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Compound taking dibenzo six-membered ring as core and applications thereof on OLED

A dibenzo six-membered ring and compound technology, which is applied in the field of OLED applications, can solve problems such as complex manufacturing processes and affecting the angular distribution of OLED radiation spectrum, and achieve high refractive index, good application effects, industrialization prospects, and high The effect of carrier mobility

Active Publication Date: 2019-03-29
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 taking dibenzo six-membered ring as core and applications thereof on OLED
  • Compound taking dibenzo six-membered ring as core and applications thereof on OLED
  • Compound taking dibenzo six-membered ring as core and applications thereof on OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the synthesis of intermediate A:

[0053]

[0054] The specific preparation method is as follows: Weigh raw material K and raw material L, and dissolve them in a mixed solvent of toluene and ethanol with a volume ratio of 2:1; under an inert atmosphere, add Na 2 CO 3 Aqueous solution, Pd(PPh 3 ) 4 ; The mixed solution of the above reactants is reacted at a reaction temperature of 95 to 110 ° C for 10 to 24 hours, cooled and filtered the reaction solution, the filtrate is rotary evaporated, and passed through a silica gel column to obtain intermediate A; the mole of the raw material L and the raw material K The ratio is 1:(1.0~2.0), Na 2 CO 3 The molar ratio with raw material L is (1.0~3.0):1, Pd(PPh 3 ) 4 The molar ratio with raw material L is (0.006~0.02):1;

[0055] Take the synthesis of intermediate A1 as an example:

[0056]

[0057] In a 250ml three-neck flask, add 0.01mol of raw material L1 and 0.015mol of raw material K1, and dissolve ...

Embodiment 2

[0062] Embodiment 2: the synthesis of compound 1:

[0063]

[0064] Add 0.1mol raw material M and 0.1mol raw material O to the there-necked flask successively, in 80ml 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;

[0065] 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 98.70% and a yield of 75.3%; elemental analysis structure (molecular formu...

Embodiment 3

[0066] Embodiment 3: the synthesis of compound 9:

[0067]

[0068] The preparation method of compound 9 is the same as Example 2, and the difference is that the raw material M1 is replaced with the raw material M2, and the raw material N1 is replaced by the raw material N2; the 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, 87.24; H, 5.85; N, 6.91. ESI-MS(m / z)(M + ): The theoretical value is 605.78, and the measured value is 605.50.

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Abstract

The invention discloses a compound taking a dibenzo six-membered ring as a core and applications thereof on an organic electroluminescent device. One of the branch chains of the compound is phenyl, biphenyl or naphthyl, and the other two are aza five-membered rings. The compound has high glass transition temperature and molecular thermal stability; the compound has low absorption and high refractive index in a visible light field, and can effectively enhanced the light extraction efficiency of an OLED device after being applied to a CPL of the OLED device; and the compound has shallow HOMO level and high hole mobility, so that the compound can be used as the hole injection / transport layer material of the OLED device, holes can be effectively transmitted to the side of a luminescent layer,and therefore, the composite efficiency of the holes and electrons on the luminescent layer can be enhanced, and the luminous efficiency and service life of the OLED device can be increased.

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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IPC IPC(8): C07D401/04C07D401/10C07D401/14C07D405/14C07D409/14C07D413/04C07D413/10C07D413/14H01L51/50H01L51/54
CPCC07D401/04C07D401/10C07D401/14C07D405/14C07D409/14C07D413/04C07D413/10C07D413/14H10K85/624H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 吴秀芹李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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