Semiconductor materials prepared from bridged bithiazole copolymers

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.

1 . A compound of formula 
       
         
           
           
               
               
           
         
         wherein 
         A 1  and A 2  are independently S or Se, 
         E is selected from the group consisting of 
       
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are independently 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  is —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  is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, 
 a is an integer of from 1 to 10, and 
 R 8  is H, C 1-20 -alkyl, or —Z 2 —C 6-14 -aryl,
 wherein 
 Z 2  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 R 6  is C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl, 
 X 2  is —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  are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 9  is H, C 1-20 -alkyl, or —Z 5 —C 6-14 -aryl,
 wherein 
 Z 5  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 Ar 1  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic hetrocyclic residue, each optionally substituted with 1 to 5 substituents R a , wherein R a  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 2  and Ar 3  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 R b  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 7  is 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  is —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  are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 11  is H, C 1-20 -alkyl or —Z 8 —C 6-14 -aryl, 
  wherein 
  Z 8  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 Ar 4  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R c , wherein R c  is independently 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 5  and Ar 6  at 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 R d  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 10  is C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy, 
 
 
         R 3 , R 4  and R 5  are independently 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  is —[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  is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, 
 b is an integer of from 1 to 10, and 
 R 14  is H, C 1-20 -alkyl, or —Z 10 —C 6-14 -aryl,
 wherein 
 Z 10  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 R 12  is C 1-30 -alkyl, C 2-30 -alkenyl or C 1-30 -haloalkyl, 
 X 5  is —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  is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, 
 Z 12  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 15  is H, C 1-20 -alkyl, or —Z 13 —C 6-14 -aryl,
 wherein 
 Z 13  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 Ar 7  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R e , wherein R e  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 8  and Ar 9  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 R f  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 13  is 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  is —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  are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 18  is H, C 1-20 -alkyl or —Z 16 —C 6-14 -aryl, 
  wherein 
  Z 16  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 Ar 10  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R g , wherein R g  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 11  and Ar 12  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 R h  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 17  is 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 independently R 22  or CN,
 wherein R 22  has the same meaning as R 1 , 
 
         G 1  and G 2  are independently phenylene or a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R i , wherein R i  is selected from the group consisting of a halogen, a —CN, a —NO 2 , a OH, a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a —Z 17 —O—C 1-30 -alkyl, a —Z 17 —S—C 1-30 -alkyl, a —Z 17 —C 3-10 -cycloalkyl, a —Z 17 —C 5-10 -cycloalkenyl, a —Z 17 —C 8-10 -cycloalkynyl, a —Z 17 —C 6-14 -aryl, a —Z 17 -monovalent 3 to 12 membered aliphatic heterocyclic residue and a —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 are optionally substituted with 1 to 4 substituents R j , wherein R j  is selected from the group consisting of a halogen, a —CN, a —NO 2 , a *═O, a —OH, a —NH 2 , a —NH(C 1-20 -alkyl), a —N(C 1-20 -alkyl) 2 , a —N(C 1-20 -alkyl)-C 6-14 -aryl, a —N(C 6-14 -aryl) 2 , a —S(O) m H, a —S(O) m —C 1-20 -alkyl, a —S(O) 2 OH, a —S(O) m —OC 1-20 -alkyl, a —S(O) m —OC 6-14 -aryl, a —CHO, a —C(O)—C 1-20 -alkyl, a —C(O)—C 6-14 -aryl, a —C(O)OH, a —C(O)—OC 1-20 -alkyl, a —C(O)—OC 6-14 -aryl, a —C(O)NH 2 , a —C(O)NH—C 1-20 -alkyl, a —C(O)N(C 1-20 -alkyl) 2 , a —C(O)NH—C 6-14 -aryl, a —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, a —C(O)N(C 6-14 -aryl) 2 , a —C(S)NH 2 , —C(S)NH—C 1-20 -alkyl, a —C(S)N(C 1-20 -alkyl) 2 , a —C(S)N(C 6-14 -aryl) 2 , a —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, a —C(S)NH—C 6-14 -aryl, a —S(O) m NH 2 , a —S(O) m NH(C 1-20 -alkyl), a —S(O) m N(C 1-20 -alkyl) 2 , a —S(O) m NH(C 6-14 -aryl), a —S(O) m N(C 1-20 -alkyl)-C 6-14 -aryl, a —S(O) m N(C 6-14 -aryl) 2 , a SiH 3 , a SiH(C 1-20 -alkyl) 2 , a SiH 2 (C 1-20 -alkyl) and a Si(C 1-20 -alkyl) 3 ,
 wherein m is an integer of 0, 1 or 2, 
 
 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 R k  is selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl, a C 2-20 -alkynyl, a C 1-20 -alkoxy, a —S—C 1-20 -alkyl, and a C 1-20 -haloalkyl, and 
 Z 17  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
         L is C 6-24 -arylene or a bivalent 5 to 18 membered aromatic heterocyclic residue, each optionally substituted with 1 to 4 substituents R l , wherein R l  is selected from the group consisting of a halogen, a —CN, a —NO 2 , a *═O, a OH, a *═C(C 1-30 -alkyl) 2 , a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, 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 5-10 -cycloalkenyl, a —Z 18 —C 8-10 -cycloalkynyl, 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 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 are optionally substituted with 1 to 4 substituents R m , wherein R m  is selected from the group consisting of a halogen, a —CN, a —NO 2 , a *═O, a —OH, a —NH 2 , a —NH(C 1-20 -alkyl), a —N(C 1-20 -alkyl) 2 , a —N(C 1-20 -alkyl)-C 6-14 -aryl, a —N(C 6-14 -aryl) 2 , a —S(O) m H, a —S(O) o —C 1-20 -alkyl, a —S(O) 2 OH, a —S(O) o —OC 1-20 -alkyl, a —S(O) o —OC 6-14 -aryl, a —CHO, a —C(O)—C 1-20 -alkyl, a —C(O)—C 6-14 -aryl, a —C(O)OH, a —C(O)—OC 1-20 -alkyl, a —C(O)—OC 6-14 -aryl, a —C(O)NH 2 , a —C(O)NH—C 1-20 -alkyl, a —C(O)N(C 1-20 -alkyl) 2 , a —C(O)NH—C 6-14 -aryl, a —C(O)N(C 1-20 -alkyl)-C 6-14 -aryl, a —C(O)N(C 6-14 -aryl) 2 , a —C(S)NH 2 , a —C(S)NH—C 1-20 -alkyl, a —C(S)N(C 1-20 -alkyl) 2 , a —C(S)N(C 6-14 -aryl) 2 , a —C(S)N(C 1-20 -alkyl)-C 6-14 -aryl, a —C(S)NH—C 6-14 -aryl, a —S(O) o NH 2 , a —S(O) o NH(C 1-20 -alkyl), a —S(O) o N(C 1-20 -alkyl) 2 , a —S(O) o NH(C 6-14 -aryl), a —S(O) o N(C 1-20 -alkyl)-C 6-14 -aryl, a —S(O) o N(C 6-14 -aryl) 2 , a SiH 3 , a SiH(C 1-20 -alkyl) 2 , a SiH 2 (C 1-20 -alkyl) and a Si(C 1-20 -alkyl) 3 , 
 wherein o is an integer of 0, 1 or 2, 
 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 are 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 2-20 -alkenyl, a C 2-20 -alkynyl, a C 1-20 -alkoxy, a —S—C 1-20 -alkyl, and a C 1-20 -haloalkyl, and 
 Z 18  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
       
       or 
       L is 
       
         
           
           
               
               
           
         
         wherein 
         R 23  and R 24  are independently 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  is —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  is C 1-6 -alkylene, C 2-6 -alkenylene or C 1-6 -haloalkylene, 
 c is an integer of from 1 to 10, and 
 R 27  is H, C 1-20 -alkyl, or —Z 20 —C 6-14 -aryl,
 wherein 
 Z 20  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 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 —, —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  are C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 28  is 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 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 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, 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  is —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  are independently C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, and 
 R 30  is H, C 1-20 -alkyl or —Z 26 —C 6-14 -aryl, 
  wherein 
  Z 26  is C 1-6 -alkylene, C 2-6 -alkenylene, C 1-6 -haloalkylene or a covalent bond, 
 
 
 Ar 16  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R q , wherein R q  is selected from the group consisting of a halogen, CN, a C 1-6 -alkyl, a C 1-6 -alkoxy and a C 1-6 -haloalkyl, 
 Ar 17  and Ar 18  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 R r  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 29  is C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy, 
 
       
       q and s are independently an integer of 0, 1, 2, 3, 4 or 5, 
       r is an integer of 0, 1 or 2, and 
       n is an integer of from 1 to 10,000. 
     
     
         2 . The compound of  claim 1 , wherein A 1  and A 2  are S. 
     
     
         3 . The compound of  claim 1 , wherein E is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1 , wherein E is 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 1 , wherein E is 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , wherein R 1  and R 2  are independently H, C 1-30 -alkyl, C 1-30 -haloalkyl, —X 1 —R 6  or —X 2 —Ar 1 ,
 wherein 
 X 1  is —[Z 1 —O] a —, —[Z 1 —S—] a —, or —[S—Z 1 ] a —S—,
 wherein 
 Z 1  is C 1-6 -alkylene or C 1-6 -haloalkylene, and 
 a is an integer of from 1 to 10, 
 
 R 6  is C 1-30 -alkyl or C 1-30 -haloalkyl, 
 X 2  is —Z 3 —O—Z 4 —, —Z 3 —S—Z 4 —, C 1-30 -alkylene or C 1-30 -haloalkylene,
 wherein Z 3  and Z 4  are independently C 1-6 -alkylene or C 1-6 -haloalkylene, 
 
 and 
 Ar 1  is C 6-14 -aryl, optionally substituted with 1 to 5 substituents R a , wherein R a  is selected from the group consisting of a halogen, a C 1-6 -alkyl, and a C 1-6 -alkoxy. 
 
     
     
         7 . The compound of  claim 1 , wherein R 1  and R 2  are independently a C 1-30 -alkyl. 
     
     
         8 . The compound of  claim 1 , 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  is a covalent bond, 
 Ar 7  is C 6-14 -aryl or monovalent 5 to 14 membered aromatic heterocyclic residue, each optionally substituted with 1 to 5 substituents R e , wherein R e  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 8  and Ar 9  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 R f  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 13  is C 1-20 -alkyl, C 2-20 -alkenyl, C 1-20 -haloalkyl or C 1-20 -alkoxy. 
 
     
     
         9 . The compound 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. 
 
     
     
         10 . The compound of  claim 1 , wherein G 1  and G 2  are independently a phenylene
 or, a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue selected from the group consisting of   
       
         
           
           
               
               
           
         
         wherein phenylene or monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue are optionally substituted with 1 to 2 substituents R i , wherein R i  is selected from the group consisting of a C 1-30 -alkyl, a —Z 17 —O—C 1-30 -alkyl, a —Z 17 —S—C 1-30 -alkyl, a —Z 17 —C 3-10 -cycloalkyl, a —Z 17 —C 6-14 -aryl, a —Z 17 -monovalent 3 to 12 membered aliphatic heterocyclic residue and a —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 are optionally substituted with 1 to 4 substituents wherein is independently 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 are optionally substituted with 1 to 4 substituents R k , wherein R k  is independently selected from the group consisting of a C 1-20 -alkyl, a C 1-20 -alkoxy, and a C 1-20 -haloalkyl, 
 and 
 Z 17  is C 1-6 -alkylene, C 1-6 -haloalkylene or a covalent bond. 
 
       
     
     
         11 . The compound of  claim 1 , wherein G 1  and G 2  are independently a monocyclic bivalent 5 to 8 membered aromatic heterocyclic residue 
       
         
           
           
               
               
           
         
         which is substituted with 1 to 2 substituents R i , wherein R i  is selected from the group consisting of a C 1-30 -alkyl and a —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 R j  is selected from the group consisting of a halogen, a —CN and a *═O, 
 C 6-14 -aryl is optionally substituted with 1 to 4 substituents R k , wherein R k  is selected from the group consisting of a C 1-20 -alkyl and a C 1-20 -alkoxy, and 
 Z 17  is a covalent bond. 
 
       
     
     
         12 . The compound of  claim 1 , wherein R i  is C 1-30 -alkyl. 
     
     
         13 . The compound of  claim 1 , wherein
 L is a bivalent 5 to 18 membered aromatic heterocyclic residue optionally substituted with 1 to 4 substituents R l , wherein R l  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, 
   or   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  re 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. 
 
       
     
     
         14 . The compound 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
 wherein R l  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 
 R t  is hydrogen or C 1-30 -alkyl, 
 
         or 
         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 1-6 -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 1-30 -alkenylene, C 1-30 -haloalkylene or a covalent bond,
 wherein Z 21  and Z 22  are independently C 1-6 -alkylene, C 1-6 -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. 
 
       
     
     
         15 . The compound of  claim 1 , wherein
 L is   
       
         
           
           
               
               
           
         
         
           wherein 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, 
 
         
         or 
         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 3-30 -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 1-30 -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. 
 
       
     
     
         16 . The compound of  claim 1 , wherein
 R l  is selected from the group consisting of a C 1-30 -alkyl and a —Z 18 —C 6-14 -aryl,
 wherein 
 C 1-30 -alkyl and C 6-14 -aryl are 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 6-14 -aryl 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 and a C 1-20 -alkoxy, and 
 Z 18  is a covalent bond, 
   and   R 23  and R 24  are independently H, C 1-30 -alkyl, C 1-30 -haloalkyl, —X 7 —R 25  or —X 8 —Ar 13 ,
 wherein 
 X 7  is —[Z 19 —O] c —, —[Z 19 —S—] c —, or —[S—Z 19 ] c —S—,
 wherein 
 Z 19  is C 1-6 -alkylene or C 1-6 -haloalkylene, and 
 c is an integer of from 1 to 10, 
 
 R 25  is C 1-30 -alkyl or C 1-30 -haloalkyl, 
 X 8  is —Z 21 —O—Z 22 —, —Z 21 —S—Z 22 —, C 1-30 -alkylene or C 1-30 -haloalkylene,
 wherein Z 21  and Z 22  are independently C 1-6 -alkylene or C 1-6 -haloalkylene, 
 
 and 
 Ar 13  is C 6-14 -aryl, optionally substituted with 1 to 5 substituents R o , wherein R o  is selected from the group consisting of a halogen C 1-6 -alkyl and a C 1-6 -alkoxy. 
   
     
     
         17 . The compound of  claim 1 , wherein R l  is C 1-30 -alkyl,
 and   R 23  and R 24  are independently H, C 1-30 -alkyl or C 1-30 -haloalkyl.   
     
     
         18 . The compound of  claim 1 , wherein q, r and s are an integer of 0 or 1, and q, r and s are not all 0 at the same time. 
     
     
         19 . The compound of  claim 1 , wherein n is an integer of from 1 to 5000. 
     
     
         20 . An electronic device comprising the compound of  claim 1 . 
     
     
         21 . The electronic device of  claim 20 , wherein the electronic device is an organic field effect transistor. 
     
     
         22 . An organic semiconducting material comprising the compound of  claim 1 .