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Phthalocyanine compound, photosensitive resin composition, photosensitive resin layer, color filter and display device

A technology of compounds and phthalocyanines, applied in the field of display devices, can solve the problems of reduced pattern formability, reduced sensitivity, insufficient substrate adhesion, etc., and achieve excellent brightness and contrast

Pending Publication Date: 2021-05-04
SAMSUNG SDI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Since a charge-coupled device (CCD) image sensor uses a photosensitive resin layer for a color filter that requires a film thickness of less than or equal to about 1.5 microns, the photosensitive resin composition should be prepared by including a large amount of colorant, And thus have the problem of insufficient adhesion to the substrate or insufficient curing due to reduced sensitivity, significant decrease in pattern formability (such as loss of color due to dye elution in exposed areas), and the like

Method used

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  • Phthalocyanine compound, photosensitive resin composition, photosensitive resin layer, color filter and display device
  • Phthalocyanine compound, photosensitive resin composition, photosensitive resin layer, color filter and display device
  • Phthalocyanine compound, photosensitive resin composition, photosensitive resin layer, color filter and display device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0264] Synthesis Example 1: Synthesis of compounds represented by Chemical Formula 1-1

[0265] 3,4,5,6-Tetrachlorophthalonitrile (5 g), 2-isopropyl-phenol (2.56 g), K 2 CO 3 (3.9 g) and N,N-dimethylformamide (25 mL) were placed in a 100 mL flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

[0266] 4-(2-Isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.73 g), phthalonitrile (0.35 g), 1,8-diazabicycloundec-7-ene (2.08 g) and 1-pentenol (15 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solid, add zinc acetate (0.50 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the re...

Synthetic example 2

[0270] Synthesis Example 2: Synthesis of compounds represented by Chemical Formula 1-2

[0271] 4-(2-Isopropyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 2.91 g), phthalonitrile (0.70 g), 1,8-diazabicycloundec-7-ene (4.16 g) and 1-pentenol (30 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solids, add zinc acetate (1.00 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the resulting precipitate was filtered and dried in vacuo. The dried solid was purified by column chromatography. Dichloromethane was appropriately added to the purified solid and dissolved, and methanol was added thereto to crystallize it. The crystalline solid was filtered and vacuum dried to obtain the compound represented by Chemical Formula 1-2.

[0272] [chemical formula 1-2]

[0273]

[0274] Maldi-tof MS:1090.96m / z

Synthetic example 3

[0275] Synthesis Example 3: Synthesis of compounds represented by Chemical Formula 1-3

[0276] 3,4,5,6-Tetrachlorophthalonitrile (5 g), 2-tert-butyl-phenol (2.83 g), K 2 CO 3 (3.9 g) and N,N-dimethylformamide (25 mL) were placed in a 100 mL flask and stirred while heating at 70°C. When the reaction was complete, ethyl acetate (EA) was used for extraction. After extraction, the resultant was concentrated and purified by column chromatography. After purification, the resultant was dried in vacuo to obtain 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile.

[0277] 4-(2-tert-butyl-phenoxy)-3,5,6-trichloro-phthalonitrile (2 g), 3,4,5,6-tetrachlorophthalonitrile ( 0.70 g), phthalonitrile (0.34 g), 1,8-diazabicycloundec-7-ene (2.01 g) and 1-pentenol (15 g) were placed in a 100 ml flask and Heat to 90°C to dissolve the solid, add zinc acetate (0.48 g), and stir the result while heating to 140°C. When the reaction was complete, methanol was used for precipitation, and the...

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Abstract

The present invention provides: a phthalocyanine compound exhibiting the shortest wavelength with respect to the full width at half maximum of the maximum absorption wavelength in the range of 600 nm to 620 nm; a photosensitive resin composition containing a phthalocyanine compound; a photosensitive resin layer produced using the photosensitive resin composition; a color filter including a photosensitive resin layer; and a display device comprising the color filter. The phthalocyanine compound has excellent green spectral characteristics, a high molar extinction coefficient and excellent solubility in an organic solvent.

Description

[0001] Cross References to Related Applications [0002] This application claims Korean Patent Application No. 10-2019-0135770 filed at KIPO on October 29, 2019 and Korean Patent Application No. 1 filed at KIPO on Aug. 19, 2020 10-2020-0104060, the entire contents of which are incorporated herein by reference. technical field [0003] The present disclosure relates to a phthalocyanine-based compound, a photosensitive resin composition containing the compound, a photosensitive resin layer, a color filter, and a display device. Background technique [0004] Among many types of displays, liquid crystal display devices have advantages in brightness, thinness, low cost, low operating power consumption, and improved adhesion to integrated circuits, and have been more widely used in laptop computers, monitors, and TV screen. The liquid crystal display device includes: a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed; and an upper su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22G03F7/004G03F7/027G02B5/22
CPCC07D487/22G03F7/004G03F7/027G02B5/223G03F7/0007G03F7/105C09B67/009C09B47/0671C09B47/0675G03F7/0045C09B47/10C09B47/18
Inventor 辛明晔许洙荣权智慧朴宗姬权章玄柳智铉郑义树郑周昊
Owner SAMSUNG SDI CO LTD
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