CN101040221B - Composition for forming bottom anti-reflective coating containing aromatic sulfonic acid ester compound and light photoacid-generating agent - Google Patents
Composition for forming bottom anti-reflective coating containing aromatic sulfonic acid ester compound and light photoacid-generating agent Download PDFInfo
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- CN101040221B CN101040221B CN2005800346117A CN200580034611A CN101040221B CN 101040221 B CN101040221 B CN 101040221B CN 2005800346117 A CN2005800346117 A CN 2005800346117A CN 200580034611 A CN200580034611 A CN 200580034611A CN 101040221 B CN101040221 B CN 101040221B
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- China
- Prior art keywords
- lower layer
- compound
- preventing film
- reflection preventing
- layer reflection
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- -1 aromatic sulfonic acid ester compound Chemical class 0.000 title claims abstract description 141
- 239000000203 mixture Substances 0.000 title claims abstract description 102
- 239000003795 chemical substances by application Substances 0.000 title abstract description 10
- 239000006117 anti-reflective coating Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 79
- 239000002253 acid Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000004065 semiconductor Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 87
- 229920005575 poly(amic acid) Polymers 0.000 claims description 56
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 31
- 239000004593 Epoxy Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003380 propellant Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000002790 naphthalenes Chemical class 0.000 claims description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
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- 150000003457 sulfones Chemical class 0.000 description 6
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 5
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- 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
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- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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Abstract
To provide a bottom anti-reflective coating forming composition for forming a bottom anti-reflective coating which is used in a lithography process for manufacturing a semiconductor device and can be developed with an alkaline developing solution for a photoresist, and a method for forming a photoresist pattern using the bottom anti-reflective coating forming composition. A composition for forming a bottom anti-reflective coating which comprises a polyamide acid, a crosslinkable compound having two or more epoxy groups, an aromatic sulfonic acid ester compound, a photoacid-generating agent and a solvent.
Description
Technical field
The present invention relates to the formation method of the photoresist figure of a kind of composition of the formation lower layer reflection preventing film that in the photo-mask process of semiconductor devices manufacturing, uses and a kind of composition that uses this formation lower layer reflection preventing film.In more detail, relate to a kind of composition that is used to form the formation lower layer reflection preventing film of the lower layer reflection preventing film that the alkaline-based developer that uses in the development of available photoresist develops.In addition, the formation method that relates to photoresist figure a kind of composition that uses this formation lower layer reflection preventing film, that undertaken by photoresist and lower layer reflection preventing film are developed simultaneously.
Background technology
In the manufacturing of semiconductor devices, carry out microfabrication by the photoetching of using photoresist.Microfabrication is; by on semiconductor substrates such as silicon wafer, forming the film of photoresist; on this film, see through the mask graph irradiation ultraviolet radiation isoreactivity light of describing component graphics; develop; resulting photoresist figure is carried out etch processes as diaphragm to substrate, thus in the job operation of substrate surface formation corresponding to the micro concavo-convex of above-mentioned figure.But in these photo-mask processs, irreflexive influence that the influence of the standing wave that produces from the reflection of substrate owing to the light that uses in the exposure or the step difference of substrate cause produces the problem that the dimensional accuracy of so-called photoresist figure reduces.Therefore, in order to address this problem, the method for lower layer reflection preventing film (bottom anti-reflective coating) just is being set between photoresist and substrate in broad research.
In order to prevent to mix, often use the heat cross-linking composition to form these lower layer reflection preventing films with the photoresist that is coated with thereon.Consequently, make antireflection film be insoluble to the alkaline-based developer that photoresist is used, removing of the lower layer reflection preventing film of semiconductor substrate first being processed must utilize dry ecthing to carry out (for example, with reference to patent documentation 1).
But when utilizing dry ecthing to remove lower layer reflection preventing film, photoresist also is removed by etching.Its result produces the problem that is difficult to guarantee the thickness of the photoresist of necessity in substrate processing.Under the situation of the photoresist that uses film in order to improve resolution, there is the problem of especially severe.
In addition, the ion injecting process in the semiconductor devices manufacturing is to be template, to import the operation of impurity to semiconductor substrate with the photoresist figure, for fear of the wounded substrate surface, can not carry out the dry ecthing operation when forming the figure of photoresist.Therefore, in the formation of the photoresist figure that is used for ion injecting process, can not make the antireflection film that must utilize dry ecthing to remove be used for the lower floor of photoresist.Up to now, the photoresist figure that in ion injecting process, uses as template, because of its live width very wide, the irreflexive influence that is exposed the exposure irradiation light that the step difference of the influence of the standing wave that irradiates light produces from the reflection of substrate or substrate causes seldom, therefore by using adding that the photoresist of dyestuff is arranged or using antireflection film, can solve the problem that reflection produces on the photoresist upper strata.But along with the development of the miniaturization of dimension of picture, the photoresist that uses in the ion injecting process also begins to need fine figure in recent years, and photoresist lower floor need use antireflection film.
From such present situation, the lower layer reflection preventing film that expectation exploitation is dissolved in the alkaline-based developer that uses in the development of photoresist and can develops simultaneously and remove with photoresist.But up to now, people are to having carried out studying (for example, with reference to patent documentation 2, patent documentation 3, patent documentation 4, patent documentation 5, patent documentation 6) with the photoresist lower layer reflection preventing film of removing that develops simultaneously.But it is, also insufficient at aspects such as the applicability of microfabrication, formed graphics shapes.
Patent documentation 1: No. 6156479 instructions of United States Patent (USP)
Patent documentation 2: No. 2686898 communique of Jap.P.
Patent documentation 3: the spy opens flat 9-78031 communique
Patent documentation 4: the spy opens flat 11-72925 communique
Patent documentation 5: the international pamphlet that discloses No. 03/057678
Patent documentation 6: the international pamphlet that discloses No. 03/058345
Summary of the invention
The present invention is the invention in view of foregoing, and its purpose is to provide a kind of composition that is dissolvable in water the lower layer reflection preventing film of the alkaline-based developer that uses in the development of photoresist and is used to form this lower layer reflection preventing film.
That is, the object of the present invention is to provide a kind of composition of the formation lower layer reflection preventing film that in the manufacturing of semiconductor devices, uses.And, a kind of lower layer reflection preventing film is provided, it does not mix, can be dissolved in alkaline-based developer, can develop simultaneously with photoresist and remove, can give the photoresist figure of good shape with the photoresist that is coated with, is formed at the upper strata.In addition, the object of the present invention is to provide a kind of formation method of the photoresist figure that in the manufacturing of making semiconductor devices, uses of the composition that uses this formation lower layer reflection preventing film.
Present inventors further investigate in view of above-mentioned present situation, found that, utilize the composition that contains aromatic sulphonic acid ester compounds and light acid propellant, can form excellent lower membrane antireflection film, thereby finish the present invention.
Promptly, the present invention, as the 1st scheme, it is a kind of composition that forms lower layer reflection preventing film, it is the composition that is used to form the formation lower layer reflection preventing film of the lower layer reflection preventing film that develops with photoresist by alkaline-based developer, it is characterized in that, contain: polyamic acid, cross-linked compound, aromatic sulphonic acid ester compounds, light acid propellant and solvent with the epoxy radicals more than 2 with structure shown in formula (1) and the formula (2)
In the formula, A
1And A
2The organic group of representing 4 valencys, B
1The organic group of representing 3 valencys, B
2The organic group of expression divalent;
As the 2nd scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that, and then contain light-absorbing compound;
As the 3rd scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that, and then contain the aromatic carboxy acid compound;
As the 4th scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned cross-linked compound is the compound with 2～4 epoxy radicals;
As the 5th scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned light acid propellant is salt compounded of iodine compound or sulfonium salt compound;
As the 6th scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned aromatic sulphonic acid ester compounds is the compound with structure shown in the formula (3),
In the formula, Ar represents to be selected from phenyl ring, naphthalene nucleus or the anthracene nucleus that the group in the alkoxy carbonyl of alkoxy, hydroxyl, nitro, cyano group, amino, halogen, carboxyl and carbon number 1～6 of alkyl, carbon number 1～6 of carbon number 1～6 replaces, R
1And R
2The alkyl of representing hydrogen atom or carbon number 1～6 respectively independently, perhaps, R
1And R
2Can mutually combine and form the ring of carbon number 3～8;
As the 7th scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned aromatic sulphonic acid ester compounds is the compound with the structure shown in 2～4 above-mentioned formulas (3);
As the 8th scheme, be as the composition of the described formation lower layer reflection preventing film of the 2nd scheme, it is characterized in that above-mentioned light-absorbing compound is the naphthoate compound;
As the 9th scheme, be as the composition of the described formation lower layer reflection preventing film of the 8th scheme, it is characterized in that above-mentioned naphthoate compound is the compound that naphthoic acid compound and epoxy compound reaction are produced;
As the 10th scheme, be as the composition of the described formation lower layer reflection preventing film of the 3rd scheme, it is characterized in that above-mentioned aromatic carboxy acid compound is the aromatic carboxy acid compound with phenol hydroxyl;
As the 11st scheme, be as the composition of the described formation lower layer reflection preventing film of the 3rd scheme, it is characterized in that above-mentioned aromatic carboxy acid compound is the naphthoic acid compound with phenol hydroxyl;
As the 12nd scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned polyamic acid is the polyamic acid with structure shown in formula (4) and the formula (5),
In the formula, A
1And A
2The organic group of representing 4 valencys;
As the 13rd scheme, be as the composition of the described formation lower layer reflection preventing film of the 1st scheme, it is characterized in that above-mentioned polyamic acid is the polyamic acid with structure shown in formula (6) and the formula (7),
In the formula, B
1The organic group of representing 3 valencys, B
2The organic group of expression divalent;
As the 14th scheme, be a kind of formation method of the photoresist figure that in the manufacturing of semiconductor devices, uses, comprise: be coated on the composition of each described formation lower layer reflection preventing film of the 1st scheme～the 13rd scheme on the semiconductor substrate and toast the operation that forms lower layer reflection preventing film, in the operation that forms the photoresist layer on the above-mentioned lower layer reflection preventing film, to by the operation of the semiconductor-based board to explosure of above-mentioned lower layer reflection preventing film and the lining of above-mentioned photoresist layer, the operation of after this exposure, utilizing alkaline-based developer to develop.
The composition of the formation lower layer reflection preventing film of the application of the invention can form a kind of lower layer reflection preventing film that does not mix, is dissolved in the alkaline-based developer that uses in the development of photoresist with photoresist, can develop simultaneously and remove with photoresist.
By the lower layer reflection preventing film that the composition that forms lower layer reflection preventing film of the present invention forms, can remove with not carrying out dry ecthing.Therefore what can be used for comprising ion injecting process etc. causes production process of semiconductor device to the responsive operation of substrate surface damage by dry ecthing.
In addition, the lower layer reflection preventing film that forms by the composition that forms lower layer reflection preventing film of the present invention that contains aromatic sulphonic acid ester compounds and light acid propellant, the acidity that can easily its acidity be adjusted into photoresist is same level, therefore can form the photoresist figure of more straight rectangle.
Embodiment
The composition of formation lower layer reflection preventing film of the present invention contains: polyamic acid, the cross-linked compound with the epoxy radicals more than 2, aromatic sulphonic acid ester compounds, light acid propellant and solvent with the structure shown in above-mentioned formula (1) and the above-mentioned formula (2).In addition, the composition of formation lower layer reflection preventing film of the present invention can contain light-absorbing compound, aromatic carboxy acid compound and surfactant etc.
As long as the ratio of the solid constituent in the composition of formation lower layer reflection preventing film of the present invention can make each composition uniform dissolution, just be not particularly limited, for example be 1～50 quality % or be 3～30 quality % or be 5～25 quality % or be 10～15 quality %.Said herein solid constituent is meant the material that removes solvent composition from total composition of the composition that forms lower layer reflection preventing film.
Composition to formation lower layer reflection preventing film of the present invention carries out specific description below.
＜polyamic acid 〉
The composition of formation lower layer reflection preventing film of the present invention contains: the polyamic acid with structure shown in structure shown in the above-mentioned formula (1) and the above-mentioned formula (2).
In above-mentioned formula (1), A
1The organic group of representing 4 valencys, B
1The organic group of representing 3 valencys.As A
1, (in the formula, X represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m for example can to list formula (8)～(16)
1Expression 0,1 or 2).
As carbon number is 1～5 alkyl, is methyl, ethyl, isopropyl, cyclopentyl and n-pentyl etc.As carbon number is 1～5 alkoxy, is methoxyl, ethoxy, isopropoxy, cyclopentyloxy and n-pentyl oxygen base etc.
As B
1, for example can list, (in the formula, Y represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m in formula (17)～(24)
2Expression 0,1 or 2).
In formula (2), A
2The organic group of representing 4 valencys, B
2The organic group of expression divalent.As A
2, can list for example formula (8)～(16).
As B
2, (in the formula, Z represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m for example can to list formula (25)～(34)
3Expression 0,1 or 2).
As the weight-average molecular weight of the polyamic acid that uses among the present invention, proofread and correct with polystyrene, be for example 1000～100000 or 1500～50000 or 2000～30000 or 5000～10000.Weight-average molecular weight less than 1000 situation under, the lower layer reflection preventing film of formation increases the situation that its result causes lower layer reflection preventing film to mix with photoresist sometimes to the solubleness of the solvent that uses in the photoresist.Weight-average molecular weight greater than 100000 situation under, the dissolubility of the alkaline developer that uses in the development of the lower layer reflection preventing film of formation to photoresist becomes insufficient, has the lower layer reflection preventing film residue sometimes after development.
Method to the polyamic acid that contains in the composition that obtains formation lower layer reflection preventing film of the present invention is not particularly limited, and can use known method to make.For example, by with diamine compound, with tetrabasic carboxylic acid or as tetracarboxylic dianhydride's compound of its derivant, dicarboxylic acid dihalide etc. react, polymerization, can make polyamic acid.In addition, carry out polymerization, come synthesizing polyamides acid silyl ester, utilize acid that the silicyl esteratic site is decomposed then, can make polyamic acid by using dimethyl silanyl diamine compound and tetracarboxylic dianhydride's compound.
The polyamic acid that contains in the composition of formation lower layer reflection preventing film of the present invention, can by (a) tetracarboxylic dianhydride compound with (b) have the diamine compound of at least one carboxyl and (c) diamine compound manufacturing.
(a) tetracarboxylic dianhydride compound that uses in the manufacturing to the polyamic acid that uses among the present invention does not have restriction especially.(a) tetracarboxylic dianhydride's compound can use a kind ofly, perhaps also can use simultaneously more than 2 kinds.As object lesson, can list pyromellitic dianhydride, 3,3 ', 4,4 '-bibenzene tetracarboxylic dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic acid dianhydride, 3,3 ', 4,4 '-diphenyl ether tetracarboxylic acid dianhydride, 4,4 '-(hexafluoro isopropylidene) two O-phthalic acid dianhydrides and 3,3 ', 4, aromatic tetracarboxylic acid's dianhydrides such as 4 '-diphenyl sulfone tetracarboxylic acid dianhydride; 1,2,3,4-cyclo-butane tetracarboxylic acid dianhydride, 1,2-dimethyl-1,2,3,4-cyclo-butane tetracarboxylic acid dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclo-butane tetracarboxylic acid dianhydride, 1,2,3,4-cyclopentane tetracarboxylic acid dianhydride, 1,2,3,4-cyclohexane tetracarboxylic acid dianhydride, and 3,4-dicarboxyl-1,2,3, the alicyclic ring shape tetracarboxylic dianhydride that 4-tetrahydrochysene-1-naphthalene succinic dianhydride is such; 1,2,3, the aliphatics tetracarboxylic dianhydride that 4-ethylene-dimalonic acid dianhydride is such.
(b) that uses in the manufacturing to the polyamic acid that uses among the present invention has the diamine compound of at least one carboxyl, is not particularly limited.(b) as diamine compound, for example can list, have the diamine compound of 1～3 carboxyl with at least one carboxyl.(b) have the diamine compound of at least one carboxyl, can use a kind, perhaps also can use simultaneously more than 2 kinds.As object lesson, can list 2, the 4-diaminobenzoic acid, 2, the 5-diaminobenzoic acid, 3, the 5-diaminobenzoic acid, 4, the 6-diaminostilbene, the 3-phthalic acid, 2, the 5-diaminostilbene, the 4-phthalic acid, two (4-amino-3-carboxyl phenyl) ether, two (4-amino-3,5-dicarboxyl phenyl) ether, two (4-amino-3-carboxyl phenyl) sulfone, two (4-amino-3,5-dicarboxyl phenyl) sulfone, 4,4 '-diamido-3,3 '-dicarboxylate biphenyl, 4,4 '-diamido-3,3 '-dicarboxyl-5,5 '-dimethyl diphenyl, 4,4 '-diamido-3,3 '-dicarboxyl-5,5 '-dimethoxy-biphenyl, 1, two (4-amino-3-carboxyl phenoxy group) benzene of 4-, 1, two (4-amino-3-carboxyl phenoxy group) benzene of 3-, two [4-(4-amino-3-carboxyl phenoxy group) phenyl] sulfone, two [4-(4-amino-3-carboxyl phenoxy group) phenyl] propane, and 2, two [4-(4-amino-3-carboxyl phenoxy group) phenyl] HFC-236fa of 2-etc.
In addition, (c) diamine compound that uses in the manufacturing as the polyamic acid that uses among the present invention does not have restriction especially.(c) diamine compound can use a kind ofly, perhaps also can use simultaneously more than 2 kinds.As object lesson, can list 2, the 4-diaminophenol, 3, the 5-diaminophenol, 2, the 5-diaminophenol, 4, the 6-diamino resorcin, 2,5-diamido quinhydrones, two (3-amino-4-hydroxy phenyl) ether, two (4-amino-3-hydroxy base) ether, two (4-amino-3, the 5-dihydroxy phenyl) ether, two (3-amino-4-hydroxy phenyl) methane, two (4-amino-3-hydroxy base) methane, two (4-amino-3, the 5-dihydroxy phenyl) methane, two (3-amino-4-hydroxy phenyl) sulfone, two (4-amino-3-hydroxy base) sulfone, two (4-amino-3, the 5-dihydroxy phenyl) sulfone, 2, two (the 3-amino-4-hydroxy phenyl) HFC-236fa of 2-, 2, two (the 4-amino-3-hydroxy base) HFC-236fa of 2-, 2, two (the 4-amino-3 of 2-, the 5-dihydroxy phenyl) HFC-236fa, 4,4 '-diamido-3,3 '-dihydroxybiphenyl, 4,4 '-diamido-3,3 '-dihydroxy-5,5 '-dimethyl diphenyl, 4,4 '-diamido-3,3 '-dihydroxy-5,5 '-dimethoxy-biphenyl, 1, two (the 3-amino-4-hydroxy phenoxy group) benzene of 4-, 1, two (the 3-amino-4-hydroxy phenoxy group) benzene of 3-, 1, two (the 4-amino-3-hydroxy oxygen base) benzene of 4-, 1, two (the 4-amino-3-hydroxy oxygen base) benzene of 3-, two [4-(3-amino-4-hydroxy phenoxy group) phenyl] sulfone, two [4-(3-amino-4-hydroxy phenoxy group) phenyl] propane, and 2, two [4-(the 3-amino-4-hydroxy phenoxy group) phenyl] HFC-236fa etc. of 2-have the diamine compound of phenol hydroxyl; 1,3-diamido-4-sulfydryl benzene, 1,3-diamido-5-sulfydryl benzene, 1,4-diamido-2-sulfydryl benzene, two (4-amino-3-sulfydryl phenyl) ether, and 2, two (3-amino-4-sulfydryl phenyl) HFC-236fa etc. of 2-have the diamine compound of benzenethiol base, 1,3-diaminobenzene-4-sulfonic acid, 1,3-diaminobenzene-5-sulfonic acid, 1,4-diaminobenzene-2-sulfonic acid, two (4-aminobenzene-3-sulfonic acid) ether, 4,4 '-benzidine-3,3 '-disulfonic acid, and 4,4 '-diamido-3,3 '-dimethyl diphenyl-6,6 '-disulfonic acid etc. have sulfonic diamine compound; 3,5-diaminobenzoic acid-tertiary butyl ester, 3,5-diaminobenzoic acid ethoxyl methyl ester, 3,5-diaminobenzoic acid methyl ester, 3,5-diaminobenzoic acid n-pro-pyl ester, and 3,5-diaminobenzoic acid isobutyl etc. contains the diamine compound of carboxylic acid ester groups.In addition, can list, p-phenylenediamine (PPD), m-phenylene diamine, 4,4 '-methylene-two (2, the 6-diethylaniline), 4,4 '-methylene-two (2-isopropyl-6-methylaniline), 4,4 '-methylene-two (2, the 6-diisopropyl aniline), 2,4,6-trimethyl-1, the 3-phenylenediamine, 2,3,5,6-tetramethyl-1, the 4-phenylenediamine, o-tolidine, between tolidine, 3,3 ', 5,5 '-tetramethyl benzidine, two [4-(3-amino-benzene oxygen) phenyl] sulfone, 2, two [4-(3-amino-benzene oxygen) phenyl] propane of 2-, 2, two [4-(3-amino-benzene oxygen) phenyl] HFC-236fa of 2-, 4,4 '-diamido-3,3 '-dimethyl dicyclohexyl methyl hydride, 4,4 '-diamino-diphenyl ether, 3,4-diamino-diphenyl ether, 4,4 '-diaminodiphenyl-methane, 2, two (4-anilino-) HFC-236fa of 2-, 2, two (3-anilino-) HFC-236fa of 2-, 2, two (3-amino-4-toluyl) HFC-236fa of 2-, 1, two (4-amino-benzene oxygen) benzene of 4-, 1, two (4-amino-benzene oxygen) benzene of 3-, two (4-aminophenyl) sulfone, two [4-(4-amino-benzene oxygen) phenyl] sulfone, 2, two [4-(4-amino-benzene oxygen) phenyl] propyl group of 2-, and 2, diamine compounds such as two [4-(4-amino-benzene oxygen) phenyl] HFC-236fa of 2-.
In the manufacturing of polyamic acid used in the present invention, in the total diamines compound that uses, (b) has the ratio that diamine compound occupied of at least one carboxyl, be for example 1～99 quality %, perhaps be for example 5～80 quality %, perhaps be for example 10～60 quality %, or be 20～50 quality %, or be 30～40 quality %.Have at (b) under the situation of ratio less than aforementioned proportion of diamine compound of at least one carboxyl, the lower layer reflection preventing film of formation becomes insufficient to the dissolubility of alkaline-based developer.
The polyamic acid of Shi Yonging has the diamine compound of at least one carboxyl by (a) tetracarboxylic dianhydride compound, (b) and (c) under the situation that diamine compound is made in the present invention, the total mole number of the diamine compound that uses and the ratio of the total mole number of tetracarboxylic dianhydride's compound are preferably 0.8～1.2.Identical with common polycondensation reaction, this mol ratio approaches 1 more, and the degree of polymerization of the polyamic acid of generation is big more, and molecular weight increases.
In the manufacturing of polyamic acid, the temperature of reaction when diamine compound and the reaction of tetracarboxylic dianhydride's compound can be selected-20 ℃～150 ℃, preferred-5 ℃～100 ℃ arbitrary temp.Temperature of reaction is 5 ℃～40 ℃, and the reaction time is the polyamic acid that can obtain high molecular under 1～48 hour the condition.In order to obtain the good polyamic acid of low-molecular-weight and storage stability, more preferably under 40 ℃～80 ℃, the reaction time is more than 10 hours.
The reaction of diamine compound and tetracarboxylic dianhydride's compound can be carried out in solvent.As the solvent that can use at this moment, can list N, dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, the N-vinyl pyrrolidone, the N-methyl caprolactam, dimethyl sulfoxide (DMSO), tetramethylurea, pyridine, dimethyl sulfone, the hexamethyl sulfoxide, metacresol, butyrolactam, ethyl acetate, butyl acetate, ethyl lactate, 3-methoxypropionic acid methyl esters, 2-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 2-methoxy propyl acetoacetic ester, the 3-ethoxyl ethyl propionate, the 2-ethoxyl ethyl propionate, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, the diglycol methyl ethyl ether, the propylene glycol dimethyl ether, the dipropylene glycol dimethyl ether, the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, the diglycol monotertiary methyl ether, carbiphene, propylene glycol monomethyl ether, propylene glycol list ethylether, the dipropylene glycol monomethyl ether, dipropylene glycol list ethylether, propylene glycol monomethyl ether, the carbitol acetic acid esters, ethyl cellosolve acetate, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, with 2-heptanone etc.They can be used alone, but also also mix together.And then, even can not dissolve the solvent of polyamic acid, also can be in the scope that the polyamic acid that is generated by polyreaction is not separated out, with above-mentioned solvent mixing use.
The solution that contains the polyamic acid that obtains like this can be directly used in the preparation of the composition that forms lower layer reflection preventing film.In addition, polyamic acid also can be dropped in the poor solvents such as methyl alcohol, ethanol, and precipitate and separate is used.
The polyamic acid that contains in the composition as formation lower layer reflection preventing film of the present invention can list, and has the polyamic acid of structure shown in above-mentioned formula (4) and the above-mentioned formula (5).Polyamic acid with structure shown in above-mentioned formula (4) and the above-mentioned formula (5) for example can be by making (a) tetracarboxylic dianhydride's compound and 3, and 5-diaminobenzoic acid and two (4-aminophenyl) sulfone react and obtain.
The polyamic acid that contains in the composition as formation lower layer reflection preventing film of the present invention can also list, and has the polyamic acid of structure shown in above-mentioned formula (6) and the above-mentioned formula (7).Polyamic acid with structure shown in above-mentioned formula (6) and the above-mentioned formula (7), for example can by make 4,4 '-(hexafluoro isopropylidene) two O-phthalic acid dianhydrides with (b) have the diamine compound of at least one carboxyl and (c) diamine compound react and obtain.
The polyamic acid that contains in the composition as formation lower layer reflection preventing film of the present invention, preferably use except its distal portion, substantially by the polyamic acid of the formation of the structure shown in structure shown in the above-mentioned formula (1) and the above-mentioned formula (2) or substantially by the polyamic acid of the formation of the structure shown in structure shown in the above-mentioned formula (4) and the above-mentioned formula (5) or the polyamic acid that constitutes by the structure shown in structure shown in the above-mentioned formula (6) and the above-mentioned formula (7) substantially.
The polyamic acid that contains in the composition as formation lower layer reflection preventing film of the present invention, can list for example following polyamide acid (35)～(43) (in the formula, p
1, p
2, p
3And p
4The ratio of each structure in the expression polyamic acid).Herein, formula (35)～(42) are by a kind of tetracarboxylic dianhydride's compound and two kinds of polyamic acids that diamine compound is made, and formula (43) is by two kinds of tetracarboxylic dianhydride's compounds and two kinds of polyamic acids that diamine compound is made.
＜cross-linked compound 〉
The composition of formation lower layer reflection preventing film of the present invention contains the cross-linked compound with the epoxy radicals more than 2.
As this type of cross-linked compound,, just be not particularly limited so long as have the compound of the epoxy radicals more than 2.It for example is compound with 2～4 epoxy radicals.
Concrete example as cross-linked compound with the epoxy radicals more than 2, can list, three (2, the 3-glycidyl) isocyanuric acid ester, 1, the 4-butanediol diglycidyl ether, 1,2-epoxy-4-(epoxy ethyl) cyclohexane, T 55, the diglycol diglycidyl ether, 2,6-diglycidyl phenyl glycidyl ether, 1,1, [p-(2 for 3-three, the 3-glycidoxy) phenyl] propane, 1,2-cyclohexane cyclohexanedimethanodibasic 2-glycidyl ester, 4,4 '-di-2-ethylhexylphosphine oxide (N, N-diglycidylaniline), 3,4-epoxycyclohexyl methyl-3,4-7-oxa-bicyclo[4.1.0 formic ether, trimethylolethane trimethacrylate glycidol ether and bisphenol-A-diglycidyl ether, with pentaerythrite polyglycidyl ether etc.
In addition, as compound, can use polymkeric substance with epoxy radicals with the epoxy radicals more than 2.As this base polymer,, just can use so long as have the polymkeric substance of epoxy radicals with being not particularly limited.Polymkeric substance with epoxy radicals for example can be made by the addition polymerization that use has an addition polymerization monomer of epoxy radicals.In addition, compound with epoxy radicals such as macromolecular compound that also can be by having hydroxyl and chloropropylene oxide, toluenesulfonic acid ethylene oxidic ester reacts and makes.Can list for example multipolymer of polyacrylic acid ethylene oxidic ester, glycidyl methacrylate and Jia Jibingxisuanyizhi, the polymkeric substance of the addition polymerization of the multipolymer of glycidyl methacrylate and styrene and methacrylic acid-2-hydroxyethyl ester etc.; Or the polymkeric substance of polycondensation such as epoxy novolac.As the weight-average molecular weight of this base polymer, be for example 500～200000, perhaps be 1000～50000.
As compound, can also list and have amino epoxy resin as YH-434, YH434L (Dongdu changes into (strain) system) with at least 2 epoxy radicals; Epoxy resin with cyclohexene oxide structure is as エ Port リ one De GT-401, same GT-403, same GT-301, same GT-302, セ ロ キ サ イ De 2021, セ ロ キ サ イ De 3000 (ダ イ セ Le chemical industry (strain) system); Bisphenol A type epoxy resin is as: エ ピ コ one ト 1001, with 1002, with 1003, with 1004, with 1007, with 1009, with 1010, with 828 (above be that ジ ヤ パ Application エ Port キ シ レ ジ Application (strain) is made); Bisphenol f type epoxy resin is as エ ピ コ one ト 807 (ジ ヤ パ Application エ Port キ シ レ ジ Application (strain) system); Phenol novolac-type epoxy resin is as: エ ピ コ one ト 152, with 154 (above be ジ ヤ パ Application エ Port キ シ レ ジ Application (strain) system), EPPN201, with 202 (above make for Japanese chemical drug (strain)); Cresols novolac-type epoxy resin is as EOCN102, EOCN103S, EOCN104S, EOCN1020, EOCN1025, EOCN1027 (above is Japanese chemical drug (strain) system), エ ピ コ one ト 180S75 (ジ ヤ パ Application エ Port キ シ レ ジ Application (strain) system); Alicyclic ring shape epoxy resin is as デ Na コ one Le EX-252 (Na ガ セ ケ system テ Star Network ス (strain) system), CY175, CY177, CY179 (above is the CIBA-GEIGYA.G system), ア ラ Le ダ イ ト CY182, same CY192, same CY184 (above is CIBA-GEIGY A.G system), エ ピ Network ロ Application 200, with 400 (above is big Japanese イ Application キ chemical industry (strain) system), エ ピ コ one ト 871, with 872 (above is ジ ヤ パ Application エ Port キ シ レ ジ Application (strain) system), ED-5661, ED-5662 (above is セ ラ ニ one ズ コ one テ イ Application グ (strain) system); The aliphatic poly glycidol ether is as デ Na コ one Le EX-611, same EX-612, same EX-614, same EX-622, same EX-411, same EX-512, same EX-522, same EX-421, same EX-313, same EX-314, same EX-321 commercially available compounds such as (Na ガ セ ケ system テ Star Network ス (strain) systems).
As compound with the epoxy radicals more than 2, under the situation of the compound that uses non-polymer, the compound that preferred use for example has 2～10 or 2～4 or 2～3 or 3～5 epoxy radicals.
The content of the cross-linked compound in the composition of formation lower layer reflection preventing film of the present invention with the epoxy radicals more than 2, with respect to 100 mass parts polyamic acids for example is 5～70 mass parts, or be 10～60 mass parts, be preferably 15～45 mass parts or be 20～40 mass parts.Under the situation of content less than above-mentioned value of the cross-linked compound with the epoxy radicals more than 2, the degree of cure deficiency of lower layer reflection preventing film might be dissolved in the photoresist solvent, causes mixing.Under the situation of content greater than above-mentioned value of cross-linked compound, be difficult to obtain the sufficient dissolubility of using in the development to photoresist of alkaline-based developer sometimes with the epoxy radicals more than 2.
＜aromatic sulphonic acid ester compounds 〉
The composition of formation lower layer reflection preventing film of the present invention contains the aromatic sulphonic acid ester compounds.
So long as the aromatic sulphonic acid ester compounds, just there is no particular limitation.For example can list, have the sulfonic alkyl ester compounds and the aryl sulfonate compound of the aromatic hydrocarbon ring of phenyl ring, naphthalene nucleus, anthracene nucleus, fluorenes ring and aphthacene ring etc.In addition, can list, have the sulfonic alkyl ester compounds and the aryl sulfonate compound of heteroaromatic of pyridine ring, furan nucleus, quinoline ring, thiphene ring, pyrimidine ring and quinoxaline ring and thiadiazoles (thiadiazole) ring etc.
The aromatic sulphonic acid ester compounds that contains in the composition of formation lower layer reflection preventing film of the present invention can obtain with known method.For example,, make the reaction of aromatic sulfonyl compound and alcoholic compound or phenolic compounds, obtain the aromatic sulphonic acid ester compounds by in the presence of alkali.
Here, as the aromatic sulfonyl compound, have no particular limits, can list for example benzene sulfonyl chloride, the 4-toluene sulfochloride, the 2-nitrobenzene sulfonyl chloride, 2, the 5-two chloro phenylsulfonyl chloride, 1, the 3-benzene-disulfo-chloride, 4-(2-phthalimide) phenyl sulfonic acid chloride, 2,4, the 6-trimethylbenzene chloride, 1,3,5-benzene three sulfonic acid chlorides, 2,3,5,6-tetramethylbenzene sulfonic acid chloride, 4-(trifluoromethyl) benzene sulfonyl chloride, the pentamethylbenzene sulfonic acid chloride, 4-n-propylbenzene sulfonic acid chloride, 4-ethylbenzene sulfonic acid chloride, 4-n-butylbenzene sulfonic acid chloride, 4-biphenyl sulfonic acid chloride, 4-tert-butyl benzene sulfonic acid chloride, 4-styrene sulfonic acid chloride, 4,4 '-di-2-ethylhexylphosphine oxide (benzene sulfonyl chloride), 4,4 '-biphenyl disulfonic acid chloride and 4, the benzene sulfonyl chloride compound of 4 '-two (chlorine sulphonyl) diphenyl ether etc., naphthalene-1-sulfonic acid chloride, naphthalene-2-sulfonic acid chloride, 2,6-naphthalene disulfonic acid chloride and 1, the naphthalene sulfonyl chloride compound of 5-naphthalene disulfonic acid chloride etc.In addition, can list the anthracene sulfonyl chloride compound and the fluorenes-2 of 2-anthracene sulfonic acid chloride and 9-anthracene sulfonic acid chloride etc., the fluorenes sulfonyl chloride compound of 7-disulfonic acid chloride etc.In addition, can list, thiophene-2-sulfonic acid chloride, 8-quinoline sulfuryl chloride, 5-quinoline sulfuryl chloride, 2-dibenzofurans sulfonic acid chloride, benzene-2,1, the sulfonyl chloride compound with heteroaromatic of 3-triazole-4-sulfonic acid chloride, coumarone-4-sulfonic acid chloride and 5-isoquinoline sulfonic acid chloride etc.
In addition,, have no particular limits, can use the compound that can generate aromatic sulfonic acid ester with the reaction of aromatic sulfonyl compound as alcoholic compound and phenolic compounds.
As alcoholic compound, for example can list, methyl alcohol, ethanol, n-amyl alcohol, cyclohexanol, ring octanol, naphthalane-2-alcohol, 2-ethyl-1-hexanol, 2-ethyl-1,3-hexanediol, 1,2-cyclohexane diol, 2,2,2 tfifluoroethyl alcohol, 1H, 1H-perfluor-1-octanol, 1, the aliphatic alcohol compound of 2-cyclohexanedimethanol and 2-tridecanol etc.In addition, can list benzyl alcohol, 9-hydroxymethyl anthracene, phenylethyl alcohol, 1, the alcoholic compound with aromatic hydrocarbon ring or heteroaromatic of 2-benzene dimethanol, 2-hydroxymethyl thiophene and 2-naphthalene methyl alcohol etc.
As phenolic compounds, for example can list phenol, cresols, beta naphthal and hydroxyl anthracene etc.
As the aromatic sulphonic acid ester compounds in the composition of formation lower layer reflection preventing film of the present invention, can use compound with the structure shown in the above-mentioned formula (3).In above-mentioned formula (3), Ar represents to be selected from phenyl ring, naphthalene nucleus or the anthracene nucleus that the group in the alkoxy carbonyl of alkoxy, hydroxyl, nitro, cyano group, amino, halogen, carboxyl and carbon number 1～6 of alkyl, carbon number 1～6 of carbon number 1～6 replaces.R
1And R
2The alkyl of representing hydrogen atom or carbon number 1～6 respectively independently.In addition, R
1And R
2Can mutually combine and form the ring of carbon number 3～8.As alkyl, methyl, ethyl, isopropyl, n-hexyl and cyclopentyl etc. are arranged.As alkoxy, methoxyl, ethoxy, isopropoxy, n-hexyl oxygen base and cyclopentyloxy etc. are arranged.As alkoxy carbonyl, methoxycarbonyl, ethoxy carbonyl, isopropyl oxygen base carbonyl and cyclopentyloxy carbonyl etc. are arranged.As R
1And R
2The ring of the carbon number 3～8 that forms has cyclopropyl rings, cyclobutyl ring and cyclohexyl ring etc.As halogen, fluorine-based, chloro, bromo and iodo are arranged.
Compound with the structure shown in the above-mentioned formula (3), compound that for example can be by making the structure shown in (44) that has formula and the compound shown in the formula (45) react and obtain.Said compound with structure shown in the formula (44) is an alcoholic compound, can use various alcoholic compounds.
As the aromatic sulphonic acid ester compounds in the composition of formation lower layer reflection preventing film of the present invention, can use compound with the structure shown in 2～4 or 2～3 the above-mentioned formulas (3).Such compound, the alcoholic compound that for example can be by making the structure with 2～4 above-mentioned formulas (44) and the compound of above-mentioned formula (45) react and obtain.
Alcoholic compound as the structure with 2～4 above-mentioned formulas (44) for example can list, ethylene glycol, 1,2-propylene glycol, 1, ammediol, 1,2,3-propane triol, diglycol, triethylene glycol, pentaerythrite, 1,3-benzene dimethanol, 1,4-benzene dimethanol, 1,2-cyclohexane diol, 1,4-cyclohexane diol, 1,3-cyclopentane glycol, 1,2-dicyclohexyl-1,2-ethylene glycol, 1,2-diphenyl-1,2-ethylene glycol, 3,4-furans glycol, 1,4-diox-2,3-two pure and mild 1,4-diox-2,5-two pure and mild trimethylolpropanes etc.
As the compound of above-mentioned formula (45), can list above-mentioned benzene sulfonyl chloride compound, above-mentioned naphthalene sulfonyl chloride compound and above-mentioned anthracene sulfonyl chloride compound.
Have under the situation of the compound of structure shown in 2～4 above-mentioned formulas (3) by compound and next synthesizing of the reaction of the compound shown in the above-mentioned formula (45) with structure shown in the above-mentioned formula (44), the compound of above-mentioned formula (45) can only use a kind of, also can be used in combination more than 2 kinds.
When forming lower layer reflection preventing film, carry out roasting procedure as described later like that by the composition that forms lower layer reflection preventing film of the present invention.Therefore, the aromatic sulphonic acid ester compounds that uses in the composition of formation lower layer reflection preventing film of the present invention more preferably can be because of the easy compound that decomposes of heat.The aromatic sulphonic acid ester compounds that uses in the composition as formation lower layer reflection preventing film of the present invention preferably uses its thermal decomposition to begin the aromatic sulphonic acid ester compounds of temperature more than 100 ℃ or more than 150 ℃ or more than 200 ℃ or more than 220 ℃ or more than 245 ℃.Here said thermal decomposition begins temperature, is meant by TG to measure the temperature that weight that (thermogravimetric quantitative determination) obtain begins to reduce.
The concrete example of the aromatic sulphonic acid ester compounds that uses in the composition as formation lower layer reflection preventing film of the present invention; for example can list; 1; two (tolysulfonyl oxygen) propane of 3-; 1; two (tolysulfonyl oxygen) ethane of 2-; 1; 4-two adjacent tosyls-2; the adjacent isopropylidene threitol of 3-; the triethylene glycol xylene sulfonate; 2; 3-dihydroxy butane-1; 4-two bases two (p-toluenesulfonic esters); four (tolysulfonyl oxygen methyl) methane; 1; 2-propane diol two p-toluenesulfonic esters; 1; 2,4-trimethylbenzene sulfonyl butane triol; 2,3-butanediol two p-toluenesulfonic esters; diglycol two p-toluenesulfonic esters; N; two (2-(tosyl oxygen) ethyl) toluene-4-sulfonamide and 1 of N-, 3-diamantane dimethanol two p-toluenesulfonic esters; 1-benzyl oxygen-3-(tolysulfonyl oxygen)-2-propyl alcohol etc.
In the composition of formation lower layer reflection preventing film of the present invention, the aromatic sulphonic acid ester compounds may be used singly or in combination of two or more.In addition, as its content,, for example be 0.1～100 mass parts with respect to the polyamic acid of 100 mass parts, perhaps be 1～50 mass parts, perhaps be 2～30 mass parts, perhaps be 3～20 mass parts, perhaps be 5～15 mass parts.The content of aromatic sulphonic acid ester compounds is during greater than above-mentioned value, the figure of photoresist is big, occurs the shape of undercutting (under cut) sometimes, in addition, lower layer reflection preventing film is low with respect to the dissolution velocity of alkaline-based developer, goes wrong when removing lower layer reflection preventing film sometimes.
＜light acid propellant 〉
The composition of formation lower layer reflection preventing film of the present invention contains light acid propellant.
As light acid propellant, so long as when the photoresist with the upper strata exposes with KrF excimer laser (wavelength 248nm) and Ar excimer laser (wavelength 193nm) etc., the acidic compound by the effect of this light just can use any.
As such light acid propellant, for example can list salt compound, sulfimine compound and disulfonyl basic weight n-formyl sarcolysine hydride compounds etc.
As salt compound, for example can list salt compounded of iodine compounds such as diphenyl hexafluorophosphoric acid salt compounded of iodine, diphenyl trifluoromethayl sulfonic acid salt compounded of iodine, diphenyl nine fluorine normal butane sulfonic acid salt compounded of iodine, diphenyl perfluor normal octane sulfonic acid salt compounded of iodine, diphenyl camphorsulfonic acid salt compounded of iodine, two (4-tert-butyl-phenyl) camphorsulfonic acid salt compounded of iodine and two (4-tert-butyl-phenyl) trifluoromethayl sulfonic acid salt compounded of iodine, and triphenyl hexafluoro-antimonic acid sulfonium salt, triphenyl nine fluorine normal butane sulfonic acid sulfonium salts, triphenyl camphorsulfonic acid sulfonium salt, and sulfonium salt compound such as triphenyl trifluoromethayl sulfonic acid sulfonium salt.
As sulfimine compound, can list for example N-(fluoroform sulfonyloxy) succinimide, N-(nine fluorine normal butane sulfonyloxies) succinimide, N-(camphor sulfonyloxy) succinimide and N-(fluoroform sulfonyloxy) naphthalimide etc.
As disulfonyl basic weight n-formyl sarcolysine hydride compounds; for example can list; two (trifluoromethyl sulfonyl) diazomethane, two (cyclohexyl sulfonyl) diazomethane, two (phenyl sulfonyl) diazomethane, two (p-toluenesulfonyl) diazomethane, two (2,4-dimethyl benzene sulfonyl) diazomethane, and methyl sulphonyl-p-toluenesulfonyl diazomethane.
In the composition of formation lower layer reflection preventing film of the present invention, these light acid propellants can only use a kind of, also can will be used in combination more than 2 kinds.As the content of light acid propellant, with respect to 100 mass parts polyamic acids, be for example 0.01～20 mass parts, or 0.05～10 mass parts, or 0.1～5 mass parts for example, or 0.5～3 mass parts.By the interpolation light acid propellant, the acidity of scalable lower layer reflection preventing film, thus, the shape of may command photoresist layer.That is,, can form the photoresist figure of rectangular shape by adding light acid propellant.
＜solvent 〉
The solvent that uses in the composition as formation lower layer reflection preventing film of the present invention is so long as the solvent of energy dissolved solid composition can use.As such solvent, for example can use, the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, methylcellosolve acetate, ethyl cellosolve acetate, the diglycol monotertiary methyl ether, carbiphene, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol propyl ether acetic acid esters, toluene, dimethylbenzene, methyl ethyl ketone, cyclopentanone, cyclohexanone, the 2 hydroxy propanoic acid ethyl ester, 2-hydroxy-2-methyl ethyl propionate, ethoxy ethyl acetate, hydroxyl ethyl acetate, 2-hydroxy-3-methyl methyl butyrate, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, the 3-ethoxyl ethyl propionate, 3-ethoxy-propionic acid methyl esters, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N, dinethylformamide, N,N-dimethylacetamide, and N-Methyl pyrrolidone etc.These solvents can use separately, also capable of being combined 2 kinds with on use.And then, also can mix use with high boiling solvents such as propylene glycol single-butyl ether, propylene glycol single-butyl ether acetic acid esters.
The solution of lower layer reflection preventing film resin combination of modulation can be that the filtrator etc. of 0.2 μ m～0.05 μ m filters the back and uses using the aperture.Tiao Zhi lower layer reflection preventing film resin combination at room temperature also has excellent extended storage stability like this.
＜light-absorbing compound 〉
The composition of formation lower layer reflection preventing film of the present invention can contain light-absorbing compound.
As light-absorbing compound,, just be not particularly limited so long as the light wavelength place that uses in the exposure of photoresist has the compound of absorption.The preferred compound that uses with aromatic ring structures such as anthracene nucleus, naphthalene nucleus, phenyl ring, quinoline ring and triazine rings.
Have the viewpoint of very big absorption from light,, can use the naphthoate compound as light-absorbing compound to wavelength 248nm.For example can list 2-hydroxyl-3-2-methyl naphthoate, 6-hydroxyl-2-naphthoic acid benzyl ester, 3-hydroxyl-7-methoxyl-2-naphthoic acid propyl diester and 3,7-dihydroxy-2-naphthoic acid ethyl ester etc.
In addition, as the naphthoate compound outside above-mentioned, can list, utilize methyl alcohol, ethanol, n-amyl alcohol, 9-hydroxymethyl anthracene, the alcoholic compound of cyclohexanol and benzyl alcohol etc., with the 1-naphthoic acid, the 2-naphthoic acid, 1-hydroxyl-2-naphthoic acid, 3-hydroxyl-2-naphthoic acid, 3,7-dihydroxy-2-naphthoic acid, 1, the 2-naphthalenedicarboxylic acid, 1, the 3-naphthalenedicarboxylic acid, 1, the 4-naphthalenedicarboxylic acid, 1, the 5-naphthalenedicarboxylic acid, 1, the 6-naphthalenedicarboxylic acid, 1, the 7-naphthalenedicarboxylic acid, 1, the 8-naphthalenedicarboxylic acid, 2, the 3-naphthalenedicarboxylic acid, 2, the 6-naphthalenedicarboxylic acid, 6-hydroxyl-1-naphthoic acid, 1-hydroxyl-2-naphthoic acid, 3-hydroxyl-2-naphthoic acid, 6-hydroxyl-2-naphthoic acid, 1-bromo-2-hydroxyl-3-naphthoic acid, 1-bromo-4-hydroxyl-3-naphthoic acid, 1,6-two bromo-2-hydroxyl-3-naphthoic acids, 3-hydroxyl-7-methoxyl-2-naphthoic acid, 1,4,5, the 8-naphthalenetetracarbacidic acidic, 3,5-dihydroxy-2-naphthoic acid, 1,4-dihydroxy-2-naphthoic acid, 2-ethoxy-1-naphthoic acid, the naphthoic acid compound of 6-acetoxyl group-2-naphthoic acid etc. carries out esterification and the naphthoate compound that obtains.
In addition, can list the naphthoate compound that the reaction of above-mentioned naphthoic acid compound and epoxy compound obtains.In this reaction, between the carboxyl of naphthoic acid compound and epoxide ring, react, obtain the naphthoate compound.
As epoxy compound, can list, three (2, the 3-glycidyl) isocyanuric acid ester, 1, the 4-butanediol diglycidyl ether, 1,2-epoxy-4-(epoxy ethyl) cyclohexane, T 55, the diglycol diglycidyl ether, 2,6-diglycidyl phenyl glycidyl ether, 1,1, (p-(2 for 3-three, the 3-glycidoxy) propane phenyl), 1,2-cyclohexane cyclohexanedimethanodibasic 2-glycidyl ester, 4,4 '-di-2-ethylhexylphosphine oxide (N, N-diglycidylaniline), 3,4-epoxycyclohexyl methyl-3,4-7-oxa-bicyclo[4.1.0 formic ether, the trimethylolethane trimethacrylate glycidol ether, bisphenol-A-diglycidyl ether, reach compounds such as pentaerythrite polyglycidyl ether.In addition,, can list, contain the polymkeric substance that glycidyl methacrylate etc. has the epoxy radicals structure as epoxy compound.
The reaction of above-mentioned naphthoic acid compound and above-mentioned epoxy compound can be carried out in organic solvents such as benzene,toluene,xylene, ethyl lactate, butyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether and N-Methyl pyrrolidone.In this reaction, also can use quaternary ammonium salts such as benzyltriethylammoinium chloride, tetrabutylammonium chloride and tetraethylammonium bromide as catalyzer.Temperature of reaction, reaction time depend on compound, concentration of use etc., and the reaction time can suitably be selected in 20 ℃～200 ℃ scope from 0.1～100 hour, temperature of reaction.Using under the situation of catalyzer, can be to use in the scope of 0.001～30 quality % in the gross mass with respect to the compound that uses.
Light-absorbing compound as the reaction by above-mentioned naphthoic acid compound and above-mentioned epoxy compound obtains for example can list, and has the polymkeric substance of the structural unit shown in following formula (46) and the formula (47), the compound shown in the formula (48) etc.In the formula (48); Np represents the naphthalene nucleus that can be replaced by following radicals, and described group is: carbon number is that 1～5 alkyl, carbon number are that 1～5 alkoxy, fluorine atom, chlorine atom, bromine atoms, iodine atom, nitro, amino, hydroxyl, carboxyl, phenoxy group, acetyl group or carbon number are 1～5 alkoxy carbonyl.Compound shown in the formula (48) can obtain by three (2, the 3-glycidyl) isocyanuric acid esters and naphthoic acid compound are reacted.
In addition, as light-absorbing compound, be preferably by three (2, the 3-glycidyl) isocyanuric acid ester, with 1-hydroxyl-2-naphthoic acid, 3-hydroxyl-2-naphthoic acid, 3,7-dihydroxy-2-naphthoic acid, 1, the 2-naphthalenedicarboxylic acid, 1, the 4-naphthalenedicarboxylic acid, 1, the 5-naphthalenedicarboxylic acid, 2, the 3-naphthalenedicarboxylic acid, 2, the 6-naphthalenedicarboxylic acid, 6-hydroxyl-1-naphthoic acid, 3-hydroxyl-2-naphthoic acid, 1-bromo-2-hydroxyl-3-naphthoic acid, 1-bromo-4-hydroxyl-3-naphthoic acid, 1,6-two bromo-2-hydroxyl-3-naphthoic acids, 1,4,5, the 8-naphthalenetetracarbacidic acidic, 3,5-dihydroxy-2-naphthoic acid and 1, the naphthoate compound that the naphthoic acid compound reaction of 4-dihydroxy-2-naphthoic acid etc. obtains.
Light-absorbing compound can be used alone or in combination of two or more kinds.Under the situation of using light-absorbing compound, as its content,, be for example 1～300 mass parts with respect to 100 mass parts polyamic acids, or 3～200 mass parts, or 5～100 mass parts, or 10～50 mass parts.Under the situation of content greater than above-mentioned value of light-absorbing compound, lower layer reflection preventing film reduces the dissolubility of alkaline-based developer sometimes.By changing the kind and the content of light-absorbing compound, can adjust the attenuation coefficient (k value) of lower layer reflection preventing film.
＜aromatic carboxy acid compound 〉
The composition of formation lower layer reflection preventing film of the present invention can contain the aromatic carboxy acid compound.By using the aromatic carboxy acid compound, can adjust the dissolution velocity of the lower layer reflection preventing film of formation to alkaline-based developer.
As the aromatic carboxy acid compound, there is no particular limitation, for example can use, and has the aromatic carboxy acid compound of the aromatic rings of phenyl ring, naphthalene nucleus, anthracene nucleus, pyridine ring, thiphene ring, quinoxaline ring, quinoline ring and benzothiazole ring etc.
As the aromatic carboxy acid compound, for example can list benzoic acid, pyromellitic acid, phthalic acid, trimellitic acid, 4-sulfosalicylic phthalate, mellitic acid, 2,3-naphthalenedicarboxylic acid, 3,3 ', 4,4 '-bibenzene tetracarboxylic, 3,3 ', 4,4 '-benzophenone tetracarboxylic acid, 3,3 ', 4,4 '-diphenyl ether tetracarboxylic acid, 3,3 ', 4,4 '-diphenyl sulfone tetracarboxylic acid, 2-naphthoic acid, thiophene-2-carboxylic acid and 9-anthroic acid etc.
In addition, from deliquescent viewpoint, can use aromatic carboxy acid compound with phenol hydroxyl to alkaline-based developer.
As aromatic carboxy acid compound with phenol hydroxyl, for example can list, hydroxybenzoic acid, 4-hydroxyl phthalic, 3,4-dihydroxy phthalic acid and 4, the benzoic acid compounds with phenol hydroxyl of 5-dihydroxy phthalic acid etc., with 2-hydroxyl-3-naphthoic acid, 2-hydroxyl-1-naphthoic acid, 8-hydroxyl-1-naphthoic acid and 3, the naphthoic acid compound with phenol hydroxyl of 7-dihydroxy-2-naphthoic acid etc. etc.
The aromatic carboxy acid compound can be used alone or in combination of two or more kinds.Under the situation of using the aromatic carboxy acid compound, as its content,, for example be 1～100 mass parts with respect to the polyamic acid of 100 mass parts, or 3～50 mass parts, perhaps for example be 5～30 mass parts, or 10～20 mass parts.Under aromatic carboxy acid compound's the situation of content greater than above-mentioned value, lower layer reflection preventing film is excessive to the dissolubility of alkaline-based developer sometimes, causes producing the problem of the bad grade of graphics shape.
The composition of formation lower layer reflection preventing film of the present invention as required, can contain surfactant, rheology control agent and bonding assistant etc.
As surfactant, for example can list polyoxyethylene alkyl ether classes such as polyoxyethylene lauryl ether, polyoxyethylene octadecyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether; Polyoxyethylene alkylaryl ether classes such as polyoxyethylene octyl phenol ether, polyoxyethylene nonylphenyl ether; Polyoxyethylene polyoxypropylene block polymer class; Sorbitan fatty ester classes such as sorbitan monolaurate, sorbitan-monopalmityl ester, anhydrosorbitol monostearate, dehydrating sorbitol monooleate, anhydrosorbitol trioleate, anhydrosorbitol tristearate; Non-ionics such as polyoxyethylene sorbitan fatty acid ester such as polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate; エ Off ト Star プ EF301, EF303, EF325 ((strain) ジ エ system コ system), メ ガ Off ア Star Network F171, F173 (big Japanese イ Application キ chemical industry (strain) system), Off ロ ラ one De FC430, FC431 (Sumitomo ス リ one エ system (strain) system), ア サ ヒ ガ one De AG710, サ one Off ロ Application S-382, SC101, SC102, SC103, SC104, SC105, the fluorine class surfactant of SC106 (Asahi Glass (strain) system) etc., organic siloxane polymer KP341 (SHIN-ETSU HANTOTAI's chemical industry (strain) system) etc.The use level of these surfactants in whole compositions of the composition of formation lower layer reflection preventing film of the present invention, is generally below the 0.2 quality %, is preferably below the 0.1 quality %.These surfactants can add separately, also combination more than 2 kinds are added.
Below, the use of the composition of formation lower layer reflection preventing film of the present invention is described.
On semiconductor substrate (for example silicon/silicon dioxide is substrate coated, silicon nitride substrate, silicon wafer substrate, glass substrate and ito substrate etc.), utilize suitable coating processes such as spin coating, coating to be coated with the composition of formation lower layer reflection preventing film of the present invention, then, form lower layer reflection preventing film by baking.As the condition of baking, suitably select 0.3～60 minute from 80 ℃～300 ℃ of baking temperatures, stoving time.Be preferably 150 ℃～250 ℃, 0.5～2 minute.
As the dissolution velocity of the alkaline-based developer that uses in the development of formed lower layer reflection preventing film to photoresist, be per second 0.1nm～50nm, be preferably per second 0.2nm～40nm, more preferably per second 0.3nm～20nm.Under the dissolution velocity situation littler than this, it is elongated to remove the lower layer reflection preventing film time necessary, causes throughput rate to reduce.Under the dissolution velocity situation bigger than this, the lower layer reflection preventing film of the unexposed subordinate's layer of resist also can dissolve, and the result causes can't obtaining the resist figure sometimes.
By the lower layer reflection preventing film that the composition that forms lower layer reflection preventing film of the present invention forms, the baking condition in the time of can forming by change is controlled the dissolution velocity of lower layer reflection preventing film to alkaline-based developer.When stoving time was constant, baking temperature was high more, can form the lower layer reflection preventing film more little to the dissolution velocity of alkaline-based developer.
Then, on lower layer reflection preventing film, form the photoresist layer.The formation of photoresist layer can promptly be undertaken by the coating and the baking of photoresist agent solution on lower layer reflection preventing film by general method.
As the photoresist that forms on the lower layer reflection preventing film of the present invention, so long as the material of the light sensitization of use in the exposure is got final product, there is no particular restriction, can use in minus and the positive light anti-etching agent any.As such photoresist, the phenolic novolac of containing and 1 are arranged, the positive light anti-etching agent of 2-naphthoquinones diazido sulphonic acid ester, contain to have and decompose the bonding agent of the group that can improve alkali dissolution speed and the chemical amplifying type photoresist of light acid propellant through acid, contain through acid and decompose the low molecular compound of the alkali dissolution speed that can improve photoresist and the chemical amplifying type photoresist of alkali solubility bonding agent and light acid propellant, contain to have and decompose the bonding agent of the group that can improve alkali dissolution speed and decompose the low molecular compound of the alkali dissolution speed that can improve photoresist and the chemical amplifying type photoresist of light acid propellant etc. through acid through acid.In addition, for example can list the system trade name APEX-E of シ プ レ one society, Sumitomo Chemical (strain) system trade name PAR710, SHIN-ETSU HANTOTAI's chemical industry (strain) system trade name SEPR430 etc.
Then, seeing through specific mask exposes.In exposure, can use KrF excimer laser (wavelength 248nm), ArF excimer laser (wavelength 193nm) and F2 excimer laser (wavelength 157nm) etc.After exposure, as required, back heating (post exposurebake) also can expose.
Then, utilize alkaline-based developer to develop.Thus, using under the situation of positive light anti-etching agent for example, the photoresist of exposed portion and the lower layer reflection preventing film of underclad portion thereof can be removed by development, form the photoresist figure.
The alkaline-based developer that uses in the development as photoresist, for example can list the alkaline aqueous solutions such as aqueous solution of amines such as the aqueous solution of quaternary ammonium hydroxides such as the aqueous solution of alkali metal hydroxides such as potassium hydroxide, NaOH, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, choline, monoethanolamine, propylamine, ethylenediamine.And then, also can in these developer solutions, add surfactant etc.As the condition of developing, temperature can suitably be selected from 10～300 seconds from 5 ℃～50 ℃, time.
Lower layer reflection preventing film by the composition that forms lower layer reflection preventing film of the present invention forms as alkaline-based developer, can use the tetramethylammonium hydroxide aqueous solution of widely used 2.38 quality %, at room temperature, easily develops.
Lower layer reflection preventing film of the present invention can be used as following layer: the interactional layer that is used to prevent semiconductor substrate and photoresist; Be used for preventing that material that uses at photoresist or the material that generates from producing the layer of ill-effect to substrate when photoresist exposes; Be used to prevent the material that when heated baking, produces layer to the diffusion of the photoresist on upper strata by substrate; Be used to reduce that the semiconductor substrate dielectric layer causes to the restraining barrier of the poisoning effect of photoresist layer.
Below, be described more specifically the present invention by embodiment, but the present invention is not so limited.
Embodiment
Embodiment 1
(synthesizing of polyamic acid)
With 4,4 '-(hexafluoro isopropylidene) diphthalic anhydrides 17.8g, 3,5-diaminobenzoic acid 3.12g and two (4-aminophenyl) sulfone 4.92g obtain to contain the solution [A] of polyamic acid in propylene glycol monomethyl ether 145.6g, 80 ℃ of reactions 20 hours.The polyamic acid that obtains has the structure shown in formula (49) and the formula (50).
(synthesizing of light-absorbing compound)
With 3 of 19.0g, 7-dihydroxy-2-naphthoic acid, 10g three (2, the 3-glycidyl) isocyanuric acid ester and 0.552g benzyltriethylammoinium chloride obtain to contain the solution [a] of the light-absorbing compound shown in the formula (51) in the 118g cyclohexanone, 130 ℃ of reactions 24 hours.
(forming the preparation of compositions of lower layer reflection preventing film)
Contain 4 of the solution [a] that adds 4.15g in the solution [A] of polyamic acid and contain light-absorbing compound, 1.13g at 25.0g, 4 '-di-2-ethylhexylphosphine oxide (N, the N-diglycidylaniline), 3 of 0.825g, 1 of 7-dihydroxy naphthlene formic acid, 0.206g, two (tolysulfonyl oxygen) propane of 3-, the triphenyl trifluoromethayl sulfonic acid sulfonium salt of 0.124g, the propylene glycol monomethyl ether of 82.8g, the propylene glycol monomethyl ether of 127g and the cyclohexanone of 10.0g, at room temperature stirred 30 minutes, preparation forms the solution [1] of the composition of lower layer reflection preventing film.
In addition, to 1, two (tolysulfonyl oxygen) propane of 3-carry out thermogravimetric quantitative determination (operative installations: セ イ コ one イ Application ス Star Le メ Application Star (strain) system SSC/5200, condition determination: 30 ℃～400 ℃ of measurement ranges, 10 ℃ of programming rate per minutes), its weight temperature of beginning to reduce is 250 ℃ as a result.(evaluation of lower layer reflection preventing film)
Use spinner, the solution [1] that forms the composition of lower layer reflection preventing film is coated on the silicon wafer substrate, on electric hot plate, 175 ℃ of bakings 1 minute, form the lower layer reflection preventing film of thickness 40nm.The lower layer reflection preventing film that obtains is insoluble to propylene glycol, ethyl lactate and propylene glycol monomethyl ether.Use the beam split ellipsometer to measure this lower layer reflection preventing film, the result be 1.80 in the refractive index at wavelength 248nm place (n value), attenuation coefficient (k value) is 0.44.In addition, the refractive index (n value) at wavelength 193nm place is 1.52, attenuation coefficient (k value) is 0.44.
In addition, be under 170 ℃ and 180 ℃ at baking temperature, with above-mentioned same operation, formed lower layer reflection preventing film.And, confirm that these lower layer reflection preventing films are insoluble to ethyl lactate and propylene glycol monomethyl ether.
Then, use resist development analyser (リ ソ テ Star Network ジ ヤ パ Application (strain) system) to measure the dissolution velocity of lower layer reflection preventing film to alkaline-based developer (2.38% tetramethylammonium hydroxide aqueous solution: chemical industry (strain) system, trade name NMD-3 are answered in Tokyo).Dissolution velocity at 175 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 1.74nm.In addition, the dissolution velocity at 170 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 2.35nm; Dissolution velocity at 180 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 1.48nm.
Use spinner, be coated on the solution [1] that forms the composition of lower layer reflection preventing film on the silicon wafer substrate after, on electric hot plate, 175 ℃ of bakings 1 minute, form the lower layer reflection preventing film of thickness 40nm.See through the mask set, expose, make on this lower layer reflection preventing film, to form ArF positive light anti-etching agent film, line/space figure of formation 70nm with ArF excimer laser (wavelength 193nm).Heat after 60 seconds the exposure carrying out under 110 ℃, use 2.38% tetramethylammonium hydroxide aqueous solution (chemical industry (strain) system, trade name NMD-3 are answered in Tokyo) to carry out the oar formula (paddle) in 60 seconds then and develop.The exposed portion of lower layer reflection preventing film also dissolves with photoresist, does not also find the residual film of lower layer reflection preventing film in line/gap of 70nm.As the figure that forms, photoresist and lower layer reflection preventing film all are the shape of rectangle.
Comparative example 1
(forming the preparation of compositions of lower layer reflection preventing film)
In the solution that contains polyamic acid [A] of 25.0g, add 4 of solution [a] that 4.15g contains light-absorbing compound, 1.13g, 4 '-di-2-ethylhexylphosphine oxide (N, the N-diglycidylaniline), 3 of 0.825g, the propylene glycol monomethyl ether of 7-dihydroxy naphthlene formic acid, 82.8g, the propylene glycol monomethyl ether of 127g and the cyclohexanone of 10.0g, at room temperature stirred 30 minutes, preparation forms the solution [2] of the composition of lower layer reflection preventing film.
(evaluation of lower layer reflection preventing film)
Use spinner, be coated on the solution [2] of the composition of this formations lower layer reflection preventing film on the silicon wafer substrate after, on electric hot plate, 175 ℃ of bakings 1 minute, the lower layer reflection preventing film of formation thickness 40nm.The lower layer reflection preventing film that obtains is insoluble to propylene glycol, ethyl lactate and propylene glycol monomethyl ether.Use the beam split ellipsometer to measure this lower layer reflection preventing film, the result is for the refractive index (n value) at wavelength 248nm place is 1.82, attenuation coefficient (k value) is 0.42, and the refractive index (n value) at wavelength 193nm place is 1.51, attenuation coefficient (k value) is 0.42.
In addition, be to have formed lower layer reflection preventing film with same method under 170 ℃ and 180 ℃ at baking temperature.And, confirm that these lower layer reflection preventing films are insoluble to ethyl lactate and propylene glycol monomethyl ether.
Then, use resist development analyser (リ ソ テ Star Network ジ ヤ パ Application (strain) system) to measure the dissolution velocity of lower layer reflection preventing film to 2.38% tetramethylammonium hydroxide aqueous solution (Tokyo answers chemical industry (strain) to make trade name NMD-3).The dissolution velocity of the lower layer reflection preventing film that forms under 60 seconds at 175 ℃ of baking temperatures, stoving time is per second 2.40nm.In addition, the dissolution velocity at 170 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 2.65nm; Dissolution velocity at 180 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 2.03nm.
Use spinner, be coated on the solution [2] that forms the composition of lower layer reflection preventing film on the silicon wafer substrate after, on electric hot plate,, form the lower layer reflection preventing film of thickness 40nm 175 ℃ of bakings 1 minute.See through the mask set, expose, make on this lower layer reflection preventing film, to form ArF positive light anti-etching agent film, line/space figure of formation 70nm with ArF excimer laser (wavelength 193nm).Heat after 60 seconds in exposure under 110 ℃, use 2.38% tetramethylammonium hydroxide aqueous solution (chemical industry (strain) system, trade name NMD-3 are answered in Tokyo) then, carry out oar formula development in 60 seconds.The photoresist layer is root effect (footing) shape.In addition, lower layer reflection preventing film is dissolving fully not, finds residual film.
Comparative example 2
(forming the preparation of compositions of lower layer reflection preventing film)
In the solution that contains polyamic acid [A] of 25.0g, add 4 of solution [a] that 4.15g contains light-absorbing compound, 1.13g, 4 '-di-2-ethylhexylphosphine oxide (N, the N-diglycidylaniline), 3 of 0.825g, the triphenyl trifluoromethayl sulfonic acid sulfonium salt of 7-dihydroxy naphthlene formic acid, 0.124g, the propylene glycol monomethyl ether of 82.8g, the propylene glycol monomethyl ether of 127g and the cyclohexanone of 10.0g, at room temperature stirred 30 minutes, preparation forms the solution [3] of the composition of lower layer reflection preventing film.
(evaluation of lower layer reflection preventing film)
Use spinner, be coated on the solution [3] of the composition of this formations lower layer reflection preventing film on the silicon wafer substrate after, on electric hot plate, 175 ℃ of bakings 1 minute, the lower layer reflection preventing film of formation thickness 40nm.The lower layer reflection preventing film that obtains is insoluble to propylene glycol, ethyl lactate and propylene glycol monomethyl ether.Use the beam split ellipsometer to measure this lower layer reflection preventing film, the result is for the refractive index (n value) at wavelength 248nm place is 1.80, attenuation coefficient (k value) is 0.44, and the refractive index (n value) at wavelength 193nm place is 1.50, attenuation coefficient (k value) is 0.44.
In addition, be to have formed antireflection film with same method under 170 ℃ and 180 ℃ at baking temperature.And, confirm that these lower layer reflection preventing films are insoluble to ethyl lactate and propylene glycol monomethyl ether.
Then, use resist development analyser (リ ソ テ Star Network ジ ヤ パ Application (strain) system) to measure the dissolution velocity of lower layer reflection preventing film to 2.38% tetramethylammonium hydroxide aqueous solution (Tokyo answers chemical industry (strain) to make trade name NMD-3).Dissolution velocity at 175 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 2.00nm.In addition, the dissolution velocity at 170 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 2.35nm; Dissolution velocity at 180 ℃ of baking temperatures, 1 minute following lower layer reflection preventing film that forms of stoving time is per second 1.82nm.
Use spinner, be coated on the solution [3] that forms the composition of lower layer reflection preventing film on the silicon wafer substrate after, on electric hot plate,, form the lower layer reflection preventing film of thickness 40nm 175 ℃ of bakings 1 minute.See through the mask set, expose, make on this lower layer reflection preventing film, to form ArF positive light anti-etching agent film, line/space figure of formation 70nm with ArF excimer laser (wavelength 193nm).Heat after 60 seconds in exposure under 110 ℃, use 2.38% tetramethylammonium hydroxide aqueous solution (chemical industry (strain) system, trade name NMD-3 are answered in Tokyo) then, carry out oar formula development in 60 seconds.The photoresist layer is a root effect shape.In addition, lower layer reflection preventing film is dissolving fully not, finds residual film.
Claims (14)
1. composition that forms lower layer reflection preventing film, it is the composition that is used to form the formation lower layer reflection preventing film of the lower layer reflection preventing film that develops with photoresist by alkaline-based developer, it is characterized in that, contain: the weight-average molecular weight with structure shown in formula (1) and the formula (2) is 1000～100000 polyamic acid, cross-linked compound with the epoxy radicals more than 2, it is aromatic sulphonic acid ester compounds more than 100 ℃ that thermal decomposition begins temperature, light acid propellant and solvent
In the formula, A
1And A
2Represent the group shown in following formula (8)～(16), B
1Represent the group shown in following formula (17)～(24), B
2Represent the group shown in following formula (25)～(34),
In the formula, X represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m
1Expression 0,1 or 2;
In the formula, Y represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m
2Expression 0,1 or 2;
In the formula, Z represents that carbon number is that 1～5 alkyl, chlorine atom, bromine atoms, fluorine atom, carbon number are 1～5 alkoxy, hydroxyl, carboxyl, phenoxy group, trifluoromethyl or nitro, m
3Expression 0,1 or 2.
2. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, and then contains light-absorbing compound.
3. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, and then contains the aromatic carboxy acid compound.
4. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned cross-linked compound is the compound with 2～4 epoxy radicals.
5. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned light acid propellant is salt compounded of iodine compound or sulfonium salt compound.
6. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned aromatic sulphonic acid ester compounds is the compound with structure shown in the formula (3),
In the formula, Ar represents to be selected from phenyl ring, naphthalene nucleus or the anthracene nucleus that the group in the alkoxy carbonyl of alkoxy, hydroxyl, nitro, cyano group, amino, halogen, carboxyl and carbon number 1～6 of alkyl, carbon number 1～6 of carbon number 1～6 replaces, R
1And R
2The alkyl of representing hydrogen atom or carbon number 1～6 respectively independently, perhaps, R
1And R
2Can mutually combine and form the ring of carbon number 3～8.
7. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned aromatic sulphonic acid ester compounds is the compound with the structure shown in 2～4 above-mentioned formulas (3).
8. the composition of formation lower layer reflection preventing film as claimed in claim 2 is characterized in that, above-mentioned light-absorbing compound is the naphthoate compound.
9. the composition of formation lower layer reflection preventing film as claimed in claim 8 is characterized in that, above-mentioned naphthoate compound is the compound by the reaction of naphthoic acid compound and epoxy compound is produced.
10. the composition of formation lower layer reflection preventing film as claimed in claim 3 is characterized in that, above-mentioned aromatic carboxy acid compound is the aromatic carboxy acid compound with phenol hydroxyl.
11. the composition of formation lower layer reflection preventing film as claimed in claim 3 is characterized in that, above-mentioned aromatic carboxy acid compound is the naphthoic acid compound with phenol hydroxyl.
12. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned polyamic acid is the polyamic acid with structure shown in formula (4) and the formula (5),
In the formula, A
1And A
2The expression with claim 1 in identical implication.
13. the composition of formation lower layer reflection preventing film as claimed in claim 1 is characterized in that, above-mentioned polyamic acid is the polyamic acid with structure shown in formula (6) and the formula (7),
In the formula, B
1, B
2The expression with claim 1 in identical implication.
14. the formation method of a photoresist figure that uses in the manufacturing of semiconductor devices comprises: be coated on the composition of each described formation lower layer reflection preventing film of claim 1～13 on the semiconductor substrate and toast the operation that forms lower layer reflection preventing film, in the operation that forms the photoresist layer on the above-mentioned lower layer reflection preventing film, to by the operation of the semiconductor-based board to explosure of above-mentioned lower layer reflection preventing film and the lining of above-mentioned photoresist layer, the operation of after this exposure, utilizing alkaline-based developer to develop.
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| JP2004299715 | 2004-10-14 | ||
| JP299715/2004 | 2004-10-14 | ||
| PCT/JP2005/017734 WO2006040922A1 (en) | 2004-10-14 | 2005-09-27 | Composition for forming bottom anti-reflective coating containing aromatic sulfonic acid ester compound and light photoacid-generating agent |
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| CN103163736A (en) * | 2004-09-03 | 2013-06-19 | 日产化学工业株式会社 | Composition including polyamide acid for forming lower layer reflection preventing film |
| WO2006040922A1 (en) * | 2004-10-14 | 2006-04-20 | Nissan Chemical Industries, Ltd. | Composition for forming bottom anti-reflective coating containing aromatic sulfonic acid ester compound and light photoacid-generating agent |
| CN101473270B (en) * | 2006-06-19 | 2014-08-06 | 日产化学工业株式会社 | Composition containing hydroxylated condensation resin for forming film under resist |
| US8088548B2 (en) * | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
| US8039201B2 (en) | 2007-11-21 | 2011-10-18 | Az Electronic Materials Usa Corp. | Antireflective coating composition and process thereof |
| JP2013137334A (en) * | 2010-04-21 | 2013-07-11 | Nissan Chem Ind Ltd | Resist underlayer film-forming composition for lithography comprising resin containing polyimide structure |
| KR20140045556A (en) * | 2011-07-12 | 2014-04-16 | 닛산 가가쿠 고교 가부시키 가이샤 | Composition liquid crystal alignment treatment agent, liquid crystal alignment film, and liquid crystal display element |
| CN103975418B (en) * | 2011-10-10 | 2017-03-08 | 布鲁尔科技公司 | Spin coating carbon composition for lithographic printing processing |
| CN106233207B (en) * | 2014-04-25 | 2020-04-10 | 日产化学工业株式会社 | Composition for forming resist underlayer film and method for forming resist pattern using same |
| US10203602B2 (en) * | 2016-09-30 | 2019-02-12 | Rohm And Haas Electronic Materials Korea Ltd. | Coating compositions for use with an overcoated photoresist |
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| US6455416B1 (en) * | 2000-10-24 | 2002-09-24 | Advanced Micro Devices, Inc. | Developer soluble dyed BARC for dual damascene process |
| CN1502062A (en) * | 2001-04-10 | 2004-06-02 | 日产化学工业株式会社 | Composition for forming antireflection film for lithography |
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| JPH0572736A (en) * | 1991-09-18 | 1993-03-26 | Hitachi Chem Co Ltd | Production of fluorine-contained polyimide resin film pattern |
| JP3031214B2 (en) * | 1995-09-11 | 2000-04-10 | 信越化学工業株式会社 | Anti-reflective coating material |
| US6927012B2 (en) * | 2001-07-26 | 2005-08-09 | Nissan Chemical Industries, Ltd. | Polyamic acid resin composition |
| TWI358612B (en) * | 2003-08-28 | 2012-02-21 | Nissan Chemical Ind Ltd | Polyamic acid-containing composition for forming a |
| WO2006040922A1 (en) * | 2004-10-14 | 2006-04-20 | Nissan Chemical Industries, Ltd. | Composition for forming bottom anti-reflective coating containing aromatic sulfonic acid ester compound and light photoacid-generating agent |
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| US6455416B1 (en) * | 2000-10-24 | 2002-09-24 | Advanced Micro Devices, Inc. | Developer soluble dyed BARC for dual damascene process |
| CN1502062A (en) * | 2001-04-10 | 2004-06-02 | 日产化学工业株式会社 | Composition for forming antireflection film for lithography |
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| KR101195468B1 (en) | 2012-10-30 |
| TWI375868B (en) | 2012-11-01 |
| JP4525940B2 (en) | 2010-08-18 |
| TW200622498A (en) | 2006-07-01 |
| KR20070065316A (en) | 2007-06-22 |
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