CN113804867B - Method for testing photoresist resin component - Google Patents
Method for testing photoresist resin component Download PDFInfo
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- CN113804867B CN113804867B CN202111138814.8A CN202111138814A CN113804867B CN 113804867 B CN113804867 B CN 113804867B CN 202111138814 A CN202111138814 A CN 202111138814A CN 113804867 B CN113804867 B CN 113804867B
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- photoresist resin
- acid
- protecting group
- molecular weight
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 122
- 239000011347 resin Substances 0.000 title claims abstract description 119
- 229920005989 resin Polymers 0.000 title claims abstract description 119
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000012360 testing method Methods 0.000 title abstract description 14
- 125000006239 protecting group Chemical group 0.000 claims abstract description 54
- 238000001212 derivatisation Methods 0.000 claims abstract description 53
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 26
- 150000002500 ions Chemical class 0.000 claims description 25
- 238000010586 diagram Methods 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000012445 acidic reagent Substances 0.000 claims description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 9
- 238000004949 mass spectrometry Methods 0.000 claims description 7
- FUGYGGDSWSUORM-UHFFFAOYSA-N para-hydroxystyrene Natural products OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012159 carrier gas Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 238000004817 gas chromatography Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 4
- 239000012953 triphenylsulfonium Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 230000005540 biological transmission Effects 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- VPHBYBUYWBZLEX-UHFFFAOYSA-N 1,2-dipropylbenzene Chemical compound CCCC1=CC=CC=C1CCC VPHBYBUYWBZLEX-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- ICMVGKQFVMTRLB-UHFFFAOYSA-N 4-phenylbutanenitrile Chemical group N#CCCCC1=CC=CC=C1 ICMVGKQFVMTRLB-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 2
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- JLUOZBQVJZLHPN-UHFFFAOYSA-N tert-butyl(phenyl)iodanium Chemical class CC(C)(C)[I+]C1=CC=CC=C1 JLUOZBQVJZLHPN-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000010998 test method Methods 0.000 claims 1
- 238000004458 analytical method Methods 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 238000004364 calculation method Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- 230000010355 oscillation Effects 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- 230000009471 action Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003534 oscillatory effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/44—Resins; Plastics; Rubber; Leather
- G01N33/442—Resins; Plastics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Materials For Photolithography (AREA)
Abstract
The application provides a method for testing photoresist resin components, which comprises the steps of obtaining the structure and molecular weight of a protecting group R in photoresist resin, obtaining the weight average molecular weight of the photoresist resin before and after derivatization treatment by adopting gel permeation chromatography, and obtaining the protecting rate of the protecting group R in the photoresist resin by calculation according to the formula of the application, thereby obtaining the components of each monomer in the photoresist resin; the method can accurately obtain the components of each monomer in the photoresist resin, provides a theoretical basis for determining the performance of the photoresist resin, and has the advantages of simplicity, convenience, high sensitivity, high analysis speed, high accuracy, small error and the like.
Description
Technical Field
The application relates to the technical field of photoresist resin, in particular to a method for testing photoresist resin components.
Background
Photoresist resin is a key material for manufacturing advanced integrated circuits at present, is a framework of photoresist, and has a decisive influence on the performance of the photoresist. The photoresist resin comprises a polymer taking p-hydroxystyrene as a main structure, and the general structural formula is shown as follows:
the type and proportion of the protective group R containing the functional group in the photoresist resin are closely related to the resin performance, so that the accurate knowledge of the structure and the protective rate of the protective group R in the photoresist resin and the acquisition of the structure and the components of each monomer in the photoresist resin are particularly important.
Disclosure of Invention
The application aims to provide a method for testing photoresist resin components, so as to accurately obtain the protection rate of a protecting group R in photoresist resin, and further obtain the structure and the components of each monomer in the photoresist resin.
The application provides a method for testing a photoresist resin component, which comprises the following steps:
s1, taking photoresist resin to be tested, and adding a solvent for dissolution to obtain a first solution to be tested;
the structural formula of the photoresist resin is shown as a formula (I):
wherein R is a protecting group, a and b are mole percentages of two structures in the photoresist resin, a+b=100 mol%;
s2, taking the first solution to be tested, and adding an acidic reagent to carry out a derivatization reaction to obtain a second solution to be tested;
s3, obtaining the structure and molecular weight M of the protecting group R R ；
S4, detecting a first solution to be detected and a second solution to be detected by adopting Gel Permeation Chromatography (GPC), and respectively obtaining chromatograms before and after the photoresist resin to be detected is subjected to derivatization treatment to obtain the weight average molecular weight Mw before the photoresist resin is subjected to derivatization treatment and the weight average molecular weight Mw after the photoresist resin is subjected to derivatization treatment;
according to the formulaCalculating the protection rate A of the protecting group R, and according to the formulaCalculating to obtain values of a and b, thereby determining the photoresist resin component;
wherein M is 0 Is the molecular weight of the para-hydroxystyrene monomer.
According to the method for testing the photoresist resin component, the molecular weight of the protecting group R in the photoresist resin is obtained, the weight average molecular weight of the photoresist resin before and after derivatization treatment is obtained by adopting gel permeation chromatography, and the protecting rate of the protecting group R in the photoresist resin is obtained by calculation according to the formula of the application, so that the components of all monomers in the photoresist resin are obtained; the method can accurately obtain the components of each monomer in the photoresist resin, provides a theoretical basis for determining the performance of the photoresist resin, and has the advantages of simplicity, convenience, high sensitivity, high analysis speed, high accuracy, small error and the like.
Drawings
In order to more clearly illustrate the embodiments of the application or the technical solutions in the prior art, the drawings used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the application, and other embodiments may be obtained according to these drawings to those skilled in the art.
FIG. 1 is a gel permeation chromatogram of the first test solution in example 1.
FIG. 2 is a gel permeation chromatogram of the second test solution in example 1.
Fig. 3 is a total ion flow diagram of the photoresist resin to be measured before and after derivatization in example 2, wherein fig. a is a total ion flow diagram of the photoresist resin to be measured before derivatization, and fig. B is a total ion flow diagram of the photoresist resin to be measured after derivatization.
FIG. 4 is a mass spectrum of the chromatographic peak with a retention time of 6.88min in FIG. 3B.
FIG. 5 is a gel permeation chromatogram of the first test solution of example 2.
FIG. 6 is a gel permeation chromatogram of the second test solution of example 2.
Detailed Description
The following description of the embodiments of the present application will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present application, but not all embodiments. Based on the embodiments of the present application, all other embodiments obtained by the person skilled in the art based on the present application are included in the scope of protection of the present application.
The application provides a method for testing a photoresist resin component, which comprises the following steps:
s1, taking photoresist resin to be tested, and adding a solvent for dissolution to obtain a first solution to be tested;
the structural formula of the photoresist resin is shown as a formula (I):
wherein R is a protecting group, a and b are mole percentages of two structures in the photoresist resin, a+b=100 mol%;
s2, taking the first solution to be tested, and adding an acidic reagent to carry out a derivatization reaction to obtain a second solution to be tested;
s3, obtaining the structure and molecular weight M of the protecting group R R ；
S4, detecting a first solution to be detected and a second solution to be detected by adopting gel permeation chromatography, and respectively obtaining chromatograms before and after the derivatization treatment of the photoresist resin to be detected, and obtaining the weight average molecular weight Mw before the derivatization treatment of the photoresist resin and the weight average molecular weight Mw after the derivatization treatment of the photoresist resin;
according to the formulaCalculating the protection rate A of the protecting group R, and according to the formulaCalculating to obtain values of a and b, thereby determining the photoresist resin component;
wherein M is 0 Is the molecular weight of the para-hydroxystyrene monomer.
In the application, after the photoresist resin is dissolved in the dissolving step S1, the solid content of the photoresist resin in the first solution to be tested is 6-40%; preferably, the solid content of the photoresist resin in the first solution to be tested is 15-25%, more preferably, the solid content of the photoresist resin in the first solution to be tested is 20%.
In the present application, step S3, if the structure of the protecting group R in the photoresist resin is known, the molecular weight M of the protecting group R can be directly obtained R The method comprises the steps of carrying out a first treatment on the surface of the If the structure of the protecting group R in the photoresist resin is unknown, the structure and the molecular weight M of the protecting group R can be obtained by using a detection method such as gas chromatography-mass spectrometry (GC-MS) R 。
In the application, the photoresist resin is a p-hydroxystyrene polymer with higher boiling point and higher difficulty in detecting the structure, and the dissolved first to-be-detected solution containing the photoresist resin is added with an acidic reagent for derivatization reaction to decompose the photoresist resin, so that the main part of the photoresist resin polymer is the photoresist resinThe chain is unchanged, the protective group R drops to be changed into R ', the boiling point of R ' is lower, the difficulty of structural detection is reduced, the structural formula of R ' can be determined by detecting a second solution to be detected after the derivatization reaction, the structure of the protective group R is determined, and the molecular weight M of the protective group R is obtained R The derivatization reaction has the following reaction formula:
in the present application, in step S4, the route for obtaining the weight average molecular weight before and after the photoresist resin derivatization treatment is not limited, so long as the purpose of the present application can be achieved, for example, the chromatogram before the photoresist resin derivatization treatment and the chromatogram after the photoresist resin derivatization treatment can be analyzed by astm a software, GPC software or OMNISEC software, so as to obtain the weight average molecular weight Mw before the photoresist resin derivatization treatment and the weight average molecular weight Mw after the photoresist resin derivatization treatment.
The protection rate A of the protecting group R is the mole percentage of the protecting group R in the photoresist resin, namelyThe protection ratio a=b×100% of the protecting group R based on a+b=1.
According to the method for testing the photoresist resin component, the molecular weight of the protecting group R in the photoresist resin is obtained, the weight average molecular weight of the photoresist resin before and after derivatization treatment is obtained by adopting gel permeation chromatography, the protecting rate A of the protecting group R in the photoresist resin is obtained through calculation according to the formula of the application, and the values of a and b are further obtained, so that the component of the photoresist resin is determined; the method can accurately obtain the components of each monomer in the photoresist resin, and has the advantages of simplicity, convenience, high sensitivity, high analysis speed, high accuracy and the like.
In the present application, the protecting group R is a functional group-containing protecting group, and in some embodiments of the present application, the protecting group R may be selected from any of C1-C10 alkyl, C3-C10 cycloalkyl, C4-C10 bicycloalkyl, C3-C10 heterocycloalkyl, C2-C10 ester, C1-C10 alkyl containing at least one N, S or O, C1-C10 alkyl substituted with at least one halogen, C3-C10 cycloalkyl containing at least one N, S or O, C3-C10 cycloalkyl substituted with at least one halogen.
In some embodiments of the present application, step S3 includes:
detecting a first solution to be detected and a second solution to be detected by adopting gas chromatography-mass spectrometry to respectively obtain total ion flow diagrams before and after the derivatization treatment of the photoresist resin to be detected, comparing the total ion flow diagrams, determining a plurality of chromatographic peaks in the total ion flow diagrams after the derivatization treatment of the photoresist resin, analyzing the structural formula of the chromatographic peaks, thereby determining the structural formula of the protecting group R and obtaining the molecular weight M of the protecting group R R 。
According to the method for analyzing the structural formula, a person skilled in the art can obtain the structural formula by adopting a conventional structural formula analyzing means according to the obtained chromatographic peak, and the analyzing means is not limited as long as the purpose of the method can be achieved.
In some embodiments of the application, the gas chromatography-mass spectrometry is used in combination with gas chromatography conditions comprising:
the chromatographic column filler is unsubstituted or partially substituted dimethyl polysiloxane or dimethyl arylene siloxane copolymer; sample inlet temperature: 250-350 ℃, carrier gas: helium (He); carrier gas flow rate: 1.0-2.0mL/min; sample injection volume: 0.1-1.0. Mu.L; column temperature procedure: heating to 260-360 deg.C at the initial temperature of 30-60deg.C at the speed of 5-20deg.C/min, and maintaining for 5-30min;
transmission line temperature between gas chromatography and mass spectrometry: 250-320 ℃;
the mass spectrometry conditions included: the electron bombards the ion source (EI ion source), the ionization voltage is 60-80eV, the ion source temperature is 200-300 ℃, the ion is scanned completely, and the scanning range m/z is 50-650.
In some embodiments of the application, the partially substituted dimethylpolysiloxane is diphenyl or phenyl, the mole percent of which is 5-50%, or the mole percent of which is 5-20% cyanopropylbenzene or dipropylbenzene; the partially substituted dimethyl arylene siloxane copolymer has a substituent of diphenyl, and the molar percentage of the substituent is 5-50%.
The inventors found in the study that if the structure of the protecting group R in the photoresist resin is unknown, the structural formula and the molecular weight M of the protecting group R can be obtained by adopting the gas chromatography-mass spectrometry combination method R . The application adopts a gas chromatography-mass spectrometry method, and the first solution to be detected and the second solution to be detected are detected by reasonably selecting chromatographic conditions and mass spectrometry conditions to respectively obtain total ion flow diagrams before and after the derivatization treatment of the photoresist resin to be detected, and the total ion flow diagrams after the derivatization treatment of the photoresist resin are compared to determine that a plurality of chromatographic peaks in the total ion flow diagrams after the derivatization treatment of the photoresist resin are chromatographic peaks of R 'after the derivatization reaction, analyze the chromatographic peaks and determine the structural formula of R', thereby determining the structural formula of a protecting group R and obtaining the molecular weight M of the protecting group R R 。
The application adopts gas chromatography-mass spectrometry to carry out qualitative determination on the protecting group R in the photoresist resin to be detected, and is judged by accurately finding out protecting group molecules which fall off after the photoresist resin to be detected is subjected to derivatization reaction, and the protecting group R is not influenced by complex matrixes, and the sensitivity and the accuracy of the gas chromatography-mass spectrometry are high, and the result is accurate and reliable.
In some embodiments of the present application, in step S4, the chromatographic conditions of the gel permeation chromatography include:
chromatographic column: a crosslinked polystyrene-divinylbenzene gel chromatographic column; mobile phase: tetrahydrofuran; flow rate: 0.5-2.0mL/min; column temperature: 35-40 ℃; molecular weight detection range: 0-30000. Preferably, the flow rate is 1.0mL/min.
The application adopts a gel permeation chromatography method, and can accurately obtain the weight average molecular weight Mw before the photoresist resin derivatization treatment and the weight average molecular weight Mw after the photoresist resin derivatization treatment by reasonably selecting chromatographic conditions.
The application adopts gel permeation chromatography to quantify the protecting group R in the photoresist resin to be tested, and the protecting rate of the protecting group R is calculated by a formula by combining the qualitative result of the protecting group R of the photoresist resin to be tested and the molecular weight change of the main body of the photoresist resin before and after the derivatization reaction, so as to further determine the components of the photoresist resin.
In some embodiments of the present application, the kind of the solvent is not particularly limited in step S1 as long as the object of the present application can be achieved, and for example, the solvent may be at least one selected from the group consisting of an alcohol solvent, a ketone solvent, an ether solvent, an ester solvent, an aromatic hydrocarbon solvent and a halogenated hydrocarbon solvent. Specifically, the alcohol solvent comprises at least one of methanol, ethanol, propanol, butanol, ethylene glycol and isopropanol; the ketone solvent comprises at least one of acetone, methyl butanone and methyl isobutyl ketone; the ether solvent comprises at least one of diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane, ethylene glycol dimethyl ether, cyclopentyl methyl ether, isopropyl ether, anisole and methyl tertiary butyl ether; the ester solvent comprises at least one of methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and ethyl lactate; the aromatic solvent comprises at least one of toluene and xylene; the halogenated hydrocarbon solvent comprises at least one of dichloromethane, carbon tetrachloride, 1, 2-dichloroethane and chloroform.
The amount of the solvent used in the present application is not particularly limited as long as the object of the present application can be achieved, and the ratio of the mass of the resist resin to be measured to the volume of the solvent is, for example, 1g (1-10) mL.
In the present application, the acidic reagent is a reagent containing or capable of generating H + In some embodiments of the present application, the present application is not particularly limited in the kind of the acidic reagent in step S2 as long as the object of the present application can be achieved, for example, the acidic reagent may be selected from at least one of an organic acid, an inorganic acid, and a photoacid generator. Specifically, the describedThe organic acid comprises at least one of formic acid, glacial acetic acid, oxalic acid, maleic acid, citric acid, tartaric acid and p-toluenesulfonic acid; the inorganic acid comprises at least one of hydrochloric acid, sulfuric acid and phosphoric acid; the photoacid generator includes at least one of tert-butylphenyl iodonium salt perfluorooctane sulfonic acid, triphenylsulfonium perfluorobutane sulfonic acid, and triphenylsulfonium trifluorosulfonic acid. Wherein, when the acidic reagent is a photoacid generator, the conditions of the derivatization reaction include light irradiation, and the conditions of the light irradiation are not limited as long as the object of the present application can be achieved.
The amount of the acidic reagent used in the present application is not particularly limited as long as the object of the present application can be achieved, and the ratio of the mass of the photoresist resin in the first solution to be tested to the mass of the acidic reagent is, for example, 1g (0.01-0.1 g); preferably, the ratio of the mass of the photoresist resin in the first test solution to the mass of the acidic reagent is 1g (0.02-0.05 g).
In some embodiments of the present application, in step S1, the dissolution is an oscillatory dissolution, and the present application is not particularly limited as long as the object of the present application can be achieved, for example, the oscillatory dissolution has an oscillation time of 10 to 120min and an oscillation frequency of 50 to 500 rpm. In the application, the step S1 adopts an oscillation dissolution mode, so that the dissolution speed of the photoresist resin to be tested can be improved, and the dissolution efficiency of the photoresist resin can be improved.
In some embodiments of the application, in step S2, the derivatization reaction conditions comprise: the oscillating reaction, the oscillating time, the oscillating frequency and the reaction temperature of the oscillating reaction are not particularly limited as long as the purpose of the application can be achieved, for example, the oscillating time of the oscillating reaction is 10-1200min, the oscillating frequency is 50-500 rpm, and the reaction temperature is 30-100 ℃; preferably, the oscillation time is 240-480min, the oscillation frequency is 150-300 rpm, and the reaction temperature is 50-80 ℃. In the application, the derivatization reaction in the step S2 adopts the oscillating reaction mode and the oscillating condition, so that the speed of the derivatization reaction can be increased, and the efficiency of the derivatization reaction can be increased.
Instrument: gas chromatograph-mass spectrometer: thermo Scientific, ITQ1100; gel permeation chromatograph: waters,1515 separation unit, 2414 differential detector; thermostatic water bath rotary oscillator: SHZ-BS, a Hengzhou Chuan laboratory instruments Co., ltd.
The experimental materials and methods used in the examples below are conventional materials and methods unless otherwise specified.
Example 1
Materials: the photoresist resin to be tested (purchased from japan shot chemistry) has the following structural formula:
product information provided by merchants: the protecting group R is tert-butoxycarbonyl, the protecting group R has a protecting ratio of 29.7%, theoretical value a=0.703, b=0.297.
S1, weighing 15g of the photoresist resin to be tested in a 100mL ultra-clean bottle, adding 15g of Propylene Glycol Monomethyl Ether Acetate (PGMEA), placing in a constant-temperature water bath rotary oscillator, and oscillating and dissolving for 20min at room temperature, wherein the oscillating frequency is 200 r/min, so as to obtain a first solution to be tested;
s2, taking 10g of a first solution to be tested in a 60mL ultra-clean bottle, adding 0.1g of p-toluenesulfonic acid, placing in a constant-temperature water bath rotary oscillator for derivatization reaction, oscillating for 360min, oscillating at 200 r/min and water bath temperature of 70 ℃ to obtain a second solution to be tested;
s3, obtaining the molecular weight M of the protecting group R R ＝101；
S4, detecting the first solution to be detected by adopting gel permeation chromatography to obtain a chromatogram shown in the figure 1; detecting the second solution to be detected by adopting gel permeation chromatography to obtain a chromatogram shown in figure 2; chromatographic conditions for gel permeation chromatography include:
chromatographic column: waters Styragel HR 0.5.5, waters Styragel HR 1, waters Styragel HR 3; mobile phase: tetrahydrofuran; flow rate: 1.0mL/min; column temperature: 38 ℃; molecular weight detection range: 0-30000;
analyzing fig. 1 and 2 by GPC software to obtain a weight average molecular weight Mw before derivatization of the photoresist resin=10586 and a molecular weight distribution index (PDI) =1.45, and obtaining a weight average molecular weight Mw after derivatization of the photoresist resin=8499 and a pdi=1.45;
according to the formulaWherein M is 0 For the molecular weight of the p-hydroxystyrene monomer, the protection ratio of the protecting group R is calculated +.>According to the formula->And a+b=1, calculated as b=0.295, a=0.705; />
Example 2
Materials: the photoresist resin to be tested (from Shanghai Tongchen electronic materials Co., ltd.) has an unknown structural formula.
S1, weighing 15g of the photoresist resin to be tested in a 100mL ultra-clean bottle, adding 15g of Ethyl Lactate (EL), placing in a constant-temperature water bath rotary oscillator, oscillating and dissolving for 20min at room temperature, and obtaining a first solution to be tested at an oscillating frequency of 200 r/min;
s2, taking 10g of a first solution to be tested in a 60mL ultra-clean bottle, adding 0.1g of glacial acetic acid, placing in a constant-temperature water bath rotary oscillator for derivatization reaction, oscillating for 300min, oscillating at 200 r/min and at 70 ℃ in a water bath to obtain a second solution to be tested;
s3, detecting a first solution to be detected and a second solution to be detected by adopting gas chromatography-mass spectrometry, wherein the chromatographic conditions of the gas chromatography comprise: chromatographic column: TR-5MS column (30 m. Times.0.25 mm. Times.0.25 μm); sample inlet temperature: 300 ℃; carrier gas: he; carrier gas flow rate: 1.0mL/min; sample injection volume: 1 μl; column temperature procedure: heating to 310 ℃ at the initial temperature of 40 ℃ at the speed of 10 ℃/min, and keeping for 10min;
transmission line temperature between gas chromatography and mass spectrometry: 280 ℃;
the mass spectrometry conditions included: EI ion source, ionization voltage 70 deg.C, ion source temperature 250 deg.C, ion full scanning, scanning range m/z 50-650;
respectively obtaining total ion flow diagrams before and after the derivatization treatment of the photoresist resin to be detected, as shown in fig. 3, wherein the diagram A of fig. 3 is a total ion flow diagram before the derivatization of the photoresist resin to be detected, the diagram B is a total ion flow diagram after the derivatization of the photoresist resin to be detected, chromatographic peaks with retention time of 5.5-6.0min in the diagram A and the diagram B are chromatographic peaks of ethyl lactate, the diagram A and the diagram B of fig. 3 are compared, more chromatographic peaks with retention time of 6.88min are determined in the diagram B, a mass spectrogram of the chromatographic peaks is shown in fig. 4, and a compound of the chromatographic peaks is determined to be 2, 3-dihydropyran through spectral library retrieval and spectrogram analysis, and the structural formula of the photoresist resin to be detected is determined as follows:
obtaining the molecular weight M of the protecting group R R ＝85；
S4, detecting the first solution to be detected by adopting gel permeation chromatography to obtain a chromatogram shown in FIG. 5; detecting the second solution to be detected by gel permeation chromatography to obtain a chromatogram shown in FIG. 6; chromatographic conditions for gel permeation chromatography include:
chromatographic column: waters Styragel HR 0.5.5, waters Styragel HR 1, waters Styragel HR 3; mobile phase: tetrahydrofuran; flow rate: 1.0mL/min; column temperature: 38 ℃; molecular weight detection range: 0-30000;
analysis is carried out on fig. 5 and 6 by adopting GPC software to obtain weight average molecular weights Mw before derivatization treatment of the photoresist resin=15417 and pdi=1.49, and weight average molecular weights Mw after derivatization treatment of the photoresist resin= 11736 and pdi=1.50;
according to the formulaWherein M is 0 For the molecular weight of the p-hydroxystyrene monomer, the protection ratio of the protecting group R is calculated +.>According to the formula->And a+b=1, and b=0.448 and a=0.552 are calculated, and the structural formula of the photoresist resin is determined as follows:
examples 3 to 4
The photoresist resin (from Shanghai Toosendan electronic materials Co., ltd.) of a known structure was used separately, and the same method for testing the photoresist resin composition as in example 1 was used, and the variation of the relevant test parameters and the results of testing the photoresist resin composition are shown in Table 1.
TABLE 1
Through tests, the application can accurately obtain the components of each monomer in the photoresist resin, the maximum error value is 0.67%, and the error values are all less than 1%.
In summary, the method for testing the photoresist resin component provided by the application obtains the molecular weight of the protecting group R in the photoresist resin, obtains the weight average molecular weight of the photoresist resin before and after derivatization treatment by adopting gel permeation chromatography, and obtains the protecting rate of the protecting group R in the photoresist resin by calculation according to the formula of the application, thereby obtaining the components of each monomer in the photoresist resin; the method can accurately obtain the components of each monomer in the photoresist resin, provides a theoretical basis for determining the performance of the photoresist resin, and has the advantages of simplicity, convenience, high sensitivity, high analysis speed, high accuracy, small error and the like.
It is noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising one … …" does not exclude the presence of other like elements in a process, method, article, or apparatus that comprises the element.
In this specification, each embodiment is described in a related manner, and identical and similar parts of each embodiment are all referred to each other, and each embodiment mainly describes differences from other embodiments. In particular, for system embodiments, since they are substantially similar to method embodiments, the description is relatively simple, as relevant to see a section of the description of method embodiments.
The foregoing description is only of the preferred embodiments of the present application and is not intended to limit the scope of the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application are included in the protection scope of the present application.
Claims (9)
1. A method of testing a photoresist resin component comprising the steps of:
s1, taking photoresist resin to be tested, and adding a solvent for dissolution to obtain a first solution to be tested;
the structural formula of the photoresist resin is shown as a formula (I):
wherein R is a protecting group, a and b are mole percentages of two structures in the photoresist resin, a+b=100 mol%;
s2, taking the first solution to be tested, and adding an acidic reagent to carry out a derivatization reaction to obtain a second solution to be tested;
s3, obtaining the structure and molecular weight M of the protecting group R R ；
S4, detecting a first solution to be detected and a second solution to be detected by adopting gel permeation chromatography, and respectively obtaining chromatograms before and after the derivatization treatment of the photoresist resin to be detected, and obtaining the weight average molecular weight Mw before the derivatization treatment of the photoresist resin and the weight average molecular weight Mw after the derivatization treatment of the photoresist resin;
according to the formulaCalculating the protection rate A of the protecting group R, and according to the formulaCalculating to obtain values of a and b, thereby determining the photoresist resin component;
wherein M is 0 Is the molecular weight of the para-hydroxystyrene monomer;
the protecting group R is selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C4-C10 bicycloalkyl, C2-C10 ester, C1-C10 alkyl containing at least one N or O, C1-C10 alkyl substituted by at least one halogen, C3-C10 cycloalkyl containing at least one N or O, C3-C10 cycloalkyl substituted by at least one halogen.
2. The method of claim 1, wherein step S3 comprises:
detecting the first solution to be detected and the second solution to be detected by adopting gas chromatography-mass spectrometry to respectively obtain the light to be detectedComparing total ion flow diagrams before and after photoresist resin derivatization treatment with total ion flow diagrams, determining chromatographic peaks which are more than those in the total ion flow diagrams after photoresist resin derivatization treatment, analyzing the structural formula of the chromatographic peaks, thereby determining the structural formula of the protecting group R and obtaining the molecular weight M of the protecting group R R 。
3. The method of claim 2, wherein the gas chromatography-mass spectrometry is used, and gas chromatography conditions comprise:
the chromatographic column filler is unsubstituted or partially substituted dimethyl polysiloxane or dimethyl arylene siloxane copolymer; sample inlet temperature: 250-350 ℃, carrier gas: helium gas; carrier gas flow rate: 1.0-2.0mL/min; sample injection volume: 0.1-1.0. Mu.L; column temperature procedure: heating to 260-360 deg.C at the initial temperature of 30-60deg.C at the speed of 5-20deg.C/min, and maintaining for 5-30min;
transmission line temperature between gas chromatography and mass spectrometry: 250-320 ℃;
the mass spectrometry conditions included: the electron bombards the ion source, the ionization voltage is 60-80eV, the ion source temperature is 200-300 ℃, the ion is scanned completely, and the scanning range m/z is 50-650.
4. A method according to claim 3 wherein the partially substituted dimethylpolysiloxane is diphenyl or phenyl in a mole percentage of 5-50%, or is cyanopropylbenzene or dipropylbenzene in a mole percentage of 5-20%; the partially substituted dimethyl arylene siloxane copolymer has a substituent of diphenyl, and the molar percentage of the substituent is 5-50%.
5. The method according to claim 1, wherein in step S4, the chromatographic conditions of the gel permeation chromatography include:
chromatographic column: a crosslinked polystyrene-divinylbenzene gel chromatographic column; mobile phase: tetrahydrofuran; flow rate: 0.5-2.0mL/min; column temperature: 35-40 ℃; molecular weight detection range: 0-30000.
6. The method according to any one of claims 1 to 5, wherein in step S1, the solvent is selected from at least one of an alcohol solvent, a ketone solvent, an ether solvent, an ester solvent, an aromatic hydrocarbon solvent, and a halogenated hydrocarbon solvent.
7. The method of claim 6, wherein the alcoholic solvent comprises at least one of methanol, ethanol, propanol, butanol, ethylene glycol, and isopropanol; the ketone solvent comprises at least one of acetone, methyl butanone and methyl isobutyl ketone; the ether solvent comprises at least one of diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, dioxane, ethylene glycol dimethyl ether, cyclopentyl methyl ether, isopropyl ether, anisole and methyl tertiary butyl ether; the ester solvent comprises at least one of methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, propylene glycol monomethyl ether acetate and ethyl lactate; the aromatic solvent comprises at least one of toluene and xylene; the halogenated hydrocarbon solvent comprises at least one of dichloromethane, carbon tetrachloride, 1, 2-dichloroethane and chloroform.
8. The method according to any one of claims 1-5, wherein in step S2, the acidic reagent is selected from at least one of an organic acid, an inorganic acid, and a photoacid generator.
9. The method of claim 8, wherein the organic acid comprises at least one of formic acid, glacial acetic acid, oxalic acid, maleic acid, citric acid, tartaric acid, and p-toluene sulfonic acid; the inorganic acid comprises at least one of hydrochloric acid, sulfuric acid and phosphoric acid;
the photoacid generator includes at least one of tert-butylphenyl iodonium salt perfluorooctane sulfonic acid, triphenylsulfonium perfluorobutane sulfonic acid, and triphenylsulfonium trifluorosulfonic acid.
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| 电子束光刻胶成膜树脂研究进展;李虎;刘敬成;徐文佳;穆启道;郑祥飞;纪昌玮;刘仁;刘晓亚;;信息记录材料(第01期);全文 * |
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