4-AMINOCARBAZOLE COMPOUND AND USE THEREOF

• US 20140296519A1
• Filed: 10/25/2012
• Published: 10/02/2014
• Est. Priority Date: 10/26/2011
• Status: Active Grant

• Current Assignee: Tosoh Corporation
• Original Assignee: Tosoh Corporation
• Inventors: Matsumoto, Naoki, Miyazaki, Takanori
• Granted Patent: US 9,172,045 B2
• Time in Patent Office: Days
• US Class Current: 544/212
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C09B 57/008 Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• 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 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 : characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 : Hole transporting layers
• CPC Class Codes: H10K 85/615 : Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A 4-aminocarbazole compound represented by formula (1):

wherein Ar¹-Ar⁴ represent substituted or unsubstituted aryl, thienyl, pyridyl, benzothienyl, dibenzothienyl, dibenzofuranyl, 4-carbazolyl, dibenzothienylphenyl, dibenzofuranylphenyl or 9-carbazolylphenyl group; R¹-R⁷ represent substituted or unsubstituted aryl, heteroaryl or heteroarylphenyl group, or alkyl, alkoxy, cyano group, or hydrogen or halogen atom; n is integer of 0-2; and X represents substituted or unsubstituted (n+1)-valent aromatic hydrocarbon, heteroaromatic or heteroarylphenyl group. The 4-aminocarbazole compound provides an organic EL device exhibiting enhanced emitting efficiency and durability.

Claims

1. A 4-aminocarbazole compound represented by the following general formula (1):

2. The 4-aminocarbazole compound according to claim 1, wherein R¹ through R⁷ independently represent an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, a hydrogen atom or a halogen atoms.

3. The 4-aminocarbazole compound according to claim 1, wherein R¹ through R⁷ independently represent a phenyl group, a methylphenyl group, a methoxyphenyl group, a biphenylyl group, a dibenzothienyl group, a dibenzofuranyl group, a methyl group, a methoxy group or a hydrogen atom.

4. The 4-aminocarbazole compound according to claim 1, wherein R¹ through R⁷ independently represent a phenyl group, a methylphenyl group, a methoxyphenyl group or a hydrogen atom.

5. The 4-aminocarbazole compound according to claim 1, wherein R⁴, R⁵, R⁶ and R⁷ represent a hydrogen atom.

6. The 4-aminocarbazole compound according to claim 1, wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ represent a hydrogen atom.

7. The 4-aminocarbazole compound according to claim 1, wherein Ar¹ through Ar⁴ independently represent an aryl group having 6 to 30 carbon atoms, a dibenzothienyl group, a dibenzofuranyl group, a 4-carbazolyl group, a dibenzofuranylphenyl group or a dibenzothienylphenyl group or a 9-carbazolylphenyl group, and these groups may independently have at least one substituent selected from the group consisting of a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 3 to 11 carbon atoms.

8. The 4-aminocarbazole compound according to claim 1, wherein Ar¹ through Ar⁴ independently represent a phenyl group, a biphenylyl group, a terphenylyl group, a fluorenyl group, a benzofluorenyl group, a dibenzothienyl group, a dibenzofuranyl group, a dibenzofuranylphenyl group, a dibenzothienylphenyl group or a 9-carbazoylphenyl group, and these groups may independently have at least one substituent selected from the group consisting of a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group and a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms;

or Ar¹ through Ar⁴ independently represent a 4-carbazolyl group which may independently have at least one substituent selected from the group consisting of a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 3 to 11 carbon atoms.

9. The 4-aminocarbazole compound according to claim 1, wherein Ar¹ through Ar⁴ independently represent a phenyl group, a methylphenyl group, a methoxyphenyl group, a biphenylyl group, a terphenylyl group, a 9,9′

-dimethylfluorenyl group, a 11,11′

-dimethylbenzo[a]fluorenyl group, a dibenzothienyl group, a dibenzofuranyl group, a dibenzothienylphenyl group, a 4-(9-carbazoyl)phenyl group, a 9-phenylcarbazol-4-yl group, a 9-biphenylylcarbazol-4-yl group, a 9-quinolylcarbazol-4-yl group or a 9-dibenzothienylcarbazol-4-yl group.

10. The 4-aminocarbazole compound according to claim 1, wherein X represents an aromatic group selected from the group consisting of (n+1)-valent benzene, (n+1)-valent biphenyl, (n+1)-valent naphthalene, (n+1)-valent phenanthrene, (n+1)-valent fluorene, (n+1)-valent naphthylbenzene, (n+1)-valent pyridine, (n+1)-valent pyrimidine, (n+1)-valent 1,3,5-triazine, (n+1)-valent quinoline, (n+1)-valent dibenzothiophene, (n+1)-valent dibenzofuran, (n+1)-valent pyridylbenzene, (n+1)-valent imidazolylbenzene, (n+1)-valent benzoimidazolylbenzene and (n+1)-valent benzothiazolylbenzene, and these aromatic groups may independently have at least one substituent selected from the group consisting of a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group and a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group and a halogen atom.

11. The 4-aminocarbazole compound according to claim 1, wherein X represents an aromatic group selected from the group consisting of (n+1)-valent benzene, (n+1)-valent biphenyl, (n+1)-valent quinoline, (n+1)-valent dibenzothiophene, (n+1)-valent 1,3,5-triazine and (n+1)-valent pyridylbenzene, and these aromatic groups may independently have at least one substituent selected from the group consisting of a methyl group, an ethyl group, a straight, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group and a straight, branched or cyclic alkoxy group having 3 to 18 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cyano group and a halogen atom.

12. The 4-aminocarbazole compound according to claim 1, wherein X represents (n+1)-valent benzene, (n+1)-valent biphenyl, (n+1)-valent quinoline, (n+1)-valent dibenzothiophene, (n+1)-valent 2,4-diphenyl-1,3,5-triazine or (n+1)-valent pyridylbenzene.

13. The 4-aminocarbazole compound according to claim 1, wherein n represents an integer of 0 or 1.

14. An organic electroluminescent device having at least one layer selected from the group consisting of a luminescent layer, a hole transport layer and a hole injection layer, said at least one layer comprising a 4-aminocarbazole compound as claimed in claim 1.

15. A hole transport material or a hole injection material, which comprises a 4-aminocarbazole compound as claimed in claim 1.