WO2022024554A1 - Coloring composition, cured product, color filter, solid-state imaging device, image display device, and resin and method for producing same - Google Patents
Coloring composition, cured product, color filter, solid-state imaging device, image display device, and resin and method for producing same Download PDFInfo
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- WO2022024554A1 WO2022024554A1 PCT/JP2021/021714 JP2021021714W WO2022024554A1 WO 2022024554 A1 WO2022024554 A1 WO 2022024554A1 JP 2021021714 W JP2021021714 W JP 2021021714W WO 2022024554 A1 WO2022024554 A1 WO 2022024554A1
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- resin
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 34
- 238000003384 imaging method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 7
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- DDHQTWZKAJOZQL-UHFFFAOYSA-N naphthalene-1,4,5-tricarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O DDHQTWZKAJOZQL-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- BTHGHFBUGBTINV-UHFFFAOYSA-N naphthalene-2,3,6-tricarboxylic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 BTHGHFBUGBTINV-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000011242 organic-inorganic particle Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical group C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical group 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- RRCCWYJNLXYHMI-UHFFFAOYSA-N sulfanylmethanediol Chemical compound OC(O)S RRCCWYJNLXYHMI-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical group S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
- C08F8/16—Lactonisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
Definitions
- the present disclosure relates to a coloring composition, a cured product, a color filter, a solid-state image sensor, an image display device, a resin, and a method for producing the same.
- a color filter is an indispensable component of a solid-state image sensor or an image display device.
- the solid-state image sensor and the image display device may generate noise due to the reflection of visible light. Therefore, a light-shielding film is provided on the solid-state image sensor or the image display device to suppress the generation of noise.
- a method for producing such a color filter or a light-shielding film a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin is used to form a colored composition layer.
- a method of exposing and developing this colored photosensitive composition layer to form a pattern is known.
- the one described in Patent Document 1 or 2 is known.
- An object to be solved by the embodiment according to the present disclosure is to provide a coloring composition having excellent liquid stability. Further, a problem to be solved by another embodiment according to the present disclosure is to provide a cured product of the coloring composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter. It is to be. Further, a problem to be solved by another embodiment according to the present disclosure is to provide a novel resin and a method for producing the same.
- a coloring composition containing a pigment, a resin represented by the following formula (1), and a solvent containing a pigment, a resin represented by the following formula (1), and a solvent.
- R 1 independently represents a divalent linking group
- R 2 independently represents a hydrogen atom or a monovalent substituent
- L 1 represents a (n + 1) -valent linking group.
- a group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 1 represents a polymer chain obtained by polymerizing an ethylenically unsaturated compound.
- R 1 independently represents a divalent linking group
- R 2 independently represents a hydrogen atom or a monovalent substituent
- L 2 represents a (n + 1) -valent linking group.
- a group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 2 represents an acid group and a polymer chain having a structure represented by the above formula (2).
- ⁇ 11> A cured product obtained by drying or curing the coloring composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> A color filter comprising the cured product according to ⁇ 11>.
- ⁇ 13> A solid-state image sensor having the color filter according to ⁇ 12>.
- ⁇ 15> A resin represented by the following formula (3).
- R 1 independently represents a divalent linking group
- R 2 independently represents a hydrogen atom or a monovalent substituent
- L 2 represents a (n + 1) -valent linking group.
- a group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 2 represents an acid group and a polymer chain having a structure represented by the following formula (2).
- R 3 represents a hydrogen atom or an alkyl group
- X 1 represents a monovalent substituent
- L represents an integer of 1 or more.
- the black pigment is not particularly limited, and known ones can be used.
- carbon black, titanium black, graphite and the like can be mentioned, with carbon black and titanium black being preferable, and titanium black being more preferable.
- Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable. Titanium black can modify the surface as needed for the purpose of improving dispersibility and suppressing cohesion.
- the resin described in JP-A-2017-032685, the resin described in JP-A-2017-075248, and the resin described in JP-A-2017-066240 can also be used.
- the resin having an acid group preferably contains a repeating unit having an acid group in the side chain, and more preferably contains 5 mol% to 70 mol% of the repeating unit having an acid group in the side chain in all the repeating units of the resin. ..
- the upper limit of the content of the repeating unit having an acid group in the side chain is preferably 50 mol% or less, more preferably 30 mol% or less.
- the lower limit of the content of the repeating unit having an acid group in the side chain is preferably 10 mol% or more, more preferably 20 mol% or more.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to, and the contents thereof are incorporated in the present specification.
- the resin used in the present disclosure preferably contains a repeating unit derived from the compound represented by the following formula (X).
- the amine value of the resin having an amino group as a basic group is preferably 30 mgKOH / g to 200 mgKOH / g.
- the lower limit is more preferably 40 mgKOH / g or more, and particularly preferably 50 mgKOH / g or more.
- the upper limit is more preferably 250 mgKOH / g or less, further preferably 200 mgKOH / g or less, and particularly preferably 150 mgKOH / g or less.
- the weight average molecular weight (Mw) of the resin having an amino group is preferably 5,000 to 100,000.
- the number average molecular weight (Mn) of the resin having an amino group is preferably 1,000 to 20,000.
- the resin used as the dispersant is a graft resin.
- the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the contents thereof are incorporated in the present specification.
- the resin used as the dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less and a side chain having 40 to 10,000 atoms, and basic nitrogen is contained in at least one of the main chain and the side chain.
- a resin having an atom is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
- the resin B used in the present disclosure is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (b-1) and the repeating unit represented by the formula (b-10). ..
- Ar 1 represents a group containing an aromatic carboxyl group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- Ar 10 represents a group containing an aromatic carboxyl group
- L 11 represents -COO- or -CONH-
- L 12 represents a trivalent linking group
- P 10 represents a polymer. Represents a chain.
- aromatic tricarboxylic acid anhydride examples include benzenetricarboxylic acid anhydride (1,2,3-benzenetricarboxylic acid anhydride, trimellitic acid anhydride [1,2,4-benzenetricarboxylic acid anhydride], etc.).
- aromatic tetracarboxylic acid anhydrides include pyromellitic dianhydride, ethylene glycol dianhydride trimellitic acid ester, propylene glycol dianhydride trimellitic acid ester, butylene glycol dianhydride trimellitic acid ester, 3,3.
- Specific examples of the group containing an aromatic carboxyl group represented by Ar 1 include a group represented by the formula (Ar-1), a group represented by the formula (Ar-2), and a group represented by the formula (Ar-3). Examples include the base.
- n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
- n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
- n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , the above formula (Q-). It represents a group represented by 1) or a group represented by the above formula (Q-2).
- L 1 represents -COO- or -CONH-, and preferably -COO-.
- the divalent linking group represented by L 2 in the formula (b-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these.
- a group that combines two or more of the above can be mentioned.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched, or cyclic.
- the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- the alkylene group and the arylene group may have a substituent.
- substituent include a hydroxy group and the like.
- the divalent linking group represented by L 2 is preferably a group represented by —OL 2a —O—.
- L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group, and —O—, —CO—, —COO—, —OCO—, Examples thereof include a group in combination with at least one selected from the group consisting of -NH- and -S-.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched or cyclic.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and the like.
- L 11 represents -COO- or -CONH-, and preferably -COO-.
- the trivalent linking group represented by L 12 in the formula (b-10) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and two of these.
- a group that combines species or more can be mentioned.
- the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
- the aliphatic hydrocarbon group may be linear, branched or cyclic.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
- the hydrocarbon group may have a substituent.
- substituent include a hydroxy group and the like.
- the trivalent linking group represented by L 12 is preferably a group represented by the following formula (L12-1), and more preferably a group represented by the formula (L12-2).
- the trivalent linking group represented by L 12a and L 12b is a group consisting of a hydrocarbon group; a hydrocarbon group and -O-, -CO-, -COO-, -OCO-, -NH- and -S-.
- a group that is a combination of at least one selected from the above can be mentioned.
- the divalent linking group represented by LP2 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-. Examples thereof include -SO 2- , -CO-, -O-, -COO-, -OCO-, -S-, -NHCO-, -CONH-, and a group consisting of a combination of two or more of these.
- RP4 represents a hydrogen atom or a substituent.
- Substituents include hydroxy group, carboxy group, alkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkylthioether group, arylthioether group, heteroarylthioether group and (meth) acryloyl.
- Examples thereof include a group, an oxetanyl group, a blocked isocyanate group and the like.
- the blocked isocyanate group in the present disclosure is a group capable of generating an isocyanate group by heat, and for example, a group in which a blocking agent and an isocyanate group are reacted to protect the isocyanate group can be preferably exemplified.
- Compounds having two hydroxy groups and one thiol group in the molecule include, for example, 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-.
- a polymerizable monomer having an ethylenically unsaturated group is radically polymerized in the presence of a hydroxy group-containing thiol compound (preferably a compound having two hydroxy groups and one thiol group in the molecule) to form 2 in one terminal region.
- a vinyl polymer having two hydroxy groups was synthesized, and the synthesized vinyl polymer was combined with one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides.
- a method of reacting and producing is radically polymerized in the presence of a hydroxy group-containing thiol compound (preferably a compound having two hydroxy groups and one thiol group in the molecule) to form 2 in one terminal region.
- a vinyl polymer having two hydroxy groups was synthesized, and the synthesized vinyl polymer was combined with one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid
- a polymerizable monomer having a hydroxy group may be radically polymerized, and then a compound having an isocyanate group (for example, a compound having an isocyanate group and the above-mentioned functional group A) may be reacted. .. This allows the functional group A to be introduced into the polymer chain P10 .
- the resin B can also be synthesized according to the method described in paragraphs 0120 to 0138 of JP-A-2018-101039.
- Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and Solsparse series manufactured by Japan Lubrizol Co., Ltd. (for example, DISPERBYK-111, 161 etc.). For example, Solsparse 76500) and the like. Further, the pigment dispersants described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification. The resin described as the dispersant can also be used for purposes other than the dispersant. For example, it can also be used as a binder.
- the coloring composition according to the present disclosure only one kind of resin may be used, or two or more kinds of resins may be used in combination.
- the total amount thereof is preferably in the following range.
- the content of the resin is preferably 5% by mass to 40% by mass, preferably 10% by mass, based on the total solid content of the coloring composition from the viewpoint of suppressing development residue, stability of dispersion liquid, and adhesiveness. It is more preferably% to 30% by mass, and particularly preferably 10% by mass to 25% by mass.
- the content of the resin used as the dispersant is preferably smaller than the content of the resin represented by the above formula (1).
- the coloring composition according to the present disclosure may contain a pigment derivative (hereinafter, also simply referred to as "derivative").
- the pigment derivative include compounds having a structure in which a part of the chromophore is replaced with an acid group or a basic group.
- the chromogens constituting the pigment derivative include quinoline skeleton, benzoimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthracinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone skeleton, perylene skeleton, thioindigo skeleton, and iso.
- Ions, phosphonium ions and the like can be mentioned.
- the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimidemethyl group.
- the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
- the coloring composition according to the present disclosure preferably contains a photopolymerization initiator.
- the coloring composition according to the present disclosure contains a polymerizable compound, it is preferable that the coloring composition according to the present disclosure further contains a photopolymerization initiator.
- the coloring composition according to the present disclosure is preferably a photosensitive coloring composition, and more preferably a negative type photosensitive coloring composition.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible light region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (above, IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure27, Irgacure29. (Manufactured by the company) and the like.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369, Irger Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
- an oxime compound having a fluorene ring can also be used.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a benzofuran skeleton can also be used.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 nm to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 nm to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1,000 to 300,000, and more preferably 2,000 to 300,000 from the viewpoint of sensitivity. Is more preferable, and 5,000 to 200,000 is particularly preferable.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- a bifunctional or trifunctional or higher photoradical polymerization initiator may be used as the photopolymerization initiator.
- two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the colored composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
- diglycerin EO ethylene oxide modified (meth) acrylate
- pentaerythritol tetraacrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- NK Ester A-TMMT 1,6-Hexanediol Diacrylate
- RP-1040 manufactured by Nippon Kayaku Co., Ltd.
- Aronix TO-2349 Toa Synthetic Co., Ltd.
- NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- 8UH-1006, 8UH-1012 manufactured by Taisei Fine Chemical Co., Ltd.
- Light Acrylate POB-A0 manufactured by Kyoeisha Chemical Co.
- a polymerizable compound having a fluorene skeleton can also be used.
- examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
- a polymerizable compound having an amino structure or a sulfide structure in the molecule described in JP-A-63-260909 and JP-A No. 01-105238.
- the polymerizable compounds include UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, and AH-600. , T-600, AI-600, LINK-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) and the like can also be used.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the pore diameter of the filter is preferably 0.01 ⁇ m to 7.0 ⁇ m, more preferably 0.01 ⁇ m to 3.0 ⁇ m, and even more preferably 0.05 ⁇ m to 0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), Kitts Micro Filter Co., Ltd., etc. can be used.
- the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, the volume resistance value of the pixel is preferably 109 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example. The volume resistance value of the pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest).
- the exposure illuminance can be appropriately set, preferably 1,000 W / m 2 to 100,000 W / m 2 (for example, 5,000 W / m 2 , 15,000 W / m 2 , or 35, It can be selected from the range of 000 W / m 2 ).
- the oxygen concentration and the exposure illuminance may be appropriately combined with each other, and for example, the illuminance may be 10,000 W / m 2 when the oxygen concentration is 10% by volume, the illuminance may be 20,000 W / m 2 when the oxygen concentration is 35% by volume, and the like.
- the pattern formation by the dry etching method is a step of forming a colored composition layer on a support using the colored composition according to the present disclosure and curing the entire colored composition layer to form a cured product layer.
- the photoresist layer it is preferable to further perform a prebaking treatment.
- a prebaking treatment it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
- a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
- the description in paragraphs 0010 to 0067 of JP2013-064993 can be referred to, and this content is incorporated in the present specification.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a lower refractive index than each colored pixel. Examples of the image pickup apparatus having such a structure are described in JP-A-2012-227478, JP-A-2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No.
- R 1 independently represents a divalent linking group
- R 2 independently represents a hydrogen atom or a monovalent substituent
- L 2 represents a (n + 1) -valent linking group.
- a group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 2 represents an acid group and a polymer chain having a structure represented by the following formula (2).
- the preferred embodiment of the resin represented by the formula (3) in the resin according to the present disclosure is the same as the preferred embodiment of the resin represented by the above-mentioned formula (3).
- the preferred embodiment of the structure represented by the formula (2) in the resin according to the present disclosure is the same as the preferred embodiment of the structure represented by the above-mentioned formula (2).
- the method for producing the resin represented by the formula (3) in the resin according to the present disclosure is not particularly limited, but includes the above steps (i-1) and (i-2), or the above steps.
- a production method including (ii-1) and step (ii-2) is preferably mentioned.
- the method for producing a resin represented by the formula (3) and the above steps (i-1) and (i-2) are included, or the above steps (ii-1) and (ii-2) are performed.
- the manufacturing method including the above is the same as described above, and the preferred embodiment is also the same.
- -AM-2 manufacturing method In a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer, 75 parts by mass of methyl methacrylate, 75 parts by mass of n-butyl acrylate, and 68.1 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) are charged, and nitrogen gas is charged. The inside of the reaction vessel was replaced with. The inside of the reaction vessel is heated to 70 ° C., 9 parts by mass of 3-mercapto-1,2-propanediol is added, and 0.18 parts by mass of AIBN (azobisisobutyronitrile) is further added, and the mixture is reacted for 12 hours. rice field.
- PMEA propylene glycol monomethyl ether acetate
- This dispersion treatment is repeated 10 times, and each dispersion R1 to R15 (red dispersion), dispersion Y1 (yellow dispersion), and comparative dispersions RM1 and RM2 (red dispersion) are repeated. ) was obtained respectively.
- PR254 C.I. I. Pigment Red 254
- PR264 C.I. I. Pigment Red 264
- PR272 C.I. I. Pigment Red 272
- PR122 C.I. I. Pigment Red 122 PO71: C.I. I. Pigment Orange 71
- Photopolymerization initiator F3 A compound having the following structure.
- Viscosity increase rate (%) [(Viscosity after standing (V1) -Initial viscosity (V0)) / Initial viscosity (V0)] ⁇ 100 A: 0 ⁇ viscosity increase rate ⁇ 3% B: 3% ⁇ Viscosity increase rate ⁇ 5% C: 5% ⁇ Viscosity increase rate ⁇ 10% D: 10% ⁇ Viscosity increase rate ⁇ 15% E: 15% ⁇ Viscosity increase rate
- composition layer an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 1.1 ⁇ m were arranged in a 4 mm ⁇ 3 mm region on the substrate via a mask pattern. Then, light having a wavelength of 365 nm was irradiated with an exposure amount of 500 mJ / cm 2 for exposure.
- the composition layer after exposure was paddle-developed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Then, it was rinsed with water in a spin shower and then washed with pure water.
- Example G80 to Example G97 A coloring composition was prepared in the same manner as in Example G1 except that the types and amounts of the dispersion liquid, the resin, the polymerizable compound, the photopolymerization initiator and the solvent were changed to those shown in Table 9, and the above was also prepared. Evaluation was performed. The pigment content in the coloring compositions of Examples G80 to G97 was 62.6% by mass with respect to the total solid content of the coloring compositions. The performance evaluation result was the same as that of Example G9.
- E5 Aronix TO-2349 (manufactured by Toagosei Co., Ltd.)
- F1 IRGACURE-OXE01 (manufactured by BASF), a compound having the following structure.
- F2 IRGACURE-OXE02 (manufactured by BASF), a compound having the following structure.
- F4 IRGACURE 369 (manufactured by BASF), a compound having the following structure.
- F5 A compound having the following structure.
- Examples B1 to B5, and Comparative Examples BM1 and BM2 A colored composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 12, and the above evaluation was performed. The evaluation results are shown in Table 12.
- the pigment content in the coloring compositions of Examples B1 to B5, and Comparative Examples BM1 and Comparative Example BM2 was 63% by mass with respect to the total solid content of the coloring composition.
- the coloring compositions of Examples were superior in liquid stability as compared with the coloring compositions of Comparative Examples. Further, as shown in Tables 6 to 12, the colored compositions of Examples were excellent in the adhesion of the obtained cured product and the ability to suppress the development residue.
- Example R1 and the coloring composition of Example B1 were sequentially patterned to form red, green and blue coloring patterns (Bayer patterns).
- the Bayer pattern is a red element, two green elements, and one blue element as disclosed in US Pat. No. 3,971,065.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. It was confirmed that no matter which of the coloring compositions prepared in the examples was used, the solid-state image sensor was excellent in adhesion in the cured film, and a solid-state image sensor having suitable image recognition ability was obtained.
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Abstract
Description
このようなカラーフィルタや遮光膜の製造方法として、着色剤と、重合性化合物と、光重合開始剤と、アルカリ可溶性樹脂とを含む着色感光性組成物を用いて着色組成物層を形成し、この着色感光性組成物層を露光及び現像してパターンを形成する方法が知られている。
また、従来のブロック共重合体としては、特許文献1又は2に記載のものが知られている。 A color filter is an indispensable component of a solid-state image sensor or an image display device. The solid-state image sensor and the image display device may generate noise due to the reflection of visible light. Therefore, a light-shielding film is provided on the solid-state image sensor or the image display device to suppress the generation of noise.
As a method for producing such a color filter or a light-shielding film, a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin is used to form a colored composition layer. A method of exposing and developing this colored photosensitive composition layer to form a pattern is known.
Further, as a conventional block copolymer, the one described in Patent Document 1 or 2 is known.
特許文献2:特開2001-81129号公報 Patent Document 1: Japanese Patent Application Laid-Open No. 2007-321141 Patent Document 2: Japanese Patent Application Laid-Open No. 2001-81129
また、本開示に係る他の実施形態が解決しようとする課題は、上記着色組成物の硬化物、上記硬化物を備えるカラーフィルタ、又は、上記カラーフィルタを備える固体撮像素子若しくは画像表示装置を提供することである。
更に、本開示に係る他の実施形態が解決しようとする課題は、新規な樹脂及びその製造方法を提供することである。 An object to be solved by the embodiment according to the present disclosure is to provide a coloring composition having excellent liquid stability.
Further, a problem to be solved by another embodiment according to the present disclosure is to provide a cured product of the coloring composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter. It is to be.
Further, a problem to be solved by another embodiment according to the present disclosure is to provide a novel resin and a method for producing the same.
<1> 顔料、下記式(1)で表される樹脂、及び、溶剤、を含む着色組成物。 The means for solving the above problems include the following aspects.
<1> A coloring composition containing a pigment, a resin represented by the following formula (1), and a solvent.
<4> 上記吸着性基が、酸基である<3>に記載の着色組成物。
<5> 上記樹脂が、下記式(3)で表される樹脂である<2>に記載の着色組成物。 <3> The coloring composition according to <1> or <2>, wherein P 1 has an adsorptive group.
<4> The coloring composition according to <3>, wherein the adsorptive group is an acid group.
<5> The coloring composition according to <2>, wherein the resin is a resin represented by the following formula (3).
<7> 上記P1を形成する上記エチレン性不飽和化合物が、酸基を有し、かつ、エチレン性不飽和基と上記酸基とを連結する最小の原子数が6~20である化合物を含む<1>~<4>のいずれか1つに記載の着色組成物。
<8> 上記樹脂の重量平均分子量が、3,000~15,000である<1>~<7>のいずれか1つに記載の着色組成物。
<9> 上記P1における上記エチレン性不飽和化合物由来のモノマー単位の数が、2~10である<1>~<4>のいずれか1つに記載の着色組成物。
<10> 重合性化合物を更に含む<1>~<9>のいずれか1つに記載の着色組成物。
<11> <1>~<10>のいずれか1つに記載の着色組成物を乾燥又は硬化してなる硬化物。
<12> <11>に記載の硬化物を備えるカラーフィルタ。
<13> <12>に記載のカラーフィルタを有する固体撮像素子。
<14> <12>に記載のカラーフィルタを有する画像表示装置。
<15> 下記式(3)で表される樹脂。 <6> The above R 1 is an alkylene group having 3 to 6 carbon atoms, the above R 2 is a hydrogen atom or an alkyl group, n is 1, and m is an integer of 4 to 20. <1> to <5> The coloring composition according to any one of.
<7> A compound in which the ethylenically unsaturated compound forming P 1 has an acid group and the minimum number of atoms connecting the ethylenically unsaturated group and the acid group is 6 to 20. The coloring composition according to any one of <1> to <4>.
<8> The coloring composition according to any one of <1> to <7>, wherein the resin has a weight average molecular weight of 3,000 to 15,000.
<9> The coloring composition according to any one of <1> to <4>, wherein the number of monomer units derived from the ethylenically unsaturated compound in P 1 is 2 to 10.
<10> The coloring composition according to any one of <1> to <9>, which further contains a polymerizable compound.
<11> A cured product obtained by drying or curing the coloring composition according to any one of <1> to <10>.
<12> A color filter comprising the cured product according to <11>.
<13> A solid-state image sensor having the color filter according to <12>.
<14> An image display device having the color filter according to <12>.
<15> A resin represented by the following formula (3).
工程(i-1):ヒドロキシ基を有するメルカプト化合物の存在下、エチレン性不飽和化合物を重合し、末端にヒドロキシ基を有する樹脂を作製する工程
工程(i-2):上記末端にヒドロキシ基を有する樹脂のヒドロキシ基に、ポリエステル樹脂鎖を形成する工程
工程(ii-1):ヒドロキシ基を有するメルカプト化合物のヒドロキシ基に、ポリエステル樹脂鎖を形成し、メルカプト基を有するポリエステル樹脂を作製する工程
工程(ii-2):上記メルカプト基を有するポリエステル樹脂の存在下、エチレン性不飽和化合物を重合する工程 <16> The method for producing a resin according to <15>, which comprises the following steps (i-1) and (i-2), or includes the following steps (ii-1) and (ii-2).
Step (i-1): A step of polymerizing an ethylenically unsaturated compound in the presence of a mercapto compound having a hydroxy group to prepare a resin having a hydroxy group at the terminal Step (i-2): A hydroxy group at the terminal. Step of forming a polyester resin chain on the hydroxy group of the resin (ii-1): Step of forming a polyester resin chain on the hydroxy group of the mercapto compound having a hydroxy group to produce a polyester resin having a mercapto group. (Ii-2): Step of polymerizing an ethylenically unsaturated compound in the presence of the polyester resin having a mercapto group.
また、本開示に係る他の実施形態によれば、上記着色組成物の硬化物、上記硬化物を備えるカラーフィルタ、又は、上記カラーフィルタを備える固体撮像素子若しくは画像表示装置が提供される。
更に、本開示に係る他の実施形態によれば、新規な樹脂及びその製造方法が提供される。 According to the embodiment according to the present disclosure, a coloring composition having excellent liquid stability is provided.
Further, according to another embodiment according to the present disclosure, there is provided a cured product of the coloring composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter.
Further, according to another embodiment according to the present disclosure, a novel resin and a method for producing the same are provided.
なお、本開示において、数値範囲を示す「~」とはその前後に記載される数値を下限値及び上限値として含む意味で使用される。
本開示中に段階的に記載されている数値範囲において、一つの数値範囲で記載された上限値又は下限値は、他の段階的な記載の数値範囲の上限値又は下限値に置き換えてもよい。また、本開示中に記載されている数値範囲において、その数値範囲の上限値又は下限値は、実施例に示されている値に置き換えてもよい。
更に、本開示において組成物中の各成分の量は、組成物中に各成分に該当する物質が複数存在する場合、特に断らない限り、組成物中に存在する該当する複数の物質の合計量を意味する。
また、本開示における基(原子団)の表記において、置換及び無置換を記していない表記は、置換基を有さないものと共に置換基を有するものをも包含するものである。例えば「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含するものである。
本開示において、特別な記載がない限り、「Me」はメチル基を、「Et」はエチル基を、「Pr」はプロピル基を、「Bu」はブチル基を、「Ph」はフェニル基を、それぞれ表す。
本開示において、「(メタ)アクリル」は、アクリル及びメタクリルの両方を包含する概念で用いられる語であり、「(メタ)アクリロイル」は、アクリロイル及びメタクリロイルの両方を包含する概念として用いられる語である。
また、本開示において、「工程」の用語は、独立した工程だけではなく、他の工程と明確に区別できない場合であっても、その工程の所期の目的が達成されれば本用語に含まれる。
本開示において「全固形分」とは、組成物の全組成から溶剤を除いた成分の総質量をいう。また、「固形分」とは、上述のように、溶剤を除いた成分であり、例えば、25℃において固体であっても、液体であってもよい。
また、本開示において、「質量%」と「重量%」とは同義であり、「質量部」と「重量部」とは同義である。
更に、本開示において、2以上の好ましい態様の組み合わせは、より好ましい態様である。
また、本開示における重量平均分子量(Mw)及び数平均分子量(Mn)は、特に断りのない限り、TSKgel GMHxL、TSKgel G4000HxL、TSKgel G2000HxL(何れも東ソー(株)製の商品名)のカラムを使用したゲルパーミエーションクロマトグラフィ(GPC)分析装置により、溶剤THF(テトラヒドロフラン)、示差屈折計により検出し、標準物質としてポリスチレンを用いて換算した分子量である。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。
本明細書において、染料とは、溶剤に対して溶解しやすい化合物を意味する。
以下、本開示を詳細に説明する。 The contents of the present disclosure will be described in detail below. The description of the constituents described below may be based on the representative embodiments of the present disclosure, but the present disclosure is not limited to such embodiments.
In the present disclosure, "-" indicating a numerical range is used to mean that the numerical values described before and after the numerical range are included as the lower limit value and the upper limit value.
In the numerical range described stepwise in the present disclosure, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of the numerical range described in another stepwise description. .. Further, in the numerical range described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
Further, in the present disclosure, the amount of each component in the composition is the total amount of the plurality of applicable substances present in the composition when a plurality of the substances corresponding to each component are present in the composition, unless otherwise specified. Means.
Further, in the notation of a group (atomic group) in the present disclosure, the notation that does not describe substitution or non-substitution includes those having no substituent as well as those having a substituent. For example, the "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In the present disclosure, "Me" is a methyl group, "Et" is an ethyl group, "Pr" is a propyl group, "Bu" is a butyl group, and "Ph" is a phenyl group, unless otherwise specified. , Represent each.
In the present disclosure, "(meth) acrylic" is a term used in a concept that includes both acrylic and methacrylic, and "(meth) acryloyl" is a term that is used as a concept that includes both acryloyl and methacrylic. be.
Further, in the present disclosure, the term "process" is included in this term not only as an independent process but also as long as the intended purpose of the process is achieved even if it cannot be clearly distinguished from other processes. Is done.
In the present disclosure, the "total solid content" means the total mass of the components excluding the solvent from the total composition of the composition. Further, the "solid content" is a component excluding the solvent as described above, and may be, for example, a solid or a liquid at 25 ° C.
Further, in the present disclosure, "% by mass" and "% by weight" are synonymous, and "parts by mass" and "parts by weight" are synonymous.
Further, in the present disclosure, a combination of two or more preferred embodiments is a more preferred embodiment.
Further, for the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the present disclosure, unless otherwise specified, columns of TSKgel GMHxL, TSKgel G4000HxL, and TSKgel G2000HxL (all trade names manufactured by Toso Co., Ltd.) are used. The molecular weight is detected by the solvent THF (tetrahydrofuran) and the differential refractometer by the gel permeation chromatography (GPC) analyzer and converted using polystyrene as the standard substance.
As used herein, the term pigment means a compound that is difficult to dissolve in a solvent.
As used herein, the term dye means a compound that is easily soluble in a solvent.
Hereinafter, the present disclosure will be described in detail.
本開示に係る着色組成物は、顔料、下記式(1)で表される樹脂、及び、溶剤、を含む。 (Coloring composition)
The coloring composition according to the present disclosure contains a pigment, a resin represented by the following formula (1), and a solvent.
本発明者らは、詳細な検討を行った結果、顔料を含む従来の着色組成物では、着色組成物の液安定性が十分でなく、顔料の凝集及び沈殿等が多く発生する場合があることを見出した。
本発明者らが鋭意検討した結果、上記構成を採用することにより、液安定性に優れる着色組成物が得られることを見出した。
上記式(1)で表される樹脂を含むことにより、顔料における共役鎖構造等と極性の近いと推定されるP1におけるポリマー鎖が顔料に配位又は吸着するとともに、上記式(1)で表される樹脂における-O-R1-CO-からなる構成繰り返し単位であるポリエステル構造が、立体反発性基として機能し、顔料同士の凝集を抑制することにより、液安定性に優れると推定している。 In recent years, as the number of pixels of an image sensor has increased, the pattern has become finer and thinner. Along with this, the pigment concentration in the coloring composition used for the color filter tends to be relatively increased, and the amount of the curable component and the developable component tends to be reduced.
As a result of detailed studies, the present inventors may find that the conventional coloring composition containing a pigment does not have sufficient liquid stability of the coloring composition, and a large amount of pigment aggregation and precipitation may occur. I found.
As a result of diligent studies by the present inventors, it has been found that a colored composition having excellent liquid stability can be obtained by adopting the above structure.
By containing the resin represented by the above formula ( 1 ), the polymer chain in P1 which is presumed to have a polarity close to that of the conjugated chain structure in the pigment is coordinated or adsorbed on the pigment, and the above formula (1) is used. It is presumed that the polyester structure, which is a structural repeating unit consisting of -OR 1 -CO- in the represented resin, functions as a steric repulsive group and suppresses aggregation between pigments, thereby excellent in liquid stability. ing.
本開示に係る着色組成物は、上記式(1)で表される樹脂を含む。
式(1)におけるR1はそれぞれ独立に、液安定性、及び、現像残渣抑制性の観点から、二価の炭化水素基であることが好ましく、アルキレン基であることがより好ましく、直鎖アルキレン基であることが特に好ましい。
上記アルキレン基は、直鎖状であっても、分岐鎖状であっても、環構造を有していてもよい。
上記R1の炭素数は、液安定性、及び、現像残渣抑制性の観点から、1~10であることが好ましく、2~8であることがより好ましく、3~6であることが更に好ましく、4~6であることが特に好ましい。
式(1)のR2における一価の置換基としては、特に制限はなく、炭素数1~20の位以下の置換基が好ましく挙げられる。また、上記一価の置換基としては、例えば、アルキル基、アリール基、アシル基、アルキルアミノカルボニル基、アルコキシカルボニル基、アルコキシアルキル基、カルボキシアルキル基、アルコキシカルボニルアルキル基、ハロゲン原子置換アルキル基等が挙げられる。
式(1)におけるR2はそれぞれ独立に、液安定性、現像残渣抑制性、及び、密着性の観点から、水素原子、アルキル基、アシル基、又は、アルキルアミノカルボニル基であることがより好ましく、水素原子、炭素数1~8のアルキル基、炭素数1~8のアシル基、又は、炭素数2~9のアルキルアミノカルボニル基であることがより好ましく、水素原子、炭素数1~8のアルキル基、炭素数1~4のアシル基、又は、炭素数2~5のアルキルアミノカルボニル基であることが更に好ましく、水素原子であることが特に好ましい。
式(1)におけるL1は、液安定性、現像残渣抑制性、及び、密着性の観点から、硫黄原子を含む(n+1)価の連結基であることが好ましく、P1と硫黄原子で連結する(n+1)価の連結基であることがより好ましく、P1側の末端に硫黄原子を有する(n+1)価の脂肪族炭化水素基であることが更に好ましく、P1側の末端に硫黄原子を有するアルキレン基であることが特に好ましい。
また、上記L1の炭素数は、液安定性、及び、現像残渣抑制性の観点から、2~10であることが好ましく、2~6であることがより好ましく、2~4であることが更に好ましく、2又は3であることが特に好ましい。
式(1)におけるnは、液安定性、及び、現像残渣抑制性の観点から、1~4の整数であることが好ましく、1~3の整数であることがより好ましく、1又は2であることが更に好ましく、1であることが特に好ましい。
式(1)におけるmは、液安定性、及び、現像残渣抑制性の観点から、2~25の整数であることが好ましく、4~20の整数であることがより好ましく、6~15の整数であることが更に好ましく、8~12の整数であることが特に好ましい。 <Resin represented by the formula (1)>
The coloring composition according to the present disclosure contains a resin represented by the above formula (1).
Independently, R 1 in the formula (1) is preferably a divalent hydrocarbon group, more preferably an alkylene group, and a linear alkylene, from the viewpoint of liquid stability and development residue inhibitory property. It is particularly preferable that it is a group.
The alkylene group may be linear, branched or chain-like, or may have a ring structure.
The carbon number of R 1 is preferably 1 to 10, more preferably 2 to 8, and even more preferably 3 to 6 from the viewpoint of liquid stability and development residue inhibitory property. It is particularly preferably 4 to 6.
The monovalent substituent in R2 of the formula (1) is not particularly limited, and a substituent having 1 to 20 carbon atoms or less is preferably mentioned. Examples of the monovalent substituent include an alkyl group, an aryl group, an acyl group, an alkylaminocarbonyl group, an alkoxycarbonyl group, an alkoxyalkyl group, a carboxyalkyl group, an alkoxycarbonylalkyl group, and a halogen atom substituted alkyl group. Can be mentioned.
It is more preferable that R 2 in the formula (1) is a hydrogen atom, an alkyl group, an acyl group, or an alkylaminocarbonyl group independently from the viewpoint of liquid stability, development residue inhibitory property, and adhesion. , A hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an acyl group having 1 to 8 carbon atoms, or an alkylaminocarbonyl group having 2 to 9 carbon atoms, more preferably a hydrogen atom, 1 to 8 carbon atoms. It is more preferably an alkyl group, an acyl group having 1 to 4 carbon atoms, or an alkylaminocarbonyl group having 2 to 5 carbon atoms, and particularly preferably a hydrogen atom.
From the viewpoint of liquid stability, development residue inhibitory property, and adhesion, L 1 in the formula (1) is preferably a (n + 1) -valent linking group containing a sulfur atom, and is linked to P 1 by a sulfur atom. It is more preferably a (n + 1) -valent linking group, and further preferably a (n + 1) -valent aliphatic hydrocarbon group having a sulfur atom at the end on the P 1 side, and a sulfur atom at the end on the P 1 side. It is particularly preferable that it is an alkylene group having.
Further, the carbon number of L 1 is preferably 2 to 10, more preferably 2 to 6, and preferably 2 to 4 from the viewpoint of liquid stability and development residue inhibitory property. More preferably, it is particularly preferably 2 or 3.
From the viewpoint of liquid stability and development residue inhibitory property, n in the formula (1) is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and is 1 or 2. It is more preferably 1, and it is particularly preferable that it is 1.
From the viewpoint of liquid stability and development residue inhibitory property, m in the formula (1) is preferably an integer of 2 to 25, more preferably an integer of 4 to 20, and an integer of 6 to 15. Is more preferable, and an integer of 8 to 12 is particularly preferable.
上記P1を形成するエチレン性不飽和化合物としては、特に制限はなく、公知のエチレン性不飽和化合物を用いることができる、例えば、(メタ)アクリレート化合物、(メタ)アクリル酸、スチレン化合物、(メタ)アクリルアミド化合物、(メタ)アクリロニトリル化合物、ビニルエステル化合物、ビニルエーテル化合物、オレフィン化合物、(メタ)アリル化合物等が挙げられる。
中でも、液安定性、現像残渣抑制性、及び、密着性の観点から、(メタ)アクリレート化合物、(メタ)アクリル酸、及び、スチレン化合物よりなる群から選ばれた少なくとも1種の化合物が好ましく、(メタ)アクリレート化合物、及び、(メタ)アクリル酸よりなる群から選ばれた少なくとも1種の化合物がより好ましく、(メタ)アクリレート化合物が特に好ましい。
上記P1が有するエチレン性不飽和化合物由来のモノマー単位の数は、特に制限はないが、液安定性、及び、現像残渣抑制性の観点から、2~20が好ましく、2~10がより好ましく、2~6が更に好ましく、2~4が特に好ましい。
また、上記P1の形成には、1種単独のエチレン性不飽和化合物を用いてもよいし、2種以上のエチレン性不飽和化合物を用いてもよい。
上記P1におけるL1側とは反対側の末端構造は、特に制限はなく、樹脂の製造時の反応終了条件(クエンチ条件)や単離条件に応じ、公知の末端構造となる。例えば、水素原子、ヒドロキシ基、アルコキシ基、カルボキシ基、アミノ基等が挙げられる。 The polymer chain obtained by polymerizing the ethylenically unsaturated compound in P 1 of the formula (1) is not particularly limited as long as it is a polymer chain having two or more monomer units derived from the ethylenically unsaturated compound.
The ethylenically unsaturated compound forming P 1 is not particularly limited, and known ethylenically unsaturated compounds can be used, for example, (meth) acrylate compound, (meth) acrylic acid, styrene compound, ( Examples thereof include (meth) acrylamide compound, (meth) acrylonitrile compound, vinyl ester compound, vinyl ether compound, olefin compound, (meth) allyl compound and the like.
Among them, at least one compound selected from the group consisting of (meth) acrylate compound, (meth) acrylic acid, and styrene compound is preferable from the viewpoint of liquid stability, development residue inhibitory property, and adhesion. At least one compound selected from the group consisting of (meth) acrylate compound and (meth) acrylic acid is more preferable, and (meth) acrylate compound is particularly preferable.
The number of monomer units derived from the ethylenically unsaturated compound contained in P 1 is not particularly limited, but is preferably 2 to 20 and more preferably 2 to 10 from the viewpoint of liquid stability and development residue inhibitory property. 2 to 6 are more preferable, and 2 to 4 are particularly preferable.
Further, for the formation of P 1 , one kind of ethylenically unsaturated compound may be used alone, or two or more kinds of ethylenically unsaturated compounds may be used.
The terminal structure on the side opposite to the L 1 side in P 1 is not particularly limited, and has a known terminal structure depending on the reaction termination conditions (quenching conditions) and isolation conditions at the time of resin production. For example, a hydrogen atom, a hydroxy group, an alkoxy group, a carboxy group, an amino group and the like can be mentioned.
上記吸着性基としては、酸基、ヒドロキシ基、芳香族基、色素構造を有する基等が挙げられる。中でも、液安定性、現像残渣抑制性、及び、密着性の観点から、酸基が好ましく、カルボキシ基、カルボキシ基の塩、スルホン酸基、スルホン酸基の塩、リン酸基、及び、リン酸基の塩よりなる群から選ばれた少なくとも1種の基がより好ましく、カルボキシ基が特に好ましい。
また、上記吸着性基を有するモノマー単位としては、液安定性、現像残渣抑制性、及び、密着性の観点から、吸着性基を有する(メタ)アクリレート化合物由来のモノマー単位、又は、(メタ)アクリル酸由来のモノマー単位であることが好ましく、吸着性基を有する(メタ)アクリレート化合物由来のモノマー単位であることがより好ましく、カルボキシ基を有する(メタ)アクリレート化合物由来のモノマー単位であることが特に好ましい。
更に、上記吸着性基を有する(メタ)アクリレート化合物は、液安定性、現像残渣抑制性、及び、密着性の観点から、(メタ)アクロキシ基及び吸着性基以外に、エステル結合を更に有することが好ましい。 Further, the P 1 preferably has an adsorptive group, and more preferably has a monomer unit having an adsorptive group, from the viewpoints of liquid stability, development residue inhibitory property, and adhesion.
Examples of the adsorptive group include an acid group, a hydroxy group, an aromatic group, and a group having a dye structure. Among them, an acid group is preferable from the viewpoint of liquid stability, development residue inhibitory property, and adhesion, and a carboxy group, a carboxy group salt, a sulfonic acid group, a sulfonic acid group salt, a phosphoric acid group, and a phosphoric acid. At least one group selected from the group consisting of groups of salts is more preferred, and carboxy groups are particularly preferred.
The monomer unit having an adsorptive group is a monomer unit derived from a (meth) acrylate compound having an adsorptive group, or (meth) from the viewpoint of liquid stability, development residue inhibitory property, and adhesion. It is preferably a monomer unit derived from acrylic acid, more preferably a monomer unit derived from a (meth) acrylate compound having an adsorptive group, and more preferably a monomer unit derived from a (meth) acrylate compound having a carboxy group. Especially preferable.
Further, the (meth) acrylate compound having an adsorptive group further has an ester bond in addition to the (meth) achromi group and the adsorptive group from the viewpoint of liquid stability, development residue inhibitory property, and adhesion. Is preferable.
なお、エチレン性不飽和基と上記酸基とを連結する最小の原子数の具体例としては、例えば、後述するA-22のP1を形成するエチレン性不飽和化合物では、上記最小の原子数は8となる。また、上記エチレン性不飽和化合物が(メタ)アクリル酸の場合、上記最小の原子数は、0であり、上記エチレン性不飽和化合物が2-カルボキシエチル(メタ)アクリレートの場合、上記最小の原子数は、4である。 Further, the ethylenically unsaturated compound forming P 1 has an acid group from the viewpoints of liquid stability, development residue inhibitory property, and adhesion, and has an ethylenically unsaturated group and the acid group. It is preferable to contain a compound having a minimum number of atoms of 4 to 30 for linking with, and having an acid group, and the minimum number of atoms for linking the ethylenically unsaturated group and the above acid group is 6 to 20. It is more preferable to contain a compound of 6 to 12, and it is particularly preferable to contain a compound having an acid group and having a minimum number of atoms connecting the ethylenically unsaturated group and the acid group.
As a specific example of the minimum number of atoms connecting the ethylenically unsaturated group and the above acid group, for example, in the ethylenically unsaturated compound forming P1 of A -22 described later, the minimum number of atoms is described. Is 8. When the ethylenically unsaturated compound is (meth) acrylic acid, the minimum number of atoms is 0, and when the ethylenically unsaturated compound is 2-carboxyethyl (meth) acrylate, the minimum number of atoms is present. The number is four.
式(2)におけるX1は、液安定性、現像残渣抑制性、及び、密着性の観点から、吸着性基を有することが好ましく、末端に吸着性基を有することがより好ましい。上記X1における吸着性基の好ましい態様は、上記P1における吸着性基の好ましい態様と同様である。
式(2)におけるX1の炭素数は、液安定性、現像残渣抑制性、及び、密着性の観点から、1~50であることが好ましく、1~40であることがより好ましく、4~30であることが更に好ましく、6~25であることが特に好ましい。
式(2)におけるX1は、液安定性、現像残渣抑制性、及び、密着性の観点から、炭素原子、水素原子及び酸素原子よりなる一価の置換基であることが好ましい。
また、式(2)におけるX1は、液安定性、現像残渣抑制性、及び、密着性の観点から、1以上の吸着性基と1以上の二価又は三価のアルキレン基と1以上のエステル結合と必要に応じてエーテル結合とを組み合わせた基であることが好ましく、1以上の吸着性基と1以上の二価のアルキレン基と1以上のエステル結合とを組み合わせた基であることがより好ましく、1以上の吸着性基と2以上の二価のアルキレン基と2以上のエステル結合とを組み合わせた基であることが特に好ましい。
式(2)におけるLは、液安定性、及び、現像残渣抑制性の観点から、2~20が好ましく、2~10がより好ましく、2~6が更に好ましく、2~4が特に好ましい。
また、上記P1が上記式(2)で表される構造を有する場合、上記P1は、上記式(2)で表される構造を1種のみ有していても、2種以上有していてもよい。 R 3 in the formula (2) is preferably a hydrogen atom or a methyl group, and more preferably a methyl group.
From the viewpoint of liquid stability, development residue inhibitory property, and adhesion, X 1 in the formula (2) preferably has an adsorptive group, and more preferably has an adsorptive group at the terminal. The preferred embodiment of the adsorptive group in X1 is the same as the preferred embodiment of the adsorptive group in P1 .
The carbon number of X1 in the formula (2) is preferably 1 to 50, more preferably 1 to 40, and 4 to 40, from the viewpoints of liquid stability, development residue inhibitory property, and adhesion. It is more preferably 30 and particularly preferably 6 to 25.
X 1 in the formula (2) is preferably a monovalent substituent composed of a carbon atom, a hydrogen atom and an oxygen atom from the viewpoint of liquid stability, development residue inhibitory property, and adhesion.
Further, X 1 in the formula (2) has one or more adsorptive groups, one or more divalent or trivalent alkylene groups and one or more from the viewpoints of liquid stability, development residue inhibitory property, and adhesion. It is preferably a group in which an ester bond and an ether bond are combined, if necessary, and a group in which one or more adsorptive groups, one or more divalent alkylene groups and one or more ester bonds are combined. More preferably, it is a group in which one or more adsorptive groups, two or more divalent alkylene groups and two or more ester bonds are combined.
From the viewpoint of liquid stability and development residue inhibitory property, L in the formula (2) is preferably 2 to 20, more preferably 2 to 10, further preferably 2 to 6, and particularly preferably 2 to 4.
Further, when the P 1 has a structure represented by the formula (2), the P 1 has two or more types even if it has only one structure represented by the formula (2). You may be.
本開示における化合物又は樹脂の酸価は、水酸化ナトリウム水溶液を用いた中和滴定により求める。具体的には、得られた化合物又は樹脂を溶媒に溶解させた溶液に、電位差測定法を用いて水酸化ナトリウム水溶液で滴定し、樹脂の固形1gに含まれる酸のミリモル数を算出し、次に、その値を水酸化カリウム(KOH)の分子量56.1をかけることにより求める。なお、酸価の単位は、mgKOH/gである。 When the resin represented by the above formula (1) has an acid group, preferably a carboxy group, the acid value of the resin represented by the above formula (1) is liquid stability, development residue inhibitory property, and adhesion. From the above viewpoint, 30 mgKOH / g to 200 mgKOH / g is preferable, 40 mgKOH / g to 100 mgKOH / g is more preferable, 50 mgKOH / g to 90 mgKOH / g is further preferable, and 60 mgKOH / g to 80 mgKOH / g is particularly preferable.
The acid value of the compound or resin in the present disclosure is determined by neutralization titration using an aqueous sodium hydroxide solution. Specifically, the obtained compound or resin is titrated with an aqueous solution of sodium hydroxide using a potential difference measurement method in a solution dissolved in a solvent to calculate the number of millimoles of acid contained in 1 g of solid resin, and then the following is carried out. Is determined by multiplying the value by the molecular weight of potassium hydroxide (KOH) of 56.1. The unit of acid value is mgKOH / g.
式(3)におけるL2は、液安定性、現像残渣抑制性、及び、密着性の観点から、(n+1)価の脂肪族炭化水素基であることが更に好ましく、二価又は三価の脂肪族炭化水素基であることがより好ましく、直鎖アルキレン基であることが特に好ましい。
また、上記L2の炭素数は、液安定性、及び、現像残渣抑制性の観点から、2~10であることが好ましく、2~6であることがより好ましく、2~4であることが更に好ましく、2又は3であることが特に好ましい。 The preferred embodiments of R 1 , R 2 , m and n in the formula (3) are the same as the preferred embodiments of R 1 , R 2 , m and n in the formula (1).
From the viewpoint of liquid stability, development residue inhibitory property, and adhesion, L 2 in the formula (3) is more preferably a (n + 1) -valent aliphatic hydrocarbon group, and is a divalent or trivalent fat. It is more preferably a group hydrocarbon group, and particularly preferably a linear alkylene group.
Further, the carbon number of L 2 is preferably 2 to 10, more preferably 2 to 6, and preferably 2 to 4 from the viewpoint of liquid stability and development residue inhibitory property. More preferably, it is particularly preferably 2 or 3.
上記P2における酸基としては、上記吸着性基として記載した酸基が挙げられる。中でも、液安定性、現像残渣抑制性、及び、密着性の観点から、カルボキシ基が好ましい。
上記P2における上記式(2)で表される構造の好ましい態様は、上述した式(2)で表される構造の好ましい態様と同様である。
また、上記P2は、上記式(2)で表される構造を、1種単独で有していてもよいし、2種以上有していてもよい。
上記P2における硫黄原子(S)側とは反対側の末端構造は、特に制限はなく、樹脂の製造時の反応終了条件(クエンチ条件)や単離条件に応じ、公知の末端構造となる。例えば、水素原子、ヒドロキシ基、アルコキシ基、カルボキシ基、アミノ基等が挙げられる。 From the viewpoint of liquid stability, development residue inhibitory property, and adhesion, the P 2 preferably has an acid group in X 1 in the above formula (2), and the acid group is X 1 in the above formula (2). It is more preferable to have an acid group at the end of the.
Examples of the acid group in P 2 include the acid group described as the adsorptive group. Of these, a carboxy group is preferable from the viewpoints of liquid stability, development residue inhibitory property, and adhesion.
The preferred embodiment of the structure represented by the above formula ( 2 ) in P2 is the same as the preferred embodiment of the structure represented by the above formula (2).
Further, the P 2 may have one type of structure represented by the above formula (2) alone, or may have two or more types.
The terminal structure on the side opposite to the sulfur atom (S) side in P 2 is not particularly limited, and has a known terminal structure depending on the reaction termination conditions (quenching conditions) and isolation conditions at the time of resin production. For example, a hydrogen atom, a hydroxy group, an alkoxy group, a carboxy group, an amino group and the like can be mentioned.
下記具体例において、※は、ポリエステルブロックとL1との連結位置を表し、*は、L1とP1との連結位置、P1におけるモノマー単位同士の連結位置又はP1における末端構造との連結位置を表す。また、下記具体例におけるL1における※の数は、nの数を表す。更に、P1におけるL1側とは反対側の末端構造は、特に示しておらず、上述した構造であればよい。
また、具体例としては、下記メタクリレート化合物由来のモノマー単位を対応するアクリレート化合物由来のモノマー単位に変更したものも好ましく挙げられる。 Specific examples of the resin represented by the above formula (1) include, but needless to say, the following resins.
In the following specific example, * represents the connection position between the polyester block and L 1 , and * indicates the connection position between L 1 and P 1 , the connection position between the monomer units in P 1 , or the terminal structure in P 1 . Represents the connection position. Further, the number of * in L1 in the following specific example represents the number of n. Further, the terminal structure on the side opposite to the L 1 side in P 1 is not particularly shown, and the above-mentioned structure may be used.
Further, as a specific example, a monomer unit derived from the following methacrylate compound is preferably changed to a monomer unit derived from the corresponding acrylate compound.
上記式(1)で表される樹脂の含有量は、液安定性、現像残渣抑制性、及び、密着性の観点から、着色組成物の全固形分中に対し、5質量%~40質量%であることが好ましく、5質量%~30質量%であることがより好ましい。 The coloring composition according to the present disclosure may contain one kind of resin represented by the above formula (1) alone, or may contain two or more kinds.
The content of the resin represented by the above formula (1) is 5% by mass to 40% by mass with respect to the total solid content of the coloring composition from the viewpoint of liquid stability, development residue inhibitory property, and adhesion. Is preferable, and 5% by mass to 30% by mass is more preferable.
工程(i-1):ヒドロキシ基を有するメルカプト化合物の存在下、エチレン性不飽和化合物を重合し、末端にヒドロキシ基を有する樹脂を作製する工程
工程(i-2):上記末端にヒドロキシ基を有する樹脂のヒドロキシ基に、ポリエステル樹脂鎖を形成する工程
工程(ii-1):ヒドロキシ基を有するメルカプト化合物のヒドロキシ基に、ポリエステル樹脂鎖を形成し、メルカプト基を有するポリエステル樹脂を作製する工程
工程(ii-2):上記メルカプト基を有するポリエステル樹脂の存在下、エチレン性不飽和化合物を重合する工程 The method for producing the resin represented by the formula (1) is not particularly limited, but when the resin represented by the above formula (3) is produced, the following steps (i-1) and (i-2) are particularly limited. , Or a production method including the following steps (ii-1) and (ii-2) is preferably mentioned, and a production method including the following steps (i-1) and (i-2) is more preferable. Can be mentioned.
Step (i-1): A step of polymerizing an ethylenically unsaturated compound in the presence of a mercapto compound having a hydroxy group to prepare a resin having a hydroxy group at the terminal Step (i-2): A hydroxy group at the terminal. Step of forming a polyester resin chain on the hydroxy group of the resin (ii-1): Step of forming a polyester resin chain on the hydroxy group of the mercapto compound having a hydroxy group to produce a polyester resin having a mercapto group. (Ii-2): Step of polymerizing an ethylenically unsaturated compound in the presence of the polyester resin having a mercapto group.
上記工程(i-1)においては、ヒドロキシ基を有するメルカプト化合物が連鎖移動剤として作用し、メルカプト基より生じる硫黄ラジカルよりエチレン性不飽和化合物が重合し、末端にヒドロキシ基を有する樹脂が得られる。
上記工程(ii-2)においては、メルカプト基を有するポリエステル樹脂が連鎖移動剤として作用し、メルカプト基より生じる硫黄ラジカルよりエチレン性不飽和化合物が重合し、式(1)で表される樹脂が得られる。
上記エチレン性不飽和化合物は、特に制限はないが、上述したエチレン性不飽和化合物を好適に用いることができる。また、その使用量は、所望の式(1)で表される樹脂に応じ適宜選択することができる。
上記ポリエステル樹脂鎖の形成に用いる単量体としては、ヒドロキシカルボン酸化合物、及び、ラクトン化合物を好適に用いることができる。また、その使用量は、所望の式(1)で表される樹脂に応じ適宜選択することができる。
また、上記各工程においては、必要に応じ、公知の溶剤、重合触媒、重縮合触媒等を用いることができ、また、公知の反応装置により行うことができる。更に、上記各工程における反応温度、反応時間も適宜設定することができる。
また、必要に応じ、各工程後に、公知の精製処理を行ってもよい。 As the mercapto compound having a hydroxy group, hydroxyalkylthiol or dihydroxyalkylthiol is preferably mentioned, and hydroxyalkylthiol is more preferably mentioned.
In the above step (i-1), the mercapto compound having a hydroxy group acts as a chain transfer agent, and the ethylenically unsaturated compound is polymerized from the sulfur radical generated from the mercapto group to obtain a resin having a hydroxy group at the terminal. ..
In the above step (ii-2), the polyester resin having a mercapto group acts as a chain transfer agent, and the ethylenically unsaturated compound is polymerized from the sulfur radical generated from the mercapto group to obtain the resin represented by the formula (1). can get.
The ethylenically unsaturated compound is not particularly limited, but the above-mentioned ethylenically unsaturated compound can be preferably used. Further, the amount to be used can be appropriately selected according to the desired resin represented by the formula (1).
As the monomer used for forming the polyester resin chain, a hydroxycarboxylic acid compound and a lactone compound can be preferably used. Further, the amount to be used can be appropriately selected according to the desired resin represented by the formula (1).
Further, in each of the above steps, a known solvent, polymerization catalyst, polycondensation catalyst and the like can be used, if necessary, and a known reaction apparatus can be used. Further, the reaction temperature and the reaction time in each of the above steps can be appropriately set.
Further, if necessary, a known purification treatment may be performed after each step.
本開示に係る着色組成物は、顔料を含む。
顔料は、無機顔料、有機顔料のいずれでもよいが有機顔料であることが好ましい。また、顔料には、無機顔料又は有機-無機顔料の一部を有機発色団で置換した材料を用いることもできる。無機顔料や有機-無機顔料を有機発色団で置換することで、色相設計をしやすくできる。
本開示に係る着色組成物は、カラーフィルタにおける着色画素形成用の着色組成物として好ましく用いることができる。着色画素としては、例えば、赤色画素、緑色画素、青色画素、マゼンタ色画素、シアン色画素、イエロー色画素などが挙げられる。中でも、緑色画素が好ましく挙げられる。 <Pigment>
The coloring composition according to the present disclosure contains a pigment.
The pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment. Further, as the pigment, an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can also be used. By replacing the inorganic pigment or the organic-inorganic pigment with an organic chromophore, the hue design can be facilitated.
The coloring composition according to the present disclosure can be preferably used as a coloring composition for forming colored pixels in a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, a yellow color pixel and the like. Among them, green pixels are preferably mentioned.
有機顔料の具体例としては以下に示すものが挙げられる。 Organic pigments include phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, diketopyrrolopyrrole pigments, pyrolopyrrolop pigments, isoindrin pigments, quinophthalone pigments, triarylmethane pigments, xanthene pigments and methine pigments. , Kinolin pigments and the like.
Specific examples of the organic pigment include those shown below.
C.I.Pigment Orange 2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73等(以上、オレンジ色顔料)、
C.I.Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:2,81:3,83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,270,272,279,294(キサンテン系、Organo Ultramarine、Bluish Red),295(モノアゾ系),296(ジアゾ系),297(アミノケトン系)等(以上、赤色顔料)、
C.I.Pigment Green 7,10,36,37,58,59,62,63,64(フタロシアニン系),65(フタロシアニン系),66(フタロシアニン系)等(以上、緑色顔料)、
C.I.Pigment Violet 1,19,23,27,32,37,42,60(トリアリールメタン系),61(キサンテン系)等(以上、紫色顔料)、
C.I.Pigment Blue 1,2,15,15:1,15:2,15:3,15:4,15:6,16,22,29,60,64,66,79,80,87(モノアゾ系),88(メチン系)等(以上、青色顔料)。 Color Index (CI) Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34, 35,35: 1,36,36: 1,37,37: 1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86, 93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,125,126,127,128, 129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174 175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215,228,231,232 (methine type), 233 (quinoline type), 234 ( Amino ketone type), 235 (amino ketone type), 236 (amino ketone type), etc. (above, yellow pigment),
C. I. Pigment Orange 2,5,13,16,17: 1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73, etc. (The above is orange pigment),
C. I. Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48: 1,48: 2,48: 3,48: 4, 49,49: 1,49: 2,52: 1,52: 2,53: 1,57: 1,60: 1,63: 1,66,67,81: 1,81: 2,81: 3, 83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184 185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,270,272,279,294 (xanthene system) , Organo Ultramarine, Bluesh Red), 295 (monoazo type), 296 (diazo type), 297 (aminoketone type), etc. (above, red pigment),
C. I. Pigment Green 7,10,36,37,58,59,62,63,64 (phthalocyanine type), 65 (phthalocyanine type), 66 (phthalocyanine type), etc. (above, green pigment),
C. I. Pigment Violet 1,19,23,27,32,37,42,60 (triarylmethane type), 61 (xanthene type), etc. (above, purple pigment),
C. I. Pigment Blue 1,2,15,15: 1,15: 2,15: 3,15: 4,15: 6,16,22,29,60,64,66,79,80,87 (monoazo system), 88 (methine-based) and the like (above, blue pigment).
更に、上記顔料は、感度、及び、分光特性の観点から、フタロシアニン顔料を含むことが好ましく、緑色のフタロシアニン顔料を含むことがより好ましい。 Further, the coloring composition according to the present disclosure preferably contains a green pigment as a pigment, and more preferably contains a green pigment and a yellow pigment, from the viewpoint of further exerting the effect in the present disclosure.
Further, the pigment preferably contains a phthalocyanine pigment, and more preferably contains a green phthalocyanine pigment, from the viewpoint of sensitivity and spectral characteristics.
また、緑色顔料としては、1分子中のハロゲン原子数が平均10個~14個であり、臭素原子数が平均8個~12個であり、塩素原子数が平均2個~5個であるハロゲン化亜鉛フタロシアニン化合物を用いることもできる。具体例としては、国際公開第2015/118720号に記載の化合物、中国特許出願公開第106909027号明細書に記載の化合物、リン酸エステルを配位子として有するフタロシアニン化合物などを用いることもできる。
また、緑色顔料としては、特開2019-8014号公報、又は、特開2018-180023号公報に記載の緑色顔料を使用してもよい。
中でも、緑色顔料は、緑色の画素に適した分光特性を有する膜を形成しやすいという理由から、C.I.Pigment Green 58及びC.I.Pigment Green 36よりなる群から選ばれた少なくとも1種の化合物を含むことが好ましく、C.I.Pigment Green 58を含むことがより好ましい。 As the green pigment, known ones can be used. For example, phthalocyanine compounds such as Color Index (CI) Pigment Green 7, 10, 36, 37, 58, 59, 62, 63 can be mentioned.
Further, as a green pigment, a halogen having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. A zinc phthalocyanine compound can also be used. As specific examples, the compound described in International Publication No. 2015/118720, the compound described in Chinese Patent Application Publication No. 1069090227, the phthalocyanine compound having a phosphate ester as a ligand, and the like can also be used.
Further, as the green pigment, the green pigment described in JP-A-2019-8014 or JP-A-2018-180023 may be used.
Among them, the green pigment easily forms a film having spectral characteristics suitable for green pixels, and therefore, C.I. I. Pigment Green 58 and C.I. I. It preferably contains at least one compound selected from the group consisting of Pigment Green 36, C.I. I. It is more preferable to include Pigment Green 58.
着色組成物の全固形分中における緑色顔料の含有量は、10質量%~80質量%であることが好ましい。下限は、15質量%以上であることがより好ましく、20質量%以上であることが特に好ましい。上限は、70質量%以下であることがより好ましく、60質量%以下であることが特に好ましい。 The green pigment may be used alone or in combination of two or more.
The content of the green pigment in the total solid content of the coloring composition is preferably 10% by mass to 80% by mass. The lower limit is more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is more preferably 70% by mass or less, and particularly preferably 60% by mass or less.
RY5~RY7が表すアルキル基の炭素数は、1~10が好ましく、1~6がより好ましく、1~4が更に好ましい。上記アルキル基は、直鎖、分岐及び環状のいずれであってもよく、直鎖又は分岐が好ましく、直鎖がより好ましい。上記アルキル基は、置換基を有していてもよい。置換基は、ハロゲン原子、ヒドロキシ基、アルコキシ基、シアノ基及びアミノ基が好ましく挙げられる。 In formula (Y), RY1 and RY2 independently represent -OH or -NR Y5 RY6 , and RY3 and RY4 independently represent = O or = NR Y7 , respectively, RY5 to R. Y7 independently represents a hydrogen atom or an alkyl group.
The number of carbon atoms of the alkyl group represented by RY5 to RY7 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear. The alkyl group may have a substituent. Preferred examples of the substituent include a halogen atom, a hydroxy group, an alkoxy group, a cyano group and an amino group.
また、黄色顔料として、特開2018-62644号公報に記載の化合物を用いることもできる。なお、この化合物は、顔料誘導体として用いることもできる。
更に、特開2018-155881号公報に記載されているように、C.I.Pigment Yellow 129を、耐候性改良の目的で添加してもよい。 Further, as the yellow pigment, the quinophthalone compound described in paragraphs 0011 to 0034 of JP2013-54339, the quinophthalone compound described in paragraphs 0013 to 0058 of JP2014-26228, and JP-A-2019-8014. The yellow pigment described, the quinophthalone compound described in Japanese Patent No. 6607427, the compound described in Korean Publication No. 10-2014-0034963, the compound described in JP-A-2017-095706, Taiwan Patent Application Publication No. 201920495. The compound described in Japanese Patent Publication No. 6607427, the compound described in Japanese Patent No. 6607427, and the like can also be used.
Further, as the yellow pigment, the compound described in JP-A-2018-62644 can also be used. In addition, this compound can also be used as a pigment derivative.
Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
顔料の含有量は、着色組成物中の全固形分に対し、40質量%以上であり、現像残渣抑制性、分散液安定性、及び、密着性の観点から、45質量%以上であることが好ましく、50質量%以上であることがより好ましく、60質量%以上であることが特に好ましい。また、上限は80質量%以下であることが好ましい。 The coloring composition according to the present disclosure may contain one kind of pigment alone or two or more kinds of pigments.
The content of the pigment is 40% by mass or more with respect to the total solid content in the coloring composition, and is 45% by mass or more from the viewpoint of developing residue inhibitory property, dispersion liquid stability, and adhesion. It is more preferably 50% by mass or more, and particularly preferably 60% by mass or more. Further, the upper limit is preferably 80% by mass or less.
本開示に係る着色組成物は、樹脂を含む。樹脂は、例えば、顔料などの粒子を着色組成物中で分散させる用途及びバインダーの用途で配合される。なお、主に顔料などの粒子を分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外の目的で使用することもできる。また、上記式(1)で表される樹脂は、上述したように分散剤として作用すると推定している。 <Resin>
The coloring composition according to the present disclosure contains a resin. The resin is blended, for example, for the purpose of dispersing particles such as pigments in a coloring composition and for the purpose of a binder. A resin mainly used for dispersing particles such as pigments is also referred to as a dispersant. However, such use of the resin is an example, and it can be used for purposes other than such use. Further, it is presumed that the resin represented by the above formula (1) acts as a dispersant as described above.
更に、樹脂への酸性官能基の導入方法としては、分散剤(特にエチレン性不飽和基を有する分散剤など)又はアルカリ可溶性樹脂において、エポキシ基の開環反応で生じたヒドロキシ基に酸無水物を反応させて酸基を導入する方法も挙げられる。 The method for introducing an acidic functional group into a resin is not particularly limited, and examples thereof include the method described in Japanese Patent No. 6349629.
Further, as a method for introducing an acidic functional group into the resin, in a dispersant (particularly a dispersant having an ethylenically unsaturated group) or an alkali-soluble resin, an acid anhydride is added to the hydroxy group generated by the ring opening reaction of the epoxy group. There is also a method of introducing an acid group by reacting with each other.
樹脂Bにおいて、芳香族カルボキシ基は繰り返し単位の主鎖に含まれていてもよく、繰り返し単位の側鎖に含まれていてもよい。現像性及び色抜けに優れるという理由から、芳香族カルボキシ基は繰り返し単位の主鎖に含まれていることが好ましい。詳細は不明だが、主鎖近くに芳香族カルボキシ基が存在することで、これらの特性がより向上するものと推測される。なお、本明細書において、芳香族カルボキシル基とは、芳香族環にカルボキシル基が1個以上結合した構造の基のことである。芳香族カルボキシ基において、芳香族環に結合したカルボキシ基の数は、1個~4個であることが好ましく、1個~2個であることがより好ましい。 Further, as the dispersant, a resin having an aromatic carboxy group (hereinafter, “resin B”) is preferably mentioned.
In the resin B, the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit. The aromatic carboxy group is preferably contained in the main chain of the repeating unit because of its excellent developability and color loss. Details are unknown, but it is speculated that the presence of aromatic carboxy groups near the main chain will further improve these properties. In addition, in this specification, an aromatic carboxyl group is a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring. Among the aromatic carboxy groups, the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
式(b-10)中、Ar10は芳香族カルボキシル基を含む基を表し、L11は、-COO-又は-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。 In formula (b-1), Ar 1 represents a group containing an aromatic carboxyl group, L 1 represents -COO- or -CONH-, and L 2 represents a divalent linking group.
In formula (b-10), Ar 10 represents a group containing an aromatic carboxyl group, L 11 represents -COO- or -CONH-, L 12 represents a trivalent linking group, and P 10 represents a polymer. Represents a chain.
式(Ar-2)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1又は2であることがより好ましく、2であることが更に好ましい。
式(Ar-3)中、n3及びn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1又は2であることがより好ましく、1であることが更に好ましい。ただし、n3及びn4の少なくとも一方は1以上の整数である。
式(Ac-3)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基又は上記式(Q-2)で表される基を表す。 In the formula (Ar-1), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
In the formula (Ar-2), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
In the formula (Ar-3), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
In the formula (Ac-3), Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , the above formula (Q-). It represents a group represented by 1) or a group represented by the above formula (Q-2).
表すことが好ましい。 In the formula (b-10), L 11 represents -COO- or -CONH-, and preferably -COO-.
上記式において、RP3は、水素原子又はメチル基を表す。
上記式において、LP1は、単結合又はアリーレン基を表し、LP2は、単結合又は二価の連結基を表す。LP1は、単結合であることが好ましい。LP2が表す2価の連結基としては、アルキレン基(好ましくは炭素数1~12のアルキレン基)、アリーレン基(好ましくは炭素数6~20のアリーレン基)、-NH-、-SO-、-SO2-、-CO-、-O-、-COO-、-OCO-、-S-、-NHCO-、-CONH-、及びこれらの2以上を組み合わせてなる基が挙げられる。
RP4は、水素原子又は置換基を表す。置換基としては、ヒドロキシ基、カルボキシ基、アルキル基、アリール基、ヘテロアリール基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルキルチオエーテル基、アリールチオエーテル基、ヘテロアリールチオエーテル基、(メタ)アクリロイル基、オキセタニル基、ブロックイソシアネート基等が挙げられる。なお、本開示におけるブロックイソシアネート基とは、熱によりイソシアネート基を生成することが可能な基であり、例えば、ブロック剤とイソシアネート基とを反応させイソシアネート基を保護した基が好ましく例示できる。ブロック剤としては、オキシム化合物、ラクタム化合物、フェノール化合物、アルコール化合物、アミン化合物、活性メチレン化合物、ピラゾール化合物、メルカプタン化合物、イミダゾール系化合物、イミド系化合物等を挙げることができる。ブロック剤については、特開2017-067930号公報の段落0115~0117に記載された化合物が挙げられ、この内容は本明細書に組み込まれる。また、ブロックイソシアネート基は、90℃~260℃の熱によりイソシアネート基を生成することが可能な基であることが好ましい。 In the above formula, RP1 and RP2 each represent an alkylene group. As the alkylene group represented by RP1 and RP2 , a linear or branched alkylene group having 1 to 20 carbon atoms is preferable, and a linear or branched alkylene group having 2 to 16 carbon atoms is more preferable. , A linear or branched alkylene group having 3 to 12 carbon atoms is more preferable.
In the above formula, RP3 represents a hydrogen atom or a methyl group.
In the above formula, LP1 represents a single bond or an arylene group, and LP2 represents a single bond or a divalent linking group. L P1 is preferably a single bond. The divalent linking group represented by LP2 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-. Examples thereof include -SO 2- , -CO-, -O-, -COO-, -OCO-, -S-, -NHCO-, -CONH-, and a group consisting of a combination of two or more of these.
RP4 represents a hydrogen atom or a substituent. Substituents include hydroxy group, carboxy group, alkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkylthioether group, arylthioether group, heteroarylthioether group and (meth) acryloyl. Examples thereof include a group, an oxetanyl group, a blocked isocyanate group and the like. The blocked isocyanate group in the present disclosure is a group capable of generating an isocyanate group by heat, and for example, a group in which a blocking agent and an isocyanate group are reacted to protect the isocyanate group can be preferably exemplified. Examples of the blocking agent include oxime compounds, lactam compounds, phenol compounds, alcohol compounds, amine compounds, active methylene compounds, pyrazole compounds, mercaptan compounds, imidazole compounds, imide compounds and the like. Examples of the blocking agent include the compounds described in paragraphs 0115 to 0117 of JP-A-2017-06793, the contents of which are incorporated in the present specification. Further, the blocked isocyanate group is preferably a group capable of generating an isocyanate group by heat of 90 ° C to 260 ° C.
エチレン性不飽和基を有する重合性モノマーをヒドロキシ基含有チオール化合物(好ましくは分子内に2つのヒドロキシ基と1つのチオール基を有する化合物)の存在下にて、ラジカル重合して片末端領域に2つのヒドロキシ基を有するビニル重合体を合成し、この合成したビニル重合体と、芳香族テトラカルボン酸無水物及び芳香族トリカルボン酸無水物よりなる群から選ばれる一種以上の芳香族酸無水物とを反応させて製造する方法。 [Synthesis method (1)]
A polymerizable monomer having an ethylenically unsaturated group is radically polymerized in the presence of a hydroxy group-containing thiol compound (preferably a compound having two hydroxy groups and one thiol group in the molecule) to form 2 in one terminal region. A vinyl polymer having two hydroxy groups was synthesized, and the synthesized vinyl polymer was combined with one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides. A method of reacting and producing.
ヒドロキシ基含有化合物(好ましくは分子内に2つのヒドロキシ基と1つのチオール基を有する化合物)と、芳香族テトラカルボン酸無水物及び芳香族トリカルボン酸無水物よりなる群から選ばれる一種以上の芳香族酸無水物と、を反応させたのち、得られた反応物の存在下で、エチレン性不飽和基を有する重合性モノマーをラジカル重合して製造する方法。合成方法(2)においては、ヒドロキシ基を有する重合性モノマーをラジカル重合した後、更にイソシアネート基を有する化合物(例えば、イソシアネート基と上述した官能基Aとを有する化合物)とを反応させてもよい。これによって、ポリマー鎖P10に官能基Aを導入することができる。 [Synthesis method (2)]
One or more aromatics selected from the group consisting of hydroxy group-containing compounds (preferably compounds having two hydroxy groups and one thiol group in the molecule) and aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides. A method for producing a polymerizable monomer having an ethylenically unsaturated group by radical polymerization in the presence of the obtained reactant after reacting with an acid anhydride. In the synthesis method (2), a polymerizable monomer having a hydroxy group may be radically polymerized, and then a compound having an isocyanate group (for example, a compound having an isocyanate group and the above-mentioned functional group A) may be reacted. .. This allows the functional group A to be introduced into the polymer chain P10 .
樹脂の含有量は、現像残渣抑制性、分散液安定性、及び、密着性の観点から、着色組成物の全固形分中に対し、5質量%~40質量%であることが好ましく、10質量%~30質量%であることがより好ましく、10質量%~25質量%であることが特に好ましい。
また、分散剤として用いられる上記樹脂の含有量は、上記式(1)で表される樹脂の含有量よりも少ないことが好ましい。 In the coloring composition according to the present disclosure, only one kind of resin may be used, or two or more kinds of resins may be used in combination. When two or more types are used in combination, the total amount thereof is preferably in the following range.
The content of the resin is preferably 5% by mass to 40% by mass, preferably 10% by mass, based on the total solid content of the coloring composition from the viewpoint of suppressing development residue, stability of dispersion liquid, and adhesiveness. It is more preferably% to 30% by mass, and particularly preferably 10% by mass to 25% by mass.
Further, the content of the resin used as the dispersant is preferably smaller than the content of the resin represented by the above formula (1).
本開示に係る着色組成物は、顔料誘導体(以下、単に「誘導体」ともいう。)を含有することができる。
顔料誘導体としては、発色団の一部分を、酸基又は塩基性基で置換した構造を有する化合物が挙げられる。顔料誘導体を構成する発色団としては、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、フタロシアニン骨格、アンスラキノン骨格、キナクリドン骨格、ジオキサジン骨格、ペリノン骨格、ペリレン骨格、チオインジゴ骨格、イソインドリン骨格、イソインドリノン骨格、キノフタロン骨格、スレン骨格、金属錯体系骨格等が挙げられ、キノリン骨格、ベンゾイミダゾロン骨格、ジケトピロロピロール骨格、アゾ骨格、キノフタロン骨格、イソインドリン骨格及びフタロシアニン骨格が好ましく、アゾ骨格及びベンゾイミダゾロン骨格がより好ましい。酸基としては、スルホ基、カルボキシ基、リン酸基及びこれらの塩が挙げられる。塩を構成する原子又は原子団としては、アルカリ金属イオン(Li+、Na+、K+など)、アルカリ土類金属イオン(Ca2+、Mg2+など)、アンモニウムイオン、イミダゾリウムイオン、ピリジニウムイオン、ホスホニウムイオンなどが挙げられる。塩基性基としては、アミノ基、ピリジニル基及びその塩、アンモニウム基の塩、並びにフタルイミドメチル基が挙げられる。塩を構成する原子又は原子団としては、水酸化物イオン、ハロゲンイオン、カルボン酸イオン、スルホン酸イオン、フェノキシドイオンなどが挙げられる。 <Pigment derivative>
The coloring composition according to the present disclosure may contain a pigment derivative (hereinafter, also simply referred to as "derivative").
Examples of the pigment derivative include compounds having a structure in which a part of the chromophore is replaced with an acid group or a basic group. The chromogens constituting the pigment derivative include quinoline skeleton, benzoimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthracinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone skeleton, perylene skeleton, thioindigo skeleton, and iso. Indoline skeleton, isoindolinone skeleton, quinophthalone skeleton, slene skeleton, metal complex skeleton, etc. Preferably, the azo skeleton and the benzoimidazolone skeleton are more preferable. Examples of the acid group include a sulfo group, a carboxy group, a phosphoric acid group and salts thereof. The atoms or groups of atoms that make up the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions, imidazolium ions, and pyridiniums. Ions, phosphonium ions and the like can be mentioned. Examples of the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimidemethyl group. Examples of the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
顔料誘導体の含有量は、顔料100質量部に対して、1質量部~30質量部が好ましく、3質量部~20質量部がより好ましい。顔料誘導体は、1種のみを用いてもよいし、2種以上を併用してもよい。 The coloring composition according to the present disclosure may contain one pigment derivative alone or two or more pigment derivatives.
The content of the pigment derivative is preferably 1 part by mass to 30 parts by mass, and more preferably 3 parts by mass to 20 parts by mass with respect to 100 parts by mass of the pigment. As the pigment derivative, only one kind may be used, or two or more kinds may be used in combination.
本開示に係る着色組成物は、光重合開始剤を含むことが好ましい。特に、本開示に係る着色組成物が重合性化合物を含む場合は、本開示に係る着色組成物は更に光重合開始剤を含むことが好ましい。また、本開示に係る着色組成物は、感光性着色組成物であることが好ましく、ネガ型感光性着色組成物であることがより好ましい。
光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視光領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。 <Photopolymerization initiator>
The coloring composition according to the present disclosure preferably contains a photopolymerization initiator. In particular, when the coloring composition according to the present disclosure contains a polymerizable compound, it is preferable that the coloring composition according to the present disclosure further contains a photopolymerization initiator. Further, the coloring composition according to the present disclosure is preferably a photosensitive coloring composition, and more preferably a negative type photosensitive coloring composition.
The photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible light region is preferable. The photopolymerization initiator is preferably a photoradical polymerization initiator.
本開示に係る着色組成物は、重合性化合物を含むことが好ましい。重合性化合物としては、ラジカル、酸又は熱により架橋可能な公知の化合物を用いることができる。本開示において、重合性化合物は、例えば、エチレン性不飽和結合基を有する化合物であることが好ましい。エチレン性不飽和結合基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本開示で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。 <Polymerizable compound>
The coloring composition according to the present disclosure preferably contains a polymerizable compound. As the polymerizable compound, a known compound that can be crosslinked by radicals, acids or heat can be used. In the present disclosure, the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond group. Examples of the ethylenically unsaturated bonding group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group. The polymerizable compound used in the present disclosure is preferably a radically polymerizable compound.
本開示に係る着色組成物は、環状エーテル基を有する化合物を含有することができる。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられる。環状エーテル基を有する化合物は、エポキシ基を有する化合物であることが好ましい。エポキシ基を有する化合物としては、1分子内にエポキシ基を1つ以上有する化合物が挙げられ、エポキシ基を2つ以上有する化合物が好ましい。エポキシ基は、1分子内に1~100個有することが好ましい。エポキシ基の上限は、例えば、10個以下とすることもでき、5個以下とすることもできる。エポキシ基の下限は、2個以上が好ましい。エポキシ基を有する化合物としては、特開2013-011869号公報の段落0034~0036、特開2014-043556号公報の段落0147~0156、特開2014-089408号公報の段落0085~0092に記載された化合物、特開2017-179172号公報に記載された化合物を用いることもできる。これらの内容は、本明細書に組み込まれる。 <Compound having a cyclic ether group>
The coloring composition according to the present disclosure can contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The compound having a cyclic ether group is preferably a compound having an epoxy group. Examples of the compound having an epoxy group include a compound having one or more epoxy groups in one molecule, and a compound having two or more epoxy groups is preferable. It is preferable to have 1 to 100 epoxy groups in one molecule. The upper limit of the epoxy group may be, for example, 10 or less, or 5 or less. The lower limit of the epoxy group is preferably two or more. Examples of the compound having an epoxy group are described in paragraphs 0034 to 0036 of JP2013-011869A, paragraphs 0147 to 0156 of JP-A-2014-0435556, and paragraphs 0083 to 0092 of JP-A-2014-089408. Compounds, compounds described in JP-A-2017-179172 can also be used. These contents are incorporated in the present specification.
本開示に係る着色組成物は、シランカップリング剤を含有することができる。この態様によれば、得られる膜の支持体との密着性をより向上させることができる。本開示において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基及びエポキシ基が好ましい。シランカップリング剤の具体例としては、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-603)、N-β-ミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-903)、3-メタクリロキシプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-502)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-503)等がある。また、シランカップリング剤の具体例については、特開2009-288703号公報の段落0018~0036に記載の化合物、特開2009-242604号公報の段落0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。 <Silane coupling agent>
The coloring composition according to the present disclosure may contain a silane coupling agent. According to this aspect, the adhesion of the obtained membrane to the support can be further improved. In the present disclosure, the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups. Further, the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group. , A phenyl group and the like, preferably an amino group, a (meth) acryloyl group and an epoxy group. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N-β-aminoethyl-γ-amino. Propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N-β-minoethyl-γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), γ -Aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxypropyl Methyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-503) and the like. Specific examples of the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. The contents of are incorporated herein by reference.
本開示に係る着色組成物は、溶剤を含有する。
溶剤としては、有機溶剤が好ましく挙げられる。
有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、シクロヘキサノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミドなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。 <Solvent>
The coloring composition according to the present disclosure contains a solvent.
As the solvent, an organic solvent is preferably mentioned.
Examples of the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, hydrocarbon-based solvents and the like. For these details, paragraph 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein. Further, an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethylcarbitol acetate, butylcarbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-dimethylpropaneamide and the like. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 parts by mass (parts) with respect to the total amount of organic solvent. Per millision) or less, 10 mass ppm or less, or 1 mass ppm or less).
本開示に係る着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。着色組成物の全固形分中における重合禁止剤の含有量は、0.0001質量%~5質量%が好ましい。 <Polymerization inhibitor>
The coloring composition according to the present disclosure may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, first cerium salt, etc.). Of these, p-methoxyphenol is preferable. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001% by mass to 5% by mass.
本開示に係る着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤については、国際公開第2015/166779号の段落0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。 <Surfactant>
The coloring composition according to the present disclosure may contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used. As for the surfactant, the surfactant described in paragraphs 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
本開示に係る着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤は、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などを用いることができる。これらの詳細については、特開2012-208374号公報の段落0052~0072、特開2013-068814号公報の段落0317~0334、特開2016-162946号公報の段落0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の市販品としては、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂(株)製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落0049~0059に記載された化合物を用いることもできる。 <UV absorber>
The coloring composition according to the present disclosure may contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound and the like can be used. For details of these, the compounds described in paragraphs 0052 to 0072 of JP2012-208374A, paragraphs 0317 to 0334 of JP2013-066814, and paragraphs 0061 to 0080 of JP2016-162946 can be used. These contents are incorporated herein by reference. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.). Examples of the benzotriazole compound include the MYUA series (The Chemical Daily, February 1, 2016) manufactured by Miyoshi Oil & Fat Co., Ltd. Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
本開示に係る着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。リン系酸化防止剤としてはトリス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]エチル]アミン、トリス[2-[(4,6,9,11-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサホスフェピン-2-イル)オキシ]エチル]アミン、亜リン酸エチルビス(2,4-ジ-tert-ブチル-6-メチルフェニル)などが挙げられる。酸化防止剤の市販品としては、例えば、アデカスタブ AO-20、アデカスタブ AO-30、アデカスタブ AO-40、アデカスタブ AO-50、アデカスタブ AO-50F、アデカスタブ AO-60、アデカスタブ AO-60G、アデカスタブ AO-80、アデカスタブ AO-330(以上、(株)ADEKA製)などが挙げられる。また、酸化防止剤は、特許第6268967号公報の段落0023~0048に記載された化合物、韓国公開特許第10-2019-0059371号公報に記載の化合物等を使用することもできる。 <Antioxidant>
The coloring composition according to the present disclosure may contain an antioxidant. Examples of the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like. As the phenol compound, any phenol compound known as a phenolic antioxidant can be used. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable. As the above-mentioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable. Further, as the antioxidant, a compound having a phenol group and a phosphite ester group in the same molecule is also preferable. Further, as the antioxidant, a phosphorus-based antioxidant can also be preferably used. As a phosphorus-based antioxidant, Tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosphepine-6] -Il] Oxy] Ethyl] amine, Tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like. Commercially available products of antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, and Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like. Further, as the antioxidant, the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in Japanese Patent No. 10-2019-0059371, and the like can also be used.
本開示に係る着色組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落0237)の記載、特開2008-250074号公報の段落0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本開示に係る着色組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100℃~250℃で加熱するか、又は酸/塩基触媒存在下で80℃~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。また、特開2018-155881号公報に記載されているように、C.I.Pigment Yellow129を耐候性改良の目的で添加してもよい。 <Other ingredients>
The coloring composition according to the present disclosure is, if necessary, a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, a filler, a defoaming agent). , Flame retardant, leveling agent, peeling accelerator, fragrance, surface tension modifier, chain transfer agent, etc.) may be contained. By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraphs 0183 and later of JP2012-003225A (paragraph 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs 0101 to JP-A-2008-250074. The descriptions of 0104, 0107 to 0109, etc. can be taken into consideration, and these contents are incorporated in the present specification. In addition, the coloring composition according to the present disclosure may contain a latent antioxidant, if necessary. The latent antioxidant is a compound whose site that functions as an antioxidant is protected by a protecting group and is heated at 100 ° C to 250 ° C or at 80 ° C to 200 ° C in the presence of an acid / base catalyst. Examples thereof include compounds in which the protecting group is desorbed by heating and the compound functions as an antioxidant. Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219. Examples of commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation). Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
本開示に係る着色組成物は、色素多量体を用いることもできる。色素多量体は、溶剤に溶解して用いられる染料であることが好ましい。また、色素多量体は、粒子を形成していてもよい。色素多量体が粒子である場合は通常溶剤に分散した状態で用いられる。粒子状態の色素多量体は、例えば乳化重合によって得ることができ、特開2015-214682号公報に記載されている化合物及び製造方法が具体例として挙げられる。色素多量体は、一分子中に色素構造を2以上有するものであり、色素構造を3以上有することが好ましい。上限は、特に限定はないが、100以下とすることもできる。一分子中に有する複数の色素構造は、同一の色素構造であってもよく、異なる色素構造であってもよい。色素多量体の重量平均分子量(Mw)は、2,000~50,000が好ましい。下限は、3,000以上がより好ましく、6,000以上が更に好ましい。上限は、30,000以下がより好ましく、20,000以下が更に好ましい。色素多量体は、特開2011-213925号公報、特開2013-041097号公報、特開2015-028144号公報、特開2015-030742号公報、国際公開第2016/031442号等に記載されている化合物を用いることもできる。
染料の含有量は、顔料の含有量よりも少ないことが好ましい。 Further, the coloring composition according to the present disclosure may contain a dye. As the dye, a Kochi dye can be used, and for example, the methine dye described in JP-A-2019-73695, the methine dye described in JP-A-2019-073696, and the methine dye described in JP-A-2019-73697. Examples of the methine dye of the above, the methine dye described in JP-A-2019-73698, and the like.
As the coloring composition according to the present disclosure, a dye multimer can also be used. The dye multimer is preferably a dye that is used by dissolving it in a solvent. Further, the dye multimer may form particles. When the dye multimer is a particle, it is usually used in a state of being dispersed in a solvent. The dye multimer in the particle state can be obtained, for example, by emulsion polymerization, and the compounds and production methods described in JP-A-2015-214682 are specific examples. The dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less. The plurality of dye structures contained in one molecule may have the same dye structure or may have different dye structures. The weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000. The lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more. The upper limit is more preferably 30,000 or less, further preferably 20,000 or less. The dye multimer is described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, International Publication No. 2016/031442, and the like. Compounds can also be used.
The content of the dye is preferably less than the content of the pigment.
本開示に係る着色組成物の収容容器としては、特に限定はなく、公知の収容容器を用いることができる。また、収容容器として、原材料又は着色組成物中への不純物混入を抑制することを目的に、容器内壁を6種6層の樹脂で構成する多層ボトルや6種の樹脂を7層構造にしたボトルを使用することも好ましい。このような容器としては例えば特開2015-123351号公報に記載の容器が挙げられる。また、収容容器の内壁は、容器内壁からの金属溶出を防ぎ、組成物の保存安定性を高めたり、成分変質を抑制するなど目的で、ガラス製やステンレス製などにすることも好ましい。本開示に係る着色組成物の保存条件としては特に限定はなく、従来公知の方法を用いることができる。また、特開2016-180058号公報に記載された方法を用いることもできる。 <Accommodation container>
The container for containing the colored composition according to the present disclosure is not particularly limited, and a known container can be used. In addition, as a storage container, a multi-layer bottle having a container inner wall made of 6 types and 6 layers of resin and a bottle having 6 types of resin having a 7-layer structure for the purpose of suppressing impurities from being mixed into raw materials or coloring compositions. It is also preferable to use. Examples of such a container include the container described in JP-A-2015-123351. Further, the inner wall of the storage container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the composition, and suppressing the deterioration of the components. The storage conditions of the coloring composition according to the present disclosure are not particularly limited, and conventionally known methods can be used. Further, the method described in JP-A-2016-180058 can also be used.
本開示に係る着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解及び/又は分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液又は分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。 <Preparation method of coloring composition>
The coloring composition according to the present disclosure can be prepared by mixing the above-mentioned components. In preparing the coloring composition, all the components may be dissolved and / or dispersed in a solvent at the same time to prepare a coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to prepare a coloring composition.
本開示に係る硬化物は、本開示に係る着色組成物を乾燥又は硬化してなる硬化物である。本開示においては、本開示に係る着色組成物を乾燥して含有される溶剤を少なくとも一部除去し流動性が失われた乾燥物も、硬化物に含めるものとする。また、硬化の前に乾燥を行い、硬化物を形成してもよい。
本開示に係る硬化物は、カラーフィルタなどに好適に用いることができる。具体的には、カラーフィルタの着色層(画素)として好ましく用いることができ、より具体的には、カラーフィルタの赤色着色層(赤色画素)として好ましく用いることができる。
本開示に係る硬化物は、膜状の硬化物であることが好ましく、その膜厚は、目的に応じて適宜調整できる。例えば、膜厚は、20μm以下が好ましく、10μm以下がより好ましく、5μm以下が更に好ましい。膜厚の下限は、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.3μm以上が更に好ましい。 (Cursed product)
The cured product according to the present disclosure is a cured product obtained by drying or curing the coloring composition according to the present disclosure. In the present disclosure, the cured product also includes a dried product in which at least a part of the solvent contained in the colored composition according to the present disclosure is dried and the fluidity is lost. Further, it may be dried before curing to form a cured product.
The cured product according to the present disclosure can be suitably used for a color filter or the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a red colored layer (red pixel) of a color filter.
The cured product according to the present disclosure is preferably a film-like cured product, and the film thickness thereof can be appropriately adjusted according to the intended purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, still more preferably 0.3 μm or more.
次に、本開示に係るカラーフィルタについて説明する。本開示に係るカラーフィルタは、上述した本開示に係る硬化物を備える。より好ましくは、カラーフィルタの画素として、本開示に係る硬化膜を有する。本開示に係るカラーフィルタは、CCD(電荷結合素子)やCMOS(相補型金属酸化膜半導体)などの固体撮像素子や画像表示装置などに用いることができる。 (Color filter)
Next, the color filter according to the present disclosure will be described. The color filter according to the present disclosure includes the cured product according to the present disclosure described above. More preferably, the pixel of the color filter has a cured film according to the present disclosure. The color filter according to the present disclosure can be used for a solid-state image pickup device such as a CCD (charge-coupled device) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
次に、本開示に係る着色組成物を用いたカラーフィルタの製造方法について説明する。カラーフィルタの製造方法は、上述した本開示に係る着色組成物を用いて支持体上に着色組成物層を形成する工程と、フォトリソグラフィ法又はドライエッチング法により着色組成物層に対してパターンを形成する工程と、を経て製造できる。本開示に係る着色組成物は、現像残渣の発生も抑制することができるので、フォトリソグラフィ法により着色組成物層に対してパターンを形成してカラーフィルタを製造する場合において特に効果的である。 <Manufacturing method of color filter>
Next, a method for manufacturing a color filter using the coloring composition according to the present disclosure will be described. The method for producing a color filter includes a step of forming a coloring composition layer on a support using the coloring composition according to the present disclosure described above, and a pattern on the coloring composition layer by a photolithography method or a dry etching method. It can be manufactured through the process of forming. Since the coloring composition according to the present disclosure can also suppress the generation of development residues, it is particularly effective in the case of producing a color filter by forming a pattern on the coloring composition layer by a photolithography method.
まず、フォトリソグラフィ法によりパターンを形成してカラーフィルタを製造する場合について説明する。この製造方法は、本開示に係る着色組成物を用いて支持体上に着色組成物層を形成する工程と、着色組成物層をパターン状に露光する工程と、着色組成物層の未露光部を現像除去してパターン(画素)を形成する工程と、を含むことが好ましい。必要に応じて、着色組成物層をベークする工程(プリベーク工程)、及び、現像されたパターン(画素)をベークする工程(ポストベーク工程)を設けてもよい。 -Photolithography method-
First, a case where a pattern is formed by a photolithography method to manufacture a color filter will be described. This production method includes a step of forming a colored composition layer on a support using the colored composition according to the present disclosure, a step of exposing the colored composition layer in a pattern, and an unexposed portion of the colored composition layer. It is preferable to include a step of developing and removing the above to form a pattern (pixel). If necessary, a step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
次に、着色組成物層をパターン状に露光する(露光工程)。例えば、着色組成物層に対し、ステッパー露光機やスキャナ露光機などを用いて、所定のマスクパターンを有するマスクを介して露光することで、パターン状に露光することができる。これにより、露光部分を硬化することができる。 << Exposure process >>
Next, the colored composition layer is exposed in a pattern (exposure step). For example, the colored composition layer can be exposed in a pattern by exposing the colored composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
次に、ドライエッチング法によりパターンを形成してカラーフィルタを製造する場合について説明する。ドライエッチング法でのパターン形成は、本開示に係る着色組成物を用いて支持体上に着色組成物層を形成し、この着色組成物層の全体を硬化させて硬化物層を形成する工程と、この硬化物層上にフォトレジスト層を形成する工程と、フォトレジスト層をパターン状に露光したのち、現像してレジストパターンを形成する工程と、このレジストパターンをマスクとして硬化物層に対してエッチングガスを用いてドライエッチングする工程と、を含むことが好ましい。フォトレジスト層の形成においては、更にプリベーク処理を施すことが好ましい。特に、フォトレジスト層の形成プロセスとしては、露光後の加熱処理、現像後の加熱処理(ポストベーク処理)を実施する形態が望ましい。ドライエッチング法でのパターン形成については、特開2013-064993号公報の段落0010~0067の記載を参酌でき、この内容は本明細書に組み込まれる。 -Dry etching method-
Next, a case where a pattern is formed by a dry etching method to manufacture a color filter will be described. The pattern formation by the dry etching method is a step of forming a colored composition layer on a support using the colored composition according to the present disclosure and curing the entire colored composition layer to form a cured product layer. A step of forming a photoresist layer on the cured product layer, a step of exposing the photoresist layer in a pattern and then developing to form a resist pattern, and a step of using this resist pattern as a mask for the cured product layer. It is preferable to include a step of dry etching using an etching gas. In forming the photoresist layer, it is preferable to further perform a prebaking treatment. In particular, as a process for forming the photoresist layer, it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development. Regarding the pattern formation by the dry etching method, the description in paragraphs 0010 to 0067 of JP2013-064993 can be referred to, and this content is incorporated in the present specification.
本開示に係る固体撮像素子は、本開示に係る硬化物を有し、上述した本開示に係るカラーフィルタを有することが好ましい。本開示に係る固体撮像素子の構成としては、本開示に係る膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。 (Solid image sensor)
The solid-state image sensor according to the present disclosure preferably has the cured product according to the present disclosure and preferably has the color filter according to the present disclosure described above. The configuration of the solid-state image pickup device according to the present disclosure is not particularly limited as long as it includes the film according to the present disclosure and functions as a solid-state image pickup device, and examples thereof include the following configurations.
器(携帯電話等)の他、車載カメラや監視カメラ用としても用いることができる。
また、本開示に係る固体撮像素子は、特開2019-211559号公報に記載されているように、固体撮像素子の構造内に紫外線吸収層(UVカットフィルタ)を設けることにより、カラーフィルタの耐光性を改良してもよい。 On the substrate, there are a plurality of photodiodes constituting the light receiving area of a solid-state image pickup device (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and a transfer electrode made of polysilicon or the like. A device protective film made of silicon nitride or the like formed on the photodiode and the transfer electrode so as to have a light-shielding film in which only the light-receiving part of the photodiode is open, and to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. And has a color filter on the device protective film. Further, a configuration having a condensing means (for example, a microlens or the like; the same applies hereinafter) on the device protective film under the color filter (near the substrate), a configuration having a condensing means on the color filter, and the like. There may be. Further, the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern. In this case, the partition wall preferably has a lower refractive index than each colored pixel. Examples of the image pickup apparatus having such a structure are described in JP-A-2012-227478, JP-A-2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No. 2018/0040656. Equipment is mentioned. The image pickup device provided with the solid-state image pickup device according to the present disclosure can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
Further, as described in Japanese Patent Application Laid-Open No. 2019-21159, the solid-state image sensor according to the present disclosure is provided with an ultraviolet absorbing layer (UV cut filter) in the structure of the solid-state image sensor, whereby the light resistance of the color filter is reduced. The sex may be improved.
本開示に係る画像表示装置は、本開示に係る硬化物を有し、上述した本開示に係るカラーフィルタを有することが好ましい。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本開示が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。 (Image display device)
The image display device according to the present disclosure preferably has the cured product according to the present disclosure and preferably has the color filter according to the present disclosure described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. For details on the definition of image display devices and the details of each image display device, see, for example, "Electronic Display Devices (Akio Sasaki, Kogyo Chosakai Co., Ltd., published in 1990)", "Display Devices (Junaki Ibuki, Industrial Books). Co., Ltd. (issued in 1989) ”. Further, the liquid crystal display device is described in, for example, "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)". The liquid crystal display device to which the present disclosure is applicable is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
本開示に係る樹脂は、下記式(3)で表される樹脂である。
下記式(3)で表される樹脂は、顔料を分散する分散剤として好適に用いることができる。 (Resin represented by the formula (3))
The resin according to the present disclosure is a resin represented by the following formula (3).
The resin represented by the following formula (3) can be suitably used as a dispersant for dispersing the pigment.
また、本開示に係る樹脂における式(2)で表される構造の好ましい態様は、上述した式(2)で表される構造の好ましい態様と同様である。
また、本開示に係る樹脂における式(3)で表される樹脂の製造方法は、特に制限はないが、上記工程(i-1)及び工程(i-2)を含むか、又は、上記工程(ii-1)及び工程(ii-2)を含む製造方法が好ましく挙げられる。
式(3)で表される樹脂の製造方法、及び、上記工程(i-1)及び工程(i-2)を含むか、又は、上記工程(ii-1)及び工程(ii-2)を含む製造方法については、上述したものと同様であり、好ましい態様も同様である。 The preferred embodiment of the resin represented by the formula (3) in the resin according to the present disclosure is the same as the preferred embodiment of the resin represented by the above-mentioned formula (3).
Further, the preferred embodiment of the structure represented by the formula (2) in the resin according to the present disclosure is the same as the preferred embodiment of the structure represented by the above-mentioned formula (2).
The method for producing the resin represented by the formula (3) in the resin according to the present disclosure is not particularly limited, but includes the above steps (i-1) and (i-2), or the above steps. A production method including (ii-1) and step (ii-2) is preferably mentioned.
The method for producing a resin represented by the formula (3) and the above steps (i-1) and (i-2) are included, or the above steps (ii-1) and (ii-2) are performed. The manufacturing method including the above is the same as described above, and the preferred embodiment is also the same.
本実施例において、「%」、「部」とは、特に断りのない限り、それぞれ「質量%」、「質量部」を意味する。なお、高分子化合物において、特別に規定したもの以外は、分子量は重量平均分子量(Mw)であり、構成単位の比率はモル百分率である。
重量平均分子量(Mw)は、ゲル浸透クロマトグラフィー(GPC)法によるポリスチレン換算値として測定した値である。
また、実施例において使用した式(1)で表される樹脂であるA-1~A-49はそれぞれ、上述したA-1~A-49と同じ樹脂である。 Hereinafter, the present disclosure will be described in detail by way of examples, but the present disclosure is not limited thereto.
In this embodiment, "%" and "part" mean "% by mass" and "part by mass", respectively, unless otherwise specified. In the polymer compound, except for those specified specifically, the molecular weight is the weight average molecular weight (Mw), and the ratio of the constituent units is the molar percentage.
The weight average molecular weight (Mw) is a value measured as a polystyrene-equivalent value by a gel permeation chromatography (GPC) method.
Further, A-1 to A-49, which are the resins represented by the formula (1) used in the examples, are the same resins as A-1 to A-49 described above, respectively.
フラスコに、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の27.6質量部を導入し、ライトエステルHO-MS(N)(2-メタクリロイロキシエチルコハク酸、共栄社化学(株)製)の10.0質量部、メルカプトエタノール5.00質量部を導入し、窒素をフラスコ内に流しながら、混合物を90℃まで昇温した。更に、V-601(2,2’-アゾビス(2-メチルプロピオン酸)ジメチル、富士フイルム和光純薬(株)製)0.302質量部を追加後、2時間同温度で加熱した。更にV-601を0.302質量部追加し、90℃に昇温し3時間加熱し、重合反応を終了した。
次いで、得られた重合反応物に対して、カプロラクトン73.5質量部、酸化水酸化n-ブチルすず0.042質量部を添加し90℃で2時間、110℃で6時間加熱撹拌したのち、PGMEAを添加して固形分30質量%溶液を得た。 (Synthesis Example 1: Production of A-12)
27.6 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was introduced into the flask, and 10.0 of light ester HO-MS (N) (2-methacryloxyethyl succinic acid, manufactured by Kyoeisha Chemical Co., Ltd.). A mass portion and 5.00 parts by mass of mercaptoethanol were introduced, and the temperature of the mixture was raised to 90 ° C. while flowing nitrogen into the flask. Further, 0.302 parts by mass of V-601 (2,2'-azobis (2-methylpropionic acid) dimethyl, manufactured by Wako Pure Chemical Industries, Ltd.) was added and heated at the same temperature for 2 hours. Further, 0.302 parts by mass of V-601 was added, the temperature was raised to 90 ° C. and the mixture was heated for 3 hours to complete the polymerization reaction.
Next, 73.5 parts by mass of caprolactone and 0.042 parts by mass of n-butyl oxide oxide were added to the obtained polymerization reaction product, and the mixture was heated and stirred at 90 ° C. for 2 hours and 110 ° C. for 6 hours. PGMEA was added to obtain a solid content 30% by mass solution.
フラスコに、プロピレングリコールモノメチルエーテルアセテート(PGMEA)の30.6質量部を導入し、ライトエステルHO-MS(N)(共栄社化学(株)製)の15.4質量部、メルカプトヘキサノール5.00質量部を導入し、窒素をフラスコ内に流しながら、混合物を90℃まで昇温した。更に、V-601の0.347質量部を追加後、2時間同温度で加熱した。更にV-601の0.347質量部を追加し、90℃に昇温し3時間加熱し、重合反応を終了した。
次いで、得られた重合反応物に対して、カプロラクトン47.6質量部、酸化水酸化n-ブチルすず0.024質量部を添加し90℃で2時間、110℃で6時間加熱撹拌した、反応を終了した。
次いで、得られた反応物に対して4HBAGE(4-ヒドロキシブチルアクリレートグリシジルエーテル、三菱ケミカル(株)製)9.57質量部とドデシルジメチルアミン1.07質量部を添加し90℃で48時間加熱して反応を終了した。PGMEAを添加して固形分30質量%溶液を得た。 (Synthesis Example 2: Production of A-48)
30.6 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was introduced into the flask, 15.4 parts by mass of light ester HO-MS (N) (manufactured by Kyoeisha Chemical Co., Ltd.), and 5.00 parts by mass of mercaptohexanol. The section was introduced and the mixture was heated to 90 ° C. while flowing nitrogen into the flask. Further, after adding 0.347 parts by mass of V-601, the mixture was heated at the same temperature for 2 hours. Further, 0.347 parts by mass of V-601 was added, the temperature was raised to 90 ° C. and the mixture was heated for 3 hours to complete the polymerization reaction.
Next, 47.6 parts by mass of caprolactone and 0.024 parts by mass of n-butyl oxide oxide were added to the obtained polymerization reaction product, and the mixture was heated and stirred at 90 ° C. for 2 hours and 110 ° C. for 6 hours. Was finished.
Next, 9.57 parts by mass of 4HBAGE (4-hydroxybutyl acrylate glycidyl ether, manufactured by Mitsubishi Chemical Corporation) and 1.07 parts by mass of dodecyldimethylamine were added to the obtained reaction product, and the mixture was heated at 90 ° C. for 48 hours. And the reaction was finished. PGMEA was added to obtain a solid content 30% by mass solution.
使用する原料を対応するヒドロキシ基を有するメルカプト化合物、エチレン性不飽和化合物、及び、ヒドロキシカルボン酸化合物又はラクトン化合物を用いた以外は、合成例1と同様にして、:A-1~A-11及びA-13~A-45をそれぞれ作製した。 (Synthesis Example 3: Production of A-1 to A-11 and A-13 to A-45)
Similar to Synthesis Example 1, except that the raw material used is a mercapto compound having a corresponding hydroxy group, an ethylenically unsaturated compound, and a hydroxycarboxylic acid compound or a lactone compound: A-1 to A-11. And A-13 to A-45 were prepared, respectively.
使用する原料を対応するヒドロキシ基を有するメルカプト化合物、エチレン性不飽和化合物、ヒドロキシカルボン酸化合物又はラクトン化合物、及び、エポキシ基を有するエチレン性不飽和化合物を用いた以外は、合成例2と同様にして、:A-47~A-49をそれぞれ作製した。 (Synthesis Example 4: Production of A-47 to A-49)
The same as in Synthesis Example 2 except that the mercapto compound having a hydroxy group, the ethylenically unsaturated compound, the hydroxycarboxylic acid compound or the lactone compound, and the ethylenically unsaturated compound having an epoxy group were used as the raw materials to be used. : A-47 to A-49 were prepared respectively.
緑色顔料(G顔料)としてC.I.Pigment Green 58を8.75質量部と、黄色顔料(Y顔料)としてC.I.Pigment Yellow 185を3.85質量部と、表1又は表2に記載の誘導体を表1又は表2に記載の量(分散液G1ではなし)と、樹脂として樹脂A-1(固形分30%のPGMEA溶液)の11.55質量部(固形分3.465質量部相当)と、溶剤としてプロピレングリコールモノメチルエーテルアセテートの67.3質量部とを混合したのち、直径0.3mmのジルコニアビーズ230質量部を加えて、ペイントシェーカーを用いて5時間分散処理を行い、ビーズをろ過で分離して分散液G1を製造した。 <Preparation of dispersion G1>
C.I. as a green pigment (G pigment). I. Pigment Green 58 with 8.75 parts by mass and C.I. as a yellow pigment (Y pigment). I. Pigment Yellow 185 in an amount of 3.85 parts by mass, the derivative shown in Table 1 or Table 2 in the amount shown in Table 1 or Table 2 (not the dispersion liquid G1), and resin A-1 (solid content 30%) as a resin. 11.55 parts by mass (equivalent to 3.465 parts by mass of solid content) and 67.3 parts by mass of propylene glycol monomethyl ether acetate as a solvent, and then 230 parts by mass of zirconia beads having a diameter of 0.3 mm. The parts were added and subjected to a dispersion treatment for 5 hours using a paint shaker, and the beads were separated by filtration to produce a dispersion liquid G1.
樹脂の種類、誘導体の種類及び配合量、並びに、溶剤の種類をそれぞれ下記表1又は表2に記載の通り変更した以外は、分散液G1と同様にして各分散液を製造した。なお、各分散液における溶剤の添加量は67.3質量部である。 <Manufacturing of dispersions G2 to G63, and comparative dispersions GM1 and GM2>
Each dispersion was produced in the same manner as the dispersion G1 except that the type of resin, the type and blending amount of the derivative, and the type of solvent were changed as shown in Table 1 or Table 2 below, respectively. The amount of the solvent added to each dispersion is 67.3 parts by mass.
<比較樹脂>
AM-1:下記の方法により製造した樹脂
AM-2:下記の方法により製造した樹脂 The details of the abbreviations shown in Tables 1 and 2 other than those described above are shown below.
<Comparative resin>
AM-1: Resin manufactured by the following method AM-2: Resin manufactured by the following method
1-ドデカノール62.6質量部、ε-カプロラクトン287.4質量部、モノブチルスズオキシド0.1質量部を120℃で4時間加熱、撹拌した。次に、トリメリット酸無水物64.5質量部を加え、120℃で2時間反応させた。プロピレングリコールモノメチルエーテルアセテートを加えて、固形分濃度を30%に調整し、酸価91mgKOH/g、重量平均分子量1,200の樹脂AM-1を得た。 -AM-1 manufacturing method-
62.6 parts by mass of 1-dodecanol, 287.4 parts by mass of ε-caprolactone and 0.1 parts by mass of monobutyltin oxide were heated and stirred at 120 ° C. for 4 hours. Next, 64.5 parts by mass of trimellitic acid anhydride was added, and the mixture was reacted at 120 ° C. for 2 hours. Propylene glycol monomethyl ether acetate was added to adjust the solid content concentration to 30% to obtain a resin AM-1 having an acid value of 91 mgKOH / g and a weight average molecular weight of 1,200.
ガス導入管、温度計、コンデンサー、撹拌機を備えた反応容器に、メチルメタクリレート75質量部、n-ブチルアクリレート75質量部、プロピレングリコールモノメチルエーテルアセテート(PGMEA)68.1質量部を仕込み、窒素ガスで反応容器内を置換した。反応容器内を70℃に加熱して、3-メルカプト-1,2-プロパンジオール9質量部を添加し、更にAIBN(アゾビスイソブチロニトリル)0.18質量部を加え、12時間反応させた。固形分測定により95%が反応したことを確認した。続いて、ピロメリット酸無水物14.6質量部、PGMEA105.5質量部、反応触媒として1、8-ジアザビシクロ-[5.4.0]-7-ウンデセン(DBU)0.3質量部を追加し、120℃で7時間反応させた。酸価測定により、98%以上の酸無水物がハーフエステル化していることを確認し、反応を終了した。PGMEAを加えて固形分濃度を30%に調整し、酸価41mgKOH/g、重量平均分子量8,800の樹脂(AM-2)を得た。 -AM-2 manufacturing method-
In a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer, 75 parts by mass of methyl methacrylate, 75 parts by mass of n-butyl acrylate, and 68.1 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) are charged, and nitrogen gas is charged. The inside of the reaction vessel was replaced with. The inside of the reaction vessel is heated to 70 ° C., 9 parts by mass of 3-mercapto-1,2-propanediol is added, and 0.18 parts by mass of AIBN (azobisisobutyronitrile) is further added, and the mixture is reacted for 12 hours. rice field. It was confirmed by solid content measurement that 95% had reacted. Subsequently, 14.6 parts by mass of pyromellitic acid anhydride, 105.5 parts by mass of PGMEA, and 0.3 parts by mass of 1,8-diazabicyclo- [5.4.0] -7-undecene (DBU) as a reaction catalyst were added. Then, the reaction was carried out at 120 ° C. for 7 hours. By measuring the acid value, it was confirmed that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated. PGMEA was added to adjust the solid content concentration to 30% to obtain a resin (AM-2) having an acid value of 41 mgKOH / g and a weight average molecular weight of 8,800.
S-1~S-4:下記化合物 <Derivative (pigment derivative)>
S-1 to S-4: The following compounds
PGMEA:プロピレングリコールモノメチルエーテルアセテート
PGME:プロピレングリコールモノメチルエーテル <Solvent>
PGMEA: Propylene Glycol Monomethyl Ether Acetate PGME: Propylene Glycol Monomethyl Ether
G顔料及びY顔料の種類並びに配合量をそれぞれ下記表3に記載の通り変更した以外は、分散液G9と同様にして各分散液を作製した。 <Preparation of dispersion liquids G64 to G79>
Each dispersion was prepared in the same manner as the dispersion G9, except that the types and blending amounts of the G pigment and the Y pigment were changed as shown in Table 3 below.
<緑色顔料(G顔料)>
PG36:C.I.Pigment Green 36
PG58:C.I.Pigment Green 58
PG7:C.I.Pigment Green 7
PG59:C.I.Pigment Green 59
PG62:C.I.Pigment Green 62
PG63:C.I.Pigment Green 63 The details of the abbreviations shown in Table 3 are shown below.
<Green pigment (G pigment)>
PG36: C.I. I. Pigment Green 36
PG58: C.I. I. Pigment Green 58
PG7: C.I. I. Pigment Green 7
PG59: C.I. I. Pigment Green 59
PG62: C.I. I. Pigment Green 62
PG63: C.I. I. Pigment Green 63
PY129:C.I.Pigment Yellow 129
PY139:C.I.Pigment Yellow 139
PY150:C.I.Pigment Yellow 150
PY185:C.I.Pigment Yellow 185
PY215:C.I.Pigment Yellow 215 <Yellow pigment (Y pigment)>
PY129: C.I. I. Pigment Yellow 129
PY139: C.I. I. Pigment Yellow 139
PY150: C.I. I. Pigment Yellow 150
PY185: C.I. I. Pigment Yellow 185
PY215: C.I. I. Pigment Yellow 215
表4の記載の各成分を表4に記載の量で配合した混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間更に混合及び分散した。その後更に、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2,000kg/cm3の圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返し、各分散液R1~R15(赤色(Red)分散液)、分散液Y1(黄色(Yellow)分散液)、並びに、比較分散液RM1及びRM2(赤色(Red)分散液)をそれぞれ得た。 <Preparation of dispersions R1 to R15, Y1 and comparative dispersions RM1 and RM2>
A mixed solution containing each component shown in Table 4 in the amount shown in Table 4 was further mixed and dispersed by a bead mill (zirconia beads 0.3 mm diameter) for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment is repeated 10 times, and each dispersion R1 to R15 (red dispersion), dispersion Y1 (yellow dispersion), and comparative dispersions RM1 and RM2 (red dispersion) are repeated. ) Was obtained respectively.
PR254:C.I.Pigment Red 254
PR264:C.I.Pigment Red 264
PR272:C.I.Pigment Red 272
PR122:C.I.Pigment Red 122
PO71:C.I.Pigment Orange 71 The details of the abbreviations shown in Table 4 other than those described above are shown below.
PR254: C.I. I. Pigment Red 254
PR264: C.I. I. Pigment Red 264
PR272: C.I. I. Pigment Red 272
PR122: C.I. I. Pigment Red 122
PO71: C.I. I. Pigment Orange 71
表5の記載の各成分を表5に記載の量で配合した混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間更に混合及び分散した。その後更に、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2,000kg/cm3の圧力下で流量500g/minとして分散処理を行った。この分散処理を10回繰り返し、各分散液B1~B5(青色(Blue)分散液)、及び、比較分散液BM1~BM3(青色(Blue)分散液)をそれぞれ得た。 <Preparation of dispersions B1 to B5 and comparative dispersions BM1 and BM2>
A mixed solution containing each component shown in Table 5 in the amount shown in Table 5 was further mixed and dispersed by a bead mill (zirconia beads 0.3 mm diameter) for 3 hours. After that, a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to perform a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3 . This dispersion treatment was repeated 10 times to obtain each dispersion liquid B1 to B5 (blue (Blue) dispersion liquid) and comparative dispersion liquids BM1 to BM3 (blue (Blue) dispersion liquid), respectively.
以下に、上述した以外の表5に記載の略称の詳細を示す。
PB15:6:C.I.Pigment Blue 15:6
PV23:C.I.Pigment Violet 23 The unit of the numerical value in each component column of Table 5 is a mass part.
The details of the abbreviations shown in Table 5 other than those described above are shown below.
PB15: 6: C.I. I. Pigment Blue 15: 6
PV23: C.I. I. Pigment Violet 23
<着色組成物の調製>
以下の原料を混合して、着色組成物を調製した。
下記表6又は表7に記載の分散液:39.4質量部
樹脂C1:0.58質量部
重合性化合物E1:0.54質量部
光重合開始剤F3:0.33質量部
界面活性剤H1:4.17質量部
p-メトキシフェノール:0.0006質量部
プロピレングリコールモノメチルエーテルアセテート(PGMEA):7.66質量部
なお、実施例G1~G63、並びに、比較例GM1及びGM2の着色組成物における顔料の含有量はそれぞれ、着色組成物の全固形分に対し、62.6質量%であった。 (Examples G1 to G63, and Comparative Examples GM1 and GM2)
<Preparation of coloring composition>
The following raw materials were mixed to prepare a coloring composition.
Dispersion solution shown in Table 6 or Table 7 below: 39.4 parts by mass Resin C1: 0.58 parts by mass Polymerizable compound E1: 0.54 parts by mass Photopolymerization initiator F3: 0.33 parts by mass Surface active agent H1 : 4.17 parts by mass p-methoxyphenol: 0.0006 parts by mass propylene glycol monomethyl ether acetate (PGMEA): 7.66 parts by mass In the coloring compositions of Examples G1 to G63 and Comparative Examples GM1 and GM2. The content of each of the pigments was 62.6% by mass with respect to the total solid content of the coloring composition.
光重合開始剤F3:下記構造の化合物。 Polymerizable compound E1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
Photopolymerization initiator F3: A compound having the following structure.
上記で得られた着色組成物(分散液又は硬化性組成物)の初期粘度(V0)を、東機産業(株)製「RE-85L」にて測定した。次いで、この着色組成物を45℃、3日間の条件にて静置した後、静置後の粘度(V1)を測定した。下記式から静置後の着色組成物の粘度上昇率(%)を算出し、下記評価基準に従って液安定性を評価した。粘度上昇率(%)の数値が小さいほど、液安定性が良好であるといえる。着色組成物の粘度は25℃に温度調整を施した状態で測定した。
粘度上昇率(%)=[(静置後の粘度(V1)-初期粘度(V0))/初期粘度(V0)]×100
A:0≦粘度上昇率≦3%
B:3%<粘度上昇率≦5%
C:5%<粘度上昇率≦10%
D:10%<粘度上昇率≦15%
E:15%<粘度上昇率 <Liquid stability (dispersion liquid stability)>
The initial viscosity (V0) of the coloring composition (dispersion liquid or curable composition) obtained above was measured with "RE-85L" manufactured by Toki Sangyo Co., Ltd. Then, this coloring composition was allowed to stand at 45 ° C. for 3 days, and then the viscosity (V1) after standing was measured. The viscosity increase rate (%) of the colored composition after standing was calculated from the following formula, and the liquid stability was evaluated according to the following evaluation criteria. It can be said that the smaller the value of the viscosity increase rate (%) is, the better the liquid stability is. The viscosity of the coloring composition was measured in a state where the temperature was adjusted to 25 ° C.
Viscosity increase rate (%) = [(Viscosity after standing (V1) -Initial viscosity (V0)) / Initial viscosity (V0)] × 100
A: 0 ≤ viscosity increase rate ≤ 3%
B: 3% <Viscosity increase rate ≤ 5%
C: 5% <Viscosity increase rate ≤ 10%
D: 10% <Viscosity increase rate ≤ 15%
E: 15% <Viscosity increase rate
シリコンウエハ上にCT-4000(富士フイルムエレクトロニクスマテリアルズ(株)製)を膜厚が0.1μmとなるようにスピンコート法で塗布し、ホットプレートを用いて220℃で1時間加熱して下地層を形成した。この下地層付きのシリコンウエハ上に各着色組成物をスピンコート法で塗布し、その後、ホットプレートを用いて100℃で2分間加熱して、膜厚1μmの組成物層を得た。この組成物層に対して、i線ステッパーFPA-3000i5+(キヤノン(株)製)を使用し、一辺1.1μmの正方ピクセルがそれぞれ基板上の4mm×3mmの領域に配列されたマスクパターンを介して、365nmの波長の光を200mJ/cm2の露光量で照射して露光した。露光後の組成物層に対し、テトラメチルアンモニウムハイドロオキサイドの0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにて水を用いてリンスを行い、更に純水にて水洗いを行った。その後、水滴を高圧のエアーで飛ばし、シリコンウエハを自然乾燥させたのち、ホットプレートを用いて200℃で300秒間ポストベークを行い、パターンを形成した。パターン間の残差の有無を観察して現像性を評価した。
パターンの形成領域外(未露光部)を走査型電子顕微鏡(SEM)(倍率10,000倍)で観察し、未露光部5μm×5μmの面積(1エリア)あたりの直径0.1μm以上の残渣を数え、下記評価基準に従って残渣を評価した。
A:1エリアあたりの残渣が全くない。
B:1エリアあたりの残渣の数が10個未満である。
C:1エリアあたりの残渣の数が10個以上20個未満である。
D:1エリアあたりの残渣の数が20個以上30個未満である。
E:1エリアあたりの残渣の数が30個以上である。
F:現像が全くできなかった。 <Developability (development residue suppression)>
CT-4000 (manufactured by Fujifilm Electronics Materials Co., Ltd.) is applied on a silicon wafer by the spin coating method so that the film thickness is 0.1 μm, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum. Each colored composition was applied onto the silicon wafer with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 1 μm. For this composition layer, an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 1.1 μm were arranged in a 4 mm × 3 mm region on the substrate via a mask pattern. Then, light having a wavelength of 365 nm was irradiated with an exposure amount of 200 mJ / cm 2 for exposure. The composition layer after exposure was paddle-developed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Then, it was rinsed with water in a spin shower and then washed with pure water. Then, water droplets were blown off with high-pressure air, the silicon wafer was naturally dried, and then post-baked at 200 ° C. for 300 seconds using a hot plate to form a pattern. The developability was evaluated by observing the presence or absence of residuals between patterns.
The outside of the pattern formation area (unexposed area) was observed with a scanning electron microscope (SEM) (magnification 10,000 times), and a residue having a diameter of 0.1 μm or more per 5 μm × 5 μm area (1 area) of the unexposed area. Was counted, and the residue was evaluated according to the following evaluation criteria.
A: There is no residue per area.
B: The number of residues per area is less than 10.
C: The number of residues per area is 10 or more and less than 20.
D: The number of residues per area is 20 or more and less than 30.
E: The number of residues per area is 30 or more.
F: Development was not possible at all.
シリコンウエハ上にCT-4000(富士フイルムエレクトロニクスマテリアルズ(株)製)を膜厚が0.1μmとなるようにスピンコート法で塗布し、ホットプレートを用いて220℃で1時間加熱して下地層を形成した。この下地層付きのシリコンウエハ上に各着色組成物をスピンコート法で塗布し、その後、ホットプレートを用いて100℃で2分間加熱して、膜厚0.5μmの組成物層を得た。この組成物層に対して、i線ステッパーFPA-3000i5+(キヤノン(株)製)を使用し、一辺1.1μmの正方ピクセルがそれぞれ基板上の4mm×3mmの領域に配列されたマスクパターンを介して、365nmの波長の光を500mJ/cm2の露光量で照射して露光した。露光後の組成物層に対し、テトラメチルアンモニウムハイドロオキサイドの0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにて水を用いてリンスを行い、更に純水にて水洗いを行った。その後、水滴を高圧のエアーで飛ばし、シリコンウエハを自然乾燥させたのち、ホットプレートを用いて220℃で300秒間ポストベークを行い、パターンを形成した。得られたパターンについて、光学顕微鏡を用いて観察し、全パターン中密着しているパターンをカウントして密着性を評価した。
A:すべてのパターンが密着している。
B:密着しているパターンが、全パターンの95%以上100%未満である。
C:密着しているパターンが、全パターンの90%以上95%未満である。
D:密着しているパターンが、全パターンの85%以上90%未満である。
E:密着しているパターンが、全パターンの85%未満である。 <Adhesion>
CT-4000 (manufactured by Fujifilm Electronics Materials Co., Ltd.) is applied on a silicon wafer by the spin coating method so that the film thickness is 0.1 μm, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum. Each colored composition was applied onto the silicon wafer with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 0.5 μm. For this composition layer, an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 1.1 μm were arranged in a 4 mm × 3 mm region on the substrate via a mask pattern. Then, light having a wavelength of 365 nm was irradiated with an exposure amount of 500 mJ / cm 2 for exposure. The composition layer after exposure was paddle-developed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Then, it was rinsed with water in a spin shower and then washed with pure water. Then, water droplets were blown off with high-pressure air, the silicon wafer was naturally dried, and then post-baked at 220 ° C. for 300 seconds using a hot plate to form a pattern. The obtained patterns were observed using an optical microscope, and the patterns that were in close contact with each other were counted to evaluate the adhesion.
A: All patterns are in close contact.
B: The patterns that are in close contact with each other are 95% or more and less than 100% of all patterns.
C: The number of closely adhered patterns is 90% or more and less than 95% of all patterns.
D: The number of closely adhered patterns is 85% or more and less than 90% of all patterns.
E: The number of patterns in close contact is less than 85% of all patterns.
分散液を表8に記載のものに変更した以外は、実施例G1と同様にして、着色組成物を作製し、また、上記評価を行った。評価結果を表8に示す。
なお、実施例G64~実施例G79の着色組成物における顔料の含有量はそれぞれ、着色組成物の全固形分に対し、63質量%であった。 (Example G64 to Example G79)
A colored composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 8, and the above evaluation was performed. The evaluation results are shown in Table 8.
The pigment content in the coloring compositions of Examples G64 to G79 was 63% by mass with respect to the total solid content of the coloring compositions.
分散液、樹脂、重合性化合物、光重合開始剤及び溶剤の種類及び量を表9に記載のものに変更した以外は、実施例G1と同様にして、着色組成物を作製し、また、上記評価を行った。
なお、実施例G80~実施例G97の着色組成物における顔料の含有量はそれぞれ、着色組成物の全固形分に対し、62.6質量%であった。
性能評価結果は、実施例G9と同等の結果だった。 (Example G80 to Example G97)
A coloring composition was prepared in the same manner as in Example G1 except that the types and amounts of the dispersion liquid, the resin, the polymerizable compound, the photopolymerization initiator and the solvent were changed to those shown in Table 9, and the above was also prepared. Evaluation was performed.
The pigment content in the coloring compositions of Examples G80 to G97 was 62.6% by mass with respect to the total solid content of the coloring compositions.
The performance evaluation result was the same as that of Example G9.
樹脂C-1:下記樹脂のPGMEA溶液(固形分30%)
樹脂C-2:下記樹脂のPGMEA溶液(固形分30%) The details of the abbreviations shown in Table 9 other than those described above are shown below.
Resin C-1: PGMEA solution of the following resin (solid content 30%)
Resin C-2: PGMEA solution of the following resin (solid content 30%)
F1:IRGACURE-OXE01(BASF社製)、下記構造の化合物。
F2:IRGACURE-OXE02(BASF社製)、下記構造の化合物。
F4:IRGACURE 369(BASF社製)、下記構造の化合物。
F5:下記構造の化合物。 E5: Aronix TO-2349 (manufactured by Toagosei Co., Ltd.)
F1: IRGACURE-OXE01 (manufactured by BASF), a compound having the following structure.
F2: IRGACURE-OXE02 (manufactured by BASF), a compound having the following structure.
F4: IRGACURE 369 (manufactured by BASF), a compound having the following structure.
F5: A compound having the following structure.
分散液、樹脂、重合性化合物、光重合開始剤及び溶剤の種類及び量を表10に記載のものに変更した以外は、実施例G1と同様にして、着色組成物(硬化性組成物)を作製し、また、上記各評価を行った。評価結果を表10に示す。 (Example G98 to Example G111)
The coloring composition (curable composition) was prepared in the same manner as in Example G1 except that the types and amounts of the dispersion liquid, the resin, the polymerizable compound, the photopolymerization initiator and the solvent were changed to those shown in Table 10. It was prepared and each of the above evaluations was performed. The evaluation results are shown in Table 10.
分散液を表11に記載のものに変更した以外は、実施例G1と同様にして、着色組成物を作製し、また、上記評価を行った。評価結果を表11に示す。
なお、実施例R1~実施例R15、実施例Y1、並びに、比較例RM1及びRM2の着色組成物における顔料の含有量はそれぞれ、着色組成物の全固形分に対し、63質量%であった。 (Examples R1 to R15, Example Y1, and Comparative Examples RM1 and RM2)
A colored composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 11, and the above evaluation was performed. The evaluation results are shown in Table 11.
The pigment content in the coloring compositions of Examples R1 to R15, Example Y1, and Comparative Examples RM1 and RM2 was 63% by mass with respect to the total solid content of the coloring composition.
分散液を表12に記載のものに変更した以外は、実施例G1と同様にして、着色組成物を作製し、また、上記評価を行った。評価結果を表12に示す。
なお、実施例B1~実施例B5、並びに、比較例BM1及び比較例BM2の着色組成物における顔料の含有量はそれぞれ、着色組成物の全固形分に対し、63質量%であった。 (Examples B1 to B5, and Comparative Examples BM1 and BM2)
A colored composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 12, and the above evaluation was performed. The evaluation results are shown in Table 12.
The pigment content in the coloring compositions of Examples B1 to B5, and Comparative Examples BM1 and Comparative Example BM2 was 63% by mass with respect to the total solid content of the coloring composition.
また、上記表6~表12に示すように、実施例の着色組成物は、得られる硬化物の密着性、及び、現像残渣抑制性にも優れるものであった。 As shown in Tables 6 to 12, the coloring compositions of Examples were superior in liquid stability as compared with the coloring compositions of Comparative Examples.
Further, as shown in Tables 6 to 12, the colored compositions of Examples were excellent in the adhesion of the obtained cured product and the ability to suppress the development residue.
シリコンウェハ上に、実施例G33の着色組成物を製膜後の膜厚が0.4μmになるようにスピンコート法で塗布した。次いで、ホットプレートを用いて、100℃で2分間加熱した。次いで、i線ステッパー露光装置FPA-3000i5+(キヤノン(株)製)を用い、1,000mJ/cm2で1.0μm四方のドットパターンのマスクを介して露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにてリンスを行い、更に純水にて水洗した。次いで、ホットプレートを用いて、200℃で5分間加熱することで、シリコンウェハ上に、実施例G33の着色組成物を硬化してなるパターンを形成した。同様に実施例R1の着色組成物、実施例B1の着色組成物を順次パターニングし、赤、緑及び青の着色パターン(Bayerパターン)を形成した。
なお、Bayerパターンとは、米国特許第3,971,065号明細書に開示されているような、一個の赤色(Red)素子と、二個の緑色(Green)素子と、一個の青色(Blue)素子とを有する色フィルタ素子の2×2アレイを繰り返したパターンである。
得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。実施例で作製したいずれの着色組成物を使用した場合でも、固体撮像素子は硬化膜における密着性に優れ、また、好適な画像認識能を有する固体撮像素子が得られたことが確認された。 (Example 201: Fabrication of solid-state image sensor)
The colored composition of Example G33 was applied onto a silicon wafer by a spin coating method so that the film thickness after film formation was 0.4 μm. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), exposure was performed at 1,000 mJ / cm 2 via a mask with a 1.0 μm square dot pattern. Then, paddle development was performed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and then washed with pure water. Then, by heating at 200 ° C. for 5 minutes using a hot plate, a pattern formed by curing the colored composition of Example G33 was formed on a silicon wafer. Similarly, the coloring composition of Example R1 and the coloring composition of Example B1 were sequentially patterned to form red, green and blue coloring patterns (Bayer patterns).
The Bayer pattern is a red element, two green elements, and one blue element as disclosed in US Pat. No. 3,971,065. ) It is a pattern in which a 2 × 2 array of color filter elements having an element is repeated.
The obtained color filter was incorporated into a solid-state image sensor according to a known method. It was confirmed that no matter which of the coloring compositions prepared in the examples was used, the solid-state image sensor was excellent in adhesion in the cured film, and a solid-state image sensor having suitable image recognition ability was obtained.
本明細書に記載された全ての文献、特許出願、及び、技術規格は、個々の文献、特許出願、及び、技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書中に参照により取り込まれる。 The disclosure of Japanese Patent Application No. 2020-128455, filed July 29, 2020, is incorporated herein by reference in its entirety.
All documents, patent applications, and technical standards described herein are to the same extent as if the individual documents, patent applications, and technical standards were specifically and individually stated to be incorporated by reference. Is incorporated herein by reference.
Claims (16)
- 顔料、
下記式(1)で表される樹脂、及び、
溶剤、を含む
着色組成物。
式(1)中、R1はそれぞれ独立に、二価の連結基を表し、R2はそれぞれ独立に、水素原子、又は、一価の置換基を表し、L1は(n+1)価の連結基を表し、nは1~10の整数を表し、mは2~30の整数を表し、P1はエチレン性不飽和化合物を重合してなるポリマー鎖を表す。 Pigment,
The resin represented by the following formula (1) and
A coloring composition containing a solvent.
In formula (1), R 1 independently represents a divalent linking group, R 2 independently represents a hydrogen atom or a monovalent substituent, and L 1 represents a (n + 1) -valent linking group. A group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 1 represents a polymer chain obtained by polymerizing an ethylenically unsaturated compound. - 前記P1が、下記式(2)で表される構造を有する請求項1に記載の着色組成物。
式(2)中、R3は水素原子又はアルキル基を表し、X1は一価の置換基を表し、Lは1以上の整数を表す。 The coloring composition according to claim 1, wherein P 1 has a structure represented by the following formula (2).
In formula (2), R 3 represents a hydrogen atom or an alkyl group, X 1 represents a monovalent substituent, and L represents an integer of 1 or more. - 前記P1が、吸着性基を有する請求項1又は請求項2に記載の着色組成物。 The coloring composition according to claim 1 or 2, wherein P 1 has an adsorptive group.
- 前記吸着性基が、酸基である請求項3に記載の着色組成物。 The coloring composition according to claim 3, wherein the adsorptive group is an acid group.
- 前記樹脂が、下記式(3)で表される樹脂である請求項2に記載の着色組成物。
式(3)中、R1はそれぞれ独立に、二価の連結基を表し、R2はそれぞれ独立に、水素原子、又は、一価の置換基を表し、L2は(n+1)価の連結基を表し、nは1~10の整数を表し、mは2~30の整数を表し、P2は、酸基及び前記式(2)で表される構造を有するポリマー鎖を表す。 The coloring composition according to claim 2, wherein the resin is a resin represented by the following formula (3).
In formula (3), R 1 independently represents a divalent linking group, R 2 independently represents a hydrogen atom or a monovalent substituent, and L 2 represents a (n + 1) -valent linking group. A group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 2 represents an acid group and a polymer chain having a structure represented by the above formula (2). - 前記R1が炭素数3~6のアルキレン基であり、前記R2が水素原子又はアルキル基であり、nが1であり、mが4~20の整数である請求項1~請求項5のいずれか1項に記載の着色組成物。 Claims 1 to 5, wherein R 1 is an alkylene group having 3 to 6 carbon atoms, R 2 is a hydrogen atom or an alkyl group, n is 1, and m is an integer of 4 to 20. The coloring composition according to any one item.
- 前記P1を形成する前記エチレン性不飽和化合物が、酸基を有し、かつ、エチレン性不飽和基と前記酸基とを連結する最小の原子数が6~20である化合物を含む請求項1~請求項4のいずれか1項に記載の着色組成物。 Claimed to include a compound in which the ethylenically unsaturated compound forming P 1 has an acid group and the minimum number of atoms connecting the ethylenically unsaturated group and the acid group is 6 to 20. The coloring composition according to any one of 1 to 4.
- 前記樹脂の重量平均分子量が、3,000~15,000である請求項1~請求項7のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 7, wherein the resin has a weight average molecular weight of 3,000 to 15,000.
- 前記P1における前記エチレン性不飽和化合物由来のモノマー単位の数が、2~10である請求項1~請求項4のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 4, wherein the number of monomer units derived from the ethylenically unsaturated compound in P 1 is 2 to 10.
- 重合性化合物を更に含む請求項1~請求項9のいずれか1項に記載の着色組成物。 The coloring composition according to any one of claims 1 to 9, further comprising a polymerizable compound.
- 請求項1~請求項10のいずれか1項に記載の着色組成物を乾燥又は硬化してなる硬化物。 A cured product obtained by drying or curing the coloring composition according to any one of claims 1 to 10.
- 請求項11に記載の硬化物を備えるカラーフィルタ。 A color filter comprising the cured product according to claim 11.
- 請求項12に記載のカラーフィルタを有する固体撮像素子。 A solid-state image sensor having the color filter according to claim 12.
- 請求項12に記載のカラーフィルタを有する画像表示装置。 An image display device having the color filter according to claim 12.
- 下記式(3)で表される樹脂。
式(3)中、R1はそれぞれ独立に、二価の連結基を表し、R2はそれぞれ独立に、水素原子、又は、一価の置換基を表し、L2は(n+1)価の連結基を表し、nは1~10の整数を表し、mは2~30の整数を表し、P2は、酸基及び下記式(2)で表される構造を有するポリマー鎖を表す。
式(2)中、R3は水素原子又はアルキル基を表し、X1は一価の置換基を表し、Lは1以上の整数を表す。 A resin represented by the following formula (3).
In formula (3), R 1 independently represents a divalent linking group, R 2 independently represents a hydrogen atom or a monovalent substituent, and L 2 represents a (n + 1) -valent linking group. A group is represented, n represents an integer of 1 to 10, m represents an integer of 2 to 30, and P 2 represents an acid group and a polymer chain having a structure represented by the following formula (2).
In formula (2), R 3 represents a hydrogen atom or an alkyl group, X 1 represents a monovalent substituent, and L represents an integer of 1 or more. - 下記工程(i-1)及び工程(i-2)を含むか、又は、下記工程(ii-1)及び工程(ii-2)を含む請求項15に記載の樹脂の製造方法。
工程(i-1):ヒドロキシ基を有するメルカプト化合物の存在下、エチレン性不飽和化合物を重合し、末端にヒドロキシ基を有する樹脂を作製する工程
工程(i-2):前記末端にヒドロキシ基を有する樹脂のヒドロキシ基に、ポリエステル樹脂鎖を形成する工程
工程(ii-1):ヒドロキシ基を有するメルカプト化合物のヒドロキシ基に、ポリエステル樹脂鎖を形成し、メルカプト基を有するポリエステル樹脂を作製する工程
工程(ii-2):前記メルカプト基を有するポリエステル樹脂の存在下、エチレン性不飽和化合物を重合する工程 The method for producing a resin according to claim 15, which comprises the following steps (i-1) and (i-2), or includes the following steps (ii-1) and (ii-2).
Step (i-1): A step of polymerizing an ethylenically unsaturated compound in the presence of a mercapto compound having a hydroxy group to prepare a resin having a hydroxy group at the terminal Step (i-2): A hydroxy group at the terminal. Step of forming a polyester resin chain on the hydroxy group of the resin (ii-1): Step of forming a polyester resin chain on the hydroxy group of the mercapto compound having a hydroxy group to produce a polyester resin having a mercapto group. (Ii-2): Step of polymerizing an ethylenically unsaturated compound in the presence of the polyester resin having a mercapto group.
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WO2024024657A1 (en) * | 2022-07-29 | 2024-02-01 | 富士フイルム株式会社 | Curable composition, light-blocking film, solid-state imaging element, image display device, infrared sensor, and method for manufacturing cured film |
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US4031290A (en) * | 1972-05-01 | 1977-06-21 | Ppg Industries, Inc. | Mercaptan blocked thermosetting copolymers |
JP2009165925A (en) * | 2008-01-11 | 2009-07-30 | Toyo Ink Mfg Co Ltd | Polyester dispersant, and pigment composition employing the same |
JP2012036379A (en) * | 2010-07-14 | 2012-02-23 | Toyo Ink Sc Holdings Co Ltd | Dispersant for pigment, and pigment composition using the same |
WO2018155104A1 (en) * | 2017-02-23 | 2018-08-30 | 富士フイルム株式会社 | Photosensitive composition, cured film, color filter, solid-state imaging element and image display device |
JP2020042085A (en) * | 2018-09-07 | 2020-03-19 | コニカミノルタ株式会社 | Electrostatic image development toner |
JP2020050854A (en) * | 2018-09-21 | 2020-04-02 | 東洋インキScホールディングス株式会社 | Colored composition, photosensitive colored composition, color filter and color liquid crystal display device |
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Patent Citations (6)
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US4031290A (en) * | 1972-05-01 | 1977-06-21 | Ppg Industries, Inc. | Mercaptan blocked thermosetting copolymers |
JP2009165925A (en) * | 2008-01-11 | 2009-07-30 | Toyo Ink Mfg Co Ltd | Polyester dispersant, and pigment composition employing the same |
JP2012036379A (en) * | 2010-07-14 | 2012-02-23 | Toyo Ink Sc Holdings Co Ltd | Dispersant for pigment, and pigment composition using the same |
WO2018155104A1 (en) * | 2017-02-23 | 2018-08-30 | 富士フイルム株式会社 | Photosensitive composition, cured film, color filter, solid-state imaging element and image display device |
JP2020042085A (en) * | 2018-09-07 | 2020-03-19 | コニカミノルタ株式会社 | Electrostatic image development toner |
JP2020050854A (en) * | 2018-09-21 | 2020-04-02 | 東洋インキScホールディングス株式会社 | Colored composition, photosensitive colored composition, color filter and color liquid crystal display device |
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WO2024024657A1 (en) * | 2022-07-29 | 2024-02-01 | 富士フイルム株式会社 | Curable composition, light-blocking film, solid-state imaging element, image display device, infrared sensor, and method for manufacturing cured film |
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