Green electroluminescent compounds and organic electroluminescent device using the same

A compound and electroluminescence technology, applied in electroluminescence light sources, preparation of organic compounds, silicon organic compounds, etc., can solve the problem of not mentioning the 2- and 7-position substituted asymmetric compounds of diarylamino groups

Inactive Publication Date: 2013-07-24
GRACEL DISPLAY INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this publication only describes compounds substituted by aryl groups (such as phenyl and naphthyl) at the 9- and 10-positions, rather than by alkyl groups, and it does not mention diarylamino groups directly at all. Asymmetric compounds substituted at the 2- and 7-positions of anthracene

Method used

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  • Green electroluminescent compounds and organic electroluminescent device using the same
  • Green electroluminescent compounds and organic electroluminescent device using the same
  • Green electroluminescent compounds and organic electroluminescent device using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0210] [Preparation Example 1] Preparation of Compound (1023)

[0211]

[0212] Preparation of compound (A)

[0213] Bromocyclohexane (44.1g, 270.7mmol) was dissolved in dry tetrahydrofuran solvent (500ml), and 2.5M n-butyllithium (in n-hexane) (130mL, 324.9mmol) was added at -78°C in. After stirring for 1 hour, 2,7-dichloroanthracene-9,10-dione (30.0 g, 108.3 mmol) was added thereto, and the resulting mixture was stirred while slowly warming to room temperature. After 17 hours, water was added, the mixture was stirred for 30 minutes and extracted with 500 mL of vinyl acetate. The extract was washed with 500 mL of water, and the organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dried to obtain compound (A) (21.3 g, 47.8 mmol).

[0214] Preparation of compound (B)

[0215] Compound (A) (21.3g, 47.8mmol), potassium iodide (31.7g, 191.2mmol), sodium hydrogen phosphate (40.5g, 382.4mmol) and acetic acid (300mL) wer...

Embodiment 1

[0591] [Example 1] Preparation of OLED using the organic EL compound of the present invention

[0592] OLED devices were prepared using the EL materials of the present invention.

[0593] First, a transparent electrode ITO film (15Ω / □) (2) prepared from glass for OLED (manufactured by Samsung Corning) (1) was ultrasonically washed in trichloroethylene, acetone, ethanol, and distilled water, Next, store it in isopropanol until use.

[0594] Then, the ITO substrate was mounted on the substrate holder of the vacuum vapor deposition device, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2 -TNATA) is placed in a unit of the vacuum vapor deposition device, and then the exhaust gas makes the vacuum degree in the reaction chamber up to 10 -6 torr. A current was applied to the cell to evaporate 2-TNATA, providing vapor deposition of a 60 nm thick hole injection layer (3) on the ITO substrate.

[0595]

[0596] Then, inject N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-d...

Embodiment 2

[0612] [Example 2] The EL performance of the prepared OLED

[0613] respectively at 5000cd / m 2 and 20000cd / m 2 The luminous efficiencies of the OLEDs prepared in Example 1 and Comparative Examples 1-2 were measured as follows. The OLEDs prepared in Example 1 and Comparative Examples 1-2 included the organic EL compound of the present invention and the traditional electroluminescent compound respectively. The results are shown in Table 3. Since the electroluminescent performance in the high brightness region is very important, especially for green electroluminescent materials, the high brightness (about 20000cd / m 2 )The data.

[0614] table 3

[0615]

[0616] As can be seen from Table 3, when the organic EL compound of the present invention is used in a green electroluminescent device, the device exhibits a significantly improved Luminous efficiency.

[0617] Specifically, even at high brightness (20000cd / m 2 ), the efficiency reduction of the high-performance electro...

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Abstract

The present invention relates to novel organic electroluminescent compounds, organic electroluminescent devices and organic solar cells comprising the same. Specifically, the organic electroluminescent compounds according to the invention are represented by Chemical Formula (1) : wherein, R 1 and R 2 independently represent hydrogen, deuterium, linear or branched (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C3-C15)cycloalkyl, tri(C1-C20)alkylsilyl, di(C1-C20)alkyl(C6-C20)arylsilyl, tri(C6-C20)arylsilyl, adamantyl, (C7-C15)bicycloalkyl or (C4-C20)heteroaryl, and the alkyl, alkenyl, alkynyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl or heteroaryl of R 1 and R 2 may be further substituted by one or more substituent(s) selected from deuterium, linear or branched (C1-C20)alkyl, (Cl-C20)alkenyl, (C1-C20)alkynyl, halogen, phenyl, fluorenyl, naphthyl and anthryl. The electroluminescent compounds according to the present invention are green electroluminescent compounds, of which the luminous efficiency and device lifetime have been maximized.

Description

technical field [0001] The present invention relates to novel organic electroluminescent compounds, as well as organic electroluminescent devices using them in the electroluminescent layer and organic solar cells using them. Specifically, the organic electroluminescent compound of the present invention is characterized in that it is represented by the chemical formula (1): [0002] [0003] chemical formula 1 [0004] Among them, R 1 and R 2 Independently represent hydrogen, deuterium, straight chain or branched (C1-C20) alkyl, (C2-C20) alkenyl, (C2-C20) alkynyl, (C3-C15) cycloalkyl, three (C1-C20) ) Alkylsilyl, Di(C1-C20)alkyl(C6-C20)arylsilyl, Tri(C6-C20)arylsilyl, Adamantyl, (C7-C15)bicycloalkyl or (C4-C20)heteroaryl, and R 1 and R 2 The alkyl, alkenyl, alkynyl, cycloalkyl, trialkylsilyl, dialkylarylsilyl, triarylsilyl, adamantyl, bicycloalkyl or heteroaryl groups can be further represented by One or more selected from deuterium, straight chain or branched (C1-C20...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C217/84C07F7/08C07D213/74C07D215/38C07D295/30C09K11/06H01L51/50H01L51/54H01L51/42H01L51/46
CPCC09K11/06C09K2211/1014H01L51/0077C09K2211/1037H01L51/0058H01L51/0061H01L51/006C09K2211/1029C09K2211/1044H01L51/0081C07C2101/14C09K2211/1092Y02E10/549C09K2211/1033C07C211/61H05B33/14C07C2601/14C09B57/008H10K85/626H10K85/636H10K85/633H10K85/30H10K85/324
Inventor 金保罗李美爱金侈植李秀镛赵英俊权赫柱金奉玉金圣珉尹胜洙
Owner GRACEL DISPLAY INC
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