CN110016060A - A kind of cavitation material, OLED display panel and electronic equipment comprising it - Google Patents
A kind of cavitation material, OLED display panel and electronic equipment comprising it Download PDFInfo
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- CN110016060A CN110016060A CN201810016465.4A CN201810016465A CN110016060A CN 110016060 A CN110016060 A CN 110016060A CN 201810016465 A CN201810016465 A CN 201810016465A CN 110016060 A CN110016060 A CN 110016060A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/331—Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni
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- Optics & Photonics (AREA)
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- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a kind of cavitation material, the cavitation material includes the compound with structure shown in formula (I).Transmission speed, the excellent electrochemical stability of cavitation material provided by the invention hole with higher or carrier.Cavitation material provided by the invention can be improved the transmission rate of hole and carrier for the hole mobile material of OLED, and be used as hole-injecting material with dopant material doping, can obtain more holes；Realizing reduces device voltage, improves the effect of device efficiency and service life.
Description
Technical field
The invention belongs to Organic Light Emitting Diode preparation fields, and in particular to a kind of phospha cyclopentadinyl compound, the sky comprising it
Cave barrier material, electron transport material and OLED display panel and electronic equipment.
Background technique
OLED display screen is to utilize display screen made of organic electroluminescent LED.It is right due to being provided simultaneously with self-luminous
It is higher than degree, thickness is thin, fast response time, can be made into flexible panel, the excellent characteristics such as simple structure, it is considered to be it is follow-on flat
Face display technology.The structure of OLED device is general are as follows: cathode (Cathode)/electron injecting layer (EIL)/electron transfer layer
(ETL)/luminescent layer (EML)/hole transmission layer (HTL)/hole injection layer (HIL)/anode (Anode).
There are also some problems to need to improve for existing OLED device, such as: improving OLED device efficiency；Improve OLED device
Service life；Reduce the operating voltage etc. of OLED device.
How high performance OLED functional material is obtained, it is most important to the performance for improving OLED device, to OLED function
Material property has claimed below: high carrier mobility rate, can reduce device drive voltage, improves device efficiency；When long
Between be deposited at a temperature of thermal stability it is good, this is most important to OLED industrial production；High glass transition temperature (Tg), suitable
Under the conditions of tend to form unformed film, this is most important to device lifetime；Material is easily prepared and is purified, and can reduce increased costs
Economic benefit.
Cavitation material disclosed in the prior art (including hole-injecting material HIL and/or hole mobile material HTL) material base
Originally there are following a few classes: triarylamine derivative, spirobifluorene derivative, carbazole derivates etc..But in order to meet the device of continuous improvement
Part performance requirement needs to develop novel hole mobile material while having high material thermal stability, and high Tg temperature is high
Carrier mobility, and the characteristics such as good solubility in organic solvent.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of cavitation material, the cavitation material includes
Compound with structure shown in formula (I):
In formula (I), R1、R2It is each independently selected fromShown compound
Any a kind；
Wherein, n1、n2It is each independently selected from 1 or 0；
Wherein, R '1、R’2、R’3、R’4、R’5、R’6、R’7、R’8Be each independently selected from hydrogen, deuterium ,-CHO,-CN、-NO2、 -OH、-COOR13、Appointing in substituted or unsubstituted linear chain or branched chain alkyl
1 kind of meaning；
Wherein, Y be oxygen, sulphur,In any a kind；
The R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18Selected from substituted or unsubstituted
Alkyl.
Cavitation material provided by the invention has ferrocene structure, and ferrous iron therein is easy to provide electronics, forms three
Note, and total is around present in the big pi bond of the cyclopentadiene conjugation of ferrocene, so that its hole centered on ferrocene
It is transmitted, obtains high hole transport rate and high carrier transport rate.
On the other hand, since ferrocene itself is to light, heat and its stabilization, and ferrocene has and stablizes reversible redox
Center (such as Formula II), during photoelectric conversion, the compound with ferrocene center can be stabilized, and improve the longevity of device
Life.
Preferably, substituted or unsubstituted linear chain or branched chain alkyl of the present invention includes substituted or unsubstituted C1~C4
Linear paraffin group, the branched paraffin group of substituted or unsubstituted C3~C40, substituted or unsubstituted C3~C40 ring
Shape alkane group, the linear chain or branched chain alkenyl group of substituted or unsubstituted C2~C40, substituted or unsubstituted C2~C40
Linear chain or branched chain alkynyl group, the carbon aromatic group of substituted or unsubstituted C5~C60, substituted or unsubstituted C5~C60
Any a kind in heteroaromatic group.
The linear paraffin group of the C1~C4 includes methyl, ethyl, propyl, butyl.
The branched paraffin group of the C3~C40 illustratively includes 2- methyl butyl, 3- ethylhexyl, the 5- ethyl last of the ten Heavenly stems
Base, 3- methyl dodecyl, 2- methyl, 3- ethyl eicosyl, 5- propyl, any a kind in 10- methyl tetracontyl.
The cyclic alkane group of the C3~C40 illustratively include cyclobutyl, cyclopenta, cyclohexyl, ring undecyl,In any a kind.
The linear chain or branched chain alkenyl group of the C2~C40 illustratively includes vinyl, acrylic, allyl, butylene
Any a kind in base, 3- methylhexene base.
The linear chain or branched chain alkynyl group of the C2~C40 illustratively includes acetenyl, propinyl, appointing in pentynyl
1 kind of meaning.
The carbon aromatic group of the C5~C60 illustratively includes phenyl, naphthalene, fluorenyl, anthryl, phenanthryl, anthraquinonyl, wheel
Any a kind in alkene.
The heteroaromatic group of the C5~C60 illustratively includes pyridyl group, pyrrole radicals, indyl, quinolyl, furans
Base, thienyl, thiazolyl, imidazole radicals, any a kind in pyrazinyl.
Preferably, R ' of the present invention1、R’2、R’3、R’4、R’5、R’6、R’7、R’8In, between adjacent group bridging or
Annelation obtains saturated rings or aromatic rings.
Annelation, which obtains aromatic rings, between adjacent group can expand pi bond, further increase the biography of electronics or carrier
Defeated speed.
Preferably, the R1、R2It is each independently selected from In any a kind.
Above structure has electron supplying capacity, and ferrocene grafting above structure can be improved ferrocene molecular weight and increase it
Stability.
Preferably, the compound with structure shown in formula (I) includes any a kind or at least 2 in following compound
The combination of kind:
Preferably, cavitation material of the present invention is hole-injecting material and/or hole mobile material.
When the cavitation material is hole-injecting material, compound provided by formula (I) can make as material of main part
With being doped with p-type dopant material.
Preferably, the hole-injecting material further includes p-type dopant material.
Preferably, the content of dopant material is 1~5wt% in the hole-injecting material.
The second object of the present invention is to provide a kind of OLED display panel, the OLED display panel include first electrode and
Second electrode, setting includes the lamination of luminescent layer and the first functional layer between the first electrode and second electrode.
First functional layer includes hole injection layer and/or hole transmission layer；
The material of the hole injection layer includes cavitation material described in the first purpose；
The material of the hole transmission layer includes cavitation material described in the first purpose.
Preferably, the lamination further include electron injecting layer, hole blocking layer, electron transfer layer, in electronic barrier layer
Any a kind or at least two kinds of of combination.
Preferably, the OLED display panel successively includes first electrode, hole injection layer, hole transport from the bottom to top
Layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and second electrode.
The material of the hole injection layer includes cavitation material described in the first purpose；
The material of the hole transmission layer includes cavitation material described in the first purpose.
Preferably, the first electrode is anode, and the second electrode is cathode.
The three of the object of the invention are to provide a kind of electronic equipment, including OLED display panel described in the second purpose.
Compared with prior art, the present invention have it is following the utility model has the advantages that
For cavitation material provided by the invention centered on ferrocene, ferrous iron easily becomes ferric iron release electronics, in conjunction with
The conjugation group connecting with Ferrocene Conjugated, obtains the transmission speed of higher hole or carrier；Simultaneously because ferrocene
Light, electricity are stablized, and exists in redox reaction and stablizes reversible reaction center, therefore impart provided by the invention
The excellent electrochemical stability of cavitation material.Hole mobile material of the cavitation material provided by the invention for OLED can be improved
The transmission rate in hole and carrier, and it is used as hole-injecting material with dopant material doping, more holes can be obtained；It is real
Device voltage is now reduced, the effect of device efficiency and service life is improved.
Specific embodiment
Of the invention for ease of understanding, it is as follows that the present invention enumerates embodiment.Those skilled in the art are it will be clearly understood that the implementation
Example is only to aid in the understanding present invention, should not be regarded as a specific limitation of the invention.
Embodiment 1
A kind of compound HT1Preparation method, including walk as follows
It is rapid:
Synthesis condition are as follows:
1.38g di-ferrocene boric acid, 4g anhydrous K are added in 200mL bottle with two necks3PO4Powder, 3.5g bromo triphenylamine,
Anhydrous Isosorbide-5-Nitrae-the dioxane of 100mL, drum nitrogen 30min, adds 0.15g Pd (PPh3)4, flow back under the conditions of being protected from light 101 DEG C anti-
It should for 24 hours.Device is cooled to room temperature, and a large amount of water are added, then filter out by solid, is recrystallized after dry with Isosorbide-5-Nitrae-dioxane
Five times, then distillation obtains 1.6g Tan solid (48% yield).
Characterize data:
126 DEG C of Tg (DSC), purity 99.9%；
1H NMR (400MHz, DMSO) δ 7.23 (d, 4H), 7.01 (m, 8H), 6.62 (d, 4H), 6.52 (d, 4H), 6.46
(m, 8H), 4.30 (m, 4H), 4.17 (m, 4H).
Embodiment 2
A kind of compound HT2Preparation method, including walk as follows
It is rapid:
Synthesis condition is same as Example 1, Tan solid, yield 43%.
Characterize data: 128 DEG C of Tg (DSC), purity 99.9%；
1H NMR(400MHz,DMSO)δ7.55(d,4H),7.50(d,4H),7.40(d,4H),7.30(d,4H),7.08
(m,4H),6.98(m,4H),4.27(m,4H),4.15(m,4H)。
Embodiment 3
A kind of compound HT3Preparation method, including walk as follows
It is rapid:
Synthesis condition is same as Example 1, Tan solid, yield 45%.
Characterize data: 124 DEG C of Tg (DSC), purity 99.9%；
1H NMR(400MHz,DMSO)δ7.23(d,4H),6.82-6.81(m,8H),6.52(d,4H),6.50(m,4H),
6.34(d,4H),4.26(m,4H),4.13(m,4H),3.80(s,4H)。
Embodiment 4
A kind of compound HT4Preparation method, include the following steps:
Synthesis condition are as follows:
2.6g raw material A, 4g anhydrous K are added in 200mL bottle with two necks3PO4Powder, the anhydrous Isosorbide-5-Nitrae-dioxy of 4g raw material B, 100mL
Six rings, drum nitrogen 30min, add 0.1g Pd (PPh3)4, for 24 hours, device is cooled to room to back flow reaction under the conditions of being protected from light 90 DEG C
Temperature is added a large amount of water, then filters out by solid, is recrystallized to give intermediate C with Isosorbide-5-Nitrae-dioxane after drying.
KOAc 1.74g, B are sequentially added in 50mL reaction flask2(pin)24.5g, Pd2pda350mg,
Xphos110mg, EtOH 15mL, side stirring are just added intermediate C 2.8g, react 1h at 60 DEG C, be cooled to room temperature, diatomite
Filtering, ethyl acetate washing are purified with silica gel column chromatography after merging filtrate vacuum distillation, obtain intermediate D.
5.6g raw material D, 4g anhydrous K are added in 200mL bottle with two necks3PO4Powder, the anhydrous Isosorbide-5-Nitrae-dioxy of 4g raw material E, 100mL
Six rings, drum nitrogen 30min, add 0.1g Pd (PPh3)4, it is protected from light, for 24 hours, device is cooled to room to back flow reaction under the conditions of 101 DEG C
Temperature is added a large amount of water, then filters out by solid, is recrystallized 5 times after dry with Isosorbide-5-Nitrae-dioxane, then distillation obtains 5g
Tan solid, gross production rate 38%.
Characterize data:
Purity 99.9%, 130 DEG C of Tg (DSC)；
1H NMR (400MHz, DMSO) δ 7.55-7.50 (m, 4H), 7.40 (d, 2H), 7.30 (d, 2H), 7.30 (d, 2H),
7.08 (t, 2H), 6.82-6.81 (m, 4H), 6.52-6.50 (m, 4H), 6.34 (d, 2H), 4.32-4.28 (m, 4H), 4.20-
4.18 (m, 4H), 3.81 (s, 2H).
Embodiment 5
A kind of compound HT5Preparation method, include the following steps:
HT5 synthesis condition is same as Example 4, Tan solid, yield 40%.
Characterize data: purity 99.9%, 129 DEG C of Tg (DSC)；
1H NMR (400MHz, DMSO) δ 7.54 (d, 2H), 7.50 (d, 2H), 7.41 (d, 2H), 7.30 (d, 2H), 7.23
(d, 2H), 7.08 (m, 2H), 7.01-6.90 (m, 6H), 6.62 (m, 2H), 6.52 (m, 2H), 6.46 (d, 4H), 4.31-4.26
(m, 4H), 4.21-4.18 (m, 4H).
Embodiment 6
A kind of compound HT6Preparation method, include the following steps:
HT6 synthesis condition is same as Example 4, Tan solid, yield 39%.
Characterize data: purity 99.9%, 128 DEG C of Tg (DSC)；
1H NMR (400MHz, DMSO) δ 7.57 (d, 2H), 7.51 (d, 2H), 7.40 (d, 2H), 7.31 (d, 2H), 7.22
(d, 2H), 7.06-7.0 (m, 4H), 6.82-6.80 (m, 4H), 6.52 (m, 2H), 6.49 (m, 2H), 6.32 (d, 2H), 3.80
(s, 2H), 4.31-4.26 (m, 4H), 4.21-4.18 (m, 4H).
Application examples and comparative example
A kind of OLED device is provided, from the bottom to top successively includes anode (ITO, 80nm)/hole injection layer/hole transport
Layer/luminescent layer (TCTA:Ir (ppy)3(8%), 20nm)/electron transfer layer (BPhen (40%): LiQ (60%), 30nm)/yin
Pole (Mg/Ag, 20nm)；The selection of the material of hole injection layer and hole transmission layer is as shown in table 1:
1 device architecture of table
In application examples and comparative example, the corresponding structural formula of the abbreviation of material is as follows:
Performance test
The test of luminous efficiency, test method are carried out during the OLED that application examples is provided are as follows: device performance (LE, V) number
It is measured according under 1000nits brightness, the service life, (LT95) data were in current density 40mA/cm2Under the conditions of be calculated.
The performance test results are as shown in table 2:
2 device performance of table
The performance of table 2 confirms that material height of the invention is suitable as hole-injecting material or hole in OLED device
Transmission material, compared to control compounds obtain higher efficiency (48Cd/A or more, and when hole transport and hole injection be all
When the compound of the present invention, in 70Cd/A or more), longer service life (60 hours or more, and when hole transport and hole injection all
When being the compound of the present invention, at 171 hours or more), (4.4V is hereinafter, and when hole transport and hole are injected for lower voltage
When being all the compound of the present invention, in 3.6V or less).
The Applicant declares that the present invention is explained by the above embodiments detailed process equipment and process flow of the invention,
But the present invention is not limited to the above detailed process equipment and process flow, that is, it is above-mentioned detailed not mean that the present invention must rely on
Process equipment and process flow could be implemented.It should be clear to those skilled in the art, any improvement in the present invention,
Addition, selection of concrete mode of equivalence replacement and auxiliary element to each raw material of product of the present invention etc., all fall within of the invention
Within protection scope and the open scope.
Claims (13)
1. a kind of cavitation material, which is characterized in that the cavitation material includes the compound with structure shown in formula (I):
In formula (I), R1、R2It is each independently selected fromAny the 1 of shown compound
Kind；
Wherein, n1、n2It is each independently selected from 1 or 0；
Wherein, R '1、R’2、R’3、R’4、R’5、R’6、R’7、R’8Be each independently selected from hydrogen, deuterium ,-CHO,-CN、-NO2、 -OH、-COOR13、Appointing in substituted or unsubstituted linear chain or branched chain alkyl
1 kind of meaning；
Wherein, Y be oxygen, sulphur,In any a kind；
The R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18Selected from substituted or unsubstituted hydrocarbon
Base.
2. cavitation material as described in claim 1, which is characterized in that the substituted or unsubstituted linear chain or branched chain alkyl packet
It includes the linear paraffin group of substituted or unsubstituted C1~C4, the branched paraffin group of substituted or unsubstituted C3~C40, replace
Or the cyclic alkane group of unsubstituted C3~C40, substituted or unsubstituted C2~C40 linear chain or branched chain alkenyl group, take
Generation or the linear chain or branched chain alkynyl group of unsubstituted C2~C40, substituted or unsubstituted C5~C60 carbon aromatic group, take
Any a kind in the heteroaromatic group of generation or unsubstituted C5~C60.
3. cavitation material as described in claim 1, which is characterized in that the R '1、R’2、R’3、R’4、R’5、R’6、R’7、R’8
In, bridging or annelation obtain saturated rings or aromatic rings between adjacent group.
4. cavitation material as described in claim 1, which is characterized in that the R1、R2It is each independently selected fromIn any a kind.
5. cavitation material as described in claim 1, which is characterized in that the compound with structure shown in formula (I) includes
Any a kind or at least two kinds of of combination in following compound:
6. cavitation material as described in claim 1, which is characterized in that the cavitation material is hole-injecting material and/or sky
Hole transport materials.
7. cavitation material as described in claim 1, which is characterized in that the hole-injecting material further includes p-type dopant material.
8. cavitation material as claimed in claim 7, which is characterized in that the content of dopant material is in the hole-injecting material
1~5wt%.
9. a kind of OLED display panel, which is characterized in that the OLED display panel includes first electrode and second electrode, described
Setting includes the lamination of luminescent layer and the first functional layer between first electrode and second electrode；
First functional layer includes hole injection layer and/or hole transmission layer；
The material of the hole injection layer includes cavitation material described in one of claim 1~8；
The material of the hole transmission layer includes cavitation material described in one of claim 1~6.
10. OLED display panel as claimed in claim 9, which is characterized in that the lamination further includes electron injecting layer, hole
Barrier layer, electron transfer layer, any a kind or at least two kinds of of combination in electronic barrier layer.
11. OLED display panel as claimed in claim 9, which is characterized in that the OLED display panel is from the bottom to top successively
Including first electrode, hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electricity
Sub- implanted layer and second electrode；
The material of the hole injection layer includes cavitation material described in one of claim 1~10；
The material of the hole transmission layer includes cavitation material described in one of claim 1~7.
12. OLED display panel as claimed in claim 9, which is characterized in that the first electrode is anode, second electricity
Extremely cathode.
13. a kind of electronic equipment, which is characterized in that including OLED display panel described in one of claim 9~12.
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| CN201810016465.4A CN110016060A (en) | 2018-01-08 | 2018-01-08 | A kind of cavitation material, OLED display panel and electronic equipment comprising it |
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| CN201810016465.4A CN110016060A (en) | 2018-01-08 | 2018-01-08 | A kind of cavitation material, OLED display panel and electronic equipment comprising it |
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| CN106674026A (en) * | 2016-12-28 | 2017-05-17 | 上海天马有机发光显示技术有限公司 | Hole-transmission material, OLED (Organic Light Emitting Diode) display panel comprising same and electronic equipment |
| CN107033180A (en) * | 2015-07-14 | 2017-08-11 | 上海和辉光电有限公司 | A kind of compound for luminescent material |
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2018
- 2018-01-08 CN CN201810016465.4A patent/CN110016060A/en active Pending
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| CN1684564A (en) * | 2004-04-12 | 2005-10-19 | 通用电气公司 | Opto-electroactive device comprising a metallocene and method |
| CN107033180A (en) * | 2015-07-14 | 2017-08-11 | 上海和辉光电有限公司 | A kind of compound for luminescent material |
| KR20170051260A (en) * | 2015-10-29 | 2017-05-11 | 기초과학연구원 | N-Heterocyclic carbene metallocene compounds and method for preparing the same |
| CN106674026A (en) * | 2016-12-28 | 2017-05-17 | 上海天马有机发光显示技术有限公司 | Hole-transmission material, OLED (Organic Light Emitting Diode) display panel comprising same and electronic equipment |
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| CHANG SU: "Synthesis and charge–discharge properties of a ferrocene-containing", 《JOURNAL OF MATERIALS CHEMISTRY》 * |
| K.R. JUSTIN THOMAS等，: "Star-shaped polyferrocenes based on thiophene and triphenylamine: synthesis, spectroscopy and electrochemistry", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
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