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Sensitizer for chemical amplified positive photoresist and application in preparation of chemical amplified positive photoresist

A positive photoresist, chemical amplification technology, applied in optomechanical equipment, patterned surface photoengraving process, optics, etc., can solve problems such as difficult to put into practical application, difficult two-photon absorption cross section, and many synthesis steps. , to achieve the effect of large two-photon absorption cross section and sensitization efficiency, flexible compatibility and easy synthesis

Active Publication Date: 2012-11-07
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, the structural design of the single-component two-photon acid generators used in the above systems is restricted by the acid-generating groups in the molecule, and it is difficult to increase the two-photon absorption cross-section. Moreover, there are many synthesis steps and harsh conditions, making it difficult to put into practical application.

Method used

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  • Sensitizer for chemical amplified positive photoresist and application in preparation of chemical amplified positive photoresist
  • Sensitizer for chemical amplified positive photoresist and application in preparation of chemical amplified positive photoresist
  • Sensitizer for chemical amplified positive photoresist and application in preparation of chemical amplified positive photoresist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A preparation method of a straight-chain or multi-branched benzylidene cycloalkanone two-photon dye with triphenylamine as an electron donor:

[0034] In the general formula M1, A1, A2, A3, and A4 are all hydrogen atoms, It is the synthetic method of the dyestuff S1 of cyclopentanone as follows:

[0035] Add 20ml of absolute ethanol to a 100ml three-necked flask, add 2.73g (0.01mol) of p-dianilinobenzaldehyde, 0.42g (0.005mol) of cyclopentanone and 0.06g of NaOH under stirring, react at 60°C for 3h, and the solution gradually changes from The yellow color turned into red, and a large amount of red crystals were precipitated, and 2.9 g of the crude product was obtained by filtration, and S12.7 g (yield 86%) was obtained by recrystallization from absolute ethanol.

[0036] Elemental analysis calculated value (C43H 34N2O): C, 86.84; H, 5.76; N, 4.71; O, 2.69

[0037] Found: C, 86.80; H, 5.80; N, 4.71; O, 2.71

[0038] Mass Spectrum EI-MS: m / z 594.27

Embodiment 2

[0040] A preparation method of a straight-chain or multi-branched benzylidene cycloalkanone two-photon dye with triphenylamine as an electron donor:

[0041] In the general formula M2, A1, A2 and A3 are hydrogen atoms, Be the synthetic method of the dyestuff S12 of cyclobutanone as follows:

[0042] Add 15ml of absolute ethanol to a 100ml three-necked flask, add 2.73g (0.01mol) of p-dianilinobenzaldehyde, 1.4g (0.02mol) of cyclobutanone and 0.05g of NaOH under stirring, react at room temperature for 8 hours, filter out the orange precipitate, Use volume fraction 0.3% ethanol / dichloro as eluting agent, silica gel stationary phase carries out chromatographic separation, obtains pure product 2-(4-dianilinobenzylidene) cyclobutanone (m 1) 2.75g (yield 80%) .

[0043] Add 2.6g (0.008mol) of the intermediate product m 1 , 1.2g (0.004mol) of dicarboxanilinobenzene and 0.06g NaOH into 25ml of absolute ethanol, heat and back-distill for 3 hours, the system gradually turns red and a ...

Embodiment 3

[0048] A preparation method of a straight-chain or multi-branched benzylidene cycloalkanone two-photon dye with triphenylamine as an electron donor:

[0049] In the general formula M3, A1 and A2 are hydrogen atoms, Be the synthetic method of the dyestuff S13 of cyclopentanone as follows:

[0050] Add 15ml of absolute ethanol to a 100ml three-necked flask, add 2.73g (0.01mol) of p-dianilinobenzaldehyde, 1.6g (0.02mol) of cyclopentanone and 0.05g of NaOH under stirring, react at room temperature for 8 hours, filter out the orange precipitate, Using 0.3% ethanol / dichloride as eluent by volume fraction, chromatographic separation was carried out on silica gel stationary phase to obtain 2.6 g (73% yield) of pure product 2-(4-dianilinobenzylidene)cyclopentanone (m2).

[0051] Add 2.0g (0.006mol) of the intermediate product m2, 0.65g (0.002mol) of triformylanilide and 0.06g NaOH into 25ml of absolute ethanol, heat and back-distill for 3 hours, the system gradually turns red and a d...

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Abstract

The invention discloses a sensitizer for a chemical amplified positive photoresist and an application in preparation of the chemical amplified positive photoresist. The sensitizer comprises a straight-chain or highly-branched benzylidene napthene ketone two-photon dye with triphenylamine as an electron donor or a straight-chain or highly-branched benzylidene alkane ketone two-photon dye with triphenylamine as an electron donor. The straight-chain or branched-chain benzylidene (ring) alkane molecular structure in the sensitizer has only one triphenylamine nitrogen -containing electronic donor group. The invention is characterized in that the triphenylamine group in the sensitizer will not neutralize acid generated by an acid generator, doesn't inhibit chemical amplification process catalyzed by acid, and can be used to prepare the chemical amplified positive photoresist. In addition, the sensitizer has large two-photon absorption cross section, is simply synthesized, has low cost, and can be used to prepare the chemical amplified positive photoresist for two-photon processing. The sensitizer is used to sensitize a commercial photo-acid generator for acid generation such that a prepared photoresist has high machining resolution and low machining energy threshold.

Description

technical field [0001] The invention belongs to the field of chemically amplified positive photoresists, in particular to a sensitizer with a large two-photon absorption cross-section that can be used for chemically amplified positive photoresists, and its preparation of chemically amplified positive photoresists. applications in photoresists. Background technique [0002] Two-photon processing technology has the advantages of strong material penetration and high spatial resolution, and has broad application prospects in the field of three-dimensional ultrafine micromachining. The preparation of the corresponding photoresist is the key content of the development of two-photon processing technology. At present, the materials used in the research of two-photon processing are mainly: 1) Commercial negative photoresist, such as the radical polymerization photoresist SCR500 of Japan Synthetic Rubber Co., Ltd., and the cationic polymerization photoresist SU of MicroChem Corporati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/039
Inventor 吴飞鹏袁浩赵榆霞
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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