CN109678868A - A kind of red phosphorescent compound and its organic luminescent device using the compound - Google Patents
A kind of red phosphorescent compound and its organic luminescent device using the compound Download PDFInfo
- Publication number
- CN109678868A CN109678868A CN201811325889.5A CN201811325889A CN109678868A CN 109678868 A CN109678868 A CN 109678868A CN 201811325889 A CN201811325889 A CN 201811325889A CN 109678868 A CN109678868 A CN 109678868A
- Authority
- CN
- China
- Prior art keywords
- phosphorescent compound
- compound
- red phosphorescent
- layer
- independently selected
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
-
- 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
-
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
-
- 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
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The present invention relates to a kind of red phosphorescent compound and using the organic light emission tube device of the compound, more specifically, it is related to a kind of soluble phosphorescent compound with excellent excitation purity and high brightness and luminous efficiency and the OLED device using the compound.A kind of phosphorescent compound, shown in structural formula as I,In above-mentioned structural formula I, R is independently selected from flowering structure:Wherein, Ar is independently selected from one of C6-C30 aryl, C2-C30 heteroaryl.The C6-C30 aryl is selected from one of phenyl, naphthalene, xenyl, terphenyl and phenanthryl.The C2-C30 heteroaryl is selected from one of pyridyl group, bipyridyl, quinolyl, isoquinolyl, phenanthroline and triazine radical.The present invention uses chemical formula shown in I as the luminescent layer of organic light emitting diode device, has excellent excitation purity and brightness and extended durability effect.
Description
Technical field
It is more specifically related to the present invention relates to a kind of red phosphorescent compound and using the organic light emission tube device of the compound
And a kind of soluble phosphorescent compound with excellent excitation purity and high brightness and luminous efficiency and use the compound
OLED device.
Background technique
Recently, the demand of flat-panel monitor (such as liquid crystal display and Plasmia indicating panel) is being increased.But these
Flat-panel monitor has lower response time and relatively narrow visual angle compared with cathode-ray tube (CRT).
Organic Light Emitting Diode (OLED) device be able to solve problem above and take up an area lesser next-generation flat-panel monitor it
One.
The element of 0LED device can be formed on flexible base board (such as plastic base).In addition, OLED device is at visual angle, drive
There is advantage in terms of dynamic voltage, energy consumption and excitation purity.Outside side, OLED device is enough to generate full-colour image.
In general, the light emitting diode of OLED device includes anode, hole injection layer (HIL), hole transporting layer (HTL), shine material
The bed of material (EML), electron supplying layer (ETL), electron injecting layer (EIL) and cathode.
OLED device shines in the following manner: by the cathode as electron injection electrode and by the sun as hole injecting electrode
Pole respectively injects electrons and holes in light emitting compound layer, to make electronics and hole-recombination to generate exciton, and makes exciton
Ground state is transitted to by excitation state.
Principle of luminosity can be divided into fluorescence radiation and phosphorescence shines.In fluorescence radiation, the organic molecule of singlet excited state
Ground state is transitted to, light is thus issued.On the other hand, in phosphorescence shines, the organic molecule of triplet state excited state transits to base
Thus state issues light.
When luminous material layer transmitting corresponds to the light of band gap, the singlet exciton with 0 spin and three lines with 1 spin
State exciton is generated with the ratio of 1:3.The ground state of organic material is singlet, this allows singlet exciton to transit to ground state and companion
With luminous.But since the OLED device for using fluorescent material with luminous transition cannot occur for triplet excitons
Internal quantum efficiency is limited within 25%.
On the other hand, if Quantum geometrical phase momentum is very high, singlet and triplet state mixing are so that in singlet and three
Intersystem crossing is generated between line state, and triplet excitons can also transit to ground state and with luminous.Phosphor material can make
With triplet excitons and singlet exciton, so that being imitated using the interior quantum that the OLED device of phosphor material can have 100%
Rate.
Recently, by iridium complex, such as bis- (2- phenylchinoline) (acetylacetone,2,4-pentanedione) iridium (III) (Ir (2-phq) 2
(acac)), bis- (2- benzo [b] thiophene -2- yl pyridines) (acetylacetone,2,4-pentanedione) iridium (III) (Ir (btp) 2 (acac)) and three (2- benzene
Base quinoline) introducing of iridium (III) Ir (2-phq) 3 dopant.
In order to obtain high current luminous efficiency (Cd/A) using phosphor material, excellent internal quantum, high colour purity are needed
Degree and long-life.In particular, referring to Fig.1, excitation purity is higher, that is, CIE (X) is higher, and colour sensitivity is poorer.As a result, in height
Under internal quantum efficiency, very difficult acquisition luminous efficiency.Therefore, it is necessary to excellent excitation purity (CIE (X) >=0.65) and Gao Faguang
The novel red phosphor compound of efficiency.
On the other hand, other than above-mentioned iridium complex, for example, 4,4-N, N carbazole biphenyl (CBP) or other metal complexes
Object is used as red phosphorescent compound.However, these compounds do not have ideal solubility in a solvent, thus cannot be by molten
Liquid technique forms luminescent layer.Luminescent layer should be formed by depositing operation, and therefore, manufacturing process is extremely complex, process efficiency
Also extremely low.In addition, the waste material in depositing operation is very more, production cost is caused to increase.
Summary of the invention
The object of the present invention is to provide a kind of red phosphorescent compound and its use the organic luminescent device of the compound, the present invention
Phosphorescent compound have excellent pure colorimetric, high brightness and excellent luminous efficiency
It is a further object to provide the red phosphorescent compounds for being suitable for solution process.
It is a further object to provide the OLED with improved luminous efficiency.
Will be discussed below other features and advantages of the present invention, Partial Feature and advantage will be apparent from the description it is understandable, or
Person can be known by implementing the invention.The objectives and other advantages of the invention will be by specification and its claim and attached
Specifically noted structure is realized or is reached in figure.
In order to realize these and other advantages and the purpose of the present invention, as this paper is embodied and is broadly described, this hair
It is bright that a kind of red phosphorescent compound of following formula is provided,
In above-mentioned structural formula I, Z is independently selected from flowering structure:
Wherein, Ar is independently selected from C6-C30 aryl, C2-C30 heteroaryl.
Further, the C6-C30 aryl is selected from one of phenyl, naphthalene, xenyl, terphenyl and phenanthryl.
Further, the C2-C30 heteroaryl be selected from pyridyl group, bipyridyl, quinolyl, isoquinolyl, phenanthroline and
One of triazine radical.
Further, the Ar is independently selected from one of following group: (any one of following group can be replaced to have work originally
The position of property hydrogen)
Further, the phosphorescent compound is independently selected from following compounds:
Further, the organic electroluminescence device sequentially include deposition anode, hole injection layer, hole transmission layer,
Luminescent layer, electron transfer layer, electron injecting layer and cathode, material of main part of the phosphorescent compound as luminescent layer.
The present invention has the advantages that the present invention uses chemical formula shown in I as the luminescent layer of organic light emitting diode device, tool
There are excellent excitation purity and brightness and extended durability effect.
Detailed description of the invention
Fig. 1 is organic electroluminescent LED lighting coloration and visibility relationship figure.
Specific embodiment
In order to be easy to understand the technical means, the creative features, the aims and the efficiencies achieved by the present invention, below with reference to figure
Show and specific embodiment, the present invention is further explained.
It is existing since the red phosphorescent compound of structural formula as I all has excellent pure colorimetric, high brightness and excellent luminous efficiency
By taking RH-001, RH-007, RH-091 and RH-097 preparation method and test result as an example, it was demonstrated that technical solution provided by the invention
With the technical effect reached.
In following embodiments, NPB 4,4 '-bis- [N- (1- naphthalene)-N- phenylamino] biphenyl, CBP 4,4 '-N, the N click of '-two
Biphenyl, CuPc are CuPc, and LiF lithium fluoride, ITO is tin indium oxide, and Alq3 is three (8-hydroxyquinoline) aluminium.
LC-MS: liquid chromatograph-mass spectrometer, M/Z: proton number/charge number ratio.
Following formula is compound copper (II) phthalocyanine (CuPc) used in embodiments of the invention, NPB, (btp) 2Ir
(acac), the structural formula of Alq3 and CBP.
Form example
1. the synthesis of intermediate compound I -1:
Adjacent cyanophenol (30g, 0.25mol) is added in the flask of original place.Acetone (500mL) and potassium carbonate is then added
(41.8g,0.3mol).Then methyl bromoacetate (38.5g, 0.25mol) is added dropwise at 2 DEG C into reaction flask, but answers system
Heating, back flow reaction four hours.Reaction solution is filtered, acetone soln part is evaporated to obtain intermediate compound I -1 (43.3g, 90%).
192.2 (M+H of LC-MS:M/Z)+。
2. the synthesis of intermediate compound I -2:
Intermediate compound I -1 (40g, 0.21mol) is dissolved in 2000mL round-bottomed flask with the methylene chloride of 800mL.Delay at room temperature
Slow be added chlorosulphonyl isocyanate (33.4ml, 0.38mol) is stirred two hours afterwards.100ml dilute hydrochloric acid is added in concentration of reaction solution,
It is stirred one hour under the conditions of 100 DEG C of temperature.Cooling reaction solution is neutralized to room temperature with saturated sodium bicarbonate solution.Filtering is precipitated
Solid obtain intermediate compound I -2 (39.3g, 80%) LC-MS:M/Z 235.2 (M+H)+。
3. the synthesis of intermediate compound I -3:
Intermediate compound I -2 (30g, 0.128mol) is dissolved in the methanol of 600mL, is added in the round-bottomed flask of 1000mL.Then by 2M hydrogen
Sodium oxide molybdena (200mL) is slowly added dropwise in reaction system.Mixed liquor is stirred at reflux reaction three hours, then cools to room temperature.With
Dilute hydrochloric acid adjusts the pH value of reaction solution to 3, later concentration of reaction solution.Methanol is slowly added dropwise in remaining solid, filter solid is crossed,
It is dried to obtain 203.2 (M+H of intermediate compound I -3 (21.0g, 81%) LC-MS:M/Z)+。
4. the synthesis of intermediate compound I -4:
Intermediate compound I -3 (20g, 98.9mmol) is dissolved in 500mL round-bottomed flask with 300mL phosphorus oxychloride.It is cooled to -30
DEG C, it is slowly added to N, N- diisopropylethylamine (25.6g, 0.2mol).Heating is cooled to room temperature after being stirred at reflux reaction 36 hours.
Then reaction solution is poured into ice water, is extracted with ethyl acetate.The organic phase being obtained by extraction is washed with saturated sodium bicarbonate solution,
And it is removed water with sodium sulphate.Organic phase that treated is concentrated and dried to obtain intermediate compound I -4 (10.6g, 45%).LC-MS:M/Z
240.1(M+H)+。
5. the synthesis of intermediate compound I -5:
Intermediate compound I -4 (10.0g, 41.8mmol) is added in 500ml reaction flask, (9- phenyl -9H- carbazole -3- base) boric acid
(12.0g, 41.8mmol), potassium carbonate (14.5g, 104.6mmol), tetra-triphenylphosphine palladium (2.4g, 2.1mmol), 1,4- dioxy
Six rings (140mL) and water (70mL).Reaction system is warming up to 60 DEG C, reacts ten hours under nitrogen protection.Reaction solution is poured into
In 450mL methanol, the solid of precipitation is filtered.With the solid of chlorobenzene solution modeling, with the funnel mistake that diatomite and silica white are housed
Filter.The orange liquid concentration being obtained by filtration is evaporated and obtains intermediate compound I -5 (12.1g, yield 65%) LC- with recrystallizing methanol
446.9 (M+H of MS:M/Z)+。
The synthesis of 6.RH-001:
Intermediate compound I -5 (5g, 11.2mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (3.3g,
12.3mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.8g,
33.6mmol) and ortho-xylene (80mL).Reaction system is warming up to 120 DEG C, reacts 12 hours under nitrogen protection.Reaction is completed
Afterwards, reaction solution is cooled to room temperature, is extracted with o-dichlorohenzene and water.Organic layer is dry with anhydrous magnesium sulfate, and concentration recrystallizes institute
Crude product crosses silicagel column and obtains RH-001 (6.4g, yield 84%).LC-MS:M/Z 677.8 (M+H)+。
7. the synthesis of intermediate compound I -6:
It is reacted in 500ml
Intermediate compound I -4 (10.0g, 41.8mmol) is added in bottle, 9- (4- xenyl) -3- boric acid carbazole (15.2g, 41.8mmol), carbon
Sour potassium (14.5g, 104.6mmol), tetra-triphenylphosphine palladium (2.4g, 2.1mmol), 1,4- dioxane (140mL) and water
(70mL).Reaction system is warming up to 60 DEG C, reacts ten hours under nitrogen protection.Reaction solution is poured into 450mL methanol, filtering analysis
Solid out.With the solid of chlorobenzene solution modeling, filtered with the funnel equipped with diatomite and silica white.The orange liquid being obtained by filtration
Body concentration is evaporated and obtains 523.0 (M+H of intermediate compound I -6 (13.1g, yield 60%) LC-MS:M/Z with recrystallizing methanol)+。
The synthesis of 8.RH-007:
Intermediate compound I -6 (5g, 9.6mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (2.8g,
10.5mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.2g,
28.7mmol) and ortho-xylene (80mL).Reaction system is warming up to 120 DEG C, reacts 12 hours under nitrogen protection.Reaction is completed
Afterwards, reaction solution is cooled to room temperature, is extracted with o-dichlorohenzene and water.Organic layer is dry with anhydrous magnesium sulfate, and concentration recrystallizes institute
Crude product crosses silicagel column and obtains RH-007 (5.5g, yield 80%).LC-MS:M/Z 753.9 (M+H)+。
9. the synthesis of intermediate compound I -7:
Intermediate compound I -4 (10.0g, 41.8mmol) is added in 500ml reaction flask, (9- phenyl -9H- carbazole -2- base) boric acid
(12.0g, 41.8mmol), potassium carbonate (14.5g, 104.6mmol), tetra-triphenylphosphine palladium (2.4g, 2.1mmol), 1,4- dioxy
Six rings (140mL) and water (70mL).Reaction system is warming up to 60 DEG C, reacts ten hours under nitrogen protection.Reaction solution is poured into
In 450mL methanol, the solid of precipitation is filtered.With the solid of chlorobenzene solution modeling, with the funnel mistake that diatomite and silica white are housed
Filter.The orange liquid concentration being obtained by filtration is evaporated and obtains intermediate compound I -7 (13.1g, yield 70%) LC- with recrystallizing methanol
446.9 (M+H of MS:M/Z)+。
The synthesis of 10.RH-091:
Intermediate compound I -7 (5g, 11.2mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (3.3g,
12.3mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.8g,
33.6mmol) and ortho-xylene (80mL).Reaction system is warming up to 120 DEG C, reacts 12 hours under nitrogen protection.Reaction is completed
Afterwards, reaction solution is cooled to room temperature, is extracted with o-dichlorohenzene and water.Organic layer is dry with anhydrous magnesium sulfate, and concentration recrystallizes institute
Crude product crosses silicagel column and obtains RH-091 (6.5g, yield 85%).LC-MS:M/Z 677.8 (M+H)+。
11. the synthesis of intermediate compound I -8:
Intermediate compound I -4 (10.0g, 41.8mmol) is added in 500ml reaction flask, 9- (4- xenyl) -2- boric acid carbazole
(15.2g, 41.8mmol), potassium carbonate (14.5g, 104.6mmol), tetra-triphenylphosphine palladium (2.4g, 2.1mmol), 1,4- dioxy
Six rings (140mL) and water (140mL).Reaction system is warming up to 60 DEG C, reacts ten hours under nitrogen protection.Reaction solution is poured into
In 450mL methanol, the solid of precipitation is filtered.With the solid of chlorobenzene solution modeling, with the funnel mistake that diatomite and silica white are housed
Filter.The orange liquid concentration being obtained by filtration is evaporated and obtains intermediate compound I -8 (14.0g, yield 64%) LC- with recrystallizing methanol
523.0 (M+H of MS:M/Z)+。
The synthesis of 12.RH-097:
Intermediate compound I -8 (5g, 9.6mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (2.8g,
10.5mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.2g,
28.7mmol) and ortho-xylene (80mL).Reaction system is warming up to 120 DEG C, reacts 12 hours under nitrogen protection.Reaction is completed
Afterwards, reaction solution is cooled to room temperature, is extracted with o-dichlorohenzene and water.Organic layer is dry with anhydrous magnesium sulfate, and concentration recrystallizes institute
Crude product crosses silicagel column and obtains RH-097 (6.1g, yield 85%).LC-MS:M/Z 753.9 (M+H)+。
Embodiment
1. first embodiment
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.Hereafter, on ITO substrate with
With's
Sequentially form the layer of organic substance.
At 0.9 ma, brightness is equal to 1284cd/m2(5.7V).At this time, CIEx=0.658, y=0.330.
2. the second embodiment
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.Hereafter, on ITO substrate with
WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1193cd/m2(5.9V).At this time, CIEx=0.658, y=0.329.
3. third embodiment
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.Hereafter, on ITO substrate with
WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1262cd/m2(5.8V).At this time, CIEx=0.659, y=0.330.
4. the 4th embodiment
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.Hereafter, on ITO substrate with
With's
Sequentially form the layer of organic substance.
At 0.9 ma, brightness is equal to 1163cd/m2(6.0V).At this time, CIEx=0.657, y=0.329.
5. comparative example
Pattern ito glass substrate, with the light emitting region with 3mm × 3mm.Then, wash patterned ito glass base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.On an ito substrate with
WithSequence shape
At the layer of organic substance.
At 0.9 ma, brightness is equal to 780cd/m2(7.5V).At this time, CIEx=0.659, y=0.329.
Increase (becoming much larger with the X value of chromaticity coordinate) visibility with the excitation purity of organic electroluminescence device as shown in Figure 1
It reduces.
According to the embodiment above and comparative example, efficiency, chromaticity coordinate, and the characteristic of brightness are shown in table 1 below.
Table 1
As shown in table 1, or even when excitation purity is high, which also expeditiously runs at low voltage.Further, with comparative example phase
Than the current efficiency of the second embodiment increases by 50% or more.
The basic principles, main features and advantages of the present invention have been shown and described above.The technical staff of the industry
It should be appreciated that the present invention is not limited to the above embodiments, the above embodiments and description only describe the present invention
Principle, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these variation and
Improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention is by appended claims and its is equal
Object defines.
Claims (6)
1. a kind of red phosphorescent compound, it is characterised in that: shown in its structural formula as I,
In above-mentioned structural formula I, Z is independently selected from flowering structure:
Wherein, Ar is independently selected from one of C6-C30 aryl, C2-C30 heteroaryl.
2. red phosphorescent compound according to claim 1, it is characterised in that: the C6-C30 aryl be selected from phenyl,
One of naphthalene, xenyl, terphenyl and phenanthryl.
3. red phosphorescent compound according to claim 1, it is characterised in that: the C2-C30 heteroaryl is selected from pyridine
One of base, bipyridyl, quinolyl, isoquinolyl, phenanthroline and triazine radical.
4. red phosphorescent compound according to claim 1, it is characterised in that: the Ar is independently selected from following:
5. red phosphorescent compound described in any one of -4 according to claim 1, it is characterised in that: the phosphorescent compounds
Object is independently selected from following compounds:
6. a kind of organic electroluminescent LED device using red phosphorescent compound described in any one of claim 1-5
Part, it is characterised in that: the organic electroluminescence device sequentially include deposition anode, hole injection layer, hole transmission layer,
Luminescent layer, electron transfer layer, electron injecting layer and cathode, material of main part of the red phosphorescent compound as luminescent layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811325889.5A CN109678868A (en) | 2018-11-08 | 2018-11-08 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811325889.5A CN109678868A (en) | 2018-11-08 | 2018-11-08 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109678868A true CN109678868A (en) | 2019-04-26 |
Family
ID=66185805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811325889.5A Pending CN109678868A (en) | 2018-11-08 | 2018-11-08 | A kind of red phosphorescent compound and its organic luminescent device using the compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109678868A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330481A (en) * | 2019-07-03 | 2019-10-15 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and the organic luminescent device using the compound |
| CN110746962A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN111423447A (en) * | 2019-10-23 | 2020-07-17 | 宇瑞(上海)化学有限公司 | Red phosphorescent compound and organic light-emitting device |
| CN111560023A (en) * | 2019-10-23 | 2020-08-21 | 宇瑞(上海)化学有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN113912615A (en) * | 2021-10-27 | 2022-01-11 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic component and electronic device comprising same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012145173A1 (en) * | 2011-04-08 | 2012-10-26 | Universal Display Corporation | Substituted oligoazacarbazoles for light emitting diodes |
| CN106397460A (en) * | 2015-07-29 | 2017-02-15 | 环球展览公司 | Organic electroluminescent materials and devices |
| WO2017030307A1 (en) * | 2015-08-20 | 2017-02-23 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic apparatus comprising same |
| KR20180022608A (en) * | 2016-08-23 | 2018-03-06 | 주식회사 엘지화학 | Compound and organic light emitting device containing the same |
-
2018
- 2018-11-08 CN CN201811325889.5A patent/CN109678868A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012145173A1 (en) * | 2011-04-08 | 2012-10-26 | Universal Display Corporation | Substituted oligoazacarbazoles for light emitting diodes |
| CN106397460A (en) * | 2015-07-29 | 2017-02-15 | 环球展览公司 | Organic electroluminescent materials and devices |
| WO2017030307A1 (en) * | 2015-08-20 | 2017-02-23 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic apparatus comprising same |
| KR20180022608A (en) * | 2016-08-23 | 2018-03-06 | 주식회사 엘지화학 | Compound and organic light emitting device containing the same |
Non-Patent Citations (1)
| Title |
|---|
| 张飞飞 等: "咔唑类化合物研究新进展", 《有机化学》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110330481A (en) * | 2019-07-03 | 2019-10-15 | 浙江华显光电科技有限公司 | A kind of red phosphorescent compound and the organic luminescent device using the compound |
| CN110330481B (en) * | 2019-07-03 | 2022-04-08 | 浙江华显光电科技有限公司 | Red phosphorescent compound and organic light-emitting device using same |
| CN110746962A (en) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN111423447A (en) * | 2019-10-23 | 2020-07-17 | 宇瑞(上海)化学有限公司 | Red phosphorescent compound and organic light-emitting device |
| CN111560023A (en) * | 2019-10-23 | 2020-08-21 | 宇瑞(上海)化学有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
| CN113912615A (en) * | 2021-10-27 | 2022-01-11 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic component and electronic device comprising same |
| CN113912615B (en) * | 2021-10-27 | 2022-05-17 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic component and electronic device comprising same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109678868A (en) | A kind of red phosphorescent compound and its organic luminescent device using the compound | |
| CN110467630A (en) | A kind of phosphorescent compound and the organic light emitting diode device using the compound | |
| CN109678867B (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN109593097B (en) | Phosphorescent host compound and organic electroluminescent device using same | |
| CN109678875A (en) | A kind of phosphorescent compound and the organic light emitting diode device using the compound | |
| CN110437242A (en) | A kind of red phosphorescent compound and the organic electroluminescence device using the compound | |
| CN109694371A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN110330481B (en) | Red phosphorescent compound and organic light-emitting device using same | |
| CN110437241A (en) | A kind of red phosphorescent host compound and the organic luminescent device using the compound | |
| KR20120033017A (en) | Novel compounds for organic electronic material and organic electroluminescent 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 | |
| CN110903305A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN107353298A (en) | The aromatic amine derivant and its organic luminescent device of a kind of class formation containing carbazole | |
| CN110903301A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN106029636A (en) | Materials for organic light-emitting devices | |
| CN110452271A (en) | Red phosphorescent compound and the organic electroluminescence device for using the compound | |
| CN111689984A (en) | Compound containing multi-heterocyclic structure and application thereof | |
| CN109503607A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN111662298A (en) | Novel compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device | |
| CN109678876A (en) | A kind of red phosphorescent compound and its organic luminescent device using the compound | |
| CN108997438A (en) | Red phosphorescent compound and the organic light emitting diode device for using the compound | |
| CN110903300A (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN109438468A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN110872301A (en) | Phosphorescent compound and organic light emitting diode 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: 20190426 |