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Copolymer film forming resin containing benzoxazine structure and deep UV negativity chemical amplification type photo resist

A technology of film-forming resin and benzoxazine, which is applied in the field of deep ultraviolet negative chemically amplified photoresist composition, and can solve problems such as swelling, film shrinkage, thermal stability, etc.

Active Publication Date: 2010-07-28
成都金桨高新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the actual application of photoresist, the negative photoresist is insoluble in the developer due to the crosslinking reaction of the exposed part. The biggest problem it has is mainly the swelling problem, and the shrinkage of the film occurs during baking. and thermal stability

Method used

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  • Copolymer film forming resin containing benzoxazine structure and deep UV negativity chemical amplification type photo resist
  • Copolymer film forming resin containing benzoxazine structure and deep UV negativity chemical amplification type photo resist
  • Copolymer film forming resin containing benzoxazine structure and deep UV negativity chemical amplification type photo resist

Examples

Experimental program
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Effect test

Embodiment 1

[0090] A copolymer film-forming resin containing a benzoxazine structure, which is prepared from the following comonomers and their contents, in the presence of a free radical initiator, by heating for copolymerization:

[0091] 90 grams of p-hydroxystyrene;

[0092] Styrene 5 grams;

[0093] 3-Phenyl-3,4-dihydro-6-(vinyl)-1,3-benzoxazine 7 g.

[0094] The preparation method is: in a 500mL three-neck flask equipped with a mechanical stirrer, condenser, thermometer and nitrogen inlet, add 90 grams of p-hydroxystyrene, 5 grams of styrene, 3-phenyl-3,4-dihydro- 7 grams of 6-(vinyl)-1,3-benzoxazine, 250 grams of tetrahydrofuran, 2 grams of azobisisobutyronitrile, nitrogen flow for 10 minutes under stirring, then heated to 60-70 ° C, and the reaction was refluxed for 4 ~24 hours later, then cooled to room temperature. The polymer solution is precipitated with methanol, then dissolved with acetone, and then precipitated with methanol, repeated 2 to 3 times, and finally vacuum-dried...

Embodiment 2

[0096] A copolymer film-forming resin containing a benzoxazine structure, which is prepared from the following comonomers and their contents, in the presence of a free radical initiator, by heating for copolymerization:

[0097] 100 grams of p-acetoxystyrene;

[0098] 6 grams of methyl methacrylate;

[0099] 3-Phenyl-3,4-dihydro-6-(vinyl)-1,3-benzoxazine 20 g.

[0100] The preparation method is: in a 500mL three-neck flask equipped with a mechanical stirrer, condenser, thermometer and nitrogen inlet, add 100 grams of p-acetoxystyrene, 6 grams of methyl methacrylate, 3-phenyl-3, 20 grams of 4-dihydro-6-(vinyl)-1,3-benzoxazine, 250 grams of tetrahydrofuran, 2.6 grams of azobisisobutyronitrile, nitrogen for 10 minutes under stirring, and then heated to 60-70 °C, the reaction was refluxed for 4-24 hours, and then cooled to room temperature. The polymer solution was precipitated with methanol, then dissolved with acetone, and then precipitated with methanol, repeated 2 to 3 time...

Embodiment 3

[0102] A copolymer film-forming resin containing a benzoxazine structure, which is prepared from the following comonomers and their contents, in the presence of a free radical initiator, by heating for copolymerization:

[0103] 100 grams of p-acetoxystyrene;

[0104] 10 grams of p-tert-butylstyrene;

[0105] 8 grams of methyl methacrylate;

[0106] 3-Phenyl-3,4-dihydro-6-(vinyl)-1,3-benzoxazine 7 g.

[0107] The preparation method is: in a 500mL three-neck flask equipped with a mechanical stirrer, a condenser, a thermometer and a nitrogen inlet, add 100 grams of p-acetoxystyrene, 10 grams of p-tert-butylstyrene, and 8 grams of methyl methacrylate. gram, 3-phenyl-3,4-dihydro-6-(vinyl)-1,3-benzoxazine 7 grams, tetrahydrofuran 250 grams, azobisisobutyronitrile 1.25 grams, nitrogen flow under stirring 10 minutes, then heated to 60 ~ 70 ° C, the reaction was refluxed for 4 ~ 24 hours, and then cooled to room temperature. The polymer solution is precipitated with methanol, then...

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Abstract

The invention relates to a copolymer film-forming resin containing a benzoxazine structure. The copolymer film-forming resin is prepared by a polyreaction of a comonomer in a solvent in the presence of a radical initiator and corresponding post treatment. The comonomer comprises a monomer containing hydroxystyrene (40-90 parts by weight), a monomer containing the benzoxazine structure (5-40 partsby weight), acrylate monomers or / and styrene monomers (1-40 parts by weight); the molecular weight of the copolymer film-forming resin is 2000-40000, and the molecular weight distribution is 1.3-3. Anegative photoresist mainly consists of the film-forming resin, a photoacid generator, a crosslinking agent, a solvent, organic base and a dissolution inhibitor. The invention improves the heat resistance and the heat stability of the film-forming resin by introducing the benzoxazine structure in a main chain (or a side chain) of poly(p-hydroxystyrene), and solves the problems of shrinkage and heat stability of photoresist films in baking.

Description

technical field [0001] The present invention relates to a preparation method of a copolymer film-forming resin (also known as "film-forming agent") containing a benzoxazine structure, and a deep ultraviolet (DUV) negative agent configured by using the film-forming resin. Chemically amplified photoresist compositions. Background technique [0002] Photoresist, also known as photoresist, refers to an etching-resistant thin film material whose solubility is changed by irradiation or radiation of exposure sources such as ultraviolet light, excimer laser beams, electron beams, ion beams, and X-rays. Photoresist is mainly used in the microfabrication process of integrated circuits and semiconductor discrete devices in the electronics industry. It uses photochemical reactions to transfer the required micrographics from the mask plate to the substrate to be processed after exposure and development, and then Etching, diffusion, ion implantation, metallization and other processes. T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F212/14C08F212/32C08F8/32C08F222/40C08F216/12G03F7/038
Inventor 杨刚
Owner 成都金桨高新材料有限公司
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