CN108997239A - A kind of compound of cyano-containing and application thereof and organic electroluminescence device - Google Patents

A kind of compound of cyano-containing and application thereof and organic electroluminescence device Download PDF

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CN108997239A
CN108997239A CN201810828333.1A CN201810828333A CN108997239A CN 108997239 A CN108997239 A CN 108997239A CN 201810828333 A CN201810828333 A CN 201810828333A CN 108997239 A CN108997239 A CN 108997239A
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layer
compound
cyano
electroluminescence device
organic electroluminescence
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黄锦海
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Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Taoe Chemical Technology Co Ltd
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    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract

The present invention provides a kind of compounds of cyano-containing, have the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, it can be applied to organic electroluminescence device, solar battery, Organic Thin Film Transistors or organophotoreceptorswith field, have the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device of the compound production based on cyano-containing.

Description

A kind of compound of cyano-containing and application thereof and organic electroluminescence device
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of compound of cyano-containing and application thereof, also It is related to a kind of organic electroluminescence device.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, so that Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency Luminescent material.
Speed in OLED material, due to the speed of most electroluminescent organic material transporting holes than transmitting electronics Fastly, it be easy to cause the electrons and holes quantity of luminescent layer uneven, the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines) Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines, Simultaneously as lower electron mobility, so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, above it is restricted in application.Cause This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility With great value.
Summary of the invention
It is the compound for having the following structure Formulas I the present invention provides a kind of compound of cyano-containing:
Wherein, Ar1-Ar3The aryl of alkyl, substitution or unsubstituted C6-C30 independently selected from C1-C12；Z1-Z3 Independently selected from N or CH；R1-R5At least one is CN, remaining is H or F.
Optionally, Ar1And Ar2Independently selected from benzene, biphenyl, naphthalene, aminomethyl phenyl；
Ar3Selected from phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, Fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, 9,9- are Spirofluorene-based, replace or Unsubstituted dibenzothiophene, substitution or unsubstituted dibenzofuran group.
Optionally, the compound of the cyano-containing specifically includes the compound of following structural 1-48:
The compound of cyano-containing of the invention can be applied to organic electroluminescence device, solar battery, organic film Transistor or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer Layer, at least one layer of compound containing such as above-mentioned cyano-containing in the organic layer.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking Layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer.
Preferably, wherein the layer where the compound of the cyano-containing as described in structural formula I is that electron transfer layer and electronics are infused Enter at least one layer in layer.
The compound of cyano-containing as described in structural formula I is used alone, or is used in mixed way with other compounds；Such as structural formula The compound of cyano-containing described in I can be used alone one such compound, can also be simultaneously using two in structural formula I Kind or two or more compounds；A kind of compound of cyano-containing selected from structural formula 1-48 is used alone, or uses two simultaneously Kind or more selected from structural formula 1-48 cyano-containing compound.
Still optionally further, organic electroluminescence device of the invention includes anode, hole transmission layer, luminescent layer, electronics Transport layer, electron injecting layer and cathode wherein contain one or more kinds of structures in electron transfer layer or electron injecting layer The compound of Formulas I；It is further preferred that containing one or more kinds of structural formula 1- in electron transfer layer or electron injecting layer 48 compound.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the invention can be used and take when being had the compound of structural formula I using the present invention With other materials, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer, and Obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance can effectively be transferred to hole on luminescent layer from anode.It may include that other small molecules and macromolecule are organic Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8, Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained Object, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as Ir, Pt, Os, Cu, Au), polyethylene click The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone, and a variety of can also mix Object uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.Except of the invention has structural formula I Outside compound, it is also an option that the following compound of collocation, but not limited to this, oxa- oxazole, thiazole compound, three nitrogen Azole compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, contain sila at three nitrogen piperazine class compounds Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine replace Benzene-like compounds, benzimidazoles compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention In, except it is of the invention there is Compounds of structural formula I in addition to, be mainly selected from the compound of alkali metal or alkali metal, or be selected from alkaline earth The compound or alkali metal complex of metal or alkaline-earth metal, can choose following compound, and but not limited to this, alkali gold Category, alkaline-earth metal, rare earth metal, the oxide of alkali metal or halide, the oxide of alkaline-earth metal or halide, rare earth The organic complex of the oxide or halide of metal, alkali metal or alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, Magnesia, these compounds, which can be used alone, to be used with mixture, can also match with other electroluminescent organic materials It closes and uses.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows the compound of cyano-containing of the present invention as described in structural formula I, has preferable thermal stability, high Luminous efficiency, high luminance purity.Using the compound production organic electroluminescence device have electroluminescent efficiency well and The advantage that excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention,
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as sending out Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 4
The synthetic method of intermediate 4-1
In flask, sequentially add intermediate 2- (the bromo- phenyl of the chloro- 5- of 3-) -4,6- diphenyl -1,3,5-triazines (4g, 9.5mmol), 3- cyanophenylboronic acid pinacol ester (2.6g, 11.4mmol), potassium carbonate (2.7g, 20mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (400mL) and water (20mL), are heated to reflux 12 hours under nitrogen protection, cooling, are extracted with methylene chloride It takes, dry, concentration, crude product obtains 3.1g, yield 75% with re crystallization from toluene.
The synthetic method of compound 4
In flask, intermediate 4-1 (2.5g, 5.6mmol), 9- phenanthrene boric acid (1.5g, 6.7mmol), carbonic acid are sequentially added Potassium (1.3g, 10mmol), palladium acetate (0.1g), X-phos (0.3g), toluene (20mL), ethyl alcohol (10mL) and water (10mL), It is heated to reflux under nitrogen protection 12 hours, cools down, is extracted with dichloromethane, drying, being concentrated, crude product is obtained through column chromatographic purifying 2g, yield 62%.
Embodiment 2
The synthetic route of compound 6
For its synthetic method such as compound 4, raw materials used is intermediate 4-1 and 2- benzophenanthrene boric acid, yield 53%.
Embodiment 3
The synthesis of compound 17
For synthetic method such as compound 4, raw materials used is intermediate 4-1 and 9, two fluorenes -2- boric acid of 9'- spiral shell, yield 69%.
Embodiment 4
The synthetic route of compound 24
The synthetic method of intermediate 24-1
Its synthetic method only replaces 3- cyano benzene with 4- cyanophenylboronic acid pinacol ester as the synthesis of intermediate 4-1 Pinacol borate, yield 70%.
The synthetic method of compound 24
For its synthetic method as the synthesis of compound 4, raw materials used is intermediate 24-1 and 9- phenanthrene boric acid, yield 54%.
Embodiment 5
The synthesis of compound 37
For its synthetic method as the synthesis of compound 4, raw materials used is intermediate 24-1 and 9,9 '-spiral shell, two fluorenes -2- boron Acid, yield 59%.
Embodiment 6
The synthetic route of compound 45
The synthetic method of intermediate 45-1
For its synthetic method as the synthesis of intermediate 4-1, raw materials used is the fluoro- phenyl boric acid of 4- cyano -5-, yield 82%.
The synthetic method of compound 45
Its synthetic method is raw materials used to replace intermediate 4-1, yield by intermediate 45-1 as the synthesis of compound 4 49%.
Embodiment 7-12
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share Department) successively pass through: deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, NPB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq of 37.5nm thickness is deposited on the hole transport layer3The C545T that weight ratio is 1% is adulterated as luminescent layer 140。
Then, 37.5nm thickness the compounds of this invention is deposited on the light-emitting layer as electron transfer layer 150.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure 20mA/cm2Current density under efficiency such as table 1.
Comparative example 1-2
In addition to electron transfer layer uses Alq respectively3It is replaced outside the compounds of this invention with ETM1, other and embodiment 7-12 mono- Sample.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometer measure 20mA/cm2Current density under efficiency such as table 1.
1 test result of table
Embodiment Compound Power efficiency (lm/W) Color
7 4 6.3 Green light
8 6 6.5 Green light
9 17 6.1 Green light
10 24 6.2 Green light
11 37 6.1 Green light
12 45 6.4 Green light
Comparative example 1 Alq3 5.0 Green light
Comparative example 2 ETM1 5.3 Green light
As shown in Table 1, under the same conditions, using the effect of the organic electroluminescence device of the compound of the present invention preparation Rate is higher than comparative example, as described above, the compound of the present invention has high stability, organic electroluminescence prepared by the present invention Part has high efficiency and optical purity.
Structural formula described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be within the scope of protection determined by the claims.

Claims (8)

1. a kind of compound of cyano-containing, which is characterized in that have the following structure the compound of Formulas I:
Wherein, Ar1-Ar3The aryl of alkyl, substitution or unsubstituted C6-C30 independently selected from C1-C12；Z1-Z3Independently Selected from N or CH；R1-R5At least one is CN, remaining is H or F.
2. the compound of cyano-containing as described in claim 1, which is characterized in that Ar1And Ar2Independently selected from benzene, biphenyl, naphthalene, Aminomethyl phenyl；
Ar3Selected from phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene Base, (9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- is Spirofluorene-based, replaces or does not take Dibenzothiophene, substitution or the unsubstituted dibenzofuran group in generation.
3. the compound of cyano-containing as described in claim 1, which is characterized in that specifically include the chemical combination of following structural 1-48 Object:
4. application of the compound of cyano-containing described in claim 1 in organic electroluminescence device.
5. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole At least one layer in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, which is characterized in that institute It states at least one layer of containing as described in claim 1 based on the compound of cyano-containing in organic layer.
6. organic electroluminescence device as claimed in claim 5, which is characterized in that be used alone a kind of selected from such as claim The compound of the cyano-containing of structural formula 1-48 described in 3, or structure as claimed in claim 3 is selected from using two or more simultaneously The compound of the cyano-containing of formula 1-48.
7. organic electroluminescence device as claimed in claim 5, which is characterized in that cyano-containing as described in claim 1 Layer where compound is at least one layer in electron transfer layer and electron injecting layer.
8. organic electroluminescence device as claimed in claim 5, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201810828333.1A 2018-07-25 2018-07-25 A kind of compound of cyano-containing and application thereof and organic electroluminescence device Pending CN108997239A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109535093A (en) * 2018-12-24 2019-03-29 上海道亦化工科技有限公司 A kind of trisubstituted benzene based compound and organic electroluminescence device
WO2019201621A1 (en) * 2018-04-18 2019-10-24 Novaled Gmbh Compound, method for preparing the same, organic semiconducting layer, organic electronic device, display device and lighting device comprising the same
EP3805206A1 (en) * 2019-10-08 2021-04-14 Novaled GmbH Compound and an organic semiconducting layer, an organic electronic device, a display device and a lighting device comprising the same
CN112851591A (en) * 2019-11-28 2021-05-28 南京高光半导体材料有限公司 Triphenylene-based organic compound, organic electroluminescent material and device
CN113549023A (en) * 2021-08-25 2021-10-26 武汉天马微电子有限公司 Organic compound and application thereof
WO2022103031A1 (en) * 2020-11-12 2022-05-19 주식회사 랩토 Triazine or pyrimidine derivative and organic electroluminescent element comprising same

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019201621A1 (en) * 2018-04-18 2019-10-24 Novaled Gmbh Compound, method for preparing the same, organic semiconducting layer, organic electronic device, display device and lighting device comprising the same
CN109535093A (en) * 2018-12-24 2019-03-29 上海道亦化工科技有限公司 A kind of trisubstituted benzene based compound and organic electroluminescence device
EP3805206A1 (en) * 2019-10-08 2021-04-14 Novaled GmbH Compound and an organic semiconducting layer, an organic electronic device, a display device and a lighting device comprising the same
WO2021069595A1 (en) * 2019-10-08 2021-04-15 Novaled Gmbh Compound and an organic semiconducting layer, an organic electronic device, a display device and a lighting device comprising the same
CN114555580A (en) * 2019-10-08 2022-05-27 诺瓦尔德股份有限公司 Compound, and organic semiconductor layer, organic electronic device, display device, and lighting device each comprising same
CN112851591A (en) * 2019-11-28 2021-05-28 南京高光半导体材料有限公司 Triphenylene-based organic compound, organic electroluminescent material and device
CN112851591B (en) * 2019-11-28 2022-09-23 南京高光半导体材料有限公司 Triphenylene-based organic compound, organic electroluminescent material and device
WO2022103031A1 (en) * 2020-11-12 2022-05-19 주식회사 랩토 Triazine or pyrimidine derivative and organic electroluminescent element comprising same
KR20220065123A (en) * 2020-11-12 2022-05-20 주식회사 랩토 Triazine or Pyrimidine derivatives, and organic electroluminescent device including the same
KR102517278B1 (en) * 2020-11-12 2023-04-05 주식회사 랩토 Triazine or Pyrimidine derivatives, and organic electroluminescent device including the same
CN113549023A (en) * 2021-08-25 2021-10-26 武汉天马微电子有限公司 Organic compound and application thereof

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