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Mazarine electroluminescent compound, and preparation method and application thereof

An electroluminescence and compound technology, which is applied in the field of organic electroluminescence and can solve the problems of high device startup voltage and rare organic light-emitting materials.

Active Publication Date: 2016-01-13
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the problem that the existing deep blue light-emitting organic light-emitting materials are rare and the starting voltage of the device is too high, the present invention provides a new type of blue fluorescent material using phenanthroimidazole as the core. The non-centrosymmetric structure of the imidazole ring has The electron-withdrawing properties of n-type materials can also connect electron donors and acceptor groups through molecular modification; phenanthrene is a condensed ring compound with three benzene rings, and a high conjugation system is conducive to reducing the non-radiative transition of molecules and improving fluorescence Quantum yield, also has certain advantages in terms of photothermal stability

Method used

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  • Mazarine electroluminescent compound, and preparation method and application thereof
  • Mazarine electroluminescent compound, and preparation method and application thereof
  • Mazarine electroluminescent compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The dark blue organic luminescent material prepared in this example is: 2-(4-dibenzofuran-4-phenyl)-1-(4-methoxyphenyl)phenanthroimidazole, whose molecular formula is C 40 h 26 N 2 o 2 , the structural formula is:

[0036]

[0037] Concrete preparation steps are as follows:

[0038]

[0039] 1. Preparation of precursor dibenzofuran-4-pinacol borate

[0040]Under the protection of argon, dissolve 10-12g of dibenzofuran in 100-200mL of tetrahydrofuran solvent, and stir evenly at a speed of 650r / min to obtain a mixed solution; put the reaction system in a dry ice acetone bath to keep low temperature, Add 30-45 mL of n-butyllithium n-hexane solution dropwise to the above mixed solution at a rate of 10 drops / min to 20 drops / min. As for adding 25–30 g of 1,2-dibromoethane to the tetrahydrofuran solvent in the dry ice acetone bath, after the dropwise addition, the system naturally returns to room temperature and stirs for 10–15 hours, then removes the solvent with c...

Embodiment 2

[0046] The dark blue organic luminescent material prepared in this example is: 2-(4-dibenzothiophene-4-phenyl)-1-(4-methoxyphenyl)phenanthroimidazole, whose molecular formula is C 40 h 26 N 2 OS, the structural formula is:

[0047]

[0048] The preparation method comprises the following steps:

[0049]

[0050] 1. Preparation of precursor dibenzothiophene-4-pinacol borate

[0051] The method was as described in step 1 of Example 1, and the reactant was replaced by dibenzothiophene from dibenzofuran to obtain white powder B, namely dibenzothiophene-4-pinacol borate.

[0052] 2. Preparation of precursor 2-(4-bromophenyl)-1-(4-methoxyphenyl)-phenanthroimidazole

[0053] Method is the same as step 2 of embodiment 1.

[0054] 3. Preparation of 2-(4-dibenzothiophene-4-phenyl)-1-(4-methoxyphenyl)phenanthroimidazole

[0055] The method is as described in step 3 of Example 1, except that the reactant is changed from product A to product B to obtain white powder E, namely 2-...

Embodiment 3

[0057] Preparation of non-doped electroluminescent device A by using dark blue organic hair material 2-(4-dibenzofuran-4-phenyl)-1-(4-methoxyphenyl)phenanthroimidazole as light-emitting layer material ,Specific steps are as follows:

[0058] 1. Clean the ITO glass in an organic solvent, dry it with nitrogen, and expose it to an ultraviolet-ozone atmosphere for 30 minutes.

[0059] 2. At 4.0 x 10 –4 Under the vacuum degree of Pa, the materials of the hole blocking layer, the hole transport layer, the light emitting layer and the electron transport layer are sequentially evaporated at a rate of 0.1-0.2nm / s, and finally LiF / Al is used as the cathode. The structure of the device is as follows: ITO / MoOx(2nm) / NPB(40nm) / luminescent material D(30nm) / TPBi(40nm) / LiF(1nm) / Al(100nm), see Image 6 Middle (a). Among them, NPB is N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine; TPBi is 1,3,5-tris (1-Phenyl-1H-benzimidazol-2-yl)benzene.

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Abstract

The invention discloses a mazarine electroluminescent compound, and a preparation method and application thereof. The mazarine electroluminescent compound has a structure as shown in a formula I which is described in the specification. In the formula, X is O or S; R1 is H, halogen, a cyano group, an alkyl group, an alkyloxy group or a phosphate radical; and R2 is H, a diphenylphosphine oxide radical, a diphenylamino group or a carbazolyl group. The compound as shown in the formula I is prepared by preparing a dibenzofuran(or dibenzothiophene)-4-pinacol borate precursor and a phenanthroimidazole precursor at first and then carrying out a coupling reaction. The preparation method for the compound is easy to operate and has high yield; the compound has mazarine fluorescence and good monochromaticity; and an OLED device prepared with the compound as a luminescent material has mazarine emission, starting voltage of 3.6 V and maximum external quantum efficiency of 1.63%.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a novel compound as a light-emitting layer material, a preparation method of the compound and related devices. Background technique [0002] Organic electroluminescent devices (organic EL elements), as the most promising generation of display products, gradually reveal their unique advantages in the fields of portable equipment and lighting. Compared with traditional light sources, organic electroluminescent devices have the characteristics of surface light source, large size and bendability, environmental friendliness (mercury-free), high power efficiency conversion, and low cost. In commercial use, full-color display and white lighting are inseparable from three primary colors: red, green, and blue. At present, red and green light-emitting materials with excellent comprehensive properties have been continuously reported and continuously refreshed the effici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C07D409/10C09K11/06H01L51/54
CPCC09K11/06C07D405/10C07D409/10C09K2211/1092C09K2211/1088C09K2211/1044H10K85/6576H10K85/6574H10K85/6572
Inventor 陈硕方岱宁裴永茂
Owner PEKING UNIV
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