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Aromatic amine derivatives and organic electroluminescent device using same

an organic electroluminescent device and amine technology, applied in the direction of luminescent compositions, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of reducing a current efficiency, increasing an operating voltage, and changing the color of emitted, so as to improve the yield of organic el devices and prolong the life. , the effect of less liabl

Inactive Publication Date: 2008-05-08
IDEMITSU KOSAN CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides an aromatic amine derivative that can be used as a material for an organic EL device. This amine derivative has a specific substituent that reduces the operating voltage, prevents crystallization, and improves the yield and lifetime of the organic EL device. The amine derivative has an amino group substituted with an aryl group having a thiophene structure, which interacts with the electrode and facilitates the injection of charges. The amine unit also has steric hindrance, reducing interaction between molecules and increasing the yield. The invention also provides an organic EL device containing this amine derivative as a hole transporting material. The amine derivative is reduced in voltage, less prone to crystallization, and has a high yield in producing the organic EL device.

Problems solved by technology

Usually, when an organic EL device is operated or stored under high temperature environment, brought about are adverse effects such as a change in a color of emitted light, a reduction in a current efficiency, a rise in an operating voltage and a reduction in an emission lifetime.
However, if they have a lot of aromatic groups in a molecule, crystallization is liable to be caused in forming a thin film using the above hole transporting materials to produce an organic EL device, and the problems that an outlet of a crucible used for vapor deposition is clogged and that defects of a thin film originating in crystallization are caused to bring about a reduction in a yield of an organic EL device have been brought about.
Further, compounds having more aromatic groups in a molecule have usually a higher glass transition temperature (Tg) but have a higher sublimation temperature, and it is considered that the phenomena that decomposition is caused in vapor deposition and that a deposited film is unevenly formed are brought about, so that the problem that the lifetime is short has been involved therein.
These compounds are unstable and hard to be refined, and therefore a purity thereof is not enhanced.
When thiophene is bonded directly to amine, an electron state of amine is varied to a large extent, and therefore the satisfactory performances are not exhibited.
A 2-position or a 3-position in thiophene has a high reactivity and is electrically unstable.
Further, polar groups necessary for polymerization reduce the performances of the device such as a lifetime and the like, and therefore the above compounds are not preferred.

Method used

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  • Aromatic amine derivatives and organic electroluminescent device using same
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  • Aromatic amine derivatives and organic electroluminescent device using same

Examples

Experimental program
Comparison scheme
Effect test

synthetic example 1

Synthesis of Intermediate 1

[0178] A three neck flask of 1000 mL was charged with 47 g of 4-bromobiphenyl, 23 g of iodine, 9.4 g of periodic acid dihydrate, 42 ml of water, 360 mL of acetic acid and 11 mL of sulfuric acid under argon flow, and the mixture was stirred at 65° C. for 30 minutes and then reacted at 90° C. for 6 hours. The reaction product was poured into ice and water and filtered. The filtered matter was washed with water and then with methanol, whereby 67 g of a white powder was obtained. The principal peaks of m / z=358 and 360 versus C12H15BrI=359 were obtained by analysis of FD-MS (field desorption mass spectrum), and therefore it was identified as Intermediate 1.

synthetic example 2

Synthesis of Intermediate 2

[0179] A three neck flask of 300 mL was charged with 10 g of p-terphenyl, 12 g of iodine, 4.9 g of periodic acid dihydrate, 20 mL of water, 170 mL of acetic acid and 22 mL of sulfuric acid under argon flow, and the mixture was stirred at 65° C. for 30 minutes and then reacted at 90° C. for 6 hours. The reaction product was poured into ice and water and filtered. The filtered matter was washed with water and then with methanol, whereby 18 g of a white powder was obtained. The principal peak of m / z=482 versus C18H12I2=482 was obtained by analysis of FD-MS, and therefore it was identified as Intermediate 2.

synthetic example 3

Synthesis of Intermediate 3

[0180] A reaction vessel of 50 L was charged with 750 g of phenylboronic acid, 1000 g of 2-bromothiophene, 142 g of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 9 L of a 2 M solution of sodium carbonate (Na2CO3) and 15 L of dimethoxyethane under argon flow, and then they were reacted at 80° C. for 8 hours. The reaction solution was extracted with toluene / water, and the extract was dried on anhydrous sodium sulfate. This was concentrated under reduced pressure, and a crude product obtained was refined through a column, whereby 786 g of a white powder was obtained.

[0181] A reaction vessel of 20 L was charged with 786 g of the compound obtained above and 8 L of DMF (dimethylforamide) under argon flow, and then 960 g of NBS (N-bromosuccinimide) was slowly added thereto to carry out reaction at room temperature for 12 hours. The reaction solution was extracted with hexane / water, and the extract was dried on anhydrous sodium sulfate. This was concentrate...

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Abstract

The present invention provides a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer in the above organic thin film layer, particularly a hole injecting layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Use of the aromatic amine derivative described above materialize an organic electroluminescence device which reduces an operating voltage and makes molecules less liable to be crystallized and which enhances a yield in producing the organic EL device and has a long lifetime.

Description

BACKGROUND OF THE INVENTION [0001] The present invention relates to an aromatic amine derivative and an organic electroluminescence (EL) device using the same, specifically to an aromatic amine derivative which reduces the operating voltage and inhibits the molecules from being crystallized by using an aromatic amine derivative having a specific substituent for a hole transporting material and which enhances a yield in producing an organic EL device and improves a lifetime of the organic EL device. RELATED ART [0002] An organic EL device is a spontaneous light emitting device making use of the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Since an organic EL device of a laminate type driven at a low voltage was reported by C. W. Tang et al. of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987 and the like...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C211/54C07D409/10C07D409/14H10K99/00
CPCC07D333/58C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014H01L51/50H01L51/006H01L51/0061H01L51/0074H01L51/5048H05B33/14C09K2211/1092H10K85/636H10K85/633H10K85/6576H10K50/14H10K50/15H10K85/631H10K50/00
Inventor YABUNOUCHI, NOBUHIROKAWAMURA, MASAHIROKAWAMURA, HISAYUKIHOSOKAWA, CHISHIOMATSUNAMI, SHIGEYUKIYOSHINAGA, TADAHIKOKIJIMA, YASUNORI
Owner IDEMITSU KOSAN CO LTD
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