CN110467642A - Red phosphorescent compound and the organic electroluminescence device for using the compound - Google Patents
Red phosphorescent compound and the organic electroluminescence device for using the compound Download PDFInfo
- Publication number
- CN110467642A CN110467642A CN201910682406.5A CN201910682406A CN110467642A CN 110467642 A CN110467642 A CN 110467642A CN 201910682406 A CN201910682406 A CN 201910682406A CN 110467642 A CN110467642 A CN 110467642A
- Authority
- CN
- China
- Prior art keywords
- organic electroluminescence
- electroluminescence device
- layer
- phosphorescent compound
- red phosphorescent
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention discloses red phosphorescent compound and use the organic electroluminescence device of the compound, in the organic electroluminescence device for including the anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and the cathode that are sequentially deposited each other, dopant of the phosphorescent compound represented by following formula I as luminescent layer is can be used in organic electroluminescence device:Wherein, R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from H, C1~C6 alkyl, one kind of C5~C8 naphthenic base.The red phosphorescence material has high efficiency, high color purity and narrow spectrum effects.
Description
Technical field
The present invention relates to a kind of organic electroluminescence devices, in particular to red phosphorescent compound and use its
Organic electroluminescence device.Particularly, the present invention relates to the red of the dopant for the luminescent layer for being used as organic electroluminescence device
Phosphor.
Background technique
In recent years, as the size of display device is increasing, the flat-panel monitor for occupying less space is had increasing need for
Part.The flat-panel display device includes organic electroluminescence device, also referred to as Organic Light Emitting Diode (OLED).Organic electroluminescence hair
With the development of huge speed, many prototypes have been disclosed in the technology of optical device.
When charge is injected into the organic layer formed between electron injection electrode (cathode) and hole injecting electrode (anode)
When, organic electroluminescence device shines.More specifically, shine when electrons and holes form a clock synchronization, newly generated electron hole
To decaying.Organic electroluminescence device can be formed in flexible transparent substrate such as plastics.It can also be shown than plasma
It is driven under the lower voltage of required voltage (voltage for being less than or equal to 10V) in plate or inorganic EL (EL) display
Organic electroluminescence device.Organic electroluminescence device is advantageous in that, is consumed compared with other display devices less
Energy and excellent color be provided show.Moreover, because organic electroluminescence device using three colors (it is i.e. green, it is blue and red
Color), it can be with reproduced picture, so organic electroluminescence device is broadly considered the next-generation face that can reproduce clear image
Color display device.
The process description for manufacturing Organic Light Emitting Diode (EL) device is as follows:
(1) on the transparent substrate by anode material coating.Generally make anode material using tin indium oxide (ITO).
(2) deposition of hole implanted layer (HIL) on anode material.Hole injection layer is by with 10 nanometers (nm) to 30 (nm)
Copper phthalocyanine (CuPc) layer of thickness is formed.
(3) hollow transport layer (HTL) is then deposited.Hole transmission layer is mainly by 4,4 '-bis- [N- (1- naphthalene)-N- phenylaminos
Base] biphenyl (NPB) formation, it is first handled with vacuum evaporation, is then applied to the thickness with 30 nanometers (nm) to 60 nanometers (nm).
(4) hereafter, organic luminous layer is formed.At this time, if it is desired, dopant can be added.In the case where green light,
Organic luminous layer is generally by being evaporated in vacuo to three (8-hydroxyquinoline acid) aluminium with 30 nanometers (nm) to 60 nanometers (nm) thickness
(Alq3) it is formed.And it uses, MQD (N- methyl quinacridine copper) is used as dopant (or impurity).
(5) electron transfer layer (ETL) and electron injecting layer (EIL) are sequentially formed on organic luminous layer, or in organic hair
Electron injection/transport layer is formed on photosphere.In the case where green light, the Alq3 of step (4) has excellent electron-transport energy
Power.Therefore, it is not necessary to which ground needs electron injection and transport layer.
(6) last coated cathode layer, over the entire structure coat protective layer.
According to the method for forming luminescent layer in said structure, determines and issue (or display) indigo plant respectively, it is green, red color
Luminescent device.As luminescent material, exciton is formed by the recombination of the electrons and holes from each electrode injection.Singlet exciton
Emit fluorescence, triplet excitons emit phosphorescence.The singlet exciton for emitting fluorescence has 25% formation possibility, and emits phosphorus
The triplet excitons of light have 75% formation possibility.Therefore, compared with singlet exciton, triplet excitons provide bigger
Luminous efficiency.In such phosphor material, red phosphorescence material can have bigger luminous efficiency than fluorescent material.Cause
This, as improve organic electroluminescence device efficiency an important factor for, red phosphorescence material is being widely studied.
When using such phosphorescene materials, high-luminous-efficiency, high color purity and extended durability are needed.Most especially
Ground increases (i.e. the X value of cie color coordinate becomes much larger) with excitation purity when using red phosphorescence material, it is seen that and degree reduces,
So as to cause being difficult to provide high-luminous-efficiency.Therefore, it is necessary to develop can provide excellent chromaticity coordinate (the CIE excitation purity of X=
0.63 or more), the red phosphorescence material of the luminous efficiency of raising and extended durability.
Summary of the invention
To solve described problem the object of the present invention is to provide red phosphorescent compound and using the red phosphorus
The organic electroluminescence device of optical compounds, which substantially obviate the limitation and disadvantage due to the relevant technologies caused by one or
Multiple problems.
To solve described problem another object of the present invention is to by the way that formula (I) compound represented to be incorporated into
Dopant is used as in the luminescent layer of organic electroluminescence device, so that providing has high color purity, high brightness and long wearing
Organic electroluminescence device.
It can achieve the purpose of the present invention by providing red phosphorescent compound shown in following formula (I).
Red phosphorescent compound represented by a kind of following formula (I):
Wherein, R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from H, C1~C6 alkyl, one kind of C5~C8 naphthenic base.
Further, C1~C6 alkyl or C5~C8 naphthenic base be selected from methyl, ethyl, propyl, isopropyl, butyl,
One of isobutyl group, tert-butyl, n-pentyl, cyclopenta and cyclohexyl.
Further, C1~C6 alkyl or the hydrogen atom of C5~C8 naphthenic base are all replaced D-atom.
Further, the La group is selected from one of following structural:
Further, the red phosphorescent compound, wherein formula (I) is any of following structural: a:
In another aspect of the invention, the anode including being sequentially deposited each other, hole injection layer, hole transport are provided
Layer, luminescent layer, electron transfer layer, the organic electroluminescence device of electron injecting layer and cathode, the wherein organic electroluminescence
Dopant of any of the above-mentioned phosphorescent compound as luminescent layer can be used in part.
The main body material of any one of Al and Zn metal complex and carbazole derivates as luminescent layer may be used herein
Material, the amount ranges of dopant can be in 0.1%~50% range of weight ratio.When the amount of the dopant used is in above range
When interior, efficiency of the invention can be improved.And the ligand of every kind of Al and Zn metal complex may include quinolyl, biphenyl
Base, isoquinolyl, phenyl, methylquinoline base, dimethyl quinoline base, dimethyl-isoquinolyl, wherein carbazole derivates can wrap
Include CBP.
Detailed description of the invention
Fig. 1 illustrates to indicate to increase (becoming much larger with the X value of chromaticity coordinate) with the excitation purity of organic electroluminescence device
The figure that visibility reduces.
Fig. 2 illustrates compound copper (II) phthalocyanine (CuPc) used in embodiments of the invention, NPB, (btp) 2Ir
(acac), the structural formula of Alq3 and BAlq.
Specific embodiment
In detail below referring to the preferred embodiments of the invention, their example is instantiated in attached drawing.
The method to form red phosphorescent compound according to the present invention is described below.
Form example
1. the synthesis of intermediate Sub-1
Under nitrogen protection, 1- chlorine isoquinolin (10.0g, 61.1mmol) is added into there-necked flask, 3,5- dimethyl benzene boron
Sour (11.0g, 73.3mmol), 2M- potassium carbonate (120mL) are dissolved in tetrahydrofuran (120mL).Nitrogen is replaced 30 minutes, is added
Catalyst tetra-triphenylphosphine palladium (5mol%).Reaction system is warming up to 80 DEG C, is stirred at reflux 12 hours.It is cooled to room temperature, adds
Water quenching reaction, extracts reaction solution with ethyl acetate and saturated salt solution.With saturated common salt water washing two to three times, take organic
Phase.It is concentrated after organic phase anhydrous magnesium sulfate drying.Intermediate Sub-1 can be obtained by silica gel column chromatography separating-purifying
(10.4g, yield 73%).LC-MS:M/Z 234.3(M+H)+
2. the synthesis of intermediate Sub-2
Under nitrogen protection, the chloro- 6- propyl isoquinolin (10.0g, 48.6mmol) of 1-, 3,5- diformazan are added into there-necked flask
Base phenyl boric acid (8.8g, 58.3mmol), 2M- potassium carbonate (120mL) are dissolved in tetrahydrofuran (120mL).Nitrogen is replaced 30 minutes,
It is added catalyst tetra-triphenylphosphine palladium (5mol%).Reaction system is warming up to 80 DEG C, is stirred at reflux 12 hours.It is cooled to room
Temperature adds water quenching reaction, extracts reaction solution with ethyl acetate and saturated salt solution.With saturated common salt water washing two to three times, take
Organic phase.It is concentrated after organic phase anhydrous magnesium sulfate drying.Intermediate Sub-2 can be obtained by silica gel column chromatography separating-purifying
(9.4g, yield 70%).LC-MS:M/Z 276.4(M+H)+
3. the synthesis of intermediate Sub-3
Under nitrogen protection, the chloro- 6- isopropyl quinoline (10.0g, 48.6mmol) of 1-, 3,5- bis- are added into there-necked flask
Methylphenylboronic acid (8.8g, 58.3mmol), 2M- potassium carbonate (120mL) are dissolved in tetrahydrofuran (120mL).Nitrogen replaces 30 points
Clock is added catalyst tetra-triphenylphosphine palladium (5mol%).Reaction system is warming up to 80 DEG C, is stirred at reflux 12 hours.It is cooled to
Room temperature adds water quenching reaction, extracts reaction solution with ethyl acetate and saturated salt solution.It is arrived three times with saturated common salt water washing two,
Take organic phase.It is concentrated after organic phase anhydrous magnesium sulfate drying.Intermediate Sub-3 can be obtained by silica gel column chromatography separating-purifying
(9.6g, yield 72%).LC-MS:M/Z 276.4(M+H)+
4. the synthesis of intermediate Sub-4
Under nitrogen protection, the chloro- 6- isobutyl group isoquinolin (10.0g, 45.5mmol) of 1-, 3,5- bis- are added into there-necked flask
Methylphenylboronic acid (8.2g, 54.6mmol), 2M- potassium carbonate (120mL) are dissolved in tetrahydrofuran (120mL).Nitrogen replaces 30 points
Clock is added catalyst tetra-triphenylphosphine palladium (5mol%).Reaction system is warming up to 80 DEG C, is stirred at reflux 12 hours.It is cooled to
Room temperature adds water quenching reaction, extracts reaction solution with ethyl acetate and saturated salt solution.It is arrived three times with saturated common salt water washing two,
Take organic phase.It is concentrated after organic phase anhydrous magnesium sulfate drying.Intermediate Sub-4 can be obtained by silica gel column chromatography separating-purifying
(9.0g, yield 68%).LC-MS:M/Z 290.4(M+H)+
5. the synthesis of dichloro crosslinking Dimer Complex
By the monohydrate (4.0g, 13.4mmol) of iridous chloride, intermediate Sub-1 (6.9g, 29.5mmol) and diethyl
The ratio of alcohol list ether and distilled water is the mixed solution of 3/1 (120mL/40mL), is added in two mouthfuls of dry round-bottomed flasks, adds
Hot back flow reaction 24 hours, is then added suitable distilled water, then the solid of precipitation is filtered, and with methanol and petroleum ether
Solid obtains dichloro crosslinking Dimer Complex (5.7g, yield 61%).LC-MS:M/Z 1385.5(M+H)+
The synthesis of 6.RD-004
Dichloro is crosslinked Dimer Complex (3.0g, 2.2mmol), 3,7- diethyl -3,7- dimethyl -4,6- diketone
(1.6g, 6.5mmol), natrium carbonicum calcinatum (1.1g, 10.8mmol) and cellosolvo 80mL are added in twoport round-bottomed flask,
Then heating reflux reaction 6 hours stop heating, are down to room temperature, suitable distilled water is added, filters out solid.Solid is molten
Solution in methylene chloride, crosses short column of silica gel.Solvent is removed at reduced pressure conditions, and the solid being concentrated to get successively uses methanol and petroleum
Ether washing, obtains RD-004 (2.5g, yield 65%) required product.LC-MS:M/Z 897.2(M+H)+
7. the synthesis of dichloro crosslinking Dimer Complex
By the monohydrate (4g, 13.4mmol) of iridous chloride, intermediate Sub-2 (8.1g, 29.5mmol) and diethanol
The ratio of single ether and distilled water is the mixed solution of 3/1 (120mL/40mL), is added in two mouthfuls of dry round-bottomed flasks, is heated
Back flow reaction 24 hours, suitable distilled water is then added, then the solid of precipitation is filtered, and solid with methanol and petroleum ether
Body obtains dichloro crosslinking Dimer Complex (6.0g, yield 58%).LC-MS:M/Z 1553.9(M+H)+
The synthesis of 8.RD-055
Dichloro is crosslinked Dimer Complex (3.0g, 1.9mmol), 3,7- diethyl -3,7- dimethyl -4,6- diketone
(1.4g, 5.8mmol), natrium carbonicum calcinatum (1.0g, 9.7mmol) and cellosolvo 80mL are added in twoport round-bottomed flask,
Then heating reflux reaction 6 hours stop heating, are down to room temperature, suitable distilled water is added, filters out solid.Solid is molten
Solution in methylene chloride, crosses short column of silica gel.Solvent is removed at reduced pressure conditions, and the solid being concentrated to get successively uses methanol and petroleum
Ether washing, obtains RD-055 (2.4g, yield 63%) required product.LC-MS:M/Z 981.4(M+H)+
9. the synthesis of dichloro crosslinking Dimer Complex
By the monohydrate (4g, 13.4mmol) of iridous chloride, intermediate Sub-3 (8.1g, 29.5mmol) and diethanol
The ratio of single ether and distilled water is the mixed solution of 3/1 (120mL/40mL), is added in two mouthfuls of dry round-bottomed flasks, is heated
Back flow reaction 24 hours, suitable distilled water is then added, then the solid of precipitation is filtered, and solid with methanol and petroleum ether
Body obtains dichloro crosslinking Dimer Complex (6.2g, yield 60%).LC-MS:M/Z 1553.9(M+H)+
The synthesis of 10.RD-081
Dichloro is crosslinked Dimer Complex (3g, 1.9mmol), 3,7- diethyl -3,7- dimethyl -4,6- diketone (1.4g,
5.8mmol), natrium carbonicum calcinatum (1.0g, 9.7mmol) and cellosolvo 80mL are added in twoport round-bottomed flask, then plus
Hot back flow reaction 6 hours stops heating, is down to room temperature, suitable distilled water is added, filters out solid.Solid is dissolved in two
In chloromethanes, short column of silica gel is crossed.Solvent is removed at reduced pressure conditions, and the solid being concentrated to get successively is washed with methanol and petroleum ether
It washs, obtains RD-081 (2.4g, yield 63%) required product.LC-MS:M/Z 981.4(M+H)+
11. the synthesis of dichloro crosslinking Dimer Complex
By the monohydrate (4g, 13.4mmol) of iridous chloride, intermediate Sub-4 (8.5g, 29.5mmol) and diethanol
The ratio of single ether and distilled water is the mixed solution of 3/1 (120mL/40mL), is added in two mouthfuls of dry round-bottomed flasks, is heated
Back flow reaction 24 hours, suitable distilled water is then added, then the solid of precipitation is filtered, and solid with methanol and petroleum ether
Body obtains dichloro crosslinking Dimer Complex (5.8g, yield 54%).LC-MS:M/Z 1610.0(M+H)+
The synthesis of 12.RD-107
Dichloro is crosslinked Dimer Complex (3g, 1.9mmol), 3,7- diethyl -3,7- dimethyl -4,6- diketone is anhydrous
Sodium carbonate (1.0g, 9.3mmol) and cellosolvo 80mL are added in twoport round-bottomed flask, and then heating reflux reaction 6 is small
When, stop heating, is down to room temperature, suitable distilled water is added, filters out solid.In methylene chloride by solid dissolution, silicon is crossed
Glue short column.Solvent is removed at reduced pressure conditions, and the solid being concentrated to get successively uses methanol and petroleum ether, obtains RD-107
(2.2g, yield 58%) required product.LC-MS:M/Z 1009.4(M+H)+
The example of preferred embodiment described below is to describe the present invention.It will be apparent that the present invention not only office
It is limited to proposed embodiment.
Embodiment 1
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass
Substrate.The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6 support.Hereafter, on an ito substrate with WithThe layer for sequentially forming organic substance.At 0.9 ma, brightness is equal to 1030cd/m2(6.4V).At this time, CIEx
=0.684, y=0.315.
Embodiment 2
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass
Substrate.The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6 support.Hereafter, on an ito substrate with WithThe layer for sequentially forming organic substance.At 0.9 ma, brightness is equal to 1139cd/m2(6.4V).At this time, CIEx
=0.683, y=0.314.
Embodiment 3
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass
Substrate.The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6 support.Hereafter, on an ito substrate with WithThe layer for sequentially forming organic substance.At 0.9 ma, brightness is equal to 1231cd/m2(6.2V).At this time, CIEx
=0.682, y=0.318.
Embodiment 4
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass
Substrate.The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6 support.Hereafter, on an ito substrate with WithThe layer for sequentially forming organic substance.At 0.9 ma, brightness is equal to 1179cd/m2(6.3V).At this time, CIEx
=0.685, y=0.313.
Comparative example
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass
Substrate.The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6 support.Hereafter, on an ito substrate with WithThe layer for sequentially forming organic substance.At 0.9 ma, brightness is equal to
780cd/m2(7.5V).At this time, CIEx=0.659, y=0.329.
It is shown in table 1 below according to above-described embodiment and comparative example efficiency, chromaticity coordinate and the characteristic of brightness.
Table 1
As shown in table 1, or even when excitation purity is high, which also expeditiously runs at low voltage.Also, with comparison
Example is compared, and the current efficiency of embodiment increases by 30% or more.
Those skilled in the art will be, it is evident that without departing from the spirit and scope of the invention, the present invention can have
Many modifications and variations.Therefore it is desired that arriving, the present invention is covered in the range and its suitable range of accessory claim and mentions
The modifications and variations of the invention supplied.
Industrial applicability
Luminescent layer by using formula (I) compound represented as organic electroluminescence device, present invention offer have
The organic electroluminescence device of excellent excitation purity and brightness and extended durability.
Claims (8)
1. a kind of red phosphorescent compound, which is characterized in that its structural formula is shown in formula I,
Wherein, R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from H, C1~C6 alkyl, one kind of C5~C8 naphthenic base.
2. red phosphorescent compound as described in claim 1, which is characterized in that C1~C6 alkyl or C5~C8 naphthenic base
Selected from one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl, n-pentyl, cyclopenta and cyclohexyl.
3. red phosphorescent compound as claimed in claim 2, which is characterized in that C1~C6 alkyl or C5~C8 naphthenic base
Hydrogen atom all replaced D-atom.
4. red phosphorescent compound as described in claim 1, which is characterized in that the La group is in following structural
It is a kind of:
5. red phosphorescent compound as described in claim 1, wherein formula (I) is any of following structural:
。
6. a kind of organic electroluminescence device, it is characterised in that: the device includes the anode being sequentially deposited each other, hole injection
Layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode；The organic electroluminescence device includes right
It is required that any compound is as dopant in 1-5.
7. organic electroluminescence device as claimed in claim 6, wherein using Al or Zn metal complex and carbazole derivates
Any one of material of main part as luminescent layer, and wherein the amount ranges of dopant in 0.1%~50% range of weight ratio
It is interior.
8. organic electroluminescence device as claimed in claim 6, wherein the ligand of every kind of Al and Zn metal complex includes quinoline
Quinoline base, xenyl, isoquinolyl, phenyl, methylquinoline base, dimethyl quinoline base, dimethyl-isoquinolyl, and wherein carbazole spreads out
Biology includes CBP.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910682406.5A CN110467642A (en) | 2019-07-26 | 2019-07-26 | Red phosphorescent compound and the organic electroluminescence device for using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910682406.5A CN110467642A (en) | 2019-07-26 | 2019-07-26 | Red phosphorescent compound and the organic electroluminescence device for using the compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110467642A true CN110467642A (en) | 2019-11-19 |
Family
ID=68508421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910682406.5A Pending CN110467642A (en) | 2019-07-26 | 2019-07-26 | Red phosphorescent compound and the organic electroluminescence device for using the compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110467642A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113493482A (en) * | 2020-04-01 | 2021-10-12 | 北京夏禾科技有限公司 | Organic light-emitting materials containing cyano-substituted ancillary ligands |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104277075A (en) * | 2013-07-01 | 2015-01-14 | 环球展览公司 | Ancillary ligands for organometallic complexes, device comprising the same, and formulation |
| CN109956977A (en) * | 2017-12-25 | 2019-07-02 | 北京夏禾科技有限公司 | The metal complex of the ligand containing heterocyclic substituted, and electroluminescent device and compound formulas comprising the complex compound |
| CN110036499A (en) * | 2016-12-27 | 2019-07-19 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
| CN110343136A (en) * | 2018-04-02 | 2019-10-18 | 三星电子株式会社 | Organo-metallic compound and organic luminescent device and diagnosis composition including it |
| CN110922429A (en) * | 2018-09-20 | 2020-03-27 | 北京夏禾科技有限公司 | Organic luminescent material containing novel auxiliary ligand |
-
2019
- 2019-07-26 CN CN201910682406.5A patent/CN110467642A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104277075A (en) * | 2013-07-01 | 2015-01-14 | 环球展览公司 | Ancillary ligands for organometallic complexes, device comprising the same, and formulation |
| CN110036499A (en) * | 2016-12-27 | 2019-07-19 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
| CN109956977A (en) * | 2017-12-25 | 2019-07-02 | 北京夏禾科技有限公司 | The metal complex of the ligand containing heterocyclic substituted, and electroluminescent device and compound formulas comprising the complex compound |
| CN110343136A (en) * | 2018-04-02 | 2019-10-18 | 三星电子株式会社 | Organo-metallic compound and organic luminescent device and diagnosis composition including it |
| CN110922429A (en) * | 2018-09-20 | 2020-03-27 | 北京夏禾科技有限公司 | Organic luminescent material containing novel auxiliary ligand |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113493482A (en) * | 2020-04-01 | 2021-10-12 | 北京夏禾科技有限公司 | Organic light-emitting materials containing cyano-substituted ancillary ligands |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1783133B1 (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| US8623519B2 (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| EP1783132B1 (en) | Red phosphorescent compounds and organic electromuninescent devices using the same | |
| CN101160369B (en) | Red phosphorescene compounds and organic electroluminescence devices using the same | |
| CN110452271A (en) | Red phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN110467630A (en) | A kind of phosphorescent compound and the organic light emitting diode device using the compound | |
| US20070128468A1 (en) | Red phosphorescent compounds and organic electroluminescent devices using the same | |
| CN111777633B (en) | Boron-containing compound and organic electroluminescent device containing same | |
| CN108997438B (en) | Red phosphorescent compound and organic light emitting diode device using the same | |
| CN110746401A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN111153888A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN109988193A (en) | Green phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN112079876A (en) | Organic compound and organic electroluminescent device using same | |
| CN111116673A (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| CN110724168A (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| CN109810146A (en) | Green phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN110467642A (en) | Red phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN110964063A (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| CN110872301A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN109988192A (en) | Green phosphorescent compound and the organic electroluminescence device for using the compound | |
| KR101799033B1 (en) | Red color phosphorescent host material and Organic electroluminescent display device using the same | |
| CN109206457A (en) | Red phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN109776616A (en) | Green phosphorescent compound and the organic electroluminescence device for using the compound | |
| KR20150055356A (en) | Phosphorescene host compounds and organic light emitting device comprising the same | |
| CN110746464A (en) | Red phosphorescent compound and organic electroluminescent device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20191119 |