CN109796382A - The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions - Google Patents
The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions Download PDFInfo
- Publication number
- CN109796382A CN109796382A CN201910145900.8A CN201910145900A CN109796382A CN 109796382 A CN109796382 A CN 109796382A CN 201910145900 A CN201910145900 A CN 201910145900A CN 109796382 A CN109796382 A CN 109796382A
- Authority
- CN
- China
- Prior art keywords
- acid
- photo
- salty
- chain
- acid generator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of salty photo-acid generator of long flexible chain, preparation method and photoetching compositions, the salty photo-acid generator of long flexible chain has the following structure logical formula (I) or (II):(I)(II) in formula, one or both of A I, S；X is the chain-like groups of a length of 1~20 atom containing chain；naIt is 2 or 3；R be H, Cl, Br, I or carbon atom number 1~20 alkyl or alkoxy it is one or more, substitution number of the R on phenyl ring is 1~5.The present invention connects multiple salt structural units in a photosensitizer molecule, by extending carbochain, photosensitizer can be made preferably to be dissolved in photoresist solution, be allowed to be uniformly distributed；Intramolecular contains multiple sulfosalts and improves the sour efficiency of unit production；The anion of sulfonic fluoropolymer has enough acidity, and chemical iodine can occur with resin；And the structure of long-chain can increase the concentration of light acid within a certain area, and can control the range of acid diffusion to a certain extent.
Description
Technical field
The present invention relates to a kind of photo-acid generators and preparation method thereof, and in particular to a kind of salty photic production of long flexible chain
Sour agent and preparation method thereof.
Background technique
Three important parameters of photoresist include resolution ratio, sensitivity, line width roughness, they determine photoresist in core
Process window when piece manufactures.As semiconductor core piece performance is constantly promoted, exponentially type increases the integrated level of integrated circuit, collection
It is constantly reduced at the figure in circuit.In order to make smaller size of figure, it is necessary to which the performance for improving above three photoresist refers to
Mark.According to Rayleigh equation formula, the resolution ratio of photoresist can be improved using the light source of short wavelength in a lithographic process.Photoetching process
Optical source wavelength from 365nm(I- line) develop to 248nm(KrF), 193nm(ArF), 13nm(EUV).For the spirit for improving photoresist
Sensitivity, KrF, ArF of mainstream, EUV lithography glue use chemical amplification type photosensitive resin at present.As a result, with chemical amplifying type light
The matched photosensitizer of ming tree lipid phase (photo-acid generator) is widely used in high-end photoresist.
Studies have shown that control light acid diffusion is to improve resolution ratio and reduce line after chemical amplification photo etching glue exposure
The important means of broad and rough rugosity.In photoetching glue formula, the dosage of photo-acid generator is all fewer, generally 5% in amount of resin
Within.Since the structure of light acid itself and the structure difference of resin are larger, light acid how to be allowed to be evenly distributed in photoresist film,
The problem of considering is needed when being the design of light acid structure.
As photoetching gum resin is gradually transferred to acrylic resin systems from phenolic resin system, an acidity how is obtained
Suitably, producing the high-efficient photo-acid generator of acid also becomes a new problem.Existing photo-acid generator is generally small molecule
Salt compounded of iodine or sulfosalt, such as diphenyl iodine hexafluorophosphate, triphenyl sulphur perfluoro butyl sulfosalt, they can not be applied
In the photoetching gum resin newly developed.Therefore, develop one kind have high acid efficiency, dissolubility it is good and have it is good acid diffusion
The photo-acid generator of efficiency is the emphasis of photoresist research.
Summary of the invention
Goal of the invention of the invention is to provide a kind of salty photo-acid generator of long flexible chain, to be suitable for new photoresist
Development and Application；Another object of the present invention is to provide the preparation methods of the salty photo-acid generator of this long flexible chain.
To achieve the above object of the invention, the technical solution adopted by the present invention is that: a kind of salty photic production acid of long flexible chain
Agent has the following structure logical formula (I) or (II):
(I)
(II)
Sulfonic fluoropolymer anion in the compound with multiple salt cations and a tool backbone；
A is one or both of I, S；
naIt is 2 or 3；
R be H, Cl, Br, I or carbon atom number 1~20 alkyl or alkoxy one or more, substitution of the R on phenyl ring
Number is 1~5；
Contain chain-like groups in X, the general structure of X is expressed as 、、、、Or, wherein n is chain length, a length of 1~20 atom of chain.
The salty photo-acid generator of long flexible chain of the invention, compound molecule is by 2 cation groups and 1 anion
Group is constituted.
The salt cation general structure is (III) or (IV):
(III),(IV)
Wherein, R is hydrogen, methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, the third oxygen
One of base, isopropoxy, n-butoxy, isobutoxy or tert-butoxy, fluorine, chlorine, bromine, iodine are a variety of.
Salt cation group is preferred are as follows:
、、、、、、、、、、、、、、、、、、、、、、、、、、、、、。
The sulfonic fluoropolymer anion of the tool backbone, general structure is (V) or (VI):
(V),(VI)
In formula, X is the carbochain of straight chain, the carbochain for having branch, the carbochain with ehter bond, the carbochain with ester bond, tool silicon ether structure
Carbochain, the carbochain of tool sulfone or sulfoxide structure, tool sulphur, the carbochain of silicon or oxygen heteroatom or comprising a kind of in above structure unit or
A variety of long-chains.
Anionic group is preferred are as follows:
、、、、、、、、、、、、、、、
、、、、、、、、。
The preparation method of the above-mentioned salty photo-acid generator of long flexible chain, by excessive 2- under Catalyzed by p-Toluenesulfonic Acid
Bromo-2,2-difluoroethanol and diacid compounds are heated to reflux 2~30h in toluene solution, after reaction solution obtain esterification produce
Object two (bromo- 2, the 2- difluoroethoxy of 2-) two acid esters；The ester is dissolved in acetonitrile, and sodium dithionite/sodium bicarbonate is added dropwise
Aqueous solution adds rear reaction solution heating stirring 12~for 24 hours at 40~80 DEG C, then cools down, and solid sodium chloride is added to being saturated,
Use acetonitrile extraction；Organic phase, which merges, is added pure water, then excessive hydrogen peroxide is added dropwise, then react at room temperature 12~for 24 hours；After fully reacting
With acetonitrile extraction 2 times, organic phase is dry with anhydrous sodium sulfate, and two (2- sodium sulfonate -2,2- difluoroethoxies) two are obtained after concentration
Acid esters sulfonate sodium；After being dissolved into clear liquid with methanol, then the aqueous solution of sulfosalt or salt compounded of iodine is added dropwise, stirring 12 is protected from light after dripping off
~for 24 hours, it then uses chloroform extraction 3 times, organic phase is concentrated to get the salty photo-acid generator of long-chain.
Using the salty photo-acid generator of long flexible chain of the invention, photoetching compositions can be prepared.For example, a kind of light
The formula of photoresist composition are as follows: be calculated in mass percent, contain: acid activity resin 1 ~ 20%, photo-acid generator 0.01 ~ 10%, acid
Inhibitor 0.001 ~ 10%, solvent 60 ~ 99%.Photo-acid generator therein is using the salty photic production acid of long flexible chain of the invention
Agent.In addition, additional photo-acid generator can be added again when prepared by photoetching compositions to obtain better lithographic results, and
The photosensitizer of present aspect is used together.Optional photo-acid generator are as follows: triphenyl sulfosalt, three p-methylphenyl sulfosalts, three pairs
Tert-butyl-phenyl sulfosalt, three (3,5- 3,5-dimethylphenyl) sulfosalts, three (3,5- di-tert-butyl-phenyl) sulfosalts, three are (to first
Phenyl) sulfosalt, three (to tert .- butoxyphenyl) sulfosalts, three (to n-butoxyphenyl) sulfosalts, diphenyl is (to second
Phenyl) sulfosalt, diphenyl (cyclohexyl phenyl) sulfosalt, diphenyl (to n-butoxyphenyl) sulfosalt, diphenyl
Salt compounded of iodine, di-p-tolyl salt compounded of iodine, two pairs of tert-butyl-phenyl salt compounded of iodine, two pairs of ethoxyl phenenyl salt compounded of iodine, two pairs of positive fourth oxygen
Base phenyl sulfosalt；Its coordination anion is trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methyl benzenesulfonic acid or naphthalene sulfonic acids.
Photoresist configuration method are as follows: at room temperature, in a clean vial, acid is successively added according to formula rate
Reactive resin, photo-acid generator, acid inhibitor and solvent, mixture are protected from light concussion 16-96 hours in bottle, keep it sufficiently molten
Solution.Then photoresist solution successively is filtered with 0.5 micron and nylon material below and the filter of UPE material.Filtrate is collected
In a clean vial, lithography experiments are carried out after the completion.
Acid activity resin is polymerized by multiple functional groups, includes acid activity group and polar group.Acid activity tree
The general structure of rouge is as follows:
The molecular weight of acid activity film-forming resin is 3000 ~ 100000, and molecular weight distribution is between 1.0-3.0.Wherein acid activity base
The content of the monomer of group is between 30%-70%, and the content of monomer of polar group is between 70-30%.Preferably 50:50.
Containing the acid-labile group of different substituents, specially acid activity (methyl) acrylate, structure in acid activity resin
To meet at least one of chemical general formula monomer, specific acid activity monomer structure general formula is as follows:
R1The carbochain of=H or carbon atom number in 1-20.R2=acid-sensitive level Four carbon.
Specifically, R2It is a kind of level Four ester of carbon atom number between 6-30, the carbon atom being connected with ester bond oxygen atom
Hydrogen atom all replaced by other groups, preferred structure be tertiary butyl ester, substituted tert-butyl ester, alkyl-substituted adamantane
Ester, alkyl-substituted adamantane derivative ester, alkyl-substituted norbornyl ester, alkyl-substituted norborneol derivative ester, alkyl
Substituted cyclic alkyl ester, alkyl-substituted cyclic alkyl derivative ester etc. are one such or a variety of.
Contain one or more polar groups, specially (methyl) acrylate of polar functionalities, knot in acid activity resin
Structure is to meet at least one of chemical general formula monomer, and specific polar monomer general structure is as follows:
R3The carbochain of=H or carbon atom number in 1-20.R4(methyl) acrylate of=polar functionalities.
Specifically, R4For carbon atom number between 6 ~ 30 the ring-type, caged of hydroxyl or straight chain type containing carbon structure and all kinds of
Lactone structure, possible structure are the Buddha's warrior attendant alkyl ester containing one or more independent hydroxyls, the ring containing one or more independent hydroxyls
Own ester, the ring pentyl ester containing one or more independent hydroxyls, the polycyclic ester type compound containing one or more independent hydroxyls, containing 1 or
The caged ester type compound of multiple independent hydroxyls, preferred structure are butyrolactone, valerolactone, replace valerolactone, caprolactone, substitution
Caprolactone, the lactone containing adamantane structure, the lactone containing multiring structure, the lactone containing cage structure etc. are one such or more
Kind.
Acid activity film-forming resin the preparation method is as follows: under the conditions of comonomer is existing for the radical initiator, molten
Polymerization reaction is carried out in agent to be prepared.In the polymerization reaction of acid activity film-forming resin, initiator is azo initiator, peroxidating
The radical initiator of object, preferred azo initiator are azodiisobutyronitrile or azobisisoheptonitrile, preferred peroxide
Radical initiator be tert-butyl hydroperoxide pivalate, tertiary fourth oxygen hydrogen peroxide, benzoic acid hydrogen peroxide or peroxide benzene
Formyl etc.；The initiator amount is the 0.3% ~ 15% of comonomer gross mass；The adding manner of initiator is that monomer is first added
And partial solvent, it is then heated to polymerization temperature, then initiator solution is added dropwise.The temperature of polymerization reaction according to the solvent that uses and
Initiator is different, controls between 60 ~ 160 DEG C, and polymerization time is different also according to the solvent used and initiator, control 4 ~
Between 32 hours.
The copolyreaction of acid activity film-forming resin can be carried out in various solvents or multi-solvents mixing species, preferred solvent
For methanol, ethyl alcohol, dioxane, acetone, methyl ethyl ketone, tetrahydrofuran, methyltetrahydrofuran, benzene,toluene,xylene, chlorine
Imitative, dichloroethanes, trichloroethanes etc..
After the copolyreaction of acid activity film-forming resin, can pure water, methanol, methanol/water mixture, ethyl alcohol, ethyl alcohol/
Aqueous mixtures, isopropanol, iso-propanol/water mixture, normal heptane, n-hexane, hexamethylene, pentane, petroleum ether, ether, methyl
The organic or inorganic solvents kind precipitation and separation such as tertbutyl ether, the yield for being dried in vacuo rear copolymer is 50% ~ 80%.
The sour dispersion inhibitor used is a kind of nitrogenous compound, including primary amine, secondary amine and tertiary amine compound, is especially had
There are the amine compounds of hydroxyl, ehter bond, ester bond, amido bond, lactonic ring, cyano or sulfonic acid ester bond, preferred structure is diethylamine, three
One of the fatty amines or aromatic amine such as ethamine, ethanol amine, triethanolamine, aniline, phenyl ethylamine are a variety of.
The more sulfosalt photo-acid generators of above-mentioned acid activity resin, long flexible chain and acid diffusion suppression can be dissolved comprising one kind
The organic solvent of preparation, preferably solvent are propylene glycol methyl ether acetate, propylene glycol list Acetic Ester, dihydroxypropane single-ether, the third two
Alcohol methyl ether acetate, tirethylene glycol methyl ether, tirethylene glycol ether, butyl acetate, acetic acid peopentyl ester, ethyl lactate, methyl
One of ethyl ketone and methyl iso-butyl ketone (MIBK) are a variety of.
Due to the above technical solutions, the present invention has the following advantages over the prior art:
The present invention connects multiple photosensitive structure units in a light acid molecule, by extending carbochain, can make photosensitizer preferably
It is dissolved in photoresist solution, is allowed to be uniformly distributed；Intramolecular contains multiple sulfosalts and improves the sour efficiency of unit production；Fluorine-containing sulphur
The anion of acid has enough acidity, and chemical iodine can occur with resin；And the structure of long-chain can be in certain area
The interior concentration for increasing light acid, and the range of acid diffusion can be controlled to a certain extent.
Specific embodiment
Compound experiment is carried out by following reaction route in embodiment:
The synthesis of embodiment one: two (bromo- 2, the 2- difluoroethoxy of 2-) succinate (3)
Be added in the vial of the 250mL equipped with oil water separator and condenser pipe 41g 2- bromo-2,2-difluoroethanol (1),
The toluene of 10g succinic acid (2), 2.92g p-methyl benzenesulfonic acid and 90mL, mixed liquor are heated to reflux 8h under stiring.After reaction
Cooling, reaction solution is washed 3 times with 50mL aqueous sodium carbonate, 50mL saturated common salt water washing 1 time, organic phase anhydrous sodium sulfate
It is dry, esterification products two (bromo- 2, the 2- difluoroethoxy of 2-) succinate (3) total 21g, yield 61% are obtained after concentration.Nuclear-magnetism knot
Fruit:1H NMR(CDCl3, δ) and 2.69, s, 4H；4.91, t, 4H.
The synthesis of embodiment two: two (2- sodium sulfonate -2,2- difluoroethoxy) succinate (4)
In the round-bottomed bottle of 500mL, the dissolution of (bromo- 2, the 2- difluoroethoxy of the 2-) succinate (3) of 20g bis- and 80mL second is added
Nitrile, stirring and dissolving.17.3g sodium dithionite and 12.5g sodium bicarbonate and 80mL aqueous solution are added dropwise under nitrogen protection, adds
Reaction solution heating stirring 16h at 70 DEG C afterwards.Then it cools down, suitable solid sodium chloride is added to saturation.Reaction liquid layer, water
Mutually use 30mL acetonitrile extraction 2 times.Organic phase merging is transferred in 500mL round-bottomed bottle, and the pure water of 100mL is added.Mixed liquor is in nitrogen
30% hydrogen peroxide of 11.2g is added dropwise under gas, 16h is then stirred at room temperature.It is layered after reaction, water phase 50mL acetonitrile extraction 2
Secondary, organic phase merging is dry with anhydrous sodium sulfate, and two (2- sodium sulfonate -2,2- difluoroethoxy) succinates are obtained after concentration
(4) total 12.3g, yield 55%.Nuclear-magnetism result:1H NMR(DMSO, δ) 2.75, s, 4H；4.99, t, 4H.
Embodiment three: benzyltriphenylphosphonium chloride sulfosalt (5) synthesis
The anhydrous methylene chloride of 9.0g diphenyl sulfoxide and 60mL, reaction is added in the there-necked flask of 250mL under nitrogen protection
Liquid is cooled to 0 DEG C or less.Keep reaction solution at 0 DEG C hereinafter, 14.5g trim,ethylchlorosilane is added dropwise.Slowly heating after being added dropwise
To room temperature, continue to stir 1h.Then reaction solution is again but to 0 DEG C hereinafter, at this temperature, be added dropwise the tetraphenylphosphonium chloride of the 2M of 67mL
The tetrahydrofuran solution of magnesium.It is to slowly warm up to room temperature after being added dropwise, continues to stir 2h.Then a small amount of water of reaction solution quenches anti-
It answers, the aqueous hydrochloric acid solution of the 0.2N of 75mL is added.Mixed liquor with the ether of 30mL wash it is secondary after, water phase is benzyltriphenylphosphonium chloride
The aqueous solution of sulfosalt (5), be placed on be protected from light place it is spare.
Example IV: the synthesis of bi triphenyl sulfosalt two (2- sulfonic acid -2,2- difluoroethoxy) succinate (6)
The first of 10g bis- (2- sodium sulfonate -2,2- difluoroethoxy) succinate (4) and 70mL is added in the round-bottomed bottle of 250mL
Alcohol, stirring and dissolving.Then under the conditions of being protected from light, the aqueous solution of benzyltriphenylphosphonium chloride sulfosalt (5) well prepared in advance is added dropwise.It is added dropwise
After continue to be protected from light stirring 16h.After use 30mL chloroform extraction 3 times, merge organic phase, then washed with 30mL pure water
It washs 2 times.Layering, removes water phase, and organic phase is concentrated to get bi triphenyl sulfosalt two (2- sulfonic acid -2,2- difluoroethoxy) fourth two
Acid esters (6) total 16.5g, yield 80%.Nuclear-magnetism result:1H NMR(DMSO, δ) 2.75, s, 4H；4.99, t, 4H；7.5-8.0 m,
30H。
Embodiment five: a kind of modulation containing above-mentioned positivity chemical amplification photoetching glue formula, formula composition are as follows:
Acid activity resin includes 2 kinds of acid activity groups and 2 kinds of polar groups, ratio 50:50.
Photosensitizer (photo-acid generator) is the product of example IV.
Sour dispersion inhibitor is N, N- dibutyl aniline.
Solvent is PGMEA:PGME=6:4.
Specific formula modulator approach:
In a new clean 100mL vial, 8.5g acid activity resin, two (2- of 0.11g bi triphenyl sulfosalt is added
Sulfonic acid -2,2- difluoroethoxy) succinate, 0.05gN, N- dibutyl aniline, 54gPGMEA, 36gPGME.At room temperature, it mixes
Object shakes 24 hours in bottle, dissolves it sufficiently.Then photoetching successively is filtered with 0.22 micron and 0.02 micron of filter
Sol solution.Lithography experiments are carried out after the completion.
Lithography experiments method: the photoresist of above-mentioned preparation is rotated on 8 " silicon wafers with 2000 ~ 3000 revs/min of speed
Film is toasted 90 seconds on 120 DEG C of hot plates, is then exposed on exposure machine, exposure intensity 10-50mJ/cm2.In 110 DEG C of heat after exposure
It is toasted on plate 90 seconds, finally develops 60 seconds in 2.38%TMAH developer solution, then dry in Electron microscopy photoetching knot
Fruit.
It is provided by the invention preferably to dissolve and be distributed in the photoresist comprising the more sulfosalt photo-acid generators of long flexible chain；
Unit can be improved and produce sour efficiency, chemical iodine can occur with resin；And the structure of long-chain can increase within a certain area
The concentration of light acid, and the range of acid diffusion can be controlled to a certain extent.
Claims (8)
1. a kind of salty photo-acid generator of long flexible chain, it is characterised in that: have the following structure logical formula (I) or (II):
(I)
(II)
Sulfonic fluoropolymer anion in the compound with multiple salt cations and a tool backbone；
A is one or both of I, S；
naIt is 2 or 3；
R be H, Cl, Br, I or carbon atom number 1~20 alkyl or alkoxy one or more, substitution of the R on phenyl ring
Number is 1~5；
Contain chain-like groups in X, the general structure of X is expressed as 、、、、Or, wherein n is chain length, a length of 1~20 atom of chain.
2. the salty photo-acid generator of long flexible chain according to claim 1, it is characterised in that: the salt cation knot
Structure general formula is (III) or (IV):
(III),(IV)
Wherein, R is hydrogen, methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, tert-butyl, methoxyl group, ethyoxyl, the third oxygen
One of base, isopropoxy, n-butoxy, isobutoxy or tert-butoxy, fluorine, chlorine, bromine, iodine are a variety of.
3. the salty photo-acid generator of long flexible chain according to claim 2, it is characterised in that: the salt cation choosing
From:
、、、、、、、、、、、、、、、、、、、、、、、、、、、、、。
4. the salty photo-acid generator of long flexible chain according to claim 1, it is characterised in that: the tool backbone
Sulfonic fluoropolymer anion, general structure be (V) or (VI):
(V),(VI)
In formula, X is the carbochain of straight chain, the carbochain for having branch, the carbochain with ehter bond, the carbochain with ester bond, tool silicon ether structure
Carbochain, the carbochain of tool sulfone or sulfoxide structure, tool sulphur, the carbochain of silicon or oxygen heteroatom or comprising a kind of in above structure unit or
A variety of long-chains.
5. the salty photo-acid generator of long flexible chain according to claim 4, it is characterised in that: the tool backbone
Sulfonic fluoropolymer anion is selected from:
、、、、、、、、、、、、、、、、、、、、、、、。
6. a kind of preparation method of the salty photo-acid generator of long flexible chain described in claim 1, it is characterised in that: to toluene
Under sulfonic acid catalysis excessive 2- bromo-2,2-difluoroethanol and diacid compounds are heated to reflux 2~30h in toluene solution, tied
Reaction solution obtains esterification products two (bromo- 2, the 2- difluoroethoxy of 2-) two acid esters after beam；The ester is dissolved in acetonitrile, the company of dropwise addition two
Sodium sulfite/sodium bicarbonate aqueous solution adds rear reaction solution heating stirring 12~for 24 hours at 40~80 DEG C, then cools down, add
Enter solid sodium chloride to being saturated, uses acetonitrile extraction；Organic phase, which merges, is added pure water, then excessive hydrogen peroxide is added dropwise, and then room temperature is anti-
Answer 12~for 24 hours；It is used acetonitrile extraction 2 times after fully reacting, organic phase is dry with anhydrous sodium sulfate, and two (2- sulfonic acid are obtained after concentration
Sodium -2,2- difluoroethoxy) two acid esters sulfonate sodiums；After being dissolved into clear liquid with methanol, then the water of sulfosalt or salt compounded of iodine is added dropwise
Solution is protected from light stirring 12~for 24 hours after dripping off, then use chloroform extraction 3 times, it is salty photic that organic phase is concentrated to get long-chain
Acid agent.
7. a kind of photoetching compositions, it is characterised in that: in the photoetching compositions, include at least a kind of claim 1-4
In any salty photo-acid generator of long flexible chain, a kind of film-forming resin with acid activity, a kind of acid diffusion inhibit
Agent and organic solvent.
8. photoetching compositions according to claim 8, it is characterised in that: the photoetching compositions also include other light
Quick dose, other photosensitizers are selected from triphenyl sulfosalt, three p-methylphenyl sulfosalts, three couples of tert-butyl-phenyl sulfosalts, three
(3,5- 3,5-dimethylphenyl) sulfosalt, three (3,5- di-tert-butyl-phenyl) sulfosalts, three (p-methoxyphenyl) sulfosalts, three
(to tert .- butoxyphenyl) sulfosalt, three (to n-butoxyphenyl) sulfosalts, diphenyl (to ethoxyl phenenyl) sulfosalt, two
Phenyl (cyclohexyl phenyl) sulfosalt, diphenyl (to n-butoxyphenyl) sulfosalt, diphenyl iodnium, di-p-tolyl iodine
Salt, two pairs of tert-butyl-phenyl salt compounded of iodine, two pairs of ethoxyl phenenyl salt compounded of iodine, two pairs of n-butoxyphenyl sulfosalts；It is coordinated
Anion is trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methyl benzenesulfonic acid or naphthalene sulfonic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910145900.8A CN109796382A (en) | 2019-02-27 | 2019-02-27 | The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910145900.8A CN109796382A (en) | 2019-02-27 | 2019-02-27 | The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109796382A true CN109796382A (en) | 2019-05-24 |
Family
ID=66561378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910145900.8A Pending CN109796382A (en) | 2019-02-27 | 2019-02-27 | The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109796382A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111077731A (en) * | 2019-12-24 | 2020-04-28 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator containing trumpet-shaped tea alcohol structure and preparation method thereof |
| CN112661755A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from isocorynanthine and preparation method thereof |
| CN113698329A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for 193nm immersion lithography and intermediate thereof |
| CN113703285A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for 193nm immersion lithography and photoresist composition |
| CN113698330A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Preparation method of photoacid generator for 193nm immersion lithography |
| CN113754573A (en) * | 2021-08-25 | 2021-12-07 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for immersion ArF photoetching and intermediate thereof |
| CN113801048A (en) * | 2021-08-25 | 2021-12-17 | 上海芯刻微材料技术有限责任公司 | Preparation method of immersion type photoacid generator for ArF photoetching |
| CN113801042A (en) * | 2021-08-25 | 2021-12-17 | 上海新阳半导体材料股份有限公司 | Multi-onium salt type photoacid generator for dry-method ArF light source photoetching |
| CN113820918A (en) * | 2021-08-25 | 2021-12-21 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for immersion ArF photoetching and photoresist composition |
| CN113820919A (en) * | 2021-08-25 | 2021-12-21 | 上海新阳半导体材料股份有限公司 | Application of multi-onium salt type photoacid generator for dry-process ArF light source photoetching |
| CN114315584A (en) * | 2021-12-30 | 2022-04-12 | 宁波南大光电材料有限公司 | Photosensitizer and preparation method thereof |
| CN114315531A (en) * | 2021-12-31 | 2022-04-12 | 宁波南大光电材料有限公司 | Photosensitizer with high photosensitive activity and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1717998A (en) * | 2005-07-13 | 2006-01-11 | 河南省农业科院植物保护研究所 | Pesticide composition contg. imidacloprid and phoxim |
| CN102883704A (en) * | 2010-03-15 | 2013-01-16 | 莱雅公司 | Composition containing a dibenzoylmethane screening agent and a hydrophilic or water-soluble merocyanin uv-screening agent, and a process for the radiation-photostabilization of the dibenzoylmethane screening agent |
| US20150301449A1 (en) * | 2014-04-22 | 2015-10-22 | Shin-Etsu Chemical Co., Ltd. | Photoacid generator, chemically amplified resist composition, and patterning process |
-
2019
- 2019-02-27 CN CN201910145900.8A patent/CN109796382A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1717998A (en) * | 2005-07-13 | 2006-01-11 | 河南省农业科院植物保护研究所 | Pesticide composition contg. imidacloprid and phoxim |
| CN102883704A (en) * | 2010-03-15 | 2013-01-16 | 莱雅公司 | Composition containing a dibenzoylmethane screening agent and a hydrophilic or water-soluble merocyanin uv-screening agent, and a process for the radiation-photostabilization of the dibenzoylmethane screening agent |
| US20150301449A1 (en) * | 2014-04-22 | 2015-10-22 | Shin-Etsu Chemical Co., Ltd. | Photoacid generator, chemically amplified resist composition, and patterning process |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111077731A (en) * | 2019-12-24 | 2020-04-28 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator containing trumpet-shaped tea alcohol structure and preparation method thereof |
| CN112661755A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Sulfonium salt photo-acid generator synthesized from isocorynanthine and preparation method thereof |
| CN113820918A (en) * | 2021-08-25 | 2021-12-21 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for immersion ArF photoetching and photoresist composition |
| CN113820919A (en) * | 2021-08-25 | 2021-12-21 | 上海新阳半导体材料股份有限公司 | Application of multi-onium salt type photoacid generator for dry-process ArF light source photoetching |
| CN113698330A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Preparation method of photoacid generator for 193nm immersion lithography |
| CN113754573A (en) * | 2021-08-25 | 2021-12-07 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for immersion ArF photoetching and intermediate thereof |
| CN113801048A (en) * | 2021-08-25 | 2021-12-17 | 上海芯刻微材料技术有限责任公司 | Preparation method of immersion type photoacid generator for ArF photoetching |
| CN113801042A (en) * | 2021-08-25 | 2021-12-17 | 上海新阳半导体材料股份有限公司 | Multi-onium salt type photoacid generator for dry-method ArF light source photoetching |
| CN113698329A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for 193nm immersion lithography and intermediate thereof |
| CN113703285A (en) * | 2021-08-25 | 2021-11-26 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for 193nm immersion lithography and photoresist composition |
| CN113820919B (en) * | 2021-08-25 | 2024-02-02 | 上海新阳半导体材料股份有限公司 | Application of multi-onium salt type photoacid generator for ArF light source dry lithography |
| CN113820918B (en) * | 2021-08-25 | 2023-08-25 | 上海芯刻微材料技术有限责任公司 | Photoacid generator for immersion ArF lithography and photoresist composition |
| CN113801042B (en) * | 2021-08-25 | 2022-09-27 | 上海新阳半导体材料股份有限公司 | Multi-onium salt type photoacid generator for dry-process photoetching of ArF light source |
| WO2023024231A1 (en) * | 2021-08-25 | 2023-03-02 | 上海新阳半导体材料股份有限公司 | Polyonium salt photoacid generator for arf light source dry lithography, preparation method therefor and application thereof |
| CN113801048B (en) * | 2021-08-25 | 2023-08-11 | 上海芯刻微材料技术有限责任公司 | Preparation method of photo-acid generator for immersion ArF lithography |
| CN114315584A (en) * | 2021-12-30 | 2022-04-12 | 宁波南大光电材料有限公司 | Photosensitizer and preparation method thereof |
| CN114315531A (en) * | 2021-12-31 | 2022-04-12 | 宁波南大光电材料有限公司 | Photosensitizer with high photosensitive activity and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109796382A (en) | The salty photo-acid generator of long flexible chain, preparation method and photoetching compositions | |
| TWI483076B (en) | Positive resist composition, method of forming resist pattern using the same, and polymeric compound | |
| TWI505033B (en) | Positive resist composition, method of forming resist pattern and polymeric compound | |
| TWI474115B (en) | Positive resist composition, method of forming resist pattern, polymer compound | |
| CN102186890B (en) | Fluorine-containing sulfonates having polymerizable anions and manufacturing method therefor, fluorine-containing resins, resist compositions, and pattern-forming method using same | |
| TWI465849B (en) | Resist composition, method of forming resist pattern, compound and acid generator including the compound | |
| TWI449717B (en) | Positive resist composition, method of forming resist pattern | |
| TWI474116B (en) | Positive resist composition and method of forming resist pattern | |
| TWI403846B (en) | Positive resist composition, method of forming resist pattern, and polymeric compound | |
| TWI493291B (en) | Positive resist composition and method of forming resist pattern | |
| TWI461844B (en) | Resist composition, method of forming resist pattern, novel compound, and acid generator | |
| TWI465848B (en) | Positive resist composition, method of forming resist pattern, and polymeric compound | |
| TWI475319B (en) | Resist composition, method of forming resist pattern, polymeric compound, and compound | |
| TWI464532B (en) | Resist composition, method of forming resist pattern, compound and acid generator | |
| TWI501029B (en) | Method of producing polymeric compound | |
| TWI594073B (en) | Negative tone-development resist composition and method of forming resist pattern | |
| CN110058489A (en) | A kind of photoetching compositions and preparation method thereof | |
| TWI486342B (en) | Resist composition, method of forming resist pattern, novel compound, and acid generator | |
| TWI471687B (en) | Resist composition, method of forming resist pattern, novel compound, and acid generator | |
| TWI534531B (en) | Resist composition, method of forming resist pattern, and polymeric compound | |
| CN101408728B (en) | Resist composition, method of forming resist pattern, novel compound and method of producing the same | |
| TWI494695B (en) | Positive resist composition and method of forming resist pattern | |
| CN109991811A (en) | A kind of acid dispersion inhibitor and preparation method thereof and photoetching compositions | |
| JP5756672B2 (en) | Photoacid generator and photoresist containing the same | |
| TWI394005B (en) | Positive resist composition, method of forming resist pattern, and polymeric compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20201224 Address after: 315800 21 Qingshan Road, Chaiqiao street, Beilun District, Ningbo City, Zhejiang Province Applicant after: NINGBO NANDA OPTOELECTRONIC MATERIAL Co.,Ltd. Address before: 7 / F, Yueliangwan International Center, 9 Cuiwei street, Suzhou Industrial Park, Suzhou, Jiangsu Province Applicant before: JIANGSU NATA OPTO-ELECTRONIC MATERIAL Co.,Ltd. |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190524 |