Heteroacene compounds for organic electronics

Patent metadata

Field	Value
Publication number	US-9780315-B2
Application number	US-201314649039-A
Country	US
Kind code	B2
Filing date	Nov 25, 2013
Priority date	Dec 3, 2012
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The present invention provides compounds 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, and A is a mono- or polycyclic ring system, which may contain at least one heteroatom, and an electronic device comprising the compounds as semiconducting material.

First claim

The invention claimed is:

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.

Assignees

• Basf Se

Inventors

• Jiao Chongjun
• Doi Iori
• Kirner Hans Jürg
• Zhou Mi
• Weitz Thomas
• Mishra Ashok Kumar

Classifications

• H01L51/0074 Primary

  Electricity · mapped topic

• H01L51/0545

  Electricity · mapped topic

• C07D495/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title

• H01L51/0558

  Electricity · mapped topic

• H10K10/466

  Lateral bottom-gate IGFETs comprising only a single gate · CPC title