Elarylamine derivative, hole transport material comprising the same, and organic electroluminescence device using the same

A derivative, arylamine technology, applied in the field of arylamine derivatives

Inactive Publication Date: 2020-08-11
FLASK CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is thought that improving not only the main body but also the hole transport material can contribute to higher efficiency and longer life. However, conventional hole transport materials have durability and triplet energy (T 1 ) compromise of durability, high triplet energy (T 1 ) and hole transport properties, the development of all hole transport materials is still an issue

Method used

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  • Elarylamine derivative, hole transport material comprising the same, and organic electroluminescence device using the same
  • Elarylamine derivative, hole transport material comprising the same, and organic electroluminescence device using the same
  • Elarylamine derivative, hole transport material comprising the same, and organic electroluminescence device using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] [Example 1] Synthesis of T4DBFHPB

[0081] (i) 4DBFNCPh 2 Synthesis

[0082]

[0083] Add 2.47g (10mmol) of 4-BrDBF, 1.68ml (10mmol) of benzophenone imine, 2.5mg (2.6mmol) of tertiary BuONa, and 50ml of dry toluene to a 25ml three-necked flask, and carry out N for 1 hour. 2 bubbling. After that, add Pd 2 (dba) 3 370 mg (0.4 mmol) and ± BINAP 560 mg (0.9 mmol), stirred at 90°C under nitrogen. After confirming the consumption of the raw material by TLC, it was cooled to room temperature, filtered through a glass filter filled with silica gel, concentrated, and dried under reduced pressure to obtain the target product.

[0084] Yield 3.39g, yield 98%

[0085] MS: [M + ]=348.1m / z

[0086] (ii) 4DBFNH 2 Synthesis

[0087]

[0088] Add 4DBFNCPH to a 100ml eggplant flask 2 3.39 mg (9.8 mmol), 50 ml of THF and 50 ml of 2M HClaq were stirred under reflux for 5 hours. The disappearance of the raw material and the production of the target product were confirmed...

Embodiment 2

[0103] [Example 2] Synthesis of TDBFBP

[0104]

[0105] In a 30ml four-necked flask, add 1.048g (3.0mmol) of B4DBFNH synthesized in Example 1, 468mg (1.5mmol) of 3,3'-dibromobiphenyl, 750mg (7.8mmol) of tertiary BuONa and 30ml of dry toluene to carry out 2 hours 2 bubbling. After that, add Pd 2 (dba) 3 137mg (0.15mmol) and t-Bu 3 P + BF 4 - 87 mg (0.3 mmol), stirred under reflux for 22 hours under nitrogen flow. The disappearance of the raw material was confirmed by TLC, and it returned to normal temperature. Thereafter, extraction was performed three times with 100 ml of toluene, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification was carried out by silica column chromatography (developing solvent: toluene / hexane=1 / 1) to obtain 1.082 g of the target product at a yield of 78%. Target identification through 1 H-NMR, 13 C-NMR and MS to carry out.

[0106] 1 H-NMR (400MHz, CDCl 3 )δ=7.92(dd, J=8.0, 1.1Hz, ...

Embodiment 3

[0109] [Example 3] Synthesis of TDBFP

[0110]

[0111] Add B4DBFNH 2.795g (8.0mmol), 1,3-dibromobenzene 944mg (4.0mmol), tertiary BuONa 2.000g (20.8mmol) and dry toluene 80ml in a 100ml four-necked flask, and carry out 2 hours N 2 bubbling. After that, add Pd 2 (dba) 3 366mg (0.40mmol) and t-Bu 3 P + BF 4 - 232mg (0.8mmol), stirred under reflux for 22 hours under nitrogen flow. After confirming disappearance of the raw material by TLC, Celite filtration was performed, and the filtrate was concentrated. Purified by silica gel chromatography (developing solvent: toluene), concentrated, and washed with methanol to obtain 2.866 g of the target product in a yield of 93%. Target identification through 1 H-NMR, 13 C-NMR and MS to carry out.

[0112] 1 H-NMR (600MHz, CDCl 3 )δ=7.90(d, J=7.6Hz, 4H), 7.60-7.56(m, 4H), 7.41-7.35(m, 8H), 7.34-7.29(m, 4H), 7.14(d, J=6.9Hz , 4H), 7.06(t, J=7.9Hz, 1H), 6.84(t, J=7.6Hz, 4H), 6.71(t, J=2.4Hz, 1H), 6.60(dd, J=7.9, 2.4Hz ,2H)...

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Abstract

Provided are: an elarylamine derivative which has high triplet energy and can be used as a main material of an organic EL element, particularly a hole transport material; and an organic EL element using the elarylamine derivative. The elarylamine derivative is represented by general formula (1). In the general formula (1), each of R1-R9 independently represents a hydrogen atom, an alkyl group having 1-6 carbon atoms in a straight chain or a branched chain, an alkoxy group having 1-6 carbon atoms in a straight chain or a branched chain, or a mono-or di-alkylamino group having 1-6 carbon atoms in a straight chain or a branched chain; x is an oxygen atom, a sulfur atom or an alkylene group (-CR8R9-); Ar is a substituent represented by general formula (2), wherein R10-R37 are each independently a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, a linear or branched alkoxy group having 1-6 carbon atoms, or a linear or branched mono-or di-alkylamino group having 1-6 carbon atoms.

Description

technical field [0001] The present invention relates to an arylamine derivative having high triplet energy, a hole transport material containing the arylamine derivative, and an organic EL device using the arylamine derivative. Background technique [0002] In an organic EL element, by applying a voltage between a pair of electrodes, holes are injected from the anode into a light-emitting layer containing an organic compound as a light-emitting material, and electrons are injected from a cathode into a light-emitting layer containing an organic compound as a light-emitting material. The injected electrons and holes are recombined to form excitons in the light-emitting organic compound, and light emission can be obtained from the excited organic compound. [0003] The subject of such an organic EL element is improvement of luminous efficiency and improvement of durability. Among the excitons formed by organic compounds are singlet excitons (E S1 ) and triplet excitons (E T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91H01L51/54H01L51/50
CPCC07D307/91H10K85/624H10K85/636H10K85/633H10K85/6574H10K50/155H10K50/00
Inventor 笹部久宏城户淳二镰田嵩弘伊藤望荒木卓
Owner FLASK CORPORATION
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