Indole derivative and application thereof to organic electroluminescence

A derivative, indole technology, applied to indole derivatives and their application in the field of organic electroluminescence display technology, can solve the problems of short lifespan of OLED devices, achieve high glass transition temperature and improve lifespan , the effect of high stability

Active Publication Date: 2015-06-24
BEIJING ETERNAL MATERIAL TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Recently, it has been reported in the literature that the breakage of the C-N bond in the molecule of commonly used hole transport materials is a very important factor leading to the short life of OLED devices (Adv. Mater. 2010, 22, 3762–3777), so the development of stable and efficient Hole-like materials with a small number of C-N bonds in the molecule will improve device efficiency and prolong device life, which has very important practical application value

Method used

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  • Indole derivative and application thereof to organic electroluminescence
  • Indole derivative and application thereof to organic electroluminescence
  • Indole derivative and application thereof to organic electroluminescence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Synthesis of M1

[0070] The structural formula and synthetic route of the compound M1 to be prepared in this embodiment are as follows:

[0071] Synthesis of key intermediate M-1 (refer to the literature J.Org.Chem.2008,Vol.73,4638-4643 synthesis)

[0072]

[0073] Step A: In a 250ml three-neck flask, under the protection of nitrogen, add 4.71g (40.2mmol) of indole and 30ml of anhydrous DMF. Cool down to 0℃ in a cold bath, and add 1.95g (48.8mmol) of NaH (content 60%) in batches , Add 10ml of anhydrous DMF, keep at 0℃ and react for 15min, add 4.8ml (60.0mmol) of methyl iodide, slowly rise to room temperature, and react overnight (18h). Pour the reaction solution into a mixture of ethyl acetate and water, separate the layers, extract the aqueous phase with a small amount of ethyl acetate, combine the organic phases, dry with anhydrous MgSO4, filter and spin dry the filtrate to obtain an oil, which is subjected to column chromatography 5.51 g of yellow oily N-methylindole was...

Embodiment 2

[0079] Synthesis of M2

[0080] In this example, compound M2 is prepared, and its structural formula and synthetic route are as follows:

[0081]

[0082] The synthesis of intermediate M-2 is similar to that of M-1. In step A, ethyl iodide can be used instead of methyl iodide.

[0083] The synthesis of M2 adopts a method similar to that in Example 1, using an equivalent amount of 4-(9H-carbazol-9-yl)phenylboronic acid instead of 9-phenyl-9H-carbazole-3-boronic acid, and other conditions remain unchanged. Obtain M2 (white solid, yield 67%)

Embodiment 3

[0085] Synthesis of M3

[0086] In this example, compound M3 is prepared, and its structural formula and synthetic route are as follows:

[0087]

[0088] The synthesis of intermediate M-3 is similar to that of M-1, but in step A, iodobutane can be used instead of methyl iodide.

[0089] Synthesis of M3 adopts a method similar to that in Example 1, using an equivalent amount of triphenylamine 4-boronic acid instead of 9-phenyl-9H-carbazole-3-boronic acid, and other conditions remain unchanged to obtain M3 (white solid, yield 50 %)

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Abstract

The invention relates to a compound shown as formula (I). R1 is selected from C1-20 aliphatic straight chain or branched chain alkyl or C6-30 aryl radical; R2 is selected from C4-40 substituted or unsubstituted aromatic amino, carbazolyl, dibenzothienyl, indolyl or dibenzofuryl; L is selected from the single bond, C4-40 substituted aromatic amine, C4-40 substituted carbazole, C4-40 substituted indole, C4-40 substituted dibenzofuran, C4-40 substituted dibenzothiophene, substituted or unsubstituted diphenyl ether, O, N or S; R3-R6 is independently selected from H atom, C1-20 of aliphatic straight chain or branched chain alkyl or C6-30 aromatic groups, or a ring formed by connecting two adjacent groups; and n is selected from an integer of 2-5. The invention also protects the application of the compound in organic light emitting devices, especially as a hole transport / injection material in OLED devices.

Description

Technical field [0001] The invention relates to an organic compound, in particular to an indole derivative used in an organic electroluminescence device and its application in the field of organic electroluminescence display technology. Background technique [0002] At present, the hole injection and transport materials used in organic electroluminescent devices are generally triarylamine derivatives (for example, Idemitsu Patent: Publication No. CN1152607C, Publication Date 2004, 6, 2). Its general structural characteristics are: The injection material has at least three triarylamine structural units in a molecule, and two Ns are separated by a benzene ring, such as structural formula 1. As a transport material, the triarylamine structural unit in a molecule is generally Two, and two N are separated by biphenyl. In this type of material, the typical example is NPB. [0003] [0004] In recent years, there have been some new developments in the research of this type of material. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/82C07D209/86C07D209/14C07D209/04C07D409/14C07D405/14C07D209/36C07D209/30C07D209/40H01L51/54
Inventor 王星范洪涛李艳蕊
Owner BEIJING ETERNAL MATERIAL TECH
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