Material for organic electroluminescence device and organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-9306171-B2
Application number	US-201213705742-A
Country	US
Kind code	B2
Filing date	Dec 5, 2012
Priority date	Dec 5, 2011
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

A material for organic electroluminescence device having a specific central skeleton to which a cyano-substituted aromatic hydrocarbon group or a cyano-substituted heterocyclic group is bonded at its specific position is described. Further described is an organic electroluminescence device including an organic thin film layer between an anode and a cathode. The organic thin film layer include an light emitting layer and at least one layer of the organic thin film layer contains the material for organic electroluminescence device. The material for organic electroluminescence device realizes an organic electroluminescence device with good emission efficiency.

First claim

What is claimed is:

1. A material for organic electroluminescence device represented by formula (I):

wherein:
each of A 1 and A 2 independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, wherein the heterocyclic group is selected from the group consisting of a dibenzofuran ring residue and a dibenzothiophene ring residue;
A 3 represents a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms;
each of A 1 , A 2 , and A 3 is optionally substituted with at least one group selected from the group consisting of a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an aralkyl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 ring atoms, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a spirobifluorenyl group, and a fluoranthenyl group, the at least one optional group being optionally further substituted with at least one of the optional groups;
m represents an integer of 0 to 3;
each of X 1 to X 8 and Y 1 to Y 8 independently represents N or CR a ;
each R a independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, or a halogen atom, provided that one of X 5 to X 8 and one of Y 1 to Y 4 are bonded to each other via A 3 or directly; and
the formula (I) satisfies at least one of the following requirements (i) and (ii):
(i) at least one of A 1 and A 2 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms, wherein the heterocyclic group is selected from the group consisting of a dibenzofuran ring residue and a dibenzothiophene ring residue; and
(ii) at least one of X 1 to X 4 and Y 5 to Y 8 represents CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 represents a cyano-substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a cyano-substituted heterocyclic group having 5 to 30 ring atoms, provided that when two or more R a groups exist, the R a groups may be the same or different.

2. The material for organic electroluminescence device according to claim 1 , which satisfies the requirement (i) but does not satisfy the requirement (ii).

3. The material for organic electroluminescence device according to claim 1 , which satisfies the requirement (ii) but does not satisfy the requirement (i).

4. The material for organic electroluminescence device according to claim 1 , which satisfies both the requirements (i) and (ii).

5. The material for organic electroluminescence device according to claim 1 , wherein at least one of A 1 and A 2 represents a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano-substituted phenanthryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl group, a cyano-substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9′-spirobi[9H-fluorene]-2-yl group, a cyano-substituted 9,9-dimethylfluorenyl group, or a cyano-substituted triphenylenyl group.

6. The material for organic electroluminescence device according to claim 1 , wherein A 1 is substituted by a cyano group, and A 2 is not substituted by a cyano group.

7. The material for organic electroluminescence device according to claim 1 , wherein at least one of X 1 to X 4 and Y 5 to Y 8 represents CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 represents a cyano-substituted phenyl group, a cyano-substituted naphthyl group, a cyano-substituted phenanthryl group, a cyano-substituted dibenzofuranyl group, a cyano-substituted dibenzothiophenyl group, a cyano-substituted biphenyl group, a cyano-substituted terphenyl group, a cyano-substituted 9,9-diphenylfluorenyl group, a cyano-substituted 9,9′-spirobi[9H-fluorene]-2-yl group, a cyano-substituted 9,9-dimethylfluorenyl group, or a cyano-substituted triphenylenyl group.

8. The material for organic electroluminescence device according to claim 1 , wherein X 6 and Y 3 are bonded to each other via A 3 or directly.

9. The material for organic electroluminescence device according to claim 1 , wherein X 6 and Y 2 are bonded to each other via A 3 or directly.

10. The material for organic electroluminescence device according to claim 1 , wherein X 7 and Y 3 are bonded to each other via A 3 or directly.

11. The material for organic electroluminescence device according to claim 1 , wherein m represents 0.

12. The material for organic electroluminescence device according to claim 1 , wherein m represents 1.

13. An organic electroluminescence device comprising an organic thin film layer comprising one or more layers between a cathode and an anode, wherein the organic thin film layer comprises a light emitting layer, and at least one layer of the organic thin film layer comprises the material for organic electroluminescence device according to claim 1 .

14. The organic electroluminescence device according to claim 13 , wherein the light emitting layer comprises the material for organic electroluminescence device.

15. The organic electroluminescence device according to claim 13 , wherein the light emitting layer comprises a phosphorescent material selected from ortho metallated complexes of a metal selected from iridium (Ir), osmium (Os), and platinum (Pt).

16. The organic electroluminescence device according to claim 1 , which further comprises a layer adjacent to the light emitting layer between the cathode and the light emitting layer, and the layer adjacent to the light emitting layer comprises the material for organic electroluminescence device.

17. The organic electroluminescence device according to claim 1 , which further comprises a blocking layer adjacent to the light emitting layer between the cathode and the light emitting layer, and the blocking layer comprises the material for organic electroluminescence device.

18. The material for organic electroluminescence device according to claim 1 , wherein the monocyclic hydrocarbon group having 6 or less ring carbon atoms is selected from the group consisting of a phenylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexylene group, and a cyclopentylene group.

19. The material for organic electroluminescence device according to claim 1 , wherein the monocyclic heterocyclic group having 6 or less ring atoms is selected from the group consisting of a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a furylene group, and a thiophenylene group.

Assignees

• Mizuki Yumiko
• Ito Mitsunori
• Inoue Tetsuya
• Hibino Kumiko
• Nishimura Kazuki
• Yoshida Kei
• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Mitsunori
• Inoue Tetsuya
• Hibino Kumiko
• Nishimura Kazuki
• Yoshida Kei

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C09K2211/1011

  Condensed systems · CPC title