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Bipolar phosphorescent host compounds, preparation method, application and electroluminescent device

An electroluminescent device and phosphorescent host technology, applied in the field of electroluminescent devices and bipolar phosphorescent host compounds, can solve the problem that the phosphorescent OLED cannot be well applied in industrial production, the efficiency of the phosphorescent light-emitting device cannot be further improved, and the adjacent Problems such as poor energy level matching of the active layer can achieve the effect of increasing the lifespan, reducing the degree of structural conjugation, and reducing the efficiency roll-off.

Active Publication Date: 2014-01-22
TCL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its relatively small molecular weight and relatively small structural distortion, its glass transition temperature is only 84 °C, which cannot be well applied to the industrial production of phosphorescent OLEDs.
At the same time, the HOMO / LUMO of the benzimidazole / carbazole phosphorescent host compound does not match well with the energy level of the adjacent active layer, which reduces the recombination probability of holes and electrons, so that the efficiency of phosphorescent light-emitting devices cannot be further improved.

Method used

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  • Bipolar phosphorescent host compounds, preparation method, application and electroluminescent device
  • Bipolar phosphorescent host compounds, preparation method, application and electroluminescent device
  • Bipolar phosphorescent host compounds, preparation method, application and electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0053] Preparation of bis(1-(N-phenylbenzimidazolyl)-3-(carbazolyl))benzene (DmBICP):

[0054] Dissolve 3-bromocarbazole (1.0 mmol), 3-pinacol borate carbazole (1.0 mmol) in toluene (50 ml) solution, and add 2M potassium carbonate aqueous solution (5.0 ml) and ethanol (5.0 ml ), and at the same time add the catalyst Pd(PPh3)4 (0.08 mmol), heated to 70 ~ 180 ℃ in the nitrogen environment, protected from light and refluxed for 3 ~ 48 hours; then cooled to room temperature, washed with water, extracted with dichloromethane, combined organic phase, dried over anhydrous sodium sulfate, filtered, removed the organic solvent, and recrystallized with dichloromethane and n-hexane to obtain a white solid powder, namely dicarbazole intermediate (0.8 mmol). Yield: 80.0%. MS (APCI): calcd for C 24 h 16 N 2 : 332.1, found, 333.4 (M+1) +

[0055] Dissolve the white solid powder (1.0 mmol) obtained in the previous step and the electron-withdrawing group halide 3-bromophenyl-N-phenylbenz...

Embodiment 2

[0057] Preparation of bis(1-(N-phenylbenzimidazolyl)-2-(carbazolyl))benzene (DoBICP):

[0058] A method similar to compound DmBICP was employed, except that 2-bromophenyl-N-phenylbenzimidazole was used instead of 3-bromophenyl-N-phenylbenzimidazole as the starting material in the Ullmann reaction. Bis(1-(N-phenylbenzimidazolyl)-2-(carbazolyl))benzene (DoBICP) white solid powder can be obtained, yield: 55%. MS (APCI): calcd for C 62 h 40 N 6 : 868.3, found, 869.5 (M+1) + .

Embodiment 3

[0060]Preparation of bis(1-(N-phenylbenzimidazolyl)-4-(carbazolyl))benzene (DpBICP):

[0061] A method similar to compound DmBICP was employed, except that 4-bromophenyl-N-phenylbenzimidazole was used as the starting material instead of 3-bromophenyl-N-phenylbenzimidazole in the Ullmann reaction. Bis(1-(N-phenylbenzimidazolyl)-4-(carbazolyl))benzene (DpBICP) white solid powder can be obtained, yield: 68%. MS (APCI): calcd for C 62 h 40 N 6 : 868.3, found, 869.2 (M+1) + .

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Abstract

The invention discloses bipolar phosphorescent host compounds, a preparation method, an application and an electroluminescent device. The bipolar phosphorescent host compounds are bisbenzimidazole and dicarbazole derivatives and have a structural general formula shown in a drawing in the specification, wherein in the structural general formula, when R1, R2 or R3 is a formula in the specification, the other two are H; when R1, R2 or R3 is a formula in the specification, the other two are H. The bisbenzimidazole / dicarbazole derivatives contain the same di(9-phenylcarbazole)group and benzimidazole group. The bipolar phosphorescent host compounds, the preparation method, the application and the electroluminescent device have the beneficial effects that the two groups of carbazole and benzimidazole are connected by adopting 3-position of carbazole through typical Suzuki reaction, so that the triplet levels of the bipolar phosphorescent host compounds can still well meet blue phosphorescent devices due to lower reduction of the conjugated structures of the bipolar phosphorescent host compounds while the bipolar phosphorescent host compounds maintain the bipolar transmission performances of the two groups.

Description

Technical field [0001] The present invention involves the field of organic lighting materials, especially a bilateral phosphor -optic subjectized compound, preparation method and application and electro -luminous devices. Background technique [0002] Because the two groups of phenazole and phenylzole have relatively good cavities and electronic transmission rates and relatively high triple -state energy levels, they are widely used in the main material of Blu -ray Phosphorus light emitting.Literature (J. Mater. Chem. 2012, 22, 13223) reported that the bipolar light main material of a triple -state energy level up to 3.0 EV was connected by a single pyramazole group through the position of benzo.Blu -ray Phosphorus Optical Firpic forms a luminous layer, and its maximum external quantum efficiency of its device reaches 18.7%.However, because the molecular weight is relatively small and its structural distortion is relatively small, its glass -changing conversion temperature is onl...

Claims

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Application Information

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IPC IPC(8): C07D403/14C09K11/06H01L51/54
CPCC09K11/06C07D403/14C09K2211/1044H10K85/6572
Inventor 黄宏申智渊付东
Owner TCL CORPORATION
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