Metal complexes, organic electroluminescent devices, organic electroluminescent materials

A technology for electroluminescent materials and metal complexes, which is applied in the fields of luminescent materials, electro-solid devices, organic chemistry, etc., can solve the problems of low maximum external quantum efficiency, difficult ligand design of heavy metal complexes, etc., and achieves easy sublimation purification, Effects of improved external quantum efficiency and improved thermal stability

Active Publication Date: 2021-08-31
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the maximum external quantum efficiency of existing red phosphorescent materials is low, usually in the range of about 15%.
The main reason for this situation is that red light comes from transitions between energy levels with narrow energy gaps, and heavy metal complexes with narrow band gaps have certain difficulties in ligand design.

Method used

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  • Metal complexes, organic electroluminescent devices, organic electroluminescent materials
  • Metal complexes, organic electroluminescent devices, organic electroluminescent materials
  • Metal complexes, organic electroluminescent devices, organic electroluminescent materials

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Effect test

preparation example Construction

[0177] [Preparation method of metal complex]

[0178] Although the metal complex of the present invention is a new type of metal complex, its preparation method can be prepared by those skilled in the art under suitable conditions according to the technical knowledge in this field.

[0179] The aforementioned compounds LA1-LA1150 can be prepared by referring to the preparation methods of isoquinoline in patents CN104370968 and US20130146848. Specifically, the substituted o-cyanophenylethynyl trimethylsilane was prepared by reacting the substituted o-iodobenzonitrile as the starting material with trimethylsilyne under palladium catalyzed conditions, and the alkyne-containing intermediate was prepared under the alkaline condition of sodium ethoxide Substituted o-cyano-styryl ethyl ether is prepared by the following addition reaction, and the acetal product is easily ring-closed with the ortho-position imino group to prepare substituted isoquinoline ligands LA1-LA1150.

[0180] ...

Embodiment 1

[0204] Preparation of LA816:

[0205] The preparation method of LA816 comprises the steps:

[0206] The first step: preparation of intermediate L1

[0207]

[0208] 27.1 g (0.1 mol) of raw material L0 (4-isopropyl-2-iodobenzonitrile, CAS: 1369880-78-3), 0.11 mol of trimethylsilyne and 5 mmol of palladium acetate, 10 mmol of phosphide Copper, 10 mmol of triphenylphosphine, 50 mL of triethylamine and 200 mL of acetonitrile were stirred and reacted at room temperature for 4 hours under nitrogen protection. Concentrate to dryness under reduced pressure, decolorize the residue with a short silica gel column, and rinse with petroleum ether to obtain 23.0 g of product formula L1, yellow oil, yield: 96%.

[0209] The second step: the preparation of intermediate L2

[0210]

[0211] Put 200mL of ethanol into a 500mL reaction bottle, under the protection of nitrogen, add 11.0g of broken sodium blocks, stir and dissolve until the sodium blocks disappear, after 1 hour, add 23.0g ...

Embodiment 2

[0216] Preparation of LA2057:

[0217]

[0218] 18.0g (0.1mol) of raw material L3 (1-(o-aminophenyl)-3-methyl-1-butanol, CAS: 1341805-79-5), 83.3mmol of 3,5-dimethylphenethyl Ketone and 2 mmol of nickel catalyst (CAS: 757176-61-7), 0.1 mol of sodium tert-butoxide and 150 mL of toluene, under nitrogen protection, stirred and heated to reflux for 24 hours. Concentrated to dryness under reduced pressure, the residue was separated and purified by silica gel column to obtain 14.9g product formula LA2057, yellow oil, yield: 62%, 1 H-NMR: (δ, CDCl 3 ),8.20-8.18(d,1H),8.17-8.15(dd,2H),8.06-8.04(d,1H),7.74-7.68(m,2H),7.47-7.44(dd,1H),7.13(s ,1H), 3.17-3.10(m,2H), 2.43(s,6H), 1.53-1.50(m,1H), 1.01(s,6H).

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Abstract

The invention discloses a novel metal complex, an organic electroluminescent device and an organic electroluminescent material containing the metal complex. The molecular formula of the metal complex of the present invention is: M (L A ) m‑n (L C ) n , wherein, M is the metal element Ir; m is the oxidation valence state of metal M, n is an integer greater than 1 and n is less than m; the metal complex electroluminescence device proposed by the present invention emits red light, has high external quantum efficiency, and at the same time The thermal stability of the material is good, the service life of the device is improved, and the material is easy to prepare and purify, so it is an ideal choice as a light-emitting material of an organic electroluminescent device.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence display. Background technique [0002] Organic electroluminescent materials are divided into two categories: organic electroluminescent materials and organic electrophosphorescent materials. Among organic electrophosphorescent materials, organic electrogreen phosphorescent materials are the earliest studied and the most mature type of materials. In 2004, Hino et al. produced phosphorescent devices by spin coating, and the maximum external quantum efficiency was 29cd / A. Adachi et al. doped (ppy)2Ir(acac) into TAZ and used HMTPD as the hole transport layer to obtain a green light device with a maximum external quantum efficiency of 20% and an energy efficiency of 65lm / W. [0003] However, for red phosphorescent materials, with the development of technology, materials with high external quantum efficiency and high color purity are required. However, the maximum external quantum...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/12
Inventor 曹建华邵哲温世文郭剑隋岩何伟壮
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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