Tetraphenyl porphyrin derivative and its application in organic electroluminescent device

A technology of tetraphenylporphyrin and its derivatives, which is applied in the application field of tetraphenylporphyrin derivatives and their luminescent materials in organic electroluminescent devices, and can solve the problem of not having carrier transport performance, external quantum Low efficiency, poor stability and other issues, to achieve the effect of being conducive to mass industrial production of devices, high luminous efficiency and good stability

Inactive Publication Date: 2005-06-29
吉林吉大瑞博光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, their external quantum efficiencies are relatively low, and the

Method used

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  • Tetraphenyl porphyrin derivative and its application in organic electroluminescent device
  • Tetraphenyl porphyrin derivative and its application in organic electroluminescent device
  • Tetraphenyl porphyrin derivative and its application in organic electroluminescent device

Examples

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example 1

[0035] Example 1: Synthesis of Compound 1-1-01

[0036] Using 150 milliliters of N,N-dimethylformamide as a solvent, add 3.0 grams of sodium hydride, 10 grams of carbazole and 20.0 grams of 1,4-dibromobutane, and react under reflux for 6 hours. Cooling, add 50 milliliters of methanol and fully stir and filter, the collected filtrate is concentrated and evaporated to dryness, and the crude product uses cyclohexane as the eluent aluminum oxide as the stationary phase column chromatography to obtain the product N-(4-bromobutyl ) carbazole 8.2 grams. Yield 45.4%.

[0037] 10.0 grams of compound 3-methoxy-4-hydroxybenzaldehyde, 4.4 grams of pyrrole and 600 milliliters of N, N-dimethylformamide were heated to reflux for 2 hours, cooled and stilled, 200 milliliters of distilled water was added, filtered, and the crude product was used Dichloromethane was used as the eluent and aluminum oxide was used as the stationary phase column chromatography to obtain 3.5 grams of the product t...

example 2

[0042] Example 2: Synthesis of Compound 1-1-02

[0043] The synthesis of compound 1-1-02 was the same as in Example 1. Just use 1,5-dibromopentane instead of 1,4-dibromobutane. The product tetrakis-[3-methoxy-4-(N-carbazole)pentyloxy]phenylporphyrin. Mass spectrum molecular ion peak: 1739. Elemental analysis according to chemical formula C 116 h 106 N 8 o 8 Calculated: C: 80.0%; H: 6.1%; N: 6.4%; O: 7.4%; found: C: 79.8%; H: 6.2%; N: 6.5%;

example 3

[0044] Example 3: Synthesis of Compound 1-1-03

[0045] The synthesis of compound 1-1-03 was the same as in Example 1. Just use 1,6-dibromohexane instead of 1,4-dibromobutane. The product tetrakis-[3-methoxy-4-(N-carbazole)hexyloxy]phenylporphyrin. Mass spectrum molecular ion peak: 1795. Elemental analysis according to chemical formula C 120 h 114 N 8 o 8 Calculated: C: 80.0%; H: 6.4%; N: 6.2%; O: 7.1%; Experimental values: C: 80.2%; H: 6.3%; N: 6.1%;

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Abstract

The invention relates to a (1) or (2) and its application in preparation of organic EL device. M is Zn or Pt; three substituent group or R1, R2, R3 are different or the same and at least one of them is alkoxy substituent carbazole derivative shown as (3); R10 and R11 are different or the same, as alkyl of C1-4 (n=4-12); the other two substituent group is H and alkoxy and alkyl (C1-C4) or alkoxy substituent carbazole derivative shown as (3). The device made by the invention has high efficiency of EL, outstanding solubility and filmibility, easy to be mixed with polymer, benefiting for research to EL device, can be used to prepare red luminous, with simple technique, benefit for industrialized batch production .

Description

technical field [0001] The invention relates to an organic electroluminescent material and its application, in particular to a tetraphenylporphyrin derivative and its application as a luminescent material in an organic electroluminescent device. Background technique [0002] The phenomenon of organic electroluminescence has been discovered for more than 30 years. Before 1987, the application of organic electroluminescence devices was limited due to the huge defects (turn-on voltage>200V). In the past ten years, due to continuous breakthroughs in materials and device technology, organic electroluminescence has reached or is close to the practical stage. [0003] In 1965, Gurnee et al first published a patent on organic electroluminescent devices (U.S. Pat. No. 3,172,862, 3,173,050). In 1973, Dresner also published a patent on organic electroluminescent devices (U.S. Pat. No. 3,170,167). Polyaromatic ring organic compounds such as anthracene, tetracene, pentacene, etc. ar...

Claims

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Application Information

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IPC IPC(8): C07D487/22H05B33/14
Inventor 王悦霍成郭建华
Owner 吉林吉大瑞博光电科技有限公司
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