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Organic photoelectric material and organic electroluminescent device containing material

An organic optoelectronic material and electroluminescence technology, applied in the field of material science, can solve the problems of limiting the luminous efficiency, service life and operating voltage of devices, preventing the full practical application of OLED technology, etc., and achieve good industrialization prospects, good application effects, power Efficiency and Quantum Efficiency Improvement Effects

Active Publication Date: 2016-07-27
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Hole injection materials or hole transport materials are major obstacles to the full practical application of OLED technology, which directly limit the luminous efficiency, service life and operating voltage of the device.
At present, the main hole injection materials or hole transport materials are triarylamine derivatives or carbazole derivatives, but their service life, efficiency and operating voltage need to be improved.

Method used

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  • Organic photoelectric material and organic electroluminescent device containing material
  • Organic photoelectric material and organic electroluminescent device containing material
  • Organic photoelectric material and organic electroluminescent device containing material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 110

[0053] Example 110, 10'-(9-(dibenzo[b,d]furan-4-yl)-9H-carbazole-3,6-diyl)bis(9,9-dimethyl-9, 10-dihydroacridine) (compound 1) synthesis:

[0054]

[0055] Preparation of compound 1-a:

[0056] Take 3,6-dibromocarbazole (32.5g, 0.1mol), potassium carbonate (20.7g, 0.15mol), cuprous iodide (1.9g, 0.01mol), o-phenanthroline (3.6g, 0.02mol) , 4-iododibenzofuran (38.2g, 0.13mol) and 400g DMF, under the protection of nitrogen, the mixture was reacted at 120°C for 15.0 hours. After the reaction was completed, the insoluble matter was filtered off, the filtrate was desolvated under reduced pressure until there was no fraction, and the residue was purified by column chromatography with petroleum ether ethyl acetate mixture (volume ratio 7:1), and then recrystallized by toluene ethanol to obtain the compound 1-a (29.9 g, 60.89%), GC-MS: 491.23, calculated 491.18.

[0057] Preparation of Compound 1:

[0058] Take compound 1-a (24.5g, 0.05mol), potassium carbonate (20.7g, 0.15mol)...

Embodiment 310

[0060] Example 310, 10'-((9-(dibenzo[b,d]furan-4-yl)-9H-carbazole-3,6-diyl)bis(4,1-phenylene)) Synthesis of bis(9,9-dimethyl-9,10-dihydroacridine) (compound 3):

[0061]

[0062] Preparation of compound 3

[0063] Get compound 1-a (24.5g, 0.05mol), (4-(9,9-dimethylacridin-10(9H)-yl) phenyl) phenylboronic acid (36.2g, 0.11mol), potassium carbonate ( 20.73g, 0.15mol) and 100g of water were dissolved with 200mL of toluene and 100mL of ethanol, and stirred under nitrogen gas for 1 hour to remove the oxygen in the reaction flask. Then add Pd(PPh 3 ) 4 0.58g (0.5mmol), reflux under vigorous stirring, and the reaction process was tracked and detected by TLC. After the reaction was completed, the aqueous phase was extracted with 200 mL of ethyl acetate, and the organic phase was desolvated under reduced pressure until there was no fraction. The residue was purified by column chromatography with pure toluene, and then recrystallized by toluene ethanol to obtain compound 3 (37.8 ...

Embodiment 81

[0065] Example 810-(4-(9-(dibenzo[b,d]furan-4-yl)-6-(4'-(9,9-dimethylacridin-10(9H)-yl) -[1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine (compound 8) Synthesis:

[0066]

[0067] Preparation of Compound 8-b

[0068] Get compound 1-a (24.5g, 0.05mol), (4-(9,9-dimethylacridin-10(9H)-yl) phenyl) phenylboronic acid (6.5g, 0.02mol), potassium carbonate ( 10.4 g, 0.075 mol) and 100 g of water were dissolved with 200 mL of toluene and 100 mL of ethanol, and stirred under nitrogen gas for 1 hour to remove oxygen in the reaction flask. Then add Pd(PPh 3 ) 4 0.12g (0.1mmol), reflux under vigorous stirring, and the reaction process was tracked and detected by TLC. After the reaction was completed, the aqueous phase was extracted with 200 mL of ethyl acetate, the organic phase was desolvated under reduced pressure until there was no fraction, and the residue was purified by column chromatography with petroleum ether ethyl acetate mixture (volume ra...

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Abstract

The invention discloses an organic photoelectric material.The general structural formula of the organic photoelectric material is as shown in the formula (I), wherein R1 is selected from a phenyl group, C7-14 alkyl phenyl groups, C10-60 polycyclic conjugate aromatic groups and aromatic heterocyclic radicals at least containing one of N, S and O; carbazole and acridine structural units of a matrix structure are connected through X and Y, wherein X and Y are both independently selected from a C-N single bond, phenylene, biphenylene, C6-24 polycyclic conjugate arylidene and aromatic heterocyclic radicals at least containing one of N and O, and R2, R3, R4 and R5 are independently selected from a hydrogen group, a halogen group, a cyano group, a nitro group, C1-10 alkyl groups, substituted or unsubstituted C1-12 alkoxyl groups, a phenyl group, C7-14 alkyl phenyl or C7-14 alkyl methoxyphenyl.

Description

technical field [0001] The invention relates to the field of material science, and more particularly relates to an organic photoelectric material and an organic electroluminescent device containing the material. Background technique [0002] The research on organic electroluminescent devices began in the 1960s, and OLEDs did not flourish until the end of the 1980s. OLED has the advantages of full solid-state, low-voltage drive, active light emission, fast response, wide viewing angle, large light-emitting area, light-emitting wavelength covering the entire visible light region, and rich colors. It has great advantages in the field of full-color large-area display and has become an extremely Flat panel display devices in the foreground. The luminous brightness of an organic electroluminescent device is proportional to the product of the concentration of holes and electrons and the recombination probability of excitons. In order to obtain higher luminous efficiency, not only ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D405/14C09K2211/1088C09K2211/1029H10K85/6574H10K85/6572H10K50/00
Inventor 林存生慈振华张善国王子宁胡葆华孟凡民
Owner VALIANT CO LTD
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