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Material for organic electroluminescent elements, and organic electroluminescent element using same

一种发光元件、有机电场的技术，应用在发光材料、电气元件、有机化学等方向，能够解决未示出碳硼烷化合物有用性等问题

Inactive Publication Date: 2016-08-17
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] However, the usefulness of carborane compounds bonded to the 1- or 2- or 3-position of dibenzothiophene is not shown

Method used

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  • Material for organic electroluminescent elements, and organic electroluminescent element using same
  • Material for organic electroluminescent elements, and organic electroluminescent element using same
  • Material for organic electroluminescent elements, and organic electroluminescent element using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0133] Compound 1 was synthesized according to the following reaction formula.

[0134] [chemical 13]

[0135]

[0136] Under a nitrogen atmosphere, 35.0 g (0.243 mol) of m-carborane and 200 mL of 1,2-dimethoxyethane (DME) were added, and the resulting DME solution was cooled to 0°C. 96.8 mL of a 2.69 M n-butyllithium hexane solution was added dropwise, followed by stirring for 30 minutes while cooling in an ice bath. After adding 70 mL of pyridine and stirring at room temperature for 10 minutes, 75.6 g (0.763 mol) of copper (I) chloride was added and stirred at 65° C. for 30 minutes. Then, 73.9 g (0.280 mol) of 2-bromodibenzothiophene was added, and it stirred at 95 degreeC overnight. After cooling the reaction solution to room temperature, the precipitated crystals were collected by filtration, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 8.0 g (24.5 mmol, yield 10.0%) of Inte...

Embodiment 2

[0144] On a glass substrate formed with an anode of indium tin oxide (ITO) with a film thickness of 70 nm, the -5Pa vacuum degree to laminate each film. First, copper phthalocyanine (CuPC) was formed as a hole injection layer on ITO with a thickness of 30 nm. Next, diphenylnaphthyldiamine (NPD) was formed to a thickness of 15 nm as a hole transport layer. Then, on the hole transport layer, compound 1 as the host material of the light-emitting layer and iridium complex [bis(4,6 -di-fluorophenyl)-pyridinate-N, C2']picolinate (III)] (Iridium(III)bis(4,6-di-fluorophenyl)-pyridinate-N,C2']picolinate, FIrpic), The light emitting layer was formed with a thickness of 30 nm. The concentration of FIrpic was 20%. Then, Alq was formed with a thickness of 25nm 3 as an electron transport layer. Furthermore, lithium fluoride (LiF) was formed as an electron injection layer with a thickness of 1.0 nm on the electron transport layer. Finally, aluminum (Al) was formed as an electrode with...

Embodiment 3～ Embodiment 9

[0147] Compound 13, Compound 25, Compound 26, Compound 29, Compound 36, Compound 45, and Compound 57 were used instead of Compound 1 as the host material of the light-emitting layer in Example 2, and an organic EL was produced in the same manner as in Example 2. element.

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PUM

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Abstract

Disclosed are: an organic electroluminescent element (organic EL element) which has a simple configuration and improved luminous efficiency, while ensuring sufficient driving stability; and a material for organic EL elements. This material for organic EL elements is a carborane compound which has one or more carborane rings and one or more dibenzothiophene rings, and wherein at least one dibenzothiophene ring has a structure that is bonded with a carborane ring at the 1-position, the 2-position or the 3-position. This organic EL element comprises organic layers between a positive electrode and a negative electrode which are laminated on a substrate, and at least one of the organic layers contains the above-described carborane compound.

Description

technical field [0001] The present invention relates to an organic electroluminescent element using a carborane compound as a material for an organic electroluminescent element. Specifically, the present invention relates to a thin-film device that emits light by applying an electric field to a light-emitting layer containing an organic compound. ). Background technique [0002] Generally, the simplest structure of an organic electroluminescence device (hereinafter referred to as an organic EL (Electroluminescence) device) is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. That is, the organic EL element utilizes the phenomenon that when an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode, and these recombine in the light emitting layer to emit light. [0003] In recent years, the development of organic EL elements using organic thin films has been prog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50
CPCC07D333/76C07D409/04C07D409/08C07D409/14C07F5/027C09K11/025C09K11/06C09K2211/1007C09K2211/1029C09K2211/185H10K85/654H10K85/6576H10K85/6572H10K85/322H10K85/324H10K85/342H10K50/11H10K2101/10C07D209/82C09K2211/1092H10K50/16H10K50/171H10K50/12H10K50/18H10K50/81H10K50/828
Inventor 小川淳也多田匡志上田季子甲斐孝弘
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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