US 11,839,155 B2
Organic semiconducting compounds
William Mitchell, Chandler's Ford (GB); Agnieszka Pron, Eastleigh (GB); Mansoor D'Lavari, Southampton (GB); Kane Heard, Southampton (GB); Jonathan Snow, Salisbury (GB); Ignasi Burgues, Southampton (GB); and Quentin Huaulme, Southampton (GB)
Assigned to RAYNERGY TEK INC., Hsinchu (TW)
Appl. No. 17/042,662
Filed by RAYNERGY TEK INCORPORATION, Hsinchu (TW)
PCT Filed Mar. 26, 2019, PCT No. PCT/EP2019/057499
§ 371(c)(1), (2) Date Sep. 28, 2020,
PCT Pub. No. WO2019/185578, PCT Pub. Date Oct. 3, 2019.
Claims priority of application No. 18164638 (EP), filed on Mar. 28, 2018.
Prior Publication US 2022/0320445 A1, Oct. 6, 2022
Int. Cl. H10K 85/60 (2023.01); C07D 495/04 (2006.01); C07D 495/22 (2006.01); H10K 85/20 (2023.01); H10K 10/46 (2023.01); H10K 30/30 (2023.01)
CPC H10K 85/6576 (2023.02) [C07D 495/04 (2013.01); C07D 495/22 (2013.01); H10K 85/211 (2023.02); H10K 85/655 (2023.02); H10K 85/657 (2023.02); H10K 10/488 (2023.02); H10K 30/30 (2023.02)] 25 Claims
 
1. A compound of formula I

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wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
Ar1, Ar2 are a group selected from the following formulae

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Ar3 is a group selected from the following formulae and their mirror images

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Ar4 is a group selected from the following formulae and their mirror images

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Ar5 is a group selected from the following formulae and their mirror images

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Ar6,7 are arylene or heteroarylene that has from 5 to 20 ring atoms, is mono- or polycyclic, optionally contains fused rings, and is unsubstituted or substituted by one or more identical or different groups R1 or LS, or CY1═CY2 or —C≡C—,
U1, U2 are CR1R2, SiR1R2, GeR1R2, C═CR1R2, NR1 or C═O,
V1 is CR3 or N,
W1, W2, W3 are S, O, Se or C═O,
W4 is S, O, Se, C═O or NR1,
R1-9 is 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 LS,
and the pair of R1 and R2, together with the C, Si or Ge atom to which they are attached, may also form a spiro group with 5 to 20 ring atoms which is mono- or polycyclic, does optionally contain fused rings, and is unsubstituted or substituted by one or more identical or different groups LS,
RT1, RT2 are an electron withdrawing group,
Y1, Y2 are H, F, Cl or CN,
LS is 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, —NR0R00, —C(═O)NHR0, —C(═O)NR0R00, —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,
R0, R00 are H or straight-chain or branched alkyl with 1 to 20 C atoms that is optionally fluorinated,
X0 is halogen,
a, b are 0 or an integer from 1 to 10,
k is an integer from 1 to 10,
m is 0 or an integer from 1 to 10,
wherein at least one of RT1 and RT2 is an electron withdrawing group of formula TG

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Ar8 is bi- or polycyclic arylene or heteroarylene having from 5 to 20 ring atoms which is optionally substituted with one or more groups L,
L is 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, —NR0R00, —C(═O)NHR0, —C(═O)NR0R00, —SO3R0, —SO2R0, —OH, —NO2, —CF3, —SF5,
Z1, Z2 are O or C(CN)2,
and wherein at least one group Ar3 denotes thieno[3,2-b]thiophene and/or at least one of the groups Ar4 and Ar5 denotes thieno[3,2-b]thiophene that is optionally substituted with R3.