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Ionic type cyclometalated iridium complex liquid crystal luminescent material and application thereof in non-doped polarizing red electroluminescent device with single luminescent layer

A technology of iridium complexes and luminescent materials, applied in luminescent materials, liquid crystal materials, electric solid devices, etc., can solve the problem of low luminous efficiency, etc., and achieve the effect of inhibiting luminescence quenching

Active Publication Date: 2016-05-25
漳州思美科新材料有限公司
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Problems solved by technology

[0006] Aiming at the defects of concentration quenching and low luminous efficiency in the existing cyclometal platinum complex liquid crystal luminescent materials, the purpose of the present invention is to provide a kind of phenylpyridine as the anion ligand and bipyridine derivative as the NN ligand. Ionic ring metal iridium complex liquid crystal luminescent material; this material consists of iridium complexes to form a luminescent core, and biphenyl derivatives are used as mesogens to jointly construct a non-planar structure cyclometal iridium complex liquid crystal light emitting material with high luminous efficiency ; This cyclometallic iridium complex liquid crystal luminescent material with an octahedral structure is beneficial to suppress the luminous quenching phenomenon of the material and improve the luminous efficiency of the material

Method used

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  • Ionic type cyclometalated iridium complex liquid crystal luminescent material and application thereof in non-doped polarizing red electroluminescent device with single luminescent layer
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  • Ionic type cyclometalated iridium complex liquid crystal luminescent material and application thereof in non-doped polarizing red electroluminescent device with single luminescent layer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation scheme of cyclometal iridium complex formula 1: the synthetic route of cyclometal iridium complex liquid crystal luminescent material (formula 1) is as follows:

[0032]

[0033] Reactionconditions:(a)Pd(PPh 3 ) 4 ,2MK 2 CO 3 , THF, reflux, overnight. (b) BBr 3 ,CH 2 Cl 2 ,-78℃-roomtemperature,20h.(c)1,2-bis(2-(p-tolyloxy)ethoxy)ethane(or1,6-dibromohexane),K 2 CO 3 ,KI,acetone,reflux,24h.(d)3or4,K 2 CO 3 ,KI,acetone,reflux,24h.(e)LiAlH 4 ,THF,roomtemperature,8h.(f)2,2'-bipyridine-4,4'-dicarbonyldichloride,Et 3 N,CH 2 Cl 2 ,reflux,overnight.(g)(ppy)4 IrCl 2 ,KPF 6 ,MeOH / CH 2 Cl 2 , reflux, overnight.

[0034] Preparation of Compound 1:

[0035] Add 4-ethoxy-2,3-difluorophenylboronic acid (5.0g, 24.8mmol), 1-iodo(4-pentylcyclohexyl)benzene (9.0g, 25.3mmol), Pd (PPh 3 ) 4 (0.25mmol, 0.29g), K 2 CO 3 solution (2M, 15 mL), toluene (45 mL) and ethanol (15 mL), and the mixture was refluxed overnight under argon atmosphere. After the r...

Embodiment 2

[0059] Testing of liquid crystal properties of cyclometalated iridium complex luminescent materials:

[0060] The liquid crystal properties of cyclometalated iridium complexes Ir1 and Ir2 were tested by differential scanning calorimetry (DSC), polarized light microscopy (POM) and X-ray diffraction (XRD). Such as Figure 4 As shown, both Ir1 and Ir2 exhibit multiple phase transition points in the process of heating and cooling; and POM can observe that the iridium complex has fluidity and birefringence in the process of cooling ( Figure 4 ), which indicates that these two iridium complexes have liquid crystal properties. Further, the liquid crystal texture of the iridium complex was confirmed by temperature-changing XRD test. if Figure 6 As shown, at room temperature, Ir2 exhibits strong diffraction peaks at 1.32°, 2.63° and 4.01°, respectively, which is a typical ordered crystal structure. When the temperature is raised to 180°C, there are only weak diffraction peaks at ...

Embodiment 3

[0062] Test of Aggregation-Induced Emission (AIE) Performance of Cyclometallic Iridium Complex Liquid Crystal Luminescent Material:

[0063] Dissolve the iridium complex Ir1 in THF to prepare a concentration of 10 -4 M solution; take 1mL of the solution and place it in 8 volumetric flasks; add different volumes of water to make the water content 0%, 30%, 40%, 50%, 60%, 70%, 80% and 90% . At room temperature, test the fluorescence spectra of these 8 groups of mixed solutions. Such as image 3 As shown, when the water content gradually increases, the luminescence intensity of the complexes gradually increases, especially the complex Ir1 exhibits a strong red light in the solid state. This shows that this iridium complex has AIE performance and can obtain high-efficiency luminescence in the solid state, which provides a new design idea for improving the luminescence efficiency of liquid crystal light-emitting materials in high concentrations and solid films.

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Abstract

The invention discloses an ionic type cyclometalated iridium complex liquid crystal luminescent material and an application thereof. The cyclometalated iridium complex liquid crystal luminescent material adopts phenylpyridine as an anionic ligand and a bipyridyl derivative as an N N ligand; the cyclometalated iridium complex liquid crystal luminescent material adopts a non-planar structure built with a cyclometalated iridium complex as a luminescent core and a biphenyl derivative as a liquid crystal unit. The cyclometalated iridium complex is taken as the luminescent layer, and the non-doped polarizing red electroluminescent device with the single luminescent layer and the polarization ratio being 4 is obtained with a rubbing alignment method.

Description

technical field [0001] The invention relates to a class of ionic cyclometal iridium complex liquid crystal luminescent material and its application, in particular to the application of ionic cyclometal iridium complex liquid crystal luminescent material in non-doped single luminescent layer polarized OLEDs, which belongs to polarized electroluminescent materials and application fields. Background technique [0002] The 21st century is an era of rapid development of display technology. Since C.W.Tang et al first reported organic light-emitting diodes (OLEDs) with small-molecule thin-film double-layer structures using octahydroxyquinoline aluminum (Alq3) as the light-emitting layer in 1987, OLEDs have been known for their active light emission, high brightness, ultra-light, ultra-thin, and non-toxic. The advantages of limited viewing angle, flexible display and large-screen display are considered to be the development direction of next-generation display technology and genera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06C09K19/40H01L51/54
CPCC09K11/06C09K19/067C09K19/40C07F15/0033C09K2211/185H10K85/731H10K85/342
Inventor 王亚飞
Owner 漳州思美科新材料有限公司
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