Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof

A technology of iridium complexes and phosphorescent materials, applied in luminescent materials, compounds containing elements of Group 8/9/10/18 of the periodic table, chemical instruments and methods, etc. Agglomeration and other problems, to achieve the effects of low cost, good luminescence performance, and simple synthesis process

Inactive Publication Date: 2011-10-26
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reasons for this situation are: (1) The energy level difference of the compounds corresponding to red light emission is small, which increases the difficulty in the design of ligands for red light materials; (2) In the red light material system, there is a strong π-π bond interaction, or strong charge transfer properties, will aggravate the aggregation of molecules and easily lead to quenching phenomenon

Method used

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  • Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof
  • Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof
  • Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of 2-acenaphthylene-5-yl-4-phenyl-quinoline

[0042] Take g aluminum trichloride and 20mL dichloromethane to react for 2h in an ice bath until the aluminum trichloride is completely dissolved, add 1.54g acenaphthylene, and then slowly dropwise dissolve in the dichloromethane solution with mL of acetyl chloride. Pour into a large amount of water, stir overnight, extract with dichloromethane, spin to dry and pass through a column with silica gel (petroleum ether) to obtain a light yellow solid with a yield of 80% 1-acenaphthylene-5-yl-ethanone. Take 0.1g phosphorus pentoxide and 20ml m-cresol into a 100mL single-necked flask and react at 140℃ for 2h, and then take 0.196g 1-acenaphthylene-5-yl-ethanone and 0.197g 2-amino group. In 20ml m-cresol of benzophenone, react at 180°C for 6h. After cooling, it was poured into 300ml of 40% sodium hydroxide solution, extracted with ethyl acetate, spin-dried and passed through the column with silica gel (pure oil et...

Embodiment 2

[0043] Example 2: Synthesis of 6-(4-phenyl-quinolin-2-yl)-benzo[de]isochrome-1,3-dione

[0044] Take 0.357g 2-Acenaphthen-5-yl-4-phenyl-quinoline and 1g potassium dichromate and put them into 10mL acetic acid. After reacting at 120°C for 30 minutes, it was taken out, filtered off with suction, the filter cake was washed with water, the filtrate was extracted with ethyl acetate, and recrystallized with acetic anhydride to obtain the pale yellow product 6-(4-phenyl-quinolin-2-yl)- Benzo[de]isochrome-1,3-dione, the yield is 83%

Embodiment 3

[0045] Example 3: Synthesis of 2-Butyl-6-(4-phenyl-quinolin-2-yl)-benzo[de]isoquinoline-1,3-dione

[0046] Dissolve 5 in 20 mL of ethanol, then add 2 mL of n-butylamine, and then reflux for reaction overnight at 80°C. Then spin off all the solvents and wash off excess n-butylamine with 20 mL of 10% dilute hydrochloric acid. The yellow product 2-butyl-6-(4-phenyl-quinolin-2-yl)-benzo[de]isoquinoline-1,3-dione was obtained with a yield of 95%

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Abstract

The invention relates to a class of phosphorescent iridium complexes with wavelengths from infrared to near-infrared range, particularly relates to a class of bicyclo metal iridium complexes (C^N)2Ir(L^Y) and ionic metal iridium complexes (C^N)2Ir(N^N)<+>Z<->, with structures represented by formula (I) and formula (II) respectively, wherein R1 and R2 are independently one of hydrogen atom, halogen atom, cyan group, nitro group, acyl group, C1-18 linear chain, branched chain or cyclic aliphatic alkyl group, substituted alkyl group, alkoxy group, aryloxy, alkylthio group, arylthio, aliphatic amine group, aromatic amine group, substituted siloxane group, substituted silicon group, aryl group, substituted aryl group, heterocyclic aryl group or substituted heterocyclic aryl group; C^N is a phenylquinoline substituted naphthalene derivative; L^Y is one of N-COOH, 8-hydroxyquinolines, beta-diketones, N^NH and other compounds; N^N is one of dipyridine, diquinoline, 1,10-o-phenanthroline and derivatives thereof and other compounds; and Z is hexafluorophosphate radical or perchlorate radical. The bicyclo metal iridium complexes (C^N)2Ir(L^Y) are shown in formula (I), and the ionic metal iridium complexes (C^N)2Ir(N^N)<+>Z<-> are shown in formula (II).

Description

Technical field [0001] The invention belongs to the technical field of optoelectronic materials. Specifically relates to a class of iridium complexes ranging from red light to near infrared and a preparation method thereof Background technique [0002] Since Tang et al. reported a double-layer organic electroluminescence device with high brightness and low working voltage in 1987, thin film electroluminescence devices have been developed rapidly, and organic electroluminescence has attracted great attention due to its excellent performance. . To achieve application and industrialization of organic electroluminescence, one of the key factors is to improve luminous efficiency and brightness. The improvement of its efficiency and brightness not only depends on the performance of the designed device, but also the choice of materials. effect. The heavy metal atoms in the heavy metal complexes can increase the spin-orbit coupling, thereby shortening the phosphorescence lifetime, inc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00H01L51/50H01L51/54
Inventor 梅群波郭远辉黄维王玲霞翁洁娜范曲立
Owner NANJING UNIV OF POSTS & TELECOMM
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