CN107188829B - It is a kind of using perfluoro phenylene as the oled light electric material of core and its application - Google Patents
It is a kind of using perfluoro phenylene as the oled light electric material of core and its application Download PDFInfo
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- CN107188829B CN107188829B CN201710348355.3A CN201710348355A CN107188829B CN 107188829 B CN107188829 B CN 107188829B CN 201710348355 A CN201710348355 A CN 201710348355A CN 107188829 B CN107188829 B CN 107188829B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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Abstract
The present invention relates to a kind of using perfluoro phenylene as the oled light electric material of core and its application, has the molecular structure as shown in formula I:
Description
Technical field
The present invention relates to a kind of oled light electric material and its applications more particularly to a kind of using perfluoro phenylene as core
Oled light electric material and its application.
Background technique
In recent years, some photoelectric materials for OLED device are increasingly known, it is known that aromatic diamines are derivative
Object is used as hole mobile material in OLED device, when using such material, needs to improve device and applies voltage to obtain enough
Light emission luminance, this results in the shortening of device lifetime, and increases power consumption.To solve these problems, by adulterating electronics
Acceptor compound can make in OLED device hole injection and hole transport significantly improve (document: He Gufeng,
Appl.Phys.lett.85(2004)3911-3913).Under same luminous efficiency, the addition of electron acceptor compound can
With reduction OLED device operating voltage by a relatively large margin.Strong electron acceptor compound such as four cyano quinone bismethane (TCNQ) or
Tetra- fluoro of 2,3,5,6--four cyano -1,4- benzoquinones bismethane (F4TCNQ).
For the existing method (i.e. P doping) for improving hole transport by doping electron acceptor compound, material used
The physical property of material be during sublimation purification or vacuum evaporation it is of problems, be directed to vapo(u)rability fluorine extremely rambunctious
The four cyano benzoquinones bismethane (TCNQ or F4TCNQ) of change is easy to diffuse in sublimation process to set since its molecular weight is smaller
In standby, lead to contaminated equipment or device, so that this kind of dopant cannot be used in batch production device.
Currently, research and relevant report about p-type dopant material at home, international all few, research in this respect
Urgent need further strengthens.
Summary of the invention
The present invention provides one kind for deficiency existing for existing p-type dopant material in the hole transmission layer of OLED device
Using perfluoro phenylene as the oled light electric material of core and its application.
The technical scheme to solve the above technical problems is that
It is a kind of using perfluoro phenylene as the oled light electric material of core, which is characterized in that have the molecule as shown in formula I
Structure:
Wherein, group shown in the Ar expression II:
R described in formula II1-R5It is independent any in chlorine, fluorine, nitro, trifluoromethyl, isothiocyano or cyano
It is a kind of.
Further, with molecular structure as follows:
The beneficial effect of oled light electric material provided by the invention is:
1) such material has by force by introducing strong electrophilic malononitrile and other on the basis of perfluoro phenylene
The aryl group of electron-withdrawing ability, after such material is used as the dopant material of OLED device hole-transporting layer, in work
Lower voltage is set during making and is obtained with enough light emission luminance, it is thus possible to greatly improve the luminous effect of OLED device
Rate and service life.
2) such material shows higher thermal stability and glass transition temperature, easy to form good amorphous thin
Film, controlling is strong during high-temperature vacuum is deposited.
The synthetic route of above-mentioned oled light electric material is as follows:
Specific reaction process are as follows: aromatic ketone compound and malononitrile are under nitrogen or inert gas shielding, with zinc chloride, chlorine
Change calcium, lithium hydride, potassium carbonate or cesium carbonate and alkaline environment is provided, is reacted 1-5 hours under conditions of 50~100 DEG C.
The above reaction raw materials substance and the substance for providing alkaline environment are that the art often uses substance or commercially available
Substance.
The organic electroluminescence device in functional layer comprising above-mentioned oled light electric material is also claimed in the present invention.
Further, the functional layer refers to hole transmission layer.
Further, the hole transmission layer is made of host material and dopant, wherein the dopant refers to right
It is required that oled light electric material described in 1 or 2.
Further, specific structure include the transparent matrix layer being sequentially overlapped from the bottom to top, anode layer, hole injection layer,
Hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer.
The effect of each layer and common used material are described below in organic electroluminescence device:
Anode layer has the function of injecting holes into hole transmission layer, and anode layer is usually constituted by the following substances: as aluminium,
The metals such as gold, silver, nickel, palladium or platinum；The gold such as indium oxide, tin oxide, zinc oxide, indium tin composite oxides, indium zinc composite oxide
Belong to oxide；The metal halides such as cupric iodide；Carbon black；Or partially electronically conductive macromolecule etc..
Hole injection layer is for promoting hole to be injected into luminescent layer by anode layer, and hole injection layer is by host material and Ben Fa
The oled light electric material of bright offer is formed as dopant.Wherein, host material is selected from phthalocyanine copper complex (CuPc), 4,4 ',
4 " ,-three (N-3- tolyl-N- phenyl-amido) triphenylamines (m-MTDATA), 4,4 ', 4 " ,-three (N- (2- naphthalene)-N- phenyl-
Amido) triphenylamine (2-TNATA), N, N, N ', N '-four (4- methoxyl group-phenyl) benzidine (MeO-TPD), (2,2 ' 7,7 '-four-
Two fluorenes (spiral shell-TTB) of (N, N- diphenylamines) -9,9- spiral shell, three (terphenyl -4- base) amine, N, N '-diphenyl-N, N '-(1- naphthalene) -
One of 1,1 '-biphenyl -4,4 '-diamines (NPB).
Hole transmission layer is the high efficiency from anode layer injection hole and can effectively transmit injected holes material.
It is low, stable to the permeability height, hole mobility height, property of visible light that therefore, it is necessary to the ionization potentials of the material, it is also necessary to make
The light being not likely to produce when for or using becomes the impurity of trap (trap).It is in contact additionally, due to luminescent layer, needs hole transport
Layer does not make the light delustring for carrying out light emitting layer, and forms exciplex not between luminescent layer and reduce efficiency, common hole
Transmission material can be enumerated with N, and N '-diphenyl-N, N '-(1- naphthalene) -1,1 '-biphenyl -4,4 '-diamines (NPB) are representative
Aromatic diamine containing more than two tertiary amines, triphen amine have aromatic amine compounds, the carbazole of star radial configuration
Analog derivative etc..
Luminescent layer is formed by luminescent substance, wherein between the electrode for being applied with electric field, this luminescent substance because of hole and
Electronics in conjunction with and excite, thus show by force shine.Usual luminescent layer contain as luminescent substance doping type material and
Host material.High efficiency electroluminescent device in order to obtain, a kind of dopant material can be used in luminescent layer, or uses a variety of doping
Material.Dopant material can be simple fluorescence or phosphor material, or be formed by different fluorescence and phosphorescence matched combined, luminescent layer
It can be single emitting layer material, or the recombination luminescence layer material being superimposed.The material of main part of luminescent layer is not only
Ambipolar charge transport quality is needed to have, while needing appropriate energy rank, excitation energy is efficiently transferred to object hair
Luminescent material, this kind of materials can enumerate diphenylethyllene aryl derivatives, stibene derivative, carbazole derivates,
Triarylamine derivatives, anthracene derivant, pyrene derivatives, coronene derivative etc..Relative to material of main part, guest materials is mixed
Entering weight is preferably 0.01%-20%.This kind of materials can enumerate the metal complexs such as iridium, nail, platinum, rhenium, palladium.
The material of electron transfer layer can select any made by having in the electroluminescent material of electronic transport property
With such material can be enumerated such as benzimidazoles such as 1,3,5- tri- (1- naphthalene -1H- benzimidazolyl-2 radicals-yl) benzene (TPBI)
Derivative, the metal complexs such as three (8-hydroxyquinoline) aluminium (Alq3), 2- (4- 2-methyl-2-phenylpropane base) -5- (4,4 "-xenyl) -1,3,
The oxadiazole derivatives such as 4- oxadiazoles (PBD), the phenanthroline derivative such as 4,7- diphenyl -1,10- ferrosins (BPhen), three
Zole derivatives, quinoline, quinoxaline derivant etc..
Metal, alloy, conductive compound and their mixing that work function is less than 4eV can be selected in cathode layer materials
Object.Its concrete example is aluminium, calcium, magnesium, lithium, magnesium alloy, aluminium alloy etc..It is comparatively ideal in order to efficiently obtain electroluminescence
It is that the transmitance of at least one of electrode is set as 10% or more.Cathode layer can by dry method such as vacuum evaporation, vapor deposition or
Sputtering is formed.
The beneficial effect of organic electroluminescence device provided by the invention is to can be realized high brightness, is easily formed a film, efficiently
Rate, the general effect of low-voltage.
Specific embodiment
Principles and features of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and
It is non-to be used to limit the scope of the invention.
One, the preparation method of oled light electric material
The concrete structure formula of the photoelectric material of embodiment 1-6 synthesis is as follows:
Embodiment 1: the preparation of compound 1
Into three-necked flask be added 16.1g (30mmol) (perfluoro -1,4- phenylene) two ((perfluoro phenyl) ketone),
4.0g (60mmol) malononitrile, 0.4g (3mmol) zinc chloride and 150mL glacial acetic acid, under nitrogen protection, mixture is heated to 100
DEG C, it is stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained filter cake MeOH/H2O 95:
5 washings, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS26F14N4, detected value [M+1] +=935.11, calculated value
933.99。
Embodiment 2: the preparation of compound 2
19.1g (30mmol) (perfluoro -1,4- phenylene) two ((fluoro- 4- tri- of 2,3,5,6- tetra- is added into three-necked flask
Trifluoromethylphenyl) ketone), 4.0g (60mmol) malononitrile, 0.4g (3mmol) potassium carbonate and 150mL glacial acetic acid, nitrogen protection
Under, mixture is heated to 100 DEG C, is stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained
Filter cake MeOH/H2O 95:5 washing, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS28F18N4, detected value [M+1] +=735.05, calculated value
733.98。
Embodiment 3: the preparation of compound 3
17.7g (30mmol) (perfluoro -1,4- phenylene) two ((4- cyano -2,3,5,6- four is added into three-necked flask
Fluorophenyl) ketone), 4.0g (60mmol) malononitrile, 0.33g (3mmol) calcium chloride and 150mL glacial acetic acid, under nitrogen protection, mix
It closes object and is heated to 100 DEG C, be stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained filter cake
It is washed with MeOH/H2O 95:5, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS28F12N6, detected value [M+1] +=649.01, calculated value
648.00。
Embodiment 4: the preparation of compound 4
17.7g (30mmol) (perfluoro -1,4- phenylene) two ((fluoro- 4- nitre of 2,3,5,6- tetra- is added into three-necked flask
Base phenyl) ketone), 4.0g (60mmol) malononitrile, 0.33g (3mmol) calcium chloride and 150mL glacial acetic acid, under nitrogen protection, mix
It closes object and is heated to 100 DEG C, be stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained filter cake
Use MeOH/H2O 95:5 washing, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS26F12N6O4, detected value [M+1] +=688.24, calculated value
687.98。
Embodiment 5: the preparation of compound 5
18.4g (30mmol) (perfluoro -1,4- phenylene) two is added into three-necked flask, and ((the fluoro- 4- of 2,3,5,6- tetra- is different
Thiocyanogen phenyl) ketone), 4.0g (60mmol) malononitrile, 0.33g (3mmol) calcium chloride and 150mL glacial acetic acid, nitrogen protection
Under, mixture is heated to 100 DEG C, is stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained
Filter cake MeOH/H2O 95:5 washing, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS28F12N6S2, detected value [M+1] +=712.98, calculated value
711.94。
Embodiment 6: the preparation of compound 6
17.1g (30mmol) (perfluoro -1,4- phenylene) two ((chloro- 2,3,5,6- tetrafluoro of 4- is added into three-necked flask
Phenyl) ketone), 4.0g (60mmol) malononitrile, 0.33g (3mmol) calcium chloride and 150mL glacial acetic acid, under nitrogen protection, mixing
Object is heated to 100 DEG C, is stirred to react 5 hours.Then reaction solution is slowly poured into 300g ice water, is filtered, gained filter cake is used
MeOH/H2O 95:5 washing, reduced vacuum is dry, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are identified using DEI-MS26Cl2F12N4, detected value [M+1] +=666.97, calculated value
665.93。
Dopant material of the compounds of this invention in luminescent device, as hole transmission layer.To the compounds of this invention 1-6 into
The test of row hot property, test result are as shown in table 1.
The heat stability testing data of 1 compound 1-6 of table
Note: glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry
Instrument) measurement, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 0.5% in nitrogen atmosphere, in Japanese Shimadzu
It is measured on the TGA-50H thermogravimetric analyzer of company, nitrogen flow 20mL/min；Highest occupied molecular orbital HOMO energy level
And minimum occupied molecular orbital lumo energy is by photoelectron emissions spectrometer (AC-2 type PESA) and ultraviolet specrophotometer
(UV) it obtained by measuring and calculation, tests as atmospheric environment.
By upper table data it is found that there is compound provided by the invention suitable HOMO, lumo energy to be suitable as OLED
Hole mobile material in device；Compound thermal stability with higher provided by the invention in upper table, so that made
OLED device containing the compounds of this invention is promoted.
Two, organic electroluminescence device
We use the obtained photoelectric material of embodiment 1-6 as the dopant material of hole injection layer and have made device one
To device six, the preparation process of organic electroluminescence device is as follows:
A) anode layer cleaned on transparent substrate layer: being cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively,
Then it is handled 2 minutes in plasma cleaner；
B) co-evaporation hole injection layer, NPB are prepared as host material, 1-6 of the embodiment of the present invention on the anode layer
Compound 1-6 is respectively as dopant material, and doping is than (weight of compound 1 accounts for compound 1 and NPB total weight for 5%
5%), with a thickness of 30nm；
C) on hole injection layer, TCTA, film thickness 10nm, this layer of organic material are deposited by vacuum evaporation mode
It is used as hole transmission layer.
D) the co-evaporation luminescent layer on hole transmission layer, CBP is as material of main part, Ir (ppy)3It is adulterated as phosphorescence
Material, phosphor material doping ratio are 5% (quality of phosphor material account for phosphor material and material of main part total weight 5%), thickness
Degree is 30nm；
E) on doping type luminescent layer compound, compound-material Alq3 is deposited by vacuum evaporation mode, with a thickness of
30nm, this layer of organic material are used as electron transfer layer；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, with a thickness of 0.5nm, which is electron injection
Layer；
G) on electron injecting layer, Al layers of vacuum evaporation cathode, with a thickness of 100nm, which is cathode layer.
For the technical effect of better photoelectric material more provided by the invention, we have also carried out two comparative examples
Experiment, with embodiment 1-6 the difference is that the hole injection layer 3 of 1 organic electroluminescence device of comparative example only has NPB as empty
Hole injection material, undope any dopant production hole injection layer.The hole injection layer of 2 organic electroluminescence device of comparative example
Using NPB as host material, 5% F4TCNQ is adulterated, makes hole injection layer instead of the compounds of this invention.
We have carried out performance test to the organic electroluminescence device of embodiment 1-6 and comparative example 1,2, as a result such as table 2
It is shown:
The performance test data of 2 embodiment 1-6 of table and the organic electroluminescence device of comparative example 1,2
From the point of view of result by table 2, photoelectric material of the present invention makes applied to electroluminescent device, obtains good table
Existing, material of the present invention is used as the hole injection layer p-type dopant material of electroluminescent device, either efficiency, brightness
It is obviously improved with driving voltage than known electroluminescent materials, the driving voltage of especially device is greatly reduced.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (5)
1. a kind of using perfluoro phenylene as the oled light electric material of core, which is characterized in that it is with molecule as follows
Structure:
2. a kind of organic electroluminescence device, which is characterized in that include oled light electricity material described in claim 1 in its functional layer
Material.
3. organic electroluminescence device according to claim 2, which is characterized in that the functional layer refers to that hole is injected
Layer.
4. organic electroluminescence device according to claim 3, which is characterized in that the hole injection layer is by host material
It is formed with dopant, wherein the dopant refers to oled light electric material described in claim 1.
5. organic electroluminescence device according to claim 4, which is characterized in that its specific structure include from the bottom to top according to
Transparent matrix layer, anode layer, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, the electron injecting layer of secondary superposition
And cathode layer.
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| US5006435A (en) * | 1988-10-05 | 1991-04-09 | Fuji Xerox Co., Ltd. | Electrophotographic photosensitive member with additive in charge generating layer |
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