CN109956933A - A kind of organic compound containing pyridine and its application on organic electroluminescence device - Google Patents
A kind of organic compound containing pyridine and its application on organic electroluminescence device Download PDFInfo
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Abstract
The present invention relates to a kind of organic compound containing pyridine and its applications in OLED device, shown in the structure of the compounds of this invention such as general formula (1):
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of organic compound containing pyridine and its are having
Application in organic electroluminescence devices.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.OLED luminescent device including electrode material film layer and is clipped in different electricity like the structure of sandwich
Organic functional material between the film layer of pole, various different function materials are overlapped mutually depending on the application collectively constitutes OLED hair together
Optical device.OLED luminescent device is as current device, when applying voltage to its two end electrodes, and passes through electric field action organic layer function
Can positive and negative charge in film layer when, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
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 is complicated, and using surface coating simple process, luminous efficiency improves 30% or more,
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 with following
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.
Proposing high performance research to OLED luminescent device at present includes: the driving voltage for reducing device, the hair for improving device
Light efficiency, the service life for improving device etc..In order to realize OLED device performance continuous promotion, not only need from OLED device
The innovation of part structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance
OLED functional material.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of organic compound containing pyridine and
Its application on organic electroluminescence device.The compounds of this invention contains pyridine structure, glass transition temperature with higher
With molecule thermal stability, visible regime absorb it is low, refractive index is high, be applied to OLED device CPL layer after, can effectively mention
Rise the light extraction efficiency of OLED device；And since quinoxaline, benzimidazole and benzoxazoles group have deep HOMO energy level,
Wide forbidden band (Eg) energy level can be used as hole barrier/electron transport layer materials of OLED device, and hole is stopped to be transmitted from luminescent layer
To electronic shell side, the multiplicity of hole and electronics in luminescent layer is improved, to promote the luminous efficiency of OLED device and make
Use the service life.
Technical scheme is as follows: a kind of organic compound containing pyridine, the structure of the organic compound
As shown in general formula (1):
In general formula (1), p, m, n independently be expressed as number 0,1 or 2；And m+n+p >=3；
In general formula (1), Ar1、Ar2、Ar3Independently be expressed as singly-bound, substituted or unsubstituted C6-60Arlydene contains
There are one of one or more heteroatomic substituted or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom be nitrogen, oxygen or
Sulphur；The Ar1、Ar2、Ar3It can be identical or different；
R1、R2、R3It is optionally by one or more R4Substituted or unsubstituted quinoxalinyl, by one or more R4Replace
Or unsubstituted benzimidazolyl, by one or more R4Substituted or unsubstituted benzoxazolyl；R1、R2、R3Different phases
Together；
Z is expressed as N atom or C-H identical or differently；
R4It is expressed as substituted or unsubstituted C6To C30Aryl and containing one or more heteroatomic substituted or unsubstituted
C5To C30One of heteroaryl；The hetero atom is nitrogen, oxygen or sulphur.
On the basis of above scheme, the present invention can also be improved as follows.
Preferably, a kind of organic compound containing pyridine, the R1、R2、R3Independently be expressed as general formula (2),
General formula (3), general formula (4), general formula (5), general formula (6), general formula (7), general formula (8), general formula (9), general formula (10) or general formula (11) institute
Show structure；
Wherein, the Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar13、Ar14Being expressed as independently
Hydrogen atom, C1-10Linear or branched alkyl group, substituted or unsubstituted C6-60Aryl, containing one or more heteroatomic substitutions or
One of unsubstituted 5~60 unit's heteroaryl；The hetero atom is nitrogen, oxygen or sulphur；Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、
Ar10、Ar11、Ar12、Ar13、Ar14It can be identical or different；R4 is expressed as phenyl, xenyl, naphthalene or pyridyl group；Q be 0,1 or
2。
Preferably, a kind of organic compound containing pyridine, the structure of the organic compound such as formula (I-1)~(I-
5) any shown in:
Preferably, a kind of organic compound containing pyridine, the Ar1、Ar2、Ar3Independently be expressed as C1-10
Linear or branched alkyl group, halogen atom, protium, deuterium, the substituted or unsubstituted phenylene of tritium atom；C1-10Linear or branched alkyl group,
Halogen atom, protium, deuterium, the substituted or unsubstituted naphthylene of tritium atom；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium,
The substituted or unsubstituted sub- dibiphenylyl of tritium atom；Anthrylene；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, tritium are former
The substituted or unsubstituted sub-pyridyl group of son；Sub- carbazyl；Furylidene；Sub- quinolyl；Sub- naphthyridines base；Sub- dibenzofuran group；
Sub- dibenzothiophene；One of sub- 9,9- dimethyl fluorenyl or Asia N- phenyl carbazole base；
The Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar13、Ar14Independently be expressed as C1-10Directly
Chain or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted phenyl of tritium atom；C1-10Linear or branched alkyl group, halogen
Atom, protium, deuterium, the substituted or unsubstituted naphthalene of tritium atom；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, tritium atom
Substituted or unsubstituted dibiphenylyl；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, tritium atom are substituted or unsubstituted
Pyridyl group；Carbazyl；Furyl；Pyrimidine radicals；Pyrazinyl；Pyridazinyl；Dibenzofurans；9,9- dimethyl fluorene；N- phenyl carbazole；
Quinolyl；One of isoquinolyl or naphthyridines base.
Preferably, a kind of organic compound containing pyridine, the concrete structure formula of the organic compound are as follows:
Any one.
The application also provides a kind of preparation method of organic compound containing pyridine, and the preparation method is related to anti-
Answer equation are as follows:
(1) it under nitrogen atmosphere, weighs raw material A and is dissolved in DMF, addAnd palladium acetate, stirring are mixed
Object is closed, adds aqueous potassium phosphate solution, it is small that the mixed solution of above-mentioned reactant is heated to reflux 5-15 under the conditions of 120-150 DEG C
When；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, it is pure that gained residue crosses silicagel column
Change, obtains compound intermediate I；
The raw material A withMolar ratio be 1:1.0~3, the molar ratio of palladium acetate and raw material A is
The molar ratio of 0.001~0.04:1, potassium phosphate and raw material A is 1.0~4.0:1, and toluene dosage is that every gram of raw material A uses 30-
50ml toluene；
(2) it under nitrogen atmosphere, weighs intermediate compound I and is dissolved in DMF, addAnd palladium acetate, stirring
Mixture adds aqueous potassium phosphate solution, and the mixed solution of above-mentioned reactant is heated to reflux 10- under the conditions of 120-150 DEG C
24 hours；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, gained residue crosses silica gel
Column purification obtains compound intermediate II；
The intermediate compound I withMolar ratio be 1:1.0~3, the molar ratio of palladium acetate and intermediate compound I
For 0.001~0.04:1, the molar ratio of potassium phosphate and intermediate compound I is 1.0~4.0:1, and toluene dosage is that every gram of intermediate compound I uses
10-40ml toluene；
(3) it under nitrogen atmosphere, weighs intermediate II and is dissolved in DMF, addAnd palladium acetate, it stirs
Mixture is mixed, aqueous potassium phosphate solution is added, the mixed solution of above-mentioned reactant is heated to reflux under the conditions of 120-150 DEG C
10-24 hours；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, gained residue crosses silicon
Rubber column gel column purifying, obtains target compound；
The intermediate II withMolar ratio be 1:1.0~3, mole of palladium acetate and intermediate II
Than for 0.001~0.04:1, the molar ratio of potassium phosphate and intermediate II is 1.0~4.0:1, toluene dosage is every gram of intermediate II
Use 15-50ml toluene.
A kind of organic compound containing pyridine is applied to prepare organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes at least one layer of function
Layer contains the organic compound containing pyridine.
Preferably, a kind of organic electroluminescence device, including hole blocking layer/electron transfer layer, the hole blocking layer/
Electron transfer layer contains the organic compound containing pyridine.
Preferably, a kind of organic electroluminescence device, including CPL layers, described CPL layers containing described containing pyridine
Organic compound.
The present invention also provides a kind of illumination or display element, the illumination or display element contain the organic electroluminescence hair
Optical device.
The present invention is beneficial to be had the technical effect that
The structure of organic compound of the invention contains quinoxaline or benzimidazole or benzoxazoles rigid radical, improves
Material structure stability；Material of the present invention contains strong electron-withdrawing pyridine, quinoxaline or benzimidazole on space structure
Or benzoxazoles group, and quinoxaline or benzimidazole or benzoxazoles group intersect and separate, and group is avoided freely to revolve
Turn, so that material density with higher, obtains higher refractive index；Meanwhile so that material of the present invention all have it is very high
Tg temperature；The vapor deposition temperature of material of the present invention under vacuum conditions is generally less than 350 DEG C, both ensure that material in volume production duration
Time evaporation material does not decompose, and reduces the heat radiation due to vapor deposition temperature to the influence of crust deformation that MASK is deposited.
Material of the present invention applies the electrons and holes transmission that device is not involved at CPL layers in OLED device, but to material
Thermal stability, membrane crystallization and optical transport (high refractive index) have very high requirement.As above analysis, pyridine, quinoxaline
Or benzimidazole or benzoxazoles are rigid radical, improve the stability of material；High Tg temperature, ensure that material in film
It is not crystallized under state；Low vapor deposition temperature is the premise that material can be applied to volume production；High refractive index is then material energy of the present invention
Applied to CPL layers of main factor.
For material of the present invention due to having deep HOMO energy level, high electron mobility can effectively stop hole or energy from hair
Photosphere is transferred to electronic shell side, so that the combined efficiency of hole and electronics in luminescent layer is improved, to promote OLED device
Luminous efficiency and service life.After the CPL layer for being applied to OLED device, the light that can effectively promote OLED device takes the present invention
Efficiency out.To sum up, 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/electron transfer layer, 7, electron injecting layer, 8, cathode layer, 9, CPL layers；
Fig. 2 is the refraction index test figure of compound 6；
Fig. 3-1 is the crystalline state for the membrane material that compound 1 is formed；
Fig. 3-2 is the crystalline state for the membrane material that well known materials CBP is formed；
Fig. 3-3 is the crystalline state for the membrane material that compound 1 is formed after testing 72 hours；
Fig. 3-4 is the crystalline state for the membrane material that CBP is formed after testing 72 hours；
Fig. 3-5 is the crystalline state for the membrane material that compound 1 is formed after testing 200 hours；
Fig. 4 is the efficiency curve diagram that device measures at different temperatures.
Specific embodiment
Embodiment 1:
IntermediateSynthesis
(1) with R1、R2Or R3For when being expressed as general formula (2) structure,
1) in there-necked flask, it is passed through nitrogen, raw material B, I-Ar is added4, sodium hydride, cuprous iodide and Phen be dissolved in
In 1,3-Dimethyl-2-imidazolidinone, it is stirred to react 30h, after reaction, adds water and is extracted with dichloromethane, organic layer is used
Anhydrous sodium sulfate is dry, and the mixture with petroleum ether and ethyl acetate is eluent elution, and column chromatographic purifying obtains intermediate M；
2) it under nitrogen atmosphere, weighs intermediate M and is dissolved in tetrahydrofuran, then by Br-Ar2-B(OH)2And four (triphenyl
Phosphine) palladium addition, mixture is stirred, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant in reaction temperature
It is heated to reflux at 80 DEG C 20 hours；After reaction, cooling, mixed liquor is extracted with dichloromethane, extract anhydrous sodium sulfate
It is dried, and is concentrated under reduced pressure, thickened solid is crossed into silica gel column purification, obtains compound intermediate N；
3) under nitrogen atmosphere, weigh intermediate N and be dissolved in n,N-Dimethylformamide (DMF), then will be bis- (pinacol root
Base) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate addition, mixture is stirred, it will be above-mentioned anti-
The mixed solution of object is answered to be heated to reflux at 150 DEG C of reaction temperature 10 hours；After reaction, it cools down and filters mixture
And it is dry in vacuum drying oven.Residue obtained is crossed into silica gel column separating purification, obtains compound intermediate B；
(2) with R1、R2Or R3For when being expressed as general formula (3) structure,
1) it under nitrogen atmosphere, weighs raw material B and is dissolved in tetrahydrofuran, then by Ar5-B(OH)2And tetrakis triphenylphosphine palladium
It is added, stirs mixture, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant at 80 DEG C of reaction temperature
It is heated to reflux 15 hours；After reaction, cooling, mixed liquor is extracted with dichloromethane, at extract anhydrous sodium sulfate drying
Reason, and be concentrated under reduced pressure, thickened solid is crossed into silica gel column purification, obtains compound intermediate P；
2) under nitrogen atmosphere, intermediate P, I-Ar is added2- Br, sodium hydride, cuprous iodide and Phen are dissolved in 1,3-
In dimethyl-2-imidazolinone, it is stirred to react 30h, after reaction, adds water and is extracted with dichloromethane, organic layer is with anhydrous
Sodium sulphate is dry, and the mixture with petroleum ether and ethyl acetate is eluent elution, and column chromatographic purifying obtains intermediate Q；
3) under nitrogen atmosphere, weigh intermediate Q and be dissolved in n,N-Dimethylformamide (DMF), then will be bis- (pinacol root
Base) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate addition, mixture is stirred, it will be above-mentioned anti-
The mixed solution of object is answered to be heated to reflux at 120-150 DEG C of reaction temperature 10 hours；After reaction, cooling and by mixture
It filters and dry in vacuum drying oven.Residue obtained is crossed into silica gel column separating purification, obtains compound intermediate B；
(3) with R1、R2Or R3It is expressed as general formula (4) structure,
1) under nitrogen atmosphere, raw material C, I-Ar is added7, sodium hydride, cuprous iodide and Phen be dissolved in 1,3- diformazan
In base -2- imidazolone, it is stirred to react 30h, after reaction, adds water and is extracted with dichloromethane, organic layer anhydrous slufuric acid
Sodium is dry, and the mixture with petroleum ether and ethyl acetate is eluent elution, and column chromatographic purifying obtains intermediate X；
2) it under nitrogen atmosphere, weighs intermediate X and is dissolved in tetrahydrofuran, then by Ar6-B(OH)2And four (triphenylphosphine)
Palladium is added, and stirs mixture, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant in 80 DEG C of reaction temperature
Under be heated to reflux 15 hours；After reaction, cooling, mixed liquor is extracted with dichloromethane, and extract is dry with anhydrous sodium sulfate
Processing, and be concentrated under reduced pressure, thickened solid is crossed into silica gel column purification, obtains compound intermediate Y；
3) it under nitrogen atmosphere, weighs intermediate Y and is dissolved in n,N-Dimethylformamide, then by Br-Ar2-B(OH)2And vinegar
Sour palladium is added, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in 150 DEG C of reaction temperature
Under be heated to reflux 24 hours；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, gained is residual
Excess crosses silica gel column purification, obtains Compound Compound intermediate Z；
4) under nitrogen atmosphere, weigh intermediate Z and be dissolved in n,N-Dimethylformamide (DMF), then will be bis- (pinacol root
Base) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate addition, mixture is stirred, it will be above-mentioned anti-
The mixed solution of object is answered to be heated to reflux at 150 DEG C of reaction temperature 10 hours；After reaction, it cools down and filters mixture
And it is dry in vacuum drying oven.Residue obtained is crossed into silica gel column separating purification, obtains compound intermediate B；
By taking the synthesis of intermediate B 1 as an example
(1) in 250mL there-necked flask, it is passed through nitrogen, 0.02mol raw material B1,0.03mol raw material E1,0.04mol hydrogen is added
Change sodium, 0.004mol cuprous iodide and 0.01mol Phen to be dissolved in 100ml 1,3-Dimethyl-2-imidazolidinone, stir
It mixes reaction 20-30h to add water after reaction and be extracted with dichloromethane, organic layer is dry with anhydrous sodium sulfate, uses petroleum ether
Mixture with ethyl acetate is eluent elution, and the volume ratio of petroleum ether and ethyl acetate is 1:100, column chromatography in eluent
Purifying, obtains intermediate X 1；HPLC purity 99.7%, yield 78.5%.
Elemental analysis structure (molecular formula C13H9BrN2): theoretical value C, 57.17；H,3.32；Br,29.25；N,10.26；It surveys
Examination value: C, 57.19；H,2.33；Br,29.26；N,10.32.ESI-MS(m/z)(M+): theoretical value 271.99, measured value are
272.05。
(2) in 250mL there-necked flask, it is passed through nitrogen, 0.04mol intermediate X 1 is added, the THF of 100ml, 0.05mol are former
Expect F1,0.0004mol tetrakis triphenylphosphine palladium, then 0.06mol K is added in stirring2CO3Aqueous solution (2M), is heated to 80 DEG C,
Back flow reaction 10 hours, sample contact plate, fully reacting.Natural cooling is extracted with 200ml methylene chloride, layering, extract liquor nothing
Aqueous sodium persulfate dries, filters, and filtrate revolving crosses silica gel column purification, obtains intermediate Y1, HPLC purity 99.8%, yield
88.2%.
Elemental analysis structure (molecular formula C19H13BrN2): theoretical value C, 65.35；H,3.75；Br,22.88；N,8.02；It surveys
Examination value: C, 65.44；H,3.83；Br,22.92；N,8.08.ESI-MS(m/z)(M+): theoretical value 348.03, measured value are
348.11。
(3) in 500mL there-necked flask, it is passed through nitrogen, the N that 0.05mol intermediate Y1 is dissolved in 300ml, N- diformazan is added
In base formamide (DMF), then (1,1 '-bis- (diphenylphosphines) two is luxuriant by 0.06mol bis- (pinacol foundation) two boron, 0.0005mol
Iron) dichloro palladium (II) and 0.125mol potassium acetate be added, mixture is stirred, by the mixed solution of above-mentioned reactant in reaction temperature
It is heated to reflux 10 hours at 120-150 DEG C of degree；After reaction, cool down and be added 200ml water and by mixture filtering and true
It is dry in empty baking oven.Residue obtained is crossed into silica gel column separating purification, obtains compound intermediate B1；HPLC purity
99.2%, yield 81.2%.Elemental analysis structure (molecular formula C25H25BN2O2): theoretical value C, 75.77；H,6.36；B,2.73；
N,7.07；O,8.07；Test value: C, 75.82；H,6.44；B,2.75；N,7.14；O,8.15.ESI-MS(m/z)(M+): it is theoretical
Value is 396.20, measured value 396.23.Intermediate B is prepared with the synthetic method of intermediate B 1, specific structure is as shown in table 1.
Table 1
Embodiment 2: the synthesis of compound 1:
In 250mL there-necked flask, it is passed through nitrogen, 0.01mol intermediate A 1, the DMF of 150ml, 0.03mol intermediate is added
Then 0.02mol ﹒ L is added in B2,0.0002mol palladium acetate, stirring-1 K3PO4Aqueous solution is heated to 150 DEG C, back flow reaction 24
Hour, sample contact plate, fully reacting.Natural cooling is extracted with 200ml methylene chloride, layering, and extract liquor is dry with anhydrous sodium sulfate
Dry, filtering, filtrate revolving crosses silica gel column purification, obtains intermediate 1, HPLC purity 99.2%, yield 53.6%.
Elemental analysis structure (molecular formula C16H9Cl2N6): theoretical value C, 56.16；H,2.65；N,20.47；Cl,20.72；It surveys
Examination value: C, 56.22；H,2.69；N,20.49；Cl,20.77.ESI-MS(m/z)(M+): theoretical value 341.02, measured value are
341.05。
In 250mL there-necked flask, it is passed through nitrogen, 0.01mol intermediate 1, the DMF of 150ml, 0.06mol intermediate is added
Then 0.02mol ﹒ L is added in B4,0.0002mol palladium acetate, stirring-1 K3PO4Aqueous solution is heated to 150 DEG C, back flow reaction 24
Hour, sample contact plate, fully reacting.Natural cooling is extracted with 200ml methylene chloride, layering, and extract liquor is dry with anhydrous sodium sulfate
Dry, filtering, filtrate revolving crosses silica gel column purification, obtains intermediate 1, HPLC purity 98.9%, yield 52.6%.
Elemental analysis structure (molecular formula C32H19N9): theoretical value C, 72.58；H,3.62；N,23.80；Test value: C,
72.62；H,3.69；N,23.87.ESI-MS(m/z)(M+): theoretical value 529.18, measured value 529.21.
Embodiment 3: the synthesis of compound 6:
The preparation method of compound 6 is with embodiment 2, the difference is that replacing intermediate B 2 with intermediate B 1.Element point
Analyse structure (molecular formula C38H23N9): theoretical value C, 75.36；H,3.83；N,20.81；Test value: C, 75.39；H,3.85；N,
20.85。ESI-MS(m/z)(M+): theoretical value 605.21, measured value 605.29.
Embodiment 4: the synthesis of compound 26:
The preparation method of compound 26 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 5.Element point
Analyse structure (molecular formula C50H31N9): theoretical value C, 79.24；H,4.12；N,16.63；Test value: C, 79.29；H,4.15；N,
16.65。ESI-MS(m/z)(M+): theoretical value 757.27, measured value 757.29.
Embodiment 5: the synthesis of compound 28:
The preparation method of compound 28 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 6.Element point
Analyse structure (molecular formula C62H39N9): theoretical value C, 81.83；H,4.32；N,13.85；Test value: C, 81.88；H,4.37；N,
13.87。ESI-MS(m/z)(M+): theoretical value 909.33, measured value 909.38.
Embodiment 6: the synthesis of compound 42:
The preparation method of compound 42 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 7.Element point
Analyse structure (molecular formula C38H23N9): theoretical value C, 75.36；H,3.83；N,20.81；Test value: C, 75.38；H,3.87；N,
20.88。ESI-MS(m/z)(M+): theoretical value 605.21, measured value 605.29.
Embodiment 7: the synthesis of compound 48:
The preparation method of compound 48 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 8.Element point
Analyse structure (molecular formula C50H31N9): theoretical value C, 79.24；H,4.12；N,16.63；Test value: C, 79.27；H,4.15；N,
16.66。ESI-MS(m/z)(M+): theoretical value 757.27, measured value 757.35.
Embodiment 8: the synthesis of compound 52:
The preparation method of compound 52 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 9.Element point
Analyse structure (molecular formula C50H31N9): theoretical value C, 79.24；H,4.12；N,16.63；Test value: C, 79.28；H,4.16；N,
16.65。ESI-MS(m/z)(M+): theoretical value 757.27, measured value 757.33.
Embodiment 9: the synthesis of compound 79:
The preparation method of compound 79 is with embodiment 3, the difference is that replacing intermediate B 4 with intermediate B 13.Element
Analyze structure (molecular formula C50H31N9): theoretical value C, 79.24；H,4.12；N,16.63；Test value: C, 79.27；H,4.13；N,
16.69。ESI-MS(m/z)(M+): theoretical value 757.27, measured value 757.35.
Embodiment 10: the synthesis of compound 87:
In 250mL there-necked flask, it is passed through nitrogen, 0.01mol intermediate A 2, the DMF of 150ml, 0.03mol intermediate is added
Then 0.02mol ﹒ L is added in B3,0.0002mol palladium acetate, stirring-1 K3PO4Aqueous solution is heated to 150 DEG C, back flow reaction 24
Hour, sample contact plate, fully reacting.Natural cooling is extracted with 200ml methylene chloride, layering, and extract liquor is dry with anhydrous sodium sulfate
Dry, filtering, filtrate revolving crosses silica gel column purification, obtains intermediate 1, HPLC purity 99.2%, yield 53.6%.
Elemental analysis structure (molecular formula C23H14Cl2N4): theoretical value C, 66.20；H,3.38；N,13.43；Cl,16.99；
Test value: C, 66.22；H,3.39；N,13.49；Cl,17.07.ESI-MS(m/z)(M+): theoretical value 416.06, measured value
It is 416.15.
In 250mL there-necked flask, it is passed through nitrogen, 0.01mol intermediate 1, the DMF of 150ml, 0.06mol intermediate is added
Then 0.02mol ﹒ L is added in B5,0.0002mol palladium acetate, stirring-1 K3PO4Aqueous solution is heated to 150 DEG C, back flow reaction 24
Hour, sample contact plate, fully reacting.Natural cooling is extracted with 200ml methylene chloride, layering, and extract liquor is dry with anhydrous sodium sulfate
Dry, filtering, filtrate revolving crosses silica gel column purification, obtains intermediate 1, HPLC purity 98.9%, yield 52.6%.
Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value: C,
80.97；H,4.29；N,14.85.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.29.
Embodiment 11: the synthesis of compound 89:
The preparation method is the same as that of Example 10 for compound 89, the difference is that replacing intermediate B 5 with intermediate B 8.Element
Analyze structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value: C, 80.98；H,4.27；N,
14.86。ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.32.
Embodiment 12: the synthesis of compound 98:
The preparation method is the same as that of Example 10 for compound 98, the difference is that replacing intermediate B 5 with intermediate B 11.Element
Analyze structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value: C, 80.97；H,4.29；N,
14.87。ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.33.
Embodiment 13: the synthesis of compound 116:
The preparation method of compound 116, the difference is that replacing intermediate A 1 with intermediate A 3, uses B13 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.96；H,4.29；N,14.87.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.33.
Embodiment 14: the synthesis of compound 128:
The preparation method of compound 128, the difference is that replacing intermediate A 1 with intermediate A 4, uses B5 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.97；H,4.32；N,14.88.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.35.
Embodiment 15: the synthesis of compound 145:
The preparation method of compound 145, the difference is that replacing intermediate A 1 with intermediate A 5, uses B5 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.98；H,4.31；N,14.89.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.34.
Embodiment 16: the synthesis of compound 149:
The preparation method of compound 149, the difference is that replacing intermediate A 1 with intermediate A 4, uses B8 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.96；H,4.33；N,14.86.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.31.
Embodiment 17: the synthesis of compound 153:
The preparation method of compound 153, the difference is that replacing intermediate A 1 with intermediate A 2, uses B12 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.98；H,4.31；N,14.89.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.34.
Embodiment 18: the synthesis of compound 157:
The preparation method of compound 157, the difference is that replacing intermediate A 1 with intermediate A 2, uses B5 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.95；H,4.34；N,14.86.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.31.
Embodiment 19: the synthesis of compound 179:
The preparation method of compound 179, the difference is that replacing intermediate A 1 with intermediate A 6, uses B5 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C52H33N7): theoretical value C, 82.63；H,4.40；N,12.97；Test value:
C,82.68；H,4.47；N,13.05.ESI-MS(m/z)(M+): theoretical value 755.28, measured value 755.32.
Embodiment 20: the synthesis of compound 197:
The preparation method of compound 197, the difference is that replacing intermediate A 1 with intermediate A 6, uses B9 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C52H33N7): theoretical value C, 82.63；H,4.40；N,12.97；Test value:
C,82.698；H,4.45；N,13.03.ESI-MS(m/z)(M+): theoretical value 755.28, measured value 755.36.
Embodiment 21: the synthesis of compound 203:
The preparation method of compound 203, the difference is that replacing intermediate A 1 with intermediate A 2, uses B6 with embodiment 3
Replace intermediate B 4.Elemental analysis structure (molecular formula C51H32N8): theoretical value C, 80.93；H,4.26；N,14.81；Test value:
C,80.99；H,4.38；N,14.85.ESI-MS(m/z)(M+): theoretical value 756.27, measured value 756.36.
Organic compound of the invention, used as CPL layer material, has high Tg (gamma transition temperature in luminescent device
Degree) temperature and high refractive index.Hot property and refraction index test are carried out respectively to the compounds of this invention and current material, as a result such as table
Shown in 2.Wherein the refraction index test figure of compound 6 is as shown in Figure 2.
Table 2
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.
By upper table data it is found that the materials such as CBP, Alq3 and TPBi that comparison is applied at present, organic compound of the invention
With high glass transition temperature, high refractive index, simultaneously because rigid containing pyridine, quinoxaline or benzimidazole or benzoxazoles
Property group, ensure that the thermal stability of material.Therefore, the present invention is being applied to OLED device by the organic material of core of pyridine
After the CPL layer of part, the light extraction efficiency of device can be effectively improved, and ensure that the long-life of OLED device.
Below by way of device embodiments 1~23 and device comparative example 1 OLED material that the present invention will be described in detail synthesizes in device
Application effect in part.Device embodiments 2~23 of the present invention, the device compared with device embodiments 1 of device comparative example 1
Manufacture craft it is identical, and use identical baseplate material and electrode material, the film thickness of electrode material is also kept
Unanimously, except that the CPL layer material in 2~20 pairs of devices of device embodiments converts；21~23 pairs of device embodiments
Hole barrier/electron transport layer materials of device convert, the performance test results of each embodiment obtained device such as 3 institute of table
Show.
Device embodiments 1: a kind of electroluminescent device, preparation step include: as shown in Figure 1
A) the ito anode layer 2 on transparent OLED device substrate 1 is cleaned, it is clear with deionized water, acetone, EtOH Sonicate respectively
It washes each 15 minutes, is then handled 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited by vacuum evaporation mode, with a thickness of 10nm,
This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited by vacuum evaporation mode, with a thickness of 80nm, the layer
For hole transmission layer 4；
D) luminescent layer 5 is deposited on hole transmission layer 4, CBP is used as material of main part, Ir (ppy)3As doping material
Material, Ir (ppy)3Mass ratio with CBP is 1:9, with a thickness of 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited by vacuum evaporation mode, with a thickness of 40nm, this layer
Organic material is used as hole barrier/electron transfer layer 6；
F) on hole barrier/electron transfer layer 6, vacuum evaporation electron injecting layer LiF, with a thickness of 1nm, which is electricity
Sub- implanted layer 7；
G) on electron injecting layer 7, Mg:Ag/Ag layers of vacuum evaporation cathode, it is 9:1, thickness that Mg:Ag, which adulterates mass ratio,
15nm, Ag thickness 3nm, the layer are cathode layer 8；
H) on cathode layer 8, the compound 1 of CPL material embodiment of the present invention preparation is deposited by vacuum evaporation mode,
With a thickness of 50nm, this layer of organic material is used as CPL layer 9.
After the production for completing electroluminescent device according to above-mentioned steps, the current efficiency of measurement device and service life, result
It is shown in Table 3.The molecular structural formula of associated materials is as follows:
Device embodiments 2: the CPL layer material of electroluminescent device becomes the compound 6 of preparation of the embodiment of the present invention.Device
Embodiment 3: the CPL layer material of electroluminescent device becomes the compounds of this invention 26.Device embodiments 4: electroluminescent device
CPL layer material becomes the compounds of this invention 28.Device embodiments 5: the CPL layer material of electroluminescent device becomes chemical combination of the present invention
Object 42.Device embodiments 6: the CPL layer material of electroluminescent device becomes the compounds of this invention 48.Device embodiments 7: electroluminescent hair
The CPL layer material of optical device becomes the compounds of this invention 52.Device embodiments 8: the CPL layer material of electroluminescent device becomes this
Invention compound 79.Device embodiments 9: the CPL layer material of electroluminescent device becomes the compounds of this invention 87.Device embodiments
10: the CPL layer material of electroluminescent device becomes the compounds of this invention 89.Device embodiments 11: the CPL layer of electroluminescent device
Material becomes the compounds of this invention 98.Device embodiments 12: the CPL layer material of electroluminescent device becomes the compounds of this invention
116.Device embodiments 13: the CPL layer material of electroluminescent device becomes the compounds of this invention 128.Device embodiments 14: electroluminescent
The CPL layer material of luminescent device becomes the compounds of this invention 145.Device embodiments 15: the CPL layer material of electroluminescent device becomes
For the compounds of this invention 149.Device embodiments 16: the CPL layer material of electroluminescent device becomes the compounds of this invention 153.Device
Part embodiment 17: the CPL layer material of electroluminescent device becomes the compounds of this invention 157.Device embodiments 18: electroluminescent cell
The CPL layer material of part becomes the compounds of this invention 179.Device embodiments 19: the CPL layer material of electroluminescent device becomes this hair
Bright compound 197.Device embodiments 20: the CPL layer material of electroluminescent device becomes the compounds of this invention 203.Device is implemented
Example 21: hole barrier/electron transport layer materials of electroluminescent device become the compounds of this invention 42.Device embodiments 22: electricity
Hole barrier/electron transport layer materials of electroluminescence device become the compounds of this invention 48.Device embodiments 23: electroluminescent cell
Hole barrier/electron transport layer materials of part become the compounds of this invention 52.Device comparative example 1: the CPL layer of electroluminescent device
Material becomes well known materials Alq3.The detection data of gained electroluminescent device is shown in Table 3.
Table 3
It can be seen that and of the present invention shine applied to OLED by the organic compound of core of pyridine by the result of table 3
After element manufacturing, compared with device comparative example 1, light, which takes out, to be obviously improved, under same current density, device brightness and device
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 is used
Service life is also improved.
In order to illustrate material membrane phase crystallization-stable performance of the present invention, by material compound 1 of the present invention and well known materials CBP
It has carried out film and has accelerated crystallization experiment: using vacuum evaporation mode, 1 He of compound for preparing the embodiment of the present invention being deposited respectively
CBP is vaporized on alkali-free glass, and is packaged in glove box (water oxygen content < 0.1ppm), by sample after encapsulation double 85
It is placed under the conditions of (85 DEG C of temperature, humidity 85%), periodically observes material with microscope (LEICA, DM8000M, 5*10 multiplying power)
Expect the crystalline state of film, experimental result is as shown in table 4, and material surface form is as shown in Fig. 3-1 to 3-5:
Table 4
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 2,8,21 and device comparative example 1 and carries out efficiency test in -10~80 DEG C of sections, acquired results are as shown in table 5 and Fig. 4.
Table 5
From the data of table 5 and Fig. 4 it is found that device embodiments 2,8,21 are material of the present invention and the device that known materials are arranged in pairs or groups
Structure is compared with device comparative example 1, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
To sum up, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (11)
1. a kind of organic compound containing pyridine, which is characterized in that the structure of the organic compound such as general formula (1) institute
Show:
In general formula (1), p, m, n independently be expressed as number 0,1 or 2；And m+n+p >=3；
In general formula (1), Ar1、Ar2、Ar3Independently be expressed as singly-bound, substituted or unsubstituted C6-60Arlydene contains one
Or one of multiple heteroatomic substituted or unsubstituted 5~60 yuan of heteroarylidenes；The hetero atom is nitrogen, oxygen or sulphur；Institute
State Ar1、Ar2、Ar3It can be identical or different；
R1、R2、R3It is optionally by one or more R4Substituted or unsubstituted quinoxalinyl, by one or more R4Replace or not
Substituted benzimidazolyl, by one or more R4Substituted or unsubstituted benzoxazolyl；R1、R2、R3It is identical when different；
Z is expressed as N atom or C-H identical or differently；
R4It is expressed as substituted or unsubstituted C6To C30Aryl and contain one or more heteroatomic substituted or unsubstituted C5Extremely
C30One of heteroaryl；The hetero atom is nitrogen, oxygen or sulphur.
2. a kind of organic compound containing pyridine according to claim 1, which is characterized in that the R1、R2、R3Point
It is not independent to be expressed as general formula (2), general formula (3), general formula (4), general formula (5), general formula (6), general formula (7), general formula (8), general formula
(9), structure shown in general formula (10) or general formula (11)；
Wherein, the Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar13、Ar14Independently be expressed as hydrogen original
Son, C1-10Linear or branched alkyl group, substituted or unsubstituted C6-60Aryl does not take containing one or more heteroatomic substitutions or
One of 5~60 unit's heteroaryls in generation；The hetero atom is nitrogen, oxygen or sulphur；Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、
Ar11、Ar12、Ar13、Ar14It can be identical or different；R4 is expressed as phenyl, xenyl, naphthalene or pyridyl group；Q is 0,1 or 2.
3. a kind of organic compound containing pyridine according to claim 1, which is characterized in that the organic compound
Structure such as formula (I-1)~(I-5) in it is any shown in:
4. a kind of organic compound containing pyridine according to claim 2, which is characterized in that the Ar1、Ar2、Ar3
Independently be expressed as C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, the substituted or unsubstituted phenylene of tritium atom；
C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, the substituted or unsubstituted naphthylene of tritium atom；C1-10Linear chain or branched chain alkane
The substituted or unsubstituted sub- dibiphenylyl of base, halogen atom, protium, deuterium, tritium atom；Anthrylene；C1-10Linear or branched alkyl group, halogen
Plain atom, protium, deuterium, the substituted or unsubstituted sub-pyridyl group of tritium atom；Sub- carbazyl；Furylidene；Sub- quinolyl；Sub- naphthyridines
Base；Sub- dibenzofuran group；Sub- dibenzothiophene；One of sub- 9,9- dimethyl fluorenyl or Asia N- phenyl carbazole base；
The Ar4、Ar5、Ar6、Ar7、Ar8、Ar9、Ar10、Ar11、Ar12、Ar13、Ar14Independently be expressed as C1-10Straight chain or
Branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted phenyl of tritium atom；C1-10Linear or branched alkyl group, halogen atom,
Protium, deuterium, the substituted or unsubstituted naphthalene of tritium atom；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, tritium atom replace or
Unsubstituted dibiphenylyl；C1-10Linear or branched alkyl group, halogen atom, protium, deuterium, the substituted or unsubstituted pyridine of tritium atom
Base；Carbazyl；Furyl；Pyrimidine radicals；Pyrazinyl；Pyridazinyl；Dibenzofurans；9,9- dimethyl fluorene；N- phenyl carbazole；Quinoline
Base；One of isoquinolyl or naphthyridines base.
5. a kind of organic compound containing pyridine according to claim 1, which is characterized in that the organic compound
Concrete structure formula are as follows:
Any one.
6. a kind of a kind of any one of Claims 1 to 5 preparation method of the organic compound containing pyridine, feature exist
In the reaction equation that the preparation method is related to are as follows:
(1) it under nitrogen atmosphere, weighs raw material A and is dissolved in DMF, addAnd palladium acetate, it is stirred
Object adds aqueous potassium phosphate solution, and it is small that the mixed solution of above-mentioned reactant is heated to reflux 5-15 under the conditions of 120-150 DEG C
When；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, it is pure that gained residue crosses silicagel column
Change, obtains compound intermediate I；
The raw material A withMolar ratio be 1:1.0~3, the molar ratio of palladium acetate and raw material A is 0.001~
The molar ratio of 0.04:1, potassium phosphate and raw material A is 1.0~4.0:1, and toluene dosage is that every gram of raw material A uses 30-50ml toluene；
(2) it under nitrogen atmosphere, weighs intermediate compound I and is dissolved in DMF, addAnd palladium acetate, it is stirred
Object adds aqueous potassium phosphate solution, and it is small that the mixed solution of above-mentioned reactant is heated to reflux 10-24 under the conditions of 120-150 DEG C
When；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, it is pure that gained residue crosses silicagel column
Change, obtains compound intermediate II；
The intermediate compound I withMolar ratio be 1:1.0~3, the molar ratio of palladium acetate and intermediate compound I is
The molar ratio of 0.001~0.04:1, potassium phosphate and intermediate compound I is 1.0~4.0:1, and toluene dosage is that every gram of intermediate compound I uses
10-40ml toluene；
(3) it under nitrogen atmosphere, weighs intermediate II and is dissolved in DMF, addAnd palladium acetate, stirring are mixed
Object is closed, aqueous potassium phosphate solution is added, the mixed solution of above-mentioned reactant is heated to reflux 10-24 under the conditions of 120-150 DEG C
Hour；After reaction, Jia Shui is cooled down, mixture is filtered and is dried in a vacuum drying oven, gained residue crosses silicagel column
Purifying, obtains target compound；
The intermediate II withMolar ratio be 1:1.0~3, the molar ratio of palladium acetate and intermediate II is
The molar ratio of 0.001~0.04:1, potassium phosphate and intermediate II is 1.0~4.0:1, and toluene dosage is that every gram of intermediate II uses
15-50ml toluene.
7. a kind of a kind of described in any item organic compounds containing pyridine of Claims 1 to 5 are applied to prepare Organic Electricity
Electroluminescence device.
8. 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 described in any item organic compounds containing pyridine of claim 1-5.
9. a kind of organic electroluminescence device according to claim 8, including hole blocking layer/electron transfer layer, special
Sign is that the hole blocking layer/electron transfer layer contains described in any item the organising containing pyridine of claim 1-5
Close object.
10. a kind of organic electroluminescence device according to claim 8, including CPL layers, which is characterized in that it is CPL layers described
Contain the described in any item organic compounds containing pyridine of claim 1-5.
11. a kind of illumination or display element, which is characterized in that contain claim 8~10 any for the illumination or display element
Organic electroluminescence device described in.
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| CN111153890A (en) * | 2020-01-15 | 2020-05-15 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting material, preparation method thereof and organic electroluminescent device |
| WO2020199998A1 (en) * | 2019-03-29 | 2020-10-08 | 吉林省元合电子材料有限公司 | 1,3,5-triazine compound and composition, and application thereof |
| CN113943280A (en) * | 2021-10-20 | 2022-01-18 | 京东方科技集团股份有限公司 | Compound containing benzo-heterocycle structure, electroluminescent device, and display device |
| CN114605402A (en) * | 2020-12-09 | 2022-06-10 | 江苏三月科技股份有限公司 | Organic compound containing triazine structure and application thereof |
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