WO2023020372A1 - Composé aza-spirobifluorène, préparation le comprenant, élément électroluminescent organique et dispositif d'affichage ou d'éclairage - Google Patents

Composé aza-spirobifluorène, préparation le comprenant, élément électroluminescent organique et dispositif d'affichage ou d'éclairage Download PDF

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Publication number
WO2023020372A1
WO2023020372A1 PCT/CN2022/111980 CN2022111980W WO2023020372A1 WO 2023020372 A1 WO2023020372 A1 WO 2023020372A1 CN 2022111980 W CN2022111980 W CN 2022111980W WO 2023020372 A1 WO2023020372 A1 WO 2023020372A1
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Prior art keywords
compound
substituted
unsubstituted
azaspirobifluorene
layer
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PCT/CN2022/111980
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English (en)
Chinese (zh)
Inventor
张震
王子兴
王志盛
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上海弗屈尔光电科技有限公司
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Publication of WO2023020372A1 publication Critical patent/WO2023020372A1/fr

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    • 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
    • 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
    • C07D405/14—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 three or more hetero rings

Definitions

  • the invention relates to an azaspirobifluorene compound, in particular to such azaspirobifluorene compound and a preparation containing it, an organic light-emitting element and a display or lighting device, and belongs to the field of organic semiconductor light-emitting.
  • the hole-blocking material should have a lower HOMO energy level, a higher electron mobility rate, a higher triplet energy level, a higher oxidation potential and a wider band gap to improve its electron transport ability and hole And the blocking ability of excitons, the excitons are confined in the light-emitting layer, reducing the loss of light energy, thereby greatly improving the efficiency of organic light-emitting devices.
  • the object of the present invention is to provide a nitrogen spirobifluorene compound which has improved electron transport ability and hole and excitation
  • the blocking ability of electrons makes excitons confined in the light-emitting layer, reducing energy loss, thereby further improving the efficiency and life of organic light-emitting devices, and reducing the operating voltage.
  • the present invention provides a kind of azaspirobifluorene compound, its structural formula is as shown in the following formula (I):
  • Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; one of X1 to X9 is N, and the others are C-R1; R1 to R3 are independently selected from H, D, F, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C1-C40 cycloalkyl, substituted Or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C1-C40 heteroaryl, substituted or unsubstituted C1-C60 silicon, substituted Or one of unsubstituted C6-C60 aromatic fused rings, substituted or unsubstituted C1-C60 heteroaromatic condensed rings,
  • the azaspirobifluorene compound of the present invention is selected from any one of the following structures, but it does not mean that the present invention is limited thereto:
  • the above groups that are not deuterated can be partially or fully deuterated; the groups that are not fluorinated can be partially or fully fluorinated.
  • the above groups that are not deuterated can be partially or fully deuterated; the groups that are not fluorinated can be partially or fully fluorinated.
  • the azaspirobifluorene compound of the present invention is selected from any one of the following structures, but it does not mean that the present invention is limited thereto:
  • the present invention also provides a preparation, wherein the preparation comprises the above-mentioned azaspirobifluorene compound and at least one solvent, and the solvent may be an unsaturated hydrocarbon solvent known to those skilled in the art (such as toluene, xylene, homo Trimethylbenzene, tetrahydronaphthalene, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.), halogenated saturated hydrocarbon solvents (such as carbon tetrachloride, chloroform, dichloromethane, dichloromethane, Chloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.), halogenated unsaturated hydrocarbon
  • the present invention also provides an organic light-emitting element, which includes a cathode layer, an anode layer, and an organic functional layer, and the organic functional layer is at least one layer in a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • the organic functional layer comprises the above-mentioned azaspirobifluorene compound.
  • the light-emitting layer of the organic light-emitting element contains the azaspirobifluorene compound of the present invention and at least one guest material, wherein the volume ratio of the azaspirobifluorene compound to the guest material is 99:1 to 1: 99; the guest material is a fluorescent material or a phosphorescent material.
  • the light-emitting layer of the organic light-emitting element contains the azaspirobifluorene compound as the first host, another organic compound as the second host, and the azaspirobifluorene compound and the second host
  • the volume ratio is 8:2 to 2:8, and the guest material is a fluorescent material or a phosphorescent material.
  • the electron transport layer of the organic light-emitting element contains the azaspirobifluorene compound of the present invention; the azaspirobifluorene compound can form an electron transport layer alone, or together with a dopant to form an electron transport layer;
  • the electron transport layer contains a dopant, the volume ratio of the azaspirobifluorene compound to the dopant is 2:8-8:2; the dopant is an n-type dopant.
  • the organic light-emitting element of the present invention can be classified as top-emitting, bottom-emitting or double-sided emitting.
  • the azaspirobifluorene compound of the present invention can also be applied to OLEDs for lighting, flexible OLEDs, and the like.
  • the present invention also provides a display or lighting device, which includes the above-mentioned organic light-emitting element.
  • the azaspirobifluorene compound of the present invention is applied to organic light-emitting devices, which improves device efficiency, lifespan, film-forming performance, etc., and the spirobifluorene compound of the present invention has a higher triplet state energy level, enabling energy transfer More fully, the transfer of electrons and holes is more balanced, resulting in higher efficiency and lifetime of the device while maintaining a low operating voltage.
  • the main feature of the azaspirobifluorene compound of the present invention is that a substituted triazine group and a substituted pyridine unit are simultaneously introduced, and it is unexpectedly found that the azaspirobifluorene compound of the present invention has the following remarkable effects:
  • the azaspirobifluorene compound of the present invention has a higher glass transition temperature
  • the azaspirobifluorene compound of the present invention is applied to organic light-emitting devices, which can improve the efficiency of the device. efficiency and longevity;
  • the azaspirobifluorene compound of the present invention can better balance the transfer of holes and electrons, thereby reducing the operating voltage of organic light-emitting devices.
  • Fig. 2 is a current efficiency-brightness graph of Embodiment 6 of the blue light device of the present invention.
  • the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known or unknown materials, particularly preferably selected from the following structures, but does not represent the present invention Limited to the following structures:
  • the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants.
  • the preferred p-type dopant of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:
  • the electron transport layer can be selected from one of the reference compounds ET-1 to ET-6 or a spirobifluorene compound similar in structure and the azaspirobifluorene compound of the present invention, but It does not mean that the present invention is limited to the following structures:
  • the electron transport layer can be formed of organic materials together with one or more n-type dopants such as LiQ.
  • the light-emitting layer is composed of BH-1 as the host and BD-1 as the guest material, and the blue light device is prepared
  • the light-emitting layer is composed of GH-1 as the host and GD-1 as the guest material, and the green light device is prepared
  • Embodiment 1 the synthesis of compound 1
  • Embodiment 2 the synthesis of compound 2
  • Embodiment 3 the synthesis of compound 3
  • Embodiment 4 the synthesis of compound 4
  • Embodiment 5 the synthesis of compound 5
  • Embodiment 6 the synthesis of compound 6
  • Embodiment 7 the synthesis of compound 7
  • Embodiment 8 the synthesis of compound 8
  • Table 1 shows the performance test results of the organic light-emitting devices in blue light comparative devices 1-15 and blue light device examples 1-14, wherein the lifetime of LT95 is based on the lifetime of the device in comparative example 1 as 100% for comparison.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention relève du domaine de l'optoélectronique organique, et concerne en particulier un composé aza-spirobifluorène et un élément électroluminescent organique l'utilisant. Le composé aza-spirobifluorène a une structure telle que représentée par la formule (I), dans laquelle Ar1 et Ar2 sont indépendamment choisis parmi un groupe aryle en C6-C30 substitué ou non substitué et un groupe hétéroaryle en C2-C30 substitué ou non substitué ; les informations de description détaillées et les éléments photoélectriques organiques correspondants peuvent être consultés en se référant à la description spécifique de la présente invention. Le composé aza-spirobifluorène selon la présente invention est utilisé en tant que matériau de couche de transport d'électrons d'un dispositif électroluminescent organique ou dans une couche électroluminescente, de telle sorte que l'efficacité de courant de l'élément électroluminescent est améliorée, la durée de vie est prolongée de manière significative, et en particulier, la tension de commande est réduite.
PCT/CN2022/111980 2021-08-14 2022-08-12 Composé aza-spirobifluorène, préparation le comprenant, élément électroluminescent organique et dispositif d'affichage ou d'éclairage WO2023020372A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202110933623.4 2021-08-14
CN202110933623.4A CN115894446A (zh) 2021-08-14 2021-08-14 一种氮杂螺二芴化合物及包含其的制剂、有机发光元件及显示或照明装置

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WO2023020372A1 true WO2023020372A1 (fr) 2023-02-23

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831581A (zh) * 2017-02-10 2017-06-13 上海大学 一种氮杂螺二芴衍生物及其制备方法
CN107021926A (zh) * 2017-06-12 2017-08-08 江苏三月光电科技有限公司 一种含有氮杂螺芴和含氮六元杂环的化合物及其在oled上的应用
CN108963099A (zh) * 2018-08-20 2018-12-07 上海大学 一种用于有机电致发光元件的组合物及有机电致发光元件
CN108997342A (zh) * 2018-08-20 2018-12-14 上海大学 一种多氮杂螺二芴化合物及含有该化合物的有机光电器件
CN110229071A (zh) * 2019-06-06 2019-09-13 北京诚志永华显示科技有限公司 芴衍生物有机电致发光器件
CN110776496A (zh) * 2019-11-18 2020-02-11 苏州久显新材料有限公司 3,4-二氮杂螺芴类衍生物及其合成方法和含有3,4-二氮杂螺芴类衍生物的电子器件
CN111244306A (zh) * 2018-11-29 2020-06-05 宇瑞(上海)化学有限公司 一种顶发射有机发光二极管单元
CN112390780A (zh) * 2019-08-18 2021-02-23 北京夏禾科技有限公司 含氮杂螺二芴的电子传输材料

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831581A (zh) * 2017-02-10 2017-06-13 上海大学 一种氮杂螺二芴衍生物及其制备方法
CN107021926A (zh) * 2017-06-12 2017-08-08 江苏三月光电科技有限公司 一种含有氮杂螺芴和含氮六元杂环的化合物及其在oled上的应用
CN108963099A (zh) * 2018-08-20 2018-12-07 上海大学 一种用于有机电致发光元件的组合物及有机电致发光元件
CN108997342A (zh) * 2018-08-20 2018-12-14 上海大学 一种多氮杂螺二芴化合物及含有该化合物的有机光电器件
CN111244306A (zh) * 2018-11-29 2020-06-05 宇瑞(上海)化学有限公司 一种顶发射有机发光二极管单元
CN110229071A (zh) * 2019-06-06 2019-09-13 北京诚志永华显示科技有限公司 芴衍生物有机电致发光器件
CN112390780A (zh) * 2019-08-18 2021-02-23 北京夏禾科技有限公司 含氮杂螺二芴的电子传输材料
CN110776496A (zh) * 2019-11-18 2020-02-11 苏州久显新材料有限公司 3,4-二氮杂螺芴类衍生物及其合成方法和含有3,4-二氮杂螺芴类衍生物的电子器件

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