US 10,593,547 B2Granted

Photocurable composition, and methods using the same for forming cured product pattern and for manufacturing optical component, circuit board and imprinting mold

AssigneeCanon Kabushiki Kaisha

InventorsToshiki Ito, Takeshi Honma, Shiori Yonezawa

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Abstract

A photocurable composition contains a polymerizable compound (A) satisfying OA=NA/(NC,A−NO,A), wherein NA, NC,A and NO,A represent the total number of atoms, the number of carbon atoms, and the number of oxygen atoms, respectively, in (A); and a non-polymerizable component (E) containing at least one compound (X) including a photopolymerization initiator (B), in a proportion of 10% to 50% relative to the total weight of (A) and (E). The component (E) has a weight average molecular weight of 250 or less. The compound (X) satisfies OX=NX/(NC,X−NO,X). NX, NC,X and NO,X represent the total number of atoms, the number of carbon atoms, and the number of oxygen atoms, respectively, in the corresponding compound (X). The composition satisfies: OA−OE>1.00; and OAE<3.40. OE and OAE represent the molar fraction weighted averages of OX's and of OA and OE, respectively.

Claims22

Dependent claims

A photocurable composition comprising:

a polymerizable compound (A) having a parameter OA=NA/(NC,A−NO,A), where OA represents the Ohnishi parameter OA of the polymerizable compound (A), NA represents the total number of atoms in the molecule of the polymerizable compound (A), NC,A represents the number of carbon atoms in the molecule of the polymerizable compound (A), and NO,A represents the number of oxygen atoms in the molecule of the polymerizable compound (A);
and
a non-polymerizable component (E) in a proportion in the range of more than 10% to 50% by weight relative to the total weight of the polymerizable compound (A) and the non-polymerizable component (E), wherein the non-polymerizable component (E) has a weight average molecular weight of 250 or less, the non-polymerizable component (E) contains at least one non-polymerizable compound (X) including a photopolymerization initiator (B), and the at least one non-polymerizable compound (X) has a parameter OX=NX/(NC,X−NO,X), where OX represents the Ohnishi parameters OX of compounds (X) contained in the non-polymerizable component (E), NX represents the total number of atoms in the molecule of the corresponding compound (X), NC,X represents the number of carbon atoms in the molecule of the corresponding compound (X), and NO,X represents the number of oxygen atoms in the molecule of the corresponding compound (X),
wherein the photocurable composition satisfies the following relational expressions (1) and (2):
OA−OE>1.00 (1), and
OAE<3.40 (2),
wherein OE represents the molar fraction weighted average of the parameters OX of the at least one non-polymerizable compound (X), and OAE represents the molar fraction weighted average of the parameters OA and OE, and the non-polymerizable component (E) is nonvolatile organic compound.

4 more elements

A cured product including a photocurable composition cured on a substrate by irradiating the photocurable composition with light while the photocurable composition is in contact with a mold to receive a pattern from the mold, wherein the photocurable composition is prepared by a process comprising:

presenting a photocurable composition having:
a polymerizable compound (A) having a parameter OA=NA/(NC,A−NO,A), where OA represents the Ohnishi parameter OA of the polymerizable compound (A), NA represents the total number of atoms in the molecule of the polymerizable compound (A), NC,A represents the number of carbon atoms in the molecule of the polymerizable compound (A), and NO,A represents the number of oxygen atoms in the molecule of the polymerizable compound (A), and
a non-polymerizable component (E) containing at least one non-polymerizable compound (X) including a photopolymerization initiator (B), in a proportion in the range of more than 10% to 50% by weight relative to the total weight of the polymerizable compound (A) and the non-polymerizable component (E), wherein the non-polymerizable component (E) has a weight average molecular weight of 250 or less, and the at least one non-polymerizable compound (X) has a parameter OX=NX/(NC,X−NO,X), where OX represents the Ohnishi parameters OX of compounds (X) contained in the non-polymerizable component (E), NX represents the total number of atoms in the molecule of the corresponding compound (X), NC,X represents the number of carbon atoms in the molecule of the corresponding compound (X), and NO,X represents the number of oxygen atoms in the molecule of the corresponding compound (X),
wherein the photocurable composition satisfies the following relational expressions (1) and (2):
OA−OE>1.00 (1), and
OAE<3.40 (2),
wherein OE represents the molar fraction weighted average of the parameters OX of the at least one non-polymerizable compound (X), and OAE represents the molar fraction weighted average of the parameters OA and OE.

4 more elements

An optical component including a photocurable composition cured on a substrate by irradiating the photocurable composition with light while the photocurable composition is in contact with a mold to receive a pattern from the mold, wherein the photocurable composition is prepared by a process comprising:

presenting a photocurable composition having:
a polymerizable compound (A) having a parameter OA=NA/(NC,A−NO,A), where OA represents the Ohnishi parameter OA of the polymerizable compound (A), NA represents the total number of atoms in the molecule of the polymerizable compound (A), NC,A represents the number of carbon atoms in the molecule of the polymerizable compound (A), and NO,A represents the number of oxygen atoms in the molecule of the polymerizable compound (A), and
a non-polymerizable component (E) containing at least one non-polymerizable compound (X) including a photopolymerization initiator (B), in a proportion in the range of more than 10% to 50% by weight relative to the total weight of the polymerizable compound (A) and the non-polymerizable component (E), wherein the non-polymerizable component (E) has a weight average molecular weight of 250 or less, and the at least one non-polymerizable compound (X) has a parameter OX=NX/(NC,X−NO,X), where OX represents the Ohnishi parameters OX of compounds (X) contained in the non-polymerizable component (E), NX represents the total number of atoms in the molecule of the corresponding compound (X), NC,X represents the number of carbon atoms in the molecule of the corresponding compound (X), and NO,X represents the number of oxygen atoms in the molecule of the corresponding compound (X),
wherein the photocurable composition satisfies the following relational expressions (1) and (2):
OA−OE>1.00 (1), and
OAE<3.40 (2),
wherein OE represents the molar fraction weighted average of the parameters OX of the at least one non-polymerizable compound (X), and OAE represents the molar fraction weighted average of the parameters OA and OE.

4 more elements

A circuit board having a substrate etched or ion implantated using, as a mask, a photocurable composition cured on the substrate by irradiating the photocurable composition with light while the photocurable composition is in contact with a mold to receive a pattern from the mold, wherein the photocurable composition is prepared by a process comprising:

presenting a photocurable composition having:
a polymerizable compound (A) having a parameter OA =NA/(NC,A−NO,A), where OA represents the Ohnishi parameter OA of the polymerizable compound (A), NA represents the total number of atoms in the molecule of the polymerizable compound (A), NC,A represents the number of carbon atoms in the molecule of the polymerizable compound (A), and NO,A represents the number of oxygen atoms in the molecule of the polymerizable compound (A), and
a non-polymerizable component (E) containing at least one non-polymerizable compound (X) including a photopolymerization initiator (B), in a proportion in the range of more than 10% to 50% by weight relative to the total weight of the polymerizable compound (A) and the non-polymerizable component (E), wherein the non-polymerizable component (E) has a weight average molecular weight of 250 or less, and the at least one non-polymerizable compound (X) has a parameter OX=NX/(NC,X−NO,X), where OX represents the Ohnishi parameters OX of compounds (X) contained in the non-polymerizable component (E), NX represents the total number of atoms in the molecule of the corresponding compound (X), NC,X represents the number of carbon atoms in the molecule of the corresponding compound (X), and NO,X represents the number of oxygen atoms in the molecule of the corresponding compound (X),
wherein the photocurable composition satisfies the following relational expressions (1) and (2):
OA−OE>1.00 (1), and
OAE<3.40 (2),
wherein OE represents the molar fraction weighted average of the parameters OX of the at least one non-polymerizable compound (X), and OAE represents the molar fraction weighted average of the parameters OA and OE.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/506,214Filed 18 Aug 2015
Priority: JP 2014-17122426 Aug 2014
Published: US 2017/0287695 A15 Oct 2017
Granted: 17 Mar 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C08F 222/102
Of polyhydric alcohols or polyhydric phenols: of dialcohols, e.g. ethylene glycol diacrylate or 1,4-butanediol dimethacrylate
C08F 2/44
Processes of polymerisation: polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
C08F 2/48
Polymerisation initiated by wave energy or particle radiation: by ultraviolet or visible light
C08F 2/50
By ultraviolet or visible light: with sensitising agents