Electroluminescent materials and devices
Provided are an electroluminescent material and device. The electroluminescent material is a compound having an indole- and pyrrole-fused azamacrocycle structure segment which is connected to quinazoline having a substitution on a specific ring, quinoxaline having a substitution on a specific ring, or a similar structure thereof, and can be used as the host material in the electroluminescent device. These novel compounds can obtain a lower driving voltage, effectively improve device efficiency, greatly prolong device lifetime, and provide better device performance. Further provided are an electroluminescent device and a compound formulation.
1. A compound, having a structure of H-L-E;
wherein H has a structure represented by Formula 1-a:
wherein A 1 to A 3 are, at each occurrence identically or differently, selected from CR, and X 1 to X 10 are, at each occurrence identically or differently, selected from CR x ;
wherein E has a structure represented by Formula 2-a, or Formula 2-c:
wherein in Formula 2-a, Y 1 to Y 3 are, at each occurrence identically or differently, selected from CR y , and Y 4 is selected from CR z ;
wherein in Formula 2-c, Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y or CR z , and at least one of Y 1 , Y 2 and Y 4 is selected from CR z ;
L is a single bond;
wherein R, R x , and R y are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, and combinations thereof;
wherein R z is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms.
2. The compound according to claim 1 , wherein the H has a structure represented by Formula 1-a:
wherein A 1 to A 3 are, at each occurrence identically or differently, selected from CR, and X to X 10 are, at each occurrence identically or differently, selected from CR x ;
wherein R and R x are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
3. The compound according to claim 2 , wherein R and R y are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and combinations thereof.
4. The compound according to claim 2 , wherein at least one of R and R x is selected from deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.
5. The compound according to claim 1 , wherein the His selected from the group consisting of the following structures:
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
6. The compound according to claim 1 , wherein the E has a structure represented by Formula 2-a or Formula 2-c:
wherein in Formula 2-a, Y 1 to Y 3 are, at each occurrence identically or differently, selected from CR y , and Y 4 is selected from CR z ;
wherein in Formula 2-c, Y 1 , Y 3 , and Y 4 are, at each occurrence identically or differently, selected from CR y , and Y 2 is selected from CR z
wherein R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;
wherein R z is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms.
7. The compound according to claim 6 , wherein in the structures represented by Formula 2-a or Formula 2-c, the R y connected to the aza six-membered ring is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms.
8. The compound according to claim 5 , wherein the E is selected from the group consisting of the following structures:
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
9. The compound according to claim 8 , wherein the compound is selected from the group consisting of the following Compounds, wherein the following Compound each has a structure of H-L-E, wherein H, L, and E are selected from structures in the following table, respectively, wherein L-0 is a single bond:
Compound
H
L
E
1
H-1
L-0
E-1
5
H-1
L-0
E-5
9
H-1
L-0
E-9
13
H-1
L-0
E-13
17
H-1
L-0
E-17
21
H-1
L-0
E-21
25
H-1
L-0
E-25
29
H-1
L-0
E-29
33
H-1
L-0
E-33
37
H-1
L-0
E-37
41
H-1
L-0
E-41
45
H-1
L-0
E-45
47
H-1
L-0
E-47
49
H-1
L-0
E-49
51
H-1
L-0
E-51
53
H-1
L-0
E-53
55
H-1
L-0
E-55
56
H-1
L-0
E-56
57
H-1
L-0
E-57
59
H-1
L-0
E-59
60
H-1
L-0
E-60
61
H-1
L-0
E-61
63
H-1
L-0
E-63
64
H-1
L-0
E-64
65
H-1
L-0
E-65
67
H-1
L-0
E-67
68
H-1
L-0
E-68
69
H-1
L-0
E-69
71
H-1
L-0
E-71
72
H-1
L-0
E-72
73
H-1
L-0
E-73
75
H-1
L-0
E-75
76
H-1
L-0
E-76
77
H-1
L-0
E-77
79
H-1
L-0
E-79
80
H-1
L-0
E-80
81
H-1
L-0
E-81
83
H-1
L-0
E-83
84
H-1
L-0
E-84
85
H-1
L-0
E-85
87
H-1
L-0
E-87
88
H-1
L-0
E-88
89
H-1
L-0
E-89
91
H-1
L-0
E-91
92
H-1
L-0
E-92
93
H-1
L-0
E-93
95
H-1
L-0
E-95
96
H-1
L-0
E-96
97
H-1
L-0
E-97
99
H-1
L-0
E-99
100
H-1
L-0
E-100
101
H-1
L-0
E-101
103
H-1
L-0
E-103
104
H-1
L-0
E-104
105
H-1
L-0
E-105
107
H-1
L-0
E-107
108
H-1
L-0
E-108
109
H-1
L-0
E-109
111
H-1
L-0
E-111
112
H-1
L-0
E-112
113
H-1
L-0
E-113
115
H-1
L-0
E-115
116
H-1
L-0
E-116
117
H-1
L-0
E-117
119
H-1
L-0
E-119
120
H-1
L-0
E-120
121
H-1
L-0
E-121
123
H-1
L-0
E-123
124
H-1
L-0
E-124
125
H-1
L-0
E-125
126
H-1
L-0
E-126
127
H-1
L-0
E-127
128
H-1
L-0
E-128
129
H-1
L-0
E-129
130
H-1
L-0
E-130
131
H-1
L-0
E-131
132
H-1
L-0
E-132
133
H-1
L-0
E-133
134
H-1
L-0
E-134
135
H-1
L-0
E-135
136
H-1
L-0
E-136
137
H-1
L-0
E-137
138
H-1
L-0
E-138
139
H-1
L-0
E-139
140
H-1
L-0
E-140
141
H-1
L-0
E-141
142
H-1
L-0
E-142
143
H-1
L-0
E-143
144
H-1
L-0
E-144
146
H-1
L-0
E-146
171
H-1
L-0
E-171
172
H-1
L-0
E-172
173
H-1
L-0
E-173
174
H-1
L-0
E-174
175
H-1
L-0
E-175
176
H-1
L-0
E-176
189
H-1
L-0
E-189
190
H-1
L-0
E-190
191
H-1
L-0
E-191
192
H-1
L-0
E-192
193
H-1
L-0
E-193
194
H-1
L-0
E-194
195
H-1
L-0
E-195
196
H-1
L-0
E-196
197
H-1
L-0
E-197
198
H-1
L-0
E-198
199
H-1
L-0
E-199
200
H-1
L-0
E-200
207
H-1
L-0
E-207
208
H-1
L-0
E-208
209
H-1
L-0
E-209
210
H-1
L-0
E-210
211
H-1
L-0
E-211
212
H-1
L-0
E-212
213
H-1
L-0
E-213
214
H-1
L-0
E-214
215
H-1
L-0
E-215
216
H-1
L-0
E-216
749
H-102
L-0
E-1
750
H-103
L-0
E-1
751
H-104
L-0
E-1
752
H-105
L-0
E-1
753
H-106
L-0
E-1
754
H-107
L-0
E-1
755
H-108
L-0
E-1
756
H-109
L-0
E-1
757
H-110
L-0
E-1
758
H-111
L-0
E-1
759
H-112
L-0
E-1
760
H-113
L-0
E-1
761
H-114
L-0
E-1
762
H-115
L-0
E-1
763
H-116
L-0
E-1
764
H-117
L-0
E-1
765
H-118
L-0
E-1
983
H-102
L-0
E-134
984
H-103
L-0
E-134
985
H-104
L-0
E-134
986
H-105
L-0
E-134
987
H-106
L-0
E-134
988
H-107
L-0
E-134
989
H-108
L-0
E-134
990
H-109
L-0
E-134
991
H-110
L-0
E-134
992
H-111
L-0
E-134
993
H-112
L-0
E-134
994
H-113
L-0
E-134
995
H-114
L-0
E-134
996
H-115
L-0
E-134
997
H-116
L-0
E-134
998
H-117
L-0
E-134
999
H-118
L-0
E-134
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
10. An electroluminescent device, comprising:
an anode,
a cathode, and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to claim 1 .
11. The electroluminescent device according to claim 10 , wherein the organic layer is an emissive layer, and the compound is a host material.
12. The electroluminescent device according to claim 11 , wherein the emissive layer further comprises at least one phosphorescent material.
13. The electroluminescent device according to claim 12 , wherein the phosphorescent material is a metal complex comprising at least one ligand, wherein the ligand comprises any one of the following structures:
wherein
R a , R b , and R c , at each occurrence identically or differently, represent mono-substitution, multiple substitutions or non-substitution;
X b is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR N1 , and CR C1 R C2 ;
X c and X d are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NR N2 ;
R a , R b , R c , R N1 , R N2 , R C1 , and R C2 are, at each occurrence identically or differently, selected from the group consisting of, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
in the structure of the ligand, adjacent substituents can be optionally joined to form a ring.
14. The electroluminescent device according to claim 12 , wherein the phosphorescent material is a metal complex comprising at least one ligand, wherein the ligand is represented by the following structure:
wherein R 1 to R 7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
15. The electroluminescent device according to claim 13 , wherein the phosphorescent material is an Ir complex, a Pt complex or an Os complex.
16. A compound formulation, comprising the compound according to claim 1 .
17. The compound according to claim 4 , wherein at least one of R and R x is selected from deuterium, phenyl, biphenyl or pyridyl.
18. The compound according to claim 1 , wherein in Formula 2-c, Y 2 is selected from CR z , and Y 1 , Y 3 and Y 4 are each independently selected from CR y ; or Y 1 and Y 4 are selected from CR z , and Y 2 and Y 3 are each independently selected from CR y .
19. The compound according to claim 1 , wherein the R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and combinations thereof;
the R z is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 18 carbon atoms.
20. The compound according to claim 1 , wherein the R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, phenyl, biphenyl, naphthyl, and combinations thereof;
the R z is, at each occurrence identically or differently, selected from phenyl, biphenyl, naphthyl, or combinations thereof.
21. The compound according to claim 1 , wherein the R y is selected from deuterium, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl or phenylpyridyl.
22. The electroluminescent device according to claim 15 , wherein the phosphorescent material is an Ir complex and has a structure of Ir(L a )(L b )(L c );
wherein L a , L b , and L c are, at each occurrence identically or differently, selected from any one of the above ligands.
23. The electroluminescent device according to claim 15 , wherein the Ir complex is selected from the group consisting of the following structures:
wherein X f is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR N3 , and CR C3 R C4 ;
wherein X e is, at each occurrence identically or differently, selected from CR d or N;
R a , R b , and R c , at each occurrence identically or differently, represent mono-substitution, multiple substitutions or non-substitution;
R a , R b , R c , R a , R N3 , R C3 , and R C4 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
24. The compound according to claim 1 , wherein E has a structure represented by Formula 2-a.