Organic electroluminescence device

• US 5,336,546 A
• Filed: 02/03/1993
• Issued: 08/09/1994
• Est. Priority Date: 07/12/1991
• Status: Expired due to Fees

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Hosokawa, Chishio, Hironaka, Yoshio, Kusumoto, Tadashi, Tokailin, Hiroshi
• Primary Examiner(s): Ryan, Patrick J.
• Assistant Examiner(s): Jewik, Patrick
• Application Number:
  US07/971,817
• Time in Patent Office: 552 Days
• Field of Search: 548/136, 548/145, 313/504, 313/505, 313/506, 313/503, 428/209, 428/690, 428/917, 428/691, 428/216, 428/460, 252/301.16, 252/301.24, 252/301.28, 252/301.31, 252/301.21
• US Class Current: 428/209
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 85/60 Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6565 Oxadiazole compounds
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/24917 including metal layer
• CPC Class Codes: Y10T 428/31688 Next to aldehyde or ketone condensation product

Abstract

An organic electroluminescence device including an oxadiazole or thiadiazole compound interposed between two electrons. The compound is of the formula ##STR1## wherein Z¹ and Z² are each an unsubstituted or substituted aromatic group; Y¹ and Y² are each an unsubstituted or substituted aromatic group; Q is --O--, --CH₂ --, --CH₂ --CH₂ --; or --C(CH₃)₂ ; and X is --O-- or --S--. The organic electroluminescence device has a high brightness, a high luminous efficiency and a long service life.

Claims

1. In an organic electroluminescence device, the improvement comprising the device containing a compound represented by the formula:

##STR34## wherein Z¹ and Z² are each an unsubstituted aromatic group or an aromatic group being substituted with C_1-5 alkyl groups, C_1-5 alkyloxy groups, cyano groups, chlorines, bromines or fluorines;

Y¹ and Y² are each an unsubstituted aromatic group or an aromatic group being substituted with C_1-5 alkyl groups;

Z is --O--, --CH₂ --, --CH₂ --CH₂ --, or --C(CH₃)₂ --; and

X is --O-- or --S--.

3. The organic electroluminescence device according to claim 1, wherein the compound is sandwiched between a pair of electrodes.

4. The organic electroluminescence device according to claim 3, wherein the device is in the form of a laminate comprising in the following order:

an anode, a hole injecting layer, a light emitting layer, an electron injecting layer and a cathode, said light emitting layer or said electron injecting layer comprising said compound.

5. The organic electroluminescence device according to claim 3, wherein the device is in the form of a laminate comprising in the following order:

an anode, a light emitting layer, an electron injecting layer and a cathode, said light emitting layer or said electron injecting layer comprising said compound.

9. The organic electroluminescence device according to claim 1, wherein the device comprises an electron injecting layer which comprises said compound.

11. The organic electroluminescence device according to claim 1, wherein Z¹ and Z² are each selected from the group consisting of ##STR36## wherein R is a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a t-pentyl group, a neopentyl group, a cyano group, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group, an isopentoxy group, a neopentoxy group, chlorine bromine or fluorine;

and n is 1 to 5.

12. The organic electroluminescence device according to claim 11, wherein Y¹ and Y² are each selected from the group consisting of ##STR37## wherein R'"'"' is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a t-pentyl group, and a neopentyl group;

and n is 1 to 4.

15. The organic electroluminescence device according to claim 1, wherein X is S.

2. In an organic electroluminescence device, the improvement comprising the device containing a compound represented by the formula:

##STR35## wherein Z¹ and Z² are each an unsubstituted aromatic group or an aromatic group being substituted with C_1-5 alkyl groups, C_1-5 alkyloxy groups, cyano groups, chlorines, bromines or fluorines;

Y¹ and Y² are each an unsubstituted aromatic group or an aromatic group being substituted with C_1-5 alkyl groups;

Q is --O--, --CH₂ --, --CH₂ --CH₂ --, or --C(CH₃)₂ --; and

X is --O-- or --S--.

6. The organic electroluminescence device according to claim 2, wherein the compound is sandwiched between a pair of electrodes.

7. The organic electroluminescence device according to claim 6, wherein the device is in the form of a laminate comprising in the following order:

an anode, a hole injecting layer, a light emitting layer, an electron injecting layer and a cathode, said light emitting layer or said electron injecting layer comprising said compound.

8. The organic electroluminescence device according to claim 6, wherein the device is in the form of a laminate comprising in the following order:

an anode, a light emitting layer, an electron injecting layer and a cathode, said light emitting layer or said electron injecting layer comprising said compound.

10. The organic electroluminescence device, according to claim 2 wherein the device comprises an electron injecting layer which comprises said compound.

13. The organic electroluminescence device according to claim 2, wherein Z¹ and Z² are each selected from the group consisting of ##STR38## wherein R is a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a t-pentyl group, a neopentyl group, a cyano group, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group, an isopentoxy group, a neopentoxy group, chlorine, bromine or fluorine;

and n is 1 to 5.

14. The organic electroluminescence device according to claim 13, wherein Y¹ and Y² are each selected from the group consisting of ##STR39## wherein R'"'"' is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a t-pentyl group, and a neopentyl group;

and n is 1 to 4.

16. The organic electroluminescence device according to claim 2, wherein X is S.

17. An electroluminescence device comprising an oxadiazole compound which sandwiched between a pair of electrodes, said compound being selected from the group consisting of 4,4'"'"'-bis (5-phenyl-1,3,4-oxadiazole-2-yl)diphenylether, 4,4'"'"'-bis(5-(p-diphenyl)-1,3,4-oxadiazole-2-yl)diphenylether, 4,4'"'"'-bis(5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl)diphenylether, 4,4'"'"'-bis[2-(5-(p-diphenyl)-1,3,4-oxadiazole-2-yl)vinyl]diphenylether, 4,4'"'"'-bis[2-(5-phenyl-1,3,4-oxadiazole-2-yl)vinyl]diphenylether, 4,4'"'"'bis(5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl)diphenylmethane, 4,4'"'"'-bis(5-(1-naphthyl)-1,3,4-oxadiazole-2yl)diphenylether, 4,4'"'"'-bis[5-(2-naphthyl)-1,3,4-oxadiazole-2-yl]diphenylether, 4,4'"'"'-bis[5-(4-cyanophenyl)-1,3,4-oxadiazole-2-yl]diphenylether, 1,1'"'"'-oxybis[p-(5-phenyl-1,3,4-oxadiazole-2-yl)diphenyl],1,1'"'"'-oxybis[p-(5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2-yl)diphenyl],1,1'"'"'-oxybis[p-(5-(p-diphenyl)-1,3,4-oxadiazole-2-yl)diphenyl],1,1'"'"'-oxybis[p-(5-(1-napthyl)-1,3,4-oxadiazole-2yl)diphenyl], and 1,1'"'"'-oxybis[p-(5-(2-naphthyl)-1,3,4-oxadiazole-2yl)diphenyl].

19. The electroluminescence device according to claim 17, wherein said oxadizole compound is selected from the group consisting of 4,4'"'"'-bis(5-phenyl-1,3,4-oxadiazole-2-yl)diphenylether, 4,4'"'"'-bis(5-(p-diphenyl)-1,3,4-oxadiazole-2yl)diphenylether, 4,4'"'"'-bis(5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2yl)diphenylether, 4,4'"'"'-bis[2-(5-(p-diphenyl)-1,3,4-oxadiazole-2yl)vinyl]diphenylether, 4,4'"'"'-bis[2-(5-phenyl-1,3,4-oxadiazole-2yl)vinyl]diphenylether, 4,4'"'"'-bis(5-(4-tert-butylphenyl)-1,3,4-oxadiazole-2yl)diphenylmethane and 4,4'"'"'-bis(5-(1-naphthyl)-1,3,4-oxadiazole-2yl)diphenylether.

18. An electroluminescence device comprising a thiadiazole compound which is sandwiched between a pair of electrodes, said compound being selected from the group consisting of 4,4'"'"'-bis(5-phenyl-1,3,4-thiadiazole-2-yl)diphenylether, 4,4'"'"'-bis[5-(p-diphenyl)-1,3,4-thiadiazole-2-yl]diphenylether, 4,4'"'"'-bis[5-(4-tert-butylphenyl)-1,3,4-thiadiazole-2-yl]diphenylether, 4,4'"'"'-bis[5-(4-cyanophenyl)-1,3,4-thiadiazole-2yl]diphenylether, 4,4'"'"'-bis[5-chlorophenyl)-1,3,4-thiadiazole-2yl]diphenylether, 4,4'"'"'-bis[5-(p-methoxyphenyl)-1,3,4-thiadiazole-2-yl]diphenylether, 4,4'"'"'-bis[5-(4-tert-butoxyphenyl)-1,3,4-thiadiazole-2yl]diphenylether, 4,4'"'"'-bis[5-(1-naphthyl)-1,3,4-thiadiazole-2yl]diphenylether, 4,4'"'"'-bis[5-(2-naphthyl)-1,3,4-thiadiazole-2yl]diphenylether, 4,4'"'"'bis[2-(5-phenyl-1,3,4-thiadiazole-2-yl)vinyl]diphenylether, 4,4'"'"'-bis[2-(5-(p-diphenyl)-1,3,4-thiadiazole-2-yl)vinyl]diphenylether, 1,1'"'"'-oxybis[p-(5-(4-tert-butylphenyl)--1,3,4-thiadiazole-2yl)diphenyl], 1,1'"'"'-oxybis[p-(5-(p-diphenyl)-1,3,4-thiadiazole-2-yl)diphenyl],and 1,1'"'"'-oxybis[p-(5-(1-naphthyl)-1,3,4-thiadiazole-2yl)diphenyl].

20. The electroluminescence device according to claim 18, wherein said thiadiazole compound is selected from the group consisting of

4,4'"'"'-bis(5-(1-naphthyl)-1,3,4-thiadiazole-2yl)diphenylether,

4,4'"'"'-bis(5-phenyl-1,3,4-thiadiazole-2-yl)diphenylether,

4,4'"'"'-bis(5-(p-methoxyphenyl)-1,3,4-thiadiazole-2-yl)diphenylether,

4,4'"'"'-bis(5-(4-cyanophenyl)-1,3,4-thiadiazole-2-yl)diphenylether,

4,4'"'"'-bis(5-(m-chlorophenyl)-1,3,4-thiadiazole-2yl)diphenylether and 1,1'"'"'-oxybis(p-(5-(1-naphthyl)-1,3,4-thiadiazole-2-yl)diphenyl.