CN109134461A - A kind of azepine anthracene derivant and its organic electroluminescence device - Google Patents

A kind of azepine anthracene derivant and its organic electroluminescence device Download PDF

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CN109134461A
CN109134461A CN201811155255.XA CN201811155255A CN109134461A CN 109134461 A CN109134461 A CN 109134461A CN 201811155255 A CN201811155255 A CN 201811155255A CN 109134461 A CN109134461 A CN 109134461A
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unsubstituted
compound
aryl
anthracene derivant
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of azepine anthracene derivant and its organic electroluminescence device, belongs to organic photoelectrical material technical field.The compound has structure shown in formula (I), and one end in the present invention is introducing naphthazine structure, increases the transporting of carrier；In specific position, bridged linkage is introduced, compound molecular weight on the one hand can be increased, the material made has the function of high glass-transition temperature and can prevent crystallization, on the other hand make this kind of compound have certain distortion on stereoeffect, improve its film forming；Overseas Chinese federation's structure the other end introduce the acceptant electronics of cyano class structure, further increase the transporting of carrier.It is used the compound as luminescent layer material of main part and manufactured organic electroluminescence device, shows the advantage that driving voltage is low, luminous efficiency is high, be the luminous organic material of function admirable.

Description

A kind of azepine anthracene derivant and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of azepine anthracene derivant and its organic electroluminescence hair Optical device
Background technique
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as: cathode-ray tube (cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel, PDP it) involves great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is with organic matter for hair The novel electroluminescent device of luminescent material, as a kind of completely new display technology possess in various performances existing display technology without With the advantage of rival, it is simple by feat of its preparation process, have it is all solid state, wide from main light emission, brightness height, high-resolution, visual angle (170 degree or more), fast response time, thin, small in size, light-weight, the usable flexible base board of thickness, low-voltage direct-current drive (3- 10V), low in energy consumption, operating temperature range is wide etc. so that its application market is very extensive, such as lighting system, communication system, vehicle Load display, portable electronic device, fine definition show even military field.
Electroluminescent organic material is constantly realized in recent years to be broken through, and the progress to attract people's attention is achieved, to traditional Display material constitutes strong challenge.After flexible OLED commercialization, associated scientific research and business in the world at present Strength is all in the work for the development this respect done one's utmost.Although electroluminescent organic material research have been achieved with it is huge at Fruit, but there are also some urgent problems to be solved during commercialized by OLED.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is that phosphorus is adulterated in fluorescent host material The method of method and fluorescent host material doping fluorescent (organic matter comprising nitrogen) dopant of luminescent material (organic metal).It is common Material of main part can generally be divided into it is several, as hole transport material of main part, electron-transport material of main part, bipolar host material, Inertia material of main part, fluorescence complex material of main part and phosphorescent complexes material of main part.
In the organic luminescent device prepared using phosphor material, contain trianilino group using TPD etc. mostly
Main body luminescent material of the material as luminescent layer.However, the thermal stability of this kind of materials is poor, cause using phosphorus The service life of the organic luminescent device of luminescent material is shorter, thus reduces the usage degree of such material.How new performance is designed Better material is adjusted, and is always those skilled in the art's urgent problem to be solved.
Summary of the invention
The object of the present invention is to provide a kind of azepine anthracene derivant and preparation method thereof and organic electroluminescence device, this hairs The compound stability of bright offer is good, and carrier transmission performance is good, and glass transition temperature is high, good film-forming property, and synthetic method is simply easy Operation using organic electroluminescence device prepared by the derivative there is good luminous efficiency and service life to show.
Present invention firstly provides a kind of azepine anthracene derivants, have structure shown in following general formula (I):
A is indicated by general formula (II):
(Ⅱ)
Wherein R1Selected from H, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C30 aryl, take One of generation or the heteroaryl of unsubstituted C3~C30；X1Same or different is selected from C or N, and at least one is N；
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of heteroaryl；
B is indicated by general formula (III):
(Ⅲ)
Wherein R2、R3Independently selected from H, CN, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~ One of the aryl of C30, heteroaryl of substituted or unsubstituted C3~C30, R2、R3At least one is cyano；Wherein R4It is selected from Hydrogen, halogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted One of the heteroaryl of C3~C30；Wherein X is selected from C or N.
Preferably, the R3Any one in general formula as follows:
Wherein X1, X2, X3, X4, X5, X6, X7 are independently selected from any one in halogen, CN, trifluoromethyl.
Preferably, any one of the L in singly-bound or structure as follows:
Wherein R5、R6Alkyl, substituted or unsubstituted independently selected from H, halogen or substituted or unsubstituted C1~C10 The aryl of C6~C18, one of the heteroaryl of substituted or unsubstituted C3~C18；X1、X2Independently selected from CR7R8、O、 S、NR9In any one, R7、R8Independently selected from H, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6 Any one in~C18 aryl, substituted or unsubstituted C3~C18 heteroaryl, R7、R8It is not simultaneously H, R7、R8It can connect into Ring, R9Selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C18 aryl, substituted or unsubstituted C3 Any one in~C18 heteroaryl；X3It is selected from one of CH or N same or differently.
Preferably, the R2For cyano.
Preferably, the R3Any one in H, CN or structure as follows:
Preferably, any one of the azepine anthracene derivant in structure as follows:
。
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with And several organic function layers between the anode and the cathode, the organic function layer contain the azepine Anthracene derivant any one or at least two combination.
Preferably, the organic function layer includes luminescent layer, and the luminescent layer includes the azepine anthracene derivant Any one or at least two combination.
Preferably, the azepine anthracene derivant is used as material of main part in luminescent layer.
Beneficial effects of the present invention:
In order to improve the efficiency and stability of OLED device in the prior art, the problems such as service life is short, the present invention is first A kind of simple compounds is provided, which has structure shown in formula (I).One end in the present invention is in the knot for introducing naphthazine Structure increases the transporting of carrier；In specific position, bridged linkage is introduced, compound molecular weight on the one hand can be increased, so that To material have the function of high glass-transition temperature and can prevent crystallization, on the other hand make this kind of compound in sky Between have certain distortion in stereochemical structure, improve its film forming；It is easy to connect in introducing fluorenes alkenes knot in the other end of overseas Chinese federation's structure Nucleophobic structure further increases the transporting of carrier.The compound is used as luminescent layer material of main part and is made Organic electroluminescence device, show the advantage that driving voltage is low, luminous efficiency is high, be the organic light emission material of function admirable Material.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and those skilled in the art The meaning that member is generally understood is identical.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl or naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the total of the group that one or more aromatic core carbon are substituted by hetero atom in aryl Claim, the hetero atom includes but is not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaryl can be monocycle or condensed ring, and example can wrap Include pyridyl group, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow Oxazolyl, acridinyl etc., but not limited to this.
Divalent aryl of the present invention refers to respectively remove a hydrogen atom on two aromatic core carbon of aromatic hydrocarbon molecule after, be left Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more aromatic core carbon in divalent aryl are replaced to obtain by hetero atom Group general name, the hetero atom includes but is not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic Heteroaryl or divalent fused ring heteroaryl, such as can be selected from sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc., But not limited to this.
In substituted alkyl of the present invention, substituted aryl, substituted heteroaryl etc., the substituent group can be independent Selected from D-atom, cyano, nitro, halogen atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, C1- The aryl of C30, the aryloxy group of C1-C30, the arylthio of C1-C30, C3-C30 heteroaryl, the silylation of C1~C30, C2~ Alkylamino radical, aryl amine of C6~C30 of C10 etc., such as D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl Base, tert-butyl, methoxyl group, methyl mercapto, phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrene Base, fluorenyl, 9,9- dimethyl fluorenyl, benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl click Oxazolyl, furyl, thienyl, triphenyl silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine base, acridinyl, piperazine Piperidinyl, pyridyl group, pyrazinyl, triazine radical, pyrimidine radicals etc., but not limited to this.
Present invention firstly provides a kind of azepine anthracene derivants, have the structural formula as shown in formula (I):
A is indicated by general formula (II):
Wherein R1Selected from H, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C30 aryl, take One of generation or the heteroaryl of unsubstituted C3~C30；X1Same or different is selected from CH or N, and at least one For N；
L is selected from the divalent of singly-bound, the divalent aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of heteroaryl；
B is indicated by general formula (III):
(Ⅲ)
Wherein R2、R3Independently selected from H, CN, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~ One of the aryl of C30, heteroaryl of substituted or unsubstituted C3~C30, R2、R3At least one is cyano；Wherein R4It is selected from Hydrogen, halogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted One of the heteroaryl of C3~C30；Wherein X is selected from C or N.
Preferably, the R3Any one in general formula as follows:
Wherein X1, X2, X3, X4, X5, X6, X7 are independently selected from any one in halogen, CN, trifluoromethyl.
Preferably, any one of the L in singly-bound or structure as follows:
Wherein R5、R6Alkyl, substituted or unsubstituted independently selected from H, halogen or substituted or unsubstituted C1~C10 The aryl of C6~C18, one of the heteroaryl of substituted or unsubstituted C3~C18；X1、X2Independently selected from CR7R8、O、 S、NR9In any one, R7、R8Independently selected from H, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6 Any one in~C18 aryl, substituted or unsubstituted C3~C18 heteroaryl, R7、R8It is not simultaneously H, R7、R8It can connect into Ring, R9Selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C18 aryl, substituted or unsubstituted C3 Any one in~C18 heteroaryl；X3It is selected from one of CH or N same or differently.
Preferably, the R2For CN.
Preferably, the R5Selected from any one in H, CN or structure as follows:
Preferably, any one of the azepine anthracene derivant in structure as follows:
。
Some specific structure types of azepine anthracene derivant of the present invention are enumerated above, but the present invention does not limit to It is all based on structure shown in formula (I) in these listed chemical structures, various substituent groups be group as defined above all It should be included.
Azepine anthracene derivant of the present invention, preparation method are as follows:
Bromide containing A and the coupling of the boric acid ester compound containing L, the bromide of gained compound and B is coupled To the azepine anthracene derivant.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is easy to operate, is readily produced.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device is those skilled in the art Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, cathode and are located at Several organic function layers between the anode and cathode include that the azepine anthracene derivant is appointed in the organic function layer It anticipates a kind of or at least two combinations.The organic function layer may include hole injection layer, hole transmission layer, electronic blocking At least one layer in layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, the preferably described organic function layer packet Include luminescent layer, the luminescent layer include the azepine anthracene derivant any one or at least two combination, it is preferred that institute The azepine anthracene derivant stated is as luminescent layer material of main part.
The present invention is not particularly limited the source of raw material employed in following embodiment, can for commercial product or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1:
The preparation of compound 1
The preparation of compound 1-3
It is in round-bottomed flask that compound 1-1 (5.16g, 20mmol), 1-2 (4.28g, 20mmol) and sodium ethoxide is completely molten Then solution heats in 100ml ethyl alcohol and stirs acquired solution.After reaction terminates, diluted with tetrahydrofuran by depressurizing Lower concentration products therefrom and the residue that obtains, and with water and salt water washing.Organic solvent layer is collected, is removed through anhydrous magnesium sulfate Then moisture, filtration residue are concentrated under reduced pressure.The solution silica gel chromatography of concentration is with prepare compound 1-3 6.81g, yield 75%.
The preparation of compound 1
Under the protection of nitrogen, 1-3 (45.38g, 100mmol) is added into 2L reaction kettle, 1-4 (38.22g, 100.08mmol), potassium carbonate (1.24g, 9.00mmol), toluene 200mL stirring.Reactor temperature is raised to 70 DEG C, and Pd is added (PPh3)4(1.04g, 0.90mmol), distilled water 100mL stirring, is stirred at reflux 11h, sufficiently reacts.It is whole that 70mL distilled water is added It after only reacting, is filtered under diminished pressure, is washed with distilled water solid, then use acetone, toluene, THF is recrystallized, risen again after obtaining solid China, re crystallization from toluene obtain 1 47.26g of compound, yield 75%.Mass spectrum m/z:630.15 (calculated value: 630.16).It is theoretical Constituent content (%) C40H18F4N4: C, 76.19；H, 2.88；F, 12.05；N, 8.88 actual measurement constituent content (%): C, 76.18；H, 2.87；F, 12.06；N, it is target product 1 that 8.89 above-mentioned confirmations, which obtain product,.
Embodiment 2:
The preparation of compound 16
The preparation of compound 16
1-2 in embodiment 1 is replaced with into 16-2 as shown above, 1-4 replaces with 16-4 as shown above, obtains compound 16.Mass spectrum m/z:508.17 (calculated value: 508.18).Theoretical elemental content (%) C36H20N4: C, 85.02；H, 3.96；N, 11.02 actual measurement constituent content (%): C, 85.03；H, 3.97；N, 11.03.It is target product 16 that above-mentioned confirmation, which obtains product,.
Embodiment 3:
The preparation of compound 27
The preparation of compound 27
1-2 in embodiment 1 is replaced with into 27-2 as shown above, 1-4 replaces with 27-4 as shown above, obtains compound 27.Mass spectrum m/z:588.14 (calculated value: 588.15).Theoretical elemental content (%) C40H20N4S:C, 81.61；H, 3.42；N, 9.52；S, 5.45 actual measurement constituent content (%): C, 81.62；H, 3.43；N, 9.53；S, 5.44.It is mesh that above-mentioned confirmation, which obtains product, Mark product 27.
Embodiment 4:
The preparation of compound 36
The preparation of compound 36
1-2 in embodiment 1 is replaced with into 36-2 as shown above, 1-4 replaces with 36-4 as shown above, obtains compound 36.Mass spectrum m/z:698.25 (calculated value: 698.26).Theoretical elemental content (%) C51H30N4: C, 87.66；H, 4.33；N, 8.02 Survey constituent content (%): C, 87.67；H, 4.34；N, 8.03.It is target product 36 that above-mentioned confirmation, which obtains product,.
Embodiment 5:
The preparation of compound 48
The preparation of compound 48
1-2 in embodiment 1 is replaced with into 48-2 as shown above, 1-4 replaces with 48-4 as shown above, obtains compound 48.Mass spectrum m/z:508.17 (calculated value: 508.18).Theoretical elemental content (%) C36H20N4: C, 85.02；H, 3.96；N, 11.02 actual measurement constituent content (%): C, 85.03；H, 3.95；N, 11.03.It is target product 48 that above-mentioned confirmation, which obtains product,.
Embodiment 6:
The preparation of compound 57
The preparation of compound 57
1-4 in embodiment 1 is replaced with into 57-4 as shown above, obtains compound 57.Mass spectrum m/z:720.16 (calculated value: 720.18.Theoretical elemental content (%) C46H20F4N4O:C, 76.66；H, 2.80；F, 10.54；N, 7.77；O, 2.22 actual measurement elements Content (%): C, 76.65；H, 2.81；F, 10.53；N, 7.76；O, 2.23.It is target product 57 that above-mentioned confirmation, which obtains product,.
Embodiment 7:
The preparation of compound 70
The preparation of compound 70
1-2 in embodiment 1 is replaced with into 70-2 as shown above, 1-4 replaces with 70-4 as shown above, obtains compound 70.Mass spectrum m/z:665.19 (calculated value: 665.20).Theoretical elemental content (%) C42H24F5N3: C, 75.78；H, 3.63；F, 14.27；N, 6.31 actual measurement constituent content (%): C, 75.77；H, 3.64；F, 14.28；N, 6.32.Above-mentioned confirmation obtains product Target product 70.
Embodiment 8:
The preparation of compound 84
The preparation of compound 84
1-2 in embodiment 1 is replaced with into 84-2 as shown above, 1-4 replaces with 84-4 as shown above, obtains compound 84.Mass spectrum m/z:458.15 (calculated value: 458.16).Theoretical elemental content (%) C32H18N4: C, 83.82；H, 3.96；N, 12.22 actual measurement constituent content (%): C, 83.83；H, 3.95；N, 12.23.It is target product 84 that above-mentioned confirmation, which obtains product,.
Embodiment 9:
The preparation of compound 111
The preparation of compound 111
1-2 in embodiment 1 is replaced with into 111-2 as shown above, 1-4 replaces with 111-4 as shown above, obtains compound 111.Mass spectrum m/z:524.20 (calculated value: 524.21).Theoretical elemental content (%) C37H24N4: C, 84.71；H, 4.61；N, 10.68 actual measurement constituent content (%): C, 84.72；H, 4.62；N, 10.69.It is target product 111 that above-mentioned confirmation, which obtains product,.
Embodiment 10:
The preparation of compound 118
The preparation of compound 118
1-2 in embodiment 1 is replaced with into 118-2 as shown above, 1-4 replaces with 118-4 as shown above, obtains compound 118.Mass spectrum m/z:763.17 (calculated value: 763.18).Theoretical elemental content (%) C49H22F5N3O:C, 77.06；H, 2.90；F, 12.44；N, 5.50；O, 2.09 actual measurement constituent content (%): C, 77.05；H, 2.91；F, 12.43；N, 5.51；O, 2.08.It is above-mentioned Confirm that obtaining product is target product 118.
Embodiment 11:
The preparation of compound 126
The preparation of compound 126
1-2 in embodiment 1 is replaced with into 126-2 as shown above, 1-4 replaces with 126-4 as shown above, obtains compound 126.Mass spectrum m/z:712.16 (calculated value: 712.18).Theoretical elemental content (%) C46H21F5N2O:C, 77.53；H, 2.97；F, 13.33；N, 3.93；O, 2.24 actual measurement constituent content (%): C, 77.54；H, 2.98；F, 13.32；N, 3.94；O, 2.25.It is above-mentioned Confirm that obtaining product is target product 126.
Embodiment 12:
The preparation of compound 136
The preparation of compound 136
1-2 in embodiment 1 is replaced with into 136-2 as shown above, 1-4 replaces with 136-4 as shown above, obtains compound 136.Mass spectrum m/z:769.31 (calculated value: 769.32).Theoretical elemental content (%) C45H21F4N3: C, 79.52；H, 3.11；F, 11.88；N, 6.18 actual measurement constituent content (%): C, 79.53；H, 3.12；F, 11.87；N, 6.17.Above-mentioned confirmation obtains product Target product 136.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa.Then by treated, ito substrate steams Plating.Successively vapor deposition hole injection layer 2-TNATA/50nm, vapor deposition hole transmission layer NPB/30nm, vapor deposition main body CBP: doping Ir (piq)2(acac) 10% mixing/30nm, then vapor deposition electron transfer layer TPBi/30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 1-12]
To compare the CBP in Application Example change into shown compound 1 in embodiment 1-12,16,27,36,48,57, 70、84、111、118、126、136。
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that the compound of the present invention is applied to organic electroluminescence device as luminescent layer material of main part In, it is luminous organic material of good performance that luminous efficiency is high.
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim Defined by the case where spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (9)

1. a kind of azepine anthracene derivant, which is characterized in that have structure shown in following general formula (I):
A is indicated by general formula (II):
Wherein R1Selected from H, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C30 aryl, replace or not One of substituted heteroaryl of C3~C30；X1Same or different is selected from CH or N, and at least one is N；
L is selected from the divalent heteroaryl of singly-bound, the divalent aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 One of base；
B is indicated by logical formula (III):
Wherein R2、R3Independently selected from H, CN, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C6~C30 Aryl, one of the heteroaryl of substituted or unsubstituted C3~C30, R2、R3At least one is cyano；Wherein R4Selected from hydrogen, Halogen, the alkyl of substituted or unsubstituted C1~C30, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3 One of the heteroaryl of~C30；Wherein X is selected from C or N.
2. azepine anthracene derivant according to claim 1, which is characterized in that the R3Appointing in general formula as follows It anticipates one kind:
Wherein X1, X2, X3, X4, X5, X6, X7 are independently selected from any one in halogen, CN, trifluoromethyl.
3. azepine anthracene derivant according to claim 1, which is characterized in that the L is selected from singly-bound or knot as follows Any one in structure:
Wherein R5、R6Independently selected from H, halogen, the alkyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C6~ One of the aryl of C18, heteroaryl of substituted or unsubstituted C3~C18；X1、X2Independently selected from CR7R8、O、S、NR9In Any one, R7、R8Independently selected from H, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C18 virtue Any one in base, substituted or unsubstituted C3~C18 heteroaryl, R7、R8It is not simultaneously H, R7、R8Cyclization, R can be connected9Choosing It is miscellaneous from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C18 aryl, substituted or unsubstituted C3~C18 Any one in aryl；X3It is selected from one of CH or N same or differently.
4. azepine anthracene derivant according to claim 1, which is characterized in that the R2For CN.
5. azepine anthracene derivant according to claim 1, which is characterized in that the R3Selected from H, CN or knot as follows Any one in structure:
6. azepine anthracene derivant according to claim 1, it is characterised in that the azepine anthracene derivant is selected from as follows Any one in structure:
7. a kind of organic electroluminescence device, including anode, cathode and several between the anode and the cathode A organic function layer, which is characterized in that include that the described in any item naphthazines of claim 1~6 spread out in the organic function layer Biology any one or at least two combination.
8. a kind of organic electroluminescence device according to claim 7, which is characterized in that the organic function layer includes hair Photosphere, the luminescent layer include include the described in any item azepine anthracene derivants of claim 1~6 any one or at least two Combination.
9. a kind of organic electroluminescence device according to claim 7, which is characterized in that the azepine anthracene derivant is being sent out It is used as material of main part in photosphere.
CN201811155255.XA 2018-09-30 2018-09-30 A kind of azepine anthracene derivant and its organic electroluminescence device Withdrawn CN109134461A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109293610A (en) * 2018-10-31 2019-02-01 长春海谱润斯科技有限公司 A kind of dibenzofuran derivative and its organic electroluminescence device
CN110615758A (en) * 2019-10-15 2019-12-27 江南大学 Preparation method of 9-di (4-pyridine) ethylene-fluorene with aggregation-induced emission effect

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109293610A (en) * 2018-10-31 2019-02-01 长春海谱润斯科技有限公司 A kind of dibenzofuran derivative and its organic electroluminescence device
CN109293610B (en) * 2018-10-31 2021-09-07 长春海谱润斯科技股份有限公司 Dibenzofurane derivative and organic electroluminescent device thereof
CN110615758A (en) * 2019-10-15 2019-12-27 江南大学 Preparation method of 9-di (4-pyridine) ethylene-fluorene with aggregation-induced emission effect
CN110615758B (en) * 2019-10-15 2022-06-10 江南大学 Preparation method of 9-di (4-pyridine) ethylene-fluorene with aggregation-induced emission effect

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