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A kind of photosensitive resin, positive photoresist and application

A positive photoresist and photosensitive resin technology, applied in the field of photolithography, can solve the problems of turbidity, limited improvement, and difficult to peel off the photoresist, and achieve the effect of high heat resistance stability and good photosensitive performance.

Active Publication Date: 2020-10-09
上海飞凯电子材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the prior art, shallow cross-linking of novolac resin is used to increase its glass transition temperature to increase its flow temperature to 130-135°C, but the improvement is limited, and the above problems still cannot be avoided.
Alternatively, the existing technology uses deep ultraviolet exposure treatment to make the photoresist deeply cross-linked to improve its heat resistance, but the photoresist after treatment will be difficult to peel off
U.S. Patent No. 4,439,516 uses polyp-hydroxystyrene to replace the novolac resin on the basis of ordinary diazonaphthoquinone-based positive photoresists. Although this method can greatly improve the thermal stability of the photoresist, the diazo Naphthoquinone sulfonate has basically no solvent-inhibiting effect on poly(p-hydroxystyrene) in alkaline developer, so it cannot be used to prepare microscale devices with micron-scale details
Further, if the photosensitive resin is formed by mixing polyp-hydroxystyrene with novolac resin, the photosensitive resin can indeed increase the thermal stability of the photoresist, but once it is mixed with the photosensitive compound, it will phase separate and produce turbidity

Method used

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  • A kind of photosensitive resin, positive photoresist and application
  • A kind of photosensitive resin, positive photoresist and application
  • A kind of photosensitive resin, positive photoresist and application

Examples

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preparation example Construction

[0046] During the preparation of the photosensitive resin, the above-mentioned vinyl phenolic monomers can be used for free radical polymerization, but there are many side reactions of phenolic free radical polymerization. The side reaction of deprotonation of phenolic hydroxyl group will occur in anionic polymerization, and the side reaction of electrophilic addition of benzene ring will easily occur in cationic polymerization. Therefore, the embodiments of the present invention preferably use acetyl groups or other groups to protect vinylphenol monomers, and carry out free radical, active free radical, anionic, or cationic polymerization reactions, and then remove the protective groups to obtain the desired polyhydroxybenzene Ethylene homopolymer or copolymer. In principle, various polyhydroxystyrene homopolymers or copolymers prepared from the above-mentioned monomers can utilize diazonaphthoquinone sulfonyl chloride, such as 2-diazo-1-naphthoquinone-5-sulfonyl chloride or ...

Embodiment 1

[0063] This example provides three kinds of p-hydroxystyrene-styrene copolymers, the preparation method of which is as follows: add 8.0 kg of propylene glycol mono-n-propyl ether and 2.0 kg of p-acetylstyrene into a 20-liter reactor, mix well Finally, 0.020 kg of benzoyl peroxide was added as an initiator, 0.020 kg of dimer-methylstyrene was used as a chain transfer catalyst, and the temperature was raised to 80° C. and kept at a temperature of 3 hours for polymerization. Cool to room temperature, quickly disperse and precipitate in 8 kg of methanol, and filter to separate the resin. The resin is dispersed in 4 kg of methanol, and 1.2 kg of ammonia water with a mass fraction of 25-28% is slowly added for ammonolysis. Stir at room temperature until the resulting polyparaacetylstyrene resin precipitate dissolves. Heat to 80°C and keep it warm until the ester carbonyl group disappears in the infrared spectrum. Under high-speed stirring, the resin was dissolved and dispersed in ...

Embodiment 2

[0067] This example provides a p-hydroxystyrene-p-acetoxystyrene copolymer, the specific preparation method of which is as follows: 8 kg of propylene glycol mono-n-propyl ether and 2 kg of p-acetyl styrene. After mixing evenly, add 0.10 kg of benzoyl peroxide as an initiator, 0.05 kg of dimer-methylstyrene (i.e. methylstyrene dimer) as a chain transfer catalyst, heat up to 80°C and keep it warm for 3 hours for polymerization reaction. After cooling to room temperature, the reaction solution was dispersed in 40 kg of deionized water under slow and then high-speed stirring, then vacuum filtered, and washed with a small amount of anhydrous methanol. Disperse the obtained poly(p-acetoxystyrene) powder in 8 kg of anhydrous methanol, add 20 g of p-toluenesulfonic acid monohydrate, and reflux under a nitrogen atmosphere. As the acetyl group is gradually alcoholysed, the system polymer Gradually dissolve methanol to form a uniform solution, take samples, and use Fourier transform in...

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Abstract

The invention discloses light sensitive resin, positive photoresist and an application, and belongs to the technical field of the photoresist. The light sensitive resin has the chemical structural formulas which are as shown in the specification, wherein a, b and c are molar fractions of corresponding monomers; b is greater than 0.1 and less than 0.5; c is greater than 0 and less than 0.15; a+b+cis equal to 1; R<1>, R<2>, R<3> and R<4> are all hydrogen, methyl or ethyl; R<6>, R<7> and R<8> are all hydrogen or methyl; R<9> is a formula as shown in the specification or a formula as shown in thespecification; and R<5> is nitrile group, phenyl, naphthyl, or a mono-substituted phenyl, di-substituted phenyl or tri-substituted phenyl comprising methyl, ethyl, nitrile group, methoxyl, oxethyl oracetoxyl, or a mono-substituted naphthyl, di-substituted naphthyl or tri-substituted naphthyl comprising methyl, ethyl, nitrile group, methoxyl, oxethyl or acetoxyl, or 9-carbazolyl, 1-indolyl, 1-pyrrolyl, or N-pyrrolidone alkyl. The light sensitive rein can be used as the photoresist and has high heat resistance stability.

Description

technical field [0001] The invention relates to the technical field of photolithography, in particular to a photosensitive resin, a positive photoresist and applications thereof. Background technique [0002] Photoresist, also known as photoresist, is usually used for micro-nano-scale processing of substrates such as semiconductors, metals, and dielectric layers based on radiation imaging technology. Specifically, when applying, first coat a layer of photoresist on the substrate, dry to remove the solvent, and then place the substrate in a photolithography machine for exposure processing, and the light passes through a light-shielding mask plate engraved with a binary geometric pattern Projected on the surface of the photoresist, and then post-baking, developing, drying and other processes to obtain the photoresist relief pattern, to achieve micro-nano processing of the substrate. Photoresists are divided into positive photoresists and negative photoresists. For positive ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/039G03F7/004C08F112/14C08F212/14C08F212/08C08F8/34
CPCC08F8/34C08F112/14C08F212/14C08F2800/20C08F2810/50G03F7/004G03F7/039C08F212/08
Inventor 李成红黄杰胡林云李敬舟潘长松李启文徐孝伟仇凯王海群
Owner 上海飞凯电子材料有限公司
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