US 11,925,101 B2
Organic semiconducting compound and the organic photoelectric components using the same
Wei-Long Li, Hsinchu (TW); Yu-Tang Hsiao, Hsinchu (TW); Chia-Hua Tsai, Hsinchu (TW); and Chuang-Yi Liao, Hsinchu (TW)
Assigned to RAYNERGY TEK INCORPORATION, Hsinchu (TW)
Filed by RAYNERGY TEK INCORPORATION, Hsinchu (TW)
Filed on Sep. 9, 2022, as Appl. No. 17/930,868.
Claims priority of provisional application 63/244,362, filed on Sep. 15, 2021.
Prior Publication US 2023/0126747 A1, Apr. 27, 2023
Int. Cl. H10K 30/00 (2023.01); C08G 61/12 (2006.01); H10K 30/82 (2023.01); H10K 85/10 (2023.01); H10K 85/40 (2023.01)
CPC H10K 85/113 (2023.02) [C08G 61/126 (2013.01); H10K 30/451 (2023.02); H10K 30/82 (2023.02); H10K 85/151 (2023.02); H10K 85/40 (2023.02); C08G 2261/124 (2013.01); C08G 2261/1412 (2013.01); C08G 2261/1424 (2013.01); C08G 2261/146 (2013.01); C08G 2261/148 (2013.01); C08G 2261/149 (2013.01); C08G 2261/18 (2013.01); C08G 2261/228 (2013.01); C08G 2261/3223 (2013.01); C08G 2261/3241 (2013.01); C08G 2261/3246 (2013.01); C08G 2261/3247 (2013.01); C08G 2261/91 (2013.01)] 12 Claims
OG exemplary drawing
 
1. An organic compound of the following formula:

OG Complex Work Unit Chemistry
wherein
A0 is an electron withdrawing group;
A1 is electron withdrawing group which is different from A0 and is selected from the following formulae;

OG Complex Work Unit Chemistry
R4-R6 are selected from the group consisting of the following groups:
halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituted alkyl, C1-C30 nitro-substituted alkyl, C1-C30 hydroxy-substituted alkyl, C3-C30 keto-substituted alkyl, unsubstituted aromatic group, unsubstituted heterocyclic group, unsubstituted fused ring group, unsubstituted fused heterocyclic group, aromatic group substituted with at least one Ra, heterocyclic group substituted with at least one Ra, fused ring group substituted with at least one Ra, and fused heterocyclic group substituted with at least one Ra;
X is selected from the group consisting of O, S, or Se;
Ar6 and A7 are selected from the group consisting of unsubstituted aromatic group, unsubstituted heterocyclic group, unsubstituted fused ring group, unsubstituted fused heterocyclic group, aromatic group substituted with at least one Ra, heterocyclic group substituted with at least one Ra, fused ring group substituted with at least one Ra, and fused heterocyclic group substituted with at least one Ra;
Ar8 is selected from the group consisting of hydrogen atom, halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituted alkyl, C1-C30 nitro-substituted alkyl, C1-C30 hydroxy-substituted alkyl, C3-C30 keto-substituted alkyl, unsubstituted aromatic group, unsubstituted heterocyclic group, unsubstituted fused ring group, unsubstituted fused heterocyclic group, aromatic group substituted with at least one Rb, heterocyclic group substituted with at least one Rb, fused ring group substituted with at least one Rb, and fused heterocyclic group substituted with at least one Rb;
Ra and Rb are selected from the group consisting of hydrogen atom, halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituted alkyl, C1-C30 nitro-substituted alkyl, C1-C30 hydroxy-substituted alkyl, and C3-C30 keto-substituted alkyl; and
h is an integer selected from 1 to 8;
A2 is selected from the group consisting of

OG Complex Work Unit Chemistry
wherein
R7-R8 are selected from the group consisting of halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituted alkyl, C1-C30 nitro-substituted alkyl, C1-C30 hydroxy-substituted alkyl, C3-C30 keto-substituted alkyl, unsubstituted aromatic group, unsubstituted heterocyclic group, unsubstituted fused ring group, unsubstituted fused heterocyclic group, aromatic group substituted with at least one Rb, heterocyclic group substituted with at least one Rb, fused ring group substituted with at least one Rb, and fused heterocyclic group substituted with at least one Rb;
R9-R14 are selected from the group consisting of hydrogen atom, halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituted alkyl, C1-C30 nitro-substituted alkyl, C1-C30 hydroxy-substituted alkyl, C3-C30 keto-substituted alkyl, unsubstituted aromatic group, unsubstituted heterocyclic group, unsubstituted fused ring group, unsubstituted fused heterocyclic group, aromatic group substituted with at least one Rb, heterocyclic group substituted with at least one Rb, fused ring group substituted with at least one Rb, and fused heterocyclic group substituted with at least one Rb;
wherein Rb is selected from the group consisting of hydrogen atom, halogen, cyano group, C1-C30 linear alkyl, C3-C30 branched alkyl, C1-C30 silyl group, C2-C30 ester group, C1-C30 alkoxy, C1-C30 thioalkyl, C1-C30 haloalkyl, C2-C30 alkene, C2-C30 alkyne, C2-C30 cyano-substituent alkyl, C1-C30 nitro-substituent alkyl, C1-C30 hydroxy-substituent alkyl, and C3-C30 keto-substituent alkyl; and
X is selected from O, S, or Se,
Ar0, A1, Ar2, π0, π1, and π2 are electron donating groups which are independent from one another;
d, e, f are integers independent from one another and selected from 0 to 5; and
a, b, c are real numbers, wherein a+b+c=1, 0<a≤1, 0<b≤1 and 0<c≤1.