# US 11,898,075 B2 · Yellow light emitting device

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- Number: US 11,898,075 B2
- Document ID: US11898075B2
- Status: Granted
- Kind: B2
- Application number: 16/982,423
- Filed: 2019-03-19
- Published: 2021-02-25
- Granted: 2024-02-13
- Earliest claimed: 2018-03-20
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Hannah Stephanie Mangold; Sorin Ivanovici; Martin Koenemann; Siang Fu Hong; Chia Wei Tsai; Yen Te Lee; Wei Cheng Chou
- Web page: https://patentgrep.com/patent/US11898075B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- H10H 20/8512: {Wavelength conversion materials}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- H10H 20/882: {Scattering means (H10H20/82 takes precedence)}
- Y02B 20/00: Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10H: INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
- Y02B: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS

## Abstract

A yellow light emitting device may have a light source and a color converter wherein at most 1% of the total emitted radiant power of the yellow light emitting device is emitted in a wavelength range shorter than 520 nm, as well as the use of the yellow light emitting device.

## Claims

### Claim 1

A yellow light emitting device, comprising:
(i) a light source comprising a blue light emitting diode with a center wavelength of emission in a range of from 400 nm to 480 nm, and/or a white light emitting diode having a correlated color temperature between in a range of from 2 700 to 30 000 K;
(ii) a color converter comprising an organic fluorescent dye in a polymer matrix, the organic fluorescent dye comprising a structural unit of formula (I)
wherein one or more CH groups of the six-membered ring of the benzimidazole structure are optionally replaced by nitrogen and wherein
n1 is a number from 0 to (10-p1) for each structural unit of the formula (1), p1 being a number of the CH groups replaced by nitrogen in the six-membered ring of the benzimidazole structure,
X1 is a chemical bond, O, S, SO, SO2, or NR1, and
R is an aliphatic radical, cycloaliphatic radical, aryl, or heteroaryl, or an aromatic or heteroaromatic ring or ring system, fused to other aromatic rings of the structural unit of the formula (I), or F, Cl, Br, CN, or H when X1 is not a chemical bond, two R radicals optionally being joined to give one cyclic radical,
X1 and R, when n1>one, optionally being the same or different;
R1 is independently hydrogen, C1-C18-alkyl or cycloalkyl, the carbon chain of which optionally comprising an —O—, —S—, —CO—, —SO— and/or —SO2— moiety, or aryl or heteroaryl
wherein the organic fluorescent dye absorbs at least a part of light emitted by the light source and emits light comprising a wavelength in a range of from 520 to 590 nm,
wherein the organic fluorescent dye in the color converter has a weight percentage satisfying equation (A)
20[%×μm]≤w1×d≤100[%×μm] (A),
wherein w1 is the weight percentage of the organic fluorescent dye in the polymer matrix, based on total polymer weight, and d is thickness of the color converter in μm,
wherein at most 1% of total emitted radiant power of the yellow light emitting device is emitted in a wavelength range shorter than 520 nm, and
wherein the yellow-light emitting device has a luminous efficiency of at least 80 lumen/watt.

### Claim 2 (depends on 1)

The device of claim 1, wherein at most 0.8% of the total emitted radiant power is emitted in a wavelength range shorter than 520 nm.

### Claim 3 (depends on 1)

The device of claim 1, having a wall plug efficiency from at least 25%.

### Claim 4 (depends on 1)

The device of claim 1, wherein the light source is a white light emitting diode having a correlated color temperature in a range of from 2 700 to 30 000 K, and
wherein the yellow light's luminous efficiency is greater than 70% of a luminous efficiency of the white light emitting diode.

### Claim 5 (depends on 1)

The device of claim 1, suitable to emit a light spectrum having chromaticity coordinates x,y according to the 1931 CIE standard colorimetric system with an ellipse of an equation and parameters:
(
(
x
-
h
)
⁢
⁢
cos
⁡
(
A
)
+
(
y
-
k
)
⁢
⁢
sin
⁡
(
A
)
)
2
(
a
2
)
+
(
(
x
-
h
)
⁢
⁢
sin
⁡
(
A
)
-
(
y
-
k
)
⁢
⁢
cos
⁡
(
A
)
)
2
(
b
2
)
=
1
,
wherein h and k, and a and b are the shifts and semi-axis in x and y directions respectively and A is an angle measured from x axis, wherein h is 0.52, k is 0.46, a is 0.25, b is 0.03, and A is −42.

### Claim 6 (depends on 1)

The device of claim 1, wherein the organic fluorescent dye comprises a compound of formula (I-5) and/or (I-7):

### Claim 7 (depends on 1)

The device of claim 1, wherein the color converter comprises a further organic fluorescent dye (A) comprising
(a) a perylene-3,4,9,10-tetracarboxylic acid diimide compound of formula (II)
wherein
R21 and R22 are independently C1-C30-alkyl, C3-C8-cycloalkyl, C6-C14-aryl, hetaryl, or C6-C14-aryl-C1-C10-alkylene, the (hetero)aromatic ring being optionally substituted by a C1-C10-alkyl;
(b) an aryloxy-substituted perylene-3,4,9,10-tetracarboxylic acid diimide compound of formula (III)
wherein
q is 1 to 4,
R30 is aryloxy optionally substituted by halogen, C1-C10-alkyl, or C6-C10-aryl, the R30 radicals being at one or more position indicated by *,
R31 and R32 are independently C1-C30-alkyl, C3-C8-cycloalkyl, C6-C14-aryl, hetaryl, or C6-C14-aryl-C1-C10-alkylene, where the (hetero)aromatic ring being optionally substituted by C1-C10-alkyl;
(c) a core-cyanated naphthoylbenzimidazole compound of formula (IV)
wherein
one of R43 or R44 is independently cyano and the other radical R43 or R44 is cyano, phenyl, 4-cyanophenyl, or phenyl comprising 1, 2, or 3 C1-C10-alkyl substituents,
R47, R48, R49, and R410 are independently of each other are hydrogen, cyano, phenyl, 4-cyanophenyl, or phenyl comprising 1, 2, or 3 C1-C10-alkyl substituents,
and/or
(d) a perylene-3,4,9,10-tetracarboxylic acid diimide compound with rigid 2,2′-biphenoxy bridges of formula (V)
wherein
R51 and R52 are independently hydrogen, C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkyloxy, C6-C24-aryl, C6-C24-aryloxy,
R53, R54, R55, R56, R57, R58, R59, R510, R511, R512, R513, R514, R515, R516, R517 and R518 are independently hydrogen, halogen, cyano, hydroxyl, mercapto, nitro, -NE51E52, —NRAr51CORA52, —CONRAr51RAr52, —SO2NRA51RA52, —COORAr51, —SO3RAr52, C1-C30-alkyl, polyalkyleneoxy, C1-C30-alkoxy, C1-C30-alkylthio, C3-C20-cycloalkyl, C3-C20-cycloalkoxy, C6-C24-aryl, C6-C24-aryloxy, or C6-C24-arylthio,
wherein R53 and R54, R54 and R55, R55 and R56, R56 and R57, R57 and R58, R58 and R59, R59 and R510, R511 and R512, R512 and R513, R513 and R514, R55 and R515, R515 and R516, R516 and R517, and/or R517 and R518, together with the carbon atoms of the biphenylyl moiety to which they are bonded, optionally form a further fused ring system,
wherein E51 and E52 are independently hydrogen, C1-C18-alkyl, C2-C18-alkenyl, C2-C18-alkynyl, C3-C20-cycloalkyl, or C6-C10-aryl, and
RAr51 and RAr52 are independently hydrogen, C1-C18-alkyl, C3-C20-cycloalkyl, heterocyclyl, C6-C20-aryl, or heteroaryl.

### Claim 8 (depends on 7)

The device of claim 7, wherein the further organic fluorescent dye comprises the compound of formula (II) and/or the compound of formula (III).

### Claim 9 (depends on 7)

The device of claim 7, wherein R21 and R22 in the compound of formula II are independently C1-C18-alkyl, phenyl, or naphthyl, the phenyl or naphthyl being optionally substituted by 1, 2, or 3 C1-C4-alkyl radicals.

### Claim 10 (depends on 7)

The device of claim 7, wherein in the compound of formula (III) is present, and
R30 is phenoxy, optionally substituted by 1 or 2 fluorine, chlorine, C1-C10-alkyl, or phenyl,
R31 and R32 are each independently C1-C10-alkyl, 2,6-di(C1-C10-alkyl)phenyl, or 2,4-di(C1-C10-alkyl)phenyl, and
q is 2, 3, or 4.

### Claim 11 (depends on 7)

The device of claim 7, wherein the color converter comprises the further organic fluorescent dye (A) in an amount satisfying equation (B)
5[%×μm]≤w2×d≤80[%×μm] (B),
wherein w2 is a weight percentage based on a combined weight of all further organic fluorescent dyes and the total polymer weight, and d is a thickness of the color converter in μm.

### Claim 12 (depends on 1)

The device of claim 1, wherein the polymer matrix comprises a polystyrene, polycarbonate, polyacrylate, polymethylmethacrylate, polymethacrylate, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl chloride, polybutene, silicone, epoxy resin, polyvinyl alcohol, poly(ethylene vinylalcohol)-copolymer, polyacrylonitrile, polyvinylidene chloride, polystyrene acrylonitrile, polybutylene terephthalate, polyethylene terephthalate, 2,5-furandicarboxylate polyester, polyvinyl butyrate, polyvinyl chloride, polyamide, polyoxymethylene, polyimide, and/or polyetherimide.

### Claim 13 (depends on 1)

The device of claim 1, wherein the color converter comprises a light scattering agent.

### Claim 14 (depends on 1)

The device of claim 1, wherein the color converter comprises an inorganic luminescent material comprising quantum dots, garnets, silicates, sulfides, nitrides, and/or oxynitrides.

### Claim 15 (depends on 1)

The device of claim 1, wherein the polymer matrix comprises polystyrene, polycarbonate, polyethylene terephthalate, or polyethylene furanoate.

### Claim 16 (depends on 1)

The device of claim 1, wherein the color converter comprises a poly(methyl methacrylate)-based scattering agent, silicone-based scattering agent, or TiO2.

### Claim 17 (depends on 1)

A workspace configured for handling material sensitive to light at wavelengths below 520 nm, the workspace comprising:
the device of claim 1.

### Claim 18

A method of providing yellow light, wherein at most 1% of total radiant power is within a spectral range of less than 520 nm, the method comprising:
arranging, to receive at least a part of light emitted by a light source comprising a blue light emitting diode with a center wavelength of emission in a range of from 400 nm to 480 nm and/or a white light emitting diode having a correlated color temperature in a range of from 2 700 to 30 000 K;
a color converter comprising an organic fluorescent dye in a polymer matrix, the organic fluorescent dye comprising a structural unit of formula (I)
wherein one or more CH groups of the six-membered ring of the benzimidazole structure is optionally replaced by nitrogen,
n1 is a number from 0 to (10-p1) for each structural unit of the formula (I); p1 being a number of the CH units replaced by nitrogen in the six-membered ring of the benzimidazole structure,
X1 is a chemical bond, O, S, SO, SO2, or NR1, and
R is an aliphatic radical, cycloaliphatic radical, aryl, or heteroaryl, or an aromatic or heteroaromatic ring or ring system, fused to other aromatic rings of the structural unit of the formula (I), or F, Cl, Br, CN, or H when X1 is not a chemical bond, two R radicals being optionally joined to give one cyclic radical,
X1 and R, when n1>one, being the same or different,
R1 is independently hydrogen, C1-C18-alkyl, or cycloalkyl, the carbon chain of which optionally comprising an —O—, —S—, —CO—, —SO—, and/or —SO2 moiety, or aryl or heteroaryl, and
wherein the organic fluorescent dye is capable of absorbing at least a part of the light emitted by the light source and emitting light comprising a wavelength in a range of from 520 to 590 nm,
wherein the organic fluorescent dye has a weight percentage in the color converter satisfying equation (A)
20[%×μm]≤w1×d≤100[%×μm] (A),
wherein w1 is a weight percentage of the organic fluorescent dye in the polymer matrix based on total polymer weight, and d is a thickness of the color converter in μm.

### Claim 19 (depends on 18)

The method of claim 18, wherein the organic fluorescent dye comprises a compound of formula (I-5) and/or (I-7):