Organic electroluminescent element and electronic device
An organic EL device with high emission efficiency, an electronic equipment including the organic EL device, and a compound providing the organic EL device are provided. The compound is represented by formula (1): wherein Ar 1 represents a substituted or unsubstituted naphthalene ring; the substituent on the naphthalene ring is at least one selected from a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a group represented by —Si(R 101 )(R 102 )(R 103 ), and a group represented by —Z—R a ; R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by —Si(R 101 )(R 102 )(R 103 ), an aryl group, or a heteroaryl group; R 11 to R 18 each independently represent a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a group represented by —Si(R 101 )(R 102 )(R 103 ), or a group represented by —Z—R a ; each Z represents a single bond, an arylene group, a heteroarylene group, or a divalent linking group in which 2 to 4 groups selected from the above groups are linked together; R a represents a group represented by —N(R 104 )(R 105 ), an aryl group, or a heteroaryl group; and R 101 to R 105 each represent a hydrogen atom, an alkyl group, a cycloalkyl group, aryl group, or a heteroaryl group; provided that at least one selected from the substituent on the naphthalene ring and R 11 to R 18 represents a group represented by —Z—R a .
1. A compound is represented by any of formulae (3) and (4-2):
wherein:
R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), 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
R 11 to R 18 , and R 25 to R 36 each independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a group represented by —Z—R a ;
R 101 to R 105 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
Ar 2 and Ar 1 each independently represent 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
the group represented by —Z—R a is represented by formula (b):
—Z 2 —HAr (b);
—HAr in formula (b) is a group selected from the following groups:
Z 1 and Z 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
each R c independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms which has an aryl group having 6 to 30 ring carbon atoms, an amino group, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a cyano group, or a nitro group;
when more than one R c occurs in each group, groups R c may be the same or different;
R d represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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
each p1 independently represents an integer of 0 to 4, each p2 independently represents an integer of 0 to 3, p3 represents an integer of 0 to 2, p4 represents an integer of 0 to 7, and p5 represents an integer of 0 to 5,
provided that one to four selected from R 11 to R 18 and R 25 to R 30 of formula (3) each represent a group represented by —Z—R a .
2. The compound according to claim 1 , wherein only one or two selected from R 11 to R 18 and R 25 to R 30 in formula (3), and only one or two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by formula (b).
3. The compound according to claim 1 , wherein R 28 in formula (3) is represented by formula (b).
4. The compound according to claim 1 , wherein Z 1 is a single bond.
5. The compound according to claim 1 , wherein Ar 2 and Ar 3 each represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
6. The compound according to claim 1 , wherein L 1 and L 2 are both single bonds, and Ar 2 and Ar 3 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
7. A material for organic electroluminescence devices, the material comprising the compound according to claim 1 .
8. An organic electroluminescence device, comprising:
an organic thin film layer between a cathode and an anode,
wherein:
the organic thin film layer comprises one or more layers comprising a light emitting layer; and
at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) according to claim 1 .
9. The organic electroluminescence device according to claim 8 , wherein the light emitting layer comprises the compound represented by formula (3) or (4-2).
10. The organic electroluminescence device according to claim 8 , wherein the at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) and an anthracene derivative represented by formula (5):
wherein:
Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted fused ring group having 8 to 50 ring atoms; and
R 101 to R 108 are each independently selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.
11. The organic electroluminescence device according to claim 8 , wherein the organic thin film layer comprises an electron transporting layer, and the electron transporting layer comprises said compound represented by formula (3) or (4-2).
12. The organic electroluminescence device according to claim 8 , wherein the organic thin film layer comprises a hole transporting layer comprising the compound represented by formula (3) or (4-2).
13. The organic electroluminescence device according to claim 8 , wherein the organic thin film layer comprises an electron transporting layer and a blocking layer between the electron transporting layer and the light emitting layer, and the blocking layer comprises the compound represented by formula (3) or (4-2).
14. An electronic equipment, comprising the organic electroluminescence device according to claim 8 .
15. A compound represented by formula (2):
wherein:
R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), 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 each of R 11 to R 24 independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted furyl group, thienyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, or xanthenyl group, or a group represented by —Z—R a ;
each Z represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted dibenzofuranylene group or a substituted or unsubstituted dibenzothiophenylene group, or a divalent linking group in which 2 to 4 groups selected from the above groups are linked together;
when more than one Z occurs, groups Z may be the same or different;
R a represents a group represented by a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted furyl group, thienyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, or xanthenyl group;
when more than one R a occurs, groups R a may be the same or different;
R 101 to R 103 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms; and
when R 1 to R 2 , R 11 to R 24 , and R 101 to R 103 of formula (2) have a substituent, the substituent represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 ring carbon atoms, an aryl group having 6 to 24 ring carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a halogen atom, a cyano group, or a nitro group, and the substituent is not substituted with further substituent and adjacent groups of substituents is not bonded to each other to form a ring structure;
provided that one to four selected from R 11 to R 24 each represents a group represented by —Z—R a .
16. The compound according to claim 15 , wherein the group represented by —Z—R a is represented by any of formulae (b) to (c):
—Z 2 —HAr (b)
—Z 3 —Ar 4 (c)
wherein:
Z 2 and Z 3 are the same as Z defined above, or a divalent linking group in which 2 to 4 groups selected from the above groups are linked together;
HAr represents a substituted or unsubstituted furyl group, thienyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, or xanthenyl group; and
Ar 4 represents a substituted or unsubstituted aryl group having 14 to 30 ring carbon atoms.
17. The compound according to claim 16 , wherein only one or two selected from R 11 to R 24 in formula (2) is each independently represented by any of formulae (b) to (c).
18. The compound according to claim 16 , wherein only one or two selected from R 11 to R 24 in formula (2) is represented by formula (b).
19. The compound according to claim 16 , wherein only one or two selected from R 11 to R 24 in formula (2) is represented by formula (c).
20. The compound according to claim 16 , wherein R 23 in formula (2) is represented by any of formulae (b) to (c).
21. A compound is represented by any of formulae (3) and (4-2):
wherein:
R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), 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 11 to R 18 , R 25 to R 27 , R 29 to R 33 , and R 35 to R 36 each independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si(R 101 )(R 102 ) (R 103 ), a group represented by —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a group represented by —Z—R a ;
each Z represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the above groups are linked together;
when more than one Z occurs, groups Z may be the same or different;
R a represents a group represented by —N(R 104 )(R 105 ), 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;
when more than one R a occurs, groups R a may be the same or different;
R 101 to R 105 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
the group represented by —Z—R a , and is represented by any of formulae (a) to (c):
Z 1 to Z 3 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
Ar 2 and Ar 3 each independently represent 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;
HAr represents a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;
R 28 in formula (3) is represented by any of the formulae (a) to (c); and
Ar 4 represents a substituted or unsubstituted aryl group having 14 to 30 ring carbon atoms,
provided that one to three selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 of formula (3) each represent a group represented by —Z—R a .
22. The compound according to claim 21 , wherein the group represented by —Z—R a is represented by formula (b), and —HAr in formula (b) is a group selected from the following groups:
wherein each R c independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms which has an aryl group having 6 to 30 ring carbon atoms, an amino group, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a cyano group, or a nitro group;
when more than one R c occurs in each group, groups R c may be the same or different;
R d represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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
each p1 independently represents an integer of 0 to 4, each p2 independently represents an integer of 0 to 3, p3 represents an integer of 0 to 2, p4 represents an integer of 0 to 7, and p5 represents an integer of 0 to 5.
23. The compound according to claim 21 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are each independently represented by any of formulae (a) to (c).
24. The compound according to claim 21 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by formula (a).
25. The compound according to claim 21 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by formula (b).
26. The compound according to claim 21 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by formula (c).
27. The compound according to claim 21 , wherein the compound is represented by formulae (3-1):
wherein R 1 , R 2 , R 11 to R 18 , R 25 to R 27 , R 29 to R 30 , R 35 , R 36 , Z 1 , L 1 , L 2 , Ar 2 , and Ar 3 are as defined above.
28. The compound according to claim 21 , wherein the compound is represented by formulae (3-2):
wherein R 1 , R 2 , R 11 , R 12 , R 14 to R 18 , R 25 to R 27 , R 29 to R 30 Z 1 , L 1 , L 2 , Ar 2 , and Ar 3 are as defined above, and more than one Z 1 , L 1 , L 2 , Ar 2 and Ar 3 may be the same or different, respectively.
29. The compound according to claim 21 , wherein Z 1 is a single bond.
30. The compound according to claim 21 , wherein Ar 2 and Ar 3 each represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
31. The compound according to claim 21 , wherein L 1 and L 2 are both single bonds, and Ar 2 and Ar 3 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
32. A material for organic electroluminescence devices, the material comprising the compound according to claim 21 .
33. An organic electroluminescence device, comprising:
an organic thin film layer between a cathode and an anode,
wherein:
the organic thin film layer comprises one or more layers comprising a light emitting layer; and
at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) according to claim 21 .
34. The organic electroluminescence device according to claim 33 , wherein the light emitting layer comprises the compound represented by formula (3) or (4-2).
35. The organic electroluminescence device according to claim 33 , wherein the at least one layer of the organic thin film layer comprises the compound represented by formula (3) or (4-2) and an anthracene derivative represented by formula (5):
wherein Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted fused ring group having 8 to 50 ring atoms; and
R 101 to R 108 are each independently selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.
36. The organic electroluminescence device according to claim 33 , wherein the organic thin film layer comprises an electron transporting layer, and the electron transporting layer comprises said compound represented by formula (3) or (4-2).
37. The organic electroluminescence device according to claim 33 , wherein the organic thin film layer comprises a hole transporting layer comprising the compound represented by formula (3) or (4-2).
38. The organic electroluminescence device according to claim 33 , wherein the organic thin film layer comprises an electron transporting layer and a blocking layer between the electron transporting layer and the light emitting layer, and the blocking layer comprises the compound represented by formula (3) or (4-2).
39. An electronic equipment, comprising the organic electroluminescence device according to claim 33 .
40. A compound is represented by any of formulae (3-1) and (4-2):
wherein:
R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), 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
R 11 to R 18 , R 25 to R 27 , R 29 to R 33 , and R 35 to R 36 each independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si(R 101 )(R 102 )(R 103 ), a group represented by —N(R 104 )(R 105 ), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a group represented by —Z—R a ;
R 101 to R 105 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
the group represented by —Z—R a , and is represented by any of formulae (a) to (c):
Z 1 to Z 3 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
Ar 2 and Ar 3 each independently represent 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;
HAr represents a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; and
Ar 4 represents a substituted or unsubstituted aryl group having 14 to 30 ring carbon atoms,
provided that one to three selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 of formula (3-1), and one or two selected from R 11 to R 18 , R 31 to R 33 , and R 35 to R 36 of formula (4-2) each represent a group represented by —Z—R a .
41. The compound according to claim 40 , wherein:
the group represented by —Z—R a is represented by formula (b):
—Z 2 —HAr (b);
Z 2 independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group in which 2 to 4 groups selected from the arylene group and the heteroarylene group are linked together;
—HAr in formula (b) is a group selected from the following groups:
each R c independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms which has an aryl group having 6 to 30 ring carbon atoms, an amino group, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a cyano group, or a nitro group;
when more than one R c occurs in each group, groups R c may be the same or different;
R d represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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
each p1 independently represents an integer of 0 to 4, each p2 independently represents an integer of 0 to 3, p 3 represents an integer of 0 to 2, p4 represents an integer of 0 to 7, and p5 represents an integer of 0 to 5.
42. The compound according to claim 40 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3-1), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are each independently represented by any of the formulae (a) to (c).
43. The compound according to claim 40 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3-1), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by the formula (a).
44. The compound according to claim 40 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3-1), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by the formula (b).
45. The compound according to claim 40 , wherein only one or two selected from R 11 to R 18 , R 25 to R 27 , and R 29 to R 30 in formula (3-1), and only two selected from R 11 to R 12 and R 14 to R 18 and R 31 to R 33 and R 35 to R 36 in formula (4-2) are represented by the formula (c).
46. The compound according to claim 40 , wherein the compound is represented by formula (3-2):
wherein R 1 , R 2 , R 11 , R 12 , R 14 to R 18 , R 25 to R 27 , R 29 to R 30 Z 1 , L 1 , L 2 , Ar 2 , and Ar 3 are as defined above, and more than one Z 1 , L 1 , L 2 , Ar 2 and Ar 3 may be the same or different, respectively.
47. The compound according to claim 40 , wherein Z 1 is a single bond.
48. The compound according to claim 40 , wherein Ar 1 and Ar 3 each represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
49. The compound according to claim 40 , wherein L 1 and L 2 are both single bonds, and Ar 2 and Ar 3 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
50. A material for organic electroluminescence devices, the material comprising the compound according to claim 40 .
51. An organic electroluminescence device, comprising:
an organic thin film layer between a cathode and an anode,
wherein:
the organic thin film layer comprises one or more layers comprising a light emitting layer; and
at least one layer of the organic thin film layer comprises the compound represented by formula (3-1) or (4-2) according to claim 40 .
52. The organic electroluminescence device according to claim 51 , wherein the light emitting layer comprises the compound represented by formula (3-1) or (4-2).
53. The organic electroluminescence device according to claim 51 , wherein the at least one layer of the organic thin film layer comprises the compound represented by formula (3-1) or (4-2) and an anthracene derivative represented by formula (5):
wherein Ar 11 and Ar 12 each independently represent a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted fused ring group having 8 to 50 ring atoms; and
R 101 to R 108 are each independently selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.
54. The organic electroluminescence device according to claim 51 , wherein the organic thin film layer comprises an electron transporting layer, and the electron transporting layer comprises said compound represented by formula (3-1) or (4-2).
55. The organic electroluminescence device according to claim 51 , wherein the organic thin film layer comprises a hole transporting layer comprising the compound represented by formula (3-1) or (4-2).
56. The organic electroluminescence device according to claim 51 , wherein the organic thin film layer comprises an electron transporting layer and a blocking layer between the electron transporting layer and the light emitting layer, and the blocking layer comprises the compound represented by formula (3-1) or (4-2).
57. An electronic equipment, comprising the organic electroluminescence device according to claim 51 .