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A kind of ring metal iridium complex and its preparation method and application

An iridium complex, cyclic metal technology, applied in indium organic compounds, chemical instruments and methods, platinum group organic compounds, etc., can solve the problems of difficult purification of polymer materials, poor film-forming properties, limited applications, etc., to improve electron injection. and transmission ability, prevent the change of luminous color, improve the effect of luminous performance

Active Publication Date: 2021-10-29
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Polymer phosphorescent materials generally adopt the method of spin coating or inkjet printing, but because the purification of polymer materials is difficult, the efficiency of polymer electroluminescent devices is not high and the life is short (Nat Commun., 2013, 4, 1; Chem. Mater., 2010, 23, 326)
The best way to overcome each other's shortcomings is to synthesize small-molecule phosphorescent materials that can be produced by spin coating or inkjet printing. Application in this method

Method used

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  • A kind of ring metal iridium complex and its preparation method and application
  • A kind of ring metal iridium complex and its preparation method and application
  • A kind of ring metal iridium complex and its preparation method and application

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Embodiment 1

[0064] The invention provides a kind of preparation method of ring metal iridium complex, comprises the following steps:

[0065] Synthesis of S1, Ir-1-Br

[0066] Add 600mg (1.92mmol) of dibenzothienylpyridine, 21mL of ethylene glycol monoethyl ether and 7mL of water into a 100mL three-neck flask, and quickly add 260mg (0.76mmol) of IrCl under nitrogen protection 3 ·3H 2 O, 100 ℃ constant temperature reaction 20h. After cooling, a yellow solid was produced, which was filtered by suction, washed with water and a little ethanol, and dried in vacuo to obtain 347 mg of an orange powder, which was directly used in the next reaction without further separation and purification.

[0067] In a 100mL three-necked flask, add 82mg (0.054mmoL) of the previous step reaction product, 6-((6-(4-bromophenoxy)hexyl)oxy)picolinic acid 65mg (0.164mmoL), sodium carbonate 74mg ( 0.54mmoL) and ethylene glycol monoethyl ether 30mL. Under the protection of argon, heat up to 135°C for reflux reacti...

Embodiment 2

[0078] The invention provides a kind of preparation method of ring metal iridium complex, comprises the following steps:

[0079] Synthesis of S1, Ir-2-Br

[0080] Add 512mg (1.49mmol) of 2-bromodibenzothienylpyridine, 21mL of ethylene glycol monoethyl ether and 7mL of water into a 100mL three-neck flask, and quickly add 211mg (0.59mmol) of IrCl under argon protection 3 ·3H 2 O, 100 ℃ constant temperature reaction 20h. After cooling, an orange-yellow solid was produced, which was filtered with suction, washed with water and a little absolute ethanol successively, and dried in vacuo to obtain 540 mg of an orange-yellow powder. The product was directly used in the next reaction without further separation and purification.

[0081] In a 100 mL three-neck flask, add 200 mg (0.11 mmol) of the reaction product of the previous step, 67 mg (0.55 mmol) of picolinic acid, 157 mg (1.1 mmol) of sodium carbonate and 30 mL of ethylene glycol monoethyl ether in sequence. Under the protecti...

Embodiment 3

[0092] The invention provides a kind of preparation method of ring metal iridium complex, comprises the following steps:

[0093] Synthesis of S1, Ir-3-Br

[0094] Add 512mg (1.49mmol) of 2-bromodibenzothienylpyridine, 21mL of ethylene glycol monoethyl ether and 7mL of water into a 100mL three-necked flask, and quickly add 211mg (0.59mmol) of IrCl3·3H2O under the protection of argon, at 100°C Constant temperature reaction 20h. After cooling, an orange-yellow solid was produced, which was filtered with suction, washed with water and a little absolute ethanol successively, and dried in vacuo to obtain 540 mg of an orange-yellow powder. The product was directly used in the next reaction without further separation and purification.

[0095] In a 100mL three-necked flask, 170mg (0.093mmoL) of the reaction product of the previous step, 109mg (0.279mmoL) of 6-((6-(4-bromophenoxy)hexyl)oxy)picolinic acid, and 98mg of sodium carbonate ( 0.93mmoL) and ethylene glycol monoethyl ether ...

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Abstract

The invention discloses a cyclometal iridium complex and its preparation method and application. The preparation method of the cyclometal iridium complex is: any of Ir-1-Br, Ir-2-Br or Ir-3-Br One with 1,3-bis(6-carbazolylhexyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborinyl)benzene, carbonic acid Potassium aqueous solution, toluene and ethanol are mixed, tetrakis(triphenylphosphine) palladium is added under the protection of an inert gas, and the reaction is heated; after cooling, washing with water, extraction with dichloromethane, drying, and purification by column chromatography, the cyclometal iridium complex is obtained , ie Ir‑1, Ir‑2 or Ir‑3. The cyclometalated iridium complex is used in an organic green light device, and the organic green light device includes an indium tin oxide conductive glass, a hole injection layer, a light emitting layer, a cathode injection layer and a cathode layer that are sequentially stacked, and the light emitting layer Cyclometallic iridium complexes are used.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a ring metal iridium complex and its preparation method and application. Background technique [0002] The luminescence mechanism of organic electrophosphorescence is different from that of organic electrofluorescence. The former can use triplet and singlet excitons to emit light at the same time, and the internal quantum efficiency can theoretically reach 100%, breaking through the maximum internal quantum efficiency of fluorescent materials. 25% theoretical limit (Adv. Mater., 2002, 14, 701; Phys. Rev. B, 1999, 60, 14422; Chem. Soc. Rev., 2012, 41:4797). In particular, the heavy metal Ir has a strong spin-orbit coupling, which allows the originally forbidden triplet transition to be allowed. The strong interaction between heavy metals and ligands enables complexes containing transition metals to make singlet and triplet transitions. The state is mixed, which...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00H01L51/50H01L51/54
CPCC07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 梁爱辉刘志谦周文静胡斯帆
Owner JIANGXI NORMAL UNIV