Organic hole transporting and blue light emitting electroluminescent materials

• US 6,387,545 B1
• Filed: 04/14/1999
• Issued: 05/14/2002
• Est. Priority Date: 04/14/1999
• Status: Expired due to Term

• Current Assignee: Industrial Technology Research Institute
• Original Assignee: Industrial Technology Research Institute
• Inventors: Liu, Jia-Ming, Lu, Po-Yen, Hsieh, Huan-Lurn, Wang, Ying-Chuan
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US09/292,773
• Time in Patent Office: 1,126 Days
• Field of Search: 428/690, 428/704, 428/917, 313/504, 313/506, 564/307, 564/395, 564/405, 564/433
• US Class Current: 428/690
• CPC Class Codes: C07C 211/54 having amino groups bound to two or three six-membered aromatic rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

A tertiary amine imparted quaterphenyl compound represented by the following formula:

where R₁ and R₂, which can be different or the same, are hydrogen, C₁-C₅ alkyl, or C₆-C₁₂ aryl, and R₃ is hydrogen, C₁-C₅ alkyl, a vinyl group, or an aryl vinyl group. The tertiary amine-imparted quaterphenyl compound exhibits good blue light luminescence and hole-transportability, and can be used in forming a hole-transporting layer, a blue light emitting layer, or a combined hole-transporting and light emitting layer of a light emitting organic electroluminescent device. Examples of the quaterphenyl compounds include N-quaterphenyl-4-yl-N,N-diphenylamine, N-(4′-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine, or N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine.

Claims

1. A tertiary amine imparted quaterphenyl compound represented by the following formula:

where R₁ and R₂, which can be different or the same, are hydrogen, C₁-C₅ alkyl, or C₆-C₁₂ aryl, and R₃ is hydrogen, C₁-C₅ alkyl, a vinyl group, or an aryl vinyl group.

2. The tertiary amine imparted quaterphenyl compound according to claim 1 which is N-(4′

-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine.

3. The tertiary amine imparted quaterphenyl compound according to claim 1 which is N-quaterphenyl-4-yl-N,N-diphenylamine, N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine, or N-(4′

-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine.

4. The tertiary amine imparted quaterphenyl compound according to claim 1 which is synthesized according to the following reaction:

5. The tertiary amine imparted quaterphenyl compound according to claim 1 which is synthesized according to the following reaction:

6. The tertiary amine imparted quaterphenyl compound according to claim 1 which is N-quaterphenyl-4-yl-N,N-diphenylamine.

7. A blue color organic electroluminescent device comprising an electron-transporting layer and a hole-transporting layer, wherein said hole-transporting layer also provides light emitting function to serve dual functions as a combined hole-transporting and light-emitting layer;

further wherein said combined hole-transporting and light-emitting layer contains a tertiary amine imparted quaterphenyl compound represented by the following formula;

 

where R₁ and R₂, which can be different or the same, are hydrogen, C₁C₅ alkyl, or C₆-C₁₂ aryl, and R₃ is hydrogen, C₁-C₅ alkyl, a vinyl group, or an aryl vinyl group.

8. The blue color organic electroluminescent device according to claim 7 wherein said tertiary amine imparted quaterphenyl compound is N-quaterphenyl-4-yl-N,N-diphenylamine, N-(4′

-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine, or N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine.

9. The blue color organic electroluminescent device according to claim 7 wherein said electron-transport layer comprises a metal chelate, 1,3,4-oxadiazole or 1,2,4-triazole or a derivative thereof, a thiopyran sulfone or a derivative thereof, or bis(benzimidazolyl)perylenedicarboximide.

10. The blue color organic electroluminescent device according to claim 9 wherein said metal chelate is aluminum tris(8hydroxyquinoline) or bis (10-hydroxybenzo[h]-quinolinato)beryllium.

11. A blue color organic electroluminescent device comprising an electron-transporting layer, a light emitting layer, and a hole-transporting layer, wherein at least one of said hole-transporting layer and said light emitting layer comprises a tertiary amine imparted quaterphenyl compound represented by the following formula:

where R₁ and R₂, which can be different or the same, are hydrogen, C₁-C₅ alkyl, or C₆-C₁₂ aryl, and R₃ is hydrogen, C₁-C₅ alkyl, a vinyl group, or an aryl vinyl group.

12. The blue color organic electroluminescent device according to claim 11 wherein said tertiary amine imparted quaterphenyl compound is N-quaterphenyl-4-yl-N,N-diphenylamine, N-(4′

-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine, or N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine.

13. The blue color organic electroluminescent device according to claim 11 wherein said electron-transport layer comprises a metal chelate, 1,3,4-oxadiazole or 1,2,4-triazole or a derivative thereof, a thiopyran sulfone or a derivative thereof, or bis(benzimidazolyl)perylenedicarboximide.

14. The blue color organic electroluminescent device according to claim 13 wherein said metal chelate is aluminum tris(8-hydroxyquinoline) or bis(10-hydroxybenzo[h]quinolinato)beryllium.

15. The blue color organic electroluminescent device according to claim 11 wherein said tertiary amine imparted quaterphenyl compound is N-quaterphenyl-4-yl-N,N-diphenylamine.

16. A process for imparting hole-transportability to a blue light emitting organic electroluminescent compound so that said blue light emitting organic electroluminescent compound can be used in a hole-transporting layer, a blue light emitting layer, or a combined hole-transporting and blue light emitting layer of a multi-layered organic electroluminescent device, said process comprising the step of incorporating a tertiary amino group into said blue light emitting organic electroluminescent compound;

wherein said blue light emitting organic electroluminescent compound with hole-transportability is represented by the following formula;

 

where R₁ and R₂, which can be different or the same, are hydrogen, C₁-C₅ alkyl, or C₆-C₁₂ aryl, and R₃ is hydrogen, C₁-C₅ alkyl, a vinyl group, or an aryl vinyl group.

17. The process for imparting hole-transportability to a blue light emitting organic electroluminescent compound according to claim 16, wherein said blue organic electroluminescent compound with hole-transportability is N-quaterphenyl-4-yl-N,N-diphenylamine, N-(4′

-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine, or N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine.

18. The process for imparting hole-transportability to a blue light emitting organic electroluminescent compound according to claim 16 which is represented by the following reaction:

19. The process for imparting hole-transportability to a blue light emitting organic electroluminescent compound according to claim 16 which is represented by the following reaction:

where X is Cl, Br, or I.

20. The process for imparting hole-transportability to a blue light emitting organic electroluminescent compound according to claim 16, wherein said blue organic electroluminescent compound with hole-transportability is N-quaterphenyl-4-yl-N,N-diphenylamine.