CN106279148A - Promote OLED high temperature, the material of high current density performance and application thereof - Google Patents
Promote OLED high temperature, the material of high current density performance and application thereof Download PDFInfo
- Publication number
- CN106279148A CN106279148A CN201510268251.2A CN201510268251A CN106279148A CN 106279148 A CN106279148 A CN 106279148A CN 201510268251 A CN201510268251 A CN 201510268251A CN 106279148 A CN106279148 A CN 106279148A
- Authority
- CN
- China
- Prior art keywords
- compound
- oled
- deposited
- preparation
- following structure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
Abstract
The invention provides a kind of promote OLED high temperature, high current density performance material, it is characterised in that comprise the compound shown in a kind of formula 1: wherein: X1, X2 are the atom with mating capability or the H including N, O, S；R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.Present invention also offers the preparation method of a kind of described compound, the application of described material, a kind of device containing described material and preparation method thereof.The device that technique scheme occurs in actual application in order to solve OLED under high temperature, high current density, the problem such as the life-span of performance short, job insecurity.
Description
Technical field
The present invention relates to a kind of material, particularly relate to a kind of lifting OLED high temperature, high current density table
Existing material and application thereof.
Background technology
At present, display screen with TFT (Thin Film Transistor, TFT)-LCD is
Main, due to the display that it is non-self luminescence, it is therefore necessary to through backlight throw light, and sequentially penetrate
Polarizer in TFT-LCD panel, glass substrate, liquid crystal layer, colored filter, glass substrate, polarisation
The relevant 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 in actual application that reaction rate is slow, power consumption, narrow viewing angle
Etc. shortcoming, it is not enough to become perfect display screen.
Comparatively speaking, OLED is as a kind of novel flat panel display, and it is with traditional LCD display side
Formula is compared, it is not necessary to backlight, uses the thinnest coating of organic material and glass substrate, when there being electric current to pass through,
These organic materials will be luminous.Therefore, OLED has self-luminous, simple in construction, ultra-thin, response speed
Spend fast, wide viewing angle, low-power consumption and the characteristics such as Flexible Displays can be realized, achieving the biggest development in recent ten years
And progress, it is described as " illusion display ".
Wherein, CN103413893 discloses a kind of OLED, this OLED include substrate,
Transparent anode, hole injection layer, luminescent layer, electron injecting layer and negative electrode, wherein luminescent layer is by host fluorescence material
Material and the doping of object phosphor material form, and host fluorescence material uses the polyfluorene having hole and electron transporting groups concurrently
Class material.OLED provided by the present invention can effectively reduce hole and the potential barrier of electronics injection, tool
There are higher quantum efficiency and carrier transport ability.
Wherein, CN102185113 discloses a kind of OLED, and the maximum feature of this OLED is
A kind of organic material and a kind of transition metal oxide has only been selected in the middle of anode and negative electrode.Present invention utilizes
Organic material luminosity, engineering properties, thermal property；It is simultaneously to have to reduce only with a kind of organic material
The problem of aging of machine material, other functional layer uses metal-oxide to be the spy utilizing its stability and electric conductivity
Point.
It is true that although the continuous of OLED range of application expands, but still Shortcomings, and determine OLED
One of Fundamentals that performance is good and bad or problem of materials, therefore, design and synthesize a kind of novel OLED material
Material, to overcome its deficiency occurred in actual application, is the emphasis in OLED research work.
Summary of the invention
The device occurred in actual application for OLED under high temperature, high current density, performance
The problems such as life-span short, job insecurity, the invention provides a kind of lifting OLED high temperature, high electric current
The material of density performance, can be used for electron transfer layer, luminescent layer and hole transmission layer, the one obtained with this
OLED has good serviceability.
On the one hand, subject of the present invention be a kind of promote OLED high temperature, high current density performance material
Material, it is characterised in that comprise the compound shown in a kind of formula 1:
Wherein: X1, X2 are the atom with mating capability or the H including N, O, S；
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
In a preferred embodiment of the invention, R1, R2, R3 preferably are selected from following structure:
Wherein, R5 is selected from H base, alkyl, aromatic radical, aromatic radical.
In a preferred embodiment of the invention, described R5 preferably is selected from the group of following structure:
Wherein, X1, X2 are the atom with mating capability or the H including N, O, S.
In the another one preferred embodiment of the present invention, it is preferable that the compound shown in formula 1 is following knot
Structure:
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
In another preferred embodiment of the present invention, described compound preferably is selected from following structure:
Second aspect, subject of the present invention is the preparation method of a kind of compound described above, and its syntheti c route is:
I-1 isMidbody compound, with I-2 for even
Connect R1, R2, R3 midbody compound of-Br, reacting generating compound (I)；
Its preparation process includes:
Step 1: add the I-2 of I-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium three in a reservoir
Tert-butyl group phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: protection is heated to reflux 20-30 hour under compression ring border, then cools down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound.
Wherein it is preferred to, protection gas is nitrogen, and the time of being heated to reflux is 24 hours.
The third aspect, subject of the present invention is lifting OLED high temperature described above, high current density table
Existing material is in the application of electron transfer layer, luminescent layer and hole transmission layer.
Fourth aspect, subject of the present invention is that to comprise lifting OLED high temperature described above, high electric current close
The device of the material of degree performance, and preparation method thereof, including:
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently, obtain
Described device；Wherein, CBP Yu NPB is following structure:
Above-mentioned theme of the present invention, has advanced meaning in OLED field, described compound due to
What the structure of its uniqueness, especially B1 and B2 contained has the atom of mating capability, in actual application,
Metal complex can be formed, therefore can significantly improve high temperature lifetime, control moving of active metal ion
Move so that thus obtained device has under high temperature and high current density, the beneficial effect of life-span upgrading.
Detailed description of the invention
The invention provides a kind of promote OLED high temperature, high current density performance material, its feature
It is, comprises the compound shown in a kind of formula 1:
Wherein: X1, X2 are the atom with mating capability or the H including N, O, S；
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
In a preferred embodiment of the invention, R1, R2, R3 preferably are selected from following structure:
Wherein, R5 is selected from H base, alkyl, aromatic radical, aromatic radical.
In a preferred embodiment of the invention, described R5 preferably is selected from the group of following structure:
Wherein, X1, X2 are the atom with mating capability or the H including N, O, S.
In the another one preferred embodiment of the present invention, it is preferable that the compound shown in formula 1 is following knot
Structure:
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
In another preferred embodiment of the present invention, described compound preferably is selected from following structure:
The present invention breathes out the preparation method additionally providing a kind of compound described above, and its syntheti c route is:
I-1 isMidbody compound, with I-2 for even
Connect R1, R2, R3 midbody compound of-Br, reacting generating compound (I)；
Its preparation process includes:
Step 1: add the I-2 of I-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium three in a reservoir
Tert-butyl group phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: protection is heated to reflux 20-30 hour under compression ring border, then cools down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound.
Wherein it is preferred to, protection gas is nitrogen, and the time of being heated to reflux is 24 hours.
Present invention also offers lifting OLED high temperature described above, the material of high current density performance exists
The application of electron transfer layer, luminescent layer and hole transmission layer.
Present invention also offers and comprise lifting OLED high temperature described above, the material of high current density performance
The device of material, and preparation method thereof, including:
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently, obtain
Described device；Wherein, CBP Yu NPB is following structure:
Embodiment 1
1, the preparation method of compound (I1)
Step 1: add the I1-2 of I1-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium in a reservoir
Tri-butyl phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: be heated to reflux under nitrogen environment 24 hours, then cool down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound I1.
Molecular weight characterization MS 460.1688；
H-NMR:9.23 (2H), 9.03 (2H), 8.42 (2H), 8.30 (2H), 8.21 (2H), 8.17 (1H),
7.92 (4H), 7.81 (1H), 7.65 (1H).
2, the device containing above-claimed cpd
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I1), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently,
To described device.
Embodiment 2
1, the preparation method of compound (I2)
Step 1: add the I2-2 of I2-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium in a reservoir
Tri-butyl phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: be heated to reflux under nitrogen environment 24 hours, then cool down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound I2.
Molecular weight characterization MS 420.1531；
H-NMR:9.23 (2H), 9.03 (2H), 8.42 (1H), 8.30 (2H), 8.21 (2H), 8.17 (2H),
7.92 (2H), 7.81 (2H), 7.65 (2H).
2, the device containing above-claimed cpd
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I2), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently,
To described device.
Embodiment 3
1, the preparation method of compound (I3)
Step 1: add the I3-2 of I3-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium in a reservoir
Tri-butyl phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: be heated to reflux under nitrogen environment 24 hours, then cool down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound I3.
Molecular weight characterization MS 482.1783；
H-NMR:9.23 (2H), 9.03 (2H), 8.42 (2H), 8.30 (2H), 8.21 (2H), 8.17 (2H),
7.92 (2H), 7.81 (2H), 7.65 (2H), 7.55 (2H), 7.42 (2H).
2, the device containing above-claimed cpd
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I3), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently,
To described device.
Embodiment 4
1, the preparation method of compound (I4)
Step 1: add the I4-2 of I4-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium in a reservoir
Tri-butyl phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: be heated to reflux under nitrogen environment 24 hours, then cool down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound I4.
Molecular weight characterization MS 422.1531；
H-NMR:9.23 (2H), 9.03 (2H), 8.42 (1H), 8.30 (2H), 8.21 (2H), 8.17 (2H),
7.92 (2H), 7.81 (2H).
2, the device containing above-claimed cpd
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I4), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently,
To described device.
Embodiment 5
1, the preparation method of compound (I5)
Step 1: add the I5-2 of I5-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium in a reservoir
Tri-butyl phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: be heated to reflux under nitrogen environment 24 hours, then cool down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound I5.
Molecular weight characterization MS 427.1688；
H-NMR:9.23 (2H), 9.03 (2H), 8.42 (2H), 8.30 (2H), 8.21 (2H), 8.17 (1H),
7.92 (2H), 7.81 (1H), 7.65 (1H), 8.34 (2H), 8.26 (2H).
2, the device containing above-claimed cpd
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I5), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently,
To described device.
Comparative example
Device containing Alq3
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with 20-40nm's subsequently
Alq3, is deposited with 0.5-2nmLiF the most again, is deposited with the metal Al of 100-200nm subsequently, obtains described device.
Device comparison and detection result
Embodiment 1:ITO/NPB/CBP:Ir (ppy) 3/ compound (I1)/LiF/Al；
Embodiment 2:ITO/NPB/CBP:Ir (ppy) 3/ compound (I2)/LiF/Al；
Embodiment 3:ITO/NPB/CBP:Ir (ppy) 3/ compound (I3)/LiF/Al；
Embodiment 4:ITO/NPB/CBP:Ir (ppy) 3/ compound (I4)/LiF/Al；
Embodiment 5:ITO/NPB/CBP:Ir (ppy) 3/ compound (I5)/LiF/Al；
Comparative example: ITO/NPB/CBP:Ir (ppy) 3/Alq3/LiF/Al.
Under 1000nits, OLED result is as follows:
Lifetime tests under 3000nits, at 50-80 degree Celsius of lower high temperature test
| Device | Cd/A | Driver Voltage | CIEx | CIEy | T90(hours) |
| Comparative example | 10cd/A | 4.6V | 0.33 | 0.64 | 50 |
| 1 | 20cd/A | 4.5V | 0.33 | 0.64 | 123 |
| 2 | 15cd/A | 4.4V | 0.33 | 0.64 | 145 |
| 3 | 19cd/A | 4.3V | 0.33 | 0.64 | 113 |
| 4 | 15cd/A | 4.5V | 0.33 | 0.64 | 127 |
| 5 | 12cd/A | 4.7V | 0.33 | 0.64 | 138 |
Being described in detail the specific embodiment of the present invention above, but it is intended only as example, the present invention is also
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 the most all among scope of the invention.Therefore, without departing from the spirit of the present invention and model
Enclose lower made impartial conversion and amendment, all should contain within the scope of the invention.
Claims (9)
1. one kind promotes OLED high temperature, the material of high current density performance, it is characterised in that comprise one
Compound shown in formula 1:
Wherein: X1, X2 are the atom with mating capability or the H including N, O, S；
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
Material the most according to claim 1, it is characterised in that R1, R2, R3 are selected from following structure:
Wherein, R5 is selected from H base, alkyl, aromatic radical, aromatic radical.
Material the most according to claim 2, it is characterised in that described R5 is selected from the group of following structure:
Wherein, X1, X2 are the atom with mating capability or the H including N, O, S.
Material the most according to claim 1, it is characterised in that the compound shown in formula 1 is following structure:
R1, R2, R3 are polycyclic aromatic hydrocarbyl group or H.
Material the most according to claim 1, it is characterised in that described compound is selected from following structure:
6. the preparation method of a compound as claimed in claim 1, it is characterised in that its syntheti c route is:
I-1 isMidbody compound, with I-2 for even
Connect R1, R2, R3 midbody compound of-Br, reacting generating compound (I)；
Its preparation process includes:
Step 1: add the I-2 of I-1,0.1mol of 0.1mol, potassium tert-butoxide, palladium three in a reservoir
Tert-butyl group phosphine tetrafluoroborate and the toluene of 1000mL；
Step 2: protection is heated to reflux 20-30 hour under compression ring border, then cools down；
Step 3: remove toluene, adds dichloromethane, washing, is dried, and thick product crosses post, then uses dichloromethane
Alkane and ethyl alcohol recrystallization purification obtain described compound.
Preparation method the most according to claim 6, it is characterised in that described protection gas is nitrogen；Described heating
Return time is 24 hours.
8. an OLED, at least includes electron transfer layer, luminescent layer and hole transmission layer, and its feature is,
Described electron transfer layer, luminescent layer and hole transmission layer include material as claimed in claim 1.
9. the preparation method of a device as claimed in claim 8, it is characterised in that including:
Step 1: by transparent anode electrode ito substrate ultrasonic cleaning 5-10 minute in isopropanol, and expose
20-30 minute under ultraviolet light, process 5-10 minute with plasma subsequently；
Step 2:, the ito substrate after processing puts into evaporated device, first one layer of 30-50nm's of evaporation
NPB, then mixes the Ir (ppy) 3 of evaporation, CBP, and 5--10%, is deposited with the institute of 20-40nm subsequently
State compound (I), be deposited with 0.5-2nmLiF the most again, be deposited with the metal Al of 100-200nm subsequently, obtain
Described device；Wherein, CBP Yu NPB is following structure:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510268251.2A CN106279148A (en) | 2015-05-22 | 2015-05-22 | Promote OLED high temperature, the material of high current density performance and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510268251.2A CN106279148A (en) | 2015-05-22 | 2015-05-22 | Promote OLED high temperature, the material of high current density performance and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106279148A true CN106279148A (en) | 2017-01-04 |
Family
ID=57633212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510268251.2A Pending CN106279148A (en) | 2015-05-22 | 2015-05-22 | Promote OLED high temperature, the material of high current density performance and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106279148A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
| CN107915732A (en) * | 2017-12-08 | 2018-04-17 | 北京鼎材科技有限公司 | Naphthyridines substitutes anthracene derivant and organic electroluminescence device |
| CN108165264A (en) * | 2018-02-11 | 2018-06-15 | 上海升翕光电科技有限公司 | A kind of organic luminescent compounds and its preparation method and application |
| CN111253393A (en) * | 2020-02-05 | 2020-06-09 | 北京大学 | Long-life triplet exciton confinement material and application thereof in OLED (organic light emitting diode) device |
| US20210253947A1 (en) * | 2019-05-31 | 2021-08-19 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Blue thermally activated delayed fluorescence material, synthesis method thereof, and use thereof |
| CN113444112A (en) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | Heterocyclic compounds and their use in organic electroluminescent devices |
| CN114929687A (en) * | 2019-12-10 | 2022-08-19 | 诺瓦尔德股份有限公司 | Acridine compound, and organic semiconductor layer, organic electronic device and display device comprising same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1405893A1 (en) * | 2001-06-06 | 2004-04-07 | Sanyo Electric Co., Ltd. | Organic electroluminescence device and luminance material |
| CN101258221A (en) * | 2005-09-08 | 2008-09-03 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| CN101529611A (en) * | 2006-10-16 | 2009-09-09 | 东丽株式会社 | Light-emitting device |
| CN102473848A (en) * | 2009-12-21 | 2012-05-23 | 出光兴产株式会社 | Organic electroluminescent element using pyrene derivative |
-
2015
- 2015-05-22 CN CN201510268251.2A patent/CN106279148A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1405893A1 (en) * | 2001-06-06 | 2004-04-07 | Sanyo Electric Co., Ltd. | Organic electroluminescence device and luminance material |
| CN101258221A (en) * | 2005-09-08 | 2008-09-03 | 东丽株式会社 | Light-emitting device material and light-emitting device |
| CN101529611A (en) * | 2006-10-16 | 2009-09-09 | 东丽株式会社 | Light-emitting device |
| CN102473848A (en) * | 2009-12-21 | 2012-05-23 | 出光兴产株式会社 | Organic electroluminescent element using pyrene derivative |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
| CN107915732A (en) * | 2017-12-08 | 2018-04-17 | 北京鼎材科技有限公司 | Naphthyridines substitutes anthracene derivant and organic electroluminescence device |
| CN107915732B (en) * | 2017-12-08 | 2019-06-21 | 北京鼎材科技有限公司 | Naphthyridines replaces anthracene derivant and organic electroluminescence device |
| CN108165264A (en) * | 2018-02-11 | 2018-06-15 | 上海升翕光电科技有限公司 | A kind of organic luminescent compounds and its preparation method and application |
| US20210253947A1 (en) * | 2019-05-31 | 2021-08-19 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Blue thermally activated delayed fluorescence material, synthesis method thereof, and use thereof |
| US11898074B2 (en) * | 2019-05-31 | 2024-02-13 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Blue thermally activated delayed fluorescence material, synthesis method thereof, and use thereof |
| CN114929687A (en) * | 2019-12-10 | 2022-08-19 | 诺瓦尔德股份有限公司 | Acridine compound, and organic semiconductor layer, organic electronic device and display device comprising same |
| CN111253393A (en) * | 2020-02-05 | 2020-06-09 | 北京大学 | Long-life triplet exciton confinement material and application thereof in OLED (organic light emitting diode) device |
| CN111253393B (en) * | 2020-02-05 | 2022-01-25 | 北京大学 | Long-life triplet exciton confinement material and application thereof in OLED (organic light emitting diode) device |
| CN113444112A (en) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | Heterocyclic compounds and their use in organic electroluminescent devices |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106279148A (en) | Promote OLED high temperature, the material of high current density performance and application thereof | |
| US8409728B2 (en) | Organic electroluminescence device | |
| JP2008244430A (en) | Image display system | |
| CN103922995A (en) | Organic electroluminescence device and display device | |
| CN101747262A (en) | Electron transporting-injection material and organic electroluminescent device using the same | |
| CN105694859B (en) | organic electronic luminescent material | |
| CN106699753A (en) | Compound and application thereof | |
| Cao et al. | Electroplex emission from a layer of a mixture of a europium complex and tris (8-quinolinolato) aluminum | |
| CN106316925A (en) | Organic electroluminescence compound and application thereof | |
| CN103700775A (en) | Organic electroluminescence device and preparation method thereof | |
| Shi et al. | High-performance inverted organic light-emitting diodes with extremely low efficiency roll-off using solution-processed ZnS quantum dots as the electron injection layer | |
| CN106800526A (en) | A kind of electroluminescent organic material and its application with cyclic diketones as core | |
| CN104078623B (en) | A kind of organic electroluminescence device, organic electroluminescence display device and method of manufacturing same | |
| CN105646459A (en) | Compound and preparation method and application thereof | |
| CN105884810A (en) | Compound and material and organic electroluminescent device comprising same | |
| CN109970804B (en) | Organic metal iridium complex and application thereof | |
| CN105789481B (en) | Organic electroluminescence device | |
| KR20110051747A (en) | Organic light emitting diode device | |
| CN105646458A (en) | Compound and preparation method and application thereof | |
| Zhang et al. | Study on energy relation between blue and red emissive layer of organic light-emitting diodes by inserting spacer layer | |
| CN107188860B (en) | Compound applied to OLED field | |
| CN106318378A (en) | Organic electroluminescent compound and application thereof | |
| CN106318379A (en) | Organic electroluminescent compound and application thereof | |
| CN106299142A (en) | There is compound of heat stability and hole stability and its preparation method and application | |
| CN105646479B (en) | A kind of compound and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170104 |