Star-shaped adamantane derivative molecular glasses, and preparation method and application thereof

A technology of molecular glass and adamantane, which is applied in the field of materials, can solve problems such as not being suitable for the requirements of scribe lines, and achieve the effect of simple synthesis process

Active Publication Date: 2014-05-21
国科天骥(北京)新材料技术有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional photoresist host materials usually use low-molecular-weight polymers with a molecular weight of 5,000 to 15,000 Daltons. Such polymer materials usually affect the edge roughness or Line width roughness, not suitable for finer line requirements

Method used

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  • Star-shaped adamantane derivative molecular glasses, and preparation method and application thereof
  • Star-shaped adamantane derivative molecular glasses, and preparation method and application thereof
  • Star-shaped adamantane derivative molecular glasses, and preparation method and application thereof

Examples

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Effect test

example 1

[0059] A preparation method of star adamantane derivative molecular glass, comprising the following steps:

[0060] 1) Preparation of 1,3,5,7-tetrakis-(7,8-dimethoxybiphenyl)adamantane, the synthetic route is as follows:

[0061]

[0062] Under the protection of high-purity nitrogen, 1,3,5,7-tetra-p-iodophenyladamantane (472.1mg, 0.5mmol, 1.0eq), Pd(PPh 3 ) 4 (57.8mg, 0.05mmol, 0.1eq) and redistilled toluene 10ml, after stirring and dissolving, add 3,4-dimethoxyphenyl pinacol borane (660mg2.50mmol, 5.0 eq) ethanol solution 3ml and 2M Na 2 CO 3 1ml of aqueous solution, the reaction solution was heated at 50-70°C and refluxed for 12h, cooled to room temperature, and 0.5ml of H 2 o 2 Excess borate was quenched, stirred for 1 h, and extracted with dichloromethane / water. The organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and recrystallized in toluene to obtain 376 mg of a white solid with a yield...

example 2

[0073] A preparation method of star adamantane derivative molecular glass, comprising the following steps:

[0074] 1) Preparation of 1,3,5,7-tetrakis-(7,8,9-trimethoxybiphenyl)adamantane, the synthetic route is as follows:

[0075]

[0076] Under nitrogen protection, 1,3,5,7-tetraiodophenyladamantane (472.1mg, 0.5mmol, 1.0eq), Pd(PPh 3 ) 4 (57.8mg, 0.05mmol, 0.1eq) and redistilled toluene 10ml, stirred and dissolved, then added 3,4,5-trimethoxyphenylboronic acid (530mg, 2.50mmol, 5.0eq) in ethanol solution 3ml with a syringe and 2M Na 2 CO 3 solution 1ml, the reaction solution was heated at 50-70°C and refluxed for 12h, cooled to room temperature, and 0.5ml H 2 o 2 Excess boronate was quenched and stirred for 1 h. Extract with dichloromethane / water, combine the organic layers, dry over anhydrous sodium sulfate, concentrate under reduced pressure to remove the solvent, recrystallize in toluene to obtain 398 mg of white solid, yield 72%. 1 H NMR (400MHz, CDCl 3 )δ(pp...

example 3

[0086] Steps 1) and 2) are the same as in Example 1.

[0087] 3) Preparation of 1,3,5,7-tetrakis-(7-hydroxy-8-acetate adamantyl biphenyl)adamantane, the synthetic route is as follows:

[0088]

[0089] AD in the reaction formula represents Substituents.

[0090] Add 1,3,5,7-tetrakis-(7,8-dihydroxybiphenyl)adamantane (875mg, 1.0mmol, 1.0eq), tetrabutylammonium bromide (400mg, 1.2mmol ,1.2eq), K 2 CO 3 (2.8g, 20mmol) and N-methylpyrrolidone (NMP, 50ml), stirred at room temperature for 2 hours, slowly added NMP (10ml ) solution, heated to 60°C for 48h. After the reaction is complete, cool to room temperature, the reaction solution is extracted with ethyl acetate / water, the organic phase is washed once with 3wt% oxalic acid solution and water respectively, the organic layers are combined, dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure, and the residue is washed with Ethyl acetate / n-hexane mixed solvent was recrystallized to obtain 1...

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Abstract

The invention discloses star-shaped adamantane derivative molecular glasses having the following structure shown in the description, wherein substituents R1-R12 are respectively hydrogen, hydroxy, alkoxy or acid sensitivity substituents; the substituents R1-R12 can be different or the same, but the substituents at a same benzene ring cannot both be hydrogen. The invention also discloses a preparation method of the star-shaped adamantane derivative molecular glasses. The method is simple in synthesis process, products of the steps of a reaction all can be separated from the system through a recrystallization or precipitation method. The molecular glasses can be used as photoresist main body materials made into thin films, and also can be used for photoetching.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a star-shaped adamantane derivative molecular glass with relatively high glass transition temperature and good film-forming performance and a synthesis method thereof. Background technique [0002] Photoresist (also known as photoresist) is a kind of etching-resistant thin film material whose solubility changes after energy radiation such as beam, electron beam, ion beam or x-ray. It is used in the microfabrication of integrated circuits and semiconductor discrete devices. also has wide application. By coating photoresist on semiconductors, conductors and insulators, the part left after exposure and development can protect the bottom layer, and then use etchant to etch to transfer the required fine patterns from the mask to the substrate. Therefore, photoresist is a key material in microfabrication technology. With the improvement of the technical demand for integ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/96C07C68/00C07C69/712C07C67/31G03F7/004
CPCC07C69/712C07C69/96C07C2602/42C07C2602/44C07C2603/74G03F7/004
Inventor 李嫕郝青山陈金平曾毅于天君
Owner 国科天骥(北京)新材料技术有限责任公司
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