US 6,586,152 B1 · Agent for reducing substrate dependence

Abstract

The present invention relates to an agent for reducing substrate dependence useful as an ingredient of a resist composition used for preparation of semiconductor devices and the like, which comprises a compound shown by the following general formula [1]: wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1.

Claims40

Dependent claims

A method for reducing substrate dependence of a resist composition, which comprises the steps of:

incorporating into the resist composition, as an agent for reducing substrate dependence, a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
applying the resist composition to a special substrate being selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film, wherein the resist composition is one containing a) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, b) an acid generator.

A method for reducing substrate dependence of a resist composition, which comprises the steps of:

incorporating into the resist composition, as an agent for reducing substrate dependence, a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
applying the resist composition to a special substrate being selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film, wherein the resist composition is one containing a) a polymer soluble in an aqueous alkaline developing solution, b) an acid generator, c) a cross-linking compound which can make the polymer soluble in an aqueous alkaline developing solution hardly soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid.

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, and
c) an acid generator;
wherein the polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid is a compound shown by the general formula [2] or [3]:
wherein R and R1 are independently a hydrogen atom or a methyl group, R2 and R3 are independently a hydrogen atom, a lower alkyl group or an aryl group, except for the case where R2 and R3 are both hydrogen atoms, and R2 and R3 may form together an alkylene ring;
R4 is a lower alkyl group or an aralkyl group;
R5 is a cyano group;
a carboxylic group which may be esterified or a phenyl group which may be substituted;
m and n′ are a natural number;
and k is 0 or a natural number provided that m>k;
wherein R6 and R21 are independently a hydrogen atom or a methyl group;
R7 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acyloxy group, a 5- or 6-membered saturated heterocyclic oxy group or a group shown by the formula of R8O—CO—(CH2)z—O— in which R8 is an alkyl group or z is 0 or a natural number;
R22 is a cyano group, a phenyl group which may have a substituent or a carboxyl group which may be esterified;
p and r are natural number;
f is 0 or a natural number, provided that p>f;
with the proviso that when R7 is a hydrogen atom, a lower alkyl group, a lower alkoxy group except for one which is easily changed into a hydroxy group by an acid, an acyloxy group or a group R8O—CO—(CH2)z—O— (in which R8 and z have the same meaning as above) except for a case where R8 is a group labile by an acid, R22 is a phenyl group having a substituent which is easily changed into a hydroxy group or a group of —COOR45 (in which R45 is an alkyl group labile by an acid) an that when R7 is an alkoxy group which is easily changed into a hydroxy group, a 5- or 6-membered saturated oxy group or a group of R8O—CO—(CH2)z—O— (in which R8 and z have the same meaning as above) in which R8 is labile by an acid, R22 is a cyano group, a phenyl group which may have a substituent or a carboxyl group which may be esterified.

17 more elements

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, and
c) an acid generator;
wherein the acid generator is a compound represented by the general formula [8], [9], [11], [12], [13] and [15];
wherein R9 and R10 are independently an alkyl group or a haloalkyl group and A′ is a sulfonyl group or a carbonyl group;
wherein R11 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a haloalkyl group, and R12 is an alkyl group, a haloalkyl group or a group shown by the following general formula [10]:
wherein R13 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a halogen group, and q is 0 or an integer of 1 to 3;
wherein R14 is a hydrogen atom, a halogen atom, an alkyl group or a trifluoromethyl group and R15 is an alkyl group, an aralkyl group, an alkoxy group, a phenyl group or a tolyl group;
wherein R16 is an alkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, R17 and R18 are independently a hydrogen atom, an alkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, and R19 is a fluoroalkyl group, a trifluoromethylphenyl group, a methyl group or tolyl group;
wherein R29 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, Q′ is a sulfonyl group or a carbonyl group, R30 and R31 are independently a hydrogen atom, a methyl group, a methoxy group, a nitro group, a cyano group, a hydroxy group or a group shown by the following general formula [14]:
wherein R33 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, Q′ is a sulfonyl group or a carbonyl group, and R32 us a hydrogen atom, a methyl group or an ethyl group;
wherein R34 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, R35 is a hydrogen atom, a methyl group, a fluoroalkyl group, a methoxy group, a nitro group, a cyano group, a hydroxy group or a group shown by the above general formula [14].

13 more elements

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer soluble in an aqueous alkaline developing solution,
c) an acid generator, and
d) a cross-linking compound which can make a polymer hardly soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid.

5 more elements

Dependencies are inferred from the claim text.

Facts

Application

09/592,851Filed 12 Jun 2000

Priority

JP 11-16319110 Jun 1999

Granted

1 Jul 2003

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

G03F 7/0048
Photosensitive materials: characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
G03F 7/0045
Photosensitive materials: with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
G03F 7/038
Photosensitive materials: macromolecular compounds which are rendered insoluble or differentially wettable
G03F 7/039
Photosensitive materials: macromolecular compounds which are photodegradable, e.g. positive electron resists

Abstract

Claims40

Dependent claims

A method for reducing substrate dependence of a resist composition, which comprises the steps of:

incorporating into the resist composition, as an agent for reducing substrate dependence, a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
applying the resist composition to a special substrate being selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film, wherein the resist composition is one containing a) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, b) an acid generator.

A method for reducing substrate dependence of a resist composition, which comprises the steps of:

incorporating into the resist composition, as an agent for reducing substrate dependence, a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
applying the resist composition to a special substrate being selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film, wherein the resist composition is one containing a) a polymer soluble in an aqueous alkaline developing solution, b) an acid generator, c) a cross-linking compound which can make the polymer soluble in an aqueous alkaline developing solution hardly soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid.

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, and
c) an acid generator;
wherein the polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid is a compound shown by the general formula [2] or [3]:
wherein R and R1 are independently a hydrogen atom or a methyl group, R2 and R3 are independently a hydrogen atom, a lower alkyl group or an aryl group, except for the case where R2 and R3 are both hydrogen atoms, and R2 and R3 may form together an alkylene ring;
R4 is a lower alkyl group or an aralkyl group;
R5 is a cyano group;
a carboxylic group which may be esterified or a phenyl group which may be substituted;
m and n′ are a natural number;
and k is 0 or a natural number provided that m>k;
wherein R6 and R21 are independently a hydrogen atom or a methyl group;
R7 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, an acyloxy group, a 5- or 6-membered saturated heterocyclic oxy group or a group shown by the formula of R8O—CO—(CH2)z—O— in which R8 is an alkyl group or z is 0 or a natural number;
R22 is a cyano group, a phenyl group which may have a substituent or a carboxyl group which may be esterified;
p and r are natural number;
f is 0 or a natural number, provided that p>f;
with the proviso that when R7 is a hydrogen atom, a lower alkyl group, a lower alkoxy group except for one which is easily changed into a hydroxy group by an acid, an acyloxy group or a group R8O—CO—(CH2)z—O— (in which R8 and z have the same meaning as above) except for a case where R8 is a group labile by an acid, R22 is a phenyl group having a substituent which is easily changed into a hydroxy group or a group of —COOR45 (in which R45 is an alkyl group labile by an acid) an that when R7 is an alkoxy group which is easily changed into a hydroxy group, a 5- or 6-membered saturated oxy group or a group of R8O—CO—(CH2)z—O— (in which R8 and z have the same meaning as above) in which R8 is labile by an acid, R22 is a cyano group, a phenyl group which may have a substituent or a carboxyl group which may be esterified.

17 more elements

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]:
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer which becomes soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid, and
c) an acid generator;
wherein the acid generator is a compound represented by the general formula [8], [9], [11], [12], [13] and [15];
wherein R9 and R10 are independently an alkyl group or a haloalkyl group and A′ is a sulfonyl group or a carbonyl group;
wherein R11 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a haloalkyl group, and R12 is an alkyl group, a haloalkyl group or a group shown by the following general formula [10]:
wherein R13 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a halogen group, and q is 0 or an integer of 1 to 3;
wherein R14 is a hydrogen atom, a halogen atom, an alkyl group or a trifluoromethyl group and R15 is an alkyl group, an aralkyl group, an alkoxy group, a phenyl group or a tolyl group;
wherein R16 is an alkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, R17 and R18 are independently a hydrogen atom, an alkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, and R19 is a fluoroalkyl group, a trifluoromethylphenyl group, a methyl group or tolyl group;
wherein R29 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, Q′ is a sulfonyl group or a carbonyl group, R30 and R31 are independently a hydrogen atom, a methyl group, a methoxy group, a nitro group, a cyano group, a hydroxy group or a group shown by the following general formula [14]:
wherein R33 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, Q′ is a sulfonyl group or a carbonyl group, and R32 us a hydrogen atom, a methyl group or an ethyl group;
wherein R34 is an alkyl group, a fluoroalkyl group, a phenyl group, a substituted phenyl group or an aralkyl group, R35 is a hydrogen atom, a methyl group, a fluoroalkyl group, a methoxy group, a nitro group, a cyano group, a hydroxy group or a group shown by the above general formula [14].

13 more elements

A coated substrate comprising:

a special substrate made of a material selected from the group consisting of SiN, TiN, SiON, BPSG and a strong basic organic anti-reflective film;
and
a resist film obtained by coating a resist composition on said substrate, said resist composition comprising:
a) a compound shown by the following general formula [1]
wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1, wherein an amount of the compound to be used is 0.5 to 30 wt % relative to the total amount of the resist composition,
b) a polymer soluble in an aqueous alkaline developing solution,
c) an acid generator, and
d) a cross-linking compound which can make a polymer hardly soluble in an aqueous alkaline developing solution by a chemical change by an action of an acid.

5 more elements

Dependencies are inferred from the claim text.

Agent for reducing substrate dependence

Life of this patent

Abstract

Claims40

Agent for reducing substrate dependence

Life of this patent

Abstract

Claims40