Source: http://www.google.com/patents/US7829259?dq=5,973,252
Timestamp: 2017-12-17 22:20:56
Document Index: 779217747

Matched Legal Cases: ['§371', '§119', 'Application No. 2003', 'Application No. 2003', 'Application No. 2004', 'Application No. 093130121', 'Application No. 093115553', 'Application No. 2004']

Patent US7829259 - Resin for photoresist composition, photoresist composition and method for ... - Google Patents
A resin for photoresist compositions is disclosed with excellent resolution and line edge roughness characteristics. A photoresist composition and a method for forming a resist pattern using such a resin are also disclosed. The resin has a hydroxyl group bonded to a carbon atom at a polymer terminal,...http://www.google.com/patents/US7829259?utm_source=gb-gplus-sharePatent US7829259 - Resin for photoresist composition, photoresist composition and method for forming resist pattern
Publication number US7829259 B2
Application number US 12/365,752
Also published as US7592123, US20070065748, US20090142700, WO2004108780A1
Publication number 12365752, 365752, US 7829259 B2, US 7829259B2, US-B2-7829259, US7829259 B2, US7829259B2
Inventors Hideo Hada, Masaru Takeshita, Shogo Matsumaru, Hiroaki Shimizu
Patent Citations (54), Non-Patent Citations (7), Referenced by (2), Classifications (21), Legal Events (1)
Resin for photoresist composition, photoresist composition and method for forming resist pattern
US 7829259 B2
wherein R1 and R2 each represent, independently, an alkyl group, a halogen atom, or a halogenated alkyl group, and at least one of R1 and R2 is an electron attractive group selected from the group consisting of halogen atoms and halogenated alkyl groups.
2. The resin for a photoresist composition according to claim 1, wherein
a —S—(CH2)m—C(CF3)2—OH group is introduced at a terminal of a principal chain of the resin,
wherein m represents an integer from 2 to 4.
3. A photoresist composition, comprising a resin for a photoresist composition according to claim 1.
4. A photoresist composition according to claim 3, further comprising an acid generator component (B).
5. A photoresist composition according to claim 4, wherein the component (B) comprises (b-0) an onium salt that comprises a fluorinated alkylsulfonate ion as an anion.
6. A photoresist composition according to claim 4, wherein the component (B) comprises a sulfonium compound represented by either of general formulas (b-1) and (b-2) shown below:
7. A photoresist composition according to claim 6, wherein said component (B) further comprises (b-0) an onium salt that comprises a fluorinated alkylsulfonate ion as an anion.
8. A photoresist composition according to claim 3, further comprising a nitrogen-containing organic compound.
applying the photoresist composition according to claim 3 to a surface of a substrate;
This application is a continuation of U.S. application Ser. No. 10/557,694, filed Nov. 22, 2005, which is the US National Phase filing under 35 U.S.C. §371 of PCT/JP2004/008004, filed on Jun. 2, 2004, which claims priority under 35 U.S.C. §119(a)-(d) to Japanese Patent Application No. 2003-160478, filed Jun. 5, 2003; Japanese Patent Application No. 2003-428853, filed Dec. 25, 2003; and Japanese Patent Application No. 2004-57449, filed Mar. 2, 2004. The contents of these applications are incorporated herein by reference in their entireties.
The present invention relates to a resin for a photoresist composition, a photoresist composition, and a method for forming a photoresist composition.
Until recently, polyhydroxystyrenes or derivatives thereof in which the hydroxyl groups are protected with acid dissociable, dissolution inhibiting groups, which display high transparency relative to a KrF excimer laser (248 nm), have been used as the base resin component of chemically amplified resists. However, these days, the miniaturization of semiconductor elements has progressed even further, and the development of processes that use ArF excimer lasers (193 nm) to produce very fine resist patterns of 130 nm or less is being vigorously pursued.
The present invention takes the above circumstances into consideration, with an object of providing a resin that can be used in a photoresist composition which exhibits favorable resolution and LER characteristics, and enables a reduction in the level of defects, as well as providing a photoresist composition and a method for forming a resist pattern that use such a resin.
In this description, the term “structural unit” refers to a monomer unit which contributes to the formation of a polymer (resin).
BEST MODE FOR CARRYING OUT THE INVENTION Resin for Resist Composition
The above description of a resin having a hydroxyl group bonded to a carbon atom, wherein the carbon atom in the α-position to the hydroxyl group has at least one electron attractive group can be expressed more specifically, and ideally, as a resin having a —CR1R2OH group, wherein R1 and R2 each represent, independently, an alkyl group, halogen atom, or halogenated alkyl group, and at least one of R1 and R2 is an electron attractive group selected from the group consisting of halogen atoms and halogenated alkyl groups.
In this resin for a photoresist composition, the proportion of structural units (M1) that include the aforementioned —CR1R2OH group bonded to a polymer terminal (hereafter, this group may also be referred to as the “terminal structure”) is preferably at least 1 mol % (and preferably 2 mol % or higher) relative to the combined 100 mol % of all the structural units other than the structural units (M1) within the photoresist composition resin (resin for a photoresist composition).
The terminal structure can be introduced at a polymer terminal, for example, by adding a chain transfer agent containing a —CR1R2OH group during production of the polymer by radical polymerization using a monomer and a polymerization initiator. In this case, the structural unit (M1) containing the terminal structure is a structural unit (M1) derived from the chain transfer agent.
The chain transfer agent is represented, for example, by a general formula X—R′—CR1R2OH.
In this formula, X represents a hydroxyl group or thiol group, and this type of chain transfer agent bonds to the polymer terminal through elimination of the hydrogen atom of the hydroxyl group or thiol group. Accordingly, the structural unit (M1) in this case is the unit generated when the hydrogen atom is removed from the hydroxyl group or thiol group of the group X within the formula X—R′—CR1R2OH. In terms of reactivity, X is most preferably a thiol group.
Furthermore, R′ represents a bivalent aliphatic hydrocarbon group (which may be a straight-chain, branched-chain, or cyclic group) or a bivalent aromatic hydrocarbon group, and of these, a straight-chain or branched-chain aliphatic hydrocarbon group is preferred.
Preferred chain transfer agents can be represented by the general formula SH—(CH2)m—C(CF3)2—OH (wherein, m represents an integer from 2 to 4). Accordingly, preferred forms for the structural unit (M1) can be represented by a general formula —S—(CH2)m—C(CF3)2—OH.
Examples of suitable chain-like alkoxyalkyl groups include 1-ethoxyethyl groups, 1-methoxymethylethyl groups, 1-isopropoxyethyl groups, 1-methoxypropyl groups, and 1-n-butoxyethyl groups; examples of suitable tertiary alkyloxycarbonyl groups include tert-butyloxycarbonyl groups and tert-amyloxycarbonyl groups; examples of suitable tertiary alkyl groups include chain-like tertiary alkyl groups such as tert-butyl groups and tert-amyl groups, and tertiary alkyl groups that contain an aliphatic polycyclic group, such as 2-methyl-2-adamantyl groups and 2-ethyl-2-adamantyl groups; examples of suitable tertiary alkoxycarbonylalkyl groups include tert-butyloxycarbonylmethyl groups and tert-amyloxycarbonylmethyl groups; and examples of suitable cyclic ether groups include tetrahydropyranyl groups and tetrahydrofuranyl groups. As follows is a description of specific examples of preferred (meth)acrylate-based resins of the present invention.
(a1): Structural units derived from a (meth)acrylate ester containing an acid dissociable, dissolution inhibiting group.
The resin may also contain the structural units (a2) and (a3) described below, and resins that contain the structural units (a1) and (a2) are preferred, and resins that contain (a1), (a2), and (a3) are even more desirable.
(a2): Structural units derived from a (meth)acrylate ester containing a lactone ring.
Normally, in addition to the aforementioned terminal structure, a small quantity of structural units derived from the radical polymerization initiator are also introduced at the polymer terminals.
In the structural unit (a1), there are no particular restrictions on the acid dissociable, dissolution inhibiting group. Typically, groups that form cyclic or chain-like tertiary alkyl esters with the side-chain carboxyl group of a (meth)acrylate are widely known, and of these, aliphatic monocyclic or polycyclic group-containing acid dissociable, dissolution inhibiting groups are preferred, and aliphatic polycyclic group-containing acid dissociable, dissolution inhibiting groups are particularly desirable.
The aforementioned groups R2 and R3 each preferably represent, independently, a lower alkyl group of 1 to 5 carbon atoms. Of the structural units represented by the formula (II), cases in which R2 and R3 are both methyl groups are preferred industrially, and specific examples include structural units derived from 2-(1-adamantyl)-2-propyl (meth)acrylate.
Furthermore, the group —COOR4 may be bonded to either position 3 or 4 of the tetracyclododecanyl group shown in the formula, and the bonding position cannot be further specified. Similarly, the carboxyl group residue of the (meth)acrylate structural unit may be bonded at either position 8 or 9 in the formula, and the bonding position cannot be further specified.
Examples of the structural unit (a2) include structural units in which either a monocyclic group formed from a lactone ring, or an aliphatic polycyclic ring containing a lactone ring, is bonded to an ester side chain of a (meth)acrylate ester. Here, the term lactone ring refers to a single ring that contains a —O—C(O)— structure, and this ring is counted as the first ring. Accordingly, the case in which the only ring structure is the lactone ring is referred to as a monocyclic group, and groups containing other ring structures are described as polycyclic groups regardless of the structure of the other rings.
In order to satisfy the above pKa numerical range, a configuration of the first aspect is preferred, and a structure in which the substituent is a —CR1R2OH group (wherein, R1 and R2 each represent, independently, an alkyl group, halogen atom, or halogenated alkyl group, and at least one of R1 and R2 is an electron attractive group selected from the group consisting of halogen atoms and halogenated alkyl groups) is particularly desirable.
Specific examples of (b-0) include diphenyliodonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, (4-methoxyphenyl)phenyliodonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, tri(4-methylphenyl) sulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, (4-methylphenyl)diphenylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, dimethyl(4-hydroxynaphthyl) trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, monophenyldimethylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, diphenylmonomethylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, triphenylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, (4-methoxyphenyl)diphenylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, (p-tert-butylphenyl)diphenylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, tri(p-tert-butylphenyl)sulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate, and (4-trifluoromethylphenyl)diphenylsulfonium trifluoromethanesulfonate, heptafluoropropanesulfonate or nonafluorobutanesulfonate.
In the present invention, iminosulfonate-based acid generators, which represent a different acid generator from the aforementioned (b-0) salts, can also be used favorably.
In the present invention, by combining at least one compound selected from the above sulfonium compounds 1 and 2, with an aforementioned resin for a resist composition according to the present invention, a particularly superior defect reduction effect is achieved. Here, the term “defect” refers to scum and general resist pattern abnormalities detected by inspection of a resist pattern following developing, from directly above the resist pattern, using a surface defect inspection device (brand name: KLA) from KLA Tencor Corporation. These types of defects can cause reductions in process yields, and a deterioration in the product performance, and consequently represent an extremely large problem. A number of factors are thought to cause these defects, including the resist resolution performance, irregularities in the alkali solubility arising from insoluble matter or impurities within the resist, and the surface state of the resist.
Furthermore, the blend ratio (weight ratio) between the (b-0) salt and the one or more compounds selected from amongst the sulfonium compounds 1 and 2 is preferably within a range from 1:9 to 9:1, and preferably from 1:5 to 5:1, and even more preferably from 1:2 to 2:1. By mixing the acid generators using this type of ratio, a resin with particularly superior LER and developing defect characteristics can be obtained. Using a mixture of a sulfonium compound represented by the general formula (b-1) and a (b-0) salt is the most preferred configuration.
Examples of suitable solvents include γ-butyrolactone, ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone and 2-heptanone; polyhydric alcohols and derivatives thereof such as ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol, or the monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether or monophenyl ether of dipropylene glycol monoacetate; cyclic ethers such as dioxane; and esters such as methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methyl methoxypropionate, and ethyl ethoxypropionate. Mixed solvents of propylene glycol monomethyl ether acetate (PGMEA) and a polar solvent are preferred. The mixing ratio within this type of mixed solvent can be determined on the basis of the co-solubility of the PGMEA and the polar solvent, but is preferably within a range from 1:9 to 8:2, and even more preferably from 2:8 to 5:5
More specifically, in those cases where ethyl lactate (EL) is added as the polar solvent, the weight ratio of PGMEA:EL is preferably within a range from 2:8 to 5:5, and even more preferably from 3:7 to 4:6. Furthermore, as the organic solvent, a mixed solvent of at least one of PGMEA and EL, together with γ-butyrolactone is also preferred. In such cases, the weight ratio between the former and latter components is preferably within a range from 70:30 to 95:5. There are no particular restrictions on the quantity used of the component (C), which is set in accordance with the resist film thickness so as to produce a concentration that enables favorable application of the composition to a substrate, and is typically sufficient to produce a solid fraction concentration within the resist composition of 2 to 20% by weight, and preferably from 5 to 15% by weight.
Namely, a positive photoresist composition of the present invention is first applied to the surface of a substrate such as a silicon wafer using a spinner or the like, a prebake is conducted under temperature conditions of 80 to 150° C. for 40 to 120 seconds, and preferably for 60 to 90 seconds, and then following selective exposure of an ArF excimer laser through a desired mask pattern using, for example, an ArF exposure apparatus, PEB (post exposure baking) is conducted under temperature conditions of 80 to 150° C. for 40 to 120 seconds, and preferably for 60 to 90 seconds. Subsequently, developing is conducted using an alkali developing solution such as a 0.1 to 10% by weight aqueous solution of tetramethylammonium hydroxide. In this manner, a resist pattern which is faithful to the mask pattern can be obtained.
0.1 mols of a monomer containing a 50/30/20 (mol %) mixture of γ-butyrolactone methacrylate (the monomer that corresponds with the unit of the general formula (VII) wherein R is a methyl group), 2-methyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is a methyl group), and 3-hydroxy-1-adamantyl acrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a hydrogen atom) was dissolved in 150 ml of THF (tetrahydrofuran), a radical polymerization was initiated at 70° C. using AIBN (in a quantity equivalent to 4 mol % relative to 100 mol % of the above monomer), the compound represented by a chemical formula (XIV) shown below (pKa value of the terminal structure: approximately 7) was added as a polymerization chain transfer agent, in a quantity equivalent to 2 mol % relative to 100 mol % of the combination of the above monomer and AIBN, and a polymerization reaction was conducted.
Following completion of the polymerization reaction, the reaction solution was poured into 2,000 ml of n-heptane, the resulting mixture was stirred for 30 minutes at 25° C., and the precipitated solid was recovered by filtration. This solid was then redissolved in 200 ml of THF, and once again poured into 2,000 ml of n-heptane, stirred for 30 minutes at 25° C., and the resulting precipitated resin was recovered by filtration. The weight average molecular weight of the resin was 10,000.
Subsequently, the thus obtained chemically amplified positive photoresist composition was applied to the surface of a silicon wafer using a spinner, and was then prebaked (PAB treatment) and dried for 90 seconds at 120° C. on a hotplate, thereby forming a resist layer with a film thickness of 250 nm.
This film was then selectively irradiated with an ArF excimer laser (193 nm) through a mask pattern, using an ArF exposure apparatus (NSR-S302, manufactured by Nikon Corporation, NA (numerical aperture)=0.60, ⅔ annular illumination).
The film was then subjected to PEB treatment at 120° C. for 90 seconds, subsequently subjected to puddle development for 60 seconds at 23° C. in a 2.38% by weight aqueous solution of tetramethylammonium hydroxide, and was then washed for 20 seconds with water, and dried.
Furthermore, when the 3σ value, which is a measure of the line edge roughness of the line and space pattern, was determined, the result was 7.2 nm.
Defects were measured using a surface defect inspection device KLA2132 (brand name) from KLA Tencor Corporation, and the number of defects within the wafer was evaluated. Three wafers were tested, and the average value was determined. The result revealed 3 defects.
With the exception of altering the proportion of the chain transfer agent represented by the above chemical formula (XIV) from 2 mol % to 3 mol %, a resist composition resin with a weight average molecular weight of 10,000 was obtained in the same manner as the example 1.
With the exception of altering the conditions so that the weight average molecular weight of the resist composition resin was 7,000, a resist composition resin was obtained in the same manner as the example 2.
With the exception of altering the monomer composition to a 50/30/20 (mol %) mixture of norbornanelactone acrylate (the monomer that corresponds with the unit of the general formula (V) wherein R is a hydrogen atom), 2-ethyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is an ethyl group), and 3-hydroxy-1-adamantyl acrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a hydrogen atom), a resist composition resin with a weight average molecular weight of 7,000 was obtained in the same manner as the example 3.
With the exception of altering the monomer composition to a 40/40/20 (mol %) mixture of norbornanelactone methacrylate (the monomer that corresponds with the unit of the general formula (VI) wherein R is a methyl group), 2-ethyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is an ethyl group), and 3-hydroxy-1-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a methyl group), a resist composition resin with a weight average molecular weight of 6,400 was obtained in the same manner as the example 1.
With the exception of altering the conditions so that the weight average molecular weight of the resist composition resin was 4,800, a resist composition resin was obtained in the same manner as the example 1.
With the exception of using 1.5 parts by weight of triphenylsulfonium nonafluorobutanesulfonate and 1.5 parts by weight of the compound represented by a chemical formula (XV) shown below as the component (B), evaluation was conducted in the same manner as the example 5. The results are summarized in Table 1.
With the exceptions of altering the monomer composition to a 40/40/20 (mol %) mixture of γ-butyrolactone acrylate (the monomer that corresponds with the unit of the general formula (VII) wherein R is a hydrogen atom), 2-methyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is a methyl group), and 3-hydroxy-1-adamantyl acrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a hydrogen atom), and altering the proportion of the chain transfer agent represented by the above chemical formula (XIV) to 3 mol %, a resist composition resin with a weight average molecular weight of 7,000 was obtained in the same manner as the example 1. This resin was then evaluated in the same manner as the example 1. The results are summarized in Table 1.
With the exceptions of altering the monomer composition to a 40/40/15/5 (mol %) mixture of γ-butyrolactone methacrylate (the monomer that corresponds with the unit of the general formula (VII) wherein R is a methyl group), 2-methyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is a methyl group), 3-hydroxy-1-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a methyl group), and tricyclodecanyl methacrylate (the monomer that corresponds with the structural unit of the general formula (IX) wherein R is a methyl group), and altering the proportion of the chain transfer agent represented by the above chemical formula XIV to 3 mol %, a resist composition resin with a weight average molecular weight of 7,000 was obtained in the same manner as the example 1. This resin was then evaluated in the same manner as the example 1. The results are summarized in Table 1.
With the exception of not using the chain transfer agent, the same method as the example 1 was used to produce a resist composition resin, and subsequently, a resist composition was then prepared with the same composition as that described in the example 1, and a positive photoresist composition was prepared using the same method as the example 1.
With the exception of not using the chain transfer agent, the same method as the example 4 was used to produce a resist composition resin, and subsequently, a resist composition was then prepared with the same composition as that described in the example 1, and a positive photoresist composition was prepared using the same method as the example 1. Evaluation was then conducted in the same manner as the example 1. The results are summarized in Table 1.
With the exception of not using the chain transfer agent, the same method as the example 5 was used to produce a resist composition resin, and subsequently, a resist composition was then prepared with the same composition as that described in the example 1, and a positive photoresist composition was prepared using the same method as the example 1. Evaluation was then conducted in the same manner as the example 1. The results are summarized in Table 1.
DOF LER Collapse Defects
(nm) Shape (nm) (nm) (number)
Example 1 500 Rectangular 7.2 57 3
Example 2 550 Rectangular (slight 6.5 55 2
Example 3 500 Rectangular 5.1 58 1
Example 4 500 Rectangular 6 60 1
Example 5 500 Very rectangular 5.5 55 1
Example 6 500 Rectangular 6.1 60 1
Example 7 500 Very rectangular 5 55 1
Example 8 500 Rectangular 7 62 1
Example 9 400 Very rectangular 6.5 55 1
Comparative 500 Rectangular 9.8 72 10
Comparative 550 Rectangular 8 69 12
Comparative 500 Rectangular (slight 8 65 15
example 3 base broadening)
With the exceptions of altering the monomer composition to a 40/40/20 (mol %) mixture of γ-butyrolactone acrylate (the monomer that corresponds with the unit of the general formula (VII) wherein R is a hydrogen atom), 2-ethyl-2-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (I) wherein R is a methyl group and R1 is an ethyl group), and 3-hydroxy-1-adamantyl methacrylate (the monomer that corresponds with the unit of the general formula (VIII) wherein R is a methyl group), and altering the proportion of the chain transfer agent represented by the above chemical formula XIV to 2.5 mol %, a resist composition resin with a weight average molecular weight of 7,000 was obtained in the same manner as the example 1.
Subsequently, the thus obtained positive photoresist composition was applied to the surface of a silicon wafer using a spinner, and was then prebaked (PAB treatment) and dried for 90 seconds at 90° C. on a hotplate, thereby forming a resist layer with a film thickness of 220 nm.
The film was then subjected to PEB treatment at 90° C. for 90 seconds, subsequently subjected to puddle development for 60 seconds at 23° C. in a 2.38% by weight aqueous solution of tetramethylammonium hydroxide, and was then washed for 20 seconds with water, and dried, thereby yielding a contact hole (CH) pattern) with a hole diameter of 300 nm and a pitch of 500 nm. The sensitivity (Eop) was 18.5 mJ/cm2.
The present invention provides a photoresist composition and a method for forming a resist pattern that offer improved resolution and LER characteristics, and reduced levels of defects, and is consequently extremely useful industrially.
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U.S. Classification 430/270.1, 430/914, 526/224, 430/908, 526/85, 430/326, 526/78
International Classification G03F7/039, H01L21/027, G03F7/028, C08F220/28, G03F7/033, H01L21/30, C08F2/38, G03F7/004
Cooperative Classification G03F7/0045, G03F7/0397, Y10S430/109, Y10S430/115