Biscarbazole derivative and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-10147889-B2
Application number	US-201615165142-A
Country	US
Kind code	B2
Filing date	May 26, 2016
Priority date	Feb 7, 2011
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

A biscarbazole derivative having a specific group, which is represented by formula (1):

and an organic electroluminescence device in which a plurality of organic thin-film layers including a light emitting layer are disposed between a cathode and an anode, and at least one of the organic thin-film layers include the biscarbazole derivative. The organic electroluminescence device exhibits high emission efficiency and has a long lifetime. In formula (1), each of A 1 and A 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; each of Y 1 to Y 16 independently represents C(R) or a nitrogen atom; each of R groups independently represents a hydrogen atom, etc.; and each of L 1 and L 2 independently represents a single bond, etc.; provided that at least one of A 1 , A 2 and R represents a substituted or unsubstituted fluoranthenyl group, etc.

First claim

What is claimed is:

1. A biscarbazole derivative represented by formula (1):

wherein:
-L 1 -A 1 and -L 2 -A 2 are different from each other;
A 1 represents a substituted or unsubstituted triphenylenyl group;
A 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms;
each of Y 1 to Y 16 independently represents C(R) or a nitrogen atom, and each of R groups independently represents a hydrogen atom, a substituent, or a valence bonded to a carbazole skeleton; and
each of L 1 and L 2 independently represents a single bond, or a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
when A 2 has a substituent, the substituent represents a fluorine atom, a cyano group, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, a linear, branched, or cyclic, divalent, unsaturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a pyrrolyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a thienyl group, a residue of an indole ring, a residue of a carbazole ring, a residue of a furan ring, a residue of a thiophene ring, a residue of an oxazole ring, a residue of an oxadiazole ring, a residue of a benzoxazole ring, a residue of a thiazole ring, a residue of a thiadiazole ring, a residue of a benzothiazole ring, a residue of a triazole ring, a residue of an imidazole ring a residue of a benzimidazole ring, a residue of a pyran ring, a residue of a dibenzofuran ring, or a residue of a benzo[c]dibenzofuran ring.

2. The biscarbazole derivative according to claim 1 , wherein said biscarbazole derivative is represented by formula (2), (3) or (4):

wherein each of A 1 , A 2 , Y 1 to Y 16 , L 1 , and L 2 is as defined in formula (1).

3. The biscarbazole derivative according to claim 1 , wherein when A 2 has a substituent, the substituent represents a fluorine atom, a cyano group, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, a linear, branched, or cyclic, divalent, unsaturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

4. The biscarbazole derivative according to claim 1 , wherein A 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted benzo[c]phenanthrenyl group, a substituted or unsubstituted benzo[a]triphenylenyl group, a substituted or unsubstituted naphtho[1,2-c]phenanthrenyl group, a substituted or unsubstituted naphtho[1,2-a]triphenylenyl group, a substituted or unsubstituted dibenzo[a,c]triphenylenyl group, or a substituted or unsubstituted benzo[b]fluoranthenyl group.

5. The biscarbazole derivative according to claim 1 , wherein A 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

6. The biscarbazole derivative according to claim 1 , wherein at least one of L 1 and L 2 represents a substituted or unsubstituted, divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

7. The biscarbazole derivative according to claim 1 , wherein each of L 1 and L 2 represents a single bond.

8. The biscarbazole derivative according to claim 1 , wherein at least one of L 1 and L 2 represents a single bond or a substituted or unsubstituted phenylene group.

9. The biscarbazole derivative according to claim 1 , wherein when A 2 has a substituent, the substituent represents a fluorine atom a cyano group, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or a substituted or unsubstituted, linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms.

10. The biscarbazole derivative according to claim 1 , wherein when R group represents a substituent, the substituent represents a fluorine atom, a cyano group, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, a linear, branched, or cyclic, divalent, unsaturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear, branched, or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 2 to 30 ring carbon atoms.

11. A material for an organic electroluminescence device comprising the biscarbazole derivative according to claim 1 .

12. The biscarbazole derivative according to claim 1 ,
wherein each of L 1 and L 2 represents a single bond; and
A 2 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group,
when A 2 has a substituent, the substituent represents a fluorine atom, a cyano group, a substituted or unsubstituted, linear, branched, or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched, or cyclic alkylene group having 1 to 20 carbon at

Assignees

• Idemitsu Kosan Co

Inventors

• Inoue Tetsuya
• Ito Mitsunori
• Gorai Kumiko
• Nishimura Kazuki
• Ikeda Kiyoshi

Classifications

• H01L2251/301

  Electricity · mapped topic

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H01L51/5016

  Electricity · mapped topic