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Monomolecular resin based on 1,4-disubstituted pillar[5]arene derivative, and positive photoresist and application thereof

A technology of positive photoresist and aromatic hydrocarbon derivatives, applied in the field of materials, can solve problems such as the inability to meet the requirements of scribing lines, and achieve the effects of easy separation and purification, good rigid structure, and high glass transition temperature

Active Publication Date: 2018-07-31
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional photoresist host materials use polymer resins with a molecular weight of 5,000 to 15,000 Daltons. Studies have shown that polymer resin materials usually affect the resolution of photolithographic patterns due to factors such as large molecular volume, polydisperse molecular weight, and entanglement of molecular chains. and edge roughness, unable to meet the requirements of finer scribe lines

Method used

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  • Monomolecular resin based on 1,4-disubstituted pillar[5]arene derivative, and positive photoresist and application thereof
  • Monomolecular resin based on 1,4-disubstituted pillar[5]arene derivative, and positive photoresist and application thereof
  • Monomolecular resin based on 1,4-disubstituted pillar[5]arene derivative, and positive photoresist and application thereof

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preparation example Construction

[0045] The preparation method of 1,4-dihydroxyl substituted pillar [5] arene, as follows:

[0046]Add 1,4-dimethoxy-substituted column[5]arene (10g, 13.3mmol, 1.0eq) and 300ml of dichloromethane into a 500mL three-necked flask, dissolve under a nitrogen atmosphere, and then at -78°C, use a constant Add 50ml of boron tribromide (33.3g, 133mmol, 10.0eq) dichloromethane solution dropwise into the reaction solution through the drop funnel; the reaction solution was reacted at -78°C for 1 hour and then gradually warmed to room temperature, and continued to react for 12 hours , 50ml of water was slowly added dropwise to the reaction system to quench the reaction, the residue was filtered to obtain a white solid, the solid was washed with water and dichloromethane respectively, and finally recrystallized with acetone to obtain 7.7g of a white solid with a yield of 95%.

[0047] 1H NMR (400MHz, DMSO-d 6 )δ (ppm) 7.98 (s, 10H), 6.67 (s, 10H), 3.61 (s, 10H); MS (MALDI-TOF): m / z=610, ca...

Embodiment 1

[0049] The synthetic route of 1,4-di-tert-butyl carbonate group substituted pillar [5] arene derivative monomolecular resin, as shown in (Formula 5):

[0050]

[0051] In the formula, Boc represents substituent, Indicates the bond to the oxygen in the host structure.

[0052] The preparation method of 1,4-di-tert-butyl carbonate group substituted column [5] arene derivative monomolecular resin is as follows:

[0053] Mix 1,4-dihydroxy-substituted pillar[5]arene (3.1g, 5.0mmol, 1.0eq), Boc anhydride (di-tert-butyl dicarbonate) (16.4g, 75mmol, 15.0eq) and 300ml dry tetrahydrofuran, Stir and dissolve under nitrogen atmosphere to obtain the first mixed solution; add the catalyst DMAP (61.0mg, 0.5mmol, 0.1eq) to the first mixed solution to initiate the reaction, and stir at room temperature for 24h; obtain the second reaction solution; The second reaction solution was extracted with ethyl acetate / water, the organic phase was washed three times with saturated aqueous sodium ...

Embodiment 2

[0059] The synthesis route of 1,4-bis(α-adamantyl acetate) substituted pillar[5]arene derivative monomolecular resin is shown in (Formula 6):

[0060]

[0061] In the formula, AD represents substituent, Indicates the bond to the oxygen in the host structure.

[0062] The preparation method of 1,4-bis (alpha-adamantyl acetate) substituted column [5] arene derivative monomolecular resin is as follows:

[0063] 1,4-dihydroxy substituted pillar [5] arene (1.5g, 2.5mmol, 1.0eq), tetrabutylammonium bromide (970mg, 3.0mmol, 1.2eq), K 2 CO 3 (6.9g, 50mmol, 20eq) and N-methylpyrrolidone (NMP, 150ml) were mixed, stirred at room temperature for half an hour to obtain the first mixed solution; slowly dropwise added α-bromoacetic acid to the first mixed solution The NMP (100ml) solution of adamantyl ester (8.6g, 30mmol, 12.0eq) was warmed up to 60°C for 24h to obtain the second mixed solution; the second mixed solution was cooled to room temperature and washed with ethyl acetate / w...

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Abstract

The invention discloses a monomolecular resin based on a 1,4-disubstituted pillar[5]arene derivative. The monomolecular resin has a structure as shown in a formula which is described the specification. In the formula, the substituents R and R' are hydrogen atoms or acid-sensitive substituents respectively, and R and R' cannot be hydrogen atoms at the same time. The monomolecular resin based on the1,4-disubstituted pillar[5]arene derivative is simple in synthesis process and high in yield; intermediates and the product are easy to separate and purify during synthesis; the monomolecular resin is suitable for industrial production; the monomolecular resin can effectively inhibit the crystallization of molecules and are easy for film formation; and the monomolecular resin has the characteristics of good rigid structure, high glass transition temperature and good thermal stability and can well meet the requirements of photolithography process. The monomolecular resin of the invention can be used as a photoresist main body material and cooperated with other additives for preparation of a positive photoresist. Photoresist films of different thicknesses can be prepared through spin coating of the photoresist.

Description

technical field [0001] The invention belongs to the technical field of materials; in particular, it relates to a monomolecular resin based on 1,4-disubstituted pillar [5] arene derivatives, a positive photoresist and applications thereof. Background technique [0002] With the rapid development of the semiconductor industry, the resolution required by lithography technology is getting higher and higher, from the earliest g-line (436nm) lithography, i-line (365nm) lithography, deep ultraviolet 248nm lithography, to the current 193nm lithography, and the most promising next-generation extreme ultraviolet (EUV, 13.5nm) lithography, the resolution of lithography technology has developed from micron to nanometer. As a key material in photolithography technology, photoresist plays an important role in device microfabrication. Photoresist transfers the required micrographics from the mask to On the substrate to be processed, pattern transfer is realized, and the resolution that th...

Claims

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Application Information

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IPC IPC(8): C07C69/96C07C69/712C07D309/12G03F7/004
CPCC07C69/712C07C69/96C07D309/12G03F7/004
Inventor 陈金平李嫕曾毅于天君
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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