A star-shaped 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, polydispersity of molecular weight, large molecular volume, etc., and achieves good thermal stability, high glass transition temperature, The effect of the synthesis process is simple

Active Publication Date: 2016-08-31
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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  • A star-shaped tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof
  • A star-shaped tetraphenylethylene derivative molecular glass, positive photoresist, positive photoresist coating and application thereof
  • A star-shaped 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-butylcarbonate base biphenyl) ethylene molecular glass, the method comprises 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, tetrakis(4-bromophenyl)ethylene (648mg, 1.0mmol, 1.0eq), Pd(PPh 3 ) 4 (116mg, 0.1mmol, 0.1eq) and redistilled toluene 15ml, after stirring and dissolving, add 3,4-dimethoxyphenyl pinacol borane (1320mg, 5.00mmol, 5.0 eq) ethanol solution 3ml and 2MNa 2 CO 3 1ml of aqueous solution, the reaction solution was heated to reflux at 50-70°C for 12h, cooled to room temperature, extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, recrystallized in ethanol to obtain 658mg of white solid , yield 75%. 1 HNMR (400MHz, CDCl 3 )δ(ppm)7.57(d,J=8.2Hz,16H),7.20-7.08(m,8H),6...

Embodiment 2

[0069] Four-(8-acetate adamantyl biphenyl) preparation method of ethylene molecular glass, the method may further comprise the steps:

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

[0071]

[0072] Under the protection of high-purity nitrogen, tetrakis(4-bromophenyl)ethylene (648mg, 1.0mmol, 1.0eq), Pd(PPh 3 ) 4 (116mg, 0.1mmol, 0.1eq) and redistilled toluene 15ml, after stirring and dissolving, add 4-methoxyphenyl pinacol borane (1170mg, 5.00mmol, 5.0eq) dissolved in the reaction flask with a syringe Ethanol solution 3ml and 2M Na 2 CO 3 1ml of aqueous solution, the reaction solution was heated to reflux at 50-70°C for 12h, cooled to room temperature, extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, recrystallized in ethanol to obtain 545mg of white solid , yield 72%. 1 HNMR (400MHz, CDCl 3 )δ(ppm)7.57(d,J=8.2Hz,8H...

Embodiment 3

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

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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 field of material technology, and in particular relates to a star-shaped tetraphenylethylene derivative molecular glass, a positive photoresist, a positive photoresist coating and an application 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. The rapid development of the semiconductor industry has put forward higher an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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