WO2021085372A1 - 樹脂組成物、化合物（ｚ）、光学フィルターおよびその用途 - Google Patents

樹脂組成物、化合物（ｚ）、光学フィルターおよびその用途 Download PDF

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WO2021085372A1
WO2021085372A1 PCT/JP2020/040085 JP2020040085W WO2021085372A1 WO 2021085372 A1 WO2021085372 A1 WO 2021085372A1 JP 2020040085 W JP2020040085 W JP 2020040085W WO 2021085372 A1 WO2021085372 A1 WO 2021085372A1
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group
compound
formula
atom
resin
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French (fr)
Japanese (ja)
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洋介 内田
勝也 長屋
仁視 大崎
泰典 川部
広幸 下河
一登 中村
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JSR Corp
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JSR Corp
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Priority to KR1020227013997A priority Critical patent/KR20220097889A/ko
Priority to CN202080073048.9A priority patent/CN114616291B/zh
Priority to JP2021553598A priority patent/JP7663505B2/ja
Publication of WO2021085372A1 publication Critical patent/WO2021085372A1/ja
Anticipated expiration legal-status Critical
Priority to JP2024228694A priority patent/JP7816477B2/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C08K5/3447—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • 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
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/26—Reflecting filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/28—Interference filters

Definitions

  • a near-infrared cut filter those manufactured by various methods have been conventionally used.
  • a near-infrared cut filter in which a resin is used as a base material and a near-infrared absorbing dye is contained in the resin is known (see, for example, Patent Document 1).
  • the near-infrared cut filter described in Patent Document 1 may not always have sufficient near-infrared absorption characteristics.
  • R g and R h are each independently a hydrogen atom, an ⁇ C (O) R i group or any of the following L b to L f
  • Q 1 is any of the following L b to L g
  • Q 2 is a hydrogen atom or any of the following L b to L f
  • Q 3 is either a hydroxyl group or the following L b to L f
  • R i is any of the following L b to L f.
  • Z B is a halogen atom or a group represented by any of the following formulas (A-1) to (A-2), and Y B and Y C are formed by being bonded to each other.
  • the compound (Z) used in one embodiment of the present invention not only has sharp absorption in a wavelength region of 850 nm or more, but also has excellent durability. Therefore, according to one embodiment of the present invention. , Not only a near-infrared cut filter (NIR-CF) but also an optical filter such as DBPF or IRPF can be easily manufactured.
  • NIR-CF near-infrared cut filter
  • DBPF DBPF
  • IRPF optical filter
  • a 5- to 6-membered alicyclic group which may contain at least one nitrogen atom, oxygen atom or sulfur atom; or a heteroaromatic group having 3 to 14 carbon atoms which contains at least one nitrogen atom, oxygen atom or sulfur atom.
  • Groups; may be formed, and these alicyclic groups, aromatic hydrocarbon groups and heteroaromatic groups may have an aliphatic hydrocarbon group having 1 to 9 carbon atoms or a halogen atom.
  • R g and R h are each independently a hydrogen atom, an ⁇ C (O) R i group, or any of the above L b to L f , and Q 1 is any of the above L b to L g .
  • Q 2 is a hydrogen atom or any of the L b to L f
  • Q 3 is either a hydroxyl group or the L b to L f
  • R i is any of the L b to L f. is there.
  • each R 5 and R 6 independently represents a monovalent organic group having 1 to 12 carbon atoms
  • Z is a single bond, -O -, - S -, - SO 2 -, - It represents CO-, -CONH-, -COO- or a divalent organic group having 1 to 12 carbon atoms, where e and f independently represent an integer of 0 to 4, and n represents 0 or 1.
  • antioxidants examples include 2,6-di-tert-butyl-4-methylphenol, 2,2'-dioxy-3,3'-di-tert-butyl-5,5'-dimethyldiphenylmethane, and the like. Tetrakiss [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane can be mentioned.
  • a resin layer (1) having a thickness of 0.1 mm, a length of 210 mm and a width of 210 mm.
  • Example 1 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.110 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 11.
  • Example 9 In Example 4, 0.06 parts by mass of the following compound (z-273) (absorption maximum wavelength in dichloromethane) was used instead of 0.05 parts by mass of compound (z-191). A substrate was obtained in the same manner as in Example 4. In the same manner as in Example 4, the spectral characteristics of compound (z-273) in dichloromethane were measured, and Xa, Ta to Tf of the obtained substrate were measured. The results are shown in Tables 10 and 11, respectively.
  • Example 1 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.110 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 11.
  • Example 15-2 In Example 1, 0.04 parts by mass of the following compound (z-363) (absorption maximum wavelength in dichloromethane) was used instead of 0.04 parts by mass of compound (z-25). A substrate was obtained in the same manner as in Example 1. In the same manner as in Example 1, the spectral characteristics of compound (z-363) in dichloromethane were measured, and Xa, Ta to Tf of the obtained substrate were measured. The results are shown in Tables 10 and 11, respectively.
  • Example 15-5 Except for the fact that in Example 1, 0.04 parts by mass of the following compound (z-366) (absorption maximum wavelength in dichloromethane) was used instead of 0.04 parts by mass of the compound (z-25).
  • a substrate was obtained in the same manner as in Example 1.
  • the spectral characteristics of compound (z-366) in dichloromethane were measured, and Xa, Ta to Tf of the obtained substrate were measured. The results are shown in Tables 10 and 11, respectively.
  • Example 1 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.110 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 11.
  • Example 16 In a container, 100 parts by mass of the resin A obtained in Resin Synthesis Example 1, 0.56 parts by mass of the compound (x-1), 0.68 parts by mass of the compound (x-2), and dichloromethane as the compound (X). In addition, a solution having a resin concentration of 20% by mass was prepared and filtered through a millipore filter having a pore size of 5 ⁇ m to obtain a resin solution (E16-1). Similarly, 100 parts by mass of resin A, 0.42 parts by mass of the following compound (z-128) (maximum absorption wavelength in dichloromethane: 942 nm), and dichloromethane are added as compound (Z), and the resin concentration is 20 parts by mass. % Was prepared and filtered through a millipore filter having a pore size of 5 ⁇ m to obtain a resin solution (E16-2).
  • Example 2 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.226 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 12.
  • Example 20 In a container, 100 parts by mass of the resin A obtained in Resin Synthesis Example 1, 0.57 parts by mass of the compound (x-3), 0.68 parts by mass of the compound (x-4), and dichloromethane as the compound (X). In addition, a solution having a resin concentration of 20% by mass was prepared and filtered through a millipore filter having a pore size of 5 ⁇ m to obtain a resin solution (E20-1). Similarly, 100 parts by mass of resin A, 0.42 parts by mass of the following compound (z-72) (maximum absorption wavelength in dichloromethane: 937 nm), and dichloromethane are added as compound (Z), and the resin concentration is 20 parts by mass. % Was prepared and filtered through a millipore filter having a pore size of 5 ⁇ m to obtain a resin solution (E20-2).
  • the resin composition (2) is applied to both sides of a transparent glass support "OA-10G" (thickness 200 ⁇ m) manufactured by Nippon Electric Glass Co., Ltd., which is cut to a size of 200 mm ⁇ 200 mm, and the thickness after drying is about. After applying with spin coating so as to be 1 ⁇ m, the solvent is volatilized and removed by heating on a hot plate at 80 ° C. for 2 minutes to form a glass support and a coating resin layer (1) and a coating resin layer (2) described later. An adhesive layer that functions as an adhesive layer was formed.
  • OA-10G thickness 200 ⁇ m
  • a resin solution (E21-1) was applied to one side of the glass support on which the adhesive layer was formed so that the film thickness after drying was 10 ⁇ m, and the temperature was 80 ° C. on a hot plate. The solvent was volatilized and removed by heating for 5 minutes to form a coating resin layer (2). Further, using a spin coater, a resin solution (E21-2) was applied to the other surface of the glass support on which the adhesive layer was formed so that the film thickness after drying was 10 ⁇ m, and 80 on a hot plate. The solvent was volatilized and removed by heating at ° C. for 5 minutes to form the coating resin layer (1).
  • Example 2 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.226 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 12.
  • Example 2 a total of 28 dielectric multilayer films (I ) in which silica (SiO 2 ) layers and titanium (TiO 2 ) layers are alternately laminated on one side of the obtained base material. ), And a total of 24 layers of dielectric multilayer film (II) formed by alternately laminating silica (SiO 2 ) layers and titania (TiO 2 ) layers on the other surface of the base material. , An optical filter having a thickness of about 0.226 mm was obtained.
  • the design of the dielectric multilayer film was carried out using the same design parameters as in Example 1 in consideration of the wavelength dependence of the refractive index of the base material and the like, as in Example 1. The spectral transmittance measured from the vertical direction of the obtained optical filter was measured, and Tg and Th were determined. The results are shown in Table 12.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Optical Filters (AREA)
PCT/JP2020/040085 2019-11-01 2020-10-26 樹脂組成物、化合物（ｚ）、光学フィルターおよびその用途 Ceased WO2021085372A1 (ja)

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Application Number Priority Date Filing Date Title
KR1020227013997A KR20220097889A (ko) 2019-11-01 2020-10-26 수지 조성물, 화합물 (z), 광학 필터 및 그 용도
CN202080073048.9A CN114616291B (zh) 2019-11-01 2020-10-26 树脂组合物、化合物、光学滤波器、及光学传感装置
JP2021553598A JP7663505B2 (ja) 2019-11-01 2020-10-26 樹脂組成物、化合物（ｚ）、光学フィルターおよびその用途
JP2024228694A JP7816477B2 (ja) 2019-11-01 2024-12-25 樹脂組成物、化合物（ｚ）、光学フィルターおよびその用途

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JP2019199897 2019-11-01
JP2019-199897 2019-11-01
JP2020135282 2020-08-07
JP2020-135282 2020-08-07

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021070782A (ja) * 2019-11-01 2021-05-06 Jsr株式会社 樹脂組成物、樹脂層および光学フィルター
JP2021134350A (ja) * 2020-02-21 2021-09-13 Jsr株式会社 樹脂組成物、化合物（Ｚ）、基材（ｉ）、光学フィルターおよびその用途
WO2025142714A1 (ja) * 2023-12-25 2025-07-03 株式会社日本触媒 樹脂組成物、その製造方法、その用途、成形体の製造方法、及び、撮像素子の製造方法

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TWI831649B (zh) 2023-03-03 2024-02-01 大立光電股份有限公司 成像鏡頭、相機模組與電子裝置
TWI829562B (zh) * 2023-03-21 2024-01-11 澤米科技股份有限公司 雙通帶濾光元件
KR20250105164A (ko) * 2023-12-29 2025-07-08 (주)이녹스첨단소재 웨이퍼 이면 연삭용 점착 필름

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