Fused heterocyclic aromatic derivative, organic electroluminescence element material, and organic electroluminescence element using same
A compound represented by the following formula (1). In the formula, A 1 is O, S, Si(Ar 1 )(Ar 2 ), P(═O)(Ar 3 )(Ar 4 ), a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group including 5 to 30 ring atoms.
1. A compound represented by the following formula (1):
wherein in the formula (1),
X 1 to X 3 are independently O or S;
Y 1 to Y 4 and Y 21 to Y 24 are independently C(Ra 1 ) or N;
of Y 5 to Y 12 , one of Y 5 to Y 8 and one of Y 9 to Y 12 are carbon atoms which are bonded to each other, and the remaining Y 5 to Y 12 are independently C(Ra 1 ) or N;
one of Y 13 to Y 16 which bonds to A 1 is a carbon atom, and the remaining Y 13 to Y 16 are independently C(Ra 1 ) or N;
one of Y 17 to Y 20 which bonds to A 1 is a carbon atom, and the remaining Y 17 to Y 20 are independently C(Ra 1 ) or N,
provided that one of (a) to (c) is met:
(a) at least one of Y 1 to Y 4 is N,
(b) at least one of Y 21 to Y 24 is N,
(c) at least one of Y 1 to Y 4 is N, and at least one of Y 21 to Y 24 is N;
A 1 is a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms, or a divalent group of a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted dioxanyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted morpholinyl group, a substituted or unsubstituted piperazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted triazolyl group, an substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyranyl group, or a substituted or unsubstituted benzo[c]dibenzofuranyl group;
n is an integer of 1 to 4;
Ra 1 is a hydrogen atom, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, a substituted or unsubstituted a pyrrolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted dioxanyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted morpholinyl group, a substituted or unsubstituted piperazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyranyl group, or a substituted or unsubstituted benzo[c]dibenzofuranyl group,
when Ra 1 has a substituent the substituent is an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a fluoroalkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring atoms, an aryloxy group having 6 to 30 ring atoms, an aralkyl group having 7 to 30 carbon atoms, a silyl group, an alkylsilyl group having 1 to 6 carbon atoms, a fluoro group or a cyano group; and
when A 1 has a substituent, the substituent is a heteroaryl group including 3 to 30 ring carbon atoms.
2. The compound according to claim 1 , which is represented by the following formula (2):
wherein in the formula (2),
X 1 to X 3 are the same as X 1 to X 3 in the formula (1), respectively;
Y 1 to Y 4 , Y 9 , Y 10 , Y 12 , Y 13 , Y 15 , Y 16 and Y 21 to Y 24 are independently C(Ra 2 ) or N;
one of Y 5 to Y 8 which bonds to the ring comprising Y 9 , Y 10 and Y 12 is a carbon atom, and the remaining Y 5 to Y 8 are independently C(Ra 2 ) or N;
one of Y 17 to Y 20 which bonds to A 2 is a carbon atom, and the remaining Y 17 to Y 20 are independently C(Ra 2 ) or N;
provided that one of (a) to (c) is met:
(a) at least one of Y 1 to Y 4 is N,
(b) at least one of Y 21 to Y 24 is N,
(c) at least one of Y 1 to Y 4 is N, and at least one of Y 21 to Y 24 is N;
A 2 is the same as A 1 in the formula (1);
n is the same as n in the formula (1); and
Ra 2 is the same as Ra 1 in the formula (1).
3. The compound according to claim 2 , which is represented by the following formula (3):
wherein in the formula (3),
Y 1 to Y 5 , Y 7 to Y 10 , Y 12 , Y 13 , Y 15 , Y 16 to Y 18 and Y 20 to Y 24 are independently C(Ra 2 ) or N;
provided that one of (a) to (c) is met:
(a) at least one of Y 1 to Y 4 is N,
(b) at least one of Y 21 to Y 24 is N,
(c) at least one of Y 1 to Y 4 is N, and at least one of Y 21 to Y 24 is N; and
X 1 to X 3 , A 2 , n, Ra z are the same as X 1 to X 3 , A 2 , n, Ra z in the formula (2), respectively.
4. The compound according to claim 3 , which is represented by the following formula (4):
wherein in the formula (4),
X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 and n are the same as X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 and n in the formula (3), respectively.
5. The compound according to claim 4 , which is represented by the following formula (5):
wherein in the formula (5),
Z 1 to Z 4 are independently C(Ra z ) or N;
X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , and Y 20 to Y 24 are the same as X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , and Y 20 to Y 24 in the formula (4), respectively; and
Ra z is the same as Ra z in the formula (2).
6. The compound according to claim 1 , wherein A 1 is a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms.
7. The compound according to claim 1 , wherein A 1 is a divalent group of a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted furyl group a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted dioxanyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted morpholinyl group, a substituted or unsubstituted piperazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted triazolyl group, an substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyranyl group, or a substituted or unsubstituted benzo[c]dibenzofuranyl group.
8. The compound according to claim 2 , wherein A 2 is a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms.
9. The compound according to claim 2 , wherein A 2 is a divalent group of a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolidinyl group, a substituted or unsubstituted dioxanyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted morpholinyl group, a substituted or unsubstituted piperazinyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted triazolyl group, an substituted or unsubstituted imidazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyranyl group, or a substituted or unsubstituted benzo[c]dibenzofuranyl group.
10. The compound according to claim 1 , wherein A 1 is a substituted or unsubstituted arylene group including 6 to 30 ring carbon atoms and the substituent is a heteroaryl group having 3 to 30 ring carbon atoms.
11. The compound according to claim 1 , wherein at least one of Y 1 to Y 4 and Y 21 to Y 24 is N.
12. The compound according to claim 1 , wherein at least one of Y 1 to Y 4 is N.
13. The compound according to claim 1 , wherein at least one of Y 21 to Y 24 is N.
14. The compound according to claim 1 , wherein at least one of Y 1 to Y 4 is N, and at least one of Y 21 to Y 24 is N.
15. A material for an organic electroluminescence device comprising the compound according to claim 1 .
16. An organic electroluminescence device comprising one or more organic thin film layers including an emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers comprises the material for an organic electroluminescence device according to claim 15 .
17. The organic electroluminescence device according to claim 16 , wherein the emitting layer comprises the material for an organic electroluminescence device.
18. The organic electroluminescence device according to claim 17 , wherein the emitting layer comprises the material for an organic electroluminescence device as a host material for the emitting layer.
19. The organic electroluminescence device according to claim 16 , wherein an electro-transporting region is provided between the emitting layer and the cathode, and the electro-transporting region comprises the material for an organic electroluminescence device.
20. The organic electroluminescence device according to claim 16 , wherein the emitting layer comprises a phosphorescent material.
21. The organic electroluminescence device according to claim 20 , wherein the phosphorescent material is a compound containing a metal selected from iridium (Ir), osmium (Os) and platinum (Pt).
22. The organic electroluminescence device according to claim 21 , wherein the compound containing a metal is an ortho-metalized complex.
23. The organic electroluminescence device according to claim 16 , wherein an electron-injecting layer is provided between the emitting layer and the cathode, and the electro-injecting layer comprises a nitrogen-containing heterocyclic derivative.
24. A compound represented by the following formula (11):
wherein in the formula (11),
X 1 to X 3 are O;
Y 1 to Y 4 and Y 21 to Y 24 are independently C(Ra 1 ) or N;
of Y 5 to Y 12 , one of Y 5 to Y 8 and one of Y 9 to Y 12 are carbon atoms which are bonded to each other, and the remaining Y 5 to Y 12 are independently C(Ra 1 ) or N;
one of Y 13 to Y 16 which bonds to A 1 is a carbon atom, and the remaining Y 13 to Y 16 are independently C(Ra 1 ) or N;
one of Y 17 to Y 20 which bonds to A 1 is a carbon atom, and the remaining Y 17 to Y 20 are independently C(Ra 1 ) or N;
A 1 is a substituted or unsubstituted phenylene group, an unsubstituted dibenzofuran group or an unsubstituted aza-dibenzofuran group;
n is an integer of 1 to 4;
Ra 1 is a hydrogen atom, an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted dibenzofuran group; and
when A 1 has a substituent, the substituent is a heteroaryl group including 3 to 30 ring carbon atoms.
25. The compound according to claim 24 , which is represented by the following formula (12):
wherein in the formula (12),
X 1 to X 3 are the same as X 1 to X 3 in the formula (11), respectively;
Y 1 to Y 4 , Y 9 , Y 10 , Y 12 , Y 13 , Y 15 , Y 16 and Y 21 to Y 24 are independently C(Ra 2 ) or N;
one of Y 5 to Y 8 which bonds to the ring comprising Y 9 , Y 10 and Y 12 is a carbon atom, and the remaining Y 5 to Y 8 are independently C(Ra 2 ) or N;
one of Y 17 to Y 20 which bonds to A 2 is a carbon atom, and the remaining Y 17 to Y 20 are independently C(Ra 2 ) or N;
A 2 is the same as A 1 in the formula (11);
n is the same as n in the formula (11); and
Ra z is the same as Ra 1 in the formula (11).
26. The compound according to claim 25 , which is represented by the following formula (13):
wherein in the formula (13),
Y 1 to Y 5 , Y 7 to Y 10 , Y 12 , Y 13 , Y 15 , Y 16 to Y 18 and Y 20 to Y 24 are independently C(Ra 2 ) or N; and
X 1 to X 3 , A 2 , n, Ra z are the same as X 1 to X 3 , A 2 , n, Ra z in the formula (12), respectively.
27. The compound according to claim 26 , which is represented by the following formula (14):
wherein in the formula (14),
X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 and n are the same as X 1 to X 3 , Y 1 to Y 5 , Y 7 , Y 8 , Y 17 , Y 18 , Y 20 to Y 24 , A 2 and n in the formula (13), respectively.
28. The compound according to claim 24 , wherein at least one of Y 1 to Y 4 and Y 21 to Y 24 is N.
29. The compound according to claim 24 , wherein at least one of Y 1 to Y 4 is N.
30. The compound according to claim 24 , wherein at least one of Y 21 to Y 24 is N.
31. The compound according to claim 24 , wherein at least one of Y 1 to Y 4 is N, and at least one of Y 21 to Y 24 is N.
32. The compound according to claim 24 , wherein Y 1 to Y 4 and each of Y 5 to Y 8 that is not the carbon atom which is bonded to one of one of Y 9 to Y 12 are independently C(Ra 1 ).
33. A material for an organic electroluminescence device comprising the compound according to claim 24 .
34. An organic electroluminescence device comprising one or more organic thin film layers including an emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers comprises the material for an organic electroluminescence device according to claim 33 .
35. The organic electroluminescence device according to claim 34 , wherein the emitting layer comprises the material for an organic electroluminescence device.
36. The organic electroluminescence device according to claim 35 , wherein the emitting layer comprises the material for an organic electroluminescence device as a host material for the emitting layer.
37. The organic electroluminescence device according to claim 34 , wherein an electro-transporting region is provided between the emitting layer and the cathode, and the electro-transporting region comprises the material for an organic electroluminescence device.
38. The organic electroluminescence device according to claim 34 , wherein the emitting layer comprises a phosphorescent material.
39. The organic electroluminescence device according to claim 38 , wherein the phosphorescent material is a compound containing a metal selected from iridium (Ir), osmium (Os) and platinum (Pt).
40. The organic electroluminescence device according to claim 39 , wherein the compound containing a metal is an ortho-metalized complex.
41. The organic electroluminescence device according to claim 34 , wherein an electron-injecting layer is provided between the emitting layer and the cathode, and the electro-injecting layer comprises a nitrogen-containing heterocyclic derivative.