CN109824659A - A kind of organic compound and its application based on heteroaryl amine structure - Google Patents
A kind of organic compound and its application based on heteroaryl amine structure Download PDFInfo
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Abstract
The invention discloses a kind of organic compound based on heteroaryl amine structure and its applications, contain different types of heteroaryl and amido class formation in the compounds of this invention structure simultaneously, there is shallower lumo energy, higher glass transition temperature and molecule thermal stability;Visible regime absorb it is low, refractive index is high, be applied to OLED device CPL layer after, can effectively promote the light extraction efficiency of OLED device.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of organic compound containing heteroaryl amine structure
And its application on OLED.
Background technique
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity
Depending on etc. large scales application field extension.But due between the external quantum efficiency and internal quantum efficiency of OLED there are huge spread,
Greatly restrict the development of OLED.Therefore, the light extraction efficiency for how improving OLED becomes research hotspot.Ito thin film and glass
The interface of the interface of glass substrate and glass substrate and air can be totally reflected, and be emitted to before OLED device to exterior space
Light account for about the 20% of organic material film EL total amount, it is thin that remaining about 80% light is mainly limited in organic material in the form of guided wave
In film, ito thin film and glass substrate.It can be seen that the light extraction efficiency of conventional OLED device is lower (about 20%), this is seriously constrained
The development and application of OLED.How to reduce total reflection effect in OLED device, improve optically coupling to before device to exterior space
Ratio (light extraction efficiency) cause the extensive concern of people.
Currently, realize improve OLED external quantum efficiency a kind of important method be substrate light output surface formed as fold,
The structures such as photonic crystal, lenticule display (MLA) and addition surface coating.First two structure will affect the radiation spectrum of OLED
Angular distribution, the third structure fabrication processes are complicated, and use surface coating simple process, luminous efficiency improve 30% with
On, especially people pay close attention to.According to optical principle, when light transmission superrefraction rate is n1Substance to refractive index be n2Substance when (n1
> n2), only in arcsin (n2/n1) angle in can just be incident on refractive index be n2Substance in, absorptivity B can be to
Under formula calculate:
If n1=nGeneral OLED organic material=1.70, n2=nGlass=1.46, then 2B=0.49.Assuming that the light whole quilt propagated outward
Metal electrode reflection, then only 51% luminous energy is by the organic film of high refractive index and the waveguide of ITO layer institute, can equally calculate light from
Substrate of glass injects to transmitance when air.When therefore going out the outside of device from the light emission that organic layer issues, only about 17%
Luminous energy seen by people.Therefore, the status low for current OLED device light extraction efficiency, needs to increase in the device structure
Add one layer CPL layers, i.e. light extraction material, according to optical absorption, refraction principle, the refractive index of this surface coating material should be got over
It is high better.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of based on the organic of heteroaryl amine structure
Compound and its application.The compounds of this invention contains heteroaryl amine structure, and glass transition temperature with higher is led in visible light
Domain refractive index is high, after the CPL layer for being applied to OLED device, can effectively promote the light extraction efficiency of OLED device;And it can make
For the electronic blocking layer material of OLED device, electronics is stopped to be transferred to hole transmission layer side from luminescent layer, improves hole and electricity
Multiplicity of the son in luminescent layer, to promote the luminous efficiency and service life of OLED device.
Technical scheme is as follows:
A kind of organic compound based on heteroaryl amine structure, shown in the structure of the organic compound such as general formula (1):
L1、L2、L3Independently be expressed as singly-bound, substituted or unsubstituted 6~60 yuan arylene, containing one or more
A heteroatomic substituted or unsubstituted 5~60 yuan of inferior heteroaryls;L1、L2With L3It can be identical or different;
In general formula (1), R1、R2Separately it is expressed as structure shown in general formula (2) or general formula (3): R3Independently earth's surface
It is shown as general formula (2), general formula (3), general formula (4), general formula (5), general formula (6), structure shown in general formula (7) or general formula (8);
General formula (2), general formula (3), in general formula (4), X1、X2、X3Separately it is expressed as-O- ,-S- ,-C (R10)
(R11)-、-N(R12)-;
General formula (6), general formula (7), in general formula (8), it is identical when Z occurs every time or be differently expressed as nitrogen-atoms or C (R13);
At least one Z is expressed as nitrogen-atoms;R13It is expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, C1-10Alkane
Base, C1-10Alkoxy, substituted or unsubstituted 6~60 yuan of aryl, containing one or more heteroatomic substituted or unsubstituted
5~60 unit's heteroaryls;
General formula (2), general formula (3), general formula (4), in general formula (5), R4~R9Separately be expressed as hydrogen atom, protium atom,
D-atom, tritium atom, halogen, cyano, C1-10Alkyl, C1-10Alkoxy, substituted or unsubstituted 6~60 yuan of aryl, contain
One or more heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls;R4、R7、R8、R9It is also separately expressed as leading to
One of formula (9);
General formula (9) passes through CM1-CM2Key, CM2-CM3Key, CM3-CM4Key is connect with general formula (2);
General formula (9) passes through CM5-CM6Key, CM6-CM7Key, CM7-CM8Key is connect with general formula (4);
General formula (9) passes through CM9-CM10Key, CM10-CM11Key, CM11-CM12Key, CM13-CM14Key, CM14-CM15Key, CM15-CM16Key
It is connect with general formula (5);
The R10~R12Independently be expressed as C1-10Alkyl, C1-10Alkoxy, substituted or unsubstituted 6~60
First aryl contains one of one or more heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls, R10With R11It can phase
Mutually bond cyclization;
6~60 yuan of substituted aryl, replace 5~60 unit's heteroaryls substituent group optionally from protium atom, D-atom,
Tritium atom, halogen atom, cyano, C1-20Alkyl, C1-10Alkoxy, 6~20 yuan of aryl, contain one or more hetero atoms
One of 5~20 unit's heteroaryls or a variety of;
Hetero atom in the heteroaryl is selected from nitrogen, oxygen or sulphur.
Preferred embodiment, the structure of the organic compound are any in general formula (I-1)~(I-19):
Further preferably, the L1、L2、L3Independently be expressed as singly-bound, substituted or unsubstituted phenylene, substitution
Or unsubstituted naphthylene, substituted or unsubstituted sub- dibiphenylyl, substituted or unsubstituted sub- terphenyl, replaces or do not take
The anthryl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted sub-pyridyl group, substitution or
It is unsubstituted Asia carbazyl, substituted or unsubstituted furylidene, substituted or unsubstituted sub- pyrimidine radicals, substituted or unsubstituted
Sub- pyrazinyl, substituted or unsubstituted sub- pyridazinyl, substituted or unsubstituted sub- dibenzofuran group, substituted or unsubstituted Asia
Fluorenyl, substituted or unsubstituted Asia N- phenyl carbazole base, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted sub- isoquinoline
Quinoline base, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnoline base, takes substituted or unsubstituted sub- quinazolyl
One of generation or unsubstituted dibenzothiophene, substituted or unsubstituted sub- naphthyridines base;
The R10、R11Independently be expressed as one of methyl, phenyl, dibiphenylyl;R12It is expressed as phenyl, naphthalene
Base, dibiphenylyl, terphenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, benzoxazolyl,
Benzothiazolyl, benzimidazolyl, quinoxalinyl, cinnoline base, quinazolyl, naphthyridines base, fluorenyl, N- phenyl carbazole base, hexichol
And one of furyl or dibenzothiophene;
The R13It is expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, methyl, ethyl, propyl, isopropyl
Base, tert-butyl, phenyl, naphthalene, dibiphenylyl, terphenyl, fluorenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, quinoline
Base, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, quinazolyl, cinnoline base, naphthyridines base,
One of fluorenyl, dibenzofuran group, N- phenyl carbazole base or dibenzothiophene;
The R4~R9Independently be expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, methyl,
Ethyl, propyl, isopropyl, tert-butyl, phenyl, naphthalene, dibiphenylyl, terphenyl, fluorenyl, pyridyl group, pyrimidine radicals, pyrazine
Base, pyridazinyl, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, quinazolyl,
One of cinnoline base, naphthyridines base, fluorenyl, dibenzofuran group, N- phenyl carbazole base or dibenzothiophene;
The substituent group is optionally from protium atom, D-atom, tritium atom, halogen atom, cyano, C1-20Alkyl, C1-10Alkane
Oxygroup, contains one of one or more heteroatomic 5~20 unit's heteroaryls or a variety of at 6~20 yuan of aryl;
Hetero atom in the heteroaryl is selected from nitrogen, oxygen or sulphur.
Further preferably, the concrete structure formula of the organic compound is with any one of flowering structure:
The second aspect of the invention is to provide a kind of preparation method of above-mentioned organic compound, has such spy
Sign,
The preparation reaction equation of compound shown in general formula (1) is as follows:
Above-mentioned reaction equation specific is dissolved with toluene the preparation method comprises the following steps: weigh raw material A and intermediate B;Add Pd2
(dba)3、P(t-Bu)3, sodium tert-butoxide;Under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted at 95-110 DEG C
10-24 hours, cooling and filtering reacting solution, filtrate revolving crossed silicagel column, obtains product D;The molar ratio of intermediate B and raw material A
For 1:(1.2-3.0), Pd2(dba)3Molar ratio with intermediate B is (0.006-0.02): 1, P (t-Bu)3With rubbing for intermediate B
You are than being (0.006-0.02): 1, the molar ratio of sodium tert-butoxide and intermediate B is (1.0-3.0): 1;
Wherein, intermediate B the preparation method comprises the following steps:
Above-mentioned reaction specific adds Pd the preparation method comprises the following steps: weigh raw material I and raw material II is dissolved with toluene2(dba)3、P
(t-Bu)3And sodium tert-butoxide;Under an inert atmosphere, the mixed solution of above-mentioned reactant is reacted at 90-110 DEG C of reaction temperature
10-24 hours, cooling, filtering reacting solution, filtrate revolving crossed silicagel column, obtains intermediate B;Mole of raw material II and raw material I
Than for 1:(1.0-1.5);Pd2(dba)3It is (0.006-0.02) with the molar ratio of raw material II: 1, sodium tert-butoxide and raw material II are rubbed
You are than being (2.0-3.0): 1;P(t-Bu)3Molar ratio with raw material II is (2.0-3.0): 1;
What above-mentioned reaction mainly utilized is the substitution reaction between amine compound and halogen atom in the present invention, each object
The dosage when dosage of matter is a substitution reaction, it is aminated by a substitution reaction change when there are multiple substitution reaction
It closes object structure and a substitution reaction is repeated several times.
The third aspect of the invention is to provide a kind of organic electroluminescence device, and the organic electroluminescence device includes
At least one layer of functional layer contains the organic compound based on heteroaryl amine structure.
The fourth aspect of the invention is to provide a kind of organic electroluminescence device, and the organic electroluminescence device includes
CPL layers, described CPL layers contains the organic compound based on heteroaryl amine structure.
The fifth aspect of the invention is to provide a kind of organic electroluminescence device, and the organic electroluminescence device includes
Electronic barrier layer, the electronic barrier layer contain the organic compound based on heteroaryl amine structure.
The sixth aspect of the invention is to provide a kind of illumination or display element, and the illumination or display element contain described
Organic electroluminescence device.
The beneficial of above scheme has the technical effect that
Organic compound of the invention contains the heteroaryl amine groups of high refractive index, improves the refractive index of integral material;
It is simultaneously tertiary aromatic amine structure, so that the lumo energy of material is shallower, in CVD processing procedure, material will not absorb electronics and go bad;This
On space structure, center amine groups intersect with three heteroaryl branched groups and separate invention organic compound, avoid point
Sub mutually accumulation, so that organic compound of the present invention all has very high Tg and molecule thermal stability;Three-dimensional steric configuration makes
Obtaining the compounds of this invention intermolecular interaction reduces, and leads to the vapor deposition temperature of material of the present invention under vacuum conditions generally all
Less than 340 DEG C, evaporation film-forming should not be crystallized, and not only ensure that material long-time evaporation material in volume production does not decompose, but also reduce
Since the heat radiation of vapor deposition temperature is to the influence of crust deformation that MASK (mask plate) is deposited.
Organic compound of the present invention applies the electrons and holes transmission that device is not involved at CPL layers in OLED device, but
There is very high requirement to the thermal stability, membrane crystallization and refractive index of material.As above analysis, benzo heteroaryl are rigid base
Group, improves the thermal stability of material;High Tg ensure that material does not crystallize under filminess;Three heteroaryls make in amine
Molecular Geometries more three-dimensional is obtained, so that material has lower vapor deposition temperature, it is the premise that material can be applied to volume production;
High refractive index is then the main factor that material of the present invention can apply to CPL layers.Organic compound of the present invention is led in visible light
Domain absorption is low, refractive index is high, after the CPL layer for being applied to OLED device, can effectively promote the light extraction efficiency of OLED device.It is comprehensive
On, compound of the present invention has good application effect and industrialization prospect in OLED luminescent device.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device;
Wherein, 1, OLED device substrate, 2, anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, sky
Cave barrier layer, 7, electron transfer layer, 8, electron injecting layer, 9, cathode layer, 10, CPL layers;
Fig. 2 is the refraction index test figure of compound 2;
Fig. 3 is the film Acceleration study comparison diagram of compound 2 and Alq3;
Fig. 4 is the efficiency that device embodiments 1,18,34,41,50,65,76 and device comparative example 1 measure at different temperatures
Curve graph;
Fig. 5 is Alq3 and LiF evaporation film photo after CVD processing procedure;
Fig. 6 is the compounds of this invention 6 and LiF the evaporation film photo after CVD processing procedure.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of intermediate B -1:
In the there-necked flask of 250ml, lead under nitrogen protection, raw material II -1 0.012mol raw material 1-1,0.010mol be added,
150ml toluene is stirred, and is then added 5 × 10-5molPd2(dba)3, 5 × 10-5mol P(t-Bu)3, the 0.03mol tert-butyl alcohol
Sodium is heated to 105 DEG C, back flow reaction 24 hours, samples contact plate, display is without bromo-derivative residue, fully reacting;Naturally cool to room
Temperature, filtering, filtrate rotate to no fraction, cross neutral silica gel column, obtain target product intermediate B -1;HPLC purity 99.9% is received
Rate 78.0%;Elemental analysis structure (molecular formula C26H17N3O2): theoretical value C, 77.41;H,4.25;N,10.42;O,7.93;It surveys
Examination value: C, 77.42;H,4.24;N,10.43;O,7.91.ESI-MS(m/z)(M+): theoretical value 403.13, measured value are
403.44。
Such as table 1 of intermediate B synthesis material needed for embodiment:
Table 1
Embodiment 1: the synthesis of compound 2:
In the there-necked flask of 250ml, lead under nitrogen protection, 0.012mol raw material A -1,0.01mol intermediate B -1 be added,
150ml toluene is stirred, and is then added 5 × 10-5molPd2(dba)3, 5 × 10-5mol P(t-Bu)3, the 0.03mol tert-butyl alcohol
Sodium is heated to 105 DEG C, back flow reaction 24 hours, samples contact plate, display is without bromo-derivative residue, fully reacting;Naturally cool to room
Temperature, filtering, filtrate rotate to no fraction, cross neutral silica gel column, obtain target product, HPLC purity 99.7%, yield 74.2%.
Elemental analysis structure (molecular formula C50H32N4O2) theoretical value: C, 83.31;H,4.47;N,7.77;O,4.44;Test value: C,
83.33;H,4.48;N,7.76;O,4.43.ESI-MS(m/z)(M+): theoretical value: 720.25, measured value: 720.56.
Target compound is prepared with above-mentioned synthetic method, specific structure is as shown in table 2.
Table 2
Organic compound of the invention uses in luminescent device, as CPL layer material, has shallow HOMO energy level, high Tg
(glass transition temperature), high refractive index.HOMO, LUMO, hot property and refractive index are carried out respectively to the compound of embodiment preparation
Test, testing result is as shown in table 3, wherein Fig. 2 be compound 2 refraction index test figure.
Table 3
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;Refractive index is surveyed by ellipsometer (U.S.'s J.A.Woollam Co. model: ALPHA-SE)
Amount, is tested as atmospheric environment.Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu Corporation
It is measured on TGA-50H thermogravimetric analyzer, nitrogen flow 20mL/min;Highest occupied molecular orbital HOMO energy level is by light
Electron spectrum (IPS-3) test, is tested as atmospheric environment, and Eg actual measurement is tested by ultraviolet spectra, LUMO=HOMO+Eg.
By upper 3 data of table it is found that the materials such as Alq3 for applying at present of comparison, organic compound of the invention have be shallower than-
The lumo energy of 3ev, in oled panel application processing procedure, need that LiF is deposited after CPL film thickness, then carried out under the conditions of CVD
TFE encapsulation, lumo energy is more shallow, and under CVD energy, CPL material is easier and LiF reacts, and novel substance is formed, to make
Entire covering layer material color blackening, influences the light extraction efficiency of device, and as shown in Figure 5, Figure 6, Fig. 5 is that Alq3 and LiF is deposited
Film blackening photo after CVD processing procedure, Fig. 6 are the compounds of this invention 6 and LiF the evaporation film photo after CVD processing procedure, and material is without change
Change.
Organic compound of the invention simultaneously has high glass transition temperature, high refractive index, simultaneously because containing heteroaryl
Base or benzo heteroaryl rigid radical pi-conjugated greatly, ensure that the thermal stability of material.Therefore, the present invention is with heteroaryl amine
The organic material of core can effectively improve the light extraction efficiency of device, and ensure that after the CPL layer for being applied to OLED device
The long-life of OLED device.
In the devices below by way of device embodiments 1-80 and comparative example 1 OLED material that the present invention will be described in detail synthesizes
Application effect.The complete phase of manufacture craft of device embodiments 2-80 and comparative example 1 device compared with device embodiments 1 of the present invention
Together, and identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that right
Electronic blocking (EB) layer or covering CPL layer material in device are replaced.The structure composition of each embodiment obtained device such as table 4
Shown, the performance test results of each embodiment obtained device are as shown in table 5.
Device embodiments 1
2/ hole injection layer of transparent substrate layer 1/ITO anode layer, 3 (HAT-CN, thickness 10nm)/hole transmission layer 4 (HT-1,
Thickness 60nm)/electronic barrier layer 5 (EB-1, thickness 20nm)/luminescent layer 6 (GH1, GH2 and GD-1 according to 45:45:10 weight
Than blending, thickness 40nm)/hole barrier/electron transfer layer 7 (ET-1 and Liq, according to the weight ratio blending of 1:1, thickness
40nm)/electron injecting layer 8 (LiF, thickness 1nm)/cathode layer 9 (Mg and Ag, according to the weight ratio blending of 9:1, thickness 15nm)/
CPL layer 10 (compound 2, thickness 70nm).
Specific preparation process is as follows:
As shown in Figure 1, transparent substrate layer 1 is transparent PI film, ito anode layer 2 (film thickness 150nm) is washed, i.e.,
Neutralizing treatment, pure water, drying are successively carried out, then carries out ultraviolet-ozone washing to remove the organic residue on the transparent surface ITO
Object.On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, the HAT-CN that film thickness is 10nm is deposited
It is used as hole injection layer 3.Then the HT-1 of 60nm thickness is deposited as hole transmission layer 4.20nm thickness is then deposited
EB-1 is as electronic barrier layer 5.After above-mentioned electron-blocking materials vapor deposition, the luminescent layer 6 of OLED luminescent device, knot are made
Structure includes OLED luminescent layer 6 used GH-1, GH-2 as material of main part, and GD-1 adulterates ratio as dopant material, dopant material
Example is 10% weight ratio, and luminescent layer film thickness is 40nm.After above-mentioned luminescent layer 6, continue vacuum evaporation electron transport layer materials
For ET-1 and Liq.The vacuum evaporation film thickness of the material is 40nm, this layer is hole barrier/electron transfer layer 7.Hole barrier/
On electron transfer layer 7, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is electron injecting layer
8.On electron injecting layer 8, by vacuum deposition apparatus, the Mg:Ag electrode layer that film thickness is 15nm is made, this layer is cathode layer 9
It uses.On cathode layer 9, the compound 2 of vacuum evaporation 70nm, as CPL layer 10.OLED luminescent device is completed as described above
Afterwards, anode and cathode is connected with well known driving circuit, the current efficiency of measurement device and the service life of device, as a result
As shown in table 4.
Table 4
Table 5
It can be seen that the organic compound of the structure of amine containing heteroaryl of the present invention is sent out applied to OLED by the result of table 5
After optical device production, compared with device comparative example 1, light, which takes out, to be obviously improved, under same current density, device brightness and device
Part efficiency is all improved, and since brightness and efficiency get a promotion, power consumption relative reduction of the OLED device in the case where determining brightness makes
It is also improved with the service life.
In order to illustrate material membrane phase crystallization-stable performance of the present invention, by material compound of the present invention 2,146,177,215,
247,353,462 and well known materials Alq3 has carried out film and accelerates crystallization experiment: using vacuum evaporation mode, respectively by 2,146,
177,215,247,353,462 and Alq3 is vaporized on alkali-free glass, and is carried out in glove box (water oxygen content < 0.1ppm)
Encapsulation, sample after encapsulation is placed under the conditions of double 85 (85 DEG C of temperature, humidity 85%), periodically with microscope (LEICA,
DM8000M, 5*10 multiplying power) observation material membrane crystalline state, experimental result is as shown in table 6, material surface form such as Fig. 3 institute
Show.
Table 6
Title material | After material filming | After experiment 72 hours | After experiment 600 hours |
Compound 2 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 146 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 177 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 215 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 247 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 353 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Compound 462 | Smooth surface morphology even uniform | Smooth surface morphology even uniform, nodeless mesh | Smooth surface morphology even uniform, nodeless mesh |
Alq3 | Smooth surface morphology even uniform | Surface forms the round crystal plane of several dispersions | Surface checking |
The membrane crystallization stability of the above description of test, material of the present invention is significantly larger than well known materials, is being applied to OLED device
Service life after part has beneficial effect.
Work limitation rate is also more stable at low temperature for the OLED device of further material preparation of the present invention, by device reality
It applies example 1,18,34,41,50,65,76 and device comparative example 1 and carries out efficiency test, acquired results such as table 7 in -10~80 DEG C of sections
With shown in Fig. 4.
Table 7
From the data of table 7 and Fig. 4 it is found that device embodiments 1,18,34,41,50,65,76 are material of the present invention and known
The device architecture of material adapted is compared with device comparative example 1, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency
It is steady to increase.
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 (8)
1. a kind of organic compound based on heteroaryl amine structure, which is characterized in that the structure of the organic compound is such as logical
Shown in formula (1):
L1、L2、L3Independently be expressed as singly-bound, substituted or unsubstituted 6~60 yuan arylene, containing one or more miscellaneous
Substituted or unsubstituted 5~60 yuan of inferior heteroaryls of atom;L1、L2With L3It can be identical or different;
In general formula (1), R1、R2Separately it is expressed as structure shown in general formula (2) or general formula (3): R3Separately it is expressed as
Structure shown in general formula (2), general formula (3), general formula (4), general formula (5), general formula (6), general formula (7) or general formula (8);
General formula (2), general formula (3), in general formula (4), X1、X2、X3Separately it is expressed as-O- ,-S- ,-C (R10)(R11)-、-N
(R12)-;
General formula (6), general formula (7), in general formula (8), it is identical when Z occurs every time or be differently expressed as nitrogen-atoms or C (R13);At least
One Z is expressed as nitrogen-atoms;R13It is expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, C1-10Alkyl,
C1-10Alkoxy, substituted or unsubstituted 6~60 yuan of aryl, containing one or more heteroatomic substituted or unsubstituted 5
~60 unit's heteroaryls;
General formula (2), general formula (3), general formula (4), in general formula (5), R4~R9It is former to be separately expressed as hydrogen atom, protium atom, deuterium
Son, tritium atom, halogen, cyano, C1-10Alkyl, C1-10Alkoxy, substituted or unsubstituted 6~60 yuan of aryl, contain one
Or multiple heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls;R4、R7、R8、R9Also separately it is expressed as general formula (9)
One of;
General formula (9) passes through CM1-CM2Key, CM2-CM3Key, CM3-CM4Key is connect with general formula (2);
General formula (9) passes through CM5-CM6Key, CM6-CM7Key, CM7-CM8Key is connect with general formula (4);
General formula (9) passes through CM9-CM10Key, CM10-CM11Key, CM11-CM12Key, CM13-CM14Key, CM14-CM15Key, CM15-CM16Key and logical
Formula (5) connection;
The R10~R12Independently be expressed as C1-10Alkyl, C1-10Alkoxy, substituted or unsubstituted 6~60 yuan of virtues
Base contains one of one or more heteroatomic substituted or unsubstituted 5~60 unit's heteroaryls, R10With R11It can mutual key
It is looped;
6~60 yuan of substituted aryl, the substituent group of 5~60 unit's heteroaryls replaced are optionally former from protium atom, D-atom, tritium
Son, halogen atom, cyano, C1-20Alkyl, C1-10Alkoxy, 6~20 yuan of aryl, containing one or more heteroatomic 5~
One of 20 unit's heteroaryls are a variety of;
Hetero atom in the heteroaryl is selected from nitrogen, oxygen or sulphur.
2. organic compound according to claim 1, which is characterized in that the structure of the organic compound is general formula (I-
1) any in~(I-19):
3. organic compound according to claim 1 or 2, which is characterized in that the L1、L2、L3Being expressed as independently
Singly-bound, substituted or unsubstituted naphthylene, substituted or unsubstituted sub- dibiphenylyl, replaces substituted or unsubstituted phenylene
Or unsubstituted sub- terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrene
Base, substituted or unsubstituted sub-pyridyl group, substituted or unsubstituted sub- carbazyl, substituted or unsubstituted furylidene, substitution
Or it is unsubstituted sub- pyrimidine radicals, substituted or unsubstituted sub- pyrazinyl, substituted or unsubstituted sub- pyridazinyl, substituted or unsubstituted
Sub- dibenzofuran group, substituted or unsubstituted fluorenylidene, substituted or unsubstituted Asia N- phenyl carbazole base, replace or do not take
It is the sub- quinolyl in generation, substituted or unsubstituted sub- isoquinolyl, substituted or unsubstituted sub- quinazolyl, substituted or unsubstituted
Quinoxalinyl, substituted or unsubstituted cinnoline base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted sub- naphthyridines
One of base;
The R10、R11Independently be expressed as one of methyl, phenyl, dibiphenylyl;R12It is expressed as phenyl, naphthalene, two
Xenyl, terphenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, benzoxazolyl, benzo thiophene
Oxazolyl, benzimidazolyl, quinoxalinyl, cinnoline base, quinazolyl, naphthyridines base, fluorenyl, N- phenyl carbazole base, dibenzofurans
One of base or dibenzothiophene;
The R13Be expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, methyl, ethyl, propyl, isopropyl,
It is tert-butyl, phenyl, naphthalene, dibiphenylyl, terphenyl, fluorenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazinyl, quinolyl, different
Quinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, quinazolyl, cinnoline base, naphthyridines base, fluorenyl,
One of dibenzofuran group, N- phenyl carbazole base or dibenzothiophene;
The R4~R9Independently be expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, methyl, ethyl,
Propyl, isopropyl, tert-butyl, phenyl, naphthalene, dibiphenylyl, terphenyl, fluorenyl, pyridyl group, pyrimidine radicals, pyrazinyl, pyridazine
Base, quinolyl, isoquinolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinoxalinyl, quinazolyl, cinnoline base,
One of naphthyridines base, fluorenyl, dibenzofuran group, N- phenyl carbazole base or dibenzothiophene;
The substituent group is optionally from protium atom, D-atom, tritium atom, halogen atom, cyano, C1-20Alkyl, C1-10Alcoxyl
Base, contains one of one or more heteroatomic 5~20 unit's heteroaryls or a variety of at 6~20 yuan of aryl;
Hetero atom in the heteroaryl is selected from nitrogen, oxygen or sulphur.
4. organic compound according to claim 1, which is characterized in that the concrete structure formula of the organic compound be with
Any one of flowering structure:
5. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes at least one layer of functional layer
Contain the organic compound based on heteroaryl amido class formation described in any one of Claims 1 to 4.
6. organic electroluminescence device according to claim 5, including CPL layers, which is characterized in that described CPL layers contains
The organic compound based on heteroaryl amine based structures.
7. organic electroluminescence device according to claim 5, including electronic barrier layer, which is characterized in that the electronics
Contain the organic compound based on heteroaryl amine structure in barrier layer.
8. a kind of illumination or display element, which is characterized in that the illumination or display element contain any one of claim 5~7
The organic electroluminescence device.
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