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Thiophene derivative and organic electroluminescent element

a technology of thiophene and derivative, which is applied in the direction of discharge tube luminescnet screen, thermoelectric device, natural mineral layered product, etc., can solve the problems of unfavorable light emission efficiency, unsatisfactory light emission efficiency, and significant difficulty in introducing a sulfonic group to all polybenzo[c]thiophene units, etc., to achieve excellent light emission efficiency and water resistance

Inactive Publication Date: 2006-03-16
DAI NIPPON PRINTING CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a thiophene derivative that can be used to form an efficient and water-resistant organic positive hole layer in an organic EL element. Additionally, a polymer containing this thiophene derivative as a monomer unit is also provided. The polymer is soluble in organic solvents, making it easy to apply on a substrate to form the organic positive hole transporting layer. The resulting organic EL element is significantly less affected by moisture, leading to improved performance.

Problems solved by technology

Polybenzo[c]thiophene sulfonic acid is a useful conductive polymer material, however, polybenzo[c]thiophene sulfonic acid is basically synthesized by sulfonation of polybenzo[c]thiophene in the presence of sulfuric acid and it is significantly difficult to introduce a sulfonic group to all polybenzo[c]thiophene units.
In the case of synthesizing a copolymer of benzo[c]thiophene sulfonic acid and other monomer in order to exhibit various functions, sulfonation is performed after the copolymerizing process, thus, the monomer structure to be copolymerized with polybenzo[c]thiophene may be unnecessarily affected by the sulfonation, which is not efficient.
Generally, an organic El element is easily affected by moisture, and a performance of element is easily deteriorated by moisture.
However, as aforementioned, since the organic positive hole transporting layer is formed with the coating liquid containing water and the material for forming the organic positive hole transporting layer is a hydrophilic material, it is significantly difficult to completely remove even a minute amount of moisture from the organic positive hole transporting layer.
However, there are problems that such an effort is cumbersome and requires high production costs.

Method used

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  • Thiophene derivative and organic electroluminescent element
  • Thiophene derivative and organic electroluminescent element
  • Thiophene derivative and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0036] 5.27 parts of dibromo-o-toluene was heated to reflux in 70 parts of toluene in the presence of phosphorus trisulfide for 8 hours to obtain benzo[c]thiophene. 0.86 parts of thus obtained benzo[c]thiophene was heated to reflux with 0.56 parts of cuprous bromide in dehydrated methylene chloride for 5 hours to obtain 0.47 parts of dibromobenzothiophene. The bromide was sulfonated by fuming sulfuric acid. The sulfide was heated to reflux with an excessive amount of dibutyl sulfate in dehydrated tetrahydrofuran for 12 hours. Then, an unreacted product and impurity were removed, dried under reduced pressure, and thus obtained a thiophene derivative of the present invention represented by the formula 1a (brown powder, decomposition temperature: 157° C. (elimination of a dibutyl group), melting point: 270° C.):

[0037] The results of elementary analysis and NMR analysis of the compound represented by the formula 1a are as follows.

[Elementary Analysis]

[0038] Calculated value C=33.7, ...

examples 2 to 4

[0042] In Example 2, in the same manner as in Example 1 except that dimethyl sulfate was used instead of dibutyl sulfate, a thiophene derivative 1b of the present invention in which the butyl group represented by the formula 1a was a methyl group was obtained.

[0043] In Example 3, in the same manner as in Example 1 except that diethyl sulfate was used instead of dibutyl sulfate, a thiophene derivative 1c of the present invention in which the butyl group represented by the formula 1a was an ethyl group was obtained.

[0044] In Example 4, in the same manner as in Example 1 except that dipropyl sulfate was used instead of dibutyl sulfate, a thiophene derivative id of the present invention in which the butyl group represented by the formula 1a was a propyl group was obtained.

[0045] The analysis results are shown in Table 1.

TABLE 1EstereliminationMeltingElementary analysisCom-temperaturepoint(measured value)pound(° C.)(° C.)CHSOExample 21b149-15125527.81.416.511.9Example 31c15325031.12...

example 5

[0046] 4.3 parts of the thiophene derivative represented by the formula 1a obtained in Example 1 and 2.4 parts of 2, 5-dibromothiophene were heated to reflux in dimethyl formamide in the presence of nickel chloride and triphenyl sulfone for 4 hours, thus obtained 0.7 parts of a copolymer represented by the following formula 2a, wherein a weight average molecular weight (measured by GPC, polystyrene standard) of the obtained copolymer obtained was 20,000 and the copolymer was soluble to toluene by 1 mass % or more:

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Abstract

The present invention provides a thiophene derivative useful for a material for forming an organic positive hole layer of an organic EL element excellent in light emitting efficiency, water resistance or the like, a polymer having the thiophene derivative as a monomer unit, and an organic EL element. The object can be solved by a thiophene derivative represented by the following formula (1), a polymer comprising the thiophene derivative, and an organic EL element, an organic positive hole transporting layer of which comprises the polymer: wherein, each “X” is a halogen atom, which may be same or different from each other; and “R” is an alkyl group.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention relates to a thiophene derivative and an organic electroluminescent (hereinafter it is simply referred to as “EL”) element. Particularly, it relates to a novel thiophene derivative which is useful for producing an organic electroluminescent element, a polymer thereof, and an organic EL element. [0003] 2. Description of the Related Art [0004] An organic EL element comprises a couple of electrodes facing each other and an organic light emitting layer disposed between the couple of electrodes, wherein the organic light emitting layer emits light when an electron injected from one electrode and a positive hole injected from another electrode recombine in the organic light emitting layer. Research and development of such an element fully started when M. Pope, H. P. Kallmann et al. found light emission of a single crystal of anthracene generated by impressing direct voltage in 1963. In 1987, an organ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H05B33/12C07D333/72C08G75/00C09K11/06H05B33/14
CPCC07D333/72C08G61/126C09K11/06H05B33/14H01L51/0036H01L51/0043H01L51/5048C09K2211/1458H10K85/113H10K85/151H10K50/14C08G61/121C08G61/122H10K50/11
Inventor ITOH, KIYOSHI
Owner DAI NIPPON PRINTING CO LTD
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