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CN-121986126-A - Copolymer, photosensitive resin composition, material for forming pattern, cured product, and image display device

CN121986126ACN 121986126 ACN121986126 ACN 121986126ACN-121986126-A

Abstract

A copolymer comprising a repeating structural unit A1 represented by the following general formula (1) and a repeating structural unit A2 represented by the following general formula (2). (in the formula (1) and the formula (2), R 1 is hydrogen or methyl, A 1 is a chemical structure having an alkoxysilyl group at the end, A 2 is a chemical structure having a group other than an alkoxysilyl group at the end which generates a hydroxyl group by acid dissociation.)

Inventors

  • TAKEUCHI Yutaro
  • OKURA YUKI

Assignees

  • 大阪有机化学工业株式会社

Dates

Publication Date
20260505
Application Date
20241011
Priority Date
20231012

Claims (17)

  1. 1. A copolymer comprising a repeating structural unit A1 represented by the following general formula (1) and a repeating structural unit A2 represented by the following general formula (2), In the formula (1) and the formula (2), R 1 is hydrogen or methyl, a 1 is a chemical structure having an alkoxysilyl group at the end, and a 2 is a chemical structure having a group other than an alkoxysilyl group at the end, which generates a hydroxyl group by acid dissociation.
  2. 2. The copolymer according to claim 1, wherein the copolymer further comprises a repeating structural unit A3 containing an acidic group at the terminal of the side chain.
  3. 3. The copolymer according to claim 2, wherein the structural unit A3 is a structural unit represented by the following general formula (3), In the formula (3), R 1 is hydrogen or methyl, and X 1 is a single bond or a linking group having 1 to 10 carbon atoms.
  4. 4. The copolymer according to claim 1 or 2, wherein the structural unit A2 is a structural unit represented by the following formula (II), In the formula (II), R 1 is hydrogen or methyl, R 2 is (poly) oxyalkylene group having 2 to 4 carbon atoms, R 3 is a chemical structure represented by the following general formula (4), R 4 is hydrogen, hydrocarbon group having 1 to 10 carbon atoms or phenyl group, R 7 is hydrogen, hydrocarbon group having 1 to 10 carbon atoms or phenyl group which may be substituted by phenyl group, In the formula (4), R 5 is a hydrocarbon group having 1 to 10 carbon atoms, and R 6 is hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, a phenyl group or a cyclohexyl group.
  5. 5. The copolymer according to claim 1 or 2, wherein the structural unit A1 is a structural unit represented by the following general formula (I), In the formula (I), R 1 is hydrogen or methyl, X 2 is alkylene having 1 to 10 carbon atoms, R 8 is alkoxy having 1 to 10 carbon atoms, R 9 is hydrocarbon having 1 to 10 carbon atoms, and a is an integer of 1 to 3.
  6. 6. The copolymer according to claim 1 or 2, wherein the weight average molecular weight Mw of the copolymer is 3000 to 20000.
  7. 7. The copolymer according to claim 2, wherein in the copolymer, when the molar ratio of the structural unit A1, the structural unit A2, and the structural unit A3 is k:l:m, k:l:m=30 to 80:5 to 40:10 to 40.
  8. 8. A photosensitive resin composition comprising: a polymer comprising at least a repeating structural unit A1 represented by the following general formula (1), A polymer comprising at least a repeating structural unit A2 represented by the following general formula (2), and A photoacid generator (B), In the formula (1) and the formula (2), R 1 is hydrogen or methyl, a 1 is a chemical structure having an alkoxysilyl group at the end, and a 2 is a chemical structure having a group other than an alkoxysilyl group at the end, which generates a hydroxyl group by acid dissociation.
  9. 9. The photosensitive resin composition according to claim 8, further comprising a monomer (C) having at least one of an unsaturated double bond and an alkoxysilyl group in a molecule.
  10. 10. The photosensitive resin composition according to claim 8 or 9, wherein the polymer in the photosensitive resin composition is a copolymer comprising the repeating structural unit A1 and the repeating structural unit A2.
  11. 11. The photosensitive resin composition according to claim 10, wherein the copolymer is a copolymer further comprising a structural unit A3 represented by the following general formula (3), In the formula (3), R 1 is hydrogen or methyl, and X 1 is a single bond or a linking group having 1 to 10 carbon atoms.
  12. 12. The photosensitive resin composition according to claim 8 or 9, further comprising a photopolymerization initiator (D).
  13. 13. The photosensitive resin composition according to claim 8 or 9, further comprising a monofunctional alcohol containing no carboxyl group and no N-H bond as a solvent.
  14. 14. A material for pattern formation comprising the photosensitive resin composition according to claim 8 or 9.
  15. 15. A cured product obtained from the photosensitive resin composition according to claim 8 or 9.
  16. 16. The cured product according to claim 15, wherein the cured product is a photo spacer, a spacer material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarizing film material.
  17. 17. An image display device comprising the cured product of claim 15.

Description

Copolymer, photosensitive resin composition, material for forming pattern, cured product, and image display device Technical Field The application relates to a copolymer, a photosensitive resin composition, a material for forming patterns, a cured product and an image display device. The present application claims priority based on japanese patent application No. 2023-177122 filed on 10/12 of 2023, and all the contents described in the above japanese patent application are incorporated herein by reference. Background As a micromachining technique used for forming a circuit pattern in a large scale integrated circuit (LSI), forming a spacer arranged between substrates constituting a liquid crystal display, and the like, there is photolithography. Many proposals have been made for photosensitive resin compositions for use in photolithography. Patent document 1 discloses a negative photosensitive resin composition containing an alkali-soluble resin, a photo radical polymerization initiator, and a photopolymerizable monomer including a photopolymerizable monomer having an isocyanuric acid skeleton and a photopolymerizable monomer having a fluorene skeleton. Patent document 2 discloses a photosensitive resin composition used as a spacer forming material. The photosensitive resin composition described in patent document 2 includes a binder polymer, a photopolymerizable compound including a photopolymerizable compound having an ethylenically unsaturated group and an isocyanurate ring structure, a photopolymerization initiator, and a mercapto group-containing hydrogen donor. Patent document 3 discloses a photosensitive resin composition comprising an alkali-soluble resin, a crosslinking agent, a photopolymerization initiator, and an acid catalyst. The alkali-soluble resin contained in the photosensitive resin composition disclosed in patent document 3 is a (meth) acrylate copolymer, and contains a repeating structural unit having a side chain of a constant length or more and a carboxyl group at the end of the side chain. Prior art literature Patent literature Patent document 1 Japanese patent application laid-open No. 2019-124929 Patent document 2 International publication No. 2013/115262 Patent document 3 International publication No. 2023/090286 Disclosure of Invention When the photolithography process is schematically described, the photosensitive resin composition is applied to the substrate, followed by (pre-baking), exposure, development, and (post-baking). In view of heat resistance of a target product to be subjected to photolithography, it is desirable to perform a series of steps of photolithography in a low-temperature (e.g., 150 ℃ or less) environment. In addition, it is preferable that the hardness of the formed cured product is high even under such a temperature environment. Further, it is desired to form a pattern having a small line width and a via hole having a small opening diameter by photolithography. In view of the above, an object of the present invention is to provide a photosensitive resin composition which forms a cured product having high hardness even when photolithography is performed at a low temperature and has excellent patterning properties (photolithographic properties), and a copolymer constituting the photosensitive resin composition. A copolymer comprising a repeating structural unit A1 represented by the following general formula (1) and a repeating structural unit A2 represented by the following general formula (2). (In the formula (1) and the formula (2), R 1 is hydrogen or methyl, A 1 is a chemical structure having an alkoxysilyl group at the end, A 2 is a chemical structure having a group other than an alkoxysilyl group at the end which generates a hydroxyl group by acid dissociation.) A photosensitive resin composition comprising: a polymer comprising at least a repeating structural unit A1 represented by the following general formula (1), A polymer comprising at least a repeating structural unit A2 represented by the following general formula (2), and Photoacid generator (B). (In the formula (1) and the formula (2), R 1 is hydrogen or methyl, A 1 is a chemical structure having an alkoxysilyl group at the end, A 2 is a chemical structure having a group other than an alkoxysilyl group at the end which generates a hydroxyl group by acid dissociation.) The copolymer can provide a photosensitive resin composition which can form a cured product having high hardness even when photolithography is performed at a low temperature and which has excellent patterning properties (photolithographic properties). Further, according to the photosensitive resin composition, a cured product having high hardness can be formed even when photolithography is performed at a low temperature, and a photosensitive resin composition having excellent patterning properties (photolithography properties) can be provided. Detailed Description [ Summary of the embodiments ] First, embodiments of the copolyme