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Negative Photosensitive Resin Composition Cured Film Element Provided With Cured Film Display Device Provided With Cured Film And Method For Producing Same

Abstract: Provided is a negative photosensitive resin composition which is highly sensitive and suppresses the formation of a development residue due to a pigment and which enables the achievement of a cured film having excellent heat resistance and light blocking properties. A negative photosensitive resin composition which contains (A) an alkali-soluble resin (B) a radically polymerizable compound (C1) a photopolymerization initiator and (D1) a pigment and which is configured such that: the radically polymerizable compound (B) contains (B1) a flexible chain-containing radically polymerizable compound; the flexible chain-containing radically polymerizable compound (B1) contains a compound having (I) a structure derived from a compound that has at least three hydroxy groups in each molecule (II) at least three ethylenically unsaturated double bond groups and (III) at least one aliphatic chain; the average molecular weight of the aliphatic chain is 40-500; and the content ratio of the pigment (D1) is 5-70% by mass in the total solid content.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
22 March 2019
Publication Number
19/2019
Publication Type
INA
Invention Field
PHYSICS
Status
Email
patent@depenning.com
Parent Application

Applicants

TORAY INDUSTRIES, INC.
1-1, Nihonbashi-Muromachi 2-chome, Chuo-ku, Tokyo 103-8666

Inventors

1. TANIGAKI, Yugo
c/o Toray Industries, Inc., Shiga Plant, 1-1, Sonoyama 1-chome, Otsu-shi, Shiga 520-8558
2. ISHIKAWA, Akihiro
c/o Toray Industries, Inc., Shiga Plant, 1-1, Sonoyama 1-chome, Otsu-shi, Shiga 520-8558
3. MIYOSHI, Kazuto
c/o Toray Industries, Inc., Shiga Plant, 1-1, Sonoyama 1-chome, Otsu-shi, Shiga 520-8558

Specification

WE CLAIM:
1. A negative-type photosensitive resin composition
comprising: an alkali-soluble resin (A); a radical-
polymerizable compound (B); a photopolymerization initiator
(C1); and a pigment (D1),
wherein the radical-polymerizable compound (B) includes a flexible chain-containing radical-polymerizable compound (B1),
the flexible chain-containing radical-polymerizable compound (B1) includes a compound having (I) a structure derived from a compound having at least three hydroxyl groups in the molecule, (II) at least three ethylenically unsaturated double bond groups, and (III) at least one aliphatic chain,
the aliphatic chain has an average molecular weight of 40 to 500, and
the content of the pigment (D1) is 5 to 70 mass% of the total solid content.
2. A negative-type photosensitive resin composition as
set forth in claim 1,
wherein the alkali-soluble resin (A) includes a first resin (A1), and
the first resin (A1) includes at least one selected from the group consisting of a polyimide (A1-1), a polyimide precursor (A1-2), polybenzoxazole (A1-3), and a

polybenzoxazole precursor (A1-4).
3. A negative-type photosensitive resin composition as set forth in claim 1 or 2, wherein the flexible chain-containing radical-polymerizable compound (B1) includes a compound represented by general formula (27) and/or a compound represented by general formula (28): [Chemical formula 1]
wherein, in general formula (27), X28 is a divalent organic group; Y28 to Y33 are each independently a direct bond or a group represented by general formula (24), and at least one of Y28 to Y33 is a group represented by general formula (24); P12 to P17 are each independently a hydrogen atom or a group represented by general formula (25), and at

least three of P12 to P17 are groups represented by general formula (25); a, b, c, d, e, and f are each independently 0 or 1, and g is an integer of 0 to 10; wherein, in general formula (28), X29 is a divalent organic group; X30 and X31 are each independently a direct bond or an alkylene chain containing 1 to 10 carbon atoms; Y34 to Y37 are each independently a direct bond or a group represented by general formula (24), and at least one of Y34 to Y37 is a group represented by general formula (24); R65 and R66 are each independently a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms; P18 to P21 are each independently a hydrogen atom or a group represented by general formula (25), and at least three of P18 to P21 are groups represented by general formula (25); and h, i, j, and k are each independently 0 or 1, and l is an integer of 0 to 10:
[Chemical formula 2]
wherein, in general formula (24), R60 is a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms; Z17

represents a group represented by general formula (29) or a group represented by general formula (30); a is an integer of 1 to 10, b is an integer of 1 to 4, c is 0 or 1, d is an integer of 1 to 4, and e is 0 or 1; when c is 0, d is 1; wherein, in general formula (25), R61 to R63 are each independently a hydrogen atom, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 15 carbon atoms; and wherein, in general formula (30), R67 is a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms.
4. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 3, wherein the flexible chain-containing radical-polymerizable compound (B1) includes a compound represented by general formula (23): [Chemical formula 3]
wherein, in general formula (23), X17 is a divalent organic group; Y17 to Y22 are each independently a direct bond or a group represented by general formula (24), and at

least one of Y17 to Y22 is a group represented by general formula (24); P1 to P6 are each independently a hydrogen atom or a group represented by general formula (25), and at least three of P1 to P6 are groups represented by general formula (25); and a, b, c, d, e, and f are each independently 0 or 1:
[Chemical formula 4]
wherein, in general formula (24), R60 is a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms; Z17 represents a group represented by general formula (29) or a group represented by general formula (30); a is an integer of 1 to 10, b is an integer of 1 to 4, c is 0 or 1, d is an integer of 1 to 4, and e is 0 or 1; when c is 0, d is 1; wherein, in general formula (25), R61 to R63 are each independently a hydrogen atom, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 15 carbon atoms; and wherein, in general formula (30), R67 is a hydrogen atom or an alkyl group containing 1 to 10 carbon

atoms.
5. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 4, wherein the flexible chain-containing radical-polymerizable compound (B1) has at least one lactone-modified chain and/or at least one lactam-modified chain.
6. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 5,
wherein the radical-polymerizable compound (B) further includes a flexible chain-containing bifunctional radical-polymerizable compound (B2),
the flexible chain-containing bifunctional radical-polymerizable compound (B2) includes a compound having (I) a structure derived from a compound having at least two hydroxyl groups in the molecule, (II) two ethylenically unsaturated double bond groups, and (III) at least one lactone-modified chain and/or lactam-modified chain, and
the average molecular weights of the lactone-modified chain and the lactam-modified chain are 40 to 500.
7. A negative-type photosensitive resin composition as
set forth in any one of claims 1 to 6, wherein the pigment
(D1) includes one or more selected from the group
consisting of a black organic pigment (D1a-1), a black
inorganic pigment (D1a-2), and a mixture of two or more
color pigments (D1a-3).

8. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 7, wherein the alkali-soluble resin (A) includes an alkali-soluble resin (A) that has no ethylenically unsaturated double bond group.
9. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 8,
wherein the alkali-soluble resin (A) further comprises a second resin (A2), and
the second resin (A2) includes one or more selected from the group consisting of polysiloxane (A2-1), polycyclic side chain-containing resin (A2-2), acrylic resin (A2-3), and acid-modified epoxy resin (A2-4).
10. A negative-type photosensitive resin composition as set forth in any one of claims 1 to 9, wherein the flexible chain-containing radical-polymerizable compound (B1) accounts for 10 to 50 parts by mass, relative to the total quantity of the alkali-soluble resin (A) and the radical-polymerizable compound (B) which accounts for 100 parts by mass.
11. A negative-type photosensitive resin composition as set forth in any one of claims 7 to 10, wherein the black organic pigment (D1a-1) includes one or more selected from the group consisting of a benzofuranone based black pigment (D1a-1a), a perylene based black pigment (D1a-1b), and an azo based black pigment (D1a-1c).

12. A negative-type photosensitive resin composition as
set forth in claims 7 to 11,
wherein the black organic pigment (D1a-1) further includes a covering layer (DC), and
the covering layer (DC) includes one or more selected from the group consisting of a silica covering layer (DC-1), a metal oxide covering layer (DC-2), and a metal hydroxide covering layer (DC-3).
13. A negative-type photosensitive resin composition
comprising: an alkali-soluble resin (A); a radical-
polymerizable compound (B); a photopolymerization initiator
(C1); and a pigment (D1),
wherein the content of the pigment (D1) is 5 to 70 mass% of the total solid content,
the pigment (D1) includes, as a black organic pigment (D1a-1), one or more selected from the group consisting of a benzofuranone based black pigment (D1a-1a), a perylene based black pigment (D1a-1b), and an azo based black pigment (D1a-1c),
the radical-polymerizable compound (B) includes a flexible chain-containing radical-polymerizable compound (B1),
the flexible chain-containing radical-polymerizable compound (B1) includes a compound having (I) a structure derived from a compound having at least three hydroxyl

groups in the molecule, (II) at least three ethylenically unsaturated double bond groups, and (III) at least one aliphatic chain,
the aliphatic chain has an average molecular weight of 40 to 500, and
the flexible chain-containing radical-polymerizable compound (B1) includes one or more selected from the group consisting of a compound represented by general formula (27) and a compound represented by general formula (28):
[Chemical formula 5]
wherein, in general formula (27), X28 is a divalent organic group; Y28 to Y33 are each independently a direct bond or a group represented by general formula (24), and at

least one of Y28 to Y33 is a group represented by general formula (24); P12 to P17 are each independently a hydrogen atom or a group represented by general formula (25), and at least three of P12 to P17 are groups represented by general formula (25); a, b, c, d, e, and f are each independently 0 or 1, and g is an integer of 0 to 10; wherein, in general formula (28), X29 is a divalent organic group; X30 and X31 are each independently a direct bond or an alkylene chain containing 1 to 10 carbon atoms; Y34 to Y37 are each independently a direct bond or a group represented by general formula (24), and at least one of Y34 to Y37 is a group represented by general formula (24); R65 and R66 are each independently a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms; P18 to P21 are each independently a hydrogen atom or a group represented by general formula (25), and at least three of P18 to P21 are groups represented by general formula (25); and h, i, j, and k are each independently 0 or 1, and l is an integer of 0 to 10:

wherein, in general formula (24), R60 is a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms; Z17 represents a group represented by general formula (29) or a group represented by general formula (30); a is an integer of 1 to 10, b is an integer of 1 to 4, c is 0 or 1, d is an integer of 1 to 4, and e is 0 or 1; when c is 0, d is 1; wherein, in general formula (25), R61 to R63 are each independently a hydrogen atom, an alkyl group containing 1 to 10 carbon atoms, or an aryl group containing 6 to 15 carbon atoms; and wherein, in general formula (30), R67 is a hydrogen atom or an alkyl group containing 1 to 10 carbon atoms.
14. A cured film formed by curing a negative-type photosensitive resin composition as set forth in any one of claims 1 to 13.
15. A cured film as set forth in claim 14, wherein the optical density per micrometer of film thickness is 0.3 to 5.0.

16. An element comprising the cured film as set forth in either claim 14 or 15.
17. A display device comprising the cured film as set forth in either claim 14 or 15.
18. A display device as set forth in claim 17, wherein an aperture ratio of an opening of a pixel dividing layer in a display area is 20% or less.
19. A display device as set forth in claim 17 or 18 in the form of an organic EL display device or a liquid crystal display device.
20. A production method for the display device as set forth in any one of claims 17 to 19, comprising:

(1) a step for forming a coating film of the negative-type photosensitive resin composition as set forth in any one of claims 1 to 13 on a substrate;
(2) a step for applying active actinic ray to the coating film of the negative-type photosensitive resin composition through a photomask;
(3) a step for developing it with an alkaline solution to form a pattern of the negative-type photosensitive resin composition; and
(4) a step for heating the pattern to produce a cured pattern of the negative-type photosensitive resin composition.

Documents

Application Documents

# Name Date
1 201947011069.pdf 2019-03-22
2 201947011069-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [22-03-2019(online)].pdf 2019-03-22
3 201947011069-STATEMENT OF UNDERTAKING (FORM 3) [22-03-2019(online)].pdf 2019-03-22
4 201947011069-PRIORITY DOCUMENTS [22-03-2019(online)].pdf 2019-03-22
5 201947011069-POWER OF AUTHORITY [22-03-2019(online)].pdf 2019-03-22
6 201947011069-FORM 1 [22-03-2019(online)].pdf 2019-03-22
7 201947011069-DRAWINGS [22-03-2019(online)].pdf 2019-03-22
8 201947011069-DECLARATION OF INVENTORSHIP (FORM 5) [22-03-2019(online)].pdf 2019-03-22
9 201947011069-COMPLETE SPECIFICATION [22-03-2019(online)].pdf 2019-03-22
10 201947011069-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [22-03-2019(online)].pdf 2019-03-22
11 Abstract_201947011069.jpg 2019-03-25
12 201947011069-Proof of Right (MANDATORY) [03-04-2019(online)].pdf 2019-04-03
13 Correspondence by Agent_Form1_04-04-2019.pdf 2019-04-04
14 201947011069-FORM 3 [30-08-2019(online)].pdf 2019-08-30