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WO2023035820A1 - Matériau électroluminescent organique contenant b-n et son utilisation dans un dispositif électroluminescent - Google Patents

Matériau électroluminescent organique contenant b-n et son utilisation dans un dispositif électroluminescent Download PDF

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Publication number
WO2023035820A1
WO2023035820A1 PCT/CN2022/110124 CN2022110124W WO2023035820A1 WO 2023035820 A1 WO2023035820 A1 WO 2023035820A1 CN 2022110124 W CN2022110124 W CN 2022110124W WO 2023035820 A1 WO2023035820 A1 WO 2023035820A1
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Prior art keywords
carbon atoms
group
organic electroluminescent
substituted
atom
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Ceased
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PCT/CN2022/110124
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English (en)
Chinese (zh)
Inventor
白科研
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to the field of luminescent materials, in particular to a class of B-N-containing organic electroluminescent materials and their application in electroluminescent devices.
  • OLED Organic Light Emission Diodes
  • the current commercial OLED device is a multi-layer sandwich structure, including anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer and cathode.
  • the anode generates holes and enters the light-emitting layer through the hole injection layer and the transport layer, while the electrons move from the cathode to the light-emitting layer through the electron injection layer and the transport layer, and the holes and electrons recombine in the light-emitting layer to generate excitons. These excitons transition from an excited state to a ground state, thereby emitting visible light.
  • OLED devices use the principle of additive color, that is, the light-emitting layer is divided into blue light-emitting layer, green light-emitting layer and red light-emitting layer, and different light-emitting layers use organic materials with different light-emitting colors.
  • OLED devices When OLED devices are applied to displays, they are required to have low driving voltage, high luminous efficiency and long life. Therefore, in the gradual improvement of display performance, organic materials have experienced from fluorescent materials to phosphorescent materials, and then to thermally induced Development of active delayed fluorescent materials (TADF).
  • TADF active delayed fluorescent materials
  • green and red light materials are phosphorescent materials, which can use both singlet excitons and triplet excitons to emit light, so the internal quantum efficiency can reach 100%.
  • phosphorescent materials contain heavy metals, which are expensive and expensive. Poor stability and other issues; and the blue light material is a fluorescent material, which can only use singlet excitons to emit light.
  • TADF singlet-triplet energy level difference
  • ⁇ EST singlet-triplet energy level difference
  • TADF materials have relatively low Strong charge transfer characteristics (CT), the spectral half-wave width is too wide, which is not conducive to high color purity display.
  • the present invention provides a type of B-N organic light emitting material and its application in organic light emitting devices.
  • the material introduces electron-withdrawing-N structural units, which can effectively strengthen the multiple resonance effect of the B-N structure, expand the range of multiple resonance effects, increase the ⁇ conjugated plane, and adjust the luminescent spectrum;
  • the group is fixed by the introduced electron-withdrawing group to form a large rigid ⁇ planar structure, which can effectively suppress the vibration in the molecule, and obtain a high-efficiency organic light-emitting material with a narrow half-wave width, which meets the needs of commercialization.
  • the present invention also provides a class of organic electroluminescent materials containing a B-N structure, the general structural formula of which is as shown in one of formulas (I), (II), and (III):
  • X 1 to X 4 are independently selected from electron-withdrawing units
  • substitutions in Ar 1 to Ar 10 are independently hydrogen, deuterium, cyano, nitro, halo, hydroxyl, alkylthio with 1 to 4 carbon atoms, and alkane with 1 to 30 carbon atoms group, cycloalkyl group with 1 to 20 carbon atoms, aryloxy group with 6 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, alkylamino group with 1 to 30 carbon atoms, 6 carbon atoms Arylamino groups with 6 to 30 carbon atoms, aralkylamino groups with 6 to 30 carbon atoms, heteroarylamino groups with 2 to 24 carbon atoms, alkylsilyl groups with 1 to 30 carbon atoms, arylamino groups with 6 to 30 carbon atoms silyl group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, alkynyl group having 2 to 24 carbon atoms, aralkyl group having 7
  • the aryl group is selected from phenyl, naphthyl, anthracenyl, binaphthyl, phenanthrenyl, dihydrophenanthrene, perylenyl, perylenyl, naphthacene, pentacene, benzoperylene, benzocyclopentadienyl , one or more of spirofluorenyl and fluorenyl.
  • the aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, dihydrophenanthrene, tetracene, pentacene, benzoperylene, benzocyclopentadienyl, spirofluorenyl and fluorenyl one or more of.
  • the heteroaryl group is selected from pyrrolyl, imidazolyl, thienyl, furyl, 1,2-thiazolyl, 1,3-thiazolyl, 1,2,3-oxadiazolyl, 1,2,4- Oxadiazolyl, thiadiazolyl, selendiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrazinyl, pyrimidinyl, 1,3,5 -Triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, indole, isoindole, benzimidazole, naphthimidazole, phenanthrenzimidazole, benzotriazole, purine , benzoxazole, naphthoxazole, phenanthroxazole, benzothiadiazolyl, benzoselenodiazolyl, benzotriazolyl, quinolinyl, isoquinolyl,
  • Ar 1 , Ar 2 , Ar 4 , Ar 6 , Ar 8 , Ar 10 in structural formula (a)-(i) are independently selected from one of the formulas Ar-1 to Ar-28, Ar 3 , Ar 5 independently selected from one of the formulas Ar-29 to Ar-65, Ar 7 selected from one of the formulas Ar-66 to Ar-93, and Ar 9 selected from one of the formulas Ar-94 to Ar-99.
  • P 1 represents the site connected to the boron atom
  • P 2 , P 3 , P 4 , and P 5 represent the sites connected to X 1 , X 2 , X 3 , X 4 and the nitrogen atom, respectively
  • the dotted line is the key for the corresponding connection
  • R1 are independently selected from a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a fluorine atom, a cyano group, a linear or branched C1-8 alkyl group, a C6-10 substituted or unsubstituted aryl group, One of C5-10 substituted or unsubstituted heteroaryl groups, or R 1 are bonded to each other with a single bond or -CC- to form a ring; the heteroatoms in the heteroaryl group are selected from One or more of N, O or S, the aryl or heteroaryl is substituted by C1-C4 alkyl.
  • R 1 are independently selected from a hydrogen atom, straight-chain or branched C1-4 alkyl, phenyl, or R 1 are bonded to each other with a single bond or -CC- to form a ring .
  • Ar 1 and Ar 2 are shown as one of Ar-1 to Ar-16, Ar-19 to Ar-26, and Ar 4 is shown as Ar-1, Ar-4, Ar-6, Ar-8, Ar-10, Ar-11, Ar-16, Ar-25, Ar 3 and Ar 5 are Ar-29, Ar-32, Ar-34, One of Ar-36, Ar-37, Ar-38, Ar-54, Ar-59, Ar-64.
  • the second invention of the present invention is to provide an organic electroluminescent device, said organic electroluminescent device comprising at least one layer of organic electroluminescent material containing B-N condensed ring in the functional layer;
  • B-N fused-ring organic electroluminescence material is used as the light-emitting layer material
  • the B-N fused-ring organic electroluminescent material is used as a dopant material or a sensitizer material for the light-emitting layer;
  • the invention provides a kind of B-N organic luminescent material and its application in organic luminescent devices.
  • this type of material introduces electron-withdrawing-N structural units, which can effectively strengthen the multiple resonance effect of the B-N structure, expand the range of multiple resonance effects, increase the ⁇ conjugated plane, and adjust the luminescence spectrum;
  • the aromatic group is fixed by the introduced electron-withdrawing group to form a large rigid ⁇ planar structure, which can effectively suppress the vibration in the molecule, and obtain a high-efficiency organic light-emitting material with a narrow half-wave width, which meets the needs of commercialization.
  • Fig. 1 is a schematic structural diagram of an organic electroluminescent bottom-emitting device of the present invention.
  • the present invention does not require the synthesis method of materials.
  • the following examples are given, but not limited thereto.
  • the raw materials used in the following synthesis are commercially available products unless otherwise specified.
  • Embodiment 6 is a diagrammatic representation of Embodiment 6
  • Embodiment 7 is a diagrammatic representation of Embodiment 7:
  • the organic electroluminescent bottom-emitting device is prepared by using the BN organic electroluminescent material of the present invention, and the structure of the device is shown in FIG. 1 .
  • the transparent conductive ITO glass substrate 10 (with the anode 20 on it) is washed with deionized water, ethanol, acetone, and deionized water in sequence, dried at 80 ° , and then treated with oxygen plasma for 30 minutes.
  • Embodiment 8-embodiment 12 and comparative example 1 are identical to Embodiment 8-embodiment 12 and comparative example 1:
  • Example 8-Example 12 and Comparative Example 1 The fabrication of the organic electroluminescent devices of Example 8-Example 12 and Comparative Example 1 is the same as that of Example 7, except that the guest materials in the light-emitting layer are Structure 2, Structure 8, Structure 121, and Structure 122, Structure 134 and Comparative Example 1.
  • Comparative Example 1 The chemical structures of Comparative Example 1 and Comparative Example 2 materials are as follows:
  • Example 12 2.4 37 535 36 Comparative example 1 2.2 63 524 61 Comparative example 2 3.7 5.1 459 33
  • the B-N organic electroluminescent material of the present invention is applied in organic electroluminescent devices, and has a narrow half-wave width, that is, it will have higher color purity in top-emitting devices.
  • the device luminescent wavelength of the B-N organic electroluminescent material of the present invention is obviously red-shifted, located in the green light region (>500nm), and emits light The color can be adjusted, which is different from conventional B-N organic electroluminescent materials (comparative example 2, emission wavelength: 459nm).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un matériau électroluminescent organique contenant B-N et son utilisation dans un dispositif électroluminescent, le matériau présentant des structures telles que représentées dans les formules générales (I), (II) et (III). Le matériau sur la base d'une structure B-N comporte un motif structural de retrait d'électrons N introduit dans celle-ci, de telle sorte que l'effet de résonance multiple de la structure B-N puisse être efficacement amélioré, que le plan conjugué Π soit augmenté et que le spectre électroluminescent soit ajusté ; et le groupe aromatique sur l'arylamine est fixé par le groupe de retrait d'électrons introduit pour former une grande structure plane Π rigide, de sorte que la vibration dans les molécules puisse être efficacement supprimée, qu'un matériau électroluminescent organique efficace ayant une largeur de demi-onde étroite puisse être obtenu, répondant ainsi aux exigences commerciales.
PCT/CN2022/110124 2021-09-13 2022-08-04 Matériau électroluminescent organique contenant b-n et son utilisation dans un dispositif électroluminescent Ceased WO2023035820A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN202111067045.7 2021-09-13
CN202111067045 2021-09-13
CN202210637944.4A CN115806563A (zh) 2021-09-13 2022-06-08 一类含b-n的有机电致发光材料及其在电致发光器件中的应用
CN202210637944.4 2022-06-08

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117003784A (zh) * 2023-10-07 2023-11-07 吉林大学 基于五元杂环结构的含硼氮多环芳香烃、制备方法和有机电致发光器件

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116162103A (zh) * 2023-02-23 2023-05-26 清华大学 一种有机化合物及其应用
CN117209451B (zh) * 2023-09-15 2024-06-11 石家庄市田航科技有限公司 一种蓝色荧光材料及其制备方法和应用

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109155368A (zh) * 2016-04-26 2019-01-04 学校法人关西学院 有机电场发光元件
CN110407859A (zh) * 2019-07-18 2019-11-05 清华大学 一种发光材料及其应用以及包含其的有机电致发光器件
KR20190127529A (ko) * 2018-12-19 2019-11-13 머티어리얼사이언스 주식회사 유기전계발광소자
WO2019235402A1 (fr) * 2018-06-04 2019-12-12 学校法人関西学院 Composés aromatiques polycycliques et polymères de ceux-ci
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
CN112480154A (zh) * 2020-11-26 2021-03-12 深圳大学 一种手性热活化延迟荧光材料及其圆偏振电致发光器件
CN112898324A (zh) * 2019-12-03 2021-06-04 北京鼎材科技有限公司 化合物、其应用和有机电致发光器件
CN113929709A (zh) * 2020-06-29 2022-01-14 江苏三月科技股份有限公司 一种含硼氮有机化合物及包含其的有机电致发光器件
WO2022018181A1 (fr) * 2020-07-24 2022-01-27 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
CN114773366A (zh) * 2022-03-22 2022-07-22 苏州大学 一种羰基稠合的硼氮衍生物及其制备方法和应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102690280B1 (ko) * 2018-06-11 2024-07-30 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물 및 그의 다량체

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109155368A (zh) * 2016-04-26 2019-01-04 学校法人关西学院 有机电场发光元件
WO2019235402A1 (fr) * 2018-06-04 2019-12-12 学校法人関西学院 Composés aromatiques polycycliques et polymères de ceux-ci
KR20190127529A (ko) * 2018-12-19 2019-11-13 머티어리얼사이언스 주식회사 유기전계발광소자
CN110407859A (zh) * 2019-07-18 2019-11-05 清华大学 一种发光材料及其应用以及包含其的有机电致发光器件
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
CN112898324A (zh) * 2019-12-03 2021-06-04 北京鼎材科技有限公司 化合物、其应用和有机电致发光器件
CN113929709A (zh) * 2020-06-29 2022-01-14 江苏三月科技股份有限公司 一种含硼氮有机化合物及包含其的有机电致发光器件
WO2022018181A1 (fr) * 2020-07-24 2022-01-27 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques
CN112480154A (zh) * 2020-11-26 2021-03-12 深圳大学 一种手性热活化延迟荧光材料及其圆偏振电致发光器件
CN114773366A (zh) * 2022-03-22 2022-07-22 苏州大学 一种羰基稠合的硼氮衍生物及其制备方法和应用

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117003784A (zh) * 2023-10-07 2023-11-07 吉林大学 基于五元杂环结构的含硼氮多环芳香烃、制备方法和有机电致发光器件
CN117003784B (zh) * 2023-10-07 2024-01-05 吉林大学 基于五元杂环结构的含硼氮多环芳香烃、制备方法和有机电致发光器件

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CN115806563A (zh) 2023-03-17
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