CN109678876A - 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
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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, Z 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 cyano fluorobenzene (30g, 0.25mol) is added and is equipped in the round-bottomed flask of stirrer and is dissolved with anhydrous dimethyl sulfoxide.
Then triethylamine (76.4g, 0.76mol) and methyl thioglycolate (26.7g, 0.25mol) is added.Mixed solution is warming up to 100
DEG C reaction three hours, reaction solution is poured into ice water later.Filter be precipitated solid and be dried to obtain intermediate compound I -1 (36.5g,
70%).208.3 (M+H of LC-MS:M/Z)+。
2. the synthesis of intermediate compound I -2:
Intermediate compound I -1 (35g, 0.17mol) and carbamide (50.7g, 0.84mol) are added in 2L round-bottomed flask.At 200 DEG C
At a temperature of react two hours.It is cooled to room temperature to pyroreaction liquid, sodium hydroxide solution is added.Reaction solution is filtered to remove miscellaneous
Matter obtains intermediate compound I -2 (27.6g, 75%) with being concentrated and dried after the acidification of 2M hydrochloric acid solution.LC-MS:M/Z 219.2 (M+H)+。
3. the synthesis of intermediate compound I -3:
Intermediate compound I -2 (25g, 0.11mol) and phosphorus oxychloride (300mL) are added in 1000ml round-bottomed flask.Mixed solution stirs
Mix back flow reaction six hours.Reaction solution pours into after being cooled to room temperature and stirs to get sediment in ice water.During filtering precipitate obtains
Mesosome I-3 (24.8g, 85%).256.1 (M+H of LC-MS:M/Z)+。
4. the synthesis of intermediate compound I -4:
Intermediate compound I -3 (10g, 39.2mmol) is added in round-bottomed flask, (9- phenyl -9H- carbazole -3- base) boric acid (11.3g,
39.2mmol), tetra-triphenylphosphine palladium (1.4g, 1.2mmol), sodium hydroxide (3.9g, 98mmol) and tetrahydrofuran (200mL)
With the mixed solvent of deionized water (100mL).Reaction system is heated to 80 DEG C of back flow reactions.It is cooled to room temperature after the reaction was completed,
With distilled water dilute reaction solution.Reaction solution then is extracted with methylene chloride and water, with the dry organic phase of anhydrous magnesium sulfate and is concentrated.
It is purified with silica gel column chromatography, intermediate compound I -4 (14.5g, 80%) is obtained after recrystallization.462.9 (M+H of LC-MS:M/Z)+。
The synthesis of 5.RH-001:
Intermediate compound I -4 (5g, 10.8mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (3.2g,
11.9mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.6g,
32.5mmol) 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 80%).LC-MS:M/Z 693.8 (M+H)+。
6. the synthesis of intermediate compound I -5:
Intermediate compound I -3 (10g, 39.2mmol) is added in round-bottomed flask, (9- phenyl -9H- carbazole -3- base) boric acid (14.2g,
39.2mmol), tetra-triphenylphosphine palladium (1.4g, 1.2mmol), sodium hydroxide (3.9g, 98mmol) and tetrahydrofuran (200mL)
With the mixed solvent of deionized water (100mL).Reaction system is heated to 80 DEG C of back flow reactions.It is cooled to room temperature after the reaction was completed,
With distilled water dilute reaction solution.Reaction solution then is extracted with methylene chloride and water, with the dry organic phase of anhydrous magnesium sulfate and is concentrated.
It is purified with silica gel column chromatography, intermediate compound I -5 (15.8g, yield 75%) is obtained after recrystallization.539.1 (M+H of LC-MS:M/Z)+。
The synthesis of 7.RH-007:
Intermediate compound I -5 (5g, 9.3mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (2.7g,
10.2mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.1g,
27.9mmol) 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 (5.4g, yield 75%).LC-MS:M/Z 769.9 (M+H)+。
8. the synthesis of intermediate compound I -6:
Intermediate compound I -3 (10g, 39.2mmol) is added in round-bottomed flask, (9- phenyl -9H- carbazole -2- base) boric acid (11.3g,
39.2mmol), tetra-triphenylphosphine palladium (1.4g, 1.2mmol), sodium hydroxide (3.9g, 98mmol) and tetrahydrofuran (200mL)
With the mixed solvent of deionized water (100mL).Reaction system is heated to 80 DEG C of back flow reactions.It is cooled to room temperature after the reaction was completed,
With distilled water dilute reaction solution.Reaction solution then is extracted with methylene chloride and water, with the dry organic phase of anhydrous magnesium sulfate and is concentrated.
It is purified with silica gel column chromatography, intermediate compound I -6 (13.6g, 78%) is obtained after recrystallization.462.9 (M+H of LC-MS:M/Z)+。
The synthesis of 9.RH-091:
Intermediate compound I -6 (5g, 10.8mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (3.2g,
11.9mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.6g,
32.5mmol) 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 (5.6g, yield 75%).LC-MS:M/Z 693.8 (M+H)+。
10. the synthesis of intermediate compound I -7:
2,4 dichloro benzene simultaneously [4,5] thiophene [3,2-d] pyrimidine (10g, 39.2mmol), (9- phenyl-are added in round-bottomed flask
9H- carbazole -2- base) boric acid (14.2g, 39.2mmol), tetra-triphenylphosphine palladium (1.4g, 1.2mmol), sodium hydroxide (3.9g,
98mmol) and the mixed solvent of tetrahydrofuran (200mL) and deionized water (100mL).It is anti-to 80 DEG C of reflux to heat reaction system
It answers.It is cooled to room temperature after the reaction was completed, with distilled water dilute reaction solution.Reaction solution then is extracted with methylene chloride and water, with nothing
The dry organic phase of water magnesium sulfate is simultaneously concentrated.It is purified with silica gel column chromatography, intermediate compound I -7 (14.7g, yield is obtained after recrystallization
70%).539.1 (M+H of LC-MS:M/Z)+。
The synthesis of 11.RH-097:
Intermediate compound I -7 (5g, 9.3mmol) is added in 250ml three-necked flask, 7H- dibenzo [c, g] carbazole (2.7g,
10.2mmol), tris(dibenzylideneacetone) dipalladium (4mol%), tri-tert-butylphosphine (8mol%), potassium tert-butoxide (3.1g,
27.9mmol) 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 70%).LC-MS:M/Z 769.9 (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
RH-001+(btp)2Ir (acac) ((5%)WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1263cd/m2(5.9V).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 base
Plate.
The substrate is then placed in vacuum chamber.Normal pressure is set as 1 × 10-6Support.Hereafter, on ITO substrate with
RH-007+(btp)2Ir (acac) (5%)WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1172cd/m2(6.1V).At this time, CIEx=0.658, y=0.331.
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
RH-091+(btp)2Ir (acac) (5%)WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1249cd/m2(6.0V).At this time, CIEx=0.659, y=0.331.
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
RH-097+(btp)2Ir (acac) (5%)WithIt is suitable
The layer of sequence formation organic substance.
At 0.9 ma, brightness is equal to 1121cd/m2(6.1V).At this time, CIEx=0.659, 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
CPB+(btp)2Ir (acac) (5%)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 40% 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.
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| 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 |
| 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 |
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