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Novolak-type phenolic hydroxyl-containing resin and resist film

一种酚醛清漆型、羟基树脂的技术，应用在仪器、光机械设备、有机化学等方向，能够解决耐热性、显影性不充分、不能够应对市场要求性能等问题，达到耐热性及耐干蚀刻性优异的效果

Active Publication Date: 2021-04-20
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The most widely used phenolic hydroxyl group-containing resin in photoresist applications is cresol novolac type resin, but as mentioned above, it cannot meet the current market requirements of high-level and diversified development. Performance, heat resistance , Developability is also insufficient (see Patent Document 1)

Method used

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  • Novolak-type phenolic hydroxyl-containing resin and resist film
  • Novolak-type phenolic hydroxyl-containing resin and resist film
  • Novolak-type phenolic hydroxyl-containing resin and resist film

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0158] Hereinafter, specific examples will be given to further describe the present invention in detail. It should be noted that the number average molecular weight (Mn), weight average molecular weight (Mw), and polydispersity (Mw / Mn) of the synthesized resin are values ​​measured by GPC under the following measurement conditions, and the purity, dimer and trimer The body content was calculated from the area ratio of the GPC spectrum obtained under the following measurement conditions.

[0159] [Measurement conditions of GPC]

[0160] Measuring device: "HLC-8220 GPC" manufactured by Tosoh Corporation

[0161] Column: Showa Denko "Shodex KF802" (8.0mmФ×300mm) + Showa Denko "Shodex KF802" (8.0mmФ×300mm)

[0162] + Showa Denko "Shodex KF803" (8.0mmФ×300mm) + Showa Denko "Shodex KF804" (8.0mmФ×300mm)

[0163] Column temperature: 40°C

[0164] Detector: RI (differential refractometer)

[0165] Data processing: "GPC-8020Model II Version4.30" manufactured by Tosoh Corporation ...

manufacture example 14

[0195] Production example 1 Production of tetrafunctional phenolic compound (A-1)

[0196] Into a 100 ml two-necked flask equipped with a cooling tube, 73 g (0.6 mol) of 2,5-xylenol and 20 g (0.15 mol) of terephthalaldehyde were charged and dissolved in 300 ml of 2-ethoxyethanol. After adding 10 g of sulfuric acid while cooling in an ice bath, heating and stirring were performed in an oil bath at 80° C. for 2 hours to make it react. After the reaction, water was added to the resulting solution to reprecipitate the crude product. The precipitated crude product was redissolved in acetone and reprecipitated in water, and the precipitate was collected by filtration and vacuum-dried to obtain 62 g of a tetrafunctional phenol compound (A-1) as a light red powder. use 1 H-NMR confirmed the production of a compound represented by the following structural formula. In addition, the purity calculated from the GPC spectrum was 98.2%. The GPC chart of 4 functional phenolic compounds (A...

Embodiment 2、3 and comparative example 1、2

[0205] About the novolac type phenolic hydroxyl-containing resin obtained in Example 1 and Comparative Production Examples 1 and 2, a photosensitive composition was prepared in the following manner, and various evaluations were performed. The results are shown in Table 1.

[0206] Preparation of photosensitive composition

[0207] 7 g of the above-mentioned novolac-type phenolic hydroxyl-containing resin was dissolved in 15 g of propylene glycol monomethyl ether acetate, and 3 g of a photosensitizer was added to the solution and dissolved. This was filtered through a 0.2 μm membrane filter to obtain a photosensitive composition.

[0208] The photosensitizer used Toyo Gosei Kogyo Co., Ltd. "P-200" (4,4'-[1-[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenyl]ethylidene Base] the condensation product of 1 mole of bisphenol and 2 moles of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride).

[0209] Preparation of composition for heat resistance test

[0210] 7 g of the above-mentioned...

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Abstract

Provides a novolac type phenolic hydroxyl-containing resin and a resist film that are excellent in developability, heat resistance, and dry etching resistance. A novolak-type phenolic hydroxyl-containing resin is characterized in that it has the following structural formula (1) [wherein, Ar represents an arylene group. R 1 Each is independently any of a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, and a halogen atom, and m is each independently an integer of 1-3. ] the structural part (I) shown or the following structural formula (2) [wherein, Ar represents an arylene group. R 1 Each is independently any of a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, and a halogen atom, and m is each independently an integer of 1-3. ] as a repeating unit.

Description

technical field [0001] The present invention relates to a novolak-type phenolic hydroxyl-containing resin excellent in developability, heat resistance, and dry etching resistance, and to a resist film using the same. Background technique [0002] In addition to being used in adhesives, molding materials, coatings, photoresist materials, epoxy resin raw materials, and curing agents for epoxy resins, phenolic hydroxyl-containing resins have excellent heat resistance and moisture resistance. , as a curable composition with phenolic hydroxyl-containing resin itself as the main agent, or as a curing agent for epoxy resins, it is widely used in electrical / electronic fields such as semiconductor sealing materials and insulating materials for printed circuit boards. [0003] Among them, in the field of photoresists, a variety of resist pattern formation methods that are subdivided according to applications and functions have been continuously developed. Along with this, the performa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/15C07C37/20C08G8/20C08L61/12G03F7/023G03F7/11
CPCC07C37/20C08L61/12C08G8/04C08G8/20G03F7/0236G03F7/094C07C39/15G03F7/023G03F7/11C08G8/14
Inventor 今田知之佐藤勇介
Owner DIC CORP