CN103666455A - Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof - Google Patents

Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof Download PDF

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CN103666455A
CN103666455A CN201310636393.0A CN201310636393A CN103666455A CN 103666455 A CN103666455 A CN 103666455A CN 201310636393 A CN201310636393 A CN 201310636393A CN 103666455 A CN103666455 A CN 103666455A
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刘屹东
高涛
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WEIMING PHOTOELECTRIC YANCHENG Co Ltd
Fangyuan Global Yancheng Photoelectric Technology Co Ltd
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Fangyuan Global Yancheng Photoelectric Technology Co Ltd
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Abstract

The invention provides a novel spirofluorene xanthene organic electroluminescent material and a preparation method thereof. The material is synthesized by connecting a functional group to the 2 position of spirofluorene xanthenes as a center unit, and has a structure represented by a general formula in the specification; and in the general formula, R represents a secondary amino group, a pyrryl group, an indolyl group, a carbazyl group, a benzimidazolyl group, or derivative groups of the above groups. The compound has the advantages of simple synthetic method, easy processing, easy purification and low cost. The above organic electroluminescent compound emits blue light, can be used in luminescent materials, can be used as a hole transport material or an electron transfer material, and is hopeful to be widely used in organic light-emitting diode devices, organic electrical storage devices, organic solar batteries, organic laser diode devices and organic field effect transistors.

Description

A kind of novel spiral shell fluorenes oxa anthracenes luminous organic material and preparation thereof
Technical field
The invention belongs to organic synthesis field, relate to spiral shell fluorenes-9 of 2 replacements of the efficiently synthetic a kind of novelty of a kind of single stage method, 9 '-oxa anthracene compound, can be applied in organic electroluminescent field it.
Background technology
As the extremely important part of modern science and technology, flat panel display is more and more significant on the impact of human lives and production, and relevant research also more and more causes people's attention.There is huge variation in the main flow technique of display such as monochromatic cathode-ray tube (CRT), colour liquid crystal display device (LCD), flat plasma display part (PDP), electroluminescence display device (FED), but all there is the shortcoming that cannot make up, cannot meet people's demand to the high-performance flat-panel monitor that more lightly nimble, performance is more excellent in informationized society.
Organic electroluminescence device (OLED) has ultra-thin, complete solidifies, luminous, color is abundant, response is fast, driving voltage is low, reduce power consumption, efficiency is high, production cost is low, good temp characteristic, material range of choice is wide and can realize many outstanding performances such as soft demonstration a little, be expected to become the core component of flat panel display of new generation, thereby become one of the study hotspot in organic electronics and optoelectronic information field.
As far back as 20 beginnings of the century, people have just found organic electroluminescent phenomenon.Pope in 1963 etc. have reported the electroluminescent device of based single crystal anthracene for the first time, but the thickness of monocrystalline reaches 20 μ m, and driving voltage, up to 400 V, is therefore failed to cause and studied widely interest.The people such as the Deng Qingyun of Kodak in 1987 use oxine aluminium (Alq 3) as luminescent layer, obtained compared with low dc voltage (approximately 10 v) drive under, after the organic EL device of high brightness, caused various countries scientists' very big interest, the people such as the nineteen ninety Burroughes of Cambridge University have reported the electroluminescent of polymer p-phenylene vinylene (PPV) first, Uchida in 1992 etc. find blue light material poly alkyl fluorene first, are also important breakthroughs in blue light emitting material field.
Spiral shell fluorenes xanthene has good luminous quantum efficiency and charge transport properties, preferably thermostability and morphological stability.The spiral shell fluorenes xanthene of usining is expected to become practical organic optoelectronic material as structural motif builds organic materials as core.Yet Patents is all the photoelectric material with the spiral shell fluorenes xanthene kernel of phenolic hydroxy group, with the photoelectric material of the spiral shell fluorenes xanthene kernel of the derivative containing secondary amine, pyrryl, indyl, carbazyl, benzimidazolyl-or described group, have no report.Therefore, the present invention by simple single stage method synthetic a series of based on spiral shell fluorenes xanthene, be that to take the derivatives group of secondary amine, pyrryl, indyl, carbazyl, benzimidazolyl-or described group be substituent material to core, blue light-emitting, is having wide practical use aspect electronics or photoelectric material.
Summary of the invention
Technical problem: the object of the present invention is to provide a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material and preparation thereof, the spiral shell fluorenes xanthene of 2 replacements, substituting group is the derivatives group of secondary amine, pyrryl, indyl, carbazyl, benzimidazolyl-or described group.Prepare serial spiral shell fluorenes oxa anthracenes luminous organic material, can be used for the luminescent layer of organic electroluminescence device.
Technical scheme: the present invention is a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material and preparation thereof, and this material is spiral shell fluorenes-9 of 2 replacements, and 9 '-xanthene, has as chemical formula 1structure,
Formula 1in: R represents the derivatives group of secondary amine, pyrryl, indyl, carbazyl, benzimidazolyl-or described group.
As preferably, above-mentioned chemical formula 1the corresponding raw material of middle R is: ,
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,
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.
As preferably, above-mentioned chemical formula 1concrete structure is as follows:
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、
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、
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、
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、
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、 。
The preparation method of above-mentioned material comprises the steps:
(1) by compound 2-bromine spiral shell fluorenes-9,9 '-xanthene, highly basic and compound R-H add in dry weak polar solvent, under room temperature, stir certain hour;
(2) organic palladium catalyzer and organic phosphine catalyzer are added in dry weak polar solvent and stirred;
(3) step (1) and step (2) solution mix and blend are refluxed;
(4) reaction finishes, and is cooled to room temperature, extraction, water washing, is dried, filters, revolves steaming, with eluent, carries out column chromatography, isolates high-purity product 1.
The preparation method of above-mentioned material, the highly basic of described step (1) is sodium tert-butoxide, potassium tert.-butoxide, sodium ethylate, potassium ethylate, propyl carbinol sodium, propyl carbinol potassium; The weak polar solvent of described step (1) is one or more the mixture of toluene, THF, DMF, DMSO, DMA; The organic palladium catalyzer of described step (2) is Pd (PPh 3) 4, PdCl 2(dppf), Pd (OAc) 2, organic phosphine catalyzer is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine; The eluent of described step (4) is the mixture of methylene dichloride and sherwood oil.
The preparation method of above-mentioned material, the highly basic of described step (1) and compound 2-bromine spiral shell fluorenes-9, the amount of substance ratio of 9 '-xanthene is 1:1 ~ 2:1, compound R-H and 2-bromine spiral shell fluorenes-9, the amount of substance of 9 '-xanthene is than being 0.8:1 ~ 2:1.
The preparation method of above-mentioned material, described step (1) churning time is 5 min ~ 10 h; The return time of step (3) is 5h ~ 20 h.
Above-mentioned material, is characterized in that this material blue light-emitting.
Beneficial effect:
Patent of the present invention is by the synthetic a series of new compounds of simple single stage method, and the method is simple, gentle to reaction conditions, easily realizes industrial mass production.This compounds blue light-emitting, can be applied to luminescent material, simultaneously, such material can be used as hole mobile material, electron transport material etc., is expected to be widely used in organic light emitting diode device, Organic Electricity memory device, organic solar batteries, organic laser diode component, organic field-effect tube.
Embodiment
Content for a better understanding of the present invention, further illustrates technical scheme of the present invention below by concrete enforcement, comprises concrete synthetic route.But these embodiment do not limit the present invention.
Embodiment 1: compound 1-1synthetic
In 50mL three-necked flask, add compound 2(1.72 g, 4.1 mmol), compound 3(0.90 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol), in 15 mL anhydrous toluene solutions, stir 30 min under room temperature, make solution a.In the dry dry toluene of 10 mL, add Pd (OAc) 2(23 mg, 0.1 mmol) and tri-butyl phosphine (83 mg, 0.41 mmol), make solution b.Solution b is added in solution a, and 10 h reflux.Be cooled to room temperature, with toluene extraction, water washing, dry MgSO for organic layer 4remove moisture, filter, revolve steaming.10 methylene dichloride of mL 1:10 and the mixed solvent of sherwood oil carry out column chromatography as eluent, obtain white solid, and productive rate is 55%, and wavelength is the ultra violet lamp blue light-emitting of 254 nm, HPLC (100% methyl alcohol), R t=6.18 min; Ms Calcd:549; Ms Found:550 (M+1) +.
Embodiment 2: compound 1-2synthetic
Figure DEST_PATH_IMAGE045
In 50mL three-necked flask, add compound 2(1.72 g, 4.1 mmol), compound 4(0.75 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol), in 15mL anhydrous toluene solution, stir 30 min under room temperature, make solution a.In the dry dry toluene of 10 mL, add Pd (OAc) 2(23 mg, 0.1 mmol) and tri-butyl phosphine (83 mg, 0.41 mmol), make solution b.Solution b is added in solution a, and 10 h reflux.Be cooled to room temperature, with toluene extraction, water washing, dry MgSO for organic layer 4remove moisture, filter, revolve steaming.10 methylene dichloride of mL 1:10 and the mixed solvent of sherwood oil carry out column chromatography as eluent, obtain white solid, and productive rate is 55%, and wavelength is the ultra violet lamp blue light-emitting of 254 nm, HPLC (100% methyl alcohol), R t=6.43 min; Ms Calcd:513; Ms Found:514 (M+1) +.
Embodiment 3: compound 1-3synthetic
Figure DEST_PATH_IMAGE046
In 50mL three-necked flask, add compound 2(1.72 g, 4.1 mmol), compound 5(1.15 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol), in 15mL anhydrous toluene solution, stir 30 min under room temperature, make solution a.In the dry dry toluene of 10mL, add Pd (OAc) 2(23 mg, 0.1 mmol) and tri-butyl phosphine (83 mg, 0.41 mmol), make solution b.Solution a is added in solution b, and 10 h reflux.Be cooled to room temperature, with toluene extraction, water washing, dry MgSO for organic layer 4remove moisture, filter, revolve steaming.10 methylene dichloride of mL 1:10 and the mixed solvent of sherwood oil carry out column chromatography as eluent, obtain white solid, and productive rate is 60%, and wavelength is the ultra violet lamp blue light-emitting of 254 nm, HPLC (100% methyl alcohol), R t=3.37 min; Ms Calcd:611; Ms Found:612 (M+1) +.

Claims (8)

1. novel spiral shell fluorenes oxa anthracenes luminous organic material and a preparation thereof, is characterized in that this material is spiral shell fluorenes-9 of 2 replacements, and 9 '-xanthene, has as chemical formula 1structure,
Figure 2013106363930100001DEST_PATH_IMAGE001
In formula: R represents the derivatives group of secondary amine, pyrryl, indyl, carbazyl, benzimidazolyl-or described group.
2. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 1 and preparation thereof, is characterized in that, the corresponding raw material of described chemical formula side group R is preferably: ,
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, ,
Figure 2013106363930100001DEST_PATH_IMAGE005
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, ,
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,
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,
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.
3. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 1 and preparation thereof, is characterized in that this compound has following structure:
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、
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、
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。
4. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 1 and preparation thereof, is characterized in that the preparation of described material comprises the steps:
(1) by compound 2-bromine spiral shell fluorenes 9,9 '-xanthene, highly basic and compound R-H add in dry weak polar solvent, under room temperature, stir certain hour;
(2) organic palladium catalyzer and organic phosphine catalyzer are added in dry weak polar solvent and stirred;
(3) step (1) and step (2) solution mix and blend are refluxed;
(4) reaction finishes, and is cooled to room temperature, extraction, water washing, is dried, filters, revolves steaming, with eluent, carries out column chromatography, isolates high-purity compound 1.
5. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 4 and preparation thereof, the highly basic that it is characterized in that described step (1) is sodium tert-butoxide, potassium tert.-butoxide, sodium ethylate, potassium ethylate, propyl carbinol sodium, propyl carbinol potassium; The weak polar solvent of described step (1) is one or more the mixture of toluene, THF, DMF, DMSO, DMA; The organic palladium catalyzer of described step (2) is Pd (PPh 3) 4, PdCl 2(dppf), Pd (OAc) 2, organic phosphine catalyzer is trimethyl-phosphine, triphenylphosphine, tri-butyl phosphine; The eluent of described step (4) is the mixture of methylene dichloride and sherwood oil.
6. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 4 and preparation thereof, the highly basic and compound 2-bromine spiral shell fluorenes-9 that it is characterized in that described step (1), the amount of substance of 9 '-xanthene is than being 1:1 ~ 2:1, compound R-H and 2-bromine spiral shell fluorenes-9, the amount of substance of 9 '-xanthene is than being 0.8:1 ~ 2:1.
7. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 4 and preparation thereof, is characterized in that described step (1) churning time is 5 min ~ 10 h; The return time of step (3) is 5 h ~ 20 h.
8. a kind of novel spiral shell fluorenes oxa anthracenes luminous organic material according to claim 1 and preparation thereof, is characterized in that described material blue light-emitting.
CN201310636393.0A 2013-12-03 2013-12-03 Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof Pending CN103666455A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108137527A (en) * 2015-10-07 2018-06-08 株式会社Lg化学 Noval chemical compound and the Organic Light Emitting Diode for including it
JP2020506896A (en) * 2017-04-13 2020-03-05 エルジー・ケム・リミテッド Heterocyclic compound and organic light emitting device containing the same
CN110872284A (en) * 2018-08-30 2020-03-10 上海和辉光电有限公司 Oxadiazole-substituted oxygen-containing spirofluorene organic material, preparation method and OLED device
KR102100581B1 (en) * 2019-01-30 2020-04-14 두산솔루스 주식회사 Organic light-emitting compound and organic electroluminescent device using the same
CN113402561A (en) * 2021-05-24 2021-09-17 浙江工业大学 High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof
US11127904B2 (en) 2017-09-29 2021-09-21 Lg Chem, Ltd. Compound, coating composition comprising same, organic light emitting device using same, and manufacturing method thereof
KR20220129519A (en) * 2019-03-28 2022-09-23 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
CN115583888A (en) * 2022-12-12 2023-01-10 烟台显华科技集团股份有限公司 Naphthyl substituted arylamine compound and application thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108137527A (en) * 2015-10-07 2018-06-08 株式会社Lg化学 Noval chemical compound and the Organic Light Emitting Diode for including it
CN108137527B (en) * 2015-10-07 2021-08-20 株式会社Lg化学 Novel compound and organic light emitting diode comprising the same
US11450819B2 (en) 2017-04-13 2022-09-20 Lg Chem, Ltd. Heterocyclic compound and organic light-emitting element including same
JP2020506896A (en) * 2017-04-13 2020-03-05 エルジー・ケム・リミテッド Heterocyclic compound and organic light emitting device containing the same
US11127904B2 (en) 2017-09-29 2021-09-21 Lg Chem, Ltd. Compound, coating composition comprising same, organic light emitting device using same, and manufacturing method thereof
CN110872284A (en) * 2018-08-30 2020-03-10 上海和辉光电有限公司 Oxadiazole-substituted oxygen-containing spirofluorene organic material, preparation method and OLED device
CN110872284B (en) * 2018-08-30 2023-05-02 上海和辉光电股份有限公司 Oxadiazole-substituted oxygen-containing spirofluorene organic material, preparation method and OLED device
KR102100581B1 (en) * 2019-01-30 2020-04-14 두산솔루스 주식회사 Organic light-emitting compound and organic electroluminescent device using the same
KR20220129519A (en) * 2019-03-28 2022-09-23 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR102576227B1 (en) * 2019-03-28 2023-09-08 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
CN113402561A (en) * 2021-05-24 2021-09-17 浙江工业大学 High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof
CN113402561B (en) * 2021-05-24 2023-09-08 浙江工业大学 High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof
CN115583888A (en) * 2022-12-12 2023-01-10 烟台显华科技集团股份有限公司 Naphthyl substituted arylamine compound and application thereof

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