WO2020215564A1 - Matériau semi-conducteur organique, procédé de préparation correspondant et utilisation associée - Google Patents

Matériau semi-conducteur organique, procédé de préparation correspondant et utilisation associée Download PDF

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WO2020215564A1
WO2020215564A1 PCT/CN2019/103104 CN2019103104W WO2020215564A1 WO 2020215564 A1 WO2020215564 A1 WO 2020215564A1 CN 2019103104 W CN2019103104 W CN 2019103104W WO 2020215564 A1 WO2020215564 A1 WO 2020215564A1
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organic
emitting material
organic light
substituted
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PCT/CN2019/103104
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马晓宇
汪康
王永光
王进政
贺金新
王铁
李贺
毕岩
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吉林奥来德光电材料股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • An organic electroluminescence (EL) device generally consists of two opposed electrodes and at least one layer of organic light emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and the cathode to form electron and hole pairs, causing the organic compound with fluorescence or phosphorescence characteristics to emit light.
  • the purpose of the present disclosure includes, for example, to provide an organic light-emitting material and a preparation method and application thereof.
  • the organic light-emitting material is a connection structure of asymmetric anthracene and triarylamine derivatives with good hole transport properties, and can be used as an electron transport material.
  • the luminous efficiency and luminous brightness are improved, thereby greatly improving the performance of various aspects of the organic electroluminescent device.
  • the present disclosure provides an organic light-emitting material, which has a structure shown in formula (1):
  • R 1 and R 2 are each independently selected from any of the following groups:
  • the R 3 is a substituted or unsubstituted C 6 to C 18 phenyl group, a substituted or unsubstituted C 10 to C 14 fused ring aryl group, or a substituted or unsubstituted C 3 to C 11 heterocyclic group;
  • Ring A is C 3 ⁇ C 60 cycloalkyl, C 3 ⁇ C 60 cycloalkenyl, C 3 ⁇ C 60 cycloalkynyl, C 6 ⁇ C 60 aryl, C 6 ⁇ C 60 heteroaryl , C 10 ⁇ C 60 fused ring group or C 10 ⁇ C 60 spiro ring group;
  • R 1 and R 2 are each independently selected from any of the following groups: C 1 to C 30 alkyl, C 3 to C 30 cycloalkyl, C 6 to C 30 Aryl group, C 7 ⁇ C 30 aralkyl group, C 8 ⁇ C 30 aralkenyl group, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl mercapto group, C 6 ⁇ C 30 hetero An aryl group, a C 10 -C 30 fused ring group, a C 6 -C 30 aryl-substituted silyl group, or a C 2 -C 30 heteroaryl-substituted silyl group.
  • R 1 and R 2 are each independently selected from any of the following groups:
  • R 3 is a substituted or unsubstituted C 7 to C 12 phenyl group, a substituted or unsubstituted C 10 fused ring aryl group, or a substituted or unsubstituted C 5 to C 10 heterocyclic group.
  • R 1 and R 2 are each independently selected from any of the following groups: C 1 ⁇ C 10 alkyl, C 3 ⁇ C 12 cycloalkyl, C 6 ⁇ C 12 Aryl group, C 7 ⁇ C 12 aralkyl group, C 8 ⁇ C 14 aralkenyl group, C 6 ⁇ C 12 arylamino group, C 6 ⁇ C 12 aryl mercapto group, C 6 ⁇ C 12 hetero Aryl, C 10 ⁇ C 20 fused ring group, C 6 ⁇ C 12 aryl substituted silyl group or C 2 ⁇ C 12 heteroaryl substituted silyl group;
  • R 3 is a substituted or unsubstituted C 9 to C 11 phenyl group, a substituted or unsubstituted C 14 condensed ring aryl group, or a substituted or unsubstituted C 10 to C 11 heterocyclic group.
  • the present disclosure also provides a method for preparing an organic light-emitting material, including the following steps:
  • X is I, Br or Cl
  • R 1 , R 2 , R 3 , L, a, and b are all consistent with the range defined by formula (1).
  • the preparation method includes the following steps:
  • the preparation method includes the following steps:
  • the present disclosure also provides an electron transport layer containing the organic light-emitting material described in the present disclosure.
  • the present disclosure also provides an organic electroluminescent device containing the organic light-emitting material described in the present disclosure.
  • the organic electroluminescent device of the present disclosure includes a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode; for example, the organic layer It includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic light-emitting material described in the present disclosure is a material used as an electron transport layer of an organic electroluminescent device.
  • the organic electroluminescent device described in the present disclosure is selected from the group consisting of flat panel displays, flat luminous bodies, surface-emitting OLED luminous bodies for lighting, flexible luminous bodies, copiers, printers, LCD backlights or The light source, display board and logo of the measuring machine.
  • the present disclosure also provides the application of the organic electroluminescent device described in the present disclosure in the preparation of organic solar cells, electronic paper, organic photoreceptors or organic transistors.
  • the organic light-emitting material provided by the present disclosure is a compound with a novel structure prepared by introducing anthracene as the core molecule and the strong electron-drawing group structure of imidazole compounds with different substituents. Therefore, the organic light-emitting material represented by formula (1) of the present disclosure retains the high triplet energy level and good thermal stability of anthracene, and has a lower LUMO energy level, such as between -2.6eV and -3.0eV , Thereby reducing the energy barrier of electron injection. Therefore, the organic electroluminescent device using the organic light-emitting material of the present disclosure as the electron transport material has better luminous efficiency.
  • the organic electroluminescent device prepared in the present disclosure using the organic light-emitting material of the present disclosure as an electron transport material can achieve good luminous efficiency and longevity. Therefore, the organic light-emitting material provided in the present disclosure is very important in the practical OLED industry.
  • the organic electroluminescent device of the present disclosure is a flat panel display, a flat luminous body, a surface-emitting OLED luminous body for lighting, a flexible luminous body, a copier, a printer, an LCD backlight or a measuring machine type light source, a display board, a logo, etc., suitable for use .
  • the preparation method of the organic light-emitting material provided by the present disclosure is simple and easy to implement, and has a high yield.
  • the present disclosure provides an organic light-emitting material, the structural formula of which is shown in formula (1):
  • R 1 and R 2 are each independently selected from any of the following groups:
  • the R 3 is a substituted or unsubstituted C 6 to C 18 phenyl group, a substituted or unsubstituted C 10 to C 14 fused ring aryl group, or a substituted or unsubstituted C 3 to C 11 heterocyclic group;
  • L is hydrogen, aryl or heteroaryl
  • Ring A is C 3 ⁇ C 60 cycloalkyl, C 3 ⁇ C 60 cycloalkenyl, C 3 ⁇ C 60 cycloalkynyl, C 6 ⁇ C 60 aryl, C 6 ⁇ C 60 heteroaryl , C 10 ⁇ C 60 fused ring group or C 10 ⁇ C 60 spiro ring group;
  • a is an integer of 0-5, and b is an integer of 1-4.
  • R 1 and R 2 are each independently selected from any of the following groups: C 1 to C 30 alkyl, C 3 to C 30 cycloalkyl, C 6 to C 30 Aryl group, C 7 ⁇ C 30 aralkyl group, C 8 ⁇ C 30 aralkenyl group, C 6 ⁇ C 30 arylamino group, C 6 ⁇ C 30 aryl mercapto group, C 6 ⁇ C 30 hetero An aryl group, a C 10 -C 30 fused ring group, a C 6 -C 30 aryl-substituted silyl group, or a C 2 -C 30 heteroaryl-substituted silyl group.
  • R 1 and R 2 are each independently selected from any of the following groups:
  • R 3 is a substituted or unsubstituted C 7 to C 12 phenyl group, a substituted or unsubstituted C 10 fused ring aryl group, or a substituted or unsubstituted C 5 to C 10 heterocyclic group.
  • R 1 and R 2 are each independently selected from any of the following groups: C 1 ⁇ C 10 alkyl, C 3 ⁇ C 12 cycloalkyl, C 6 ⁇ C 12 Aryl group, C 7 ⁇ C 12 aralkyl group, C 8 ⁇ C 14 aralkenyl group, C 6 ⁇ C 12 arylamino group, C 6 ⁇ C 12 aryl mercapto group, C 6 ⁇ C 12 hetero Aryl, C 10 ⁇ C 20 fused ring group, C 6 ⁇ C 12 aryl substituted silyl group or C 2 ⁇ C 12 heteroaryl substituted silyl group;
  • R 3 is a substituted or unsubstituted C 9 to C 11 phenyl group, a substituted or unsubstituted C 14 condensed ring aryl group, or a substituted or unsubstituted C 10 to C 11 heterocyclic group.
  • L is hydrogen, phenyl, pyridyl, pyrimidinyl, or pyrazinyl.
  • R 3 is any one of the following structures:
  • the organic light-emitting material is any one of the following structures:
  • the present disclosure also provides a method for preparing an organic light-emitting material, including the following steps:
  • X is I, Br or Cl
  • R 1 , R 2 , R 3 , L, a, and b are all consistent with the range defined by formula (1).
  • the preparation method includes the following steps:
  • the preparation method includes the following steps:
  • the present disclosure also provides an electron transport layer containing the organic light-emitting material described in the present disclosure.
  • the present disclosure also provides an organic electroluminescent device containing the organic light-emitting material described in the present disclosure.
  • the organic electroluminescent device of the present disclosure includes a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode; for example, the organic layer It includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic layer of the present disclosure has a single-layer structure
  • the organic layer is a light-emitting layer
  • the organic layer when the organic layer is a multilayer structure, the organic layer includes a light-emitting layer; the light-emitting layer preferably includes a phosphorescent host and a fluorescent host , One or more of phosphorescent doped materials and fluorescent doped materials.
  • the organic light-emitting material having the formula (1) of the present disclosure is a material for the electron transport layer of the organic electroluminescence device.
  • the above-mentioned organic layer may include the above-mentioned hole injection layer, hole transport layer, light-emitting layer, hole blocking layer, and electron transport layer at the same time, and these multilayer structures may be in accordance with the above-mentioned thin film evaporation, electron beam evaporation or Evaporation methods such as physical vapor deposition can also use various polymer material solvent engineering instead of evaporation methods, such as spin-coating, tape-casting, doctor-blading , Screen-Printing, ink-jet printing or thermal imaging (Thermal-Imaging) methods to reduce the number of layers.
  • the organic electroluminescent device described in the present disclosure is selected from the group consisting of flat panel displays, flat luminous bodies, surface-emitting OLED luminous bodies for lighting, flexible luminous bodies, copiers, printers, LCD backlights or The light source, display board and logo of the measuring machine.
  • the present disclosure also provides the application of the organic electroluminescent device described in the present disclosure in the preparation of organic solar cells, electronic paper, organic photoreceptors or organic transistors.
  • the organic light-emitting material provided by the present disclosure is a compound with a novel structure prepared by introducing anthracene as the core molecule and the strong electron-drawing group structure of imidazole compounds with different substituents. Therefore, the organic light-emitting material represented by formula (1) of the present disclosure retains the high triplet energy level and good thermal stability of anthracene, and has a lower LUMO energy level, such as between -2.6eV and -3.0eV , Thereby reducing the energy barrier of electron injection. Therefore, the organic electroluminescent device using the organic light-emitting material of the present disclosure as the electron transport material has better luminous efficiency.
  • the organic electroluminescent device prepared in the present disclosure using the organic light-emitting material of the present disclosure as an electron transport material can achieve good luminous efficiency and longevity. Therefore, the organic light-emitting material provided in the present disclosure is very important in the practical OLED industry.
  • the organic electroluminescent device of the present disclosure is a flat panel display, a flat luminous body, a surface-emitting OLED luminous body for lighting, a flexible luminous body, a copier, a printer, an LCD backlight or a measuring machine type light source, a display board, a logo, etc., suitable for use .
  • the preparation method of the organic light-emitting material provided by the present disclosure is simple and easy to implement, and has a high yield.
  • the coating thickness of Fisher Company is The ITO glass substrate is cleaned twice in distilled water, ultrasonically cleaned for 30 minutes, and then repeatedly cleaned with distilled water for two times, ultrasonically cleaned for 10 minutes, after the distilled water cleaning is completed, ultrasonically cleaned with isopropanol, acetone, methanol in order, and then dried , Transfer to the plasma cleaning machine, wash the above-mentioned substrate for 5 minutes, and send it to the vapor deposition machine.
  • the organic electroluminescence device includes an anode, a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, an auxiliary material layer, and a cathode.
  • the anode is indium tin oxide
  • the hole injection layer is (HAT-CN) with a thickness of 60nm
  • the hole transport layer is [two-[4-(N,N-xylyl-amino)-benzene with a thickness of 30nm Base] cyclohexane (TAPC)
  • the organic light-emitting layer has a thickness of 10 nm, which includes 90% of 4,4'-bis(carbazol-9-yl)-biphenyl, CBP) as the light-emitting host material, and doped with 10% bis(1-phenyl-isoquinoline)(acetylacetone) iridium(III)(Ir(ppy) 2 (acac)) luminescent material
  • the electron transport layer is any of the compounds 001-030 with a thickness of 50nm One
  • the auxiliary material layer is LiF with a thickness of 1 nm
  • the cathode is aluminum. The organic vapor deposition speed is maintained during
  • the organic electroluminescent device was prepared according to the same method as the organic electroluminescent device preparation example 1, and the structure of the electron transport layer compound was as follows:
  • the organic electroluminescence device prepared above was subjected to a forward DC bias voltage, and the organic electroluminescence characteristics were measured using the PR-650 photometric measuring equipment of Photo Research Company, and the reference gray scale of McScience Company was used at 5000cd/m 2
  • the life measuring device measured the life of T95. The results are shown in Table 2.
  • the organic light-emitting material provided by the present disclosure is a strong electron-withdrawing group structure of imidazole compounds with anthracene as the core molecule and introduced different substituents. Therefore, the organic light-emitting material represented by formula (1) of the present disclosure retains the high triplet energy level and good thermal stability of anthracene, and has a lower LUMO energy level, such as between -2.6eV and -3.0eV , Thereby reducing the energy barrier of electron injection. Therefore, the organic electroluminescent device using the organic light-emitting material of the present disclosure as the electron transport material has better luminous efficiency.
  • the organic electroluminescent device prepared in the present disclosure using the organic light-emitting material of the present disclosure as an electron transport material can achieve good luminous efficiency and longevity. Therefore, the organic light-emitting material provided in the present disclosure is very important in the practical OLED industry.
  • the organic electroluminescent device of the present disclosure is a flat panel display, a flat luminous body, a surface-emitting OLED luminous body for lighting, a flexible luminous body, a copier, a printer, an LCD backlight or a measuring machine type light source, a display board, a logo, etc., suitable for use .
  • the organic light-emitting material provided by the present disclosure is a compound with a novel structure prepared by introducing anthracene as the core molecule and the strong electron-drawing group structure of imidazole compounds with different substituents. Therefore, the organic light-emitting material represented by formula (1) of the present disclosure retains the high triplet energy level and good thermal stability of anthracene, and has a lower LUMO energy level, thereby reducing the energy barrier of electron injection. Therefore, the organic electroluminescent device using the organic light-emitting material of the present disclosure as the electron transport material has better luminous efficiency.
  • the organic electroluminescent device prepared in the present disclosure using the organic light-emitting material of the present disclosure as an electron transport material can achieve good luminous efficiency and longevity. Therefore, the organic light-emitting material provided in the present disclosure is very important in the practical OLED industry. The role of.
  • the preparation method of the organic light-emitting material provided by the present disclosure is simple and easy to implement, and has a high yield.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention se rapporte au domaine technique des matériaux photoélectriques organiques, et concerne en particulier un matériau électroluminescent organique, un procédé de préparation correspondant et une utilisation associée. Le matériau électroluminescent organique a une structure représentée par la formule (1). Le matériau électroluminescent organique selon la présente invention est un composé d'une nouvelle structure préparé à l'aide de l'anthracène en tant que molécule noyau et par introduction d'une structure de groupe attracteur d'électrons forts d'un composé imidazole ayant différents groupes de substitution. Par conséquent, le matériau électroluminescent organique représenté par la formule (1) selon la présente invention conserve un niveau d'énergie de triplet élevé et une bonne stabilité thermique de l'anthracène, et a un faible niveau d'énergie LUMO tel qu'un niveau d'énergie entre -2,6 eV et -3,0 eV, et une barrière d'énergie d'injection d'électrons réduite. Le matériau électroluminescent organique fourni par la présente invention peut être utilisé en tant que matériau de transport d'électrons dans un dispositif électroluminescent organique, de sorte que le dispositif électroluminescent organique obtenu présente une bonne efficacité lumineuse, et par conséquent le matériau électroluminescent organique fourni par la présente invention joue un rôle très important dans l'industrie des diodes électroluminescentes organiques (OLED) ayant une grande facilité de mise en œuvre. Le procédé de préparation du matériau électroluminescent organique selon la présente invention est simple et pratique, et le rendement est élevé. (I)
PCT/CN2019/103104 2019-04-22 2019-08-28 Matériau semi-conducteur organique, procédé de préparation correspondant et utilisation associée WO2020215564A1 (fr)

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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109879811A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 有机发光材料及制备方法和应用
CN110627659A (zh) * 2019-09-26 2019-12-31 吉林奥来德光电材料股份有限公司 有机发光化合物及其制备方法和器件
CN111004183B (zh) * 2019-12-27 2022-04-22 阜阳欣奕华材料科技有限公司 一种有机电致发光化合物、电子传输材料和有机电致发光器件
CN113620885A (zh) * 2020-05-08 2021-11-09 北京夏禾科技有限公司 含氘原子的电子传输材料及其应用
CN113831292A (zh) * 2021-10-13 2021-12-24 上海传勤新材料有限公司 一种含有苯并咪唑和蒽的有机电子传输材料及其应用

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012108877A1 (fr) * 2011-02-11 2012-08-16 University Display Corporation Dispositif électroluminescent organique et matériaux pour utilisation dans celui-ci
CN103531714A (zh) * 2012-07-30 2014-01-22 昆山维信诺显示技术有限公司 电子传输层、含该层的有机电致发光器件及其制备
JP2015106658A (ja) * 2013-11-29 2015-06-08 出光興産株式会社 有機エレクトロルミネッセンス素子および電子機器
CN104710410A (zh) * 2015-01-23 2015-06-17 北京鼎材科技有限公司 一种联苯并咪唑衍生物、其制备方法及其应用
CN108359441A (zh) * 2018-03-23 2018-08-03 吉林奥来德光电材料股份有限公司 一种有机发电致光材料及其制备方法和应用
CN108586352A (zh) * 2017-12-21 2018-09-28 北京燕化集联光电技术有限公司 一种有机材料及其在有机电致发光器件中的应用
CN109309166A (zh) * 2017-07-28 2019-02-05 北京鼎材科技有限公司 有机电致发光器件以及含有2,6,9,10-位四取代的蒽化合物
CN109314189A (zh) * 2016-06-02 2019-02-05 株式会社Lg化学 有机发光元件
CN109879811A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 有机发光材料及制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170075122A (ko) * 2015-12-22 2017-07-03 삼성디스플레이 주식회사 유기 발광 소자
US11264576B2 (en) * 2016-12-19 2022-03-01 Idemitsu Kosan Co., Ltd. Specifically substituted ladder type compounds for organic light emitting devices
CN109384726A (zh) * 2018-06-28 2019-02-26 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机电致发光器件
CN108794404B (zh) * 2018-06-28 2020-08-21 吉林奥来德光电材料股份有限公司 一种蒽类有机发光化合物及其制备方法以及有机电致发光器件

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012108877A1 (fr) * 2011-02-11 2012-08-16 University Display Corporation Dispositif électroluminescent organique et matériaux pour utilisation dans celui-ci
CN103531714A (zh) * 2012-07-30 2014-01-22 昆山维信诺显示技术有限公司 电子传输层、含该层的有机电致发光器件及其制备
JP2015106658A (ja) * 2013-11-29 2015-06-08 出光興産株式会社 有機エレクトロルミネッセンス素子および電子機器
CN104710410A (zh) * 2015-01-23 2015-06-17 北京鼎材科技有限公司 一种联苯并咪唑衍生物、其制备方法及其应用
CN109314189A (zh) * 2016-06-02 2019-02-05 株式会社Lg化学 有机发光元件
CN109309166A (zh) * 2017-07-28 2019-02-05 北京鼎材科技有限公司 有机电致发光器件以及含有2,6,9,10-位四取代的蒽化合物
CN108586352A (zh) * 2017-12-21 2018-09-28 北京燕化集联光电技术有限公司 一种有机材料及其在有机电致发光器件中的应用
CN108359441A (zh) * 2018-03-23 2018-08-03 吉林奥来德光电材料股份有限公司 一种有机发电致光材料及其制备方法和应用
CN109879811A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 有机发光材料及制备方法和应用

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