IP Library › Granted Patent US 9,570,688

Granted Patent B2

US 9,570,688 · App. 14/620,755 · Granted Feb 14, 2017

Semiconductor materials prepared from bridged bithiazole copolymers

Inventors: Ashok Kumar Mishra (Singapore, SG); Subramanian Vaidyanathan (Basel, CH); Hiroyoshi Noguchi (Singapore, SG); Florian Doetz (Singapore, SG); Bo Zhu (Shanghai, CN); Johan Sebastian Basuki (Sydney, AU)

Assignees: BASF SE; Polyera Corporation

H01L51/0071 C07D495/04 C07D513/04 C07D513/14 C08G61/123 C08G61/124 C08G61/126 H01L51/0036 H01L51/0068 H01L51/0074 C08G2261/124 C08G2261/226 C08G2261/228 C08G2261/3223 C08G2261/3243 C08G2261/3246 C08G2261/3327 C08G2261/344 C08G2261/364 C08G2261/414 C08G2261/596 C08G2261/92 H01L51/0508 H01L51/0545

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Quick Facts

Patent No.: US 9,570,688
App. No.: 14/620,755
Granted: Feb 14, 2017
Kind: B2

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Abstract

The present invention provides semiconducting compounds, oligomers and polymers of formula wherein A 1 and A 2 can be the same or different and are S or Se, E is selected from the group consisting of The compounds, oligomers and polymers of formula of formula (1) are suitable for use in electronic devices such as organic field effect transistors.

Claims (333)

1. An oligomer or polymer of formula

wherein

A 1 and A 2 can be the same or different and are S or Se,

E is selected from the group consisting of

wherein

R 1 is H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-20 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 1 —R 6 , —X 2 —Ar 1 , —X 2 —Ar 2 —Ar 1 , —X 2 —Ar 2 —R 7 or —X 2 —Ar 2 —Ar 3 —R 7 ,

wherein

X 1 at each occurrence is independently —O—, —[Z 1 —O] a —, —[O—Z 1 ] a —O—, —S—, —[Z 1 —S—] a —, [S—Z 1 ] a —S—, —S(O), —C(O)—, —C(O)O—, —C(O)NR 8 —, C(O)S—, —O(CO)—, —S(CO)—, —NR 8 C(O)— or —NR 8 —,

wherein

Z 1 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

a at each occurrence is independently an integer from 1 to 10 and

R 8 at each occurrence is independently H, C 1-20 -alkyl, or —Z 2 —C 6-14 -aryl,

wherein

Z 2 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 6 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 2 at each occurrence is independently —Z 3 —O—Z 4 —, —Z 3 —S—Z 4 —, —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 9 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 9 C(O)—, —NR 9 —, —Z 3 —SiR 9 2 —Z 4 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 3 and Z 4 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 9 at each occurrence is independently H, C 1-20 -alkyl, or —Z 5 —C 6-14 -aryl,

wherein

Z 5 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 1 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R a , wherein each R a is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 2 and Ar 3 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R b , wherein each R b is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl, and

R 7 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -halaolkyl, C 1-20 -alkoxy, —X 3 —Ar 4 , —X 3 —Ar 5 —Ar 4 , —X 3 —Ar 5 —R 10 , or —X 3 —Ar 5 —Ar 6 —R 10 ,

wherein

X 3 at each occurrence is independently —Z 6 —O—Z 7 —, —Z 6 —S—Z 7 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 11 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 11 C(O)—, —NR 11 , —Z 6 —SiR 11 2 —Z 7 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 6 and Z 7 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 11 at each occurrence is independently H, C 1-20 -alkyl or —Z 8 —C 6-14 -aryl,

wherein

Z 8 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 4 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R c , wherein each R c is independently selected from the group consisting of halogen, CN, —C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 5 and Ar 6 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R d , wherein each R d is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl, and

R 10 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy,

R 3 , R 4 and R 5 can be the same or different and are H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-20 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 4 —R 12 , —X 5 —Ar 7 , —X 5 —Ar 8 —Ar 7 , —X 5 —Ar 8 —R 13 or —X 5 —Ar 8 —Ar 9 —R 13 ,

wherein

X 4 at each occurrence is independently —[Z 9 —O] b —, —[Z 9 —S—] b —, —S(O)—, —C(O)—, —C(O)O—, —C(O)NR 14 — or C(O)S—,

wherein

Z 9 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

b at each occurrence is independently an integer from 1 to 10 and

R 14 at each occurrence is independently H, C 1-20 -alkyl, or —Z 10 —C 6-14 -aryl,

wherein

Z 10 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 12 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 5 at each occurrence is independently —Z 11 —O—Z 12 , —Z 11 —S—Z 12 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 15 , —C(O)S—, —Z 11 —SiR 15 2 —Z 12 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 11 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

Z 12 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 15 at each occurrence is independently H, C 1-20 -alkyl, or —Z 13 —C 6-14 -aryl,

wherein

Z 13 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 haloalkylene or a covalent bond,

Ar 7 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R e , wherein each R e is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 8 and Ar 9 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R f , wherein each R f is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl and

R 13 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl, C 1-20 -alkoxy, —X 6 —Ar 10 , —X 6 —Ar 11 —Ar 10 , —X 6 —Ar 11 —R 16 , or —X 6 —Ar 11 —Ar 12 —R 17 ,

wherein

X 6 at each occurance is independently —Z 14 —O—Z 15 —, —Z 14 —S—Z 15 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 18 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 18 C(O)—, —NR 18 —, —Z 14 —SiR 18 2 —Z 15 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 14 and Z 15 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 18 at each occurrence is independently H, C 1-20 -alkyl or —Z 16 —C 6-14 -aryl,

wherein

Z 16 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 10 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R g , wherein each R g is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 11 and Ar 12 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R h , wherein each R h is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl and

R 17 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 alkoxy,

R 19 is O or C(CN) 2 , and

R 20 and R 21 are the same or different and are R 22 or CN,

wherein R 22 has the same meaning as R 1 ,

G 1 and G 2 are the same or different and are phenylene or a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue, which phenylene and monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue are optionally substituted with 1 to 4 substituents R i , wherein each R i is independently selected from the group consisting of halogen, —CN, —NO 2 , OH, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, —Z 17 —O—C 1-30 -alkyl, —Z 17 —S—C 1-30 -alkyl, —Z 17 —C 3-10 -cycloalkyl, —Z 17 —C 5-10 -cycloalkenyl, —Z 17 —C 8-10 -cycloalkynyl, —Z 17 —C 6-14 -aryl, —Z 17 -monovalent 3 to 12 membered aliphatic heterocyclic residue and —Z 17 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R j , wherein each R j is independently selected from the group consisting of haloagen, —CN, —NO 2 , *═O, —OH, —NH 2 , —NH(C 1-20 -alkyl), —N(C 1-20 -alkyl) 2 , —N(C 1-20 -alkyl)-C 6-14 -aryl, —N(C 6-14 -aryl) 2 , —S(O) m H, —S(O) m —C 1-20 -alkyl, —S(O) 2 OH, —S(O) m —OC 1-20 -alkyl, —S(O) m —OC 6-14 -aryl, —CHO, —C(O)—C 1-20 -alkyl, —C(O)—C 6-14 -aryl, —C(O)OH, —C(O)—OC 1-20 -alkyl, —C(O)—OC 6-14 -aryl, —C(O)NH 2 , —C(O)NH—C 1-20 -alkyl, —C(O)N(C 1-20 -alkyl) 2 , —C(O)NH—C 6-14 aryl, —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(O)N(C 6-14 -aryl) 2 , —C(S)NH 2 , —C(S)NH—C 1-20 -alkyl, —C(S)N(C 1-20 -alkyl) 2 , —C(S)N(C 6-14 -aryl) 2 , —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(S)NH—C 6-14 -aryl, —S(O) m NH 2 , —S(O) m NH(C 1-20 -alkyl), —S(O) m N(C 1-20 -alkyl) 2 , —S(O) m NH(C 6-14 -aryl), —S(O) m N(C 1-20 -alkyl)-C 6-14 -aryl, —S(O) m N(C 6-14 -aryl) 2 , SiH 3 , SiH(C 1-20 -alkyl) 2 , SiH 2 (C 1-20 -alkyl) and Si(C 1-20 -alkyl) 3 , and

wherein C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, —C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R k , wherein each R k is independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 1-20 -alkoxy, —S—C 1-20 -alkyl, C 1-20 -haloalkyl,

wherein

Z 17 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

m at each occurrence is independently 0, 1 or 2,

L is C 6-24 -arylene or a bivalent 5 to 18 membered aromatic heterocyclic residue, wherein C 6-24 -arylene and bivalent 5 to 18 membered aromatic heterocyclic residue are optionally substituted with 1 to 4 substituents R l , wherein each R l is independently selected from the group consisting of halogen, —CN, —NO 2 , *═O, OH, *═C(C 1-30 -alkyl) 2 , C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, —Z 18 —O—C 1-30 -alkyl, —Z 18 —S—C 1-30 -alkyl, —Z 18 —C 3-10 -cycloalkyl, —Z 18 —C 5-10 -cycloalkenyl, —Z 18 —C 8-10 -cycloalkynyl, —Z 18 —C 6-14 -aryl, —Z 18 -monovalent 3 to 12 membered aliphatic heterocyclic residue and —Z 18 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R m , wherein each R m is independently selected from the group consisting of halogen, —CN, —NO 2 , *═O, —OH, —NH 2 , —NH(C 1-20 -alkyl), —N(C 1-20 -alkyl) 2 , —N(C 1-20 -alkyl)-C 6-14 -aryl, —N(C 6-14 -aryl) 2 , —S(O) o H, —S(O) o —C 1-20 -alkyl, —S(O) 2 OH, —S(O) o —OC 1-20 -alkyl, —S(O) o —OC 6-14 -aryl, —CHO, —C(O)—C 1-20 -alkyl, —C(O)—C 6-14 -aryl, —C(O)OH, —C(O)—OC 1-20 -alkyl, —C(O)—OC 6-14 -aryl, —C(O)NH 2 , —C(O)NH—C 1-20 -alkyl, —C(O)N(C 1-20 -alkyl) 2 , —C(O)NH—C 6-14 -aryl, —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(O)N(C 6-14 -aryl) 2 , —C(S)NH 2 , —C(S)NH—C 1-20 -alkyl, —C(S)N(C 1-20 -alkyl) 2 , —C(S)N(C 6-14 -aryl) 2 , —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(S)NH—C 6-14 -aryl, —S(O) o NH 2 , —S(O) o NH(C 1-20 -alkyl), —S(O) o N(C 1-20 -alkyl) 2 , —S(O) o NH(C 6-14 -aryl), —S(O) o N(C 1-20 -alkyl)-C 6-14 -aryl, —S(O) o N(C 6-14 -aryl) 2 , SiH 3 , SiH(C 1-20 -alkyl) 2 , SiH 2 (C 1-20 -alkyl) and Si(C 1-20 -alkyl) 3 , and

wherein C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, —C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R n , wherein each R n is independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 1-20 -alkoxy, —S—C 1-20 -alkyl, C 1-20 -haloalkyl,

wherein

Z 18 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

o at each occurrence is independently 0, 1 or 2,

L is

wherein

R 23 and R 24 can be the same or different and are H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-20 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 7 —R 25 , —X 8 —Ar 13 , —X 8 —Ar 14 —Ar 13 , —X 8 —Ar 14 —R 26 or —X 8 —Ar 14 —Ar 15 —R 26 ,

wherein

X 7 at each occurrence is independently —O—, —[Z 19 —O] c —, —[O—Z 19 ] c —O—, —S—, —[Z 19 —S—] c —, —[S—Z 19 ] c —S—, —S(O), —C(O)—, —C(O)O—, —C(O)NR 27 —, C(O)S—, —O(CO)—, —S(CO)—, —NR 27 C(O)— or —NR 27 —,

wherein

Z 19 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

c at each occurrence is independently an integer from 1 to 10 and

R 27 at each occurrence is independently H, C 1-20 -alkyl, or —Z 20 —C 6-14 -aryl,

wherein

Z 20 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 25 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 8 at each occurrence is independently —Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 28 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 28 C(O)—, —NR 28 —, —Z 21 —SiR 28 2 —Z 22 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 21 and Z 22 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 28 at each occurrence is independently H, C 1-20 -alkyl, or —Z 23 —C 6-14 -aryl,

wherein

Z 23 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 12 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic hetrocyclic residue, each optionally substituted with 1 to 5 substituents R o , wherein each R o is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 14 and Ar 15 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R p , wherein each R p is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl, and

R 26 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl, C 1-20 -alkoxy, —X 9 —Ar 16 , —X 9 —Ar 17 —Ar 16 , —X 9 —Ar 17 —R 29 , or —X 9 —Ar 17 —Ar 18 —R 29 ,

wherein

X 9 at each occurrence is independently —Z 24 —O—Z 25 —, —Z 24 —S—Z 25 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 30 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 30 C(O)—, —NR 30 —, —Z 24 —SiR 30 2 —Z 25 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 24 and Z 25 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 30 at each occurrence is independently H, C 1-20 -alkyl or —Z 26 —C 6-14 -aryl,

wherein

Z 26 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 16 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R q , wherein each R q is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

Ar 17 and Ar 18 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R r , wherein each R r is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl, and

R 29 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy,

q and s are the same or different and are 0, 1, 2, 3, 4 or 5,

r is 0, 1 or 2,

and

n is an integer from 2 to 10,000.

2. The oligomer or polymer of formula (1) of claim 1 wherein E is

3. An oligomer or polymer of formula (1)

wherein

A 1 and A 2 can be the same or different and are S or Se,

E is selected from the group consisting of

wherein

R 1 is H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 cycloakynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 1 —R 6 , —X 2 —Ar 1 , —X 2 —Ar 2 —Ar 1 , —X 2 —Ar 2 R 7 or —X 2 —Ar 2 —Ar 3 —R 7 ,

wherein

X 1 at each occurrence is independently —O—, —[Z 1 —O] a —, —[O—Z 1 ] a —O—, —S—, —[Z 1 —S—] a —, —[S—Z 1 ] a —S—, —S(O), —C(O)—, —C(O)O—, —C(O)NR 8 —, C(O)S—, —O(CO)—, —S(CO)—, —NR 8 C(O)— or —NR 8 —,

wherein

Z 1 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

a at each occurrence is independently an integer from 1 to 10 and

R 8 at each occurrence is independently H, C 1-20 -alkyl, or —Z 2 —C 6-14 -aryl,

wherein

Z 2 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 6 at each occurrence is independently C 1-30 -alkyl, C 2-30 alkenyl or C 1-30 -haloalkyl,

wherein

Z 3 and Z 4 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 9 at each occurrence is independently H, C 1-20 -alkyl, or —Z 5 —C 6-14 -aryl,

wherein

Z 5 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 2 and Ar 3 at each occurrence are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue each optionally substituted with 1 to 4 substituents R b , wherein each R b is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl and

R 7 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl, C 1-20 -alkoxy, —X 3 —Ar 4 , —X 3 —Ar 5 —Ar 4 , ——X 3 —Ar 5 —R 10 , or —X 3 —Ar 5 —Ar 6 —R 10 ,

wherein

X 3 at each occurrence is independently —Z 6 —O—Z 7 —, —Z 6 —S—Z 7 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 11 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 11 C(O)—, —NR 11 —, —Z 6 —SiR 11 2 —Z 7 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 6 and Z 7 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 11 at each occurrence is independently H, C 1-20 -alkyl or —Z 8 —C 6-14 aryl,

wherein

Z 8 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 4 at each occurrence is independently C 6-14 -aryl movalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R c , wherein each R c is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

R 10 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy,

R 4 and R 5 can be the same or different and are H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-20 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 4 —R 12 , —X 5 —Ar 7 , —X 5 —Ar 8 —Ar 7 , —X 5 —Ar 8 —R 13 or —X 5 —Ar 8 —Ar 9 —R 13 ,

wherein

X 4 at each occurrence is independently —[Z 9 —O] b —, —[Z 9 —S—] b —, —S(O)—, —C(O)—, —C(O)O—, —C(O)NR 14 — or C(O)S—,

wherein

Z 9 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

b at each occurrence is independently an integer from 1 to 10 and

R 14 at each occurrence is independently H, C 1-20 -alkyl, or —Z 10 —C 6-14 -aryl,

wherein

Z 10 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 12 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 5 at each occurrence is independently —Z 11 —O—Z 12 , —Z 11 —S—Z 12 —, —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 15 , —C(O)S—, —Z 11 —SiR 15 2 —Z 12 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 11 at each occurrence is independently C 1-6 alkylene, C 2-6 alkenylene or C 1-6 -haloalkylene,

Z 12 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 15 at each occurrence is independently H, C 1-20 -alkyl, or 13 Z 13 —C 6-14 -aryl,

wherein

Z 13 at each occurrence is independently C 1-6 -alkylene, C 2-6 alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 7 at each occurrence is independently C 6-14 aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R e ,wherein each R e is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

wherein

X 6 at each occurrence is independently —Z 14 —O—Z 15 —, —Z 14 —S—Z 15 , —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 18 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 18 C(O)—, —NR 18 —, —Z 14 —SiR 18 2 —Z 15 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 14 and Z 15 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 18 at each occurrence is independently H, C 1-20 -alkyl or —Z 16 —C 6-14 -aryl,

wherein

Z 16 at each occurrence is independently C 1-6 -alkylene, C 2-6 alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 17 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy,

R 19 is O or C(CN) 2 , and

R 20 and R 21 are the same or different and are R 22 or CN,

wherein R 22 has the same meaning as R 1 ,

G 1 and G 2 are same or different and are phenylene or a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue, which phenylene and monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue are optionally substituted with 1 to 4 substituents R i , wherein each R i is independently selected from the group consisting of halogen, —CN, —NO 2 , OH, C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, —Z 17 —O—C 1-30 -alkyl, —Z 17 —C 1-30 -alkyl, —Z 17 —C 3-10 -cycloalkyl, —Z 17 —C 5-10 -cycloalkenyl, —Z 17 —C 8-10 -cycloalkynyl, —Z 17 —C 6-14 -aryl, —Z 17 -monovalent3 to 12 membered aliphatic heterocyclic residue and —Z 17 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R j , wherein each R j is independently selected from the group consisting of halogen, —CN, —NO 2 , *═O, —OH, —NH 2 , —NH(C 1-20 -alkyl), —N(C 1-20 -alkyl) 2 , —N(C 1-20 -alkyl)-C 6-14 -aryl, —N(C 6-14 -aryl) 2 , —S(O) m H, —S(O) m —C 1-20 -alkyl, —S(O) 2 OH, —S(O) m —OC 1-20 -alkyl, —S(O) m —OC 6-14 -aryl, —CHO, —C(O)—C 1-20 -alkyl, —C(O)—C 6-14 -aryl, —C(O)OH, —C(O)—OC 1-20 -alkyl, —C(O)—OC 6-14 -aryl, —C(O)NH 2 , —C(O)NH—C 1-20 -alkyl, —C(O)N(C 1-20 -alkyl) 2 , —C(O)NH—C 6-14 -aryl, —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(O)N(C 6-14 -aryl) 2 , —C(S)NH 2 , —C(S)NH—C 1-20 -alkyl, —C(S)N(C 1-20 -alkyl) 2 ,—C(S)N(C 6-14 -aryl) 2 , —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(S)NH—C 6-14 -aryl, —S(O) m NH 2 , —S(O) m NH(C 1-20 -alkyl), —S(O) m N(C 1-20 -alkyl) 2 , —S(O) m NH(C 6-14 aryl), —S(O) m N(C 1-20 -alkyl)-C 6-14 -aryl, —S(O) m N(C 6-14 aryl) 2 , SiH 3 , SiH(C 1-20 -alkyl) 2 , SiH 2 (C 1-20 -alkyl) and Si(C 1-20 -alkyl) 3 , and

wherein

Z 17 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

m at each occurrence is independently 0, 1 or 2,

wherein C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R m , wherein each R m is independently selected from the group consisting of halogen, —CN, —NO 2 , *═O, —OH, —NH 2 , —NH(C 1-20 -alkyl), —N(C 1-20 -alkyl) 2 , —N(C 1-20 -alkyl)-C 6-14 -aryl, —N(C 6-14 -aryl) 2 , —S(O) o H, —S(O) o —C 1-20 -alkyl, —S(O) 2 OH, —S(O) o —OC 1-20 -alkyl, —S(O) o —OC 6-14 -aryl, —CHO, —C(O)—C 1-20 -alkyl, —C(O)—C 6-14 -aryl, —C(O)OH, —C(O)—OC 1-20 -alkyl, —C(O)—OC 6-14 -aryl, —C(O)NH 2 , —C(O)NH—C 1-20 -alkyl, —C(O)N(C 1-20 -alkyl) 2 , —C(O)NH—C 6-14 -aryl, —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(O)N(C 6-14 -aryl) 2 , —C(S)NH 2 , —C(S)NH—C 1-20 alkyl, —C(S)N(C 1-20 -alkyl) 2 , —C(S)N(C 6-14 -aryl) 2 , —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, —C(S)NH—C 6-14 -aryl, —S(O) o NH 2 , —S(O) o NH(C 1-20 -alkyl), —S(O) o N(C 1-20 -alkyl) 2 , —S(O) o NH(C 6-14 -aryl), —S(O) o N(C 1-20 -alkyl)-C 6-14 -aryl, —S(O) o N(C 6-14 -aryl) 2 , SiH 3 , SiH(C 1-20 -alkyl) 2 , SiH 2 (C 1-20 -alkyl) and Si(C 1-20 -alkyl) 3 , and

wherein C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, —C 8-10 -cycloalkynyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R n , wherein each R n is independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 1-20 -alkoxy, —S—C 1-20 -alkyl, C 1-20 -haloalkyl,

wherein

Z 18 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

o at each occurrence is independently 0, 1 or 2,

L is

wherein

Z 19 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

c at each occurrence is independently an integer from 1 to 10 and

R 27 at each occurrence is independently H, C 1-20 -alkyl, or —Z 20 —C 6-14 -aryl,

wherein

Z 20 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 25 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 8 at each occurrence is independently —Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, —S(O)—, —C(O)—, —C(O)O—, —(CO)NR 28 , —C(O)S—, —O(CO)—, —S(CO)—, —NR 28 C(O)—, —NR 28 —, —Z 21 —SiR 28 2 —Z 22 —, C 1-30 -alkylene, C 2-30 -haloalkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 21 and Z 22 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 28 at each occurrence is independently H, C 1-20 -alkyl, or —Z 23 —C 6-14 -aryl,

wherein

Z 23 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 12 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R o , wherein each R o is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

wherein

Z 24 and Z 25 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

R 30 at each occurrence is independently H, C 1-20 -alkyl or —Z 26 —C 6-14 -aryl,

wherein

Z 26 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 16 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue. each optionally substituted with 1 to 5 substituents R q , wherein each R q is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

R 29 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy,

q and s are the same or different and are 0, 1, 2, 3, 4 or 5,

r is 0, 1 or 2,

and

n is an integer from 2 to 10,000,

wherein R 3 is —X 5 —Ar 7 , —X 5 —Ar 8 —Ar 7 , —X 5 Ar 8 —R 13 or —X 5 —Ar 8 —Ar 9 —R 13 ,

wherein

X 5 at each occurrence is a covalent bond,

R 13 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy.

4. The oligomer or polymer of formula (1) of claim 1 , wherein R 3 is —X 5 —Ar 8 —R 13 ,

wherein

X 5 is a covalent bond,

Ar 8 is C 6-14 -arylene, and

R 13 is C 1-20 -alkyl.

5. The oligomer or polymer of formula (1) of claim 1 , wherein G 1 and G 2 are the same or different and are phenylene,

or, a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue selected from the group consisting of

which phenylene or monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue are optionally substituted with 1 to 2 substituents R i , wherein each R i is independently selected from the group consisting of C 1-30 -alkyl, —Z 17 —O—C 1-30 -alkyl, —Z 17 —S—C 1-30 -alkyl, —Z 17 —C 3-10 -cycloalkyl, —Z 17 —C 6-14 -aryl, —Z 17 -monovalent 3 to 12 membered aliphatic heterocyclic residue and —Z 17 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein C 1-30 -alkyl, C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R j , wherein each R j is independently selected from the group consisting of halogen, —CN and *═O, and

wherein C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R k , wherein each R k is independently selected from the group consisting of C 1-20 -alkyl, C 1-20 -alkoxy, C 1-20 -haloalkyl,

wherein

Z 17 at each occurrence is independently C 1-6 -alkylene, C 1-6 -haloalkylene or a covalent bond.

6. The oligomer or polymer of formula (1) of claim 1 , wherein G 1 and G 2 are the same or different and are a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue which monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue is

which monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue is substituted with 1 to 2 substituents R i , wherein each R i is independently selected from the group consisting of C 1-30 -alkyl and —Z 17 —C 6-14 -aryl,

wherein C 1-30 -alkyl and C 6-14 -aryl are optionally substituted with 1 to 4 substituents R j , wherein each R j is independently selected from the group consisting of halogen, —CN and *═O, and

wherein C 6-14 -aryl is optionally substituted with 1 to 4 substituents R k , wherein each R k is independently selected from the group consisting of C 1-20 -alkyl and C 1-20 -alkoxy,

wherein

Z 17 at each occurrence is a covalent bond.

7. The oligomer or polymer of formula (1) of claim 1 , wherein each R i is independently C 1-30 -alkyl.

8. The oligomer or polymer of formula (1) of claim 1 , wherein

L is a bivalent 5 to 18 membered aromatic heterocyclic residue, wherein the bivalent 5 to 18 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R l , wherein each R l is independently selected from the group consisting of C 1-30 -alkyl, —Z 18 —O—C 1-30 -alkyl, —Z 18 —S—C 1-30 -alkyl, —Z 18 —C 3-10 -cycloalkyl, —Z 18 —C 6-14 -aryl, —Z 18 -monovalent 3 to 12 membered aliphatic heterocyclic residue and —Z 18 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein C 1-30 -alkyl, C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R m , wherein each R m is independently selected from the group consisting of halogen, —CN and *═O, and

wherein C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R n , wherein each R n is independently selected from the group consisting of C 1-20 -alkyl, C 1-20 -alkoxy, C 1-20 -haloalkyl,

wherein

Z 18 at each occurrence is independently C 1-6 -alkylene, C 1-6 -haloalkylene or a covalent bond,

L is

wherein

R 23 and R 24 are the same or different and are H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 1-30 -haloalkyl, —X 7 —R 25 , —X 8 —Ar 13 , —X 8 —Ar 14 —Ar 13 , —X 8 —Ar 14 —R 26 or —X 8 —Ar 14 —Ar 15 —R 26 ,

wherein

X 7 at each occurrence is independently —O—, —[Z 19 —O] c —, —[O—Z 19 ] c —O—, —S—, —[Z 19 —S—] c — or —[S—Z 19 ] c —S—,

wherein

Z 19 at each occurrence is independently C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene,

c at each occurrence is independently an integer from 1 to 10 and

R 25 at each occurrence is independently C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 8 at each occurrence is independently —Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, C 1-30 alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein

Z 21 and Z 22 at each occurrence are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and

Ar 13 at each occurrence is independently C 6-14 -aryl or monovalent 5 to 14 membered aromatic hetrocyclic residue, each optionally substituted with 1 to 5 substituents R o , wherein each R o is independently selected from the group consisting of halogen, CN, C 1-6 -alkyl, C 1-6 -alkoxy and C 1-6 -haloalkyl,

R 26 at each occurrence is independently C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy.

9. The oligomer or polymer of formula (1) of claim 1 , wherein

L is a bivalent 5 to 18 membered aromatic heterocyclic residue selected from the group consisting of

wherein the bivalent 5 to 18 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R 1 , wherein each R 1 is selected from the group consisting of a C 1-30 -alkyl, a —Z 18 —O—C 1-30 -alkyl, a —Z 18 —S—C 1-30 -alkyl, a —Z 18 —C 3-10 -cycloalkyl, a —Z 18 —C 6-14 -aryl, a —Z 18 -monovalent 3 to 12 membered aliphatic heterocyclic residue and a —Z 18 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein

C 1-30 -alkyl, C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R m , wherein R m is selected from the group consisting of a halogen, a —CN and a *═O,

C 3-10 -cycloalkyl, C 6-14 -aryl, monovalent 3 to 12 membered aliphatic heterocyclic residue and monovalent 5 to 14 membered aromatic heterocyclic residue is optionally substituted with 1 to 4 substituents R n , wherein R n is selected from the group consisting of a C 1-20 -alkyl, a C 1-20 -alkoxy, and a C 1-20 -haloalkyl, and

Z 18 is C 1-6 -alkylene, C 1-6 -haloalkylene or a covalent bond, and

wherein R t is hydrogen or C 1-30 -alkyl,

L is

wherein

R 23 and R 24 are independently H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 1-30 -haloalkyl, —X 7 —R 25 , —X 8 —Ar 13 , —X 8 —Ar 14 —Ar 13 , —X 8 —Ar 14 —R 26 or X 8 —Ar 14 —Ar 15 —R 26 ,

wherein

X 7 is —O—, —[Z 19 —O] c —, —[O—Z 19 ] c —O—, —S—, —[Z 19 —S—] c — or —[S—Z 19 ] c —S—,

wherein

Z 19 is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, and

c is an integer of from 1 to 10,

R 25 is C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 8 is —Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein Z 21 and Z 22 are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

Ar 13 is C 6-14 -aryl or monovalent 5 to 14 membered aromatic hetrocyclic residue, each optionally substituted with 1 to 5 substituents R o , wherein R o is selected from the group consisting of a halogen, a CN, a C 1-6 -alkyl, a C 1-6 -alkoxy and a C 1-6 -haloalkyl,

Ar 14 and Ar 15 are independently C 6-14 -arylene or bivalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R p , wherein R p is selected from the group consisting of a halogen, a CN, a C 1-6 -alkyl, a C 1-6 -alkoxy and a C 1-6 -haloalkyl, and

R 26 is C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy.

10. The oligomer or polymer of formula (1) of claim 1 , wherein

L is

wherein each R 1 is selected from the group consisting of a C 1-30 -alkyl, a —Z 18 —O—C 1-30 -alkyl, a —Z 18 —S—C 1-30 -alkyl, a —Z 18 —C 3-10 -cycloalkyl, a —Z 18 —C 6-14 -aryl, a —Z 18 -monovalent 3 to 12 membered aliphatic heterocyclic residue and a —Z 18 -monovalent 5 to 14 membered aromatic heterocyclic residue,

wherein

Z 18 is C 1-6 -alkylene, C 1-6 -haloalkylene or a covalent bond,

L is

wherein R 23 and R 24 independently H, halogen, —CN, C 1-30 -alkyl, C 2-30 -alkenyl, C 1-30 -haloalkyl, —X 7 —R 25 , —X 8 —Ar 13 , —X 8 —Ar 14 —Ar 13 , —X 8 —Ar 14 —R 26 or —X 8 —Ar 14 —Ar 15 —R 26 ,

wherein

X 7 is —O—, —[Z 19 —O] c —, —[O—Z 19 ] c —, —S—, —[Z 19 —S—] c — or —[S—Z 19 ] c —S—,

wherein

Z 19 is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, and

c is an integer of from 1 to 10,

R 25 is C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl,

X 8 is Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, C 1-30 -alkylene, C 2-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,

wherein Z 21 and Z 22 are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond,

R 26 is C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy.

11. The oligomer or polymer of formula (1) of claim 1 , wherein q, r and s are 0 or 1, with the proviso that q, r and s are not all 0 at the same time.

12. The oligomer or polymer of formula (1) of claim 1 , wherein n is an integer from 2 to 5000.

13. An electronic device comprising the oligomer or polymer of formula (1) of claim 1 .

14. The electronic device of claim 13 , wherein the electronic device is an organic field effect transistor.

15. The oligomer or polymer of formula (1) of claim 4 , wherein Ar 8 is phenylene.

16. The oligomer or polymer of formula (1) of claim 1 , wherein n is an integer from 2 to 1000.

17. The oligomer or polymer of formula (1) of claim 1 , wherein n is an integer from 2 to 100.

18. The oligomer or polymer of formula (1) of claim 1 , wherein n is an integer from 2 to 30.

19. The oligomer or polymer of formula (1) of claim 1 , wherein R 3 is H, halogen, —CN, C 2-30 -alkenyl, C 2-20 -alkynyl, C 3-10 -cycloalkyl, C 5-10 -cycloalkenyl, C 8-10 -cycloalkynyl, C 1-30 -haloalkyl, monovalent 3 to 12 membered aliphatic heterocyclic residue, —X 4 —R 12 , —X 5 —Ar 7 , —X 5 —Ar 8 —Ar 7 , —X 5 —Ar 8 —R 13 or —X 5 —Ar 8 —Ar 9 —R 13 .

20. The oligomer or polymer of formula (1) of claim 1 , wherein each R i is independently n-octyl, n-(2-ethyl)hexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-icosyl (C 20 ).

21. The oligomer or polymer of formula (1) of claim 1 , wherein each R i is n-dodecyl.

Assignments (6)

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