Polymer compound and organic semiconductor device using the same

Patent metadata

Field	Value
Publication number	US-10239886-B2
Application number	US-201515325542-A
Country	US
Kind code	B2
Filing date	Jul 15, 2015
Priority date	Jul 23, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

A polymer compound comprising a structural unit represented by the formula (1):

wherein a ring A and a ring B represent a heterocyclic ring. A ring C represents a condensed aromatic heterocyclic ring not having a line-symmetric axis and a rotational axis. Z 1 and Z 2 represent a group represented by the formula (Z-1), a group represented by the formula (Z-2), a group represented by the formula (Z-3), a group represented by the formula (Z-4), a group represented by the formula (Z-5), a group represented by the formula (Z-6) or a group represented by the formula (Z-7).

R represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group or a monovalent heterocyclic group.].

First claim

The invention claimed is:

1. A polymer compound comprising a structural unit represented by the formula (1):

wherein
a ring A and a ring B each independently represent a heterocyclic ring, and the heterocyclic ring optionally has a substituent;
a ring C represents a condensed aromatic heterocyclic ring not having a line-symmetric axis and a rotational axis, and the aromatic heterocyclic ring optionally has a substituent;
Z 1 and Z 2 each independently represent a group represented by the formula (Z-1), a group represented by the formula (Z-2), a group represented by the formula (Z-3), a group represented by the formula (Z-4), a group represented by the formula (Z-5), a group represented by the formula (Z-6) or a group represented by the formula (Z-7);

wherein
R represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent; and when a plurality of R are present, they may be the same or different.

2. The polymer compound according to claim 1 , wherein the structural unit represented by the formula (1) is a structural unit represented by the formula (2):

wherein
a ring A, a ring B, Z 1 and Z 2 represent the same meaning as described above;
X 3 represents an oxygen atom, a sulfur atom or a selenium atom; and
a ring D represents an aromatic hydrocarbon ring selected from the group consisting of a benzene ring and a condensed ring obtained by condensation of 2 to 4 benzene rings, and the aromatic hydrocarbon ring optionally has a substituent.

3. The polymer compound according to claim 2 , wherein the structural unit represented by the formula (2) is a structural unit represented by the formula (3):

wherein
a ring A, a ring B, X 3 , Z 1 and Z 2 represent the same meaning as described above;
R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, a monovalent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group, a cycloalkylcarbonyl group, an alkoxycarbonyl group or a cycloalkoxycarbonyl group, and of these groups, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, a monovalent heterocyclic group, a silyl group, an amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylcarbonyl group, a cycloalkylcarbonyl group, an alkoxycarbonyl group and a cycloalkoxycarbonyl group each optionally have a substituent.

4. The polymer compound according to claim 3 , wherein the structural unit represented by the formula (3) is a structural unit represented by the formula (4):

wherein
R 1 , R 2 , X 3 , Z 1 and Z 2 represent the same meaning as described above;
X 1 and X 2 each independently represent an oxygen atom, a sulfur atom or a selenium atom; and
Y 1 represents a nitrogen atom or a group represented by —CR 5 ═, and Y 2 represents a nitrogen atom or a group represented by —CR 6 ═, R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, a monovalent heterocyclic group or a halogen atom, and of these groups, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group and a monovalent heterocyclic group each optionally have a substituent.

5. The polymer compound according to claim 4 , wherein X 1 , X 2 and X 3 each represent a sulfur atom.

6. The polymer compound according to claim 4 , wherein Y 1 and Y 2 represent a group represented by —CH═.

7. The polymer compound according to claim 1 , wherein Z 1 and Z 2 represent a group represented by formula (Z-1).

8. The polymer compound according to claim 1 , further comprising a structural unit represented by the formula (5):
Ar   (5)

wherein
Ar represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.

9. The polymer compound according to claim 8 , wherein the polymer compound is an alternate copolymer of the structural unit represented by the formula (1) and the structural unit represented by the formula (5).

10. A compound represented by the formula (6):

wherein
a ring A and a ring B each independently represent a heterocyclic ring, and the heterocyclic ring optionally has a substituent other than R 7 and R 8 ;
X 3 represents an oxygen atom, a sulfur atom or a selenium atom;
Z 1 and Z 2 each independently represent a group represented by the formula (Z-1), a group represented by the formula (Z-2), a group represented by the formula (Z-3), a group represented by the formula (Z-4), a group represented by the formula (Z-5), a group represented by the formula (Z-6) or a group represented by the formula (Z-7);
R 1 and R 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, a monovalent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group, a cycloalkylcarbonyl group, an alkoxycarbonyl group or a cycloalkoxycarbonyl group, and of these groups, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group, a monovalent heterocyclic group, a silyl group, an amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylcarbonyl group, a cycloalkylcarbonyl group, an alkoxycarbonyl group and a cycloalkoxycarbonyl group each optionally have a substituent; R 7 and R 8 each independently represent a hydrogen atom, a halogen atom, a silyl group, a hydroxyl group, a carboxyl group, a borate residue, a boric acid residue or an organotin residue, and of these groups, a silyl group optionally has a substituent;

wherein
R represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, a cycloalkylthio group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent; and when a plurality of R are present, they may be the same or different.

11. The compound according to claim 10 , wherein the compound represented by the formula (6) is a compound represented by the formula (7):

Assignees

• Sumitomo Chemical Co

Inventors

• Kashiki Tomoya
• Yoshikawa Eiji

Classifications

• C08G2261/51

  Charge transport · CPC title

• C07F7/2208

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C08G61/123

  derived from five-membered heterocyclic compounds · CPC title

• H01L51/0036

  Electricity · mapped topic

• H01L51/42

  Electricity · mapped topic