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Spirobifluorene trifluoromethylpyridine iridium complex and its preparation method and application

A technology of spirobifluorene trifluoromethylpyridine iridium and trifluoromethylpyridine iridium, which is applied to the spirobifluorene trifluoromethylpyridine iridium complex and the fields of preparation and application thereof, and can solve the problem that the color purity needs to be improved, the electroporation The problem of high wavelength dependence of luminescence

Active Publication Date: 2018-04-13
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

White light devices have high luminous efficiency, but the electroluminescence wavelength has a high dependence on voltage, the color coordinates are (0.31,0.41), and the color purity needs to be improved

Method used

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  • Spirobifluorene trifluoromethylpyridine iridium complex and its preparation method and application
  • Spirobifluorene trifluoromethylpyridine iridium complex and its preparation method and application
  • Spirobifluorene trifluoromethylpyridine iridium complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Preparation of two orange-emitting iridium complexes 5 and 6

[0045] Bis[2-(9,9'-spirobifluoren-2-yl)-5-trifluoromethylpyridine-C 3 , N]iridium (pentanedione) (complex 5) and bis[2-(9,9'-spirobifluoren-2-yl)-5-trifluoromethylpyridine-C 3 , N] the synthesis of iridium (2-pyridine acid) (complex 6):

[0046] (1) Under the protection of argon, 2-bromo-9,9'-spirobifluorene (compound 1) (11.85 g, 30 mmol) was dissolved in 230 ml tetrahydrofuran in a 100 mL round bottom flask successively, and cooled to -78 °C. After n-butyllithium (1.6M, 28.1ml, 45mmol) was added dropwise, the reaction was carried out for 1 hour, and trimethyl borate (8.83g, 45mmol) was added in one portion. After reacting for 30 minutes, the temperature was raised to room temperature, and the reaction was continued for 30 minutes. The mixture was treated with dilute acid, extracted with ether, dried, concentrated, and the solid was separated by silica gel column chromatography to obtain 9,9-s...

Embodiment 2

[0054] Example 2: Application of two orange light-emitting iridium complexes 5 and 6 in orange organic electroluminescent devices

[0055] Orange device structures and designs based on two novel iridium complexes 5 and 6, such as Figure 2-a and Figure 2-b shown, respectively, device A1 (sfp-5CF 3 -py) 2 Ir(acac) and device B1(sfp-5CF 3 -py) 2 Ir (pic).

[0056] Among them, PEDOT:PSS refers to poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid), which is used as a hole injection layer and spin-coated on ITO glass; PVK refers to polyvinylcarbazole, which has a void The host material for hole transport; PBD is 2-tert-butylbenzene-5-biphenyl-1,3,4-dioxazole as the electron transport material. The light-emitting layer is composed of PVK:PBD:complex 5 (or complex 6), the weight ratio of PVK / PBD is 3 / 2, iridium complex 5 or 6 is doped in the mixture of PVK and PBD with 2w%, and then spin Apply over PEDOT:PSS layer. 1,3,5-Tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPB...

Embodiment 3

[0058] Example 3: Application of two orange light-emitting iridium complexes 5 and 6 in white organic electroluminescent devices

[0059] The structure and design of white light-emitting devices based on two new iridium complexes 5 and 6, such as Figure 4-a and Figure 4-b As shown, respectively, the device WOLED (white organic electroluminescence) 1 (sfp-5CF 3 -py) 2 Ir(acac) and device WOLED 2(sfp-5CF 3 -py) 2 Ir (pic).

[0060] Among them, PEDOT:PSS is poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid), which is used as a hole injection layer and spin-coated on ITO glass; PVK is polyvinylcarbazole, which has a hole Transferred body material. The orange light-emitting layer is composed of PVK:complex 5 or 6 (8% by mass), which is spin-coated on the PEDOT:PSS layer. The blue light-emitting layer is composed of CBP:FIrPic (mass ratio 8%), CBP is 4,4'-N,N'-dicarbazole biphenyl, and FIrPic is difluorophenylpyridine iridium pyridine acid, which is vacuum-copolyme...

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Abstract

The invention relates to a spirobifluorene trifluoromethylpyridine iridium complex, a preparation method and application thereof. The structural formula of the spirobifluorene trifluoromethylpyridinium iridium complex is as follows: the two orange light-emitting iridium complexes of the present invention combine a vertical, large-volume, larger sterically hindered spirobifluorene and a red-shifted luminescent wavelength The introduction of the trifluoromethyl group to the phenylpyridine improves the orange luminous efficiency and luminous performance of materials and devices, and can adjust the luminous color. The invention also provides a preparation method of the spirobifluorene trifluoromethylpyridine iridium complex and its application in orange and white organic electroluminescent devices. The orange and white electroluminescence devices based on the two orange light-emitting iridium complexes of the present invention show good stability at high current density; the performance of this type of orange light-emitting materials is excellent, and the devices have good light-emitting performance.

Description

technical field [0001] The present invention relates to spirobifluorene trifluoromethylpyridine iridium complexes and their preparation methods and applications, in particular to two orange luminescent iridium complexes, namely spirobifluorene trifluoromethylpyridinium iridium pentanedione and spirobifluorene trifluoromethylpyridinium iridium A picoline iridium pyridine acid and a preparation method thereof, and a white light-emitting device based on two independent light-emitting layers of the two orange-emitting and blue-emitting difluorophenylpyridine iridium pyridine acids (FIrPic). Background technique [0002] White organic electroluminescence (WOLED) has potential applications in backlight display, full-color display, and solid-state luminescence. When phosphorescent materials are used, the efficiency of white light devices and full-color active matrix display have been significantly improved. The most common white light device is composed of three primary colors of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/1011C09K2211/1029H10K85/00H10K85/654H10K50/11Y02B20/00
Inventor 张文官
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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