Diketopyrrolopyrrole polymers for use in organic semiconductor devices

A polymer, comprising:

• a unit of formula *A*;
• a unit of formula *COM1*;
• and
• optionally, a unit of formula*COM2*,
• wherein A is a repeating unit of formula (I)
• wherein
• a is 1, 2, or 3,
• a′ is 0, 1, 2, or 3,
• b is 0, 1, 2, or 3,
• b′ is 1, 2, or 3,
• c is 0, 1, 2, or 3,
• c′ is 0, 1, 2, or 3,
• d is 0, 1, 2, or 3,
• d′ is 0, 1, 2, or 3,
• with the proviso that b′ is not 0, if a′ is 0,
• R1 and R2 are the same or different and are (a) hydrogen, (b) a C1-C100 alkyl group, (c) —COOR103, (c) a C1-C100 alkyl group which is at least one of (i) substituted by at least one halogen atom, hydroxyl group, nitro group, —CN, or C6-C18 aryl group and (ii) interrupted by —O—, —COO—, or —S—, (d) a C7-C100 arylalkyl group, (e) a carbamoyl group, (f) C5-C12 cycloalkyl, which is optionally substituted one to three times with at least one selected from the group consisiting of C1-C8 alkyl and C1,-C8 alkoxy, (g) a C6-C24 aryl group which is optionally substituted one to three times with at least one selected from the group consisting of C1,-C8 alkyl, C1-C8 thioalkoxy, and C1-C8 alkoxy, or (h) pentafluorophenyl,
• R103 is C1-C50 alkyl,
• Ar1and Ar1′ are independently of each other
• wherein one of X3 and X4 is N and the other is CR99,
• Ar2, Ar2′, Ar3, Ar3′, Ar4, and Ar4′ have the meaning of Ar1, or are independently of each other
• R99, R104, and R104′ are independently of each other (i) hydrogen, (j) halogen, (k) a C1-C25 alkyl group which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (1) C7-C25 arylalkyl, or (m) a C1-C25 alkoxy group,
• R105and R105′ independently of each other are (n) hydrogen, (o) halogen, (p) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (q) C7-C25 arylalkyl, or (r) C1-C18 alkoxy,
• R107 is (s) H, (t) C6-C18 aryl, C6-C18 aryl which is substituted by C1-C18 alkyl or C1-C18 alkoxy, (u) C1-C18 alkyl, or (v) C1-C18 alkyl which is interrupted by —O—,
• -COM1- is a repeating unit of formula
• wherein R9 is C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, C1-C25 perfluoroalkyl, C1-C25 alkoxy, or CN,
• -COM2- is a second repeating unit -COM1- , which is different from the first repeating unit -COM1-, a second repeating unit -A-, which is different from the first repeating unit -A-, or a repeating unit of formula
• wherein one of X5 and X6 is N and the other is CR114,
• R110 is (w) a C1-C25 alkyl group which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (x) C7-C25 arylalkyl, or (y) a C1-C25 alkoxy group
• R111, R111′, R112,and R112′ are independently of each other (z) hydrogen, (aa) halogen, (ab) a C1-C25 alkyl group which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (ac) C7-C25 arylalkyl, or (ad) a C1-C25 alkoxy group,
• R113 is (ae) C6-C18 aryl, (af) C6-C18 aryl which is substituted by C1-C18 alkyl, (ag) C1-C18 alkoxy or C1-C18 alkyl, or (ah) C1-C18 alkyl which is interrupted by —O—,
• R114, R114′, R115 and R115′ are independently of each other (ai) H or (aj) a C1-C25 alkyl group which is optionally interrupted by at least one oxygen atom,
• p is 0, 1, 2, or 3,
• r is 0 or 1,
• s is 0 or 1,
• one of R106 and R108 is hydrogen and the other is hydrogen, CN, C1-C8 alkyl, or —COOR109,
• R109 is (ak) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (al) C7-C25 arylalkyl, or (am) C6-C24 aryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy;
• R3 and R3′ are independently of each other (an) hydrogen, (ao) halogen, (ap) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (aq) C7-C25 arylalkyl, or (ar) C1-C25 alkoxy,
• R4 and R4′ are independently of each other (as) halogen, (at) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (au) C7-C25 arylalkyl, or (av) C1-C25 alkoxy;
• or two neighboring R4 and R4′ groups form a ring with each other,
• X1 and X2 are independently of each other —O—, —S—, —NR8—, —Si(R11)(R11′)—, —C(R7)(R7′)—,—C(═O)—,
• X5 is —O— or —NR8—,
• R5 and R5′ are independently of each other (aw) hydrogen, (ax) halogen, (ay) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (az) C6-C24 aryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy, (ba) C7-C25 arylalkyl, (bb) CN, or (bc) C1-C25 alkoxy,
• or R5 and R5′ together form a ring,
• R55 and R55′ are independently of each other (bd) H, (be) F, (bf) C1-C18 alkyl, (bg) C1-C18 alkyl which is interrupted by O, (bh) C1-C18 alkoxy, (bi) C1-C18 alkoxy which is interrupted by O, (bj) C1-C18 perfluoroalkyl, (bk) C6-C24 aryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy, or (bl) C2-C20 heteroaryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy,
• R6 is (bm) H, (bn) C1-C18 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, (bo) C1-C18 perfluoroalkyl, (bp) C6-C24 aryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy, (bq) C2-C20 heteroaryl which is optionally substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy, or (br) CN,
• R7 and R7′ are independently of each other (bs) hydrogen, (bt) C1-C35 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, or (bu) C7-C25 arylalkyl,
• R8 and R8′ are independently of each other (by) hydrogen, (bw) C6-C18 aryl, (bx) C6-C18 aryl which is substituted by C1-C18 alkyl or C1-C1 8alkoxy, (by) C1-C25 alkyl which is optionally interrupted by at least one selected from the group consisting of an oxygen atom and a sulfur atom, or (bz) C7-C25 arylalkyl,
• R11 and R11′ are independently of each other (ca) C1-C35 alkyl group, (cb) C7C25 arylalkyl, or (cc) a phenyl group, which are each optionally substituted one to three times with at least one selected from the group consisting of C1-C8alkyl and C1-C8alkoxy,
• with the proviso that the following polymer is excluded
• (Mn=22.7 K;
• polydispersity=2.1).