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Anthracene derivative and organic electroluminescence device using the anthracene derivative

An anthracene derivative and electroluminescence technology, applied in the field of anthracene derivatives, can solve problems such as decreased efficiency and achieve the effect of high luminous efficiency

Active Publication Date: 2019-05-14
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, Patent Documents 4 to 6 disclose light-emitting materials of anthracene derivatives having 3-fluorenyl or 4-fluorenyl as substituents. When these materials are used, the effect of lowering the voltage can be confirmed, but there is a disadvantage of lowering the efficiency. , thus seeking further high efficiency

Method used

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  • Anthracene derivative and organic electroluminescence device using the anthracene derivative
  • Anthracene derivative and organic electroluminescence device using the anthracene derivative
  • Anthracene derivative and organic electroluminescence device using the anthracene derivative

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0343] Synthesis Example 1 [Synthesis of Intermediate A]

[0344] Intermediate A was synthesized according to the following scheme.

[0345] 【Chemical 86】

[0346]

[0347] (A-1) Synthesis of ethyl 4-bromo-2-iodobenzoate

[0348] Under an argon atmosphere, 36 mL of tetramethylpiperidine was added to 500 mL of THF (tetrahydrofuran), cooled to 0° C., 90 mL of 2.6 M n-BuLi hexane solution was added dropwise, and stirred at 0° C. for 10 minutes.

[0349] In another flask, a 1.6 M t-BuLi pentane solution was added dropwise to 440 mL of a THF solution (0.5 M) of zinc chloride at 0° C. under an argon atmosphere, followed by stirring for 30 minutes. After the tetramethylpiperidine solution was cooled to -78°C, the di-tert-butylzinc solution prepared in another flask was added dropwise. After raising the temperature of the reaction solution to 0°C, it was stirred for 30 minutes, and then cooled to -78°C again. After adding 22.9 g of ethyl 4-bromobenzoate dropwise, stirring was c...

Synthetic example 2

[0356] Synthesis Example 2 [Synthesis of Intermediate B]

[0357] Intermediate B was synthesized according to the following scheme.

[0358] 【Chemical 87】

[0359]

[0360] In the synthesis of the intermediate (A), the intermediate (B) was synthesized in the same manner as the intermediate (A) except that methyl 2-bromobenzoate was used instead of ethyl 4-bromobenzoate.

Synthetic example 3

[0361] Synthesis Example 3 [Synthesis of Intermediate C]

[0362] Intermediate C was synthesized according to the following scheme.

[0363] 【Chemical 88】

[0364]

[0365] (C-1) Synthesis of 2-acetyl-1-naphthyl trifluoromethanesulfonate

[0366] Under an argon atmosphere, 186 g of 1'-hydroxy-2'-naphthophenone and 18.2 g of 4-dimethylaminopyridine were added to the flask, 4 L of dichloromethane was added, and the flask was cooled to -78°C. After adding 161 g of 2,6-lutidine, 339 g of trifluoromethanesulfonic anhydride was added dropwise. Stirring was continued for 5 hours while raising the temperature to room temperature. The precipitated solid was collected by filtration, washed with water and methanol, and dried to obtain 286 g of triphenylene trifluoromethanesulfonate (90% yield).

[0367] (C-2) Synthesis of 2-acetylnaphthalene-1-boronic acid pinacol ester

[0368] Under an argon atmosphere, add 2-acetyl-1-naphthyl trifluoromethanesulfonate 286g, biboronic acid pina...

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Abstract

An anthracene derivative represented by the following formula (1). In formula (1), R 11 ~R 20 Either of the used with L 1 for bonding, not for use with L 1 The linkers are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the like. L 1 It is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and the like. Z is a structure represented by the following formula (2). In formula (2), R 1 , R 3 and R 4 Either of the used with L 1 for bonding, not for use with L 1 Bonder, R 2 , and R 5 ~R 10 Each independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and the like. Among them, R 5 ~R 8 At least one of the groups of two adjacent groups in the group is bonded to each other to form a saturated or unsaturated hydrocarbon ring.

Description

technical field [0001] The present invention relates to an anthracene derivative, an organic electroluminescence element comprising the anthracene derivative, and an electronic device comprising the element. Background technique [0002] The use of organic electroluminescent (EL) elements as solid-state light-emitting inexpensive large-area full-color display elements is considered to be promising, and a large number of developments are underway. In general, an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. When an electric field is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side. In addition, the electrons and holes generate an excited state when they recombine in the light-emitting layer, and release energy in the form of light when returning from the excited state to the ground state. [0003] Conventional organic EL elements have...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/66C07D307/91C09K11/06H01L51/50
CPCC07C13/66C07D307/91C09K11/06C09K2211/1011C09K2211/1088C09K2211/1092C07D333/76C07D401/10C07D235/18C07D239/26C07D409/10C07D251/24C07D271/04C07D209/86C07D213/22C07D307/77C09B57/00C09B57/001C09B1/00C09B3/02C07C2603/18C07C2603/24C07C2603/26C07C2603/40C07C2603/42C07C2603/52C07C2603/94C09K11/025C09K2211/1007H10K85/623H10K85/622H10K85/636H10K85/626H10K85/633H10K85/6574H10K50/11H10K2101/10C07C13/567C07C13/58C09K2211/1014
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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