CN117800968A - Perylene diimide derivative and application thereof - Google Patents
Perylene diimide derivative and application thereof Download PDFInfo
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- CN117800968A CN117800968A CN202311809630.9A CN202311809630A CN117800968A CN 117800968 A CN117800968 A CN 117800968A CN 202311809630 A CN202311809630 A CN 202311809630A CN 117800968 A CN117800968 A CN 117800968A
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- perylene diimide
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- diimide derivative
- dye
- perylene
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- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical class C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000011342 resin composition Substances 0.000 claims description 16
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical group C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 12
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 7
- -1 perylene diimide compound Chemical class 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 15
- 238000011161 development Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- 239000000049 pigment Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QWCGXANSAOXRFE-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanamine Chemical compound COCCOCCN QWCGXANSAOXRFE-UHFFFAOYSA-N 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011077 uniformity evaluation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Optical Filters (AREA)
Abstract
The invention relates to a perylene diimide derivative and application thereof, wherein the chemical structural general formula (I) of the perylene diimide derivative is as follows:
Description
Technical Field
The invention belongs to the technical field of dye compounds, and relates to a perylene diimide derivative and application thereof.
Background
With the development of liquid crystal display technology, liquid Crystal Displays (LCDs) having low power consumption, no radiation, etc. have become the mainstream of the display market. Color filters are key devices for color display of LCDs, which must pass through Color Filters (CF) to produce color changes in the liquid crystal display. In the prior art, the manufacturing method of the color filter comprises the following steps: dyeing, pigment dispersion, printing, electrodeposition, inkjet, microcell electrolysis, electrophotography, thin film decomposition, multilayer interference film method, and the like. For example, color filters of medium and small size are generally manufactured by pigment dispersion, and specifically include: a black matrix is formed on a glass substrate, a layer of photoresist raw material is coated on the glass substrate with the black matrix, and a color photoresist pattern is formed after processes such as mask masking, exposure, development, etching, stripping and the like, for example, a red photoresist pattern can be formed first, the steps for forming the color photoresist pattern are repeatedly executed, and then a green photoresist pattern and a blue photoresist pattern can be formed, and then a color filter is formed through operations such as curing the color photoresist pattern, preparing a protective layer and the like.
Color Filters (CF) are an important component of liquid crystal displays and image sensors, and pigments or dyes as colorants have a critical effect on their optical properties and stability. Because of poor solubility of pigment, the pigment is easy to aggregate to cause large particles, increases light scattering and refraction, and causes low color purity and narrow color gamut. The dye in molecular state has good solubility in common organic solvents (such as Propylene Glycol Methyl Ether Acetate (PGMEA)) for preparing the color filter, avoids the defects of low transmittance and contrast caused by light scattering and refraction effects, and has the advantage of high color purity. Meanwhile, along with the requirements of the industry on high resolution, high light transmittance, high color purity, wide color gamut and high stability of the color filter. Therefore, dye-colorant-based color photoresists and color filters have been the focus of research in industry and academia in recent years.
Among the currently used main red colorants are azo (pigment red 242), pyrrolopyrrole dione (pigment red 242), anthraquinone (pigment red 177) and perylene diimide (pigment red 179), and these conventional red pigments or dyes have been difficult to meet the industrial requirements. Therefore, development of novel red dye with high color purity, wide color gamut and high stability is urgently needed.
Among them, perylene diimide structure is widely used and studied because of its advantages of high color strength, easy modification, excellent stability, and the like. Chinese patent application CN110003207a mentions that perylene diimide dyes with better solubility properties are prepared by introducing phenoxy into the bay site of perylene diimide, introducing trimethylphenyl or tri-hydrophilic chain phenyl into the imide site, and then polymerizing, the solubility is improved to some extent, but the existing perylene diimide dyes still have some defects as follows:
(1) The existing perylene diimide dye has poor absorption in the blue light wave band of 400-460nm, so that the color purity of red is insufficient, and the color gamut is narrower;
(2) The existing perylene diimide dye still has poor solubility in common organic solvents (such as Propylene Glycol Methyl Ether Acetate (PGMEA)) for preparing color filters, and undissolved particles can enhance light scattering and reduce brightness and contrast;
(3) The existing perylene diimide dye is still poor in heat resistance, so that the existing perylene diimide dye is difficult to maintain good light color when the color filter is post-baked at 230 ℃;
(4) The existing perylene diimide dyes are still poor in solvent resistance, resulting in difficulty in maintaining good light color when the color filter is developed.
Meanwhile, jeong Yun Kim et al (Jeong Yun Kim, synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter, J Incl Phenom Macrocycl Chem (2015) 82:203-212) synthesized six novel red perylene diimide dyes by changing the bay and imide functional groups of perylene diimide, which enhanced the solubility and at the same time improved the absorption of the prepared color filter at 650 nm. However, the synthesized dye still has the problems of poor absorption of 400-460nm, poor thermal stability and the like.
Martin Koenemann et al (Martin Koenemann, MULTIPLE CHROMOPHORES WITH A PERYLENEDIIMIDE SKELETON, EP3101087A 1) synthesized better optical performance perylene diimide dyes for use in color converters for Light Emitting Diodes (LEDs) or Organic Light Emitting Diodes (OLEDs) by introducing naphthalimide derivatives at the bay and imide positions of the perylene diimide. But only in the field of color converters, and does not improve the thermal stability and solvent resistance required in the field of color photoresists.
Disclosure of Invention
The invention aims to provide a perylene diimide derivative and application thereof, and the perylene diimide derivative has the advantages of high color purity, high light transmittance, strong heat resistance, strong light resistance, excellent solubility and the like when being used as a dye.
The aim of the invention can be achieved by the following technical scheme:
one of the technical schemes of the invention provides a perylene diimide derivative, which is characterized in that the chemical structural general formula (I) is as follows:
wherein R is 1 、R 2 Each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted group of:
c1 to C100 chain alkyl, C1 to C100 branched alkyl, C1 to C100 alkenyl, C1 to C100 chain alkynyl, C3 to C100 cycloalkyl, C4 to C100 cycloalkenyl, C4 to C100 cycloalkynyl, C1 to C100 alkoxy, C1 to C100 branched alkoxy, C1 to C100 thioalkoxy, C6 to C100 aryl, C3 to C100 heteroaryl, C4 to C100 aryloxy, one of the 400-500nm strongly absorbing naphthalimide groups, and R 1 、R 2 At least one of them is a naphthalimide group with strong absorption of 400-500 nm;
R 3 、R 4 each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted group of:
c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy.
Further, the naphthalimide group is selected from any one of groups represented by the general formula (II):
wherein the dotted line represents R 1 、R 2 A bond to a perylene diimide nucleus of formula (I), M 1 、M 2 Each independently selected from a hydrogen atom, or a substituted or unsubstituted group of:
c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy, and M 1 、M 2 At least one of which is an amine functional group.
Further, the compound is selected from any one of the groups represented by the following formulas (B-1) to (B-24), wherein the dotted line represents M 1 、M 2 Linkage to the naphthalimide parent nucleus in general formula (II):
further, R 3 、R 4 Each independently selected from any one of groups represented by the general formula (III), wherein the dotted line represents R 3 、R 4 Linkage to the perylene diimide nucleus of general formula (I):
wherein Y is 1 ～Y 5 Each independently represents a hydrogen atom, a substituted or unsubstituted group of the following formula: c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy.
Further, R 3 、R 4 Each independently selected from any one of the groups represented by the following formulas (A-1) to (A-12), wherein the dotted line represents R 3 、R 4 Linkage to the perylene diimide nucleus of general formula (I):
further, the chemical structural formula of the perylene diimide derivative is any one of the formulas (1) to (201):
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the second technical scheme of the invention provides application of a perylene diimide derivative in preparation of perylene diimide dye for optical filters.
Further, the optical filter is used for display and sensing devices, and is particularly applied to display and sensing devices such as liquid crystal displays and image sensors.
A third aspect of the present invention provides a perylene diimide dye comprising a perylene diimide derivative as described in any one of the above. Specifically, the dye further comprises a solvent commonly used in the existing perylene diimide dye, and the solvent can be exemplified by propylene glycol methyl ether acetate and the like.
The fourth technical scheme of the invention provides a photosensitive resin composition, which comprises the perylene diimide derivative, a polyfunctional monomer, an alkali-soluble resin, a photoinitiator and a solvent. The specific types of polyfunctional monomers, alkali-soluble resins, photoinitiators and solvents used in the preparation of the optical filters are all conventional in the art, and do not belong to the innovative protection point of the present invention. In addition, conventional additives such as F-556 and KH570 may be added to the resin composition during the actual preparation of the optical filter.
Compared with the prior art, the invention has the following advantages:
(1) Aiming at the problems that the existing perylene diimide dye is poor in absorption in a blue light wave band of 400-460nm, so that the red color purity is insufficient and the color gamut is narrower, the invention modifies a blue light absorption module such as naphthalimide and derivatives thereof at the bay position of perylene diimide to enhance the absorption of 400-460nm, introduces a color assisting group alkoxy group which forms p-pi conjugation with a parent nucleus to increase the electron cloud density of the parent nucleus, thereby leading the absorption to be red shifted and realizing the improvement of the optical property of the dye and obtaining the dye with excellent color purity and light stability;
(2) Aiming at the problem that the existing perylene diimide dye still has insufficient solubility in common organic solvents (such as Propylene Glycol Methyl Ether Acetate (PGMEA)) for preparing a color filter, the invention introduces functional groups with large steric hindrance structures at the imide position of perylene diimide and the periphery of naphthalimide and enhances the solubility of perylene diimide by the functional groups with better solubility in industrial solvents;
(3) Aiming at the problem of poor heat resistance of the existing perylene diimide dye, the invention introduces a steric hindrance functional group at the periphery of the naphthalimide of the perylene diimide, reduces the planeness thereof, inhibits the aggregation behavior of the naphthalimide at high temperature, so that the perylene diimide dye maintains good light color stability at high temperature, thereby enhancing the heat stability of the perylene diimide;
(4) Aiming at the problem of poor solvent resistance of the existing perylene diimide dye, the invention changes the perylene diimide compound into a dendritic structure based on the strategy, enhances the interaction between the perylene diimide compound and resin, and can protect the core parent nucleus of the center, thereby enhancing the solvent resistance.
Detailed Description
The present invention will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical scheme of the present invention, and a detailed implementation manner and a specific operation process are given, but the protection scope of the present invention is not limited to the following examples.
In the following examples, unless otherwise indicated, the starting materials or processing techniques are all conventional commercially available in the art.
Example 1:
the synthesis of the compound (8) is shown in the following specific synthetic process route:
the specific synthesis scheme is as follows:
a mixture of 4-bromonaphthalene anhydride (1 mmol), p-bromophenol (2 mmol) and ethanol (30 mL) was stirred at 90℃under nitrogen for 24h, after the reaction was completed, cooled to room temperature, the mixture was poured into cold water, and after filtration to give a solid, 2- (2-methoxyethoxy) ethylamine (1 mmol), sodium tert-butoxide (1.5 mmol), tetrakis triphenylphosphine palladium (0.05 mmol) and toluene (10 mL) were added, heated at 80℃under reflux for 24h, after the reaction was completed, cooled to room temperature, the mixture was poured into cold water, and the solid was filtered to give a dry solid. With dichloromethane: petroleum ether = 4: the eluent of 1 is separated and purified on a silica gel column to obtain an intermediate 1.
A mixture of brominated perylene diimide (2 mmol), 2, 6-isopropylaniline (6 mmol) and propionic acid (30 mL) was stirred at 140 ℃ under nitrogen protection for 48h, cooled to room temperature after the reaction was completed, poured into cold water, filtered to give a solid, washed 3 times with water and methanol, dried in vacuo, and then dried with dichloromethane: petroleum ether = 1: and (3) purifying by column chromatography to obtain an intermediate 2.
Intermediate 1 (2 mmol), intermediate 2 (1 mmol), potassium carbonate (3 mmol), N-methylpyrrolidone (50 mL) were reacted at 120℃for 24h, after the reaction was completed, cooled to room temperature, and the mixture was poured into water and diluted hydrochloric acid 1:1, filtering to obtain a solid, washing with water and methanol for 3 times, vacuum drying, and separating and purifying on a silica gel column by using methylene dichloride as an eluent. 1.09g of a red solid was obtained in 71.8% yield.
After high-resolution mass spectrum, ESI source and positive ion mode detection, the molecular formula of the compound (8) is C 94 H 82 N 6 O 14 The detection value is 1519.5978, and the theoretical value is 1519.5923; detecting element content (%): c,74.30; h,5.42; n,5.52; o,14.76. Theoretical element content (%): c,74.29; h,5.44; n,5.53; o,14.74. The above analysis shows that the obtained product is the expected product.
The preparation of the compounds of the general formulae (I) and (II) according to the invention is similar to that described in example 1, except that the starting reactants are replaced by the reactants shown in Table 1. The synthesis of the compounds according to examples 2 to 35 can be accomplished by referring to the preparation method of example 1, the specific compounds used are shown in Table 1, and the specific results are shown in Table 2.
TABLE 1
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TABLE 2
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The other compounds claimed in the present application are obtained by referring to the preparation methods of the examples listed above, and are not exemplified here.
Example 1-1
Preparation of Red photosensitive resin composition D1
The perylene diimide dye prepared in example 1 above, i.e., the compound of formula (8), was formulated into a colored photosensitive resin composition D1, and it was subjected to photolithographic development to compare the relevant properties of the photosensitive resin composition. In particular using methods well known to those skilled in the art.
The formula comprises the following components:
200 parts by weight of a colorant L1 (comprising a compound of formula (8) and a solvent Q1 in a mass ratio of 1:39), 50 parts by weight of a polyfunctional monomer M1, 50 parts by weight of a polyfunctional monomer M2, 100 parts by weight of an alkali-soluble resin N, 0.2 part by weight of an additive 01, 0.3 part by weight of an additive 02 and 5 parts by weight of a photoinitiator P were added to about 100 parts by weight of the solvent Q1 and about 50 parts by weight of the solvent Q2, and the mixture was sufficiently dissolved and mixed to control the solid content to about 20%, thereby obtaining a red photosensitive resin composition.
Wherein,
polyfunctional monomer M1: dipentaerythritol hexaacrylate (analytically pure), available from sand dama corporation;
polyfunctional monomer M2: trimethylolpropane trimethacrylate (analytically pure), purchased from taiwan double bond chemical industry;
alkali-soluble resin N: trade name Sarbox SB400 (analytically pure), available from sartomer company;
additive 01: f-556 (trade name, available from DIC Co.);
additive 02: KH570 (γ -methacryloxypropyl trimethoxysilane), purchased from carbofuran;
photoinitiator P: IRGACURE OXE 01 (trade name, available from Basf Co.);
solvent Q1: PGMEA (propylene glycol methyl ether acetate), purchased from dow chemical;
solvent Q2: PM (propylene glycol methyl ether), available from Dow chemical.
Comparative example 2-1
Preparation of Red photosensitive resin composition E1
200 parts by weight of a colorant L5 (comprising a dye A and a solvent Q1 in a ratio of 1:39), 50 parts by weight of a polyfunctional monomer M1, 50 parts by weight of a polyfunctional monomer M2, 100 parts by weight of an alkali-soluble resin N, 0.2 part by weight of an additive 01, 0.3 part by weight of 02 and 5 parts by weight of a photoinitiator P were added to about 100 parts by weight of the solvent Q1 and about 50 parts by weight of the solvent Q2, and the mixture was sufficiently dissolved and mixed to control the solid content to about 20% to obtain a red photosensitive resin composition.
Dye a has the formula:
the performance test of the photosensitive resin composition includes the following steps:
cleaning and drying the glass sheet, and coating the glass sheet with a rotary coating machine to obtain a uniform film layer with the thickness of 1.5-2.0 mu m. Pre-baking at 90deg.C for 120s, exposing with 365nm ultraviolet light with exposure of 40mJ/cm 2 Mask filmThe plate was 180 μm from the coating film, followed by development at 23℃for 50s, followed by post-baking at 230℃for 20min to obtain a filter, after which the subsequent correlation properties were tested, and the results are shown in Table 3.
Performance testing and evaluation method:
(1) Chromaticity: and detecting by adopting a Konica Minolta CM-5 spectrocolorimeter.
(2) System compatibility: the photosensitive resin composition is placed in an environment of 0-10 ℃ and kept in a dark place, the viscosity change (at least six months) of the photosensitive resin composition is tested, and photoetching is carried out according to the process conditions, and whether particles appear on the surface of a color film is inspected under an optical microscope (Optical Microscope, which is called OM hereinafter) of which the x500 times is used.
The evaluation criteria were as follows:
o: viscosity change value < + -5% mPa.s and no particles on x500 surface;
delta: viscosity change value < + -10% mPa.s and no particles on x500 surface;
x: viscosity change value > + -10% mPa.s or x500 surface has particles;
(3) Heat resistance test: verifying heat resistance of the photosensitive resin composition by chromatic aberration, post-baking at 230 ℃ for 20min, repeating the post-baking twice, and measuring the film thickness by an XP-2 step instrument; the color difference is the color difference value between the second post-baked sample and the first post-baked sample, and is measured by Meinada CM-5, if delta E ab Less than 3, the heat resistance is better;
(4) Solvent resistance evaluation:
soaking post-baked sample in isopropanol at room temperature for 5min, baking in oven at 150deg.C for 30min, and measuring color difference before and after, if delta E ab < 3, good solvent resistance is indicated.
(5) Evaluation of anti-transfer dyeing properties:
according to the manufacturing process of the color filter, green or blue pixels are first prepared on Thin Film Transistor (TFT) glass. Then coating a sample, drying the surface of the color filter after development is finished, measuring the color difference before and after the pixel, and if delta E ab And < 3, it shows good transfer resistance.
(6) Line width, edge trim, and development process margin:
line width and edge uniformity were tested by 500 times OM, and mask line width was 140 μm.
During process margin evaluation, other process conditions are fixed, and edge uniformity and edge residue or edge peeling conditions of images obtained in the development time of 40s-100s are examined, wherein peeling performance judgment is judged by referring to a measuring method of adhesive force in the field.
The edge line uniformity evaluation criteria are as follows:
o: the development 50s has neat edge line and no residue at the edge;
delta: the edge of the developed 50s image has burrs, and is irregular or has residues at the edge;
x: image deletion
Specific criteria for development process margin evaluation are as follows:
o: the development is carried out for 40-100s, the edge lines are neat, no residue and no stripping are generated at the edge;
delta: the development is carried out for 50-80s, the edge lines are neat, no residue and no stripping are generated at the edge;
x: the development 50-80s has irregular edge, or has residues at the edge, or has stripping at the edge;
the above alkaline developer is aqueous solution of alkaline compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate, ammonia water, diethylamine or tetramethylammonium hydroxide, [ OH ] - ]The concentration is 0.2-1.0%, preferably 0.4-0.6%.
The evaluation results are shown in Table 3
Examples 1-2 to examples 1-35 preparation of red photosensitive resin compositions D2-D35 reference example 1-1, which was prepared by the same method and materials except for the colorant. The specific evaluation results are shown in Table 3.
TABLE 3 Table 3
The comparison of the experimental results shows that the dyes of examples 1-1 to 1-35 are better in solubility in the color photoresist solvent PGMEA, and the color filters prepared using these dyes are better in color purity, heat resistance and solvent resistance, as compared with the dye a of the comparative example. Meanwhile, the photosensitive resin compositions D1 to D35 using these dyes have good process properties such as system compatibility, edge trim, development process margin, and the like, similar to the photosensitive resin composition E1 using the dye formula (a) of the comparative example.
In combination with the above, the invention improves the optical property of the traditional perylene diimide dye and improves the molecular color purity of the dye; solves the problems of poor thermal stability and solvent resistance in accordance with industrial production requirements and poor solubility and compatibility in a color photoresist system, screens out perylene diimide compounds with better performance, and is used as dye in display and sensing device filters of liquid crystal displays, image sensors and the like.
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present invention.
Claims (10)
1. A perylene diimide derivative is characterized in that the chemical structural general formula (I) is as follows:
wherein R is 1 、R 2 Each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted group of:
c1 to C100 chain alkyl, C1 to C100 branched alkyl, C1 to C100 alkenyl, C1 to C100 alkynyl, C3 to C100 cycloalkyl, C4 to C100 cycloalkenyl, C4 to C100 cycloalkynylAlkoxy of C1 to C100, branched alkoxy of C1 to C100, thioalkoxy of C1 to C100, aryl of C6 to C100, heteroaryl of C3 to C100, aryloxy of C4 to C100, one of the naphthalimide groups with strong absorption at 400-500nm, and R 1 、R 2 At least one of them is a naphthalimide group with strong absorption of 400-500 nm;
R 3 、R 4 each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted group of:
c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy.
2. A perylene diimide derivative according to claim 1, wherein said naphthalimide group is selected from any one of groups represented by general formula (II):
wherein the dotted line represents R 1 、R 2 A bond to a perylene diimide nucleus of formula (I), M 1 、M 2 Each independently selected from a hydrogen atom, or a substituted or unsubstituted group of:
c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy, and M 1 、M 2 At least one of which is an amine functional group.
3. A kind of according to claim 2A perylene diimide derivative, characterized in that the amine group is selected from any one of the groups represented by the following formulas (B-1) to (B-24), wherein the dotted line represents M 1 、M 2 Linkage to the naphthalimide parent nucleus in general formula (II):
4. a perylene diimide derivative as defined in claim 1, wherein R 3 、R 4 Each independently selected from any one of groups represented by the general formula (III), wherein the dotted line represents R 3 、R 4 Linkage to the perylene diimide nucleus of general formula (I):
wherein Y is 1 ～Y 5 Each independently represents a hydrogen atom, a substituted or unsubstituted group of the following formula: c1 to C60 chain alkyl, C1 to C60 branched alkyl, C1 to C60 alkenyl, C1 to C60 chain alkynyl, C3 to C60 cycloalkyl, C4 to C60 cycloalkenyl, C4 to C60 cycloalkynyl, C1 to C60 alkoxy, C1 to C60 branched alkoxy, C1 to C60 thioalkoxy, C6 to C60 aryl, C3 to C60 heteroaryl, C4 to C60 aryloxy.
5. A perylene diimide derivative as defined in claim 4, wherein R 3 、R 4 Each independently selected from any one of the groups represented by the following formulas (A-1) to (A-12), wherein the dotted line represents R 3 、R 4 With perylene diimides of the general formula (I)The connection bond of the parent core:
6. the perylene diimide derivative according to claim 1, wherein the chemical structural formula thereof is any one of the formulae (1) to (201):
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7. use of a perylene diimide derivative as defined in any of claims 1 to 6 in the preparation of a perylene diimide dye for optical filters.
8. The use of perylene diimide derivatives as defined in claim 7, wherein the filter is used in display and sensing devices.
9. A perylene diimide dye comprising the perylene diimide derivative as defined in any one of claims 1 to 6.
10. A photosensitive resin composition comprising the perylene diimide derivative as set forth in any one of claims 1 to 6, a polyfunctional monomer, an alkali-soluble resin, a photoinitiator, and a solvent.
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