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CN-122003643-A - Photosensitive resin composition, method for producing pattern, cured product, electronic component, and display device

CN122003643ACN 122003643 ACN122003643 ACN 122003643ACN-122003643-A

Abstract

The purpose of the present invention is to provide a photosensitive resin composition which has excellent heat resistance, little film reduction during development, and high sensitivity. The present invention provides a photosensitive resin composition comprising (a) at least one resin selected from the group consisting of polyimide, polyamideimide, polybenzoxazole, and precursors thereof (hereinafter referred to as "(a resin"), (b) an amine compound, and (c) a photoacid generator, wherein the amine compound is a primary amine or a secondary amine, and the photosensitive resin composition comprises (b) 35 parts by mass of the amine compound per 100 parts by mass of the resin (a).

Inventors

  • KOSHIMIZU Noboru
  • Zhuang Siyou
  • Paddy wall is bravely firm

Assignees

  • 东丽株式会社

Dates

Publication Date
20260508
Application Date
20241220
Priority Date
20231222

Claims (18)

  1. 1. A photosensitive resin composition comprising: (a) One or more resins (hereinafter referred to as "(a) resins") selected from the group consisting of polyimide, polyamideimide, polybenzoxazole, and precursors thereof, (B) Amine compound (C) The photo-acid generator is used for generating a photo-acid, The amine compound (b) is primary amine or secondary amine, The photosensitive resin composition contains 35 parts by mass or more of the (b) amine compound per 100 parts by mass of the (a) resin.
  2. 2. The photosensitive resin composition according to claim 1, wherein the acid equivalent of the (a) resin is 500 g/mol or more, and The carboxylic acid equivalent of the resin (a) is 500 g/mol or more, or the resin (a) does not have carboxyl groups.
  3. 3. The photosensitive resin composition according to claim 2, wherein the (a) resin is a resin containing an amide bond in a repeating unit, and is a polyimide precursor, a polyamideimide precursor, or a polybenzoxazole precursor.
  4. 4. The photosensitive resin composition according to claim 3, wherein the (a) resin has an electron-withdrawing group which is one or more groups selected from the group consisting of a nitro group, a cyano group, a sulfo group and a sulfonyl group.
  5. 5. The photosensitive resin composition according to claim 1, wherein the (b) amine compound is a monoamine compound.
  6. 6. The photosensitive resin composition according to any one of claims 1 to 5, wherein the (b) amine compound is a primary amine.
  7. 7. The photosensitive resin composition according to any one of claims 1 to 5, wherein the (b) amine compound is an aliphatic amine.
  8. 8. The photosensitive resin composition according to any one of claims 1 to 5, wherein the pKb of the (b) amine compound is 6 or less.
  9. 9. The photosensitive resin composition according to any one of claims 1 to 5, wherein the boiling point of the (b) amine compound at 1 atmosphere is 100 ℃ or more and 300 ℃ or less.
  10. 10. The photosensitive resin composition according to claim 1, wherein the (a) resin has an electron withdrawing group, The (a) resin comprises a resin selected from the group consisting of (A1) A polyimide or polyamideimide (hereinafter referred to as "(a 1) resin") comprising a constituent unit represented by the formula (1), (A2) A polyimide precursor or a polyamideimide precursor (hereinafter referred to as "(a 2) resin") comprising a constituent unit represented by the formula (2), (A3) A polyamide imide (hereinafter referred to as "(a 3) resin") comprising a constituent unit represented by the formula (3), (A4) Polybenzoxazole (hereinafter referred to as "(a 4) resin") containing a constituent unit represented by formula (4) (A5) A polybenzoxazole precursor (hereinafter referred to as "(a 5) resin") containing a constituent unit represented by the formula (5) More than one resin in the group. [ Chemical 1] In the formula (1), L 1 is a single bond, a sulfonyl group, > C (CF 3 ) 2 , an oxygen atom or a divalent organic group having 1 to 20 carbon atoms) L 1 is bonded to any one of X 1 ～X 4 and X 5 ～X 8 , X n (n=1 to 8) is C-R n （n=1～8）.R n (n=1 to 8) and is a group selected from the group consisting of a hydrogen atom, an electron withdrawing group and a monovalent organic group having 1 to 20 carbon atoms, and R n (n=2 to 3, 6 to 7) has an electron withdrawing group when L 1 is not a sulfonyl group or > C (CF 3 ) 2 ). Indicating the bonding site. ) [ Chemical 2] In the formula (2), L 2 is a single bond, a sulfonyl group, > C (CF 3 ) 2 , an oxygen atom or a divalent organic group having 1 to 20 carbon atoms) L 2 is bonded to any one of X 11 ～X 14 and X 15 ～X 18 , X n (n=11 to 18) is C-R n （n=11～18）.R n (n=9 to 18) and is a group selected from the group consisting of a hydrogen atom, an electron withdrawing group and a monovalent organic group having 1 to 20 carbon atoms, and R n (n=12 to 13, 16 to 17) has an electron withdrawing group when L 2 is not a sulfonyl group nor > C (CF 3 ) 2 ). Indicating the bonding site. ) [ Chemical 3] In the formula (3), L 3 is an amide bond, L 3 is connected to any one position of X 19 ～X 22 , X n (n=19 to 22) is C-R n （n=19～22）.R n (n=19 to 22) and each independently is a group selected from the group consisting of a hydrogen atom, an electron withdrawing group and a monovalent organic group having 1 to 20 carbon atoms, and any one or more of R n (n=20 to 21) has an electron withdrawing group. Indicating the bonding site. ) [ Chemical 4] In the formula (4), L 4 is a single bond, a sulfonyl group, > C (CF 3 ) 2 , an oxygen atom or a divalent organic group having 1 to 20 carbon atoms) L 4 is bonded to any one of X 31 ～X 35 and X 36 ～X 40 , X n (n=23 to 40) is C-R n （n=23～40）.R n (n=23 to 40) and is a group independently selected from the group consisting of a hydrogen atom, an electron withdrawing group and a monovalent organic group having 1 to 20 carbon atoms, and R n (n=33, 38) has an electron withdrawing group when L 4 is neither a sulfonyl group nor > C (CF 3 ) 2 ). 1 Is connected to any one of the X 23 ～X 26 positions. 2 Is connected to any one of the X 27 ～X 30 positions. 1 And 2 Indicating the bonding site. ) [ Chemical 5] In the formula (5), L 5 is a single bond, a sulfonyl group, > C (CF 3 ) 2 , an oxygen atom or a divalent organic group having 1 to 20 carbon atoms) L 5 is bonded to any one of X 49 ～X 53 and X 54 ～X 58 , X n (n=41 to 58) is C-R n （n=41～58）.R n (n=41 to 58) and is a group independently selected from the group consisting of a hydrogen atom, an electron withdrawing group and a monovalent organic group having 1 to 20 carbon atoms, and when L 5 is neither a sulfonyl group nor > C (CF 3 ) 2 ), any one or more of R n (n=51, 58) has an electron withdrawing group. 3 Is connected to any one of the X 41 ～X 44 positions. 4 Is connected to any one of the X 45 ～X 48 positions. 3 And 4 Indicating the bonding site).
  11. 11. The photosensitive resin composition according to claim 10, wherein when the (a) resin has the (a 1) resin, at least one of R n (n=1 to 8) has an electron withdrawing group, When the resin (a) has the resin (a 2), at least one of R n (n=11 to 18) has an electron withdrawing group, When the resin (a) has the resin (a 3), at least one of R n (n=19 to 22) has an electron withdrawing group, When the resin (a) has the resin (a 4), at least one of R n (n=23 to 40) has an electron withdrawing group, When the resin (a) includes the resin (a 5), any one or more of R n (n=41 to 58) has an electron withdrawing group.
  12. 12. The photosensitive resin composition according to any one of claims 1 to 5, 10 and 11, wherein at least one of the following conditions (p1α) and the following conditions (1α) is satisfied, The content of (P1 alpha) fluorine element in the structure of the resin (a) is 10,000 mass ppm or less; the content of the fluorine element (1 alpha) in all solid components of the photosensitive resin composition is 1,000 mass ppm or less.
  13. 13. The photosensitive resin composition according to any one of claims 1 to 5, 10 and 11, wherein the (b) amine compound is an amine salt, The amine salt is a compound containing a cationic species having a primary amine structure or a secondary amine structure, and an anionic species.
  14. 14. A method of manufacturing a pattern, comprising: a step of applying the photosensitive resin composition according to any one of claims 1 to 5, 10 and 11 to a substrate; Exposing the coated object through a photomask; A step of heating the coating material while or after the exposure of the photomask is interposed; Developing the heated coating material, and For the coating after development and heating the product.
  15. 15. A cured product obtained by curing the photosensitive resin composition according to any one of claims 1 to 5, 10 and 11.
  16. 16. The cured product according to claim 15, wherein the content of the (b) amine compound in the cured product is 0.001 mass% or more and 1.00 mass% or less relative to 100 mass% of the cured product.
  17. 17. An electronic component having the cured product according to claim 15.
  18. 18. A display device having the cured product according to claim 15.

Description

Photosensitive resin composition, method for producing pattern, cured product, electronic component, and display device Technical Field The invention relates to a photosensitive resin composition, a pattern manufacturing method, a cured product, an electronic part and a display device. Background Polyimide, polybenzoxazole, or the like, which is excellent in heat resistance, electrical insulation, and mechanical properties, is widely used as a surface protective film or an interlayer insulating film used for electronic parts, an insulating layer of an organic electroluminescent element, and a planarization film of a thin film transistor (Thin Film Transistor, TFT) substrate. In recent years, photosensitive resin compositions which impart photosensitive properties to these resins themselves or their precursors have been used. By using the photosensitive resin composition, the patterning process can be simplified, and the complicated manufacturing process can be shortened. The photosensitive resin composition includes a positive material having an exposed portion which is easily soluble in a developer and capable of patterning, and a negative material having a composition itself which is easily soluble and an exposed portion which is insoluble in a developer. As a positive photosensitive resin composition, for example, a photosensitive resin composition obtained by adding a quinone diazide compound to polyimide, polyamideimide, polybenzoxazole, or a precursor of these is known (for example, refer to patent document 1). As a negative photosensitive resin composition, a photosensitive resin composition obtained by adding a photopolymerizable compound and a photopolymerization initiator to polyimide, polyamideimide, polybenzoxazole, and precursors thereof is known (for example, refer to patent document 2). Prior art literature Patent literature Patent document 1 Japanese patent laid-open publication No. 2011-180773 Patent document 2 Japanese patent application laid-open No. 2021-120714 Disclosure of Invention Problems to be solved by the invention In recent years, in the progress of high integration and large-sized semiconductor devices, there has been a demand for a sealing resin package having a reduced thickness, a reduced size, and a uniform film thickness, and there has been a demand for resins having higher sensitivity, heat resistance, and a reduced film thickness reduction during development, and the like, than before. However, the technique described in patent document 1 has a problem that the difference in the dissolution contrast between the unexposed material and the exposed portion is small, and there is a limit in the reduction in the film thickness during development, or a problem that the heat resistance is lowered due to the quinone diazide compound remaining in the film after development. In addition, in the technique described in patent document 2, since (meth) acrylate is used as a photopolymerization initiator, there is a problem in that heat resistance is lowered. The purpose of the present invention is to provide a photosensitive resin composition which has excellent heat resistance, little film reduction during development, and high sensitivity. Technical means for solving the problems In order to solve the above problems, the photosensitive resin composition of the present invention has the following structures [1] to [18 ]. [1] A photosensitive resin composition comprising: (a) One or more resins (hereinafter referred to as "(a) resins") selected from the group consisting of polyimide, polyamideimide, polybenzoxazole, and precursors thereof, (B) Amine compound (C) The photo-acid generator is used for generating a photo-acid, The amine compound (b) is primary amine or secondary amine, The photosensitive resin composition contains 35 parts by mass or more of the (b) amine compound per 100 parts by mass of the (a) resin. [2] The photosensitive resin composition according to item [1], wherein the acid equivalent of the resin (a) is 500 g/mol or more, and The carboxylic acid equivalent of the resin (a) is 500 g/mol or more, or the resin (a) does not have carboxyl groups. [3] The photosensitive resin composition according to [1] or [2], wherein the (a) resin is a resin containing an amide bond in a repeating unit, and is a polyimide precursor, a polyamideimide precursor, or a polybenzoxazole precursor. [4] The photosensitive resin composition according to any one of [1] to [3], wherein the (a) resin has an electron-withdrawing group which is one or more groups selected from the group consisting of a nitro group, a cyano group, a sulfo group and a sulfonyl group. [5] The photosensitive resin composition according to any one of [1] to [4], wherein the (b) amine compound is a monoamine compound. [6] The photosensitive resin composition according to any one of [1] to [5], wherein the (b) amine compound is a primary amine. [7] The photosensitive resin composition according to any one of [1] to [6]