Search

CN-122029489-A - Photosensitive resin composition, cured product, display device, and electronic component

CN122029489ACN 122029489 ACN122029489 ACN 122029489ACN-122029489-A

Abstract

The purpose of the present invention is to provide a photosensitive resin composition which has good solubility in a diluent, can suppress contamination of an opening after curing, can suppress foaming during lamination, and has good light-emitting characteristics even after a reliability test of a cured product, a cured product obtained by curing the photosensitive resin composition, and a display device and an electronic component each comprising the cured product of the resin composition. The photosensitive resin composition of the present invention contains a resin (a) (hereinafter referred to as a resin (a)), a photosensitive agent (B), and a solvent (C) which contain a specific structural unit, and the total content of the specific diamine residues is 30 to mol% to 100 to mol% when the total amount of the diamine residues of the resin (a) is 100 mol%.

Inventors

  • SAEKI AKINORI
  • Gui Bencong
  • KOSHINO MIKA
  • Wang Lang of the Department
  • MASAHIRO KITADA

Assignees

  • 东丽株式会社

Dates

Publication Date
20260512
Application Date
20250116
Priority Date
20240131

Claims (20)

  1. 1. A photosensitive resin composition comprising a resin (A) (hereinafter referred to as resin (A)), a sensitizer (B), and a solvent (C) each comprising at least one of a structural unit represented by formula (1), a structural unit represented by formula (19), and a structural unit represented by formula (70), When the total amount of diamine residues in the resin (a) is 100 mol%, the total amount of diamine residues represented by any one of the formulas (2) to (4) is 30 mol% to 100 mol%; [ chemical 1] (In the formula (1), the formula (19) and the formula (70), Y 1 independently represents an acid dianhydride residue with 2-40 carbon atoms having any one of an aliphatic structure with 2-20 carbon atoms, an alicyclic structure with 4-40 carbon atoms and an aromatic structure with 6-40 carbon atoms, Z 1 independently represents a diamine residue represented by any one of the formula (2) to the formula (4), and R 1 independently represents a hydrogen atom, an alkyl group with 1-20 carbon atoms or a monovalent group with 2-20 carbon atoms having an ethylenically unsaturated double bond; Indicating a bond [ Chemical 2] (In the formula (2), the formula (3) and the formula (4), X 1 is a direct bond or a divalent group represented by the formula (5), R 2 is an alkyl group having 1 to 4 carbon atoms, X 2 is a divalent group represented by the formula (6) or the formula (7), k is 0 or 1, Represents a bond to an imide structure, an amide structure, an amic acid ester structure, or an amic acid structure) [ Chemical 3] (In the formula (5), Represents a bond to a nitrogen atom; represents a bond to an aromatic ring [ Chemical 4] (In the formula (6) and the formula (7), R 3 independently represents an alkyl group having 1 to 4 carbon atoms, a represents 1 or 2, b represents an integer of 1 to 3, R 4 and R 5 independently represent a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom, Represents a bond to an aromatic ring, wherein R 4 and R 5 do not have the same structure).
  2. 2. The photosensitive resin composition according to claim 1, wherein the resin (a) contains a diamine residue represented by formula (2), wherein the total number of carbons of R 3 in formula (6) is 1 to 5, and wherein the total number of carbons of R 4 and the number of carbons of R 5 in formula (7) is 3 to 10.
  3. 3. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) contains a diamine residue represented by formula (2), and when a=1 is represented by formula (6-1) and a=2 is represented by formula (6-2), conditions 1 and 2 are satisfied, and the carbon number of R 4 in formula (7) is different from the carbon number of R 5 ; In the formula (6-1), the total number of carbon atoms of R 11 ～R 14 is different from the total number of carbon atoms of R 15 ～R 18 ; condition 2 in the formula (6-2), the total number of carbon atoms of R 19 ～R 22 is different from the total number of carbon atoms of R 25 ～R 28 ; [ chemical 5] (In the formula (6-1) and the formula (6-2), R 11 ～R 28 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, wherein the formula (6-1) and the formula (6-2) satisfy the condition of the formula (6).
  4. 4. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) comprises a diamine residue represented by formula (2), and X 2 is a divalent group represented by any one of formula (8) to formula (13) and formula (76) to formula (83); [ chemical 6] In the formulae (8), (13), (76) and (83), Represents a bond to an aromatic ring).
  5. 5. The photosensitive resin composition according to claim 1 or claim 2, wherein in the formulae (1), (19) and (70), Y 1 each independently represents an acid dianhydride residue having a carbon number of 8 to 40 having a diphenyl ether structure.
  6. 6. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) has a structure represented by formula (84); [ chemical 7] (In the formula (84), R 29 represents a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms; indicating the bonding site to the nitrogen atom).
  7. 7. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) comprises a structural unit (a) and/or a structural unit (b), and the resin (a) comprises a structural unit (c) and/or a structural unit (d), The resin (a) comprises at least one of a structural unit (a) and a structural unit (c); The structural unit (a) is a structural unit represented by formula (1), formula (19) or formula (70) in which Z 1 in formula (1), formula (19) and formula (70) is represented by formula (2) and two X 1 existing in formula (2) are both direct bonds, The structural unit (b) is a structural unit represented by formula (48), formula (49) or formula (71) in which Z 3 is represented by formula (45) and two X 1 existing in formula (45) are both direct bonds, The structural unit (c) is a structural unit represented by formula (1), formula (19) or formula (70) wherein Z 1 is represented by formula (2) and at least one X 1 of two X 1 present in formula (2) is a divalent group represented by formula (1), formula (19) or formula (70) represented by formula (5), Structural unit (d), structural unit represented by formula (48), formula (49) and formula (71) wherein Z 3 is represented by formula (45) and at least one X 1 of two X 1 present in formula (45) is a structural unit represented by formula (48), formula (49) or formula (71) of a divalent group represented by formula (5), [ Chemical 8] (In the formulae (48), (49) and (71), Y 1 and R 1 are in the same range as those described in the formulae (1), (19) and (70), and Z 3 independently represents a diamine residue represented by the formula (45); Indicating a bond [ Chemical 9] (In the formula (45), X 1 is a direct bond or a divalent group represented by the formula (5), R 2 and k are the same ranges as those described in the formula (2), and X 3 is a divalent organic group represented by any one of the formulas (64) to (69); represents a bond to an imide structure, an amide structure, an amic acid ester structure, or an amic acid structure) [ Chemical 10] ( Represents a bond to an aromatic ring).
  8. 8. The photosensitive resin composition according to claim 7, wherein when the total amount of the constituent units of the polyimide contained in the resin (a) is 100 mol%, the total content of the constituent units (a) and (b) is 20 to mol to 95 mol%, and the total content of the constituent units (c) and (d) is 5 to mol to 80 mol%.
  9. 9. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) further comprises at least one of a structural unit represented by formula (50), a structural unit represented by formula (51), and a structural unit represented by formula (72); [ chemical 11] (In the formula (50), the formula (51) and the formula (72), Y 1 and R 1 are in the same range as those described in the formula (1), the formula (19) and the formula (70)), and Z 5 independently represents a diamine residue represented by the formula (46) or the formula (47); Indicating a bond [ Chemical 12] (In the formula (46) and the formula (47), X 4 represents a direct bond or-C (CH 3 ) 2 -; t represents any integer of 0 to 2; Represents a bond to an imide structure, an amide structure, an amic acid ester structure, or an amic acid structure).
  10. 10. The photosensitive resin composition according to claim 9, wherein when the total amount of the structural units of polyimide contained in the resin (a) is 100 mol%, the total content of the structural unit represented by formula (50), the structural unit represented by formula (51), and the structural unit represented by formula (72) is 1: 1 mol% to 30: 30 mol%.
  11. 11. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) contains an acid dianhydride residue having 4 to 20 carbon atoms containing an alicyclic structure.
  12. 12. The photosensitive resin composition according to claim 11, wherein the total content of the acid dianhydride residues having 4 to 20 carbon atoms including an alicyclic structure is 20 to mol% to 100 mol% based on 100 mol% of the total content of the acid dianhydride residues of the resin (a).
  13. 13. The photosensitive resin composition according to claim 11, wherein the resin (a) contains at least one acid dianhydride residue selected from the group consisting of formula (15), formula (16), and formulae (85) to (94); [ chemical 13] In the formulae (15), (16) and (85) to (94), Represents a bond to an imide structure, an amide structure, an amic acid ester structure, or an amic acid structure).
  14. 14. The photosensitive resin composition according to claim 1 or claim 2, wherein the imide ring closure of the resin (a) is 50% or less.
  15. 15. The photosensitive resin composition according to claim 1 or claim 2, wherein the resin (a) has an esterification rate of 10% or more and 100% or less.
  16. 16. The photosensitive resin composition according to claim 1 or claim 2, wherein the solvent (C) contains the solvent represented by formula (17) and/or the solvent (C1) represented by formula (18); [ chemical 14] (In the formula (17) and the formula (18), R 6 independently represents an alkyl group having 1 to 6 carbon atoms, R 7 represents an alkyl group having 2 to 6 carbon atoms).
  17. 17. The photosensitive resin composition according to claim 1 or claim 2, wherein the solvent (C) comprises a solvent (C2) having a hydroxyl group and having a boiling point of 100 ℃ to 200 ℃ inclusive at atmospheric pressure.
  18. 18. The photosensitive resin composition according to claim 1 or claim 2, wherein the photosensitive resin composition comprises both a solvent represented by formula (17) and/or a solvent (C1) (hereinafter, referred to as a solvent (C1)) represented by formula (18), and a solvent (C2) (hereinafter, referred to as a solvent (C2)) having a hydroxyl group and having a boiling point of 100 ℃ to 200 ℃ inclusive at atmospheric pressure, The content ratio of the solvent (C1) to the solvent (C2) in the photosensitive resin composition is 1 to 1000 inclusive, where X is the mass of the solvent (C1) and Y is the mass of the solvent (C2).
  19. 19. A cured product obtained by curing the photosensitive resin composition according to claim 1 or 2.
  20. 20. A display device comprising the cured product according to claim 19.

Description

Photosensitive resin composition, cured product, display device, and electronic component Technical Field The invention relates to a photosensitive resin composition, a cured product, a display device and an electronic component. Background Conventionally, photosensitive polyimide and/or photosensitive polybenzoxazole which are excellent in heat resistance, electrical insulation, mechanical properties, and the like and can be patterned by photolithography have been widely used in a planarizing layer of a deposition layer of an organic Electroluminescence (EL) display device or a thin film transistor (Thin Film Transistor, TFT) substrate, a surface protective film of a semiconductor element, or an interlayer insulating film of an electronic component, and many proposals have been made so far (for example, refer to patent document 1 and patent document 2). When a film excellent in heat resistance and mechanical properties is obtained by thermally dehydrating and ring-closing a coating film of a polyimide resin or a polybenzoxazole resin, high-temperature calcination at about 350 ℃ is generally required. In addition, the operation of thermally dehydrating and ring-closing a coating film of a polyimide resin or a polybenzoxazole resin to obtain a film excellent in heat resistance and mechanical properties is sometimes referred to as calcination (curing), and the change of the coating film is sometimes referred to as hardening. In addition, in view of the low temperature process resistance and the reliability of the semiconductor package, a polyimide resin, a polybenzoxazole resin, and a polyamide-imide resin, which are used in recent years, for a memory device, a molded resin used for manufacturing the semiconductor package, and the like, can be cured by firing at 250 ℃ or less in a surface protective film or an interlayer insulating film, and are required to have high mechanical properties, chemical resistance, and adhesion. In addition, the demands for high reliability of organic EL display devices are strict year by year, and materials for planarizing layers and insulating layers are also demanded to have high light emission characteristics even after reliability test under accelerated conditions such as light irradiation. Polyimide, polybenzoxazole, and any of these precursors used in conventional photosensitive polyimide and/or photosensitive polybenzoxazole generally have a fluorine-containing group such as trifluoromethyl group in the resin structure, but there is a problem that fluorine-containing residues generated during curing or dry etching adhere to the electrode in the opening portion to increase the contact resistance of the electrode. In contrast, a method of using an organic insulating film containing no fluorine (for example, see patent document 3) or a method of using a polyimide precursor containing no fluorine, in which a specific structure is introduced into the main chain, to achieve both suppression of contamination of the electrode and high sensitivity (for example, see patent document 4) has been disclosed. On the other hand, for example, a method of providing an organic EL display device excellent in long-term reliability by using a photosensitive resin composition having a molar ratio S/C of sulfur to carbon within a specific range obtained when a cross section of a cured film is measured by an electron beam microanalyzer (for example, refer to patent document 5), or a method of providing a photosensitive resin composition having high sensitivity and being soluble in a gamma-butyrolactone solvent by using a resin having a specific structure containing no halogen atom in a molecule (for example, refer to patent document 6) have been disclosed. Prior art literature Patent literature Patent document 1 Japanese patent laid-open publication No. 2002-91343 Patent document 2 Japanese patent laid-open publication No. 2002-116715 Patent document 3 Japanese patent laid-open No. 2009-177113 Patent document 4 Japanese patent laid-open publication No. 2003-76007 Patent document 5 International publication No. 2016/047483 Patent document 6 International publication No. 2009/081950 Disclosure of Invention Problems to be solved by the invention However, conventional polyimide, polybenzoxazole, and any of these precursors having no fluorine group such as trifluoromethyl group have had a problem that they have poor solubility in an organic solvent, and even if they are dissolved in a part of aprotic polar solvents such as N-methyl-2-pyrrolidone or γ -butyrolactone, they have poor solubility in propylene glycol monomethyl ether widely used as a diluent in photolithography steps. The resins disclosed in patent documents 3 and 4 have problems in terms of solubility to propylene glycol monomethyl ether. Patent document 5 discloses a photosensitive resin composition containing a fluorine-containing polyimide precursor, and as a result of studies by the pen and others, there is a problem that contamination