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A kind of hybrid metal complex and its application in electro-organic light-emitting device

A technology of organic light-emitting layers and complexes, applied in the field of organic electroluminescent devices, can solve the problems of short lifespan and luminous lifespan gap.

Active Publication Date: 2022-07-01
冠能光电材料(深圳)有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage is that the device lifetime of this type of hybrid light-emitting materials is not as good as that of triligand organometallic complexes.
[0015] Compared with LED light-emitting diodes, organic OLED light-emitting diodes have energy-saving, eye-protecting and flexible display and lighting properties, but there is still a big gap in luminous lifetime.

Method used

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  • A kind of hybrid metal complex and its application in electro-organic light-emitting device
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  • A kind of hybrid metal complex and its application in electro-organic light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Example 1: Preparation of per-deuterated acetylacetone

[0115]

[0116] feed ratio

[0117]

[0118] Experimental procedure: Weigh potassium tert-butoxide into a 5000mL three-necked flask, add 1500ml DMF solvent to dissolve it completely, vacuumize it, and put it in N 2 The temperature was raised to 50°C under protection, and then 560 g of deuterated ethyl acetate was gradually added dropwise; after the dropwise addition, acetone-d6 was gradually dropped into the three-necked flask, and finally stirred at reflux (57°C) overnight. Stop the reaction and cool to room temperature with 20% H 2 SO 4 The aqueous solution was neutralized until the reaction liquid was neutral, the solid was removed by filtration, washed with toluene, the filtrate was washed with water 5 times, the solvent was spin-dried, and the substrate was distilled under reduced pressure to obtain 150 g of a yellow oily product with a yield of 70% and a purity of 70%. is 98%. HRMS detection showed...

Embodiment 2

[0119] Example 2: Partially deuterated isovalerylacetone preparation:

[0120]

[0121] feed ratio

[0122]

[0123] Experimental procedure: Weigh potassium tert-butoxide into a 5000mL three-necked flask, add 1700ml DMF to dissolve it completely, vacuumize it, and put it under N 2 The temperature was raised to 50°C under protection, and then methyl isovalerate was gradually added dropwise; after the dropwise addition, acetone-d6 was gradually dropped into the three-necked flask, and finally stirred at 50°C overnight. Stop the reaction and cool to room temperature with 20% H 2 SO 4 The aqueous solution was neutralized until the reaction solution was neutral, the solid was removed by filtration, washed with toluene, and the filtrate was washed with water for 5 times. After the solvent was spin-dried, the substrate was distilled under reduced pressure to obtain 206 g of a yellow oily product with a yield of 70%. The purity is 98%. HRMS detection showed that the molecula...

Embodiment 3

[0124] Example 3: Synthesis of green light organometallic complex A1 and its comparative sample

[0125] 3.1 Synthesis of organometallic iridium complex comparative sample G-103 (without deuterium):

[0126]

[0127] Synthesis of G103-1

[0128] feed ratio

[0129]

[0130] Experimental procedure: 38.80g BMP, 35.80g BBA, 1.00g palladium acetate, 4.67g triphenylphosphine, 67.80g potassium carbonate, 370mL ethylene glycol dimethyl ether and 245mL distilled water were added to a 1000mL three-necked flask, and then at room temperature Replaced with nitrogen for 4 times, heated to reflux and stirred for 16 h, then cooled to room temperature, then added 200 mL of ethyl acetate for extraction, after layering, the aqueous layer was extracted with 200 mL of ethyl acetate, the organic layers were combined, and 400 mL of saturated common salt was used. After washing with water, the aqueous layer was discarded after separation, the organic layer was dried over anhydrous sodium sul...

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Abstract

The invention discloses an organometallic electroluminescence complex, which is composed of a main ligand with luminescence properties, a deuterium-substituted auxiliary ligand and a metal to form an organometallic electroluminescence complex, which can be applied to organic luminescence. device OLED. The disclosed metal complex has the following chemical formula: wherein metal M=Ir, Eu, Os; it is characterized in that the auxiliary ligand contains deuterated atoms, and its enhanced hyperconjugation increases the stability of the luminescent material and prolongs the life of the luminescent material. The service life of the applied OLED device. The invention also discloses a method for preparing part or all of the deuterium-containing acyl ketone compounds. Some or all of the deuterium-containing acyl ketone compounds may also contain cross-linkable functional groups, which is beneficial to obtain an insoluble and insoluble cross-linked structure light-emitting material after film formation, and improves the stability of the OLED light-emitting device.

Description

technical field [0001] The present invention relates to novel electroluminescent organic metal heterocomplexes and organic electroluminescent devices prepared therefrom. The disclosed organometallic complex adopts part or all of deuterated auxiliary ligands, thereby increasing its hyperconjugation effect, expanding the conjugated structure of the original most fragile acyl ketone auxiliary ligand in the luminescent ligands, and is conducive to improving the luminescence. The stability of material properties is applied to organic light-emitting OLED devices to obtain light-emitting OLED display and lighting devices with increased lifespan. After further introducing a cross-linkable structure into the auxiliary ligand, an insoluble and infusible cross-linked structure can also be obtained, which is beneficial to the preparation of multi-layer OLED devices by solution film formation. The fixation can avoid the problems of solution erosion and thermal morphology change, and incre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 李晓常殷正凯丰田上野和則
Owner 冠能光电材料(深圳)有限责任公司