Compound with dibenzo-6-membered ring as core and application thereof in organic light emission diode device

A dibenzo six-membered ring and electroluminescent device technology, which is applied in the field of OLED applications, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, and achieve good application effects and industrialization prospects. High, improve the effect of luminous efficiency and service life

Active Publication Date: 2019-04-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, and the process of using a surface covering layer is simple, and the luminous efficiency is increased by more than 30%, which is particularly concerned by people.

Method used

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  • Compound with dibenzo-6-membered ring as core and application thereof in organic light emission diode device
  • Compound with dibenzo-6-membered ring as core and application thereof in organic light emission diode device
  • Compound with dibenzo-6-membered ring as core and application thereof in organic light emission diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of compound 1:

[0047]

[0048] Add 0.1mol of raw material M1 and 0.1mol of raw material O1 to the there-necked flask successively, in 80ml of sodium ethylate solution, under room temperature, stir for 12 hours until the reaction solution turns orange-yellow; then, filter the reaction mixture, and obtain The filter cake was washed with 3% hydrochloric acid solution, and the resulting product was crystallized with ethanol to obtain bright yellow crystalline intermediate C1;

[0049] Add 0.05mol of the above-prepared intermediate to the three-neck flask, add 0.05mol of raw material N1, then add 100ml of dry acetic acid, stir, heat to 90°C, and reflux for 10 hours until the ring closure reaction is completed; evaporate the reaction mixture under reduced pressure Acetic acid was separated, and the residue was recrystallized with ethanol to obtain compound 1 with a HPLC purity of 99.50% and a yield of 76.3%; elemental analysis structure (molec...

Embodiment 2

[0050] Embodiment 2: the synthesis of compound 9:

[0051]

[0052] The preparation method of compound 9 is the same as Example 1, and the difference is that raw material M1 is replaced by raw material M2, raw material O2 is replaced by raw material O1, raw material N2 is replaced by raw material N1; elemental analysis structure (molecular formula C 44 h 35 N 3 ): Theoretical value: C, 87.24; H, 5.82; N, 6.94; Test value: C, 87.25; H, 5.84; N, 6.91. ESI-MS(m / z)(M + ): The theoretical value is 605.78, and the measured value is 605.48.

Embodiment 3

[0053] Embodiment 3: the synthesis of compound 15:

[0054]

[0055] The preparation method of compound 15 is the same as Example 1, and the difference is that raw material O3 is used to replace raw material O1, and raw material N3 replaces raw material N1; Elemental analysis structure (molecular formula C 51 h 43 N 3 ): Theoretical value: C, 87.77; H, 6.21; N, 6.02; Test value: C, 87.75; H, 6.22; N, 6.03. ESI-MS(m / z)(M + ): The theoretical value is 697.93, and the measured value is 697.43.

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Abstract

The invention discloses a compound with a dibenzo-6-membered ring as a core and an application thereof in an organic light emission diode device. The organic compound contains the dibenzo-6-membered ring, and two benzene are connected by an alkylene group substituted by an oxygen atom, a sulfur atom, and a C1-10 linear chain or branched alkyl group, an aryl-substituted alkylene group, an aryl-substituted alkyl group or an aryl-substituted tertiary amine group. The compound of the invention has high glass transition temperature and molecular thermal stability; the compound is low in absorptionand high in refractive index in a visible light field, and can effectively improve the light extraction efficiency of an OLED device after being applied to a CPL layer of the OLED device; and the compound of the invention is shallow in HOMO energy level and high in hole mobility, can be used as a hole injection/transport layer material of the OLED device, and can effectively transfer holes to oneside of a light-emitting layer, thereby enhancing the recombination efficiency of the holes and electrons in the light-emitting layer, and the luminous efficiency and service life of the OLED device are further improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound material with a dibenzo-6-membered ring as the central skeleton and its application in the field of OLEDs. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting devic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D401/14C07D405/14C07D409/14C07D413/10C07D413/14C07D417/14C07D403/10C07D403/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/10C07D401/14C07D403/10C07D403/14C07D405/14C07D409/14C07D413/10C07D413/14C07D417/14C09K2211/1029C09K2211/1011C09K2211/1014C09K2211/1007C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1092C09K2211/1088H10K85/626H10K85/631H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572
Inventor 吴秀芹张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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