Optical film, composition for forming colored layer, dipyrromethene cobalt complex and display device

Patent metadata

Field	Value
Publication number	US-2025089549-A1
Application number	US-202418765193-A
Country	US
Kind code	A1
Filing date	Jul 5, 2024
Priority date	Jan 7, 2022
Publication date	Mar 13, 2025
Grant date	—

Abstract

An optical film includes: a transparent substrate; and a colored layer laminated on at least one side of the transparent substrate, the colored layer containing a dye (A), the dye (A) containing a colorant having a wavelength of maximum absorption in the range of 470 nm to 530 nm, the colorant containing a dipyrromethene cobalt complex having a structure represented by formula (I), in which R 1 to R 7 are combined such that a free energy change between before and after the reaction, calculated by applying R 1 to R 7 in the formula (I) to a predetermined reaction formula (II) using a quantum chemical calculation program Gaussian 16 with a calculation method B3LYP and a basis function 6-31G (d,p) (however, a basis function LanL2DZ is assigned to elements having an atomic number greater than that of Kr in the periodic table), is 0.92 kcal/mol or greater.

First claim

What is claimed is:

1 . An optical film, comprising:
a transparent substrate; and a colored layer laminated on at least one side of the transparent substrate, the colored layer containing a dye (A), the dye (A) containing a colorant having a wavelength of maximum absorption in the range of 470 nm to 530 nm, the colorant containing a dipyrromethene cobalt complex having a structure represented by the following formula (I), in which R 1 to R 7 in the following formulas (I) and (II) are each independently a monovalent group selected from the group consisting of a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an alkylthio group, an aromatic hydrocarbon group, a heterocyclic group, a hydroxyl group, a mercapto group, a nitro group, a substituted amino group, an unsubstituted amino group, a cyano group, a sulfo group, an ester group and an acyl group, wherein the colorant satisfies at least one of the following conditions (1) to (4): (1) The colorant has a wavelength of maximum absorption in the range of 470 nm to 530 nm, and, when thermogravimetric measurement is performed for the dipyrromethene cobalt complex under conditions of a gas flow rate of 500 mL/min and a temperature increase rate of 10° C./min, a 5% weight loss temperature when the gas is air and a 5% weight loss temperature when the gas is nitrogen are both 300° C. or higher, and when thermogravimetric measurement is performed under conditions of a nitrogen flow rate of 500 mL/min and a temperature increase rate of 10° C./min, a 50% weight loss temperature is 360° C. or higher and 470° C. or lower; (2) The colorant has a wavelength of maximum absorption of 489 nm to 500 nm and a full width at half maximum of an absorption peak of 22 nm or less in acetone solution with a concentration of 5.0×10 −6 M, and has a full width at half maximum of an absorption peak of 30 nm or less; (3) The colorant has a wavelength of maximum absorption in the range of 470 nm to 530 nm, and contains a dipyrromethene cobalt complex in which R 1 to R 7 are combined such that a free energy change between before and after the reaction, calculated by applying R 1 to R 7 in the formula (I) to the following reaction formula (II) using a quantum chemical calculation program Gaussian 16 with a calculation method B3LYP and a basis function 6-31G (d,p) (however, a basis function LanL2DZ is assigned to elements having an atomic number greater than that of Kr in the periodic table), is 0.92 kcal/mol or greater; and (4) The colorant has a wavelength of maximum absorption in the range of 470 nm to 530 nm, and contains a dipyrromethene cobalt complex in which R 1 to R 7 are combined such that a free energy change between before and after the reaction, calculated by applying R 1 to R 7 in the formula (I) to the following reaction formula (II) using a quantum chemical calculation program Gaussian 16 with a calculation method B3LYP and a basis function 6-31G (d,p) (however, a basis function LanL2DZ is assigned to elements having an atomic number greater than that of Kr in the periodic table), is −1.0 kcal/mol or greater, and at least one of R 1 to R 4 is a hydrogen atom or a halogen atom.

2 . The optical film of claim 1 , wherein
the colorant satisfies the condition (2).

3 . The optical film of claim 1 , wherein,
when thermogravimetric measurement is performed for the dipyrromethene cobalt complex of the condition (1) under conditions of a gas flow rate of 500 mL/min and a temperature increase rate of 10° C./min, a difference between a 50% weight loss temperature when the gas is air and a 50% weight loss temperature when the gas is nitrogen is 10° C. or less.

4 . The optical film of claim 1 , wherein,
in the reaction formula (II) in which boron dipyrromethene having a structure represented by the following formula (III) reacts with singlet oxygen, the dipyrromethene cobalt complex of the condition (2) has a free energy change ΔG between before and after reaction, calculated using a quantum chemical calculation program Gaussian 16 with a calculation method B3LYP and a basis function 6-31G (d,p) (however, a basis function LanL2DZ is assigned to elements in which R 5 in the formula (I) has an atomic number greater than that of Kr), of −1.0 kcal/mol or greater:

where R 1 to R 7 in formula (III) each represent the same monovalent groups as R 1 to R 7 in the formula (I).

5 . The optical film of claim 1 , wherein,
in the dipyrromethene cobalt complex of the condition (3), at least one of R 1 to R 4 is a hydrogen atom or a halogen atom.

6 . The optical film of claim 1 , wherein,
in the dipyrromethene cobalt complex of the condition (3) or (4), R 1 and R 3 are each independently a hydrogen atom or a halogen atom and R 2 and R 4 are each independently an alkyl group having 1 to 4 carbon atoms, or R 1 and R 3 are each independently an alkyl group having 1 to 4 carbon atoms and R 2 and R 4 are each independently a halogen atom.

7 . The optical film of claim 1 , wherein,
in the dipyrromethene cobalt complex, R 5 is a hydrogen atom.

8 . The optical film of claim 1 , wherein,
in the dipyrromethene cobalt complex of the conditions (1) to (3), R 1 to R 4 are alkyl groups, and a sum of carbon numbers of R 1 and R 2 is 3 or greater and a sum of carbon numbers of R 3 and R 4 is 3 or greater.

9 . The optical film of claim 1 , wherein
the dipyrromethene cobalt complex has a structure represented by the following formula (I-1):

where R 1 to R 5 in formula (I-1) each represent the same monovalent groups as R 1 to R 5 in the formula (I), and R 8 and R 9 each independently represent an alkyl group having 1 to 6 carbon atoms.

10 . The optical film of claim 9 , wherein
an acetone solution of the dipyrromethene cobalt complex has a molar absorption coefficient of 190,000 L/(mol·cm) or greater.

11 . The optical film of claim 10 , wherein,
in the dipyrromethene cobalt complex, R 8 and R 9 are each independently a methyl group or an ethyl group.

12 . A composition for forming a colored layer, the composition comprising:
a dye (A); a photopolymerizable compound (B); and a photopolymerization initiator (C), the dye (A) containing a colorant, the colorant containing a dipyrromethene cobalt complex having a structure represented by the following formula (I), in which R 1 to R 7 in the following formulas (I) and (II) are each independently a monovalent group selected from the group consisting of a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an alkylthio group, an aromatic hydrocarbon group, a heterocyclic group, a hydroxyl group, a mercapto group, a nitro group, a substituted amino group, an unsubstituted amino group, a cyano group, a sulfo group, an ester group and an acyl group, wherein the colorant satisfies at least one of the following conditions (1) to (4): (1) The colorant has a wavelength of maximum absorption in the range of 470 nm to 530 nm, and, when thermogravimetric measurement is performed for the dipyrromethene cobalt complex under conditions of a gas flow rate of 500 mL/min and a temperature increase rate of 10° C./min, a 5% weight loss temperature when the gas is air and a 5% weight loss temperature when the gas is nitrogen are both 300° C. or higher, and when thermogravimetric measurement is performed un

Assignees

• Toppan Holdings Inc

Inventors

• Tagami Hanae
• Furukawa Shigeki
• SHIMADA Erika
• Ishimaru Yoshiko
• FUTAMATA Kai
• Ishikawa Shinya

Classifications

• B32B2551/00

  Optical elements · CPC title

• B32B2307/40

  having particular optical properties · CPC title

• B32B2307/7244

  Oxygen barrier · CPC title

• B32B2255/28

  Multiple coating on one surface · CPC title

• B32B2255/26

  Polymeric coating · CPC title