CN115784953A - Compound for preparing positive resist and preparation method thereof - Google Patents
Compound for preparing positive resist and preparation method thereof Download PDFInfo
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- CN115784953A CN115784953A CN202310043379.3A CN202310043379A CN115784953A CN 115784953 A CN115784953 A CN 115784953A CN 202310043379 A CN202310043379 A CN 202310043379A CN 115784953 A CN115784953 A CN 115784953A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 30
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006138 lithiation reaction Methods 0.000 claims abstract description 15
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010791 quenching Methods 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims 3
- 239000000047 product Substances 0.000 abstract description 10
- 239000012467 final product Substances 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- XRJQBFBLXDVKCZ-UHFFFAOYSA-N [Li]C1=CC(F)=CC(F)=C1 Chemical compound [Li]C1=CC(F)=CC(F)=C1 XRJQBFBLXDVKCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000007789 gas Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- -1 aromatic halogen compound Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- VTZWUMHFBYQZRF-UHFFFAOYSA-N 1-(3,5-difluorophenyl)sulfinyl-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(S(=O)C=2C=C(F)C=C(F)C=2)=C1 VTZWUMHFBYQZRF-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005034 decoration Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Images
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The invention relates to the technical field of organic chemical synthesis, in particular to a compound for preparing positive resist and a preparation method thereof; the preparation method mainly comprises two steps, wherein N-butyl lithium and 3, 5-difluorobromobenzene are subjected to lithiation reaction to generate 3, 5-difluorophenyl lithium, the 3, 5-difluorophenyl lithium is further reacted with thionyl chloride to generate a target product, and the two steps of reaction are carried out in N 2 Under protection, the reaction is carried out in a low-temperature reaction kettle; the synthesis reaction process provided by the invention is simple and convenient, few by-products are obtained, the final product can be obtained through simple purification, and the final product has high purity and good yield.
Description
Technical Field
The invention relates to the technical field of organic chemical synthesis, in particular to a compound for preparing a positive resist and a preparation method thereof.
Background
With the rapid development of electronic industries such as semiconductors, especially the development of large-scale and super-large-scale integrated circuits in recent years, the application of resists is also more extensive.
Resists are classified into positive resists, which cause a coating layer to undergo a photocrosslinking reaction under irradiation of light, and negative resists, which become insoluble in a developer solution in a region exposed to the radiation; when positive resists are exposed image-wise to radiation, the coating undergoes a photodegradation reaction by the irradiation of light, resulting in an increase in solubility, and is washed away during development, leaving the resist in the dark areas.
The resist needs catalytic amount of acid to participate in the reaction during the use process, and the acid is easily affected by alkaline substances existing in the substrate and air from the outside, so that the use effect is poor. Therefore, many of the methods for producing resists disclosed so far focus on preventing or suppressing the influence of the basic substance on the acid by using the compound for producing a resist and other polymer-forming resins, but little attention has been paid to the method for producing the compound for producing a resist.
Positive resists are used in high precision instruments and have high requirements for the purity of the resist. As a compound for preparing a positive resist, improvement of purity and yield of the compound is particularly important for industrial production and application. Currently, the preparation method of the compound is generally to react the aromatic halogen compound with Mg powder to generate Grignard reagent, and then react with thionyl chloride. The grignard reagent generated in the reaction has relatively mild reaction conditions, but has poor selectivity and a large amount of byproducts, so that the compound prepared by the reaction has poor yield and low purity, and a final product meeting electronic-grade requirements can be obtained through a complicated post-treatment process. It is thus seen that it is important to develop a process for producing a compound for use in the production of a positive resist, which process ensures both yield and product purity, in place of the old process.
It has been found that in the reaction of aromatic halogen compounds, when a lithium compound participates in the reaction, the reaction speed is high and the byproducts are less. However, different lithiated compounds have different chemical properties, and the reaction conditions are relatively different and harsh, and the reaction results are directly influenced by reaction conditions such as lithiation temperature, lithiation time and the like, and when lithium diisopropylamide which reacts with an aromatic halide compound reacts with the aromatic halide compound, ortho-lithiation tends to occur. In order to solve the above-mentioned technical problems encountered in the preparation of a compound for a positive resist, the present patent has conducted a one-step research and study on how to improve a compound for preparing a positive resist and a preparation method thereof using a lithiation reaction.
Disclosure of Invention
An object of the present invention is to provide a compound for use in the preparation of a positive resist.
Another object of the present invention is to provide a method for preparing a compound for use in the preparation of a positive resist.
The technical scheme adopted for realizing the purpose of the invention is as follows:
the invention provides a compound for preparing a positive resist, which has a structure shown in the following formula (I):
（I）。
the invention also provides a compound for preparing the positive resist and a preparation method thereof, and the compound comprises the following steps:
(1) The molar parts of the prepared raw materials are respectively as follows: 1-3 parts of n-butyl lithium, 2 parts of 3, 5-difluorobromobenzene and 0.5-2 parts of thionyl chloride;
preferably, 2.1-2.3 parts of n-butyllithium and 1.1 parts of thionyl chloride;
(2) Preparing an instrument: low-temperature reaction kettle, reflux condenser, stirrer and distillation kettle
(3) The synthetic route is as follows:
the method comprises the following two steps:
step 1:
reacting 3, 5-difluorobromobenzene with anhydrous tetrahydrofuran in N 2 Adding the mixture into a low-temperature reaction kettle under protection, mixing, reducing the temperature of the system to-10 ℃ by using the reaction kettle, and continuously stirring in the temperature reduction process; then N is added 2 Slowly dropwise adding n-butyl lithium under protection; continuously cooling to the lithiation temperature in a low-temperature reaction tank, wherein the lithiation temperature is-80 to-30 ℃, and is preferably-78 to-70 ℃; the lithiation time is 0.5 to 1h, and the reaction is always in N 2 Under the protection of the catalyst.
Step 2:
taking thionyl chloride at N 2 Dropping the mixture into a low-temperature reaction kettle under protection, and keeping the temperature at-30 to 10 ℃, preferably-30 to-20 ℃; continuously reacting for 0.5 to 3h, preferably 1.5 to 2h; after the raw materials are completely reacted, closing the nitrogen protection, opening a feed port, and adding a proper amount of saturated ammonium chloride aqueous solution to quench the reaction; and (3) quenching to obtain a 5,5' -sulfinylbis (1, 3-difluorobenzene) mixed solution which is a product obtained in the step (2), and crystallizing and purifying to obtain a finished product which is the compound for preparing the positive resist.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a compound for preparing positive resist and a preparation method thereof, n-butyllithium is used for participating in the reaction, and the synthesis reaction process is simple and convenient; by controlling the lithiation temperature and the lithiation time, n-butyllithium has good selectivity in the reaction process, strong target property and no substitution reaction of other sites, so that few byproducts are obtained, a final product, namely a compound for preparing a positive resist, can be obtained by simple purification, and the final product has high purity and good yield and has great significance for subsequent application.
Drawings
FIG. 1 is a gas chromatogram of a compound obtained in step 1 of example 1 of the present invention;
FIG. 2 is a liquid chromatogram of a compound for use in the preparation of a positive resist according to example 1 of the present invention;
FIG. 3 is a gas chromatogram of the compound obtained in step 1 of example 2 of the present invention;
FIG. 4 is a liquid chromatogram of a compound for use in the preparation of a positive resist according to example 2 of the present invention;
FIG. 5 is a gas chromatogram of the compound obtained in step 1 of example 3 of the present invention;
FIG. 6 is a liquid chromatogram of a compound used for preparing a positive resist of example 3 of the present invention;
FIG. 7 is a gas chromatogram of the compound obtained in step 1 of example 4 of the present invention;
FIG. 8 is a liquid chromatogram of a compound used for preparing a positive resist according to example 4 of the present invention;
FIG. 9 is a gas chromatogram of the compound obtained in step 1 of example 5 of the present invention;
fig. 10 is a liquid chromatogram of a compound for preparing a positive resist of example 5 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the embodiments and features of the embodiments of the present invention may be combined with each other without conflict.
Example 1 preparation of example 1
Step 1: 20mmol of 3, 5-difluorobromobenzene and anhydrous tetrahydrofuran are added in N 2 Adding into a low-temperature reaction kettle under protection, mixing, reducing the temperature of the system to-10 ℃ by using the reaction kettle, continuously stirring, and adding N 2 Under the protection of 22mmol (1.1M, 20ml) of n-butyllithium is slowly dropped into the reaction kettle, the temperature of the reaction kettle is continuously reduced to-78 ℃, the reaction kettle is stirred for 0.5h, the purity of the compound obtained by the reaction in the step 1 is 93.81 percent,the gas chromatogram is shown in FIG. 1.
Step 2: adding 11mmol of thionyl chloride in N 2 Dropping into a low-temperature reaction kettle under protection, keeping the temperature at-20 ℃, and continuously reacting for 2 hours; after the raw materials are completely reacted, the nitrogen protection is closed, a feeding port is opened, and a proper amount of saturated ammonium chloride aqueous solution is added to quench the reaction.
Extracting the mixed solution obtained after the reaction to obtain an organic phase, controlling the temperature below 55 ℃, and concentrating the organic phase under reduced pressure until no fraction is obtained; adding methanol into the concentrated and dried system, cooling the system to 5 to-5 ℃, and crystallizing for 2 hours; the system is filtered, and a filter cake is dried to obtain 5,5' -sulfinylbis (1, 3-difluorobenzene), the liquid phase purity of the crude target compound reaches 97.77%, the molar yield reaches 67.5% (calculated by 3, 5-difluorobromobenzene), and a liquid chromatogram is shown in figure 2.
Example 2 preparation of example 2
Step 1: 20mmol of 3, 5-difluorobromobenzene and anhydrous tetrahydrofuran in N 2 Mixing in a low-temperature reaction kettle under protection, reducing the temperature of the system to-10 ℃ by using the reaction kettle, continuously stirring, and then adding N 2 Slowly adding 18mmol (1M, 18ml) of n-butyllithium dropwise under protection, continuously cooling the low-temperature reaction tank to-78 ℃, stirring for 0.5h, wherein the purity of the compound obtained by the reaction in the step 1 is 90.26%, and a gas chromatogram is shown in figure 3.
Step 2: 16mmol of thionyl chloride in N 2 Dropwise adding the mixture into a low-temperature reaction kettle under the protection of gas, keeping the temperature at-20 ℃, and continuously reacting for 2 hours; and (3) when the raw materials are completely reacted, closing the nitrogen protection, opening a feeding port, and adding a proper amount of saturated ammonium chloride aqueous solution to quench the reaction.
Extracting the quenched reaction solution to obtain an organic phase, controlling the temperature below 55 ℃, and concentrating the organic phase under reduced pressure until no fraction is obtained; adding methanol into the concentrated and dried system, cooling the system to 5 to-5 ℃, and crystallizing for 2 hours; the system is filtered, and a filter cake is dried to obtain 5,5' -sulfinylbis (1, 3-difluorobenzene), the liquid phase purity of the crude target compound reaches 93.23%, the molar yield reaches 56.4% (calculated by 3, 5-difluorobromobenzene), and a liquid chromatogram is shown in figure 4.
Example 3 preparation of examples 3-7
Examples 3-5 the same equipment as in example 1 was used for the preparation of the same raw material parts and preparation, except that the lithiation temperature and lithiation time in step 1 and the reaction temperature and time in step 2 were used in example 1, and the specific conditions were as shown in table 1 below; examples 3-5, gas chromatograms of the compound obtained in step 1 are shown in FIGS. 5, 7 and 9, and the purity is 92.36%, 80.81% and 76.36%, respectively; examples 3-5 the final reaction was completed and the final product liquid chromatogram was obtained as shown in FIGS. 6, 8 and 10.
Examples 6-7 differ from example 1 in the number of parts of starting materials used in their preparation, the equipment used and the reaction conditions were exactly the same, and the molar parts of starting materials used in their preparation are shown in table 2 below:
TABLE 1 examples 3-5 reaction conditions
TABLE 2 examples 6-7 molar fractions of formulated materials
Example 4 comparison of yield and purity of step 2 product
TABLE 3 yield, purity of step 2 product
Through gas chromatography detection of the mixture solution obtained after the reaction in the step 1, the peak forming time of the compound obtained in the step 1 is about 3.2min, and the data detected by the gas chromatography show that the compound after the reaction in the step 1 has the lowest purity of example 5, 76.36% and the highest purity of example 1, and the purity can reach 93.81%.
By combining the data in table 3, it can be seen that when the number of raw materials and the number of instruments used for preparation are the same, and the lithiation temperature, the lithiation time, the reaction temperature in step 2, and the reaction time in step 2 are all within the preferable range of the present invention, the product yield can reach more than 55%, the purity can reach more than 90%, and the highest purity can reach 97.5%; when the reaction conditions are the same and the parts of the prepared raw materials are different, the yield of the product is over 50 percent and the purity is over 90 percent when the parts of the n-butyl lithium, the 3, 5-difluorobromobenzene and the thionyl chloride are in the preferable range of the invention; it can be seen from the above experiments that the yield of the product can still reach more than 30% and the purity can reach more than 68% within the limit of the invention, even if the yield is not in the preferable range.
In conclusion, in the step 1 of preparing the compound of the positive resist, n-butyllithium is selected to participate in the reaction, compared with the traditional method of using Mg powder to generate the Grignard reagent, the solution obtained after the reaction in the step 1 has fewer by-products and high purity, and when subsequent experiments are carried out, the post-treatment and purification process of the final product is simpler, so that the purity and yield of the target product can be effectively improved.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. A compound for use in the preparation of a positive resist, characterized in that the compound has a structure represented by the following formula (I):
（I）。
2. a method for producing a compound for use in the production of a positive resist, having the structure of the compound according to claim 1, characterized in that: the reactants firstly have lithiation reaction with n-butyl lithium and then react with thionyl chloride, and the reaction formula is as follows:
step 1:
step 2:
3. the method for producing a compound for use in the production of a positive resist according to claim 2, characterized in that: the molar ratio of reactants n-butyllithium, 3, 5-difluorobromobenzene and thionyl chloride is as follows: 1 to 3:2:0.5 to 2.
4. A method for preparing a compound for use in the preparation of a positive resist according to claim 3, wherein: the molar ratio of reactants n-butyllithium, 3, 5-difluorobromobenzene and thionyl chloride is as follows: 2.1 to 2.3:2:1.1.
5. the method for producing a compound for use in the production of a positive resist according to any one of claims 2 to 4, characterized in that:
step 1: reacting 3, 5-difluorobromobenzene with anhydrous tetrahydrofuran in N 2 Adding into a low-temperature reaction kettle under protection, mixing, reducing the temperature of the system to-10 ℃ by using the reaction kettle, continuously stirring, and adding N 2 Slowly dripping n-butyllithium under protection, cooling the reaction tank to-80 to-30 ℃ at a low temperature, and stirring for 0.5 to 1h;
step 2: adding thionyl chloride into N 2 Dropping the mixture into a low-temperature reaction kettle under protection, keeping the temperature at minus 30 to 10 ℃, continuously reacting for 0.5 to 3 hours, closing nitrogen protection after the raw materials completely react, opening a feed inlet, and adding a proper amount of saturated ammonium chloride aqueous solution to quench the reaction.
6. The method for producing a compound for use in the production of a positive resist according to any one of claims 2 to 4, characterized in that:
step 1: reacting 3, 5-difluorobromobenzene with anhydrous tetrahydrofuran in N 2 Adding into a low-temperature reaction kettle under protection, mixing, reducing the temperature of the system to-10 ℃ by using the reaction kettle, continuously stirring, and adding N 2 Slowly dripping n-butyllithium under protection, continuously cooling the reaction tank at a low temperature to-78 to-70 ℃, and stirring for 0.5 to 1h;
step 2: adding thionyl chloride into N 2 Under protection, dropwise adding the mixture into a low-temperature reaction kettle, keeping the temperature at minus 30 to minus 20 ℃, continuously reacting for 1.5 to 2h, after the raw materials completely react, closing nitrogen protection, opening a feeding port, and adding a proper amount of saturated ammonium chloride aqueous solution to quench the reaction.
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| JP2009132687A (en) * | 2007-10-24 | 2009-06-18 | Semiconductor Energy Lab Co Ltd | Organometallic complex, and light-emitting element, light-emitting device and electronic device obtained by using the complex |
| CN102317294A (en) * | 2009-08-18 | 2012-01-11 | 株式会社Lg化学 | Novel compound, catalyst composition comprising same, and method for preparing a cyclic olefin polymer using same |
| US20160376233A1 (en) * | 2015-06-26 | 2016-12-29 | Tokyo Ohka Kogyo Co., Ltd. | Positive-type resist composition, method for forming resist pattern, photo-reactive quencher, and polymeric compound |
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| JP2022126072A (en) * | 2021-02-18 | 2022-08-30 | サンアプロ株式会社 | Production method of sulfonium salt |
-
2023
- 2023-01-29 CN CN202310043379.3A patent/CN115784953A/en active Pending
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| CN1820061A (en) * | 2003-07-07 | 2006-08-16 | 科文有机半导体有限公司 | Mixtures of organic emissive semiconductors and matrix materials, their use and electronic components comprising said materials |
| JP2009132687A (en) * | 2007-10-24 | 2009-06-18 | Semiconductor Energy Lab Co Ltd | Organometallic complex, and light-emitting element, light-emitting device and electronic device obtained by using the complex |
| CN102317294A (en) * | 2009-08-18 | 2012-01-11 | 株式会社Lg化学 | Novel compound, catalyst composition comprising same, and method for preparing a cyclic olefin polymer using same |
| CN107548385A (en) * | 2015-03-13 | 2018-01-05 | 陶氏环球技术有限责任公司 | Utilize the olefin oligomerization process of the catalyst comprising the chromium complex with the part containing phosphorus ring |
| US20160376233A1 (en) * | 2015-06-26 | 2016-12-29 | Tokyo Ohka Kogyo Co., Ltd. | Positive-type resist composition, method for forming resist pattern, photo-reactive quencher, and polymeric compound |
| JP2022126072A (en) * | 2021-02-18 | 2022-08-30 | サンアプロ株式会社 | Production method of sulfonium salt |
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| Title |
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| JORDAN BERREUR等, 《CHEMISTRY—A EUROPEAN JOURNAL》/ONE-STEP OXIDATIVE MONOFLUORINATION OF ELECTRON-DEFICIENT SULFOXIDES TO ACCESS HIGHLY LEWIS ACIDIC SULFUR(VI) CATIONS, vol. 28, no. 69, pages 298 - 299 * |
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