Carbazole group-containing azafluorene orange-light ionic-type iridium (III) complexes, and preparation method and applications thereof

A technology based on azafluorene and carbazole, which is applied in the field of organic electroluminescence display and can solve the problem of high cost

Active Publication Date: 2015-11-04
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, most of the currently reported OLEDs are based on neutral iridium complexes, and the preparation of devices requires a vacuum evaporation process, which is costly.

Method used

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  • Carbazole group-containing azafluorene orange-light ionic-type iridium (III) complexes, and preparation method and applications thereof
  • Carbazole group-containing azafluorene orange-light ionic-type iridium (III) complexes, and preparation method and applications thereof
  • Carbazole group-containing azafluorene orange-light ionic-type iridium (III) complexes, and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of complex Ir1:

[0034] The auxiliary ligand 9,9-bis(9-ethylcarbazol-3-yl)-4,5-diazafluorene (ECAF) (0.42 g) containing 0.76 mmol of bicarrier groups was mixed with 0.33 mmol[Ir(ppy) 2 Cl] 2 (0.35 g) of the mixture was dissolved in 30 ml of ethylene glycol monoethyl ether, and reacted at 130° C. for 10 hours under the protection of nitrogen. Then cool to room temperature, add 20mL of deionized aqueous solution that is dissolved with 0.87g ammonium hexafluorophosphate to the above-mentioned solution under stirring, produce a large amount of precipitation, suction filtration, the precipitation is passed through the column chromatography column (eluent is dichloromethane / Acetone=10:1) was purified to obtain the corresponding complex [Ir(ppy) 2 (ECAF)] PF 6 (Ir1).

Embodiment 2

[0036] Synthesis of complex Ir2:

[0037] The auxiliary ligand 9,9-bis(9-ethylhexylcarbazol-3-yl)-4,5-diazafluorene (EHCAF) (0.49g) containing 0.76mmol of bicarrier groups was mixed with 0.33mmol [Ir(ppy) 2 Cl] 2 (0.35g) of the mixture was dissolved in 30ml of ethylene glycol monoethyl ether, and reacted at 150°C for 12 hours under the protection of nitrogen. Then cool to room temperature, add 20mL of deionized aqueous solution that is dissolved with 0.87g ammonium hexafluorophosphate to the above-mentioned solution under stirring, produce a large amount of precipitation, suction filtration, the precipitation is passed through the column chromatography column (eluent is dichloromethane / Acetone=10:1) was purified to obtain the corresponding complex [Ir(ppy) 2 (EHCAF)]PF 6 (Ir2).

Embodiment 3

[0039] Synthesis of complex Ir3:

[0040] The auxiliary ligand 9,9-bis(9-phenylcarbazol-3-yl)-4,5-diazafluorene (PCAF) (0.49 g) containing 0.76 mmol of bicarrier groups was mixed with 0.33 mmol[Ir(ppy) 2 Cl] 2 (0.35 g) of the mixture was dissolved in 30 ml of ethylene glycol monoethyl ether, and reacted at 160° C. for 15 hours under the protection of nitrogen. Then cool to room temperature, add 20mL of deionized aqueous solution that is dissolved with 0.87g ammonium hexafluorophosphate to the above-mentioned solution under stirring, produce a large amount of precipitation, suction filtration, the precipitation is passed through the column chromatography column (eluent is dichloromethane / Acetone=10:1) was purified to obtain the corresponding complex [Ir(ppy) 2 (PCAF)]PF 6 (Ir3).

[0041] In the above-mentioned embodiment, the deionized aqueous solution of ammonium hexafluorophosphate can be replaced by an aqueous solution of ammonium tetrafluoroborate, and the chemical fo...

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Abstract

The invention discloses carbazole group-containing azafluorene orange-light ionic-type iridium (III) complexes including hexafluorophosphoric acid-[di(2-phenylpyridine)]-[9,9-di(9-ethyl carbazole-3-yl)-4,5-diazafluorene] iridium (III) (Ir1), hexafluorophosphoric acid-[di(2-phenylpyridine)]-[9,9-di(9-ethyl hexyl carbazole-3-yl)-4,5-diazafluorene] iridium (III) (Ir2), and hexafluorophosphoric acid-[di(2-phenylpyridine)]-[9,9-di(9-phenylcarbazole-3-yl)-4,5-diazafluorene] iridium (III) (Ir3). When doping concentration of the complex Ir1 is 10%, maximum illumination brightness 907cd / m2 and current efficiency 8.35cd / A are achieved, the maximum peak of an electroluminescence spectrum is observed at 568nm, color coordinates (CIE) x=0.45, and y=0.53, orange light is emitted, and relatively weak efficiency roll off of parts is observed. Electroluminescence devices made from the complex Ir2 and Ir3 possess similar performance.

Description

technical field [0001] The invention relates to an organic electroluminescence material and its application in an organic electroluminescence device, belonging to the technical field of organic electroluminescence display. Background technique [0002] Organic Electroluminescence Devices (Organic Electroluminescence Devices or Organic Light-Emitting Diodes, hereinafter referred to as OLEDs) are widely used in various fields due to their ultra-thin, fully cured, self-illuminating, fast response, good temperature characteristics, and flexible displays. Has a wide range of applications. [0003] Research on OLEDs began in the 1960s. In 1963, Pope et al. (J.Chem.Phys.1963,38:2042-2043) studied the blue electroluminescence of anthracene single crystal (10-20 μm), because the anthracene single crystal light-emitting layer was thick and the electrodes used Due to the constraints of materials (silver colloid and sodium chloride solution), the luminous starting voltage of the devic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/1029C09K2211/185C09K2211/1007H10K85/342
Inventor 张付力翟滨李素芝杨晓燕曹广秀
Owner SHANGQIU NORMAL UNIVERSITY
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