Biphenyl derivative, material for organic electroluminescence device, and organic electroluminescence device using the same

1. A biphenyl derivative represented by the following general formula (I):

wherein, Ar 1 and Ar 2 represent a condensed aromatic hydrocarbon group comprising 3 rings or more, and Ar 3 represents an unsubstituted phenyl group or a condensed aromatic hydrocarbon group comprising 2 rings or more, wherein when any of Ar 1 to Ar 3 represents an anthracene-9-yl group, the 10th position of said anthracene-9-yl group is substituted with R 1 to R 3 ;

R 1 to R 3 each independently represents, a substituted or unsubstituted aromatic hydrocarbon group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic heterocyclic group having ring carbon atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having ring carbon atoms of 7 to 50, a substituted or unsubstituted aryloxy group having ring carbon atoms of 6 to 50, a substituted or unsubstituted arylthio group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 2 to 50, a silyl group which may be substituted with a substituted or unsubstituted alkyl group having ring carbon atoms of 1 to 50 or a substituted or unsubstituted aryl group having ring carbon atoms of 6 to 50, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxy group;

R 4 represents, a substituted or unsubstituted aromatic hydrocarbon group having ring carbon atoms of 6 to 10, a substituted or unsubstituted aromatic heterocyclic group having ring carbon atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having ring carbon atoms of 7 to 50, a substituted or unsubstituted aryloxy group having ring carbon atoms of 6 to 50, a substituted or unsubstituted arylthio group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 2 to 50, a silyl group which may be substituted with a substituted or unsubstituted alkyl group having ring carbon atoms of 1 to 50 or a substituted or unsubstituted aryl group having ring carbon atoms of 6 to 50, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxy group; a to d each independently represents an integer for 0 to 3;

wherein when Ar 3 is an unsubstituted phenyl group and c represents an integer of 1 to 3, the substituted or unsubstituted aromatic hydrocarbon group represented by R 3 is selected from the group consisting of a phenyl group, a 1-naphtyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a 1-chrysenyl group, a 2-chrysenyl group, a 6-chrysenyl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a 4-phenylnaphthalene-1-yl group, a 6-phenylnaphthalene-2-yl group, a 4-(naphthalene-2-yl)phenyl group, a 3-(naphthalene-2-yl)phenyl group, a 2-(naphthalene-2-yl)phenyl group, a 4-(naphthalene-1-yl)phenyl group, a 3-(naphthalene-1-yl)phenyl group, a 2-(naphthalene-1-yl)phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a p-t-butyiphenyl group, p-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphtyl group, a 4-methyl-1-naphtyl, a 4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a 4″-t-butyl-p-terphenyl-4-yl group.

2. The biphenyl derivative according to claim 1 represented by the following general formula (II):

3. The biphenyl derivative according to claim 1 represented by the following general formula (III):

4. The biphenyl derivative according to any one of claims 1 to 3 , wherein Ar 3 represents a condensed aromatic hydrocarbon group comprising 2 rings or more in the general formulae (I) to (III).

5. The biphenyl derivative according to any one of claims 1 to 3 , wherein Ar 3 represents a condensed aromatic hydrocarbon group comprising 3 rings or more in the general formulae (I) to (III).

6. The biphenyl derivative according to any one of claims 1 to 3 , wherein at least one of Ar 1 to Ar 3 represents a pyrenyl group in the general formulae (I) to (III).

7. The biphenyl derivative according to any one of claims 1 to 3 , wherein at least one of Ar 1 to Ar 3 represents a substituted anthracene-9-yl group comprising a substituted or unsubstituted aromatic hydrocarbon group having ring carbon atoms of 6 to 50 at the 10th position thereof.

8. The biphenyl derivative according to any one of claims 1 to 3 , which is a host material for an organic electroluminescent device.

9. An organic electroluminescent device, comprising:

at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrodes consisting of an anode and a cathode,

wherein the organic thin film layer comprises, singly or as a component of a mixture, at least one compound selected from the group consisting of the biphenyl derivatives as claimed in claim 1 .

10. The organic electroluminescent device according to claim 9 , wherein, the light emitting layer comprises the biphenyl derivatives represented by the general formula (I) singly or as a component of a mixture.

11. The organic electroluminescent device according to claim 10 , wherein, the light emitting layer comprises the biphenyl derivatives represented by the general formula (I) as a main component.

12. The organic electroluminescent device according to claim 9 , wherein, the light emitting layer further comprises an arylamine compound.

13. The organic electroluminescent device according to claim 12 , wherein, the arylamine compound is represented by general formula (A)

wherein Ar 3 represents a group selected from a phenyl group, a biphenyl group, a terphenyl group, a stilbene group and a distyrylaryl group,

Ar 4 and Ar 5 each represents a hydrogen atom, an aromatic hydrocarbon group having carbon atoms of 6 to 20, and

Ar 3 , Ar 4 and Ar 5 may have substituent, and

p represents an integer of 1 to 4.

14. The organic electroluminescent device according to claim 9 , wherein, the light emitting layer further comprises a styrylamine compound.

15. The organic electroluminescent device according to claim 14 , wherein, the styrylamine compound is represented by general formula (B)

wherein Ar 6 to Ar 8 each represents a substituted or unsubstituted aryl group having ring carbon atoms of 6 to 40, and

q represents an integer of 1 to 4.

16. The biphenyl derivative according to claim 1 , wherein at least two of Ar 1 to Ar 3 represent a substituted anthracene-9-yl group.

17. The biphenyl derivative according to claim 1 , wherein each of Ar 1 to Ar 3 represent a substituted anthracene-9-yl group.

18. The biphenyl derivative according to claim 1 , wherein Ar 1 and Ar 2 each independently represent a 9-phenanthryl group, a 9-anthryl group, or a 1-pyrenyl group.

19. The biphenyl derivative according to claim 1 , wherein Ar 3 represents a unsubstituted phenyl group, a 1-naphthyl group, a 2-naphtyl group, a 9-phenanthryl group, a 9-anthryl group, or a 1-pyrenyl group.