CN109694371A - 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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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,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.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 0LED 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 is directed to a kind of phosphorescence host compound and a kind of OLED device using the compound, they are solved substantially
Limitation and defect bring one or more problem in the prior art.
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, 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 the shining as organic light emitting diode device of chemical formula shown in I
Layer has 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:
By the bromo- 2,4- dimethoxy quinoline (40g, 148.6mmol) of 8-, ethyl 2- (4,4,5,5- in the flask of 2000mL
Two oxygroup -2- base of tetramethyl -1,3,2-) benzoic acid (45.2g, 163.5mmol), potassium carbonate (51.4g, 371.6mmol), four
Triphenylphosphine palladium (5mol%) is dissolved in 1,4 dioxane (400mL) and water (200mL).Mixture heats back under nitrogen protection
Stream 12 hours.
Obtained mixture is added in 750ml methanol, the solid being wherein precipitated is filtered and is dissolved in chlorobenzene, with silica gel/silicon
Diatomaceous earth filtering obtains intermediate compound I -1 (34.2g, yield 68%) with recrystallizing methanol after concentration removes organic solvent.LC-MS:
M/Z 339.4(M+H)+。
2. the synthesis of intermediate compound I -2:
Intermediate compound I -1 (34g, 100.5mmol) is dissolved in anhydrous tetrahydro furan in 1000mL milliliters of round-bottomed flask
(400mL).Under conditions of -70 DEG C, be slowly added dropwise ether do solvent 1.5M methyUithium solution (140.7mL,
211.0mmol)) and keep the temperature -70 DEG C at a temperature of stir 2 hours.When the reactions are completed, 150mL ice water is added and 250mL is full
And ammonium chloride solution.Organic layer is obtained by extraction, and twice with distilled water flushing, organic phase is concentrated and dried.By normal heptane/toluene
It is recrystallized to give colorless solid intermediate compound I -2 (26.1g, yield 80%).LC-MS:M/Z 325.4 (M+H)+。
3. the synthesis of intermediate compound I -3:
Intermediate compound I -2 (26g, 80.2mmol) is dissolved with 350mL anhydrous methylene chloride in the round-bottomed flask of 1000mL,
Boron trifluoride ether (12.5g, 88.2mmol) is then slowly added dropwise for about ten minutes.Mixture is heated to 50 DEG C, and stirring 2 is small
When.Synthetic is cooled to room temperature, distilled water is added, three times with ether extraction.Have obtained in anhydrous magnesium sulfate is dry
Machine layer.It is concentrated and dried, is purified to obtain intermediate -3 (12.3g, yield 50%) with silicagel column.307.4 (M+H of LC-MS:M/Z)+。
4. the synthesis of intermediate compound I -4:
Intermediate compound I -3 (12g, 39.2mmol) is dissolved in glacial acetic acid (150mL) in 1000mL round-bottomed flask, then plus
Enter sodium iodide (23.5g, 156.7mmol), after mixture is stirred to react 1 hour at 60 DEG C, distillation under pressure removes solvent.
The residue therefrom extracted is dissolved in methylene chloride (200mL), is then cleaned with sodium thiosulfate solution.It has been obtained by extraction
Machine layer is dry with anhydrous magnesium sulfate, is concentrated under reduced pressure.Gained mixture without purification be added to equipped with phosphoryl chloride phosphorus oxychloride (36.6g,
In 150ml flask 274.2mmol), flowed next time 4 hours in 120 DEG C of temperature conditions of nitrogen protection.Reaction mixture is by slowly
Ground pours into excessive ice to complete reaction, filters the solid of precipitation.Obtained solid water and methanol is dry after cleaning, and obtains
Mesosome I-4 (10.7g, yield 87%).LC-MS:M/Z 316.2 (M+H)+。
5. the synthesis of intermediate compound I -5:
Intermediate compound I -4 (10.0g, 31.7mmol) is added in 500mL reaction flask, (9- phenyl -9H- carbazole -3- base) boron
Sour (9.1g, 31.7mmol), potassium carbonate (11.0g, 79.3mmol), tetra-triphenylphosphine palladium (5mol%), 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 first
In alcohol, the solid of precipitation is filtered.With the solid of chlorobenzene solution modeling, filtered with the funnel equipped with diatomite and silica white.Filtering
Obtained orange liquid concentration is evaporated and obtains intermediate compound I -5 (11.2g, yield 68%) LC-MS:M/Z with recrystallizing methanol
523.0(M+H)+。
The synthesis of 6.RH-001:
Intermediate compound I -5 (5g, 9.6mmol) is added in 250mL three-necked flask, 7H- dibenzo [c, g] carbazole (3.1g,
11.5mmol), 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-001 (6.0g, yield 83%).LC-MS:M/Z 753.9 (M+H)+。
7. the synthesis of intermediate compound I -6:
Intermediate compound I -4 (10.0g, 31.7mmol) is added in 500mL reaction flask, 9- (4- xenyl) -3- boric acid carbazole
(11.5g, 31.7mmol), potassium carbonate (11.0g, 79.3mmol), 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 -6 (12.0g, yield 63%) with recrystallizing methanol.LC-
599.1 (M+H of MS:M/Z)+。
The synthesis of 8.RH-007:
Intermediate compound I -6 (5g, 8.4mmol) is added in 250mL three-necked flask, 7H- dibenzo [c, g] carbazole (2.7g,
10.0mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (2.8g,
25.1mmol) 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 (5.6g, yield 81%).LC-MS:M/Z 830.0 (M+H)+。
9. the synthesis of intermediate compound I -7:
Intermediate compound I -4 (10.0g, 31.7mmol) is added in 500mL reaction flask, (9- phenyl -9H- carbazole -2- base) boron
Sour (9.1g, 31.7mmol), potassium carbonate (11.0g, 79.3mmol), tetra-triphenylphosphine palladium (5mol%), 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 first
In alcohol, the solid of precipitation is filtered.With the solid of chlorobenzene solution modeling, filtered with the funnel equipped with diatomite and silica white.Filtering
Obtained orange liquid concentration is evaporated and obtains intermediate compound I -7 (11.4g, yield 69%) LC-MS:M/Z with recrystallizing methanol
523.0(M+H)+。
The synthesis of 10.RH-091:
Intermediate compound I -7 (5g, 9.6mmol) is added in 250mL three-necked flask, 7H- dibenzo [c, g] carbazole (3.1g,
11.5mmol), 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-091 (6.0g, yield 83%).LC-MS:M/Z 753.9 (M+H)+。
11. the synthesis of intermediate compound I -8:
Intermediate compound I -4 (10.0g, 31.7mmol) is added in 500mL reaction flask, 9- (4- xenyl) -2- boric acid carbazole
(11.5g, 31.7mmol), potassium carbonate (11.0g, 79.3mmol), 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 -8 (12.3g, yield 65%) with recrystallizing methanol.LC-
599.1 (M+H of MS:M/Z)+。
The synthesis of 12.RH-097:
Intermediate compound I -8 (5g, 8.4mmol) is added in 250mL three-necked flask, 7H- dibenzo [c, g] carbazole (2.7g,
10.0mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (2.8g,
25.1mmol) 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 (5.4g, yield 80%).LC-MS:M/Z 830.0 (M+H)+。
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 1191d/m2(6.1V).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 1087cd/m2(6.2V).At this time, CIEx=0.659y=0.331.
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 1202cd/m2(6.0V).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 1098cd/m2(6.1V).At this time, CIEx=0.630, y=0.329.
5. 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 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: 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. 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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Cited By (6)
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| CN109438468A (en) * | 2018-11-26 | 2019-03-08 | 浙江华显光电科技有限公司 | A kind of phosphorescence host compound and its organic electroluminescence device using the compound |
| 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 |
| CN110951482A (en) * | 2019-10-23 | 2020-04-03 | 宇瑞(上海)化学有限公司 | Phosphorescent compound and organic electroluminescent device using same |
| 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 |
| CN109678875B (en) * | 2018-11-08 | 2022-05-20 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using same |
| CN109678867B (en) * | 2018-11-08 | 2022-05-20 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using the same |
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| CN109678875B (en) * | 2018-11-08 | 2022-05-20 | 浙江华显光电科技有限公司 | Phosphorescent compound and organic light emitting diode device using same |
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| 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 |
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Application publication date: 20190430 |