Polymer compound and organic semiconductor device using the same

Patent metadata

Field	Value
Publication number	US-9796811-B2
Application number	US-201414909181-A
Country	US
Kind code	B2
Filing date	Aug 21, 2014
Priority date	Aug 23, 2013
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

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

wherein Ring A and Ring B represent each independently a heterocyclic ring, and the heterocyclic ring may have a substituent, Ring C represents an aromatic hydrocarbon ring obtained by condensing two or more benzene rings, the aromatic hydrocarbon ring has at least one of an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group, and these groups may have a substituent, Z 1 and Z 2 represent each independently 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) or a group represented by the formula (Z-5),

wherein R represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group or a mono-valent heterocyclic group, and these groups may have a substituent, and when there exist a plurality of R, these may be the same or different.

First claim

The invention claimed is:

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

wherein
Ring A and Ring B represent each independently a heterocyclic ring, and the heterocyclic ring may have a substituent;
Ring C represents an aromatic hydrocarbon ring obtained by condensing two or more benzene rings, the aromatic hydrocarbon ring has two of an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group, and these groups may have a substituent;
Z 1 and Z 2 represent each independently 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) or a group represented by the formula (Z-5); and

wherein
R represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group or a mono-valent heterocyclic group, and these groups may have a substituent, and when there exist a plurality of R, these 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 (2a):

wherein
Ring A, Ring B, Z 1 and Z 2 represent the same meaning as described above; and
R 1 , R 2 , R 3 and R 4 represent each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and these groups may have a substituent; and here two selected from the group consisting of R 1 , R 2 , R 3 and R 4 is an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group.

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

wherein
R 1 , R 2 , R 3 , R 4 , Z 1 and Z 2 represent the same meaning as described above;
X 1 and X 2 represent each independently an oxygen atom, a sulfur atom or a selenium atom;
Y 1 and Y 2 represent each independently a nitrogen atom or a group represented by —CR 5 ═; and
R 5 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group or a halogen atom, and these groups may have a substituent.

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

wherein
Ring A, Ring B, Z 1 and Z 2 represent the same meaning as described above; and
R 1a , R 2a , R 3a and R 4a represent each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and these groups may have a substituent; and here two selected from the group consisting of R 1a , R 2a , R 3a and R 4a in the formula (2b) is an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group, and two selected from the group consisting of R 1a , R 2a , R 3a and R 4a in the formula (2c) is an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group.

5. The polymer compound according to claim 3 , wherein X 1 and X 2 are sulfur atoms.

6. The polymer compound according to claim 3 , wherein Y 1 and Y 2 are groups represented by —CH═.

7. The polymer compound according to claim 1 , wherein Z 1 and Z 2 are groups represented by the formula (Z-1).

8. The polymer compound according to claim 1 , further comprising a structural unit represented by the formula (4) (different from the structural unit represented by the formula (1)):

wherein
Ar represents an arylene group or a di-valent heterocyclic group, and these groups may have a substituent.

9. The polymer compound according to claim 8 , wherein the polymer compound is an alternative copolymer composed of the structural unit represented by the formula (1) and the structural unit represented by the formula (4).

10. A compound represented by the formula (5a):

wherein
Ring A and Ring B represent each independently a heterocyclic ring, and the heterocyclic ring may have a substituent;
Z 1 and Z 2 represent each independently 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) or a group represented by the formula (Z-5);
R 1 , R 2 , R 3 and R 4 represent each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and these groups may have a substituent; and here two selected from the group consisting of R 1 , R 2 , R 3 and R 4 is an alkyl group, an alkoxy group, an alkylthio group, an amino group or a hydroxyl group; and

wherein
R represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group or a mono-valent heterocyclic group, and these groups may have a substituent; and when there exist a plurality of R, these may be the same or different.

11. The compound according to claim 10 , wherein the compound represented by the formula (5a) is a compound represented by the formula (6a):

wherein
R 1 , R 2 , R 3 , R 4 , Z 1 and Z 2 represent the same meaning as described above;
R 6 and R 7 represent each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group, a halogen atom, a silyl group, an amino group, an alkenyl group, an alkynyl group, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, an alkylcarbonyl group, an alkoxycarbonyl group, a borate residue, a boric acid residue or an organotin residue, and these groups may have a substituent;
X 1 and X 2 represent each independently an oxygen atom, a sulfur atom or a selenium atom;
Y 1 and Y 2 represent each independently a nitrogen atom or a group represented by —CR 5 ═; and
R 5 represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a mono-valent heterocyclic group or a halogen atom, and these groups

Assignees

• Sumitomo Chemical Co

Inventors

• Kashiki Tomoya
• Terai Hiroki

Classifications

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/146

  Side-chains containing halogens · CPC title

• H01L51/5012

  Electricity · mapped topic