Metal complex and electron transport material using same

A technology of electron transport materials and metal complexes, applied in the direction of 1/11 group organic compounds without C-metal bonds, materials of organic semiconductor devices, lithium organic compounds, etc. Research on multilayer structure durability and other issues, to achieve the effect of excellent luminous efficiency, excellent durability, and high electron injection

Pending Publication Date: 2022-05-13
DAIDEN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, one of the reasons why it is difficult to manufacture laminates with different solubility of constituent materials of each layer is that almost all conductive polymers and spin-coatable organic semiconductors are only soluble in solvents such as toluene, chloroform, and tetrahydrofuran. If the hole transport layer or light-emitting layer is formed in a high solvent, if the next layer is formed with the same solvent, the hole transport layer or light-emitting layer of the base will be etched, and a flat interface with few defects cannot be formed. layered structure
However, the formation of multilayer structures or the improvement of durability by the wet method have not been sufficiently studied

Method used

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  • Metal complex and electron transport material using same
  • Metal complex and electron transport material using same
  • Metal complex and electron transport material using same

Examples

Experimental program
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Effect test

preparation example Construction

[0322] As the solvent or dispersion medium used in the preparation for the formation of the light-emitting layer, the same substances as those described in the formation of the hole injection layer 4 and the hole transport layer 5 can be used, but can be selected according to the hole transport layer 5 to be formed. The formed hole transport layer 5 is insoluble in the solvent.

[0323] Next, the electron-transporting layer 7 is formed on the light-emitting layer 6 according to the following steps, for example.

[0324] (a) The first process

[0325] First, a liquid material for forming an electron transport layer containing a metal complex represented by the above formulas (1) to (3) and, if necessary, a dopant such as a metal alkoxide is prepared.

[0326] As the solvent used for the preparation of the liquid material for forming the electron transport layer, a solvent that hardly swells or dissolves the constituent materials of the light emitting layer 6 is preferable, and...

Embodiment

[0342] Compound identification was performed by thin layer chromatography analysis, FAB, MS or ASAP-TOF-MS. FAB and MS were measured using JMS700 manufactured by JEOL Ltd. ASAP-TOF-MS used LCT Premier XE manufactured by Waters Corporation.

[0343] Also, for several ligands and complexes, DMSO-d6 was used as a deuterated solvent, and NMR (400 MHz) was measured with JNM-LA400 manufactured by JEOL Ltd.

[0344] In addition, as the silica gel C300 used for column chromatography, Wakosil C300 (C300) manufactured by Wako Pure Chemical Industries, Ltd., and Chromatorex NH manufactured by Fuji Silysia Chemical Co., Ltd. were used. 2 (NH 2 ).

[0345] [1] Synthesis of metal complexes

[0346] [A] Metal complex represented by formula (1)

[0347] [A-1] Synthesis of L101-M complex (M=Cs, Rb)

[0348] [A-1-1] Synthesis of Ligand L101

[0349] (1-1-1) Synthesis of intermediates: Synthesis of N-(3-chlorophenyl)-3-methoxy-2-nitrosoaniline

[0350] [chemical formula 39]

[0351] ...

Embodiment 3

[0602] The relative lifetime is based on the lifetime of Example 3 [material complex (L301-Cs)+dopant (LiOBu)+electroinjection layer] (100).

[0603] (4) Examples, Comparative Examples

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Abstract

Provided is a novel metal complex which can be used as an electron transport material. The metal complex is represented by formula (1) to formula (3). RA1-RA9, RC1-RC8, and RE1-RE6 are each independently a single bond, an alkylene group, an arylene group, a heteroarylene group, or a group represented by-RP1-P (= O) RP2-RP3-, RB1-RB9, RD1-RD8, and RF1-RF6 are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an amino group, a cyano group, a halogen atom, or a hydroxyl group; one or more groups selected from the group consisting of RB1 to RB9, one or more groups selected from the group consisting of RD1 to RD8, and one or more groups selected from the group consisting of RF1 to RF6 are phenanthroline groups; m is alkali metal or alkaline earth metal, Z is 1 or 2, and X is O or S.

Description

technical field [0001] The present invention relates to novel alkali metal complexes and alkaline earth metal complexes. In addition, the present invention also relates to an electron transport material for an organic electroluminescent device using the novel metal complex. More specifically, the present invention relates to an electron transport material that can be formed using a wet method in the production of an organic electroluminescent element having a multilayer structure, and has excellent electron injection properties, electron transport properties, and durability. Background technique [0002] An organic electroluminescent element (hereinafter, sometimes referred to as an "organic EL element") in which a light-emitting organic layer (organic electroluminescent layer) is provided between the anode and the cathode can operate at a DC low voltage compared with an inorganic EL element. Driven, with the advantages of high brightness and luminous efficiency, has attrac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07F9/6561H01L51/50H01L51/54H01L51/56H05B33/10C07F1/02C07D519/00C07F1/00
CPCC07D471/04C07F9/6561H05B33/10C07D519/00C07F1/005H10K85/30H10K50/165H10K50/16H10K2102/00H10K2102/301H10K71/00C07F9/5728C07F9/5765C07F9/65583C07F1/00H10K85/60C07F1/02
Inventor 坂井由美渡边正敬大和健太郎李承周
Owner DAIDEN CO LTD
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