or Ge (R has the same limitation as R1 to R7 in [Chemical Formula 1].

[0067] In this invention, specific examples of alkoxy groups may include, but are not limited to, methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, etc.

[0068] In this invention, silyl groups may include -SiH3, alkylsilyl, arylsilyl, alkylarylsilyl, arylheteroarylsilyl, heteroarylsilyl, etc. Arylsilyl refers to a silyl group in which one, two, or three hydrogen atoms of -SiH3 are replaced by aryl groups; alkylsilyl refers to a silyl group in which one, two, or three hydrogen atoms of -SiH3 are replaced by alkyl groups; alkylarylsilyl refers to a silyl group containing one or two alkyl groups and two or one corresponding aryl group by replacing at least one hydrogen atom of -SiH3 with alkyl and aryl groups; arylheteroarylsilyl refers to a silyl group containing one or two aryl groups and two or one corresponding heteroaryl group by replacing at least one hydrogen atom of -SiH3 with aryl and heteroaryl groups; and heteroarylsilyl refers to a silyl group in which one, two, or three hydrogen atoms of -SiH3 are replaced by heteroaryl groups. Examples of arylsilyl compounds may include monoarylsilyl compounds, substituted or unsubstituted diarylsilyl compounds, or substituted or unsubstituted triarylsilyl compounds, and are also applicable to alkylsilyl compounds and heteroarylsilyl compounds.

[0069] In this document, the aryl group in each of the arylsilyl, heteroarylsilyl and arylheteroarylsilyl groups can be a monocyclic aryl or a polycyclic aryl, and the heteroaryl group in each of the arylsilyl, heteroarylsilyl and arylheteroarylsilyl groups can be a monocyclic heteroaryl or a polycyclic heteroaryl.

[0070] In addition, specific examples of silyl groups may include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, etc., and one or more hydrogen atoms of the silyl group may be replaced by the same substituents as in the case of aryl groups.

[0071] In this invention, the amino group can include -NH2, alkylamino, arylamino, alkylarylamino, arylheteroarylamino, heteroarylamino, etc. An arylamino is an amino group in which one or two hydrogen atoms of -NH2 are replaced by an aryl group; an alkylamino is an amino group in which one or two hydrogen atoms of -NH2 are replaced by an alkyl group; and an alkylarylamino is an amino group in which one hydrogen atom of -NH2 is replaced by an alkyl group and the other hydrogen atom is replaced by an aryl group. An arylheteroarylamino is an amino group in which one hydrogen atom of -NH2 is replaced by an aryl group and the other hydrogen atom is replaced by a heteroaryl group; and a heteroarylamino is an amino group in which one or two hydrogen atoms of -NH2 are replaced by a heteroaryl group. Examples of arylamino groups can include substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, or substituted or unsubstituted triarylamino groups, and this also applies to alkylamino and heteroarylamino groups.

[0072] In this document, the aryl group in each of the arylamine, heteroarylamine, and arylheteroarylamine groups can be a monocyclic aryl or a polycyclic aryl, and the heteroaryl group in each of the arylamine, heteroarylamine, and arylheteroarylamine groups can be a monocyclic heteroaryl or a polycyclic heteroaryl.

[0073] In this invention, germanium-based (or germanyl) may include -GeH3, alkylgermanium-based, arylgermanium-based, heteroarylgermanium-based, alkylarylgermanium-based, alkylheteroarylgermanium-based, arylheteroarylgermanium-based, etc. It is defined in accordance with the description provided for silane, and can be applied to various substituents obtained by substituting silicon (Si) atoms in silane with germanium (Ge) atoms.

[0074] Furthermore, specific examples of germanium groups may include trimethylgermanane, triethylgermanane, triphenylgermanane, trimethoxygermanane, dimethoxyphenylgermanane, diphenylmethylgermanane, diphenylvinylgermanane, methylcyclobutylgermanane, dimethylfuranylgermanane, etc., and one or more hydrogen atoms of the germanium group may be replaced by the same substituents as in the case of aryl groups.

[0075] In this invention, the cycloalkyl, aryl, and heteroaryl groups among cycloalkyloxy, aryloxy, heteroaryloxy, cycloalkylthio, arylthio, and heteroarylthio groups are the same as the examples of cycloalkyl, aryl, and heteroaryl groups described above. Specific examples of aryloxy groups may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc., and specific examples of arylthio groups may include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc. However, aryloxy and arylthio groups are not limited thereto.

[0076] In this invention, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0077] According to one embodiment of the invention, the polycyclic compound represented by [Chemical Formula 1] can be any of the compounds represented by the following chemical formulas; however, the scope of the invention is not limited thereto.

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] Furthermore, another aspect of the present invention relates to an organic light-emitting device comprising: a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein the organic layers, preferably the light-emitting layers, contain a compound represented by [Chemical Formula 1] as a dopant.

[0086] The light-emitting layer has a structure consisting of a host and a dopant. In addition to the compound according to the invention, the light-emitting layer may also contain other host or dopant materials, and in this document, based on about 100 parts by weight of the host, the dopant content may generally be selected in the range of about 0.01 parts by weight to about 20 parts by weight; however, the dopant content is not limited thereto.

[0087] In addition to the compounds according to the invention, the light-emitting layer may also contain various dopant materials and host materials, and thus, one or more different compounds may be mixed or layered as dopant materials and host materials in the light-emitting layer.

[0088] Therefore, when a compound represented by [Chemical Formula 1] is used as a fluorescent or delayed fluorescence dopant in the light-emitting layer, the light-emitting layer in the organic light-emitting device according to the present invention may contain an anthracene compound represented by the following [Chemical Formula 2] as the host material.

[0089] [Chemical Formula 2]

[0090]

[0091] In [Chemical Formula 2],

[0092] R 21 To R 28 They may be the same as or different from each other, and each independently is selected from any of the following: hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups.

[0093] Ar1 and Ar3 may be identical or different from each other, and each is independently a single bond or selected from any of the following: substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 Heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30A divalent cyclic group fused with aromatic rings.

[0094] Ar2 and Ar4 may be identical or different from each other, and each is independently selected from any of the following: substituted or unsubstituted C6-C. 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C3-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups.

[0095] D n It refers to the number of hydrogen atoms replaced by deuterium atoms in [Chemical Formula 2], and n is an integer from 0 to 60.

[0096] According to one embodiment of the invention, the anthracene compound represented by [Chemical Formula 2] can be any of the compounds represented by the following chemical formulas; however, the scope of the invention is not limited thereto.

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The organic layer of the organic light-emitting device according to the present invention can be formed as a single-layer structure, but it can also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic layer can 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 to this, and it may also include fewer or more organic layers, and preferred organic material layer structures of the organic light-emitting device according to the present invention will be described in more detail in the examples described below.

[0120] In addition to the compounds according to the invention, the organic light-emitting device according to one embodiment of the invention may also include various host materials and dopant materials in the light-emitting layer, and thus, one or more different compounds may be mixed or layered as dopant materials and host materials in the light-emitting layer.

[0121] Furthermore, according to one embodiment of the invention, in addition to the compound according to the invention, the dopant may also contain at least one organometallic compound, which may be used in combination or layered.

[0122] Therefore, in an organic light-emitting device according to one embodiment of the present invention, the light-emitting layer can be formed to include a first host, a second host, an organometallic compound, and a boron-based thermally activated delayed fluorescent emitter material.

[0123] In this paper, organometallic compounds are used as sensitizers, and boron-based thermally activated delayed fluorescent emitters are used as luminescent dopants. The sensitizer compound receives excitons from the first and second hosts and transfers them to the luminescent dopant.

[0124] Therefore, excitons are transferred from the sensitizer to the luminescent dopant compound via Dexter energy transfer (DET) or Forster resonance transfer (FRET) mechanisms, and the energy of the excitons transferred to the luminescent dopant compound can be emitted as light during the transition to the ground state. In this paper, excitons in the sensitizer can be formed by transferring from the first and second hosts via the FRET mechanism, or by transferring excitons generated from the host via the DET mechanism.

[0125] Therefore, energy can be easily transferred between the sensitizer and the luminescent dopant through the FRET and DET mechanisms, and triplet-triplet annihilation is suppressed, thus enabling the fabrication of high-efficiency organic light-emitting devices.

[0126] Using the compound of [Chemical Formula 1] according to the present invention as a boron-based thermally activated delayed fluorescence emitter, Forster energy transfer from the triplet state of the phosphorus photosensitizer to the singlet state of the boron-based thermally activated delayed fluorescence emitter can be achieved, and as a result, the lifetime of the device can be improved by reducing the number of long-lived triplet excitons involved in device degradation.

[0127] Furthermore, due to the high molar extinction coefficient of the compound, the fluorescence resonance energy transfer rate from the phosphor photosensitizer to the emitter can be increased, and the emission spectrum can be narrowed due to the multiple resonance effect. As a result, efficiency and lifetime can be improved by effects such as enhanced color purity.

[0128] An embodiment of the organic light-emitting device according to the present invention will be described in more detail below.

[0129] The organic light-emitting device of the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. Depending on the requirements, the organic light-emitting device of the present invention may further include 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, as well as a hole blocking layer or an electron blocking layer. Furthermore, as described above, depending on the device characteristics, it may also include organic layers with various functions, such as a capping layer.

[0130] Meanwhile, the specific structure of the organic light-emitting device according to one embodiment of the present invention, its manufacturing method, and the materials of each organic layer can be studied as follows.

[0131] First, the material for the anode electrode is coated onto the substrate to form the anode. In this paper, substrates commonly used in organic light-emitting devices can be used as the substrate, and organic substrates or transparent plastic substrates with excellent transparency, surface smoothness, ease of handling, and water resistance are preferred. As materials for the anode electrode, transparent materials with excellent conductivity such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO) are used.

[0132] A hole injection layer is formed by coating a hole injection layer material onto the anode electrode using vacuum thermal deposition or spin coating. Then, a hole transport layer material is formed by coating the hole injection layer onto the hole transport layer using vacuum thermal deposition or spin coating.

[0133] There are no particular limitations on the hole injection layer material, as long as it is commonly used in the art. Examples 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), etc.

[0134] There are no particular restrictions on the hole transport layer material, as long as it is commonly used in the field. Examples may include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-(1,1-biphenyl)-4,4'-diamine (TPD), N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD), etc.

[0135] Subsequently, a hole-assist layer and an emissive layer are sequentially laminated on the hole transport layer. The hole-blocking layer can optionally be formed as a thin film on the emissive layer using vacuum deposition or spin coating. When holes cross the organic emissive layer and flow into the cathode, the device lifetime and efficiency decrease; the hole-blocking layer prevents this problem by using materials with very low highest occupied molecular orbitals (HOMO) levels. The hole-blocking materials used in this paper are not particularly limited, but they need to have a higher ionization potential than the emissive compound while also possessing electron transport capabilities. Representative examples may include BAlq, BCP, TPBI, etc.

[0136] Materials used for hole blocking layers include BAlq, BCP, Bphen, TPBI, TAZ, BeBq2, OXD-7, Liq, etc., but the materials are not limited to these.

[0137] After depositing an electron transport layer on a hole blocking layer using vacuum deposition or spin coating, 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. As a result, an organic light-emitting device according to an embodiment of the present invention is completed.

[0138] In this paper, 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 metals for forming the cathode. In order to obtain a top-emitting light-emitting device, a transmission cathode using ITO or IZO can be used.

[0139] As materials for the electron transport layer, known electron transport materials that serve to stably transport electrons injected from the cathode can be used. Examples of known electron transport materials can include materials such as quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, BAlq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), and... Diazole derivatives (PBD, BMD, BND, etc.).

[0140] Furthermore, each of the organic layers can be formed using either monomolecular deposition or solution methods. In this context, monomolecular deposition refers to a method of forming a thin film by vaporizing the material used for each of the layers under vacuum or reduced pressure via heating, etc., while solution methods refer to a method of forming a thin film by mixing the material used for each of the layers with a solvent and then applying methods such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, or spin coating to the mixture.

[0141] Furthermore, 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 reality or augmented reality, etc.

[0142] Preferred synthetic examples of compounds and device embodiments are provided below to aid in understanding the invention. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

[0143] Synthesis Example 1: Synthesis of [Compound 2]

[0144] Synthesis Example 1-1: Synthesis of A-1

[0145]

[0146] Will <a-1a> （20 g）、 <a-1b>12.3 g of Pd(dba)3 (1.4 g), 1.3 g of P(t-Bu)3HBF4 (1.3 g), 10.8 g of t-BuONa (10.8 g), and 250 mL of toluene were introduced into the reactor, and the mixture was stirred under reflux for 6 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by column chromatography to obtain the desired product. <a-1>(21 g, 83.6%).

[0147] Synthesis Example 1-2: Synthesis of A-2

[0148]

[0149] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <a-2>The difference lies in the use <a-2a>replace <a-1a>and use <a-1>replace <a-1b>(Yield 79%)

[0150] Synthetic Examples 1-3: Synthesis of [Compound 2]

[0151]

[0152] Will <a-2>(3 g), BI3 (9.86 g), BPh3 (2.44 g), and 1,2,4-trichlorobenzene (120 mL) were introduced into the reactor, and the mixture was stirred at 180 °C for 6 hours. The temperature was then lowered to 120 °C, and N,N-diisopropylethylamine (13.1 mL) was added, followed by stirring for 1 hour. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by column chromatography to obtain [compound 2] (0.6 g, 19.5%).

[0153] MS (MALDI-TOF): m / z 611.32 [M + ]

[0154] Synthesis Example 2: Synthesis of [Compound 7] and [Compound 8]

[0155] Synthesis Example 2-1: Synthesis of B-1

[0156]

[0157] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <b-1>The difference lies in the use <b-1a>replace <a-1a>and use <b-1b>replace <a-1b>(Yield 77%)

[0158] combine Example 2-2: Synthesis of B-2

[0159]

[0160] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <b-2>The difference lies in the use <b-1>replace <a-1a>and use <a-1>replace <a-1b>(Yield 80%)

[0161] Synthesis Example 2-3: Synthesis of B-3

[0162]

[0163] In <b-2>After 15 g of BBr3 and 200 mL of dichloromethane were introduced into the reactor, BBr3 (10.4 g) was added dropwise while the mixture was stirred at -78 °C. The temperature was then raised to room temperature, and the mixture was stirred for 24 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by column chromatography to obtain the desired product. <b-3>(7.3g, 49.6%).

[0164] Synthesis Example 2-4: Synthesis of B-4

[0165]

[0166] Will <b-3> （10 g）、 <b-4a>11 g of potassium carbonate (7.8 g), 0.04 g of CuI, 0.15 g of Fe(III)(acac) and 400 mL of NMP were introduced into the reactor, and the mixture was stirred under reflux at 180 °C for 10 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by column chromatography to obtain the desired product. <b-4>(2.7 g, 22.8%).

[0167] Synthetic Examples 2-5: Synthesis of [Compound 7] and [Compound 8]

[0168]

[0169] [Compound 7] and [Compound 8] were obtained by synthesis in the same manner as in Synthetic Examples 1-3, except that [compound 7] was used. <b-4>replace <a-2>(Yields were 11% and 6% respectively)

[0170] MS (MALDI-TOF): m / z 854.55 [M + ]

[0171] Synthesis Example 3: Synthesis of [Compound 9] and [Compound 10]

[0172] Synthesis Example 3-1: Synthesis of C-1

[0173]

[0174] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <c-1>The difference lies in the use <c-1a>replace <a-1b>(Yield 72%)

[0175] Synthesis Example 3-2: Synthesis of C-2

[0176]

[0177] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <c-2>The difference lies in the use <b-1>replace <a-1a>and use <c-1>replace <a-1b>(Yield 64%)

[0178] Synthesis Example 3-3: Synthesis of C-3

[0179]

[0180] The result was obtained by synthesizing in the same manner as in synthetic examples 2-3. <c-3>The difference lies in the use <c-2>replace <b-2>(Yield 51%)

[0181] Synthesis Example 3-4: Synthesis of C-4

[0182]

[0183] The product was obtained by synthesizing in the same manner as in synthetic examples 2-4. <c-4>The difference lies in the use <c-3>replace <b-3>(Yield 23%)

[0184] Synthetic Examples 3-5: Synthesis of [Compound 9] and [Compound 10]

[0185]

[0186] [Compound 9] and [Compound 10] were obtained by synthesis in the same manner as in Synthetic Examples 1-3, the difference being the use of... <c-4>replace <a-2>(Yields were 8% and 5% respectively)

[0187] MS (MALDI-TOF): m / z 965.56 [M + ]

[0188] Synthesis Example 4: Synthesis of [Compound 13]

[0189] Synthesis Example 4-1: Synthesis of D-1

[0190]

[0191] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <d-1>The difference lies in the use <d-1a>replace <a-1a>and use <d-1b>replace <a-1b>(Yield 67%)

[0192] Synthesis Example 4-2: Synthesis of D-2

[0193]

[0194] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <d-2>The difference lies in the use <a-2a>replace <a-1a>and use <d-1>replace <a-1b>(Yield 73%)

[0195] Synthetic Example 4-3: Synthesis of [Compound 13]

[0196]

[0197] [Compound 13] was obtained by synthesis in the same manner as in Synthetic Examples 1-3, except that [compound 13] was obtained by using [method / method]. <d-2>replace <a-2>(Yield 18%)

[0198] MS (MALDI-TOF): m / z 667.29 [M + ]

[0199] Synthesis Example 5: Synthesis of [Compound 39]

[0200] Synthesis Example 5-1: Synthesis of E-1

[0201]

[0202] Under a nitrogen atmosphere <e-1b>(26.4 g), cesium carbonate (50.6 g), and NMP (120 mL) were introduced into the reactor and then stirred. Then, [the following was added] <e-1a>(10 g), and the mixture was stirred at 120 °C for 24 hours. Afterwards, the temperature was lowered to 0 °C, 6 N HCl (55 mL) was added, and the product was extracted with toluene. After the reaction was complete, the organic layer was washed with water, concentrated under reduced pressure, and then purified by column chromatography to obtain... <e-1>(25.3 g, 87%).

[0203] Synthesis Example 5-2: Synthesis of E-2

[0204]

[0205] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <e-2>The difference lies in the use <d-1a>replace <a-1a>(Yield 75%)

[0206] Synthesis Example 5-3: Synthesis of E-3

[0207]

[0208] The result was obtained by synthesizing in the same manner as in Synthesis Example 1-1. <e-3>The difference lies in the use <e-1>replace <a-1a>and use <e-2>replace <a-1b>(Yield 75%)

[0209] Synthetic Example 5-4: Synthesis of [Compound 39]

[0210]

[0211] [Compound 39] was obtained by synthesis in the same manner as in Synthetic Examples 1-3, except that [compound 39] was obtained by using [method / method]. <e-3>replace <a-2>(Yield 19.3%)

[0212] MS (MALDI-TOF): m / z 833.46 [M + ]

[0213] Examples 1 to 7: Fabrication of Organic Light-Emitting Devices

[0214] The ITO glass was patterned to have a 2 mm × 2 mm luminescent area, and then cleaned. The ITO glass was mounted in a vacuum chamber, and the base pressure was set to 1 × 10⁻⁶. -7 Then, on ITO, an electron acceptor having the following structural formula [acceptor-1] and [chemical formula F] are deposited at a deposition ratio of 2:98 ([acceptor-1]:[chemical formula F]) as a hole injection layer (100 Å). [chemical formula F] is deposited at 550 Å as a hole transport layer, followed by the deposition of [chemical formula G] at 50 Å as an electron blocking layer. As a light-emitting layer, the host [BH-1] described below and the compound of the present invention (2 wt%) are mixed and deposited at 200 Å. Subsequently, in this order, [chemical formula H] is deposited at 50 Å as a hole blocking layer, [chemical formula E-1] and [chemical formula E-2] are deposited at a 1:1 ratio at 250 Å as an electron transport layer, [chemical formula E-2] is deposited at 10 Å as an electron injection layer, and Al is deposited at 1000 Å to fabricate an organic light-emitting device. The luminescence characteristics of organic light-emitting devices were measured at 0.4 mA.

[0215]

[0216]

[0217]

[0218] Comparative Examples 1 to 3

[0219] The organic light-emitting device was fabricated in the same manner as in the examples, except that [RD-1] to [RD-3] were used instead of the compounds used in the examples, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA. The structures of [RD-1] to [RD-3] are as follows.

[0220]

[0221] For the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 3, the external quantum efficiency and lifetime were measured, and the results are shown in Table 1 below.

[0222] [Table 1]

[0223]

[0224] As shown in [Table 1], compared with devices using compounds whose structures are in contrast to the characteristic structures of the compounds according to the present invention (Comparative Examples 1 to 3), devices using compounds according to the present invention as dopant compounds in the light-emitting layer of organic light-emitting devices can realize high-efficiency, long-lifetime organic light-emitting devices with excellent quantum efficiency and lifetime characteristics.

[0225] Industrial applicability

[0226] This invention relates to polycyclic compounds having a characteristic fused ring structure, and since high-efficiency, long-life organic light-emitting devices with excellent device characteristics such as luminous efficiency and lifetime can be realized by using the compounds as dopant materials in the light-emitting layer of organic light-emitting devices, the devices can be used in industry not only for lighting devices, but also for various display devices such as flat panel displays, flexible displays and wearable displays, as well as displays for virtual reality or augmented reality. < / b-3> < / a-1a>

Claims

1. A polycyclic compound represented by the following [Chemical Formula 1]: [Chemical Formula 1] in, In [Chemical Formula 1], X, Y1, and Y2 are each independently B or N; Z1 and Z2 may be the same as or different from each other, and each is independently selected from O, S, NR1, CR2R3, SiR4R5 and GeR6R7; Rings A1 to A4 may be identical or different from each other, and each is independently selected from any of the following: substituted or unsubstituted C6-C. 50 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Aromatic heterocycles, substituted or unsubstituted C2-C 50 Aliphatic heterocycles, and C3-C of substituted or unsubstituted heterocycles. 30 Aliphatic rings and C3-C 30 A ring fused with aromatic rings, provided that at least one of rings A1 to A4 is either substituted or unsubstituted, wherein C3-C 30 Aliphatic rings and C3-C 30 Aromatic rings that are densely packed; R is selected from any of the following: hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups; R1 through R7 may be the same as or different from each other, and each is independently selected from any of the following: substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups; Ring A1 is connected to X and Y1 to form a ring, ring A2 is connected to X and Y2 to form a ring, ring A3 is connected to Y1 and Z1 to form a ring, and ring A4 is connected to Y2 and Z2 to form a ring; R may optionally be connected to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring; R2 and R3, R4 and R5, and R6 and R7 are each optionally connected to each other to further form alicyclic or aromatic monocyclic or polycyclic rings; R1 to R7 may be optionally connected to the adjacent ring A3 or A4 to further form alicyclic or aromatic monocyclic or polycyclic rings; Adjacent rings A1 to A4 may optionally connect to each other to further form alicyclic or aromatic monocyclic or polycyclic rings; and In [Chemical Formula 1], "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium, C1-C 24 Alkyl, C1-C 24 Haloalkyl, C2-C 24 alkenyl, C2-C 24 alkynyl group, C3-C 30 cycloalkyl, C1-C 24 Heteroalkyl, C6-C 30 Aryl, C7-C 30 arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 heteroaryl, C2-C 30 Heteroarylalkyl, wherein C3-C 24 Aliphatic rings and C3-C 24 Aromatic ring fused cyclic groups, C1-C 24 Alkoxy, C1-C 30 Amine group, C1-C 30 Silyl, C1-C 30 Germanium-based, C6-C 24 Aryloxy group, C6-C 24 The substituents are arylthionyl, cyano, halogen, hydroxyl, and nitro, or are substituted by two or more of the above substituents linked together, wherein one or more hydrogen atoms of the substituents are optionally replaced by deuterium atoms, and two or more adjacent substituents are optionally linked together to further form an alicyclic or aromatic monocyclic or polycyclic ring.

2. The polycyclic compound according to claim 1, wherein ring A1 in [Chemical Formula 1] is substituted or unsubstituted, wherein C3-C 24 Aliphatic rings and C3-C 24 A ring of fused aromatic rings.

3. The polycyclic compound according to claim 1, wherein, In [Chemical Formula 1], when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

4. The polycyclic compound according to claim 1, wherein Z1 and Z2 in [Chemical Formula 1] are the same as or different from each other, and each is independently selected from any one of O, S and NR1.

5. The polycyclic compound according to claim 4, wherein at least one of Z1 and Z2 in [Chemical Formula 1] is O or S.

6. The polycyclic compound according to claim 2, wherein [Chemical Formula 1] is represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-3]: In [Chemical Formula 1-1] to [Chemical Formula 1-3], X, Y1, and Y2 are each independently B or N; Z1 and Z2 may be the same as or different from each other, and each is independently selected from O, S and NR1; Rings A2 through A4 may be identical or different from each other, and each is independently selected from any of the following: substituted or unsubstituted C6-C. 50 Aromatic hydrocarbon rings, substituted or unsubstituted C3-C 50 Aliphatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Aromatic heterocycles, substituted or unsubstituted C2-C 50 Aliphatic heterocycles, and C3-C of substituted or unsubstituted heterocycles. 30 Aliphatic rings and C3-C 30 Aromatic rings that are densely packed; R and R 19 They may be the same as or different from each other, and each independently is selected from any of the following: hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups; R1 and R 11 To R 14 They may be the same as or different from each other, and each independently is selected from any of the following: hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups; R 15 To R 18 They may be the same as or different from each other, and each is independently hydrogen or deuterium; m is an integer 2; Ring A2 is connected to X and Y2 to form a ring, ring A3 is connected to Y1 and Z1 to form a ring, and ring A4 is connected to Y2 and Z2 to form a ring; R may optionally be connected to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring; Adjacent R 11 To R 14 They can be optionally connected to each other to further form alicyclic or aromatic monocyclic or polycyclic rings; R1 may optionally be connected to the adjacent ring A3 or A4 to further form an alicyclic or aromatic monocyclic or polycyclic ring; Adjacent rings A2 and A4 may optionally be connected to each other to further form alicyclic or aromatic monocyclic or polycyclic rings; and The term "substituted or unsubstituted" in [Chemical Formulas 1-1] to [Chemical Formulas 1-3] means substituted with one or more of the following substituents: deuterium, C1-C 24 Alkyl, C1-C 24 Haloalkyl, C2-C 24 alkenyl, C2-C 24 alkynyl group, C3-C 30 cycloalkyl, C1-C 24 Heteroalkyl, C6-C 30 Aryl, C7-C 30 arylalkyl, C7-C 30 Alkyl aryl, C2-C 30 heteroaryl, C2-C 30 Heteroarylalkyl, wherein C3-C 24 Aliphatic rings and C3-C 24 Aromatic ring fused cyclic groups, C1-C 24 Alkoxy, C1-C 30 Amine group, C1-C 30 Silyl, C1-C 30 Germanium-based, C6-C 24 Aryloxy group, C6-C 24 The substituents are arylthionyl, cyano, halogen, hydroxyl, and nitro, or are substituted by two or more of the above substituents linked together, wherein one or more hydrogen atoms of the substituents are optionally replaced by deuterium atoms, and two or more adjacent substituents are optionally linked together to further form an alicyclic or aromatic monocyclic or polycyclic ring.

7. The polycyclic compound according to claim 6, wherein, In [Chemical Formula 1-1] to [Chemical Formula 1-3], when X is B, Y1 and Y2 are N, or when X is N, Y1 and Y2 are B.

8. The polycyclic compound according to claim 1, wherein at least one hydrogen atom in [Chemical Formula 1] may be replaced by deuterium.

9. The polycyclic compound according to claim 1, wherein [Chemical Formula 1] is selected from any of the following compounds: 。 10. An organic light-emitting device, comprising: First electrode; A second electrode disposed opposite to the first electrode; and An organic layer between the first electrode and the second electrode, 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 hole injection and hole transport functions, a light-emitting layer, an electron transport layer, a hole blocking layer, and a functional layer having both electron injection and electron transport functions; and The organic layer comprises at least one polycyclic compound represented by [Chemical Formula 1] according to claim 1.

11. The organic light-emitting device according to claim 10, wherein the light-emitting layer comprises a host and a dopant, and at least one of the polycyclic compounds represented by [Chemical Formula 1] is a dopant in the light-emitting layer.

12. The organic light-emitting device according to claim 11, wherein, as the dopant, one or more other compounds are mixed or layered in addition to a compound represented by [Chemical Formula 1].

13. The organic light-emitting device according to claim 11, wherein at least one anthracene compound represented by the following [Chemical Formula 2] is used as the host in the light-emitting layer in a mixed or layered manner: [Chemical Formula 2] In [Chemical Formula 2], R 21 To R 28 They may be the same as or different from each other, and each independently is selected from any of the following: hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C2-C 30 Alkyne group, 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 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 Heteroaryl, substituted or unsubstituted C3-C 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, nitro, cyano and halogen groups; Ar1 and Ar3 may be identical or different from each other, and each is independently a single bond, or a substituted or unsubstituted C6-C bond. 30 aryl, substituted or unsubstituted C2-C 30 Heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30 Aromatic ring fused divalent cyclic groups; Ar2 and Ar4 may be identical or different from each other, and each is independently selected from any of the following: substituted or unsubstituted C6-C. 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C3-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl compounds, and their substituted or unsubstituted C3-C groups. 30 Aliphatic rings and C3-C 30 Aromatic ring fused cyclic groups; D n This refers to the number of hydrogen atoms replaced by deuterium atoms in [Chemical Formula 2]; and n is an integer from 0 to 60.

14. The organic light-emitting device according to claim 13, wherein the compound represented by [Chemical Formula 2] is selected from any of the following compounds: 。 15. The organic light-emitting device according to claim 10, wherein the organic light-emitting device is used in any of the following devices: flat panel display devices; flexible display devices; monochrome or white flat panel lighting devices; monochrome or white flexible lighting devices; display devices for vehicles; and display devices for virtual reality or augmented reality.

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