Anthracene derivatives, luminescent materials and organic electroluminescent devices

1. An organic electroluminescence device comprising one or more organic thin film layers comprising a light emitting layer between a cathode and an anode,

wherein the light emitting layer comprises a host material that consists of an anthracene derivative comprising a phenanthryl group, the anthracene derivative being represented by formula (1-2):

wherein:

the phenanthryl group in formula (1-2) is one of a substituted or unsubstituted 1-phenanthryl group, a substituted or unsubstituted 2-phenanthryl group, a substituted or unsubstituted 3-phenanthryl group, and a substituted or unsubstituted 4-phenanthryl group;

L 2 represents a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 ring-forming atoms;

Ar 2 represents a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a heterocyclic group having 5 to 50 ring-forming atoms;

substituents R a and R b each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms, and the substituent R b represents a group except a substituted or unsubstituted anthracenyl group;

“p” represents an integer of 0 to 8;

“q” represents an integer of 0 to 9; and

when “p” represents 2 to 8 or “q” represents 2 to 9, a plurality of R a 's or a plurality of R b 's are identical to or different from each other.

2. The organic electroluminescence device according to claim 1 , wherein L 2 is represented by formula (3):

wherein:

a substituent R c represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms; and

“r” represents an integer of 0 to 4, and when “r” represents 2 to 4, a plurality of R c 's are identical to or different from each other.

3. The organic electroluminescence device according to claim 1 , wherein L 2 represents a substituted or unsubstituted fused aromatic ring group having 10 to 50 ring-forming carbon atoms.

4. The organic electroluminescence device according to claim 1 , wherein Ar 2 represents a substituted or unsubstituted fused aromatic ring having 10 to 50 ring-forming carbon atoms.

5. The organic electroluminescence device according to claim 1 , wherein L 2 is represented by formula (3):

and Ar 2 is represented by formula (4):

wherein:

Ar 3 represents a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a heterocyclic group having 5 to 50 ring-forming atoms;

a substituent R c or R d represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms; and

“r” and “s” each represent an integer of 0 to 4, and when “r” and/or “s” each represent/represents 2 to 4, a plurality of R c 's and/or a plurality of R d 's are identical to or different from each other.

6. The organic electroluminescence device according to claim 1 , wherein “q” represents 0.

7. The organic electroluminescence device according to claim 1 , wherein the light emitting layer further comprises at least one of a fluorescent dopant and a phosphorescent dopant.

8. The organic electroluminescence device according to claim 7 , wherein the fluorescent dopant comprises an arylamine compound.

9. The organic electroluminescence device according to claim 7 , wherein the fluorescent dopant comprises a styrylamine compound.

10. The organic electroluminescence device according to claim 7 , wherein the fluorescent dopant comprises a fused ring amine derivative represented by formula (5):

wherein:

R e represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms;

“t” represents an integer of 0 to 10; and

Ar 3 to Ar 6 each represent a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring-forming atoms.

11. The organic electroluminescence device according to claim 7 , wherein the fluorescent dopant comprises a fused ring amine derivative represented by formula (6):

wherein:

a substituent R f represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 50 carbon atoms, or a substituted or unsubstituted arylgermanium group having 6 to 50 ring-forming carbon atoms;

“u” represents an integer of 0 to 8; and

Ar 7 to Ar 10 each represent a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring-forming atoms.

12. The organic electroluminescence device according to claim 1 , wherein L 2 is a phenyl group and Ar 2 is a naphthyl group.

13. The organic electroluminescence device according to claim 1 , wherein L 2 is a phenyl group and Ar 2 is a naphthyl-substituted phenyl group.

14. The organic electroluminescence device according to claim 1 , wherein L 2 represents a substituted or unsubstituted arylene group selected from the group consisting of a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, an anthranylene group, a pentacenylene group, a perylenylene group, a picenylene group, a pyrenylene group and a pentaphenylene group, or a substituted or unsubstituted divalent heterocyclic group selected from the group consisting of a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indolinylene group, a quinolinylene group, an acridinylene group, a pyrrolidinylene group, a dioxanylene group, a piperidinylene group, a morpholidinylene group, a piperazinylene group, a triathinylene group, a carbazolylene group, a furanylene group, a thiophenylene group, an oxazolylene group, an oxadiazolylene group, a benzoxazolylene group, a thiazolylene group, a thindiazolylene group, a benzothiazolylene group, a triazolylene group, an imidazolylene group, a benzimidazolylene group, a furanylene group, a dibenzofuranylene group and a benzofuranylene group.

15. The organic electroluminescence device according to claim 1 , wherein L 2 represents a substituted or unsubstituted arylene group selected from the group consisting of a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, an anthranylene group, a pentacenylene group, a perylenylene group, a picenylene group, a pyrenylene group and a pentaphenylene group.

16. The organic electroluminescence device according to claim 1 , wherein Ar 2 represents a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a phenanthryl group, a chrysenyl group, a benzophenanthryl group, a triphenylenyl group, a benzanthranyl group, a benzochrysenyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a pentacenyl group, a picenyl group and a pentaphenyl group, or a substituted or unsubstituted heterocyclic group selected from the group consisting of a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indolinylene group, a quinolinylene group, an acridinylene group, a pyrrolidinylene group, a dioxanylene group, a piperidinylene group, a morpholidinylene group, a piperazinylene group, a triathinylene group, a carbazolylene group, a furanylene group, a thiophenylene group, an oxazolylene group, an oxadiazolylene group, a benzoxazolylene group, a thiazolylene group, a thiadiazolylene group, a benzothiazolylene group, a triazolylene group, an imidazolylene group, a benzimidazolylene group, a furanylene group, a benzofuranylene group and a dibenzofuranylene group.

17. The organic electroluminescence device according to claim 1 , wherein L 2 represents a substituted or unsubstituted arylene group selected from the group consisting of a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, an anthranylene group, a pentacenylene group, a perylenylene group, a picenylene group, a pyrenylene group, a pentaphenylene group, or a substituted or unsubstituted divalent heterocyclic group selected from the group consisting of a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indolinylene group, a quinolinylene group, an acridinylene group, a pyrrolidinylene group, a dioxanylene group, a piperidinylene group, a morpholidinylene group, a piperazinylene group, a triathinylene group, a carbazolylene group, a furanylene group, a thiophenylene group, an oxazolylene group, an oxadiazolylene group, a benzoxazolylene group, a thiazolylene group, a thiadiazolylene group, a benzothiazolylene group, a triazolylene group, an imidazolylene group, a benzimidazolylene group, a furanylene group and a dibenzofuranylene group, and Ar 2 represents a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a phenanthryl group, a chrysenyl group, a benzophenanthryl group, a triphenylenyl group, a benzanthranyl group, a benzochrysenyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a pentacenyl group, a picenyl group a pentaphenyl group, or a substituted or unsubstituted heterocyclic group selected from the group consisting of a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indolinylene group, a quinolinylene group, an acridinylene group, a pyrrolidinylene group, a dioxanylene group, a piperidinylene group, a morpholidinylene group, a piperazinylene group, a triathinylene group, a carbazolylene group, a furanylene group, a thiophenylene group, an oxazolylene group, an oxadiazolylene group, a benzoxazolylene group, a thiazolylene group, a thiadiazolylene group, a benzothiazolylene group, a triazolylene group, an imidazolylene group, a benzimidazolylene group, a furanylene group, a benzofuranylene group and a dibenzofuranylene group.

18. The organic electroluminescence device according to claim 1 , wherein L 2 represents a substituted or unsubstituted group selected from the group consisting of a phenylene group a naphthylene group, a biphenylene group, a terphenylene group and an anthranylene group, and Ar 2 represents a substituted or unsubstituted group selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a carbazolylene group, a benzoxazolylene group, a benzothiazolylene group, a benzimidazolylene group, a benzofuranylene group, furanylene group and a dibenzofuranylene group.

19. The organic electroluminescence device according to claim 1 , wherein R a and R b each independently represents a substituted or unsubstituted alkyl group selected from the group consisting of an ethyl group, a methyl group, an i-propyl group, an n-propyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group; a substituted or unsubstituted alkenyl group selected from the group consisting of a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2,2-diphenylvinyl group, a 1,2-diphenylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 2-phenylallyl group, a 3-phenylallyl group, a 3,3-diphenylallyl group, a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group; a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a phenanthryl group, a chrysenyl group, a benzophenanthryl group, a triphenylenyl group, a benzanthranyl group, a benzochrysenyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a pentacenyl group, a picenyl group and a pentaphenyl group; a substituted or unsubstituted heteroaryl group selected from the group consisting of a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranyl group, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolyl group, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a 8-isoquinolyl group, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinyl group, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinyl group, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group, a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrohn-4-yl group, a 1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a 1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a 1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a 1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a 1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a 1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a 1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2 yl group, a 1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a 1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a 1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a 1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a 1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a 1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a 2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a 2,9-phenanthrolin*5-yl group, a 2,9-phenanthrolin-6-yl group, a 2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a 2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a 2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a 2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a 2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9*yl group, a 2,8-phenanthrolin-10 71 group, a 2,7-phenanthrolin-1-yl group, a 2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a 2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a 2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a 2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinyl group, a 1-phenoxaminyl group, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a 2-t-butyl-3-indolyl group, a 4-t-butyl-3-indolyl group; a substituted or unsubstituted alkylsilyl group selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group; or a substituted or unsubstituted arylsilyl group selected from the group consisting of a triphenylsilyl group, a phenyldimethylsilyl group, a t-butyldiphenylsilyl group, a tritolylsilyl group, a trixylylsilyl group, and a trinaphthylsilyl group.

20. The organic electroluminescence device according to claim 1 , wherein R a and R b represent a substituted or unsubstituted alkyl group selected from the group consisting of an ethyl group, a methyl group, an i-propyl group, an n-propyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group, or a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a naphthyl group, a phenanthryl group, a chrysenyl group, a benzophenanthryl group, a triphenylenyl group, a benzanthranyl group, a benzochrysenyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a pentacenyl group, a picenyl group and a pentaphenyl group.

21. The organic electroluminescence device according to claim 1 , wherein R b represents a substituted or unsubstituted alkyl group selected from the group consisting of an ethyl group, a methyl group, an i-propyl group, an n-propyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group, or

a substituted or unsubstituted aryl group selected from the group consisting of a phenyl group, a phenanthryl group, a chrysenyl group, a benzophenanthryl group, a triphenylenyl group, a benzanthranyl group, a benzochrysenyl group, a biphenyl group, a naphthacenyl group, a terphenyl group, an anthranyl group, a pentacenyl group, a picenyl group and a pentaphenyl group.