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Heterocyclic compound containing heteroatom substituted fluorene and application thereof in photoelectric device

A technology of heterocyclic compounds and heteroatoms, which is applied in the field of organic electroluminescent materials, can solve the problems that OLED devices cannot meet the market demand, the light extraction effect is not good enough, and cannot be obtained at the same time, so as to achieve improved current efficiency, excellent durability, long life effect

Pending Publication Date: 2022-03-01
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the refractive index of OLED devices cannot meet the market demand, and the light extraction effect is not good enough; the difference in refractive index measured in the respective wavelength regions of blue, green and red is relatively large, so blue, green and red light-emitting devices All the light in the cannot obtain high light extraction efficiency at the same time

Method used

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  • Heterocyclic compound containing heteroatom substituted fluorene and application thereof in photoelectric device
  • Heterocyclic compound containing heteroatom substituted fluorene and application thereof in photoelectric device
  • Heterocyclic compound containing heteroatom substituted fluorene and application thereof in photoelectric device

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preparation example Construction

[0112] The preparation method of the above-mentioned heterocyclic compound provided by the present invention belongs to the prior art, and those skilled in the art can select a specific synthetic method according to conventional technical knowledge. The present invention only provides an exemplary synthetic route, but is not limited to the following synthetic route.

[0113] The representative synthetic route of the formula I compound provided by the invention is as follows:

[0114]

[0115] The above-mentioned compound provided by the present invention can be applied to the CPL layer of a top-emitting OLED device; it can also be used as an optical auxiliary layer such as a hole transport layer and an electron blocking layer.

[0116] The present invention provides a display panel, comprising an organic light-emitting device, the organic light-emitting device includes an anode, a cathode, and an organic thin layer between the anode and the cathode, the cathode is covered wi...

Embodiment 1

[0130] The synthetic route of compound M001 is as follows:

[0131]

[0132] Concrete preparation method comprises the following steps:

[0133]

[0134](1) M001-1 (0.5mmol), M001-2 (0.75mmol), K 2 CO 3 (0.5mmol), PdCl 2 (5×10 - 4 mmol), TPPDA (5×10 -4 mmol) was added into 3mL o-xylene solution and mixed, put into a 50mL flask, and reacted at 100°C for 24 hours. Cool to room temperature, then slowly add saturated MgSO to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was removed from the solvent by a rotary evaporator, and the crude product M001-3 was obtained by column chromatography.

[0135] (2) M001-3(0.5mmol), M001-4(1.5mmol), KO(t-Bu)(0.75mmol), [Pd(cinnamyl)Cl] 2 (2mol%) and Ligand (1.5mol%) were added to 3mL of toluene solution and mixed, put into a 50mL flask, and reacted at 110°C for 12 hours. Cool to room temperature, then slowly add saturated MgSO to the solution 4 The aqueous solution an...

Embodiment 2

[0139] The synthetic route of compound M029 is as follows:

[0140]

[0141] Concrete preparation method comprises the following steps:

[0142]

[0143] (1) M001-3(0.5mmol), M029-1(1.5mmol), KO(t-Bu)(0.75mmol), [Pd(cinnamyl)Cl] 2 (2mol%) and Ligand (1.5mol%) were added to 3mL of toluene solution and mixed, put into a 50mL flask, and reacted at 110°C for 12 hours. Cool to room temperature, then slowly add saturated MgSO to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was removed from the solvent by a rotary evaporator, and the crude product M029 was obtained by column chromatography.

[0144] Test the structure of the target product M029: MALDI-TOF MS (m / z) obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis: C 43 h 26 N 4 o 3 , the calculated value is 646.2, and the tested value is 646.3.

[0145] Elemental analysis: theoretical value C, 79.86; H, 4.05; N...

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Abstract

The invention provides a heterocyclic compound containing heteroatom substituted fluorene. The heterocyclic compound has a structure as shown in a formula I in the specification. The fluorene group is subjected to specific heteroatom substitution, and the prepared heterocyclic compound has the following advantages that (1) the refractive index is high, and the light extraction efficiency is high; (2) absorption is not realized in wavelength regions of blue, green and red, and the color purity is not reduced; (3) the difference in refractive index measured in each wavelength region of blue, green, and red is small; (4) the glass transition temperature is high, the decomposition temperature is high, and the material can be evaporated but cannot be thermally decomposed; and (5) a film prepared from the material is high in stability, excellent in durability and long in service life.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound containing heteroatom-substituted fluorene and its application in photoelectric devices. Background technique [0002] According to the direction in which the organic light emitting layer emits light, the OLED display can be classified into a bottom emission OLED display and a top emission OLED display. In a bottom emission OLED display, light is emitted toward a substrate, a reflective electrode is formed on an organic light emitting layer, and a transparent electrode is formed under the organic light emitting layer. If the OLED display is an active matrix OLED display, the thin film transistors formed therein partially do not transmit light, so the light emitting area is reduced. On the other hand, in a top-emitting OLED display, a transparent electrode is formed on the organic light-emitting layer, and a reflective electrod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048C07D491/147C07D495/04C07D495/14C07D519/00H01L51/54H01L51/50
CPCC07D491/048C07D519/00C07D491/147C07D495/04C07D495/14H10K85/622H10K85/615H10K85/631H10K85/626H10K85/633H10K85/657H10K85/6572H10K85/6574H10K50/18H10K50/15C09K11/06H10K85/654H10K50/11H10K50/16C07D405/14C07D409/14C07D471/04H10K50/844H10K85/636C09K2211/1018
Inventor 高威代文朋张磊高优翟露
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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