Organic electroluminescent materials and devices
A compound having a formula useful as a phosphorescent emitter in organic light emitting devices is disclosed.
1. A compound having one of the following two formulas
wherein at least one of X 5 to X 8 and X 12 to X 15 is N, and
wherein at least one of X 5 to X 8 and X 16 to X 19 is N; and
wherein Ar 1 is a 5-membered aromatic ring, and Ar 2 is a phenyl ring;
wherein X 1 to X 10 and X 12 to X 19 are each independently a C or N;
wherein one of Z 1 and Z 2 is C, and the other one is N;
wherein when Z 1 is N, X 4 is C;
wherein L 1 is selected from the group consisting of a direct bond, NR′, BR′, O, S, CR′R″, SiR′R″, alkylene, and cycloalkylene;
wherein L 2 and L 3 are each independently selected from the group consisting of NR′, BR′, O, S, CR′R″, SiR′R″, Phenylene, alkylene, and cycloalkylene;
wherein m is 0 or 1;
wherein when m=0, L 2 is not present and there is no direct bond between X 1 and Ar 1 ;
wherein when m is 1, X 1 is C; wherein R 1 to R 6 each independently represents mono to a maximum possible number of substitutions, or no substitution; and
wherein R 1 to R 6 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and wherein any two adjacent substituents are optionally joined to form into a ring.
2. The compound of claim 1 , wherein the compound has the structure of formula
3. The compound of claim 1 , wherein the compound has the structure of formula
4. An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of claim 1 .
5. The OLED of claim 4 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
6. The OLED of claim 4 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
7. The OLED of claim 4 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.
8. The OLED of claim 4 , wherein the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved.
9. The OLED of claim 4 , wherein the OLED further comprises a layer comprising carbon nanotubes.
10. A consumer product comprising an OLED of claim 4 .
11. A compound selected from the group consisting of Compounds 1-84, 92-98, 106-112, 137-163, 164, 168, 169, 170, 172, 173, 177-179, 181, 182, 186-188, 190, 191, 195-197, 199-200, 204-206, and 208 defined below:
Compound ID
X 5
X 15
X 2
R
Compounds 1 through 14 having the following structure
wherein X 2 , X 5 , X 15 , and R are as defined in this table.
1 2 3 4 5 6 7 8 9 10 11 12 13 14
N CH CH N N CH N N CH CH N N CH N
CH N CH N CH N N CH N CH N CH N N
CH CH N CH N N N CH CH N CH N N N
H H H H H H H Ph Ph Ph Ph Ph Ph Ph
Compounds 15 through 21 having the following structure
wherein X 2 , X 5 , X 15 , and R are as defined in this table.
15 16 17 18 19 20 21
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
— — — — — — —
Compounds 22 through 28 having the following structure
wherein X 2 , X 5 , X 15 , and R are as defined in this table.
22 23 24 25 26 27 28
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
— — — — — — —
Compounds 29 through 42 having the following structure
wherein X 2 , X 5 , X 15 , and R are as defined in this table.
29 30 31 32 33 34 35 36 37 38 39 40 41 42
N CH CH N N CH N N CH CH N N CH N
CH N CH N CH N N CH N CH N CH N N
CH CH N CH N N N CH CH N CH N N N
Me Me Me Me Me Me Me Ph Ph Ph Ph Ph Ph Ph
Compounds 43 through 56 having the following structure
wherein X 2 , X 5 , X 15 , and R are as defined in this table.
43 44 45 46 47 48 49 50 51 52 53 54 55 56
N CH CH N N CH N N CH CH N N CH N
CH N CH N CH N N CH N CH N CH N N
CH CH N CH N N N CH CH N CH N N N
Me Me Me Me Me Me Me Ph Ph Ph Ph Ph Ph PHh
Compound ID
X 5
X 4
X 19
R
Compounds 57 through 70 having the following structure
wherein X 4 , X 5 , X 19 , and R are as defined in this table.
57 58 59 60 61 62 63 64 65 66 67 68 69 70
N CH CH N N CH N N CH CH N N CH N
CH N CH N CH N N CH N CH N CH N N
CH CH N CH N N N CH CH N CH N N N
H H H H H H H Ph Ph Ph Ph Ph Ph Ph
Compounds 71 through 77 having the following structure
wherein X 4 , X 5 , X 19 , and R are as defined in this table.
71 72 73 74 75 76 77
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
— — — — — — —
Compounds 78 through 84 having the following structure
wherein X 4 , X 5 , X 19 , and R are as defined in this table.
78 79 80 81 82 83 84
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
— — — — — — —
Compounds 92 through 98 having the following structure
wherein X 4 , X 5 , X 19 , and R are as defined in this table.
92 93 94 95 96 97 98
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
Ph Ph Ph Ph Ph Ph Ph
Compounds 106 through 112 having the following structure
wherein X 4 , X 5 , X 19 , and R are as defined in this table.
106 107 108 109 110 111 112
N CH CH N N CH N
CH N CH N CH N N
CH CH N CH N N N
Ph Ph Ph Ph Ph Ph Ph
Compound ID
X 5
X 4
X 3
X 2
R
Compounds 137 through 154 having the following structure
wherein X 2 , X 3 , X 4 , X 5 , and R are as defined in this table.
137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154
N CH CH CH N N N CH N N CH CH CH N N N CH N
CH N CH CH N CH CH N N CH N CH CH N CH CH N N
CH CH N CH CH N CH CH CH CH CH N CH CH N CH CH CH
CH CH CH N CH CH N N N CH CH CH N CH CH N N N
H H H H H H H H H Ph Ph Ph Ph Ph Ph Ph Ph Ph
Compounds 155 through 163 having the following structure
wherein X 2 , X 3 , X 4 , X 5 , and R are as defined in this table.
155 156 157 158 159 160 161 162 163
N CH CH CH N N N CH N
CH N CH CH N CH CH N N
CH CH N CH CH N CH CH CH
CH CH CH N CH CH N N N
— — — — — — — — —
Compounds 164, 168, 169, 170, and 172 having the following structure
wherein X 2 , X 3 , X 4 , X 5 , and R are as defined in this table.
164 168 169 170 172
N N N N N
CH N CH CH N
CH CH N CH CH
CH CH CH N N
— — — — —
Compounds 173, 177-179, 181, 182, 186-188, and 190 having the following structure
wherein X 2 , X 3 , X 4 , X 5 , and R are as defined in this table.
173 177 178 179 181 182 186 187 188 190
N N N N N N N N N N
CH N CH CH N CH N CH CH N
CH CH N CH CH CH CH N CH CH
CH CH CH N N CH CH CH N N
Me Me Me Me Me Ph Ph Ph Ph Ph
Compounds 191, 195-197, 199-200, 204-206 and 208 having the following structure
wherein X 2 , X 3 , X 4 , X 5 , and R are as defined in this table.
191 195 196 197 199 200 204 205 206 208
N N N N N N N N N N
CH N CH CH N CH N CH CH N
CH CH N CH CH CH CH N CH CH
CH CH CH N N CH CH CH N N
Me Me Me Me Me Ph Ph Ph Ph Ph,
wherein Me is methyl, and Ph is phenyl.
12. The compound of claim 11 , wherein the compound is selected from the group consisting of Compounds 1 through 21, 57 through 77, and 137 through 163.
13. The compound of claim 11 , wherein the compound is selected from the group consisting of Compounds 1 through 56.
14. An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of claim 11 .
15. The OLED of claim 14 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
16. The OLED of claim 14 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
17. The OLED of claim 14 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.
18. The OLED of claim 14 , wherein the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved.
19. The OLED of claim 14 , wherein the OLED further comprises a layer comprising carbon nanotubes.
20. A consumer product comprising an OLED of claim 14 .