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A combination of a host compound and a dopant compound

A compound and dopant technology, which is applied in the direction of indium organic compounds, platinum group organic compounds, compounds of group 4/14 elements of the periodic table, etc., can solve the problems of unmentioned combinations, low glass transition temperature, and power efficiency. Advantages and other issues

Inactive Publication Date: 2016-04-27
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Although these phosphorescent host materials provide good emission characteristics, they have the following drawbacks: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during the high temperature deposition process under vacuum
Therefore, organic EL devices using conventional phosphorescent materials have no advantage in terms of power efficiency (1m / W)
(3) In addition, the operating life and luminous efficiency of organic EL devices are unsatisfactory
[0010] Korean Patent Application Laid-Open No. 2013-0054205 and No. 2011-0130475 and US2013 / 0026452A1 disclose that a heterocoordinated iridium complex having a phenylpyridine ligand and a dibenzo-containing ligand is included in a light emitting material of an organic EL device. compounds as dopant compounds, but no mention is made of combinations with specific host compounds suitable for dopant compounds

Method used

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  • A combination of a host compound and a dopant compound
  • A combination of a host compound and a dopant compound
  • A combination of a host compound and a dopant compound

Examples

Experimental program
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example 1

[0074] Example 1: Preparation of Compound D-2

[0075]

[0076] Preparation of compound 1-1

[0077] 2-Phenylpyridine (10.0g, 32.0mmol), iridium(III) chloride hydrate (IrCl 3 ·xH 2 O) (8.1 g, 29.0 mmol), 2-ethoxyethanol (220.0 mL) and H 2 O (74.0 mL) was stirred in the flask at 140 °C for 24 hours. After the reaction was complete, the mixture was cooled to room temperature and washed with H 2 Washed with O and methanol (MeOH), and then dried to obtain compound 1-1 (11.0 g, 71%).

[0078] Preparation of compound 1-2

[0079] Compound 1-1 (10.0 g, 9.0 mmol) was dissolved in dichloromethane (MC) (4.0 L) in a flask. Silver triflate (AgOTf) (5.0 g, 19.0 mmol) dissolved in MeOH (400.0 mL) was slowly added thereto and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the reaction mixture was filtered and the filtrate was dried to obtain compound 1-2 (12.0 g, 94%).

[0080] Preparation of Compound 1-3

[0081] 2-Bromopyridin...

example 2

[0085] Example 2: Preparation of Compound D-3

[0086]

[0087] Preparation of compound 2-1

[0088] 2-Bromo-5-methylpyridine (15.0g, 87.0mmol), phenylboronic acid (14.0g, 114.0mmol), Pd(PPh 3 ) 4 (3.0g, 2.6mmol), K 2 CO 3 (36.0g, 260.0mmol), toluene (300.0mL), EtOH (150.0mL) and H 2 O (130.0 mL) was stirred in the flask at 100 °C for 3 hours. After the reaction was complete, the mixture was extracted with EA, by using MgSO 4 The remaining water was removed and the mixture was distilled under reduced pressure. By column chromatography with MC / Hx=1 / 2, compound 2-1 (10.0 g, 68%) was obtained as a white solid.

[0089] Preparation of Compound 2-2

[0090] Compound 2-1 (10.0g, 30.0mmol), IrCl 3 ·xH 2 O (8.0 g, 27.0 mmol), 2-ethoxyethanol (200.0 mL) and H 2 O (70.0 mL) was stirred in the flask at 140 °C for 24 hours. After the reaction was complete, the mixture was cooled to room temperature and washed with H 2 Washed with O and MeOH, and then dried to obtain ...

example 3

[0096] Example 3: Preparation of Compound D-95

[0097]

[0098] Preparation of compound 3-1

[0099] 2-Bromo-4-methylpyridine (10.0g, 63.0mmol), dibenzo[b,d]furan-4-ylboronic acid (15.0g, 76.0mmol), Pd(PPh 3 ) 4 (2.2g, 2.0mmol), Na 2 CO 3 (20.0g, 19.0mmol), toluene (300.0mL), EtOH (150.0mL) and H 2 O (10.0 mL) was stirred in the flask at 100 °C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with EA. By using MgSO 4 The remaining water was removed and the mixture was distilled under reduced pressure. By column chromatography with MC / Hx=1 / 3, Compound 3-1 (11.0 g, 67%) was obtained as a white solid.

[0100] Preparation of Compound D-95

[0101] MeOH (200.0 mL) and EtOH (100.0 mL) were added to compound 3-1 (7.0 g, 28.0 mmol) and compound 2-3 (10.0 g, 14.0 mmol) in a flask and the mixture was stirred at reflux for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and fi...

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Abstract

The present invention relates to a specific combination of dopant compounds and host compounds. By using a combination of the dopant and host compounds according to the present invention, an organic electroluminescent device has improved current efficiency compared with conventional light-emitting material, and thus has improved power efficiency at a low driving voltage.

Description

technical field [0001] The present invention relates to a combination of a specific dopant and a host compound. Background technique [0002] An electroluminescence (EL) device is a self-luminous device, which has the advantage of providing a wider viewing angle, higher contrast ratio, and faster response time. Eastman Kodak (EastmanKodak) first developed an organic EL device by using aromatic diamine small molecules and aluminum complexes as materials for forming the light-emitting layer [see Appl. Phys. Lett .), 51, 913, 1987]. [0003] An organic EL device converts electrical energy into light by injecting charges into an organic light-emitting material and generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of an organic EL device can be composed of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emission layer (EML) (containing a host material and a dopant ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00C07D255/02C07D239/14C07F7/14H01L51/54H05B33/14
CPCC07F15/0033C07D403/10C07D487/04C07D491/048C07D495/04H10K85/654H10K85/657H10K85/342H10K85/6572H10K50/11H10K2101/10H10K85/649H10K85/631H10K50/12
Inventor K-J·李S-K·尹C-S·金H·金S-W·李S-Y·钟S-H·李J-E·杨Y-K·金Y-J·曹K-J·朴S-W·蒋
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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