WO2019107932A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019107932A1
WO2019107932A1 PCT/KR2018/014859 KR2018014859W WO2019107932A1 WO 2019107932 A1 WO2019107932 A1 WO 2019107932A1 KR 2018014859 W KR2018014859 W KR 2018014859W WO 2019107932 A1 WO2019107932 A1 WO 2019107932A1
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group
substituted
compound
unsubstituted
light emitting
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PCT/KR2018/014859
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English (en)
Korean (ko)
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홍완표
윤준
서상덕
강유진
김동헌
한시현
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주식회사 엘지화학
성균관대학교산학협력단
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Priority claimed from KR1020180147707A external-priority patent/KR102181841B1/ko
Application filed by 주식회사 엘지화학, 성균관대학교산학협력단 filed Critical 주식회사 엘지화학
Priority to CN201880041595.1A priority Critical patent/CN110785406A/zh
Publication of WO2019107932A1 publication Critical patent/WO2019107932A1/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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a compound and an organic light emitting device including the same.
  • thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
  • thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
  • the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.
  • the present invention provides a compound and an organic light emitting device comprising the same.
  • A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,
  • R1 to R8 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubsti
  • n 1 or 2
  • n 2
  • the structures in the plurality of parentheses are equal to or different from each other
  • n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.
  • a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
  • the organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.
  • FIG 1 shows an organic light emitting device according to an embodiment of the present invention.
  • the compound represented by the formula (1) combines two cyano groups at the para position with a benzene core as a center, so that the organic light emitting device emitting light in a specific wavelength range, .
  • the charge balance injected into the light emitting layer is controlled, and the organic light emitting device including the benzene core has low driving voltage, The life can be improved.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; Cyano; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the halogen group may be fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • 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 number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.
  • the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above.
  • Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group.
  • Examples of the alkylsulfoxy group include a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group.
  • aryloxy group examples include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group.
  • the present invention is not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes at least one non-carbon atom and at least one hetero atom.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
  • the "ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
  • the hetero ring includes one or more non-carbon atoms and hetero atoms.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the heteroaryl group or the heterocyclic group except that the monocyclic group is not monovalent.
  • the formula (1) is represented by the following formula (1-1) or (1-2).
  • A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
  • R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
  • R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or an alkyl group.
  • R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a methyl group.
  • adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
  • adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
  • adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form an indene ring substituted with at least one alkyl group.
  • adjacent groups among R1 to R8 and R11 to R18 in the general formula (1) are bonded to each other to form an indene ring substituted with at least one methyl group.
  • R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • R 2 and R 3 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
  • R 2 and R 3 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
  • R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one alkyl group.
  • R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one methyl group.
  • any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted alkyl group; To form an unsubstituted hydrocarbon ring.
  • any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted alkyl group; To form a ring-opened hydrocarbon ring.
  • R 3 is a substituted or unsubstituted phenyl group
  • R 2 is a substituted or unsubstituted alkyl group
  • R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
  • R 3 is a phenyl group
  • R 2 is an isopropyl group
  • R 2 and R 3 are bonded to each other to form an indene ring substituted with two methyl groups.
  • R 6 and R 7 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R 6 and R 7 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
  • R 6 and R 7 combine with each other to form an aromatic ring substituted with at least one alkyl group.
  • R 6 and R 7 combine with each other to form an indene ring substituted with at least one alkyl group.
  • R 6 and R 7 combine with each other to form an indene ring substituted with at least one methyl group.
  • any one of R6 and R7 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
  • any one of R6 and R7 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form a ring-opened hydrocarbon ring.
  • R6 is a substituted or unsubstituted phenyl group
  • R7 is a substituted or unsubstituted alkyl group
  • R6 and R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
  • R6 is a phenyl group
  • R7 is an isopropyl group
  • R6 and R7 are bonded to each other to form an indene ring substituted with two methyl groups.
  • R 12 and R 13 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R12 and R13 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
  • R 12 and R 13 combine with each other to form an aromatic ring substituted with at least one alkyl group.
  • R12 and R13 are bonded to each other to form an indene ring substituted with at least one alkyl group.
  • R 12 and R 13 combine with each other to form an indene ring substituted with at least one methyl group.
  • any one of R12 and R13 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
  • any one of R12 and R13 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
  • R13 is a substituted or unsubstituted phenyl group
  • R12 is a substituted or unsubstituted alkyl group
  • R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
  • R13 is a phenyl group
  • R12 is an isopropyl group
  • R12 and R13 are bonded to each other to form an indene ring substituted with two methyl groups.
  • R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • R16 and R17 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
  • R16 and R17 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
  • R16 and R17 are bonded to each other to form an indene ring substituted with at least one alkyl group.
  • R16 and R17 are bonded to each other to form an indene ring substituted with at least one methyl group.
  • any one of R16 and R17 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
  • any one of R16 and R17 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
  • R16 is a substituted or unsubstituted phenyl group
  • R17 is a substituted or unsubstituted alkyl group
  • R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
  • R16 is a phenyl group
  • R17 is an isopropyl group
  • R16 and R17 are bonded to each other to form an indene ring substituted with two methyl groups.
  • A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group.
  • A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; An aryl group which is substituted or unsubstituted with a fluorine atom, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a polycyclic heteroaryl group.
  • A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; A phenyl group substituted or unsubstituted by fluorine, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a carbazolyl group.
  • adjacent groups of A1 to A5 are bonded to each other to form an aromatic ring.
  • adjacent groups of A1 to A5 combine with each other to form a benzene ring.
  • adjacent groups among A11 to A15 are bonded to each other to form an aromatic ring.
  • adjacent groups among A11 to A15 are bonded to each other to form a benzene ring.
  • a 1 and A 5 combine with each other to form an aromatic ring.
  • a 1 and A 5 combine with each other to form a benzene ring.
  • A1 and A5 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
  • A1 and A5 are each ethenyl and combine with each other to form a benzene ring.
  • A2 and A3 combine with each other to form an aromatic ring.
  • A2 and A3 combine with each other to form a benzene ring.
  • A2 and A3 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
  • A2 and A3 are each an ethenyl and combine with each other to form a benzene ring.
  • A3 and A4 are bonded to each other to form an aromatic ring.
  • A3 and A4 are bonded to each other to form a benzene ring.
  • A3 and A4 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
  • A3 and A4 are each an ethenyl and combine with each other to form a benzene ring.
  • A4 and A5 combine with each other to form an aromatic ring.
  • A4 and A5 combine with each other to form a benzene ring.
  • A4 and A5 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
  • A4 and A5 are each ethenyl and combine with each other to form a benzene ring.
  • A11 and A12 combine with each other to form an aromatic ring.
  • A11 and A12 combine with each other to form a benzene ring.
  • A11 and A12 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
  • A11 and A12 are each ethenyl and combine with each other to form a benzene ring.
  • A12 and A13 are bonded to each other to form an aromatic ring.
  • A12 and A13 combine with each other to form a benzene ring.
  • A12 and A13 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
  • A12 and A13 are each ethenyl and combine with each other to form a benzene ring.
  • A13 and A14 combine with each other to form an aromatic ring.
  • A13 and A14 combine with each other to form a benzene ring.
  • A13 and A14 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
  • A13 and A14 are each an ethenyl group and combine with each other to form a benzene ring.
  • A14 and A15 combine with each other to form an aromatic ring.
  • A14 and A15 combine with each other to form a benzene ring.
  • A14 and A15 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
  • A14 and A15 are each ethenyl and combine with each other to form a benzene ring.
  • n is 1 and either one of A1 to A5 is a polycyclic heteroaryl group in the general formula (1), the remainder is hydrogen.
  • n is 1 and one of A 1 to A 5 is a carbazolyl group in the general formula (1), the other is hydrogen.
  • Formula 1 is selected from the following compounds.
  • the compound represented by Formula 1 is a retardation fluorescent compound.
  • the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence.
  • the phosphorescent light emission it means that the exciton of the excited state moves to the ground state and emits light.
  • the fluorescent emission the exciton of the excited state is in the ground state ground state, and the light is emitted.
  • the thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.
  • the thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S 1 -T 1 < / RTI > energy difference.
  • S 1 is a singlet energy level
  • T 1 is a triplet energy level.
  • a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
  • the organic material layer of the organic light emitting device may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting diode 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 diode according to an embodiment of the present invention, and may further include another organic layer.
  • the organic layer includes a light emitting layer, and the light emitting layer includes the compound.
  • the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.
  • the maximum emission wavelength of the dopant is 480 nm to 570 nm.
  • the dopant is a green dopant.
  • the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excited singlet energy and the excitation triplet energy has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also prevents a long wavelength of light emission, And may include an organic compound having a high glass transition temperature as a host.
  • the organic layer includes a light emitting layer, and the light emitting layer includes a host.
  • the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
  • the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a fluorene derivative, a phenanthrene compound, a fluoranthene compound, Include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, and pyrimidine derivatives.
  • the host may include any one or more selected from the following compounds, but is not limited thereto.
  • the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by Formula 1 as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.
  • the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include at least one selected from the group consisting of the dopant including the compound represented by the above-mentioned formula (1), the condensed aromatic ring derivative, and the heterocyclic compound Containing host at a weight ratio of 1:99 to 50:50.
  • the organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that the dopant of the light emitting layer contains the compound of the present specification, that is, the compound represented by the above formula (1).
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of 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; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer 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 include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • the toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure.
  • a glass substrate with a 40 mm x 40 mm x 0.5 mm thick ITO electrode was ultrasonically cleaned with isopropyl alcohol, acetone and DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O 2 plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top.
  • An organic layer was deposited on the ITO of the glass substrate by evaporation from a heated boat under a vacuum of about 10 -7 Torr in the following order. At this time, the deposition rate of the organic material was set at 10 nm / s.
  • Hole injection layer HAT-CN, thickness 10 nm
  • HTL Hole transport layer
  • Electron barrier layer (EBL) mCBP, thickness 15 nm
  • Emissive material layer TH1 90 wt%, Compound 1 10 wt%, thickness 35 nm
  • Hole blocking layer (HBL) B3PYMPM, thickness 10 nm
  • Electron transport layer (ETL) TPBi, thickness 25 nm
  • Electron Injection Layer LiF, thickness 80 nm
  • a capping layer (CPL) was formed and encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter.
  • An organic light emitting device was prepared using Compound 2 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using Compound 3 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using Compound 4 instead of Compound 1 as a dopant of the light emitting layer.
  • An organic light emitting device was prepared using Compound 5 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared by using Compound 6 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using Compound 8 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using Compound 9 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared by using Compound 10 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using Compound 13 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared by using Compound 14 instead of Compound 1 as a dopant of the light emitting layer.
  • An organic luminescent device was prepared using the following Compound D1 instead of Compound 1 as a dopant in the light emitting layer.
  • An organic luminescent device was prepared using the following compound D2 instead of compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using the following compound D3 instead of Compound 1 as a dopant of the light emitting layer.
  • An organic luminescent device was prepared using the following compound D4 instead of compound 1 as a dopant in the light emitting layer.
  • An organic light emitting device was prepared using the following compound D5 instead of compound 1 as a dopant of the light emitting layer.
  • An organic luminescent device was prepared using the following compound D6 instead of compound 1 as a dopant in the light emitting layer.
  • the devices of Examples 1 to 11 using the heterocyclic compound of the present invention had lower driving voltage, higher current efficiency, higher power efficiency, higher luminance, and higher lifetime characteristics than the devices of Comparative Examples 1 to 6 .

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2018/014859 2017-11-28 2018-11-28 Composé et dispositif électroluminescent organique le comprenant WO2019107932A1 (fr)

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WO2022254965A1 (fr) * 2021-06-03 2022-12-08 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent

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KR20160000331A (ko) * 2014-06-24 2016-01-04 제일모직주식회사 화합물, 이를 포함하는 유기광전자소자 및 표시장치
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US20170186973A1 (en) * 2015-12-25 2017-06-29 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent compound and organic photoelectric apparatus thereof

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