US 12,193,317 B2
Organic semiconducting compounds
Changsheng Wang, Eastleigh (GB); William Mitchell, Chandler's Ford (GB); Thomas Hodsden, London (GB); Martin Heeney, Woking (GB); and Julianna Panidi, London (GB)
Assigned to FLEXENABLE TECHNOLOGY LIMITED, Cambridge (GB)
Appl. No. 17/260,147
Filed by FLEXENABLE TECHNOLOGY LTD., Cambridge (GB)
PCT Filed Jul. 10, 2019, PCT No. PCT/EP2019/068496
§ 371(c)(1), (2) Date Jan. 13, 2021,
PCT Pub. No. WO2020/011831, PCT Pub. Date Jan. 16, 2020.
Claims priority of application No. 18183372 (ER), filed on Jul. 13, 2018.
Prior Publication US 2022/0131078 A1, Apr. 28, 2022
Int. Cl. H10K 85/10 (2023.01); C07D 495/04 (2006.01); C08G 61/12 (2006.01); H10K 85/60 (2023.01); H10K 30/30 (2023.01)
CPC H10K 85/113 (2023.02) [C07D 495/04 (2013.01); C08G 61/126 (2013.01); H10K 85/151 (2023.02); H10K 85/6576 (2023.02); C08G 2261/124 (2013.01); C08G 2261/142 (2013.01); C08G 2261/146 (2013.01); C08G 2261/18 (2013.01); C08G 2261/228 (2013.01); C08G 2261/3243 (2013.01); C08G 2261/91 (2013.01); C08G 2261/92 (2013.01); C08G 2261/94 (2013.01); C08G 2261/95 (2013.01); H10K 30/30 (2023.02)] 23 Claims
 
1. A compound comprising a unit of formula I

OG Complex Work Unit Chemistry
wherein X, Arx1 and Arx2, independently of each other and on each occurrence identically or differently, have the following meanings
X is selected from the group consisting of the following formulae, wherein Q denotes an sp2 C atom that is attached to the indacene core in formula I via the C═C double bond

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
Arx1 is selected from the group consisting of the following formulae

OG Complex Work Unit Chemistry
Arx2 is selected from the group consisting of the following formulae

OG Complex Work Unit Chemistry
V1 CR5 or N,
W1, W2 S, O, Se or C═O,
W3 S, O or NR0,
R1-7 H, F, Cl, CN, or straight-chain, branched or cyclic alkyl with 1 to 30 C atoms, in which one or more CH2 groups are optionally replaced by -O-, -S-, —C(═O)—, -C(═S)-, -C(═O)—O—, -O—C(═O)—, -NR0 —, -SiR0R00-, -CF2-, -CR0═CR00-, -CY1-CY2- or -C≡C- in such a manner that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are optionally replaced by F, Cl, Br, I or CN, and in which one or more CH2 or CH3 groups are optionally replaced by a cationic or anionic group, or aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxy or heteroaryloxy, wherein each of the aforementioned cyclic groups has 5 to 20 ring atoms, is mono- or polycyclic, does optionally contain fused rings, and is unsubstituted or substituted by one or more identical or different groups L,
Y1, Y2 H, F, Cl or CN,
L F, Cl, -NO2, -CN, -NC, -NCO, -NCS, -OCN, -SCN, R0 , OR0, SR0, -C(═O)X0, -C(═O) R0 , -C(═O)—OR0, -O—C(═O)—R0 , -NH2, -NHR0, -NR0 R00, -C(═O)NHR0, -C(═O)NR0 R00, -SO3R0 , -SO2R0 , -OH, -NO2, -CF3, -SF5, or optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 30 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, preferably F, -CN, R0 , -OR0, -SR0, -C(═O)—R0 , -C(═O)—OR0, -O-C(═O)—R0 , -O—C(═O)—OR0, -C(═O)—NHR0, or -C(═O)—NR0 R00,
R0, R00 H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X0 halogen, preferably F or Cl.