WO2015092840A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2015092840A1
WO2015092840A1 PCT/JP2013/083544 JP2013083544W WO2015092840A1 WO 2015092840 A1 WO2015092840 A1 WO 2015092840A1 JP 2013083544 W JP2013083544 W JP 2013083544W WO 2015092840 A1 WO2015092840 A1 WO 2015092840A1
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Prior art keywords
light emitting
transport layer
group
dopant
organic light
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PCT/JP2013/083544
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English (en)
Japanese (ja)
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荒谷　介和
広貴 佐久間
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株式会社日立製作所
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Priority to PCT/JP2013/083544 priority Critical patent/WO2015092840A1/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to an organic light emitting device.
  • the structure of the light emitting layer of the white light emitting organic LED includes a single layer structure and a laminated structure.
  • Patent Document 1 reports a laminated structure in which a hole transport layer is doped with a yellow dopant and a blue dopant is contained in a light emitting layer.
  • Methods of manufacturing the organic LED include a vapor deposition method and a wet method.
  • the vapor deposition method as described in Patent Document 1, it is possible to form a light emitting layer having an arbitrary laminated structure.
  • the deposition method has production problems such as low utilization efficiency of the material and difficulty in increasing the area.
  • the wet method there are production advantages such as high utilization efficiency of materials and easy enlargement, but there is a problem that it is difficult to form a laminated structure.
  • the underlayer should be insoluble in the upper layer solvent. Therefore, the range of material selection is narrow, and there is a problem that the excited state formed in the light emitting layer transfers energy to the peripheral layer to be deactivated and the light emission efficiency is lowered.
  • An object of the present invention is to provide a highly efficient white organic LED that can be formed by a wet process.
  • Patent Document 1 describes that the hole transport layer contains a yellow dopant, it does not clearly show how the yellow dopant is distributed in the hole transport layer, so that it is considered that the light emission efficiency is low.
  • the present invention relates to a first electrode, a second electrode, a light emitting layer disposed between the first electrode and the second electrode, and a charge disposed at a position adjacent to the light emitting layer.
  • An organic light emitting device having a transport layer, wherein the charge transport layer adjacent to the light emitting layer contains a light emitting dopant, and the light emitting dopant moves near the interface between the light emitting layer and the charge transport layer It is characterized by having a functional group.
  • an organic light emitting element which can be formed by a wet method and which achieves high efficiency light emission.
  • FIG. 1 is a cross-sectional view of an embodiment of the organic light emitting device in the present invention.
  • the substrate 1 is a glass substrate.
  • the present invention is not limited to the glass substrate, and a plastic substrate or a metal substrate provided with a suitable water permeability lowering protective film can also be used.
  • the light extraction layer a layer having a scattering property or a layer having a microlens can be used.
  • the lower electrode 2 is an anode.
  • Transparent electrodes such as ITO and IZO are used.
  • the invention is not limited thereto, and a laminate of Al, Ag or the like, a combination of Mo, Cr, a transparent electrode and a light diffusion layer, or the like can also be used.
  • the lower electrode is not limited to the anode, and a cathode can also be used. In that case, Al, Mo, a laminate of Al and Li, an alloy such as AlNi, or the like is used.
  • a transparent electrode such as ITO or IZO may be used.
  • the upper electrode 8 is a cathode.
  • a laminate of Al, an electron injecting LiF, a fluoride of an alkali metal such as Li20, an oxide or the like is used.
  • a co-evaporation product of Al and an alkali metal is also used.
  • a laminate of a transparent electrode such as ITO or IZO and an electron injecting electrode such as MgAg or Li can be used.
  • MgAg or Ag thin film can be used alone.
  • a buffer layer may be provided in order to reduce damage due to sputtering.
  • a metal oxide such as molybdenum oxide or vanadium oxide is used.
  • the lower electrode is a cathode as described above
  • the upper electrode is an anode.
  • a transparent electrode such as ITO or IZO is used.
  • a metal thin film such as an Ag thin film can be used.
  • a buffer layer may be provided in order to reduce damage caused by sputtering.
  • a metal oxide such as molybdenum oxide or vanadium oxide is used.
  • the hole injection layer 3 is a layer for injecting holes from the lower electrode 2.
  • a single layer or a plurality of layers may be provided.
  • the hole injection layer 3 is preferably a conductive polymer such as PEDOT (poly (3,4-ethylenedioxythiophene)): PSS (polystyrene sulfonate).
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS polystyrene sulfonate
  • polypyrrole-based and triphenylamine-based polymer materials can be used.
  • phthalocyanine compounds and starburst amine compounds which are often used in combination with a low molecular weight (weight average molecular weight of 10000 or less) material system are also applicable.
  • the hole transport layer 4 is a layer that efficiently injects holes from the hole injection layer 3 into the light emitting layer and transfers energy from the light emitting layer to efficiently emit light.
  • materials insoluble in the solvent of the upper layer of a homopolymer or copolymer such as fluorene, carbazole, or arylamine are used.
  • materials having a thiophene type or a pyrrole type as a skeleton can also be used.
  • polymers having a skeleton such as fluorene, carbazole, arylamine, thiophene or pyrrole in the side chain can also be used.
  • the hole transport layer 4 of the present invention contains a light emitting dopant.
  • the light emitting dopant of the present invention may be any of so-called fluorescent materials, phosphorescent materials, and delayed fluorescent materials.
  • the light emitting dopant includes the functionality to be present in high concentration near the interface with the light emitting layer.
  • the concentration of the light emitting dopant is not particularly limited, but preferably about 0.1 to 10 wt%.
  • the light emitting layer 5 is a layer for obtaining light emission of a desired light emission color.
  • the light emitting layer 5 contains a host and a light emitting dopant.
  • the light emitting dopant any of so-called fluorescent materials, phosphorescent materials and delayed fluorescent materials can be used. Only one kind of light emitting dopant may be used, but two or three kinds of light emitting dopants may be used.
  • the light emitting layer 5 may contain a hole transporting material or an electron transporting material in addition to the host and the light emitting dopant. They are used to improve charge balance in the light emitting layer.
  • the light emitting layer 5 may contain a binder polymer.
  • a triphenylamine derivative a carbazole derivative, a fluorene derivative or an arylsilane derivative
  • metal complexes of 8-quinolinol can also be used.
  • binder polymers such as polycarbonate, polystyrene, acrylic resin, polyamide and gelatin can also be used in combination.
  • the hole blocking layer 6 is a layer for preventing transfer of holes from the light emitting layer 5 to the electron transporting layer 7.
  • Examples of the material of the hole blocking layer 6 include bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum (hereinafter, BAlq) and tris (8-quinolinolato) aluminum (hereinafter, Alq3).
  • Tris (2,4,6-trimethyl-3- (pyridin-3-yl) phenyl) borane hereinafter, 3TPYMB
  • 1,4-bis (triphenylsilyl) benzene hereinafter, UGH2
  • oxadiazole derivative 1,4-bis (triphenylsilyl) benzene
  • UGH2 1,4-bis (triphenylsilyl) benzene
  • UGH2 1,4-bis (triphenylsilyl) benzene
  • oxadiazole derivative 1,4-bis (triphenylsilyl) benzene
  • triazole Derivatives fullerene derivatives, phenanthroline derivatives, quinoline derivatives, benzimidazole derivatives, triazine derivatives and the like can be used.
  • the electron transport layer 7 is a layer for transporting electrons to the light emitting layer 5 via the hole blocking layer 6.
  • Examples of the material of the electron transport layer 7 include bis (2-methyl-8-quinolinolato) -4- (phenylphenolato) aluminum (hereinafter, BAlq), tris (8-quinolinolato) aluminum (hereinafter, Alq3), Tris (2,4,6-trimethyl-3- (pyridin-3-yl) phenyl) borane (hereinafter, 3TPYMB), 1,4-bis (triphenylsilyl) benzene (hereinafter, UGH2), oxadiazole derivative, triazole derivative A fullerene derivative, a phenanthroline derivative, a quinoline derivative, a benzimidazole derivative, a triazine derivative or the like can be used.
  • a large amount of light emitting dopant is distributed in the vicinity of the interface between the hole transport layer 4 and the light emitting layer 5. Therefore, when the excited state formed in the light emitting layer 5 transfers energy to the hole transport layer 4, a large amount of light is emitted in the vicinity of the interface with the light emitting layer 5 of the hole transport layer 4, and the transferred energy is deactivated. Prevent being lost. Further, the light emitting dopant concentration in the hole transport layer 4 is hardly present on the hole injection layer 3 side, and is high near the light emitting layer 5.
  • the light emitting dopant can be a hole trap in the hole transport layer 4, but in the present invention, since it has the concentration distribution as described above, it does not become a hole trap up to the vicinity of the light emitting layer 5. Therefore, hole injection can be efficiently performed as compared with the case where the above concentration distribution is not provided.
  • the hole blocking layer 6 has the light emitting dopant having a functional group to be present in the vicinity of the interface with the light emitting layer 5 in high concentration. You may Such a structure can also obtain the same effect as described above.
  • At least one of the hole transport layer 4 or the electron transport layer 7 contains a light emitting dopant having a predetermined functional group.
  • a light emitting dopant having a predetermined functional group there are various forms as to how many kinds of light emitting dopants are included in each of the light emitting layer 5, the hole transporting layer 4, and the electron transporting layer 7. The form is shown in Table 1.
  • Table 1 shows an example in which a stacked structure is formed in the order of blue, red and green from the upper electrode 8 to the lower electrode 2.
  • blue, red and green are used, it is possible to realize white light emission not only in this but also in the order of blue, green and red or in the order of red, blue and green.
  • the luminous efficiency is particularly high in the order of blue, green, red, blue, red and green.
  • the electron transport layer 7 does not contain a light emitting dopant
  • the light emitting layer 5 contains a blue dopant and a red dopant
  • the hole transport layer 4 contains a green dopant.
  • the green dopant has a functional group for moving the green dopant to the vicinity of the interface between the light emitting layer 5 and the hole transport layer 4.
  • fluoroalkyl group, perfluoroalkyl group and siloxy group having fluoroalkyl group can be mentioned as the functional group.
  • the electron transport layer 7 contains a blue dopant
  • the light emitting layer 5 contains a red dopant and a green dopant
  • the hole transport layer 4 does not contain a luminescent dopant.
  • the blue dopant has a functional group for moving the blue dopant to the vicinity of the interface between the electron transport layer 7 and the light emitting layer 5.
  • an alkyl group having 4 or more carbon atoms, a hydroxy group, a carboxyl group, an amido group, an acyl group and an amino group can be mentioned as the functional group.
  • the pattern 3 has a configuration in which the electron transport layer 7 contains a blue dopant and a red dopant, the light emitting layer 5 contains a green dopant, and the hole transport layer 4 does not contain a luminescent dopant.
  • the blue dopant or the red dopant has a functional group for moving the dopant to the vicinity of the interface between the electron transport layer 7 and the light emitting layer 5.
  • an alkyl group having 4 or more carbon atoms, a hydroxy group, a carboxyl group, an amido group, an acyl group and an amino group can be mentioned as the functional group.
  • both the blue dopant and the red dopant may move to the vicinity of the interface between the electron transport layer 7 and the light emitting layer 5.
  • the electron transport layer 7 does not contain a light emitting dopant
  • the light emitting layer 5 contains a blue dopant
  • the hole transport layer 4 contains a red dopant and a green dopant.
  • the red dopant or the green dopant has a functional group for moving the dopant to the vicinity of the interface between the light emitting layer 5 and the hole transport layer 4.
  • fluoroalkyl group, perfluoroalkyl group and siloxy group having fluoroalkyl group can be mentioned as the functional group. Note that both the red dopant and the green dopant may move to the vicinity of the interface between the light emitting layer 5 and the hole transport layer 4.
  • the electron transport layer 7 contains a blue light emitting dopant
  • the light emitting layer 5 contains a red dopant
  • the hole transport layer 4 contains a green dopant.
  • the green dopant has a functional group for moving the green dopant to the vicinity of the interface between the light emitting layer 5 and the hole transport layer 4.
  • fluoroalkyl group, perfluoroalkyl group and siloxy group having fluoroalkyl group can be mentioned as the functional group.
  • the blue dopant has a functional group for moving the blue dopant to the vicinity of the interface between the electron transport layer 7 and the light emitting layer 5.
  • an alkyl group having 4 or more carbon atoms, a hydroxy group, a carboxyl group, an amido group, an acyl group and an amino group can be mentioned as the functional group.
  • the luminous efficiency is higher if the luminous dopants of each color are present with a concentration gradient than the luminous dopants contained in the organic luminous element are collectively present in a certain region. Therefore, in the case of the pattern 5, the luminous efficiency is the highest.
  • Example 1 and Comparative Example 1 In Example 1, the following materials were used for each layer.
  • a glass substrate was used as the substrate 1 and ITO was used as the lower electrode 2.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS polystyrene sulfonate
  • the dopant of Formula (1) has a fluoroalkyl group. As a result, the dopant of the formula (1) spontaneously moves toward the interface between the light emitting layer 5 and the hole transport layer 4, and as a result, the concentration of the green dopant at the interface between the light emitting layer 5 and the hole transport layer 4 It gets higher locally.
  • mCP 1-dicarbazolylbenzene
  • the blue dopant of the following formula (2) and the red dopant of Formula (3) were used for the dopant.
  • the blue dopant and the green dopant are 1% by weight with respect to the host.
  • the coating liquid for forming the light emitting layer 5 was prepared using toluene as a solvent so that the weight ratio of solid content to the solvent was 1%.
  • the light emitting layer 5 was formed by spin coating using this coating solution.
  • Comparative Example 1 an organic light emitting device was produced as a structure similar to that of Example 1 except for the following points.
  • the hole transport layer 4 does not have a light emitting dopant. Only the triphenylamine-based polymer of Example 1 is used. Further, the light emitting layer 5 has a green light emitting dopant represented by the following formula (4).
  • Example 1 A voltage was applied to the organic light emitting devices manufactured in Example 1 and Comparative Example 1, and the current and luminance flowing were measured.
  • the maximum power efficiency of the organic light emitting device of Example 1 determined from the result was 1.4 times that of the organic light emitting device of Comparative Example 1.
  • the power efficiency of the organic light emitting device of Example 1 is increased compared to the organic light emitting device of Comparative Example 1 because the blue dopant and the red dopant are excited in the light emitting layer 5 of Example 1. Thereafter, the excitation energy of the blue dopant transferred to the hole transport layer 4 contributes to the light emission of the green dopant in the hole transport layer 4, and the green dopant efficiently emits light.
  • Example 2 and Comparative Example 2 The structure of the organic light emitting device of Example 2 is the same as that of Example 1 except for the following.
  • the hole transport layer 4 does not have a light emitting dopant. Only the triphenylamine-based polymer of Example 1 is used.
  • the host material of the light emitting layer 5 used the material represented by Formula (5).
  • the light emitting dopant represented by the formula (1) was used.
  • red dopant present in the light emitting layer 5 a light emitting dopant represented by the formula (6) was used.
  • the electron transport layer 7 is composed of a host and a light emitting dopant, and the material represented by the formula (7) is used as the host, and the material represented by the formula (8) is used as the light emitting dopant.
  • the concentration of the light emitting dopant is 3 wt% with respect to the host.
  • An isopropyl alcohol was used as the solvent, and a solution having a total solid content of 1 wt% was used to form a film on the light emitting layer by spin coating.
  • the structure of the organic light emitting device of Comparative Example 2 is the same as that of Example 2 except for the following.
  • the electron transport layer 7 does not contain a light emitting dopant. It is only the host material represented by Formula (7).
  • the light emitting layer 5 contains 3 wt% of the light emitting dopant represented by the formula (8) with respect to the host.
  • a voltage was applied to the organic light emitting device produced in Example 2 and Comparative Example 2, and the current and luminance flowing were measured. As a result, the maximum power efficiency of Example 2 was 1.4 times that of Comparative Example 2.
  • the efficiency of the organic light emitting device of Example 2 is large compared to the organic light emitting device of Comparative Example 2 because the exciton formed at the interface between the light emitting layer 5 and the electron transporting layer 7 of Example 2 emits light. This is to contribute to the emission of the green dopant and the red dopant in the layer and to contribute to the emission of the blue dopant without moving to the electron transport layer 7 and quenching.
  • Example 3 The organic light emitting device of Example 3 has the same configuration as the organic light emitting device of Example 1 except for the following.
  • the dopant represented by Formula (4) was used for the hole transport layer 4 of a present Example. Unlike the formula (1), the dopant of the formula (4) does not have a fluoroalkyl group.
  • the characteristics of the organic light emitting device of this example were measured in the same manner as in Example 1. As a result, the maximum power efficiency of the organic light emitting device of this example was 1.2 times that of Comparative Example 1.
  • the efficiency of the organic light emitting device of Example 3 is large compared to the organic light emitting device of Comparative Example 1 because the blue dopant and the red dopant become excited in the light emitting layer 5 of Example 3, and thereafter This is because the excitation energy of the blue dopant transferred to the hole transport layer 4 contributes to the emission of the green dopant in the hole transport layer 4 and the green dopant efficiently emits light.
  • Example 4 the reason that the efficiency of the organic light emitting device of Example 3 is small compared to the organic light emitting device of Example 1 is that the green dopant of Example 3 does not have a fluoroalkyl group. It is distributed throughout, and as a result, the green dopant acts as a hole trap in the hole transport layer 4 to prevent the hole transport.
  • Example 4 and Comparative Example 3 The organic light-emitting device of Example 4 has the same configuration as that of Example 1 except for the following. For the hole transport layer 4, a light emitting dopant represented by the formula (9) was used.
  • a carbazole-based material which is crosslinked by heating to be insolubilized was used as a host material of the hole transport layer 4.
  • This material contains an acid generator to initiate a crosslinking reaction upon heating.
  • the hole transport layer 4 was formed into a film by spin coating from a toluene solution having a solid content of 1 wt%, and was heated at 180 ° C. for 30 minutes to be crosslinked and inactivated.
  • the organic light emitting device of Comparative Example 3 has the same configuration as the organic light emitting device of Example 4 except for the following. That is, the material represented by Formula (1) was used as a light emitting dopant of the hole transport layer 4. As a result, the maximum power efficiency of the organic light emitting device of Example 4 was 1.6 times that of the organic light emitting device of Comparative Example 3.
  • Example 4 H + generated from the acid generating material This is because ions are added to the unpaired electron of the N atom of the amide bond contained in the light emitting dopant represented by the formula (9) to prevent the decomposition of the light emitting dopant.
  • the light emitting dopant contains an element having an unpaired electron
  • the light emission efficiency is improved.
  • Table 2 shows the configurations of Example 1-4 and Comparative example 1-3.

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  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

　Le but de la présente invention est de fournir un élément électroluminescent organique à lumière blanche de type à enrobage à efficacité élevée. La présente invention porte sur un élément électroluminescent organique ayant une première électrode, une seconde électrode, une couche électroluminescente disposée entre la première électrode et la seconde électrode, et une couche de transport de charge positionnée de manière adjacente par rapport à la couche électroluminescente ; l'élément électroluminescent organique étant caractérisé par le fait que la couche de transport de charge adjacente à la couche électroluminescente contient un dopant d'émission de lumière, et le dopant d'émission de lumière possède un groupe fonctionnel pour se déplacer vers le voisinage de l'interface entre la couche électroluminescente et la couche de transport de charge.
PCT/JP2013/083544 2013-12-16 2013-12-16 Élément électroluminescent organique WO2015092840A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113258009A (zh) * 2020-04-17 2021-08-13 广东聚华印刷显示技术有限公司 复合材料及其制备方法、量子点发光二极管
WO2023054110A1 (fr) * 2021-09-29 2023-04-06 住友化学株式会社 Élément luminescent

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002093583A (ja) * 2000-08-30 2002-03-29 Eastman Kodak Co 有機発光ダイオードデバイス
JP2004134396A (ja) * 2002-09-16 2004-04-30 Eastman Kodak Co 有機白色発光ダイオードデバイス
WO2012091005A1 (fr) * 2010-12-28 2012-07-05 株式会社日立製作所 Élément électroluminescent organique et dispositif à source de lumière utilisant ledit élément, matériau de couche électroluminescente organique et liquide de revêtement destiné à former une couche électroluminescente organique et procédé de fabrication d'un élément électroluminescent organique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002093583A (ja) * 2000-08-30 2002-03-29 Eastman Kodak Co 有機発光ダイオードデバイス
JP2004134396A (ja) * 2002-09-16 2004-04-30 Eastman Kodak Co 有機白色発光ダイオードデバイス
WO2012091005A1 (fr) * 2010-12-28 2012-07-05 株式会社日立製作所 Élément électroluminescent organique et dispositif à source de lumière utilisant ledit élément, matériau de couche électroluminescente organique et liquide de revêtement destiné à former une couche électroluminescente organique et procédé de fabrication d'un élément électroluminescent organique

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113258009A (zh) * 2020-04-17 2021-08-13 广东聚华印刷显示技术有限公司 复合材料及其制备方法、量子点发光二极管
WO2023054110A1 (fr) * 2021-09-29 2023-04-06 住友化学株式会社 Élément luminescent

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