CN105143979A - Composition for forming resist underlayer film - Google Patents
Composition for forming resist underlayer film Download PDFInfo
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- CN105143979A CN105143979A CN201480021117.6A CN201480021117A CN105143979A CN 105143979 A CN105143979 A CN 105143979A CN 201480021117 A CN201480021117 A CN 201480021117A CN 105143979 A CN105143979 A CN 105143979A
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/026—Wholly aromatic polyamines
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- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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Abstract
The invention provides a novel composition for forming a resist underlayer film. The composition for forming the resist underlayer film, contains a solvent and a polymer that has a constitutional unit that can be represented by formula (1). In formula (1), X<1> represents a C6-20 divalent organic group that has at least one aromatic ring that may be substituted with a halogeno group, a nitro group, an amino group, or a hydroxy group; and X<2> represents either a methoxy group or a C6-20 organic group that has at least one aromatic ring that may be substituted with a halogeno group, a nitro group, an amino group, or a hydroxy group.
Description
Technical field
The present invention relates to photoetching process resist lower membrane formation composition.Particularly relate to for the formation of high rigidity, the composition that the resist lower membrane of bending (wiggling) of the Resist patterns formed by photoetching process is less likely to occur.
Background technology
In the manufacture of semiconductor device, photoetching process is utilized to carry out microfabrication.This photoetching process is known exists following problems: when exposing the resist layer on substrate with ultraviolet lasers such as KrF excimer laser, ArF excimer lasers, because this ultraviolet laser occurs to reflect and the impact of the standing wave of generation on the surface of the substrate, the Resist patterns with intended shape can not be formed.In order to solve this problem, adopt the method that resist lower membrane (antireflection film) is set between substrate and resist layer.And, as the composition for the formation of resist lower membrane, known use novolac resin.Such as, patent documentation 1 and the photoresist lower membrane formation material of the resin of repetitive that Patent Document 2 discloses containing the compound novolaks had having hexichol phenolic group.Further, Patent Document 3 discloses the polymkeric substance in the main chain being included in polymkeric substance with the aromatic ring that more than 3 or 3 have condensed and can the antireflection film composition of rotary coating.
In addition, the filming of resist layer be required in order to the miniaturization with Resist patterns, the resist lower membrane of also known formation at least 2 layers and the photoetching process that this resist lower membrane is used as mask material.As the material forming aforementioned at least 2 layers, organic resin (such as, acryl resin, novolac resin), silicones (such as, organopolysiloxane), inorganic silicon compound (such as, SiON, SiO can be enumerated
2).When the pattern formed by above-mentioned organic resin layer is carried out dry ecthing as mask, this pattern is needed to have elching resistant to etching gas (such as fluorocarbon).As the composition for the formation of such organic resin layer, such as, Patent Document 4 discloses the composition containing the polymkeric substance comprising heteroaromatic part.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 2006-259249 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2007-316282 publication
Patent documentation 3: Japanese Unexamined Patent Application Publication 2010-528334 publication
Patent documentation 4: Japanese Unexamined Patent Publication 2007-017976 publication
Summary of the invention
Invent problem to be solved
In addition, there is following problem: via above-mentioned photoetching process and etch process when needing the substrate processed forms Resist patterns, along with the pattern width formed narrows, the bending of irregular pattern easily occurring.Specifically, when etching target substrate processing as in the resist lower membrane of mask material use, the phenomenon that the pattern particularly formed by organic resin layer bends right and left.
For solving the means of problem
The present invention solves the problem.Namely the present invention is a kind of resist lower membrane formation composition, and comprise polymkeric substance and solvent, described polymkeric substance has the structural unit represented by following formula (1),
In formula (1), X
1represent the divalent organic base of the carbon number 6 ~ 20 with the aromatic rings that at least 1 can be replaced by halogeno-group, nitro, amino or hydroxyl, X
2represent organic group or the methoxyl of the carbon number 6 ~ 20 with the aromatic rings that at least 1 can be replaced by halogeno-group, nitro, amino or hydroxyl.
As halogeno-group above-mentioned and described later, such as chloro base, bromo base can be enumerated.As the divalent organic base with the carbon number 6 ~ 20 of at least 1 aromatic rings above-mentioned and described later, (in formula, n represents 0 or 1 can to enumerate such as phenylene, biphenylene, sub-terphenyl, fluorenylidene, naphthylene, anthrylene, sub-pyrenyl (group represented by following formula (a-1) and following formula (a-2)), sub-carbazyl (group represented by following formula (b)) and the group that represented by following formula (c).)。As the above-mentioned organic group with the carbon number 6 ~ 20 of at least 1 aromatic rings, such as phenyl, xenyl, terphenyl, fluorenyl, naphthyl, anthryl, pyrenyl, carbazyl can be enumerated, (in formula, n represents 0 or 1 for the group that represented by following formula (d-1) and following formula (d-2).)。
Aforementioned polymer also can have the structural unit represented by following formula (2),
In formula (2), X
1represent the divalent organic base of the carbon number 6 ~ 20 with the aromatic rings that at least 1 can be replaced by halogeno-group, nitro, amino or hydroxyl, R
3represent phenyl, naphthyl, anthryl, pyrenyl, thienyl or pyridine radicals, R
4represent hydrogen atom, phenyl or naphthyl, R
3and R
4when representing phenyl respectively, R
3and R
4fluorenes ring is formed together with the same carbon atom that can combine with them.
In resist lower membrane formation composition of the present invention, be further used as any composition, at least a kind in crosslinking chemical, acid compound, thermal acid generator and surfactant can be contained.
The effect of invention
Use resist lower membrane formation composition of the present invention and the resist lower membrane that formed is high rigidity, and by this resist lower membrane of application, bending (wiggling) of the pattern formed in photoetching process can be suppressed.
Embodiment
As resist lower membrane of the present invention formation with comprise in composition, the structural unit of the polymkeric substance with the structural unit represented by above-mentioned formula (1), the structural unit such as represented by following formula (1-1) ~ formula (1-10) can be enumerated.
Further, as the structural unit represented by above-mentioned formula (2), the structural unit such as represented by following formula (2-1) can be enumerated.
The weight-average molecular weight of the polymkeric substance that resist lower membrane formation composition of the present invention comprises counts such as 2 with polystyrene standard scaled value, 000 ~ 10,000.
Aforementioned polymer can by make to have the diphenol compound of 2 hydroxy phenyls and aromatics or hetero ring type compound, as required with aromatic aldehyde or aromatic ketone, under the existence of the acid catalysts such as sulfoacid compound, carry out polyreaction and synthesize.That synthesis as aforementioned polymer uses, to have 2 hydroxy phenyls diphenol compound, can enumerate such as, 3,3 ', 5,5 '-tetramethoxymethyl-4,4 '-dihydroxybiphenyl.As the aromatics that the synthesis of aforementioned polymer uses, can enumerate such as, benzene, naphthalene, anthracene, pyrene, fluorenes, meta-terphenyl.As the hetero ring type compound that the synthesis of aforementioned polymer uses, can enumerate such as, carbazole.As the aromatic aldehyde that the synthesis of aforementioned polymer uses, can enumerate such as, furfural, pyridine carboxaldehyde, benzaldehyde, naphthaldehyde, anthraldehyde, formaldehyde, salicylide, ethylalbenzene, 3-hydrocinnamicaldehyde, tolyl aldehyde, (N, N-dimethylamino) benzaldehyde, acetoxyl group benzaldehyde, 1-pyrene formaldehyde, anisaldehyde.In addition, the aromatic ketone that the synthesis of aforementioned polymer uses is diaryl ketone, can enumerate such as, diphenylketone, phenyl napthyl ketone, dinaphthyl ketone, phenyltoluene base ketone, xylyl ketone, 9-Fluorenone.The diphenol compound that the synthesis of aforementioned polymer uses is not limited to a kind of compound, and can use two or more, aromatics, hetero ring type compound, aromatic aldehyde and aromatic ketone are also not limited to a kind of compound, can use two or more.
Resist lower membrane formation composition of the present invention can contain crosslinking chemical further.As aforementioned crosslinking agent, preferred use has at least two and is cross-linked to form substituent cross-linked compound.Can enumerate such as, there is methylol, methoxy etc. and be cross-linked to form substituent, melamine based compound, substituted urea based compound and phenol system compound.Specifically, be the compounds such as methoxymethylated glycoluril, methoxymethylated melamine, can enumerate such as, tetramethoxymethylglycoluril, four butoxymethyl glycolurils, HMMM.Further, alternatively urea based compound, can enumerate such as, tetramethoxymethyl urea, four butoxymethyl ureas.As phenol system compound, can enumerate such as, tetrakis hydroxymethyl phosphonium xenol, tetramethoxymethyl xenol, tetramethoxymethyl biphenol.
As aforementioned crosslinking agent, in addition, the compound with at least two epoxy radicals can also be used.As such compound, can enumerate such as, three (2,3-glycidyl) isocyanuric acid ester, BDO diglycidyl ether, 1,2-epoxy-4-(epoxy ethyl) cyclohexane, glycerine triglycidyl group ether, diglycol diglycidyl ether, 2,6-diglycidyl phenylglycidyl ether, 1,1,3-tri-[to (2,3-glycidoxy) phenyl] propane, 1,2-cyclohexane cyclohexanedimethanodibasic diglycidyl 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 glycidyl ether, bisphenol-A-diglycidyl ether, エ ポ リ ー De (registered trademark) GT-401 of (strain) ダ イ セ Le, エ ポ リ ー De GT-403, エ ポ リ ー De GT-301, エ ポ リ ー De GT-302, セ ロ キ サ イ De (registered trademark) 2021, セ ロ キ サ イ De 3000, Mitsubishi Chemical's (strain) make 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828, 807, 152, 154, 180S75, 871, 872, the EPPN201 that Japan's chemical drug (strain) makes, EPPN202, EOCN-102, EOCN-103S, EOCN-104S, EOCN-1020, EOCN-1025, EOCN-1027, デ ナ コ ー Le (registered trademark) EX-252 that Na ガ セ ケ system テ ッ Network ス (strain) makes, デ ナ コ ー Le EX-611, デ ナ コ ー Le EX-612, デ ナ コ ー Le EX-614, デ ナ コ ー Le EX-622, デ ナ コ ー Le EX-411, デ ナ コ ー Le EX-512, デ ナ コ ー Le EX-522, デ ナ コ ー Le EX-421, デ ナ コ ー Le EX-313, デ ナ コ ー Le EX-314, デ ナ コ ー Le EX-321, the CY175 that BASF ジ ャ パ Application (strain) makes, CY177, CY179, CY182, CY184, CY192, the エ ピ Network ロ Application 200 that DIC (strain) makes, エ ピ Network ロ Application 400, エ ピ Network ロ Application 7015, エ ピ Network ロ Application 835LV, エ ピ Network ロ Application 850CRP.As the aforementioned compound with at least two epoxy radicals, in addition, the epoxy resin with amino can also be used.As such epoxy resin, can enumerate such as, YH-434, YH-434L (new daily use chemicals エ Port キ シ manufactures (strain) system).
As aforementioned crosslinking agent, in addition, the compound with at least 2 blocked isocyanate bases can also be used.As such compound, can enumerate such as, タ ケ ネ ー ト (registered trademark) B-830, タ ケ ネ ー ト B-870N that Mitsui Chemicals (strain) is made, VESTANAT (registered trademark) B1358/100 of エ ボ ニ ッ Network デ グ サ society.
As aforementioned crosslinking agent, in addition, the compound with at least 2 vinyl ether groups can also be used.As such compound, can enumerate such as, two (4-(vinyloxy methyl) cyclohexyl methyl) glutarate, three (ethylene glycol) divinyl ether, hexane diacid divinyl ester, diethylene glycol divinyl ether, 1, 2, 4-tri-(4-vinyloxy butyl) trimellitate, 1, 3, 5-tri-(4-vinyloxy butyl) trimellitate, two (4-(vinyl oxygen base) butyl) terephthalate, two (4-(vinyl oxygen base) butyl) isophthalic acid ester, ethylene glycol divinyl ether, 1, 4-butylene glycol divinyl ether, tetramethylene glycol divinyl ether, tetraethylene glycol divinyl ether, neopentyl glycol divinyl ether, trimethylolpropane tris vinyl ether, trimethylolethane trivinyl base ether, hexanediol divinyl ether, 1, 4-cyclohexanediol divinyl ether, tetraethylene glycol divinyl ether, pentaerythrite divinyl ether, pentaerythrite trivinyl ether and cyclohexanedimethanol divinyl base ether.
1 kind that selects from these various crosslinking chemicals can be added, also can combine and add two or more.Remove the solid constituent after aftermentioned solvent relative to from resist lower membrane formation composition of the present invention, containing of above-mentioned crosslinking chemical is proportional, such as 2 quality % ~ 60 quality %.
Resist lower membrane formation composition of the present invention can contain acid compound further.Above-mentioned acid compound, as promoting that the catalyzer of cross-linking reaction works, can be enumerated such as, p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridine
the mineral acids such as sulfoacid compound and carboxylic acid compound, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid such as-tosilate, salicylic acid, camphorsulfonic acid, 5-sulphosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxy benzene sulfonic acid, benzenedisulfonic acid, 1-naphthalene sulfonic aicd, citric acid, benzoic acid, hydroxybenzoic acid.Above-mentioned acid compound can be replaced, or together with above-mentioned acid compound, containing thermal acid generator.Above-mentioned thermal acid generator also as promoting that the catalyzer of cross-linking reaction works, can enumerate the quaternary ammonium salt of such as trifluoromethanesulfonic acid.1 kind that selects from these acid compounds and thermal acid generator can be added, also can combine and add two or more.Remove the solid constituent after aftermentioned solvent relative to from resist lower membrane formation composition of the present invention, above-mentioned acid compound or thermal acid generator containing proportional, such as 0.1 quality % ~ 20 quality %.
Resist lower membrane formation composition of the present invention can contain surfactant further.As above-mentioned surfactant, can enumerate such as, polyoxyethylene lauryl ether, polyoxyethylene stearyl base ether, polyoxyethylene cetyl base ether, the polyoxyethylene alkyl ether classes such as polyoxyethylene oleyl ether, NONIN HS 240, the polyoxyethylene alkylaryl ether classes such as ethylene nonyl phenyl ether, polyoxyethylene/polyoxypropylene block copolymers class, sorbitan monolaurate, sorbitan-monopalmityl ester, sorbitan monosterate, dehydrating sorbitol monooleate, anhydrosorbitol trioleate, the sorbitan fatty ester classes such as anhydrosorbitol tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, the nonionic system surfactants such as polyoxyethylene sorbitan fatty acid ester such as polyoxyethylene sorbitan tristearate, エ Off ト ッ プ (registered trademark) EF301, エ Off ト ッ プ EF303, エ Off ト ッ プ EF352 (Mitsubishi マ テ リ ア Le electronics changes into (strain) system), メ ガ Off ァ ッ Network (registered trademark) F171, メ ガ Off ァ ッ Network F173, メ ガ Off ァ ッ Network R-30, メ ガ Off ァ ッ Network R-30-N, メ ガ Off ァ ッ Network R-40, メ ガ Off ァ ッ Network R-40-LM (DIC (strain) system), Off ロ ラ ー De FC430, Off ロ ラ ー De FC431 (Sumitomo ス リ ー エ system (strain) system), ア サ ヒ ガ ー De (registered trademark) AG710, サ ー Off ロ Application (registered trademark) S-382, サ ー Off ロ Application SC101, サ ー Off ロ Application SC102, サ ー Off ロ Application SC103, サ ー Off ロ Application SC104, サ ー Off ロ Application SC105, the fluorine system surfactants such as サ ー Off ロ Application SC106 (Asahi Glass (strain) system), organic siloxane polymer KP341 (SHIN-ETSU HANTOTAI's chemical industry (strain) system).1 kind of being selected from these surfactants can be added, also can combine two or more to add.Remove the solid constituent after aftermentioned solvent relative to from resist lower membrane formation composition of the present invention, containing of aforementioned surfactants is proportional, such as 0.01 quality % ~ 5 quality %.
Resist lower membrane formation composition of the present invention can be modulated in suitable solvent by making above-mentioned each component dissolves, uses with uniform solution state.As such solvent, can enumerate such as, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, carbiphene, propylene glycol, propylene glycol monomethyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol propyl ether acetic acid esters, methylcellosolve acetate, ethyl cellosolve acetate, toluene, dimethylbenzene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 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-methoxy methyl propionate, 3-methoxypropionate, 3-ethoxyl ethyl propionate, 3-ethoxypropanoate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N, dinethylformamide, N, N-dimethyl acetamide, 1-METHYLPYRROLIDONE.These organic solvents can use a kind, or two or more combinationally uses.From above-mentioned composition, remove the ratio of the solid constituent after organic solvent for such as 0.5 quality % ~ 30 quality %, be preferably 0.8 quality % ~ 15 quality %.
Be coated with resist lower membrane formation composition of the present invention and the operation of carrying out toasting is carried out as follows: base material (such as, silicon wafer, this silicon wafer can oxidized silicon fiml, silicon nitride film, oxidation nitridation silicon fiml or aluminium, tungsten etc. metal film be coated to.) on, the coating process suitable by spinner, coating machine etc. is coated with said composition, then, uses the heating arrangements such as heating plate to toast.As baking condition, suitably select 0.3 minute ~ 10 minutes from baking temperature 100 DEG C ~ 400 DEG C, baking time.
The 1st resist lower membrane formed by foregoing sequence forms organic polysiloxane film as the 2nd resist lower membrane, described 2nd resist lower membrane forms Resist patterns.2nd resist lower membrane also can be the SiON film or SiN film that are formed by vapour deposition methods such as CVD, PVD.Also can form the antireflection film (BARC) as the 3rd resist lower membrane further in the 2nd resist lower membrane, the 3rd resist lower membrane also can be the resist shape compensation film not having antireflection ability.In the operation forming aforementioned Resist patterns, expose by the mask (reticle mask) for the formation of predetermined pattern or by directly describing to carry out.Exposure source can use such as, g ray, i ray, KrF excimer laser, ArF excimer laser, EUV, electron ray.After exposure, carry out as required exposing rear heating (PostExposureBake).Then, developed by developer solution (such as 2.38 quality % tetramethylammonium hydroxide aqueous solutions), further with washing fluid or pure water, remove the developer solution used.Then, carry out Resist patterns drying and for improving the rear baking with the adaptation of substrate.
The etching work procedure carried out after aforementioned Resist patterns is formed is undertaken by dry ecthing.As the etching gas that dry ecthing uses, for the 2nd resist lower membrane (organopolysiloxane film), such as CHF can be enumerated
3, CF
4, C
2f
6, for being formed the 1st resist lower membrane formed with composition by resist lower membrane of the present invention, such as O can be enumerated
2, N
2o, NO
2, for the surface with difference of height or recess and/or protuberance, such as CHF can be enumerated
3, CF
4, C
2f
6.Further, can argon gas, nitrogen or carbon dioxide be mixed in these gases use.
Below, for the present invention, enumerate synthesis example and embodiment is described, but the present invention is by following records restriction.
Embodiment
Following synthesis example 1 ~ synthesis example 3, compare synthesis example 1 and compare the weight-average molecular weight shown in synthesis example 2 and polydispersity based on by gel permeation chromatography (following, referred to as GPC in this instructions.) measurement result that obtains.Use Dong ソ ー (strain) GPC system processed in mensuration, condition determination is as described below.
GPC post: TSKgelSuperMultipore (registered trademark) Hz-N (Dong ソ ー (strain))
Column temperature: 40 DEG C
Solvent: tetrahydrofuran (THF)
Flow: 0.35ml/ minute
Standard sample: polystyrene (Dong ソ ー (strain))
(synthesis example 1)
3,3 ', 5 are added in 200mL four-hole boiling flask, and 5 '-tetramethoxymethyl-4,4 '-dihydroxybiphenyl (following, referred to as TMOM-BP in this instructions.) (23.83g, 0.066mol, Honshu chemical industry (strain) make), pyrene (27.00g, 0.134mol, Tokyo change into industry (strain) system), p-toluenesulfonic acid monohydrate (0.53g, 0.003mol, Tokyo change into industry (strain) system), further loading Isosorbide-5-Nitrae-two
alkane (119.84g, Northeast chemistry (strain) is made), stirs, and heats up until confirm that backflow makes it dissolve, starts polymerization.Let cool after 6 hours after 60 DEG C, in methyl alcohol (1000g, Northeast chemistry (strain) is made), make it precipitate again.The sediment that obtains is filtered, with pressure Reduction Dryer at 60 DEG C dry 12 hours, obtain having the structural unit represented by following formula (3) subject polymer (following, referred to as TMOM-Py in this instructions.)28.6g。The TMOM-Py obtained, by GPC obtain with polystyrene conversion measure weight-average molecular weight for 2600.
(synthesis example 2)
TMOM-BP (2.21g is added in 100mL four-hole boiling flask, 0.006mol, Honshu chemical industry (strain) make), carbazole (5.00g, 0.030mol, Tokyo change into industry (strain) system), 1-pyrene formaldehyde (5.76g, 0.025mol, シ グ マ ア Le De リ ッ チ society system), p-toluenesulfonic acid monohydrate (0.89g, 0.006mol, Tokyo change into industry (strain) system), further loading Isosorbide-5-Nitrae-two
alkane (25.75g, Northeast chemistry (strain) is made), stirs, and heats up until confirm that backflow makes it dissolve, starts polymerization.Let cool after 7 hours after 60 DEG C, in methyl alcohol (1000g, Northeast chemistry (strain) are made), make it precipitate again.The sediment that obtains is filtered, with pressure Reduction Dryer at 60 DEG C dry 12 hours, obtain having the 2 kinds of structural units represented by following formula (4) subject polymer (following, referred to as TMOM-Cz-PCA in this instructions.)6.3g。The TMOM-Cz-PCA obtained, by GPC obtain with polystyrene conversion measure weight-average molecular weight for 8900.
(synthesis example 3)
TMOM-BP (13.93g is added in 200mL four-hole boiling flask, 0.038mol, Honshu chemical industry (strain) make), naphthalene (10.00g, 0.078mol, Tokyo change into industry (strain) system), p-toluenesulfonic acid monohydrate (0.31g, 0.002mol, Tokyo change into industry (strain) system), further loading Isosorbide-5-Nitrae-two
alkane (56.56g, Northeast chemistry (strain) is made), stirs, and heats up until confirm that backflow makes it dissolve, starts polymerization.Let cool after 5 hours after 60 DEG C, in methyl alcohol (1000g, Northeast chemistry (strain) is made), make it precipitate again.The sediment that obtains is filtered, with pressure Reduction Dryer at 60 DEG C dry 12 hours, obtain having the structural unit represented by following formula (5) subject polymer (following, referred to as TMOM-Na in this instructions.)5.9g。The TMOM-Na obtained, by GPC obtain with polystyrene conversion measure weight-average molecular weight for 5000.
(comparing synthesis example 1)
Under a nitrogen, carbazole (6.69g is added in 100mL four-hole boiling flask, 0.040mol, Tokyo change into industry (strain) system), 9-Fluorenone (7.28g, 0.040mol, Tokyo change into industry (strain) system), p-toluenesulfonic acid monohydrate (0.76g, 0.0040mol, Tokyo changes into industry (strain) system), load Isosorbide-5-Nitrae-two further
alkane (6.69g, Northeast chemistry (strain) is made), stirs, is warming up to 100 DEG C and makes it dissolve, start polymerization.Let cool after 24 hours after 60 DEG C, add chloroform (34g, Northeast chemistry (strain) is made) and dilute, in methyl alcohol (168g, Northeast chemistry (strain) is made), make it precipitate again.The sediment obtained is filtered, at 80 DEG C, makes its dry 24 hours with pressure Reduction Dryer, obtain the subject polymer 9.37g with the structural unit represented by following formula (6).The polymkeric substance obtained, by GPC obtain with polystyrene conversion measure weight-average molecular weight for 2800.
(embodiment 1)
Mix メ ガ Off ァ ッ Network R-30 (DIC (strain) system) 0.06g as surfactant in the polymkeric substance 20g obtained in synthesis example 1, make it be dissolved in cyclohexanone 80g and become solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the resist lower membrane formation composition adopting the photoetching process of multilayer film to use.
(embodiment 2)
In the polymkeric substance 20g obtained in synthesis example 2, mix メ ガ Off ァ ッ Network R-30 (DIC (strain) system) 0.06g as surfactant, make it be dissolved in cyclohexanone 80g and become solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the resist lower membrane formation composition adopting the photoetching process of multilayer film to use.
(embodiment 3)
In the polymkeric substance 20g obtained in synthesis example 3, mix メ ガ Off ァ ッ Network R-30 (DIC (strain) system) 0.06g as surfactant, make it be dissolved in cyclohexanone 80g and become solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the resist lower membrane formation composition adopting the photoetching process of multilayer film to use.
(comparative example 1)
In the polymkeric substance 20g obtained in relatively synthesis example 1, mix メ ガ Off ァ ッ Network R-30 (DIC (strain) system) 0.06g as surfactant, make it be dissolved in cyclohexanone 80g and become solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the resist lower membrane formation composition adopting the photoetching process of multilayer film to use.
(comparative example 2)
Mix as TMOM-BP (Honshu chemical industry (strain) system) 3.0g of crosslinking chemical, the pyridine as catalyzer in the polymkeric substance 20g obtained in relatively synthesis example 1
tosilate 0.6g, メ ガ Off ァ ッ Network R-30 (DIC (strain) system) 0.06g as surfactant, make it be dissolved in cyclohexanone 80g and become solution.Then, the tygon microfilter in 0.10 μm, aperture is used to filter, further, use the tygon microfilter in 0.05 μm, aperture to filter, modulate the resist lower membrane formation composition adopting the photoetching process of multilayer film to use.
(Determination of Hardness of film)
Use spin coater, the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3, comparative example 1 and comparative example 2 is coated on silicon wafer respectively.Toast at the wafer be coated with on hot plate 240 DEG C 2 minutes at baking 1 minute or 400 DEG C, define resist lower membrane (thickness 0.25 μm).Nano impress device G200 (ア ジ レ Application ト テ Network ノ ロ ジ ー society system) is used to measure the film hardness of these resist lower membrane.The results are shown in table 1.
[table 1]
(table 1)
From the result of above-mentioned table 1, use the resist lower membrane formation composition of the embodiment 1 ~ embodiment 3 that the present invention relates at 400 DEG C, toast the resist lower membrane formed for 2 minutes, under same condition, toast formed resist lower membrane with use comparative example 1 with the resist lower membrane formation composition of comparative example 2 to compare, there is high hardness.
(dissolution test in photoresist solvent)
Use spin coater, the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3 and comparative example 1 is coated on silicon wafer respectively.Electric hot plate toasts the wafer that has been coated with 2 minutes at 400 DEG C, define resist lower membrane (thickness 0.25 μm).This resist lower membrane be impregnated in the solvent (ethyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether, cyclohexanone) that resist uses, confirm to be insoluble to these solvents.
(mensuration of optical parametric)
Spin coater is used to be coated respectively on silicon wafer by the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3.Toast at the wafer be coated with on hot plate 240 DEG C 2 minutes at baking 1 minute or 400 DEG C, define resist lower membrane (thickness 0.05
μm).Spectroscopic ellipsometers is used to determine the refractive index of these resist lower membrane when wavelength 193nm (n value) and optics absorptivity (k value, also referred to as attenuation coefficient).The results are shown in table 2.
[table 2]
(table 2)
(mensuration of thermotolerance)
Spin coater is used to be coated respectively on silicon wafer by the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3.Toast at the wafer be coated with on hot plate 400 DEG C 2 minutes, define resist lower membrane (thickness 0.2 μm).Cut these resist lower membrane from silicon wafer, obtain powder.TG/DTA (BRUKER society TG-DTA2010SR) is used to measure the thermogravimetric amount phenomenon of powder at 400 DEG C obtained.The results are shown in table 3.
[table 3]
(table 3)
(mensuration of dry etching rate)
The etcher that the mensuration of dry etching rate uses and etching gas as follows.
Etcher: RIE-10NR (サ system コ (strain) system)
Etching gas: CF4
Spin coater is used to be coated respectively on silicon wafer by the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3.Toast at the wafer be coated with on hot plate 240 DEG C 2 minutes at baking 1 minute or 400 DEG C, define resist lower membrane (thickness 0.25 μm).Then, CF is used
4gas, as etching gas, measures the dry etching rate of these resist lower membrane.In addition, use spin coater by phenol resol resins (commercially available product, by GPC obtain with polystyrene conversion measure weight-average molecular weight Mw be 2000, polydispersity Mw/Mn is 2.5) solution coat on silicon wafer, toast at the wafer be coated with on hot plate 205 DEG C 1 minute and define phenol resol resins film (thickness 0.25 μm).Then, CF is used
4gas, as etching gas, measures the dry etching rate of this phenol resol resins film.Calculating when the dry etching rate of this phenol resol resins film being set to 1.00, formed the resist lower membrane formed with composition by the resist lower membrane of modulation in embodiment 1 ~ embodiment 3 dry etching rate in the mode of dry etching rate ratio, showing the result in table 4.Dry etching rate is less, represents CF
4the elching resistant of gas is higher.
Dry etching rate ratio=(dry etching rate of resist lower membrane)/(dry etching rate of phenol resol resins film)
[table 4]
(table 4)
(confirmation of distortion generation pattern width)
Spin coater is used to be coated respectively on the silicon wafer with silicon oxide film by the resist lower membrane formation composition of modulation in embodiment 1 ~ embodiment 3 and comparative example 2 respectively.Toast at the wafer be coated with on hot plate 400 DEG C 2 minutes, form resist lower membrane (thickness 200nm).In this resist lower membrane, coating is containing the known silicon hard mask formation composition of polysiloxane, it is toasted 1 minute at 240 DEG C, forms silicon hard mask layer (thickness 45nm).Further, on this silicon hard mask layer, painting erosion resistant agent solution (PAR855S90 (Sumitomo Chemical (strain) system)), toasts it 1 minute and forms resist layer (thickness 120nm) at 100 DEG C.Use mask to be exposed at wavelength 193nm by this resist layer, carry out exposing rear heating (PEB, at 105 DEG C 1 minute), afterwards, carry out video picture and obtain Resist patterns.Then, with fluorine system gas, (composition is CF
4) carry out dry ecthing, Resist patterns is transferred to hard mask layer.Then, with oxygen system gas, (composition is O
2) carry out dry ecthing, Resist patterns is transferred to above-mentioned resist lower membrane.Then, with fluorine system gas, (composition is C further
4f
8) carry out dry ecthing, carry out the removing of silicon oxide film on silicon wafer.With each pattern form that electron microscope observation finally obtains.
Along with pattern width narrows, be called that the bending of the irregular pattern of distortion (wiggling) becomes easy generation, therefore to use in above-described embodiment 1 ~ embodiment 3 the resist lower membrane formation composition of modulation to carry out above-mentioned pattern formation process with electron microscope observation, the pattern obtained starts to bend the pattern width of (wiggling).Owing to bending (wiggling) of pattern occurring thus the loyal substrate based on pattern can not be carried out process, the pattern width (critical pattern width) bent before (wiggling) according to being about to occur pattern is therefore needed to carry out substrate processing.Pattern start the to bend value of critical pattern width of (wiggling) is narrower, can carry out finer substrate processing.The mensuration of resolution employs surveys long scan electron microscope ((strain) Hitachi Ha イ テ Network ノ ロ ジ ー ズ system).Measurement result is shown in table 5.
[table 5]
(table 5)
The resist lower membrane that the effect that the resist lower membrane formation composition that the photoetching process of employing multilayer film of the present invention uses can be provided as antireflection film also can have concurrently.In addition, can judge: resist lower membrane formation composition of the present invention has and layer CVD can form the thermotolerance of hard mask thereon.In addition, even if when pattern width narrows, also can obtain the good pattern of bending (wiggling) being difficult to occur pattern, at least can obtain good pattern not bending in the pattern width near 50nm.
Claims (6)
1. a resist lower membrane formation composition, comprises polymkeric substance and solvent, and described polymkeric substance has the structural unit represented by following formula (1),
In formula (1), X
1represent the divalent organic base of the carbon number 6 ~ 20 with the aromatic rings that at least 1 can be replaced by halogeno-group, nitro, amino or hydroxyl, X
2represent organic group or the methoxyl of the carbon number 6 ~ 20 with the aromatic rings that at least 1 can be replaced by halogeno-group, nitro, amino or hydroxyl.
2. resist lower membrane formation composition according to claim 1, in described formula (1), the divalent organic base with the carbon number 6 ~ 20 of at least 1 aromatic rings is phenylene, biphenylene, sub-terphenyl, fluorenylidene, naphthylene, anthrylene, sub-pyrenyl, sub-carbazyl or the group represented by following formula (c), the organic group with the carbon number 6 ~ 20 of at least 1 aromatic rings is phenyl, xenyl, terphenyl, fluorenyl, naphthyl, anthryl, pyrenyl, carbazyl, or the group to be represented by following formula (d-1) or following formula (d-2),
In formula (c), n represents 0 or 1;
In formula (d-1), formula (d-2), n represents 0 or 1.
3. resist lower membrane formation composition according to claim 1 and 2, described polymkeric substance also has the structural unit represented by following formula (2),
In formula (2), X
1identical with the definition implication recorded in claim 1, R
3represent phenyl, naphthyl, anthryl, pyrenyl, thienyl or pyridine radicals, R
4represent hydrogen atom, phenyl or naphthyl, R
3and R
4when representing phenyl respectively, R
3and R
4fluorenes ring is formed together with the same carbon atom that can combine with them.
4. the resist lower membrane formation composition according to any one of claims 1 to 3, also comprises surfactant.
5. the resist lower membrane formation composition according to any one of Claims 1 to 4, also comprises crosslinking chemical.
6. the resist lower membrane formation composition according to any one of Claims 1 to 5, also comprises acid compound and/or acid agent.
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| JP2013-086861 | 2013-04-17 | ||
| JP2013086861 | 2013-04-17 | ||
| PCT/JP2014/059633 WO2014171326A1 (en) | 2013-04-17 | 2014-04-01 | Composition for forming resist underlayer film |
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| CN105143979B CN105143979B (en) | 2019-07-05 |
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| JP (1) | JP6327481B2 (en) |
| KR (1) | KR102004697B1 (en) |
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| CN107340688A (en) * | 2016-04-29 | 2017-11-10 | 东友精细化工有限公司 | Hard mask composition |
| CN109212905A (en) * | 2017-06-30 | 2019-01-15 | 东友精细化工有限公司 | Hard mask composition |
| CN110192152A (en) * | 2017-01-13 | 2019-08-30 | 日产化学株式会社 | Resist lower membrane formation composition comprising amide solvent |
| CN110546570A (en) * | 2017-04-25 | 2019-12-06 | 日产化学株式会社 | composition for forming resist underlayer film using fluorene compound |
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| CN107531597A (en) * | 2015-03-06 | 2018-01-02 | 三菱瓦斯化学株式会社 | Compound, resin, lower layer film for lithography form material, lower layer film for lithography, pattern formation method and the purification process of compound or resin |
| KR102349937B1 (en) * | 2017-03-27 | 2022-01-10 | 동우 화인켐 주식회사 | Composition for hard mask |
| TW202039619A (en) * | 2019-01-11 | 2020-11-01 | 日商三菱瓦斯化學股份有限公司 | Composition for forming film, resist composition,radiation-sensitive composition, method forproducing amorphous film, method for formingresist pattern, composition for forming underlayerfilm for lithography, method for producing underlayer film for lithography, and method for forming circuit pattern |
| WO2021112194A1 (en) * | 2019-12-04 | 2021-06-10 | 三菱瓦斯化学株式会社 | Composition for forming underlayer film for lithography, underlayer film for lithography, resist pattern forming method, circuit pattern forming method, oligomer, and purification method |
| JPWO2021172296A1 (en) | 2020-02-28 | 2021-09-02 | ||
| WO2021172295A1 (en) | 2020-02-28 | 2021-09-02 | 日産化学株式会社 | Composition for forming resist underlayer film |
| JPWO2022107759A1 (en) * | 2020-11-19 | 2022-05-27 | ||
| KR20240009452A (en) | 2021-05-18 | 2024-01-22 | 닛산 가가쿠 가부시키가이샤 | Resist underlayer film forming composition |
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| CN107340688A (en) * | 2016-04-29 | 2017-11-10 | 东友精细化工有限公司 | Hard mask composition |
| CN107340688B (en) * | 2016-04-29 | 2022-05-06 | 东友精细化工有限公司 | Composition for hard mask |
| CN110192152A (en) * | 2017-01-13 | 2019-08-30 | 日产化学株式会社 | Resist lower membrane formation composition comprising amide solvent |
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| CN110546570A (en) * | 2017-04-25 | 2019-12-06 | 日产化学株式会社 | composition for forming resist underlayer film using fluorene compound |
| CN110546570B (en) * | 2017-04-25 | 2023-07-25 | 日产化学株式会社 | Composition for forming resist underlayer film using fluorene compound |
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| CN109212905B (en) * | 2017-06-30 | 2021-10-26 | 东友精细化工有限公司 | Composition for hard mask |
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| KR102004697B1 (en) | 2019-07-29 |
| JPWO2014171326A1 (en) | 2017-02-23 |
| CN105143979B (en) | 2019-07-05 |
| JP6327481B2 (en) | 2018-05-23 |
| TW201504766A (en) | 2015-02-01 |
| KR20160002741A (en) | 2016-01-08 |
| WO2014171326A1 (en) | 2014-10-23 |
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