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Molecular glass photoresist containing bisphenol A skeleton structure as well as preparation method and application thereof

A molecular glass and photoresist technology, applied in the application field of extreme ultraviolet lithography, can solve the problems of large molecular weight and non-uniformity, and achieve the effect of easy preservation and good resolution

Active Publication Date: 2013-09-18
GUOKE TIANJI (BEIJING) NEW MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the original polymer system can no longer meet the requirements of EUV lithography due to its large molecular weight and inhomogeneity, so the research and development of new photoresists is very important

Method used

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  • Molecular glass photoresist containing bisphenol A skeleton structure as well as preparation method and application thereof
  • Molecular glass photoresist containing bisphenol A skeleton structure as well as preparation method and application thereof
  • Molecular glass photoresist containing bisphenol A skeleton structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of dimethylated tetrabromobisphenol A (I-1A)

[0046]

[0047] Add 5.44g of tetrabromobisphenol A (10mmol) and 2.76g of potassium carbonate (20mmol) into a 150mL three-necked flask, then add 50mL of acetone solvent and 4.26g of methyl iodide (30mmol), and reflux at 50-60°C under argon protection 10~15h. After the reaction was completed, the acetone solvent was evaporated, washed with 50 mL of water, extracted three times with 50 mL of dichloromethane, the organic layers were combined, dried with anhydrous magnesium sulfate, filtered and rotated to obtain a crude product, and passed through silica gel with ethyl acetate / petroleum ether. Column chromatography gave 5.56 g of white solid powder with a yield of 96.2%. EI-MS (C 17 h 16 o 2 Br 4 ), m / z:572. 1 H-NMR (400MHz, CDCl 3 )δ7.30(s,4H), 3.89(s,6H), 1.60(s,6H).

Embodiment 2

[0049] Preparation of 2,2-bis(4-methoxy-3,5-bis(p-methoxyphenyl)phenyl)propane (I-1B)

[0050]

[0051] Add 5.78g of dimethylated tetrabromobisphenol A (10mmol), 9.12g of 4-methoxyphenylboronic acid (60mmol) and 0.58g of tetrakis(triphenylphosphine)palladium into a 250mL three-necked flask, and then add 75mL of 2M Potassium carbonate solution and 75mL dioxane solvent were reacted at 90-100°C for 48h under the protection of argon. After the reaction, the layers were separated, and the organic layer was rotary evaporated to remove the dioxane solvent, washed with 100 mL of distilled water, and extracted three times with 100 mL of dichloromethane; the aqueous layer was extracted three times with 50 mL of dichloromethane. All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and rotary evaporated to obtain a crude product, which was subjected to silica gel column chromatography using dichloromethane as the eluent to obtain 4.68 g of white solid powd...

Embodiment 3

[0053] Preparation of 2,2-bis(4-hydroxy-3,5-bis(p-hydroxyphenyl)phenyl)propane (I-1C)

[0054]

[0055] Add 6.81g of 2,2-bis(4-methoxy-3,5-bis(p-methoxyphenyl)phenyl)propane (10mmol) and 100mL of dichloromethane into a 250mL three-necked flask, 25.0 g of boron tribromide (100 mmol) was added under the protection of argon at ℃, and the reaction was carried out at room temperature for 12 h. After the reaction, the reaction system was added to 100mL 2N NaOH solution, the water layer was separated, acidified with 5N hydrochloric acid, extracted three times with 100mL ethyl acetate, the combined organic layers were dried with anhydrous magnesium sulfate, filtered and rotary evaporated to obtain white crystals 5.36 g, the yield is 89.8%. MALDI-TOF (C 39 h 32 o 6 ), m / z: 596.5. 1 H-NMR(400MHz,DMSO)δ9.39(s,4H),7.71(s,2H),7.28(d,J=5.25Hz,8H),6.97(s,4H),6.78(d,J=5.25 Hz,8H), 1.65(s,6H).

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Abstract

The invention relates to a series of molecular glass photoresists (I and II) based on bisphenol A as a main body structure and a preparation method thereof. The molecular glass photoresists are compounded with a photo-acid generator, a crosslinking agent, a photoresist solvent and other additives to produce positive or negative photoresists; the positive or negative photoresists are placed on a silicon wafer through a spin coating method to prepare a photoresist coating layer with uniform thickness. The photoresist formula can be used in modern lithography technologies, such as 248nm lithography, 193nm lithography, extreme ultraviolet lithography, nanoimprinting lithography and electron beam lithography, and is especially suitable for an extreme ultraviolet (EUV) photo-lithographic process.

Description

technical field [0001] The invention relates to a series of molecular glass photoresist containing bisphenol A skeleton structure, a preparation method of the compound and its application in photolithography technology, especially the application in extreme ultraviolet photolithography technology. Background technique [0002] The modern semiconductor industry requires integrated circuits to be smaller in size and higher in integration, and to move forward in accordance with Moore's Law. The internal driving force is the continuous and in-depth development of lithography technology. Since the 1980s, lithography technology has experienced the development from I-line (365nm) to deep ultraviolet (DUV, 248nm and 193nm), and the most notable next-generation extreme ultraviolet (EUV, 13.5nm) lithography technology , and the corresponding photoresist system will also change. [0003] The photoresist used in 193nm lithography is mainly a polymer system, and as the requirements of l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C41/30C07C39/15C07C37/055C07C69/96C07C68/06C07C43/21C07C39/17G03F7/038G03F7/039G03F7/16G03F7/20
CPCC07C69/96C07C39/16C07C39/17C07C43/2055C07C43/21G03F7/0002G03F7/0382G03F7/0392C07C2603/92C07C37/16C07C39/15C07C41/01C07C43/205C07C68/06G03F7/0045
Inventor 杨国强许箭陈力王双青李沙瑜
Owner GUOKE TIANJI (BEIJING) NEW MATERIAL TECH CO LTD
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