CN106753340A - A kind of benzimidazole electroluminescent organic material and its preparation method and application - Google Patents
A kind of benzimidazole electroluminescent organic material and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of benzimidazole electroluminescent organic material and its preparation method and application, the structural formula of above-mentioned electroluminescent organic material isIn the benzimidazole electroluminescent organic material that the present invention is provided, spatial configuration of molecules is distortion nonplanar structure, effectively prevent molecule in close accumulation so that the benzimidazole electroluminescent organic material that the present invention is provided has preferable film forming；Meanwhile, the benzimidazole electroluminescent organic material that the present invention is provided has good heat endurance, and glass transition temperature and decomposition temperature are all very high, apply in electroluminescent device, and device can be made to obtain more stable effect and longer service life.
Description
Technical field
The present invention relates to electroluminescent organic material technical field, more particularly to a kind of benzimidazole organic electroluminescent
Material and its preparation method and application.
Background technology
In recent years, Organic Light Emitting Diode (organic light emitting diode, OLED) turns into non-both at home and abroad
Often popular emerging flat-panel screens, because OLED display has self-luminous, wide viewing angle (up to more than 175 DEG C), short anti-
Between seasonable, high luminous efficiency, wide colour gamut, low-work voltage (3~10V), panel is thin, large scale can be made and the panel of deflection and
The characteristic such as processing procedure is simple, and it has potentiality of low cost.It is considered as the nova of super-thin plane display device of future generation.
Although the present whole world has many research institutions and company to put into substantial amounts of energy to go to research and develop organic electroluminescence
Part, but compared with the expection of people, and its industrialization level also differs greatly, and still has many key issues not solved really
Certainly, such as in terms of excitation, stability of photoluminescence, actuation techniques of having chance with and encapsulation technology, also there is a problem that certain so that have
The short life of organic electroluminescence devices, it is less efficient.
Organic luminescent device mainly has positive and negative two electrode layer, and is clipped in luminescent layer, hole transport in the middle of two electrode layers
One layer of layer and electron transfer layer etc. several layers of are constituted.The corresponding material of functional layer for being applied to organic electroluminescence device can divide
Have another name called is luminescent material, hole mobile material and electron transport material.In organic electroluminescent, electronics and hole compound and
The organic molecule for exciting, is not limited by spin selection law, in theory according to statistical distribution, is produced excited triplet state and is excited
The ratio of singlet state is 3:1.Therefore in fluorescence electroluminescent, the excited energy for having 75% is lost.But if using phosphorus
Light electroluminescent material, it is possible to make full use of all of excitation state, so as to promote OLED efficiency to increase substantially.
The content of the invention
For the above mentioned problem that existing OLED material is present, a kind of benzimidazole electroluminescent organic material is now provided
And its preparation method and application, it is desirable to provide a kind of electroluminescent organic material with good photoelectric properties, to meet panel
The requirement of manufacturing enterprise.
Concrete technical scheme is as follows：
The first aspect of the invention is to provide a kind of benzimidazole electroluminescent organic material, with such spy
Levy, above-mentioned electroluminescent organic material is with benzimidazole as parent nucleus, and its structural formula such as formula (I) is shown：
Wherein, n1=1 or 2, n2、n3Separately take from the natural number between 1-4, also, n1、n2、n3And value do not surpass
Cross 6；
Wherein, Ar1、Ar2Separately expression-Ar3- R- or-R, Ar3Selected from aromatic substituent group, R is selected from hydrogen, C1-10
Alkyl, C5-30Aryl, the amido of alkyl or aryl substitution, carbazyl, dibenzofuran group, fluorenyl, alkyl or aryl take
The carbazyl in generation, the dibenzofuran group of alkyl or aryl substitution, the fluorenyl of alkyl or aryl substitution, the base containing substitution or without taking
Dai Ji'sThe base containing substitution or without substitution baseX1Selected from former selected from oxygen atom, sulphur
Son, two (C1-10Straight chained alkyl) substitution season alkyl (or tertiary alkyl), two (C1-10Branched alkyl) substitution season alkyl (or tertiary alkane
Base), aryl substitution season alkyl (or tertiary alkyl), alkyl-substituted tertiary amine groups or aryl substitution tertiary amine groups in one kind,
Ar1、Ar2It is asynchronously hydrogen.
Above-mentioned electroluminescent organic material, also have the feature that, the above-mentioned base containing substitution
Two (C1-10Straight chained alkyl) substitution season alkyl (or tertiary alkyl), two (C1-10Branched alkyl) substitution season alkyl (or tertiary alkyl),
Aryl substitution season alkyl (or tertiary alkyl), alkyl-substituted tertiary amine groups or aryl substitution tertiary amine groups in one kind, Ar4 and
Ar5 is separately selected from the aryl of C6-8.
Above-mentioned electroluminescent organic material, also have the feature that, the above-mentioned base containing substitutionWith the base containing substitution
'sIt is quilt at least one phenyl ringOrtho position unitary substitution, i.e., above-mentioned substitution base can
By C1-C2、C2-C3、C3-C4、C1'-C2'、C2'-C3'、C3'-C4'Or C4'-C5'It is bonded and connects.
Above-mentioned electroluminescent organic material, also has the feature that, X1、X2、X3、X4Be respectively and independently selected from oxygen atom,
Sulphur atom, two (C1-10Straight chained alkyl) substitution quaternary carbon, two (C1-10Branched alkyl) substitution quaternary carbon, aryl substitution quaternary carbon, alkane
One kind in the tertiary amine groups of base substitution or the tertiary amine groups of aryl substitution.
Above-mentioned electroluminescent organic material, also has the feature that, Ar4And Ar5It is phenyl.
Preferably, R is in formula (I)
In any one.
Preferably, the electroluminescent organic material for being provided in the present invention is any in following 1-48 compounds：
It is above some specific structure types, but the benzimidazole electroluminescent organic material provided in the present invention is not
Be confined to these listed chemical constitutions, based on every (I) by formula, substitution base be as defined in the range of simple transformation chemical combination
Thing should all be included.
The second aspect of the invention is to provide the preparation method of above-mentioned electroluminescent organic material, with such spy
Levy, with reactant M as raw material, electroluminescent organic material is prepared through two step coupling reactions, the structural formula of reactant M is such as
Under：
Wherein, n1=1 or 2, n2、n3Separately take from the natural number between 1-4, also, n1、n2、n3And value do not surpass
Cross 6.
Above-mentioned preparation method, is also had the feature that, coupling reaction is selected from Liv Ullmann coupling or Suzuki coupling
One or two.
C-C couplings are completed using Suzuki coupling reaction in the present invention, completing C-N using Liv Ullmann coupling is coupled, the present invention
Suzuki coupling reaction in, with Pd (dppf)2Cl2、Pd(PPh3)4Or Pd (PPh3)2Cl2It is catalyst, with sodium hydride, the tert-butyl alcohol
Potassium, sodium tert-butoxide, butyl lithium (hexane solution), potassium acetate, potassium phosphate, potassium carbonate or cesium carbonate provide alkaline environment, in 0-
Reacted 5-30 hours under conditions of 120 DEG C；In Liv Ullmann coupling of the invention, with Cu2O or copper powder are catalyst, adjacent with 1,10-
Ferrosin is part, with 18- crown ethers -6 as phase transfer catalyst, with sodium hydride, potassium tert-butoxide, sodium tert-butoxide, butyl lithium (just oneself
Alkane solution), potassium acetate, potassium phosphate, potassium carbonate or cesium carbonate alkaline environment is provided, 5-30 is reacted under conditions of 0-120 DEG C small
When.
The third aspect of the invention is to provide above-mentioned electroluminescent organic material in organic electroluminescence device is prepared
Application.
The fourth aspect of the invention is to provide a kind of organic electroluminescence device, contains in the organic electroluminescence device
Multiple functional layers, also have the feature that, at least one functional layer contains above-mentioned electroluminescent organic material.
Prepared organic electroluminescence device generally comprises ITO Conducting Glass, the sky being sequentially overlapped in the present invention
Cave transport layer, luminescent layer (the benzimidazole electroluminescent organic material provided in the present invention is provided), electron transfer layer, electronics
Implanted layer (LiF) and cathode layer (Al), all functional layers are made of vacuum evaporation process.
It should be appreciated that making the purpose of OLED in the present invention, it is intended merely to be better described, is provided in the present invention
The electroluminescent ability that benzimidazole electroluminescent organic material has, and be not to Organic Electricity provided by the present invention
The limitation of the range of application of electroluminescent material.
The beneficial effect of such scheme is：
In the benzimidazole electroluminescent organic material that the present invention is provided, spatial configuration of molecules is distortion non-planar junction
Structure, effectively prevent molecule in close accumulation so that the benzimidazole electroluminescent organic material that the present invention is provided has preferable
Film forming；Meanwhile, the benzimidazole electroluminescent organic material that the present invention is provided has good heat endurance, vitrifying
Transition temperature and decomposition temperature are all very high, apply in electroluminescent device, can make device obtain more stable effect and
Longer service life.
Brief description of the drawings
Fig. 1 is the structural representation of the organic electroluminescence device of offer in embodiments of the invention, by lower floor to upper strata,
It is followed successively by transparent substrate layer (1), transparent electrode layer (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), electronics
Transport layer (6), electron injecting layer (7), negative electrode reflection electrode layer (8), wherein, luminescent layer (5) is related to provided in the present invention
Benzimidazole electroluminescent organic material.
Specific embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Site preparation is described, it is clear that described embodiment is only a part of embodiment of the invention, rather than whole embodiments.It is based on
Embodiment in the present invention, those of ordinary skill in the art obtained on the premise of creative work is not made it is all its
His embodiment, belongs to the scope of protection of the invention.
It should be noted that in the case where not conflicting, the embodiment in the present invention and the feature in embodiment can phases
Mutually combination.
The invention will be further described with specific embodiment below in conjunction with the accompanying drawings, but not as limiting to the invention.
The synthesis of the compound 1 of embodiment 1
The preparation of compound A：
Take 1,1'- (4,5- bis- bromo- 1,2- phenylenes) double (2- phenyl -1H- benzimidazoles) (6.2g, 10.0mmol), two
Aniline (2.1g, 12.0mmol), potassium carbonate (4.2g, 30.0mmol) and 90ml toluene, lead to nitrogen gas stirring 1 hour, anti-to remove
Answer the oxygen in bottle.It is subsequently adding Cu2O (0.3g, 2.0mmol), 1,10- phenanthroline (0.7g, 4.0mmol) and 18- crown ethers-
Flowed back under 6 (0.3g, 1.0mmol) strong stirrings, course of reaction passes through TLC tracing detections.After completion of the reaction, naturally cool to
20-25 DEG C, filtering collects filtrate decompression desolventizing to without cut, carries out column chromatography to residue with pure toluene and purifies, then through first
Benzyl carbinol is recrystallized to give compound A (4.5g, 63.56%).
The preparation of compound 1：
Take compound A (7.1g, 10.0mmol), carbazole (2.0g, 12.0mmol), potassium carbonate (4.2g, 30.0mmol) and
120ml toluene, leads to nitrogen gas stirring 1 hour, to remove the oxygen in reaction bulb.It is subsequently adding Cu2O (0.3g, 2.0mmol), 1,
Flowed back under 10- phenanthrolines (0.7g, 4.0mmol) and 18- crown ethers -6 (0.3g, 1.0mmol) strong stirring, course of reaction passes through
TLC tracing detections.After completion of the reaction, 20-25 DEG C is naturally cooled to, filtering collects filtrate decompression desolventizing to without cut, with pure
Toluene carries out column chromatography purifying to residue, then obtains compound 1 (6.6g, 83.54%) through toluene ethyl alcohol recrystallization.Further
Crude product 320 DEG C of sublimation purifications in chemical gas-phase deposition system, obtain 4.9g white solid powders, and yield is 62.03%.Make
The compound, molecular formula C are recognized with DEI-MS56H38N6, detected value [M+1]+=795.87, calculated value 794.94.
The synthesis of the compound 2 of embodiment 2
The preparation of compound 2：
Take 1,1'- (bromo- 1, the 2- phenylenes of 4-) double (2- phenyl -1H- benzimidazoles) (5.4g, 10.0mmol), 3,6- double
Tri-tert carbazole (3.1g, 11.0mmol), potassium carbonate (4.2g, 30.0mmol) and 90ml toluene, lead to nitrogen gas stirring 1 hour,
To remove the oxygen in reaction bulb.It is subsequently adding Cu2O (0.3g, 2.0mmol), 1,10- phenanthroline (0.7g, 4.0mmol) and
Flowed back under 18- crown ethers -6 (0.3g, 1.0mmol) strong stirring, course of reaction passes through TLC tracing detections.After completion of the reaction, it is natural
20-25 DEG C is cooled to, filtering collects filtrate decompression desolventizing to without cut, carries out column chromatography to residue with pure toluene and purifies,
Again compound 2 (6.3g, 85.13%) is obtained through toluene ethyl alcohol recrystallization.Further crude product is in chemical gas-phase deposition system
300 DEG C of sublimation purifications, obtain 5.4g white solid powders, and yield is 72.97%.The compound is recognized using DEI-MS, point
Minor C52H45N5, detected value [M+1]+=740.77, calculated value 739.95.
The synthesis of the compound 3 of embodiment 3
The preparation of compound B：
Take 1- (3,5- dibromo phenyl) -2- phenyl -1H- benzimidazoles (4.3g, 10.0mmol), (9- phenyl -9H- carbazoles -
2- yls) boric acid (3.7g, 13.0mmol), potassium carbonate (2.8g, 20.0mmol), 15ml water and 80ml toluene, lead to nitrogen gas stirring 1 small
When, to remove the oxygen in reaction bulb.It is subsequently adding Pd (PPh3)4(0.23g, 0.2mmol), flows back under strong stirring, reacts
Journey passes through TLC tracing detections.After completion of the reaction, 20-25 DEG C is naturally cooled to, filtering is collected filtrate decompression desolventizing to nothing and evaporated
Point, column chromatography is carried out to residue with pure toluene and is purified, then through toluene ethyl alcohol recrystallization obtain compound B (4.2g,
71.19%).
The preparation of compound 3：
Take compound B (5.9g, 10.0mmol), (4- (diphenylamines) phenyl) boric acid (3.2g, 11.0mmol), potassium carbonate
(2.8g, 20.0mmol), 15ml water and 60ml toluene, lead to nitrogen gas stirring 1 hour, to remove the oxygen in reaction bulb.Then plus
Enter Pd (PPh3)4(0.23g, 0.2mmol), course of reaction passes through TLC tracing detections.After completion of the reaction, 20-25 is naturally cooled to
DEG C, filtering collects filtrate decompression desolventizing to without cut, carries out column chromatography to residue with pure toluene and purifies, then through toluene second
Alcohol is recrystallized to give compound 3 (6.4g, 85.33%).Further crude product 320 DEG C of distillations in chemical gas-phase deposition system are carried
It is pure, 5.8g white solid powders are obtained, yield is 77.33%.The compound, molecular formula C are recognized using DEI-MS55H38N4,
Detected value [M+1]+=755.81, calculated value 754.92.
The synthesis of the compound 4 of embodiment 4
The preparation of compound 4：
Take 1,1'- (bromo- 1, the 2- phenylenes of 4-) double (2- phenyl -1H- benzimidazoles) (5.4g, 10.0mmol), 3- hexichol
And furan boronic acid (3.1g, 11.0mmol), potassium carbonate (2.8g, 20.0mmol), 15ml water and 90ml toluene, lead to nitrogen gas stirring 1
Hour, to remove the oxygen in reaction bulb.It is subsequently adding Pd (PPh3)4(0.23g, 0.2mmol), course of reaction is tracked by TLC
Detection.After completion of the reaction, 20-25 DEG C is naturally cooled to, filtering collects filtrate decompression desolventizing to without cut, with pure toluene pair
Residue carries out column chromatography purifying, then obtains compound 4 (5.5g, 87.30%) through toluene ethyl alcohol recrystallization.Further crude product
290 DEG C of sublimation purifications in chemical gas-phase deposition system, obtain 4.5g white solid powders, and yield is 71.43%.Use DEI-
MS recognizes the compound, molecular formula C44H28N4O, detected value [M+1]+=629.91, calculated value 628.72.
The synthesis of the compound 5 of embodiment 5
The preparation of compound C：
Take 1,1'- (4,5- bis- bromo- 1,2- phenylenes) double (2- phenyl -1H- benzimidazoles) (6.2g, 10.0mmol), 2-
Dibenzofurans boric acid (2.3g, 11.0mmol), potassium carbonate (2.8g, 20.0mmol), 15ml water and 90ml toluene, logical nitrogen are stirred
Mix 1 hour, to remove the oxygen in reaction bulb.It is subsequently adding Pd (PPh3)4(0.23g, 0.2mmol), flows back under strong stirring,
Course of reaction passes through TLC tracing detections.After completion of the reaction, 20-25 DEG C is naturally cooled to, filtrate decompression desolventizing is collected in filtering
To without cut, column chromatography is carried out to residue with pure toluene and is purified, then through toluene ethyl alcohol recrystallization obtain compound C (5.9g,
83.10%).
The preparation of compound 5：
Take compound C (7.1g, 10.0mmol), diphenylamines (1.9g, 11.0mmol), potassium carbonate (4.2g, 30.0mmol)
With 100ml toluene, lead to nitrogen gas stirring 1 hour, to remove the oxygen in reaction bulb.It is subsequently adding Cu2O (0.3g, 2.0mmol),
Flowed back under 1,10- phenanthroline (0.7g, 4.0mmol) and 18- crown ethers -6 (0.3g, 1.0mmol) strong stirring, course of reaction is led to
Cross TLC tracing detections.After completion of the reaction, 20-25 DEG C is naturally cooled to, filtering collects filtrate decompression desolventizing to without cut, uses
Pure toluene carries out column chromatography purifying to residue, then obtains compound 5 (6.0g, 75.94%) through toluene ethyl alcohol recrystallization.Enter one
Step crude product 330 DEG C of sublimation purifications in chemical gas-phase deposition system, obtain 4.8g white solid powders, and yield is 58.23%.
The compound, molecular formula C are recognized using DEI-MS56H37N5O, detected value [M+1]+=797.02, calculated value 795.93.
Preparation method in the present invention with reference to above-described embodiment 2 prepare compound 12 (molecular formula C50H31N5O,
DEI-MS detected values 712.70, calculated value 717.81), 18 (molecular formula C53H37N5O, DEI-MS detected values 759.32, calculated value
759.30), the preparation method with reference to embodiment 4 prepares (molecular formula C47H34N4, the DEI-MS detected value of compound 34
654.85, calculated value 654.80), with reference to embodiment 5 preparation method prepare compound 45 (molecular formula C56H35N5O,
DEI-MS detected values 735.10, calculated value 793.91).
Organic electroluminescence device embodiment
Device 1-4 is prepared with the above-mentioned electroluminescent organic material in part in embodiments of the invention 6-10, should be managed
Solution, device implementation process and result, are intended merely to preferably explain the present invention, not limitation of the present invention, above-mentioned Organic Electricity
The preparation method of electroluminescence device is as follows
A) neutralizing treatment, pure water, drying carried out successively to ito anode layer (thickness is 150nm), then carry out ultraviolet-
Ozone washing is removing the organic residue on the surface of transparent ITO-anode layer 2；
B) hole injection layer (MoO3) is deposited with ito anode layer, thickness is 10nm；
C) hole transmission layer (TAPC), thickness 80nm are deposited with hole injection layer；
D) luminescent layer (compound that the present invention is provided is deposited with hole transmission layer：Ir(ppy)3=100：10(wt:
Wt), thickness 30nm；
E) electron transfer layer (TPBI) is deposited with luminescent layer, thickness is 40nm；
F) electron injecting layer device (LiF), thickness 1nm are deposited with the electron transport layer；
G) evaporation cathode reflection electrode layer (Al) on electron injecting layer, thickness 80nm.
In the preparation of above-mentioned organic electroluminescence device, the following institute of structural formula of TAPC, Ir (pq) 2acac, TPBI, CBP
Show：
As above after completing device 1-4 and comparative device, anode and negative electrode are coupled together with known drive circuit, is measured
The principal structural layer and test result of the life-span of the current efficiency of device, luminescent spectrum and device, device 1-4 and comparative device
It is as shown in the table：
From upper table analysis, the device of the benzimidazole electroluminescent organic material provided using the present invention, no matter
It is to obtain larger carrying in the driving life-span for obtaining larger change, particularly device than known OLED material in efficiency or life-span
Rise.
Preferred embodiments of the present invention are these are only, embodiments of the present invention and protection domain is not thereby limited, it is right
For those skilled in the art, should can appreciate that all utilization description of the invention and equivalent done by diagramatic content are replaced
Change and obviously change resulting scheme, should be included in protection scope of the present invention.
Claims (8)
1. a kind of benzimidazole electroluminescent organic material, it is characterised in that the electroluminescent organic material is with benzo miaow
Azoles is parent nucleus, shown in its structural formula such as formula (I)：
Wherein, n1=1 or 2, n2、n3Separately take from the natural number between 1-4, also, n1、n2、n3And value be no more than 6；
Wherein, Ar1、Ar2Separately it is selected from-Ar3- R- or-R, Ar3Selected from C1-10The substituted or unsubstituted aryl of alkyl；R is selected
From hydrogen, C1-10Alkyl, C6-30Aryl, alkyl or aryl substitution amido, carbazyl, dibenzofuran group, fluorenyl, alkyl
Or carbazyl, the dibenzofuran group of alkyl or aryl substitution, the fluorenyl of alkyl or aryl substitution, the base containing substitution of aryl substitution
Or without substitution baseThe base containing substitution or without substitution baseX1Selected from being selected from
Oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) substitution season alkyl, two (C1-10Branched alkyl) substitution season alkyl, aryl takes
Generation season alkyl, alkyl-substituted tertiary amine groups or aryl substitution tertiary amine groups in one kind, Ar1、Ar2It is asynchronously hydrogen.
2. electroluminescent organic material according to claim 1, it is characterised in that described containing substitution baseWith the base containing substitutionIt is quilt at least one phenyl ringUnitary replaces, X2、X3It is separately former selected from oxygen atom, sulphur
Son, two (C1-10Straight chained alkyl) substitution season alkyl, two (C1-10Branched alkyl) substitution season alkyl, aryl substitution season alkyl,
One kind in alkyl-substituted tertiary amine groups or the tertiary amine groups of aryl substitution, Ar4And Ar5Separately it is selected from C6-8Aryl.
3. electroluminescent organic material according to claim 2, it is characterised in that the X1, the X2, the X3Respectively
It is independently selected from oxygen atom, sulphur atom, two (C1-10Straight chained alkyl) substitution quaternary carbon, two (C1-10Branched alkyl) substitution quaternary carbon, virtue
One kind in the tertiary amine groups of the quaternary carbon, alkyl-substituted tertiary amine groups or aryl substitution of base substitution.
4. the electroluminescent organic material according to any one of Claims 2 or 3, it is characterised in that the Ar4With the Ar5
It is phenyl.
5. the preparation method of a kind of electroluminescent organic material according to claim any one of 1-4, it is characterised in that with
Reactant M is raw material, and the electroluminescent organic material, the structural formula of the reactant M are prepared through two step coupling reactions
It is as follows：
Wherein, n1=1 or 2, n2、n3Separately take from the natural number between 1-4, also, n1、n2、n3And value be no more than 6.
6. preparation method according to claim 5, it is characterised in that the coupling reaction is selected from Liv Ullmann and is coupled or Suzuki
One or two in coupling.
7. a kind of benzimidazole electroluminescent organic material according to claim any one of 1-4 is preparing organic electroluminescence
Application in luminescent device.
8. a kind of organic electroluminescence device, including multiple functional layers, it is characterised in that at least one described functional layer contains
Benzimidazole electroluminescent organic material described in claim any one of 1-4.
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