CN109251203A - Pyrazolo indazole derivative and its application - Google Patents
Pyrazolo indazole derivative and its application Download PDFInfo
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Abstract
The invention discloses a kind of pyrazolo indazole derivative, general formula such as following formula:Wherein Ar1Selected from hydrogen or Ar1With Ar2It is respectively and independently selected from C6~C30Substituted or non-substituted aryl or condensed-nuclei aromatics group, C3~C30Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.Work as Ar1And Ar2When being respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, the substituent group thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from Si (R1)3, the R1Selected from C1~C6Alkyl.Pyrazolo indazole derivative provided by the invention can be effectively reduced the operating voltage of organic electroluminescence device, and improve the luminous efficiency of organic electroluminescence device.
Description
Technical field
The invention belongs to field of organic electroluminescence, it is more particularly related to a kind of novel pyrazolo indazole
Derivative further relates to the organic electroluminescence device for having used the pyrazolo indazole derivative.
Background technique
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, view
The a series of advantages such as angular width, light-weight, composition and simple process, compared with liquid crystal display, display of organic electroluminescence
Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but lower than response speed
The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance
The research of efficient organic material focuses more on, an excellent in efficiency service life long organic electroluminescence device be usually device architecture with
The result of the optimization collocation of various organic materials.In the most common OLED device structure, the organic of following type is generally included
Material: hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor
Body material) and corresponding material of main part etc..
The electron transport material that tradition uses in electroluminescent device is Alq3, but the electron mobility of Alq3 is relatively low
(about in 10-6cm2/Vs).In order to improve the electronic transmission performance of electroluminescence device, researcher has done a large amount of exploration
Research work.LG chemistry reports a series of derivative of pyrenes in the patent specification of China, is used as in electroluminescence device
Electron-transport and injection material improve the luminous efficiency (publication number CN 101003508A) of device.Cao Yong et al. synthesizes
FFF-Blm4(J.Am.Chem.Soc.；(Communication)；2008；130(11)；3282-3283) as electron-transport and
Injection layer material (with Ba/Al and individually use Al as cathode compared with), significantly improves the electron injection and transmission of device,
Improve electroluminescence efficiency.Kodak is at United States Patent (USP) (publication number US 2006/0204784 and US 2007/0048545)
In, mixed electronic transport layer is mentioned, using a kind of material of low lumo energy and the electron-transport material of another low bright voltage
Material and other materials such as metal material etc. adulterate.
Ideal electron transport material, it should the characteristic with following several respects: there is reversible electrochemical reducting reaction；
HOMO and lumo energy are suitable；Electron mobility is high；Good film-forming property；Tg high；It is preferably able to stop hole.From compound structure side
Face, it is desirable that molecule contains electron deficient structural unit, receives electronic capability with good；Molecular weight is sufficiently large, guarantee have compared with
High Tg, to have good thermal stability, while molecular weight cannot be too big, in favor of vacuum evaporation film forming.
The electron transport material performance being currently known is unsatisfactory, and industry is still badly in need of developing new electron transport material.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of novel pyrazolo Yin for organic electroluminescence device
Zole derivatives, to further increase the luminescent properties of organic electroluminescence device.
Another of the invention technical problems to be solved are to provide that a kind of operating voltage is low, luminous efficiency is high, the service life is long
Organic electroluminescence device.
To solve the above problems, pyrazolo indazole derivative provided by the invention has structure shown in logical formula (I) as follows:
Wherein, Ar1Selected from hydrogen, or it is selected from C6~C30Substituted or non-substituted aryl or condensed-nuclei aromatics group, C3~
C30Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, Ar2Selected from C6~C30Substituted or non-substituted aryl or
Condensed-nuclei aromatics group, C3~C30Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.Work as Ar1And Ar2Independently select
When from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, the substituent group thereon is independently selected from
Halogen, cyano, nitro, or it is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group,
Or it is selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
Specifically, as the above-mentioned Ar of definition1With Ar2Refer to when being respectively and independently selected from aryl selected from certain amount ring skeleton
Aromatics ring system of carbon atom, including single ring architecture substituent group such as phenyl etc. also include the aromatic ring substitution for being covalently attached structure
Group such as xenyl, terphenyl etc..
Specifically, as the above-mentioned Ar of definition1With Ar2Refer to when being respectively and independently selected from condensed-nuclei aromatics group with certain amount ring
Aromatics ring system of backbone carbon atoms, including condensed cyclic structure substituent group such as naphthalene, anthryl etc. also include condensed cyclic structure substituent group
The building stone such as benzene binaphthyl, naphthalene xenyl, biphenyl dianthranide base etc. that group is connected with single ring architecture aryl, further includes covalent
The thick aromatic ring substituents of connection structure are rolled into a ball such as binaphthyl.
Specifically, as the above-mentioned Ar of definition1With Ar2Refer to when being respectively and independently selected from heteroaryl or condensed hetero ring aromatic hydrocarbon group and includes
One or more is selected from B, N, O, S, P (=O), the hetero atom of Si and P and monocycle or fused ring aryl with ring carbon atom.
Further, in formula (I), preferably Ar1Selected from hydrogen, or it is selected from C6~C20Substituted aryl or condensed-nuclei aromatics base
Group, C5~C20Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, Ar2Selected from C6~C20Substituted aryl or thick
Aromatic hydrocarbon group, C5~C20Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group.
Work as Ar1And Ar2It is respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group
When, the substituent group thereon, which is independently selected from, preferably is selected from F, cyano, or is selected from C1~C5Alkyl or cycloalkyl, Si (CH3)3、
Alkenyl, alkoxy or thio alkoxy group.
Further, work as Ar1And Ar2When being respectively and independently selected from substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group,
The hetero atom is preferably one or more O, S and N.
Further, Ar1With Ar2It can be the same or different, preferably Ar1With Ar2It is different.
Further, in formula (I), work as Ar1And Ar2It is specific excellent when being independently preferably aryl or fused ring aryl group
Select group include: phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, triphenylene, pyrenyl,
Base,Base or aphthacene base；The phenyl replaced by furyl, thienyl, pyrimidine radicals, pyrrole radicals and/or pyridyl group；2- biphenyl
Base, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- three
Xenyl -4- base, m- terphenyl -3- base and m- terphenyl -2- base.Benzene binaphthyl, 4- naphthylphenyl, 6- phenylnaphthalene
Base, 7- phenyl phenanthryl.
Above-mentioned naphthalene is in group composed by 1- naphthalene and 2- naphthalene；The anthryl is selected from by 1- anthryl, 2- anthryl and 9-
In group composed by anthryl；The fluorenyl is selected from the group as composed by 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl and 9- fluorenyl
In；The fluorenyl derivative is selected from by 9,9 '-dimethyl fluorenes, in group composed by 9,9 '-spiral shell, two fluorenes and benzfluorene；The pyrenyl
In the group as composed by 1- pyrenyl, 2- pyrenyl and 4- pyrenyl；The aphthacene base is selected from by 1- aphthacene base, 2- aphthacene
In group composed by base and 9- aphthacene base.
Further, in formula (I), Ar1And Ar2When being independently preferably heteroaryl groups, specific preferred group packet
It includes: furyl, benzofurane base, thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrrole
Piperazine base, fluorenyl, indeno fluorenyl, quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, different benzo
Furyl, indyl, benzoquinoline, benzimidazole, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl
And its diazole, coffee quinoline base, at least one in coffee quinoline benzothiazolyl and benzodioxole group that derivative, phenyl replace
Kind, wherein the carbazole radical derivative can include but is not limited to 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo
At least one of carbazole and indolocarbazole.
The molecular weight of pyrazolo indazole compounds of the invention is preferably 1000 hereinafter, more preferably 450~900, into
One step is preferably 600~800, molecular size range suitable in this way, is all offered convenience to the synthesis of compound, dissolution, vapor deposition, and
And luminescent properties are more preferable.
Further, in logical formula (I) of the invention, following specific structure compounds: A1-A15 can preferably be gone out, these changes
It is only representative to close object.
The advantages of general formula compound of the present invention, is:
It 1, can when the position 2,5,7,10- of general formula compound mother nucleus structure pyrazolo indazole of the present invention exists simultaneously substituent group
The active site for protecting parent nucleus has positive effect to the stability for keeping compound, while can make Cloud Distribution mother Yu
On core, LUMO distribution is consistent with Cloud Distribution；Ar in general formula of the present invention1With Ar2It can be the same or different, when 2,7-
Bit substituent and 5 when 10- substituent group difference, reduces the symmetry of molecule, and the film forming that can be more advantageous to molecule improves.
2, the precursor structure of general formula compound of the present invention has coplanarity, and designed compound structure well
For center symmetrical structure, it is very beneficial for the transition of electronics in this way, thus can ensure that its electronic transmission performance is very good, thus
The compounds of this invention carrier transport with higher, opposite optimum is as the electron-transport in organic electroluminescence device
Material, so as to significantly reduce the operating voltage for the organic electroluminescence device for using the compounds of this invention, while compound
The high mobility being had also makes the thickness control of material have broader adjusting range, and the film thickness for increasing material can not be shown
Landing influences the operating voltage of device；
3, the precursor structure of general formula compound of the present invention has deeper LUMO, and the position 2- of pyrazolo indazole is connect with 7-
Identical substituent group, and 5- connect identical substituent group with 10-, realize the performance of good transmission electronics, together
When keep coplanar structure to be conducive to the film forming of molecule；The change for replacing ground level and electronic property, can finely tune most
The energy level and transmission performance of whole target compound, such compound are used as electron transport layer materials, can improve significantly
The luminous efficiency of device；
4, general formula compound of the invention be particularly suitable for be used as electron transport material, can preferably with luminous layer main body material
The lumo energy of material matches, and so as to which device operating voltages are effectively reduced and improve device light emitting efficiency, extends the device longevity
Life has very important practical significance in the manufacture of organic electroluminescence device.
5, the molecular weight of pyrazolo indazole compounds of the invention is preferably 1000 hereinafter, more preferably 450~900,
Further preferably 600~800, molecular size range suitable so all offers convenience to the synthesis of compound, dissolution, vapor deposition,
And luminescent properties are more preferable.
The present invention also provides the organic electroluminescence devices for using aforementioned present invention general formula compound.Of the invention is organic
EL device structure and well known device have no difference, generally comprise first electrode, second electrode and insertion described first
One layer between electrode and second electrode or mostly at organic layer, which is characterized in that the organic layer includes above-mentioned pyrazolo indazole
Derivative.As the organic layer between first electrode and second electrode, usually have electron injecting layer, electron transfer layer, luminescent layer,
The organic layers such as hole transmission layer, hole injection layer.Pyrazolo indazole derivative of the invention can be, but not limited in organic electroluminescence
It is used as electron transport material in luminescent device.
Wherein, the preferred example as organic electroluminescence device of the invention can be enumerated compound A1~A15, be used
Make the organic electroluminescence device of electron transport layer materials.Organic electroluminescence device of the invention is based on the compounds of this invention
Excellent properties can reduce device and play bright and operating voltage, improve device efficiency, extend device lifetime.
Detailed description of the invention
From the detailed description with reference to the accompanying drawing to the embodiment of the present invention, these and/or other aspects of the invention and
Advantage will become clearer and be easier to understand, in which:
Fig. 1 is the highest occupied molecular orbital (HOMO) of the compounds of this invention A1；
Fig. 2 is the lowest unoccupied molecular orbital (LUMO) of the compounds of this invention A1；
Fig. 3 is the highest occupied molecular orbital (HOMO) of the compounds of this invention A9；
Fig. 4 is the lowest unoccupied molecular orbital (LUMO) of the compounds of this invention A9.
Specific embodiment
Below with reference to following examples set forth the preparation methods of representation compound of the invention.Due to the compounds of this invention
Skeleton having the same, those skilled in the art be based on these preparation methods, can by known functional group's conversion method, readily
Synthesize other the compound of the present invention.Hereinafter, also providing the preparation method and photism of the luminescent device comprising the compound
Matter measurement.
Synthetic example:
Preparation is simple for the compounds of this invention, and raw material is easy to get, and is suitable for volume production amplification.
Various chemicals used in synthetic example for example petroleum ether, ethyl acetate, n-hexane, toluene, tetrahydrofuran,
Bis- (bromomethyl) benzene of methylene chloride, carbon tetrachloride, acetone, 1,2-, CuI, o-phthaloyl chloride, phenylhydrazine hydrochloride, trifluoroacetic acid, second
Sour, trans--diaminocyclohexane, iodobenzene, cesium carbonate, potassium phosphate, ethylenediamine, benzophenone, cyclopentanone, 9-Fluorenone, the tert-butyl alcohol
The bromo- 2- methyl naphthalene of sodium, Loprazolam, 1-, o-dibromobenzene, butyl lithium, Bromofume, o-dibromobenzene, benzoyl peroxide, 1-
(2- bromophenyl) -2- methyl naphthalene, N- bromo-succinimide, methoxyl methyl San Jia Ji phosphonium chloride, three (dibenzalacetones) two
Palladium, tetrakis triphenylphosphine palladium, 1,3- pairs of 2-phenyl-phosphine oxide nickel chloride, carbazole, 3,6- Dimethylcarbazole, 3- (2- naphthalene) -6-
The bases such as phenyl carbazole, N- phenyl carbazole -3- boric acid, 9- (2- naphthalene) carbazole -3- boric acid, the bromo- 2,5- diaminobenzene of 1,4- bis-
Industrial chemicals chemical products can be commercially available at home.The compound for the synthetic method that do not mention in the present invention all passes through
The raw produce that commercial sources obtain.
The analysis detection of intermediate and compound in the present invention uses AB SCIEX mass spectrograph (4000QTRAP) and cloth Shandong
Gram Nuclear Magnetic Resonance (400M).
The synthesis of 1. compound A1 of synthetic example
Under nitrogen protection, raw material A (26.5g, 100mmol) and propionic aldehyde (2.30eq), concentrated hydrochloric acid 300ml open stirring, add
Heat reacts 12h to flowing back, and reacts basified, and ethyl acetate extraction, organic phase is dry, crosses silicagel column, and concentration is boiled with petroleum ether
It washes, obtains intermediate M2 (20.1g, yield 59.6%).
Under nitrogen protection, to mechanical stirring is equipped with, 4- bromo biphenyl is added in intermediate B (6.7g, 20mmol) there-necked flask
(2.5eq.), potassium carbonate 5eq, Pd (Pph3)4(2%), toluene 1000ml+ ethyl alcohol 500ml+300ml water is opened stirring, is heated to
8h is reacted in reflux.Organic phase silica gel column chromatography, concentration, obtains A1 (9.0g, 93.7%) with re crystallization from toluene.
The magnetic resonance spectroscopy data of compound A1:
1H NMR(400MHz,Chloroform)δ8.40(s,2H),8.33(s,3H),7.75(s,3H),7.55(s,
4H), 7.48 (t, J=28.0Hz, 10H), 7.24 (d, J=4.0Hz, 8H)
The synthesis of 2. compound A2 of synthetic example
With compound A1, difference is to replace with 4- bromo biphenyl into the 2- bromonaphthalene of equivalent synthesis step, after reaction,
Isolated white solid 6.2g.
The magnetic resonance spectroscopy data of compound A2:
1H NMR (400MHz, Chloroform) δ 8.86 (s, 1H), 8.33 (d, J=12.0Hz, 2H), 8.20 (s, 1H),
8.08 (d, J=12.0Hz, 2H), 7.99 (s, 1H), 7.63 (s, 1H), 7.57 (d, J=12.0Hz, 2H), 7.38 (s, 2H),
7.14(s,1H),6.90(s,1H).
The synthesis of 3. compound A-13 of synthetic example
Synthesis step is to replace with 4- bromo biphenyl into 1- (4- bromobenzene) naphthalene of equivalent, react with compound A1, difference
After, isolated white solid 6.4.
1H NMR (400MHz, Chloroform) δ 9.11 (s, 2H), 8.90 (s, 2H), 8.31 (d, J=12.0Hz,
50H), 7.86 (dd, J=8.0,59.0Hz, 6H), 7.65 (s, 1H), 7.65 (s, 2H), 7.62 (s, 4H), 7.55 (s, 2H),
7.49(s,2H),7.41(s,1H).
The synthesis of 4. compound A4 of synthetic example
Synthesis step is to replace with 4- bromo biphenyl into the 2- bromine triphenylene of equivalent, reacts and tie with compound A1, difference
Shu Hou, isolated white solid 4.6g.
1H NMR (400MHz, Chloroform) δ 9.11 (s, 1H), 8.84 (s, 1H), 8.31 (d, J=10.0Hz, 3H),
8.04 (dd, J=10.0,6.0Hz, 4H), 7.96-7.96 (m, 2H), 7.85 (d, J=8.0Hz, 2H), 7.63 (s, 1H), 7.57
(d, J=10.0Hz, 3H), 7.49 (s, 1H), 7.38 (s, 1H)
The synthesis of 5. compound A-45 of synthetic example
With compound A1, difference is to replace with 4- bromo biphenyl into equal 2- bromine phenanthrene synthesis step, after reaction, separates
To white solid 5.2g.
1H NMR(400MHz,Chloroform)δ8.97(s,1H),8.56(s,2H),8.35(s,1H),8.28(s,
2H), 7.79 (t, J=8.0Hz, 4H), 7.65 (s, 2H), 7.63-7.47 (m, 4H), 7.41 (s, 1H), 7.28 (s, 1H)
The synthesis of 6. compound A6 of synthetic example
Synthesis step is the bromo- 2- phenylpyridine of the 5- that 4- bromo biphenyl is replaced with equivalent with compound A1, difference, instead
After answering, isolated 5.1g.
1H NMR(400MHz,Chloroform)δ8.97(s,1H),8.56(s,2H),8.35(s,1H),8.28(s,
2H), 8.08 (d, J=12.0Hz, 2H), 7.99 (s, 1H), 7.79 (t, J=8.0Hz, 4H), 7.63 (s, 1H), 7.60-7.47
(m, 6H), 7.33 (d, J=10.0Hz, 3H), 7.24 (s, 2H)
The synthesis of 7. compound A7 of synthetic example
Intermediate B is dissolved in chloroform, bromine (3eq) is added dropwise under room temperature, normal-temperature reaction end of reaction for 24 hours, washing, ethyl ester
Extraction, concentration, obtains yellow powder C.
Under nitrogen protection, to mechanical stirring is equipped with, it is phonetic that 5- (4 bromobenzene) is added in intermediate C (6.7g, 20mmol) there-necked flask
Pyridine (2.5eq.), potassium carbonate 5eq, Pd (Pph3)4(2%), toluene 1000ml+ ethyl alcohol 500ml+300ml water opens stirring, heating
To reflux, 8h is reacted.Organic phase silica gel column chromatography, concentration, obtains D (6.5g, 76.8%) with re crystallization from toluene.
Under nitrogen protection, to mechanical stirring is equipped with, phenyl boric acid (2.5eq.) is added in intermediate D (20mmol) there-necked flask,
Potassium carbonate 5eq, Pd (Pph3)4(2%), toluene 1000ml+ ethyl alcohol 500ml+300ml water opens stirring, is heated to flowing back, and reacts
8h.Organic phase silica gel column chromatography, concentration, obtains A7 (8.6g, 89.5%) with re crystallization from toluene.
1H NMR (400MHz, Chloroform) δ 8.97 (s, 2H), 8.56 (s, 3H), 8.35 (s, 1H), 7.88 (d, J=
10.0Hz, 2H), 7.63 (d, J=12.0Hz, 4H), 7.60-7.44 (m, 6H), 7.39 (d, J=12.0Hz, 4H), 7.27 (d, J
=12.0Hz, 2H)
The synthesis of 8. compound A-28 of synthetic example
With compound A7, difference is to replace with 5- (4 bromobenzene) pyrimidine into the 2- (4- bromophenyl) of equivalent synthesis step
3- Phenyl-benzoimidazol, after reaction, isolated white solid 5.1g.
1H NMR (400MHz, Chloroform) 8.97 (t, J=8.0Hz, 1H), 8.56 (s, 10H), 8.54 (s, 3H),
8.54-8.33 (m, 1H), 8.32 (s, 3H), 8.08 (d, J=12.0Hz, 1H), 8.33-7.86 (m, 3H), 7.83-7.74 (m,
2H), 7.67-7.52 (m, 3H), 7.52 (s, 2H), 7.52-7.34 (m, 4H), 7.27 (d, J=12.0Hz, 2H)
The synthesis of 9. compound A9 of synthetic example
Synthesis step is with compound A1, and difference is to replace with 5- (4 bromobenzene) pyrimidine into the bromobenzene of equivalent, by phenyl boric acid
Replace with 2- (4- phenyl boric acid) pyridine of equivalent, after reaction, isolated white solid 5.2g.
1H NMR(400MHz,Chloroform)δ9.29(s,2H),8.97(s,1H),8.35(s,1H),7.96(s,
2H), 7.65 (s, 2H), 7.54 (d, J=12.0Hz, 4H), 7.41 (s, 2H), 7.25 (s, 2H)
The synthesis of 10. compound A10 of synthetic example
With compound A1, difference is to replace with 5- (4 bromobenzene) pyrimidine into the 4- bromo biphenyl of equivalent synthesis step, reaction
After, isolated white solid 4.8g.
1H NMR (400MHz, Chloroform) δ 8.97 (s, 2H), 8.69 (d, J=8.0Hz, 4H), 8.37 (d, J=
10.0Hz, 3H), 8.07 (d, J=10.0Hz, 3H), 7.94 (s, 1H), 7.85 (s, 3H), 7.65 (s, 3H), 7.54 (d, J=
12.0Hz,4H),7.41(s,3H).
The synthesis of 11. compound A11 of synthetic example
With compound A1, difference is to replace with 5- (4 bromobenzene) pyrimidine into the 4- bromo biphenyl of equivalent, benzene boron synthesis step
Acid replaces with 2- (4- phenyl boric acid) pyridine of equivalent, after reaction, isolated white solid 4.9g.
1H NMR(400MHz,Chloroform)δ9.57(s,2H),9.09(s,4H),8.97(s,2H),8.35(s,
2H), 7.65 (s, 4H), 7.54 (d, J=12.0Hz, 7H), 7.41 (s, 1H), 7.25 (s, 8H)
The synthesis of 12. compound A12 of synthetic example
Synthesis step is with compound A1, and difference is to replace with 5- (4 bromobenzene) pyrimidine into the 4- bromo biphenyl of equivalent, by benzene
2- (4- phenyl boric acid) 3- Phenyl-benzoimidazol that boric acid replaces with equivalent obtains faint yellow solid 4.7g.
1H NMR (400MHz, Chloroform) δ 9.13 (s, 2H), 8.97 (s, 3H), 8.92 (s, 1H), 8.28 (d, J=
10.0Hz, 4H), 8.07 (s, 2H), 7.65 (s, 4H), 7.63-7.44 (m, 9H), 7.40 (d, J=8.0Hz, 3H), 7.25 (s,
8H).
The synthesis of 13. compound A13 of synthetic example
Synthesis step is with compound A1, and difference is to replace with 5- (4 bromobenzene) pyrimidine into the 4- bromo biphenyl of equivalent, by benzene
5- (4- phenyl boric acid) pyrimidine that boric acid replaces with equivalent obtains faint yellow solid 4.6g.
1H NMR(400MHz,Chloroform)δ9.68(s,4H),8.97(s,2H),8.35(s,2H),7.65(s,
4H), 7.54 (d, J=12.0Hz, 7H), 7.41 (s, 1H), 7.25 (s, 8H)
The synthesis of 14. compound A14 of synthetic example
With compound A1, difference is to replace with 5- (4 bromobenzene) pyrimidine into 2- (4- bromobenzene) -4- of equivalent synthesis step
Phenyl isoquinolin quinoline obtains faint yellow solid 6.6g.
1H NMR (400MHz, Chloroform) δ 8.41 (d, J=12.0Hz, 2H), 8.36-8.22 (m, 4H), 8.12-
7.67 (m, 6H), 7.80 (d, J=12.0Hz, 2H), 7.75 (dd, J=7.2,12.4Hz, 4H), 7.72 (d, J=10.0Hz,
2H), 7.70 (s, 1H), 7.71-7.46 (m, 6H), 7.34 (d, J=10.0Hz, 20H), 7.25 (d, J=12.4Hz, 6H),
7.14(s,1H),1.69(s,12H).
The synthesis of 15. compound A15 of synthetic example
For synthesis step with compound A1, difference is that the chloro- 4- phenyl of 2- that 5- (4 bromobenzene) pyrimidine is replaced with to equivalent is different
Quinoline obtains faint yellow solid 5.8g.
1H NMR (400MHz, Chloroform) δ 9.19 (s, 1H), 8.35 (dd, J=28.0,12.0Hz, 6H), 7.92
(s, 3H), 7.67 (s, 4H), 7.55 (s, 3H), 7.49 (s, 1H), 7.24 (d, J=4.0Hz, 6H)
The analysis detecting data of specific preferably synthetic structural compounds disclosed in the embodiment of the present invention arranges in table 1 below:
| Compound | Molecular formula | MS(m/e) | Elemental analysis (%) |
| A1 | C32H22N4 | 462.8 | C,83.09；H,4.79；N,12.11 |
| A2 | C28H18N4 | 410.5 | C,81.93；H,4.42；N,13.65 |
| A3 | C40H26N4 | 562.5 | C,85.38；H,4.66；N,9.96 |
| A4 | C44H26N4 | 610.4 | C,86.53；H,4.29；N,9.17 |
| A5 | C36H22N4 | 510.8 | C,84.68；H,4.34；N,10.97 |
| A6 | C30H20N6 | 464.7 | C,77.57；H,4.34；N,18.09 |
| A7 | C40H26N8 | 618.3 | C,77.65；H,4.24；N,18.11 |
| A8 | C58H38N8 | 846.1 | C,82.25；H,4.52；N,13.23 |
| A9 | C42H28N6 | 616.5 | C,81.80；H,4.58；N,13.63 |
| A10 | C44H30N4 | 614.5 | C,85.97；H,4.92；N,9.11 |
| A11 | C54H36N6 | 768.0 | C,84.35；H,4.72；N,10.93 |
| A12 | C70H46N8 | 998.2 | C,84.14；H,4.64；N,11.21 |
| A13 | C52H34N8 | 770.9 | C,81.02；H,4.45；N,14.54 |
| A14 | C60H38N8 | 870.1 | C,82.74；H,4.40；N,12.86 |
| A15 | C48H30N8 | 718.6 | C,80.20；H,4.21；N,15.59 |
Device embodiments:
The typical structure of the OLED organic electroluminescence device prepared in device embodiments are as follows:
Substrate/anode/hole injection layer (HIL)/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer
(ETL)/electron injecting layer (EIL)/cathode
Above-mentioned "/" indicates to be laminated in order between different function layer.
Device embodiments 1
The structure of organic electroluminescence device in device embodiments of the present invention are as follows:
ITO/2-TNATA(30nm)/NPB(20nm)/HTL-2(10nm)/EML(20nm)/Alq3(50nm)/LiF
(1nm)/Al。
Emitting layer material uses green phosphorescent coloring Ir (ppy)3Dyestuff, arrange in pairs or groups main body CBP.Each functional layer material molecular structure
It is as follows:
Organic electroluminescence device preparation process is as follows in the present embodiment:
The glass substrate that surface is coated with transparent conductive film is cleaned by ultrasonic in cleaning solution, in deionized water
Ultrasonic treatment, in ethyl alcohol: ultrasonic oil removing in acetone mixed solution is baked under clean environment and completely removes moisture, use is ultraviolet
Lamp performs etching and ozone treatment, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation 2-TNATA on anode tunic, adjusting evaporation rate are 0.1nm/s, form the hole injection layer with a thickness of 30nm；?
Vacuum evaporation compound N PB on hole injection layer forms the hole transmission layer with a thickness of 20nm, evaporation rate 0.1nm/s；
Luminescent layer of the vacuum evaporation EML as device on hole transmission layer, EML include material of main part and dye materials, using more
The method that source is steamed altogether, adjusting material of main part CBP evaporation rate are 0.1nm/s, and 3 evaporation rate of dye materials Ir (ppy) is according to mixing
Miscellaneous ratio setting, vapor deposition total film thickness are 20nm；
Alq3 is used to transmit layer material, evaporation rate 0.1nm/s as device electronic, vapor deposition total film thickness is 50nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 1nm as electron injecting layer, with a thickness of 150nm's
The Al layers of cathode as device.
2. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by Alq3 compound
Replace with compound A1.
3. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A2.
4. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A-45.
5. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A6.
6. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A9.
7. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A10.
8. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A11.
9. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A12.
10. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A13.
11. the compounds of this invention of device embodiments is as electron transport material
Organic electroluminescence device is prepared using method same as Example 1, difference is, Alq3 is replaced with
Compound A15.
Concrete preferred structure compound disclosed in device embodiments of the present invention is applied in organic electroluminescence device
Device performance detection data is detailed in the following table 2:
The device performance data of the device embodiments 1-11 as disclosed in table 2 are as it can be seen that in organic electroluminescence device structure
In the identical situation of middle other materials, the adjustment of electron transport material in the devices, compare device embodiments 1, can be significant
Ground reduces the operating voltage of device, and increases substantially the luminous efficiency of device.This has with the series compound in the present invention
Deeper LUMO value and preferable electron mobility are related.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can
No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (10)
1. a kind of general formula compound structure as shown in following formula (I):
Wherein, Ar1Selected from hydrogen, or it is selected from C6~C30Substituted or non-substituted aryl or condensed-nuclei aromatics group, C3~C30Take
Generation or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, Ar2Selected from C6~C30Substituted or non-substituted aryl or condensed ring virtue
Hydrocarbyl group, C3~C30Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Work as Ar1With Ar2When being respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, institute
The substituent group stated thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, or be selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
2. general formula compound according to claim 1, in formula (I):
Ar1Selected from hydrogen, or it is selected from C6~C20Substituted aryl or condensed-nuclei aromatics group, C5~C20It is substituted or non-substituted
Heteroaryl or condensed hetero ring aromatic hydrocarbon group, Ar2Selected from C6~C20Substituted aryl or condensed-nuclei aromatics group, C5~C20Substitution or
Non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Work as Ar1And Ar2When being respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, institute
The substituent group stated thereon is independently selected from F, cyano, or is selected from C1~C5Alkyl or cycloalkyl, Si (CH3)3, alkenyl, alkoxy
Or thio alkoxy group；
Work as Ar1And Ar2When being respectively and independently selected from substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, the hetero atom is
One or more O, S and N.
3. general formula compound according to claim 1, in formula (I):
Work as Ar1And Ar2When being respectively and independently selected from aryl or condensed-nuclei aromatics group, be chosen in particular from: phenyl, xenyl, terphenyl,
Naphthalene, anthryl, phenanthryl, indenyl, fluoranthene base, triphenylene, pyrenyl, base,Base or aphthacene base；By furyl, thienyl,
The phenyl that pyrimidine radicals, pyrrole radicals and/or pyridyl group replace；2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4-
Base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base and m- three
Xenyl -2- base, benzene binaphthyl, 4- naphthylphenyl, 6- phenyl napthyl, 7- phenyl phenanthryl, 9,9 '-dimethyl fluorenes, 9,9 '-spiral shells two
Fluorenes, benzfluorene；
Work as Ar1And Ar2When being respectively and independently selected from heteroaryl or condensed hetero ring aromatic hydrocarbon group, be chosen in particular from: furyl, benzofurane base,
Thienyl, tolylthiophene base, pyrrole radicals, phenylpyrrole base, pyridyl group, phenylpyridyl, pyrazinyl, fluorenyl, indeno fluorenyl, quinoline
Quinoline, triazine radical, benzofuranyl, benzothienyl, phentriazine, benzopyrazines, isobenzofuran-base, indyl, benzo quinoline
Diazole, the coffee quinoline that quinoline, benzimidazole, dibenzofuran group, dibenzothiophene, dibenzopyrrole base, carbazyl, phenyl replace
Base, coffee quinoline benzothiazolyl, benzodioxole group, 9- phenyl carbazole, 9- naphthyl carbazole benzo carbazole, dibenzo click
Azoles and indolocarbazole.
4. general formula compound according to claim 1 to 3, wherein Ar1And Ar2It is not identical.
5. general formula compound according to claim 1 to 3, wherein compound molecular weight is 450~900.
6. general formula compound according to claim 1 or 2 is selected from following concrete structure formulas:
7. general formula compound described in claims 1 to 3 any one is used as electron-transport material in organic electroluminescence device
Material.
8. structural compounds according to claim 5 are used as electron transport material in organic electroluminescence device.
9. a kind of organic electroluminescence device, including first electrode, second electrode and it is located at the first electrode and second electrode
Between one or more layers organic layer, luminescent layer and electron transfer layer are included at least in organic layer, it is characterised in that: the electronics
Comprising at least one by formula (I) compound represented in transport layer:
Wherein, Ar1Selected from hydrogen, or it is selected from C6~C30Substituted or non-substituted aryl or condensed-nuclei aromatics group, C3~C30Take
Generation or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group, Ar2Selected from C6~C30Substituted or non-substituted aryl or condensed ring virtue
Hydrocarbyl group, C3~C30Substituted or non-substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Work as Ar1And Ar2When being respectively and independently selected from substituted aryl, condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group, institute
The substituent group stated thereon is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkenyl, C1~C6
Alkoxy or thio alkoxy group, or be selected from Si (R1)3, the R1Selected from C1~C6Alkyl.
10. a kind of organic electroluminescence device, which includes first electrode, second electrode and is located at the first electrode and the
One or more layers organic layer between two electrodes includes at least luminescent layer and electron transfer layer in organic layer, which is characterized in that institute
It states in electron transfer layer comprising at least one compound selected from following specific structures:
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