CN104211867A - Acrylic copolymer with narrow molecular weight distribution and photosensitive resist composition of acrylic copolymer with narrow molecular weight distribution - Google Patents
Acrylic copolymer with narrow molecular weight distribution and photosensitive resist composition of acrylic copolymer with narrow molecular weight distribution Download PDFInfo
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- CN104211867A CN104211867A CN201410414978.2A CN201410414978A CN104211867A CN 104211867 A CN104211867 A CN 104211867A CN 201410414978 A CN201410414978 A CN 201410414978A CN 104211867 A CN104211867 A CN 104211867A
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Abstract
The invention relates to synthesis of a narrow-distribution methacrylate photosensitive polymer and a non-chemically amplified negative photosensitive resist composition capable of developing in an alkaline aqueous solution. The narrow distribution methacrylate polymer is prepared based on RAFT polymerization, and the narrow-distribution methacrylate photosensitive polymer is obtained by introducing photosensitive groups through ring-opening reaction between epoxy groups on glycidyl methacrylate (GMA) and carboxyls on the polymer. The non-chemically amplified negative photosensitive resist composition capable of developing in an alkaline aqueous solution is prepared by adding the additives such as a photoinitiator and a reactive diluent in the synthesized photosensitive polymer as the main resin.
Description
Technical field
The invention belongs to optical imaging field, relate to the synthesis of narrow ditribution methyl acrylic ester photosensitive copolymers and a kind of non-chemically amplification type negative photo glue composition that can develop in alkaline aqueous solution.
Background technology
Photoresist material, also known as photo-resist, refers under the irradiation or irradiation of energy-beam (light beam, electron beam, ionic fluid etc.), the etch resistant thin-film material that its solubleness changes.According to the changing conditions of photo-resist solubleness before and after exposure, can be divided into positive photoresist and negative photoresist two class, what after exposure, solubleness increased is positive photoresist, and after development, positive photoresist can obtain the figure identical with mask light-shielding pattern, otherwise is negative photoresist.
Photoetching technique is the critical process in integrated circuit fabrication process, and photoresist material is then key material required in photoetching technique.Along with the development of IC industry demand, photoetching technique is updated to make finer electron device, and in photoresist material component, the structure of polymkeric substance is also in continuous change.Polymkeric substance used, from early stage polyvinyl cinnamate, thermoprene, develops into the resol for G line, I line, and for the poly(4-hydroxystyrene) of deep ultraviolet and polyester ring race acrylate.
The performance of polymer architecture on photoresist material has significant impact, and therefore structure-controllable, the predictable activity/controllable free-radical polymerisation of molecular weight cause the concern of researchist in this field of photoresist material.In numerous activity/controllable free-radical polymerisation, owing to having, polymerization process activity is controlled, reaction conditions is gentle, monomer suitability is wide in RAFT polymerization, molecular weight narrow ditribution and molecular weight is measurable etc. that advantage application is comparatively extensive.
Application number is the acrylic polymers that patent document discloses a kind of low dispersed Photoimageable and the photo-corrosion-resisting agent composition of 201110360724.3, and this low polymer dispersion is by the preparation of RAFT controllable free-radical polymerisation technology.
Application number be 201210292562.9 patent documentation use dithioesters chain-transfer agent (CTA) to cause the improvement of resist polymerizing condition for EUV light, the amount of controls CTA can obtain the narrow ditribution polymkeric substance of accurate molecular weight and the transformation efficiency of this RAFT polymerization can reach more than 80% and do not have the typical harmful effect when high conversion observed in radical polymerization.
Summary of the invention
The present invention proposes a kind of synthetic method of narrow ditribution methyl acrylic ester photosensitive polymer, the molecular weight of photosensitive polymer is controlled, with the photosensitive polymer synthesized for matrix resin is for the preparation of micron-sized non-chemically amplification type photoetching compositions by the relative content changing chain-transfer agent.
Technical scheme of the present invention is as follows:
(1) synthesis of narrow ditribution methacrylate based polymers: under normal temperature condition, methacrylic acid, methacrylate-based monomer, acrylic ester monomer, initiator and chain-transfer agent are dissolved in polymer solvent, vacuumize logical nitrogen repeatedly after three times, closed reaction vessel, rises to 60 ~ 90 DEG C of insulation reaction 3 ~ 24h under magnetic stirring by solution temperature;
(2) synthesis of narrow ditribution methyl acrylic ester photosensitive polymerization: reaction vessel in step (1) is warming up to 100 ~ 130 DEG C, the mixture containing glycidyl methacrylate (GMA) is dripped, insulation reaction 8 ~ 24h in container;
(3) preparation of non-chemically amplification type photoetching compositions: resin step (2) obtained is in solvent, photoresist solution is prepared into after adding light trigger, reactive thinner, by the mode of spin coating, photoresist solution is uniformly coated on base material, after front baking, development treatment, on base material, obtains pictorial pattern.
Methacrylate-based monomer is selected in step (1): one or more in methyl methacrylate, hydroxyethyl methylacrylate, benzyl methacrylate, isobornyl methacrylate, 3-hydroxyl-1-adamantyl methacrylate, 2-ethyl-2-adamantyl methacrylate.
Acrylic ester monomer is selected in step (1): one or more in methyl acrylate, ethyl propenoate, n-butyl acrylate, tert-butyl acrylate, Propylene glycol monoacrylate.
Selecting of the middle initiator of step (1): the one in azo-bis-isobutyl cyanide, azo two cyanogen in different heptan, benzoyl peroxide.
Step (1) Chain transfer agent is 2-(dodecyl trithiocarbonic acid ester group)-2 Methylpropionic acid).
In step (1), solvent is the one in 1-Methoxy-2-propyl acetate, N-BUTYL ACETATE, DMF.
In step (1), the content of methacrylic acid accounts for 20% ~ 50% of monomer integral molar quantity; Initiator content is 0.1% ~ 1% of monomer integral molar quantity; Chain tra nsfer content is 0.3% ~ 3% of total amount of monomer; Solvent is 50% ~ 80% of total mass.
In step (2), the content of glycidyl methacrylate is 5% ~ 15% of total amount of monomer in step (1).
The one in triphenyl phosphorus, tin protochloride, 4 bromide is contained in mixture in step (2); One in Resorcinol, 4-methoxyphenol.
In step (3), base material is the one in copper sheet, iron plate, silicon plate; Light trigger is one or more in Darocure184, Darocure1173, Irgacure907, ITX; Reactive thinner is one or more in HBVE, HDDA, TPGDA, TPMTA, EOTMPTA, PT4A, DPHA; Developing solution is the one in sodium carbonate solution, sodium hydroxide solution, Tetramethylammonium hydroxide;
In step (3), the content of resin accounts for 60% ~ 80% of photoresist solution total mass; Light trigger accounts for 3% ~ 5% of total mass; Reactive thinner accounts for 5% ~ 30% of total mass; The concentration of developing solution is 1w% ~ 3w%.
Compared with prior art, its innovative point and technical benefits are mainly reflected in:
(1) utilize RAFT to be polymerized and prepare narrow ditribution methacrylate based polymers, then on polymer chain, introduce photosensitive functional group by the mode of graft glycidyl methacrylate.
(2) this synthetic method operational condition is gentle, product yield is high, monomer is applied widely, is generally applicable to the methacrylate-based monomer on market and acrylic ester monomer.
(3) the non-chemically amplification type negative photoresist adopting this photosensitive polymer to modulate, can realize the live width of micron, can meet market and to enamel the making requirement of spectral filter.
Accompanying drawing illustrates:
Fig. 1 is the infrared spectrogram in embodiment 1 before and after narrow ditribution methacrylate based polymers grafting GMA.
Fig. 2 is the nuclear magnetic spectrogram in embodiment 1 before and after narrow ditribution methacrylate based polymers grafting GMA.
Fig. 3 is the scanning electron microscope (SEM) photograph in embodiment 1 after photoetching compositions development.
Embodiment
In order to explain the present invention better, below in conjunction with specific embodiment, the present invention is further explained in detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
(1) synthesis of narrow ditribution methacrylate based polymers: add 1.52g (17.7mmol) methacrylic acid in round-bottomed flask, 2.66g (15.2mmol) benzyl methacrylate, 0.76g (7.6mmol) methyl methacrylate, 1.44g (14.4mmol) n-BMA, 0.29g (0.81mmol) 2-(dodecyl trithiocarbonic acid ester group)-2 Methylpropionic acid), 0.044g (0.27mmol) azo-bis-isobutyl cyanide, 11.88g 1-Methoxy-2-propyl acetate, vacuumize logical nitrogen repeatedly after three times, closed reaction vessel, insulation reaction 24h under magnetic stirring solution temperature being risen to 80 DEG C,
(2) synthesis of narrow ditribution methyl acrylic ester photosensitive polymerization: reaction vessel in step (1) is warming up to 125 DEG C, the mixing solutions of Resorcinol (0.03g), triphenyl phosphorus (0.03g), methyl propenoic acid glycidyl ether (0.72g) and 1-Methoxy-2-propyl acetate (1.58g) is at the uniform velocity added drop-wise in reaction vessel, insulation reaction 12h.
(3) preparation of non-chemically amplification type photoetching compositions: the resin in 4.5g step (2) is dissolved in 1g 1-Methoxy-2-propyl acetate, adds Viscoat 295 (1.5g), 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone (0.2g), isopropyl thioxanthone (0.1g) and phthalocyanine green (0.5g) is made into photoresist solution.Be spin-coated on copper sheet by sol evenning machine by photoresist solution, copper sheet front baking 0.5h in the baking oven of 75 DEG C, exposes 30s under ultraviolet exposure machine, finally with the development of 1w% sodium carbonate solution, and the image after developing with sem observation.
Embodiment 2
(1) synthesis of narrow ditribution methacrylate based polymers: add 3.04g (35.4mmol) methacrylic acid in round-bottomed flask, 5.32g (30.4mmol) benzyl methacrylate, 1.52g (15.2mmol) methyl methacrylate, 2.88g (28.8mmol) n-BMA, 0.29g (0.81mmol) 2-(dodecyl trithiocarbonic acid ester group)-2 Methylpropionic acid), 0.044g (0.27mmol) azo-bis-isobutyl cyanide, 23.76g 1-Methoxy-2-propyl acetate, vacuumize logical nitrogen repeatedly after three times, closed reaction vessel, insulation reaction 24h under magnetic stirring solution temperature being risen to 80 DEG C,
(2) synthesis of narrow ditribution methyl acrylic ester photosensitive polymerization: reaction vessel in step (1) is warming up to 125 DEG C, the mixing solutions of Resorcinol (0.05g), triphenyl phosphorus (0.05g), methyl propenoic acid glycidyl ether (1.44g) and 1-Methoxy-2-propyl acetate (3.16g) is at the uniform velocity added drop-wise in reaction vessel, insulation reaction 12h.
(3) preparation of non-chemically amplification type photoetching compositions: the resin in 4.5g step (2) is dissolved in 1g 1-Methoxy-2-propyl acetate, adds Viscoat 295 (1.5g), 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone (0.2g), isopropyl thioxanthone (0.1g) and phthalocyanine green (0.5g) is made into photoresist solution.Be spin-coated on copper sheet by sol evenning machine by photoresist solution, copper sheet front baking 0.5h in the baking oven of 75 DEG C, exposes 30s under ultraviolet exposure machine, finally with the development of 1w% sodium carbonate solution, and the image after developing with sem observation.
Embodiment 3
(1) synthesis of narrow ditribution methacrylate based polymers: add 6.08g (35.4mmol) methacrylic acid in round-bottomed flask, 10.64g (60.8mmol) benzyl methacrylate, 3.04g (3.04mmol) methyl methacrylate, 5.76g (57.6mmol) n-BMA, 0.29g (0.81mmol) 2-(dodecyl trithiocarbonic acid ester group)-2 Methylpropionic acid), 0.044g (0.27mmol) azo-bis-isobutyl cyanide, 47.52g 1-Methoxy-2-propyl acetate, vacuumize logical nitrogen repeatedly after three times, closed reaction vessel, insulation reaction 24h under magnetic stirring solution temperature being risen to 80 DEG C,
(2) synthesis of narrow ditribution methyl acrylic ester photosensitive polymerization: reaction vessel in step (1) is warming up to 125 DEG C, the mixing solutions of Resorcinol (0.07g), triphenyl phosphorus (0.07g), methyl propenoic acid glycidyl ether (2.88g) and 1-Methoxy-2-propyl acetate (6.32g) is at the uniform velocity added drop-wise in reaction vessel, insulation reaction 12h.
(3) preparation of non-chemically amplification type photoetching compositions: the resin in 4.5g step (2) is dissolved in 1g 1-Methoxy-2-propyl acetate, adds Viscoat 295 (1.5g), 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholine-1-acetone (0.2g), isopropyl thioxanthone (0.1g) and phthalocyanine green (0.5g) is made into photoresist solution.Be spin-coated on copper sheet by sol evenning machine by photoresist solution, copper sheet front baking 0.5h in the baking oven of 75 DEG C, exposes 30s under ultraviolet exposure machine, finally with the development of 1w% sodium carbonate solution, and the image after developing with sem observation.
Claims (12)
1. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer, is characterized in that carrying out according to following steps:
(1) synthesis of narrow ditribution methacrylate based polymers: under normal temperature condition, methacrylic acid, methacrylate-based monomer, acrylic ester monomer, initiator and chain-transfer agent are dissolved in polymer solvent, vacuumize logical nitrogen repeatedly after three times, closed reaction vessel, rises to 60 ~ 90 DEG C of insulation reaction 3 ~ 24h under magnetic stirring by solution temperature;
(2) synthesis of narrow ditribution methyl acrylic ester photosensitive polymer: reaction vessel in step (1) is warming up to 100 ~ 130 DEG C, the mixture containing glycidyl methacrylate (GMA) is dripped in container, insulation reaction 8 ~ 24h, obtains narrow ditribution methyl acrylic ester photosensitive polymer.
2. the preparation of non-chemically amplification type negative photo glue composition, it is characterized in that: the narrow ditribution methyl acrylic ester photosensitive polymer obtained is dissolved in solvent, add light trigger, reactive thinner is prepared into photoresist solution, by the mode of spin coating, photoresist solution is uniformly coated on base material, after front baking, development treatment, on base material, obtains pictorial pattern.
3. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that methacrylate-based monomer is selected in step (1): one or more in methyl methacrylate, hydroxyethyl methylacrylate, benzyl methacrylate, isobornyl methacrylate, 3-hydroxyl-1-adamantyl methacrylate, 2-ethyl-2-adamantyl methacrylate.
4. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that acrylic ester monomer is selected in step (1): one or more in methyl acrylate, ethyl propenoate, n-butyl acrylate, tert-butyl acrylate, Propylene glycol monoacrylate.
5. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that selecting of the middle initiator of step (1): the one in azo-bis-isobutyl cyanide, azo two cyanogen in different heptan, benzoyl peroxide.
6. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that step (1) Chain transfer agent is 2-(dodecyl trithiocarbonic acid ester group)-2 Methylpropionic acid).
7. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that in step (1), solvent is the one in 1-Methoxy-2-propyl acetate, N-BUTYL ACETATE, DMF.
8. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that the content of methacrylic acid in step (1) accounts for 20% ~ 50% of monomer integral molar quantity; Initiator content is 0.1% ~ 1% of monomer integral molar quantity; Chain tra nsfer content is 0.3% ~ 3% of total amount of monomer; Solvent is 50% ~ 80% of total mass.
9. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that the content of glycidyl methacrylate in step (2) is 5% ~ 15% of total amount of monomer in step (1).
10. the synthesis of narrow ditribution methyl acrylic ester photosensitive polymer according to claim 1, is characterized in that the one contained in mixture in step (2) in triphenyl phosphorus, tin protochloride, 4 bromide; One in Resorcinol, 4-methoxyphenol.
The preparation of 11. non-chemically amplification type negative photo glue compositions according to claim 2, is characterized in that light trigger is one or more in Darocure 184, Darocure 1173, Irgacure907, ITX; Reactive thinner is one or more in HBVE, HDDA, TPGDA, TPMTA, EOTMPTA, PT4A, DPHA; Developing solution is the one in sodium carbonate solution, sodium hydroxide solution, Tetramethylammonium hydroxide.
The preparation of 12. non-chemically amplification type negative photo glue compositions according to claim 2, is characterized in that the content of resin accounts for 60% ~ 80% of photoresist solution total mass; Light trigger accounts for 3% ~ 5% of total mass; Reactive thinner accounts for 5% ~ 30% of total mass; The concentration of developing solution is 1w% ~ 3w%.
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| CN104817656A (en) * | 2015-04-01 | 2015-08-05 | 苏州瑞红电子化学品有限公司 | Urethane-acrylate copolymer and photoresist composition thereof |
| CN104834182A (en) * | 2015-05-20 | 2015-08-12 | 杭州福斯特光伏材料股份有限公司 | Light sensitive dry film with high resolution and excellent hole covering performance |
| CN105237669A (en) * | 2015-09-11 | 2016-01-13 | 苏州瑞红电子化学品有限公司 | Preparation of 248 nm deep ultraviolet photoresist film forming resin based on RAFT polymerization method |
| CN105566552A (en) * | 2016-03-04 | 2016-05-11 | 江南大学 | Acrylate copolymer and 248nm photoresist composition made thereof |
| CN107085356A (en) * | 2017-02-17 | 2017-08-22 | 无锡德贝尔光电材料有限公司 | A kind of pure third photoresist of the photosensitive negativity of UV and preparation method thereof |
| CN107918245A (en) * | 2016-10-07 | 2018-04-17 | 捷恩智株式会社 | Curable adhensive compositions and its cured film, the display element comprising cured film |
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| CN111718439A (en) * | 2020-06-19 | 2020-09-29 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method and application thereof |
| CN113861332A (en) * | 2021-09-30 | 2021-12-31 | 宁波南大光电材料有限公司 | Photoresist resin and polymerization method thereof |
| CN113929810A (en) * | 2021-10-15 | 2022-01-14 | 厦门恒坤新材料科技股份有限公司 | Functional polymer, bottom anti-reflection coating composition and preparation method thereof |
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| CN113929810A (en) * | 2021-10-15 | 2022-01-14 | 厦门恒坤新材料科技股份有限公司 | Functional polymer, bottom anti-reflection coating composition and preparation method thereof |
| CN116199817A (en) * | 2023-04-25 | 2023-06-02 | 有研工程技术研究院有限公司 | Boc-containing gold resinate and positive photo-etching organic gold slurry and preparation method thereof |
| CN116199817B (en) * | 2023-04-25 | 2023-08-15 | 有研工程技术研究院有限公司 | Boc-containing gold resinate and positive photo-etching organic gold slurry and preparation method thereof |
| CN117164977A (en) * | 2023-09-06 | 2023-12-05 | 广东定通实业有限公司 | PE composite plastic and preparation method thereof |
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