Arylamine compound, hole-transport layer material, hole-injection layer material, light-emitting device, light-emitting apparatus, electronic apparatus, and lighting device
To provide a novel arylamine compound with a low refractive index. The provided arylamine compound includes at least one aromatic group. The aromatic group includes a first benzene ring, a second benzene ring, a third benzene ring, and at least three alkyl groups. The first benzene ring, the second benzene ring, and the third benzene ring are directly bonded in this order. The first benzene ring is bonded to nitrogen of amine. The first benzene ring may further include a substituted or unsubstituted phenyl group. The second benzene ring or the third benzene ring may further include an alkylated phenyl group. Each of first positions and third positions of two or more of the first to third benzene rings is independently bonded to another benzene ring, a benzene ring of the alkylated phenyl group, any of the at least three alkyl groups, or the nitrogen of the amine.
1. An arylamine compound represented by General Formula (G1):
wherein:
Ar 1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, and a substituted or unsubstituted naphthylphenyl group,
each of R 6 , R 7 , and R 8 independently represents an alkyl group having 1 to 4 carbon atoms,
m represents an integer of 0 to 4,
when m is greater than or equal to 2, a plurality of R 8 represents the same alkyl group or different alkyl groups,
one of R 11 to R 15 represents a substituent represented by General Formula (g1), each of the others of R 11 to R 15 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
one of R 21 to R 25 represents a substituent represented by General Formula (g2), each of the others of R 21 to R 25 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
each of R 31 to R 35 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
at least three of R 11 to R 15 , R 21 to R 25 , and R 31 to R 35 represent an alkyl group having 1 to 6 carbon atoms,
none or one of R 11 to R 15 represents the unsubstituted phenyl group or the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
none or one of R 21 to R 25 and R 31 to R 35 represents the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms, and
in at least two combinations of the three combinations R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 , at least one of R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 represents any of the substituents other than hydrogen.
2. An arylamine compound represented by General Formula (G2):
wherein:
each of p and r independently represents 1 or 2,
p+r is 2 or 3,
each of R 6 to R 9 independently represents an alkyl group having 1 to 4 carbon atoms,
each of m and n independently represents an integer of 0 to 4,
each of R 41 to R 45 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a cycloalkyl group having 5 to 12 carbon atoms,
one of R 11 to R 15 represents a substituent represented by General Formula (g1),
each of the others of R 11 to R 15 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
one of R 21 to R 25 represents a substituent represented by General Formula each of the others of R 21 to R 25 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
each of R 31 to R 35 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
at least three of R 11 to R 15 , R 21 to R 25 , and R 31 to R 35 represent the alkyl group having 1 to 6 carbon atoms,
none or one of R 11 to R 15 represents the unsubstituted phenyl group or the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
none or one of R 21 to R 25 and R 31 to R 35 represents the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms, and
in at least two combinations of the three combinations R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 , at least one of R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 represents any of the substituents other than hydrogen.
3. The arylamine compound according to claim 2 , wherein n represents 0.
4. The arylamine compound according to claim 2 , wherein p represents 1 and r represents 1.
5. An arylamine compound represented by General Formula (G3):
wherein:
each of R 1 to R 4 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, an unsubstituted phenyl group, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
each of R 6 , R 7 , and R 8 independently represents an alkyl group having 1 to 4 carbon atoms,
m represents an integer of 0 to 4,
when m is greater than or equal to 2, a plurality of R 8 represents the same alkyl group or different alkyl groups,
one of R 11 to R 15 represents a substituent represented by General Formula (g1),
each of the others of R 11 to R 15 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
one of R 21 to R 25 represents a substituent represented by General Formula (g2), each of the others of R 21 to R 25 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
each of R 31 to R 35 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
at least three of R 11 to R 15 , R 21 to R 25 , and R 31 to R 35 represent an alkyl group having 1 to 6 carbon atoms,
none or one of R 11 to R 15 represents the unsubstituted phenyl group or the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms,
none or one of R 21 to R 25 and R 31 to R 35 represents the phenyl group substituted with an alkyl group having 1 to 6 carbon atoms, and
in at least two combinations of the three combinations R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 , at least one of R 12 and R 14 , R 22 and R 24 , and R 32 and R 34 represents any of the substituents other than hydrogen.
6. The arylamine compound according to claim 5 , wherein R 3 represents a cyclohexyl group and each of R 1 , R 2 , R 4 , and R 5 represents hydrogen.
7. The arylamine compound according to claim 5 , wherein R 1 represents an unsubstituted phenyl group and each of R 2 to R 5 represents hydrogen.
8. The arylamine compound according to claim 1 ,
wherein at least one of R 12 , R 14 , R 22 , and R 24 represents any of the substituents other than hydrogen, and
wherein at least one of R 32 and R 34 represents any of the substituents other than hydrogen.
9. The arylamine compound according to claim 1 , wherein m represents 0.
10. The arylamine compound according to claim 1 , wherein the alkyl group having 1 to 6 carbon atoms is a chain alkyl group having 2 to 5 carbon atoms.
11. The arylamine compound according to claim 1 , wherein the alkyl group having 1 to 6 carbon atoms is a chain alkyl group having a branch formed of 3 to 5 carbon atoms.
12. The arylamine compound according to claim 1 , wherein the alkyl group having 1 to 6 carbon atoms is a tert-butyl group.
13. The arylamine compound according to claim 2 , wherein each of R 12 , R 14 , R 22 , R 32 , and R 34 among R 11 to R 15 , R 21 to R 25 , and R 31 to R 35 represents any of the substituents other than hydrogen, and each of the others represents hydrogen.
14. The arylamine compound according to claim 1 , wherein each of R 6 and R 7 represents a methyl group.
15. The arylamine compound according to claim 1 , wherein an ordinary refractive index of a layer formed of the arylamine compound with respect to light with a wavelength greater than or equal to 455 nm and less than or equal to 465 nm is greater than or equal to 1.50 and less than or equal to 1.75.
16. The arylamine compound according to claim 1 , wherein an ordinary refractive index of a layer formed of the arylamine compound with respect to an ordinary light with a wavelength of 633 nm is greater than or equal to 1.45 and less than or equal to 1.70.
17. A material for a hole-transport layer, comprising the arylamine compound according to claim 1 .
18. A material for a hole-injection layer, comprising the arylamine compound according to claim 1 .
19. A material for a hole-injection layer, comprising:
the arylamine compound according to claim 1 , and
an organic compound comprising a cyano group or a fluorine atom.
20. A light-emitting device comprising the arylamine compound according to claim 1 .
21. An electronic apparatus comprising:
the light-emitting device according to claim 20 ; and
at least one of a sensor, an operation button, a speaker, and a microphone.
22. A light-emitting apparatus comprising:
the light-emitting device according to claim 20 ; and
at least one of a transistor and a substrate.
23. A lighting device comprising:
the light-emitting device according to claim 20 ; and
a housing.