CN104744347A - Dianthracene compounds containing pyridyl at terminals and application thereof - Google Patents

Dianthracene compounds containing pyridyl at terminals and application thereof Download PDF

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CN104744347A
CN104744347A CN201410111568.0A CN201410111568A CN104744347A CN 104744347 A CN104744347 A CN 104744347A CN 201410111568 A CN201410111568 A CN 201410111568A CN 104744347 A CN104744347 A CN 104744347A
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compound
formula
anthracene compounds
aromatic group
replacement
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CN104744347B (en
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黄达
孙艳雪
谭玉东
靳灿辉
孙仲猛
曹林法
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JIANGSU HECHENG NEW MATERIALS Co Ltd
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JIANGSU HECHENG NEW MATERIALS Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/649—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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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Abstract

The invention provides dianthracene compounds shown in a general formula I in the specification. In the general formula I, L1 and L2 represent single bonds, substituted or unsubstituted heterocyclic aromatic groups of C2-C60 or substituted or unsubstituted hydrocarbon aromatic groups of C6-C60; L3 represents a substituted or unsubstituted heterocyclic aromatic group of C2-C60 or a substituted or unsubstituted hydrocarbon aromatic group of C6-C60; L1, L2 and L3 are shown in a formula in the specification at different time; R10, R18, R21 and R23-R28 represent hydrogen, halogen and substituted or unsubstituted alkyl or alkoxy of C1-C10. The compounds have good luminescence properties, high electron transport capacities and terrific solubility and can be used in luminescent materials, electron transport materials and hole-blocking materials in the electroluminescence field. The invention also provides an organic electroluminescence device at least comprising a pair of electrodes and organic luminescent media between the electrodes. The organic luminescent media at least comprise the dianthracene compounds.

Description

End is containing two anthracene compounds and application thereof of pyridyl
Technical field
The present invention relates to the two anthracene compounds of a kind of end containing pyridyl, this two anthracenes compounds can be applied to electroluminescent field.
Background technology
Organic electroluminescent LED (OLED) from Deng Qingyun in 1987 at Applied Physics bulletin (Appl.Phys.Lett., 1987,51,913) since publishing an article on, because its drive from main light emission, low-voltage direct-current, the advantage of all solidstate, be subject to academia and industry member is paid attention to greatly.In display field, OLED has the feature of cathode tube and liquid-crystal display concurrently, and visual angle is large, low in energy consumption, bright in luster, is described as dreamlike indicating meter of future generation.At lighting field, OLED, as the technology that uniquely really can realize area source, has luminous soft not dazzling, environmental protection, the healthy light source of the light that gets close to nature most, to be described as in human development history the lighting source of most energy-saving health.
High performance luminescent material is adopted to be the important foundation preparing OLED.Present OLED material is mainly divided into small molecule material and macromolecular material, the easy crystallization of small molecule material, and poorly soluble, macromolecular material luminous efficiency is low, is unfavorable for suitability for industrialized production.So find one and have higher photoluminescence efficiency, the organic materials with good solubility becomes the key issue of OLED material technical field.
The anthracene compounds found now, is typical luminescence system, compares the compound being suitable as electroluminescent material.9,10-diaryl anthracene has satisfactory stability and luminous efficiency, is excellent blue emitting material.2,9 '-two anthracene compounds is due to splendid steric hindrance effect, and make such compound film spectrum compare the red shift of PL solution spectrum very little, light emitting main peak remains on about 450nm.Meanwhile, document (Chem.Lett., 2008,37,1150-1151) also reports that this compounds has splendid thermostability.
But, in existing bibliographical information, 2,9 '-two anthracene compounds mostly is hydrocarbon type compound, and only possess single luminescent properties, transmission performance is poor, being applied to electroluminescent field can cause device power consumption to increase, the problems such as product life shortens, chromaticity distortion, are badly in need of the material that exploitation has luminescent properties and transmission performance concurrently.CN101395105A reports the two anthracene compounds that a class contains carbazole and benzoglyoxaline group, but complex synthetic route, the low purification difficult of solubleness, is unfavorable for suitability for industrialized production.
Compound containing pyridyl is typical electron deficiency system, has good to accept electronic capability.Compound containing pyridyl is typical electron deficiency system, has good to accept electronic capability.The class that document (Chem.Mater., 2011,23,621-630) is reported contains the electron transport material of pyridine groups, shows very high thermostability, excellent hole barrier and exciton blocking capability, splendid electron transport ability.Document (Adv.Funct.Mater., 2011,21, the electron-like transport material containing pyridine groups 1881-1886) reported, show excellent electronic transmission performance and electron injection performance, such material has good electrochemical stability simultaneously, increases the service life.
The present invention, on the basis with twist structured two anthracene derivatives, introduces the pyridyl of electron deficiency, makes compound of the present invention have good luminescent properties and good transmission performance concurrently.Overcome the shortcoming of traditional hydrocarbon type two anthracene compounds transmission performance difference.
In addition, consider the difficulty or ease of suitability for industrialized production, compound of the present invention is many containing alkyl group.
Summary of the invention
The object of the invention is the fluorescent chemicals that proposition one class is novel, described fluorescent chemicals is on the basis with twist structured two anthracene derivatives, introduce the pyridyl of electron deficiency, compound of the present invention is made to have good luminescent properties and good transmission performance concurrently, can as the luminescent layer in organic light emitting medium, electron transfer layer and hole blocking layer.
In order to complete foregoing invention object, the invention provides a kind of two anthracene compounds as shown in formula I:
Wherein,
L 1and L 2identical or different, represent the replacement of singly-bound, C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 with being mutually independent or not replacing hydrocarbon type aromatic group;
L 3represent the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 independently or do not replace hydrocarbon type aromatic group;
Prerequisite be L1, L2 different with L3 time be
R 10, R 11, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 21, R 23, R 24, R 25, R 26, R 27and R 28identical or different, represent hydrogen with being mutually independent, halogen, the substituted or unsubstituted alkyl of C1-C10, or the substituted or unsubstituted alkoxyl group of C1-C10.
In some embodiments, described L 1with L 2identical, represent singly-bound, the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 or do not replace hydrocarbon type aromatic group.
In some embodiments, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc, Rd are identical or different, represent hydrogen with being mutually independent, halogen, the replacement of C1-C30 or unsubstituted alkyl, or the replacement of C1-C30 or unsubstituted alkoxyl group.
In some embodiments, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc can be hydrogen, halogen, the substituted or unsubstituted alkyl of C1-C30, or the substituted or unsubstituted alkoxyl group of C1-C30.
In some embodiments, described L1, L2 and L3 are selected from independently of one another
In some embodiments, R 26and R 27be selected from hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl independently of one another.
On the other hand, present invention also offers two kinds of synthetic methods of two anthracene compounds of formula I, a kind of method is as follows:
1) by formula 4 compound
With formula 5 compound
By being obtained by reacting formula 2 compound
2) by formula 6 compound
With formula 7 compound
Formula 8 intermediate is obtained through suzuki linked reaction
Described formula 8 intermediate is obtained by reacting formula 3 compound by boration
3) described formula 2 compound and described formula 3 compound are obtained two anthracene compounds shown in formula I by suzuki linked reaction:
Wherein,
X 1, X 2, X 3for halogen.
Another kind method be:
1) by formula 2 compound
With formula 9 compound
Formula 10 compound is obtained by linked reaction
Formula 11 compound is obtained through bromination reaction
2) described formula 11 compound and formula 12 compound
Formula 13 compound is obtained by linked reaction
Formula 14 compound is obtained through bromination reaction
3) described formula 14 compound and formula 15 compound
Two anthracene compounds shown in general formula I are obtained by linked reaction
Wherein,
X 4for halogen.
Two anthracene compounds as shown in formula I according to the present invention are preparing in organic electroluminescence device the purposes be used as in luminescent material, electron transport material or hole barrier materials.
Another aspect of the present invention provides a kind of organic electroluminescence device, comprises the organic light emitting medium between pair of electrodes and electrode, comprises at least one two anthracene compounds of the present invention in described organic light emitting medium.
In some embodiments, described two anthracene compounds are arranged in the electron transfer layer of described organic light emitting medium.
In some embodiments, described two anthracene compounds are arranged in the luminescent layer of described organic light emitting medium.
In some embodiments, described two anthracene compounds are as blue emitting material.
In some embodiments, described two anthracene compounds are as the main body luminescent material of described luminescent layer.
The invention provides a kind of comparative approach of material electronics transmission performance, adopt the method for quantum chemistry, in certain accuracy rating, by the electron recombination energy of comparative compound, obtain the difference of the electronic transmission performance between compound.
Organic compound of the present invention has good transmission performance and luminescent properties, can be used as luminescent layer, electron transfer layer and hole blocking layer in organic electroluminescence device.
Accompanying drawing explanation
Fig. 1 represents the NMR data according to compound of the present invention of synthesis in embodiment 34.
Fig. 2 represents the NMR data according to compound of the present invention of synthesis in embodiment 36.
Fig. 3 represents the NMR data according to compound of the present invention of synthesis in embodiment 37.
Fig. 4 represents the NMR data according to compound of the present invention of synthesis in embodiment 38.
Fig. 5 represents the NMR data according to compound of the present invention of synthesis in embodiment 42.
Fig. 6 represents the NMR data according to compound of the present invention of synthesis in embodiment 44.
Fig. 7 represents the NMR data according to compound of the present invention of synthesis in embodiment 46.
Fig. 8 represents the NMR data according to compound of the present invention of synthesis in embodiment 47.
Fig. 9 represents the spectroscopic data according to compound of the present invention of synthesis in embodiment 37.
Embodiment
Embodiment 1
The preparation of compound H P-NP14-PY4
[HP-NP14-PY4]
By 1,4-dibromine naphthalene (4mmol, 1.14g), pyridine-4-boric acid (4mmol, 0.49g) and tetrakis triphenylphosphine palladium (100mg) mixing, add the mixing solutions of toluene (6ml)/ethanol (6ml)/2M Na2CO3 (1ml).This reaction system is stirred 4 hours under 100 degrees Celsius, is then cooled to room temperature.By water (50ml) diluting reaction system also with ethyl acetate (3*50ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains shallow white solid (0.56g, productive rate 50%).
Embodiment 2
The preparation of compound H P-NP14-PY3
[HP-NP14-PY3]
Replace pyridine-4-boric acid except with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-NP14-PY3.
Embodiment 3
The preparation of compound H P-NP14-PY2
[HP-NP14-PY2]
Replace pyridine-4-boric acid except with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-NP14-PY2.
Embodiment 4
The preparation of compound H P-2PH44-PY4
[HP-2PH44-PY4]
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY4.
Embodiment 5
The preparation of compound H P-2PH44-PY3
[HP-2PH44-PY3]
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY3.
Embodiment 6
The preparation of compound H P-2PH44-PY2
[HP-2PH44-PY2]
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-2PH44-PY3.
Embodiment 7
The preparation of compound H P-PH44-PY4
[HP-PH44-PY4]
Isosorbide-5-Nitrae-dibromine naphthalene is replaced except with Isosorbide-5-Nitrae-dibromobenzene, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY4.
Embodiment 8
The preparation of compound H P-PH44-PY3
[HP-PH44-PY3]
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-3-boric acid, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY3.
Embodiment 9
The preparation of compound H P-PH44-PY2
[HP-PH44-PY2]
Replace Isosorbide-5-Nitrae-dibromine naphthalene except with 4,4-'-dibromobiphenyl, replace pyridine-4-boric acid with pyridine-2-boric acid, through the reaction identical with embodiment 1, obtain compound H P-PH44-PY2.
Embodiment 10
The preparation of compound H P-AN-NP14-PY4
[HP-AN-NP14-PY4]
By HP-NP14-PY4(1mmol, 284mg) be dissolved into anhydrous tetrahydrofuran solution (10ml), 1.6M butyl lithium solution (1mmol is dripped under-78 degrees Celsius, 0.63ml), 2-bromo anthraquinone (0.5mmol, 144mg) is then added, be warming up to stirring at room temperature 2 hours, add water (20ml) and extract with methylene dichloride (3*40ml), anhydrous magnesium sulfate drying organic phase, concentrating and obtain dark solid.Dark solid be dissolved in acetic acid (30ml), and add potassiumiodide (3mmol, 500mg), a hydration sodium hypophosphite (6mmol, 1.1g), 120 degrees Celsius are stirred 3 hours, are then cooled to room temperature, have solid to separate out.Solid cold water (3*20ml) after filtering is washed, dries to obtain white solid HP-AN-NP14-PY4(300mg, productive rate 90%).
Embodiment 11
The preparation of compound H P-AN-NP14-PY3
[HP-AN-NP14-PY3]
Except replacing HP-NP14-PY4 with HP-NP14-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-NP14-PY3.
Embodiment 12
The preparation of compound H P-AN-NP14-PY2
[HP-AN-NP14-PY2]
Except replacing HP-NP14-PY4 with HP-NP14-PY2, through the reaction identical with embodiment 10, obtain compound H P-AN-NP14-PY2.
Embodiment 13
The preparation of compound H P-AN-PH44-PY4
[HP-AN-PH44-PY4]
Except replacing HP-NP14-PY4 with HP-PH44-PY4, through the reaction identical with embodiment 10, obtain compound H P-AN-PH44-PY4.
Embodiment 14
The preparation of compound H P-AN-PH44-PY3
[HP-AN-PH44-PY3]
Except replacing HP-NP14-PY4 with HP-PH44-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-PH44-PY3.
Embodiment 15
The preparation of compound H P-AN-2PH44-PY4
[HP-AN-2PH44-PY4]
Except replacing HP-NP14-PY4 with HP-2PH44-PY4, through the reaction identical with embodiment 10, obtain compound H P-AN-2PH44-PY4.
Embodiment 16
The preparation of compound H P-AN-2PH44-PY3
[HP-AN-2PH44-PY3]
Except replacing HP-NP14-PY4 with HP-2PH44-PY3, through the reaction identical with embodiment 10, obtain compound H P-AN-2PH44-PY3.
Embodiment 17
The preparation of compound H P-ANme-PH44-PY4
[HP-ANme-PH44-PY4]
Except replacing HP-NP14-PY4 with HP-PH44-PY4, replacing 2-bromo anthraquinone with bromo-6 tectoquinones of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANme-PH44-PY4.
Embodiment 18
The preparation of compound H P-ANme-PH44-PY3
[HP-ANme-PH44-PY4]
Except replacing HP-NP14-PY4 with HP-PH44-PY3, replacing 2-bromo anthraquinone with bromo-6 tectoquinones of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANme-PH44-PY3.
Embodiment 19
The preparation of compound H P-ANet-2PH44-PY4
[HP-ANet-2PH44-PY4]
Except replacing HP-NP14-PY4 with HP-2PH44-PY4, replacing 2-bromo anthraquinone by bromo-6 EAQ of 2-, through the reaction identical with embodiment 10, obtaining compound H P-ANet-2PH44-PY4.
Embodiment 20
The preparation of compound H P-AN9-PH44-PY4
[HP-AN9-PH44-PY4]
By 1,4-dibromoanthracene (4mmol, 1.34g), 4-(4-pyridyl)-phenylo boric acid (4mmol, 0.80g) with tetrakis triphenylphosphine palladium (100mg) mixing, add the mixing solutions of toluene (6ml)/ethanol (6ml)/2M Na2CO3 (1ml).This reaction system is stirred 4 hours 100 degrees Celsius of lower nitrogen protections, is then cooled to room temperature.By water (50ml) diluting reaction system also with ethyl acetate (3*50ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains yellow solid HP-AN9-PH44-PY4(0.66, productive rate 40%).
Embodiment 21
Compound H P -aN9 -pH44 -the preparation of PY3
[HP-AN9-PH44-PY3]
Replace 4-(4-pyridyl)-phenylo boric acid except with 4-(3-pyridyl)-phenylo boric acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH44-PY3.
Embodiment 22
The preparation of compound H P-AN9-PH44-PY2
[HP-AN9-PH44-PY2]
Except 4-(2-pyridyl)-phenylo boric acid replaces 4-(4-pyridyl)-phenylo boric acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH44-PY2.
Embodiment 23
The preparation of compound H P-AN9-PH43-PY4
[HP-AN9-PH43-PY4]
Replace 4-(4-pyridyl)-phenylo boric acid except with 3-(4-pyridyl)-phenylo boric acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-PH43-PY4.
Embodiment 24
The preparation of compound H P-AN9-2PH44-PY4
[HP-AN9-2PH44-PY4]
Replace 4-(4-pyridyl)-phenylo boric acid except with 4-(4-pyridyl)-biphenylboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-2PH44-PY4.
Embodiment 25
Compound H P -aN9 -2PH44 -the preparation of PY3
[HP-AN9-2PH44-PY3]
Replace 4-(4-pyridyl)-phenylo boric acid except with 4-(3-pyridyl)-biphenylboronic acid, through the reaction identical with embodiment 20, obtain compound H P-AN9-2PH44-PY3.
Embodiment 26
The preparation of compound H P-AN9-NP14-PY3
[HP-AN9-NP14-PY3]
Replace 4-(4-pyridyl)-phenylo boric acid except with 4-(3-pyridyl)-1-naphthalene boronic acids, through the reaction identical with embodiment 20, obtain compound H P-AN9-NP14-PY3.
Embodiment 27
The preparation of compound H P-AN9B-PH44-PY4
[HP-AN9B-PH44-PY4]
By compound H P-AN9-PH44-PY4(3mmol; 1.23g) be dissolved in anhydrous tetrahydro furan (25ml); 1.6M butyl lithium solution (3.6mmol is dripped under-78 degrees Celsius; 2.3ml); nitrogen protection is stirred 2 and was as a child dripped trimethyl borate (4.5mmol; 0.5ml); continue nitrogen protection and stir 2 hours; 1M hydrochloric acid soln (30ml) quencher is reacted; add water (100ml) precipitation precipitation; wash solid with normal hexane (3*20ml), obtain white powder HP-AN9B-PH44-PY4(0.78g, productive rate 70%).
Embodiment 28
The preparation of compound H P-AN9B-PH44-PY3
[HP-AN9B-PH44-PY3]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-PH44-PY3, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH44-PY3.
Embodiment 29
The preparation of compound H P-AN9B-PH44-PY2
[HP-AN9B-PH44-PY2]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-PH43-1, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH44-PY2.
Embodiment 30
The preparation of compound H P-AN9B-PH43-PY4
[HP-AN9B-PH43-PY4]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-PH43-PY4, through the reaction identical with embodiment 27, obtain compound H P-AN9B-PH43-PY4.
Embodiment 31
The preparation of compound H P-AN9B-2PH44-PY4
[HP-AN9B-2PH44-PY4]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-2PH44-PY4, through the reaction identical with embodiment 27, obtain compound H P-AN9B-2PH44-PY4.
Embodiment 32
The preparation of compound H P-AN9B-2PH44-PY3
[HP-AN9B-2PH44-PY3]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-2PH44-PY3, through the reaction identical with embodiment 27, obtain compound H P-AN9B-2PH44-PY3.
Embodiment 33
The preparation of compound H P-AN9B-NP14-PY3
[HP-AN9B-NP14-PY3]
Except replacing HP-AN9-PH44-PY4 with HP-AN9-NP14-PY3, through the reaction identical with embodiment 27, obtain compound H P-AN9B-NP14-PY3.
Embodiment 34
The preparation of compound H P-L-NP14-PY4-L-NP14-PY4
[HP-L-NP14-PY4-L-NP14-PY4]
By [HP-AN-NP14-PY4] (1mmol, 663mg), [HP-AN9B-NP14-PY4] (1mmol, 425mg) with tetrakis triphenylphosphine palladium (25mg) mixing, add the mixing solutions of toluene (2ml)/ethanol (2ml)/2M Na2CO3 (0.5ml).This reaction system is stirred 4 hours under 100 degrees Celsius, is then cooled to room temperature.By water (40ml) diluting reaction system also with ethyl acetate (3*40ml) extraction.Organic phase anhydrous magnesium sulfate drying, concentrated organic phase also crosses post with silica gel, obtains shallow white solid HP-L-NP14-PY4-L-NP14-PY4(675mg, productive rate 70%).
The NMR data of product are shown in Figure 1.
Embodiment 35
The preparation of compound H P-L-NP14-PY4-L-NP14-PY3
[HP-L-NP14-PY4-L-NP14-PY3]
Except replacing HP-AN9B-NP14-PY4 with HP-AN9B-NP14-PY3, through the reaction identical with embodiment 34, obtain compound H P-L-NP14-PY4-L-NP14-PY3.
MS(EI)m/z=963.36(M+)
Embodiment 36
The preparation of compound H P-L-PH44-PY4-L-PH44-PY4
[HP-L-PH44-PY4-L-PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH44-PY4.
The NMR data of product are shown in Figure 2.
Embodiment 37
The preparation of compound H P-L-PH44-PY4-L-PH44-PY3
[HP-L-PH44-PY4-L-PH44-PY3]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH44-PY3.
The NMR data of product are shown in Figure 3.
In the spectroscopic data diagram 9 of product.
Embodiment 38
The preparation of compound H P-L-PH44-PY4-L-PH44-PY2
[HP-L-PH44-PY4-L-PH44-PY2]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY2, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-PH44-PY2.
The NMR data of product are shown in Figure 4.
Embodiment 39
The preparation of compound H P-L-PH44-PY3-L-PH44-PY2
[HP-L-PH44-PY3-L-PH44-PY2]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY3, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY2, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY3-L-PH44-PY2.
MS(EI)m/z=813.31(M+)
Embodiment 40
The preparation of compound H P-L-PH44-PY2-L-PH44-PY3
[HP-L-PH44-PY2-L-PH44-PY3]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY2, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY2-L-PH44-PY3.
MS(EI)m/z=813.31(M+)
Embodiment 41
The preparation of compound H P-L-PH44-PY3-L-PH44-PY3
[HP-L-PH44-PY3-L-PH44-PY3]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY3, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY3-L-PH44-PY3.
MS(EI)m/z=813.31(M+)
Embodiment 42
The preparation of compound H P-L-PH44-PY2-L-2PH44-PY4
[HP-L-PH44-PY2-L-2PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY2, replacing HP-AN9B-NP14-PY4 with HP-AN9B-2PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY2-L-2PH44-PY4.
The NMR data of product are shown in Figure 5.
Embodiment 43
The preparation of compound H P-L-PH44-PY4-L-NP14-PY2
[HP-L-PH44-PY4-L-NP14-PY2]
Except replacing HP-AN-NP14-PY4 with HP-AN-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-NP14-PY2, through the reaction identical with embodiment 34, obtaining compound H P-L-PH44-PY4-L-NP14-PY2.
MS(EI)m/z=866.33(M+)
Embodiment 44
The preparation of compound H P-L-2PH44-PY4-L-2PH44-PY4
[HP-L-2PH44-PY4-L-2PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-AN-2PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-2PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-2PH44-PY4-L-2PH44-PY4.
The NMR data of product are shown in Figure 6.
Embodiment 45
The preparation of compound H P-L-2PH44-PY4-L-PH44-PY4
[HP-L-2PH44-PY4-L-PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-AN-2PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L-2PH44-PY4-L-PH44-PY4.
MS(EI)m/z=965.38(M+)
Embodiment 46
The preparation of compound H P-L1-PH44-PY3-L-PH44-PY4
[HP-L1-PH44-PY3-L-PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-ANme-PH44-PY3, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L1-PH44-PY3-L-PH44-PY4.
The NMR data of product are shown in Figure 7.
Embodiment 47
The preparation of compound H P-L2-PH44-PY4-L-PH44-PY4
[HP-L2-PH44-PY4-L-PH44-PY4]
Except replacing HP-AN-NP14-PY4 with HP-ANet-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY4, through the reaction identical with embodiment 34, obtaining compound H P-L2-PH44-PY4-L-PH44-PY4.
The NMR data of product are shown in Figure 8.
Embodiment 48
The preparation of compound H P-L2-PH44-PY4-L-PH44-PY3
[HP-L2-PH44-PY4-L-PH44-PY3]
Except replacing HP-AN-NP14-PY4 with HP-ANet-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L2-PH44-PY4-L-PH44-PY3.
MS(EI)m/z=841.35(M+)
Embodiment 49
The preparation of compound H P-L2-PH44-PY4-L-PH44-PY3
[HP-L2-PH44-PY4-L-PH44-PY3]
Except replacing HP-AN-NP14-PY4 with HP-ANet-PH44-PY4, replacing HP-AN9B-NP14-PY4 with HP-AN9B-PH44-PY3, through the reaction identical with embodiment 34, obtaining compound H P-L2-PH44-PY4-L-PH44-PY3.
MS(EI)m/z=993.41(M+)
Embodiment 50
The acquisition of the compound H P-L-NP14-PY4-L-NP14-PY4 electron recombination energy that embodiment 34 obtains
The molecular coordinates of compound H P-L-NP14-PY4-L-NP14-PY4 is input in quantum chemistry software, at b3lyp/6-31G (d, p) optimize under, obtain the ground state energy (E1) of compound respectively, containing the vertical excited energy (E2) of an electronics, containing the adiabatic excited energy (E3) of an electronics, based on the neutral molecule energy (E4) of adiabatic excited state configuration, obtained the electron recombination energy E of this compound by Reorganization Energy calculation formula E=|E1-E4|+|E2-E3|.
Embodiment 51
The acquisition of the compound H P-L-PH44-PY2-L-2PH44-PY4 electron recombination energy that embodiment 42 obtains
Replace HP-L-NP14-PY4-L-NP14-PY4 except with the molecular coordinates of compound H P-L-PH44-PY2-L-2PH44-PY4, through the operation identical with embodiment 50, obtain compound [HP-L-PH44-PY2-L-2PH44-PY4] electron recombination energy.
Embodiment 52
The acquisition of the compound H P-L2-PH44-PY4-L-PH44-PY4 electron recombination energy that embodiment 47 obtains
Replace HP-L-NP14-PY4-L-NP14-PY4 except with the molecular coordinates of compound H P-L2-PH44-PY4-L-PH44-PY4, through the operation identical with embodiment 50, obtain compound [HP-L2-PH44-PY4-L-PH44-PY4] electron recombination energy.
Comparative example
The acquisition of compd A ND electron recombination energy
Except substituting HP-L-NP14-PY4-L-NP14-PY4 with the molecular coordinates of AND, through the operation identical with embodiment 50,
Obtain compd A ND electron recombination energy.
Electron recombination energy data obtained above are as shown in following table says:
E1(a.u.) E2（a.u.） E3（a.u.） E4（a.u.） E（a.u.） Relative mobility
Embodiment 50 2512.3565397 2512.3909196 2512.3987687 2512.3510566 0.01333 1.03
Embodiment 51 2512.3559116 2512.3900936 2512.3968187 2512.3499391 0.0127 1.06
Embodiment 52 2512.3555262 2512.3878386 2512.3951449 2512.3498831 0.01295 1.05
Comparative example 1308.9535859 1308.9672428 1308.9751160 1308.9472085 0.01425 1
According to document (J.Phys.Chem.A2003,107,5241-5251), electron recombination can be less, and electronic mobility is higher.Can see from upper table, embodiment compares conventional AND, and electron recombination can show well, shows that compound of the present invention also can be applied in electroluminescent field as electron transport material.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that, under the guiding of the present invention's design, those skilled in the art can carry out various amendment and improvement, and claims summarise scope of the present invention.

Claims (15)

1. two anthracene compounds as shown in formula I:
Wherein,
L 1and L 2identical or different, represent the replacement of singly-bound, C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 with being mutually independent or not replacing hydrocarbon type aromatic group;
L 3represent the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 independently or do not replace hydrocarbon type aromatic group;
Prerequisite is L 1, L 2and L 3time different x
R 10, R 11, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 21, R 23, R 24, R 25, R 26, R 27and R 28identical or different, represent hydrogen with being mutually independent, halogen, the substituted or unsubstituted alkyl of C1-C10, or the substituted or unsubstituted alkoxyl group of C1-C10.
2. two anthracene compounds according to claim 1, is characterized in that, described L 1with L 2identical, represent singly-bound, the replacement of C2-C60 or the replacement of unsubstituting heterocycle type aromatic group or C6-C60 or do not replace hydrocarbon type aromatic group.
3. two anthracene compounds according to any one of claim 1 to 2, is characterized in that, described L 1, L 2and L 3be expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc, Rd are identical or different, represent hydrogen with being mutually independent, halogen, the replacement of C1-C30 or unsubstituted alkyl, or the replacement of C1-C30 or unsubstituted alkoxyl group.
4. two anthracene compounds according to any one of claim 1 to 2, wherein said L1, L2 and L3 are expressed as follows aromatic group with being mutually independent:
Wherein,
Ra, Rb, Rc can be hydrogen, halogen, the substituted or unsubstituted alkyl of C1-C30, or the substituted or unsubstituted alkoxyl group of C1-C30.
5. two anthracene compounds according to claim 1 and 2, wherein, described L1, L2 and L3 are selected from independently of one another
6. two anthracene compounds, wherein R according to claim 1 and 2 26and R 27be selected from hydrogen, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-or the tertiary butyl independently of one another.
7. two anthracene compounds according to claim 1 and 2, described two anthracene compounds be selected from by
the group of composition.
8. prepare a method for two anthracene compounds according to any one of claim 2 and 5-7, comprising:
1) by formula 4 compound
With formula 5 compound
By being obtained by reacting formula 2 compound
2) by formula 6 compound
With formula 7 compound
Formula 8 intermediate is obtained through suzuki linked reaction
Described formula 8 intermediate is obtained by reacting formula 3 compound by boration
3) described formula 2 compound and described formula 3 compound are obtained two anthracene compounds shown in formula I by suzuki linked reaction:
Wherein,
X 1, X 2, X 3for halogen.
9. prepare a method for two anthracene compounds according to any one of claim 1-8, comprising:
1) by formula 2 compound
With formula 9 compound
Formula 10 compound is obtained by linked reaction
Formula 11 compound is obtained through bromination reaction
2) described formula 11 compound and formula 12 compound
Formula 13 compound is obtained by linked reaction
Formula 14 compound is obtained through bromination reaction
3) described formula 14 compound and formula 15 compound
Two anthracene compounds shown in general formula I are obtained by linked reaction
Wherein,
X 4for halogen.
10. the two anthracene compounds as shown in formula I according to any one of claim 1-7 are preparing in organic electroluminescence device the purposes be used as in luminescent material, electron transport material or hole barrier materials.
11. 1 kinds of organic electroluminescence devices, comprise the organic light emitting medium between pair of electrodes and electrode, comprise the two anthracene compounds of at least one according to any one of claim 1-7 in described organic light emitting medium.
12. organic electroluminescence devices according to claim 11, is characterized in that, described two anthracene compounds are arranged in the electron transfer layer of described organic light emitting medium.
13. organic electroluminescence devices according to claim 11, is characterized in that, described two anthracene compounds are arranged in the luminescent layer of described organic light emitting medium.
14. organic electroluminescence devices according to claim 13, is characterized in that, described two anthracene compounds are as blue emitting material.
15. organic electroluminescence devices according to claim 13, is characterized in that, described two anthracene compounds are as the main body luminescent material of described luminescent layer.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5935721A (en) * 1998-03-20 1999-08-10 Eastman Kodak Company Organic electroluminescent elements for stable electroluminescent
CN101395105A (en) * 2006-03-06 2009-03-25 Lg化学株式会社 Novel anthracene derivative and organic electronic device using the same
CN101967079A (en) * 2009-07-28 2011-02-09 靳焕改 Organic material and application thereof to organic electroluminescent devices
CN102742042A (en) * 2010-01-29 2012-10-17 住友化学株式会社 Luminescent composition and light-emitting element using said composition

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