Organic electroluminescent materials and devices
A compound having the following formula is disclosed. The compound is useful as an emitter in OLED applications.
1. A compound having the formula:
wherein L 1 is O;
wherein R A , R B , R B′ , R C , and R D , each represents mono to a maximum allowable substitutions, or no substitution;
wherein each of R A , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof, with the proviso that R D cannot comprise heteroaryl unless two R D are joined to form a ring;
wherein each R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, or partially or fully deuterated variants thereof;
wherein R is partially or fully deuterated alkyl, or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;
wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;
wherein at least one of R A and R C is present and is a 5- or 6-membered aromatic ring, which may be further substituted.
2. The compound of claim 1 , wherein each R B and R B′ is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and partially or fully deuterated variants thereof.
3. The compound of claim 1 , wherein two adjacent R D substituents are joined to form a fused benzene ring.
4. The compound of claim 1 , wherein R is 2,6-disubstituted phenyl, wherein each of the substitutions is independently selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof.
5. The compound of claim 1 , wherein R is a deuterated alkyl group.
6. 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 having the formula:
wherein L 1 is O;
wherein R A , R B , R B′ , R C , and R D , each represents mono to a maximum allowable substitutions, or no substitution;
wherein each of R A , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof, with the proviso that R D cannot comprise heteroaryl unless two R D are joined to form a ring;
wherein each R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, or partially or fully deuterated variants thereof;
wherein R is partially or fully deuterated alkyl, or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;
wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;
wherein at least one of R A and R C is present and is a 5- or 6-membered aromatic, which may be further substituted.
7. The OLED of claim 6 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
8. The OLED of claim 6 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
9. The OLED of claim 6 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
and combinations thereof.
10. A consumer product comprising 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 having the formula:
wherein L 1 is O;
wherein R A , R B , R B′ , R C , and R D , each represents mono to a maximum allowable substitutions, or no substitution;
wherein each of R A , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof, with the proviso that R D cannot comprise heteroaryl unless two R D are joined to form a ring;
wherein each R B and R B′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, and partially or fully deuterated variants thereof, which may be further substituted by one or more alkyl, cycloalkyl, aryl, or partially or fully deuterated variants thereof;
wherein R is partially or fully deuterated alkyl, or aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof;
wherein any substitutions in R A , R B , R B′ , R C , and R D may be joined or fused into a ring;
wherein at least one of R A and R C is present and is a 5- or 6-membered aromatic ring, which may be further substituted.
11. A formulation comprising the compound of claim 1 .
12. The compound of claim 1 , wherein at least one R A is a 5- or 6-membered aromatic ring, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof.
13. The compound of claim 1 , wherein at least one R A is a phenyl ring, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof.
14. The compound of claim 1 , wherein exactly one of R A and R C is present and is a 5- or 6-membered aromatic ring, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof.
15. The compound of claim 1 , wherein exactly one of R A and R C is present and is a phenyl ring, which may be further substituted by one or more alkyl, cycloalkyl, aryl, heteroaryl, partially or fully fluorinated variants thereof, or partially or fully deuterated variants thereof.
16. The compound of claim 1 , wherein R is aryl, which may be substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, aryl, heteroaryl, and combinations thereof.
17. The compound of claim 16 , wherein R is aryl, which is substituted by at least one aryl.
18. The compound of claim 1 , wherein the compound is selected from the group consisting of:
19. The compound of claim 1 , the compound is selected from the group consisting of Compound y having the formula Pt(L Ay )(L Bz ), wherein each L Ay has the structure defined in the following list:
L Ay
Structure of L Ay
Ar 1 , R 1
y
L A1 to L A9900 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k
L A9901 -L A19800 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 9900
L A19801 -L A29700 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 19800
L 29701 -L A39600 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 29700
L A39601 -L A49500 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 39600
L A49501 -L A59400 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 49500
L A59401 -L A69300 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 59400
L A69301 -L A79200 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 69300
L A79201 to L A79530 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 79200
L A79531 -L A79860 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 79530
L A79861 -L A80190 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 79860
L A80191 -L A80520 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 80190
L A80521 to L A90420 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 80520
L A90421 to L A100320 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 90420
L A100321 to L A110220 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 100320
L A110221 to L A120120 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 110220
L A120121 to L A130020 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 120120
L A130021 to L A139920 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 130020
L A139921 to L A149820 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 139920
L A149821 to L A159720 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 149820
L A159721 to L A169620 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 159720
L A169621 to L A169950 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 169620
L A169951 to L A170280 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 169950
L A170281 to L A170610 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 170280
L A170610 to L A170940 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 170610
L A171271 to L A171600 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 171270
L A171601 to L A181500 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 171600
L A181501 to L A191400 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 8, 10 to 15, 18 to 78, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 181500
L A191731 to L A192060 have the structure
wherein R 1 = Rk, wherein k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = k + 191730
L A192061 to L A201960 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 192060
L A201961 to L A211860 have the structure
wherein Ar 1 = Ai and R 1 = Rk, wherein i is an integer from 1 to 19 and 21 to 30 and k is an integer from 10 to 15, 18 to 25, 27 to 30, 35 to 49, 52 to 74, 89, 90, and 93 to 330, and
wherein, y = 330(i − 1) + k + 201960
wherein each L Bz has the structure defined in the following list:
L Bz
L Bz structure
Ar 2 , Ar 3 , R 2
Z
wherein L B1 -L B30 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 1 to 19 and 21 to 30, and
z = j
wherein L B31 have the structure
z = 31
wherein L B32 -L B931 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21 to 30, and
z = 30(j − 1) + m + 31
wherein L B932 -L B961 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 931
wherein L B962 -L B1861 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 961
wherein L B1862 -L B1891 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 1861
wherein L B1892 -L B1921 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 1 to 19 and 21-30, and
z = j + 1891
wherein L B1922 -L B2821 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 1921
wherein L B2822 -L B3721 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 2821
wherein L B3722 -L B4621 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 3721
wherein L B4622 -L B4651 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 4621
wherein L B4652 -L B5551 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 4651
wherein L B5552 -L B5581 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 5551
wherein L B5582 -L B6481 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 5581
wherein L B6482 -L B7381 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 6481
wherein L B7382 have the structure
z = 7382
wherein L B7383 -L B7412 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 7382
wherein L B7413 -L B7442 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 7412
wherein L B7443 -L B7472 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 7442
wherein L B7473 -L B7502 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j +7472
wherein L B17796 -L B17825 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 1 to 19 and 21-30, and
z = j + 17795
wherein L B17826 have the structure
z = 17826
wherein L B17827 -L B18726 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 17826
wherein L B18727 -L B18756 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 18726
wherein L B18757 -L B19656 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 18756
wherein L B19657 -L B19686 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 19656
wherein L B19687 -L B19716 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 1 to 19 and 21-30, and
z = j + 19686
wherein L B19717 have the structure
z = 19717
wherein L B19718 -L B20617 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 11 to 17 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 19717
wherein L B20618 -L B20647 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 20617
wherein L B20648 -L B21547 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 20647
wherein L B21548 -L B21577 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 21547
wherein L B21578 -L B22477 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 21577
wherein L B22478 -L B22507 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 22477
wherein L B22508 -L B23407 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 22507
wherein L B23408 -L B23437 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 23407
wherein L B23438 -L B24337 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 23437
wherein L B24338 -L B24367 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 24337
wherein L B24368 -L B25267 have the structure
wherein Ar 2 = Aj and Ar 3 = Am, wherein j is an integer from 1 to 19 and 21 to 30 and m is an integer from 11 to 17 and 21-30, and
z = 30(j − 1) + m + 24367
wherein L B25268 -L B25297 have the structure
wherein Ar 2 = Aj, wherein j is an integer from 11 to 17 and 21-30, and
z = j + 25267
wherein A1 to A30 have the following structures:
and wherein R1 to R330 have the following structures:
20. The compound of claim 1 , wherein R is selected from the group consisting of