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Condensed ring organic compound and organic electroluminescent device using compound

An organic compound and luminescent technology, which is applied in the direction of silicon organic compounds, organic chemistry, and electric solid-state devices, can solve the problem of unsatisfactory hole-blocking materials, which are not conducive to high-efficiency green phosphorescent devices, and the stability needs to be further improved. and other problems, to achieve the effect of not easy to crystallize and decompose, the synthesis method is simple, and the lifespan is improved

Pending Publication Date: 2021-09-28
ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 1,3,5-tris(N-phenyl-2-benzimidazole)benzene ( TPBI) is an electron transport / hole blocking material widely used in electroluminescent devices, but its stability in the device needs to be further improved
High stability green and red phosphorescent devices can be obtained by using BAlq; however, its higher HOMO energy level (-5.9eV) and lower triplet energy level (~2.18eV) are not conducive to obtaining high-efficiency green light Phosphorescent device; the luminous efficiency of the device containing BAIq is significantly lower (about 40%) than that of the device containing BCP (T.Watanabe et al., Proc.SPIE 2001, 4105, 175)
Therefore, although BAlq can achieve a good lifetime, it is not a satisfactory hole-blocking material in general, and the reason is that the efficiency of the fabricated devices is too low

Method used

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  • Condensed ring organic compound and organic electroluminescent device using compound
  • Condensed ring organic compound and organic electroluminescent device using compound
  • Condensed ring organic compound and organic electroluminescent device using compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the preparation of compound C-19

[0053] (1) Preparation of intermediate sub-1

[0054]

[0055] 2-Chloro-3-aminopyridine: 11.0g (51.87mmol), phenanthrene-9-boronic acid: 11.52g, toluene: 105mL, ethanol: 26mL were charged in the reaction vessel, and then potassium carbonate: 15.7g was added to dissolve at H 2 O: 56 mL of the aqueous solution was irradiated with ultrasonic waves for 30 minutes while passing nitrogen gas. Add palladium acetate: 0.6 g, and stir overnight under heating and reflux. After natural cooling, ethyl acetate was added to the system for extraction, and the organic layer was concentrated to obtain a crude product. n-heptane was added to this crude product, and the precipitated solid was collected by filtration to obtain 2-(phenanthrene-9-yl)-3-aminopyridine (sub-1)13.5 (yield 96%).

[0056] (2) Preparation of intermediate sub-2

[0057]

[0058] Put intermediate sub-1: 22.5g, triethylamine: 9.6g, dichloromethane: 225ml in th...

Embodiment 2

[0065] Embodiment 2: the preparation of compound C-1

[0066]

[0067] Similar to the synthetic route of compound C-19, the dibenzofuran-4-boronic acid in the synthesis of intermediate-1 is replaced by dibenzothiophene-4-boronic acid with oxafluorenofuran-boronic acid, and after 4 steps of reaction, the obtained Compound C1, the yield of the last step reaction is 66%; LC-MS: M / Z 691.2 (M+H) + .

Embodiment 3

[0068] Embodiment 3: the preparation of compound C37

[0069]

[0070] Similar to the synthetic route of compound C-19, the dibenzofuran-4-boronic acid of the synthetic intermediate Sub-1 was replaced with naphthalene-[2,1-b]-benzofuran-6-boronic acid to synthesize the intermediate Sub -4 is replaced by 2-bromo-9-naphthyl-1,10-phenanthroline, and through 4 steps of reaction, to compound C-37, the yield of the last step is 63%; LC-MS: M / Z 701.2 (M +H) + .

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Abstract

The invention discloses a condensed ring organic compound applied to the field of organic photoelectricity and an organic light-emitting device using the compound. The molecular structural formula of the organic compound is shown as a general formula (I), wherein X is selected from CR or N; L is independently selected from a single bond, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R is independently selected from hydrogen, a deuterium atom, an alkyl group of C1-C12, an alkoxy group of C1-C8, a substituted or unsubstituted alkenyl group of C2-C8, a substituted or unsubstituted alkynyl group of C2-C8, a substituted or unsubstituted aryl group of C6-C60, and a substituted or unsubstituted heteroaryl group of C2-C60; A1, A2 and Ar are independently selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C2-C60 heteroaryl group; and n is an integer of 0-7. The organic compound can effectively promote injection and transmission of electrons, balance hole and electron transmission in a photoelectric device, and effectively improve the efficiency and service life of the device.

Description

technical field [0001] The invention relates to a condensed ring organic compound in the field of organic electroluminescence and an organic electroluminescence device using the compound. Background technique [0002] Organic electroluminescent devices (OLED: Organic Light Emission Diodes) have the advantages of wide viewing angle, fast response speed, high color quality, flexible light emission, etc., and have broad application prospects. An OLED device is generally a sandwich structure, including positive and negative electrode film layers and an organic functional material layer sandwiched between the electrode film layers. Apply voltage to the electrodes of the OLED device, positive charges are injected from the positive electrode, and negative charges are injected from the negative electrode. Under the action of the electric field, the positive and negative charges migrate in the organic layer and recombine to emit light. It has been widely used in the display panels o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D471/04H01L51/54C07F7/08
CPCC07D519/00C07D471/04C07F7/0816H10K85/622H10K85/657H10K85/6574H10K85/40H10K85/6572
Inventor 王子兴华万鸣吕良飞吴空物陈清泉赵晓宇
Owner ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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