Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
A compound of the following formula (1) and others. R 1 to R 24 , R 31 to R 35 , A 1 and A 2 are as defined in the specification, n is an integer of 0 to 3, when A 1 is an (n+1)-valent residue of benzene, n is an integer of 1 or more, and when n is 0, (A 2 ) 0 is a hydrogen atom.
1. An organic electroluminescent device comprising:
a cathode, an anode, and organic layers disposed between the cathode and the anode, wherein:
the organic layers comprise a light-emitting layer, and a first layer disposed between the light-emitting layer and the cathode, and
the first layer comprises a compound of formula (1A):
wherein,
R 1 to R 24 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms R 31 to R 35 each independently represent a hydrogen atom
A 1 represents a substituted or unsubstituted, (n+1)-valent residue of an aromatic hydrocarbon having 6 to 30 ring carbon atoms, or a substituted or unsubstituted, (n+1)-valent residue of an aromatic heterocyclic compound having 5 to 30 ring atoms,
wherein a hydrogen atom represents a protium isotope and/or a deuterium isotope,
A 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and
n represents an integer of 1 to 3.
2. The organic electroluminescent device according to claim 1 , wherein when A 1 is an (n+1)-valent residue of benzene.
3. The organic electroluminescent device according to claim 1 , wherein:
the aromatic hydrocarbon having 6 to 30 ring carbon atoms of the substituted or unsubstituted, (n+1)-valent residue of the aromatic hydrocarbon having 6 to 30 ring carbon atoms represented by A 1 is a benzene, a biphenyl, a terphenyl, a naphthalene, an anthracene, a benzanthracene, a phenanthrene, a benzophenanthrene, a phenalene, a picene, a pentaphene, a pyrene, a chrysene, a benzochrysene, a fluorene, a fluoranthene, a perylene, or a triphenyl, and
the aromatic heterocyclic compound having 5 to 30 ring atoms of the substituted or unsubstituted, (n+1)-valent residue of the aromatic heterocyclic compound having 5 to 30 ring atoms represented by A 1 is a pyrrole, a furan, a thiophene, a pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, an imidazole, an oxazole, a thiazole, a pyrazole, an isoxazole, an isothiazole, an oxadiazole, a thiadiazole, a triazole, a tetrazole, an indole, an isoindole, a benzofuran, an isobenzofuran, a benzothiophene, an isobenzothiophene, an indolizine, a quinolidine, a quinoline, an isoquinoline, a cinnoline, a phthalazine, a quinazoline, a quinoxaline, a benzimidazole, a benzoxazole, a benzothiazole, an indazole, a benzisoxazole, a benzisothiazole, a dibenzofuran, a dibenzothiophene, a carbazole, a phenanthridine, an acridine, a phenanthroline, a phenazine, a phenothiazine, a phenoxazine, a xanthene or a benzonitrile.
4. The organic electroluminescent device according to claim 1 , wherein:
the aromatic hydrocarbon having 6 to 30 ring carbon atoms of the substituted or unsubstituted, (n+1)-valent residue of the aromatic hydrocarbon having 6 to 30 ring carbon atoms represented by A 1 is a benzene, a biphenyl, a naphthalene or a phenanthrene, and
the aromatic heterocyclic compound having 5 to 30 ring atoms of the substituted or unsubstituted, (n+1)-valent residue of the aromatic heterocyclic compound having 5 to 30 ring atoms represented by A 1 is a pyridine, a dibenzofuran, a dibenzothiophene, a carbazole or a benzonitrile.
5. The organic electroluminescent device according to claim 1 , wherein:
the aryl group having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by A 2 is a monovalent residue of a benzene, a biphenyl, a terphenyl, a naphthalene, an anthracene, a benzanthracene, a phenanthrene, a benzophenanthrene, a phenalene, a picene, a pentaphene, a pyrene, a chrysene, a benzochrysene, a fluorene, a fluoranthene, a perylene, or a triphenyl, and
the heteroaryl group having 5 to 30 ring atoms of the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by A 2 is a monovalent residue of a pyrrole, a furan, a thiophene, a pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, an imidazole, an oxazole, a thiazole, a pyrazole, an isoxazole, an isothiazole, an oxadiazole, a thiadiazole, a triazole, a tetrazole, an indole, an isoindole, a benzofuran, an isobenzofuran, a benzothiophene, an isobenzothiophene, an indolizine, a quinolidine, a quinoline, an isoquinoline, a cinnoline, a phthalazine, a quinazoline, a quinoxaline, a benzimidazole, a benzoxazole, a benzothiazole, an indazole, a benzisoxazole, a benzisothiazole, a dibenzofuran, a dibenzothiophene, a carbazole, a phenanthridine, an acridine, a phenanthroline, a phenazine, a phenothiazine, a phenoxazine, a xanthene or a benzonitrile.
6. The organic electroluminescent device according to claim 1 , wherein:
the aryl group having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by A 2 is a monovalent residue of a benzene, a biphenyl, a naphthalene or a phenanthrene, and
the heteroaryl group having 5 to 30 ring atoms of the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by A 2 is monovalent residue of a pyridine, a dibenzofuran, a dibenzothiophene, a carbazole or a benzonitrile.
7. The organic electroluminescent device according to claim 1 , wherein:
R 1 to R 24 each independently is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and
the arbitrary substituent to be meant by the wording “substituted or unsubstituted” by any of R 1 to R 24 , A 1 and A 2 each is independently an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted alkyl group having 1 to 50 carbon atoms.
8. The organic electroluminescent device according to claim 1 , wherein:
R 1 to R 24 are hydrogen atoms,
A 1 is an unsubstituted (n+1)-valent residue of an aromatic hydrocarbon having 6 to 30 ring carbon atoms, or an unsubstituted (n+1)-valent residue of an aromatic heterocyclic compound having 5 to 30 ring atoms, and
A 2 is an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring atoms.
9. An organic electroluminescent device, comprising:
a cathode, an anode, and organic layers disposed between the cathode and the anode, wherein:
the organic layers comprise a light-emitting layer, and a first layer disposed between the light-emitting layer and the cathode, and
the first layer comprises a compound of formula (2):
wherein:
R 1 to R 24 each independently represent a hydrogen atom, or a substituent, and the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
R31 to R35 each independently represent a hydrogen atom,
R 41 to R 42 each are independently same as R 1 ,
m represents 0 or 1,
when m is 0, X is absent, and the two benzene rings are not crosslinked,
when m is 1, X is O or S,
p represents an integer of 0 to 5,
q represents an integer of 0 to 4.
10. The organic electroluminescent device according to claim 1 , wherein the compound represented by the formula (1A) is a compound of formula (3):
wherein:
A 2 is an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring atoms,
R 43 is the same as R 1 , and
u represents an integer of 0 to (5-n).
11. The organic electroluminescent device according to claim 1 , wherein at least one hydrogen atom in the compound represented by the formula (1A) is a deuterium atom.
12. The organic electroluminescent device according to claim 1 , wherein R 1 to R 24 are all deuterium atoms.
13. The organic electroluminescent device according to claim 1 , wherein:
n is 1,
the group represented by A 1 is unsubstituted, and
the hydrogen atoms that the group represented by A 1 has are all deuterium atoms.
14. The organic electroluminescent device according to claim 1 , wherein:
n is 1,
the group represented by A 1 is unsubstituted,
the hydrogen atoms that the group represented by A 1 has are all deuterium atoms,
the group represented by A 2 is unsubstituted, and
the hydrogen atoms that the group represented by A 2 has are all deuterium atoms.
15. The organic electroluminescent device according to claim 1 , wherein the first layer is adjacent to the light emitting layer.
16. A compound of formula (1):
wherein:
R 1 to R 24 each independently represent a hydrogen atom, or a substituent, and the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, R 31 to R 35 each independently represent a hydrogen atom
A 1 represents a substituted or unsubstituted, (n+1)-valent residue of an aromatic hydrocarbon having 6 to 30 ring carbon atoms, or a substituted or unsubstituted, (n+1)-valent residue of an aromatic heterocyclic compound having 5 to 30 ring atoms,
wherein a hydrogen atom represents a protium isotope and/or a deuterium isotope,
A 2 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and
n represents an integer of 1 to 3.
17. The compound according to claim 16 , wherein:
the aromatic hydrocarbon having 6 to 30 ring carbon atoms of the substituted or unsubstituted, mono or di-valent residue of the aromatic hydrocarbon having 6 to 30 ring carbon atoms represented by A 1 is a benzene, a biphenyl, a terphenyl, a naphthalene, an anthracene, a benzanthracene, a phenanthrene, a benzophenanthrene, a phenalene, a picene, a pentaphene, a pyrene, a chrysene, a benzochrysene, a fluorene, a fluoranthene, a perylene, or a triphenyl, and
the aromatic heterocyclic compound having 5 to 30 ring atoms of the substituted or unsubstituted, mono or di-valent residue of the aromatic heterocyclic compound having 5 to 30 ring atoms represented by A 1 is a pyrrole, a furan, a thiophene, a pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, an imidazole, an oxazole, a thiazole, a pyrazole, an isoxazole, an isothiazole, an oxadiazole, a thiadiazole, a triazole, a tetrazole, an indole, an isoindole, a benzofuran, an isobenzofuran, a benzothiophene, an isobenzothiophene, an indolizine, a quinolidine, a quinoline, an isoquinoline, a cinnoline, a phthalazine, a quinazoline, a quinoxaline, a benzimidazole, a benzoxazole, a benzothiazole, an indazole, a benzisoxazole, a benzisothiazole, a dibenzofuran, a dibenzothiophene, a carbazole, a phenanthridine, an acridine, a phenanthroline, a phenazine, a phenothiazine, a phenoxazine, a xanthene or a benzonitrile.
18. The compound according to claim 16 , wherein:
the aromatic hydrocarbon having 6 to 30 ring carbon atoms of the substituted or unsubstituted, mono or di-valent residue of the aromatic hydrocarbon having 6 to 30 ring carbon atoms represented by A 1 is a benzene, a biphenyl, a naphthalene or a phenanthrene, and
the aromatic heterocyclic compound having 5 to 30 ring atoms of the substituted or unsubstituted, mono or di-valent residue of the aromatic heterocyclic compound having 5 to 30 ring atoms represented by A 1 is a pyridine, a dibenzofuran, a dibenzothiophene, a carbazole or a benzonitrile.
19. The compound according to claim 16 , wherein:
the aryl group having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by A 2 is a monovalent residue of a benzene, a biphenyl, a terphenyl, a naphthalene, an anthracene, a benzanthracene, a phenanthrene, a benzophenanthrene, a phenalene, a picene, a pentaphene, a pyrene, a chrysene, a benzochrysene, a fluorene, a fluoranthene, a perylene, or a triphenyl, and
the heteroaryl group having 5 to 30 ring atoms of the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by A 2 is a monovalent residue of a pyrrole, a furan, a thiophene, a pyridine, a pyridazine, a pyrimidine, a pyrazine, a triazine, an imidazole, an oxazole, a thiazole, a pyrazole, an isoxazole, an isothiazole, an oxadiazole, a thiadiazole, a triazole, a tetrazole, an indole, an isoindole, a benzofuran, an isobenzofuran, a benzothiophene, an isobenzothiophene, an indolizine, a quinolidine, a quinoline, an isoquinoline, a cinnoline, a phthalazine, a quinazoline, a quinoxaline, a benzimidazole, a benzoxazole, a benzothiazole, an indazole, a benzisoxazole, a benzisothiazole, a dibenzofuran, a dibenzothiophene, a carbazole, a phenanthridine, an acridine, a phenanthroline, a phenazine, a phenothiazine, a phenoxazine, a xanthene or a benzonitrile.
20. The compound according to claim 16 , wherein:
the aryl group having 6 to 30 ring carbon atoms of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by A 2 is a monovalent residue of a benzene, a biphenyl, a naphthalene or a phenanthrene, and
the heteroaryl group having 5 to 30 ring atoms of the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms represented by A 2 is monovalent residue of a pyridine, a dibenzofuran, a dibenzothiophene, a carbazole or a benzonitrile.
21. The compound according to claim 16 , wherein:
the substituent represented by R 1 to R 24 each independently is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and
the arbitrary substituent to be meant by the wording “substituted or unsubstituted” by any of R 1 to R 24 , A 1 and A 2 each is independently an unsubstituted aryl group having 6 to 30 ring carbon atoms.
22. The compound according to claim 16 , wherein:
R 1 to R 24 are hydrogen atoms,
A 1 is an unsubstituted (n+1)-valent residue of an aromatic hydrocarbon having 6 to 30 ring carbon atoms, or an unsubstituted (n+1)-valent residue of an aromatic heterocyclic compound having 5 to 30 ring atoms, and
A 2 is an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring atoms.
23. A compound of formula (2):
wherein:
R 1 to R 24 each independently represent a hydrogen atom, or a substituent, and the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
R31 to R35 each independently represent a hydrogen atom,
R 41 to R 42 each are independently same as R 1 ,
m represents 0 or 1,
when m is 0, X is absent, and the two benzene rings are not crosslinked,
when m is 1, X is O or S,
p represents an integer of 0 to 5,
q represents an integer of 0 to 4.
24. The compound according to claim 16 , wherein the compound represented by the formula (1) is a compound of formula (3):
wherein:
A 2 is an unsubstituted aryl group having 6 to 30 ring carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring atoms,
R 43 is the same as R 1 , and
u represents an integer of 0 to (5-n).
25. The compound according to claim 16 , wherein at least one hydrogen atom in the compound represented by the formula (1) is a deuterium atom.
26. The compound according to claim 16 , wherein R 1 to R 24 are all deuterium atoms.
27. The compound according to claim 16 , wherein:
n is 1,
the group represented by A 1 is unsubstituted,
the hydrogen atoms that the group represented by A 1 has are all deuterium atoms.
28. The compound according to claim 16 , wherein:
n is 1,
the group represented by A 1 is unsubstituted,
the hydrogen atoms that the group represented by A 1 has are all deuterium atoms,
the group represented by A 2 is unsubstituted,
the hydrogen atoms that the group represented by A 2 has are all deuterium atoms.
29. A material for organic electroluminescent devices, comprising the compound of claim 16 .
30. An organic electroluminescent device having a cathode, an anode, and organic layers disposed between the cathode and the anode, wherein the organic layers comprise a light-emitting layer, and wherein:
at least one layer of the organic layers comprises the compound of claim 16 .
31. An electronic device comprising the organic electroluminescent device of claim 1 .
32. A compound of formula ET-1, ET-3, ET-4, ET-5, ET-6, ET-7, or ET-8:
33. An organic electroluminescent device comprising:
a cathode, an anode, and organic layers disposed between the cathode and the anode, wherein:
the organic layers comprise a light-emitting layer, and a first layer disposed between the light-emitting layer and the cathode, and
the first layer comprises a compound of ET-1, ET-3, ET-4, ET-5, ET-6, ET-7, or ET-8: