Heteroacene compounds for organic electronics

1. A compound of formula (1)

wherein

o is 1, 2 or 3,

p is 0, 1 or 2,

n is 0, 1 or 2,

m is 0, 1 or 2,

A is a mono -or dicyclic ring system A, which contains at least S atom,

wherein R 10 is at each occurrence C 1-30 -alkyl, wherein

at least one CH 2 -group of C 1-30 -alkyl, but not adjacent CH 2 -groups, is optionally replaced with —O— or —S—,

C 1-30 -alkyl is optionally substituted with 1 to 10 R 100 residues at each occurrence selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , —NH(R a ), —N(R a ) 2 , —NH—C(O)—(R a ), —N(R a )—C(O)—(R a ), —N[C(O)—(R a )] 2 , —C(O)—R a , —C(O)—OR a , —C(O)NH 2 , —CO(O)NH—R a , —C(O)N(R a ) 2 , —O—R a , —O—C(O)—R a , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and

wherein

R a is at each occurrence selected from the group consisting of C 1-20 -alkyl,

C 2-20 -alkenyl, C 2-20 -alkynyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl are optionally substituted with 1 to 5 residues at each occurrence selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system;

R 3 and R 11 are independently from each other at each occurrence selected from the group consisting of halogen, —CN, —NO 2 , C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

at least one CH 2 -group of CH 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl, but not adjacent CH 2 -groups, is optionally replaced with —O— or —S—, and

C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl are optionally substituted with 1 to 10 R 101 residues independently selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , —NH(R b ), —N(R b ) 2 , —NH—C(O)—(R b ), —N(R b )—C(O)—(R b ), —N[C(O)—(R b )] 2 , —C(O)—R b , —C(O)—OR b , —C(O)NH 2 , —CO(O)NH—R b , —C(O)N(R b ) 2 , —O—R b , —O—C(O)—R b , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and

wherein

R b is at each occurrence selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

C 1-20 -alkyl, C 2-20 -alkenyl or C 2-20 -alkynyl are optionally substituted with 1 to 5 residues at each occurrence selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and

C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system are optionally substituted with 1 to 5 residues independently selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl.

2. The compound of claim 1 , wherein A is

3. The compound of claim 1 , wherein R 10 is at each occurrence C 8-20 -alkyl.

4. The compound of claim 1 , wherein R 3 and R 11 are independently from each other at each occurrence selected from the group consisting of halogen, —CN, C 1-30 -alkyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

at least one CH 2 -group of C 1-30 -alkyl, but not adjacent CH 2 -groups, is optionally replaced with —O— or —S—, and

C 1-30 -alkyl is optionally substituted with 1 to 10 R 101 residues independently selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , —NH(R b ), —N(R b ) 2 , —NH—C(O)—(R b ), —N(R b )—C(O)—(R b ), —N[C(O)—(R b )] 2 , —C(O)—R b , —C(O)—OR b , —C(O)NH 2 , —CO(O)NH—R b , —C(O)N(R b ) 2 , —O—R b , —O—C(O)—R b , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and wherein

wherein

R b is at each occurrence selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

C 1-20 -alkyl, C 2-20 -alkenyl or C 2-20 -alkynyl is optionally substituted with 1 to 5 residues at each occurrence selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and

C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system are optionally substituted with 1 to 5 residues independently selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl.

5. The compound of claim 1 , wherein R 3 and R 11 are independently from each other at each occurrence selected from the group consisting of C 1-30 -alkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

at least one CH 2 -group of C 1-30 -alkyl, but not adjacent CH 2 -groups, is optionally replaced with —O— or —S—, and

C 1-30 -alkyl is optionally substituted with 1 to 10 R 101 residues independently selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , —NH(R b ), —N(R b ) 2 , —NH—C(O)—(R b ), —N(R b )—C(O)—(R b ), —N[C(O)—(R b)] 2 , —C(O)—R b , —C(O)—OR b , —C(O)NH 2 , —CO(O)NH—R b , —C(O)N(R b ) 2 , —O—R b , —O—C(O)—R b , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and wherein

wherein

R b is at each occurrence selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, wherein

C 1-20 -alkyl, C 2-20 -alkenyl or C 2-20 -alkynyl is optionally substituted with 1 to 5 residues at each occurrence selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 4-8 -cycloalkyl, C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system, and

C 6-14 -aryl, and a 5 to 14 membered heterocyclic ring system are optionally substituted with 1 to 5 residues independently selected from the group consisting of halogen, CN, —NO 2 , —OH, —NH 2 , C 1-10 -alkyl, C 2-10 -alkenyl, and C 2-10 -alkynyl.

6. The compound of claim 1 , wherein o is 1.

7. The compound of claim 1 , wherein p, n and m are 0.

8. The compound of claim 1 , wherein the compound of formula (1) is selected from the group consisting of formulae (1′a) and (1′b)

wherein R 10 is C 8-20 -alkyl.

9. An electronic device comprising the compound according to claim 1 .

10. The electronic device of claim 9 , wherein the electronic device is an organic field effect transistor (OFET).

11. A method comprising incorporating the compound according to claim 1 as a semiconducting material.