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Organic electrophosphorescent material, preparation method and applications thereof, and OLED device containing organic electrophosphorescent material

A technology of electrophosphorescence and phosphorescent materials, which is applied in the field of OLED light-emitting materials, and can solve problems such as difficult purification, strong intermolecular force of conjugated light-emitting second ligands, and insoluble problems.

Pending Publication Date: 2020-03-24
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, due to the large molecular weight of the heavy metal-secondary ligand complex itself, and the strong intermolecular force of the conjugated luminescent second ligand used, most of the organometallic complexes have sublimation, and the evaporation temperature is close to Complex decomposition temperature, insoluble and difficult to purify, etc., affect the large-scale production of OLED

Method used

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  • Organic electrophosphorescent material, preparation method and applications thereof, and OLED device containing organic electrophosphorescent material
  • Organic electrophosphorescent material, preparation method and applications thereof, and OLED device containing organic electrophosphorescent material
  • Organic electrophosphorescent material, preparation method and applications thereof, and OLED device containing organic electrophosphorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0065] Embodiments 1-5 provide iridium-based organic electrophosphorescent materials (referred to as Ir-1 to Ir-5 in sequence) with the structure of formula I, and their structural formulas are as follows:

[0066]

[0067] Taking Ir-3 as an example, its preparation method is as follows:

[0068] (1) compound (2.02g, 10mmol), phenylboronic acid (1.8g, 15mmol), potassium carbonate (5g, 50mmol), triphenylphosphine (15g, 50mmol), palladium acetate (0.15g, 0.62mmol), water (20mL) and di Oxyhexane (50mL) was mixed, under the protection of nitrogen, reflux reaction at 25°C for 24h, cooled after the reaction, adjusted the pH to 2-3 with 3% acetic acid, extracted with ethyl acetate (3×20mL), evaporated solvent, to obtain the compound 3g of the crude product; mix the above crude product with 50mL polyphosphoric acid, react at 210°C for 5h, cool after the reaction, add 50mL of ice water, adjust the pH>7 with NaOH solution (1mol / L), and use ethyl acetate Extraction (3 × 20mL), ev...

Embodiment 6-10

[0081] Embodiments 6-10 provide iridium-based organic electrophosphorescent materials (referred to as Ir-6 to Ir-10 in sequence) with the structure of formula I, and their structural formulas are as follows:

[0082]

[0083] Taking Ir-8 as an example, its preparation method is as follows:

[0084] (1) Compounds are prepared according to the preparation method of Ir-3

[0085] (2) Compound (6.62g, 30.0mmol), IrCl 3 ·H 2 O (3.7g, 10mmol), water (30mL) and 2-ethoxyethanol (90mL) were mixed, under the protection of nitrogen, reflux reaction at 120°C for 12h, the reaction formula is as follows:

[0086]

[0087] After the reaction was completed, it was filtered, washed with methanol (3×20 mL), and dried in vacuo to obtain a dimer compound;

[0088] (3) Dimer compound (9g, 10mmol) that acetylacetone (10g, 100mmol), step (2) obtains, sodium carbonate (10.6g, 100mmol) and 2-ethoxyethanol (200mL) are mixed, in 25 Reaction at ℃ for 24h, the reaction formula is as follows:...

Embodiment 11-16

[0094] Embodiments 11-16 provide iridium-based organic electrophosphorescent materials (referred to as Ir-11 to Ir-16 in sequence) having the structure of formula II, and their structural formulas are as follows:

[0095]

[0096] Taking Ir-16 as an example, its preparation method is as follows:

[0097] (1) compound (2.5g, 10mmol), phenylboronic acid (1.8g, 15mmol), potassium carbonate (5g, 50mmol), triphenylphosphine (15g, 50mmol), palladium acetate (0.15g, 0.62mmol), water (20mL) and di Oxyhexane (50mL) was mixed, under the protection of nitrogen, reflux reaction at 25°C for 24h, cooled after the reaction, adjusted the pH to 2-3 with 3% acetic acid, extracted with ethyl acetate (3×20mL), evaporated solvent, to obtain the compound 3g of the crude product; mix the above crude product with 50mL polyphosphoric acid, react at 210°C for 5h, cool after the reaction, add 50mL of ice water, adjust the pH>7 with NaOH solution (1mol / L), and use ethyl acetate Extraction (3 × ...

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Abstract

The invention provides an organic electrophosphorescent material, a preparation method and applications thereof, and an OLED device containing the organic electrophosphorescent material, wherein the organic electrophosphorescent material is a compound with a structure represented by a formula I, a formula II or a formula III, the compound with the structure represented by the formula I is a greenlight-emitting material, and the compounds with the structures represented by the formula II and the formula III are red light-emitting materials. The organic electrophosphorescent material provided by the invention is easy to sublimate and dissolve, and is beneficial to large-scale production of OLEDs; and an OLED device taking the organic electrophosphorescent material provided by the inventionas a luminescent layer object material has the advantages of high efficiency and long service life.

Description

technical field [0001] The invention belongs to the technical field of OLED luminescent materials, and in particular relates to an organic electrophosphorescent material, its preparation method, application and an OLED device containing the same. Background technique [0002] The technology of organic light emitting diodes (OLEDs) is undergoing rapid development. OLEDs originally used singlet excitons generated by electrically excited molecules to emit light. This radioluminescence from a singlet excited state is called fluorescence, but its luminescence efficiency is low. Since the introduction of organic electrophosphorescent materials of high-efficiency heavy metal complexes, phosphorescent materials using triplet radiation, especially phosphorescent materials of iridium-based metal complexes, have attracted much attention due to their high luminous efficiency and energy conversion rate, and have become promising materials. Focus in the field of electroluminescence rese...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/11
Inventor 孙加宝鄢亮亮
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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