CN117148668A - EUV/EB photoresist, preparation method and application thereof - Google Patents
EUV/EB photoresist, preparation method and application thereof Download PDFInfo
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- CN117148668A CN117148668A CN202210574006.4A CN202210574006A CN117148668A CN 117148668 A CN117148668 A CN 117148668A CN 202210574006 A CN202210574006 A CN 202210574006A CN 117148668 A CN117148668 A CN 117148668A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 55
- 239000011347 resin Substances 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 5
- -1 3, 6-dioxepinyl Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002950 monocyclic 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
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 238000001900 extreme ultraviolet lithography Methods 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 230000006196 deacetylation Effects 0.000 claims 1
- 238000003381 deacetylation reaction Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 235000012431 wafers Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000445 field-emission scanning electron microscopy Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 1
- 238000001015 X-ray lithography Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000609 electron-beam lithography Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 238000001291 vacuum drying Methods 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
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
Abstract
The invention provides an EUV/EB photoresist, a preparation method and application thereof. The photoresist composition of the present invention comprises the following components: the total mass fraction of the resin, the photoacid generator, the quencher and the solvent is 100%. The photoresist of the invention reduces LER and LWR and improves resolution and sensitivity.
Description
Technical Field
The invention relates to EUV/EB photoresist, a preparation method and application thereof.
Background
The use of photoresists is necessary and common in semiconductor manufacturing processes. In recent years, the integration level of integrated circuits has become higher and higher, and it has been required to form ultra fine (ultra fine) patterns in the sub-micron or quarter micron region. To address this need, exposure wavelengths also tend to become shorter (e.g., from g-line to i-line, or further to KrF excimer laser). Currently, development using electron beam, X-ray or EUV lithography in addition to excimer laser is under investigation and development.
Photolithography using electron beam, X-ray, or EUV light is positioned as a next-generation (next-generation) or a next-generation (next-next-generation) patterning technique, and is required to be a high-sensitivity, high-resolution resist.
In general, high-sensitivity implementation is a very important task, but when high-sensitivity implementation is sought, resolution tends to be reduced and line edge roughness (Line edge roughness, LER) is deteriorated, so that photoresist technology that meets the technical requirements in these aspects at the same time is difficult. Edge roughness means the following: the edge at the interface between the resist pattern and the substrate irregularly undulates in a direction perpendicular to the line direction due to the characteristics of the resist, and when the pattern is viewed from above, the edge appears as an uneven appearance. This unevenness is transferred in an etching step using a resist as a mask, resulting in a reduction in yield.
The sensitivity, the resolution and the roughness have the relationship of mutual trade-off, so that the balance of the sensitivity, the resolution and the roughness is improved, the difficulty is high, and the technical problem to be solved in the industry is urgent.
Disclosure of Invention
The invention aims to overcome the defect that the resolution is reduced or the roughness is increased when the sensitivity of the photoresist is improved in the prior art, and further provides an EUV/EB photoresist, a preparation method and application thereof. The photoresist of the invention reduces LER and LWR and improves resolution and sensitivity.
The invention provides a photoresist composition, which comprises the following components: the total mass fraction of the resin, the photoacid generator, the quencher and the solvent is 100%; the mass fraction of each component is the mass fraction of the component in the photoresist composition;
wherein the resin comprises structural units of the following general formula (I) and general formula (II):
wherein R is 1 And R is 2 Each independently is a substituted or unsubstituted C 1 -C 4 Alkyl, hydrogen or halogen;
R 3 、R 4 and R is 5 Each independently is hydrogen, substituted or unsubstituted C 4 -C 20 Cycloalkyl, substituted or unsubstituted C 1 -C 4 Alkyl, substituted or unsubstituted C 6 -C 22 Aryl of (a);
alternatively, R 3 、R 4 And R is 5 Any two of which together with the carbon atoms to which they are attached form a substituted or unsubstituted C 4 -C 20 Cycloalkyl;
alternatively, R 3 、R 4 And R is 5 Together form a substituted or unsubstituted C 4 -C 20 Cycloalkyl;
the substituted or unsubstituted C 1 -C 4 Alkyl, substituted or unsubstituted C 6 -C 22 And the substituted or unsubstituted C 4 -C 20 The substituents (number of substituents, for example, 1, 2 or 3) in the cycloalkyl group are each independently selected from the following groups: halogen (e.g. F, cl, br or I, e.g. F), hydroxy and oxo (=o).
R 1 And R is 2 Preferably, the halogen is F, cl, br or I, such as F.
R 1 And R is 2 In said substituted or unsubstituted C 1 -C 4 C in alkyl 1 -C 4 The alkyl groups may each independently be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl.
R 1 And R is 2 In said substituted C 1 -C 4 The alkyl group may be trifluoromethyl or hydroxymethyl.
R 3 、R 4 And R is 5 In said substituted or unsubstituted C 1 -C 4 C in alkyl 1 -C 4 The alkyl groups may each independently be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl, ethyl or isopropyl.
R 3 、R 4 And R is 5 In said substituted or unsubstituted C 6 -C 22 C in aryl of (C) 6 -C 22 Each independently may be phenyl or naphthyl.
R 3 、R 4 And R is 5 Any two of which together with the carbon atoms to which they are attached form a substituted or unsubstituted C 4 -C 20 C in cycloalkyl 4 -C 20 Cycloalkyl groups each independently can be C 4 -C 10 Saturated monocycloalkyl, C 6 -C 8 Saturated bicycloalkyl or C 8 -C 11 Saturated tricycloalkyl radicals, e.g. C 4 -C 10 Saturated monocyclic alkyl or C 8 -C 11 Saturated tricycloalkyl;
wherein, C is as follows 4 -C 10 The saturated monocyclic alkyl group may be cyclobutyl, cyclopentyl, cyclohexyl or cyclooctyl. The C is 6 -C 8 The saturated bicycloalkyl group may be a norbornyl group. The C is 8 -C 11 The saturated tricycloalkyl group may be an adamantyl group.
R 3 、R 4 And R is 5 Together form a substituted or unsubstituted C 4 -C 20 Cycloalkyl can be C 8 -C 11 Saturated tricycloalkyl groups such as adamantyl.
In the general formula (II),is->
Preferably +.> More preferably +.>
In the resin, the structural unit of the general formula (I) is
In the resin, the structural unit of the general formula (II) is preferably one or more of the following structural units:
wherein R is 3 、R 4 And R is 5 Each independently is C 1 -C 4 An alkyl group.
The structural unit of the general formula (II) is preferably one or more of the following structural units:
more preferably +.> For example->
The resin preferably further comprises structural units of the following formula (III):
wherein R is 6 Is hydrogen or C 1 -C 4 An alkyl group;
R 7 and R is 8 Together with the carbon atoms to which they are attached form a substituted or unsubstituted 5-10 membered heterocycloalkyl; the hetero atoms in the substituted or unsubstituted 5-10 membered heterocycloalkyl are independently O and/or N, and the number is 1 or 2;
the substituents (the number of substituents is, for example, 1, 2 or 3) in the substituted or unsubstituted 5-10 membered heterocycloalkyl are each independently selected from the following groups: hydroxy, oxo (=o) or C 1 -C 4 An alkyl group.
R 6 In the above, the C 1 -C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl.
The R is 7 And R is 8 The 5-10 membered heterocycloalkyl groups in the 5-10 membered heterocycloalkyl groups which together with the carbon atoms to which they are attached form a substituted or unsubstituted 5-10 membered heterocycloalkyl group each independently can be a 5-or 6-membered heterocycloalkyl group, the heteroatom being O, the number being 1, for example furyl.
The structural unit of the formula (III) is preferably
In the photoresist composition, the weight average molecular weight of the resin is preferably 4000 to 18000, more preferably 4423 to 16136.
In the photoresist composition, the molecular weight distribution index PDI of the resin is preferably 1.1 to 2.2, more preferably 1.45 to 2.
In the photoresist composition, the resin is preferably obtained by polymerizing monomers including the following monomer 1 and monomer 2:
R 1 、R 2 、R 3 、R 4 and R is 5 Is as defined above.
The molar ratio of the monomer 1 to the monomer 2 is preferably (1-5): 1, e.g., 1:1.
The monomer 1 may be
The monomer 2 may be selected from one or more of the following monomers:
wherein R is 3 、R 4 And R is 5 Each independently is C 1 -C 4 An alkyl group.
The monomer 2 may be selected from One or more of the following; more preferably, said monomer 2 is selected from +.> One or more of the following; for example, the monomer 2 is selected from +.> One or more of the following.
The monomer may also comprise monomer 3:
R 6 、R 7 and R is 8 Is as defined above.
When the monomer further comprises a monomer 3, the molar ratio of the monomer 1, the monomer 2 and the monomer 3 is preferably (5-10): (1-5): (1-5), e.g., 5:3:2.
The monomers 3 are preferably
The resin is preferably prepared by a preparation method comprising the following steps:
(1) Polymerizing the monomer in a solvent in the presence of an initiator to obtain the resin precursor; the monomers are as described above;
(2) Deacetylating the resin precursor in a solvent in the presence of triethylamine to obtain the resin; the definition of the resin is as described above.
In the process for preparing the resin, the weight ratio of the solvent to the monomer 1 in the step (1) may be a weight ratio commonly used in such a reaction in the art, and is preferably (2-8): 1, for example, 3.2:1 or 6.4:1.
In the method for preparing the resin, in the step (1), the solvent may be a solvent commonly used in such a reaction in the art, and is preferably propylene glycol monomethyl ether.
In the method for preparing the resin, in the step (1), the molar ratio of the initiator to the monomer 1 may be a molar ratio commonly used in such a reaction in the art, and is preferably (7% -14%): 1, e.g. 7%:1 or 14%:1.
in the method for preparing the resin, in the step (1), the initiator may be an initiator commonly used in such a reaction in the art, preferably azobisisobutyronitrile.
In the method for preparing a resin, in the step (1), a post-treatment step of the resin precursor, such as cooling, crystallization and filtration, may be further included.
In the method for preparing the resin, in the step (2), the solvent may be a solvent commonly used in such a reaction in the art, and is preferably propylene glycol monomethyl ether or methanol.
In a preferred embodiment of the invention, the resin is preferably obtained by polymerization of monomers of the following group (a) or (b):
group (a): the molar ratio of the monomer 1 to the monomer 2 is 1:1, a step of;
group (b): the molar ratio of the monomer 1, the monomer 2 and the monomer 3 is 5:3:2;
in the preparation method, in the step (1), the molar ratio of the initiator to the monomer 1 is (7% -14%): 1, a step of;
in the preparation method, in the step (1), the weight ratio of the solvent to the monomer 1 is (2-8): 1.
In the photoresist composition, the mass fraction of the resin may be a mass fraction conventional in the art, preferably 8% to 20%, for example, 10% to 18%.
In the photoresist composition, the mass fraction of the photoacid generator may be a mass fraction conventional in the art, preferably 0.1% to 0.6%, for example 0.36% to 0.4%.
In the photoresist composition, the photoacid generator may be a photoacid generator conventional in the art, preferably triphenylthio-trifluoromethane sulfonate.
The mass fraction of the quencher in the photoresist composition may be a mass fraction conventional in the art, preferably 0.08% to 0.12%, for example 0.09% to 0.1%.
In the photoresist composition, the quencher may be a quencher conventional in the art, preferably an organic base such as one or more of triethylamine, tributylamine, trioctylamine and tris (3, 6-dioxepinyl) amine, and further such as triethylamine.
In the photoresist composition, the amount of the solvent is not particularly limited, and is used for supplementing the content of each component in the photoresist composition to 100%, i.e., supplementing the balance with the solvent.
In the photoresist composition, the solvent may be a solvent conventional in the art, preferably one or more of Propylene Glycol Methyl Ether Acetate (PGMEA), propylene Glycol Monomethyl Ether (PGME) and Methyl Ethyl Ketone (MEK), for example, propylene glycol methyl ether acetate.
The photoresist composition is preferably composed of the following components in parts by mass: the resin, the photoacid generator, the quencher, and the solvent; wherein the types and mass fractions of the resin, the photoacid generator, the quencher and the solvent are as described above.
The invention also provides a preparation method of the photoresist composition, which comprises the following steps: and mixing the components of the photoresist composition.
The manner and time of mixing may be conventional in the art, such as stirring for 3 days. The mixing may further comprise a filtering step. The filtration may be carried out in a manner conventional in the art, preferably by filtration through an ultra high molecular weight polyethylene filter. The pore diameter of the ultra-high molecular polyethylene filter membrane is preferably 0.1 mu m.
The invention also provides a method for forming patterns by using the extreme ultraviolet lithography technology, which comprises the following steps:
(I) Coating the photoresist composition on the surface of a substrate, and baking to obtain a photoresist layer;
(II) exposing, baking and developing the photoresist layer obtained in the step 1 to obtain a photoresist pattern.
In the step (I), the substrate may be a substrate conventional in the art, preferably a silicon wafer; more preferably an 8inch silicon wafer.
In the step (I), the coating method may be a conventional method in the art, preferably spin coating by a spin coater.
In the step (I), the thickness of the EUV photoresist layer may be a thickness conventional in the art, preferably 50nm.
In the step (1), the baking temperature may be a baking temperature conventional in the art, preferably 100 to 130 ℃, for example 120 ℃.
In step (I), the baking time is preferably 50 to 70 seconds, for example 60 seconds.
In said step (II), the baking temperature may be a baking temperature conventional in the art, preferably 100-130 ℃, for example 120 ℃.
In said step (II), the baking time is preferably 50 to 70 seconds, for example 60 seconds.
In the step (II), the development may be performed as usual in the art, and the developer typically used is an aqueous solution of tetramethylammonium hydroxide (TMAH), for example, an aqueous solution of 2.38% by mass TMAH.
In the invention, the 'quencher' is an alkaline compound, mainly an amine compound, and the compound is mainly used for controlling acid diffusion and improving resolution.
As used herein, "aryl" refers to a compound having a specified number of carbon atoms (e.g., C 6 ～C 10 ) A cyclic group consisting of only carbon atoms, which is a single ring or multiple rings, and at least one ring has aromaticity (in accordance with the shock rule). Aryl groups are linked to other fragments in the molecule through aromatic or non-aromatic rings. Aryl groups include, but are not limited to, phenyl, naphthyl, and the like.
As used herein, "cycloalkyl" refers to a compound having the indicated number of carbon atoms (e.g., C 5 ～C 10 ) Saturated monocyclic, bicyclic or tricyclic cyclic groups consisting of carbon atoms onlyA bolus. Cycloalkyl includes, but is not limited to, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present invention, "heterocycloalkyl" means a saturated monocyclic, bicyclic or tricyclic cyclic group consisting of only carbon atoms, having the specified number of ring atoms (e.g., 5 to 10 membered). The heterocycloalkyl group is attached to the remainder of the molecule via a carbon atom or heteroatom. Heterocycloalkyl groups include, but are not limited to:etc. On the basis of conforming to the common knowledge in the field, the above preferred conditions can be arbitrarily combined to obtain the preferred examples of the invention.
The reagents and materials used in the present invention are commercially available.
The invention has the positive progress effects that: the photoresist composition of the invention improves the resolution and reduces the roughness while improving the sensitivity.
Detailed Description
The invention is further illustrated by means of the following examples, which are not intended to limit the scope of the invention. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
Abbreviations used in the present invention explain the following table:
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Acetone-Acetone; EA-ethyl acetate; hexane-n-Hexane; MEK-methyl ethyl ketone; THF-tetrahydrofuran; 1, 4-dioxane-1, 4-dioxane; methanol-Methanol; PGMEA-propylene glycol methyl ether acetate; PGME-propylene glycol methyl ether; AIBN-azobisisobutyronitrile; DMAB (AIBME) -dimethyl azodiisobutyrate; TPS-TF: triphenylthio-trifluoromethane sulfonate, its junctionThe structure is as follows:
1. preparation example
The resin and photoresist were prepared by taking example 2 as an example, the procedure of examples 1 and 3-30 was the same as that of example 2, the amounts of the components used in step 1 of each example were as shown in Table 1, and the amounts not shown were the same as those of example 2.
The amounts of the components used in each example "photoresist preparation step" are shown in Table 3, and the amounts not shown are the same as those of example 2.
Example 2
The preparation method of the resin comprises the following steps:
step 1: 81.1g (0.5 mol) of monomer M1 and 91.1g (0.5 mol) of monomer M2 were added to 258g of PGME solution, respectively, and after mixing, 11.5g (0.07 mol) of AIBN was added and dissolved;
step 2: after the mixture solution is moved to a reaction kettle, the temperature is raised to 70 ℃ and the mixture solution reacts for 6 hours under the protection of nitrogen;
step 3: after the reaction is finished, cooling to normal temperature;
step 4: taking out the reaction product, adding 1000g of n-hexane to precipitate, standing and removing the supernatant;
step 5: 150g of PGME was dissolved in the solution, followed by addition of 150g of methanol, 60.7g (1.2 eq based on M1) of triethylamine, and 10.8g (1.2 eq based on M1) of water, and then transferred to the reaction vessel;
step 6: under the protection of nitrogen, heating the reaction kettle to the boiling point, and reacting for 8 hours under the reflux condition of the boiling point;
step 7: after the reaction is finished, cooling to normal temperature;
step 8: taking out the reaction product, and distilling under reduced pressure to remove triethylamine and water;
step 9: 150g of acetone was added to the product to dissolve it;
step 10: dissolving, adding water to precipitate, standing, and removing supernatant;
step 11: the product is filtered under reduced pressure and then is transferred into a vacuum drying oven to be dried for 24 hours under the condition of 50 ℃;
step 12: GPC analysis of the product gave a molecular weight mw=9696, pdi=1.51.
And (3) photoresist preparation:
step 1: taking 5g of the product resin;
step 2: 44g PGMEA was added and allowed to dissolve;
step 3: 0.2g of triphenylthio-trifluoromethane sulfonate (TPS-TF) and 0.05g of triethylamine are added;
step 4: placing on a rotary stirrer for stirring for 3 days at 24 ℃;
step 5: the dissolved photoresist was filtered with a 0.1um filter to obtain photoresist.
TABLE 1 corresponding components and amounts in step 1 of each example
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In the above table "/" indicates that no addition was made, GPC analysis was performed on the products of the respective resin production examples, and the test results are shown in Table 2 below.
TABLE 2 GPC analysis results
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TABLE 3 corresponding Components and amounts in the Photoresist preparation step
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2. Effect examples
1. EUV exposure and detection
Photoresist preparation and exposure
The photoresist composition obtained from each example was coated on an 8-inch wafer at 2500RPM, and heated at 80 ℃ for 60 seconds on a hot plate to obtain a photoresist film. The average film thickness was measured at 25 points by an optical film thickness measuring system F50 (Filmetrics) and 50nm.
Extreme ultraviolet exposure was performed on an upper sea light source interference reticle stage (BL 08U 1B) and then baked at 130℃for 60 seconds.
Finally, the resultant film was developed in a 2.38wt% aqueous solution of tetramethylammonium hydroxide (TMAH), thereby obtaining a pattern.
(1) Edge roughness (Line Edge Roughness, LER) LER
LER of the 50-nm LS pattern was measured under FE-SEM (Hitachi SU 9000).
(2) Linewidth roughness (Line Width Roughness, LWR) LWR
LWR of the 50-nm LS pattern was measured under CD-SEM (HITACHI, CD-SEM, CG 5000).
(3) Sensitivity of
An Eth value was used as a sensitivity index.
Stepped 25-point exposures (e.g., 0.5 mJ/cm) with different energies were performed on 8inch wafers 2 ,1mJ/cm 2 ,1.5mJ/cm 2 ) After post baking (PEB), development was performed, and the film thickness was measured and recorded as Eth just reaching 0nm.
(4) Resolution of
Under the conditions given the above sensitivity, the limit resolution (minimum limit width when separating and resolving lines and spaces) at the exposure dose (dose of electron beam irradiation) was taken as LS resolution (nanometers).
TABLE 4 EUV Exposure and test results
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2. EB exposure and detection
Photoresist preparation and exposure
The photoresist composition obtained from each example was coated on an 8-inch wafer at 2500RPM, and heated at 80 ℃ for 60 seconds on a hot plate to obtain a photoresist film. The average film thickness was measured at 25 points by an optical film thickness measuring system F50 (Filmetrics) and 50nm.
The photoresist was exposed to an electron beam using an EB writing system Elionix ELS-G100 (Elionix, acceleration voltage 100 KeV) and baked at 130 ℃ for 60 seconds.
Finally, the resultant film was developed in a 2.38wt% aqueous solution of tetramethylammonium hydroxide (TMAH), thereby obtaining a pattern.
(1)Eop
The optimal exposure (Eop) is defined as the exposure dose (μC/cm) that provides 1:1 resolution at the top and bottom of a 50-nm 1:1 line-and-space (LS) pattern 2 )。
(2)LER
LER of the 50-nm LS pattern was measured under FE-SEM (Hitachi SU 9000).
(3)LWR
LWR of the 50-nm LS pattern was measured under CD-SEM (HITACHI, CD-SEM, CG 5000).
(4) Resolution of
Under the condition of the above EOP, the limit resolution (minimum limit width when separating and resolving lines and spaces) at the exposure dose (dose of electron beam irradiation) is taken as LS resolution (nm).
TABLE 5 EB Exposure and detection results
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According to the above embodiments, the photoresist of the present invention improves resolution and sensitivity while reducing roughness.
Claims (11)
1. A photoresist composition comprising the following components: the total mass fraction of the resin, the photoacid generator, the quencher and the solvent is 100%; the mass fraction of each component is the mass fraction of the component in the photoresist composition;
wherein the resin comprises structural units of the following general formula (I) and general formula (II):
wherein R is 1 And R is 2 Each independently is a substituted or unsubstituted C 1 -C 4 Alkyl, hydrogen or halogen;
R 3 、R 4 and R is 5 Each independently is hydrogen, substituted or unsubstituted C 4 -C 20 Cycloalkyl, substituted or unsubstituted C 1 -C 4 Alkyl, substituted or unsubstituted C 6 -C 22 Aryl of (a);
alternatively, R 3 、R 4 And R is 5 Any two of which together with the carbon atoms to which they are attached form a substituted or unsubstituted C 4 -C 20 Cycloalkyl;
alternatively, R 3 、R 4 And R is 5 Together form a substituted or unsubstituted C 4 -C 20 Cycloalkyl;
the substituted or unsubstituted C 1 -C 4 Alkyl, said substitutionOr unsubstituted C 6 -C 22 And the substituted or unsubstituted C 4 -C 20 The substituents in cycloalkyl groups are each independently selected from the following groups: halogen, hydroxy and oxo.
2. The photoresist composition according to claim 1, which meets one or more of the following conditions:
(1) In the photoresist composition, the weight average molecular weight of the resin is 4000 to 18000, preferably 4423 to 16136;
(2) In the photoresist composition, the molecular weight distribution index PDI of the resin is 1.1-2.2, preferably 1.45-2;
(3) In the photoresist composition, the mass fraction of the resin is 8-20%, such as 10-18%;
(4) The mass fraction of the photoacid generator in the photoresist composition is 0.1-0.6%, such as 0.36-0.4%;
(5) In the photoresist composition, the photoacid generator is triphenylthio-trifluoromethane sulfonate;
(6) The mass fraction of the quencher in the photoresist composition is 0.08 to 0.12%, such as 0.09 to 0.1%;
(7) In the photoresist composition, the quencher is an organic base, preferably one or more of triethylamine, tributylamine, trioctylamine and tris (3, 6-dioxepinyl) amine, such as triethylamine;
(8) In the photoresist composition, the solvent is one or more of propylene glycol methyl ether acetate, propylene glycol monomethyl ether and methyl ethyl ketone, such as propylene glycol methyl ether acetate.
3. The photoresist composition according to claim 1, which meets one or more of the following conditions:
(1)R 1 and R is 2 Wherein said halogen is F, cl, br or I, such as F;
(2)R 1 and R is 2 In said substituted or unsubstituted C 1 -C 4 C in alkyl 1 -C 4 Alkyl is each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl;
(3)R 1 and R is 2 In said substituted C 1 -C 4 Alkyl is trifluoromethyl or hydroxymethyl;
(4)R 3 、R 4 and R is 5 In said substituted or unsubstituted C 1 -C 4 C in alkyl 1 -C 4 Alkyl is each independently methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl, ethyl or isopropyl;
(5)R 3 、R 4 and R is 5 In said substituted or unsubstituted C 6 -C 22 C in aryl of (C) 6 -C 22 Each independently phenyl or naphthyl;
(6)R 3 、R 4 and R is 5 Any two of which together with the carbon atoms to which they are attached form a substituted or unsubstituted C 4 -C 20 C in cycloalkyl 4 -C 20 Cycloalkyl groups are each independently C 4 -C 10 Saturated monocycloalkyl, C 6 -C 8 Saturated bicycloalkyl or C 8 -C 11 Saturated tricycloalkyl radicals, e.g. C 4 -C 10 Saturated monocyclic alkyl or C 8 -C 11 Saturated tricycloalkyl;
wherein, C is as follows 4 -C 10 Saturated monocyclic alkyl groups are preferably cyclobutyl, cyclopentyl, cyclohexyl or cyclooctyl; the C is 6 -C 8 Saturated bicycloalkyl is preferably norbornyl; the C is 8 -C 11 Saturated tricycloalkyl groups are preferably adamantyl;
(7)R 3 、R 4 and R is 5 Together form a substituted or unsubstituted C 4 -C 20 Cycloalkyl radicals are C 8 -C 11 Saturated tricycloalkyl groups such as adamantyl;
(8) The resin further comprises structural units of the following formula (III):
wherein R is 6 Is hydrogen or C 1 -C 4 An alkyl group;
R 7 and R is 8 Together with the carbon atoms to which they are attached form a substituted or unsubstituted 5-10 membered heterocycloalkyl; the hetero atoms in the substituted or unsubstituted 5-10 membered heterocycloalkyl are independently O and/or N, and the number is 1 or 2;
the substituents in the substituted or unsubstituted 5-10 membered heterocycloalkyl are each independently selected from the group consisting of: hydroxy, oxo or C 1 -C 4 An alkyl group;
structural units of the formula (III), R 6 In the above, the C 1 -C 4 Alkyl groups may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, for example methyl; the R is 7 And R is 8 The 5-10 membered heterocycloalkyl groups in the 5-10 membered heterocycloalkyl groups which together with the carbon atoms to which they are attached form a substituted or unsubstituted 5-10 membered heterocycloalkyl group each independently can be a 5-or 6-membered heterocycloalkyl group, the heteroatom being O, the number being 1, for example furyl.
4. A photoresist composition according to claim 3, wherein the resin satisfies one or more of the following conditions:
(1) In the resin, the structural unit of the general formula (I) is
(2) In the resin, the structural unit of the general formula (II) is one or more of the following structural units:
wherein R is 3 、R 4 And R is 5 Each independently is C 1 -C 4 An alkyl group;
preferably, the structural unit of the general formula (II) is one or more of the following structural units:
more preferably +.> For example->
(3) The structural unit of the general formula (III) is
5. The photoresist composition of claim 1, wherein the resin is obtained by polymerizing monomers comprising the following monomers 1 and 2:
R 1 、R 2 、R 3 、R 4 and R is 5 Is as defined in claim 1.
6. The photoresist composition of claim 5, wherein the resin satisfies one or more of the following conditions:
(1) The molar ratio of the monomer 1 to the monomer 2 is (1-5): 1, e.g., 1:1;
(2) The monomer 1 is
(3) The monomer 2 is selected from one or more of the following monomers:
wherein R is 3 、R 4 And R is 5 Each independently is C 1 -C 4 An alkyl group;
preferably, the monomer 2 is selected from One or more of the following; more preferably, said monomer 2 is selected from +.> One or more of the following; for example, the monomer 2 is selected from +.> One or more of the following;
(4) The monomer further comprises the following monomer 3:
R 6 、R 7 and R is 8 Is as defined in claim 2;
(5) When the monomer further comprises a monomer 3, the molar ratio of the monomer 1, the monomer 2 and the monomer 3 is preferably (5-10): (1-5): (1-5), e.g., 5:3:2;
the monomers 3 are preferably
7. The photoresist composition of claim 5, wherein the method of preparing the resin comprises the steps of:
(1) Polymerizing the monomer in a solvent in the presence of an initiator to obtain the resin precursor;
(2) Deacetylation of the resin precursor in the presence of triethylamine in a solvent gives the resin.
8. The photoresist composition of claim 7, wherein the resin satisfies one or more of the following conditions:
(1) In the method for producing the resin, in the step (1), the weight ratio of the solvent to the monomer 1 is (2-8): 1, for example, 3.2:1 or 6.4:1;
(2) In the preparation method of the resin, in the step (1), the solvent is propylene glycol monomethyl ether;
(3) In the preparation method of the resin, in the step (1), the molar ratio of the initiator to the monomer 1 is (7% -14%): 1, e.g. 7%:1 or 14%:1, a step of;
(4) In the preparation method of the resin, in the step (1), the initiator is azodiisobutyronitrile;
(5) In the method for preparing the resin, in the step (1), a post-treatment step of the resin precursor, such as cooling, crystallization and filtration, may be further included;
(6) In the preparation method of the resin, in the step (2), the solvent is propylene glycol monomethyl ether and methanol;
(7) The resin is obtained by polymerizing monomers as described in the following group (a) or (b):
group (a): the molar ratio of the monomer 1 to the monomer 2 is 1:1, a step of;
group (b): the molar ratio of the monomer 1, the monomer 2 and the monomer 3 is 5:3:2;
in the preparation method, in the step (1), the molar ratio of the initiator to the monomer 1 is (7% -14%): 1, a step of;
in the preparation method, in the step (1), the weight ratio of the solvent to the monomer 1 is (2-8): 1.
9. The photoresist composition according to any one of claims 1 to 8, which comprises the following components in mass fraction: the resin, the photoacid generator, the quencher and the solvent, the solvent being the balance; wherein the types and mass fractions of the resin, the photoacid generator, the quencher, and the solvent are as defined in any one of claims 1 to 8.
10. A method of preparing a photoresist composition according to any one of claims 1 to 8, comprising the steps of: and mixing the components of the photoresist composition.
11. A method for forming a pattern using an extreme ultraviolet lithography technique, comprising the steps of:
(I) Coating the photoresist composition according to any one of claims 1 to 9 on the surface of a substrate, and baking to obtain a photoresist layer;
the substrate is preferably a silicon wafer; such as an 8inch silicon wafer;
the method of coating is preferably spin coating with a spin coater;
the thickness of the photoresist layer is preferably 50nm;
the baking temperature is preferably 100-130 ℃, for example 120 ℃;
the baking time is preferably 50-70 seconds, for example 60 seconds;
(II) exposing, baking and developing the photoresist layer obtained in the step 1 to obtain a photoresist pattern;
the baking temperature is preferably 100-130 ℃, for example 120 ℃;
the baking time is preferably 50-70 seconds, for example 60 seconds;
the developer used for the development is preferably an aqueous solution of tetramethylammonium hydroxide, for example, an aqueous solution of TMAH having a mass fraction of 2.38%.
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| CN202210574006.4A CN117148668A (en) | 2022-05-24 | 2022-05-24 | EUV/EB photoresist, preparation method and application thereof |
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