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Octaphenyl substituted polyhedral oligomeric silsesquioxane derivative molecular glass and application thereof

A technology of silsesquioxane and molecular glass, which is applied in the field of materials, can solve the problems of poor product repeatability, insufficient purity, and low modification yield, and achieve the effects of high yield, simple synthesis process, and easy separation and purification

Active Publication Date: 2018-07-24
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

In the existing research, a single molecule of POSS has been used as the photoresist host material, and the corresponding molecular host material is obtained by modifying the POSS with Si-H groups on the periphery. This method has the following limitations: 1) the periphery is The synthesis of POSS with Si-H group is difficult (less than 20% yield), and the yield of further modification is lower, which is not conducive to large-scale preparation; 2) The glass transition temperature of the obtained main molecule is low, which is suitable for photolithography process Poor; 3) The purity of the main material is not high enough, only about 70% content, high impurity content will lead to poor product repeatability, and to reach 97% purity, further separation is required, and the cost is greatly increased

Method used

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  • Octaphenyl substituted polyhedral oligomeric silsesquioxane derivative molecular glass and application thereof
  • Octaphenyl substituted polyhedral oligomeric silsesquioxane derivative molecular glass and application thereof
  • Octaphenyl substituted polyhedral oligomeric silsesquioxane derivative molecular glass and application thereof

Examples

Experimental program
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Embodiment 1

[0078] A preparation method of octaphenyl substituted clathrate silsesquioxane derivative molecular glass, comprising the following steps:

[0079] 1) Preparation of octa-(7,8-dimethoxybiphenyl)silsesquioxane, the reaction formula of the synthetic route is as follows:

[0080]

[0081] Under the protection of high-purity nitrogen, add octa(p-iodophenyl substituted) silsesquioxane (20.4g, 10mmol, 1.0eq) in a 500ml schleck reaction flask, 200ml of redistilled tetrahydrofuran, stir and dissolve, and pour into the reaction flask Add 3,4-dimethoxyphenylboronic acid (18.2g, 100mmol, 10.0eq) and 2M Na 2 CO 3 Aqueous solution 80ml, finally add catalyst Pd (PPh 3 ) 4 (577mg, 0.5mmol, 0.05eq), the reaction solution was heated to 50-70°C for 12h, cooled to room temperature, the reaction solution was extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent , the residue was...

Embodiment 2

[0091] A preparation method of octaphenyl substituted clathrate silsesquioxane derivative molecular glass, comprising the following steps:

[0092] 1) Preparation of octa-(7,8,9-trimethoxybiphenyl)silsesquioxane, the reaction formula of the synthetic route is as follows:

[0093]

[0094] Under the protection of high-purity nitrogen, add octa(p-iodophenyl substituted) silsesquioxane (20.4g, 10mmol, 1.0eq) in a 500ml schleck reaction flask, 200ml of redistilled tetrahydrofuran, stir and dissolve, and pour into the reaction flask Add 3,4,5-trimethoxyphenylpinacolborane (29.4g, 100mmol, 10.0eq) and 2M Na 2 CO 3 Aqueous solution 80ml, finally add catalyst Pd (PPh 3 ) 4 (577mg, 0.5mmol, 0.05eq), the reaction solution was heated to 50-70°C for 12h, cooled to room temperature, the reaction solution was extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent , the resi...

Embodiment 3

[0104] Step 1) and 2) are the same as in Example 1.

[0105] 3) Octa-(7,8-diadamantyl biphenyl)silsesquioxane, the reaction formula of the synthetic route is as follows:

[0106]

[0107] AD in the reaction formula represents Substituents.

[0108] Add octa-(7,8-dihydroxybiphenyl)silsesquioxane (4.0, 2.1mmol, 1.0eq), tetrabutylammonium bromide (812mg, 2.5mmol, 1.2eq) into a 100mL three-necked flask, K 2 CO 3 (4.6g, 33.6mmol, 16.0eq) and N-methylpyrrolidone (NMP, 40ml), stir evenly at room temperature, slowly add adamantyl chloroacetate (8.15g, 33.6mmol, 16.0eq) dropwise to the reaction solution NMP (20ml) solution, the temperature of the reaction system was raised 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 ...

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PUM

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Abstract

The invention discloses octaphenyl substituted polyhedral oligomeric silsesquioxane derivative molecular glass, which has the following molecular structure: the molecular structure is shown in the description, wherein substituent groups R1 to R24 are respectively hydrogen atom, hydroxyl group or acid-sensitive substituent group; the substituent groups R1 to R24 may be the same or different, but the three substituent groups on a same benzene ring cannot be hydrogen atom simultaneously. The invention further discloses application of the octaphenyl substituted polyhedral oligomeric silsesquioxanederivative molecular glass. The molecular glass can be used as a main material of a photoresist to be prepared into a thin film, and can be used for photoetching.

Description

technical field [0001] The invention relates to the field of material technology. More specifically, it relates to an octaphenyl-substituted clathrate silsesquioxane derivative molecular glass and its application. Background technique [0002] Photoresist (also known as photoresist) is a kind of etch-resistant thin film material whose solubility changes after energy radiation such as beam, electron beam, ion beam or x-ray, and is widely used in integrated circuits and semiconductor discrete devices. In micro processing. The photoresist transfers the required fine patterns from the mask plate to the substrate to be processed through the processes of coating, exposure, development, and etching to realize pattern transfer. The rapid development of the semiconductor industry has put forward higher and higher requirements for lithography technology, from the earliest g-line (436nm) lithography, i-line (365nm) lithography, deep ultraviolet 248nm lithography, to the current 193nm...

Claims

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Application Information

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IPC IPC(8): C08G77/04C08G77/38G03F7/075
CPCC08G77/045G03F7/0757
Inventor 陈金平李嫕于天君曾毅
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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