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Novel organic electroluminescent compounds and organic electroluminescent device comprising the same

A compound, electroluminescence technology, applied in electroluminescence light sources, organic chemistry, electro-solid devices, etc., can solve the problems of degradation, no advantage in power efficiency, low glass transition temperature, etc., and achieve the effect of long working life

Inactive Publication Date: 2015-02-18
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these phosphorescent host materials provide good luminescence characteristics, they have the following disadvantages: (1) They may degrade during high temperature deposition in vacuum due to their low glass transition temperature and poor thermal stability
Therefore, organic EL devices using conventional phosphorescent materials have no advantage in power efficiency (lm / W)
(3) The working life and luminous efficiency of organic EL devices using phosphorescent host materials are not satisfactory
However, the working life and luminous efficiency of devices containing this compound are not satisfactory

Method used

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  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
  • Novel organic electroluminescent compounds and organic electroluminescent device comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: the preparation of compound C-1

[0077]

[0078] Preparation of compound C-1-1

[0079] To a 2L round bottom flask (RBF) was added N-phenylcarbazole-3-boronic acid (30.0 g, 105.0 mmol), 4-bromoiodobenzene (44.0 g, 157.0 mmol), tetrakis(triphenylphosphine)palladium ( O)[Pd(PPh 3 ) 4 ] (3.5g, 3.14mmol), Na 2 CO 3 (33.0 g, 313.0 mmol), toluene (600 mL), ethanol (EtOH) (150 mL) and distilled water (150 mL), the reaction mixture was stirred at 110° C. for 2 hours. Use ethyl acetate (EA) / H 2 O to work up the reaction mixture with MgSO 4 Dry to remove moisture, distill under reduced pressure and separate by column chromatography using dichloromethane (MC) and hexane to obtain compound C-1-1 (30.0 g, 72%) as a yellow solid.

[0080] Preparation of compound C-1-2

[0081] After compound C-1-1 (30.0 g, 75.3 mmol) was added to 1L RBF and replaced with nitrogen, tetrahydrofuran (THF) (400.0 mL) was added to the flask. The solution was cooled to -78°C...

Embodiment 2

[0086] Embodiment 2: the preparation of compound C-76

[0087]

[0088] Preparation of Compound C-76-1

[0089] Add 4-(diphenylamino)phenylboronic acid (14.0g, 48.4mmol), 3-bromocarbazole (10.0g, 40.3mmol), Pd(PPh 3 ) 4 (2.4g, 2.0mmol), K 2 CO 3 (13.0 g, 96.8 mmol), toluene (200 mL), EtOH (50 mL) and distilled water (50 mL), the reaction mixture was stirred at 110 °C for 24 hours. Use EA / H 2 The reaction mixture was extracted with MgSO 4 Dry to remove moisture, distill under reduced pressure and separate by column chromatography using MC and hexane to obtain compound C-76-1 (14.0 g, 84%) as a yellow solid.

[0090] Preparation of compound C-76

[0091] Compound C-76-1 (6.0 g, 14.6 mmol) and DMF (75 mL) were added to 250 mL RBF, and stirred to dissolve. NaH (0.9 g, 60% dispersion in mineral oil, 21.9 mmol) was added to the mixture and the reaction mixture was stirred for 30 minutes. 2-Chloro-4-phenylquinazoline (4.0 g, 17.5 mmol) was slowly added to the reacti...

Embodiment 3

[0092] Embodiment 3: the preparation of compound C-77

[0093]

[0094] Compound C-76-1 (4.0 g, 10.2 mmol) and DMF (50 mL) were added to 250 mL RBF, and stirred to dissolve. NaH (0.6 g, 60% dispersion in mineral oil, 15.4 mmol) was added to the mixture, and the reaction mixture was stirred for 30 minutes. 4-([1,1'-biphenyl]-3-yl)-2-chloroquinazoline (4.0 g, 12.3 mmol) was slowly added to the reaction mixture. After the addition, the reaction mixture was stirred at 50 °C for 2 hours. The reaction mixture was quenched with methanol and filtered to obtain a solid. The resulting solid was dried in a vacuum oven and separated by column chromatography using MC and hexane to give compound C-77 (2.1 g, 30%) as a yellow solid.

[0095] The physical properties of the compounds of the present invention prepared in Examples 1-3 are listed in Table 1 below:

[0096] Table 1

[0097]

[0098] Device Example 1: Manufacturing OLED devices using the organic electroluminescent co...

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Abstract

The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device comprising the same. The organic electroluminescent compounds according to the present invention have high luminescent efficiency and a long lifespan, and thus an organic electroluminescent device having a long operating lifespan can be prepared by using the organic electroluminescent compounds according to the present invention.

Description

technical field [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the 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 first developed an organic EL device [Appl. Phys. Lett. 51, 913, 1987] by using aromatic diamine small molecules and aluminum complexes as materials for forming a light-emitting layer. [0003] The most important factor determining luminous efficiency in an organic EL device is a luminescent material. Hitherto, fluorescent materials have been widely used as light emitting materials. However, from the perspective of the mechanism of electroluminescence, compared with fluorescent materials, developing phosphorescent materials is one of the best methods to theoretically increase the luminous efficiency ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/14C07D401/14C07D405/14C07D409/14H01L51/54C07D403/04H01L27/32H05B33/14H10K99/00
CPCC09K2211/1011H01L51/0072C09K2211/1029C09K2211/1092C07D403/04C07D403/14C07D409/14C07D401/14C09K2211/1007H05B33/14C09K11/06H01L51/0074C07D405/14H01L51/0073C09K2211/1088H01L51/0059C09K2211/1044H01L51/5016H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K50/11H10K2101/10H10K85/636
Inventor 文斗铉安熙春丘宗锡金南均赵英俊权赫柱李暻周金奉玉
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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