Abstract: According to the present invention a pyrromethene boron complex or a color changing composition containing the pyrromethene boron complex is used to provide an organic light emitting material which has excellent luminous efficiency and durability and is suitable for use as a color changing material in a liquid crystal display or LED lighting.
CLAIMS
[Claim 1]
A color conversion composition for converting incident light into light having longer wavelength than the incident light, wherein the color conversion composition comprises a compound represented by formula (1) and a binder resin:
[Chem. 1]
(wherein
XisC-R7orN,
each of R1 to R7, which may be the same as or different from one another, is selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted amide group, a substituted or unsubstituted amino group, a nitro group, a
substituted or unsubstituted silyl group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine oxide group, and
each of R8 and R9, which may be the same as or different from one another, is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a halogen,
provided that at least either one of the following (A) and (B) is satisfied:
(A) at least one of R1 to R7 is an electron-withdrawing group, and
(B) each of R1, R3, R4 and R6, which may be the same as or different from one another, is hydrogen, a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, or a cyano group, X is C-R7, and R7 is either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group).
[Claim 2]
The color conversion composition according to claim 1, wherein in formula (1),
(A) is satisfied and at least one of R1 to R6 is an electron-withdrawing group. [Claim 3]
The color conversion composition according to claim 2, wherein X is C-R7 and R7 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. [Claim 4]
The color conversion composition according to claim 2 or 3, wherein X is C-R7 and R7 is represented by the following formula (2):
(wherein r is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted amino group, k is an integer of 1 to 3, and when k is 2 or more, r may be the same as or different from
one another). [Claim 5]
The color conversion composition according to claim 4, wherein in formula (2), r is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. [Claim 6]
The color conversion composition according to claim 1, wherein in formula (1), (A) is satisfied, X is C-R7, and R7 is an electron-withdrawing group. [Claim 7]
The color conversion composition according to claim 1, wherein in formula (1), (A) is satisfied and the compound represented by formula (1) is a compound represented by formula (3):
(wherein
each of R1 to R6, R8 and R9 is the same as that in formula (1),
L1 and L2 are a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and
x and y are an integer of 1 to 5,
provided that R17 is an electron-withdrawing group and at least one of R1 to R6
is an electron-withdrawing group). [Claim 8]
The color conversion composition according to any one of claims 1 to 7, wherein in formula (1), (A) is satisfied and at least one of R2 and R5 is an electron-withdrawing group. [Claim 9]
The color conversion composition according to any one of claims 1 to 8, wherein in formula (1), (A) is satisfied and the electron-withdrawing group is fluorine, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, or a cyano group. [Claim 10]
The color conversion composition according to any one of claims 1 to 9, wherein at least one of R1, R3, R4 and R6 is a substituted or unsubstituted phenyl group. [Claim 11]
The color conversion composition according to claim 1, wherein in formula (1), (B) is satisfied and R7 is represented by the following formula (2):
(wherein r is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a
substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted amino group, k is an integer of 1 to 3, and when k is 2 or more, r may be the same as or different from one another). [Claim 12]
The color conversion composition according to claim 11, wherein in formula (2), r is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. [Claim 13]
The color conversion composition according to claim 12, wherein in formula (2), r is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a halogen. [Claim 14]
The color conversion composition according to any one of claims 11 to 13, wherein in formula (2), k is 1 or 2. [Claim 15]
The color conversion composition according to any one of claims 1 to 14, wherein at least one of R1, R3, R4 and R6 is a substituted or unsubstituted alkyl group.
[Claim 16]
A pyrromethene-boron complex represented by the following formula (3):
(wherein
each of R1 to R6, which may be the same as or different from one another, is selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a halogen, a cyano group, an aldehyde group, a substituted or unsubstituted carbonyl group, a carboxyl group, a substituted or unsubstituted oxycarbonyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted amide group, a substituted or unsubstituted amino group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted siloxanyl group, a substituted or unsubstituted boryl group, and a substituted or unsubstituted phosphine
oxide group,
each of R8 and R9 is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted alkynyl group, a hydroxyl group, a thiol group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryl ether group, a substituted or unsubstituted aryl thioether group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a halogen,
L1 and L2 are a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and
x and y are an integer of 1 to 5,
provided that R17 is an electron-withdrawing group and at least one of R1 to R6 is an electron-withdrawing group). [Claim 17]
The pyrromethene-boron complex according to claim 16, wherein in formula (3), at least one of R2 and R5 is an electron-withdrawing group. [Claim 18]
The pyrromethene-boron complex according to claim 16 or 17, wherein in formula (3), at least one of R1, R3, R4 and R6 is a substituted or unsubstituted alkyl group. [Claim 19]
The pyrromethene-boron complex according to any one of claims 16 to 18, wherein in formula (3), at least one of R1, R3, R4 and R6 is a substituted or unsubstituted aryl group.
[Claim 20]
The pyrromethene-boron complex according to any one of claims 16 to 19, wherein the electron-withdrawing group is fluorine, a fluorine-containing aryl group, a fluorine-containing heteroaryl group, a fluorine-containing alkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group, or a cyano group. [Claim 21]
The pyrromethene-boron complex according to any one of claims 16 to 20, which emits light having a peak wavelength observed in the region of 500 to 580 nm, by use of excitation light. [Claim 22]
The pyrromethene-boron complex according to any one of claims 16 to 20, which emits light having a peak wavelength observed in the region of 580 to 750 nm, by use of excitation light. [Claim 23]
The color conversion composition according to any one of claims 1 to 15, wherein the compound represented by formula (1) emits light having a peak wavelength observed in the region of 500 to 580 nm, by use of excitation light. [Claim 24]
The color conversion composition according to any one of claims 1 to 15, wherein the compound represented by formula (1) emits light having a peak wavelength observed in the region of 580 to 750 nm, by use of excitation light. [Claim 25]
The color conversion composition according to any one of claims 1 to 15,
wherein the color conversion composition comprises the following luminescent materials (a) and (b) and at least one of the luminescent materials (a) and (b) is a compound represented by formula (1):
(a) a luminescent material emitting light having a peak wavelength observed in the region of 500 to 580 nm by use of excitation light, and
(b) a luminescent material emitting light having a peak wavelength observed in the region of 580 to 750 nm upon excitation by at least either one of excitation light and luminescence from the luminescent material (a).
[Claim 26]
The color conversion composition according to claim 25, wherein both of the luminescent materials (a) and (b) are a compound represented by formula (1). [Claim 27]
The color conversion composition according to claim 25 or 26, wherein a content wa of the luminescent material (a) and a content wb of the luminescent material (b) have a relationship of wa>wb. [Claim 28]
The color conversion composition according to any one of claims 1 to 15, further comprising a solvent. [Claim 29]
The color conversion composition according to any one of claims 1 to 15, wherein the binder resin is a thermoplastic resin. [Claim 30]
A color conversion film comprising a layer comprising a cured product of the color conversion composition according to any one of claims 1 to 15.
[Claim 31]
The color conversion film according to claim 30, further comprising a barrier film. [Claim 32]
A light source unit comprising a light source and the color conversion film according to claim 30 or 31. [Claim 33]
The light source unit according to claim 32, wherein the light source is a light-emitting diode having a maximum light emission in a range of 430 to 500 nm. [Claim 34]
The light source unit according to claim 33, wherein the light source is a light-emitting diode having a maximum light emission in a range of 450 to 470 nm. [Claim 35]
The light source unit according to claim 32, wherein the light source is a light-emitting diode having an emission peak wavelength in a range of 430 to 470 nm and an emission wavelength region in a range of 400 to 500 nm, and an emission spectrum of the light-emitting diode satisfies mathematical expression (1):
(wherein a is a light emission intensity at the emission wavelength peak of the emission spectrum, and |3 is a light emission intensity at a wavelength of emission wavelength peak+ 15 nm). [Claim 36]
A display comprising the color conversion film according to claim 30 or 31.
[Claim 37]
A lighting comprising the color conversion film according to claim 30 or 31.
| # | Name | Date |
|---|---|---|
| 1 | 201747042185-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [24-11-2017(online)].pdf | 2017-11-24 |
| 2 | 201747042185-STATEMENT OF UNDERTAKING (FORM 3) [24-11-2017(online)].pdf | 2017-11-24 |
| 3 | 201747042185-PROOF OF RIGHT [24-11-2017(online)].pdf | 2017-11-24 |
| 4 | 201747042185-PRIORITY DOCUMENTS [24-11-2017(online)].pdf | 2017-11-24 |
| 5 | 201747042185-POWER OF AUTHORITY [24-11-2017(online)].pdf | 2017-11-24 |
| 6 | 201747042185-FORM 1 [24-11-2017(online)].pdf | 2017-11-24 |
| 7 | 201747042185-DRAWINGS [24-11-2017(online)].pdf | 2017-11-24 |
| 8 | 201747042185-DECLARATION OF INVENTORSHIP (FORM 5) [24-11-2017(online)].pdf | 2017-11-24 |
| 9 | 201747042185-COMPLETE SPECIFICATION [24-11-2017(online)].pdf | 2017-11-24 |
| 10 | 201747042185-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [24-11-2017(online)].pdf | 2017-11-24 |
| 11 | 201747042185.pdf | 2017-11-28 |
| 12 | Correspondence By Agent_Form 1_07-12-2017.pdf | 2017-12-07 |
| 13 | 201747042185-FORM 3 [18-04-2018(online)].pdf | 2018-04-18 |
| 14 | 201747042185-FORM 18 [12-12-2018(online)].pdf | 2018-12-12 |
| 15 | 201747042185-FORM 3 [26-08-2019(online)].pdf | 2019-08-26 |
| 16 | 201747042185-FORM 3 [26-08-2019(online)]-1.pdf | 2019-08-26 |
| 17 | 201747042185-FER.pdf | 2019-11-26 |
| 18 | 201747042185-PETITION UNDER RULE 137 [16-03-2020(online)].pdf | 2020-03-16 |
| 19 | 201747042185-PETITION UNDER RULE 137 [16-03-2020(online)]-1.pdf | 2020-03-16 |
| 20 | 201747042185-OTHERS [16-03-2020(online)].pdf | 2020-03-16 |
| 21 | 201747042185-MARKED COPIES OF AMENDEMENTS [16-03-2020(online)].pdf | 2020-03-16 |
| 22 | 201747042185-MARKED COPIES OF AMENDEMENTS [16-03-2020(online)]-1.pdf | 2020-03-16 |
| 23 | 201747042185-Information under section 8(2) [16-03-2020(online)].pdf | 2020-03-16 |
| 24 | 201747042185-FORM 3 [16-03-2020(online)].pdf | 2020-03-16 |
| 25 | 201747042185-FORM 13 [16-03-2020(online)].pdf | 2020-03-16 |
| 26 | 201747042185-FORM 13 [16-03-2020(online)]-1.pdf | 2020-03-16 |
| 27 | 201747042185-FER_SER_REPLY [16-03-2020(online)].pdf | 2020-03-16 |
| 28 | 201747042185-DRAWING [16-03-2020(online)].pdf | 2020-03-16 |
| 29 | 201747042185-COMPLETE SPECIFICATION [16-03-2020(online)].pdf | 2020-03-16 |
| 30 | 201747042185-CLAIMS [16-03-2020(online)].pdf | 2020-03-16 |
| 31 | 201747042185-certified copy of translation [16-03-2020(online)].pdf | 2020-03-16 |
| 32 | 201747042185-ABSTRACT [16-03-2020(online)].pdf | 2020-03-16 |
| 33 | 201747042185-PatentCertificate22-01-2021.pdf | 2021-01-22 |
| 34 | 201747042185-IntimationOfGrant22-01-2021.pdf | 2021-01-22 |
| 1 | 201747042185searchreport_22-11-2019.pdf |