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Organic compound, charge-transporting material, and organic electroluminescent element

a charge-transporting material and organic technology, applied in the direction of organic chemistry, luminescent compositions, natural mineral layered products, etc., can solve the problems of insufficient luminous efficiency, poor electron transporting ability of devices using biphenyl derivatives, and insufficient luminous efficiency. , to achieve the effect of satisfactory durability, excellent electron transport ability, and excellent hole transport ability

Active Publication Date: 2009-07-30
PIONEER CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0016] Accordingly, an object of the present invention is to provide an organic compound and a charge transporting material exhibiting both excellent hole transporting ability and excellent electron transporting ability, showing satisfactory durability against electric oxidation / reduction, and having a high triplet excitation level. Another object of the present invention is to provide an organic electroluminescent device which uses the organic compound, emits light with a high efficiency, is highly stably driven, and has a long lifetime.
[0032] An organic compound according to the first aspect exhibits both excellent hole transporting ability and excellent electron transporting ability, shows excellent durability against electric oxidation / reduction, and has a high triplet excitation level. Accordingly, an organic electroluminescent device according to the third aspect using this organic compound can emit light with a high luminance and a high efficiency, has increased stability, can be driven highly stably, and can have a longer lifetime.
[0034] The organic compound according to the first aspect inherently shows excellent oxidation / reduction stability and can thereby be advantageously applied to an electrophotographic photoreceptor, in addition to an organic electroluminescent device.

Problems solved by technology

Sufficient luminous efficiency, however, has not yet been obtained even when phosphorescent emission is used.
However, an organic electroluminescent device using the biphenyl derivative does not yield a satisfactorily high luminous efficiency, because the recombination of charge tends to occur unevenly in the vicinity of the cathode, and the device has poor balance in charge recombination.
The compound, however, shows light emission only under a high voltage and is supposed to be insufficient in luminance and luminous efficiency,
In addition, they have a poor durability as materials for organic electroluminescent devices.
Accordingly, they are insufficient in performance for use in blue-light emitting devices and phosphorescent emitting devices.
In addition, the compounds show a poor electrochemical durability when they are not fully substituted at the 2-, 4-, and 6-positions of the pyridine ring, at the 2-, 4-, and 6-positions of the pyrimidine ring, or at the 2-, 3-, 5-, and 6-positions of the pyrazine ring.
These compounds, however, are susceptible to localization of positive or negative charges when the molecules are subjected to electric oxidation or reduction.
The compounds having such a partial structure have a poor durability against electric oxidation and reduction.
This compound is expected to have an improved durability against electric oxidation, but has a poor hole transporting ability, because it has only one carbazolyl group.
Accordingly, the compound is not in good balance between the hole transporting ability and the electron transporting ability and is not suitable as a host material for a light-emitting layer of an organic electroluminescent device.
In addition, it has a poor thermal stability.

Method used

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  • Organic compound, charge-transporting material, and organic electroluminescent element
  • Organic compound, charge-transporting material, and organic electroluminescent element
  • Organic compound, charge-transporting material, and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Syntheses of Target Compounds 1 to 3

[0318]

[0319] Concentrated sulfuric acid (11.6 ml) was added to a mixture as a solution of 2,5-difluorobenzaldehyde (10.24 g), acetophenone (8.66 g), and acetic acid (100 ml) in a dry air atmosphere, followed by stirring at 35° C. for seven hours. The mixture was combined with methanol (5 ml) and water (150 ml) to yield a precipitate, and the precipitate was collected by filtration and washed with water. This was washed in a suspended state in methanol with heating under reflux and thereby yielded Target Compound 1 (10.94 g).

[0320] Target Compound 1 (6.34 g), 1-phenacylpyridinium bromide (10.83 g), ammonium acetate (50.0 g), and acetic acid (220 ml), and N,N-dimethylformamide (220 ml) were stirred with heating under reflux in a dry air atmosphere for six hours. The resulting mixture was combined with water (440 ml) to yield a precipitate, and the precipitate was collected by filtration and washed with methanol. This was purified by washing in a s...

synthesis example 2

Syntheses of Target Compounds 4 to 7

[0324]

[0325] Concentrated sulfuric acid (11.4 ml) was added to a mixture as a solution of 4-bromobenzaldehyde (12.90 g), acetophenone (8.37 g), and acetic acid (100 ml), followed by stirring at 40° C. in a dry air atmosphere for five hours. The mixture was combined with methanol (100 ml) to yield a precipitate, and the precipitate was collected by filtration and washed with methanol. This was washed in a suspended state in methanol and thereby yielded Target Compound 4 (8.72 g).

[0326] Target Compound 4 (8.62 g), 1-phenacylpyridinium bromide (12.52 g), ammonium acetate (57.8 g), acetic acid (257 ml), and N,N-dimethylformamide (257 ml) were stirred with heating under reflux in a dry air atmosphere for 5.5 hours, followed by pouring into water (600 ml) with ice cooling to yield a precipitate. The precipitate was collected by filtration and washed with a mixed solvent of ethanol / water. This was purified by washing in a suspended state in ethanol wit...

synthesis example 3

Syntheses of Target Compounds 8 to 9

[0331]

[0332] Benzaldehyde (2.12 g), 2′,5′-difluoroacetophenone (6.25 g), ammonium acetate (19.7 g), and acetic acid (50 ml) were stirred at 100° C. in the atmosphere for five hours, followed by cooling with ice. The mixture was combined with methanol and water to yield a precipitate, and the precipitate was separated by filtration, purified by washing in a suspended state in methanol, dried with heating under reduced pressure, and thereby yielded Target Compound 8 (1.15 g).

[0333] Carbazole (3.03 g) was added to a suspension of sodium hydride (55%, 0.79 g) in anhydrous N,N-dimethylformamide (54 ml) in a nitrogen stream, followed by stirring at 80° C. for sixty minutes. The mixture was combined with Target Compound 8 (1.15 g) and stirred with heating under reflux for 4.8 hours. This was combined with water (50 ml) and methanol (50 ml) under cooling with ice to yield a precipitate, and the precipitate was separated by filtration and washed with met...

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Abstract

There are provided an organic having both excellent hole transporting property and satisfactory electron transporting and showing excellent durability against electric oxidation / reduction and a high triplet excitation level, and a charge transporting material and an organic electroluminescent device each using the organic compound. The organic compound is represented by following Formula (I): wherein Cz1 and Cz2 each represent a carbazolyl group; Z represents a direct bond or an arbitrary linkage group enabling the conjugation of nitrogen atoms in the carbazole rings of Cz1 and Cz2 with each other; and Q represents a direct bond connecting to “G” in following Formula (II): wherein Ring B1 represents a six-membered aromatic heterocyclic ring having “n” nitrogen atom(s) as hetero atom(s); “n” represents an integer of from 1 to 3; G represents a direct bond or an arbitrary linkage group connecting to Q when G connects to Q; Gs connect to carbon atoms at the ortho-position and the para-position with respect to nitrogen atom(s) in Ring B1; G represents an aromatic hydrocarbon group when G does not connect to Q; and “m” represents an integer of from 3 to 5.

Description

FIELD OF THE INVENTION [0001] The present invention relates to novel organic compounds and charge transporting materials, and organic electroluminescent devices using the organic compounds. More specifically, it relates to organic compounds and charge transporting materials which are stable even when repeatedly subjected to electric oxidation and / or reduction, and organic electroluminescent devices using the organic compounds and having a high luminous efficiency and a long lifetime. BACKGROUND OF THE INVENTION [0002] There have been developed electroluminescent devices using organic thin films. Such electroluminescent devices using organic thin films, namely, organic electroluminescent devices each generally include a substrate bearing an anode, a cathode, and one or more organic layers. The one or more organic layers are arranged between the two electrodes and include at least a light-emitting layer. Such organic layers may include a hole injection layer (anode buffer layer), a ho...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B32B9/00C09K11/00C07D401/02
CPCC07D209/86H05B33/20C07D249/08C07D401/14C07D403/14C09K11/06C09K2211/1007C09K2211/1022C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/185C09K2211/186C09K2211/188H01L51/0034H01L51/0035H01L51/0067H01L51/0072H01L51/0078H01L51/0081H01L51/0084H01L51/0085H01L51/0094H01L51/5016H01L51/5048C07D215/30H10K85/10H10K85/111H10K85/654H10K85/6572H10K85/311H10K85/324H10K85/341H10K85/342H10K85/40H10K50/14H10K50/11H10K2101/10
Inventor YABE, MASAYOSHISATO, HIDEKI
Owner PIONEER CORP
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