CN109942741A - A kind of preparation method of photoresist resin - Google Patents
A kind of preparation method of photoresist resin Download PDFInfo
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- CN109942741A CN109942741A CN201910133829.1A CN201910133829A CN109942741A CN 109942741 A CN109942741 A CN 109942741A CN 201910133829 A CN201910133829 A CN 201910133829A CN 109942741 A CN109942741 A CN 109942741A
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Abstract
The invention discloses a kind of preparation methods of photoresist resin, it is characterized by: being dissolved in the solvent containing quantitative moisture by one or more monomers with acid activity group and one or more monomers with polar group, under the conditions of existing for the initiator, ATRP reaction is carried out to be prepared, the following steps are included: the organic solvent containing quantitative moisture is heated to 50~80 DEG C by (1), the preheated organic solvent containing moisture is obtained；(2) monomer and initiator are dissolved in the organic solvent of same step (1) considerable moisture content, obtain the solution of raw material；(3) solution of raw material is added drop-wise in the preheated organic solvent containing moisture, 50~80 DEG C constant temperature back flow reaction 10~30 hours；(4) it is cooled to room temperature, with nonpolar solvent precipitated resin, filtering drying obtains photoresist resin；Wherein, the moisture content in solvent is 1~1500ppm.The present invention realizes the adjusting to the molecular weight of fluoropolymer resin by adjusting the content of water, will not introduce other impurity, and molecular weight control is more accurate.
Description
Technical field
The present invention relates to a kind of preparations of fluoropolymer resin, and in particular to a kind of preparation side of the resin for photoresist
Method.
Background technique
Photoresist is the critical material of currently manufactured Advanced Integrated Circuits.The filmogen of photoresist is all kinds of photoetching gums
Rouge.KrF photoresist is mainly using poly(4-hydroxystyrene) resin as filmogen.Since the primary structure of the resin is phenyl ring,
There is absorption at 193nm.All, ArF photoresist film forming resinous material is mainly (methyl) acrylic compounds transparent at 193nm
Resin.Meanwhile with the miniaturization of component, the litho pattern for needing to make is smaller and smaller.Production small size figure needs light
Photoresist has lower molecular weight and molecular weight distribution more evenly is just able to maintain excellent performance.Therefore, (methyl) third is grasped
The molecular weight control technology of olefin(e) acid resinoid is particularly important to preparing for ArF photoetching gum resin.
In actual polymerisation process, there are factors to will affect photoresist resinous polymer molecular weight, under normal circumstances shadow
The principal element for ringing polymer molecular weight has: polymeric reaction temperature；Monomer/catalyst ratio (nM/nNd) ；Co-catalyst dosage
(ncocatalyst/nNd) ；Molecular weight regulator etc..Adjusting for resinous polymer molecular weight, usually by change initiator or
The dosage of chain-transferring agent adjusts the molecular weight distribution of polymer.With the increase of initiator or chain-transferring agent, although realizing
The control of molecular weight, but it is also introduced into more impurity.For advanced photoresist, the introducing of impurity will affect the pure of resin
Degree, so that photoresist be made to be stain, causes the generation of defect.
Atom transferred free radical living polymerization (ATRP) is a kind of effective living control polymerization method, can carry out a mole matter
Amount design, each quasi polymer of preparation structure and molar mass distribution controllably, has potential and extensive researching value.
The traditional common solvent of ATRP polymerization reaction such as toluene etc., since it is with biggish toxicity, limits it
The process of industrialization.In recent years, ATRP polymerization reaction is carried out by using other solvents, polymerization reaction can be effectively facilitated, but
Reacting controllability reduces.
The preparation of photoetching gum resin is main or based on free radical polymerization at present, and is changed by increasing initiator point
Son amount can generate impurity introducing again, to have an adverse effect to photoresist quality.Therefore, how to obtain it is a kind of simple and effective and
The method of the control polymer molecular weight of other impurity or the problem of industry will not be introduced.
Summary of the invention
Goal of the invention of the invention is to provide a kind of preparation method of photoresist resin, in the item for not introducing other impurity
The control of polymer molecular weight is conveniently effectively realized under part.
To achieve the above object of the invention, the technical solution adopted by the present invention is that: a kind of preparation method of photoresist resin,
The photoetching gum resin be by one or more monomers with acid activity group and it is one or more have polar group
Monomer is dissolved in the solvent containing quantitative moisture, under the conditions of existing for the initiator, is carried out ATRP reaction and is prepared, including
Following steps:
(1) organic solvent containing quantitative moisture is heated to 50~80 DEG C, obtained preheated organic molten containing moisture
Agent；
(2) monomer and initiator are dissolved in the organic solvent of same step (1) considerable moisture content, obtain the solution of raw material；
(3) solution for the raw material that step (2) obtain is added drop-wise in step (1) in the preheated organic solvent containing moisture,
50~80 DEG C constant temperature back flow reaction 2~30 hours；
(4) it is cooled to room temperature after the reaction was completed, with nonpolar solvent precipitated resin, filtering drying obtains photoresist resin；
Wherein, step (1), the moisture content in (2) are 1~1500ppm.
The photoetching gum resin is formed by least two kinds of monomer polymerizations, and the amount of the substance total by monomer is monomer in terms of 100%
Dosage be respectively as follows:
Acid activity monomer: 30~70%,
Polar monomer: 70~30%,
Contain the acid activity monomer and one or more polarity lists of one or more different substituents in the photoetching gum resin
Body.
The acid activity monomer is (methyl) acrylate containing acid-labile group, general structure are as follows:
In formula, R1Carbon-containing group for H or carbon atom number in 1-20, R2For the functional group containing acid-labile group.
Specifically, R2The carbon atom number contained is between 6-30, the hydrogen atom for the carbon atom being connected with ester bond oxygen atom
All replaced by other groups, constitutes tertiary butyl ester, substituted tert-butyl ester, alkyl-substituted Buddha's warrior attendant alkyl ester, alkyl-substituted gold
Rigid alkane derivatives ester, alkyl-substituted norbornyl ester, alkyl-substituted norborneol derivative ester, alkyl-substituted cyclic alkyl
One of ester, alkyl-substituted cyclic alkyl derivative ester are a variety of.
The polar monomer is (methyl) acrylate of polar functionalities, general structure are as follows:
In formula, R3Carbon-containing group for H or carbon atom number in 1-20, R4For the functional group of polar functionalities.
Specifically, R4For the carbon atom number contained between 6 ~ 30, the composition that is connected with ester bond oxygen atom is only containing one or more
The Buddha's warrior attendant alkyl ester of vertical hydroxyl, the ring pentyl ester containing one or more independent hydroxyls, contains 1 at the cyclohexyl containing one or more independent hydroxyls
The polycyclic ester type compounds of a or multiple independent hydroxyls, the caged ester type compound containing one or more independent hydroxyls, butyrolactone,
Valerolactone replaces valerolactone, caprolactone, replaces caprolactone, the lactone containing adamantane structure, the lactone containing multiring structure, contains cage
One of lactone of shape structure is a variety of.
Preferred monomer and its dosage, the amount of the substance total by monomer are in terms of 100%:
Methacrylic acid butyrolactone: 20~40%,
3- hydroxyl -2- Adamantylmethyl acrylic ester: 10~35
1- cyclohexyl methyl acrylate: 45~70%.
In above-mentioned technical proposal, initiator is organic peroxide or azo-initiator, such as cyclohexanone peroxide, peroxide
Change one of dibenzoyl, tert-butyl hydroperoxide etc., azodiisobutyronitrile, azobisisoheptonitrile etc. or a variety of；Preferably
Azodiisobutyronitrile, dosage 5-15%.
In above-mentioned technical proposal, organic solvent is esters, ethers, alcohols, ketone, aromatics organic solvent, can be second
Acetoacetic ester, butyl acetate, butyl acetate, acetic acid peopentyl ester, ethyl lactate, propylene glycol methyl ether acetate, propylene glycol list Acetic Ester,
Dihydroxypropane single-ether, propylene glycol methyl ether acetate, tirethylene glycol methyl ether, tirethylene glycol ether, tetrahydrofuran, methyl four
Hydrogen furans, methanol, ethyl alcohol, the tert-butyl alcohol, isopropanol, acetone, cyclohexanone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), toluene, diformazan
One of benzene, paraxylene or biphenyl are a variety of.Preferably tetrahydrofuran, total dosage and the total dosage of monomer of organic solvent
Molar ratio is (510~1200): 100.
The nonpolar solvent can be one or more in pentane, n-hexane, hexamethylene, heptane or other alkane.
Preferably n-hexane.
In the present invention, the content by adjusting moisture in solvent controls the molecular weight of resinous polymer.
Due to the above technical solutions, the present invention has the following advantages over the prior art:
1, a small amount of water is added in the present invention in a solvent, is creatively divided by adjusting the content of water and realizing fluoropolymer resin
The adjusting of son amount；
2, method of the invention will not introduce other impurity, realize simplicity, and experiment shows to control using this method molecular weight more smart
Standard, polymer application performance are more excellent.
Detailed description of the invention
Fig. 1 is influence schematic diagram of the different in moisture content to polymer molecular weight in the embodiment of the present invention.
Specific embodiment
The invention will be further described with reference to the accompanying drawings and embodiments:
Embodiment one:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 200ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (1).
(5) the photoetching gum resin (1) can be obtained through GPC test, Mw=8900, PDI=1.62.
Embodiment two:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 400ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (2).
(5) the photoetching gum resin (2) can be obtained through GPC test, Mw=9200, PDI=1.57.
Embodiment three:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 500ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (3).
(5) the photoetching gum resin (3) can be obtained through GPC test, Mw=9300, PDI=1.47.
Example IV:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 600ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (4).
(5) the photoetching gum resin (4) can be obtained through GPC test, Mw=9400, PDI=1.36.
Embodiment five:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 800ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (5).
(5) the photoetching gum resin (5) can be obtained through GPC test, Mw=10000, PDI=1.50.
Embodiment six:
The preparation method of photoresist resin, comprising the following steps:
(1) water intaking point is heated to 50~80 DEG C for use in the tetrahydrofuran 35.62ml of 1257ppm into reaction flask；
(2) by 9.87g methacrylic acid butyrolactone, 7.05g 3- hydroxyl -2- Adamantylmethyl acrylic ester, 15g 1- ethyl
Cyclohexyl methacrylate and 3.58 azodiisobutyronitriles are dissolved in the tetrahydrofuran of 74.83ml, obtain the tetrahydro of raw material
Tetrahydrofuran solution；
(3) tetrahydrofuran solution for the raw material that step (2) obtain is added drop-wise to preheated four containing moisture in step (1)
In hydrogen furans, 70~80 DEG C constant temperature back flow reaction 15 hours；
(4) it is cooled to room temperature after the reaction was completed, with n-hexane precipitated resin, filtering drying obtains photoresist with resin (6).
(5) the photoetching gum resin (6) can be obtained through GPC test, Mw=10500, PDI=1.49.
Change the amount for the moisture being added, carries out multiple groups experiment respectively, as a result as shown in the table:
1 various moisture contents resinous polymer molecular weight of table and molecular weight distribution (high molecular weight)
| Experimental group | n A: n B: n C | Mw(g.mol-1) | Mw/Mn | Moisture (PPM) |
| 1 | 30:20:50 | 8900 | 1.62 | 200 |
| 2 | 30:20:50 | 9200 | 1.57 | 400 |
| 3 | 30:20:50 | 9300 | 1.47 | 500 |
| 4 | 30:20:50 | 9400 | 1.36 | 600 |
| 5 | 30:20:50 | 10000 | 1.50 | 800 |
| 6 | 30:20:50 | 10500 | 1.49 | 1257 |
In table, nAFor the dosage of methacrylic acid butyrolactone, nBFor the dosage of 3- hydroxyl -2- Adamantylmethyl acrylic ester, nCFor the dosage of 1- cyclohexyl methyl acrylate.
Fig. 1 is influence signal fit solution of the different in moisture content to polymer molecular weight, and wherein abscissa contains for moisture
Amount.
It can be seen that in the polymerization by table 1 and Fig. 1, under the conditions of same monomer ratio, polymer molecular weight is with moisture
Increase and increase, polymerization reaction can be effectively facilitated this is mainly due to the addition of water in reaction system, can make reaction speed
Rate is accelerated, and molecular weight increases.Tradition adjusts the mode of molecular weight, and molecular weight floating range is larger, and Mw error is generally in 500-
1000, the molecular weight of more a small range can be obtained in conditioning, and molecular weight is more accurate, and polymer application performance is more excellent.
It is provided only in the embodiment of the present invention using (methyl) acrylate as the resins synthesis of monomer, but the present invention can also answer
For other resins prepared in a manner of free radical polymerization, such as polystyrene resin.
Claims (10)
1. a kind of preparation method of photoresist resin, it is characterised in that: the photoetching gum resin is that had by one or more
The monomer of acid activity group and one or more monomers with polar group are dissolved in the solvent containing quantitative moisture, are being drawn
Under the conditions of sending out existing for agent, carries out ATRP reaction and is prepared, comprising the following steps:
(1) organic solvent containing quantitative moisture is heated to 50~80 DEG C, obtained preheated organic molten containing moisture
Agent；
(2) monomer and initiator are dissolved in the organic solvent of same step (1) considerable moisture content, obtain the solution of raw material；
(3) solution for the raw material that step (2) obtain is added drop-wise in step (1) in the preheated organic solvent containing moisture,
50~80 DEG C constant temperature back flow reaction 2~30 hours；
(4) it is cooled to room temperature after the reaction was completed, with nonpolar solvent precipitated resin, filtering drying obtains photoresist resin；
Wherein, step (1), the moisture content in (2) are 1~1500ppm.
2. the preparation method of photoresist resin according to claim 1, it is characterised in that: the photoetching gum resin is by extremely
Few two kinds of monomer polymerizations form, and the amount of the substance total by monomer is in terms of 100%, and the dosage of monomer is respectively as follows:
Acid activity monomer: 30~70%,
Polar monomer: 70~30%,
Contain the acid activity monomer and one or more polarity lists of one or more different substituents in the photoetching gum resin
Body.
3. the preparation method of photoresist resin according to claim 2, it is characterised in that: the acid activity monomer be containing
(methyl) acrylate of acid-labile group, general structure are as follows:
In formula, R1Carbon-containing group for H or carbon atom number in 1-20, R2For the functional group containing acid-labile group；
The polar monomer is (methyl) acrylate of polar functionalities, general structure are as follows:
In formula, R3Carbon-containing group for H or carbon atom number in 1-20, R4For the functional group of polar functionalities.
4. the preparation method of photoresist resin according to claim 3, it is characterised in that: R2The carbon atom number contained exists
Between 6-30, the hydrogen atom for the carbon atom being connected with ester bond oxygen atom is all replaced by other groups, constitutes tertiary butyl ester, takes
For tertiary butyl ester, alkyl-substituted Buddha's warrior attendant alkyl ester, alkyl-substituted adamantane derivative ester, alkyl-substituted norbornyl ester, alkane
Norborneol derivative ester that base replaces, alkyl-substituted cyclic alkyl ester, one in alkyl-substituted cyclic alkyl derivative ester
Kind is a variety of；
R4The carbon atom number contained is connected with ester bond oxygen atom between 6 ~ 30 and constitutes the Buddha's warrior attendant containing one or more independent hydroxyls
Alkyl ester, the ring pentyl ester containing one or more independent hydroxyls, contains one or more independences at the cyclohexyl containing one or more independent hydroxyls
The polycyclic ester type compound of hydroxyl, butyrolactone, valerolactone, replaces penta at the caged ester type compound containing one or more independent hydroxyls
Lactone, caprolactone, replace caprolactone, the lactone containing adamantane structure, the lactone containing multiring structure, in the lactone containing cage structure
It is one or more.
5. the preparation method of photoresist resin according to claim 1, it is characterised in that: the organic solvent is selected from second
Acetoacetic ester, butyl acetate, butyl acetate, acetic acid peopentyl ester, ethyl lactate, propylene glycol methyl ether acetate, propylene glycol list Acetic Ester,
Dihydroxypropane single-ether, propylene glycol methyl ether acetate, tirethylene glycol methyl ether, tirethylene glycol ether, tetrahydrofuran, methyl tetrahydro
Furans, methanol, ethyl alcohol, the tert-butyl alcohol, isopropanol, acetone, cyclohexanone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), toluene, dimethylbenzene,
One of paraxylene or biphenyl are a variety of.
6. the preparation method of photoresist resin according to claim 1, it is characterised in that: the initiator is organic mistake
Oxide or azo-initiator, dosage are the 5~15% of the amount of the total substance of monomer；The initiator be cyclohexanone peroxide,
One of dibenzoyl peroxide, tert-butyl hydroperoxide, azodiisobutyronitrile, azobisisoheptonitrile are a variety of.
7. the preparation method of photoresist resin according to claim 1 or 5, it is characterised in that: make in the step (1)
The molar ratio of organic solvent used in organic solvent and step (2) is 1: (2~4), the total dosage and list of organic solvent
The molar ratio of the total dosage of body is (510~1200): 100.
8. the preparation method of photoresist resin according to claim 1, it is characterised in that: to room in the step (4)
Resin solution is precipitated after temperature reaction, using the nonpolar solvent precipitated resin of 3-10 times of dosage, with uniformly stirring when precipitating
It mixes, 0.5-3h is stood after precipitating, after being separated by solid-liquid separation, refilter drying and obtain photoetching gum resin.
9. the preparation method of photoresist resin according to claim 1, it is characterised in that: to step in the step (3)
Suddenly the solution that (2) obtain is added dropwise to complete in 1-5h using mode, control is at the uniform velocity added dropwise.
10. the preparation method of photoresist resin according to claim 1, it is characterised in that: non-pole described in step (4)
Property solvent be pentane, it is n-hexane, hexamethylene, one or more in heptane.
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| CN201910133829.1A CN109942741A (en) | 2019-02-22 | 2019-02-22 | A kind of preparation method of photoresist resin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN114560768A (en) * | 2022-03-09 | 2022-05-31 | 河北凯诺中星科技有限公司 | Synthesis method of acrylate resin monomer for 193nm photoresist |
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| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN103896773B (en) * | 2012-12-26 | 2017-03-01 | 锦湖石油化学株式会社 | Acrylic monomer, polymer and the anti-corrosion agent composition comprising this polymer |
| CN108373520A (en) * | 2017-12-22 | 2018-08-07 | 江苏汉拓光学材料有限公司 | A kind of acrylate copolymer and the photoetching compositions comprising it |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1457822A2 (en) * | 2003-03-04 | 2004-09-15 | Fuji Photo Film Co., Ltd. | Positive resist composition |
| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN103896773B (en) * | 2012-12-26 | 2017-03-01 | 锦湖石油化学株式会社 | Acrylic monomer, polymer and the anti-corrosion agent composition comprising this polymer |
| CN108373520A (en) * | 2017-12-22 | 2018-08-07 | 江苏汉拓光学材料有限公司 | A kind of acrylate copolymer and the photoetching compositions comprising it |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| CN114560768A (en) * | 2022-03-09 | 2022-05-31 | 河北凯诺中星科技有限公司 | Synthesis method of acrylate resin monomer for 193nm photoresist |
| CN114560768B (en) * | 2022-03-09 | 2024-03-15 | 河北凯诺中星科技有限公司 | Synthesis method of acrylic resin monomer for 193nm photoresist |
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