WO2018048247A1 - Composé et élément électronique organique le comprenant - Google Patents

Composé et élément électronique organique le comprenant Download PDF

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WO2018048247A1
WO2018048247A1 PCT/KR2017/009879 KR2017009879W WO2018048247A1 WO 2018048247 A1 WO2018048247 A1 WO 2018048247A1 KR 2017009879 W KR2017009879 W KR 2017009879W WO 2018048247 A1 WO2018048247 A1 WO 2018048247A1
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group
substituted
unsubstituted
present specification
compound
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PCT/KR2017/009879
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Korean (ko)
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차용범
서상덕
김정범
홍성길
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주식회사 엘지화학
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Priority claimed from KR1020170113862A external-priority patent/KR102032023B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201780024267.6A priority Critical patent/CN109071449B/zh
Priority to US16/085,547 priority patent/US11306060B2/en
Priority to JP2018549326A priority patent/JP6750784B2/ja
Priority to EP17849131.2A priority patent/EP3428152B1/fr
Publication of WO2018048247A1 publication Critical patent/WO2018048247A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants

Definitions

  • the present specification relates to a compound and an organic electronic device including the same.
  • organic electronic device examples include an organic light emitting device.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present specification is to provide a compound and an organic electronic device including the same.
  • L101, L1, and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R1 to R25 Groups other than are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with adjacent groups to form a substituted or unsubstituted ring,
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the compound according to the exemplary embodiment of the present specification may be used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electric device.
  • the compound according to one embodiment of the present specification may be used in an organic electronic device including an organic light emitting device, thereby improving light efficiency.
  • the compound according to the exemplary embodiment of the present specification may be used in an organic electronic device including an organic light emitting device, thereby improving lifetime characteristics of the device by thermal stability of the compound.
  • FIG. 1 illustrates an organic light emitting device 10 according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting device 11 according to another exemplary embodiment of the present specification.
  • the core structure of the compound of Formula 1 is a spiro type compound, specifically, a dibenzofluorene structure.
  • the dibenzofluorene structure has a form with a lot of electrons compared with the structure of fluorene and benzofluorene.
  • the compound represented by the formula (1) of the present specification has a structure of a condensed ring containing N or containing N, compared to the spirobifluorene structure, because the skeleton is composed of a larger structure is excellent in terms of stability of the compound .
  • important life characteristics have a remarkably excellent effect.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the term "substituted or unsubstituted” is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Imide group; Amide group; Alkyl groups; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Silyl groups; Phosphine oxide groups; Amine groups; Aryl group; And one or two or more substituents selected from the group consisting of a heterocyclic group including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the substituents exemplified above are substituted with a substituent, or any It means that it does not have a substituent.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 50.
  • Specific examples 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-
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40.
  • Specific examples 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, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR 201 R 202 R 203 , and R 201 to R 203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 50 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C50.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • Etc When the fluorenyl group is substituted, Etc., but is not limited thereto.
  • the heterocyclic group includes one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridine group , Pyridazine group, pyrazine group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group , Benzoxazole group, benzimid
  • the heteroaryl group may be selected from examples of the heterocyclic group except that the heteroaryl group is aromatic, but is not limited thereto.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • adjacent groups are bonded to each other to form a ring
  • the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups are bonded to each other, as described above, to form a 5 to 8 membered hydrocarbon ring or a 5 to 8 membered hetero ring.
  • Monocyclic or polycyclic and may be aliphatic, aromatic or condensed form thereof, but is not limited thereto.
  • the hydrocarbon ring or heterocycle herein may be selected from the examples of the cycloalkyl group, aryl group or heteroaryl group described above, except that the hydrocarbon ring or heterocycle is monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic or condensed form thereof. But. It is not limited only to these.
  • the aromatic ring group may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • the divalent to tetravalent aromatic ring group may be monocyclic or polycyclic, meaning that the aryl group has 2 to 4 bonding positions, that is, 2 to 4 valent groups.
  • the description of the aforementioned aryl groups can be applied except that they are each 2 to 4 valent groups.
  • the amine group is represented by -NR 206 R 207 , R 206 and R 207 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, or aryl. It may be a substituent consisting of at least one of a group, and a heterocyclic group.
  • -NH 2 monoalkylamine group, dialkylamine group, N-alkylarylamine group, monoarylamine group, diarylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, mono It may be selected from the group consisting of a heteroarylamine group and diheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Diphenylamine group Ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenyl flu Orenylamine groups, N-biphenylfluorenylamine groups, and the like, but are not limited thereto.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the alkyl group in the alkylamine group, the N-alkylarylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, and N-arylheteroarylamine group is the same as the example of the aryl group described above.
  • the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3 -Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyl jade There are a period, a 2-anthracenyloxy group, a 9-anthracenyloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like, and an arylthioxy group is a phenylthioxy group, 2 -Methylphenyl thioxy group, 4-tert-butyl
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • the arylene group refers to a divalent group having two bonding positions in the aryl group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • L101, L1, and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L101 is a direct bond.
  • L101 is a substituted or unsubstituted arylene group.
  • L101 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group.
  • L101 is a substituted or unsubstituted divalent heterocyclic group.
  • L1 is a direct bond
  • L1 is a substituted or unsubstituted arylene group.
  • L1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted Ring phenanthrene group or substituted or unsubstituted fluorenylene group.
  • L1 is an phenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenylene group unsubstituted or substituted with a silyl group.
  • L1 is a phenylene group.
  • L1 is a biphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a biphenylene group unsubstituted or substituted by a silyl group.
  • L1 is a biphenylene group.
  • L1 is a terphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a terphenylene group unsubstituted or substituted by a silyl group.
  • L1 is a terphenylene group.
  • L1 is an naphthylene group which is unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a naphthylene group unsubstituted or substituted by a silyl group.
  • L1 is a naphthylene group.
  • L1 is an phenanthrene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenanthrene group unsubstituted or substituted with a silyl group.
  • L1 is a phenanthrene group.
  • L1 is an fluorenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group .
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a fluorenylene group unsubstituted or substituted by a silyl group.
  • L1 is a fluorenylene group.
  • L1 is a substituted or unsubstituted divalent heterocyclic group.
  • L1 is a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent dibenzofuran group, or a substituted or unsubstituted divalent dibenzothiophene group.
  • L1 is a divalent carbazole group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, an aryl group, or a heterocyclic group.
  • L1 is a divalent carbazole group unsubstituted or substituted with a phenyl group.
  • L1 is a divalent dibenzofuran unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzofuran group unsubstituted or substituted by a silyl group.
  • L1 is a divalent dibenzofuran group.
  • L1 is a divalent dibenzoti unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • an alkyl group a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzothiophene group substituted or unsubstituted by the silyl group.
  • L1 is a divalent dibenzothiophene group.
  • L2 is a direct bond
  • L2 is a substituted or unsubstituted arylene group.
  • L2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted Ring phenanthrene group or substituted or unsubstituted fluorenylene group.
  • L2 is an phenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenylene group unsubstituted or substituted with a silyl group.
  • L2 is a phenylene group.
  • L2 is a biphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a biphenylene group unsubstituted or substituted by a silyl group.
  • L2 is a biphenylene group.
  • L2 is a terphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a terphenylene group unsubstituted or substituted by a silyl group.
  • L2 is a terphenylene group.
  • L2 is an naphthylene group which is unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a naphthylene group unsubstituted or substituted by a silyl group.
  • L2 is a naphthylene group.
  • L2 is an phenanthrene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenanthrene group unsubstituted or substituted with a silyl group.
  • L2 is a phenanthrene group.
  • L2 is an fluorenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group .
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a fluorenylene group unsubstituted or substituted by a silyl group.
  • L2 is a fluorenylene group.
  • L2 is a substituted or unsubstituted divalent heterocyclic group.
  • L2 is a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent dibenzofuran group, or a substituted or unsubstituted divalent dibenzothiophene group.
  • L2 is a divalent carbazole group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, an aryl group, or a heterocyclic group.
  • L2 is a divalent carbazole group unsubstituted or substituted with a phenyl group.
  • L2 is a divalent dibenzofuran unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzofuran group unsubstituted or substituted by a silyl group.
  • L2 is a divalent dibenzofuran group.
  • L2 is a divalent dibenzoty unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group Oppeni.
  • L2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzothiophene group substituted or unsubstituted by the silyl group.
  • L2 is a divalent dibenzothiophene group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar1 is hydrogen
  • Ar1 is a halogen group.
  • Ar1 is fluorine
  • Ar1 is a substituted or unsubstituted alkyl group.
  • Ar1 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.
  • Ar1 is a methyl group.
  • Ar1 is an ethyl group.
  • Ar1 is an isopropyl group.
  • Ar1 is a tert-butyl group.
  • Ar1 is a substituted or unsubstituted cycloalkyl group.
  • Ar1 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group.
  • Ar1 is a cyclohexyl group.
  • Ar1 is a substituted or unsubstituted silyl group.
  • Ar1 is a silyl group unsubstituted or substituted with an alkyl group.
  • Ar1 is a trimethylsilyl group.
  • Ar1 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted quarterphenyl group , A substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • Ar1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl And a phenyl group unsubstituted or substituted with a group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenyl group, or a dimethylfluorenyl group.
  • Ar1 is a phenyl group.
  • Ar1 is a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a biphenyl group.
  • Ar1 is a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a terphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a terphenyl group.
  • Ar1 is a triphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a triphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a triphenyl group.
  • Ar1 is a naphthyl group which is unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a naphthyl group which is unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a naphthyl group.
  • Ar1 is an anthracenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is an anthracenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is an anthracenyl group.
  • Ar1 is a phenanthryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a phenanthryl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a phenanthryl group.
  • Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 is a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar1 is a fluorenyl group.
  • Ar1 is a spirobifluorenyl group.
  • Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzocarbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene Qi.
  • Ar1 is a carbazole group unsubstituted or substituted with an aryl group.
  • Ar1 is a carbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar1 is a dibenzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar1 is a dibenzocarbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar1 is a dibenzofuran group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group .
  • Ar1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzofuran group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar1 is a benzonaphthofuran group.
  • Ar1 is a dibenzofuran group.
  • Ar1 is an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a dibenzothiophene group unsubstituted or substituted with a heterocyclic group. to be.
  • Ar1 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl Dibenzothiophene group unsubstituted or substituted with a group, a phenyl group, or a naphthyl group.
  • Ar1 is a benzonaphthothiophene group.
  • Ar1 is a dibenzothiophene group.
  • Ar2 is hydrogen
  • Ar2 is a halogen group.
  • Ar2 is fluorine
  • Ar2 is a substituted or unsubstituted alkyl group.
  • Ar2 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.
  • Ar2 is a methyl group.
  • Ar2 is an ethyl group.
  • Ar2 is an isopropyl group.
  • Ar2 is a tert-butyl group.
  • Ar2 is a substituted or unsubstituted cycloalkyl group.
  • Ar2 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group.
  • Ar2 is a cyclohexyl group.
  • Ar2 is a substituted or unsubstituted silyl group.
  • Ar2 is a silyl group unsubstituted or substituted with an alkyl group.
  • Ar2 is a trimethylsilyl group.
  • Ar2 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted quarterphenyl group , A substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
  • Ar2 is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • Ar2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl And a phenyl group unsubstituted or substituted with a group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenyl group, or a dimethylfluorenyl group.
  • Ar2 is a phenyl group.
  • Ar2 is a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a biphenyl group.
  • Ar2 is a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a terphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a terphenyl group.
  • Ar2 is a triphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a triphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a triphenyl group.
  • Ar2 is a naphthyl group which is unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a naphthyl group which is unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a naphthyl group.
  • Ar2 is an anthracenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is an anthracenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is an anthracenyl group.
  • Ar2 is a phenanthryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a phenanthryl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a phenanthryl group.
  • Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar2 is a fluorenyl group.
  • Ar2 is a spirobifluorenyl group.
  • Ar2 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar2 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzocarbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene.
  • Ar2 is a carbazole group unsubstituted or substituted with an aryl group.
  • Ar2 is a carbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar2 is a dibenzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar2 is a dibenzocarbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar2 is an dibenzofuran group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group. .
  • Ar2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzofuran group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar2 is a benzonaphthofuran group.
  • Ar2 is a dibenzofuran group.
  • Ar2 is an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a dibenzothiophene group unsubstituted or substituted with a heterocyclic group. to be.
  • Ar2 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzothiophene group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar2 is a benzonaphthothiophene group.
  • Ar2 is a dibenzothiophene group.
  • Ar1 and Ar2 may be the same as or different from each other, and each independently may be any one selected from the following substituents.
  • any one or more of Ar1 and Ar2 may be represented by the following Formula 1A.
  • X is S, O, CRR ', or NR.
  • X is S.
  • X is O.
  • X is CRR '.
  • X is NR.
  • R, R ', and R26 to R29 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • any one of R30 to R33 is bonded to L1 or L2 of Formula 1, and the groups not bonded to L1 or L2 of Formula 1 of R30 to R33 are the same as or different from each other, Each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R is a phenyl group.
  • R is a biphenyl group.
  • R26 is a methyl group.
  • R26 is an ethyl group.
  • R26 is an isopropyl group.
  • R26 is a tert-butyl group.
  • R26 is a cyclohexyl group.
  • R26 is fluorine
  • R26 is a nitrile group.
  • R26 is a phenyl group.
  • R26 is a trimethylsilyl group.
  • R26 is -OCF 3 .
  • R26 is -CF 3 .
  • R26 is -C 2 F 5 .
  • R28 is a phenyl group.
  • R28 and R29 may combine with each other to form a ring.
  • R32 and R33 may combine with each other to form a ring.
  • R27 and R29 to R33 are hydrogen.
  • R26 to R33 are each hydrogen.
  • R1 to R25 Groups other than are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R1 to R25 And groups other than are each hydrogen.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 8.
  • L102, L3 and L4 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
  • L102 is a direct bond.
  • L102 is a substituted or unsubstituted arylene group.
  • L102 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group.
  • L102 is a substituted or unsubstituted divalent heterocyclic group.
  • L3 is a direct bond
  • L3 is a substituted or unsubstituted arylene group.
  • L3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted Ring phenanthrene group or substituted or unsubstituted fluorenylene group.
  • L3 is an phenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenylene group unsubstituted or substituted with a silyl group.
  • L3 is a phenylene group.
  • L3 is a biphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a biphenylene group unsubstituted or substituted by a silyl group.
  • L3 is a biphenylene group.
  • L3 is a terphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a terphenylene group unsubstituted or substituted by a silyl group.
  • L3 is a terphenylene group.
  • L3 is an naphthylene group which is unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a naphthylene group unsubstituted or substituted by a silyl group.
  • L3 is a naphthylene group.
  • L3 is an phenanthrene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenanthrene group unsubstituted or substituted with a silyl group.
  • L3 is a phenanthrene group.
  • L3 is an fluorenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group .
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a fluorenylene group unsubstituted or substituted by a silyl group.
  • L3 is a fluorenylene group.
  • L3 is a substituted or unsubstituted divalent heterocyclic group.
  • L3 is a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent dibenzofuran group, or a substituted or unsubstituted divalent dibenzothiophene group.
  • L3 is a divalent carbazole group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, an aryl group, or a heterocyclic group.
  • L3 is a divalent carbazole group unsubstituted or substituted with a phenyl group.
  • L3 is a divalent dibenzofuran unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzofuran group unsubstituted or substituted by a silyl group.
  • L3 is a divalent dibenzofuran group.
  • L3 is a divalent dibenzoty unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group Oppeni.
  • L3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzothiophene group substituted or unsubstituted by the silyl group.
  • L3 is a divalent dibenzothiophene group.
  • L4 is a direct bond
  • L4 is a substituted or unsubstituted arylene group.
  • L4 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted Ring phenanthrene group or substituted or unsubstituted fluorenylene group.
  • L4 is an phenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenylene group unsubstituted or substituted with a silyl group.
  • L4 is a phenylene group.
  • L4 is a biphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a biphenylene group unsubstituted or substituted by a silyl group.
  • L4 is a biphenylene group.
  • L4 is a terphenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a terphenylene group unsubstituted or substituted by a silyl group.
  • L4 is a terphenylene group.
  • L4 is an naphthylene group which is unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a naphthylene group unsubstituted or substituted by a silyl group.
  • L4 is a naphthylene group.
  • L4 is an phenanthrene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl Or a phenanthrene group unsubstituted or substituted with a silyl group.
  • L4 is a phenanthrene group.
  • L4 is an fluorenylene group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group .
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, nitrile group, -OCF 3 , -CF 3 , -C 2 F 5 , or trimethyl It is a fluorenylene group unsubstituted or substituted by a silyl group.
  • L4 is a fluorenylene group.
  • L4 is a substituted or unsubstituted divalent heterocyclic group.
  • L4 is a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent dibenzofuran group, or a substituted or unsubstituted divalent dibenzothiophene group.
  • L4 is a divalent carbazole group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, an aryl group, or a heterocyclic group.
  • L4 is a divalent carbazole group unsubstituted or substituted with a phenyl group.
  • L4 is a divalent dibenzofuran unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzofuran group unsubstituted or substituted by a silyl group.
  • L4 is a divalent dibenzofuran group.
  • L4 is a divalent dibenzoty unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group Oppeni.
  • L4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, or trimethyl It is a bivalent dibenzothiophene group substituted or unsubstituted by the silyl group.
  • L4 is a divalent dibenzothiophene group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ar3 is hydrogen
  • Ar3 is a halogen group.
  • Ar3 is fluorine
  • Ar3 is a substituted or unsubstituted alkyl group.
  • Ar3 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.
  • Ar3 is a methyl group.
  • Ar3 is an ethyl group.
  • Ar3 is an isopropyl group.
  • Ar3 is a tert-butyl group.
  • Ar3 is a substituted or unsubstituted cycloalkyl group.
  • Ar3 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group.
  • Ar3 is a cyclohexyl group.
  • Ar3 is a substituted or unsubstituted silyl group.
  • Ar3 is a silyl group unsubstituted or substituted with an alkyl group.
  • Ar3 is a trimethylsilyl group.
  • Ar3 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • Ar3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted quarterphenyl group , A substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
  • Ar3 is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • Ar3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl And a phenyl group unsubstituted or substituted with a group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenyl group, or a dimethylfluorenyl group.
  • Ar3 is a phenyl group.
  • Ar3 is a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a biphenyl group.
  • Ar3 is a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a terphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a terphenyl group.
  • Ar3 is a triphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a triphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a triphenyl group.
  • Ar3 is a naphthyl group which is unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a naphthyl group which is unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a naphthyl group.
  • Ar3 is an anthracenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is an anthracenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is an anthracenyl group.
  • Ar3 is a phenanthryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a phenanthryl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a phenanthryl group.
  • Ar3 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar3 is a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar3 is a fluorenyl group.
  • Ar3 is a spirobifluorenyl group.
  • Ar3 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar3 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzocarbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene.
  • Ar3 is a carbazole group unsubstituted or substituted with an aryl group.
  • Ar3 is a carbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar3 is a dibenzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar3 is a dibenzocarbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar3 is an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a dibenzofuran group unsubstituted or substituted with a heterocyclic group. .
  • Ar3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzofuran group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar3 is a benzonaphthofuran group.
  • Ar3 is a dibenzofuran group.
  • Ar3 is an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a dibenzothiophene group unsubstituted or substituted with a heterocyclic group. to be.
  • Ar3 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzothiophene group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar3 is a benzonaphthothiophene group.
  • Ar3 is a dibenzothiophene group.
  • Ar4 is hydrogen
  • Ar4 is a halogen group.
  • Ar4 is fluorine
  • Ar4 is a substituted or unsubstituted alkyl group.
  • Ar4 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert-butyl group.
  • Ar4 is a methyl group.
  • Ar4 is an ethyl group.
  • Ar4 is an isopropyl group.
  • Ar4 is a tert-butyl group.
  • Ar4 is a substituted or unsubstituted cycloalkyl group.
  • Ar4 is a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group.
  • Ar4 is a cyclohexyl group.
  • Ar4 is a substituted or unsubstituted silyl group.
  • Ar4 is a silyl group unsubstituted or substituted with an alkyl group.
  • Ar4 is a trimethylsilyl group.
  • Ar4 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • Ar4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted quarterphenyl group , A substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
  • Ar4 is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group.
  • Ar4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl And a phenyl group unsubstituted or substituted with a group, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenyl group, or a dimethylfluorenyl group.
  • Ar4 is a phenyl group.
  • Ar4 is a biphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a biphenyl group.
  • Ar4 is a terphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a terphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a terphenyl group.
  • Ar4 is a triphenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a triphenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a triphenyl group.
  • Ar4 is a naphthyl group which is unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a naphthyl group which is unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a naphthyl group.
  • Ar4 is an anthracenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is an anthracenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is an anthracenyl group.
  • Ar4 is a phenanthryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a phenanthryl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a phenanthryl group.
  • Ar4 is a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group, a phenyl group or a naphthyl group.
  • Ar4 is a fluorenyl group.
  • Ar4 is a spirobifluorenyl group.
  • Ar4 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.
  • Ar4 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzocarbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene.
  • Ar4 is a carbazole group unsubstituted or substituted with an aryl group.
  • Ar4 is a carbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar4 is a dibenzocarbazole group unsubstituted or substituted with an aryl group.
  • Ar4 is a dibenzocarbazole group unsubstituted or substituted with a phenyl group or a biphenyl group.
  • Ar4 is a dibenzofuran group unsubstituted or substituted with an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a heterocyclic group. .
  • Ar4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzofuran group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar4 is a benzonaphthofuran group.
  • Ar4 is a dibenzofuran group.
  • Ar4 is an alkyl group, a cycloalkyl group, a halogen group, a halogenated alkyl group, a nitrile group, a silyl group, -OCF 3 , an aryl group, or a dibenzothiophene group unsubstituted or substituted with a heterocyclic group. to be.
  • Ar4 is a methyl group, ethyl group, isopropyl group, tert-butyl group, cyclohexyl group, fluorine, -OCF 3 , -CF 3 , -C 2 F 5 , nitrile group, trimethylsilyl It is a dibenzothiophene group unsubstituted or substituted by the group, the phenyl group, or the naphthyl group.
  • Ar4 is a benzonaphthothiophene group.
  • Ar4 is a dibenzothiophene group.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • the compound represented by Chemical Formula 1 may have a core structure prepared as in Schemes 1 to 5 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • Substituents may be bonded as in Schemes 1 to 5, but are not limited thereto.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic electronic device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device has a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer as an organic material layer.
  • the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer comprises the compound.
  • the organic material layer includes an electron injection layer, and the electron injection layer includes the compound.
  • the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole is the Compound.
  • the organic electronic device further includes one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, and an electron blocking layer.
  • the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode.
  • Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound.
  • the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound.
  • the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, carbazolyl group or benzocarbazolyl group in addition to the organic material layer including the compound.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant may use those known in the art, for example, a metal or a metal complex.
  • the electron transport layer including the compound of Formula 1 may further include LiQ (Lithium Quinolate).
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20.
  • 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the first electrode 30, the hole injection layer 60, the hole transport layer 70, the electron blocking layer 80, the light emitting layer 40, the electron transport layer 90, and the electron injection layer The structure of the organic light emitting device in which the 100 and the second electrode 50 are sequentially stacked is illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound as a dopant material
  • Y is O or S.
  • Y is O.
  • Y is S.
  • G11 is a substituted or unsubstituted aryl group.
  • G11 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted flu Orenyl group.
  • G11 is a phenyl group unsubstituted or substituted with an aryl group.
  • G11 is a phenyl group unsubstituted or substituted with a phenyl group or a naphthyl group.
  • G11 is a phenyl group.
  • G11 is a biphenyl group.
  • G11 is a naphthyl group unsubstituted or substituted with an aryl group.
  • G11 is a naphthyl group unsubstituted or substituted with a phenyl group.
  • G11 is a phenanthryl group.
  • G12 to G15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Imide group; Amide group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted
  • G12 to G15 are each hydrogen.
  • g12, g13 and g15 are each an integer of 1 to 4
  • g14 is an integer of 1 to 3
  • g12 to g15 are each 2 or more
  • two or more G12 to G15 are each other Same or different
  • the compound represented by Formula 9 is any one selected from the following compounds.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a dopant material, and includes a compound represented by Chemical Formula 9 as a host material.
  • the weight ratio (compound represented by Formula 1 / Compound 9 represented by Formula 1) of the compound represented by Formula 1 and compound 9 is 0.005 to 0.10.
  • the compound represented by Formula 9 may be prepared by a manufacturing method described below. In the following production examples, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change the starting materials, reactants, reaction conditions and the like.
  • the compound represented by Chemical Formula 9 may have a core structure as shown in Scheme 6 below.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. Substituents may be bonded as in Scheme 6, but are not limited thereto.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It may be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • PVD physical vapor deposition
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the anode material includes metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene and periplanthene having an arylamine group, and the styrylamine compound is substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the light emitting material of the light emitting layer is formed by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • a material capable of emitting light in the visible ray region a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the electron blocking layer is a layer that can prevent the holes injected from the hole injection layer to enter the electron injection layer through the light emitting layer to improve the life and efficiency of the device, if necessary, using a known material using a known material and the electron It may be formed in a suitable portion between the injection layers.
  • the hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the compound according to the present specification may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic phosphors, organic solar cells, organic photoconductors, organic transistors, and the like.
  • the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound EB1 was vacuum deposited on the hole transport layer with a film thickness of 100 GPa to form an electron blocking layer.
  • the compound ET1 and the compound LiQ were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 kPa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • the lithium fluoride of the cathode was 0.3 ⁇ / sec
  • aluminum is deposited at a rate of 2 ⁇ / sec
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that BD 1 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that BD 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that BD 3 was used instead of compound 1 in Experimental Example 1-1.
  • T90 refers to the time it takes for the luminance to decrease to 90% from the initial luminance (5000 nits).
  • Compound 1 having the core of Compound A has excellent low voltage characteristics
  • Compounds 2 to 4 having the core of Compound B have excellent long life characteristics
  • the compound represented by Formula 1 of the present specification may represent various color coordinates by substituents such as silyl group, fluorine, aryl group and heterocyclic group. Therefore, it can be seen that the compounds according to one embodiment of the present specification can be utilized as light emitting materials having various color coordinates and the like that can respond to industrial products using light.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 100 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound HB 1 was vacuum deposited on the light emitting layer to a thickness of 50 kPa on the hole transport layer to form a hole blocking layer.
  • the compound ET 1 and the compound LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer having a thickness of 310 ⁇ m.
  • Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 ⁇ and 1,000 ⁇ to form a cathode.
  • the lithium fluoride of the cathode was 0.3 ⁇ / sec
  • aluminum is deposited at a rate of 2 ⁇ / sec
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 2 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 3 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 4 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that Compound BH was used instead of BH 1 in Experimental Example 2-1.
  • T90 refers to the time it takes for the luminance to decrease to 90% from the initial luminance (5000 nits).
  • Experimental Examples 2-1 to 2-5 using the compound represented by Formula 1 of the present specification as a dopant of the light emitting layer, and using the compound represented by Formula 9 of the present specification as a host of the light emitting layer Compared to Experimental Example 2-6, it can be seen that the low voltage, high efficiency and long life characteristics can be applied to the organic light emitting device.
  • Experimental Examples 2-1 to 2-5 using the compound represented by the formula (9) as a host of the light emitting layer have a lifespan of 10, compared to Experimental Example 2-6 using the compound BH not containing a heteroaryl group. An increase of% to 30% was obtained. Therefore, it can be seen that the compounds according to one embodiment of the present specification can be utilized as light emitting materials having various color coordinates and the like that can respond to industrial products using light.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé et un élément électronique organique comprenant celui-ci.
PCT/KR2017/009879 2016-09-09 2017-09-08 Composé et élément électronique organique le comprenant WO2018048247A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201780024267.6A CN109071449B (zh) 2016-09-09 2017-09-08 化合物和包含其的有机电子元件
US16/085,547 US11306060B2 (en) 2016-09-09 2017-09-08 Compound and organic electronic element comprising same
JP2018549326A JP6750784B2 (ja) 2016-09-09 2017-09-08 化合物およびこれを含む有機電子素子
EP17849131.2A EP3428152B1 (fr) 2016-09-09 2017-09-08 Composé et élément électronique organique le comprenant

Applications Claiming Priority (4)

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KR20160116524 2016-09-09
KR10-2016-0116524 2016-09-09
KR1020170113862A KR102032023B1 (ko) 2016-09-09 2017-09-06 화합물 및 이를 포함하는 유기 전자 소자
KR10-2017-0113862 2017-09-06

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Cited By (1)

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CN110294735A (zh) * 2018-03-23 2019-10-01 江苏三月光电科技有限公司 一种以蒽和菲为核心的化合物及其在有机电致发光器件上的应用

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WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20140115636A (ko) * 2013-03-21 2014-10-01 덕산하이메탈(주) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20140135117A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150095545A (ko) * 2014-02-13 2015-08-21 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150130206A (ko) * 2014-05-13 2015-11-23 에스에프씨 주식회사 방향족 아민기를 포함하는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20160005196A (ko) * 2014-07-03 2016-01-14 삼성디스플레이 주식회사 유기 발광 소자

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Publication number Priority date Publication date Assignee Title
WO2003012890A2 (fr) 2001-07-20 2003-02-13 Novaled Gmbh Composant electroluminescent a couches organiques
KR20140115636A (ko) * 2013-03-21 2014-10-01 덕산하이메탈(주) 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20140135117A (ko) * 2013-05-15 2014-11-25 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150095545A (ko) * 2014-02-13 2015-08-21 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20150130206A (ko) * 2014-05-13 2015-11-23 에스에프씨 주식회사 방향족 아민기를 포함하는 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20160005196A (ko) * 2014-07-03 2016-01-14 삼성디스플레이 주식회사 유기 발광 소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110294735A (zh) * 2018-03-23 2019-10-01 江苏三月光电科技有限公司 一种以蒽和菲为核心的化合物及其在有机电致发光器件上的应用
CN110294735B (zh) * 2018-03-23 2021-11-19 江苏三月科技股份有限公司 一种以蒽和菲为核心的化合物及其在有机电致发光器件上的应用

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