Resist composition, method of forming resist pattern, acid generator, photoreactive quencher, and compound

Patent metadata

Field	Value
Publication number	US-9682951-B2
Application number	US-201615077034-A
Country	US
Kind code	B2
Filing date	Mar 22, 2016
Priority date	Mar 24, 2015
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, and which includes a base component which exhibits changed solubility in a developing solution under action of acid and an acid-generator component including a compound (B0-1) represented by general formula (b0) shown below in which Ra 1 represents an aromatic ring; Ra 01 represents an alkyl group of 5 or more carbon atoms optionally having a substituent; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a substituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − represents a counteranion.

First claim

What is claimed is:

1. A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, the resist composition comprising:
an organic compound component (A) which exhibits changed solubility in a developing solution under action of acid; and
an acid-generator component (B) comprising a compound (B0-1) represented by general formula (b0) shown below:

wherein Ra 1 represents an aromatic ring; Ra 01 represents a linear alkyl group of 10 or more carbon atoms; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a substituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − represents an anion represented by any one of general formulae (b-1) to (b-3) shown below:

wherein R 101 and R 104 to R 108 each independently represents a cyclic group optionally having a substituent, a linear or branched alkyl group optionally having have a substituent or a linear or branched alkenyl group optionally having a substituent, provided that R 104 and R 105 may be mutually bonded to form a ring; R 106 and R 107 may be mutually bonded to form a ring; R 102 represents a fluorine atom or a fluorinated alkyl group of 1 to 5 carbon atoms; Y 101 represents a single bond or a divalent linking group containing an oxygen atom; V 101 to V 103 each independently represents a single bond, an alkylene group or a fluorinated alkylene group; L 101 and L 102 each independently represents a single bond or an oxygen atom; and L 103 to L 105 each independently represents a single bond, —CO—or —SO 2 —.

2. The resist composition according to claim 1 , further comprising a photoreactive quencher component (D).

3. The resist composition according to claim 2 , wherein the photoactive quencher component comprises a compound (D0-1) represented by general formula (d0) shown below:

wherein Ra 1 represents an aromatic ring; Ra 01 represents a linear alkyl group of 10 or more carbon atoms; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a substituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − is an anion represented by any one of general formulae (d1-1) to (d1-3) shown below:

wherein Rd 1 to Rd 4 each independently represents a cyclic group optionally having a substituent, a linear or branched alkyl group optionally having a substituent or a linear or branched group optionally having a substituent; provided that, the carbon atom adjacent to the sulfur atom within the Rd 2 in the formula (d1-2) does not have 2 or more fluorine atoms bonded thereto; and Yd 1 represents a single bond or a divalent linking group.

4. A method of forming a resist pattern, comprising:
forming a resist film on a substrate using the resist composition of claim 1 ;
exposing the resist film; and
developing the resist film to form a resist pattern.

5. A compound (B0-1) represented by general formula (b0) shown below:

wherein Ra 1 represents an aromatic ring; Ra 01 represents a linear alkyl group of 10 or more carbon atoms; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a sub stituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − is an anion represented by any one of general formulae (b-1) to (b-3) shown below:

wherein R 101 and R 104 to R 108 each independently represents a cyclic group optionally having a substituent, a linear or branched alkyl group optionally having have a substituent or a linear or branched alkenyl group optionally having a substituent, provided that R 104 and R 105 may be mutually bonded to form a ring; R 106 and R 107 may be mutually bonded to form a ring; R 102 represents a fluorine atom or a fluorinated alkyl group of 1 to 5 carbon atoms; Y 101 represents a single bond or a divalent linking group containing an oxygen atom; V 101 to V 103 each independently represents a single bond, an alkylene group or a fluorinated alkylene group; L 101 and L 102 each independently represents a single bond or an oxygen atom; and L 103 to L 105 independently represents a single bond, —CO—or —SO 2 —.

6. A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, the resist composition comprising:
an organic compound component (A) which exhibits changed solubility in a developing solution under action of acid,
an acid-generator component (B'), and
a photoreactive quencher (D0) comprising a compound (D0-1) represented by general formula (d0) shown below:

wherein Ra 1 represents an aromatic ring; Ra 01 represents a linear alkyl group of 10 or more carbon atoms; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a substituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − represents an anion represented by any one of general formulae (d1-1) to (d1-3) shown below:

wherein Rd 1 to Rd 4 each independently represents a cyclic group optionally having a substituent, a linear or branched alkyl group optionally having a substituent or a linear or branched group optionally having a substituent; provided that, the carbon atom adjacent to the sulfur atom within the Rd 2 in the formula (d1-2) does not have 2 or more fluorine atoms bonded thereto; and Yd 1 represents a single bond or a divalent linking group.

7. A method of forming a resist pattern, comprising:
forming a resist film on a substrate using the resist composition of claim 6 ;
exposing the resist film; and
developing the resist film to form a resist pattern.

8. A compound (D0-1) represented by general formula (d0):

wherein Ra 1 represents an aromatic ring; Ra 01 represents a linear alkyl group of 10 or more carbon atoms; Ra 02 and Ra 03 each independently represents an alkyl group of 1 to 10 carbon atoms optionally having a substituent; n1 represents an integer of 1 to 5; n2 represents an integer of 0 to 2; n3 represents an integer of 0 to 4; and X − is an anion represented by any one of general formulae (d1-1) to (d1-3) shown below:

wherein Rd 1 to Rd 4 each independently represents a cyclic group optionally having a substituent, a linear or branched alkyl group optionally having a substituent or a linear or branched group optionally having a substituent; provided that, the carbon atom adjacent to the sul

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Nagamine Takashi
• Endo Kotaro
• Shinomiya Miki

Classifications

• C07C309/19

  of a saturated carbon skeleton containing rings · CPC title

• C07C309/17

  containing carboxyl groups bound to the carbon skeleton · CPC title

• C07D493/08

  Bridged systems · CPC title

• C07C309/06

  containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton · CPC title

• C07D333/54 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring · CPC title