Conductive polymer composition, coated article, and patterning process

Patent metadata

Field	Value
Publication number	US-10295906-B2
Application number	US-201615259790-A
Country	US
Kind code	B2
Filing date	Sep 8, 2016
Priority date	Sep 25, 2015
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

A conductive polymer composition including: (A) π-conjugated conductive polymer having at least one repeating unit shown by the following general formulae (1-1), (1-2), and (1-3); (B) a dopant polymer which contains a repeating unit “a” shown by the following general formula (2) and has a weight-average molecular weight in a range of 1,000 to 500,000; and (C) an amphoteric ion compound shown by the following general formula (3). This provides a conductive polymer composition having good filterability, coating property and film-formability onto a substrate to form a conductive film with good film quality and peelability with H 2 O or an alkaline developer; and forming a conductive film which reveals antistatic performance with high charge discharging ability and does not affect an influence of acid on the adjoined layer to be contact with.

First claim

What is claimed is:

1. A conductive polymer composition comprising:
(A) a π-conjugated conductive polymer having at least one repeating unit shown by the following general formulae (1-1), (1-2), and (1-3),

wherein “X” represents S, O, Se, Te, or NR 5 ; R 1 and R 2 each independently represents a hydrogen atom, a hydroxy group, a halogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms and optionally containing a heteroatom; R 1 and R 2 may be bonded to each other at any positions to form a ring; and R 5 represents a hydrogen atom, a linear or branched saturated or unsaturated alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms;
(B) a dopant polymer which contains a repeating unit shown by the following general formula (2), and the dopant polymer has a weight-average molecular weight in a range of 1,000 to 500,000,

wherein R 3 represents a hydrogen atom or a methyl group; R 4 represents a single bond, an ester group, or a linear, branched, or cyclic hydrocarbon group having 1 to 12 carbon atoms and optionally containing either or both of an ether group and an ester group; “Z” represents a phenylene group, a naphthylene group, or an ester group; and “a” is 0≤a≤1.0; and
(C) an amphoteric ion compound shown by the following general formula (3), wherein the component (C) is present in the polymer composition in an amount of 1 to 70 parts by mass based on 100 parts by mass of the combined amounts of the component (A) and the component (B),

wherein R C1 to R C3 each independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms and optionally substituted by a heteroatom or optionally interposed by a heteroatom; R C1 and R C2 , or R C1 , R C2 , and R C3 may be bonded to each other to form a ring with A + in the formula; A + is a heteroatom and represents a monovalent cation; “k” represents an integer of 1 to 8; “L” represents a carbon atom or a heteroatom, and may contain the both of them when “k” is 2 or more; R C4 and R C5 independently represent a hydrogen atom, a hydroxy group, an amino group, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms and optionally interposed by a heteroatom; R C4 and R C5 may be bonded to each other to form a ring, and adjoining R C4 may be bonded to each other to form a ring when “k” is 2 or more; R C4 and R C5 may be bonded to an oxygen atom or a nitrogen atom to form a double bond, and when R C4 and R C5 form a double bond with the nitrogen atom, the nitrogen atom can be an ion; “L” may form a double bond with adjoining A + , and adjoining “L” may form a double bond with each other when “k” is 2 or more; any of R C1 to R C3 may be bonded to R C4 or R C5 to form a ring; and B − is a monovalent anionic functional group and represents a carboxylate ion or a sulfonate ion.

2. The conductive polymer composition according to claim 1 , wherein the repeating unit in the component (B) contains one or more repeating units selected from repeating units shown by the following general formulae (2-1) to (2-7),

wherein R 3 has the same meaning as defined above; a1, a2, a3, a4, a5, a6, and a7 are, respectively, 0≤a1≤1.0, 0≤a2≤1.0, 0≤a3≤1.0, 0≤a4≤1.0, 0≤a5≤1.0, 0≤a6≤1.0, 0≤a7≤1.0, and 0<a1+a2+a3+a4+a5+a6+a7≤1.0.

3. The conductive polymer composition according to claim 2 , wherein the component (B) further contains a repeating unit shown by the following general formula (4),

wherein “b” is 0<b<1.0.

4. The conductive polymer composition according to claim 3 , wherein the component (C) is shown by the general formula (5),

wherein R C1 to R C5 , A + , “L”, and “k” have the same meanings as defined above.

5. The conductive polymer composition according to claim 2 , wherein the component (C) is shown by the general formula (5),

wherein R C1 to R C5 , A + , “L”, and “k” have the same meanings as defined above.

6. The conductive polymer composition according to claim 2 , wherein the component (C) is in an amount of 20 to 50 parts by mass based on 100 parts by mass of the combined amounts of the component (A) and the component (B).

7. The conductive polymer composition according to claim 1 , wherein the component (B) further contains a repeating unit shown by the following general formula (4),

wherein “b” is 0<b<1.0.

8. The conductive polymer composition according to claim 7 , wherein the component (C) is shown by the general formula (5),

wherein R C1 to R C5 , A + , “L”, and “k” have the same meanings as defined above.

9. The conductive polymer composition according to claim 1 , wherein the component (C) is shown by the general formula (5),

wherein R C1 to R C5 , A + , “L”, and “k” have the same meanings as defined above.

10. The conductive polymer composition according to claim 1 , wherein the component (C) is in an amount of 20 to 50 parts by mass based on 100 parts by mass of the combined amounts of the component (A) and the component (B).

11. The conductive polymer composition according to claim 1 , further comprising a nonionic surfactant.

12. The conductive polymer composition according to claim 11 , wherein the nonionic surfactant is in an amount of 1 to 50 parts by mass based on 100 parts by mass of the combined amounts of the component (A) and the component (B).

13. An organic thin-film device comprising a laminated film formed from the conductive polymer composition according to claim 1 , wherein the laminated film is configured to be a device constituent component in the organic thin-film device.

14. The organic thin-film device according to claim 13 , wherein the film is an electrode film or a carrier transferring film.

15. A coated article, comprising a film formed from the conductive polymer composition according to claim 1 on a body to be processed.

16. The coated article according to claim 15 , wherein the body to be processed is a substrate having a chemically amplified resist film.

17. The coated article according to claim 16 , wherein the body to be processed is a substrate for obtaining a resist pattern by pattern irradiation with electron beam.

18. A patterning process comprising the steps of: forming an antistatic film on a substrate having a chemically amplified resist film by using the co

Assignees

• Shinetsu Chemical Co

Inventors

• Nagasawa Takayuki
• Hatakeyama Jun

Classifications

• H10P76/2045

  Electron beam lithography processes · CPC title

• G03F7/093 Primary

  characterised by antistatic means, e.g. for charge depletion · CPC title

• C08L65/00 Primary

  Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers · CPC title

• G03F7/2059

  using a scanning corpuscular radiation beam, e.g. an electron beam · CPC title

• C08K2201/017

  Additives being an antistatic agent · CPC title