US5382477A
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Organic electroluminescent element and process for producing the same
Assignee: Ricoh Co Ltd
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Filing: 1992-02-24
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Granted: 1995-01-17
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Expires: 2012-02-24
Abstract
Abstract There is disclosed an EL element having at least one layer made from organic materials between an electron injection electrode and a hole injection electrode, the organic materials consisting of oxadiazole series compounds which have a plurality of oxadiazole rings.
Inventors
- 👤 Shogo Saito
- 👤 Tetsuo Tsutsui
- 👤 Chihaya Adachi
- 👤 Yuji Hamada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:42
CPC Classifications
H; H05; H05B; H05B33/00; H05B33/12; H05B33/14; C; C09; C09K; C09K11/00; C09K11/06; Y; Y10; Y10S; Y10S428/00; Y10S428/917
Claims Analysis
Total Claims: 69
Claim 1
Independent Claim
100 words
An organic EL element, comprising: an electron injection electrode; a hole injection electrode; and at least one layer made from an organic material between the electron injection and the hole injection electrode, the organic material being selected from the group consisting of (i) an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings, (ii) an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings, and (iii) an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 2
Dependent Claim
100 words
An organic EL element, comprising: an electron injection electrode; a hole injection electrode; and at least one layer made from an organic material between the electron injection and the hole injection electrode, the organic material being selected from the group consisting of (i) an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings, (ii) an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings, and (iii) an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 3
Dependent Claim
50 words
An EL element in claim 1, wherein at least two layers made from organic materials are present, wherein the layers made from organic materials include an organic luminous layer and an electron transport layer, the electron transport layer being provided between the organic luminous layer and the electron injection electrode.
Claim 4
Dependent Claim
16 words
An EL element in claim 2, wherein the organic luminous layer comprises the oxadiazole series compounds.
Claim 5
Dependent Claim
30 words
An EL element in claim 3, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 6
Dependent Claim
37 words
An EL element in claim 4, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 7
Dependent Claim
31 words
An EL element in claim 5, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 8
Dependent Claim
30 words
An EL element in claim 4, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 9
Dependent Claim
30 words
An EL element in claim 3, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 10
Dependent Claim
40 words
An EL element in claim 8, wherein the number of said oxadizole rings is 2, and a biphenyl group which includes two benzene rings is substituted by the oxadiazole at either the 4- and 4'- or 2- and 2'- positions.
Claim 11
Dependent Claim
30 words
An EL element in claim 3, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 12
Dependent Claim
28 words
An EL element in claim 10, wherein the number of said oxadizole rings is 2, the carbon number of an alkyl chain between the oxadiazole rings being 1-6.
Claim 13
Dependent Claim
120 words
An EL element in claim 3, wherein the oxadiazole series compounds are selected from the group consisting of the chemical formulas shown below: ##STR30## wherein R, R 1 , R 2 and R 3 are selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 (CH 3 ) 3 C, OCH 3 , OC 2 H 5 , NH 2 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , CN, phenyl and cyclohexyl, and R' is selected from the group consisting of H, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , N(CH 3 ) 2 and an oxadiazole ring.
Claim 14
Dependent Claim
16 words
An EL element in claim 2, wherein the electron transport layer comprises the oxadiazole series compounds.
Claim 15
Dependent Claim
30 words
An EL element in claim 13, wherein the electron transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 16
Dependent Claim
37 words
An EL element in claim 14, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 17
Dependent Claim
31 words
An EL element in claim 15, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 18
Dependent Claim
30 words
An EL element in claim 14, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 19
Dependent Claim
30 words
An EL element in claim 13, wherein the electron transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 20
Dependent Claim
40 words
An EL element in claim 18, wherein the number of the oxadiazole rings is 2, a biphenyl group which includes the two benzene rings being substituted by the oxadiazole at either the 4- and 4'- or 2- and 2'- positions.
Claim 21
Dependent Claim
30 words
An EL element in claim 13, wherein the electron transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 22
Dependent Claim
28 words
An EL element in claim 20, wherein the number of the oxadiazole rings is 2, the carbon number of an alkyl chain between the oxadiazole rings being 1-6.
Claim 23
Dependent Claim
120 words
An EL element in claim 13, wherein the oxadiazole series compounds are selected from the group consisting of the chemical formulas shown below: ##STR31## wherein R, R 1 , R 2 and R 3 are selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 (CH 3 ) 3 C, OCH 3 , OC 2 H 5 , NH 2 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , CN, phenyl and cyclohexyl, and R' is selected from the group consisting of H, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , N(CH 3 ) 2 and an oxadiazole ring.
Claim 24
Dependent Claim
20 words
An EL element in claim 13, wherein the organic compound which forms the organic luminous layer is a triphenyl-amine derivative.
Claim 25
Dependent Claim
50 words
An EL element in claim 1, wherein at least two layers made from organic materials are present, wherein the layers made from organic materials include an organic luminous layer and a hole transport layer, the hole transport layer being provided between the organic luminous layer and the hole injection electrode.
Claim 26
Dependent Claim
16 words
An EL element in claim 24, wherein the organic luminous layers comprise the oxadiazole series compounds.
Claim 27
Dependent Claim
30 words
An EL element in claim 25, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 28
Dependent Claim
37 words
An EL element in claim 26, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 29
Dependent Claim
31 words
An EL element in claim 27, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 30
Dependent Claim
30 words
An EL element in claim 26, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 31
Dependent Claim
30 words
An EL element in claim 25, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 32
Dependent Claim
40 words
An EL element in claim 30, wherein the number of the oxadiazole rings is 2, the biphenyl group which consists of the two benzene rings being substituted by the oxadiazole at either 4- and 4'- or 2- and 2'- positions.
Claim 33
Dependent Claim
30 words
An EL element in claim 25, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 34
Dependent Claim
24 words
An EL element in claim 32, wherein the number of the oxadiazole rings is 2, the carbon number of the alkyl chain is 1-6.
Claim 35
Dependent Claim
18 words
An EL element in claim 25, wherein the organic compounds which form a hole transport layer are diamine.
Claim 36
Dependent Claim
116 words
An EL element in claim 25, wherein the oxadiazole series compounds are selected from the chemical formulas shown below: ##STR32## wherein R, R 1 , R 2 and R 3 are selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 (CH 3 ) 3 C, OCH 3 , OC 2 H 5 , NH 2 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , CN, phenyl and cyclohexyl, and R' is selected from the group consisting of H, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , N(CH 3 ) 2 and an oxadiazole ring.
Claim 37
Dependent Claim
16 words
An EL element in claim 24, wherein a hole transport layer comprises the oxadiazole series compound.
Claim 38
Dependent Claim
30 words
An EL element in claim 36, wherein the hole transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 39
Dependent Claim
37 words
An EL element in claim 37, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 40
Dependent Claim
31 words
An EL element in claim 38, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 41
Dependent Claim
30 words
An EL element in claim 37, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 42
Dependent Claim
30 words
An EL element in claim 36, wherein the hole transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 43
Dependent Claim
40 words
An EL element in claim 41, wherein the number of the oxadiazole rings is 2, a biphenyl group which includes the two benzene rings being substituted by the oxadiazole at either the 4- and 4'- or 2- and 2'- positions.
Claim 44
Dependent Claim
30 words
An EL element in claim 36, wherein the hole transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 45
Dependent Claim
28 words
An EL element in claim 43, wherein the number of the oxadiazole rings is 2, the carbon number of an alkyl chain between the oxadiazole rings being 0-10.
Claim 46
Dependent Claim
82 words
An EL element in claim 36, wherein the oxadiazole series compounds are selected from the group consisting of the chemical formulas shown below: ##STR33## wherein R, R1, R2 and R3 are selected from the group consisting of NH 2 , N(CH 3 ) 2 , and N(C 2 H 5 ) 2 , and R' is selected from the group consisting of H, C n H 2n+1 (n=1-10), OCH 3 , OC 2 H 5 , phenyl, cyclohexyl and an oxadiazole ring.
Claim 47
Dependent Claim
32 words
An EL element in claim 36, wherein the organic compounds which form an organic luminous layer are selected from the group consisting of 8-Hydroxyquinoline aluminum, a perylene derivative and a perinone derivative.
Claim 48
Dependent Claim
71 words
An EL element in claim 1, wherein at least three layers made from organic material are present, wherein the layers made from organic materials include an organic luminous layer, an electron transport layer and a hole transport layer, the electron transport layer being provided between the organic luminous layer and the electron injection electrode, and the hole transport layer being provided between the organic luminous layer and the hole injection electrode.
Claim 49
Dependent Claim
16 words
An EL element in claim 47, wherein the organic luminous layers comprise the oxadiazole series compounds.
Claim 50
Dependent Claim
30 words
An EL element in claim 48, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 51
Dependent Claim
37 words
An EL element in claim 49, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 52
Dependent Claim
31 words
An EL element in claim 50, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 53
Dependent Claim
30 words
An EL element in claim 49, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 54
Dependent Claim
30 words
An EL element in claim 48, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 55
Dependent Claim
39 words
An EL element in claim 53, wherein the number of the oxadiazole rings is 2, a biphenyl group which includes the two benzene rings being substituted by the oxadiazole at either 4- and 4'- or 2- and 2'- positions.
Claim 56
Dependent Claim
30 words
An EL element in claim 48, wherein the organic luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 57
Dependent Claim
28 words
An EL element in claim 55, wherein the number of the oxadiazole rings is 2, the carbon number of an alkyl chain between the oxadiazole rings being 1-6.
Claim 58
Dependent Claim
120 words
An EL element in claim 48, wherein the oxadiazole series compounds are selected from the group consisting of the chemical formulas shown below: ##STR34## wherein R, R 1 , R 2 and R 3 are selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 (CH 3 ) 3 C, OCH 3 , OC 2 H 5 , NH 2 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , CN, phenyl and cyclohexyl, and R' is selected from the group consisting of H, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , N(CH 3 ) 2 and an oxadiazole ring.
Claim 59
Dependent Claim
16 words
An EL element in claim 47, wherein the electron transport layer comprises the oxadiazole series compounds.
Claim 60
Dependent Claim
29 words
An EL element in claim 58, wherein the electron layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and one benzene ring between the oxadiazole rings.
Claim 61
Dependent Claim
37 words
An EL element in claim 59, wherein the number of said oxadiazole rings is 2, the benzene ring being substituted by the oxadiazole rings at one of ortho position (1,2), meta position (1,3) and para position (1,4).
Claim 62
Dependent Claim
31 words
An EL element in claim 60, wherein the benzene ring, which is substituted by the oxadiazole rings at the two positions, is substituted by the oxadiazole ring at one more position.
Claim 63
Dependent Claim
30 words
An EL element in claim 59, wherein the number of the oxadiazole rings is 3, the benzene ring being substituted by the oxadiazole rings at 1, 3 and 5 positions.
Claim 64
Dependent Claim
31 words
An EL element in claim 58, wherein the electron transport luminous layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and two benzene rings between the oxadiazole rings.
Claim 65
Dependent Claim
39 words
An EL element in claim 63, wherein the number of the oxadiazole rings is 2, a biphenyl group which includes the two benzene rings being substituted by the oxadiazole at either 4- and 4'- or 2- and 2'- positions.
Claim 66
Dependent Claim
30 words
An EL element in claim 58, wherein the electron transport layer comprises an oxadiazole series compound having a plurality of oxadiazole rings and an alkyl chain between the oxadiazole rings.
Claim 67
Dependent Claim
28 words
An EL element in claim 65, wherein the number of the oxadiazole rings is 2, the carbon number of an alkyl chain between the oxadiazole rings being 1-6.
Claim 68
Dependent Claim
116 words
An EL element in claim 58, wherein the oxadiazole series compounds are selected from the chemical formulas shown below: ##STR35## wherein R, R 1 , R 2 and R 3 are selected from the group consisting of H, CH 3 , C 2 H 5 , C 3 H 7 (CH 3 ) 3 C, OCH 3 , OC 2 H 5 , NH 2 , N(CH 3 ) 2 , N(C 2 H 5 ) 2 , CN, phenyl and cyclohexyl, and R' is selected from the group consisting of H, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , N(CH 3 ) 2 and an oxadiazole ring.
Claim 69
Dependent Claim
26 words
An EL element in claim 58, wherein the hole transport layer is made front diamine, the organic luminous layer being made from 1,1,4,4,tetraphenyl 1, 3 butadiene.
References Cited (Backward Citations)
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