Resist underlayer film forming composition containing low molecular weight dissolution accelerator

Patent metadata

Field	Value
Publication number	US-9645494-B2
Application number	US-44813007-A
Country	US
Kind code	B2
Filing date	Dec 11, 2007
Priority date	Dec 13, 2006
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

There is provided a resist underlayer film forming composition that is used in a lithography process for the production of semiconductor devices and that can be developed with an alkaline developer for photoresists, and a method of forming a photoresist pattern by using the resist underlayer film forming composition. The resist underlayer film forming composition used in a lithography process for a production of a semiconductor device comprising: an alkali-soluble resin (a); a polynuclear phenol (b); a compound (c) having at least two vinylether groups; and a photoacid generator (d). The alkali-soluble resin (a) may be a polymer containing a unit structure having a carboxyl group, and the polynuclear phenol (b) may be a compound having 2 to 30 phenolic hydroxyl groups in the molecule.

First claim

The invention claimed is:

1. A method of manufacturing a semiconductor device, the method comprising:
forming a resist underlayer film by using a resist underlayer film forming composition on a semiconductor substrate;
forming a resist film on the resist underlayer film; and
exposing the resist film to light and developing the resist film to form a resist pattern,
wherein the resist underlayer film forming composition comprises:
an alkali-soluble resin (a),
a polynuclear phenol (b);
a compound (c) having at least two vinylether groups, and
a photoacid generator (d),
wherein
the alkali-soluble resin (a) is a polymer containing a unit structure having a carboxyl group in an amount from 0.05 to 0.80 when all repeating units contained in the alkali-soluble resin (a) are assumed to be 1.0;
the unit structure containing a carboxyl group is derived from polymerization of acrylic acid or methacrylic acid, or is used in form of a carboxyl group substituted in an aromatic ring, and
the polynuclear phenol (b) is a compound represented by Formula (b1-1):

where each R 1 is a substituent for a hydrogen atom of a benzene ring and represents a group selected from a group consisting of a hydroxy group, a halogen atom, an alkyl group having 1 to 10 carbon atom, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 25 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, an alkylcarbonylamino group having 2 to 10 carbon atoms, an aryloxyalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atom and a combination of these substituents; R 3 represents a single bond or a divalent to tetravalent alkylene group having 1 to 10 carbon atom or arylalkylene group having 6 to 25 carbon atoms; m is an integer of 1 to 5; n represents an integer satisfying 0≦n≦5-m; and q represents an integer of 2 to 4,
a compound represented by Formula (b1-2):

where R 1 and R 2 are the same as or different from each other and individually represent the same meaning as R 1 defined in Formula (b1-1); R 4 represents a single bond or a divalent to hexavalent alkylene group having 1 to 10 carbon atom or arylalkylene group having 6 to 25 carbon atoms; m represents an integer of 1 to 5; n represents an integer satisfying 0≦n≦5-m; and k and s individually represent an integer of 1 to 3,
a compound represented by Formula (b1-3):

where R 1 and R 2 are the same as or different from each other and individually represent the same meaning as R 1 defined in Formula (b1-1); R 5 represents a single bond or a divalent alkylene group having 1 to 10 carbon atom or arylalkylene group having 6 to 25 carbon atoms; m1 represents an integer of 1 to 4; m2 represents an integer of 1 to 5; o is a number satisfying 0≦o≦4-m1; p is a number satisfying 0≦p≦5-m2; and t represents an integer of 1 to 4,
or a combination of these compounds, and
wherein a content of the alkali-soluble resin (a) in the solid content of the resist underlayer film forming composition is 49 to 90% by mass, a content of the polynuclear phenol (b) in the solid content of the resist underlayer film forming composition is 0.01 to 40% by mass, a content of the compound (c) having at least two vinylether groups in the solid content of the resist underlayer film forming composition is 0.1 to 40% by mass, and a content of the photoacid generator (d) in the solid content of the resist underlayer film forming composition is 0.1 to 10% by mass.

2. The method of manufacturing a semiconductor device according to claim 1 , wherein the compound (c) having at least two vinylether groups is represented by Formula (c1):

where R a represents a divalent organic group selected from a group consisting of an alkyl group having 1 to 10 carbon atom, an aryl group having 6 to 18 g carbon atoms, an arylalkyl group having 6 to 25 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, an alkylcarbonyloxy group having 2 to 10 carbon atoms, an alkylcarbonylamino group having 2 to 10 carbon atoms and an aryloxyalkyl group having 2 to 10 carbon atoms; R b represents a divalent to tetravalent organic group derived from an alkyl group having 1 to 10 carbon atom or an aryl group having 6 to 18 carbon atoms; and c represents an integer of 2 to 4.

3. The method of manufacturing a semiconductor device according to claim 1 , wherein an exposed part of the resist underlayer film used exhibits alkali-solubility and an exposed part of the resist film and an exposed part of the resist underlayer film are removed at the same time by development using an alkaline developer to form the resist pattern on the semiconductor substrate.

4. The method of manufacturing a semiconductor device according to claim 1 , wherein the alkali-soluble resin (a) has the carboxyl group in an amount from 0.10 to 0.60 when all repeating units contained in the alkali-soluble resin (a) are assumed to be 1.0.

5. The method of manufacturing a semiconductor device according to claim 1 , wherein during forming a resist underlayer film, the alkali-soluble resin (a), the polynuclear phenol (b), and the compound (c) having at least two vinylether groups react to form an acetal bond, and
during exposing the resist film to light and developing the resist film to form a resist pattern, the photoacid generator (d) generates an acid that breaks bonds between the alkali-soluble resin (a) and the compound (c) having at least two vinylether groups, and breaks bonds between the polynuclear phenol (b) and the compound (c) having at least two vinylether groups.

Assignees

• Kato Masakazu
• Hamada Takahiro
• Enomoto Tomoyuki
• Nissan Chemical Ind Ltd

Inventors

• Kato Masakazu
• Hamada Takahiro
• Enomoto Tomoyuki

Classifications

• H10P76/2043

  using an anti-reflective coating · CPC title

• G03F7/30

  Imagewise removal using liquid means · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/091 Primary

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title