CN108484417A - A kind of organic display material and its synthesis and application - Google Patents
A kind of organic display material and its synthesis and application Download PDFInfo
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Abstract
The present invention relates to organic electroluminescent (OLED) display field, more particularly to a kind of organic display material and its synthesis and application, the organic display material structure general formula is as follows.Above-mentioned organic display material provided by the present invention, so as to increase intermolecular distance, prevents the association between compound due to containing methyl on specific phenyl ring, reduces the probability of molecule piled up.Such material has high hole mobility, preferable thin film stability and suitable molecular entergy level, can be used in field of organic electroluminescence, be used as hole mobile material, be had broad application prospects.
Description
Technical field
The present invention relates to a kind of novel organic display materials, and its application in organic electroluminescence device, and belonging to has
Organic electro luminescent display technology field.
Background technology
Application of organic electroluminescent (OLED) material in the fields such as presentation of information material, organic optoelectronic material has
Great researching value and fine application prospect.With the development of multimedia information technology, to flat-panel display device performance
It is required that higher and higher.Current main display technology has plasma display apparatus, field emission display and organic electroluminescent
Display device (OLED).Wherein, OLED has itself luminous, low-voltage direct-current driving, all solidstate, the wide, various colors in visual angle etc.
Series of advantages, compared with liquid crystal display device, OLED does not need backlight, and visual angle is wider, low in energy consumption, and response speed is liquid
1000 times of crystal display device, therefore, OLED have broader practice foreground.
The hole mobile material reported at present is since molecular weight is generally smaller, and the glass transition temperature of material is relatively low, in material
During use, charging and discharging, material are easy crystallization repeatedly, and the homogeneity of film is destroyed, to influence the materials'use service life.
Therefore, the hole mobile material for developing stability and high efficiency improves device light emitting efficiency to reduce driving voltage, extends the device longevity
Life has critically important actual application value.
Invention content
The purpose of the present invention is to provide can carry out low voltage drive, long lifespan and the OLED element of high efficiency,
And the organic display material of such OLED element can be provided.
Specifically, present invention firstly provides a kind of novel organic display material (or being organic compound),
With the structure as shown in general formula (1)：
In general formula I, Ar is selected from：
M is selected from 1 to 4 integer；
Indicate substitution position.
Preferably, in general formula (1)：
Ar is selected from：
And/or m is 1 or 2.
As further preferred technical solution, the organic material is selected from one kind of following compound：
Above-mentioned organic material provided by the present invention on specific phenyl ring due to containing methyl, so as to increase molecule
Between distance, prevent the association between compound, reduce the probability of molecule piled up.It is less likely to occur to crystallize when vapor deposition,
OLED yield rates can be effectively improved by being applied in OLED device, reduced driving voltage, improved luminous efficiency, increase the service life.
Invention also provides the preparation method of above-mentioned organic material,
Specifically, the preparation method reaction mechanism mechanism of reaction provided by the present invention is as follows:
Include the following steps：
(a) using compound I-1 as starting material, withCoupling reaction occurs, obtains compound I-2；
(b) with dibromo condensed-nuclei aromatics coupling reaction occurs for compound I-2, obtains compound I.
Wherein, Ar and m refers specifically to generation ibid restriction about organic material.
Known common approach can be used to realize in above-mentioned step those skilled in the art, such as selects suitable catalysis
Agent, solvent determine suitable reaction temperature, time etc., and the present invention is not particularly limited this.
Preferably, above-mentioned preparation method includes the following steps：
(a) using compound I-1 as starting material, using toluene as solvent, with three (hexichol benzylacetone) two palladiums and three tertiary fourths
Base phosphine is catalyst, and sodium tert-butoxide is alkali, nitrogen protection, 100-110 DEG C of temperature control, compound I-1 withCoupling reaction occurs,
Obtain compound I-2；
(b) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide
For alkali, nitrogen protection, 110-120 DEG C of temperature control, compound I-2 and dibromo condensed-nuclei aromatics generation coupling reaction, compound I is obtained；
Wherein, Ar and m refers specifically to generation ibid restriction about organic material.
Above-mentioned dibromo condensed-nuclei aromatics, sodium tert-butoxide and three (hexichol benzylacetone) two palladiums etc. can pass through open business way
Method known per se synthesizes to obtain in diameter or document.
Invention further provides application of the above-mentioned organic material in organic electroluminescence device.
Preferably, organic material of the present invention is used as hole transmission layer in organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence device, organic function layer includes above-mentioned general formula compound,
Such compound is used as the hole mobile material in organic function layer.
Preferably, above-mentioned organic electroluminescence device is from the bottom to top successively by transparent substrate, anode layer, the hole transport
Layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode layer composition.
The material for constituting the transparent substrate is glass substrate or flexible substrate；
Substrate can use the substrate in conventional organic luminescence device, such as：Glass or plastics.
The material for constituting the anode layer is inorganic material；Wherein, the inorganic material be specially tin indium oxide (ITO),
At least one of zinc oxide, zinc tin oxide, gold, silver or copper, preferably tin indium oxide (ITO)；
Glass substrate, ITO is preferably selected to make anode material in the element manufacturing of the present invention.
The material for constituting the hole transmission layer is Formulas I compound represented；
The material for constituting the organic luminous layer is made of material of main part；
Wherein, the material of main part is any one in following compound：
Constitute any one of the material of the electron transfer layer in following compound：
The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO, one kind in Al2O3, preferably LiF.
Constitute the one kind of the material of the cathode in lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, gold and silver, preferably aluminium.
Specifically,
The thickness of the hole transmission layer is 20-40nm, preferably 30nm；
The thickness of the organic luminous layer is 10-100nm, preferably 30nm；
The thickness of the electron transfer layer is 10-30nm, preferably 40nm；
The thickness of the electron injecting layer is 5-30nm, preferably 10nm；
The thickness of the cathode is 50-110nm, preferably 60nm.
Novel OLED material provided by the invention is centered on fused ring compound, using methylic (naphthalidine is end group),
By in the active position of polycyclc aromatic compound, introducing the substituent group (N- phenyl-1-naphthylamines) with hole transport performance,
Obtain a kind of novel OLED material with hole transport performance.Such material has high hole mobility, preferable thin
Membrane stability and suitable molecular entergy level, can be used in field of organic electroluminescence, be used as hole mobile material.
Specific implementation mode
Tri-tert-butylphosphine used in the present invention, sodium tert-butoxide, three (hexichol benzylacetone) two palladiums, dibromo polycyclic aromatic hydrocarbon etc.
Industrial chemicals can conveniently be bought in chemical products market at home.
Compound synthesis in the present invention all can refer to the progress of 1 method of embodiment.It is described below in the present invention and partly leads
Want the synthetic method of compound.
Embodiment 1
The synthesis of (compound 1)
Synthetic route is as follows：
The synthesis of (compound 1)
1) synthesis of compound 1-2
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement
Amine 27.9g (purity 99%, 0.3mol), the bromo- 8- methyl naphthalenes of 44.2g1- (purity 99%, 0.2mol) and toluene 400ml.Again
3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement.After adding, agitating and heating is opened
100 DEG C are warming up to, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, rotates filtrate, is used
It after dichloromethane dissolving, is washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, revolving filter
Liquid obtains 39.6g yellow products, purity 99%, yield 85%.
2) synthesis of compound 1
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 9 are sequentially added after argon gas displacement,
10- dibromoanthracenes 26.4g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.Again 1.6ml tri- is sequentially added after argon gas displacement
Tertiary butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start be added dropwise by
The solution of 47.3gN- phenyl -8- methyl-1s-naphthylamines (purity 99%, 0.203mol) and 100ml dimethylbenzene composition, temperature control 110-
120℃.50 DEG C are cooled to, the hydrolysis of 100m deionized waters is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF,
Obtain 38.2g yellow products, purity 99%, yield 76%.
Product MS (m/e)：640.29；Elemental analysis (C48H36N2)：Theoretical value C：89.97%, H：5.66%, N：
4.37%；Measured value C：89.96%, H：5.67%, N：4.37%.
Embodiment 2：
The synthesis of (compound 2)
Synthetic route is as follows：
1) synthesis of compound 2-1
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement
Amine 27.9g (purity 99%, 0.3mol), the bromo- 8- methyl naphthalenes of 44.2g1- (purity 99%, 0.2mol) and toluene 400ml.Again
3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement.After adding, agitating and heating is opened
100 DEG C are warming up to, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, rotates filtrate, is used
It after dichloromethane dissolving, is washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, revolving filter
Liquid obtains 42g yellow products, purity 99%, yield 90%.
2) synthesis of compound 2
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 9 are sequentially added after argon gas displacement,
Bis- bromo- 2- methyl anthracene 27.5g (purity 99%, 0.0785mol) of 10- and dimethylbenzene 100ml.It is sequentially added after argon gas displacement again
1.6ml tri-tert-butylphosphines and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise
The solution being made of 47.3gN- phenyl -8- methyl-1s-naphthylamines (purity 99%, 0.203mol) and 100ml dimethylbenzene, temperature control
110-120℃.50 DEG C are cooled to, the hydrolysis of 100m deionized waters is added, stirs 10 minutes, filtering, filter cake is boiled several repeatedly with DMF
It is secondary, obtain 36g yellow products, purity 99%, yield 70%.
Product MS (m/e)：654.30；Elemental analysis (C49H38N2)：Theoretical value C：89.87%, H：5.85%, N：
4.28%；Measured value C：89.86%, H：5.87%, N：4.27%.
Embodiment 3
The synthesis of (compound 3)
Synthetic route is as follows：
(compound 3)
1) synthesis of compound 3-1
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement
Amine 27.9g (purity 99%, 0.3mol), the bromo- 8- methyl naphthalenes of 44.2g1- (purity 99%, 0.2mol) and toluene 400ml.Again
3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement.After adding, agitating and heating is opened
100 DEG C are warming up to, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, rotates filtrate, is used
It after dichloromethane dissolving, is washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, revolving filter
Liquid obtains 41g yellow products, purity 99%, yield 88%.
2) synthesis of compound 3
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 6 are sequentially added after argon gas displacement,
12- dibromos bend 24g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.Again tri- uncles of 1.6ml are sequentially added after argon gas displacement
Butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise by 47.3gN-
The solution of phenyl -8- methyl-1s-naphthylamines (purity 99%, 0.203mol) and 100ml dimethylbenzene composition, 110-120 DEG C of temperature control.Drop
Temperature is added the hydrolysis of 100m deionized waters, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, obtains 42.8g to 50 DEG C
Yellow product, purity 99%, yield 79%.
Product MS (m/e)：690.3；Elemental analysis (C52H38N2)：Theoretical value C：90.41%, H：5.54%, N：
4.05%；Measured value C：90.40%, H：5.55%, N：4.05%.
According to embodiment 1, the technical solution of embodiment 2 and embodiment 3, it is only necessary to which the corresponding raw material of simple replacement does not change
Become any substantive operations, following compound can be synthesized.
Embodiment 4 prepares device OLED-1~OLED-4
The method for preparing device OLED-1~OLED-4 is present embodiments provided, is included the following steps：
1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water
It washes, it is 30 minutes ultrasonic in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, use ultraviolet rays cleaning
Machine irradiates 10 minutes, and low energy cation beam bombarded surface is used in combination.
2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa,
It is hole transmission layer that one layer of embodiment 1 is deposited on above-mentioned anode tunic and prepares the compound 1 of gained ownership Formulas I, and evaporation rate is
0.2nm/s, vapor deposition film thickness are 30nm；
3) continue to be deposited ADN on the hole transport layer as material of main part, as the organic luminous layer of device, evaporation rate
Film thickness for 0.2nm/s, vapor deposition gained organic luminous layer is 30nm；
4) continue that electron transfer layers of the one layer of compound BCP as device is deposited on organic luminous layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 40nm；
5) continue that electron injecting layers of the one layer of LiF as device is deposited on electron transfer layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 10nm；
6) continue that cathodes of the one layer of Al as device, evaporation rate 0.2nm/s, vapor deposition is deposited on electron injecting layer
Film thickness is 60nm；OLED device provided by the invention is obtained, OLED-1 is denoted as；
According to upper identical step, by the compound 1 in step 2) replace with embodiment 2 prepare gained compound 2, obtain
To OLED-2 provided by the invention；
According to upper identical step, by the compound 1 in step 2) replace with embodiment 3 prepare gained compound 3, obtain
To OLED-3 provided by the invention；
According to upper identical step, the compound 1 in step 2) is replaced with into NPB, obtains comparative device OLED-4；
NPB (control compounds 1)
The performance test results of obtained device OLED-1 to OLED-4 are as shown in table 1.
The performance test results of table 1, OLED-1 to OLED-4
From the foregoing, it will be observed that the device OLED-1 being prepared into using organic material shown in Formulas I provided by the invention is to OLED-4's
Bright voltage is lower, brightness under the same conditions, the apparent device OLED-4 than NPB as hole mobile material of current efficiency
It is much higher, and the service life of device be obviously prolonged very much.
Although the present invention is described in conjunction with the embodiments, the invention is not limited in above-described embodiments, should manage
Solution, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise
The scope of the present invention.
Claims (10)
1. a kind of organic display material, it is characterised in that：Its structure is as shown in general formula I：
Wherein, Ar is selected from：
Wherein, m is selected from 1 to 4 integer；
Indicate substitution position.
2. organic display material according to claim 1, it is characterised in that：In general formula I:
Ar is selected from：
And/or m is 1 or 2.
3. organic display material according to claim 1 or 2, it is characterised in that：The organic material is selected from following chemical combination
One kind of object：
4. the synthetic method of claim 1-3 any one of them organic display materials, it is characterised in that：The reaction mechanism mechanism of reaction is as follows:
Specifically comprise the following steps：
(a) using compound I-1 as starting material, withCoupling reaction occurs, obtains compound I-2；
(b) with dibromo condensed-nuclei aromatics coupling reaction occurs for compound I-2, obtains compound I；
Wherein, the reference of Ar and m is the same as described in claim any one of 1-3.
5. the synthetic method of organic display material according to claim 4, it is characterised in that：Include the following steps：
(a) using compound I-1 as starting material, using toluene as solvent, with three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine
For catalyst, sodium tert-butoxide is alkali, nitrogen protection, 100-110 DEG C of temperature control, compound I-1 withCoupling reaction occurs, obtains
Compound I-2；
(b) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide is
Alkali, nitrogen protection, 110-120 DEG C of temperature control, compound I-2 occur coupling reaction with dibromo condensed-nuclei aromatics, obtain compound I.
6. application of the claim 1-3 any one of them organic display materials in organic electroluminescence device.
7. application according to claim 6, it is characterised in that：The organic display material is in the organic electroluminescence
It is used as hole transmission layer in part.
8. a kind of organic electroluminescence device, it is characterised in that：Including by any one of the claim 1-3 organic display materials
Manufactured hole transmission layer.
9. organic electroluminescence device according to claim 8, it is characterised in that：The organic electroluminescence device is under
It is supreme successively by transparent substrate, anode layer, the hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and the moon
Pole layer composition；
It is preferred that：
The material of the transparent substrate is glass substrate or plastics；
And/or；The material of the anode layer is constituted in tin indium oxide, zinc oxide, zinc tin oxide, gold, silver or copper at least
It is a kind of；
And/or；The material of main part for constituting the organic luminous layer is any one in following compound：
And/or constitute any one of the material of the electron transfer layer in following compound：
And/or；The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO or Al2O3In one kind；
And/or；Constitute the one kind of the material of the cathode in lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, gold and silver.
10. organic electroluminescence device according to claim 9, it is characterised in that：The thickness of the hole transmission layer is
20-40nm；The thickness of the organic luminous layer is 10-100nm；The thickness of the electron transfer layer is 10-30nm；The electronics
The thickness of implanted layer is 5-30nm；The thickness of the cathode is 50-110nm.
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| WO2020108422A1 (en) * | 2018-11-26 | 2020-06-04 | 常州强力电子新材料股份有限公司 | Diarylamine-substituted 9,9'-spirobifluorene compound and application thereof in oled device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102782084A (en) * | 2010-03-06 | 2012-11-14 | 默克专利有限公司 | Organic electroluminescent device |
| WO2017061779A1 (en) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Amine compound and organic light-emitting device comprising same |
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| CN102782084A (en) * | 2010-03-06 | 2012-11-14 | 默克专利有限公司 | Organic electroluminescent device |
| WO2017061779A1 (en) * | 2015-10-06 | 2017-04-13 | 주식회사 엘지화학 | Amine compound and organic light-emitting device comprising same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2020108422A1 (en) * | 2018-11-26 | 2020-06-04 | 常州强力电子新材料股份有限公司 | Diarylamine-substituted 9,9'-spirobifluorene compound and application thereof in oled device |
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