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Starlike tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof

A tetraphenylethylene, positive photoresist technology, applied in the field of materials, can solve the problems affecting the resolution of lithography patterns, molecular weight polydispersity, molecular chain entanglement, etc., and achieves good thermal stability, high glass transition temperature, The effect of easy film formation

Active Publication Date: 2015-04-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, commercial photoresist host materials usually use low-molecular-weight polymers with a molecular weight of 5,000 to 15,000 Daltons, but polymer materials usually affect photolithographic patterns due to reasons such as large molecular volume, polydisperse molecular weight, and molecular chain entanglement. resolution

Method used

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  • Starlike tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof
  • Starlike tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof
  • Starlike tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The preparation method of tetrakis-(7,8-di-tert-butyl carbonate-based biphenyl) ethylene molecular glass includes the following steps:

[0057] 1) Tetra-(7,8-dimethoxybiphenyl)ethylene, the synthetic route is as follows:

[0058]

[0059] Under the protection of high-purity nitrogen, add tetra(4-bromophenyl)ethylene (648mg, 1.0mmol, 1.0eq), Pd(PPh) into a 50ml Schleck reaction flask 3 ) 4 (116mg, 0.1mmol, 0.1eq) and 15ml of re-distilled toluene, stir to dissolve and then use a syringe to add 3,4-dimethoxyphenylpinacol borane (1320mg, 5.00mmol, 5.0 eq) ethanol solution 3ml and 2MNa 2 CO 3 1ml aqueous solution, the reaction solution was heated at 50~70℃ and refluxed for 12h, cooled to room temperature, extracted with dichloromethane / water, combined the organic layers, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, recrystallized from ethanol to obtain a white solid 658mg , The yield is 75%. 1 HNMR(400MHz, CDCl 3 )δ(ppm)7.57(d,J=...

Embodiment 2

[0069] The preparation method of tetra-(8-adamantyl acetate biphenyl) ethylene molecular glass includes the following steps:

[0070] 1) Tetra-(8-methoxybiphenyl)ethylene, the synthetic route is as follows:

[0071]

[0072] Under the protection of high-purity nitrogen, add tetra(4-bromophenyl)ethylene (648mg, 1.0mmol, 1.0eq), Pd(PPh) into a 50ml Schleck reaction flask 3 ) 4 (116mg, 0.1mmol, 0.1eq) and 15ml of re-distilled toluene, stir to dissolve and then use a syringe to add 4-methoxyphenyl pinacol borane (1170mg, 5.00mmol, 5.0eq) to the reaction flask Ethanol solution 3ml and 2MNa 2 CO 3 1ml aqueous solution, the reaction solution was heated at 50~70℃ and refluxed for 12h, cooled to room temperature, extracted with dichloromethane / water, combined the organic layers, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, recrystallized from ethanol to obtain 545mg of white solid , The yield is 72%. 1 HNMR(400MHz, CDCl 3 )δ(ppm)7.57(d,J=8....

Embodiment 3

[0081] The synthesis method of tetrakis-(8-norbornyl acetate-based biphenyl) ethylene molecular glass is the same as that in Example 2, except that the raw material α-chloroadamantyl acetate is α-chloronorbornyl acetate.

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Abstract

The invention discloses starlike tetraphenylethylene derivative molecular glass, a positive photoresist, a positive photoresist coating and application thereof. The starlike tetraphenylethylene derivative molecular glass has the molecular structure shown in the description. The molecular glass is simple in synthesis process and suitable for industrial production; the tetraphenylethylene has a spatial solid geometrical skeleton adopting a rigid structure, can effectively inhibit molecular crystallization and is easy for film formation; the molecular glass has good solubility in various polar solvents, and has the characteristics of high glass transition temperature and high thermal stability, and can better meet requirements of a photoetching process; by adopting a spin coating method, a good film can be obtained, and the molecular glass can be used as the photoresist and can be prepared into the positive photoresist for photoetching through cooperation with other additives.

Description

Technical field [0001] The invention belongs to the technical field of materials, and specifically relates to a star-shaped tetraphenylethylene derivative molecular glass, a positive photoresist, a positive photoresist coating and applications thereof. Background technique [0002] Photoresist (also known as photoresist) is a kind of etch-resistant thin film material whose solubility changes after being radiated by energy such as light beam, electron beam, ion beam or x-ray. It is used in the micro processing of integrated circuits and semiconductor discrete devices. China also has a wide range of applications. By coating photoresist on semiconductors, conductors and insulators, the part left after exposure and development protects the bottom layer, and then etching with an etchant can transfer the required fine patterns from the mask to the substrate. Therefore, photoresist is a key material in microfabrication technology. The rapid development of the semiconductor industry pu...

Claims

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Application Information

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IPC IPC(8): C07C69/96C07C68/00C07C67/31C07C69/712G03F7/039
CPCC07C69/712C07C69/96C07C2602/42C07C2602/44C07C2603/74G03F7/039
Inventor 李嫕郝青山陈金平曾毅于天君
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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