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Biphenyl substituted adamantane derivative monomolecular resin, positive photoresist composition and negative photoresist composition

A positive photoresist and negative photoresist technology, applied in optics, optomechanical equipment, instruments, etc., can solve the problem of lithography pattern resolution and edge roughness cannot meet, molecular weight polydispersity, large molecular volume, etc. problem, to achieve the effect of increased interaction, high glass transition temperature, molecular size and single

Active Publication Date: 2017-11-07
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

However, due to structural limitations such as the large molecular volume of the polymer resin itself, the polydispersity of the molecular weight, and the entanglement of molecular chains, the resolution and edge roughness of the lithography pattern cannot meet the requirements of fine scribe lines.

Method used

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  • Biphenyl substituted adamantane derivative monomolecular resin, positive photoresist composition and negative photoresist composition
  • Biphenyl substituted adamantane derivative monomolecular resin, positive photoresist composition and negative photoresist composition
  • Biphenyl substituted adamantane derivative monomolecular resin, positive photoresist composition and negative photoresist composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The preparation of 1,3,5,7-tetra-(3-bromo-4-methoxyphenyl)adamantane, the synthetic route is as follows:

[0062]

[0063] Specific steps:

[0064] Add 5.0g (i.e. 11.0mmol) of tetrabromoadamantane and 20 mL (i.e. 160mmol) of o-methoxybromobenzene into a 250ml three-neck flask equipped with a condenser tube, and connect an inverted funnel to 30% NaOH with a catheter from the upper end of the condenser tube. In aqueous solution, to absorb the HBr produced by the reaction. Under the cold water bath at 5°C, add 1.2g (ie 4.5mmol) of AlBr to the reaction system 3 , continue to stir and react under the cold water bath for 1 hour, then remove the cold water bath, return to room temperature and react for about 3 hours, and finally the reaction system is heated to 60°C in the oil bath for 4 hours, the reaction solution is cooled to room temperature, and poured into 100mL acidic ice Stir in water for 1h. After the ice melted completely, add 100ml of ethyl acetate to the mixt...

Embodiment 2

[0066] The preparation of 1,3,5,7-tetra-(2-methoxy-3',4'-dimethoxy-5-biphenyl)adamantane, the synthetic route is as follows:

[0067]

[0068] Specific steps:

[0069] Under the protection of high-purity nitrogen, add 876.0mg (i.e. 1mmol) of 1,3,5,7-tetra-(3-bromo-4-methoxyphenyl)adamantane, 36.6mg ( ie 0.05mmol) of PdCl 2 (dppf), 910mg (ie 5.0mmol) of 3,4-dimethoxyphenylboronic acid ester and 581mg (ie 10mmol) of potassium fluoride solid, the system was under nitrogen atmosphere, and finally added redistilled dioxane 15ml, the reaction solution was heated to reflux for 6h, cooled to room temperature, and extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, recrystallized in ethyl acetate to obtain 752mg of a white solid, the yield 68%. 1 H NMR (400MHz, CDCl 3 )δ(ppm)7.57(s,4H,benzene),7.36-7.38(m,8H),7.19-7.08(m,8H,benzene),6.95(s,4H,benzene),3.94(s,12H,- ...

Embodiment 3

[0071] The preparation of 1,3,5,7-tetra-(2-hydroxy-3',4'-dihydroxy-5-biphenyl)adamantane, the synthetic route is as follows:

[0072]

[0073] Specific steps:

[0074] Add 1100 mg (ie 1.0 mmol) of 1,3,5,7-tetra-(2-methoxy-3',4'-dimethoxy-5-biphenyl)adamantane into a 250 mL three-necked flask and 50ml of dichloromethane, dissolved under a nitrogen atmosphere, and at a low temperature of -78°C, add 10ml of boron tribromide-containing dichloromethane solution (concentration 0.3g / ml) dropwise to the reaction solution with a syringe, and the reaction solution is at - After reacting at 78°C for 1 hour, the temperature was gradually raised to room temperature, and the reaction was continued for 6 hours. The reaction was quenched by slowly adding 20 ml of ice water to the reaction system, and a large amount of white solid was precipitated. The reaction system was filtered to obtain a white solid, which was washed with water and dichloromethane respectively. The obtained solid was ...

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Abstract

The invention discloses a biphenyl substituted adamantane derivative monomolecular resin, and the following molecular structures of the biphenyl substituted adamantane derivative monomolecular resin are shown in the description, substituent groups Ra1-Ra20 in a formula (I) and substituent groups Rb1-Rb15 in a formula (II) respectively and independently represent a hydrogen atom, a hydroxide radical, a methoxy group, or an acidic sensitive substituent group, the substituent groups Ra1-Ra20 in the formula (I) are the same or different, the substituent groups Rb1-Rb15 in the formula (II) are the same or different, and a plurality of substituent groups on a same benzene ring are not all hydrogen atoms. The biphenyl substituted adamantane derivative monomolecular resin is excellent in solubleness in various polar solvents, is suitable for being prepared into a thin film, has a higher glass transition temperature at the same time, and can well meet the requirements of the photolithographic process; the invention further discloses a photoresist composition comprising the biphenyl substituted adamantane derivative monomolecular resin, and photoetching photoresist coatings with different thicknesses are prepared.

Description

technical field [0001] The invention relates to the field of material technology. More specifically, it relates to a biphenyl substituted adamantane derivative monomolecular resin, a positive photoresist composition and a negative photoresist composition. 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. microfabrication. By coating the photoresist on the surface of a semiconductor, conductor or insulator, the part left after exposure and development will protect the bottom layer, and then use an etchant to etch to transfer the required fine pattern from the mask to the substrate. Therefore, photoresist is a key material in device microfabrication technology. [0003] With the rapid development of the semiconductor industry, the resolu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C43/21C07C39/17C07C271/12C07C69/712C07D309/12G03F7/039G03F7/038
CPCC07C39/17C07C43/21C07C43/225C07C69/712C07C271/12C07D309/12G03F7/038G03F7/039
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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