Benzofluorene compound, material for luminescent layer using said compound and organic electroluminescent device
The present invention is capable of providing a light emitting device with excellent device lifetime while maintaining low driving voltage and good color purity by using a benzofluorene compound which is substituted with a diaryl amino group having a naphthyl and a phenyl or a heteroaryl and which is represented by general formula (1) as a material for luminescent layers of an organic electroluminescent device, for example. (In the formula, Ar is a phenyl, a heteroaryl, etc., R 1 and R 2 are fluorine or a substituted silyl, etc., n1 and n2 are an integer of 0-5, and R 3 is an alkyl, etc.)
1. A benzofluorene compound represented by the following formula (1):
wherein
Ar is each independently phenyl, naphthyl or a heteroaryl,
R 1 is each independently, an aryl, a cycloalkyl, fluorine, cyano, an alkyl substituted by fluorine, an alkoxy optionally substituted by fluorine, a substituted silyl or a substituted germyl,
R 2 is each independently, an aryl, fluorine, cyano, an alkyl substituted by fluorine, an alkoxy optionally substituted by fluorine, a substituted silyl or a substituted germyl,
n1 and n2 are each independently an integer of 0 to 5, and in the case when one naphthyl group is substituted with two or more adjacent R 1 s or in the case when one Ar group is substituted with two or more adjacent R 2 s, these may bind to form an aliphatic ring,
R 3 is each independently an alkyl or an aryl, wherein two R a s may bind to each other to form a ring, and
at least one hydrogen in the compound represented by the formula (1) may be substituted with deuterium.
2. The benzofluorene compound according to claim 1 , wherein
Ar is each independently phenyl or pyridyl,
R 1 is each independently an aryl with a carbon number of 6 to 12, a cycloalkyl with a carbon number of 3 to 6, fluorine, cyano, an alkyl with a carbon number of 1 to 6 substituted by fluorine, an alkoxy with a carbon number of 1 to 4 optionally substituted by fluorine, an alkyl-substituted silyl or an alkyl-substituted germyl,
R 2 is each independently an aryl with a carbon number of 6 to 12, fluorine, cyano, an alkyl with a carbon number of 1 to 6 substituted by fluorine, an alkoxy with a carbon number of 1 to 4 optionally substituted by fluorine, an alkyl-substituted silyl or an alkyl-substituted germyl,
n1 and n2 are each independently an integer of 0 to 3, and in the case when one naphthyl group is substituted with two or more adjacent R 1 s or in the case when one Ar group is substituted with two or more adjacent R 2 s, they may bind to form an aliphatic ring with a carbon number of 3 to 6,
R 3 is each independently an alkyl with a carbon number of 1 to 6 or an aryl with a carbon number of 6 to 12, wherein two R a s may bind to each other to form a ring, and
at least one hydrogen in the Ar and naphthyl groups in the compound represented by the formula (1) may be substituted with deuterium.
3. The benzofluorene compound according to claim 1 , wherein
Ar is each independently phenyl or pyridyl,
R 1 is each independently phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, fluorine, cyano, methyl fluoride, ethyl fluoride, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, methoxy fluoride, ethoxy fluoride, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, trimethylgermyl, triethylgermyl or t-butyldimethylgermyl,
R 2 is each independently phenyl, fluorine, cyano, methyl fluoride, ethyl fluoride, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, methoxy fluoride, ethoxy fluoride, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, trimethylgermyl, triethylgermyl or t-butyldimethylgermyl,
n1 and n2 are each independently an integer of 0 to 2, and in the case when one naphthyl group is substituted with two or more adjacent R 1 s or in the case when one Ar group is substituted with two or more adjacent R 2 s, these may bind to form an aliphatic ring with a carbon number of 5 to 6,
R 3 is each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl or phenyl, and
in the case when n1 and n2 are 0, at least one hydrogen in the Ar and naphthyl groups in the compound represented by the formula (1) may be substituted with deuterium.
4. The benzofluorene compound according to claim 1 , wherein
Ar is each independently phenyl or pyridyl,
R 1 is each independently phenyl, cyclopentyl, cyclohexyl, methylcyclopentyl, fluorine, cyano, methyl fluoride, methoxy, ethoxy, methoxy fluoride, trimethylsilyl, triethylsilyl, trimethylgermyl or triethylgermyl,
R 2 is each independently phenyl, fluorine, cyano, methyl fluoride, methoxy, ethoxy, methoxy fluoride, trimethylsilyl, triethylsilyl, trimethylgermyl or triethylgermyl,
n1 and n2 are each independently an integer of 0 to 2, and in the case when one naphthyl group is substituted with two or more adjacent R 1 s or in the case when one Ar group is substituted with two or more adjacent R 2 s, these may bind to form a cyclohexane ring, and
R 3 s are each independently methyl, ethyl or phenyl.
5. The benzofluorene compound according to claim 1 , which is represented by the following formula (1-1):
6. The benzofluorene compound according to claim 1 , which is represented by the following formula (1-51):
7. The benzofluorene compound according to claim 1 , which is represented by the following formula (1-22):
8. The benzofluorene compound according to claim 1 , which is represented by the following formula (1-20):
9. A material for a luminescent layer of a luminescent device, which comprises the benzofluorene compound according to claim 1 .
10. An organic electroluminescent device comprising a pair of electrodes of an anode and a cathode, and a luminescent layer containing the material for a luminescent layer according to claim 9 , which is disposed between the pair of electrodes.
11. The organic electroluminescent device according to claim 10 , which further comprises an electron transport layer and/or an electron injection layer that is/are disposed between the cathode and the luminescent layer, wherein at least one of the electron transport layer and electron injection layer comprises at least one compound selected from the group consisting of a quinolinol-based metal complex, a pyridine derivative, a phenanthroline derivative, a borane derivative, and a benzimidazole derivative.
12. The organic electroluminescent device according to claim 11 , wherein the electron transport layer and/or electron injection layer further comprise(s) at least one compound selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal and an organic complex of a rare earth metal.
13. A display device comprising the organic electroluminescent device according to claim 10 .
14. A lighting device comprising the organic electroluminescent device according to claim 10 .