CN111338182A - Photosensitive composition and application thereof - Google Patents
Photosensitive composition and application thereof Download PDFInfo
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- CN111338182A CN111338182A CN201811557856.3A CN201811557856A CN111338182A CN 111338182 A CN111338182 A CN 111338182A CN 201811557856 A CN201811557856 A CN 201811557856A CN 111338182 A CN111338182 A CN 111338182A
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 239000011347 resin Substances 0.000 claims abstract description 34
- 229920005989 resin Polymers 0.000 claims abstract description 34
- 239000002516 radical scavenger Substances 0.000 claims abstract description 28
- 239000000049 pigment Substances 0.000 claims abstract description 23
- 229940123457 Free radical scavenger Drugs 0.000 claims abstract description 9
- 150000001491 aromatic compounds Chemical class 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229920002120 photoresistant polymer Polymers 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- -1 polydimethylsiloxane Polymers 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002009 alkene group Chemical group 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 125000005375 organosiloxane group Chemical group 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 abstract description 29
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 18
- 230000008569 process Effects 0.000 abstract description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 8
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- IFDFMWBBLAUYIW-UHFFFAOYSA-N ethane-1,2-diol;ethyl acetate Chemical compound OCCO.CCOC(C)=O IFDFMWBBLAUYIW-UHFFFAOYSA-N 0.000 description 1
- XSQNOFMFKVYSNL-UHFFFAOYSA-N ethene;toluene Chemical compound C=C.CC1=CC=CC=C1 XSQNOFMFKVYSNL-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Images
Classifications
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- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The invention relates to a photosensitive composition and application thereof, wherein the photosensitive composition comprises a free radical scavenger, a monomer, a photoinitiator, an alkali-soluble resin and a pigment; the mass of the free radical scavenger accounts for 0.01-0.8 wt% of the total mass of the monomer and the alkali-soluble resin; the photosensitive composition is used for a color filter. According to the invention, the free radical scavenger which accounts for 0.01-0.8 wt.% of the total mass of the monomer and the alkali-soluble resin is added into the photosensitive composition, so that some free radicals generated between pre-baking and exposure are reacted, the dark reaction is weakened, the line width of the product is still stable even if the photosensitive composition is placed for a long time, the yield of the product is improved, and the photosensitive composition has good process latitude.
Description
Technical Field
The invention relates to the technical field of liquid crystal display, in particular to a photosensitive composition and application thereof.
Background
The preparation method of the color filter comprises the steps of coating a color photoresist composition on a treated glass substrate to form a coating film or a color film with a certain thickness, then prebaking, exposing a specific part area of the color film by using a mask plate through ultraviolet irradiation, carrying out cross-linking polymerization reaction on the exposed area to form a polymerization network structure due to a photoinitiator, reserving the polymerization network structure in subsequent alkali liquor development, developing, cleaning and baking the reserved pattern at high temperature to obtain the color filter, and cleaning the non-exposed area by alkali liquor, namely the steps of substrate treatment, gluing, prebaking, exposure, development and postbaking are included. The performance of the color photoresist directly affects the display performance of the lcd.
Some free radicals can appear in the color photoresist after coating and prebaking heating, however, in the production process, node quality inspection can be carried out irregularly or downtime can appear, if the time between prebaking and exposure is too long (more than 0.5h), the influence of dark reaction on the line width of a product is very obvious, and the difficulty of development is increased. And as time increases, the line width increases significantly, which seriously affects the yield of the product.
CN108535961A discloses a color photoresist composition comprising a pigment dispersion, an alkali-soluble resin, a monomer, a photoinitiator, a solvent and an additive; the pigment dispersion liquid comprises a dispersing agent, a dispersing resin and a pigment, wherein the pigment is connected with the dispersing resin, and the pigment in the pigment dispersion liquid is uniformly dispersed in the photoresist composition; in the post-baking stage of the color filter, carboxyl is generated by the dispersion resin under the heating condition, so that the carboxyl and an epoxy group in an alkali soluble resin or/and a monomer in the color photoresist are subjected to chemical reaction, and the pigment is fixed on a resin cross-linked network in the color photoresist composition, so that the agglomeration phenomenon of the pigment is improved, the quality of the color filter is improved, but if the standing time between the pre-baking and the exposure is too long, the line width of a product is increased by dark reaction, and the yield of the product is reduced.
CN107450268A discloses a color photoresist composition and a method for detecting the dielectric constant loss rate thereof. The color photoresist composition comprises a red pigment, a resin material, a photo-polymerization monomer and a photo-initiator. The resin material is a first copolymer or a second copolymer. The first copolymer comprises methyl tricyclodecylacrylate, benzene, and acrylic acid, and the second copolymer comprises dicyclopentenyl methacrylate, ethylene toluene, and acrylic acid. The weight ratio of the resin material to the sum of the resin material and the photopolymerizable monomer is 30 wt% or more. The photoinitiator includes an oxime-based photoinitiator. The color photoresist composition of the invention has better dielectric constant stability, so that the manufactured photoresist layer has better electrical characteristics. Likewise, the patent does not mention how to prevent the occurrence of dark reaction when the standing time between the pre-bake and the exposure is too long.
Therefore, there is a need in the art to develop a photosensitive composition with good process latitude, which can reduce the adverse effect of the intermittent dark reaction before the exposure after the pre-baking and improve the yield of the product.
Disclosure of Invention
In view of the disadvantages of the prior art, it is an object of the present invention to provide a photosensitive composition comprising a radical scavenger, a monomer, a photoinitiator, an alkali-soluble resin, and a pigment;
the mass of the radical scavenger is 0.01 to 0.8 wt.%, such as 0.02 wt.%, 0.05 wt.%, 0.1 wt.%, 0.15 wt.%, 0.2 wt.%, 0.25 wt.%, 0.3 wt.%, 0.35 wt.%, 0.4 wt.%, 0.45 wt.%, 0.5 wt.%, 0.55 wt.%, 0.6 wt.%, 0.65 wt.%, 0.7 wt.%, 0.75 wt.%, or 0.78 wt.% of the total mass of the monomer and the alkali-soluble resin.
According to the invention, the free radical trapping agent is added into the photosensitive composition, so that some free radicals generated between pre-baking and exposure are reacted, the dark reaction is weakened, the line width of the product is still stable even if the photosensitive composition is placed for a long time, the yield of the product is improved, and the photosensitive composition has good process latitude.
When the mass of the free radical scavenger accounts for 0.01-0.8 wt.% of the total mass of the monomer and the alkali-soluble resin, the best effect can be achieved, the content is too low, only a small amount of free radicals can be reacted, the obvious effect cannot be achieved, the content is too high, a large amount of free radicals can be trapped, the polymerization of the monomer during exposure can be affected, and the developing performance of the composition is affected.
Preferably, the mass of the radical scavenger is 0.3 to 0.8 wt.%, such as 0.35 wt.%, 0.4 wt.%, 0.45 wt.%, 0.5 wt.%, 0.55 wt.%, 0.6 wt.%, 0.65 wt.%, 0.7 wt.%, or 0.75 wt.%, etc., preferably 0.5 to 0.8 wt.%, based on the total mass of the monomer and alkali soluble resin.
Preferably, the photosensitive composition further comprises a leveling agent, and the leveling agent comprises polydimethylsiloxane and/or modified organosiloxane.
Preferably, the content of the leveling agent is 0.1 to 5 parts by weight, for example, 0.15 part by weight, 0.5 part by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, or 4.5 parts by weight, etc., preferably 1 to 3.5 parts by weight, based on 100 parts by weight of the pigment.
The content of the alkali-soluble resin is 10 to 70 parts by weight, for example, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight or the like, preferably 20 to 50 parts by weight;
the photoinitiator is contained in an amount of 0.1 to 15 parts by weight, for example, 0.15 part by weight, 0.5 part by weight, 1 part by weight, 1.5 parts by weight, 2 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight, 5 parts by weight, 5.5 parts by weight, 6 parts by weight, 7 parts by weight, 7.5 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 12.5 parts by weight, 13 parts by weight, 13.5 parts by weight, 14 parts by weight, 14.5 parts by weight, or the like, preferably 3 to 9 parts by weight;
the content of the monomer is 20 to 90 parts by weight, for example, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, 80 parts by weight, 85 parts by weight or 88 parts by weight, etc., preferably 20 to 65 parts by weight.
Preferably, the radical scavenger comprises an aromatic compound having 1 to 3 phenolic hydroxyl groups.
The aromatic group in the aromatic compound is an aromatic group of a single benzene ring or an aromatic group fused by 2-3 benzene rings.
The aromatic compound containing phenolic hydroxyl is selected, and the phenolic hydroxyl can easily capture free radicals in a system, so that the dark reaction generated between pre-baking and exposure can be weakened, the line width is stable, the yield of products is further improved, and the process tolerance is higher.
When the number of phenolic hydroxyl groups of the aromatic compound is 1-3, the addition amount of the matched free radical scavenger is 0.01-0.8 wt%, the best effect can be achieved, and when the number of phenolic hydroxyl groups is too large, a large amount of free radicals can be trapped, the polymerization of monomers in the composition during exposure is influenced, the crosslinking degree is low, and poor development is caused.
The reason why the number of benzene rings is 1 to 3 is that when the number of benzene rings is too large, the activity of the radical scavenger is lowered, and the action of the radical scavenger is impaired.
Preferably, the aromatic compound has the structure of formula (I):
in the formula (I), R is1、R2Each independently selected from a group containing a double bond or hydrogen, and R1、R2At least one of them is a group containing a double bond;
in the formula (I), R is3Selected from C1-C10 alkyl or hydrogen;
in the formula (I), m is 1 or 2.
The radical scavenger may be selected from aromatic compounds having the structure of formula (I), and the present invention does not limit the preparation method of the aromatic compounds, which may be synthesized by the prior art or commercially available to those skilled in the art.
Aromatic groups of a single benzene ring are preferred because a single benzene ring has less steric hindrance and is more likely to trap radicals. The aromatic group is substituted with a group containing double bonds, so that the aromatic compound can participate in polymerization reaction together with monomers in the composition during exposure, and the maximum utilization of raw materials is realized.
When the free radical trapping agent has the structure shown in the formula (I), the free radical trapping agent has the optimal activity, can react free radicals which initiate dark reaction in a pre-baking and exposure gap, and cannot influence the polymerization of monomers in exposure, so that the line width is stable, the product yield is high, and the optimal process tolerance is realized.
Preferably, said R is1、R2Each independently selected from an alkenoic acid group or an alkene group.
When R is1、R2When the photosensitive composition is a group with double bonds, the photosensitive composition can play a role in crosslinking in the process of participating in reaction with the monomer together to form a more compact crosslinking network, thereby being more beneficial to developing the photosensitive composition.
Preferably, the aromatic compound has the structure
The R is1、R2Each independently selected from a group containing a double bond or hydrogen, and R1、R2At least one of them is a group containing a double bond.
When the benzene ring contains two para-phenolic hydroxyl groups, the aromatic compound has the best activity, namely the effect of the free radical scavenger is the best, and the aromatic compound can generate a proper amount of free radicals to react after prebaking, so that the occurrence of dark reaction can be avoided to the greatest extent, and the polymerization of monomers during exposure cannot be influenced.
Preferably, the alkali-soluble resin includes an acrylic resin and/or an acrylate resin.
Preferably, the acid value of the alkali-soluble resin is 50 to 180mg KOH/g, for example, 55mg KOH/g, 60mg KOH/g, 70mg KOH/g, 80mg KOH/g, 90mg KOH/g, 100mg KOH/g, 110mg KOH/g, 120mg KOH/g, 130mg KOH/g, 140mg KOH/g, 150mg KOH/g, 160mg KOH/g, 170mg KOH/g, 175mg KOH/g, or the like.
Preferably, the weight average molecular weight of the alkali-soluble resin is 2000 to 20000, for example 2500, 3000, 4000, 5000, 6000, 7000, 8000, 9000, 10000, 11000, 12000, 13000, 14000, 15000, 16000, 17000, 18000, 19000, or 19500.
Preferably, the photoinitiator comprises a cleavage radical type photoinitiator and/or a cationic type photoinitiator.
Preferably, the photoinitiator comprises any one or at least two of benzoyl compounds, benzoin and derivatives, alkyl phenone compounds, acyl phosphorus oxides, benzophenone compounds, thioxanthone compounds, ketoxime ester compounds, alkyl iodonium salts and cumeneiron hexafluorophosphate.
Preferably, the photoinitiator comprises any one or at least two of 2-phenylbenzyl-2-dimethylamino-1- (4-morpholinylbenzyl) -1-butanone, 4' -bis (diethylamino) benzophenone, 1-hydroxy-cyclohexylbenzophenone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone and acylphosphorus oxide.
Preferably, the monomer includes a compound containing an unsaturated double bond, preferably an acrylate-based compound containing an unsaturated double bond.
Preferably, the monomer includes any one or a combination of at least two of 3- (trimethoxy silane) propyl acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, benzyl methacrylate, dipentaerythritol hexaacrylate, and trimethylolpropane triacrylate.
Preferably, the pigment includes any one or a combination of at least two of a red pigment, a green pigment, a blue pigment, a yellow pigment and an orange pigment.
The specific type of pigment may be well known to those skilled in the art and will not be described further herein.
Preferably, the photosensitive composition further comprises a solvent and/or an auxiliary agent.
Preferably, the solvent is contained in an amount of 250 to 270 parts by weight, for example, 255 parts by weight, 256 parts by weight, 257 parts by weight, 258 parts by weight, 259 parts by weight, 260 parts by weight, 261 parts by weight, 262 parts by weight, 263 parts by weight, 264 parts by weight, 265 parts by weight, 266 parts by weight, 267 parts by weight, 268 parts by weight, 269 parts by weight, or the like, based on 100 parts by weight of the pigment.
Preferably, the content of the assistant is 0.5 to 5 parts by weight, for example, 0.6 part by weight, 0.7 part by weight, 0.8 part by weight, 0.9 part by weight, 1 part by weight, 1.1 part by weight, 1.2 parts by weight, 1.3 parts by weight, 1.4 parts by weight, 1.5 parts by weight, 1.6 parts by weight, 1.7 parts by weight, 1.8 parts by weight, 1.9 parts by weight, 2.5 parts by weight, 3 parts by weight, 3.5 parts by weight, 4 parts by weight, 4.5 parts by weight, or 4.9 parts by weight, etc., based on 100 parts by weight of the pigment.
Preferably, the solvent comprises any one or a combination of at least two of propylene glycol methyl ether acetate, propylene glycol diacetate, ethyl 3-ethoxypropionate, propylene glycol methyl ether, ethylene glycol ethyl acetate, ethyl lactate, cyclohexanone, dicyclohexyl phthalate, dibutyl phthalate, ethylene glycol ethyl ether and cyclohexane.
Preferably, the auxiliary agent comprises any one or at least two of a sensitizer, an antifoaming agent, a coupling agent and a surfactant.
The second object of the present invention is to provide a use of the photosensitive composition according to the first object for a color filter.
Preferably, the photosensitive composition is used as a photoresist film in a color filter.
Compared with the prior art, the invention has the following beneficial effects:
(1) according to the invention, the free radical trapping agent accounting for 0.01-0.8 wt.% of the total mass of the monomer and the alkali-soluble resin is added into the photosensitive composition, so that some free radicals generated between pre-baking and exposure are reacted, the dark reaction is weakened, the line width of the product is still stable even if the photosensitive composition is placed for a long time, the yield of the product is improved, the photosensitive composition is a photosensitive composition with good process latitude, the polymerization of the monomer during exposure is not influenced, and a better line width is obtained.
(2) In the preferred technical scheme, the aromatic compound containing 1-3 phenolic hydroxyl groups and 1-3 benzene rings is selected as the free radical trapping agent, and is matched with the addition amount of the free radical trapping agent, so that the optimal effect can be achieved, free radicals for initiating a dark reaction can be reacted, and polymerization of monomers during exposure can not be influenced.
(3) In a preferred technical scheme, the free radical scavenger is selected from a compound with a structure shown in formula (I), and the free radical scavenger has optimal activity, can react free radicals which initiate dark reaction in a gap between pre-baking and exposure, and does not influence the polymerization of monomers during exposure, so that the line width is stable, the product yield is high, and the process latitude is better.
(4) In the preferred technical scheme, the benzene ring in the compound of the formula (I) contains two para-phenolic hydroxyl groups, the effect of the free radical trapping agent is optimal, free radicals which initiate dark reaction can be reacted away in the gap between pre-baking and exposure, the polymerization of monomers in exposure can not be influenced, the stability of line width and the yield of products are further improved, and the process tolerance is higher.
Drawings
FIG. 1 is a line width-standing time curve of the photosensitive composition of comparative example 1 of the present invention after the pre-bake.
FIG. 2 is a line width-standing time curve of the photosensitive composition of example 1 of the present invention after pre-bake.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
Preparation of a photosensitive composition:
40 parts by weight of an alkali-soluble resin, Sarbox SB400 (from Sartomer corporation), 65 parts by weight of dipentaerythritol hexaacrylate (from Sartomer corporation)From sartomer corporation), 100 parts by weight of a G36+ Y150 pigment (wherein G36 is 50 parts by weight and Y150 is 50 parts by weight) (available from DIC corporation), 6 parts by weight of a photoinitiator OXE-01(Basf corporation), 1.5 parts by weight of a BYK-333 leveling agent (available from BYK corporation), 260 parts by weight of propylene glycol methyl ether acetate as a solvent (available from Dow corporation), 1.5 parts by weight of a silane coupling agent OFS-6030 (available from Dow-Corning corporation), 0.6 part by weight of an aromatic compound 1
A photosensitive composition was obtained.
Example 2
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 2
Example 3
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 3
Example 4
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 4
Example 5
The difference from example 1 is that aromatic compound 1
Replacement ofIs an aromatic compound 5
Example 6
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 6
Example 7
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 7
Example 8
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 8
Example 9
The difference from example 1 is that aromatic compound 1
Substitution with aromatic Compound 9
Example 10
The difference from example 1 is that the amount of the aromatic compound 1 added is 0.525 parts by weight.
Example 11
The difference from example 1 is that the amount of the aromatic compound 1 added is 0.84 parts by weight.
Example 12
The difference from example 1 is that the amount of the aromatic compound 1 added is 0.315 parts by weight.
Example 13
The difference from example 1 is that the amount of the aromatic compound 1 added is 0.0105 parts by weight.
Example 14
20 parts by weight of an alkali-soluble resin Sarbox CD9050 (available from Sartomer Co.), 20 parts by weight of dipentaerythritol hexaacrylate (available from Sartomer Co.), 100 parts by weight of a G36+ Y156 pigment (wherein G36 is 50 parts by weight and Y150 is 50 parts by weight) (available from DIC Co.), 3 parts by weight of a photoinitiator OXE-01 (available from Basf Co.), 1 part by weight of a BYK-333 leveling agent (available from BYK Co.), 250 parts by weight of a solvent propylene glycol monomethyl ether acetate (available from Dow Co.), 0.5 part by weight of a silane coupling agent OFS-6030 (available from Dow-Corning Co.), and 0.6 part by weight of an aromatic compound 1
A photosensitive composition was obtained.
Example 15
50 parts by weight of an alkali-soluble resin Sarbox SB404 (available from Saedoma), 40 parts by weight of dipentaerythritol hexaacrylate (available from Saedoma), 100 parts by weight of a G36+ Y156 pigment (wherein G36 is 50 parts by weight and Y150 is 50 parts by weight) (available from DIC), 9 parts by weight of a photoinitiator OXE-01 (available from Basf), 3.5 parts by weight of a BYK-333 leveling agent (available from BYK), 270 parts by weight of a solvent propylene glycol monomethyl ether acetate (available from Dow), 5 parts by weight of a silane coupling agent OFS-6030 (available from Dow-Corning), and 0.6 part by weight of an aromatic compound 1
A photosensitive composition was obtained.
Example 16
Taking 10 weight parts of alkali soluble resin Sarbox SB400 (available from Sartomer company) and 20 weight parts of dipentaerythritol hexaAcrylate (available from Saedoma), 100 parts by weight of G36+ Y156 pigment (wherein G36 is 50 parts by weight and Y150 is 50 parts by weight) (available from DIC), 0.1 part by weight of photoinitiator OXE-01 (available from Basf), 0.1 part by weight of BYK-333 leveling agent (available from BYK), 260 parts by weight of propylene glycol methyl ether acetate (available from Dow), 2 parts by weight of silane coupling agent OFS-6030 (available from Dow-Corning), 0.6 part by weight of aromatic compound 1
A photosensitive composition was obtained.
Example 17
Taking 70 parts by weight of an alkali-soluble resin Sarbox SB400 (available from Sartomer company), 90 parts by weight of dipentaerythritol hexaacrylate (available from Sartomer company), 100 parts by weight of a G36+ Y156 pigment (wherein G36 is 50 parts by weight and Y150 is 50 parts by weight) (available from DIC company), 15 parts by weight of a photoinitiator OXE-01 (available from Basf company), 5 parts by weight of a BYK-333 leveling agent (available from BYK company), 260 parts by weight of a solvent propylene glycol monomethyl ether acetate (available from Dow company), 2 parts by weight of a silane coupling agent OFS-6030 (available from Dow-Corning company), 0.6 part by weight of an aromatic compound 1
A photosensitive composition was obtained.
Comparative example 1
The difference from example 1 is that the amount of the aromatic compound 1 added is 1.2 parts by weight.
Comparative example 2
The difference from example 1 is that no aromatic compound 1 was added.
Performance testing
The photosensitive compositions of examples and comparative examples were allowed to stand for different periods of time (1 hour, 2 hours, 3 hours, 4 hours, and 5 hours) after the prebaking, respectively, and the line width at each of the different periods of time was recorded, and the amount of change in line width per unit time, i.e., the line width varied with the standing time, was obtained by calculation.
In the normal process, the standing time after pre-baking is 0 hour, the line width is 5.5 μm, and the comparison is performed by taking the line width as a standard, wherein the larger the difference between the line width and 5.5 μm is, the poorer the effect is.
The line width variation with standing time test results are shown in table 1.
TABLE 1
As can be seen from Table 1, the line widths in the examples have lower variation with time than that in comparative example 2, i.e. the variation of the line width in unit time is smaller, the influence caused by dark reaction is basically avoided, which shows that the addition of the radical scavenger can effectively weaken dark reaction, comparative example 1 only increases the addition of the radical scavenger compared with example 1, although the smaller time interval between pre-baking and exposure can be obtained, the line width has larger deviation relative to the line width value of 5.5 μm when not placed, because the excessive addition of the radical scavenger affects monomer polymerization when exposed, and the line width is deteriorated, therefore, 0.01-0.8 wt.% of the radical scavenger is added into the photosensitive composition, the dark reaction can be weakened, even if placed for a longer time, the line width of the product is still stable, the yield of the product is improved, and the photosensitive composition has good process latitude, meanwhile, the monomer polymerization during exposure is not influenced, and the better line width is still maintained.
Fig. 1 is a line width-standing time change curve of the photosensitive composition of comparative example 1 after the pre-bake, and fig. 2 is a line width-standing time change curve of the photosensitive composition of example 1 after the pre-bake, and comparing the two graphs, it can be seen that the influence of the off-period dark reaction on the line width after the pre-bake and before the exposure is significantly reduced after the radical scavenger is added.
It is understood from comparative examples 1, 8 and 9 that the radical scavenger containing a single benzene ring (example 1) has a better effect and a smaller time interval than the radical scavenger containing two benzene rings (example 8) and three benzene rings (example 9), because the single benzene ring has a smaller steric hindrance and is more likely to scavenge radicals.
It is understood from comparative examples 1 to 9 that, when the aromatic compound contains one benzene ring and two para-phenolic hydroxyl groups (example 1), the time interval is the smallest, and since the steric hindrance of the single benzene ring is small, radicals are more easily trapped, and further, since the activity of the para-phenolic hydroxyl group is higher, more radicals can be generated to react with radicals causing a dark reaction, but when the number of the phenolic hydroxyl groups is too large (example 7), a large number of radicals are trapped, which may affect the polymerization of monomers in the composition during exposure, resulting in a low degree of crosslinking, and thus, side effects such as poor development may be caused.
It is understood from comparative examples 1 and 10 to 13 that the time interval is the smallest when the amount of the radical scavenger added is 0.3% to 0.8%, particularly 0.5% to 0.8%, based on the monomer and the resin, and it is presumed that the amount of the radical scavenger is too low, and only a small amount of radical is reacted, which is not enough to exert a significant effect, and that if the amount is too high, a large amount of radical can be trapped, and the dark reaction can be weakened to some extent, but polymerization of the monomer at the time of exposure is affected, which affects the developing performance of the composition.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (11)
1. A photosensitive composition, comprising a radical scavenger, a monomer, a photoinitiator, an alkali-soluble resin, and a pigment;
the mass of the free radical scavenger accounts for 0.01-0.8 wt% of the total mass of the monomer and the alkali-soluble resin.
2. A photosensitive composition according to claim 1, wherein the mass of the radical scavenger is 0.3 to 0.8 wt.%, preferably 0.5 to 0.8 wt.%, based on the total mass of the monomer and the alkali-soluble resin.
3. A photosensitive composition according to claim 1, further comprising a leveling agent comprising polydimethylsiloxane and/or a modified organosiloxane.
4. A photosensitive composition according to claim 1 or 3, wherein the content of the leveling agent is 0.1 to 5 parts by weight, preferably 1 to 3.5 parts by weight, based on 100 parts by weight of the pigment;
the content of the alkali-soluble resin is 10-70 parts by weight, preferably 20-50 parts by weight;
the content of the photoinitiator is 0.1-15 parts by weight, preferably 3-9 parts by weight;
the content of the monomer is 20 to 90 parts by weight, preferably 20 to 65 parts by weight.
5. The photosensitive composition of claim 1, wherein the radical scavenger comprises an aromatic compound having 1 to 3 phenolic hydroxyl groups; the aromatic group in the aromatic compound is an aromatic group of a single benzene ring or an aromatic group condensed by 2-3 benzene rings;
preferably, the aromatic compound has the structure of formula (I):
in the formula (I), R is1、R2Each independently selected from a group containing a double bond or hydrogen, and R1、R2At least one of them is a group containing a double bond;
in the formula (I), R is3Selected from C1-C10 alkyl or hydrogen;
in the formula (I), m is 1 or 2.
6. The photosensitive composition of claim 5, wherein R is1、R2Each independently selected from an alkenoic acid group or an alkene group.
7. The photosensitive composition of claim 5, wherein the aromatic compound has the structure
The R is1、R2Each independently selected from a group containing a double bond or hydrogen, and R1、R2At least one of them is a group containing a double bond.
8. The photosensitive composition according to claim 1, wherein the alkali-soluble resin has an acid value of 50 to 180 mg-KOH/g; the weight average molecular weight of the alkali-soluble resin is 2000-20000.
9. The photosensitive composition of claim 1, further comprising a solvent and/or an auxiliary agent;
the auxiliary agent comprises any one or at least two of a sensitizer, a defoaming agent, a coupling agent and a surfactant.
10. A photosensitive composition according to claim 9, wherein the solvent is contained in an amount of 250 to 270 parts by weight and the auxiliary is contained in an amount of 0.5 to 5 parts by weight based on 100 parts by weight of the pigment.
11. Use of the photosensitive composition according to any one of claims 1 to 10, wherein the photosensitive composition is used for a color filter;
preferably, the photosensitive composition is used as a photoresist film in a color filter.
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| JP2005338400A (en) * | 2004-05-26 | 2005-12-08 | Nippon Kayaku Co Ltd | Negative colored photosensitive composition |
| JP2017138547A (en) * | 2016-02-05 | 2017-08-10 | 凸版印刷株式会社 | Green photosensitive coloring composition, color filter using the same, and color display device |
| CN108319110A (en) * | 2017-01-17 | 2018-07-24 | 固安鼎材科技有限公司 | A kind of colour photoetching compositions and colored filter and preparation method thereof |
| CN108469717A (en) * | 2017-02-23 | 2018-08-31 | 旭化成株式会社 | Photosensitive polymer combination and photoresist laminated body |
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2018
- 2018-12-19 CN CN201811557856.3A patent/CN111338182A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005338400A (en) * | 2004-05-26 | 2005-12-08 | Nippon Kayaku Co Ltd | Negative colored photosensitive composition |
| JP2017138547A (en) * | 2016-02-05 | 2017-08-10 | 凸版印刷株式会社 | Green photosensitive coloring composition, color filter using the same, and color display device |
| CN108319110A (en) * | 2017-01-17 | 2018-07-24 | 固安鼎材科技有限公司 | A kind of colour photoetching compositions and colored filter and preparation method thereof |
| CN108469717A (en) * | 2017-02-23 | 2018-08-31 | 旭化成株式会社 | Photosensitive polymer combination and photoresist laminated body |
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