CN108558873A - A kind of aromatic amine derivant and its organic electroluminescence device - Google Patents
A kind of aromatic amine derivant and its organic electroluminescence device Download PDFInfo
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- CN108558873A CN108558873A CN201810476669.6A CN201810476669A CN108558873A CN 108558873 A CN108558873 A CN 108558873A CN 201810476669 A CN201810476669 A CN 201810476669A CN 108558873 A CN108558873 A CN 108558873A
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- 0 CC(C1)C1C(C=CC12)=CC1C2N(c(cc1)ccc1-c1ccc(C(C=C2)[N-]C3=*2C=CC2=CC=CNC32)cc1)c(cc1)ccc1OC Chemical compound CC(C1)C1C(C=CC12)=CC1C2N(c(cc1)ccc1-c1ccc(C(C=C2)[N-]C3=*2C=CC2=CC=CNC32)cc1)c(cc1)ccc1OC 0.000 description 5
- FKNGTQNTNSIAKV-XLWSPRFPSA-N C(C1)CC=CC1C(CC1)=CCC1N(c1ccc(C2CC=CCC2)cc1)c1cccc2c1C=CCC2C(CC1)=NC(C23)C1C=C[C@@H]1C2C3C=CC1 Chemical compound C(C1)CC=CC1C(CC1)=CCC1N(c1ccc(C2CC=CCC2)cc1)c1cccc2c1C=CCC2C(CC1)=NC(C23)C1C=C[C@@H]1C2C3C=CC1 FKNGTQNTNSIAKV-XLWSPRFPSA-N 0.000 description 1
- HISFJZCBXTVJRK-UHFFFAOYSA-N C1C2C(N(c3cccc4c3C=CCC4C3=CCc(c(nccc4)c4cc4)c4C=CC3)C3=CCCC4=C3C3C=CCCC3S4)=Cc3cc4ccccc4cc3C12 Chemical compound C1C2C(N(c3cccc4c3C=CCC4C3=CCc(c(nccc4)c4cc4)c4C=CC3)C3=CCCC4=C3C3C=CCCC3S4)=Cc3cc4ccccc4cc3C12 HISFJZCBXTVJRK-UHFFFAOYSA-N 0.000 description 1
- ISGKWMWQCHKHHP-UHFFFAOYSA-N CC(C)(C1C2)c3ccccc3C1=CC=C2N(c1cc(-c2ccc(CCC34C5=NC=CC3C4)c5n2)ccc1)c1cc2ccccc2cc1 Chemical compound CC(C)(C1C2)c3ccccc3C1=CC=C2N(c1cc(-c2ccc(CCC34C5=NC=CC3C4)c5n2)ccc1)c1cc2ccccc2cc1 ISGKWMWQCHKHHP-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Abstract
A kind of aromatic amine derivant of present invention offer and its organic electroluminescence device, are related to organic optoelectronic materials technology.Such compounds process for production thereof is simple, raw material is easy to get, and has high hole mobility and Tg, stability and good film-forming property, also has highest occupied molecular orbital energy level appropriate, the first hole transmission layer is can not only be used for, but also as the second hole transmission layer.When as the first hole transmission layer, the energy level difference between luminescent layer and anodic interface can be reduced；When as the second hole transmission layer, then the energy level difference between luminescent layer and the first hole transmission layer can be reduced, while can also realize point and equilibrium in luminescent layer.Applied to the luminous efficiency, excitation purity and service life that device in OLED device, can be significantly improved, moreover it is possible to which the driving voltage for reducing device is the OLED material of a kind of function admirable.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of aromatic amine derivant and its organic electroluminescence hair
Optical device.
Background technology
Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED) organic electric laser that is otherwise known as is aobvious
Show, be Dual Implantations type luminescent device, device architecture is organic by one layer or more between anode, cathode and anode and cathode
Film layer forms.To voltage is applied between two electrodes, electronics is injected into light-emitting zone from cathode side, and hole is noted from anode side
Enter to light-emitting zone, the two is combined into as exciton (exciton), and light is sent out when exciton restores to ground state, and electric energy is straight
Switch through the luminous energy for turning to organic semiconducting materials molecule.With CRT (Cathode Ray Tube, cathode-ray tube) and LCD
(Liquid Crystal Display, liquid crystal display) is compared, and has self-luminous, without backlight, high brightness, high comparison
Degree, fine definition, wide viewing angle, wide colour gamut, low-power consumption, that wide temperature, luminous efficiency is high, the reaction time is short, transparent, flexible etc. is excellent
Point is very promising photoelectric material.
OLED material can be divided into luminescent material, hole mobile material, electron transport material etc. according to the difference of function.It is empty
Hole transport materials are the hot spot of current major OLED material business research, and to improve the performance of OLED device, hole is passed
Defeated material is subdivided into the first hole transmission layer and the second hole transport layer material.The application of second hole mobile material in the devices
Position between the first hole transmission layer and luminescent layer, has between the first hole transmission layer and emitting layer material mostly
Highest occupied molecular orbital energy level, and have high T1 values, in drive voltage range have hole mobility appropriate
(hole mobility), effect mainly realize the equalizing charge in luminescent layer, improve excitation purity, the luminous efficiency of device
And service life.The second hole mobile material type being applied in producing line at present is limited, and is asked for solving above-mentioned technology
The effect is unsatisfactory for topic, and therefore, there is an urgent need to develop the second hole mobile materials for providing excellent effect.
Invention content
In view of the above-mentioned problems existing in the prior art, a kind of aromatic amine derivant of present invention offer and its organic electroluminescent
Device.
The present invention provides a kind of aromatic amine derivants, shown in structural formula such as formula (I)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two
Valence heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60
Base or Ar1With Ar2It is interconnected to nitrogenous five-ring heterocycles；Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, C3~
The substituted or unsubstituted heteroaryls of C60.
Preferably, the aromatic amine derivant has structure shown in logical formula (II) or (III)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two
Valence heteroaryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, fluorine atom, cyano, C1~C4 substitution or not
Substituted alkyl, the substituted or unsubstituted alkoxies of C1~C4, the substituted or unsubstituted aryl of C6~C30, C3~C30 substitutions or
Unsubstituted heteroaryl or the R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two groups of middle arbitrary neighborhood can be interconnected mutually
It is connected into ring；Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60.
Preferably, the L is selected from singly-bound or following group：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third
Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the Ar3Selected from hydrogen or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7Independently selected from hydrogen, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl
Base, normal-butyl, sec-butyl, isobutyl group, tertiary butyl, trifluoromethyl, phenyl.
Preferably, the aromatic amine derivant has structure shown in following general formula：
Wherein, Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60；
Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, positive fourth
Base, sec-butyl, isobutyl group, tertiary butyl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, fluorine atom, cyanogen
The substituted or unsubstituted alkyl of base, C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 are substituted or unsubstituted
The substituted or unsubstituted heteroaryl of aryl, C3~C30 or the R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Middle arbitrary neighborhood
Two groups can be connected with each other cyclization.
Most preferably, any one of the aromatic amine derivant in HT1~HT99 as follows：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode, anode and
The one or more organic matter layers being placed between the cathode and the anode；Contain the aromatic amine in the organic matter layer
Derivative.
Preferably, the second hole transmission layer is contained in the organic matter layer；Contain in second hole transmission layer
The aromatic amine derivant.
It is furthermore preferred that containing the first hole transmission layer in the organic matter layer simultaneously；First hole transmission layer
In contain the aromatic amine derivant.
Beneficial effects of the present invention：
Aromatic amine derivant provided by the invention can be formed ammonium ion free radical, make it have height under electric field action
Hole mobility；In addition, the glass transition temperature (Tg) of such compound is high, stability and film forming are all good, can be with
Transport layer softening, hole transporting material is avoided caused by the low Tg of material ooze outs from organic resin and transmission performance decline
The problems such as, it ensure that device can use steadily in the long term.Such compound has highest occupied molecular orbital energy level appropriate, i.e.,
The first hole transmission layer is can be used as, but also as the second hole transmission layer, the energy between luminescent layer and anodic interface can be reduced
It is differential, the transmission in hole is improved, when especially as the second hole transmission layer, additionally it is possible to reduce luminescent layer and the first hole transmission layer
Between energy level difference improve the excitation purity, luminous efficiency and service life of device to realize the equalizing charge in luminescent layer,
And the driving voltage for reducing device is the OLED material of a kind of function admirable.
Specific implementation mode
Present invention firstly provides a kind of aromatic amine derivant, structure formula (I) is as follows：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two
Valence heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60
Base or Ar1With Ar2It is interconnected to nitrogenous five-ring heterocycles；Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, C3~
The substituted or unsubstituted heteroaryls of C60.
Preferably, the aromatic amine derivant has structure shown in logical formula (II) or (III)：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two
Valence heteroaryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, fluorine atom, cyano, C1~C4 substitution or not
Substituted alkyl, the substituted or unsubstituted alkoxies of C1~C4, the substituted or unsubstituted aryl of C6~C30, C3~C30 substitutions or
Unsubstituted heteroaryl or the R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two groups of middle arbitrary neighborhood can be interconnected mutually
It is connected into ring；Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60.
Preferably, L is selected from singly-bound or following group：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, positive third
Base, isopropyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
Preferably, the Ar3Selected from hydrogen or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7Independently selected from hydrogen, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl
Base, normal-butyl, sec-butyl, isobutyl group, tertiary butyl, trifluoromethyl, phenyl.
Preferably, the aromatic amine derivant has structure shown in following general formula：
Wherein, Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60；
Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, positive fourth
Base, sec-butyl, isobutyl group, tertiary butyl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, fluorine atom, cyanogen
The substituted or unsubstituted alkyl of base, C1~C4, the substituted or unsubstituted alkoxies of C1~C4, C6~C30 are substituted or unsubstituted
The substituted or unsubstituted heteroaryl of aryl, C3~C30.
Aryl of the present invention refer to aromatic hydrocarbon molecule an aromatic core carbon on remove a hydrogen atom after, remaining group
General name, can be monocyclic aryl or fused ring aryl, such as can be selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthrene
Base, pyrenyl, fluorenyl or benzo phenanthryl etc., but not limited to this.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon is replaced by hetero atom
General name, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl
Base, such as pyridyl group, quinolyl, carbazyl, thienyl, benzothienyl, furyl, benzofuranyl, pyrimidine can be selected from
Base, benzo pyrimidine radicals, imidazole radicals or benzimidazolyl etc., but not limited to this.
Divalent aryl of the present invention refer to aromatic hydrocarbon molecule two aromatic core carbon on respectively remove a hydrogen atom after, be left
Bivalent group general name, can be valentbivalent monocyclic aryl or divalent fused ring aryl, such as can be selected from phenylene, sub- biphenyl
Base, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, sub- pyrenyl, fluorenylidene or sub- benzo phenanthryl etc., but not limited to this.
Divalent heteroaryl radical of the present invention refers to that one or more of divalent aryl aromatic core carbon is replaced to obtain by hetero atom
Group general name, the hetero atom includes but not limited to oxygen, sulphur or nitrogen-atoms, and the divalent heteroaryl radical can be valentbivalent monocyclic
Heteroaryl or divalent fused ring heteroaryl, such as sub-pyridyl group, sub- quinolyl, sub- carbazyl, sub- thienyl, sub- benzo can be selected from
Thienyl, furylidene, sub- benzofuranyl, sub- pyrimidine radicals, sub- benzo pyrimidine radicals, sub- imidazole radicals or sub- benzimidazolyl etc.,
But not limited to this.
Alkyl of the present invention refers to alkyl made of removing a hydrogen atom in alkane molecule, can be straight chain alkane
Base, branched alkyl, naphthenic base, such as methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, uncle can be selected from
Butyl, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refers to-O- alkyl, wherein the alkyl is as previously defined.
Nitrogenous five-ring heterocycles of the present invention refer to substituted or unsubstituted carbazole.
Specifically, any one of the aromatic amine derivant in HT1~HT99 as follows：
Some specific constructive forms of aromatic amine derivant of the present invention are enumerated above, but the present invention does not limit to
Every based on structure shown in listed general formula in these listed chemical constitutions, substituent group is that group as defined above is all answered
It is included.
The preparation method of aromatic amine derivant of the present invention can be prepared by following synthetic route：
Wherein, L is selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, C3~C30 substituted or unsubstituted two
Valence heteroaryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60
Base or Ar1With Ar2Nitrogenous five-ring heterocycles can be interconnected to；Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60,
The substituted or unsubstituted heteroaryls of C3~C60.
First, the bromo- 8- chloroquinolines of 2- react with connection pinacol borate, obtain intermediate A；Intermediate A again with I-
Suzuki reactions occur for L-Br, obtain intermediate B；Then, intermediate B and contain Ar1And Ar2Arylamine pass through Buchwald-
Hartwig coupling reactions obtain intermediate C；Under the action of ammonium hydroxide, intermediate C aminations obtain intermediate D；Intermediate D and 2-
Annulation occurs for chloro- 1,3-PD, obtains intermediate E；Finally, intermediate E again with contain Ar3Boric acid ester compound hair
Raw Suzuki reactions, you can obtain target compound (I).
The present invention does not have special limitation, use well-known to those skilled in the art the above-mentioned reaction condition respectively reacted
Reaction condition, the preparation method is simple, and raw material is easy to get.
The present invention further provides a kind of organic electroluminescence device, the organic electroluminescence device include cathode,
Anode and the one or more organic matter layers being placed between the cathode and the anode；Contain the present invention in the organic matter layer
The aromatic amine derivant；Preferably, the second hole transmission layer, second hole transport are contained in the organic matter layer
Layer contains the aromatic amine derivant between luminescent layer and anode；Preferably, contain simultaneously in the organic matter layer
There are the first hole transmission layer, first hole transmission layer to contain between second hole transmission layer and anode
There is the aromatic amine derivant.
According to the present invention, the device architecture of use is preferred, Ke Yiwei：Transparent glass is as anode；4,4', 4 "-three
[2- naphthylphenyls amino] triphenylamine (2-TNATA) is used as hole injection layer；N, N'- diphenyl-N, N'- (1- naphthalenes) -1,
1'- biphenyl -4,4'- diamines (NPB) or the compounds of this invention (HT1~HT99) are used as the first hole transmission layer；Chemical combination of the present invention
Object (HT1~HT99) is used as the second hole transmission layer；(9- carbazoles) biphenyl of 4,4'- bis- (CBP) and two (1- phenyl-isoquinolin)
(acetylacetone,2,4-pentanedione) closes iridium ((piq)2Ir (acac)) with 95:The mixture of 5 weight ratio is as luminescent layer；Bis- (2- methyl -8- hydroxyls
Base quinoline-N1, O8)-(1,1'- biphenyl -4- hydroxyls) aluminium (BAlq) be used as hole blocking layer；8-hydroxyquinoline aluminium (Alq3) conduct
Electron transfer layer；LiF is as electron injecting layer；Al is as cathode.
The organic electroluminescence device can be used for the application neck such as flat-panel monitor, lighting source, direction board, signal lamp
Domain.
By following embodiment, the present invention, but so as not to the limitation present invention are more fully explained.In the base of the description
On plinth, those of ordinary skill in the art will without creative efforts, in disclosed entire scope
Implement the present invention and prepares other compounds according to the present invention.
The present invention is not particularly limited the raw material sources employed in following embodiment, for commercial product or can adopt
It is prepared with preparation method well-known to those skilled in the art.
Embodiment 1：The preparation of intermediate A
By the bromo- 8- chloroquinolines of 12.13g (50mmol) 2-, 15.55g (60mmol) connection boric acid pinacol ester, 1.10g
(1.5mmol) [bis- (diphenylphosphino) ferrocene of 1,1'-] palladium chloride and 14.73g (150mmol) potassium acetate are dissolved in
In 328ml toluene, back flow reaction 12 hours, after being cooled to room temperature, cross diatom soil hopper, remove solvent, gained under an argon
Residue recrystallizes in heptane, filters out crystal and drying, obtains intermediate A (10.86g, 37.5mmol).
Embodiment 2：The preparation of intermediate B
The preparation of intermediate B -1：By 8.69g (30mmol) intermediate A, 8.49g (30mmol) to bromo-iodobenzene, 0.71g
(0.6mmol) tetrakis triphenylphosphine palladium, 86ml toluene, aqueous sodium carbonate (2M, 42ml) are added in flask, and back flow reaction 8 is small
When, it is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing is dry, is purified by column chromatography, in obtaining
Mesosome B-1 (7.84g, 24.6mmol).
Intermediate B -2 can be prepared to intermediate B -7 by the preparation method of intermediate B -1.
Embodiment 3：The preparation of compound HT4
Under argon atmospher, by 2.59g (10mmol) 2- bromines phenanthroline, 4.13g (10mmol) N, N, N '-triphenyl biphenyl two
Amine, 1.92g (20mmol) sodium tert-butoxide are dissolved in 100ml dehydrated toluenes, be added with stirring 0.04g (0.2mmol) palladium,
0.05g (0.2mmol) triphenylphosphine reacts 8 hours at 80 DEG C.After cooling, filtered by diatomite/silica gel funnel, filtrate
Organic solvent is removed by vacuum distillation, it is residue obtained to be recrystallized in toluene, it is dry, you can to obtain 5.20g (8.8mmol) changes
Close object HT4, yield 88%.Mass spectrum m/z：591.88 (calculated values：590.73).Theoretical elemental content (%) C42H30N4：C,
85.40；H,5.12；N,9.48.Survey constituent content (%)：C,85.38；H,5.14；N,9.50.The above results confirmation is produced
Object is target product.
Embodiment 4：The preparation of compound HT12
The preparation of compound M-1：It is under argon atmospher, 3.38g (20mmol) p-aminodiphenyl, 5.94g (20mmol) 9- is bromo-
Dibenzo [2,1-B] furans, 3.84g (40mmol) sodium tert-butoxide are dissolved in 200ml dehydrated toluenes, are added with stirring 0.08g
(0.4mmol) palladium, 0.1g (0.4mmol) triphenylphosphine, react 8 hours at 80 DEG C.After cooling, pass through diatomite/silicon
Glue funnel filters, and filtrate removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can to obtain
6.94g (18mmol) compound M-1, yield 90%.
The preparation of intermediate A -1：5.18g (20mmol) 2- bromines phenanthroline, 6.22g (24mmol) are joined into boric acid pinacol
Ester, 0.44g (0.6mmol) [bis- (diphenylphosphino) ferrocene of 1,1'-] palladium chlorides and the dissolving of 5.89g (60mmol) potassium acetate
In 131ml toluene, back flow reaction 12 hours, after being cooled to room temperature, cross diatom soil hopper, remove solvent, institute under an argon
It obtains residue to recrystallize in heptane, filters out crystal and drying, obtain intermediate A -1 (5.45g, 17.8mmol).
The preparation of intermediate F-1：By 4.59g (15mmol) intermediate A -1,4.24g (15mmol) to bromo-iodobenzene, 0.35g
(0.3mmol) tetrakis triphenylphosphine palladium, 43ml toluene, aqueous sodium carbonate (2M, 21ml) are added in flask, and back flow reaction 8 is small
When, it is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing is dry, is purified by column chromatography, in obtaining
Mesosome F-1 (4.32g, 12.9mmol).
The preparation of compound HT12：2- bromine phenanthrolines are substituted for the intermediate F-1 of equimolar amounts, by N, N, N '-three
Phenyl benzidine is replaced with the compound M-1 of equimolar amounts, other steps are same as Example 3, you can obtain chemical combination
Object HT12.Mass spectrum m/z：641.39 (calculated values：639.76).Theoretical elemental content (%) C46H29N3O：C,86.36；H,4.57；
N,6.57；O,2.50.Survey constituent content (%)：C,86.33；H,4.59；N,6.55；O,2.54.The above results confirm to obtain
Product is target product.
Embodiment 5：The preparation of compound HT23
The preparation of compound M-2：P-aminodiphenyl is replaced with to the aniline of equimolar amounts, by the bromo- dibenzo of 9- [2,1-
B] furans is replaced with the 2- bromo- 9 of equimolar amounts, 9 '-spiral shell, two fluorenes, preparation of other steps with compound M-1 in embodiment 4
It is identical, you can to obtain compound M-2.
The preparation of intermediate C-1：Under argon atmospher, the bromo- 8- chloroquinolines of 4.85g (20mmol) 2-, 8.15g (20mmol) are changed
It closes object M-2,3.84g (40mmol) sodium tert-butoxide to be dissolved in 200ml dehydrated toluenes, is added with stirring 0.09g (0.4mmol) acetic acid
Palladium, 0.10g (0.4mmol) triphenylphosphine, react 8 hours at 80 DEG C.It after cooling, is filtered by diatomite/silica gel funnel, filter
Liquid removes organic solvent by vacuum distillation, residue obtained to be recrystallized in toluene, dry, you can to obtain 9.22g
(16.2mmol) intermediate C-1, yield 81%.
The preparation of intermediate D-1：By 8.54g (15mmol) intermediates C-1,1.8ml (45mmol) ammonium hydroxide, 0.29g
The DMF of (1.5mmol) cuprous iodide, 0.15g (1.5mmol) acetylacetone,2,4-pentanedione, 9.77g (30mmol) cesium carbonate and 150ml, heating
To 90 DEG C, 15h is reacted, after cooling, is filtered, the organic solvent vacuum distillation in filtrate is fallen, is purified by column chromatography, finally
To intermediate D-1 (7.09g, 12.9mmol).
The preparation of intermediate E -1：By the chloro- 1,3- of 5.50g (10mmol) intermediate D-1,1.11g (10mmol) 2- the third two
Alcohol, 0.11g (0.5mmol) palladium, 2,4,6- collidines of 0.12g (0.5mmol), 0.11g (1mmol) trifluoroacetic acid,
Under oxygen atmosphere (1atm), 150 DEG C are warming up to, is reacted 12 hours.After reaction, it filters, filtrate concentration is pure by column chromatography
Change, obtains intermediate E -1 (5.15g, 8.3mmol).
The preparation of compound HT23：By 4.96g (8mmol) intermediate E -1,1.63g (8mmol) phenyl boric acids pinacol ester,
0.19g (0.16mmol) tetrakis triphenylphosphine palladium, 23ml toluene, aqueous sodium carbonate (2M, 11.2ml) are added in flask, reflux
Reaction 8 hours, is cooled to room temperature, is extracted with toluene, organic phase saturated common salt water washing, dry, is purified by column chromatography,
Obtain compound HT23.Mass spectrum m/z：660.75 (calculated values：661.81).Theoretical elemental content (%) C49H31N3：C,88.93；
H,4.72；N,6.35.Survey constituent content (%)：C,88.95；H,4.74；N,6.32.The above results confirm that it is mesh to obtain product
Mark product.
Embodiment 6：The preparation of compound HT34
The preparation of compound M-3：P-aminodiphenyl is replaced with to the 2- phenanthryl amine of equimolar amounts, by the bromo- dibenzo of 9-
[2,1-B] furans is replaced with the 4- bromine dibenzofurans of equimolar amounts, other steps with compound M-1 in embodiment 4
It prepares identical, you can obtain compound M-3.
The preparation of intermediate C-2：The bromo- 8- chloroquinolines of 2- are replaced with to the intermediate B -6 of equimolar amounts, by compound M-
2 are replaced with the compound M-3 of equimolar amounts, other steps are identical as the preparation method of intermediate C-1 in embodiment 5, i.e.,
Intermediate C-2 can be obtained.
The preparation of intermediate D-2：Intermediate C-1 is replaced with to the intermediate C-2 of equimolar amounts, other steps with reality
The preparation method for applying intermediate D-1 in example 5 is identical, you can obtains intermediate D-2.
The preparation of intermediate E -2：Intermediate D-1 is replaced with to the intermediate D-2 of equimolar amounts, other steps with reality
The preparation method for applying intermediate E -1 in example 5 is identical, you can obtains intermediate E -2.
The preparation of compound HT34：Intermediate E -1 is replaced with to the intermediate E -2 of equimolar amounts, by phenyl boric acid frequency which
Alcohol ester is replaced with the 4- pyridine boronic acid pinacol esters of equimolar amounts, system of other steps with compound HT23 in embodiment 5
Preparation Method is identical, you can obtains compound HT34.Mass spectrum m/z：743.17 (calculated values：740.87).Theoretical elemental content (%)
C53H32N4O：C,85.92；H,4.35；N,7.56；O,2.16.Survey constituent content (%)：C,85.94；H,4.37；N,7.52；
O,2.19.The above results confirm that it is target product to obtain product.
Embodiment 7：The preparation of compound HT48
The preparation of compound M-4：P-aminodiphenyl is replaced with to the 2- phenanthryl amine of equimolar amounts, by the bromo- dibenzo of 9-
[2,1-B] furans is replaced with the 5- bromobenzenes of equimolar amounts simultaneously [B] naphtho- [1,2-D] thiophene, other steps in embodiment 4
Preparing for compound M-1 is identical, you can obtains compound M-4.
The preparation of intermediate B -5：Compound N -1 is replaced with to the compound N -3 of equimolar amounts, by 3- methylphenylboronic acids
Pinacol ester is replaced with the 3- cyanophenylboronic acid pinacol esters of equimolar amounts, other steps with intermediate B -1 in embodiment 3
Preparation method it is identical, you can obtain intermediate B -5.
The preparation of intermediate C-3：Compound M-2 is replaced with to the compound M-4 of equimolar amounts, other steps with reality
The preparation method for applying intermediate C-1 in example 5 is identical, you can obtains intermediate C-3.
The preparation of intermediate D-3：Intermediate C-1 is replaced with to the intermediate C-3 of equimolar amounts, other steps with reality
The preparation method for applying intermediate D-1 in example 5 is identical, you can obtains intermediate D-3.
The preparation of intermediate E -3：Intermediate D-1 is replaced with to the intermediate D-3 of equimolar amounts, other steps with reality
The preparation method for applying intermediate E -1 in example 5 is identical, you can obtains intermediate E -3.
The preparation of compound HT48：Intermediate E -1 is replaced with to the intermediate E -3 of equimolar amounts, by phenyl boric acid frequency which
Alcohol ester is replaced with the 2- trifluoromethylbenzene boronic acid pinacol esters of equimolar amounts, other steps with compound in embodiment 5
The preparation method of HT23 is identical, you can obtains compound HT48.Mass spectrum m/z：749.09 (calculated values：747.84).Theoretical elemental
Content (%) C49H28F3N3S：C,78.70；H,3.77；F,7.62；N,5.62；S,4.29.Survey constituent content (%)：C,
78.73；H,3.74；F,7.66；N,5.63；S,4.33.The above results confirm that it is target product to obtain product.
Embodiment 8：The preparation of compound HT61
The preparation of intermediate C-4：Compound M-2 is replaced with to 3, the 6- diphenyl -9H- carbazoles of equimolar amounts, other
Step is identical as the preparation method of intermediate C-1 in embodiment 5, you can obtains intermediate C-4.
The preparation of intermediate D-4：Intermediate C-1 is replaced with to the intermediate C-4 of equimolar amounts, other steps with reality
The preparation method for applying intermediate D-1 in example 5 is identical, you can obtains intermediate D-4.
The preparation of intermediate E -4：Intermediate D-1 is replaced with to the intermediate D-4 of equimolar amounts, other steps with reality
The preparation method for applying intermediate E -1 in example 5 is identical, you can obtains intermediate E -4.
The preparation of compound HT61：Intermediate E -1 is replaced with to the intermediate E -4 of equimolar amounts, by phenyl boric acid frequency which
Alcohol ester is replaced with the quinoline -4- pinacol borates of equimolar amounts, system of other steps with compound HT23 in embodiment 5
Preparation Method is identical, you can obtains compound HT61.Mass spectrum m/z：702.56 (calculated values：700.85).Theoretical elemental content (%)
C51H32N4：C,87.40；H,4.60；N,7.99.Survey constituent content (%)：C,87.44；H,4.62；N,7.97.The above results
Confirm that it is target product to obtain product.
Embodiment 9：The preparation of red organic electroluminescence device 1
First, it is formed with the thickness vacuum deposition 2-TNATA of 60nm in the ITO layer (anode) for being formed in organic substrate
Hole injection layer；The first hole transmission layer is formed with the thickness vacuum evaporation NPB of 60nm on above-mentioned hole injection layer；It
Afterwards, using the thickness vacuum evaporation compound HT4 of 20nm as the second hole transmission layer on the first hole transmission layer；Then, exist
With weight ratio for 95 on above-mentioned second hole transmission layer:5 CBP and (piq)2Ir (acac) vacuum depositions are thick as luminescent layer
Degree is 30nm；Then, hole blocking layer is formed with the thickness vacuum deposition BAlq of 10nm on above-mentioned luminescent layer；In above-mentioned sky
With the thickness vacuum deposition Alq of 40nm on the barrier layer of cave3To form electron transfer layer；Then, LiF is deposited with the thickness of 0.2nm
As electron injecting layer；Finally, cathode is formed with the thickness depositing Al of 150nm.
Embodiment:10：The preparation of red organic electroluminescence device 2
Compound HT4 is replaced with compound HT12, other steps are same as Example 9.
Embodiment 11：The preparation of red organic electroluminescence device 3
Compound HT4 is replaced with compound HT23, other steps are same as Example 9.
Embodiment 12：The preparation of red organic electroluminescence device 4
Compound HT4 is replaced with compound HT34, other steps are same as Example 9.
Embodiment 13：The preparation of red organic electroluminescence device 5
Compound HT4 is replaced with compound HT48, other steps are same as Example 9.
Embodiment 14：The preparation of red organic electroluminescence device 6
Compound HT4 is replaced with compound HT61, other steps are same as Example 9.
Embodiment 15：The preparation of red organic electroluminescence device 7
Compound HT4 is replaced with compound HT70, other steps are same as Example 9.
Embodiment 16：The preparation of red organic electroluminescence device 8
Compound HT4 is replaced with compound HT89, other steps are same as Example 9.
Embodiment 17：The preparation of red organic electroluminescence device 9
Compound HT4 is replaced with compound HT98, other steps are same as Example 9.
Embodiment 18：The preparation of red organic electroluminescence device 10
NPB is replaced with compound HT4, other steps are same as Example 9.
Embodiment 19：The preparation of red organic electroluminescence device 11
NPB is replaced with compound HT12, other steps are same as Example 9.
Embodiment 20：The preparation of red organic electroluminescence device 12
NPB is replaced with compound HT23, other steps are same as Example 9.
Embodiment 21：The preparation of red organic electroluminescence device 13
NPB is replaced with compound HT34, other steps are same as Example 9.
Embodiment 22：The preparation of red organic electroluminescence device 14
NPB is replaced with compound HT48, other steps are same as Example 9.
Embodiment 23：The preparation of red organic electroluminescence device 15
NPB is replaced with compound HT61, other steps are same as Example 9.
Embodiment 24：The preparation of red organic electroluminescence device 16
NPB is replaced with compound HT70, other steps are same as Example 9.
Embodiment 25：The preparation of red organic electroluminescence device 17
NPB is replaced with compound HT89, other steps are same as Example 9.
Embodiment 26：The preparation of red organic electroluminescence device 18
NPB is replaced with compound HT98, other steps are same as Example 9.
Comparative example：The preparation of red organic electroluminescence device 21
Other than not forming the second hole transmission layer this point, luminescent device has been made in method same as Example 9.
Compound involved in the embodiment of the present invention and comparative example is as follows：
The luminescent properties for the organic electroluminescence device that the embodiment of the present invention is prepared are as shown in the table：
The above result shows that aromatic amine derivant provided by the invention, there is high hole mobility and Tg, stability and
Good film-forming property can ensure the use that long term device is stablized.Such compound also has highest occupied molecular orbital energy appropriate
Grade, when as the first hole transmission layer, can reduce the energy level difference between luminescent layer and anodic interface, as the second hole transport
When layer, then the energy level difference between luminescent layer and the first hole transmission layer can be reduced, additionally it is possible to realize the equalizing charge in luminescent layer.
Such compound is the OLED material of a kind of function admirable, can either improve the excitation purity, luminous efficiency and service life of device,
The driving voltage of device can also be reduced.
Obviously, the explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should refer to
Go out, it, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field
Bright some improvement and modification can also be carried out, these improvement and modification are also fallen within the protection scope of the claims of the present invention.
Claims (9)
1. a kind of aromatic amine derivant, which is characterized in that have the structure as shown in logical formula (I)：
Wherein, it is miscellaneous to be selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3~C30 by L
Aryl；Ar1、Ar2Independently selected from the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60, or
Person Ar1With Ar2It is interconnected to nitrogenous five-ring heterocycles；Ar3It is taken selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, C3~C60
Generation or unsubstituted heteroaryl.
2. aromatic amine derivant according to claim 1, which is characterized in that the aromatic amine derivant has general formula
(II) or structure shown in (III)：
Wherein, it is miscellaneous to be selected from singly-bound, the substituted or unsubstituted divalent aryls of C6~C30, the substituted or unsubstituted divalent of C3~C30 by L
Aryl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Replace independently selected from hydrogen, deuterium, fluorine atom, cyano, C1~C4 or unsubstituted
Alkyl, the substituted or unsubstituted alkoxies of C1~C4, the substituted or unsubstituted aryl of C6~C30, C3~C30 substitution or do not take
The heteroaryl in generation or the R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Two groups of middle arbitrary neighborhood are connected with each other cyclization；
Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60.
3. aromatic amine derivant according to claim 1, which is characterized in that the L is selected from singly-bound or following group：
Wherein, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, different
Propyl, normal-butyl, sec-butyl, isobutyl group, tertiary butyl.
4. aromatic amine derivant according to claim 1, which is characterized in that the Ar3Selected from hydrogen or following group：
Wherein, X1、X2、X3、X4、X5、X6、X7Independently selected from hydrogen, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, just
Butyl, sec-butyl, isobutyl group, tertiary butyl, trifluoromethyl, phenyl.
5. aromatic amine derivant according to claim 1, which is characterized in that the aromatic amine derivant has following logical
Structure shown in formula：
Wherein, Ar3Selected from hydrogen, the substituted or unsubstituted aryl of C6~C60, the substituted or unsubstituted heteroaryls of C3~C60；Y1、
Y2、Y3、Y4、Y5、Y6、Y7、Y8Independently selected from hydrogen, deuterium, cyano, fluorine atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl,
Sec-butyl, isobutyl group, tertiary butyl；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10Independently selected from hydrogen, deuterium, fluorine atom, cyano, C1
The substituted or unsubstituted alkyl of~C4, the substituted or unsubstituted alkoxies of C1~C4, the substituted or unsubstituted aryl of C6~C30,
The substituted or unsubstituted heteroaryls of C3~C30.
6. aromatic amine derivant according to claim 1, which is characterized in that the aromatic amine derivant is selected from following institute
Show any one in HT1~HT99：
7. a kind of organic electroluminescence device, which is characterized in that including cathode, anode and be placed in the cathode and the anode it
Between one or more organic matter layers；Spread out containing aromatic amine according to any one of claims 1 to 6 in the organic matter layer
Biology.
8. organic electroluminescence device according to claim 7, which is characterized in that contain second in the organic matter layer
Hole transmission layer；Contain aromatic amine derivant according to any one of claims 1 to 6 in second hole transmission layer.
9. organic electroluminescence device according to claim 7, which is characterized in that contain first in the organic matter layer
Hole transmission layer；Contain aromatic amine derivant according to any one of claims 1 to 6 in first hole transmission layer.
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Application publication date: 20180921 |
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