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Multiple host materials and organic electroluminescence devices including the multiple host materials

A host material and host technology, applied in the direction of luminescent materials, organic chemistry, organic chemistry methods, etc., can solve problems such as the specific combination of host materials that are not specifically disclosed, and achieve the effects of good life characteristics, low driving voltage, and high power efficiency

Pending Publication Date: 2021-09-28
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the references do not specifically disclose the specific combination of host materials claimed in the present disclosure

Method used

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  • Multiple host materials and organic electroluminescence devices including the multiple host materials
  • Multiple host materials and organic electroluminescence devices including the multiple host materials
  • Multiple host materials and organic electroluminescence devices including the multiple host materials

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0145] Example 1: Preparation of Compound C-1

[0146]

[0147] Synthesis of compound 1-1

[0148] In a flask, (9-phenyl-9H-carbazol-4-yl)boronic acid (96g, 334.3mmol), 2-bromo-1-chloro-3-nitrobenzene (71.8g, 304mmol), Pd 2 (dba) 3 (15g, 16.71mmol), S-Phos (10.9g, 26.76mmol) and K 3 PO 4 (315 g, 1.64 mol) was dissolved in 1500 mL of toluene, and the mixture was stirred at 130° C. for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound 1-1 (67 g, yield: 56.6%).

[0149] Synthesis of Compound 1-2

[0150] In a flask, compound 1-1 (23.5g, 58.9mmol), (2-chlorophenyl) boronic acid (18.4g, 117.8mmol), Pd 2 (dba) 3 (2.7mg, 2.95mmol), S-Phos (2.4mg, 5.89mmol), and K 3 PO 4 (63 g, 294.5 mmol) was dissolved in 300 mL of toluene, and the mixture was stirred at 130° C. for 12 hours. After th...

example 2

[0158] Example 2: Preparation of Compound C-29

[0159]

[0160] In a flask, compound 1-4 (4g, 9.84mmol), 3-bromo-1,1':2',1"-terphenyl (3.65g, 11.8mmol), Pd 2 (dba) 3 (448 mg, 0.492 mmol), S-Phos (448 mg, 0.984 mmol), and NaOtBu (2.84 g, 29.52 mmol) were dissolved in 50 mL of o-xylene, and the mixture was stirred at 170° C. for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and residual moisture was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound C-29 (1.5 g, yield: 24%).

[0161] compound MW M.P. C-29 643.78 282℃

example 3

[0162] Example 3: Preparation of Compound C-196

[0163]

[0164] Synthesis of Compound 3-1

[0165] Compound A (60g, 283mmol), compound B (100g, 424mmol), tetrakis (triphenylphosphine) palladium (16.3g, 14.1mmol), cesium carbonate (276g, 849mmol), 1400mL of toluene, 350mL of ethanol and 350mL Distilled water was added to the reaction vessel, and the mixture was stirred at 130 °C for 12 h. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was then separated by column chromatography to obtain compound 3-1 (38 g, yield: 41%).

[0166] Synthesis of compound 3-2

[0167] Compound 3-1 (38g, 117mmol), phenylboronic acid (35g, 234mmol), tris(dibenzylideneacetone) dipalladium (5.3g, 5.86mmol), S-Phos (4.8g, 11.7mmol), phosphoric acid Tripotassium (62 g, 293 mmol) and 600 mL of t...

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Abstract

The present disclosure relates to multiple host materials including at least one first host compound and at least one second host compound, and organic electroluminescence devices including the multiple host materials. By including a specific combination of compounds, a first host compound is represented by Formula 1, And the second host compound is represented by Formula 2. It is possible to provide the organic electroluminescence devices having improved driving voltage, luminous efficiency, power efficiency, and / or lifetime characteristics.

Description

technical field [0001] The present disclosure relates to various host materials and an organic electroluminescent device comprising the same. Background technique [0002] Small-molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al. at Eastman Kodak in 1987 by using a TPD / ALq3 bilayer consisting of an emissive layer and a charge transport layer. Since then, the development of OLEDs has been rapidly affected and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel realization. OLEDs characterized by high luminous efficiency and / or long lifetime are required for long-time use and high resolution of displays. [0003] In order to enhance luminous efficiency, driving voltage, and / or lifetime, various materials or concepts for organic layers of organic electroluminescent devices have been proposed. However, they are not satisfactory in practical use. [0004] K...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C07D519/00C07D491/16C07D495/16C07D491/06C07D403/04C07D405/14C07D409/14C07D491/048C07D495/04C07D209/56C07D405/04C07D409/04C07D409/10C07D405/10C07D401/14C07D403/10C07D491/22C07D413/04C07D417/04C07D417/14C07D417/10C07D413/10C07D413/14C07D471/04C07B59/00C09K11/06H01L51/50H01L51/54H10K99/00
CPCC07D487/06C07D519/00C07D491/16C07D495/16C07D491/06C07D403/04C07D405/14C07D409/14C07D491/048C07D495/04C07D209/56C07D405/04C07D409/04C07D409/10C07D405/10C07D401/14C07D403/10C07D491/22C07D413/04C07D417/04C07D417/14C07D417/10C07D413/10C07D413/14C07D471/04C07B59/002C09K11/06C07B2200/05C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/624H10K85/631H10K85/626H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/11C07D487/16H10K71/191H10K2101/90C07D407/10C07D407/14H10K85/656H10K50/12H10K85/622
Inventor 郑昭永全志松李琇炫赵相熙洪镇理
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC