US 12,168,661 B2
Functional materials based on stable chemical structure
Jian Li, Tempe, AZ (US); and Xinqiang Tan, Tempe, AZ (US)
Assigned to ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY, Scottsdale, AZ (US)
Filed by ARIZONA BOARD OF REGENTS, Scottsdale, AZ (US)
Filed on Feb. 18, 2021, as Appl. No. 17/178,901.
Claims priority of provisional application 63/044,434, filed on Jun. 26, 2020.
Claims priority of provisional application 62/979,596, filed on Feb. 21, 2020.
Prior Publication US 2021/0323963 A1, Oct. 21, 2021
Int. Cl. C07D 471/22 (2006.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01)
CPC C07D 471/22 (2013.01) [H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 50/11 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound of General Formula I:

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wherein:
T2 and T3 represent a Donor or an Acceptor; T1 optionally represents a Donor;
Y1 and Y2 each independently represent C, N, Si, B, or P;
wherein when Y1 and Y2 both represent C, then two groups R1 may optionally together form a fused aryl or heteroaryl ring having the following structure:

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wherein for any two adjacent Xa and Xb representing X5-X8 where a and b are integers from 5-8, then two groups R2 may optionally together form a fused aryl or heteroaryl ring having the following structure:

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wherein for any two adjacent Xc and Xd representing X9-X12 where c and d are integers from 9-12, then two groups R3 may optionally together form a fused aryl or heteroaryl ring having the following structure:

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wherein:
X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, and X16 each independently represents C, N, Si, B, or P;
U1 represents O, S, Se, NR21, P═O, As═O, Bi═O, CR21R22, C═O, SiR21R22, GeR21R22, NR21, PR21, PR21R22, R21P═O, AsR21, R21As═O, S═O, SeO2, Se═O, SeO2, BR21, BR21R22, AlR21, AlR21R22, R21Bi═O, or BiR21;
each n is independently an integer, valency permitting; and
each of R1, R2, R3, R4, R5, R21 and R22 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof;
wherein two adjacent groups R1, R2, R3, R4, R5, R21, R22, or a combination thereof may optionally together form a fused ring; and
wherein at least one of the following conditions (i)-(iii) is satisfied:
(i) two groups R1 together form a fused heteroaryl structure having the structure

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 or
(ii) X9 and X10 each represent C substituted by R3, wherein the two groups R3 are represented by the following structure:

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wherein the dashed lines indicate bonds to X9 and X10, and
X11 and X12 each represent C substituted by R3, wherein the two groups R3 are represented by the following structure:

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wherein the dashed lines indicate bonds to X11 and X12, or
(iii) at least one of Y1 and Y2 represents C, and at least one R1 is represented by the following structure:

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