Photosensitive composition for EUV light, pattern forming method, and method for manufacturing electronic device

Patent metadata

Field	Value
Publication number	US-11703758-B2
Application number	US-202017035746-A
Country	US
Kind code	B2
Filing date	Sep 29, 2020
Priority date	Apr 20, 2018
Publication date	Jul 18, 2023
Grant date	Jul 18, 2023

Abstract

A photosensitive composition for EUV light includes a predetermined resin and a photoacid generator, or includes a predetermined resin having a repeating unit having a photoacid generating group, and satisfies Requirements 1 to 3,
Requirement 1: The A value determined by Formula (1) is 0.14 or more,

A=([H]×0.04+[C]×1.0+[N]×2.1+[O]×3.6+[F]×5.6+[S]×1.5+[I]×39.5)/([H]×1+[C]×12+[N]×14+[O]×16+[F]×19+[S]×32+[I]×127)  Formula(1)

Requirement 2: The concentration of solid contents in the photosensitive composition for EUV light is 5.0% by mass or less,
Requirement 3: The content of the photoacid generator is 5% to 50% by mass with respect to the total solid content in the photosensitive composition for EUV light.

First claim

What is claimed is:

1. A photosensitive composition for EUV light, comprising:
a resin that has an increased polarity by action of an acid, thereby having an increased solubility in an alkali developer and a decreased solubility in an organic solvent; and a photoacid generator, or
a resin that has a repeating unit having a photoacid generating group, and has an increased polarity by action of an acid, thereby having an increased solubility in an alkali developer and a decreased solubility in an organic solvent, and
wherein the photosensitive composition satisfies Requirement 1 to Requirement 3 and the resin has a phenolic hydroxyl group,
Requirement 1: an A value determined by Formula (1) is 0.14 or more,
A=([H]×0.04+[C]×1.0+[N]×2.1+[O]×3.6+[F]×5.6+[S]×1.5+[I]×39.5)/([H]×1+[C]×12+[N]×14+[O]×16+[F]×19+[S]×32+[I]×127)  Formula (1)

in the formula, [H] represents a molar ratio of hydrogen atoms derived from a total solid content with respect to all atoms of the total solid content in the photosensitive composition for EUV light, [C] represents a molar ratio of carbon atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light, [N] represents a molar ratio of nitrogen atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light, [O] represents a molar ratio of oxygen atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light, [F] represents a molar ratio of fluorine atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light, [S] represents a molar ratio of sulfur atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light, and [I] represents a molar ratio of iodine atoms derived from the total solid content with respect to all the atoms of the total solid content in the photosensitive composition for EUV light,
Requirement 2: a concentration of a solid content in the photosensitive composition for EUV light is 5.0% by mass or less,
Requirement 3: a content of the photoacid generator is 5% to 50% by mass with respect to the total solid content in the photosensitive composition for EUV light.

2. The photosensitive composition for EUV light according to claim 1 , comprising:
the resin that has an increased polarity by action of an acid, thereby having an increased solubility in an alkali developer and a decreased solubility in an organic solvent; and
a photoacid generator consisting of a cationic moiety and an anionic moiety, wherein a B value determined by Formula (2) is 0 eV or more,
B value=LUMO(Polymer)−LUMO(PAG_Cation)  Formula (2)

in the formula, the LUMO (Polymer) represents an energy value of a lowest unoccupied molecular orbital level of a monomer of a repeating unit which is derived from the monomer having a lowest energy value of the lowest unoccupied molecular orbital level, the repeating unit being one of repeating units included in an amount of 5% by mass or more with respect to all the repeating units of the resin, and
the LUMO (PAG_Cation) represents an energy value of the lowest unoccupied molecular orbital level of a cationic moiety of the photoacid generator which is contained in a largest amount in the photosensitive composition for EUV light in term of a mass.

3. The photosensitive composition for EUV light according to claim 1 ,
wherein a volume of an acid generated from the photoacid generator is 240 Å 3 or more.

4. The photosensitive composition for EUV light according to claim 1 ,
wherein a glass transition temperature of the resin is higher than 90° C.

5. The photosensitive composition for EUV light according to claim 1 ,
wherein the resin has an acid group with an acid dissociation constant of 13 or less.

6. The photosensitive composition for EUV light according to claim 5 ,
wherein a content of the acid group of the resin having said acid group is 0.80 to 6.00 mmol/g.

7. The photosensitive composition for EUV light according to claim 1 ,
wherein the resin has a repeating unit having a fluorine atom or an iodine atom.

8. The photosensitive composition for EUV light according to claim 7 ,
wherein neither a structure in which a polar group is protected with a leaving group that leaves by action of an acid nor an acid group is included in the repeating unit having a fluorine atom or an iodine atom.

9. The photosensitive composition for EUV light according to claim 1 ,
wherein the resin includes a fluorine atom and an iodine atom.

10. A pattern forming method comprising:
forming a resist film on a substrate using the photosensitive composition for EUV light according to claim 1 ;
exposing the resist film with EUV light; and
developing the exposed resist film using an alkali developer to form a pattern.

11. A method for manufacturing an electronic device, comprising the pattern forming method according to claim 10 .

12. A photosensitive composition for EUV light, comprising:
a resin that has an increased polarity by action of an acid, thereby having an increased solubility in an alkali developer and a decreased solubility in an organic solvent; and a photoacid generator, or
a resin that has a repeating unit having a photoacid generating group, and has an increased polarity by action of an acid, thereby having an increased solubility in an alkali developer and a decreased solubility in an organic solvent, and
wherein the photosensitive composition satisfies Requirement 1 to Requirement 3 and the resin has a repeating unit having a structure in which a polar group is protected with a leaving group that leaves by action of an acid,
the resin has a group selected from a group consisting of Formula (Y1), Formula (Y2), Formula (Y4), and Formula (Y3-1) as the leaving group or has a repeating unit represented by Formula (A) as the repeating unit having a structure in which a polar group is protected with a leaving group that leaves by action of an acid;
—C(Rx 1 )(Rx 2 )(Rx 3 )  Formula (Y1)

—C(═O)OC(Rx 1 )(Rx 2 )(Rx 3 )  Formula (Y2)

—C(Rn)(H)(Ar)  Formula (Y4)

in the Formula (Y1), Formula (Y2), and Formula (Y4), Rx 1 to Rx 3 each independently represent an alkyl group or a cycloalkyl group and two of Rx 1 to Rx 3 optionally be bonded to each other to form a monocycle or a polycycle;
Ar represents an aromatic ring group, Rn represents an alkyl group, a cycloalkyl group, or an aryl group, and Rn and Ar optionally be bonded to each other to form a non-aromatic ring;

in the Formula (Y3-1), L 1 and L 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a group formed by combination thereof, M represents a single bond or a divalent linking group, and Q represents an alkyl group which include a heteroatom, a cycloalkyl group which include a heteroatom, an aryl group which optionally include a heteroatom, an amino group, an ammonium group, a mercapto group, a cyano group, an aldehyde group, or a group formed by combination thereof;

in Formula (A), L 1 represents a divalent linking group which optionally have a fluorine atom or an iodine atom, R 1 represents a hydrogen atom, a fluorine atom, an iodine atom, an a

Assignees

• Fujifilm Corp

Inventors

• Shirakawa Michihiro
• Furutani Hajime
• Oka Hironori

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• C08L101/04

  containing halogen atoms · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title