WO2003100524A1 - Composition de resine sensible au rayonnement, procede de production d'un substrat comprenant couche de resine a motifs, et utilisation de la composition de resine - Google Patents

Composition de resine sensible au rayonnement, procede de production d'un substrat comprenant couche de resine a motifs, et utilisation de la composition de resine Download PDF

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Publication number
WO2003100524A1
WO2003100524A1 PCT/JP2003/006599 JP0306599W WO03100524A1 WO 2003100524 A1 WO2003100524 A1 WO 2003100524A1 JP 0306599 W JP0306599 W JP 0306599W WO 03100524 A1 WO03100524 A1 WO 03100524A1
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Prior art keywords
group
radiation
resin composition
compound
sensitive resin
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PCT/JP2003/006599
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English (en)
Japanese (ja)
Inventor
Junji Kodemura
Hirokazu Higashi
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Zeon Corporation
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Priority to JP2004507917A priority Critical patent/JP3843995B2/ja
Publication of WO2003100524A1 publication Critical patent/WO2003100524A1/fr

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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition

Definitions

  • Radiation-sensitive resin composition method for producing substrate having patterned resin film, and use of resin composition
  • the present invention relates to a radiation-sensitive resin composition that changes the solubility in a developing solution by irradiation with actinic radiation such as a particle beam or an electron beam. More specifically, the present invention relates to a resin film for electronic components such as a protective film, a planarizing film, and an electric insulating film, which has a low dielectric constant, transparency, heat resistance (particularly, heat discoloration resistance), and angular resolution. The present invention relates to a radiation-sensitive resin composition suitable as a resin material for forming a resin film having excellent residual film ratio and pattern shape. Height
  • a functional resin film for electronic parts such as a flat film and an electric insulating film for maintaining electric insulation.
  • an interlayer insulating film is provided as a resin film for electronic components in order to insulate between wirings arranged in layers.
  • thermosetting resin materials have been known as resin materials for forming an insulating film for electronic components, but it is difficult to obtain an interlayer insulating film having sufficient flatness. Therefore, development of a new insulating film forming resin material capable of fine patterning is required. In recent years, as the density of wirings and devices has increased, these resin materials have been required to have excellent dielectric properties, and particularly to have a low dielectric constant. In response to such demands, an alkali-soluble alicyclic olefin resin obtained by subjecting an ester group-containing norbornene monomer to ring-opening polymerization, hydrogenating, and then hydrolyzing the ester group portion. Radiation-sensitive tree containing acid generator and cross-linking agent Fat compositions have been proposed (for example, Japanese Patent Application Laid-Open Nos.
  • the present inventors have studied the characteristics of a resin film obtained using the above-mentioned known photosensitive resin composition containing an alkali-soluble alicyclic olefin resin. Although it has excellent dielectric properties (low dielectric constant), low water absorption, flatness, solvent resistance, heat-resistant dimensional stability, etc., its transparency, resolution, exposure margin, remaining film ratio, etc. are not sufficient. It has been found that it is easy to change color by the heat treatment of the above-mentioned, and it is difficult to obtain a good pattern shape.
  • Heat treatment may be performed at a high temperature of 200 ° C. or higher.
  • the resin film formed using the above-described known radiation-sensitive resin composition is stable at a heat treatment temperature of 200 ° C. or less, It was found that discoloration was liable to occur when heat treatment was performed at a high temperature exceeding the above. For this reason, when manufacturing a transparent circuit board having a resin film made of the known radiation-sensitive resin composition as an electrical insulating film, heat treatment must be performed in an inert gas atmosphere with a very low oxygen concentration. If this is the case, the transparency of the electrical insulation film cannot be maintained.
  • An object of the present invention is to use an alicyclic resin as a base resin, and to have low dielectric constant, flatness, heat-resistant dimensional stability, good solvent resistance, transparency, heat discoloration,
  • An object of the present invention is to provide a radiation-sensitive resin composition having remarkably excellent resolution, remaining film ratio, pattern shape, exposure margin, and the like.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that in a photosensitive resin composition containing an alicyclic olefin resin, an acid generator, a crosslinking agent and a solvent, a phenolic resin having a specific structure is used.
  • a phenolic resin having a specific structure is used.
  • the compatibility of each component is good, the pattern junging performance such as resolution, exposure margin, remaining film ratio, pattern shape, etc. is improved, and transparency, heat discoloration, etc. can be significantly improved.
  • the present invention It has been led to completion on the basis of two these findings (
  • n is an integer of 1 to 4
  • A is an n-valent organic group or a carbon atom
  • B is a divalent organic group or a single bond
  • Y is A hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Z is a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, or the following formula (2)
  • R 4 to R 6 are each independently a hydrogen atom, a hydroxyl group, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms.
  • substituted Hue in represented by - a group, 1 ⁇ to 1 3 are each independently a hydrogen atom, a hydroxyl group or a number of carbon atoms;! And 6 to 6 linear, branched or cyclic alkyl groups.
  • Y and Z are both hydrogen atoms
  • n is an integer of 2 to 4
  • A is a carbon atom
  • a substrate having a patterned resin film containing:
  • the radiation-sensitive resin composition as a resin film for an electronic component is provided.
  • a method for forming a patterned resin film on a substrate including the above steps 1 to 3. According to the present invention, the method is obtained by the forming method. Further, according to the present invention, there is provided a use of the patterned resin film as a resin film for an electronic component.
  • the radiation-sensitive resin composition of the present invention contains an alicyclic resin as a base resin.
  • the (A) alicyclic olefin resin used in the present invention has a structural unit derived from an olefin monomer having an alicyclic structure (hereinafter, referred to as an “alicyclic olefin monomer”). Polymer. The polymer may contain other structural units in addition to the structural units derived from the alicyclic olefin monomer.
  • the alicyclic resin used in the present invention preferably has a polar group.
  • polar groups include acidic groups such as a carboxyl group (ie, a hydroxycarbonyl group), an acid anhydride group (a dicarboxylic acid anhydride residue), a sulfonic acid group, and a phosphoric acid group.
  • the alicyclic olefin resin is preferable because the solubility of the radiation-sensitive resin composition in an alkaline developer is increased.
  • an alicyclic resin having a polar group that is not an acidic group such as a phenolic hydroxyl group, an alcoholic hydroxyl group, or an ester group is preferable because various properties such as heat resistance of the radiation-sensitive resin composition are improved.
  • the alicyclic structure contained in the alicyclic olefin monomer may be a monocyclic or polycyclic (condensed polycyclic, bridged ring, polycyclic combination thereof, etc.).
  • the alicyclic structure is preferably polycyclic from the viewpoints of mechanical strength, heat resistance and the like. Although there is no particular limitation on the number of carbon atoms constituting the alicyclic structure, it is usually in the range of 4 to 30, preferably 5 to 20, and more preferably 5 to 15, whereby heat resistance, Various characteristics such as pattern shape are highly balanced.
  • the proportion of the structural unit derived from the alicyclic olefin monomer in the alicyclic olefin resin is appropriately selected according to the purpose of use, but is usually 30 to 100% by weight, preferably 50 to 100% by weight, more preferably is 70 to 100 weight 0/0. If the proportion of the structural unit derived from the alicyclic olefin monomer is too small, the heat resistance is poor, which is not preferable.
  • the weight average molecular weight of the alicyclic olefin resin is usually 500 to 20,000, preferably 1,000 to 15,000, as the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC). Preferably it is in the range of 1,000 to 10,000.
  • Examples of the alicyclic olefin resin used in the present invention include (i) a ring-opened polymer of an alicyclic olefin monomer, (ii) a hydrogenated product of a ring-opened polymer of an alicyclic olefin monomer, (iii) an addition polymer of an alicyclic olefin monomer, (iv) an addition polymer of an alicyclic olefin monomer and a vinyl compound, (V) a monocyclic cycloalkene polymer, and (vi) an alicyclic ring.
  • these polymers include not only homopolymers but also copolymers.
  • the alicyclic olefin resin can be used alone or in combination of two or more.
  • the method for obtaining the alicyclic resin is not particularly limited.
  • bicyclo [2.2.1] hept1-2 - E down tricyclo [4. 3. 0. I 2 '5 ] Deka 3,7 Zhen, Te Torashikuro [4. 4. 0. I 2'. 5 I 7 '10] Dodeka 3 E down, 8 - Echiriden tetracyclo [4. 4. 0. I 2 '.
  • aromatic ring of the polymer obtained by addition polymerization of aromatic olefins such as styrene, ⁇ -methylstyrene, dibielbenzene, vinyl / lenaphthalene, and biertoluene is hydrogenated to form alicyclic olefins.
  • aromatic olefins such as styrene, ⁇ -methylstyrene, dibielbenzene, vinyl / lenaphthalene, and biertoluene is hydrogenated to form alicyclic olefins.
  • aromatic olefins such as styrene, ⁇ -methylstyrene, dibielbenzene, vinyl / lenaphthalene, and biertoluene is hydrogenated to form alicyclic olefins.
  • the same structural unit as the monomer-derived structural unit may be formed.
  • an alicyclic olefin resin containing a polar group is preferable from the viewpoints of solubility in an alkali developer (alkali solubility) and heat resistance.
  • a polar group a carboxyl group or an acid anhydride group is used. Containing sulfonic, phosphoric, hydroxyl (phenolic or alcoholic), or ester groups
  • the alicyclic olefin resin having is more preferred.
  • a ring-opened polymer obtained by using a norpolene-based monomer as an alicyclic olefin monomer, a hydrogenated product of the ring-opened polymer, And an addition copolymer with a bull compound are preferable as the alicyclic resin, and a ring-opening polymer of a norbornene-based monomer or a hydrogenated product of the ring-opening polymer and containing a polar group Is more preferred.
  • alicyclic resin one (CH 2 ) k COOR (where k is 0 or an integer of 1 to 4, and R is a hydrocarbon group having 1 to 12 carbon atoms or fluorine-substituted carbon)
  • a hydrolyzate of a ring-opening polymer of a norbornene-based monomer containing a polar group such as) or a hydrolyzate of a hydrogenated product of the ring-opening polymer has good alkali solubility; Particularly preferred is that development is easy and the sensitivity is good with an alkali developing solution.
  • the polar group such as the ester group is hydrolyzed, thereby improving the alkali solubility of the ring-opening polymer or a hydrogenated product thereof, and improving the sensitivity of the radiation-sensitive resin composition.
  • norbornene-based monomers having a polar group such as an ester group include, for example, 5-acetoxybicyclo [2.2.1] 1-hept-2-ene, 5-methoxycarburbicyclo [2.2.1] hept _ 2-ene, 5-methyl-1-methoxycarbodirubicyclo [2.2.1] hept-12-ene, 5-cyanobicyclo [2.2.1] heptose 2-ene, 8-acetoxytetracyclo [4. 4. 0. I 2 ' 5.
  • I 7 ' 10 Dodeca 3-ene, 8-methoxycarbonyl tetracyclo [4. 4. 0. I 2 ' 5.
  • I 7 ' 10 Dode 3-ene, 8-ethoxycarbenyltetracyclo [4. 4. 0. 12, 5. I ?, 10 ] dodeca- 31 , 8-n-propoxycarboletetracyclo mouth [4. 4. 0. I 2 ' 5. I 7 ' 10 ] dodeca 3-ene, 8-isopropoxycarbonyltetracyclo [4.4.0. I 2 ' 5. I 7 ' 10 ] dodeca 3-ene, 8-n —Butoxycarpine Torashikuro [4. 4. 0. I 2 '. 5 I 7' 10] dodecane force one three to E down, 8-methyl-one 8-methoxycarbonyl -. Rutetorashikuro [4. 4. 0.
  • I 2 '5 1 7 '10 1 dodecamethylene one 3-E down, 8-methyl-8-ethoxy Kano repo - Rutetorashikuro [4. 4. 0. I 2 ' 5.
  • I 7 ' 10 Dodeca 3-ene, 8-methyl-8-n-propoxyl-poninoleletetracyclo [4. 4. 0. I 2 ' 5.
  • I 7 '10 Dodeka 3 E down, 8-methyl-one 8-isopropoxyphenyl carbonylation Rutetorashikuro [4. 4. 0. I 2' 5. 1 7. 10] Dodeka 3 - E down, 8 Mechinore one 8- n-butoxycarbonyltetracyclo [4. 4. 0. I 2 ' 5.
  • I 7 ' 10 Dode force 3-ene, 8- (2, 2, 2-trifluoroethoxycarbol) Tetracyclo [4. 4. 0. I 2 ' 5.
  • I 7 ' 10 Dode force 3-ene, 8-methyl -8- (2,2,2-trifluoroethoxycarbonyl) tetracyclo [4 . 4. 0. I 2 '5.
  • I 7' 10 such Dodeka 3 E emissions and the like.
  • the norponene-based monomer having an ester group is preferable, and in particular, 8-methyl-8-methoxycarbonyltetracyclo [4.4.0.I 2 '5.
  • I 7' 10] Dodeka 3-E down is preferable.
  • hydrolysis is carried out using a solvent or an acid in a solvent according to a conventional method.
  • a method can be adopted.
  • the hydrolysis rate can be controlled by adjusting the reaction temperature, the reaction time, the amount of acid or alcohol, and the like.
  • the (B) acid generator used in the present invention is a compound that generates an acid upon irradiation with actinic radiation.
  • the acid generated by irradiation with actinic radiation increases the solubility difference between the actinic radiation-irradiated portion and the unirradiated portion of the resin film formed from the radiation-sensitive resin composition, and enables patterning.
  • Examples of the acid generator that gives a positive pattern include quinonediazidesulfonic acid ester.
  • Quinonediazidesulfonic acid ester is an ester compound of a quinonediazidesulfonic acid halide such as 1,2-naphthoquinonediazido5-sulfonic acid chloride and a phenol having at least one phenolic hydroxyl group, which is generally used as a photosensitizer. It is. 2, 3, 4— 03 06599
  • Examples of the acid generator that gives a negative pattern include onium salts such as diarydomonium salts, triarylsulfonium salts, and phenyldiazonium salts; imidosulfonate derivatives; tosylate compounds; carbonate compounds derivatives thereof; organic halogen compounds such as Harogeni ⁇ triazine derivatives; alpha, a 'one-bis (sulfo - Le) Jiazometan compound; a Ichiriki Lupo two Lou ⁇ - scan / Reho sulfonyl di ⁇ zone methane compound; Compounds that generate a relatively strong acid, such as a sulfone compound; an organic phosphoric acid ester compound; an organic acid amide compound;
  • the acid generators can be used alone or in combination of two or more.
  • the acid generator is used in an amount of usually 0.5 to 100 parts by weight, preferably 1 to 50 parts by weight, more preferably 10 to 30 parts by weight, based on 100 parts by weight of the alicyclic resin. Parts by weight. If the proportion of the acid generator is too small, the residual film ratio and the resolution may be deteriorated. Conversely, if the proportion of the acid generator is too large, the heat resistance (heat discoloration resistance) and light transmission may be reduced. (Transparency) may be reduced.
  • the (C) cross-linking agent used in the present invention reacts with the alicyclic resin to form a cross-linked structure between the alicyclic resin, and specifically has two or more reactive groups. It is a compound having no radical polymerizability. Examples of the reactive group include an amino group, a carboxyl group, a hydroxyl group, an epoxy group, and an isocyanate. And a bi- / re group.
  • crosslinking agent examples include aliphatic polyamines such as hexamethylene diamine;
  • Aromatic polyamines such as 4,4'-diaminodiphenyl ether and diaminodiphenylinolesulfone; 2,6-bis (4'-azidobenzal) cyclohexanone, 4,4'-diazidodiphenylsulfone azides; nylon, hexamethylene diamine terephthalamide to poly, made of polyamide such as hexamethylene isophthalate / Reami de poly -; N, N,, ⁇ ' , N r, - such as melamine (Kisaarukokishi methyl to) Melamines; N, N ', ⁇ ", N w — (tetraanolecoxymethyl) glycol diols such as glycol diol; acrylate compounds such as ethylene glycol di (meth) acrylate and epoxy acrylate resin Hexamethylene diisocyanate polyisocyanate, isophorone diisocyanate polyisocyanate
  • N-alkoxymethylated melamine, N-alkoxymethyl ehglycol peryl, and epoxy compounds are preferable because of their good heat resistance.
  • These compounds are PL-117, PL-117, UFR65, CYMEL300, CYMEL303 (all of which are trade names, Mitsui Scitechne), Commercially available, such as B X-400, Two-strength Rack MW—30, MX290 (both are trade names, manufactured by Sanwa Chemi-Carne Earth), Epicoat Series (manufactured by Yuka Shell Epoxy) It is easy to obtain as a product.
  • a crosslinking agent and a salt compound are each independently Alternatively, two or more kinds can be used in combination.
  • the amount of the crosslinking agent used is usually 1 to 100 parts by weight, preferably 5 to 80 parts by weight, more preferably 10 to 70 parts by weight, based on 100 parts by weight of the alicyclic olefin resin. Most preferably, it is 20 to 50 parts by weight. If the proportion of the crosslinking agent used is too large or too small, the pattern Jung performance tends to decrease.
  • the (D) phenol compound used in the present invention is a compound represented by the formula (1).
  • n is an integer of 1 to 4.
  • n is an integer of 2-3.
  • A is a carbon atom
  • n is 4.
  • n is preferably 3 or 4, and more preferably 3.
  • A is an n-valent organic group or a carbon atom.
  • the n-valent organic group include an alkyl group having 1 to 6, preferably 3 to 5, and more preferably 3 to 4 carbon atoms.
  • the alkyl group may be linear, branched, or cyclic.
  • the n-valent organic group one (CH 2 —G—CH 2 ) y-(y is an integer of 1-3, preferably 1-2, and G is an oxygen atom or a sulfur atom ),
  • A is an alkyl group having 1 to 6, preferably 3 to 5, more preferably 3 to 4 carbon atoms, or the following formula (3)
  • R 7 to R 9 are each independently a hydrogen atom or a hydroxyphenylalkyl group (the alkyl moiety has 1 to 3 carbon atoms).
  • A is an alkyl group having 1 to 6, preferably 3 to 5, more preferably 3 to 4 carbon atoms, and one (CH 2 -G-CH 2 ) y- (y is , 1-3, preferably 1-2, G is an oxygen atom or a sulfur atom.),
  • a divalent phenylene group (a phenylene group is a hydroxyl group or the number of carbon atoms) It may have 1 to 3 alkyl groups as a substituent.
  • A is a trivalent phenylene group or the following formula (4)
  • A is preferably a carbon atom.
  • B is a divalent organic group or a single bond, and is preferably the following formula (5)
  • L is an oxygen atom or 1 NH—, and m is an integer of 1 to 3.
  • Y is a hydrogen atom or a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms.
  • ⁇ is a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, or a group represented by the formula (2).
  • 1 to! ⁇ 3 are each independently a hydrogen atom, a hydroxyl group, or a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms.
  • the phenolic conjugate represented by the above formula (1) has excellent compatibility with other components in the radiation-sensitive resin composition and gives a good pattern shape.
  • phenol compound used in the present invention those having two or more aromatic rings are preferably used.
  • examples of such a phenol compound include the following compounds.
  • Examples of the compound having two aromatic rings include the following phenol compounds.
  • n l
  • A 4-hydroxyphenyl
  • B single bond
  • R 1 to R 3 hydrogen atom
  • Y and methyl 2,2-bis (4 —Hydroxyphenyl) propane
  • n l
  • A 2,4-dihydroxyphenyl
  • B single bond
  • R 1 and R 2 hydrogen atom
  • R 3 hydroxyl group
  • Y and Z methyl 2,2-bis (2,4-dihydroxypheninole) propane
  • n 2
  • A —CH 2 —O—CH 2 —CH 2 —0—CH 2
  • B in formula (5)
  • Examples of the compound having three aromatic rings include the following phenol compounds.
  • B single bond
  • R i methyl group
  • R 2 and R 3 hydrogen atom
  • Y methyl group
  • Examples of the conjugate having an aliphatic ring or a heterocyclic ring in addition to the three aromatic rings include the following phenol compounds.
  • Examples of the compound having four or more aromatic rings include the following phenol compounds.
  • n l ⁇ -di (4-hydroxyphenyl) methyl
  • B single bond,! ⁇ ⁇ ! ⁇
  • Y hydrogen atom
  • ⁇ substituted phenyl group represented by formula (2)
  • R 4 R 6 in formula (2) hydrogen atom] 1,1,2,2-tetrakis (4 -Hydroxyphenyl) ethane
  • B single bond
  • R 2 and R 3 hydrogen atom
  • Y Hydrogen atom
  • n 3
  • A l, 3,5-phenylene
  • B single bond
  • Y and Y methyl group 1,3 , 5-tris [21- (4-hydroxyphene) propynole] benzene
  • n 3
  • A 2,4,6-trimethyl-1,3,5-phenylene
  • B single bond
  • R 1 and R 2 t-butyl group
  • R 3 hydrogen atom
  • Y and hydrogen 1,3,5-trimethine 1,2,4,6-tris (3,5-di-t-petit / le 4-hydroxybenzinole) benzene
  • n 2
  • A 1, 4—phenylene
  • B single bond
  • ⁇ ⁇ 3 hydrogen atom
  • Y a hydrogen atom
  • Zeta substituted Hue formula (2) - a le group [formula (2)
  • R 4 to R 6 hydrogen atom in] ⁇ , a, a ' , A'-tetrakis (4-hydroxyphenyl) -1-4-xylene,
  • n 4
  • A C
  • B divalent organic group represented by formula (5)
  • L oxygen atom
  • m 2
  • R 1 and ⁇ ⁇ ⁇ R 2 t_butyl group
  • R 3 hydrogen atom
  • Y and H hydrogen atom
  • pentaerythritol tetrakis [3- (3,5-zy-t-butyl-4-hydroxyphenyl) propionate].
  • phenolic compounds compounds that have high compatibility with the alicyclic olefin resin and are excellent in transparency, and therefore have a rich ring structure, specifically, three or more aromatic rings in one molecule Are preferable, and compounds having four aromatic rings or compounds having an aliphatic ring or a hetero ring in addition to three aromatic rings are more preferable.
  • the proportion of the (D) phenol compound used is usually 0.1 to 30 parts by weight, preferably 0.1 to 25 parts by weight, more preferably 100 to 100 parts by weight of the alicyclic resin. 0.5 to 20 parts by weight. If the proportion of the phenol compound is too small, it is difficult to obtain a sufficient effect, while if it is too large, development residues are likely to be generated.
  • the phenolic compound in which Z is a hydrogen atom is preferable because the pattern jungling performance and the transparency performance can be balanced with a small addition amount (10 parts by weight or less) in the above usage ratio.
  • a solvent capable of dissolving each of the above components may be used.
  • examples of such a solvent include alcohols such as methanol, ethanol, propanol, butanol, and 3-methoxy-13-methylptanol; cyclic ethers such as tetrahydrofuran and dioxane; methyl acetate sorb acetate; Cellosolve esters such as chinorecellosolve acetate; ethylene glycol olemonoethyl ether / ethylene glycol ethylene glycol monoester / ethylene glycol ethylene glycol monoethylene ether / propylene glycol glycolose monoethyl ether / ethylene glycol; Propylene Glycol / Remonopropyl Ether, Propylene Glycol Monobutyl Ether / Re, Diethylene Glycol / Remonomethyl 7 Reate / Re, Diethylene Glycol Remonoethyl Ether,
  • the solvent is used in an amount sufficient to uniformly dissolve the components.
  • the radiation-sensitive resin composition of the present invention contains a nonionic interface such as polyoxyethylene lauryl ether or polyoxyethylene diallate for the purpose of preventing striae yon (after coating streaks) and improving developability.
  • Activators Fluorosurfactants such as F-top series manufactured by Shin-Akita Kasei, Megafac series manufactured by Omoto Ink and Chemicals, Flip Lard series manufactured by Sumitomo 3REM, and Asahi Guard series manufactured by Asahi Glass Co .; Various surfactants, such as silane-based surfactants such as Organosiloxane Bolmer ⁇ -series manufactured by Co., Ltd .; and atrial acid copolymer-based surfactants such as Polyflow Series manufactured by Kyoeisha Yushi Kagaku Kogyo Co., Ltd. .
  • the surfactant is used as needed in an amount of usually 2 parts by weight or less, preferably 1 part by weight or less, based on 100 parts by weight of the solid content
  • a functional silane coupling agent such as ⁇ -glycidoxypropyltrimethoxysilane or the like can be added as an adhesion aid for the purpose of improving the adhesion to the substrate.
  • the proportion of the adhesion aid used is alicyclic
  • the amount is usually 20 parts by weight or less, preferably 0.05 to 10 parts by weight, particularly preferably 1 to 0 parts by weight based on 100 parts by weight of the refin resin.
  • additives such as an antistatic agent, a storage stabilizer, an antifoaming agent, a pigment and a dye may be added to the radiation-sensitive resin composition of the present invention, if necessary.
  • the components are mixed according to a conventional method and dissolved in a solvent to prepare a thigh-sensitive resin composition.
  • the solid concentration of the radiation-sensitive resin composition of the present invention may be appropriately set in consideration of the required thickness of the resin film, but is usually 5 to 40% by weight from the viewpoint of operability.
  • the radiation-sensitive resin composition is preferably used after filtering out foreign substances and the like using a filter having a pore size of about 0.1 to 1 ⁇ .
  • the radiation-sensitive resin composition of the present invention may be used for a device such as a display device or an integrated circuit device, a protective film such as a color filter for a liquid crystal display, a flattening film for flattening the device surface or wiring, It is suitable as a material for various electronic component resin films such as insulating films (including interlayer insulating films and solder resist films, which are electrical insulating films for thin-type transistor-type liquid crystal display elements and integrated circuit elements). is there.
  • the radiation-sensitive resin composition of the present invention to form a resin film on a substrate, for example, irradiating active radiation through a mask pattern to form a latent image pattern in the resin film,
  • the resin pattern is formed on the substrate by bringing the resin pattern having the above into contact with the developing solution so that the resin pattern is exposed.
  • a substrate having a patterned resin film can be manufactured.
  • a patterned resin film also referred to as a “resin pattern”
  • a method of forming a resin film on a substrate a method of applying a radiation-sensitive resin composition to a substrate surface, drying and forming a resin film directly on the substrate; polyethylene terephthalate finolem, polypropylene film, polyethylene film, etc.
  • a radiation-sensitive resin composition is applied to a support made of, dried, to form a resin film, and then a resin film with a support is superimposed on a substrate.
  • a press machine such as a press laminator, a press press, a vacuum laminator, a vacuum press, and a roll laminator.
  • the temperature at the time of thermocompression bonding is usually 30 to 2.50 ° C, preferably 70 to 200 ° C.
  • Crimping force is usually 10 kPa to 20 MPa, preferably 100 kPa to 100 OMPa.
  • Crimping time is usually 30 seconds to 5 hours, preferably 1 minute to 3 hours.
  • the pressure is usually reduced to 1 O OkPa to: LPa, preferably 40 kPa to 10 Pa.
  • the coating film is dried by heat! To obtain a resin film having no fluidity.
  • the heating conditions for forming the resin film directly on the substrate surface vary depending on the type and blending ratio of each component, but are usually about 60 to 120 ° C for about 10 to 600 seconds.
  • the heating for drying is generally referred to as "prebeta (Pre-Bake)" 5.
  • the obtained resin film is irradiated with actinic radiation to form a latent image pattern on the resin film.
  • actinic radiation is not particularly limited, and includes, for example, ultraviolet rays, far ultraviolet rays, X-rays, electron beams, and proton beam rays, and visible rays and ultraviolet rays are particularly preferable.
  • the radiation dose for irradiation can be arbitrarily set depending on the type and thickness of the resin film.
  • the pattern can be formed by irradiating with an irradiation beam through a mask or by directly drawing with an electron beam.
  • the resin film having a latent image pattern on the substrate is brought into contact with a developing solution to remove the irradiated portion and to make the latent image pattern visible (developed).
  • a developing solution to remove the irradiated portion and to make the latent image pattern visible (developed).
  • heating PEB treatment: Post Exposure Bake
  • the PEB treatment By performing the PEB treatment, development residues such as unnecessary resin components to be dissolved and removed in the developer can be reduced.
  • the alicyclic olefin resin has an alkali-soluble polar group, particularly an acidic group, because the outflow by the developer becomes easier.
  • an aqueous solution obtained by dissolving an alkaline compound in water is preferably used.
  • the alkaline compounds include inorganic hydroxides such as sodium hydroxide, hydroxylated lime, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia; and primary amines such as ethyl ethylamine and n-propylamine.
  • Secondary amines such as getylamine, di- ⁇ -propylamine; tertiary amines such as triethylamine, methyl getylamine, ⁇ -methylpyrrolidone; alcoholamines such as dimethylethanolamine and triethanolamine; Quaternary ammonium salts such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, and choline; pyrrole, piperidine, 1,8-diazabicyclo [5. 4. 0] 7-en, 1, 5-j Bicyclo [. 4.3 0] cyclic ⁇ Min such as nona one 5-E down; and the like.
  • These alkali compounds can be used alone or in combination of two or more.
  • a water-soluble organic solvent such as methanol or ethanol or a surfactant can be added to the developer.
  • the development time is usually 30 to 180 seconds.
  • the method of contacting the developing solution with the resin film having the latent image pattern is not particularly limited. For example, according to a paddle method, a spray method, a dive method, or the like.
  • the development temperature is not particularly limited, it is generally 15 to 35 ° C, preferably 20 to 30 ° C.
  • the substrate After forming the desired resin pattern on the substrate in this way, if necessary, In order to remove unnecessary development residues remaining on the substrate, on the back surface of the substrate, and on the edge of the substrate, the substrate can be brought into contact with a rinsing liquid by a conventional method.
  • the substrate in contact with the rinsing liquid is usually dried with compressed air or compressed nitrogen to remove the rinsing liquid on the substrate. Further, if necessary, the entire surface of the substrate having the resin pattern can be irradiated with active radiation.
  • the resin pattern formed on the substrate is cured by heating (post beta: Post Bake) as necessary.
  • the heating method is performed by a heating device such as a hot plate or oven.
  • the heating temperature is usually 150 to 250 ° C, preferably 180 to 220 ° C, and the heating time is, for example, usually 5 to 60 minutes when using a hot plate, and usually 30 to 90 minutes when using an oven. It is.
  • Post baking is preferably performed in a low oxygen atmosphere, specifically in an atmosphere having an oxygen concentration of 10 ppm or less.
  • a mask having a predetermined pattern was placed on the obtained silicon substrate with a coating film, and irradiated with ultraviolet rays having a wavelength of 365 nm and a light intensity of 5 mW / cm 2 in air for 40 seconds.
  • a developing treatment was performed at 25 ° C. for 60 seconds using a 0.3% aqueous solution of tetramethylammonium as a developing solution.
  • a rinsing treatment with ultrapure water was performed for 1 minute to form a thin film having a posi-type pattern.
  • the entire surface was irradiated with ultraviolet light having a light intensity at 365 nm of 5 mWZ cm 2 for 60 seconds.
  • the silicon substrate on which the pattern was formed was heated on a hot plate at 200 ° C for 30 minutes to post-bake the pattern and coating film, forming a patterned thin film (patterned resin film).
  • a substrate was obtained.
  • a stepped substrate silicon oxide film substrate having a 1 / ⁇ 1 step
  • the pattern was obtained in the same manner as in Example 1 except that 4,4 '-[1- (4- (1- (4-hydroxyphenyl) -11-methylethyl) phenyl] ethylidene] bisphenol was used as the phenol compound.
  • a silicon substrate, a glass substrate, and a stepped substrate on which a thin film was formed were obtained.
  • a patterned thin film was prepared in the same manner as in Example 1 except that 1,3,5-trimethinole 2,4,6-tris (3,5-di-t-butyl-14-hydroxybenzyl) benzene was used as the phenolic compound.
  • a silicon substrate, a glass substrate, and a substrate having a step were formed.
  • a silicon substrate, a glass substrate, and a patterned substrate-like thin film were formed in the same manner as in Example 1 except that tris- (3,5-di-t-butyl-4-hydroxybenzyl) -isocyanurate was used as the phenol compound.
  • a stepped substrate was obtained.
  • a silicon substrate, a glass substrate, and a stepped substrate having a patterned thin film formed thereon were obtained in the same manner as in Example 1 except that the phenolic conjugate was not used.
  • each of the silicon substrates obtained in Examples 1 to 6 and Comparative Example 1 was JI
  • the dielectric constant ( ⁇ ) at 10 KHz (room temperature) measured according to SC6481 is less than 2.85, and the film thickness after heating the substrate in a 220 ° C oven for 60 minutes is It has been confirmed that the thickness is 95% or more, the dielectric constant is low, and the dimensional stability under heat is excellent.
  • Each of the glass substrates obtained in Examples 1 to 6 and Comparative Example 1 had a film thickness change rate (S) of less than 10% when the substrates were immersed in dimethyl sulfoxide at 70 ° C. for 30 minutes. It was confirmed that the solvent resistance was excellent.
  • Each of the glass substrates on which the patterned thin films obtained in Examples 1 to 6 and Comparative Example 1 were formed was subjected to 400 to 800 nm using an ultraviolet-visible-near-infrared spectrophotometer (V-570) manufactured by JASCO Corporation.
  • V-570 ultraviolet-visible-near-infrared spectrophotometer
  • the minimum light transmittance (t.) At the following wavelengths was measured.
  • This rate of change in heating was used as an index of heat-resistant discoloration.
  • the film thickness of the unexposed portion before and after development for 1 minute with a 0.3% aqueous solution of tetramethylammonium hydroxide was measured using a contact-type film thickness meter.
  • XI 00 was taken as the residual film ratio (R).
  • Table 1 shows the measurement results.
  • the present invention in addition to being excellent in dielectric properties, heat discoloration resistance, flatness, solvent resistance, etc., transparency, heat discoloration resistance, resolution, remaining film ratio, etc. are remarkably improved, and the pattern shape is also improved.
  • a good radiation-sensitive resin composition is provided.
  • the resin film formed from the radiation-sensitive resin composition of the present invention is hardly discolored by heat treatment at a high temperature exceeding 200 ° C., and can maintain a high degree of transparency.
  • the patterned resin film formed using the radiation-sensitive resin composition of the present invention can be used as a transparent resin film having excellent transparency.
  • the resin film of the present invention is, for example, an electronic element such as a semiconductor element, a light emitting diode, and various kinds of memories; an overcoat material such as a hybrid IC, an MCM, and a printed wiring board; an interlayer insulating film of a multilayer circuit board; It can be suitably used for various electronic components.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)

Abstract

La présente invention a trait à une composition de résine sensible au rayonnement comprenant une résine oléfinique alicyclique, un générateur d'acide, un agent de réticulation, un composé phénolique présentant une structure déterminée, et un solvant. La composition permet d'obtenir une couche de résine présentant une faible permittivité et est excellente en termes de transparence, tenue à la décoloration thermique, résolution, maintien d'épaisseur de couche, configuration de motifs et autres. L'invention a trait également à un procédé de production d'un substrat présentant une couche de résine à motifs, comprenant l'utilisation de la composition de résine sensible au rayonnement.
PCT/JP2003/006599 2002-05-27 2003-05-27 Composition de resine sensible au rayonnement, procede de production d'un substrat comprenant couche de resine a motifs, et utilisation de la composition de resine WO2003100524A1 (fr)

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JP2004507917A JP3843995B2 (ja) 2002-05-27 2003-05-27 感放射線性樹脂組成物、パターン状樹脂膜を有する基板の製造方法、及び該樹脂組成物の利用

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006113557A (ja) * 2004-09-14 2006-04-27 Asahi Kasei Electronics Co Ltd 感光性樹脂積層体の製造方法
JP2006156821A (ja) * 2004-11-30 2006-06-15 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2007045996A (ja) * 2005-08-12 2007-02-22 Jsr Corp 樹脂組成物、カラーフィルタの保護膜の形成方法、およびカラーフィルタの保護膜
JP2007078820A (ja) * 2005-09-12 2007-03-29 Sumitomo Bakelite Co Ltd 感光性樹脂組成物、それを用いた半導体装置、表示素子
US7569260B2 (en) 2003-08-21 2009-08-04 Asahi Kasei Chemicals Corporation Photosensitive composition and cured products thereof
JP2009533707A (ja) * 2006-04-13 2009-09-17 コーロン インダストリーズ インク ポジティブ型フォトレジスト用組成物およびこれから製造されたポジティブ型フォトレジストフィルム
CN107844030A (zh) * 2016-09-20 2018-03-27 东京应化工业株式会社 抗蚀剂组合物及抗蚀图案形成方法

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JP2001188343A (ja) * 1999-12-28 2001-07-10 Nippon Zeon Co Ltd 感光性樹脂組成物
US20010033990A1 (en) * 2000-03-21 2001-10-25 Shin-Etsu Chemical Co., Ltd. Resist compositions and patterning process
WO2002029493A1 (fr) * 2000-09-29 2002-04-11 Nippon Zeon Co., Ltd. Composition de resine photosensible servant a creer une couche isolante, couche isolante d'elements electroluminescents organiques et procede de creation

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Publication number Priority date Publication date Assignee Title
JPS5720733A (en) * 1980-07-14 1982-02-03 Japan Synthetic Rubber Co Ltd Photoresist composition
JPH05165201A (ja) * 1991-12-11 1993-07-02 Tosoh Corp ネガ型レジスト材料
JPH06348005A (ja) * 1993-06-04 1994-12-22 Tokyo Ohka Kogyo Co Ltd ポジ型ホトレジスト組成物
JPH07133338A (ja) * 1993-11-11 1995-05-23 Sumitomo Chem Co Ltd 硬化性樹脂組成物
JPH07234505A (ja) * 1994-02-21 1995-09-05 Tokyo Ohka Kogyo Co Ltd ポジ型ホトレジスト組成物
JPH10307388A (ja) * 1997-05-06 1998-11-17 Jsr Corp 感放射線性樹脂組成物
JPH1152574A (ja) * 1997-08-06 1999-02-26 Jsr Corp 感放射線性樹脂組成物
JPH11258802A (ja) * 1998-03-16 1999-09-24 Fuji Photo Film Co Ltd ネガ型レジスト組成物
GB2356258A (en) * 1999-11-09 2001-05-16 Sumitomo Chemical Co Chemical amplification type resist composition
JP2001188343A (ja) * 1999-12-28 2001-07-10 Nippon Zeon Co Ltd 感光性樹脂組成物
US20010033990A1 (en) * 2000-03-21 2001-10-25 Shin-Etsu Chemical Co., Ltd. Resist compositions and patterning process
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7569260B2 (en) 2003-08-21 2009-08-04 Asahi Kasei Chemicals Corporation Photosensitive composition and cured products thereof
JP2006113557A (ja) * 2004-09-14 2006-04-27 Asahi Kasei Electronics Co Ltd 感光性樹脂積層体の製造方法
JP4578358B2 (ja) * 2004-09-14 2010-11-10 旭化成イーマテリアルズ株式会社 感光性樹脂積層体の製造方法
JP2006156821A (ja) * 2004-11-30 2006-06-15 Sumitomo Bakelite Co Ltd 樹脂組成物、樹脂層、樹脂層付きキャリア材料および回路基板
JP2007045996A (ja) * 2005-08-12 2007-02-22 Jsr Corp 樹脂組成物、カラーフィルタの保護膜の形成方法、およびカラーフィルタの保護膜
JP4735818B2 (ja) * 2005-08-12 2011-07-27 Ｊｓｒ株式会社 樹脂組成物、カラーフィルタの保護膜の形成方法、およびカラーフィルタの保護膜
JP2007078820A (ja) * 2005-09-12 2007-03-29 Sumitomo Bakelite Co Ltd 感光性樹脂組成物、それを用いた半導体装置、表示素子
JP2009533707A (ja) * 2006-04-13 2009-09-17 コーロン インダストリーズ インク ポジティブ型フォトレジスト用組成物およびこれから製造されたポジティブ型フォトレジストフィルム
CN107844030A (zh) * 2016-09-20 2018-03-27 东京应化工业株式会社 抗蚀剂组合物及抗蚀图案形成方法
CN107844030B (zh) * 2016-09-20 2023-04-25 东京应化工业株式会社 抗蚀剂组合物及抗蚀图案形成方法

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