CN108017647A - A kind of perimidine derivative and its application - Google Patents
A kind of perimidine derivative and its application Download PDFInfo
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- CN108017647A CN108017647A CN201610967545.9A CN201610967545A CN108017647A CN 108017647 A CN108017647 A CN 108017647A CN 201610967545 A CN201610967545 A CN 201610967545A CN 108017647 A CN108017647 A CN 108017647A
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- 0 C[C@](C1c2ccccc2C23c(cccc4)c4C=*C2C13)c(cc1)cc(c2ccc(ccc3c4[n]5c(cc6)c3cc6-[n](c3ccccc33)c6c3c(cccc3)c3cc6)c4c22)c1[n]2C5=O Chemical compound C[C@](C1c2ccccc2C23c(cccc4)c4C=*C2C13)c(cc1)cc(c2ccc(ccc3c4[n]5c(cc6)c3cc6-[n](c3ccccc33)c6c3c(cccc3)c3cc6)c4c22)c1[n]2C5=O 0.000 description 2
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
Abstract
The present invention relates to a kind of novel organic compound, more particularly to a kind of perimidine derivative, and further disclose it and be used to prepare the application of organic electroluminescence device.One kind nitogen-contained heterocycle derivant disclosed by the invention, the HOMO energy levels that the compound matches with emitting layer material, and with high hole migration ability with good film forming.Derivative of the present invention can be used as hole mobile material device test data and show, using organic electroluminescence device made from derivative of the present invention, can significantly reduce device and play bright and operating voltage, improve device efficiency.
Description
Technical field
The present invention relates to a kind of novel organic compound, more particularly to a kind of perimidine derivative, one is gone forward side by side
Step discloses it and is used to prepare the application of organic electroluminescence device.
Background technology
Electroluminescent (electroluminescence, EL) refers to that luminescent material under electric field action, is subject to electric current and electricity
Excitation and luminous phenomenon, it is an a kind of luminescence process that electric energy is converted into luminous energy.It can produce electroluminescent
Luminous solid material is very much, studies more and can reach using level, mainly inorganic semiconductor material.But nothing
Cost of manufacture height, processing difficulties, inefficiency, the glow color of machine El element are not easy condition, than total colouring relatively difficult to achieve, and
And the FPD of large area difficult to realize, it further limit the development of inorganxc EL device.1963, Pope and his colleague
It is found that organic electroluminescent phenomenon earliest, they have found the single layer crystal of anthracene under the driving of more than 100V voltages, Ke Yifa
Go out faint blue light.1987, doctor Deng Qingyun of Eastman Kodak et al. was prepared for brightness height, work using ultra-thin membrane technology
Low, the efficient double-deck organic electroluminescence device of voltage, OLED (OrganicLight Emitting have been opened from this
Device research prelude).
The continuous propulsion in two big fields is being illuminated and is showing now with OLED technology, and people grind for its core material
Study carefully and focus more on, the organic electroluminescence device of an excellent in efficiency long lifespan is typically device architecture and various organic materials
Optimize arranging in pairs or groups as a result, this functionalization material that various structures are just designed and developed for chemists provides great opportunity and chooses
War.
Relative to phosphor, electroluminescent organic material has lot of advantages, such as：Processing performance is good, can be with
Formed a film by the method for evaporation or spin coating on any substrate, it is possible to achieve Flexible Displays and large-area displays；It can pass through
Change the structure of molecule, adjust optical property, electric property and stability of material etc., the selection of material has very big sky
Between.Typical OLED device structure, generally comprises substrate, first electrode, second electrode and is arranged on two and interelectrode has
Machine light emitting functional layer.Material wherein for organic luminescence function layer can include according to its function：Hole-injecting material, hole
Transmission material, hole barrier materials, electron injection material, electron transport material, electron-blocking materials, light emitting host material, hair
Light guest materials etc..For the more preferable luminescent device of processability, industry has been devoted to develop new organic electroluminescence material
Expect to further improve luminous efficiency and the service life of device.
Hole-injecting material (HIM) requires its HOMO energy level between anode and hole transmission layer, is conducive to increase boundary
Hole injection between face.Hole mobile material (HTM) requires high heat endurance (high Tg), with anode or hole
Injection material has less potential barrier, and higher cavity transmission ability can vacuum evaporation formation pin-hole free films.In organic electroluminescent
The hole injection used always in device and transmission material are usually an aromatic amino-derivative, it is general to be structurally characterized in that conduct
During injection material, in a molecule one arylamine construction unit at least at more than one, and between two N with a phenyl ring every
Open；And when being used as transmission material, one arylamine construction unit is usually two in a molecule, and uses biphenyl between two N
Separate, in this kind of material, typical example is NPB.
Chinese patent CN103183638B and CN103183664B disclose a kind of hole with new mother nucleus structure and note
Enter and transmission material, the introducing of new precursor structure make such compound become the sky with superior hole injection and transport property
Hole transport materials, it can be seen that physical parameter such as carrier mobility, film forming of the precursor structure of material molecule for molecule
Stability etc. has a very big impact.However, in order to meet the needs of OLED device performance is constantly lifted, it is necessary to develop performance more
Excellent hole injection and transmission material, this development tool for OLED industries have very important significance.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of perimidine derivative, and further provide for
Said derivative is used for the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS field, and specifically, the derivative is in organic electroluminescent
In display, it is used as hole mobile material.
In order to solve the above technical problems, a kind of perimidine derivative of the present invention, has below formula
(C) structure shown in：
Wherein, the Ar1、Ar2It is independent of each other to be selected from substituted or unsubstituted C3-C30Cycloalkyl, it is substituted or unsubstituted
C6-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl；Alternatively,
The Ar1、Ar2It is independent of each other to be selected from substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C6-C30
Aryl, substituted or unsubstituted C2-C30Heteroaryl, and the Ar1、Ar2It is connected with each other cyclization.
Hetero atom in the heteroaryl or the heteroaryl amino is to be at least one selected from B, N, O, S, P, P (=O), Si
With the hetero atom of Se.
Preferably, the substituted or unsubstituted cycloalkyl is selected from C3-C6Cycloalkyl；
The substituted or unsubstituted aryl is selected from C6-C20Aryl；
The substituted or unsubstituted heteroaryl is selected from C2-C20Heteroaryl.
The C3-C30Cycloalkyl include cyclopropyl, cyclobutyl, cyclopenta and/or cyclohexyl；
The C6-C30Aryl include phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its
Derivative, fluoranthene base, triphenylene, pyrenyl, base,Base and aphthacene base；And it is highly preferred that the xenyl selects 2- to join
Phenyl, 3- xenyls and 4- xenyls, the terphenyl include p- terphenyl -4- bases, p- terphenyl -3- bases, p-
Terphenyl -2- bases, m- terphenyl -4- bases, m- terphenyl -3- bases and m- terphenyl -2- bases；The naphthyl is
In the group that 1- naphthyls and 2- naphthyls are formed；The anthryl is in the group being made of 1- anthryls, 2- anthryls and 9- anthryls；Institute
Fluorenyl is stated in the group being made of 1- fluorenyls, 2- fluorenyls, 3- fluorenyls, 4- fluorenyls and 9- fluorenyls；The fluorenyl derivative choosing
Freely 9,9 '-dimethyl fluorene, 9, in the group that 9 '-spiral shell, two fluorenes and benzfluorene are formed；
The C2-C30Heteroaryl include thiazole, benzothiazole, phenanthro- imidazoles, phenanthro- benzothiophene benzimidazole, dislike
Azoles, oxadiazoles, triazole, pyridine, pyrimidine, triazine, evil boron heterocycle, quinoline, isoquinolin, quinoxaline, quinazoline, benzoxazoles, phenanthrene
And oxazole, phenanthro- thiazole, bipyridyl, phenanthridines, phenanthroline, imidazopyridine, imidazopyrimidine, phenoxazine, phenthazine, dimethyl
Acridan, the miscellaneous benzene of 1,2,5,10- tetrahydrochysene dibenzo boron, the miscellaneous benzene of 10,10- dimethyl -5,10- tetrahydrochysene dibenzo boron, 4- biphenyl
Acyl group, furyl, thienyl, pyrrole radicals, benzofuranyl, benzothienyl, isobenzofuran-base, indyl, dibenzo furan
Mutter base, dibenzothiophene, carbazyl and its derivative, benzodioxole group；And the carbazole radical derivative can
To include but not limited to 9- phenyl carbazoles, 9- naphthyl carbazoles benzo carbazole, dibenzo-carbazole, indolocarbazole, N- Phenylindoles
And at least one of carbazole, benzofuran and carbazole.
More preferably, the Ar1And Ar2Connected by two adjacent groups to be formed interconnection be connected into substitution or it is unsubstituted
Five-membered ring, hexatomic ring or heptatomic ring, the constituting atom of the ring structure are selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or boron
Atom, and the hetero atom is preferably N, O, S, B, and preferably into pyrrole ring, piperidine ring, morpholine ring, thiomorpholine ring, piperazine
The structures such as ring, 1,4- azepine borine rings or azepines ring.
It is furthermore preferred that the Ar1With Ar2It is identical.
Optimal, the derivative is selected from structure shown in following C1-C42：
The invention also discloses the perimidine derivative to be used to prepare answering for organic electroluminescence device
With.
The perimidine derivative is used as hole mobile material.
The invention also discloses a kind of organic electroluminescence device, including substrate, and sequentially form on the substrate
Anode layer, organic luminescence function layer and cathode layer；
The organic luminescence function layer includes hole injection layer, hole transmission layer, organic luminous layer and electron transfer layer；
The hole mobile material of the hole transmission layer includes at least one perimidine derivative material
Material.
The molecular system of derivant material of the present invention based on nitrogenous ring structure, there is high triplet, separately
Outer precursor structure has flatness, its conjugacy is fine, by Gauss quantum chemical method the results show that the HOMO energy levels of parent molecule
It is evenly distributed in the electron cloud of lumo energy on whole skeleton, thus (it is female with very excellent carrier transport
The triplet of body structure is about 2.75eV).And pass through the substituent of the diaryl-amine substituted radical on precursor structure ring
Substitution, can effectively adjust molecule electron property, and then the HOMO energy levels of molecule, different structure and size can be adjusted
Diaryl-amine group can also play the molecular weight and symmetry for adjusting material molecule, can effectively improve the hole of material
Transporting and film forming stability.The HOMO of parent molecule, the Cloud Distribution figure of lumo energy molecular orbit are referring to specification
Attached drawing 1-2.
One kind nitogen-contained heterocycle derivant disclosed by the invention, the HOMO energy that the compound matches with emitting layer material
Level, and with high hole migration ability with good film forming.Derivative of the present invention can be used as hole mobile material
Device test data is shown, using organic electroluminescence device made from derivative of the present invention, can significantly reduce device
Bright and operating voltage is played, improves device efficiency.
Brief description of the drawings
In order to make the content of the present invention more clearly understood, the specific embodiment below according to the present invention and combination
Attached drawing, the present invention is described in further detail, wherein
Fig. 1 is the Cloud Distribution figure of the HOMO energy level molecular orbits of the parent molecule of the compounds of this invention；
Fig. 2 is the Cloud Distribution figure of the lumo energy molecular orbit of the parent molecule of the compounds of this invention.
Embodiment
Below with reference to following embodiments be described in detail organic electroluminescent compounds and preparation method thereof of the present invention with
And the preparation method and luminosity of the luminescent device comprising the compound.
Various chemicals such as petroleum ether, ethyl acetate, tetrahydrofuran, n-hexane, toluene, second used in the present invention
Acid, dichloromethane, DMF, 1,8- dinaphthylamine, N, the bromo- 2- iodonitrobenzenes of N'- carbonyl dimidazoles, 4-, sodium tert-butoxide, three (two benzal
Benzylacetone) two palladiums, tetra-triphenylphosphine palladium, tri-butyl phosphine toluene solution, palladium, isoamyl nitrite, zinc powder, sodium sulphate etc.
Chemical products it can be commercially available at home.
The synthesis of 1 intermediate M1 of synthetic example
1,8- dinaphthylamines (50g, 0.316mol) and 500 milliliters of dichloromethane are added into 3 liters of there-necked flasks, is added dropwise at room temperature
The mixed solution of N, N'- carbonyl dimidazoles (56.4g, 0.348mol) and 1200 milliliters of dichloromethane.After adding, room temperature reaction 2
Filtered after hour, with eluent methylene chloride filter cake, obtain compound M1 (54.5g, 94%).
The synthesis of 2 intermediate M2 of synthetic example
By the bromo- 2- iodonitrobenzenes (65.6g, 0.2mol) of intermediate M1 (18.4g, 0.1mol), 4-, sodium tert-butoxide
Two palladium (0.92g, 0.001mol) of (28.5g, 0.3mol), three (dibenzalacetone), 10% tri-butyl phosphine toluene solution
(368 milliliters) mixing of (6.06g, 0.003mol) and toluene, when stirring 24 is small under reflux conditions, after reaction, are cooled to
Room temperature, adds 500 milliliters of pure water, and organic layer is extracted with ethyl acetate, is spin-dried for after the drying of organic phase anhydrous sodium sulfate, then carries out
Post separation (eluent：Dichloromethane/n-hexane), obtain compound M2 (41.5g, 71.1%).
The synthesis of 3 intermediate M3 of synthetic example
By intermediate M2 (58.4g, 0.1mol), 580ml ethanol, iron powder (4.3g, 1mol), 290ml saturated ammonium chloride water
Solution, temperature rising reflux reaction 5h, point board monitoring reaction are completed, and filtering, filter cake is eluted with ethyl acetate, organic after filtrate liquid separation
Mutually it is spin-dried for, obtains intermediate M3 (48.2g, yield 91.9%).
The synthesis of 4 intermediate M4 of synthetic example
Intermediate M3 (5.2g, 10mmol) is dissolved in 16ml acetic acid, adds 1g copper powders, stirring is cooled to 5-10 DEG C, uses
Acetic acid (8ml) dissolving isoamyl nitrite (3.9g, 33mmol), is slowly added dropwise into system, is stirred at room temperature after being added dropwise, point
To the reaction was complete, liquid separation, organic phase is washed one time with aqueous sodium carbonate, is dried with anhydrous sodium sulfate, is spin-dried for laggard for board monitoring
Row column chromatography (eluent：Dichloromethane/petroleum ether), obtain product intermediate M4 (3.0g, yield 62.0%).
The synthesis of 5 compound C1 of synthetic example
Under nitrogen protection, by intermediate M4 (4.9g, 10mmol), (naphthalene -1- bases) amine (5.92g, 22mmol), sodium tert-butoxide
Two palladium (0.18g, 0.2mmol) of (4.8g, 50mmol), three (dibenzalacetone), 10% tri-butyl phosphine toluene solution
(100 milliliters) mixing of (1.2g, 0.6mmol) and toluene, when stirring 24 is small under reflux conditions, after reaction, are cooled to room
Temperature, adds 500 milliliters of pure water, and organic layer is extracted with ethyl acetate, is spin-dried for after the drying of organic phase anhydrous sodium sulfate, then carries out column
Separate (eluent：Dichloromethane/n-hexane), obtain compound C1 (6.6g, 76.3%).
1H NMR (500MHz, Chloroform-d) δ 9.55 (dd, J=7.5,1.4Hz, 1H), 8.81 (d, J=7.5Hz,
1H), 8.71 (dd, J=7.5,1.4Hz, 1H), 8.56 (dt, J=7.6,1.5Hz, 1H), 8.40-8.32 (m, 2H), 8.17-
8.06 (m, 3H), 7.96 (dt, J=7.6,1.6Hz, 1H), 7.96-7.83 (m, 5H), 7.83-7.76 (m, 2H), 7.78-7.69
(m,3H),7.71–7.62(m,2H),7.63–7.52(m,7H),7.51–7.44(m,2H),7.47–7.36(m,5H),7.11
(d, J=7.5Hz, 1H), 6.83 (ddd, J=27.3,7.5,1.4Hz, 2H), 6.26 (dd, J=7.5,1.5Hz, 1H).Element
Analysis：C,87.27；H,4.42；N,6.46.
The synthesis of synthetic example 6 compound C2, C3, C4, C5, C6
Using the synthetic method identical with compound C1, difference is, it is corresponding that (naphthalene -1- bases) amine is replaced into equivalent
Arylamine.
The synthesis of 7 compound C7 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the N- of equivalent
([1,1'- biphenyl] -4- bases) chromene -2- amine, after the completion of reaction, obtains compound C7 8.46g, yield 71.1%.
1H NMR (500MHz, Chloroform-d) δ 9.74-9.68 (m, 2H), 9.42 (d, J=7.5Hz, 1H), 9.14-
9.05 (m, 2H), 8.84 (dd, J=7.3,1.6Hz, 2H), 8.52 (dt, J=7.6,1.4Hz, 2H), 8.43 (d, J=7.5Hz,
1H), 8.37-8.31 (m, 2H), 7.90 (dt, J=7.2,1.6Hz, 2H), 7.87-7.79 (m, 3H), 7.76 (d, J=7.4Hz,
1H), 7.72-7.56 (m, 8H), 7.44 (t, J=7.4Hz, 4H), 7.37-7.29 (m, 2H), 7.15-7.04 (m, 2H), 6.98
(d, J=7.5Hz, 1H), 6.82-6.66 (m, 7H), 6.62 (ddd, J=7.8,4.4,2.0Hz, 2H).Elemental analysis：C,
89.06；H,4.50；N,5.01.
The synthesis of synthetic example 8 compound C8, C9, C10, C11, C12
Using the synthetic method identical with compound C7, difference is, by N- ([1,1'- biphenyl] -4- bases) chromene -
2- amine is replaced into the corresponding arylamine of equivalent.
The synthesis of 9. compound C13 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the 3,6- of equivalent
Phenyl -9H- carbazoles, after the completion of reaction, obtain compound C13 7.94g, yield 82.1%.
1H NMR (500MHz, Chloroform-d) δ 9.12-9.04 (m, 2H), 8.87 (d, J=1.3Hz, 1H), 8.75
(dd, J=7.4,1.6Hz, 1H), 8.69 (d, J=1.4Hz, 1H), 8.51-8.45 (m, 2H), 8.44-8.31 (m, 4H), 8.09
(t, J=7.1Hz, 2H), 8.08-7.98 (m, 2H), 7.70 (dd, J=7.5,1.5Hz, 1H), 7.62-7.56 (m, 8H),
7.48-7.37 (m, 9H), 7.37-7.29 (m, 4H), 7.28-7.20 (m, 2H), 6.85 (dd, J=7.4,1.5Hz, 1H), 6.30
(dd, J=7.5,1.5Hz, 1H).Elemental analysis：C,88.18；H,4.38；N,5.79.
The synthesis of synthetic example 10 compound C14, C15, C16, C17, C18
Using the synthetic method identical with compound C13, difference is, 3,6- phenyl -9H- carbazoles are replaced into equivalent
Corresponding arylamine.
The synthesis of 11 compound C19 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the N- of equivalent
(3- (5- phenylpyridine -3- bases) phenyl) phenanthrene -1- amine, after the completion of reaction, obtains compound C82 8.04g, yield 68.5%.
1H NMR (500MHz, Chloroform-d) δ 9.13 (dd, J=7.3,1.5Hz, 1H), 9.00-8.93 (m, 2H),
8.90-8.80 (m, 5H), 8.65-8.54 (m, 3H), 8.44 (dd, J=7.5,1.4Hz, 1H), 8.35 (dd, J=7.5,
2.0Hz, 2H), 8.28 (dd, J=7.4,1.5Hz, 1H), 8.12 (d, J=7.5Hz, 1H), 8.00 (t, J=7.5Hz, 1H),
7.90 (dt, J=7.5,1.5Hz, 2H), 7.83 (dt, J=7.5,2.0Hz, 1H), 7.72-7.59 (m, 5H), 7.55 (dt, J=
7.5,2.0Hz, 1H), 7.44-7.32 (m, 5H), 7.33 (s, 1H), 7.16-7.09 (m, 2H), 6.99 (d, J=7.5Hz, 1H),
6.86 (dt, J=7.5,2.0Hz, 1H), 6.82-6.65 (m, 6H), 6.48 (dd, J=7.5,1.5Hz, 1H), 6.15 (dd, J=
7.5,1.4Hz,1H).Elemental analysis：C,87.01；H,4.47；N,7.16.
The synthesis of synthetic example 12 compound C20, C21, C22, C23
Using the synthetic method identical with compound C19, difference is, by N- (3- (5- phenylpyridine -3- bases) phenyl)
Phenanthrene -1- amine is replaced into the corresponding arylamine of equivalent.
The synthesis of 13 compound C24 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the N1 of equivalent,
N1, N4- triphenylbenzene-Isosorbide-5-Nitrae-diamines, after the completion of reaction, obtain compound C246.22g, yield 62.1%.
1H NMR (500MHz, Chloroform-d) δ 9.09 (d, J=7.4Hz, 1H), 8.47 (d, J=7.5Hz, 2H),
8.02 (d, J=7.6Hz, 1H), 7.80 (d, J=7.5Hz, 2H), 7.38 (d, J=7.6Hz, 2H), 7.32-7.15 (m, 18H),
7.11-7.04 (m, 13H), 7.00 (tt, J=7.3,2.0Hz, 6H), 6.93 (d, J=7.5Hz, 1H), 6.54-6.47 (m,
2H), 6.24 (dd, J=7.5,1.5Hz, 1H).Elemental analysis：C,85.18；H,4.83；N,8.39.
The synthesis of synthetic example 14 compound C25, C26, C27
Using the synthetic method identical with compound C24, difference is, by N1, N1, N4- triphenylbenzene-Isosorbide-5-Nitrae-diamines are put
It is changed to the corresponding arylamine of equivalent.
The synthesis of 15 compound C28 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the 7H- of equivalent
Benzo [c] carbazole, after the completion of reaction, obtains compound C28 6.21g, yield 81.4%.
1H NMR (500MHz, Chloroform-d) δ 9.92 (d, J=1.3Hz, 1H), 9.25 (d, J=7.5Hz, 1H),
9.17 (d, J=7.5Hz, 1H), 8.93-8.84 (m, 2H), 8.74 (ddd, J=24.4,7.4,1.4Hz, 2H), 8.64 (dd, J
=7.5,1.4Hz, 1H), 8.48 (dd, J=7.4,1.4Hz, 1H), 8.39-8.31 (m, 2H), 8.24 (dd, J=7.5,
1.5Hz, 1H), 8.16 (dd, J=7.5,1.5Hz, 1H), 8.08-7.98 (m, 3H), 7.88-7.78 (m, 5H), 7.71 (td, J
=7.5,1.6Hz, 1H), 7.64 (dd, J=7.5,1.5Hz, 1H), 7.57-7.33 (m, 6H), 7.05 (dd, J=7.4,
1.6Hz,1H).Elemental analysis：C,86.59；H,3.96；N,7.34.
The synthesis of synthetic example 16 compound C29, C30, C31, C32
Using the synthetic method identical with compound C28, difference is, 7H- benzos [c] carbazole is replaced into equivalent phase
The arylamine answered.
The synthesis of 17 compound C33 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the click of equivalent
Azoles, after the completion of reaction, obtains compound C33 5.66g, yield 85.5%.
1H NMR (500MHz, Chloroform-d) δ 9.23 (d, J=1.5Hz, 1H), 9.01 (d, J=7.5Hz, 1H),
8.87 (d, J=7.5Hz, 1H), 8.48-8.39 (m, 3H), 8.41-8.30 (m, 3H), 8.26-8.19 (m, 3H), 8.10 (dd, J
=7.5,1.6Hz, 1H), 7.97-7.87 (m, 3H), 7.86 (dd, J=7.4,1.4Hz, 1H), 7.76 (dd, J=7.5,
1.5Hz,1H),7.49–7.37(m,6H),7.40–7.34(m,2H).Elemental analysis：C,85.18；H,3.95；N,8.45.
The synthesis of synthetic example 18 compound C34, C35, C36
Using the synthetic method identical with compound C33, difference is, carbazole is replaced into the corresponding arylamine of equivalent.
The synthesis of 19 compound C37 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the 11- of equivalent
Phenyl -11,12- dihydroxy indole [2,3-a] carbazole, after the completion of reaction, obtains compound C37 8.00g, yield 80.5%.
1H NMR (500MHz, Chloroform-d) δ 8.33 (dd, J=7.5,1.5Hz, 1H), 7.98 (dd, J=7.5,
1.4Hz, 1H), 7.72-7.56 (m, 3H), 7.53-7.41 (m, 2H), 7.30 (tdd, J=7.5,4.3,2.1Hz, 2H), 7.16
(td, J=7.4,1.5Hz, 2H), 7.08 (d, J=7.5Hz, 1H).Elemental analysis：C,85.87；H,4.06；N,8.46.
The synthesis of 20 compound C38, C39 of synthetic example
Using the synthetic method identical with compound C37, difference is, by 11- phenyl -11,12- dihydroxy indole [2,
3-a] carbazole is replaced into the corresponding arylamine of equivalent.
The synthesis of 21 compound C40 of synthetic example
Using the synthetic method identical with compound C1, difference is, (naphthalene -1- bases) amine is replaced into the 9,9- of equivalent
Dimethyl-N-(p-methylphenyl) -9H- fluorenes -2- amine, after the completion of reaction, obtains compound C40 6.04g, yield 65.2%.
1H NMR(500MHz,Chloroform-d)δ8.12–8.06(m,1H),7.85–7.70(m,3H),7.70–7.50
(m, 3H), 7.46-7.34 (m, 1H), 7.26-7.07 (m, 2H), 6.99 (dd, J=6.8,1.6Hz, 2H), 2.33 (d, J=
1.2Hz, 2H), 1.82 (s, 1H), 1.72 (d, J=1.1Hz, 2H), 1.49 (s, 1H).Elemental analysis：C,86.80；H,5.44；
N,6.04。
The synthesis of 22. compound C41, C42 of synthetic example
Using the synthetic method identical with compound C40, difference is, by 9,9- dimethyl-N -s (p-methylphenyl) -9H-
Fluorenes -2- amine is replaced into the corresponding arylamine of equivalent.
Device application examples
Compare the performance of these materials for convenience, the present invention devises a simple electroluminescence device, and device of the present invention should
The concrete structure of organic electroluminescence device is in use-case：
ITO/2-TNATA(10nm)/NPB(80nm)/EML(30nm)/ETL1(30nm)/LiF(1nm)/Al。
Hole-injecting material uses 2-TNATA；Hole mobile material uses tri-arylamine group material NPB；Emitting layer material makes
With red phosphorus photoinitiator dye (piq) 2Ir (acac), collocation feux rouges main body CBP；Electron transfer layer selects the electron transport material of commercialization
ETL1.Each functional layer uses the structural formula of material as follows：
Substrate can use the substrate in conventional organic luminescence device, such as：Glass or plastics.In the Organic Electricity of the present invention
Electroluminescence device selects glass substrate in making, and ITO makees anode material.
Hole transmission layer can use various tri-arylamine group materials, the institute in the organic electroluminescence device of the present invention makes
The hole mobile material of selection is NPB.
Cathode can use metal and its mixture structure, such as Mg：Ag、Ca：Ag etc. or electron injecting layer/gold
Belong to Rotating fields, such as LiF/Al, Li2O/Al common cathode structure.It is selected in the organic electroluminescence device of the present invention makes
Cathode material is LiF/Al.
Compound C1-C42 in the application example makes altogether respectively as the hole mobile material in organic electroluminescence device
It is for multiple organic electroluminescence devices, its structure：ITO/2-TNATA(10nm)/NPB(80nm)/EML(30nm)/ETL1
(30nm)/LiF(1nm)/Al。
Organic electroluminescence device preparation process is as follows in the present embodiment：
The glass plate for being coated with ITO (150nm) transparency conducting layer is ultrasonically treated in commercial detergent, in deionized water
Middle flushing, in acetone：Ultrasonic oil removing, is baked under clean environment and removes water completely in alcohol mixed solvent (volume ratio 1: 1)
Part, with ultraviolet light and ozone clean, and with the low energy cation beam bombarded surface of Satella (ULVAC)；
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 compound 2-TNATA on anode tunic, forms the hole injection layer that thickness is 60nm；It is true on hole injection layer
Sky evaporation the compounds of this invention C1-C42 (comparative device of hole transmission layer is used as using NPB), forms the hole that thickness is 20nm
Transport layer, evaporation rate 0.1nm/s；
Electroluminescence layer is formed on above-mentioned hole transmission layer, concrete operations are：Using as the CBP of luminescent layer material of main part
[bis- carbazoles of 4,4'-N, N'--biphenyl] are placed in the cell of vacuum phase deposition equipment, using as (piq) 2Ir of dopant
(acac) [two-(1- phenyl isoquinolin quinolines base) acetylacetone,2,4-pentanedione iridium (III)] is placed in another room of vacuum phase deposition equipment, with
Different speed evaporates two kinds of materials at the same time, and the concentration of (piq) 2Ir (acac) is 5%, and evaporation total film thickness is 30nm；
Vacuum evaporation compound ETL1 forms the electron transfer layer that thick film is 20nm on luminescent layer, its evaporation rate is
0.1nm/s；
For the LiF that vacuum evaporation thickness is 0.5nm on the electron transport layer as electron injecting layer, thickness is the Al of 150nm
Cathode of the layer as device.
Comparative device example 1
According to aforementioned preparation process, using NPB as hole mobile material, comparative device 1 is made.
Under same brightness, the voltage and current effect for the organic electroluminescence device being prepared in each application examples is measured
Rate, measurement result see the table below 1.
1 the compounds of this invention of table is used as the measurement result of hole transport layer material device
| Device number | HTL | It is required that brightness cd/m2 | Voltage V | Current efficiency Cd/A |
| 1 | C2 | 5000.00 | 4.8 | 9.3 |
| 2 | C12 | 5000.00 | 4.7 | 8.9 |
| 3 | C13 | 5000.00 | 4.6 | 9.2 |
| 4 | C16 | 5000.00 | 4.9 | 8.7 |
| 5 | C21 | 5000.00 | 4.6 | 9.3 |
| 6 | C24 | 5000.00 | 4.7 | 9.1 |
| 7 | C28 | 5000.00 | 4.8 | 9.2 |
| 8 | C33 | 5000.00 | 4.9 | 9.4 |
| 9 | C38 | 5000.00 | 4.5 | 9.2 |
| 10 | C39 | 5000.00 | 4.8 | 9.1 |
| 11 | C42 | 5000.00 | 4.7 | 9.2 |
| Comparative device 1 | ETL1/CBP | 5000.00 | 5.5 | 8.1 |
From the experimental data of table 1 as it can be seen that compared with comparative device embodiment 1, new organic materials of the invention are used for
Hole mobile material in organic electroluminescence device, the NPB that compares can effectively reduce landing voltage, improve electric current effect
Rate, is hole mobile material of good performance.This has suitable HOMO energy levels and high hole migration with material of the present invention
Rate is related, while material of the present invention has high triplet, effectively can be limited in the exciton produced in luminescent layer
Luminescent layer, to ensure the high-luminous-efficiency of device.
Obviously, the above embodiments are merely examples for clarifying the description, and the restriction not to embodiment.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of change or
Change.There is no necessity and possibility to exhaust all the enbodiments.And the obvious change thus extended out or
Among changing still in the protection domain of the invention.
Claims (10)
1. a kind of perimidine derivative, it is characterised in that there is the structure shown in below formula (C)：
Wherein, the Ar1、Ar2It is independent of each other to be selected from substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C6-
C30Aryl, substituted or unsubstituted C2-C30Heteroaryl；Alternatively,
The Ar1、Ar2It is independent of each other to be selected from substituted or unsubstituted C3-C30Cycloalkyl, substituted or unsubstituted C6-C30Virtue
Base, substituted or unsubstituted C2-C30Heteroaryl, and the Ar1、Ar2It is connected with each other cyclization.
2. perimidine derivative according to claim 1, it is characterised in that the hetero atom of the heteroaryl is
At least one hetero atom selected from B, N, O, S, P, P (=O), Si and Se.
3. perimidine derivative according to claim 1 or 2, it is characterised in that：
The substituted or unsubstituted cycloalkyl is selected from C3-C6Cycloalkyl；
The substituted or unsubstituted aryl is selected from C6-C20Aryl；
The substituted or unsubstituted heteroaryl is selected from C2-C20Heteroaryl.
4. according to claim 1-3 any one of them perimidine derivatives, it is characterised in that
The C3-C30Cycloalkyl include cyclopropyl, cyclobutyl, cyclopenta and/or cyclohexyl；
The C6-C30Aryl include phenyl, xenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its derivative
Thing, fluoranthene base, triphenylene, pyrenyl, base,Base and aphthacene base；
The C2-C30Heteroaryl include thiazole, benzothiazole, phenanthro- imidazoles, phenanthro- benzothiophene benzimidazole, oxazole, evil
Diazole, triazole, pyridine, pyrimidine, triazine, evil boron heterocycle, quinoline, isoquinolin, quinoxaline, quinazoline, benzoxazoles, phenanthro- are disliked
Azoles, phenanthro- thiazole, bipyridyl, phenanthridines, phenanthroline, imidazopyridine, imidazopyrimidine, phenoxazine, phenthazine, dimethyl dihydro
Acridine, the miscellaneous benzene of 1,2,5,10- tetrahydrochysene dibenzo boron, the miscellaneous benzene of 10,10- dimethyl -5,10- tetrahydrochysene dibenzo boron, 4- biphenyl acyl group,
Furyl, thienyl, pyrrole radicals, benzofuranyl, benzothienyl, isobenzofuran-base, indyl, dibenzofuran group,
Dibenzothiophene, carbazyl and its derivative, benzodioxole group.
5. according to claim 1-4 any one of them perimidine derivatives, it is characterised in that the Ar1And Ar2
Connected by two adjacent groups to be formed interconnection be connected into substitution or unsubstituted five-membered ring, hexatomic ring or heptatomic ring, the ring
The constituting atom of structure is selected from carbon atom, nitrogen-atoms, oxygen atom, sulphur atom or boron atom, and the hetero atom be preferably N,
O, S, B, and preferably into pyrrole ring, piperidine ring, morpholine ring, thiomorpholine ring, piperazine ring, Isosorbide-5-Nitrae-azepine borine ring or azepines
The structures such as ring.
6. according to claim 1-5 any one of them perimidine derivatives, it is characterised in that the Ar1With Ar2
It is identical.
7. according to claim 1-6 any one of them perimidine derivatives, it is characterised in that the derivative choosing
From structure shown in following C1-C42：
8. any perimidine derivatives of claim 1-7 are used to prepare answering for organic electroluminescence device
With.
9. application according to claim 8, it is characterised in that the perimidine derivative is used as hole transport
Material.
10. a kind of organic electroluminescence device, including substrate, and sequentially form anode layer, You Jifa on the substrate
Light functional layer and cathode layer；
The organic luminescence function layer includes hole injection layer, hole transmission layer, organic luminous layer and electron transfer layer；It is special
Sign is：
The hole mobile material of the hole transmission layer includes any described embedding diaza of naphthalene of at least one claim 1-7
Benzene derivative material.
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