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CN-122010854-A - Compound for preparing photoresist film, photosensitive resin composition and photosensitive laminate

CN122010854ACN 122010854 ACN122010854 ACN 122010854ACN-122010854-A

Abstract

The present invention relates to a compound for preparing a photoresist film, a photosensitive resin composition and a photosensitive laminate, wherein the compound is used as an adhesion promoter, and compared with the prior benzotriazole and a derivative thereof, the compound is easy to remove through an alkaline water development, acid etching or acid washing process before electroplating while the adhesion and the resolution are simultaneously considered, so that the corresponding photosensitive resin composition and the photosensitive laminate have good post-treatment compatibility, and the compound is suitable for the precise manufacturing of printed circuit boards.

Inventors

  • YUAN JUNLIN

Assignees

  • 珦盛新材料(珠海)有限公司

Dates

Publication Date
20260512
Application Date
20260130

Claims (10)

  1. 1. A compound for preparing a photoresist film, characterized in that the compound is represented by the following formula (I) or (II): Wherein, R 1 is an acid hydrolysis carboxyl protecting group or an alkali hydrolysis carboxyl protecting group, when R 1 is an acid hydrolysis carboxyl protecting group, the compound can be hydrolyzed under the condition of pH <2, and when R 1 is an alkali hydrolysis carboxyl protecting group, the compound can be hydrolyzed under the condition of pH > 10.
  2. 2. The compound for preparing a photoresist film according to claim 1, wherein: the acid hydrolysis carboxyl protecting group is at least one of tertiary alkyl, acetal, silane, enol, aryl or heteroaryl substituted tertiary alkyl, ketal imino, beta-keto, glycosyl and epoxy alkyl.
  3. 3. A compound for producing a photoresist film according to claim 2, wherein: The acid hydrolysis carboxyl protecting group is tert-butyl, 1-methylcyclohexyl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 1-ethoxyethyl, tert-butyldimethylsilyl, triethylsilyl or dimethylethylsilyl.
  4. 4. The compound for preparing a photoresist film according to claim 1, wherein: the basic hydrolysis carboxyl protecting group is an aromatic ring activated by an electron withdrawing group, and/or the basic hydrolysis carboxyl protecting group is p-nitrophenyl or pentafluorophenyl.
  5. 5. The compound for preparing a photoresist film according to claim 1, wherein: the alkaline hydrolysis carboxyl protecting group is 1-succinimidyl.
  6. 6. A photosensitive resin composition characterized in that: A process for producing a photoresist film comprising (A) an alkali-soluble binder polymer, (B) a photopolymerizable compound containing an ethylenically unsaturated double bond, (C) a photopolymerization initiator, (D) an auxiliary agent mixture, and (E) the compound for producing a photoresist film according to any one of claims 1 to 5.
  7. 7. The photosensitive resin composition according to claim 6, wherein: (E) The compound for preparing a photoresist film according to any one of claims 1 to 5, accounting for 50 to 1500ppm of the total weight of the photosensitive resin composition.
  8. 8. The photosensitive resin composition according to claim 6, wherein: (E) The compound for preparing a photoresist film according to any one of claims 1 to 5, accounting for 150 to 1000ppm of the total weight of the photosensitive resin composition.
  9. 9. The photosensitive resin composition according to claim 6, wherein: (A) The alkali-soluble binder polymer has a weight average molecular weight of 20K to 300K and an acid value of 100 to 260mgKOH/g.
  10. 10. A photosensitive laminate characterized by: A photosensitive resin composition according to any one of claims 6 to 9, comprising a support layer and a photosensitive resin layer.

Description

Compound for preparing photoresist film, photosensitive resin composition and photosensitive laminate Technical Field The invention belongs to the technical field of photosensitive materials, and particularly relates to a compound for preparing a photoresist film, a photosensitive resin composition and a photosensitive laminate. Background The printed wiring board is usually manufactured by photolithography, specifically, a method in which a photoresist film as a resist material is laminated on a substrate, for example, a copper-clad laminate, then pattern exposure is performed, an exposed portion of the photosensitive resin composition is polymerized and cured, an unexposed portion is removed by a developer, a resist pattern is formed on the substrate, then etching or plating treatment is performed, and after a conductor pattern is formed, the resist pattern is peeled off from the substrate. In recent years, with the development of higher density of smart devices, the line width/space (L/S) of circuits has been advanced to 15/15 μm or less. In this context, interfacial adhesion between the resist material and the copper surface becomes a critical factor affecting the pattern accuracy. Microcosmic, copper-photoresist film interfaces often have microcracks, areas with insufficient curing and strong polar group channels, which are easy to cause etching liquid to penetrate along the interfaces, thereby causing side etching and even pattern shedding. To improve adhesion, benzotriazole (BTA) and its derivatives are often added to photoresist films in the industry, however, there are some drawbacks to such compounds that have been put into use at present. For example, when BTA is used, the addition amount is precisely controlled, and if the addition amount is slightly excessive, etching defects or plating adhesion is not easily reduced due to removal by acid etching after development. For another example, carboxylated 5-carboxybenzotriazole or 4-carboxybenzotriazole is easily removed in the subsequent acid etching process, but a carboxyl group-rich layer is formed on the copper-photoresist film interface in the exposed area, and this hydrophilic carboxyl group-rich layer can constitute a permeation path of an etching solution, which is liable to cause side etching and resist pattern peeling under specific etching process conditions. For another example, the long-chain alkyl derivative of BTA is too hydrophobic, which may also make it difficult to clean the BTA in conventional processes, resulting in etching defects or reduced plating adhesion. Therefore, the existing BTA adhesion promoter is difficult to consider adhesion and aftertreatment compatibility under the same set of process frames. In summary, there is a long-standing paradox in the art of "adhesion-residue removal" in that the adhesion-promoting groups are often difficult to scavenge after introduction of the adhesion-promoting groups on the benzotriazole backbone, while the adhesion is sacrificed by introduction of the groups with easy-to-scavenge properties. The traditional scheme can not meet the triple requirements of high adhesive force, low residue and side erosion resistance in a precise graph below 15/15 mu m by adjusting the addition amount of BTA or introducing long-chain alkyl. Disclosure of Invention A first object of the present invention is to propose a compound for preparing a photoresist film that combines adhesion with post-processing compatibility. A second object of the present invention is to provide a photosensitive resin composition containing the above-mentioned compound for producing a photoresist film. A third object of the present invention is to provide a photosensitive laminate containing the above photosensitive resin composition. In order to achieve the above first object, the present invention provides a compound for preparing a photoresist film, the compound being represented by the following formula (I) or (II): Wherein, R 1 is an acid hydrolysis carboxyl protecting group or an alkali hydrolysis carboxyl protecting group, when R 1 is an acid hydrolysis carboxyl protecting group, the compound can be hydrolyzed under the condition of pH <2, and when R 1 is an alkali hydrolysis carboxyl protecting group, the compound can be hydrolyzed under the condition of pH > 10. Further, the acid hydrolyzed carboxyl protecting group is at least one selected from tertiary alkyl, acetal, silyl, enol, aryl or heteroaryl substituted tertiary alkyl, ketal imino, beta-keto, glycosyl and epoxy alkyl. Further, the acid hydrolyzed carboxyl protecting group is t-butyl, 1-methylcyclohexyl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 1-ethoxyethyl, t-butyldimethylsilyl, triethylsilyl or dimethylethylsilyl. Further, the basic hydrolysis carboxyl protecting group is a benzene ring activated by an electron withdrawing group, and/or the basic hydrolysis carboxyl protecting group is p-nitrophenyl or pentafluorophenyl. Further, the basic hydrolysis carbox