WO2014122071A1 - Augmentation de la durée de vie d'un luminophore organique à l'aide d'une excitation différente de l'excitation maximale - Google Patents

Augmentation de la durée de vie d'un luminophore organique à l'aide d'une excitation différente de l'excitation maximale Download PDF

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Publication number
WO2014122071A1
WO2014122071A1 PCT/EP2014/051900 EP2014051900W WO2014122071A1 WO 2014122071 A1 WO2014122071 A1 WO 2014122071A1 EP 2014051900 W EP2014051900 W EP 2014051900W WO 2014122071 A1 WO2014122071 A1 WO 2014122071A1
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Prior art keywords
light
luminescent material
lighting device
source
wavelength
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PCT/EP2014/051900
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English (en)
Inventor
Rifat Ata Mustafa Hikmet
Dirk VELDMAN
Ties Van Bommel
Johan Lub
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Koninklijke Philips N.V.
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Publication of WO2014122071A1 publication Critical patent/WO2014122071A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Definitions

  • the invention relates to a lighting device comprising a source of light and a luminescent material.
  • WO2012046175 describes a light-emitting arrangement comprising a light source adapted to emit light of a first wavelength, a wavelength converting member comprising an organic wavelength converting material adapted to receive light of said first wavelength and to convert at least part of the received light to light of a second wavelength, said wavelength converting member and said light source being mutually spaced apart; and a sealing structure at least partially surrounding said wavelength converting member to fonn a sealed cavity containing at least said wavelength converting member, the gas pressure within said sealed cavity being 1 * 10 5 bar ( 1 Pa) or less.
  • the organic luminescent material or organic phosphor may for instance include a perylene derivative.
  • WO2012/042434 describes a light-emitting arrangement with organic phosphor, especially a light-emitting arrangement, comprising: a light source adapted to emit light of a first wavelength; a wavelength converting member comprising an organic wavelength converting compound adapted to receive light of said first wavelength and to convert at least part of the received light to light of a second wavelength, said wavelength converting member and said light source being mutually spaced apart; and a sealing structure at least partially surrounding said wavelength converting member to form a sealed cavity containing at least said wavelength converting member, said sealed cavity containing an inert gas and oxygen gas, the concentration of oxygen gas being in the range of from 0.05 to 3 % based on the total volume within said sealed cavity.
  • WO2012/ 140542 describes a luminescent converter, a phosphor enhanced light source or a luminaire having a CRI larger than 80, especially a luminescent converter a phosphor-enhanced light source and a luminaire are provided.
  • the luminescent converter comprises a first organic luminescent material, a second organic luminescent material and a third inorganic luminescent material.
  • the first organic luminescent material, the second organic luminescent material and the inorganic luminescent material absorb a portion of light emitted by the light source and/or absorbs a portion of light emitted by at least one of the other luminescent materials.
  • the first organic luminescent material converts at least a part of the absorbed light into light of a first color distribution.
  • the second organic luminescent material converts at least a part of the absorbed light into light of a second color distribution.
  • the inorganic luminescent material converts at least a part of the absorbed light into a third color distribution to compensate self-absorption of light by at least one of the first organic luminescent material and the second organic luminescent material
  • EP0227980 describes fluorescent aroxysubstituted 3,4,9.10- perylenetetracarboxylic acid-dumides and their use for the concentration of lights in small areas.
  • Organic phosphors (herein also indicated as organic luminescent materials) are currently being considered for (remote) phosphor applications where blue light emitting diodes arc used for pumping green to red emitting phosphor in order to obtain white light.
  • Organic phosphors have a large number of advantages as compared with inorganic phosphors. The position and the band width of the luminescence spectrum can be designed with ease to be anywhere in the visible range to obtain high efficacy.
  • One of the drawbacks of the organic phosphor may be their lifetime during irradiation.
  • the molecules bleach. It is usually assumed that irradiation with shorter wavelengths has a negative influence on the lifetime of the molecules as compared to irradiation at longer wavelengths.
  • the bleaching depends on the absorbed light per molecule.
  • the lifetime of the molecule increases. For example it was found that a molecule showing a lower extinction coefficient in blue part of the spectram than in yellow, when irradiated with a blue source of light showed a factor of 7 longer lifetime than when irradiated by a yellow source of light.
  • the invention provides a lighting device comprising (i) a source of light for generating light source light having a spectral distribution with a maximum intensity at a first wavelength ( ⁇ ) within the visible wavelength range, (ii) a light converter comprising an organic luminescent material, wherein the light converter is transmissivc for at least part of the light source light, wherein the organic luminescent material is configured to provide upon excitation with the light source light luminescent material light having a wavelength within the visible wavelength range, wherein the organic luminescent material has an excitation spectrum having a maximum excitation intensity at a second wavelength ( ⁇ 2), and wherein ⁇ ⁇ 2.
  • lifetime of the organic luminescent material may substantially be increased.
  • the invention uses the application of a sub- optimal excitation to increase lifetime of an organic luminescent material. Thereby, also the lifetime of the lighting device is increased.
  • the organic luminescent material is configured to provide upon excitation with the light source light luminescent material light having a wavelength within the visible wavelength range.
  • the organic luminescent material will especially have at ⁇ a nonzero excitation intensity (i.e. ⁇ will in general be non-zero).
  • the excitation intensity is not at maximum at ⁇ but lower than the maximum (excitation intensity) at X2.
  • the organic luminescent material is configured to provide luminescent material light having a wavelength within the visible wavelength range upon excitation with the light source light.
  • the source of light is a source of light that during operation emits (light source light) at least light at a wavelength selected from the range of 200-600 ran, especially a source of light that during operation emits at least light at wavelength selected from the range of 400-600 ran, such as in the range of 400-500 nm, even more especially in the range of 440-490 nm.
  • the source of light may generate light source light with a spectral distribution with a maximum in the range of 440-490 rim. This does however not exclude the presence of light source light in other wavelength ranges.
  • the light source light especially has somewhere in the spectral distribution of the light a maximum at a specific wavelength though other wavelengths are not excluded.
  • the source of light comprises a solid state light source, such as a light emitting diode (LED) or a laser, for instance a blue light emitting diode (LED).
  • a solid state light source such as a light emitting diode (LED) or a laser, for instance a blue light emitting diode (LED).
  • the term "source of light” may especially relate to an electronic source, such as a LED light source.
  • the term “light source” may be applied.
  • the source of light may also be a luminescent material (that is excited by another source of light, especially e.g. a LED light source).
  • the light source excited a luminescent material wherein the luminescence of the luminescent material is at least partly be used by another luminescent material as excitation light.
  • the present invention especially uses the principle of direct excitation for organic luminescent materials, even when there is a plurality of organic luminescent materials available.
  • an organic luminescent material may optionally be applied herein as source of light for an inorganic luminescent material.
  • the organic luminescent material is essentially excited by the (light source light of the) source of light only.
  • the lighting device is especially configured to allow the organic luminescent material being essentially excited by the (light source light of the) source of light only.
  • the organic luminescent material may derive especially at least 90% of the excitation (energy) from the (light source light of the) source of light only, especially an LED light source, and not by other light sources.
  • a combination of different types of sources of light are applied.
  • the source of light may partially be used by the organic luminescent material (see further also below).
  • the source of light is configured to generate blue light.
  • the source of light comprises a solid state LED light source (such as a LED or laser diode).
  • the term "source of light” may also relate to a plurality of sources of light, such as 2-20 (solid state) LED source of lights.
  • the term LED may also refer to a plurality of LEDs.
  • the lighting device may especially be configured to generate white light.
  • This may in an embodiment be created by the combination of the source of light emission (i.e. light source light of the source of light), which especially includes blue light, and the emission of the organic luminescent material, which may e.g. include one or more of green, yellow, orange and red light.
  • the organic luminescent material which may e.g. include one or more of green, yellow, orange and red light.
  • other luminescent materials may be used in the lighting device to provide (white) (lighting device) light (see also below).
  • white light is known to the person skilled in the art.
  • CCT correlated color temperature
  • violet light or “violet emission” especially relates to light having a wavelength in the range of about 380-440 run.
  • blue light or “blue emission” especially relates to light having a wavelength in the range of about 440-490 ran (including some violet and cyan hues).
  • green light or “green emission” especially relate to light having a wavelength in the range of about 490-560 nm.
  • yellow light or “yellow emission” especially relate to light having a wavelength in the range of about 540- 570 nm.
  • range light or “orange emission” especially relate to light having a wavelength in the range of about 570-600.
  • red light or “red emission” especially relate to light having a wavelength in the range of about 600-750 nm.
  • the light converter comprises a material that is able to convert the light source light and/or optionally light of another source (such as another luminescent material) into emission light of the luminescent material.
  • the light converter may also be indicated as wavelength converter.
  • the light converter is especially a transmissive material that includes an organic luminescent material. This organic luminescent material may be molecularly dispersed therein.
  • the material of the light converter may also be indicated as host material. This host material hosts the organic luminescent material.
  • the light converter comprises a polymeric material (or polymeric host).
  • the light converter comprises one or more materials selected from the group consisting of PE (polyethylene), PP (polypropylene), PEN (polyethylene napthalate), PC (polycarbonate), polymethylacry!ate (PMA), polymethylmethacrylate (PMMA) (Plexiglas or Perspex), cellulose acetate butyrate (CAB), silicone, polyvinylchloride (PVC), polyethylenctcrcphthalatc (PET), (PETG) (glycol modified polyethyleneterephthalate), PDMS (polydimeihylsiloxane), and COC (cyclo olefin copolymer).
  • PE polyethylene
  • PP polypropylene
  • PEN polyethylene napthalate
  • PC polycarbonate
  • PMA polymethylacry!ate
  • PMA polymethylmethacrylate
  • PMMA polymethylmethacrylate
  • CAB
  • the light converter comprises thus in embodiments a host (or matrix) (materia!) comprising an organic luminescent material.
  • the light converter comprises polyethyleneterephthalate (PET) as material.
  • PET polyethyleneterephthalate
  • the light converter is transparent.
  • the light converter highly transmissive and shows a low degree of back scattering thus transmits light to a large extent.
  • the light converter may optionally also be translucent, such as due to surface structure and /or volume scattering.
  • the light converter is configured to allow transmission of at least part of the light source light, especially blue light (from a source of light generating (at least) blue light).
  • the material has a light transmission, even more especially outside the range where the organic luminescent molecule absorbs, in the range of 50-100 %, especially in the range of 50-90%, such as in the range of 70-90%.
  • back scattering is especially in the range 10-50% and most preferentially in the range 10-30%.
  • transmission or light permeability can be determined by providing light at a specific wavelength with a first intensity to the material and relating the intensity of the light at that wavelength measured after transmission through the material, to the first intensity of the light provided at that specific wavelength to the material (see also E-208 and E-406 of the CRC Handbook of Chemistry and Physics, 69th edition, 1088-1989).
  • the phrase "transmissive for at least part of the light source light” especially indicates that when providing light source light to one side (face) of the light converter part of the light will be transmitted through the light converter and can be found at another side (face) of the light converter (downstream). Further, part of the light may be absorbed by the light converter. When absorption occurs, the extent in which is absorbed may- depend on the wavelength of the light offered to the light converter. Hence, the spectral distribution of the light of the light source light that is transmitted through the light converter may in embodiments differ from the spectral distribution of the light source light. Hence, in an embodiment the light converter is configured in the device in a transmissive configuration, i.e.
  • the light converter is configured in the device in a reflective configuration.
  • the light converter is especially transmissivc.
  • the invention is especially directed to those type of devices wherein a light source generates light, with the light converter arranged downstream of the light source, and with light escaping from the light converter at an other side of the light converter, i.e. especially light travels through the entire light converter.
  • the light converter will be a layer or a plate, with a light source at one side, and lighting device light escaping downstream from the light converter.
  • the light converter may also be configured in reflective mode.
  • the invention also provides a lighting device comprising (i) a source of light for generating light source light having a spectral distribution with a maximum intensity at a first wavelength ( ⁇ ) within the visible wavelength range, (ii) a light converter comprising an organic luminescent material, wherein the organic luminescent material is configured to provide upon excitation with the light source light luminescent material light having a wavelength within the visible wavelength range, wherein the organic luminescent material has an excitation spectrum having a maximum excitation intensity at a second wavelength ( 2), and wherein ⁇ 12, and wherein especially the light converter is arranged in a reflective configuration.
  • the light converter may especially be radiationally coupled to the source of light, i.e. they are functionally coupled.
  • radiationally coupled especially means that the source of light and the luminescent material (i.e. the organic luminescent material comprised by the light converter) are associated with each other so that at least part of the radiation emitted by the source of light is received by the luminescent material (and at least partly converted into luminescence).
  • the light converter is arranged remote from the source of light.
  • the organic luminescent materials are arranged remote from the LED die (i.e. not in physical contact with the LED).
  • the shortest distance between the source of light (exit surface), such as a LED (die), and one or more of the luminescent materials, preferably all luminescent materials, may be larger than 0 mm, especially equal to or larger than 0.1 mm, such as 0.2 or more, and in some embodiments even equal to or larger than 10 mm, such as 10-100 mm, A remote application may further increase lifetime.
  • the present invention also includes applications wherein the light converter is in physical contact with the LED die (or other light source (surface)). At a non-zero distance, but remote from the light source may also be indicated as "in the vicinity".
  • the term light converter may refer to a system that is configured to convert light from a first wavelength into light of a second wavelength.
  • UV and or blue light (excitation wavelength) may be (at least partially) converted into visible light (of higher wavelength than the excitation wavelength).
  • the light converter may be in the form of for instance particles, flakes, a film, a plate, etc.
  • the term light converter may include a self supporting layer.
  • the light converter is selected from the group consisting of a coating, a self supporting layer, and a plate; which light converter is thus especially solid at room temperature, especially even up to 100 °C, especially even up to 150 °C, especially even up to 200°C).
  • the light converter may be flexible or may be rigid.
  • the light converter may be flat or curved (in one or two dimensions). Further, optionally the light converter may comprise outcoupling structures at at least part of the external surface of the light converter.
  • the light converter may comprise one or more parts, like layers on top of each other. Such parts may comprise different luminescent materials or luminescent materials in different concentration. However, at least part of the light converter comprises the (red) organic luminescent material.
  • the matrix may especially comprise a matrix material and the above indicated materials such as the organic luminescent material, and optionally inorganic luminescent material, etc.
  • the organic luminescent material(s) and optionally other luminescent materials may in an embodiment especially be evenly distributed throughout the matrix.
  • the light converter may also comprise two or more segments, wherein two or more segments have different compositions at least with respect to the luminescent material(s), e.g. with respect to type and/or concentration of the luminescent materiai(s).
  • the light converter comprises an organic luminescent material.
  • the organic luminescent material can be any organic luminescent material, but is especially selected from the group consisting of organic luminescent materials that have emission in the visible. However in specific embodiments (organic) luminescent material may have emission in near red and infrared.
  • especially the organic luminescent materials is configured to provide luminescent material light (upon excitation by (light source light of) a source of light, especially the source of light), having a wavelength within the visible wavelength range. Again, this does not exclude the existence of emission in other wavelength ranges, though preferably substantially all the emission (energy) is within the visible wavelength range.
  • the organic luminescent material has an excitation spectram. This excitation may comprise one or more maxima.
  • the highest maximum is at a second excitation wavelength ⁇ 2.
  • ⁇ ⁇ 2 leading to an excitation of the organic luminescent material that is shifted relative to the maximum excitation wavelength.
  • the choice of the present invention may include that relatively more organic luminescent material is needed. However, the lifetime of the device increases. Examples of specific organic luminescent materials can be found below. Note that the term "organic luminescent material” may in embodiments also relate to a plurality of different organic luminescent materials (see also below).
  • the spectral distribution of the light source light of the source of light and the excitation spectrum of the organic luminescent material have a (normalized) spectral overlap SO in the range of 0 ⁇ SO ⁇ 0.4, such as 0.01 ⁇ SO ⁇ 0.4. wherein the normalized spectral overlap is defined as:
  • ⁇ ( ⁇ ) is the intensity of the source of light as a function of wave length
  • ⁇ ( ⁇ ) is the extinction coefficient as a function of wavelength based on the excitation spectrum
  • e max is the maximum extinction coefficient in the wavelength range of 350-900 nm (i.e. ⁇ - Xy) , based on the excitation spectrum
  • ⁇ ⁇ and X y define the wavelength range of 350-900 nm.
  • the normalized spectral overlap may be 0.35 or less, such as in the range of 0.1-0.3.
  • the organic luminescent material is selected from the group consisting of:
  • organic luminescent material is especially a material according to formula (I):
  • Gi and G f independently comprise a group selected from a linear alkyl, a branched alkyl, an oxygen-containing alkyl, a cycloaikyl, a naphtyl, and Y;
  • each of A, B, C, J and Q independently comprise a group selected from hydrogen, fluorine, chlorine, isopropyl, t-butyl, methoxy, an alkyl with up to 16 carbon atoms, and an oxygen containing alkyl with up to 16 carbon atoms;
  • G 2 , G3, G4 and G5 independently comprise a group selected from hydrogen, fluorine, chorine, isopropyl, t-butyl, methoxy, alkyl with up to 16 carbon atoms, and oxygen- containing alkyl with up to 16 carbon atoms, and X;
  • each of D, E, I, L and M independently comprise a group selected from hydrogen, fluorine, chlorine, isopropyl, t-butyl, methoxy, alkyl with up to 16 carbon atoms, and an oxygen-containing alkyl with up to 16 carbon atoms;
  • At least two selected from G2, G3, G4, and G5 at least comprise X, wherein (in a specific embodiment) independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine, especially fluorine.
  • At least two of said at least two selected from G2, G3, G4, and G5 comprise two or more groups selected from fluorine and chlorine, especially fluorine.
  • G2-G5 are each independently X.
  • the linear alkyl, branched alkyl, oxygen containing alkyl (see also below), cycloalky!, and the naphtyl, as defined above for especially Gl and G6, may especially comprise up to 44 carbon atoms.
  • the alkyl (or naphty!) may also be substituted with fluorine.
  • Gl and G6 are each independently C n H? n+ i. m F m with n ⁇ 44, and m ⁇ 2n+l .
  • Other substitoents are not excluded.
  • the alkyl comprises up to 20, such as up to 10, like up to 8 carbon atoms.
  • the oxygen containing alkyl, with especially up to 44 carbon atoms, as defined above for especially Gi and G6, may in an embodiment especially relate to
  • n an integer from 1 to 44 and m ⁇ n/2.
  • the oxygen containing alkyl, with especially up to 44 carbon atoms, may also be substituted with fluorine.
  • the oxygen containing alkyl may be linear, branched, or cyclic, or may be a combination of two or more thereof.
  • the oxygen containing alkyl especially comprises an alcohol or an ether, such as an oh go ethylene oxide.
  • n is up to 20, such as up to 10, like up to 8.
  • Gl and G6 may be the same or may be different (see also below).
  • the alkyl with up to 16 carbon atoms as defined above for A, B, C, J, Q, G2, G3, G4 and G5, D, E, I, L and M, especially relate to CJHb n +i , with n being an integer from 1 to 16.
  • the alkyl may be linear, branched, or cyclic, or may be a combination of two or more thereof.
  • the alkyl with up to 16 carbon atoms may also be substituted with fluorine (see below). Other substituents are not excluded.
  • the alkyl comprises up to 10, such as up to 8 carbon atoms.
  • the oxygen containing alkyl with up to 16 carbon atoms as defined above for A, B, C, J, Q, G2, G3, G4 and G5, D, E. I, L and M, especially relates to C n H 2n+ iO m , with n being an integer from 1 to 16 and with m ⁇ n/2.
  • the alkyl may be linear, branched, or cyclic, or may be a combination of two or more thereof.
  • the oxygen containing alkyl with up to 16 carbon atoms may also be substituted with fluorine (see below). Other substituents are not excluded.
  • n is up to 10, such as up to 8.
  • the alkyl with up to 16 carbon atoms may at least partially be substituted with fluorine, and may in an embodiment especially relate to C n H 2n+ i- m F m with n being an integer from 1 to 16 and with m ⁇ 2n+l .
  • the fluorine substituted alkyl may be linear, branched, or cyclic, or may be a combination of two or more thereof. Other substituents are not excluded.
  • n is up to 10, such as up to 8.
  • A, B, C, J, Q may independently be chosen.
  • G2, G3, G4 and G5 may independently be chosen.
  • D, E, I, L and M may independently be chosen.
  • the invention also provides a light converter per se, especially a light converter comprising a matrix containing an inorganic luminescent material and an organic luminescent material as defined by formula (I), with
  • the invention also provides such organic luminescent material per se, especially an organic luminescent material as defined by formula (I), with G1,G2,G3,G4,G5,G6,X 3 Y,A,B 5 C,D,E,1 ! J,M,L as defined above (and further below).
  • organic luminescent material may have a red luminescence (upon UV and/or blue excitation) with does not extend far in the red and has a cutoff at a relative short wavelength (compared to most of the state of the art red luminescent materials similar to formula I phosphors).
  • the above described organic luminescent material is of the perylene type.
  • Perylenes are known in the art and are for instance described in US 4,845,223, US
  • the phrase "at least two selected from G2, G3, G4, and G5 at least comprise X, wherein independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine” indicates amongst others that from the four groups G2, G3, G4, and G5, at least two of these, but in embodiments also three of these, or all of these, comprise a group X as defined herein. Especially, two of these, or in embodiments three or all four of these, are X. From this group of at least two X groups, at least two X groups are each independently at least substituted with one fluroine or chlorine, especially at least substituted with one fluorine.
  • the phrase "at least substituted with one fluorine" and similar phrases may indicate that there is at least one substituent F, though there may (thus) be more.
  • the available X-groups in two or more of G2, G3, G4, and G5, may especially comprise two or more groups selected from fluorine and chlorine, i.e. contain two or more halogen substituents.
  • the phrase "independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine" also indicates that the X groups available are independently of each other substituted.
  • one of the X groups may e.g. have a fluorine at the D or M position and one of the X groups may have a fluorine at the E or L position, or a chlorine at one more of the D,E,I,L,M position, etc.
  • the two groups that at least comprise X, or more espeically the two groups that in an embodiment are X are identical.
  • the four groups comprise X, or are X especially there are two sets of identical X, but the sets are mutually different, or there is one set of identical X (all four G2-G5 are identical).
  • the emission wavelength shifts to the blue (less far red).
  • a halogen in X the emission wavelength shifts to the blue (less far red).
  • the shift to the blue may be in the range of 20 nm relatieve to the unsubstituted X groups.
  • independently at least two of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise groups selected from fluorine and chlorine.
  • G2-G5 comprising, or especially consisting of X
  • at least two of these i.e. two of two, two of the three, or three of the three, or two of the four, or three of the four, or four of the four
  • the distribution of these two or more halogens over D, E, I, L and M for each of these at least two G2-G5 may independently be chosen.
  • the two groups at least comprise X, or more espeically, when two groups are X, these two groups are in an embodiment especially identical.
  • the options Ila and lib especially independently apply to at least two of G2, G3, G4 and G5, More especially, the conditions lib especially apply to at least two, especially all four, of G2, G3, G4 and G5 (i.e. at least two of G2, G3, G4 and G5 are X, with the conditions lib).
  • Y may apply to one or both Y groups.
  • the conditions for X may apply to both X comprising groups selected from G2-G5, but may optionally apply to three or four of these four groups. This also applies for the below indicated embodiments.
  • two of the groups G2,G3, G4 and G5 are hydrogen and the two X comprising groups are identical.
  • at least one of A or B is a fluorine or chlorine
  • C J,Q are independently selected from F, CI, or H.
  • G3 and G4 may especially be hydrogen.
  • G3 and G5 may especially be hydrogen.
  • G3 and G4 may especially be hydrogen.
  • G3 and G5 may especially be hydrogen.
  • the red emitting (organic) luminescent material preferably emits 70% of the energy (Watt) below 650 nm (at RT), even more especially at least 70% of the energy below 645 nm (at RT).
  • the above described organic luminescent material may be well excitable in the blue and/or UV and/or even in the green and/or yellow.
  • the organic luminescent material may be excited by a source of blue light, such as a blue LED light source, but alternatively or additionally, the organic luminescent material may also be excited by a source of green and/or yellow light. Examples of the latter may e.g. green and/or yellow emitting luminescent materials like cerium containing garnet systems (such as YAG:Ce; see also below) or an organic yellow emitter.
  • the compound herein indicated with reference 17 (see also fig. 2b) is used in a remote (from the light source) configuration.
  • the compound herein indicated with reference 17 is embedded in a matrix comprising PET. Especially, this PET matrix may be arranged remote (from the light source / source of light).
  • one or more of Gl , G2, G3, G4, G5, and G6, especially one or more of Gl and G6, comprise a covalent link with the matrix. This may for instance be obtained by providing one or more of these groups, such as one or more of Gl and G6, with a curable group or a polymerizable group.
  • the matrix may e.g. PMMA or PET, especially PET.
  • the light converter may also comprise a plurality of organic luminescent materials according to formula I.
  • the term "organic luminescent material” may relate to a combination of different organic luminescent material all complying with formula (I).
  • the light converter optionally comprises an inorganic luminescent material (see further below).
  • the light converter may also comprise a plurality of inorganic luminescent materials.
  • the light converter may comprise one or more organic luminescent materials according to formula I, and optionally one or more other organic luminescent materials, and preferably one or more inorganic luminescent materials.
  • the light converter may further comprise one or more scattering materials (e.g. Ti0 2 , AI2O3 and/or BaSO.; particles) , and optionally other materials.
  • two of the groups G2,G3, G4 and G5 are hydrogen and the two X comprising groups are identical, the inorganic luminescent material comprises a quantum dot based luminescent material, and the matrix comprises polyethylene
  • PET terephthalate
  • At least two selected from G2, G3, G4, and G5 at least comprise X, wherein independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group as defined above, including optionally, but not necessarily, selected from fluorine and chlorine.
  • one or more of G2, G3, G4, and G5 may be halogen free.
  • one or more of D, E, I, L and M may comprise independently comprise a group selected from hydrogen, isopropyl, t-butyl, methoxy, alkyl with up to 16 carbon atoms, and an oxygen-containing alkyl with up to 16 carbon atoms.
  • Other perylene derivatives may be of interest as well.
  • organic luminescent material that may be applied, such as those that do not include halogenated groups are indicated below.
  • organic luminescent material is selected from the group comprising:
  • the lighting device may further comprise a second luminescent material.
  • This second luminescent material is not necessarily comprised by the light converter.
  • the second luminescent material is comprised by the light converter.
  • the second luminescent material comprises a second organic luminescent material.
  • the luminescent material may apply.
  • the second (organic) luminescent material is configured to provide upon excitation with the light source light
  • (second) luminescent material light having a wavelength within the visible wavelength range, wherein the second (organic) luminescent material has an excitation spectrum having a maximum excitation intensity at a third wavelength ( ⁇ 3), and wherein ⁇ 13.
  • the second luminescent material comprises an inorganic luminescent material, such as one or more of a cerium doped garnet material and a quantum dot based material.
  • an inorganic luminescent material such as one or more of a cerium doped garnet material and a quantum dot based material.
  • luminescent materials may be applied as adjacent layers or as mixtures. However, they may also be arranged remote from each other.
  • other luminescent materials may be applied.
  • the other luminescent material may be contained in the matrix as well. Alternatively or additionally, the other luminescent material may be present as coating on the light converter. Alternatively or addtionally, the luminescent material may be arranged anywhere else in the lighting device.
  • the other luminescent mateiral may especially be configured to convert at least part of the light source light into visible converter light.
  • the other luminescent material is configured to provide one or more of blue, green, yellow and orange light, more especially at least one or more of green and yellow light.
  • the other luminescent material may comprise a (garnet material), wherein M is selected from the group consisting of Sc, Y, Tb, Gd, and Lu. wherein A is selected from the group consisting of Al and Ga.
  • M at least comprises one or more of Y and Lu, and wherein A at least comprises AL
  • Embodiments of garnets especially include M3A5O12 garnets, wherein M comprises at least yttrium or lutetium and wherein A comprises at least aluminum.
  • Such garnet may be doped with cerium (Ce), with praseodymium (Pr) or a combination of cerium and praseodymium; especially however with at least Ce.
  • Particularly suitable luminescent materials are Ce doped Yttrium aluminium garnet (YAG, ⁇ 3 ⁇ 5 ⁇ 12) and Lutetium- Aluminium-Garnet (LuAG).
  • the other luminescent material may comprise one or more of selected from the group consisting of divalent europium containing nitride luminescent material or a divalent europium containing oxonitride luminescent material, such as one or more materials selected from the group consisting of (Ba,Sr,Ca)S:Eu,
  • Eu europium
  • Eu is substantially or only divalent, and replaces one or more of the indicated divalent cations.
  • Eu will not be present in amounts larger than 10% of the cation, especially in the range of about 0.5-10%, more especially in the range of about 0.5-5% relative to the cation(s) it replaces.
  • Divalent europium will in general replace divalent cations, such as the above divalent alkaline earth cations, especially Ca, Sr or Ba.
  • the material (Ba,Sr,Ca)S:Eu can also be indicated as MS:Eu, wherein M is one or more elements selected from the group consisting of barium (Ba), strontium (Sr) and calcium (Ca);
  • M comprises in this compound calcium or strontium, or calcium and strontium, more especially calcium.
  • Eu is introduced and replaces at least part of M (i.e. one or more of Ba, Sr, and Ca).
  • the material can also be indicated as wherein M is one or more elements selected from the group consisting of barium (Ba), strontium (Sr) and calcium (Ca); especially, M comprises in this compound Sr and/or Ba.
  • the second luminescent material comprises one or more materials selected from the group comprising quantum dots, quantum rods or quantum tetrapods, nano-crystals, a rare earth metal based luminescent material, and an inorganic luminescent material.
  • The may be configured to show line emission (f-f transitions) and/or broad band emission(s) (f-d transitions).
  • the second luminescent material comprises an inorganic luminescent material.
  • the inorganic luminescent material may comprise quantum Dots (QDs). Amongst other narrow band emitters quantum dots are highly suitable for this purpose.
  • Quantum dots are small crystals of semiconducting material generally having a width or diameter of only a few nanometers. When excited by incident light, a quantum dot emits light of a color determined by the size and material of the crystal. Light of a particular color can therefore be produced by adapting the size of the dots. This means that by using quantum dots any spectrum can be obtained as they are narrow band emitters.
  • quantum dots with emission in the visible range are based on cadmium selenide (CdSe) with shell such as cadmium sulfide (CdS) and zinc sulfide (ZnS).
  • Cadmium free quantum dots such as indium phosphide (InP), and copper indium sulfide (CulnS2) and/or silver indium sulfide (AgInS 2 ) can also be used.
  • Quantum dots show very narrow emission band and thus they show saturated colors. Furthermore, the emission color can easily be tuned by adapting the size of the quantum dots.
  • the quantum dots or luminescent nanoparticles which are herein indicated as light converter nanoparticles, may for instance comprise group II- VI compound
  • semiconductor quantum dots selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS.
  • the luminescent nanoparticles may for instance be group III-V compound semiconductor quantum dots selected from the group consisting of GaN, GaP, GaAs, A1N, A1P, AlAs, InN, InP, InAs, GaNP, GaNAs, GaPAs, A1NP, AINAs, AlPAs, In P, InN As, InP As, GaAlNP, GaAlNAs, GaAlPAs, Galn P,
  • the luminescent nanoparticles may for instance be I-III-VI2 chalcapyrite-type semiconductor quantum dots selected from the group consisting of CulnS 2 , CuInSe 2 , CuGaS 2 , CuGaSe 2 , AglnSi, Agln5e 2 , AgGaS 2) and AgGaSe 2 .
  • the luminescent nanoparticles may for instance be I-V-VI2 semiconductor quantum dots, such as selected from the group consisting of LiAsSe 2 , NaAsSe 2 and KAsSe 2 .
  • the luminescent nanoparticles may for instance be a group IV-VI compound semiconductor nano crystals such as SbTe.
  • the luminescent nanoparticles are selected from the group consisting of InP, CuInS 2 , CuInS3 ⁇ 4, CdTe, CdSe, CdSeTe, AglnS? and AglnSe 2 .
  • the luminescent nanoparticles may for instance be one of the group II-VI, III-V, I-III-V and IV-VI compound semiconductor nano crystals selected from the materials described above with inside dopants such as ZnSe:Mn, ZnS:Mn.
  • the dopant elements could be selected from Mn, Ag, Zn, Hu, S, P, Cu, Ce, Tb, Au, Pb, Tb, Sb, Sn and Tl.
  • the luminescent nanoparticles based luminescent material may also comprise different types of QDs, such as CdSe and ZnSe:Mn. It appears to be especially advantageous to use II-VI quantum dots.
  • the semiconductor based luminescent quantum dots comprise II-VI quantum dots, especially selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTc, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CriZnS, CdZnSe, CdZnTe, Cdi lgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, C
  • the light converter nano-particles comprise III-V QDs, more specifically an InP based quantum dots, such as a core-shell InP-ZnS QDs.
  • InP quantum dot or “InP based quantum dot” and similar terms may relate to "bare” InP QDs, but also to core-shell InP QDs, with a shell on the InP core, such as a core-shell InP-ZnS QDs, like a In -ZnS QDs dot-in- rod.
  • nanoparticles can comprise semiconductor nan crystals including a core comprising a first semiconductor material and a shell comprising a second semiconductor material, wherein the shell is disposed over at least a portion of a surface of the core.
  • a semiconductor nanocrystal including a core and shell is also referred to as a "core/shell" semiconductor nanocrystal.
  • the semiconductor nanocrystal can include a core having the formula MX, where M can be cadmium, zinc, magnesium, mercury, aluminum, gallium, indium, thallium, or mixtures thereof, and X can be oxygen, sulfur, selenium, tellurium, nitrogen, phosphorus, arsenic, antimony, or mixtures thereof.
  • materials suitable for use as semiconductor nanocrystal cores include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS,
  • the shell can be a semiconductor material having a composition that is the same as or different from the composition of the core.
  • the shell comprises an overcoat of a semiconductor material on a surface of the core semiconductor nanocrystal can include a Group IV element, a Group II-VI compound, a Group II-V compound, a Group III- VI compound, a Group III-V compound, a Group IV- I compound, a Group I-III-VI compound, a Group ll-IV-VI compound, a Group II-IV-V compound, alloys including any of the foregoing, and/or mixtures including any of the foregoing, including ternary and quaternary mixtures or alloys.
  • Examples include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS, HgSe, HsTe, InAs, inN, InP, InSb, AlAs, AIN, A1P, AiSb, TIN, TIP, TIAs, TISb, PbO, PbS, PbSe, PbTe, Ge, Si, an alloy including any of the foregoing, and/or a mixture including any of the foregoing.
  • ZnS, ZnSe or CdS overcoatings can be grown on CdSe or CdTe semiconductor nanocrystals.
  • semiconductor nanocrystal (core)shell materials include, without limitation: red (e.g., (CdSe)ZnS (core)shell), green (e.g., (CdZnSe)CdZnS (core)shel!, etc.), and blue (e.g., (CdS)CdZnS (core)shell (see further also above for examples of specific light converter nanoparticles, based on semiconductors.
  • red e.g., (CdSe)ZnS (core)shell
  • green e.g., (CdZnSe)CdZnS (core)shel!, etc.
  • blue e.g., (CdS)CdZnS (core)shell
  • the light converter nanoparticles are selected from the group consisting of core-shell nano particles, with the cores and shells comprising one or more of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, CdSeS.
  • the cores and shells comprise the same class of material, but essentially consist of different materials, like a ZnS shell surrounding a CdSe core, etc.
  • embodiments of the lighting device may be configured to substantially prevent that the one or more organic luminescent materials are excited in their maximum. Especially, all one or more organic luminescent materials are excited off-maximum. Even more especially, all one or more organic luminescent materials are directly excited by a light source, such as a LED, and are not substantially excited by another (organic) luminescent material.
  • the lighting device may include specific sets of one or more organic luminescent materials and sources of light, such that each set is optimized with respect to excitation wavelength and light source light.
  • the lighting device may be part of or may be applied in e.g. office lighting systems, household application systems, shop lighting systems, home lighting systems, accent lighting systems, spot lighting systems, theater lighting systems, fiber-optics application systems, projection systems, self-lit display systems, pixelated display systems, segmented display systems, warning sign systems, medical lighting application systems, indicator sign systems, decorative lighting systems, portable systems, automotive applications, green house lighting systems, horticulture lighting, or LCD backlighting.
  • the invention also provides in a further aspect a luminaire comprising a lighting device as defined herein.
  • the lighting device may be used as backlighting device in an LCD display device.
  • the invention provides also a LCD display device comprising the lighting device as defined herein, configured as backlighting device.
  • the invention also provides in a ftirtlier aspect a liquid crystal display device comprising a back lighting device, wherein the back lighting device comprises one or more lighting devices as defined herein.
  • substantially may also include embodiments with “entirely”, “completely”, “all”, etc. Hence, in embodiments the adjective substantially may also be removed. Where applicable, the term “substantially” may also relate to 90% or higher, such as 95% or higher, especially 99% or higher, even more especially 99.5% or higher, including 100%.
  • the term “comprise” includes also embodiments wherein the term “comprises” means “consists of.
  • the term “and/or” especially relates to one or more of the items mentioned before and after "and/or”. For instance, a phrase “item 1 and/or item 2" and similar phrases may relate to one or more of item 1 and item 2.
  • the term “comprising” may in an embodiment refer to “consisting of but may in another embodiment also refer to "containing at least the defined species and optionally one or more other species”.
  • the invention further applies to a device comprising one or more of the characterizing features described in the description and/or shown in the attached drawings.
  • the invention further pertains to a method or process comprising one or more of the characterising features described in the description and/or shown in the attached drawings.
  • Figs. 2a-2j schematically depict some organic materials that were made
  • Figs. 3a-3b show some emission spectra of some of these organic materials
  • Figs. 4a-4b schematically show some synthesis schemes
  • Fig. 5 schematically shows different excitation options
  • Fig. 6a-6c schematically show some excitation spectra and an emission spectrum of a number of organic luminescent materials
  • Figs. 7a-7d schematically depict several configurations as well as the impact on the stability.
  • Fig. 1 a schematically depicts a lighting device 1 with a light converter 100, which in this embodiment at least comprises the organic luminescent materia! 140 according to formula I.
  • the organic luminescent material 140 is in this embodiment embedded in a (polymeric) matrix, such as PET.
  • a remote version is shown, with a non-zero distance d between the luminescent material (in the light converter 100) and the light source(s), indicated with reference(s) 10.
  • the lighting device 1 comprises one or more light sources 10 which are configured to provide light source light 1 1, especially blue and/or UV light.
  • the lighting device 1 may comprise a plurality of such light sources.
  • the red luminescent material 140 When lighting device light, indicated with reference 2, of a white nature is desired, it may be necessary to us an RGB concept, wherein the red color, or at least part thereof, is provided by the red luminescent material 140, and the blue and green light are provided by one or more of the light source and a combination of the light source and another luminescent material, especially the inorganic luminescent material.
  • the inorganic luminescent material is indicated with reference 130, and provides inorganic luminescent material light 131.
  • the organic luminescent material 140 provides upon excitation by the light source light 1 1 and/or by emission of one or more other luminescent materials, such as e.g. the inorganic luminescent material light 131 , organic luminescent material light 141.
  • the light converter 100 is remote from the light source 10, and the organic luminescent material, which is embedded in the light converter 100, is thus also remote.
  • the optional inorganic luminescent material 130 can also be arranged remote, see below, but is by way of example close to the light source 10, such as in a dome and/or as layer on the LED die.
  • one light source has been depicted without the inorganic luminescent material 130.
  • all light sources 10 may be configured with at least inorganic luminescent material 130.
  • three light sources 10 have been depicted. However, more or less than three light sources may be applied.
  • the light source 10 may provide blue and/or UV light.
  • the inorganic luminescent material 130 may especially, upon excitation (by said light of the light source 10) provide one or more of blue, green, and yellow light.
  • the inorganic iuminescent material 130 may also provide red light, but especially the inorganic luminescent material 130 has a cutoff equal to or below 600 run (such as especially having a spectral distribution with at least 70% of the energy below 600 nm).
  • Fig. l a schematically depict a device with a light chamber 170, with an enclosure 171, at least partly enclosing a cavity 172, which has a transmissive part 173.
  • the reflectivity (except for a transmissive part or window) of the mixing chamber is preferably > 80%, more preferably 90%, most preferably > 95%, especially for light in the visible. This may also apply for other herein described and/or schematically depicted embodiments.
  • the transmissive part 173 comprises the light converter 100, or may especially consist of the light converter 100.
  • the surface of the non-transmissive part of the enclosure is indicated with reference 171. At least part of the surface 171 may comprise a reflector, such as a reflective coating.
  • the light converter 100 provides upon excitation light converter light 1 1 1 , which at least comprises organic luminescent material light 141 but may optionally comprise other luminescence light as well (see below).
  • the lighting device light indicated with reference 2, at least comprises light converter light 1 1 1 / organic luminescent material light 141 , but may optionally comprise one or more of the light source light 1 1 , inorganic luminescent material light 131 , and light of other luminescent materials (not depicted).
  • Fig. 1 b schematically depicts an embodiment wherein the light converter 100 may comprise an upstream layer with inorganic luminescent material 130.
  • this may be a light converter comprising two layers comprising the same matrix, but comprising different luminescent materials.
  • the distance of the layer with inorganic luminescent material 130 to the light source is indicated with dl . This distance is in this embodiment non-zero, in contrast to the embodiment schematically depicted in fig. l a.
  • upstream and downstream relate to an arrangement of items or features relative to the propagation of the light from a light generating means (here the especially the first source of light), wherein relative to a first position within a beam of light from the light generating means, a second position in the beam of light closer to the light generating means is "upstream”, and a third position within the beam of light further away from the light generating means is
  • Fig. l c schematically depicts an embodiment wherein the light converter 100 comprises the inorganic luminescent material 130, e.g. in the form of quantum dots, and the organic luminescent material 140 according to formula I.
  • Both the organic luminescent material 140 and the inorganic luminescent material 130 are in this embodiment embedded in the (remote) light converter, i.e. embedded in the (polymeric) matrix of the light converter 100
  • Figs, lb and lc schematically show embodiments in a transmissive configuration, i.e. with the source of light at one side of the light converter and lighting device light escaping at the other side of the light converter.
  • Fig, Id schematically depicts an embodiment wherein the transmissive part 173 comprises at least two types of segments, with volumes over 0.25 cm 3 , wherein the two types of segments comprise different weight ratios organic luminescent material and inorganic luminescent material.
  • first segments only comprise the organic luminescent material 140 as luminescent material and second segments only comprises inorganic luminescent material 130 as luminescent material.
  • the organic luminescent material 140 may also in this embodiment be embedded in a (polymeric) matrix, such as PET.
  • the inorganic luminescent material 130 may be embedded in a
  • polymeric matrix such as PET.
  • Fig. 1 e schematically depicts an embodiment wherein the enclosure 170 comprises a transmissive diffuser 160 (as transmissive part 173) and the light converter is applied to at least part of the non-transmissive part of the enclosure 171 .
  • the light converter 100 is arranged in a reflective configuration.
  • Fig. If schematically depicts a reflective configuration.
  • the organic luminescent material 140 and optionally the inorganic luminescent material 140 may (both) be embedded in a (polymeric) matrix.
  • the light converter 100 is arranged in a reflective configuration.
  • Figs. 2a-2j schematically depict some organic luminescent material that have been made of the perylene type, especially embodiments of the organic luminescent material 140.
  • molecules 68, 65, 53, 52, 63, 64, xl, and x2 are desired because of their optical properties, especially those having at least two halogen atoms at each X group.
  • Optical properties of some of the luminescent materials are shown in figs. 3a and 3b. These graphs show emission spectra, with amongst others emission curve of material 2 as comparison.
  • Molecule 53 is depicted in fig. 2D.
  • at least two selected from G2, G3, G4, and G5 at least comprise X, wherein independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine.
  • G2, G3, G4 and G5 comprise X, with each of these four comprise a (single) fluorine. Note that not necessarily all four of G2, G3, G4 and G5 comprise identical groups.
  • Molecule 65 is depicted in fig. 2C.
  • at least two selected from G2, G3, G4, and G5 at least comprise X, wherein independently at least one of D, E, 1.
  • L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine.
  • G2, G3, G4 and G5 comprise X, with each of these four comprise a fluorine (in fact each comprise two fluorine substituents). Note that not necessarily all four of G2, G3, G4 and G5 comprise identical groups.
  • the product was precipitated by addition of ice-water and collected by filtration. The precipitate was washed with water several times until the aqueous layer became neutral. Drying in the oven at 60°C for 3 days gave crude product used for the next step without further purification.
  • the product was first purified by column chromatography (SiCb, eluent: DCM Heptane 2/1 to DCM) to obtain a mixture of the isomeric diimides.
  • the mixture was washed with EtOH (300 mL) and toluene (300 mL) and then heated at 80°C in toluene (300 mL) over night, The diimide 2386 was recrystallized from the hot toluene solution.
  • the solid was collected through hot filtration and dried under vacuum to give compound 3 (18 g, 20% yield) as an orange powder.
  • Molecule 68 is depicted in fig. 2A.
  • at least two selected from G2, G3, G4, and G5 at least comprise X, wherein independently at least one of D, E, I, L and M of at least two of said at least two selected from G2, G3, G4, and G5 comprise a group selected from fluorine and chlorine.
  • G2 and G5 comprise X, with each of these two comprise a fluorine (in fact each comprise two fluorine substituents).
  • Fig. 5 shows in the upper part an excitation (EX) and emission (EM) spectrum of a schematical system.
  • EX excitation
  • EM emission
  • Curve "a" substantially overlaps with the excitation curve.
  • a shift of the curve, as shown with curves "b” and “c” will lead to a sub- optimal overlap of the curves.
  • On the y-axis the intensity and on the x-axis the wavelength is indicated.
  • the organic molecules are irradiated at a wavelength where their extinction coefficient is lower the lifetime of the molecule increases. It is therefore suggested using molecules and configurations for decreasing the absorbed light per molecule.
  • the light source emission peak is substantially in between the phosphor absorption peak and the phosphor emission peak (Fig. 5, curve c).
  • the source of light may in an embodiment be electronic light sources, such as LED or laser light sources.
  • such source(s) of light may also be one or more other (organic) luminescent materials.
  • ⁇ ( ⁇ ) is the intensity of the light source as a function of wave length and ⁇ ( ⁇ ) is the extinction coefficient as a function of wavelength and z mm corresponds to the maximum extinction coefficient (derived from the excitation spectrum of the organic luminescent material).
  • ⁇ ⁇ and Xy defines the wavelength range for the integral and it corresponds to the range of the emmision and excitation spectra. In the table below the values for the overlap integral is calculated using the equation above.
  • Molecule 2 Yellow 0.54 55000 (80 °C, uniaxially stretched)
  • Molecule 17 Yellow 0.32 9000 (80 °C, uniaxially stretched)
  • Fig. 6c we show the extinction coefficient (in fact excitation spectra) of molecule 17 is shown; e roax is at about 550 rim.
  • the extinction coefficient per molecule in the blue part is much lower than in the yellow part of the spectrum.
  • the lifetime is a factor of 7 longer when irradiated blue light as compared with irradiation with yellow light.
  • Figs. 7a/7b schematically depict two configurations.
  • a combination of a second luminescent material 120 here a europium doped thiogallate (green), excited with a blue source of light 10, with blue light 11
  • an (first) organic luminescent material 110 here e.g. molecule 2), excited with (light source light of) the same source of light with blue light.
  • a structure is chosen wherein the organic luminescent material 110 is also at least partly excited by the luminescence of the thiogallate luminescent material 120.
  • the two different configurations shown in Figs. 7a/7b are configured to create white light on the black body line with a color temperature of 4000K under excitation from blue LED light.
  • the excitation spectra are shown in Fig. 7c, with, EX 1 10 being the excitation of the organic luminescent material and EX 120 being the excitation curve for the second luminescent material 120, here the thiogallate.

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Abstract

La présente invention concerne un dispositif d'éclairage comprenant (i) une source de lumière permettant de générer une lumière provenant de la source de lumière ayant une distribution spectrale présentant une intensité maximale à une première longueur d'onde (λ1) située à l'intérieur de la plage des longueurs d'onde visibles, (ii) un convertisseur de lumière comprenant un matériau luminescent organique, le convertisseur de lumière permettant de transmettre au moins une partie de la lumière provenant de la source de lumière, le matériau luminescent organique étant conçu pour fournir après excitation avec la lumière de la source de lumière une lumière de matériau luminescent ayant une longueur d'onde située à l'intérieur de la plage des longueurs d'onde visibles, le matériau luminescent organique ayant un spectre d'excitation présentant une intensité d'excitation maximale à une seconde longueur d'onde (λ2), et λ1≠λ2.
PCT/EP2014/051900 2013-02-11 2014-01-31 Augmentation de la durée de vie d'un luminophore organique à l'aide d'une excitation différente de l'excitation maximale WO2014122071A1 (fr)

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EP13175795 2013-07-09
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106188092A (zh) * 2016-07-20 2016-12-07 河北大学 N‑2,6‑二异丙基苯胺苝单酰亚胺的制备方法
EP3924430A4 (fr) * 2019-02-14 2023-04-19 Lleaf Pty Ltd Contrôle photopériodique de phytochrome avec des matériaux

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Publication number Priority date Publication date Assignee Title
CN106188092A (zh) * 2016-07-20 2016-12-07 河北大学 N‑2,6‑二异丙基苯胺苝单酰亚胺的制备方法
EP3924430A4 (fr) * 2019-02-14 2023-04-19 Lleaf Pty Ltd Contrôle photopériodique de phytochrome avec des matériaux

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