CN105566320A - Pyridine-quinoline derivative, preparation method and organic light-emitting device - Google Patents
Pyridine-quinoline derivative, preparation method and organic light-emitting device Download PDFInfo
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Abstract
The invention relates to a pyridine-quinoline compound, a preparation method thereof and an organic light-emitting device made from the compound. The pyridine-quinoline derivative is obtained by connection with boronic acid derivatives with different substituting groups on the basis of difluoropyridine-[2,3-g]quinoline; the preparation process is simple, the reaction condition is mild, the pyridine-quinoline derivative can be taken as an electron transport material to be applied to organic light-emitting devices. According to the pyridine-quinoline derivative, the preparation method and the organic light-emitting device, the prepared pyridine-quinoline compound is high in efficiency, high in brightness, long in service life, better in charge transfer capacity and high in glass transition temperature and non-crystallizable when applied to organic light-emitting devices.
Description
Technical field
The present invention relates to organic photoelectrical material field, particularly relate to a class containing pyridoquinoline analog derivative, preparation method and organic luminescent device.
Background technology
Organic electroluminescence device (OLED) is a kind of novel flat panel display device, has the features such as energy-conservation, fast response time, colour stable, environmental compatibility are strong, radiationless, the life-span is long, quality is light, thickness is thin.Due to developing rapidly of photoelectric communication in recent years and MultiMedia Field, organic optoelectronic material has become the core of modern society's information and electronic industry.
Organnic electroluminescent device generally includes anode, organic luminous layer and negative electrode.In organic luminous layer, the electronics of negative electrode and the hole of anode, again in conjunction with formation exciton, when exciton becomes ground state, produce electroluminescent.
Research for organic EL Material is from nineteen fifty Bernose applies the observation of high current/voltage to the macromolecule membrane containing organic pigment.Nineteen sixty-five, people's Late Cambrian such as Pope Electroluminescence Properties of anthracene single crystal, this is the first electro optical phenomenon of organic compound.1987, the people such as the Tang of Kodak found, even if the organic luminescent device with separation function lamination formed by organic materials also can provide 1000cd/cm under the low voltage of 10V or less
2or higher high brightness.
But, adopt the Organnic electroluminescent device of existing luminescent material manufacture still to need further improvement, particularly in efficiency, purity of color etc.We find, pyridoquinoline analog derivative is applied in the little of electroluminescent organic material aspect, and the present invention furthers investigate it.
Summary of the invention
Technical problem to be solved by this invention is that the electron transport material kind in customer service prior art in organic electroluminescence device is single, and performance is difficult to the problem optimized, the diaryl pyridines providing a class simple and easy to get quinoline electron transport material.
Another object of the present invention is to provide that a kind of preparation technology is simple, reaction conditions is gentle can be used for diaryl pyridines in organic electroluminescence device and the preparation method of quinoline electron transport material.
3rd object of the present invention is using a class diaryl pyridines and quinoline derivatives is applied in organic electroluminescence device as electron transport material.
Pyridoquinoline analog derivative general formula of molecular structure provided by the invention, and have formula (1) to be expressed as:
（1）
Wherein, R is independently selected from being with or without substituent C6-C30 aryl, being with or without substituent C3-C30 heteroaryl.
Above-mentioned preferred dihalopyridine of the present invention is [2,3-g] quinoline derivatives electroluminescent organic material also, gets following aryl for R:
Above-mentioned preferred dihalopyridine of the present invention is [2,3-g] quinoline derivatives electroluminescent organic material also, gets above structure carry out analyzing and illustrating for R, and concrete structural formula corresponds to as following table 1 chemical structural formula respectively:
Table 1
| 1 | 2 | ||
| 3 | 4 | ||
| 5 | 6 | ||
| 7 | 8 | ||
| 9 | 10 | ||
| 11 | 12 | ||
| 13 | 14 |
Organic electroluminescent compounds is selected from group compound, but the invention is not restricted to described compound.
Organic electroluminescent compounds of the present invention can be prepared according to following scheme:
The invention provides a kind of organic electroluminescence device, it comprises the first electrode; Second electrode; Which floor one or more layers inserting between described first electrode and the second electrode have, described in one or more organic electroluminescent compounds of which floor having comprise chemical formula 1 represent.Which floor has comprise electroluminescence layer, and the organic electroluminescent compounds of its Chinese style (1) is used as matrix or dopant material.
When the organic electroluminescent compounds of formula (1) is used as matrix, include one or more doping agents.Be not particularly limited for the doping agent in organic electroluminescence device of the present invention.
Below in conjunction with specific embodiment, the present invention will be further described in detail, but be not limited to these embodiments.
The present invention selects pyrido [2, the 3-g] quinoline being easy to the halo synthesized as starting raw material, and its syntheti c route is shown below:
wherein, X is Cl, Br or I.
A kind of described containing dihalopyridine also [2,3-g] organic luminescent device made of quinoline derivatives, it comprises the first electrode, the second electrode and is placed in the one or more organic compound layers between described first electrode, described second electrode, it is characterized in that, organic compound layer described at least one comprises described containing dihalopyridine also [2,3-g] quinoline derivatives.
A kind of described dihalopyridine also [2,3-g] application of quinoline derivatives, it is characterized in that, described dihalopyridine also [2,3-g] quinoline derivatives is used as phosphorescent light body material, hole-injecting material or hole mobile material in described organic electroluminescence device.
A class dihalopyridine provided by the invention also [2,3-g] quinoline derivatives, preparation method and the application in organic electroluminescence device thereof.This dihalopyridine also [2,3-g] quinoline derivatives has high luminous efficiency, high luminous efficiency shows that this compound can be used as luminescent material or light emitting host material, especially can as phosphorescent light body material, for showing high-level efficiency, high brightness, long lifetime in organic electroluminescence device, there is the advantage that manufacturing cost is lower, reduce the manufacturing cost of organic electroluminescence device.
embodiment:
The present invention selects pyrido [2, the 3-g] quinoline being easy to the halo synthesized as starting raw material, and its syntheti c route is as follows:
Wherein, X is Cl, Br or I.Below to synthesize example as X for during Cl:
The synthesis of 4,9-dichloropyridine also [2,3-g] quinoline:
By Ursol D 0.50mol, 2,2-dimethyl-1,3-dioxan-4; 6-diketone 1.00mol, trimethoxy-methane 0.50mol join in the reactor of 4L, are dissolved in 2L phenyl ether, under nitrogen protection condition; react 5 hours, after reaction terminates, make solvent with anhydrous tetrahydro furan; dropwise drip phosphorus oxychloride, after reaction terminates, column chromatography sherwood oil: methylene dichloride=3:1; obtain 4; 9-dichloropyridine is [2,3-g] quinoline 0.41mol also, productive rate 81%.
For enabling above-mentioned purpose of the present invention, feature and advantage become apparent more, are described in detail below to the specific embodiment of the present invention.Set forth a lot of detail in the following description so that fully understand the present invention.But the present invention can be much different from alternate manner described here to implement, those skilled in the art can when without prejudice to doing similar improvement when intension of the present invention, therefore the present invention is by the restriction of following public concrete enforcement.
Embodiment 1: the synthesis of compound 1
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol, 4-(N; N-phenylbenzene) amino-benzene boric acid 220mmol joins in the there-necked flask of 1L, and be dissolved in 400mL toluene, add tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 77mmol compound as white solid 1, productive rate 77%.
Embodiment 2: the synthesis of compound 2
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 1-naphthalene boronic acids 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 87mmol compound as white solid 2, productive rate 87%.
Embodiment 3: the synthesis of compound 3
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; the luxuriant and rich with fragrance boric acid 220mmol of 9-joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 79mmol compound as white solid 3, productive rate 79%.
Embodiment 4: the synthesis of compound 4
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 9-anthracene boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 81mmol compound as white solid 4, productive rate 81%.
Embodiment 5: the synthesis of compound 5
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 1-pyrene boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 75mmol compound as white solid 5, productive rate 75%.
Embodiment 6: the synthesis of compound 6
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol, 9; 9-spiral shell two fluorenes-2-boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 82mmol compound as white solid 6, productive rate 82%.
Embodiment 7: the synthesis of compound 7
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol, 1; 3-ring penta 2-2-boric acid 220mmol join in the there-necked flask of 1L, are dissolved in 400mL toluene, add tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 88mmol compound as white solid 7, productive rate 88%.
Embodiment 8: the synthesis of compound 8
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 3 thienylboronic acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 89mmol compound as white solid 8, productive rate 89%.
Embodiment 9: the synthesis of compound 9
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 2-pyridine boronic acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 80mmol compound as white solid 9, productive rate 80%.
Embodiment 10: the synthesis of compound 10
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; cumarone-2-boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 84mmol compound as white solid 10, productive rate 84%.
Embodiment 11: the synthesis of compound 11
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 2-benzo [b] thienyl boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 77mmol compound as white solid 1, productive rate 83%.
Embodiment 12: the synthesis of compound 12
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; the luxuriant and rich with fragrance boric acid 220mmol of 3-joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 77mmol compound as white solid 13, productive rate 77%.
Embodiment 13: the synthesis of compound 13
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 2-benzoglyoxaline boric acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 76mmol compound as white solid 14, productive rate 76%.
Embodiment 14: the synthesis of compound 14
By 4,9-dichloropyridine also [2,3-g] quinoline 100mmol; 3-quinoline boronic acid 220mmol joins in the there-necked flask of 1L, is dissolved in 400mL toluene, adds tetra-triphenylphosphine palladium 1.5mmol under nitrogen protection; salt of wormwood 250mmol, distilled water 100mL, stirring and refluxing reacts 16 hours; be cooled to room temperature, separatory after reaction terminates, cross silica gel funnel; washing, is spin-dried for, recrystallization; filter, draw 83mmol compound as white solid 15, productive rate 83%.
By fast atom bombardment mass spectroscopy(FABMS) (FABMS) method, carry out the ultimate analysis of compound.The results are shown in Table 2, and wherein MS/FAB (M+) is the molecular weight recorded by FABMS:
Table 2
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with described claim.
Chemical formula a chemical formula b
Corning(is healthy and free from worry) society 15 Ω/cm
2(1000) ito glass substrate is cut into the size of 50mm*50mm*0.7mm.Subsequently in microwave, successively at acetone, Virahol, cleans 15 minutes in pure water respectively, in ultraviolet, clean 30 minutes again.At the 2-TNATA of thereon vacuum evaporation 80nm thickness, form hole injection layer.Above hole injection layer, the α-NPD of vacuum evaporation 30nm thickness, defines hole transporting layer.The compound that above hole transporting layer, the chemical formula a of vacuum evaporation 30nm thickness represents and the compound that chemical formula b represents (doping rate 8%), define luminescent layer.The Alq of vacuum evaporation 30nm thickness above luminescent layer
3, define electron supplying layer.Vacuum evaporation LiF0.5nm (electron injection) and Al60nm successively above electron supplying layer, has made organic luminescent device.In this comparing embodiment 1 and following Application Example 1-14, the EL evaporator adopting DOV company to manufacture carries out vacuum evaporation.
Application Example 1-14:
Adopt as the method in comparative example 1, make the organic luminescent device with structure below, difference is as luminescent layer compound, that replace compound a to adopt is compound 1-14:ITO/2-TNATA (80nm)/α-NPD (the 30nm)/compound 1 ~ 14+ compound b represented in preparation example] (25nm, wherein b content is 8.0%)/Alq
3(30nm) organic luminescent device of the structure of/LiF (0.5nm)/Al (60nm).
Measure embodiment 1: the luminescent properties of comparative sample and sample 1-14
Under similarity condition, measure the sample of comparing embodiment 1 and the sample of Application Example 1-14.Measure and adopt KEITHLEY Keithley 235 type source measuring unit, SpectrascanPR650 spectral scan colourimeter, to evaluate driving voltage, luminosity, luminous efficiency, glow color.The results are shown in Table 3:
Table 3
Represented by table 3, when according to embodiments of the present invention based on diaryl pyridines and quinoline derivatives be used as form the material of electron transfer layer time, the capacity of electron injection improves, and therefore under identical current density, driving voltage reduces.
As mentioned above, according to embodiments of the present invention based on diaryl pyridines and quinoline derivatives has superior electrical property and charge transport ability, and therefore can be used as electron transport material, dopant material, wherein said material is applicable to the fluorescent device of all colours (comprising redness, green, blueness and white).Use is based on diaryl pyridines and the organic EL device of quinoline derivatives manufacture has high-level efficiency, low voltage, high brightness and long lifetime.
Although the present invention's exemplary embodiment has carried out special description, but should be appreciated that those of ordinary skill in the art can carry out the change in various forms and details to it when not departing from the spirit of the present invention and scope that following patent requirement limits.
Claims (5)
1. pyridoquinoline analog derivative general formula of molecular structure provided by the invention, and have formula (1) to represent:
（1）
Wherein, R is independently selected from being with or without substituent C6-C30 aryl, being with or without substituent C3-C30 heteroaryl.
2. diaryl pyridines according to claim 1 quinoline derivatives electroluminescent organic material, is characterized in that, described containing diaryl pyridines and quinoline derivatives material is the one in the compound shown in following structural formula:
,
,
,
,
,
,
,
,
,
,
,
,
,
.
3. the preparation method containing pyridoquinoline electron-like transport material according to claim 1 and 2, is characterized in that, comprise the following steps:
Step S1: add pyridoquinoline class intermediate, boric acid, tetra-triphenylphosphine palladium, salt of wormwood and toluene containing R group in the reaction vessel after degassed;
Step S2: raise temperature of reaction and reflux, fully reacting;
Step S3: cooling, crosses silica gel funnel, and washing, is spin-dried for, and recrystallization obtains the electron transport material containing pyridoquinoline.
4. the preparation method containing pyridoquinoline electron-like transport material according to claim 3, it is characterized in that, starting raw material pyridoquinoline class intermediate described in step S1 is with Ursol D, 2,2-dimethyl-1,3-dioxan-4,6-diketone and trimethoxy-methane are raw material, through decarboxylation/cyclisation, reflux in the phenyl ether of high dilution, then with three oxyhalogen phosphorus substitution reactions.
5. one kind by the organic luminescent device made containing pyridoquinoline electron-like transport material according to claim 1, they one or more organic compound layers comprising the first electrode, the second electrode and be placed between described first electrode and described second electrode, it is characterized in that, organic compound layer described at least one comprises described containing pyridoquinoline electron-like transport material.
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| CN105669670A (en) * | 2016-03-04 | 2016-06-15 | 吉林奥来德光电材料股份有限公司 | Heterocyclic compound and preparation method thereof as well as organic electroluminescent device |
| CN107216329A (en) * | 2017-07-13 | 2017-09-29 | 长春海谱润斯科技有限公司 | A kind of pyridoindole derivatives and processes and the organic electroluminescence device prepared using the compound |
| CN107369775A (en) * | 2017-07-13 | 2017-11-21 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device |
| CN108570047A (en) * | 2017-03-07 | 2018-09-25 | 北京鼎材科技有限公司 | Pyridoquinoline derivative and its application |
| KR20200107855A (en) * | 2019-03-08 | 2020-09-16 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105669670A (en) * | 2016-03-04 | 2016-06-15 | 吉林奥来德光电材料股份有限公司 | Heterocyclic compound and preparation method thereof as well as organic electroluminescent device |
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| CN107369775A (en) * | 2017-07-13 | 2017-11-21 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device |
| KR20200107855A (en) * | 2019-03-08 | 2020-09-16 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR102430678B1 (en) | 2019-03-08 | 2022-08-09 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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Application publication date: 20160511 |