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Novel fused polycyclic compound and organic light-emitting device including the same

An organic light-emitting device, fused polycyclic technology, applied in organic chemistry, electro-solid devices, semiconductor devices, etc., to achieve the effect of high optical output durability

Inactive Publication Date: 2012-02-29
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, these organic compounds still need improvement in emission hue, emission efficiency, brightness and durability

Method used

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  • Novel fused polycyclic compound and organic light-emitting device including the same
  • Novel fused polycyclic compound and organic light-emitting device including the same
  • Novel fused polycyclic compound and organic light-emitting device including the same

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manufacture example

[0044] Spin-coated films of Exemplified Compounds 1-1, C-1, C-2 and C-3 were produced and their fluorescence spectra were measured. Among these compounds, C-1 showed the largest shift of the peak wavelength with respect to the peak wavelength of the fluorescence spectrum in dilute solution. The observed fluorescence spectrum is broad, extending through the green region to the yellow region. This indicates that in the unsubstituted compound, C-1 in the solid state, due to the π-electron interaction on the fused ring, the molecules are strongly associated with each other, thereby achieving an increase and stabilization of the fluorescence wavelength.

[0045] In substituted indeno Among the derivatives, the intermolecular association was most inhibited in C-3 with four aryl groups. The comparison between the exemplified compounds 1-1 and C-2, both having two aryl groups, shows that, compared with the introduction of the aryl group into R in the general formula [2] 7 and R 1...

preparation example 1

[0140] The preparation method of exemplary compound 1-1

[0141] Exemplary compound 1-1 is an example of the condensed polycyclic compound represented by the general formula [1] of the present invention, and can be produced, for example, by the following method.

[0142] (1) Synthesis of intermediate mixture 1

[0143] [chemical 8]

[0144]

[0145] Intermediate Mixture 1

[0146] Under a nitrogen atmosphere, the following compounds were mixed in cyclohexane (60 ml) and the resulting mixture was heated and stirred for 6 hours on a silicone oil bath heated to 80° C.:

[0147] : 3.00g (13.1mmol)

[0148] Bis(pinacolato) diboron: 8.01g (31.5mmol)

[0149] [Ir(OMe)COD] 2 : 0.250g (0.377mmol)

[0150] 4,4'-di-tert-butyl-2,2'-bipyridine (dtbpy): 0.202g (0.754mmol)

[0151] After cooling the mixture to room temperature, the reaction precipitate was filtered and the resulting solid was washed with heptane. Recrystallization was carried out in chloroform / methanol system an...

Embodiment 1

[0214] An organic light emitting device was prepared by the method described below.

[0215] An ITO film with a thickness of 120 nm and used as an anode was sputter-deposited on a glass substrate and used as a transparent conductive support substrate. The substrate was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol (IPA), washed with pure water, and then dried. The substrate was further washed with UV / ozone so that it could be used as a transparent conductive support substrate. Compound A represented by the following structural formula was used as a hole transport material and a chloroform solution of Compound A at a concentration of 0.1 wt% was prepared.

[0216] This solution was dropped onto an ITO electrode and spin-coated first at 500 rpm for 10 seconds and then at 1000 rpm for 40 seconds to form a film. Then, the film was dried in a vacuum oven at 80° C. for 10 minutes to completely remove the solvent in the film and thereby form a hol...

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Abstract

Provided is a fused polycyclic compound represented by general formula 1: (In general formula 1, at least one of R1 to R4 is a group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, and R1 to R4 may be the same as or different from each other.)

Description

technical field [0001] The present invention relates to a novel fused polycyclic compound and an organic light-emitting device comprising the novel condensed polycyclic compound. Background technique [0002] An organic light emitting device is composed of an anode, a cathode, and a thin film containing a fluorescent organic compound sandwiched between the anode and the cathode. When electrons and holes are respectively injected from the electrodes, excitons of the fluorescent compound are generated and the organic light emitting device emits light when the excitons return to their ground state. The recent development of organic light-emitting devices has been remarkable. Organic light emitting devices are characterized in that they can achieve high luminance at low applied voltage, wide variation in emission wavelength, and high-speed response, and enable reduction in thickness and weight of light emitting devices. Organic light-emitting devices therefore herald the possi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/62H01L51/50H10K99/00
CPCC07C13/62C07C2603/24C07C2603/54H10K85/622H10K50/11H10K85/625
Inventor 堀内贵行镰谷淳小菅哲弥齐藤章人
Owner CANON KK
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