CN107188859A - A kind of organic electroluminescent compounds and the OLED containing the compound - Google Patents
A kind of organic electroluminescent compounds and the OLED containing the compound Download PDFInfo
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- CN107188859A CN107188859A CN201610146865.8A CN201610146865A CN107188859A CN 107188859 A CN107188859 A CN 107188859A CN 201610146865 A CN201610146865 A CN 201610146865A CN 107188859 A CN107188859 A CN 107188859A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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]
- H10K50/14—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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a kind of organic electroluminescent compounds, it is Striazine derivative, with the structure as shown in formula (I)：Wherein, R1、R2、R3It is each independently the substituent for including aryl or heteroaryl.A series of Striazine derivatives that the present invention is designed can have heat endurance good as OLED luminescent materials, such luminescent material, and luminous efficiency is high, the advantages of long lifespan, with the prospect applied to AMOLED industries.
Description
Technical field
The present invention relates to a kind of compound, more particularly to a kind of organic electroluminescent compounds and containing the compound
OLED.
Background technology
At present, display screen is with TFT (Thin Film Transistor, TFT)-LCD
It is main, due to the display that it is non-spontaneous light, it is therefore necessary to pass through backlight throw light, and sequentially penetrate
Polarizer, glass substrate, liquid crystal layer, colored filter, glass substrate, polarisation in TFT-LCD panels
The correlation spare part such as plate, finally enters the eye imaging of people, can be only achieved the function of display.Just because of above-mentioned
Complicated display process, its display screen occurs in that slow reaction rate, power consumption, narrow viewing angle in actual application
The shortcomings of, it is not enough to turn into perfect display screen.
Organic electroluminescent LED (OLEDs) possesses as a kind of brand-new Display Technique in each performance
The unmatched advantage of existing Display Technique, such as have it is all solid state, from main light emission, brightness height, high-resolution,
Visual angle wide (more than 170 degree), fast response time, thickness of thin, small volume, it is lightweight, can be used flexible base board,
Low-voltage direct-current driving (3-10V), low in energy consumption, operating temperature range is wide etc. so that its application market is very
Extensively, as illuminator, communication system, car-mounted display, portable electric appts, fine definition are shown even
It is military field.
Among organic electroluminescent LED, when electronics and hole in organic molecule in conjunction with after, can be because electricity
The difference of sub- spin symmetry mode, produces the form of two kinds of excitation state, and one kind accounts for 25%, one for singlet state
It is triplet 75% to plant.It is generally believed that fluorescent material is usually the internal quantum of organic small molecule material
The limit be 25%.And phosphor material is due to Effect of Spin-orbit Coupling caused by heavy atoms effect, Ke Yili
With the energy of 75% triplet exciton, so unquestionable improve luminous efficiency.
Present invention seek to address that the technical problem such as existing display screen reaction rate is slow, power consumption, narrow viewing angle.Therefore,
Design is with finding a kind of compound, as OLED new materials to overcome it to occur in actual application
Deficiency, be the emphasis and Development Trend from now in OLED material research work.
The content of the invention
In order to preferably embody across epoch technical advantages of the OLED relative to TFT-LCD, Er Qieneng
OLED material prior art produced problem in actual application is enough solved, present invention seek to address that existing
There are the technical problems such as slow display screen reaction rate, power consumption, narrow viewing angle.There is provided one for the first aspect of the present invention
Plant organic electroluminescent compounds, it is characterised in that its structure is the Striazine derivative shown in formula (I)：
Wherein, R1、R2、R3It is each independently the substituent for including aryl or heteroaryl.
Preferably, the R1、R2、R3Be each independently C3-C20 includes taking for aryl or heteroaryl
Dai Ji.
It is further preferred that the heteroaryl contains N.
It is further preferred that the R1、R2、R3It is each independently following group：
It is further preferred that the organic electroluminescent compounds are selected from following compound：
There is provided a kind of OLED electricity containing above-mentioned organic electroluminescent compounds for the second aspect of the present invention
Son transmission layer material.
There is provided a kind of OLED hairs containing above-mentioned organic electroluminescent compounds for the third aspect of the present invention
Photosphere material.
There is provided a kind of OLED containing above-mentioned organic electroluminescent compounds is empty for the fourth aspect of the present invention
Transmit layer material in cave.
There is provided a kind of OLED devices containing above-mentioned organic electroluminescent compounds for the fifth aspect of the present invention
Part.
One kind that the technical scheme that the present invention is recorded is provided has the Striazine derivative shown in formula (I), can
For making OLED, feux rouges material of main part is particularly suitable for use as.It is a series of equal that the present invention is designed
Pyrrolotriazine derivatives, for making OLED, solve slow existing display screen reaction rate, power consumption, regard
The technical problem such as angle is narrow, in addition, also having heat endurance good, luminous efficiency is high, the advantages of long lifespan, has
Prospect applied to AMOLED industries.
Embodiment
With reference to embodiment, the present invention is further elaborated, but the present invention is not limited to following implementation
Mode.
The first aspect of the present invention is spread out there is provided a kind of organic electroluminescent compounds, the compound for s-triazine
Biology, shown in its structure such as formula (I)：
Wherein, R1、R2、R3It is each independently the substituent for including aryl or heteroaryl.
In a preferred embodiment, the R1、R2、R3Be each independently C3-C20 includes aryl
Or the substituent of heteroaryl.
In a further preferred embodiment, the heteroaryl contains N.
In a further preferred embodiment, the R1、R2、R3It is each independently following group：
In an embodiment still more preferably, the organic electroluminescent compounds are selected from following chemical combination
Thing：
There is provided a kind of OLED electronics containing above-mentioned organic electroluminescent compounds for the second aspect of the present invention
Transmit layer material.
There is provided a kind of OLED hairs containing above-mentioned organic electroluminescent compounds for the third aspect of the present invention
Photosphere material.
There is provided a kind of OLED containing above-mentioned organic electroluminescent compounds is empty for the fourth aspect of the present invention
Transmit layer material in cave.
There is provided a kind of OLED devices containing above-mentioned organic electroluminescent compounds for the fifth aspect of the present invention
Part.
With reference to specific embodiment, technical scheme is further explained and illustrated.
Embodiment 1
The synthesis of compound 1：
The preparation method of the compound 1 includes：
0.1mol intermediate As, 0.1mol intermediate Bs and 600mL tetrahydrochysene furan are added into reaction bulb
Mutter and 100ml water, and add 0.2mol potassium carbonate thereto, and add 0.5g tetra- (triphenyl) phosphine
Palladium, under nitrogen protection normal-temperature reaction 12 hours；Then, distilled water terminating reaction is added into reaction solution,
And extracted with ethanol/dichloromethane, salt washing separates organic layer, and revolving removes organic solvent, crude product mistake
Post, then purified with dichloromethane and ethyl alcohol recrystallization and obtain compound 1, yield 55%.
Compound 1 is characterized as below：
MS：551.2361
1H-NMR：1.66(6H)8.11(1H)7.97(1H)7.85(1H)7.35(1H)7.41(1H)
7.61(1H)7.28(1H)7.54(4H)7.48(2H)7.32(2H)7.21(1H)7.32(2H)
7.67(2H)7.63(1H)7.54(1H)。
Embodiment 2
The synthesis of compound 2：
The preparation method of the compound 2 includes：
0.1mol intermediate C, 0.1mol intermediate Bs and 600mL tetrahydrochysene furan are added into reaction bulb
Mutter and 100ml water, and add 0.2mol potassium carbonate thereto, and add 0.5g tetra- (triphenyl) phosphine
Palladium, under nitrogen protection normal-temperature reaction 12 hours；Then, distilled water terminating reaction is added into reaction solution,
And extracted with ethanol/dichloromethane, salt washing separates organic layer, and revolving removes organic solvent, crude product mistake
Post, then purified with dichloromethane and ethyl alcohol recrystallization and obtain compound 2, yield 45%.
Compound 2 is characterized as below：
MS：485.1892
1H-NMR：7.38(4H)7.74(4H)7.48(2H)7.32(2H)7.61(2H)7.58(4H)
7.37(2H)7.43(2H)7.30(1H)。
Embodiment 3
The synthesis of compound 3：
The preparation method of the compound 3 includes：
0.1mol intermediate As, 0.1mol intermediates D and 600mL tetrahydrochysene furan are added into reaction bulb
Mutter and 100ml water, and add 0.2mol potassium carbonate thereto, and add 0.5g tetra- (triphenyl) phosphine
Palladium, under nitrogen protection normal-temperature reaction 12 hours；Then, distilled water terminating reaction is added into reaction solution,
And extracted with ethanol/dichloromethane, salt washing separates organic layer, and revolving removes organic solvent, crude product mistake
Post, then purified with dichloromethane and ethyl alcohol recrystallization and obtain compound 3, yield 51%.
Compound 3 is characterized as below：
MS：617.2831
1H-NMR：1.66(12H)8.12(2H)7.96(2H)7.84(2H)7.35(2H)7.40(2H)
7.61(2H)7.28(2H)7.54(4H)7.48(2H)7.32(2H)7.21(1H)。
Embodiment 4
The synthesis of compound 4：
The preparation method of the compound 4 includes：
0.1mol intermediate C, 0.1mol intermediates D and 600mL tetrahydrochysene furan are added into reaction bulb
Mutter and 100ml water, and add 0.2mol potassium carbonate thereto, and add 0.5g tetra- (triphenyl) phosphine
Palladium, under nitrogen protection normal-temperature reaction 12 hours；Then, distilled water terminating reaction is added into reaction solution,
And extracted with ethanol/dichloromethane, salt washing separates organic layer, and revolving removes organic solvent, crude product mistake
Post, then purified with dichloromethane and ethyl alcohol recrystallization and obtain compound 4, yield 54%.
Compound 4 is characterized as below：
MS：551.2361
1H-NMR：1.68(6H)8.12(1H)7.98(1H)7.86(1H)7.37(1H)7.42(1H)
7.61(1H)7.32(1H)7.24(1H)7.56(4H)7.48(2H)7.32(2H)7.21(1H)
7.32(2H)7.67(2H)7.63(1H)7.54(1H)。
Application Example --- OLED
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minutes in isopropanol, and exposed to ultraviolet light
Lower 20-30 minutes, then handled 5-10 minutes with plasma.Then the ito substrate after processing is put into
Evaporated device.One layer of 30-50nm NPB is deposited first as hole transmission layer, followed by the steaming of luminescent layer
Plating, mixing evaporation, CBP, and 2--10% Ir (piq) 3, then evaporation 20-40nm Alq3 conducts
Electron transfer layer, is then deposited 0.5-2nmLiF again, and 100-200nm metal Al is finally deposited.
Application Example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minutes in isopropanol, and exposed to ultraviolet light
Lower 20-30 minutes, then handled 5-10 minutes with plasma.Then the ito substrate after processing is put into
Evaporated device.One layer of 30-50nm NPB is deposited first as hole transmission layer, followed by the steaming of luminescent layer
Plating, mixing evaporation compound CBP, and 2--10% Ir (piq) 3, then evaporation 20-40nm chemical combination
Thing 1, is then deposited 0.5-2nmLiF again, and 100-200nm metal Al is finally deposited.
Application Example 2
Change the Alq3 in comparative example into compounds 2, be used as electron transfer layer.
Application Example 3
Change the Alq3 in comparative example into compounds 3, be used as electron transfer layer.
Application Example 4
Change the Alq3 in comparative example into compounds 4, be used as electron transfer layer.
Application Example 5
Change the NPB in comparative example into compounds 1, be used as hole transmission layer.
Application Example 6
Change the NPB in comparative example into compounds 3, be used as hole transmission layer.
Application Example 7
Change the CBP in comparative example into compounds 2, be used as luminescent layer.
Application Example 8
Change the CBP in comparative example into compounds 4, be used as luminescent layer.
Wherein：
OLED is produced as follows：
Contrast Application Example：ITO/NPB/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 1：ITO/NPB/CBP：The compound 1/LiF/Al of Ir (piq) 3/；
Application Example 2：ITO/NPB/CBP：The compound 2/LiF/Al of Ir (piq) 3/；
Application Example 3：ITO/NPB/CBP：The compound 3/LiF/Al of Ir (piq) 3/；
Application Example 4：ITO/NPB/CBP：The compound 4/LiF/Al of Ir (piq) 3/；
Application Example 5：ITO/ compounds 1/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 6：ITO/ compounds 3/CBP：Ir(piq)3/Alq3/LiF/Al；
Application Example 7：ITO/NPB/ compounds 2：Ir(piq)3/Alq3/LiF/Al；
Application Example 8：ITO/NPB/ compounds 4：Ir(piq)3/Alq3/LiF/Al；
Under 1000nits, OLED result is as follows：
| Device | Cd/A | Driver Voltage |
| Contrast Application Example | 8cd/A | 4.7V |
| Application Example 1 | 15cd/A | 3.7V |
| Application Example 2 | 16cd/A | 4.0V |
| Application Example 3 | 18cd/A | 3.8V |
| Application Example 4 | 15cd/A | 4.1V |
| Application Example 5 | 16cd/A | 4.1V |
| Application Example 6 | 17cd/A | 4.3V |
| Application Example 7 | 14cd/A | 3.9V |
| Application Example 8 | 15cd/A | 4.2V |
Table 1
From upper table 1, compared with contrast Application Example common in the art, using of the present invention
Compound prepare OLED needed for driving voltage it is lower, and produce luminous flux it is bigger, therefore tool
There are more preferable luminescent properties.
The specific embodiment of the present invention is described in detail above, but it is intended only as example, and the present invention is simultaneously
It is not restricted to particular embodiments described above.To those skilled in the art, it is any to present invention progress
Equivalent modifications and substitute also all among scope of the invention.Therefore, the spirit and model of the present invention are not being departed from
Enclose lower made impartial conversion and change, all should be contained within the scope of the invention.
Claims (9)
1. a kind of organic electroluminescent compounds, it is characterised in that its structure is that the s-triazine shown in formula (I) spreads out
It is biological：
Wherein, R1、R2、R3It is each independently the substituent for including aryl or heteroaryl.
2. organic electroluminescent compounds according to claim 1, it is characterised in that the R1、R2、R3Respectively
From the substituent for including aryl or heteroaryl for independently being C3-C20.
3. organic electroluminescent compounds according to claim 2, it is characterised in that the heteroaryl contains N.
4. organic electroluminescent compounds according to claim 2, it is characterised in that the R1、R2、R3Respectively
From independently being following group：
5. organic electroluminescent compounds according to claim 4, it is characterised in that the organic electroluminescent
Compound is selected from following compound：
6. a kind of OLED electric transmissions of the organic electroluminescent compounds containing any one of claim 1-5
Layer material.
7. a kind of OLED luminescent layer materials of organic electroluminescent compounds containing any one of claim 1-5
Material.
8. a kind of OLED hole transports of the organic electroluminescent compounds containing any one of claim 1-5
Layer material.
9. a kind of OLED of the organic electroluminescent compounds containing any one of claim 1-5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610146865.8A CN107188859A (en) | 2016-03-15 | 2016-03-15 | A kind of organic electroluminescent compounds and the OLED containing the compound |
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| CN201610146865.8A CN107188859A (en) | 2016-03-15 | 2016-03-15 | A kind of organic electroluminescent compounds and the OLED containing the compound |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369669A (en) * | 2018-12-04 | 2019-02-22 | 烟台九目化学制品有限公司 | A kind of triazine biphenyl bithiophene miazines organic compound and its application |
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| CN101656301A (en) * | 2008-08-18 | 2010-02-24 | 三星移动显示器株式会社 | Organic light emitting diode employing luminescent efficiency improvement layer |
| CN103325950A (en) * | 2012-03-22 | 2013-09-25 | 陶氏环球技术有限责任公司 | Charge transport layers and films containing the same |
| CN104835921A (en) * | 2014-02-07 | 2015-08-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
| WO2015152633A1 (en) * | 2014-04-04 | 2015-10-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| CN107922359A (en) * | 2015-07-30 | 2018-04-17 | 默克专利有限公司 | Material for organic electroluminescence device |
-
2016
- 2016-03-15 CN CN201610146865.8A patent/CN107188859A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101656301A (en) * | 2008-08-18 | 2010-02-24 | 三星移动显示器株式会社 | Organic light emitting diode employing luminescent efficiency improvement layer |
| CN103325950A (en) * | 2012-03-22 | 2013-09-25 | 陶氏环球技术有限责任公司 | Charge transport layers and films containing the same |
| CN104835921A (en) * | 2014-02-07 | 2015-08-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent device |
| WO2015152633A1 (en) * | 2014-04-04 | 2015-10-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| CN107922359A (en) * | 2015-07-30 | 2018-04-17 | 默克专利有限公司 | Material for organic electroluminescence device |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369669A (en) * | 2018-12-04 | 2019-02-22 | 烟台九目化学制品有限公司 | A kind of triazine biphenyl bithiophene miazines organic compound and its application |
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