CN108089405A - Hard mask composition - Google Patents

Hard mask composition Download PDF

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Publication number
CN108089405A
CN108089405A CN201711008544.2A CN201711008544A CN108089405A CN 108089405 A CN108089405 A CN 108089405A CN 201711008544 A CN201711008544 A CN 201711008544A CN 108089405 A CN108089405 A CN 108089405A
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China
Prior art keywords
chemical formula
hard mask
formula
mentioned
mask composition
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Application number
CN201711008544.2A
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Chinese (zh)
Inventor
梁敦植
梁振锡
朴根永
崔汉永
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Dongwoo Fine Chem Co Ltd
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Dongwoo Fine Chem Co Ltd
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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
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents

Abstract

The present invention provides a kind of hard mask composition, and hard mask includes polymer, the crosslinking agent and solvent comprising the compound represented by general formula 1 of aromatic compound with composition.Heat resistance can be formed due to the crosslinking agent and hard mask that coating is enhanced simultaneously, in general formula 1, n is 1~10 integer.General formula 1

Description

Hard mask composition
Technical field
The present invention relates to hard mask compositions.More specifically, the present invention relates to include aromatic condensation object or chemical combination The hard mask composition of object.
Background technology
For example, in the fields such as semiconductor manufacturing, microelectronics, the works of circuit, wiring, insulating pattern etc integrates Degree persistently increases.Therefore, the photo-mask process for the fine pattern of said structure object is also developed together.
In general, on etch target film painting photoresist and form photoresist layer, by exposing and showing Shadow process and form photoresist pattern.Then, above-mentioned photoresist pattern is used as etching mask, by above-mentioned etching pair It as membrane part removes, so as to form predetermined pattern.After carrying out for the image transfer of above-mentioned etch target film, on Stating photoresist pattern can be removed by being ashed (ashing) and/or removing (strip) process.
Reduced to inhibit in above-mentioned exposure process the resolution ratio as caused by light reflection, can in above-mentioned etch target film and Antireflection (anti-refractive coating are formed between above-mentioned photoresist layer；ARC) layer.In this case, it can add Etching for above-mentioned ARC layer, therefore the consumption or etch quantity of above-mentioned photoresist layer or photoresist pattern can increase Add.In addition, above-mentioned etch target film thickness increase or formed etch quantity required during desired pattern it is increased in the case of, can Can not ensure the sufficient elching resistant of required above-mentioned photoresist layer or photoresist pattern.
It therefore, can in order to ensure being used to be formed the elching resistant of the photoresist of desired pattern and etching selectivity With the additional resist lower film between above-mentioned etch target film and above-mentioned photoresist layer.
Above-mentioned resist lower film has the heat resistance and chemical resistance for high-temperature process, for example, it is necessary to pass through rotation Process is applied to be formed with uniform thickness.
KR published patent the 10-2010-0082844th discloses an example that resist lower film forms composition.
Prior art literature
Patent document
KR published patent the 10-2010-0082844th
The content of the invention
Problem to be solved
The problem of the present invention, which is to provide, can form the hard of hard mask with excellent machinery, chemical characteristic and cover Mould composition.
The method to solve the problem
1. a kind of hard mask composition, it includes：The polymer of aromatic compound, comprising represented by the following general formula 1 Compound crosslinking agent and solvent,
[general formula 1]
(in general formula 1, n is 1~10 integer).
2. the hard mask composition as described in 1, in above-mentioned general formula 1, n is 2~4 integer.
3. the hard mask composition as described in 1, above-mentioned crosslinking agent is included represented by following chemical formula 1 and chemical formula 2 At least one of compound,
[chemical formula 1]
[chemical formula 2]
4. the hard mask composition as described in 1, the polymer of above-mentioned aromatic compound includes 1 table of following structural formula The repetitive unit shown,
[structural formula 1]
(in structural formula 1, A1To be selected from following chemical formula A1- 1~chemical formula A1At least one of -6,
[chemical formula A1-1]
[chemical formula A1-2]
[chemical formula A1-3]
[chemical formula A1-4]
[chemical formula A1-5]
[chemical formula A1-6]
A1To be non-substituted or be further substituted with by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or phenyl,
The B of structural formula 1 and chemical formula A1- 5 Ra is each independently the alkyl or carbon of hydrogen atom, carbon number 1~6 The aryl (aryl) of atomicity 6~30,
In the case that B includes phenyl ring, above-mentioned phenyl ring is non-substituted or by carbon number 1~6 alkyl, hydroxyl, methoxy Base or phenyl are further substituted with, and n is 1~200 integer).
5. the hard mask composition as described in 4, the A of structure above 11From following chemical formula p-1-1~chemistry At least one of compound represented by formula p-1-5, chemical formula p-2-1 and chemical formula p-2-2,
[chemical formula p-1-1]
[chemical formula p-1-2]
[chemical formula p-1-3]
[chemical formula p-1-4]
[chemical formula p-1-5]
[chemical formula p-2-1]
[chemical formula p-2-2]
6. the hard mask composition as described in 4, the B of structure above 1 is from the change represented by following chemical formula p-3 Close object,
[chemical formula p-3]
7. the hard mask composition as described in 1, the weight average molecular weight of the polymer of above-mentioned aromatic compound is 1,000 ~5,000.
8. the hard mask composition as described in 1, further includes at least one of catalyst and surfactant.
Invention effect
Using the hard mask composition of the embodiment of the present invention, it can be formed while improve heat resistance and coating homogeneity Hard mask.
The hard mask of the embodiment of the present invention includes the aromatic cross-linker with high-carbon content or carbon ratio with composition, Thus, it is possible to ensure the desired coating of hard mask composition, and more improve the etching selectivity of hard mask and heat-resisting Property.
In addition, using the hard mask formed by above-mentioned hard mask with composition, high-resolution photo-mask process can be realized, And the target pattern of desired fine line width can be formed.
Specific embodiment
The embodiment of the present invention is provided comprising the polymer of aromatic compound, the crosslinking agent comprising aromatic unit and molten The hard mask composition of agent.Above-mentioned hard mask composition can for example be coated on photoresist layer and etch target film it Between and formed as resist lower film hard mask film.By photoresist pattern by above-mentioned hard mask film part remove from And hard mask can be formed, above-mentioned hard mask can be used as to additional etching mask.
Above-mentioned hard mask film or hard mask for example may be used as spin-coating hardmask (Spin-On Hardmask：SOH).
Hereinafter, the hard mask of the embodiment of the present invention is described in detail with composition.
The polymer of aromatic compound
It, can be without particular limitation using public in the art in the hard mask composition of the embodiment of the present invention Macromolecule or resinous substances included in the carbon system SOH compositions known.
According to embodiment illustrated, in order to ensure the heat resistance of hard mask film, at least one aromatic compound can be used Base matter of the polymer (for example, condensation polymer) of object as above-mentioned hard mask composition.
In part of the embodiment, the polymer of above-mentioned aromatic compound can include the repetition list represented by structural formula 1 Member.
[structural formula 1]
In structural formula 1, A1Can be selected from following chemical formula A1- 1~chemical formula A1At least one of -6.In addition, comprising A different from each other1Repetitive unit can in order or randomly arrange.
[chemical formula A1-1]
[chemical formula A1-2]
[chemical formula A1-3]
[chemical formula A1-4]
[chemical formula A1-5]
(Ra can include the aryl (Aryl) of hydrogen atom, the alkyl of carbon number 1~6 or carbon number 6~30)
[chemical formula A1-6]
A1It can be further substituted with by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or phenyl.In addition, structural formula 1 B can be the aryl (aryl) of hydrogen atom, the alkyl of carbon number 1~6 or carbon number 6~30.In addition, B includes phenyl ring In the case of, above-mentioned phenyl ring can be further substituted with by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or phenyl.N can be 1 ~200 integer.
In part of the embodiment, chemical formula A1- 1~chemical formula A1- 5 can each derive from chemical formula p-1-1~chemical formula Compound represented by p-1-5.
[chemical formula p-1-1]
[chemical formula p-1-2]
[chemical formula p-1-3]
[chemical formula p-1-4]
[chemical formula p-1-5]
In addition, chemical formula A1- 6 can for example derive from represented by following chemical formula p-2-1 and/or chemical formula p-2-2 Compound.
[chemical formula p-2-1]
[chemical formula p-2-2]
Each phenyl ring of chemical formula p-2-1 and chemical formula p-2-2 independently can be by the alkyl of carbon number 1~6, first Oxygroup or phenyl are further substituted with.
In part of the embodiment, in structural formula 1, B can derive from the compound of following chemical formula p-3：
[chemical formula p-3]
As described above, B is the aryl of hydrogen atom, the alkyl of carbon number 1~6 or carbon number 6~30, B includes phenyl ring In the case of, above-mentioned phenyl ring can be further substituted with by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or phenyl.
For example, the compound of above-mentioned chemical formula p-3 can be represented by following chemical formula p-3-1.
[chemical formula p-3-1]
In one embodiment, the repetitive unit of structural formula 1 or the polymer (copolymer) comprising the repetitive unit can lead to Cross the contracting of the compound of the compound and above-mentioned chemical formula p-3 in the group being made of chemical formula p-1-1~chemical formula p-1-5 Reaction is closed to manufacture.
In one embodiment, the repetitive unit of structural formula 1 or the polymer (copolymer) comprising the repetitive unit can lead to Cross the contracting of the compound of the compound and above-mentioned chemical formula p-3 in the group being made of chemical formula p-2-1 and chemical formula p-2-2 Reaction is closed to manufacture.
In one embodiment, the repetitive unit of structural formula 1 or the polymer (copolymer) comprising the repetitive unit can lead to Cross compound in the group being made of chemical formula p-1-1~chemical formula p-1-5, selected from by chemical formula p-2-1 and chemical formula Compound in the group of p-2-2 compositions is manufactured with the condensation reaction of the compound of chemical formula p-3.
As described above, the polymer of embodiment illustrated includes the condensation of aromatic compound or polycyclc aromatic compound Object, therefore the carbon content (C-contents of per unit molecule：C%) can increase.Thereby, it is possible to improve to include above-mentioned polymerization The hard mask of object is for the elching resistant of etching gas or etching solution.
In the embodiment of the present invention, the weight average molecular weight of above-mentioned polymer can be about 1,000~7,000, preferably can be with It is about 1,000~5,000.In the case that the weight average molecular weight of above-mentioned polymer is below about 1,000, the heat resistance of hard mask is excessive It reduces, crackle, etch damage etc. may aggravate.In the case that the weight average molecular weight of above-mentioned polymer is more than about 7,000, composition Coating be deteriorated, possibly can not form hard mask layer or hard mask with uniform thickness or height.Above-mentioned polymer In the case that weight average molecular weight is about 5, less than 000, from the aspect of the coating of above-mentioned hard mask composition preferably.
[weight average molecular weight (Mw)/number is equal for the polydispersity index (PDI, Polydispersity index) of above-mentioned polymer Molecular weight (Mn)] it can be about 1.3~6.0, it preferably can be about 1.5~4.0.In above-mentioned polydispersity index scope, Ke Yiti The coating and heat resistance of high above-mentioned hard mask composition.
In part of the embodiment, the content of above-mentioned polymer is not particularly limited, and in composition total weight, can be about 5 ~15 weight %.The content of above-mentioned polymer is below about in the case of 5%, it is difficult to form the hard mask layer of desired thickness, firmly The heat resistance of mask may be decreased.In the case that the content of above-mentioned polymer is more than about 15 weight %, the coating of composition can It can reduce.
Crosslinking agent
The hard mask of the embodiment of the present invention further includes crosslinking agent with composition.By above-mentioned crosslinking agent, so as to It reaches the cross-linking reaction between polymer or repetitive unit adjacent included in inducing composition and further improves hard mask The mechanical properties such as heat resistance, the marresistance of layer or hard mask.
In addition, in the case of the polymer for using molecular weight relatively low to improve coating, it also can be by above-mentioned Crosslinking agent makes adjacent polymer be cross-linked to each other, so as to while predetermined coating is ensured improve heat resistance.
According to an embodiment of the invention, above-mentioned crosslinking agent can include aromatic unit and cross-linking reaction functional group.One Divide in embodiment, above-mentioned aromatic unit can be Ppolynuclear aromatic unit, and above-mentioned cross-linking reaction functional group can include aldehyde radical.
In part of the embodiment, above-mentioned aromatic unit can be pyrenyl.In the case that above-mentioned crosslinking agent includes pyrenyl, by Increase in carbon content and can be ensured that sufficient etching selectivity, and can be prevented when molecular size excessively increases by being produced Physical property caused by raw steric hindrance etc. reduces (for example, the heat resistance as caused by reducing the degree of cross linking reduces).
In illustrative embodiment, above-mentioned crosslinking agent can include the compound represented by the following general formula 1.
[general formula 1]
In general formula 1, n is 1~10 integer.In part of the embodiment, n can be 2~4 integer.When n is more than 5, Since carbon content is reduced, etching selectivity may be decreased.When n is 1, can not ensure the sufficient degree of cross linking, hard mask it is heat-resisting Property may be decreased.
As shown in general formula 1, aldehyde radical can with pyrenyl directly in conjunction with.Therefore, it is possible to improve the effect of cross-linking reaction Rate, and carbon content is made to increase and significantly improve etching selectivity.
For example, above-mentioned crosslinking agent can include at least one in the compound represented by following chemical formula 1 and chemical formula 2 Kind.
[chemical formula 1]
[chemical formula 2]
By the way that above-mentioned crosslinking agent is made to be included in hard mask composition, so as to relatively low using molecular weight as described above In the case of polymer, the desired heat resistance of hard mask can also ensure that.Therefore, it is possible to improve above-mentioned hard mask composition Coating, and the mechanical property of hard mask is made to improve together.
In addition, above-mentioned crosslinking agent includes the Ppolynuclear aromatic unit as pyrenyl, therefore there can be high-carbon content (C%) structure.Therefore, it is possible to improve tolerance of the hard mask for etching gas or etching solution, and improve and covered firmly using above-mentioned The etching selectivity of the etching work procedure of mould.
In this specification, the meaning of term " carbon content " can be the unit formula total mass number of carbon mass number and compound Ratio.In part of the embodiment, the carbon content of above-mentioned crosslinking agent can be about more than 70%.In one embodiment, above-mentioned friendship The carbon content of connection agent can be about more than 75%.
Compared with above-mentioned 100 parts by weight of polymer, the content of above-mentioned crosslinking agent can be about 0.1~20 parts by weight, preferably It can be about 1~20 parts by weight.In above range, it can make while the coating of hard mask composition is not hindered heat-resisting Property and etching selectivity improve together.
Solvent
It, can be above-mentioned poly- using can be ensured that without particular limitation in the hard mask composition of the embodiment of the present invention The sufficient deliquescent organic solvent of object and crosslinking agent is closed as solvent.
For example, propylene glycol monomethyl ether (propylene glycol monomethyl ether can be enumerated acetate；PGMEA), propylene glycol monomethyl ether (propylene glycol monomethyl ether；PGME), cyclohexanone, Ethyl lactate, gamma-butyrolacton (γ-butyrolactone；GBL), acetylacetone,2,4-pentanedione (acetyl acetone) etc., preferably can be with Use propylene glycol monomethyl ether (propylene glycol monomethyl ether acetate；PGMEA it is) etc. molten Agent is as above-mentioned solvent.
The content of above-mentioned solvent is not particularly limited, content can be except mentioned component and other additive components with Outer surplus.For example, it is contemplated that the coating of composition, dissolubility, drying property, in the total weight of hard mask composition, Content can be about 50~95 weight %, be preferably 80~95 weight %.
Additive
In part of the embodiment, above-mentioned hard mask can further include to promote to carry out by crosslinking agent with composition The catalyst of the cross-linking reaction of the repetitive unit of polymer.As above-mentioned catalyst, acid catalyst or base catalysis can be used Agent.
As above-mentioned acid catalyst, the acid catalyst of thermal activation can be used.As the example of acid catalyst, can use The organic acid of p-methyl benzenesulfonic acid monohydrate (p-toluene sulfonic acid monohydrate) etc, and can make With thermal acid generator (thermal acid generator：TAG) the compound of system.It, can be with as the example of above-mentioned thermal acid generator Enumerate p-methyl benzenesulfonic acid pyridine(pyridinium p-toluene sulfonate), 2,4,4,6- tetrabromos cyclohexadienone, Benzoin tosylate, 2- nitrobenzyl tosylats, the Arrcostab etc. of organic sulfonic acid.
For example, by the acid generated by above-mentioned thermal acid generator, crosslinking agent can react with the hydroxyl of polymer and be promoted Into cross-linking reaction.
As above-mentioned basic catalyst, NH can be used4OH or ammonium hydroxide based compound.
For example, compared with above-mentioned 100 parts by weight of polymer, the content of above-mentioned catalyst can be about 0.001~50 weight Part, it preferably can be about 0.1~20 parts by weight, more preferably can be about 1~20 parts by weight.
In part of the embodiment, above-mentioned hard mask composition can further include surfactant.As above-mentioned table Face activating agent, it is, for example, possible to use alkylbenzenesulfonate, alkyl pyridineSalt, polyethylene glycols, quaternary ammonium salt etc..It is for example, opposite In above-mentioned 100 parts by weight of polymer, the content of above-mentioned surfactant can be about 1~30 parts by weight.It, can in above range It is uniform by the adaptation of surfactant raising hard mask layer, surface while deteriorating the optical characteristics of hard mask Property etc..
Hereinafter, in order to help the present invention understanding, the experimental example including preferred embodiment and comparative example is provided, but These embodiments simply illustrate the present invention, appended claims scope are not intended to limit, in scope of the invention and technological thought In the range of embodiment can be made various changes and be changed, this it will become apparent to those skilled in the art that this The deformation and modification of sample fall within appended claims scope certainly.
Embodiment and comparative example
Manufacture the hard mask composition of the composition and content (weight %) described in table 1 below.
[table 1]
A-1：Pass through(molar ratio：90:10:10) contracting Close reaction (acid catalyst：P-methyl benzenesulfonic acid (compared with aryl alcoholic compound be 5mol%)) generation copolymer (Weight-average molecular Amount：2400)
A-2：Pass throughCondensation reaction (acid catalyst：P-methyl benzenesulfonic acid (compared with Aryl alcoholic compound be 5mol%)) generation copolymer (weight average molecular weight：2900)
A-3：Pass throughCondensation reaction (acid catalyst：P-methyl benzenesulfonic acid (compared with Aryl alcoholic compound be 5mol%)) generation copolymer (weight average molecular weight：4700)
A-4：Passing throughCondensation reaction (acid catalyst：P-methyl benzenesulfonic acid is (opposite In aryl alcoholic compound be 5mol%)) generation prepolymer in add10mol% and the copolymer that generates (are divided equally again Son amount：5500)
A-5：Passing throughCondensation reaction (acid catalyst：P-methyl benzenesulfonic acid (compared with aryl alcoholic compound be 5mol%)) generation prepolymer in addAnd it gives birth to Into copolymer (weight average molecular weight：7600)
B-1:
B-2:
B-3:
B-4:
B-5:
C：Propylene glycol monomethyl ether (propylene glycol monomethyl ether acetate； PGMEA)
D：P-methyl benzenesulfonic acid pyridine
E：Triethylene glycol
Experimental example
The heat resistance of the hard mask layer formed by the composition of table 1 or hard mask is evaluated by aftermentioned evaluation method, is applied Cloth and etching selectivity.Evaluation result is shown in table 2 below.
1. Evaluation of Heat Tolerance
The composition of the embodiment of table 1 and comparative example is dried in vacuo and is removed solvent, extracts a part of sample, Under a nitrogen, using thermogravimetric analysis (thermogravimetric analysis, TGA), while 800 DEG C are warming up to, while surveying Determine mass loss rate.
Mass loss rate={ quality of when (initial mass -800 DEG C)/initial mass } x 100%
<Heat-resisting sex determination>
◎：Mass loss rate is less than 10%
○：Mass loss rate is for 10% less than 15%
△：Mass loss rate is for 15% less than 25%
×：Mass loss rate is more than 25%
2. coating homogeneity
After the composition of the embodiment of table 1 and comparative example is dried, spin coating is carried out in a manner that thickness becomes 5um, 100 After carrying out drying in 3 minutes in DEG C air drier, surface is with the naked eye confirmed.
<Coating homogeneity judges>
○：Naked eyes do not confirm the uneven of coating surface
△：Naked eyes confirm local uneven
×：It is uneven that naked eyes confirm whole face
3. etching selectivity (E/S)
The composition of the embodiment of table 1 and comparative example is utilized respectively spin-coating method to be coated on silicon chip, 60 are carried out at 200 DEG C Second baking, forms thicknessFilm.ArF photoresists are coated on each film formed, 60 are carried out at 110 DEG C ASML (XT are used after second baking:1450G, NA 0.93) exposure sources of company are exposed respectively, then utilize TMAH (2.38wt% aqueous solutions) develops respectively, obtains the line of 60nm and gap (line and space) pattern.
The patterned test piece of acquisition at 110 DEG C is further cured 60 seconds, uses CHF3/CF4Mixed gas is to test piece point Not carry out 20 seconds dry-etchings, observe section respectively using FE-SEM, measure etching speed, judge for halogen plasma Elching resistant, i.e. etching selectivity.
<Etching selectivity is evaluated>
◎：Etching speed is less than 10A/Sec
○：Etching speed is 10A/Sec less than 11A/Sec
△：Etching speed is 11A/Sec less than 12A/Sec
×：Etching speed is more than 12A/Sec
[table 2]
It distinguishes Heat resistance Coating homogeneity Etching selectivity
Embodiment 1 ◎ ○ ◎
Embodiment 2 ○ ○ ◎
Embodiment 3 ◎ ○ ◎
Embodiment 4 ◎ ○ ◎
Embodiment 5 ◎ △ ◎
Embodiment 6 ◎ △ ◎
Comparative example 1 ○ × △
Comparative example 2 × ○ ×
Comparative example 3 × ○ △
Comparative example 4 × ○ △
With reference to table 2, in the case of the embodiment of the crosslinking agent comprising the embodiment of the present invention, compared with comparative example, obtain Significantly excellent heat resistance, coating homogeneity and etching selectivity result.
Not comprising crosslinking agent and include the relatively high (Mw (A-5) of molecular weight：7600) situation of the comparative example 1 of polymer Under, the heat resistance measured is relatively good, but coating substantially deteriorates.
Include the relatively low (Mw (A-1) of molecular weight：2400) in the case of the comparative example 2~4 of polymer, heat resistance is disliked Change, although comprising crosslinking agent, etching selectivity does not improve fully.Particularly using carbon content low and there is no aromatic series list In the comparative example 2 of the crosslinking agent (B-3) of member, the etching selectivity measured is also apparent low.
Use the relatively low (Mw (A-1) of molecular weight：2400) reality of polymer and the crosslinking agent (B-1) using chemical formula 2 In the case of applying example 1, most excellent heat resistance, coating and etching selectivity is obtained as a result, crosslinking agent using chemical formula 1 In the case of the embodiment 2 of (B-2, n=2), compared with Example 1, heat resistance slightly reduces.
On the other hand, in embodiment 5 and embodiment 6, increase with the molecular weight of polymer, coating slightly reduces.It is special In the case of not being embodiment 6 of the polymer molecular weight more than 7000, non-uniform areas compared with Example 5 is with the naked eye confirmed Increase.

Claims (8)

1. a kind of hard mask composition, it includes：
The polymer of aromatic compound；
Include the crosslinking agent of the compound represented by the following general formula 1；With
Solvent,
General formula 1
In general formula 1, n is 1~10 integer.
2. hard mask composition according to claim 1, in the general formula 1, n is 2~4 integer.
3. hard mask composition according to claim 1, the crosslinking agent includes 2 institute of following chemical formula 1 and chemical formula At least one of compound of expression,
Chemical formula 1
Chemical formula 2
4. hard mask composition according to claim 1, the polymer of the aromatic compound includes following structures Repetitive unit represented by formula 1,
Structural formula 1
In structural formula 1, A1To be selected from following chemical formula A1- 1~chemical formula A1At least one of -6,
Chemical formula A1-1
Chemical formula A1-2
Chemical formula A1-3
Chemical formula A1-4
Chemical formula A1-5
Chemical formula A1-6
A1To be non-substituted or be further substituted with by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or phenyl,
The B of structural formula 1 and chemical formula A1- 5 Ra is each independently the alkyl or carbon number of hydrogen atom, carbon number 1~6 6~30 aryl,
B include phenyl ring in the case of, above-mentioned phenyl ring for it is non-substituted or by the alkyl of carbon number 1~6, hydroxyl, methoxyl group or Phenyl is further substituted with,
N is 1~200 integer.
5. hard mask composition according to claim 4, the A of the structural formula 11From following chemical formula p-1-1~ At least one of compound represented by chemical formula p-1-5, chemical formula p-2-1 and chemical formula p-2-2,
Chemical formula p-1-1
Chemical formula p-1-2
Chemical formula p-1-3
Chemical formula p-1-4
Chemical formula p-1-5
Chemical formula p-2-1
Chemical formula p-2-2
6. hard mask composition according to claim 4, the B of the structural formula 1 derives from following chemical formula p-3 institutes table The compound shown,
Chemical formula p-3
7. hard mask composition according to claim 1, the weight average molecular weight of the polymer of the aromatic compound For 1,000~5,000.
8. hard mask composition according to claim 1, further includes in catalyst and surfactant at least It is a kind of.
CN201711008544.2A 2016-11-22 2017-10-25 Hard mask composition Withdrawn CN108089405A (en)

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Application publication date: 20180529