CN111913350A - Photosensitive polymer containing metal element, composition and application thereof - Google Patents
Photosensitive polymer containing metal element, composition and application thereof Download PDFInfo
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- CN111913350A CN111913350A CN201910388391.1A CN201910388391A CN111913350A CN 111913350 A CN111913350 A CN 111913350A CN 201910388391 A CN201910388391 A CN 201910388391A CN 111913350 A CN111913350 A CN 111913350A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 66
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 239000002184 metal Substances 0.000 title claims description 19
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 27
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003839 salts Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- -1 hydroxy, carboxy Chemical group 0.000 claims description 10
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 230000031700 light absorption Effects 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 238000001259 photo etching Methods 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- 230000008569 process Effects 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- 230000003321 amplification Effects 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 238000003199 nucleic acid amplification method Methods 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000001900 extreme ultraviolet lithography Methods 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention discloses a photosensitive polymer containing metal elements, a composition and application thereof, wherein the photosensitive polymer at least comprises the following structural units: 1) a structural unit capable of generating an acidic group; 2) a structural unit containing a metal ion; 3) structural units having an onium salt group, wherein the molar ratio of the structural units 1), 2) and 3) is (1-95): (4-99): (1-5). The photosensitive composition comprises the following components: A) the above-mentioned photosensitive polymer; B) and the solvent is one or a mixture of more of cyclohexanone, EL, PGMEA or PGME. The photosensitive polymer or the photosensitive composition can be applied to the preparation of a hardened film or a photoresist. Compared with the prior art, the thickness of the material is 38-43 mu C/cm2Under the exposure light intensity, the LWR of the photoetching pattern prepared by the photosensitive polymer is about 5, and the resolution can reach more than 80 nm.
Description
Technical Field
The invention relates to the technical field of photoetching, in particular to a photosensitive polymer containing metal elements, a composition and application thereof.
Background
Integrated Circuits (ICs) are one of the most critical technologies in the information age, and all devices related to electronic operations cannot be separated from chips from daily life to industrial production, and due to the chips with functions becoming powerful, personal computers can integrate more and more powerful functions, and mobile phones can only enter the 3G and 4G ages. Photolithography (photolithography) is a key technology that plays a significant role in the fabrication of integrated circuits. The functions of the chip can be continuously improved without departing from the development of photoetching technology materials and processes.
Photolithography is a process of transferring a predetermined pattern on a mask onto a substrate using a photochemical reaction. In the photolithography process, photoresist (photo-resist) is the most critical material. Incident light passes through the mask plate, so that patterns on the mask plate are projected onto photoresist coated on a substrate, photochemical reaction is excited, baking and development are carried out, and photoresist patterns are formed and then serve as blocking layers for selectively blocking subsequent etching or ion implantation and the like. In order to produce patterns with feature sizes of 0.2 μm and below, it is necessary to improve the sensitivity and resolution of the photoresist, and the most commonly used photoresist is a chemical-amplified resist (chemically-amplified resist) catalyzed by an acid. The main components of chemically amplified glues usually include polymeric resins (resin), Photo Acid Generators (PAG), solvents and additives (additives). The push toward the degree of integration of integrated circuits means that the photoresist is patterned to have finer dimensions. Wherein the polymer resin generally has an acid labile functional group (acid labile functional group) attached to the molecular chain, which renders the polymer insoluble in a developer. The photosensitive acid generator is a photosensitive compound which decomposes under irradiation with light to generate an acid (H)+) These acids can act as catalysts to break off acid labile groups on the polymer resin molecular chains and allow the generation of new acids during post-exposure bake (PEB). The polarity of the polymer resin changes with the shedding of the acid labile group, and the photoresist becomes soluble in a developer.
From the transition from contact exposure to projection exposure in the 80 s lithography, the resist technology shifted from broad-spectrum ultraviolet to the direction of G-line (436nm) → I-line (365nm) → KrF (248nm) → ArF (193nm) → EUV (13.5 nm). Extreme Ultraviolet (EUV) lithography refers to a lithography process in which exposure is performed using Extreme Ultraviolet light having a wavelength of 13.5 nm. The performance of a photoresist for EUV lithography is mainly represented by three parameters: resolution (R), Line Width Roughness (LWR) and Sensitivity (S) of the pattern. According to a resolution calculation formula: where R is k × NA/λ (where R represents resolution, k represents a process constant, NA represents the amount of light transmitted, and λ represents wavelength), shorter wavelengths provide higher resolution. Higher imaging resolution means finer lithographic process dimensions, and also means higher performance, lower power consumption, and higher chip integration and lower cost can be achieved.
At present, in the EUV lithography process, the conventional chemical amplification glue system is still widely used, but the chemical amplification glue system often encounters some obstacles which are difficult to avoid, for example, because the light source used by the exposure system of the EUV lithography is relatively weak compared with G-line, I-line, 248nm, 193nm, etc., the conventional chemical amplification glue system may have low sensitivity to the EUV, and in addition, the chemical amplification glue system has limitations of insufficient resolution, rough image edge, etc. The conventional chemical amplification glue system has low absorption to EUV, so that when the system is used for EUV exposure, a Photon-Shot-Noise (PSN) phenomenon is obvious particularly when the used light intensity is low, and the linewidth roughness LWR in the exposure performance of the photoresist is damaged. When conventional chemical amplification colloids are improved in response to EUV lithography, an "RLS trade-off" often occurs, i.e., improving a single one of resolution R, line width roughness LWR, and sensitivity S results in two other performance penalties.
In view of the foregoing, EUV photoresist materials that can simultaneously address all of the above limitations have not yet been developed, and development of EUV photoresists is in progress, particularly photoresists that can simultaneously improve resolution, line width roughness and sensitivity.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: a photosensitive polymer containing a metal element, which can reduce the occurrence of a photon noise dispersion phenomenon during exposure, a composition and applications thereof are provided.
In order to solve the technical problems, the invention adopts the technical scheme that: a photosensitive polymer containing a metal element, which comprises at least the following structural units:
1) a structural unit capable of generating an acidic group;
2) a structural unit containing a metal ion;
3) a structural unit having an onium salt group.
Preferably, the molar ratio of the structural units 1), 2) and 3) is (1-95): (4-99): (1-5).
Further, the structural unit 1) includes a structural unit capable of hydrolyzing under acidic conditions to generate an acidic group; preferably, the acidic groups comprise carboxyl or other acidic groups; preferably, the structural unit capable of hydrolyzing under acidic conditions to generate an acidic group contains an ester group, an ether group and/or an epoxy group; more preferably, the structural unit 1) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (1A), (1B) and (1C), Ra1, Ra2, Ra3, Ra1 ', Ra2 ', Ra3 ', Ra1 ", Ra 2", Ra3 "and Ra 4" represent substituents;
wherein, Ra1, Ra1 ', Ra 1' are selected from the following groups: non-, fully-or partially-halogenated C1-C20 linear alkyl groups, fully-or partially-halogenated C1-C10 branched alkyl groups, substituted or unsubstituted C6-C20 cyclic alkyl groups, substituted or unsubstituted C1-C20 linear alkyl groups containing 1-9 Si atoms, substituted or unsubstituted C1-C20 branched alkyl groups containing 1-9 Si atoms, and substituted or unsubstituted C3-C20 heterocycloalkyl groups containing 1-9 Si atoms;
ra2, Ra 2' and Ra4 "are selected from the group consisting of: substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cyclic alkyl, substituted or unsubstituted C3-C30 cyclic alkoxy, substituted or unsubstituted C1-C20 straight chain alkyl containing 1-9 Si atoms, substituted or unsubstituted C1-C20 branched alkyl containing 1-9 Si atoms, substituted or unsubstituted C3-C20 heterocycloalkyl containing 1-9 Si atoms;
ra 2' is selected from epoxy groups of C3-C10;
ra3, Ra 3', Ra3 "is hydrogen or methyl;
wherein, one or more hydrogen atoms of the substituent refers to a group substituted by one or more substituents selected from the group consisting of: oxo (═ O), halogen (preferably fluorine), hydroxy, carboxy, C1-C6 straight or branched alkyl unsubstituted or substituted with hydroxy or halogen, C6-C16 aryl unsubstituted or substituted with hydroxy or halogen.
Preferably, the metal ion-containing structural unit includes a structural unit containing a metal carboxylate structure; more preferably, the structural unit 2) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (2A), (2B), (2C) and (2D), Rb1、Rb2、Rb1’、Rb2’、Rb3’、Rb1”、Rb2”、Rb3”、Rb4”、Rb1”’、Rb2”’、Rb3”’、Rb4"' and Rb5"' represents a substituent;
wherein, Rb is1、Rb1’、Rb1And Rb1"' is selected from one or more of the following groups: fully or partially halogenated C1-C10 linear alkyl groups, fully or partially halogenated C1-C10 branched alkyl groups, substituted or unsubstituted C3-C30 cyclic alkyl groups;
Rb2、Rb2’、Rb2and Rb2"' is hydrogen or methyl;
Rb3’、Rb3”、Rb4”、Rb3”’、Rb4"' and Rb5"' is selected from one or more of the following groups: substituted or unsubstituted C1-C12 straight or branched alkyl or substituted or unsubstituted C6-C20 aryl;
wherein, one or more hydrogen atoms of the substituent refers to a group substituted by one or more substituents selected from the group consisting of: oxo (═ O), halogen (preferably fluorine), hydroxy, carboxy, C1-C6 straight or branched alkyl unsubstituted or substituted with hydroxy or halogen, C6-C10 aryl unsubstituted or substituted with hydroxy or halogen;
m represents a metal element selected from one or more of the following groups: lithium, sodium, magnesium, potassium, rubidium, iron, cobalt, nickel, copper, zinc, indium, tin, antimony, cesium, hafnium, zirconium.
Further, the structural unit 3) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (3A), (3B), (3C) and (3D), A-One or more selected from the group consisting of: sulfonate and nitrate radical; rd1、Rd2、Rd3、Rd4、Rd5、Rd6、Rd1’、Rd2’、Rd3’、Rd4’、Rd5’、Rd6’、Rd1”、Rd2”、Rd3”、Rd4”、Rd5”、Rd1”’、Rd2”’、Rd3"' and Rd4"' represents a substituent;
wherein, Rd1、Rd1’、Rd1And Rd1"' is selected from one or more of the following groups: fully or partially halogenated C1-C10 linear alkyl groups, fully or partially halogenated C1-C10 branched alkyl groups, substituted or unsubstituted C3-C30 cyclic alkyl groups, and substituted or unsubstituted C6-C20 aryl groups;
Rd2、Rd2’、Rd2and Rd2"' is hydrogen or methyl;
Rd3、Rd4、Rd5、Rd6、Rd3’、Rd4’、Rd5’、Rd6’、Rd3”、Rd4”、Rd5”、Rd3"' and Rd4"' is selected from one or more of the following groups: substituted or unsubstituted C1-C12 straight or branched alkyl, substituted or unsubstituted C6-C20 aryl;
wherein said substitution means that one or more hydrogen atoms of the group are substituted by one or more substituents selected from the group consisting of: halogen (preferably fluorine), hydroxy, carboxy, linear or branched C1-C6 alkyl unsubstituted or substituted by hydroxy or halogen, C6-C20 aryl unsubstituted or substituted by hydroxy or halogen.
Further, the photosensitive polymer may further include 4) a structural unit having a cyclic group; preferably, in the photosensitive polymer, the mole ratio of the structural unit 4) is 0 to 5%.
Further, the cyclic groups in the structural unit 4) include one or more of the following groups: adamantyl, aryl, alpha-pinenyl; preferably, the structural unit 4) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (4A), (4B) and (4C), Rc1、Rc1' and Rc1"one or more selected from the following group: a non-substituted or unsubstituted C1-C10 linear alkyl group, a substituted or unsubstituted C1-C10 branched alkyl group, a substituted or unsubstituted C3-C30 cyclic alkyl group, wherein said substitution means that one or more hydrogen atoms of the group are substituted with one or more substituents selected from the group consisting of: halogen (preferably fluorine), hydroxy, carboxy;
Rc2、Rc2' and Rc2"represents a substituent selected from one or more of the following groups: hydrogen, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl; wherein said substitution means that one or more hydrogen atoms of the group are substituted by one or more substituents selected from the group consisting ofAnd (3) substitution: halogen (preferably fluorine), hydroxyl, carboxyl.
Further, the photosensitive polymer satisfies one or more of the following properties:
i) the polydispersity PDI is less than or equal to 1.70;
ii) the molecular weight is 1500-180000;
iii) the glass transition temperature Tg is 65-230 ℃;
iv) light absorption in the wavelength range of less than 15nm is weak and increases with increasing molar proportion of the structural units 2) present.
The invention also comprises a photosensitive composition containing the metal element, which comprises the following components: A) a photosensitive polymer having the above structure; B) a solvent, wherein the solvent is one or more of cyclohexanone, Ethyl Lactate (EL), Propylene Glycol Methyl Ether Acetate (PGMEA), or Propylene Glycol Methyl Ether (PGME).
Further, in the photosensitive composition, the mass concentration of the component A) is 1 to 15 wt%.
The invention also comprises the application of the photosensitive polymer or the photosensitive composition in the preparation of a hardened film or a photoresist.
The invention also comprises a preparation method of the hardened film, which comprises the following steps:
s1, dissolving the photosensitive polymer in a solvent and coating the solution on a substrate;
s2, carrying out primary baking on the coated photosensitive polymer to remove the solvent;
s3, exposing the photosensitive polymer after removing the solvent;
s4, carrying out secondary baking on the exposed photosensitive polymer;
s5, developing the photosensitive polymer after the secondary baking by using a developing solution to obtain a hardened film;
wherein, the coating is performed by spin coating, the substrate is a silicon plate, the substrate is coated with hexamethyldisilazane before the photosensitive resin is coated, the first baking is performed at 80-90 ℃ for 100-120s, the exposure is performed by using an EUV exposure system, the second baking is performed at 100-120 ℃ for 60-90s, the developing solution is an alkaline aqueous developing solution, and the developing solution is preferably a tetramethylammonium hydroxide aqueous solution.
Further, the development operation is preferably for a time period of 60 s.
Further, the preparation method also comprises the step of rinsing the hardened film prepared by the operation.
The invention also provides a photoresist which is prepared from the photosensitive polymer or the photosensitive composition by the preparation method.
The invention has the beneficial effects that: the invention improves the photoresist to obtain the line width roughness of the pattern without influencing other performances, and reduces the occurrence of photon noise dispersion in the exposure process by adding the metal-containing component with strong absorption effect on EUV into the photoresist system, thereby improving the line width roughness of the pattern obtained by the photoresist. The photosensitive polymer of the invention is applied to the preparation of photoresist or hardened film at 38-43 mu C/cm2Under the exposure light intensity, the LWR of the photoetching pattern prepared by the photosensitive polymer is about 5, and the resolution can reach more than 80 nm.
Detailed Description
In order to explain the technical content, the objects and the effects of the present invention in detail, the following description will be given with reference to the embodiments.
The most key concept of the invention is as follows: according to the invention, the metal-containing component with a strong absorption effect on EUV is added into the photoresist system, so that the occurrence of photon noise dispersion in the exposure process is reduced, and the line width roughness of the pattern obtained by the photoresist is improved.
The first embodiment of the invention is as follows: a method for synthesizing a photosensitive polymer comprises the following steps: dissolving 18g of monomer M1, 7.5g of monomer M2, 12g of monomer M3 and 1.2g of monomer M4 by using 80mL of ethyl lactate, transferring the mixture into a reaction bottle, increasing the temperature of a mixed liquid system to 80 ℃, adding 0.18g of dibenzoyl peroxide (BPO), uniformly mixing, increasing the temperature of the reaction system to 100 ℃, continuing to react for 6 hours, adding 5mL of ethanol to stop the reaction, precipitating the mixed liquid after the reaction is stopped in the ethanol, and heating and drying the obtained solid in an oven at 100 ℃ for 8 hours to obtain white powdery polymer P133.5 g.
Wherein the structural formulas of M1, M2, M3 and M4 are as follows:
the number average molecular weight of the polymer P1 measured by Gel Permeation Chromatography (GPC) was 2450, and the molecular weight distribution (PDI) was 1.46, indicating that the polymer prepared by the scheme of the present invention has good polymerization controllability.
The polymer P1 is used for preparing a photosensitive composition I, and the specific preparation process is as follows: 25g of the polymer P1 described in example 1 was taken, and the polymer was dissolved in Ethyl Lactate (EL) until the polymer concentration became about 5% by mass, and filtered through a polytetrafluoroethylene filter having a pore size of 0.2 μm to obtain a photosensitive resin composition I.
The polymer I is used in photoetching, and the specific process is as follows: hexamethyldisilazane (HDMS) was spin-coated on a 12-inch silicon plate, followed by spin-coating the photosensitive resin composition I on the hexamethyldisilazane film, and baking at 90 ℃/120s to obtain a photosensitive composition film layer having a thickness of 75 to 80 nm. After obtaining the photosensitive composition film layer, Exposure was performed in an L/S pattern at an Exposure intensity of 38. mu.C/cm using an EUV Exposure apparatus (Micro Exposure Tool, Exitech, UK, NA 0.3, X-dipole)2。
After the exposure, post-exposure baking (PEB) is performed on a hot stage at 100 ℃/60s, the exposed photoresist layer is developed for 60s using an aqueous alkaline developer (2.38 wt% tetramethylammonium hydroxide (TMAH)) solution, and then rinsed with ultrapure water to obtain a photoresist pattern.
The obtained pattern was measured by CD-SEM to have an image size line width of 80nm and an image Line Width Roughness (LWR) LWR of 4.5nm, which was less than 10%.
The second embodiment of the invention is as follows: a method for synthesizing a photosensitive polymer comprises the following steps: dissolving 40g of monomer M5, 1.06g of monomer M6 and 0.49g of monomer M7 by using a mixed solution of 80mL of ethyl lactate and 20mL of propylene glycol methyl ether, transferring the dissolved solution into a reaction bottle, increasing the temperature of the mixed solution system to 85 ℃, adding 0.22g of dibenzoyl peroxide (BPO), uniformly mixing, increasing the temperature of the reaction system to 100 ℃, continuing to react for 6h, adding 6mL of ethanol to terminate the reaction, precipitating the mixed solution after the reaction is terminated in the ethanol, and heating and drying the obtained solid in an oven at 100 ℃ for 8h to obtain white powdery polymer P235.8g.
The structural formulas of M5, M6 and M7 are as follows:
the number average molecular weight of polymer P1 was 17700 and the molecular weight distribution (PDI) was 1.62 as determined by Gel Permeation Chromatography (GPC).
The polymer P2 is used for preparing a photosensitive composition II, and the specific preparation process is as follows: 25g of the polymer P2 described in example 1 was taken, and the polymer was dissolved in Ethyl Lactate (EL) until the polymer concentration became about 5% by mass, and filtered through a polytetrafluoroethylene filter having a bore diameter of 0.2. mu.m, to obtain a photosensitive resin composition II.
The polymer II is used in photoetching, and the specific process is as follows: hexamethyldisilazane (HDMS) was spin-coated on a 12-inch silicon plate, followed by spin-coating the photosensitive resin composition II on the hexamethyldisilazane film, and baking at 90 ℃/120s to obtain a photosensitive composition film layer having a thickness of 75 to 80 nm.
After obtaining a photosensitive composition film layer, Exposure was performed in an L/S pattern at an Exposure intensity of 40. mu.C/cm using an EUV Exposure apparatus (Micro Exposure Tool, Exitech, UK, NA 0.3, X-dipole)2。
After the exposure, post-exposure baking (PEB) was performed on a hot stage at 100 ℃/60s, and the exposed photoresist layer was developed for 60s with an alkaline aqueous developer (2.38 wt% Tetramethylammonium hydroxide aqueous solution, TMAH aqueous solution), and then rinsed with ultrapure water to obtain a photoresist pattern.
The resulting pattern was measured using CD-SEM, including image size and image Line Width Roughness (LWR). The test result shows that the obtained image has a line width range of 75-85nm, an LWR of 3.8-5.0nm and less than 10%.
In addition, the inspection data of the photo-etching pattern prepared by dissolving the polymer P1 or P2 in different organic solvents are shown in the following table 1, wherein the parameters in the photo-etching process are selected as in example 1 or 2 (the parameters of the polymer P1 are selected as in example 1, and the parameters of the polymer P2 are selected as in example 2):
TABLE 1 inspection data of lithography patterns prepared by dissolving polymers P1 or P2 in different organic solvents
Note: pbw in Table 1 above represents parts by weight, part by weight; the polymer (pbw) column indicates the number in parentheses as parts by weight of the compound, and likewise the organic solvent (pbw) column indicates the number in parentheses as parts by weight of the compound.
As can be seen from the above Table 1, the concentration is 38-43 μ C/cm2Under the exposure light intensity, the LWR of the photoetching pattern prepared by the photosensitive polymer is about 5, and the resolution can reach more than 80nm, so that the photosensitive polymer can be used for preparing the photoresist which can simultaneously improve the resolution, the line width roughness and the sensitivity.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent modifications made by the present invention in the specification or directly or indirectly applied to the related technical field are included in the scope of the present invention.
Claims (10)
1. A photosensitive polymer containing a metal element, characterized in that: the photosensitive polymer at least comprises the following structural units:
1) a structural unit capable of generating an acidic group;
2) a structural unit containing a metal ion;
3) a structural unit having an onium salt group.
2. The photosensitive polymer containing a metal element according to claim 1, wherein: the molar ratio of the structural units 1), 2) and 3) is (1-95): (4-99): (1-5).
3. The photosensitive polymer containing a metal element according to claim 1, wherein: the structural unit 1) comprises a structural unit which can be hydrolyzed under acidic conditions to generate an acidic group; preferably, the structural unit capable of hydrolyzing under acidic conditions to generate an acidic group contains an ester group, an ether group and/or an epoxy group; more preferably, the structural unit 1) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (1A), (1B) and (1C), Ra1, Ra2, Ra3, Ra1 ', Ra2 ', Ra3 ', Ra1 ", Ra 2", Ra3 "and Ra 4" represent substituents;
wherein, Ra1, Ra1 ', Ra 1' are selected from the following groups: non-, fully-or partially-halogenated C1-C20 linear alkyl groups, fully-or partially-halogenated C1-C10 branched alkyl groups, substituted or unsubstituted C6-C20 cyclic alkyl groups, substituted or unsubstituted C1-C20 linear alkyl groups containing 1-9 Si atoms, substituted or unsubstituted C1-C20 branched alkyl groups containing 1-9 Si atoms, and substituted or unsubstituted C3-C20 heterocycloalkyl groups containing 1-9 Si atoms;
ra2, Ra 2' and Ra4 "are selected from the group consisting of: substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cyclic alkyl, substituted or unsubstituted C3-C30 cyclic alkoxy, substituted or unsubstituted C1-C20 straight chain alkyl containing 1-9 Si atoms, substituted or unsubstituted C1-C20 branched alkyl containing 1-9 Si atoms, substituted or unsubstituted C3-C20 heterocycloalkyl containing 1-9 Si atoms;
ra 2' is selected from epoxy groups of C3-C10;
ra3, Ra 3', Ra3 "is hydrogen or methyl;
wherein, one or more hydrogen atoms of the substituent refers to a group substituted by one or more substituents selected from the group consisting of: oxo (═ O), halogen (preferably fluorine), hydroxy, carboxy, C1-C6 straight or branched alkyl unsubstituted or substituted with hydroxy or halogen, C6-C16 aryl unsubstituted or substituted with hydroxy or halogen.
4. The photosensitive polymer containing a metal element according to claim 1, wherein: the structural unit 2) comprises a structural unit containing a metal carboxylate structure; preferably, the structural unit 2) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (2A), (2B), (2C) and (2D), Rb1、Rb2、Rb1’、Rb2’、Rb3’、Rb1”、Rb2”、Rb3”、Rb4”、Rb1”’、Rb2”’、Rb3”’、Rb4"' and Rb5"' represents a substituent;
wherein, Rb is1、Rb1’、Rb1And Rb1"' is selected from one or more of the following groups: fully or partially halogenated C1-C10 straight-chain alkyl groups, fully or partially halogenated C1-C10 branched alkyl groups, substituted or notSubstituted C3-C30 cyclic alkyl;
Rb2、Rb2’、Rb2and Rb2"' is hydrogen or methyl;
Rb3’、Rb3”、Rb4”、Rb3”’、Rb4"' and Rb5"' is selected from one or more of the following groups: substituted or unsubstituted C1-C12 straight or branched alkyl or substituted or unsubstituted C6-C20 aryl;
wherein, one or more hydrogen atoms of the substituent refers to a group substituted by one or more substituents selected from the group consisting of: oxo (═ O), halogen (preferably fluorine), hydroxy, carboxy, C1-C6 straight or branched alkyl unsubstituted or substituted with hydroxy or halogen, C6-C10 aryl unsubstituted or substituted with hydroxy or halogen;
m represents a metal element selected from one or more of the following groups: lithium, sodium, magnesium, potassium, rubidium, iron, cobalt, nickel, copper, zinc, indium, tin, antimony, cesium, hafnium, zirconium.
5. The photosensitive polymer containing a metal element according to claim 1, wherein: the structural unit 3) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (3A), (3B), (3C) and (3D), A-One or more selected from the group consisting of: sulfonate and nitrate radical; rd1、Rd2、Rd3、Rd4、Rd5、Rd6、Rd1’、Rd2’、Rd3’、Rd4’、Rd5’、Rd6’、Rd1”、Rd2”、Rd3”、Rd4”、Rd5”、Rd1”’、Rd2”’、Rd3"' and Rd4"' represents a substituent;
wherein, Rd1、Rd1’、Rd1And Rd1"' is selected from one or more of the following groups: fully or partially halogenated C1-C10 linear alkyl groups, fully or partially halogenated C1-C10 branched alkyl groups, substituted or unsubstituted C3-C30 cyclic alkyl groups, and substituted or unsubstituted C6-C20 aryl groups;
Rd2、Rd2’、Rd2and Rd2"' is hydrogen or methyl;
Rd3、Rd4、Rd5、Rd6、Rd3’、Rd4’、Rd5’、Rd6’、Rd3”、Rd4”、Rd5”、Rd3"' and Rd4"' is selected from one or more of the following groups: substituted or unsubstituted C1-C12 straight or branched alkyl, substituted or unsubstituted C6-C20 aryl;
wherein said substitution means that one or more hydrogen atoms of the group are substituted by one or more substituents selected from the group consisting of: halogen (preferably fluorine), hydroxy, carboxy, linear or branched C1-C6 alkyl unsubstituted or substituted by hydroxy or halogen, C6-C20 aryl unsubstituted or substituted by hydroxy or halogen.
6. The photosensitive polymer containing a metal element according to claim 1, wherein: the photosensitive polymer further comprises 4) a structural unit having a cyclic group; preferably, in the photosensitive polymer, the mole ratio of the structural unit 4) is 0-5%; preferably, the cyclic groups in said structural unit 4) comprise one or more of the following groups: adamantyl, aryl, alpha-pinenyl; preferably, the structural unit 4) has one or more structures selected from the group consisting of structures represented by the following general formulae:
in the general formulae (4A), (4B) and (4C), Rc1、Rc1' and Rc1' selectionOne or more from the group of: a non-substituted or unsubstituted C1-C10 linear alkyl group, a substituted or unsubstituted C1-C10 branched alkyl group, a substituted or unsubstituted C3-C30 cyclic alkyl group, wherein said substitution means that one or more hydrogen atoms of the group are substituted with one or more substituents selected from the group consisting of: halogen (preferably fluorine), hydroxy, carboxy;
Rc2、Rc2' and Rc2"represents a substituent selected from one or more of the following groups: hydrogen, halogen, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl; wherein said substitution means that one or more hydrogen atoms of the group are substituted with one or more substituents selected from the group consisting of: halogen (preferably fluorine), hydroxyl, carboxyl.
7. The photosensitive polymer containing a metal element according to claim 1, wherein: the photosensitive polymer satisfies one or more of the following properties:
i) the polydispersity PDI is less than or equal to 1.70;
ii) the molecular weight is 1500-180000;
iii) the glass transition temperature Tg is 65-230 ℃;
iv) light absorption in the wavelength range of less than 15nm is weak and increases with increasing molar proportion of the structural units 2) present.
8. A photosensitive composition containing a metal element, characterized in that: comprises the following components: A) a photosensitive polymer as set forth in any one of claims 1 to 7; B) and the solvent is one or a mixture of more of cyclohexanone, EL, PGMEA or PGME.
9. Use of a photosensitive polymer according to any one of claims 1 to 7 in the preparation of a cured film or a photoresist.
10. A method for preparing a hardened film, characterized in that: the method comprises the following steps:
s1, dissolving the photosensitive polymer of any one of claims 1 to 7 in a solvent, and coating the solution on a substrate;
s2, carrying out primary baking on the coated photosensitive polymer to remove the solvent;
s3, exposing the photosensitive polymer after removing the solvent;
s4, carrying out secondary baking on the exposed photosensitive polymer;
s5, developing the photosensitive polymer after the secondary baking by using a developing solution to obtain a hardened film;
the coating is carried out by spin coating, the substrate is a silicon plate, the substrate is coated with hexamethyldisilazane before the photosensitive resin is coated, the primary baking is carried out at 80-90 ℃ for 100-120s, the exposure is carried out by adopting an EUV (extreme ultraviolet) exposure system, the secondary baking is carried out at 100-120 ℃ for 60-90s, the developing solution is an alkaline aqueous developing solution, and the developing solution is preferably a tetramethylammonium hydroxide aqueous solution.
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| US20120065291A1 (en) * | 2009-04-15 | 2012-03-15 | Jsr Corporation | Radiation-sensitive resin composition, polymer, and compound |
| JP2013083966A (en) * | 2011-09-30 | 2013-05-09 | Fujifilm Corp | Actinic ray-sensitive or radiation-sensitive resin composition, and actinic ray-sensitive or radiation-sensitive film and pattern forming method using the same |
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