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Orange optical iridium coordination compounds and application thereof in organic electro-generated white or orange optical device

A technology of orange iridium and complexes, applied in the field of organic electroluminescence, can solve problems such as high LUMO energy level, unsatisfactory, and reduced bandgap width, so as to increase electroluminescence efficiency, increase charge transport balance performance, The effect of reducing vibration frequency

Inactive Publication Date: 2014-01-08
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But when an electron-withdrawing substituent is introduced into the 5-position, the weak π-donating effect of the fluorine atom on the electron density of the HOMO will counteract the electron-withdrawing effect of the fluorine atom, thus reducing the bandgap width.
Although these methods for modifying phosphorescent emission by introducing electron-donating or electron-withdrawing groups have been recognized, the development of phosphorescent materials that can easily modify emission by modifying the electronic structure of ligands has not yet reached a satisfactory level.
[0004] In addition, the LUMO energy level of the 2-phenylbenzothiazole iridium complex is relatively high. If no modification is made, the electrons will have a higher potential barrier when injected from the cathode.

Method used

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  • Orange optical iridium coordination compounds and application thereof in organic electro-generated white or orange optical device
  • Orange optical iridium coordination compounds and application thereof in organic electro-generated white or orange optical device
  • Orange optical iridium coordination compounds and application thereof in organic electro-generated white or orange optical device

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Embodiment 1: Complex (CF 3 P-CF 3 BT) 2 Synthesis of Ir(acac)

[0049] The specific synthesis steps are as follows:

[0050]

[0051] 1: Ligand CF 3 P-CF 3 Synthesis of BT

[0052] Synthesis of 1: Dissolve 4-aminobenzotrifluoride (10.08g, 62.60mmol), 4-trifluoromethylbenzoyl chloride (10.00g, 62.60mol), and triethylamine (9.6mL) in 100ml of chloroform. At 0°C, react under the protection of argon for 30 min, then transfer to room temperature to continue the reaction for 6 h, remove the solvent, and recrystallize with ethanol to obtain 15.9 g (80%) of white flocculent solid. 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.98 (d, J = 7.7 Hz, 2H), 7.90 (s, 0H), 7.77 (d, J = 7.9 Hz, 4H), 7.64 (d, J = 8.2 Hz, 2H). 13 C NMR (101 MHz, CDCl 3 ): δ (ppm) 164.37, 144.13, 140.58, 137.69, 133.79, 127.58, 126.52, 126.48, 126.06, 126.02, 119.88.

[0053] Synthesis of 2: Dissolve 1 (13.34g, 40mol) and Lawson's reagent (22.08g, 60mmol) in 100mL of toluene, vacuumize / argon flow for ...

Embodiment 2

[0057] Example 2: In this example, the suitable R in the compound of formula 1 1 -R 4 The groups include the substituent configurations in Table 1.

[0058] Table 1

[0059]

[0060]

[0061]

Embodiment 3

[0062] Embodiment 3: the preparation of orange light organic light-emitting diode

[0063]For the given orange light embodiment, the structure of the device is: ITO / PEDOT:PSS (40nm) / PVK:OXD-7: (CF 3 P-CF 3 BT) 2 Ir(acac) (40nm) / Ca(10nm) / Al(100nm), the preparation process of the device is as follows:

[0064] 1. Spin-coat the conductive polymer PEDOT:PSS on the anode ITO at 3000r / min, and anneal at 120°C for 1h to form a 40nm-thick hole-injecting double-layer electrode;

[0065] 2. Add PVK:OXD-7:(CF 3 P-CF 3 BT) 2 Ir(acac) was made into a solution with a concentration of 15 mg / ml at 100:40:10, spin-coated on PEDOT:PSS at a speed of 2000 rpm, and annealed at 120°C for 10 minutes in nitrogen;

[0066] 3. Evaporate Ca(10nm) / Al(100nm) on the light-emitting layer as the cathode.

[0067] The properties of the obtained orange EL device are as follows: turn-on voltage: 8V, maximum brightness: 10527cd / m 2 , the highest efficiency: 11.03 cd / A (19.8V), color coordinates (0.48,0.5...

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Abstract

The invention discloses organic optical iridium coordination compounds and application thereof in an organic electro-generated white or orange optical device. The orange optical iridium coordinate compounds have a structural formula as formula 1 or formula 2 which is shown in the specification, wherein R1 can be trifluoromethyl or pentafluoroethyl, R4 can be trifluoromethyl or pentafluoroethyl or R1=R4, R2 is selected from hydrogen, methyl, ethyl and halogen or halogen-substituted methyl or ethyl, R3 is independently selected from hydrogen, methyl, ethyl, halogen or halogen-substituted methyl or ethyl or R2=R3, and the halogen is fluorine, chlorine, bromine or iodine. The invention has the advantages as follows: a fluorine-containing modified iridium coordination compound can be used for effectively lowering vibrating frequency, reducing non-radiative transition and increasing electroluminescence efficiency; a film prepared by using a fluorine atom-containing modified coordination compound has better feature; self-quenching behaviors are restrained by steric hindrance of CF3; and charge transfer balance performance is increased by very good current carrier transmission performance, so that an efficient doped organic electro-generated luminescent device can be manufactured.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to the synthesis of orange iridium complexes based on 2-phenylbenzothiazole nitrogen heterocycles as ligands and the use of such materials in white organic light-emitting diodes (WOLEDs) in the application. Background technique [0002] Heavy metal complexes with phosphorescent emission have attracted sufficient attention in organic light-emitting diodes (OLEDs) due to their good color purity, high quantum efficiency, short phosphorescence lifetime, and high photothermal stability. In particular, modified cyclic metal ligands (C ∧ N ligand) can control the luminescence of the complexes to be tunable in the entire visible light range, which is beneficial to realize full-light and white-light displays. Tuning phosphorescence emission can usually be achieved by changing the C ∧ Substituent groups on N ligands, such as ppy (2-phenyl-pyridinato-C 2 ,N)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCY02B20/181Y02B20/00
Inventor 李立东徐新军王金山田原
Owner UNIV OF SCI & TECH BEIJING
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