US5869199A
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Organic electroluminescent elements comprising triazoles
Assignee: Chemipro Kasei Kaisha Ltd
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Filing: 1994-03-17
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Granted: 1999-02-09
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Expires: 2014-03-17
Abstract
Abstract An organic electroluminescent element (device) having different layer structures. The first element is a layer of a lower-molecular 1,2,4-triazole derivative; the second element is a carrier-transport control layer for selectively transporting holes or electrons, which is interposed between an electron-transport layer and a hole-transport layer. The third element is a hole-transport wherein a dye is molecularly dispersed and an electron-transport layer, both being laminated each other. The fourth element is a layer containing a high-molecular 1,2,4-triazole derivative as a hole-transport material; and the fifth element is a hole-transport layer wherein a hole-transport material is molecularly dispersed in a high-molecular 1,2,4-triazole derivative as a resin binder. The organic electroluminescent device is excellent in luminous efficiency, luminance and stability, permitting blue light emission, multi-color light emission (three primary color), and white light.
Inventors
- 👤 Junji Kido
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 10:55
CPC Classifications
H; H05; H05B; H05B33/00; H05B33/12; H05B33/14; C; C09; C09K; C09K11/00; C09K11/06; H10; H10K; H10K50/00; H10K50/10; H10K50/11; H10K85/00; H10K85/10; H10K85/111; H10K85/141; H10K85/146; H10K85/30; H10K85/321; H10K85/324; H10K85/60; H10K85/631; H10K85/649; H10K85/656; H10K85/6565; Y; Y02; Y02B; Y02B20/00; Y10; Y10S; Y10S428/00; Y10S428/917; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
58 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises (i) a carrier-transport control layer consisting of a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR15## exhibiting electron-transport properties and hole blocking properties and (ii) at least a hole-transport layer interposed between the carrier-transport control layer and the anode.
Claim 2
Dependent Claim
58 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises (i) a carrier-transport control layer consisting of a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR15## exhibiting electron-transport properties and hole blocking properties and (ii) at least a hole-transport layer interposed between the carrier-transport control layer and the anode.
Claim 3
Dependent Claim
33 words
An organic electroluminescent element according to claim 1, wherein said hole-transport layer emits a blue light, and is a layer of poly-N-vinylcarbazole, expressed by the formula: ##STR16## wherein n denotes a polymerization degree.
Claim 4
Dependent Claim
16 words
An organic electroluminescent element according to claim 1, wherein said hole-transport layer emits a blue light.
Claim 5
Dependent Claim
86 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) a carrier-transport control layer consisting of a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR17## exhibiting electron-transport properties and hole blocking properties, (ii) a hole transport layer interposed between the carrier-transport control layer and the anode and (iii) an electron-transport layer interposed between the cathode and the carrier-transport control layer, wherein said electron-transport layer is a layer of a tris(8-quinolinolato)aluminum (III) complex of the formula: ##STR18##
Claim 6
Dependent Claim
86 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) a carrier-transport control layer consisting of a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR17## exhibiting electron-transport properties and hole blocking properties, (ii) a hole transport layer interposed between the carrier-transport control layer and the anode and (iii) an electron-transport layer interposed between the cathode and the carrier-transport control layer, wherein said electron-transport layer is a layer of a tris(8-quinolinolato)aluminum (III) complex of the formula: ##STR18##
Claim 7
Dependent Claim
33 words
An organic electrolumiscent element according to claim 4, wherein said hole-transport layer emits a blue light, and is a layer of poly-N-vinylcarbazole, expressed by the formula: ##STR19## wherein n denotes a polymerization degree.
Claim 8
Dependent Claim
151 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises a carrier-transport control layer which does not itself emit light comprising a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR20## having a function either of: a) allowing electrons injected from the cathode to pass toward the anode while blocking holes injected from the anode to prevent the holes from passing toward the cathode; or b) allowing holes injected from the anode to pass toward the cathode and electrons injected from the cathode to pass toward the anode, a hole transport layer interposed between the carrier-transport control layer and the anode, and an electron-transport layer interposed between the carrier transport control layer and the cathode, and in accordance with the function of the carrier-transport control layer a) the hole transport layer, or b) both the hole-transport layer and the electron-transport layer emit light.
Claim 9
Dependent Claim
151 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises a carrier-transport control layer which does not itself emit light comprising a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR20## having a function either of: a) allowing electrons injected from the cathode to pass toward the anode while blocking holes injected from the anode to prevent the holes from passing toward the cathode; or b) allowing holes injected from the anode to pass toward the cathode and electrons injected from the cathode to pass toward the anode, a hole transport layer interposed between the carrier-transport control layer and the anode, and an electron-transport layer interposed between the carrier transport control layer and the cathode, and in accordance with the function of the carrier-transport control layer a) the hole transport layer, or b) both the hole-transport layer and the electron-transport layer emit light.
Claim 10
Dependent Claim
39 words
An organic electroluminescent element according to claim 6, wherein the hole-transport layer is a layer of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine expressed by the formula: ##STR21## and the electron transport layer is a layer of a tris(8-quinolinolato)aluminum (III) complex of the formula: ##STR22##
Claim 11
Dependent Claim
28 words
An organic electroluminescent element according to claim 6, wherein said hole-transport layer emits light when the thickness of said carrier-transport control layer is not less than 150 Å.
Claim 12
Dependent Claim
36 words
An organic electroluminescent element according to claim 6, wherein both said electron-transport layer and said hole-transport layer emit light when the thickness of said carrier-transport control layer exceeds 50 Å and is less than 150 Å.
Claim 13
Dependent Claim
70 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) an electron-transport layer comprising 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR23## and (ii) a hole transport luminescent layer interposed between the electron-transport layer and the anode wherein said hole transport luminescent layer comprises a polymer having carrier-transport properties and at least one dye which is molecularly dispersed in the polymer.
Claim 14
Dependent Claim
70 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) an electron-transport layer comprising 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR23## and (ii) a hole transport luminescent layer interposed between the electron-transport layer and the anode wherein said hole transport luminescent layer comprises a polymer having carrier-transport properties and at least one dye which is molecularly dispersed in the polymer.
Claim 15
Dependent Claim
58 words
An organic electroluminescent element according to claim 10, wherein the electron-transport layer is composed of a single layer of a 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR24## exhibiting electron-transport properties and hole blocking properties, or two layers consisting of the layer of said 3-(4-biphenylyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole and a layer of a tris(8-quinolinolato)aluminum (III) complex expressed by the formula: ##STR25##
Claim 16
Dependent Claim
28 words
An organic electroluminescent element according to claim 10, wherein the polymer having carrier-transport properties is a poly-N-vinylcarbazole expressed by the formula: ##STR26## wherein n denotes a polymerization degree.
Claim 17
Dependent Claim
51 words
An organic electroluminescent element according to claim 10, wherein a plurality of dyes that are molecularly dispersed in the hole-transport luminescent layer, are combined such that an emission spectrum of the hole-transport luminescent layer extends over the whole range of visible light region having a wavelength of 400 to 700 nm.
Claim 18
Dependent Claim
35 words
An organic electroluminescent element according to claim 13, wherein the combined dyes are tetraphenylbutadiene expressed by the formula: ##STR27## a coumarine 6 expressed by the formula: ##STR28## and a 4-dicyanomethylene-2-methyl-6-p-dimethylaminostyryl-4H-pyran expressed by the formula: ##STR29##
Claim 19
Dependent Claim
115 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) an electron-transport layer comprising 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR30## and (ii) a hole-transport luminescent layer interposed between the electron-transport layer and the anode and wherein said hole-transport luminescent layer comprises a polymer having no carrier-transport properties and at least one dye and a hole-transport material which are molecularly dispersed in the polymer, and said hole-transport material transports holes injected from said anode to said dye and the dye is excited by excitons generated by recombination of said holes and electrons injected from said electron-transport layer into said hole-transport luminescent layer, to emit light.
Claim 20
Dependent Claim
115 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween wherein said organic layer comprises (i) an electron-transport layer comprising 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR30## and (ii) a hole-transport luminescent layer interposed between the electron-transport layer and the anode and wherein said hole-transport luminescent layer comprises a polymer having no carrier-transport properties and at least one dye and a hole-transport material which are molecularly dispersed in the polymer, and said hole-transport material transports holes injected from said anode to said dye and the dye is excited by excitons generated by recombination of said holes and electrons injected from said electron-transport layer into said hole-transport luminescent layer, to emit light.
Claim 21
Dependent Claim
19 words
An organic electroluminescent element according to claim 15, wherein the hole-transport material is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine expressed by the formula: ##STR31##
Claim 22
Dependent Claim
58 words
An organic electroluminescent element according to claim 15, wherein the electron-transport layer is composed of a single layer of a 4-(4-biphenyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole expressed by the formula: ##STR32## exhibiting electron-transport properties and hole blocking properties, or two layers consisting of the layer of said 4-(4-biphenyl)-4,5-diphenyl-1,2,4-triazole derivative!3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole and a layer of a tris(8-quinolinolato)aluminum (III) complex expressed by the formula: ##STR33##
Claim 23
Dependent Claim
51 words
An organic electroluminescent element according to claim 15, wherein a plurality of dyes that are molecularly dispersed in the hole-transport luminescent layer, are combined such that an emission spectrum of the hole-transport luminescent layer extends over the whole range of visible light region having a wavelength of 400 to 700 nm.
Claim 24
Dependent Claim
34 words
An organic electroluminescent element according to claim 18, wherein combined dyes are tetraphenylbutadiene expressed by the formula: ##STR34## a coumarine 6 expressed by the formula: ##STR35## and a 4-dicyanomethylene-2-methyl-6-p-dimethylaminostyryl-4H-pyran expressed by the formula: ##STR36##
Claim 25
Dependent Claim
76 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises a hole-transport layer which contains, as a hole-transport material, a high-molecular 1,2,4-triazole derivative expressed by the general formula: ##STR37## wherein R denotes at least one member selected from the group consisting of: a hydrogen atom, a methyl group and an ethyl group, m denotes a polymerization degree and is in the range of 3000 to 30000.
Claim 26
Dependent Claim
76 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises a hole-transport layer which contains, as a hole-transport material, a high-molecular 1,2,4-triazole derivative expressed by the general formula: ##STR37## wherein R denotes at least one member selected from the group consisting of: a hydrogen atom, a methyl group and an ethyl group, m denotes a polymerization degree and is in the range of 3000 to 30000.
Claim 27
Dependent Claim
84 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises a hole-transport layer which is formed by molecularly dispersing a hole-transport material in a high-molecular 1,2,4-triazole derivative expressed by the general formula: ##STR38## wherein R denotes at least one member selected from the group consisting of: a hydrogen atom, a methyl group and an ethyl group, m denotes a polymerization degree and is in the range of 3000 to 30000 as a resin binder.
Claim 28
Dependent Claim
84 words
An organic electroluminescent element comprising an anode, a cathode and an organic layer interposed therebetween and said organic layer comprises a hole-transport layer which is formed by molecularly dispersing a hole-transport material in a high-molecular 1,2,4-triazole derivative expressed by the general formula: ##STR38## wherein R denotes at least one member selected from the group consisting of: a hydrogen atom, a methyl group and an ethyl group, m denotes a polymerization degree and is in the range of 3000 to 30000 as a resin binder.
Claim 29
Dependent Claim
20 words
An organic electroluminescent element according to claim 21, wherein the hole-transport material is a N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine expressed by the formula: ##STR39##
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