CN109503607A - A kind of phosphorescence host compound and its organic electroluminescence device using the compound - Google Patents
A kind of phosphorescence host compound and its organic electroluminescence device using the compound Download PDFInfo
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- 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
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Abstract
The present invention relates to a kind of phosphorescence host compounds to use the organic electroluminescence device of the compound with it.A kind of phosphorescence host compound, shown in structural formula as I, structural formula is shown in formula I,In above-mentioned structural formula I, X is O or S, and Z is independently selected from flowering structure:Wherein, Ar is independently selected from one of C6-C30 aryl, C2-C30 heteroaryl.The present invention uses chemical formula shown in I as the material of main part of the luminescent layer of organic light emitting diode device (organic electroluminescence device), has excellent excitation purity and brightness and extended durability effect.
Description
Technical field
The present invention relates to a kind of phosphorescence host compounds to use the organic electroluminescence device of the compound with it.
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 monitors have lower response time and relatively narrow visual angle compared with cathode-ray tube (CRT).
Organic Light Emitting Diode (OLED) device is to be able to solve problem above and take up an area lesser next-generation FPD
One of device.
The element of OLED device can be formed on flexible base board (such as plastic base).In addition, OLED device visual angle,
There is advantage in terms of driving 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), hair
Optical material layer (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 as hole injecting electrode
Anode respectively by electrons and holes inject light emitting compound layer in, to make electronics and hole-recombination to generate exciton, and make
Exciton transits to ground state by excitation state.
Principle of luminosity can be divided into fluorescence radiation and phosphorescence shines.In fluorescence radiation, singlet excited state it is organic
Thus molecular transition issues light to ground state.On the other hand, in phosphorescence shines, the organic molecule transition of triplet state excited state
To ground state, light is thus issued.
When luminous material layer transmitting correspond to band gap light when, with 0 spin singlet exciton and with 1 spin
Triplet excitons are 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 with luminous.But since triplet excitons cannot occur to use the OLED device of fluorescent material with luminous transition
The internal quantum efficiency of part 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
Intersystem crossing is generated between triplet state, and triplet excitons can also transit to ground state and with luminous.Phosphor material can
To use triplet excitons and singlet exciton, so that can have 100% interior amount using the OLED device of phosphor material
Sub- efficiency.
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 is needed
Excitation purity 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,
Under high internal quantum efficiency, very difficult acquisition luminous efficiency.Therefore, it is necessary to excellent excitation purity (CIE (X) >=0.65) and height
The novel red phosphor compound of luminous efficiency.
On the other hand, other than above-mentioned iridium complex, for example, 4,4-N, N carbazole biphenyl (CBP) or other metals
Complex compound is used as red phosphorescent compound.However, these compounds do not have ideal solubility in a solvent, thus cannot lead to
Solution process is crossed to form luminescent layer.Luminescent layer should be formed by depositing operation, and therefore, manufacturing process is extremely complex, technique
Efficiency is 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 present invention uses the organic electroluminescence device of the compound for a kind of phosphorescence host compound with it.Their bases
Originally limitation and defect bring one or more in the prior art are solved the problems, such as.
It is an object of the present invention to provide a kind of phosphorescence host compound, the main body phosphorescent compound has excellent
Pure colorimetric, high brightness and excellent luminous efficiency.
It is a further object to provide the OLED with improved luminous efficiency.
It will be discussed below other features and advantages of the present invention, Partial Feature and advantage will be apparent from the description easily
Understand, or can be known by implementing the invention.The objectives and other advantages of the invention will be wanted by specification and its right
Ask and attached drawing in specifically noted structure realize or reach.
In order to realize these and other advantages and the purpose of the present invention, as this paper is embodied and is broadly described,
The present invention provides a kind of phosphorescence host compound of following formula:
The present invention provides a kind of phosphorescence host compound, shown in structural formula as I,
In above-mentioned structural formula I, X is O or S, and 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 is selected from pyridyl group, bipyridyl, quinolyl, isoquinolyl, phenanthroline
One of base and triazine radical.
Further, the Ar is independently selected from one of following group: (can replace any one of following group originally
The position of active hydrogen)
Further, the phosphorescent compound is independently selected from following compounds:
Further, the organic electroluminescence device sequentially includes the anode of deposition, hole injection layer, hole transport
Layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, material of main part of the phosphorescence host compound as luminescent layer.
The present invention has the advantages that the present invention uses chemical formula shown in I as organic light emitting diode device (Organic Electricity
Electroluminescence device) luminescent layer material of main part, there is 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, tie below
Diagram and specific embodiment are closed, the present invention is further explained.
Since the red phosphorescent compound of structural formula as I all has excellent pure colorimetric, high brightness and excellent luminous effect
Rate, now by taking RH-001, RH-007, RH-091 and RH-097 preparation method and test result as an example, it was demonstrated that skill provided by the invention
Art scheme and the technical effect reached.
In following embodiments, NPB 4,4 '-bis- [N- (1- naphthalene)-N- phenylamino] biphenyl, CBP 4,4 '-N, N '-
Two click 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:
Chlorosulphonyl isocyanate (44.4g, 313.8mmol) is added into 2000mL round-bottomed flask, 2- amino benzo is added dropwise
Solution of the furans -3- methyl formate (40g, 209.2mmol) in methylene chloride (1000mL).Reaction is gradually heated to room temperature,
Stirring 2 hours.It after reaction concentration, is added 6N HCl (300mL), is stirred 1 hour at 100 DEG C.Reaction mixture is cold at room temperature
But it and with saturated aqueous NaHCO3 neutralizes.Obtained solid is filtered, beige solid intermediate compound I -1 (41.7g, yield are obtained
85%) LC-MS:M/Z 235.2 (M+H)+。
2. the synthesis of intermediate compound I -2:
Intermediate compound I -1 (40.0g, 170.8mol) is dissolved in 1000mL methanol in 2000ml round-bottomed flask.By the hydrogen of 2M
Sodium hydroxide solution (300mL) is added in round-bottomed flask.After stirring three hours, room temperature is down in reaction, adjusts PH to 3 with dilute hydrochloric acid.
Methanol is slowly added dropwise in remaining enriched product concentration of reaction solution, and suction filtration obtains intermediate compound I -2 (28.3g, yield 82%).
LC-MS:M/Z 203.2 (M+H)+。
3. the synthesis of intermediate compound I -3:
By the mixed of intermediate compound I -2 (28g, 138.5mmol) and chlorethoxyfos (200mL) in 500 milliliters of round-bottomed flask
It closes, mixture flows back 8 hours.Reaction mixture is cooled to environment temperature, and pours into be formed in ice water with vigorous stirring and sink
Starch.Products therefrom is filtered, 240.1 (M+H of white solid intermediate compound I -3 (28.5g, yield 86%) LC-MS:M/Z is obtained)+。
(intermediate compound I -3 ' of sulfur-bearing can be obtained by following reaction
)
4. the synthesis of intermediate compound I -4:
Intermediate compound I -3 (10.0g, 41.8mmol) is added in 500ml reaction flask, (9- phenyl -9H- carbazole -3- base) boron
Acid ((12.0g, 41.8mmol), potassium carbonate (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 fallen
Enter in 450mL methanol, filters the solid of precipitation.With the solid of chlorobenzene solution modeling, with the funnel that diatomite and silica white are housed
Filtering.The orange liquid concentration being obtained by filtration is evaporated and obtains intermediate compound I -4 (11.9g, yield 64%) LC- with recrystallizing methanol
446.9 (M+H of MS:M/Z)+。
The synthesis of 5.RH-001:
Intermediate compound I -4 (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 (6.2g, yield 82%).LC-MS:M/Z 677.8 (M+H)+。
RH-181, LC-MS:M/Z 693.8 (M+H) are obtained by similar reaction+。
6. the synthesis of intermediate compound I -5:
Intermediate compound I -3 (10.0g, 41.8mmol) is added in 500ml reaction flask, 9- (4- xenyl) -3- 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 (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 (13.3g, yield 61%) with recrystallizing methanol.LC-
523.0 (M+H of MS:M/Z)+。
The synthesis of 7.RH-007:
Intermediate compound I -5 (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 (5.8g, yield 81%).LC-MS:M/Z 753.9 (M+H)+。
RH-187, LC-MS:M/Z 769.9 (M+H) are obtained by similar reaction+。
8. the synthesis of intermediate compound I -6:
Intermediate compound I -3 (10.0g, 41.8mmol) is added in 500ml reaction flask, (9- phenyl -9H- carbazole -2- base) boron
Sour (12.0g, 41.8mmol), potassium carbonate (14.5g, 104.6mmol), tetra-triphenylphosphine palladium (2.4g, 2.1mmol), 1,4- bis-
Six ring of oxygen (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 -6 (13.2g, yield 71%) LC- with recrystallizing methanol
446.9 (M+H of MS:M/Z)+。
The synthesis of 9.RH-091:
Intermediate compound I -6 (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)+。
RH-271, LC-MS:M/Z 693.8 (M+H) are obtained by similar reaction+。
10. the synthesis of intermediate compound I -7:
Intermediate compound I -3 (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 -7 (13.7g, yield 63%) LC- with recrystallizing methanol
523.0 (M+H of MS:M/Z)+。
The synthesis of 11.RH-097:
Intermediate compound I -7 (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 (6.2g, yield 86%).LC-MS:M/Z 753.9 (M+H)+。
RH-277, LC-MS:M/Z 769.9 (M+H) are obtained by similar reaction+。
Embodiment
1. first embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1263cd/m2(5.6V).At this time, CIEx=0.659, y=0.330.
2. the second embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1172cd/m2(5.8V).At this time, CIEx=0.660, y=0.329.
3. third embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1281cd/m2(5.7V).At this time, CIEx=0.659, y=0.329.
4. the 4th embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1179cd/m2(5.9V).At this time, CIEx=0.660, y=0.329.
5. the 5th embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1254cd/m2(5.7V).At this time, CIEx=0.659, y=0.329.
6. the 6th embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1173cd/m2(5.9V).At this time, CIEx=0.660, y=0.329.
7. the 7th embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1272cd/m2(5.8V).At this time, CIEx=0.659, y=0.330.
8. the 8th embodiment
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 × 10-6Support.Hereafter, on ITO substrate with
With
The layer for sequentially forming organic substance.
At 0.9 ma, brightness is equal to 1189cd/m2(6.0V).At this time, CIEx=0.660, y=0.330.
9. 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 × 10-6Support.On an ito substrate with
WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 780cd/m2(7.5V).At this time, CIEx=0.659, y=0.329.
Increasing (becoming much larger with the X value of chromaticity coordinate) with the excitation purity of organic electroluminescence device as shown in Figure 1 can
Degree of opinion 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 comparison
Example is compared, and the current efficiency of the second embodiment and the 6th embodiment increases by 40% or more.
Luminescent layer by using 1 compound represented of formula as organic electroluminescence device, the present invention are provided with excellent
The organic electroluminescence device of different excitation purity and brightness and extended durability.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent defines.
Claims (6)
1. a kind of phosphorescence host compound, it is characterised in that: its structural formula is shown in formula I,
In above-mentioned structural formula I, X is O or S, and Z is independently selected from flowering structure:
Wherein, Ar is independently selected from one of C6-C30 aryl, C2-C30 heteroaryl.
2. phosphorescence host 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. phosphorescence host 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. phosphorescence host compound according to claim 1, it is characterised in that: the Ar is independently selected from following:
5. phosphorescence host 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 electroluminescence device using phosphorescence host compound described in any one of claim 1-5,
Be characterized in that: the organic electroluminescence device sequentially includes the anode of deposition, hole injection layer, hole transmission layer, shines
Layer, electron transfer layer, electron injecting layer and cathode, material of main part of the phosphorescence host compound as luminescent layer.
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| CN110467630A (en) * | 2019-07-26 | 2019-11-19 | 浙江华显光电科技有限公司 | A kind of phosphorescent compound and the organic light emitting diode device using the compound |
| 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 |
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