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Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device

A compound and atomic number technology, applied in the field of compounds, to achieve high performance, good driving voltage and external quantum efficiency

Active Publication Date: 2016-04-06
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In addition, organic EL elements can obtain a variety of luminous colors by using various luminescent materials in the luminescent layer, so research on practical applications such as displays is active.

Method used

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  • Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
  • Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
  • Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0272] [chemical 40]

[0273]

[0274] Under an argon atmosphere, benzo[g]?-10-boronic acid (2.90g, 9.00mmol), (4-bromophenyl)phosphine oxide (3.21g, 9.00mmol), tris(dibenzylideneacetone) di Add 1,4-dioxane (100 mL) to palladium (0) (124 mg, 0.135 mmol), triphenylphosphine (283 mg, 1.08 mmol), and tripotassium phosphate (11.5 g, 54.0 mmol), and stir at 100 ° C for 8 Hour.

[0275] After the reaction, the mixture was diluted with water and extracted with chloroform. Next, the mixture was washed with saturated brine, dried over magnesium sulfate, and concentrated. Then, the mixture was purified by silica gel column chromatography, and then recrystallized from ethyl acetate to obtain a compound (3.24 g, 5.85 mmol, yield 65%). The result of mass analysis of this compound was m / e=554, and it was identified as the above-mentioned compound (1) (Exactmass: 554.18).

Embodiment 2

[0277] [chem 41]

[0278]

[0279] (2-1) Synthesis of intermediate (A2)

[0280] Under an argon atmosphere, raw material compound (A1) (2.00 g, 5.60 mmol) and tetrahydrofuran (50 mL) were mixed, and cooled to -78°C. Then, n-butyllithium (1.60 M hexane solution, 3.68 mL, 5.88 mmol) was added, and the temperature was raised to 0° C. over 2 hours. Next, it cooled to -78 degreeC again, trimethoxyborane (1.45g, 14.0mmol) was added, it stirred at -78 degreeC for 10 minutes, and it heated up to room temperature over 6 hours.

[0281] After the reaction, aqueous hydrochloric acid (1M, 15 mL) was added, stirred at room temperature for 1 hour, and extracted with ethyl acetate. The solution was dried over magnesium sulfate, concentrated, suspended and washed in hexane, and recovered by filtration to obtain intermediate (A2) (902 mg, 2.80 mmol, yield 50%).

[0282] (2-2) Synthesis of compound (2)

[0283] Under argon atmosphere, intermediate (A2) (850mg, 2.64mmol), (4-bromophenyl)p...

Embodiment 3

[0286] [chem 42]

[0287]

[0288] (3-1) Synthesis of intermediate (B1)

[0289] The synthesis of the intermediate (B1) was carried out as described above with reference to the synthesis example described in "J. Org. Chem., 1991, 56, p. 1210-1217".

[0290] (3-2) Synthesis of intermediate (B2)

[0291] Add carbon tetrachloride to intermediate (B1) (2.40g, 8.66mmol), N-bromosuccinimide (1.54g, 8.66mmol), iron(III) chloride hexahydrate (70mg, 0.260mmol) (600mL), stirred under reflux for 8 hours.

[0292] After completion of the reaction, the solvent was distilled off under reduced pressure, and the mixture was purified by silica gel column chromatography to obtain an intermediate (B2) (2.13 g, 5.98 mmol, yield 69%).

[0293] (3-3) Synthesis of intermediate (B3)

[0294] The intermediate (B2) (1.80 g, 5.04 mmol) and tetrahydrofuran (40 mL) were mixed under an argon atmosphere, and cooled to -78°C. Then, n-BuLi (1.60 M hexane solution, 3.31 mL, 5.29 mmol) was added, and th...

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Abstract

Provided are: an organic electroluminescent element which exhibits higher performance and has particularly good driving voltage and external quantum efficiency, while having a longer service life; and an electronic device which is provided with this organic electroluminescent element. Also provided is a compound which enables the achievement of the organic electroluminescent element and the electronic device. Specifically provided are: a compound of a specific structure having a triphenylene skeleton; an organic electroluminescent element which uses this compound; and an electronic device which is provided with this organic electroluminescent element.

Description

technical field [0001] The present invention relates to a compound, a material for an organic electroluminescence element containing the compound, an organic electroluminescence element using the compound, and an electronic device equipped with the organic electroluminescence element. Background technique [0002] Generally, an organic electroluminescent (EL) element is composed of an anode, a cathode, and one or more organic thin film layers sandwiched between the anode and the cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side into the light-emitting region, holes are injected into the light-emitting region from the anode side, and the injected electrons and holes recombine in the light-emitting region to become an excited state. When the excited state returns to the ground state emit light. [0003] In addition, organic EL elements can obtain various light-emitting colors by using various light-emitting materials i...

Claims

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Application Information

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IPC IPC(8): C07F9/53C09K11/06H01L51/50
CPCC07F9/5325C07F9/5728C07F9/65517C07F9/655354C07F9/65586C09K11/06H05B33/14C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092C09K2211/1096C07F9/58H10K85/623H10K85/622H10K50/165H10K50/16
Inventor 河村昌宏水木由美子伊藤裕胜羽山友治羽毛田匡
Owner IDEMITSU KOSAN CO LTD
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