METHOD FOR PRODUCING ACTIVE RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, METHOD FOR PRODUCING ONIUM SALT COMPOUND FOR ACTIVE RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, PATTERN FORMING METHOD, METHOD FOR PRODUCING ELECTRONIC DEVICE, AND ONIUM SALT COMPOSITION

Abstract

The present invention provides a method for producing an actinic ray-sensitive or radiation-sensitive resin composition, including (X) mixing a specific onium salt compound (1) with a specific salt compound (2) in a non-aqueous solvent (S) to obtain a specific onium salt compound (3), (Y) obtaining a specific onium salt compound (A) from the onium salt compound (3), and (Z) mixing the onium salt compound (A) with a resin (B) whose solubility in a developer changes due to action of acid; a method for producing an onium salt compound (A) for an actinic ray-sensitive or radiation-sensitive resin composition, including (X) and (Y); a pattern forming method; and a method for manufacturing an electronic device.

Claims

1. A method for producing an actinic ray-sensitive or radiation-sensitive resin composition, the method comprising: mixing an onium salt compound (1) represented by Formula (1A) or Formula (1B) with a salt compound (2) represented by Formula (2) in a non-aqueous solvent (S) to obtain an onium salt compound (3) represented by Formula (3A) or Formula (3B); obtaining an onium salt compound (A) represented by Formula (4A) or Formula (4B) from the onium salt compound (3); and mixing the onium salt compound (A) with a resin (B) whose solubility in a developer changes due to action of acid, ##STR00125## in Formulae (1A), (3A), and (4A), R.sup.1a, R.sup.1b, and R.sup.1c each independently represent an alkyl group, a cycloalkyl group, an aryl group, or *W.sub.1C(O)Ar.sup.1, two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring, and *represents a linkage site to S.sup.+, W.sub.1 represents a single bond or an alkylene group, and Ar.sup.1 represents an aryl group, in Formulae (1B), (3B), and (4B), R.sup.1d and R.sup.1e each independently represent an alkyl group, a cycloalkyl group, or an aryl group, in Formulae (1A) and (1B), Rf represents an alkyl group or an aryl group which includes one or more fluorine atoms, in Formula (2), R.sub.2.sup.+ represents an organic cation which does not have a polymer structure, and X.sup. represents Cl.sup. or Br.sup., in Formulae (3A) and (3B), X.sup. represents Cl.sup. or Br.sup., in Formulae (4A) and (4B), Z.sup.n represents an n-valent organic anion, and n represents an integer of 1 or more.

2. The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein R.sup.1a, R.sup.1b, and R.sup.1c in Formula (1A), Formula (3A), and Formula (4A) each independently represent an alkyl group which does not include a halogen atom, a cycloalkyl group, an aryl group, or *W.sub.1C(O)Ar.sup.1, where two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring, and *represents a linkage site to S.sup.+, W.sub.1 represents a single bond or an alkylene group, and Ar.sup.1 represents an aryl group.

3. The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein R.sub.2.sup.+ in Formula (2) is an organic cation represented by Formula (2B), ##STR00126## in Formula (2B), R.sup.2a to R.sup.2d each independently represent an alkyl group, a cycloalkyl group, or an aryl group.

4. The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein the non-aqueous solvent (S) contains at least one of an ester-based solvent or an ether-based solvent.

5. The method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to claim 1, wherein R.sup.1a, R.sup.1b, and R.sup.1c in Formulae (1A), (3A), and (4A) are aryl groups, where two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring.

6. A method for producing an onium salt compound (A) for an actinic ray-sensitive or radiation-sensitive resin composition, the method comprising: mixing an onium salt compound (1) represented by Formula (1A) or Formula (1B) with a salt compound (2) represented by Formula (2) in a non-aqueous solvent (S) to obtain an onium salt compound (3) represented by Formula (3A) or Formula (3B); and obtaining an onium salt compound (A) represented by Formula (4A) or Formula (4B) from the onium salt compound (3), ##STR00127## in Formulae (1A), (3A), and (4A), R.sup.1a, R.sup.1b, and R.sup.1c each independently represent an alkyl group, a cycloalkyl group, an aryl group, or *W.sub.1C(O)Ar.sup.1, two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring, and *represents a linkage site to S.sup.+, W.sub.1 represents a single bond or an alkylene group, and Ar represents an aryl group, in Formulae (1B), (3B), and (4B), R.sup.1d and R.sup.1e each independently represent an alkyl group, a cycloalkyl group, or an aryl group, in Formulae (1A) and (1B), Rf represents an alkyl group or an aryl group which includes one or more fluorine atoms, in Formula (2), R.sub.2.sup.+ represents an organic cation which does not have a polymer structure, and X.sup. represents Cl.sup. or Br.sup., in Formulae (3A) and (3B), X.sup. represents Cl.sup. or Br.sup., in Formulae (4A) and (4B), Z.sup.n represents an n-valent organic anion, and n represents an integer of 1 or more.

7. The method for producing an onium salt compound (A) according to claim 6, wherein R.sup.1a, R.sup.1b, and R.sup.1c in Formula (1A), Formula (3A), and Formula (4A) each independently represent an alkyl group which does not include a halogen atom, a cycloalkyl group, an aryl group, or *W.sub.1C(O)Ar.sup.1, where two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring, and *represents a linkage site to S.sup.+, W.sub.1 represents a single bond or an alkylene group, and Ar.sup.1 represents an aryl group.

8. The method for producing an onium salt compound (A) according to claim 6, wherein R.sub.2.sup.+ in Formula (2) is an organic cation represented by Formula (2B), ##STR00128## in Formula (2B), R.sup.2a to R.sup.2d each independently represent an alkyl group, a cycloalkyl group, or an aryl group.

9. The method for producing an onium salt compound (A) according to claim 6, wherein the non-aqueous solvent (S) contains at least one of an ester-based solvent or an ether-based solvent.

10. The method for producing an onium salt compound (A) according to claim 6, wherein R.sup.1a, R.sup.1b, and R.sup.1c in Formulae (1A), (3A), and (4A) are aryl groups, where two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring.

11. An onium salt composition including an onium salt compound, comprising: 0.001 mol % to 3 mol % of an organic cation represented by Formula (2A) with respect to 1 mol of the onium salt compound represented by Formula (4A) or Formula (4B), ##STR00129## in Formula (2A), Q represents an N atom or a P atom, m represents an integer of 1 to 4, R.sup.2e represents an alkyl group, a cycloalkyl group, or an aryl group, and a plurality of R.sup.2e's may be the same as or different from each other, and R.sup.2e's adjacent to each other may form a ring, in Formula (4A), R.sup.1a, R.sup.1b, and R.sup.1c each independently represent an alkyl group, a cycloalkyl group, an aryl group, or *W.sub.1C(O)Ar.sup.1, two of R.sup.1a, R.sup.1b, and R.sup.1c may be bonded to each other to form a ring, and *represents a linkage site to S.sup.+, W.sub.1 represents a single bond or an alkylene group, and Ar.sup.1 represents an aryl group, in Formula (4B), R.sup.1d and R.sup.1e each independently represent an alkyl group, a cycloalkyl group, or an aryl group, in Formulae (4A) and (4B), Z.sup.n represents an n-valent organic anion, and n represents an integer of 1 or more.

12. The onium salt composition according to claim 11, wherein the organic cation represented by Formula (2A) is represented by Formula (2B), ##STR00130## in Formula (2B), R.sup.2a to R.sup.2d each independently represent an alkyl group, a cycloalkyl group, or an aryl group.

13. The onium salt composition according to claim 11, wherein R.sup.1a, R.sup.1b, and R.sup.1c in Formula (4A) are aryl groups.

14. A pattern forming method comprising: obtaining an actinic ray-sensitive or radiation-sensitive resin composition by the method for producing an actinic ray-sensitive or radiation-sensitive resin composition according to claim 1; forming an actinic ray-sensitive or radiation-sensitive film on a substrate using the actinic ray-sensitive or radiation-sensitive resin composition; exposing the actinic ray-sensitive or radiation-sensitive film; and developing the exposed actinic ray-sensitive or radiation-sensitive film using a developer to form a pattern.

15. A method for manufacturing an electronic device, comprising: the pattern forming method according to claim 14.

Description

EXAMPLES

[0708] Hereinbelow, the present invention will be described in more detail with reference to Examples. The materials, the amounts of materials used, the proportions, the treatment details, and the treatment procedure in Examples below may be appropriately modified as long as the modifications do not depart from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited to Examples shown below.

Example S1: Synthesis of Compound A1

Synthesis of Intermediate Compound (3-1)

##STR00056##

[0709] A mixture of 160 mL of a 1.3 M tetrahydrofuran (THF) solution of isopropylmagnesium chloride-lithium chloride complex and 40 mL of tetrahydrofuran was cooled to 0 C., and 45.4 g of 1-bromo-4-(trifluoromethyl)benzene was added dropwise thereto. The obtained mixture was stirred at room temperature for 6 hours to prepare a Grignard reagent. The mixture was cooled to 0 C., and 12.0 g of thionyl chloride was slowly added dropwise thereto. 160 mL of 1 N hydrochloric acid was added dropwise thereto, and the mixture was extracted with 80 mL of heptane. An organic layer was washed with 200 mL of water three times, and the organic layer was concentrated under reduced pressure. 100 mL of heptane was added to the obtained crude product, and the mixture was stirred and filtered to obtain a compound A with a yield of 60%.

##STR00057##

[0710] 120 mL of a 1.0 M tetrahydrofuran (THF) solution of isopropylmagnesium chloride was cooled to 0 C., and 25.2 g of 1-bromo-4-(trifluoromethyl)benzene was added dropwise thereto. The obtained mixture was stirred at room temperature for 6 hours to prepare a Grignard reagent. 19.0 g of the compound A was dissolved in 86 mL of 4-methyltetrahydropyran, the solution was cooled to 0 C., and 62.4 g of trimethylsilyl trifluoromethanesulfonate (TMSOTf) was added dropwise thereto. The prepared Grignard reagent was added dropwise to the obtained mixture, and the mixture was stirred for 1 hour. After 86 mL of 1 N hydrochloric acid was added dropwise, extraction was carried out with 140 mL of methylene chloride. The organic layer was washed with 140 mL of water three times, and the organic layer was concentrated under reduced pressure. 200 mL of diisopropyl ether was added to the obtained crude product, and the mixture was stirred and filtered to obtain a compound (1-1) with a yield of 67%.

##STR00058##

[0711] 10 g of the compound (1-1) was dissolved in 120 g of 4-methyltetrahydropyrane, tetrabutylammonium chloride (4.2 g) was added thereto while stirring, the mixture was heated to 40 C., and the mixture was further stirred for 2 hours. After returning to room temperature (25 C.), the mixture was filtered to collect crude crystals. The crude crystals were dissolved in 21 g of acetone, 105 g of tert-butyl methyl ether was added thereto while stirring at 40 C., and crystals were precipitated. After returning to room temperature, the mixture was filtered to collect crystals, thereby obtaining a compound (3-1) with a yield of 71%. [0712] .sup.1H NMR (Acetone-d6): 8.72, 8.07 ppm [0713] .sup.19F NMR(Acetone-d6): 63.8 ppm [0714] TfO.sup. represents CF.sub.3SO.sub.3.sup..

##STR00059##

[0715] 15 g (17.9 mmol) of the compound (Z-1), 250 g of methylene chloride, and 200 g of water were mixed, and then 18 g (35.8 mmol) of the compound (3-1) was added thereto, followed by stirring at room temperature for 30 minutes. After removing the aqueous layer, the organic layer was washed once with 0.1 N hydrochloric acid and three times with water, and the organic layer was concentrated under reduced pressure. 100 g of diisopropyl ether was added to the obtained crude product, the mixture was stirred, and the filtered solid was dried under reduced pressure for 5 hours to obtain a compound A1 with a yield of 87%. [0716] .sup.1H NMR (Acetone-d6): 8.37, 8.16, 8.11, 7.61 ppm [0717] .sup.19F NMR(Acetone-d6): 63.8, 112.7, 114.4, 118.6 ppm

Examples S2 to S26: Synthesis of Compounds A2 to A26

[0718] Compounds A2 to A26 shown in Tables 1 to 3 were obtained by the same method as in Example S1, except that the onium salt compound (1), the salt compound (2), and the non-aqueous solvent (S) were changed to the compounds shown in Tables 1 to 3, and the salt compound (5) was changed to the compound shown in Tables 1 to 3.

Comparative Example RS1: Synthesis of Compound RA1

##STR00060##

[0719] An intermediate compound (3-r1) was synthesized in the same manner as in JP2014-97969A, except that the compound (1-r1) was used.

[0720] A compound RA1 was obtained by the same method as in Example S1, except that the intermediate compound (3-r1) was used as the onium salt compound (3), and the salt compound (5) was changed to the salt compound consisting of the anion contained in the onium salt compound (A) and the sodium cation, which are shown in Table 2.

Comparative Example RS2: Synthesis of Intermediate Compound (3-r3)

##STR00061##

[0721] 11.1 g of the compound (1-r3) was dissolved in 125 ml of methylene chloride, 125 ml of a 1 M potassium bromide aqueous solution was added thereto, and the mixture was stirred at room temperature for 30 minutes. After removing the aqueous layer by a liquid separation operation, the mixture was washed with 125 ml of a 1 M potassium bromide aqueous solution three times and with 125 ml of water four times. As a result of confirming the NMR of the residue after concentration under reduced pressure, only the peak of the compound (1-r3) was detected, and the compound (3-r3) could not be obtained.

[Evaluation]

[0722] The obtained compounds A2 to A26 and RA1 were evaluated as shown below. The evaluation results are listed in Tables 1 to 3.

<Evaluation of Residual Rate of Onium Salt Compound (1)>

[0723] .sup.19F NMR of a sample solution obtained by dissolving 0.2 g of the onium salt compound (A) in 0.8 g of heavy acetone (heavy methanol in the case of low solubility in heavy acetone) was measured, and the residual rate Y (mol %) of the onium salt compound (1) was calculated using Expression (2-1). For the compound A15 and the compound A19, 1,4-difluorobenzene (0.5 mol with respect to 1 mol of the onium salt compound (A)) was added as an internal standard substance P to the sample solution, .sup.1H NMR and .sup.19F NMR were measured, and the residual rate Y (mol %) of the onium salt compound (1) was calculated using the above-described Formula (2-2).

<Evaluation of Residual Rate of Onium Salt Compound (3)>

[0724] A commercially available 0.01 N silver nitrate aqueous solution was diluted 10 times with ion exchange water to prepare a 0.001 N silver nitrate aqueous solution. 100 mg of the onium salt compound (A) is weighed and dissolved in 60 ml of a mixed solvent of THF and water (THF/water=54/6 (volume ratio)) to prepare a sample solution. Using the 0.001 N silver nitrate aqueous solution prepared above, the amount of the titrant was measured with an automatic titrator (AT-510, manufactured by KYOTO ELECTRONICS MANUFACTURING Co., Ltd.) for the empty solution of only the mixed solvent and the sample solution. From the results of the obtained amount of the titrant, the residual rate X (mol %) of the onium salt compound (3) with respect to 1 mol of the onium salt compound (A) was calculated using Expression (1) described above.

<Calculation of SP Value of Non-Aqueous Solvent (S)>

[0725] The calculation was performed using calculation software HSPiP 5th Edition 5.1.08.

[0726] The values are shown in Tables 1 to 3.

TABLE-US-00001 TABLE 1 Onium salt compound (A) Chemical Residual Calculated foumula of rate Y of Residual rate Onium salt Salt Onium salt SP value of Salt onium salt onium salt X of onium salt compound compound compound Non-aqueous non-aqueous compound compound compound compound (1) (2) (3) solvent (S) solvent (S) (5) (A) (1) (mol %) (3) (mol %) Example (1)-1 (2)-1 (3)-1 (S)-1 17.8 (5)-1 A1 S1 (A)-1 0.1 <0.1 Example (1)-1 (2)-1 (3)-1 (S)-2 21.5 (5)-1 A2 S2 (A)-1 0.9 <0.1 Example (1)-1 (2)-1 (3)-1 (S)-3 17.7 (5)-2 A3 S3 (A)-2 0.1 <0.1 Example (1)-2 (2)-1 (3)-2 (S)-1 17.8 (5)-3 A4 S4 (A)-3 0.1 <0.1 Example (1)-2 (2)-2 (3)-2 (S)-1 17.8 (5)-3 A5 S5 (A)-3 1.2 <0.1 Example (1)-2 (2)-3 (3)-2 (S)-4 17.7 (5)-4 A6 S6 (A)-4 0.3 <0.1 Example (1)-3 (2)-4 (3)-2 (S)-5 17.1 (5)-5 A7 S7 (A)-5 0.3 <0.1 Example (1)-4 (2)-5 (3)-3 (S)-6 17.0 (5)-6 A8 S8 (A)-6 0.2 0.1 Example (1)-4 (2)-1 (3)-4 (S)-3 17.7 (5)-7 A9 S9 (A)-7 0.1 <0.1 Example (1)-5 (2)-6 (3)-5 (S)-4 17.7 (5)-8 A10 S10 (A)-8 0.3 <0.1 Example (1)-6 (2)-7 (3)-6 (S)-1 17.8 (5)-9 A11 S11 (A)-9 0.1 <0.1 Example (1)-7 (2)-6 (3)-7 (S)-7 17.5 (5)-10 A12 S12 (A)-10 0.2 <0.1 Example (1)-7 (2)-8 (3)-8 (S)-6 17.0 (5)-11 A13 S13 (A)-11 0.3 0.2 Example (1)-8 (2)-8 (3)-9 (S)-3 17.7 (5)-12 A14 S14 (A)-12 0.9 0.1 Example (1)-9 (2)-9 (3)-10 (S)-1 17.8 (5)-13 A15 S15 (A)-13 1.8 <0.1

TABLE-US-00002 TABLE 2 Onium salt compound (A) Chemical Residual Residual Calculated SP foumula of rate Y of rate X of Onium salt Salt value of Salt onium salt onium salt onium salt compound compound Onium salt Non-aqueous non-aqueous compound compound compound compound (1) (2) compound (3) solvent (S) solvent (S) (5) (A) (1) (mol %) (3) (mol %) Example S16 (1)-10 (2)-8 (3)-11 (S)-3 17.7 (5)-14 A16 (A)-14 0.2 0.1 Example S17 (1)-11 (2)-10 (3)-12 (S)-9 18.3 (5)-15 A17 (A)-15 0.2 <0.1 Example S18 (1)-12 (2)-11 (3)-13 (S)-8 17.5 (5)-16 A18 (A)-16 1.1 <0.1 Example S19 (1)-13 (2)-3 (3)-14 CHCl.sub.3 19.5 (5)-17 A19 (A)-17 1.5 <0.1 Example S20 (1)-14 (2)-1 (3)-15 (S)-3 17.7 (5)-18 A20 (A)-18 0.1 <0.1 Example S21 (1)-15 (2)-1 (3)-16 CH.sub.3CN 24.3 (5)-10 A21 (A)-19 1.3 <0.1 Example S22 (1)-4 (2)-7 (3)-4 (S)-7/(S)-5 = 17.1 (5)-6 A22 1:1 (mass ratio) (A)-6 0.2 0.1 Comparative (1)-2 KI (3)-R1 CH.sub.2Cl.sub.2/ (5)-3 RA1 Example RS1 H.sub.2O (A)-3 0.5 3.1 Comparative (1)-2 KBr Synthesis CH.sub.2Cl.sub.2/ Example RS2 unavailable H.sub.2O Synthesis unavailable

TABLE-US-00003 TABLE 3 Onium salt compound (A) Chemical Residual Residual Calculated foumula of rate Y of rate X of Onium salt Salt Onium salt SP value of Salt onium salt onium salt onium salt compound compound compound Non-aqueous non-aqueous compound compound compound compound (1) (2) (3) solvent (S) solvent (S) (5) (A) (1) (mol %) (3) (mol %) Example (1)-11 (2)-10 (3)-12 (S)-9 18.3 (5)-19 A23 S23 (A)-20 0.2 <0.1 Example (1)-11 (2)-10 (3)-12 (S)-9 18.3 (5)-20 A24 S24 (A)-21 0.2 <0.1 Example (1)-11 (2)-10 (3)-12 (S)-9 18.3 (5)-21 A25 S25 (A)-22 0.2 <0.1 Example (1)-11 (2)-10 (3)-12 (S)-9 18.3 (5)-22 A26 S26 (A)-23 0.2 <0.1

[0727] The structures of the Onium salt compound (1) described in Tables 1 to 3 are described below.

##STR00062## ##STR00063## ##STR00064## ##STR00065##

[0728] The structures of the Salt compounds (2) described in Tables 1 to 3 are described below. It is noted that KI and KBr are not the salt compound (2), but are described in the section of Salt compound (2) for convenience.

##STR00066## ##STR00067## ##STR00068##

[0729] The structures of the Onium salt compound (3) described in Tables 1 to 3 are described below.

##STR00069## ##STR00070## ##STR00071## ##STR00072##

[0730] The compound (3)-R1 described in Onium salt compound (3) in Comparative Example RS1 described in Table 2 is not the onium salt compound (3), but is described as Onium salt compound (3) for convenience.

[0731] The structures of the Non-aqueous solvent (S) described in Tables 1 to 3 are described below.

##STR00073##

[0732] The structures of the Salt compounds (5) described in Tables 1 to 3 are described below.

##STR00074## ##STR00075## ##STR00076## ##STR00077##

[0733] The structures of the Chemical formula of onium salt compound (A) described in Tables 1 to 3 are described below.

##STR00078## ##STR00079## ##STR00080## ##STR00081##

[0734] In the compounds A1 to A26 synthesized by the method for producing an onium salt compound according to the embodiment of the present invention, the residual amounts of the onium salt compound (1) and the onium salt compound (3) were 2 mol % or less, and the residual amounts of the raw material compound and the intermediate compound were small. On the other hand, it was found that a large amount of the onium salt compound (3) remained in the compound RA1.

<Onium Salt Composition>

[0735] The compounds A1 to A26 and the compound RA1, which are onium salt compounds, were respectively set as onium salt compositions N1 to N26 and NR1.

[0736] The compound RA1 was subjected to .sup.1H NMR measurement, but the cation represented by Formula (2A) could not be confirmed.

Reference Example RS3: Synthesis of Compound RA2

[0737] A compound RA2 was obtained by the same method as in Example S1, except that 3.5 mol % of the following compound was added to the compound (Z-1). The compound RA2 which is an onium salt compound was used as an onium salt composition NR2. Bu represents an n-butyl group.

##STR00082##

<Evaluation of Residual Rate of Organic Cation Represented by Formula (2A)>

[0738] .sup.1H NMR of a sample solution obtained by dissolving 0.2 g of the onium salt compound (A) in 0.8 g of heavy acetone (heavy methanol in the case of low solubility in heavy acetone) was measured, and the residual rate Z (mol %) was calculated using the above-described Expression (3).

[0739] The structures of the organic cations represented by Formula (2A) in each of the onium salt compositions are shown in Tables 4 and 5. The amount (mol %) of the organic cation represented by Formula (2A) with respect to 1 mol of the onium salt compound is shown in Tables 4 and 5 as Residual rate Z (mol %) of cation represented by Formula (2A).

TABLE-US-00004 TABLE 4 Residual rate Onium Organic Z of cation Onium salt cation represented salt com- represented by Formula com- Com- pound by Formula (2A) pound pound (A) (2A) (mol %) Example T1 N1 A1 A1 (Q)-1 0.008 Example T2 N2 A2 A2 (Q)-1 0.006 Example T3 N3 A3 A3 (Q)-1 0.006 Example T4 N4 A4 A4 (Q)-1 0.004 Example T5 N5 A5 A5 (Q)-2 0.010 Example T6 N6 A6 A6 (Q)-3 0.005 Example T7 N7 A7 A7 (Q)-4 0.004 Example T8 N8 A8 A8 (Q)-5 0.009 Example T9 N9 A9 A9 (Q)-1 0.008 Example T10 N10 A10 A10 (Q)-6 0.008 Example T11 N11 A11 A11 (Q)-7 0.007 Example T12 N12 A12 A12 (Q)-6 0.006 Example T13 N13 A13 A13 (Q)-1 0.006 Example T14 N14 A14 A14 (Q)-1 0.008 Example T15 N15 A15 A15 (Q)-8 0.010 Example T16 N16 A16 A16 (Q)-1 0.005 Example T17 N17 A17 A17 (Q)-9 0.009 Example T18 N18 A18 A18 (Q)-10 0.008 Example T19 N19 A19 A19 (Q)-3 0.004 Example T20 N20 A20 A20 (Q)-1 0.004 Example T21 N21 A21 A21 (Q)-1 0.006 Example T22 N22 A22 A22 (Q)-7 0.006 Comparative NR1 RA1 RA1 Example RS1 Reference NR2 RA2 RA2 (Q)-1 3.5 Example RS3

TABLE-US-00005 TABLE 5 Residual rate Onium Organic Z of cation Onium salt cation represented salt com- represented by Formula com- Com- pound by Formula (2A) pound pound (A) (2A) (mol %) Example T23 N23 A23 A23 (Q)-9 0.009 Example T24 N24 A24 A24 (Q)-9 0.009 Example T25 N25 A25 A25 (Q)-9 0.009 Example T26 N26 A26 A26 (Q)-9 0.009

[0740] The structures of the Cation represented by Formula (2A) described in Tables 4 and 5 are described below.

##STR00083## ##STR00084##

[0741] The various components used in the method for producing the actinic ray-sensitive or radiation-sensitive resin composition of Examples and Comparative Examples are shown below.

<Onium Salt Compound (A)>

[0742] As the onium salt compound (A), the above-described compounds A1 to A26 were used. In Comparative Examples, the above-described compound RA1 was used. In Reference Examples, the above-described compound RA2 was used.

<Resin (B)>

[0743] Resins B1 to B12 were used as the resin (B).

[0744] The structures of the resins B1 to B12 are shown in Tables 6 and 7 below. The content ratio (content with respect to all repeating units in the resin) of the following repeating unit is a molar ratio.

[0745] The weight-average molecular weight (Mw) and the dispersity (PDI=Mw/Mn) of the resin were measured by GPC (carrier: tetrahydrofuran (THF)) (values expressed in terms of polystyrene equivalent). In addition, the content of the repeating unit was measured by .sup.13C-nuclear magnetic resonance (NMR).

TABLE-US-00006 TABLE 6 Composition ratio Structure (molar ratio) Mw PDI B1 [00085] 34/13/53 6500 1.60 [00086] [00087] B2 [00088] 16/31/53 7200 1.58 [00089] [00090] B3 [00091] 43/11/43/3 8000 1.62 [00092] [00093] B4 [00094] 49/20/31 7800 1.71 [00095] [00096] B5 [00097] 27/21/39/13 8400 1.78 [00098] [00099] [00100] B6 [00101] 36/7/57 12000 1.53 [00102] [00103] B7 [00104] 31/7/3/59 8600 1.61 [00105] [00106] [00107] B8 [00108] 31/14/14/41 8000 1.58 [00109] [00110] [00111]

TABLE-US-00007 TABLE 7 Composition ratio Structure (molar ratio) Mw PDI B9 [00112] 50/20/30 7500 1.51 [00113] [00114] B10 [00115] 50/10/40 7000 1.58 [00116] [00117] B11 [00118] 60/40 5000 1.52 [00119] B12 [00120] 70/30 5500 1.55 [00121]

<Photoacid Generator (C)>

[0746] The photoacid generator C1 used is shown below.

[0747] The photoacid generator C1 was produced with reference to the method described in JP2013-160955A.

##STR00122##

<Acid Diffusion Control Agent (D)>

[0748] The acid diffusion control agent D1 used is shown below.

[0749] The acid diffusion control agent D1 was produced with reference to the method described in WO2020/175495A.

##STR00123##

<Hydrophobic Resin (E)>

[0750] The hydrophobic resins E1 and E2 used are shown below.

##STR00124##

<Solvent (F)>

[0751] The solvents F-1 to F-6 used are shown below. [0752] F-1: Propylene glycol monomethyl ether acetate (PGMEA) [0753] F-2: Propylene glycol monomethyl ether (PGME) [0754] F-3: -Butyrolactone [0755] F-4: Ethyl lactate [0756] F-5: Cyclohexanone [0757] F-6: 2-Heptanone

Examples 1 to 49, Comparative Example 1, and Reference Example 1

(Preparation of Actinic Ray-Sensitive or Radiation-Sensitive Resin Composition)

[0758] Each component shown in Tables 8 to 10 was dissolved in the solvent shown in Tables 8 to 10 and mixed so that the concentration of solid contents was 2.0% by mass. Next, the obtained mixed liquid was filtered initially through a polyethylene-made filter having a pore diameter of 50 nm, then through a nylon-made filter having a pore diameter of 10 nm, and lastly through a polyethylene-made filter having a pore diameter of 5 nm in this order to prepare an actinic ray-sensitive or radiation-sensitive resin composition (resist composition).

[0759] The content of each component in Tables 8 to 10 is a mass-based proportion with respect to the total solid content of each resist composition. % is based on a mass (that is, by mass). The concentration of solid contents means a mass percentage of the mass of other components excluding the solvent with respect to the total mass of each resist composition.

[0760] The types of compounds used and the mass ratios thereof are shown in Tables 8 to 10 for the solvents.

TABLE-US-00008 TABLE 8 Onium salt Photoacid Hydrophobic compound (A) Resin (B) generator (C) Acid diffusion control resin (E) Content Content Content agent (D) Content Solvent (F) Com- (% by (% by (% by Content (% (% by Content ratio position Type mass) Type mass) Type mass) Type by mass) Type mass) Type (mass ratio) Example 1 R1 A1 17.5 B1 74.1 C1 8.4 F-1/F-2 80/20 Example 2 R2 A1 17.5 B2 74.1 C1 8.4 F-1/F-2 60/40 Example 3 R3 A1 17.5 B2 73.1 C1 8.4 E1 1.0 F-1/F-2 60/40 Example 4 R4 A1 17.5 B7 74.1 C1 8.4 F-1/F-2/F-4 80/10/10 Example 5 R5 A2 17.5 B1 74.1 C1 8.4 F-1/F-2 80/20 Example 6 R6 A3 6.8 B1 80.6 C1 12.6 F-1/F-2 40/60 Example 7 R7 A3 6.8 B6 80.6 C1 12.6 F-1/F-2 60/40 Example 8 R8 A4 17.5 B1 74.1 C1 8.4 F-1/F-2/F-4 80/10/10 Example 9 R9 A4 17.5 B2 74.1 C1 8.4 F-1/F-2 70/30 Example 10 R10 A4 17.5 B7 74.1 C1 8.4 F-1/F-2/F-3 80/10/10 Example 11 R11 A5 17.5 B1 74.1 C1 8.4 F-1/F-5 90/10 Example 12 R12 A6 17.3 B1 78.4 D1 4.3 F-1/F-2 60/40 Example 13 R13 A6 17.3 B1 77.1 D1 4.3 E2 1.3 F-1/F-2 60/40 Example 14 R14 A6 17.3 B2 78.4 D1 4.3 F-1/F-3/F-4 80/10/10 Example 15 R15 A6 17.3 B6 78.4 D1 4.3 F-1/F-3/F-4 80/15/5 Example 16 R16 A7 25.6 B1 73.1 D1 1.3 F-1/F-2/F-4 80/10/10 Example 17 R17 A8 17.5 B1 74.1 C1 8.4 F-1/F-2/F-3 80/10/10 Example 18 R18 A8 17.5 B3 74.1 C1 8.4 F-1/F-2 60/40 Example 19 R19 A8 17.5 B6 74.1 C1 8.4 F-1/F-2/F-6 80/10/10 Example 20 R20 A9 17.3 B1 78.4 D1 4.3 F-1/F-2 70/30 Example 21 R21 A9 17.3 B3 78.4 D1 4.3 F-1/F-3/F-4 80/15/5 Example 22 R22 A9 17.3 B7 78.4 D1 4.3 F-1/F-2 95/5 Example 23 R23 A10 3.3 B1 84.9 C1 11.8 F-1/F-3 85/15 Example 24 R24 A10 3.3 B5 84.9 C1 11.8 F-1/F-2 40/60 Example 25 R25 A11 25.6 B1 73.1 D1 1.3 F-1/F-2/F-6/F-3 85/7/7/1

TABLE-US-00009 TABLE 9 Onium salt Photoacid Acid diffusion Hydrophobic compound (A) Resin (B) generator (C) control agent (D) resin (E) Content Content Content Content Content Solvent (F) (% by (% by (% by (% by (% by Content ratio Composition Type mass) Type mass) Type mass) Type mass) Type mass) Type (mass ratio) Example 26 R26 A11 25.6 B6 73.1 D1 1.3 F-1/F-2/F-3 75/15/10 Example 27 R27 A12 6.8 B1 80.6 C1 12.6 F-1/F-2/F-4 80/15/5 Example 28 R28 A12 6.8 B4 80.6 C1 12.6 F-1/F-3 85/15 Example 29 R29 A13 17.3 B1 78.4 D1 4.3 F-1/F-2/F-4 80/10/10 Example 30 R30 A13 17.3 B8 78.4 D1 4.3 F-1/F-2 70/30 Example 31 R31 A14 17.3 B1 78.4 D1 4.3 F-1/F-2 70/30 Example 32 R32 A14 17.3 B2 78.4 D1 4.3 F-1/F-2 80/20 Example 33 R33 A15 17.3 B1 78.4 D1 4.3 F-1/F-3 85/15 Example 34 R34 A16 15.6 B1 81.3 D1 3.1 F-1/F-2 60/40 Example 35 R35 A16 15.6 B4 81.3 D1 3.1 F-1/F-2/F-3 80/10/10 Example 36 R36 A17 15.6 B1 81.3 D1 3.1 F-1/F-2 70/30 Example 37 R37 A17 15.6 B8 81.3 D1 3.1 F-1/F-2/F-6 80/15/5 Example 38 R38 A18 17.3 B1 78.4 D1 4.3 F-1/F-2/F-5 75/20/5 Example 39 R39 A19 17.3 B1 78.4 D1 4.3 F-1/F-4 90/10 Example 40 R40 A20 20.2 B1 74.9 C1 4.9 F-1/F-2 70/30 Example 41 R41 A20 20.2 B5 74.9 C1 4.9 F-1/F-2 50/50 Example 42 R42 A21 6.8 B1 80.6 C1 12.6 F-1/F-2 80/20 Example 43 R43 A21 6.8 B4 80.6 C1 12.6 F-1/F-2/F-6 80/10/10 Example 44 R44 A1/A9 17.5/8.4 B6 74.1 F-1/F-2/F-4 80/10/10 Example 45 R45 A22 17.5 B1 74.1 C1 8.4 F-1/F-2 80/20 Comparative RR1 RA1 17.5 B1 74.1 C1 8.4 F-1/F-2/F-4 80/10/10 Example 1 Reference RR2 RA2 17.5 B1 74.1 C1 8.4 F-1/F-2 80/20 Example 1

TABLE-US-00010 TABLE 10 Acid diffusion Onium salt Photoacid control agent Hydrophobic Solvent (F) compound (A) Resin (B) generator (C) (D) resin (E) Content Content Content Content Content Content ratio (% by (% by (% by (% by (% by (mass Composition Type mass) Type mass) Type mass) Type mass) Type mass) Type ratio) Example R46 A23/A25 12.5/10.4 B9 77.1 F-1/F-2/F-3 80/10/10 46 Example R47 A23/A26 15.2/8.2 B10 76.6 F-1/F-4 60/40 47 Example R48 A24/A26 18.3/12.1 B11 69.6 F-1/F-2/F-3 80/10/10 48 Example R49 A24/A26 11.1/10.6 B12 78.3 F-1/F-2/F-3 80/10/10 49

[Pattern Formation 1: EUV Exposure and Aqueous Alkaline Solution Development]

[0761] A composition for forming an underlayer film, AL412 (manufactured by Brewer Science, Inc.), was applied to a silicon wafer and baked at 205 C. for 60 seconds to form an underlying film having a film thickness of 20 nm. Resist compositions shown in Tables 8 to 10 were applied on the underlying film and baked at 100 C. for 60 seconds to form a resist film having a film thickness of 30 nm.

[0762] The silicon wafer having the obtained resist film was subjected to a pattern irradiation using an EUV exposure device (manufactured by Exitech Ltd., Micro Exposure Tool, NA 0.3, Quadrupole, outer sigma 0.68, inner sigma 0.36). As a reticle, a mask having a line size=25 nm and a line:space=1:1 was used.

[0763] The resist film after the exposure was baked at 90 C. for 60 seconds, developed with a tetramethylammonium hydroxide aqueous solution (2.38% by mass) for 30 seconds, and then rinsed with pure water for 30 seconds. Thereafter, the resist film was spin-dried to obtain a positive tone pattern.

<Evaluation of Line Width Roughness (LWR) Performance>

[0764] In a case of observing a line-and-space pattern of 25 nm (1:1) resolved at an optimum exposure amount in a case of resolving a line pattern having an average line width of 25 nm from the upper part of the pattern using a scanning electron microscope (SEM (S-9380II, manufactured by Hitachi, Ltd.)), the line width was observed at 250 locations, and the standard deviation (a) thereof was obtained. The measurement variation of the line width was evaluated by 36, and the value of 36 was defined as LWR (nm). As the value is smaller, the performance is better.

[0765] The LWR is preferably 4.0 nm or less, more preferably 3.5 nm or less, and particularly preferably 3.2 nm or less.

[0766] The resist compositions and the results used in Tables 11 and 12 are shown.

TABLE-US-00011 TABLE 11 Example Composition LWR (nm) Example P1 R1 2.9 Example P2 R2 2.9 Example P3 R3 2.8 Example P5 R5 3.4 Example P6 R6 2.9 Example P7 R7 3.0 Example P8 R8 2.8 Example P9 R9 2.8 Example P10 R10 2.9 Example P11 R11 3.3 Example P12 R12 3.0 Example P13 R13 2.9 Example P14 R14 2.9 Example P16 R16 2.9 Example P17 R17 3.0 Example P18 R18 3.1 Example P20 R20 2.9 Example P21 R21 2.9 Example P22 R22 2.9 Example P23 R23 2.9 Example P25 R25 2.8 Example P27 R27 3.1 Example P28 R28 3.1 Example P29 R29 3.1 Example P31 R31 3.5 Example P32 R32 3.5 Example P33 R33 3.8 Example P34 R34 3.1 Example P35 R35 3.1 Example P36 R36 3.0 Example P38 R38 3.4 Example P39 R39 3.6 Example P40 R40 2.8 Example P41 R41 2.9 Example P42 R42 3.9 Example P44 R44 2.9 Example P45 R45 3.2 Comparative RR1 4.2 Example PR1 Reference RR2 4.2 Example PR2

TABLE-US-00012 TABLE 12 Example Composition LWR (nm) Example P46 R46 2.9 Example P47 R47 3.1 Example P48 R48 2.8 Example P49 R49 3.0

[Pattern Formation 2: EUV Exposure and Organic Solvent Development]

[0767] A composition for forming an underlayer film, AL412 (manufactured by Brewer Science, Inc.), was applied to a silicon wafer and baked at 205 C. for 60 seconds to form an underlying film having a film thickness of 20 nm. Resist compositions shown in Tables 8 and 9 were applied on the underlying film and baked at 100 C. for 60 seconds to form a resist film having a film thickness of 30 nm.

[0768] The silicon wafer having the obtained resist film was subjected to a pattern irradiation using an EUV exposure device (manufactured by Exitech Ltd., Micro Exposure Tool, NA 0.3, Quadrupole, outer sigma 0.68, inner sigma 0.36). As a reticle, a mask having a line size=25 nm and a line:space=1:1 was used.

[0769] The resist film after the exposure was baked at 90 C. for 60 seconds, developed with n-butyl acetate for 30 seconds, and spin-dried to obtain a negative tone pattern.

<Evaluation of LWR Performance>

[0770] The LWR performance was evaluated by the same method as described above.

[0771] The resist compositions and the results used in Table 13 are shown.

TABLE-US-00013 TABLE 13 Example Composition LWR (nm) Example N1 R1 3.0 Example N2 R2 3.0 Example N3 R3 2.9 Example N4 R4 2.9 Example N5 R5 3.5 Example N6 R6 3.0 Example N7 R7 3.1 Example N8 R8 2.9 Example N10 R10 3.0 Example N11 R11 3.4 Example N12 R12 3.1 Example N13 R13 3.0 Example N15 R15 3.0 Example N16 R16 3.0 Example N17 R17 3.1 Example N19 R19 3.0 Example N20 R20 3.0 Example N22 R22 3.0 Example N23 R23 3.0 Example N24 R24 3.0 Example N25 R25 2.9 Example N26 R26 2.9 Example N27 R27 3.2 Example N28 R28 3.2 Example N29 R29 3.2 Example N30 R30 3.2 Example N31 R31 3.6 Example N32 R33 3.9 Example N33 R34 3.2 Example N34 R35 3.2 Example N35 R36 3.1 Example N36 R37 3.2 Example N37 R38 3.5 Example N38 R39 3.7 Example N40 R40 2.9 Example N41 R41 3.0 Example N42 R42 4.0 Example N43 R43 4.0 Example N44 R44 3.0 Example N45 R45 3.3 Comparative RR1 4.3 Example NR1 Reference RR2 4.3 Example NR2

[Pattern Formation 3: Electron Beams (EB) Exposure and Aqueous Alkaline Solution Development]

[0772] The resist compositions shown in Tables 8 to 10 were uniformly applied onto a hexamethyldisilazane-treated silicon substrate using a spin coater. Then, the composition was heated and dried at 120 C. for 90 seconds on a hot plate to form a resist film with a film thickness of 35 nm.

[0773] The obtained resist film was irradiated with electron beams through a 6% halftone mask with a line width of 24 nm and a 1:1 line-and-space pattern, using an electron beam irradiation device (HL750 manufactured by Hitachi, Ltd., accelerating voltage of 50 keV). Immediately after irradiation, the resist film was heated on a hot plate at 110 C. for 60 seconds. The resist film was further developed at 23 C. for 60 seconds using a 2.38%-by-mass aqueous tetramethylammonium hydroxide (TMAH) solution, rinsed with pure water for 30 seconds, and then spin-dried to obtain a positive tone pattern.

<Evaluation of LWR Performance>

[0774] The LWR performance was evaluated by the same method as described above.

[0775] The resist compositions and the results used in Tables 14 and 15 are shown.

TABLE-US-00014 TABLE 14 Example Composition LWR (nm) Example EP1 R1 3.1 Example EP2 R2 3.1 Example EP3 R3 3.0 Example EP5 RS 3.6 Example EP6 R6 3.1 Example EP8 R8 3.0 Example EP9 R9 3.0 Example EP10 R10 3.1 Example EP11 R11 3.5 Example EP12 R12 3.2 Example EP13 R13 3.1 Example EP16 R16 3.1 Example EP18 R18 3.3 Example EP20 R20 3.1 Example EP23 R23 3.1 Example EP25 R25 3.0 Example EP27 R27 3.3 Example EP29 R29 3.3 Example EP32 R32 3.7 Example EP35 R35 3.3 Example EP39 R39 3.8 Example EP42 R42 4.1 Example EP44 R44 3.1 Example EP45 R45 3.4 Comparative RR1 4.4 Example ER1 Reference RR2 4.4 Example ER2

TABLE-US-00015 TABLE 15 Example Composition LWR (nm) Example EP46 R46 3.0 Example EP47 R47 3.1 Example EP48 R48 3.0 Example EP49 R49 3.1

[0776] The exposure with the electron beam irradiation device (HL750 manufactured by Hitachi, Ltd.) is a single-beam type, and is not a multi-beam type in which a plurality of single beams are simultaneously scanned. However, the effect of replacing the multi-beam type with the single-beam type is only on the total drawing time, and it is assumed that the evaluation results of the obtained resolution and the LWR are equivalent to the evaluation results in a case where the multi-beam type is used.

[0777] From the results of Tables 11 to 15, it was found that the resist compositions used in Examples had excellent LWR performance.

[0778] According to the present invention, it is possible to provide a method for producing an actinic ray-sensitive or radiation-sensitive resin composition having excellent LWR performance, a pattern forming method including the method for producing, and a method for manufacturing an electronic device.

[0779] In addition, according to the present invention, it is possible to provide a method for producing an onium salt compound, which can be suitably used for the actinic ray-sensitive or radiation-sensitive resin composition, and an onium salt composition.

[0780] The present invention has been described in detail with reference to specific embodiments. To those skilled in the art, it is obvious that various changes or modifications can be added without departing from the gist and scope of the present invention.