CN106478535A - A kind of material for being applied to OLED field - Google Patents
A kind of material for being applied to OLED field Download PDFInfo
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- CN106478535A CN106478535A CN201510551008.1A CN201510551008A CN106478535A CN 106478535 A CN106478535 A CN 106478535A CN 201510551008 A CN201510551008 A CN 201510551008A CN 106478535 A CN106478535 A CN 106478535A
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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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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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- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a kind of material for being applied to OLED field, it is characterised in that containing a kind of structure as led to the compound shown in formula (I)：(I)；Wherein, R is phenolic compound.Material of the present invention can apply to, in hole transmission layer in OLED, luminescent layer, electron transfer layer, finally give a kind of performance more preferably OLED.
Description
Technical field
The present invention relates to OLED field, more particularly to a kind of material for being applied to OLED field.
Background technology
TFT-LCD, as a kind of display screen, is a kind of display of non-spontaneous light, it is necessary to throw through backlight
Penetrate light, sequentially penetrate Polarizer in TFT-LCD panel, glass substrate, liquid crystal layer, colored filter,
The correlation spare part such as glass substrate, Polarizer, finally enters the eye imaging of people, reaches the function of display.?
In practical application, TFT-LCD display screen has the shortcomings that reaction rate is slow, power consumption, narrow viewing angle, be not enough to
Become perfect display screen.
OLED, as a kind of new Display Technique, with self luminous characteristic, adopts very thin organic material
Material coating and glass substrate are prepared.When there is electric current to pass through, these organic materials will light.At present,
The structure of the basic structure of OLED such as sandwich, total layer include hole transmission layer (HTL), light
Layer (EL) and electron transfer layer (ETL).When appropriate voltage is supplied power to, positive pole hole is with negative electrode electric charge just
Can combine in luminescent layer, light is produced, red, green and blue three primary colors are produced according to its formula is different, constitute basic
Color.As the characteristic of OLED is that oneself lights, therefore, visibility and brightness are all high, next to that voltage
Demand is low and power saving efficiency is high, adds fast, the lightweight, thickness of thin of reaction, and simple structure, cost are low, quilt
It is considered as one of product of 21 century most future.
Although it is true that the continuous expansion of OLED range of application, but still Shortcomings, and determine OLED
One of good and bad Fundamentals of performance or problem of materials, therefore, design and a kind of new OLED material of synthesis
Material occurs in actual application to overcome the shortcomings of which, is the emphasis in OLED research work.
Content of the invention
Based on above-mentioned background, this application provides a kind of material for being applied to OLED field, which includes one kind
The derivative compound of fluorenes, can apply to hole transmission layer in OLED, luminescent layer, electric transmission
In layer, a kind of performance more preferably OLED is finally given.
The theme of a first aspect of the present invention is a kind of material for being applied to OLED field, it is characterised in that
Containing a kind of structure as led to the compound shown in formula (I)：
Wherein, R is phenolic compound.
In one embodiment of the invention, the R is R1Or
Wherein, R1And R2For identical or different phenolic compound group.
Preferably, R1And R2It is containing 3-25 carbon or nitrogen compound, such as includes phenyl ring, naphthalene nucleus.
It is highly preferred that R1And R2Selected from following structure：
In one embodiment of the invention, the compound is selected from following structure：
The compound is prepared by Suzuki coupling reaction.
The theme of a second aspect of the present invention is the application of material described above：
A kind of OLED hole transmission layer containing material described above；
A kind of OLED luminescent layer containing material described above；
A kind of OLED electron transfer layer containing material described above；
A kind of OLED containing material described above.
Preferably, in the application of material described above, the material is preferably as ruddiness material of main part, green
Light material of main part and hole mobile material.
Specific embodiment
The invention provides a kind of material for being applied to OLED field, it is characterised in that containing a kind of structure
As led to the compound shown in formula (I)：
Wherein, R is phenolic compound.
In one embodiment of the invention, the R is R1Or
Wherein, R1And R2For identical or different phenolic compound group.
Preferably, R1And R2It is containing 3-25 carbon or nitrogen compound, such as includes phenyl ring, naphthalene nucleus.
It is highly preferred that R1And R2Selected from following structure：
In one embodiment of the invention, the compound is selected from following structure：
The compound is prepared by Suzuki coupling reaction.
Present invention also offers the application of material described above：
A kind of OLED hole transmission layer containing material described above；
A kind of OLED luminescent layer containing material described above；
A kind of OLED electron transfer layer containing material described above；
A kind of OLED containing material described above.
Preferably, in the application of material described above, the material is preferably as ruddiness material of main part, green
Light material of main part and hole mobile material.
Embodiment 1
1st, a kind of compound for being applied to OLED field, shown in its structure such as formula (I-1)：
2nd, the preparation method of the compound includes：
The toluene of 0.1mol intermediate A -1,0.1mol intermediate B -1 and 1000mL is added toward in reaction bulb,
Add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, the lower back flow reaction 24 of nitrogen protection
Hour, addition distilled water 500ml after the completion of reaction, cold filtration, extracted with dichloromethane, salt is washed, point
Go out organic layer, revolving removes organic solvent, and crude product crosses post, then is purified with dichloromethane and ethyl alcohol recrystallization
To compound (I-1)；
Wherein,
3rd, molecular weight characterization MS 549.2205
H-NMR：7.53 (2H), 7.62 (4H), 7.71 (4H), 7.46 (2H), 7.55 (4H), 7.68 (4H),
7.39 (1H), 7.32 (1H), 7.38 (1H), 7.61 (1H), 7.64 (1H), 7.41 (1H), 7.43 (1H)..
Embodiment 2
1st, a kind of compound for being applied to OLED field, shown in its structure such as formula (I-3)：
2nd, the preparation method of the compound includes：
The toluene of 0.1mol intermediate A -3,0.1mol intermediate B -3 and 1000mL is added toward in reaction bulb,
Add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, the lower back flow reaction 24 of nitrogen protection
Hour, addition distilled water 500ml after the completion of reaction, cold filtration, extracted with dichloromethane, salt is washed, point
Go out organic layer, revolving removes organic solvent, and crude product crosses post, then is purified with dichloromethane and ethyl alcohol recrystallization
To compound (I-3)；
Wherein,
3rd, molecular weight characterization MS 714.2783
H-NMR：7.53 (2H), 7.62 (4H), 7.71 (4H), 7.46 (2H), 7.55 (4H), 7.68 (4H),
7.39 (1H), 7.32 (1H), 7.38 (1H), 7.61 (1H), 7.64 (1H), 7.41 (1H), 7.43 (1H),
7.56 (2H), 7.64 (2H), 7.78 (1H), 7.69 (1H), 7.49 (1H).
Embodiment 3
1st, a kind of compound for being applied to OLED field, shown in its structure such as formula (I-5)：
2nd, the preparation method of the compound includes：
The toluene of 0.1mol intermediate A -5,0.1mol intermediate B -5 and 1000mL is added toward in reaction bulb,
Add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, the lower back flow reaction 24 of nitrogen protection
Hour, addition distilled water 500ml after the completion of reaction, cold filtration, extracted with dichloromethane, salt is washed, point
Go out organic layer, revolving removes organic solvent, and crude product crosses post, then is purified with dichloromethane and ethyl alcohol recrystallization
To compound (I-5)；
Wherein,
3rd, molecular weight characterization MS 627.2674
H-NMR：7.52 (2H), 7.61 (2H), 1.71 (3H), 2.45 (2H), 7.58 (2H), 7.77 (2H),
7.79 (2H), 7.54 (2H), 7.64 (2H), 8.32 (2H), 8.34 (2H), 7.64 (2H), 7.36 (4H),
7.38(4H).
Embodiment 4
1st, a kind of compound for being applied to OLED field, shown in its structure such as formula (I-6)：
2nd, the preparation method of the compound includes：
The toluene of 0.1mol intermediate A -6,0.1mol intermediate B -6 and 1000mL is added toward in reaction bulb,
Add potassium carbonate 200mmol and 1mmol catalyst Pd [P (C6H5)3]4, the lower back flow reaction 24 of nitrogen protection
Hour, addition distilled water 500ml after the completion of reaction, cold filtration, extracted with dichloromethane, salt is washed, point
Go out organic layer, revolving removes organic solvent, and crude product crosses post, then is purified with dichloromethane and ethyl alcohol recrystallization
To compound (I-6)；
Wherein,
3rd, molecular weight characterization MS 675.2674
H-NMR：7.52 (2H), 7.61 (2H), 7.79 (2H), 7.45 (2H), 7.31 (1H), 7.58 (2H),
7.77 (2H), 7.79 (2H), 7.54 (2H), 7.64 (2H), 8.32 (2H), 8.34 (2H), 7.64 (2H),
7.36 (4H), 7.38 (4H).
Application Example device
Contrast Application Example：
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minute in isopropanol, and is exposed to ultraviolet light
Lower 20-30 minute, subsequently 5-10 minute is processed with plasma.Subsequently the ito substrate after process is put into
Evaporated device.The NPB of one layer 30-50nm is deposited with first as hole transmission layer, followed by the steaming of luminescent layer
Plating, mixing evaporation, CBP, and the Ir (ppy) 3 of 5--10%, the Alq3 for being subsequently deposited with 20-40nm are made
For electron transfer layer, 0.5-2nmLiF is subsequently deposited with again, subsequently the metal Al of evaporation 100-200nm.
Application Example 1
Transparent anode electrode ito substrate is cleaned by ultrasonic 5-10 minute in isopropanol, and is exposed to ultraviolet light
Lower 20-30 minute, subsequently 5-10 minute is processed with plasma.Subsequently the ito substrate after process is put into
Evaporated device.The NPB of one layer 30-50nm is deposited with first as hole transmission layer, followed by the steaming of luminescent layer
Plating, mixing evaporation compound 1, and the Ir (ppy) 3 of 5--10%, the Alq3 of 20-40nm is subsequently deposited with,
Subsequently 0.5-2nmLiF is deposited with again, subsequently the metal Al of evaporation 100-200nm.
Application Example 2
CBP in comparative example is changed into compound 3, as luminescent layer.
Application Example 3
CBP in comparative example is changed into compound 5, as luminescent layer.
Application Example 4
CBP in comparative example is changed into compound 6, as luminescent layer.
Application Example 5
Alq3 in comparative example is changed into compound 1, as electron transfer layer.
Application Example 6
Alq3 in comparative example is changed into compound 3, as electron transfer layer.
Application Example 7
Alq3 in comparative example is changed into compound 5, as electron transfer layer.
Application Example 8
Alq3 in comparative example is changed into compound 6, as electron transfer layer.
Wherein：
OLED is produced as follows：
Contrast Application Example：ITO/NPB/CBP：Ir(ppy)3/Alq3/LiF/Al；
Application Example 1：ITO/NPB/ compound 1：Ir(ppy)3/Alq3/LiF/Al；
Application Example 2：ITO/NPB/ compound 3：Ir(ppy)3/Alq3/LiF/Al；
Application Example 3：ITO/NPB/ compound 5：Ir(ppy)3/Alq3/LiF/Al；
Application Example 4：ITO/NPB/ compound 6：Ir(ppy)3/Alq3/LiF/Al；
Application Example 5：ITO/NPB/CBP：3/ compound 1/LiF/Al of Ir (ppy)；
Application Example 6：ITO/NPB/CBP：3/ compound 3/LiF/Al of Ir (ppy)；
Application Example 7：ITO/NPB/CBP：3/ compound 5/LiF/Al of Ir (ppy)；
Application Example 8：ITO/NPB/CBP：3/ compound 6/LiF/Al of Ir (ppy).
Under 1000nits, OLED result is as follows：
| Device | Cd/A | Driver Voltage | CIEx | CIEy |
| Contrast Application Example | 10cd/A | 4.6V | 0.33 | 0.64 |
| Application Example 1 | 22cd/A | 4.1V | 0.33 | 0.64 |
| Application Example 2 | 17cd/A | 3.5V | 0.33 | 0.64 |
| Application Example 3 | 18cd/A | 3.7V | 0.33 | 0.64 |
| Application Example 4 | 14cd/A | 4.0V | 0.33 | 0.64 |
| Application Example 5 | 18cd/A | 3.9V | 0.33 | 0.64 |
| Application Example 6 | 16cd/A | 3.7V | 0.33 | 0.64 |
| Application Example 7 | 17cd/A | 3.8V | 0.33 | 0.64 |
| Application Example 8 | 18cd/A | 3.5V | 0.33 | 0.64 |
Specific embodiment to the present invention has been described in detail above, but which 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, any the present invention is carried out
Equivalent modifications and substitute also all among scope of the invention.Therefore, in the spirit without departing from the present invention and model
Enclose lower made impartial conversion and change, should all cover within the scope of the invention.
Claims (10)
1. a kind of material for being applied to OLED field, it is characterised in that containing a kind of structure as led to shown in formula (I)
Compound：
Wherein, R is phenolic compound.
2. material according to claim 1, it is characterised in that the R is R1OrWherein, R1And R2For identical or different phenolic compound group.
3. material according to claim 2, it is characterised in that R1And R2It is the change containing 3-25 carbon or nitrogen
Compound.
4. material according to claim 2, it is characterised in that R1And R2Comprising phenyl ring, naphthalene nucleus.
5. material according to claim 2, it is characterised in that R1And R2Selected from following structure：
6. material according to claim 1, it is characterised in that the compound is selected from following structure：
7. a kind of OLED hole transmission layer containing material described in any one in claim 1-6.
8. a kind of OLED luminescent layer containing material described in any one in claim 1-6.
9. a kind of OLED electron transfer layer containing material described in any one in claim 1-6.
10. a kind of OLED containing material described in any one in claim 1-6.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510551008.1A CN106478535A (en) | 2015-08-31 | 2015-08-31 | A kind of material for being applied to OLED field |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510551008.1A CN106478535A (en) | 2015-08-31 | 2015-08-31 | A kind of material for being applied to OLED field |
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Citations (7)
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|---|---|---|---|---|
| CN102918134A (en) * | 2009-08-10 | 2013-02-06 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103619833A (en) * | 2011-04-12 | 2014-03-05 | 罗门哈斯电子材料韩国有限公司 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| US20150060796A1 (en) * | 2013-08-27 | 2015-03-05 | Samsung Display Co., Ltd. | Organic light emitting device |
| US20150090962A1 (en) * | 2013-09-27 | 2015-04-02 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2015056993A1 (en) * | 2013-10-18 | 2015-04-23 | Rohm And Haas Electronic Materials Korea Ltd. | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same |
| KR101537500B1 (en) * | 2014-04-04 | 2015-07-20 | 주식회사 엘지화학 | Organic light emitting diode |
| CN104795503A (en) * | 2014-01-16 | 2015-07-22 | 三星显示有限公司 | Organic light-emitting device |
-
2015
- 2015-08-31 CN CN201510551008.1A patent/CN106478535A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102918134A (en) * | 2009-08-10 | 2013-02-06 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103619833A (en) * | 2011-04-12 | 2014-03-05 | 罗门哈斯电子材料韩国有限公司 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| US20150060796A1 (en) * | 2013-08-27 | 2015-03-05 | Samsung Display Co., Ltd. | Organic light emitting device |
| US20150090962A1 (en) * | 2013-09-27 | 2015-04-02 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2015056993A1 (en) * | 2013-10-18 | 2015-04-23 | Rohm And Haas Electronic Materials Korea Ltd. | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same |
| CN104795503A (en) * | 2014-01-16 | 2015-07-22 | 三星显示有限公司 | Organic light-emitting device |
| KR101537500B1 (en) * | 2014-04-04 | 2015-07-20 | 주식회사 엘지화학 | Organic light emitting diode |
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