CN107266438A - A kind of heterocyclic organic electroluminescent compounds and its organic electroluminescence device - Google Patents
A kind of heterocyclic organic electroluminescent compounds and its organic electroluminescence device Download PDFInfo
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- CN107266438A CN107266438A CN201710677387.8A CN201710677387A CN107266438A CN 107266438 A CN107266438 A CN 107266438A CN 201710677387 A CN201710677387 A CN 201710677387A CN 107266438 A CN107266438 A CN 107266438A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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Abstract
The invention provides a kind of heterocyclic organic electroluminescent compounds, it has following structure：The compound has preferable heat endurance, and high-luminous-efficiency, high luminance purity can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the compound that at least one layer contains such as structural formula I in organic layer, the organic electroluminescence device made using the heterocyclic organic electroluminescent compounds has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of heterocyclic organic electroluminescent compounds and
Its organic electroluminescence device, belongs to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer
And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer
Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed
The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environment-friendly, can be applied on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.Applying voltage-operated additionally, due to OLED
When, Joule heat can be produced so that organic material is easily crystallized, have impact on life-span and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, by efficiency
(Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154) is lifted to 100%, and its application is also big
The earth improves the efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, conventional
There is efficient and high triplet energy level as the CBP (4,4'-bis (9-carbazolyl)-biphenyl) of phosphorescent light body material,
When it is as material of main part, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.
But be due to CBP hole easily transmission and electronics hardly possible flowing characteristic so that the charge unbalance of luminescent layer, as a result reduce device
The efficiency of part.
The content of the invention
The invention provides a kind of heterocyclic organic electroluminescent compounds, it is the compound with following structural formula I：
Wherein, Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted
C3-C30 heteroaryl；
L is selected from substitution or unsubstituted C6-C30 aryl.
Preferably, Ar1And Ar2Independently selected from phenyl, xenyl, naphthyl, above aryl is further by C1-C10 alkyl
Substitution.
Preferably, L is selected from biphenyl and phenyl.
It is further preferred that described heterocyclic organic electroluminescent compounds are following structural 1-22 compound：
The heterocyclic organic electroluminescent compounds of the present invention can be applied in organic electroluminescence device, organic solar
Battery, OTFT and organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer
Include one layer or one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
More than layer, wherein the heterocyclic organic electroluminescent compounds that at least one layer contains as described in structural formula I in the organic layer：
Wherein Ar1、Ar2It is defined as described above with L.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, wherein the layer where heterocyclic organic electroluminescent compounds as described in structural formula I is luminescent layer；
Preferably, the heterocyclic organic electroluminescent compounds wherein described in structural formula I are structural formula 1-22 compound；
When heterocyclic organic electroluminescent compounds as described in structural formula I are used for luminescent device preparation, can individually it make
With can also be used in mixed way with other compounds；Heterocyclic organic electroluminescent compounds such as structural formula I can be used alone
A kind of compound therein, two or more the compound in structural formula I can also be used simultaneously.
The organic electroluminescence device of the present invention, further preferred mode is that the organic electroluminescence device includes sun
Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer
One or more kinds of structural formula I compound；It is further preferred that containing one or more kinds of structures in luminescent layer
Formula 1-22 heterocyclic organic electroluminescent compounds.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention is when having structural formula I compound using the present invention, and can arrange in pairs or groups makes
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer
Deng, and obtain blue and green light, gold-tinted, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance, can effectively be transferred to hole on luminescent layer from anode.There is I of the present invention compound except that can use
Outside, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included
Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six
(hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.In addition to the present invention is with Compounds of structural formula I, following compound, naphthalene compounds, pyrene can also be contained
Class compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene compound, pentacene class
Compound , perylene class compounds, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, benzimidazole chemical combination
Thing, furfuran compound, organic metal chelate complex, but not limited to this.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode
In, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows, heterocyclic organic electroluminescent compounds of the present invention as described in structural formula I, with preferable heat
Stability, high-luminous-efficiency, high luminance purity.The organic electroluminescent made using the heterocyclic organic electroluminescent compounds
Device has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Brightness and external quantum efficiency graph of a relation of the Fig. 1 for the organic electroluminescence device of embodiments of the invention；
Fig. 2 is a kind of organic electroluminescence device structural representation of the invention,
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transports
Layer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electron injecting layer,
190 are represented as negative electrode.
Embodiment 1
The synthesis of compound 1
Intermediate 1-1 synthesis
Added in single port bottle to bromobenzylcyanide (5g, 27.5mmol), carbazole (4.2g, 25mmol), sodium tert-butoxide
(4.8g, 50mmol), palladium, x-phos, 50ml toluene is heated to reflux 24h under nitrogen protection, cooling.Using revolving method
Remove toluene, add the dissolving of 50ml dichloromethane, after be washed with water.Organic phase is spin-dried for, and adds ethyl alcohol recrystallization, and suction filtration goes out product.
White solid 3.9g is obtained, yield is 60%.
Intermediate 1-2 synthesis
Intermediate 1-1 (1g, 3.7mmol), the bromo- PAs of 5- (0.78g, 4.5mmol), bromine are added in single port bottle
Change cuprous (0.18mmol, 27mg), phenanthroline (0.18mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorohenzene
(5mL), under nitrogen protection, in being reacted 24 hours at 130 DEG C, is cooled to after room temperature and is diluted with ethyl acetate, be filtered to remove nothing
Machine salt, column chromatography for separation is used after filtrate concentration.White solid 0.5g is obtained, yield is 31%.The synthesis of compound 1
The addition intermediate 1-2 (5g, 11.5mmol) into single port bottle, 9,9 '-spiral shell two [9H- fluorenes] -2- boric acid (4.1g,
11.5mmol), potassium carbonate (3.4g, 25mmol), tetra-triphenylphosphine palladium (50mg), tetrahydrofuran (60mL) and water (20mL),
It is heated to reflux 6 hours under nitrogen protection, raw material reaction is finished.Tetrahydrofuran is spin-dried for, product is extracted with dichloromethane.Concentration is organic
Phase, column chromatography for separation product obtains white product 6.2g, and yield is 80%.
Embodiment 2
The synthesis of compound 8
Synthetic method is with the synthesis of compound 1, except replacing 9,9 '-spiral shell two with 9,9- diphenylfluorene -4- boric acid
Outside [9H- fluorenes] -2- boric acid, yield is 74%.
Embodiment 3
The synthesis of compound 13
Intermediate 13-1 synthesis
Synthetic method is with intermediate 1-2 synthesis, raw materials used is 9- (3- cyano group benzene)-carbazoles and 2- amino -4-
Outside bromopyridine, yield is 44%.
The synthesis of compound 13
Synthetic method is with the synthesis of compound 1, raw materials used is intermediate 13-1 and 9,9- diphenylfluorene -2- boron
Acid.
Embodiment 4
The synthesis of compound 19
Intermediate 37-1 synthesis
Synthetic method is with intermediate 1-2 synthesis, except replacing the bromo- 2- amino pyrroles of 5- with the bromo- PAs of 4-
Outside pyridine, yield is 36%.
The synthesis of compound 19
Synthetic method is with the synthesis of compound 1, in addition to replacing intermediate 1-2 with intermediate 37-1, yield is
71%.
Embodiment 5-8
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, PEDOT thick spin coating 35nm on ITO:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is
Hole injection layer 130, is dried 30 minutes at 150 DEG C；
Then, it is hole mobile material 140 that the thick TAPC of 45nm are deposited on hole injection layer.
Then, TCTA is deposited, the thick electronic barrier layers 150 of 5nm are formed.
Then, the thick luminescent layers 160 of 20nm are deposited on electronic barrier layer, wherein, the compounds of this invention is luminous for main body
Material, and with weight than the Ir (piq) for 5%2Acac is used as phosphorescence doping guest materials.
Then, the thick TmPYPB of 55nm are deposited on luminescent layer and are used as electron transfer layer 170.
Finally, evaporation 0.6nm LiF are that electron injecting layer 180 and 80nm Al are used as device cathodes 190.
Prepared device (structural representation is shown in Fig. 2) measured with Photo Research PR650 spectrometers
10000cd/m2Brightness under external quantum efficiency be such as table 1.
Comparative example 1
Device prepared by comparative example is with embodiment 5-8 preparation methods, except replacing the compounds of this invention conduct with PH
Outside material of main part.The wherein brightness of the organic electroluminescence device of embodiment 5-8 and comparative example 1 and external quantum efficiency graph of a relation is shown in
Fig. 1.
Table 1
| Embodiment | Compound | Current efficiency (cd/A) | Glow color |
| 5 | 1 | 15 | Feux rouges |
| 6 | 8 | 14 | Feux rouges |
| 7 | 13 | 13 | Feux rouges |
| 8 | 19 | 14 | Feux rouges |
| Comparative example 1 | PH | 10 | Feux rouges |
The structural formula of compound described in device is as follows：
As can be seen from the table, new organic materials of the invention are used for organic electroluminescence device, can reduce work
Voltage, improves device efficiency, is the phosphorescent light body material with premium properties.As described above, the compound of the present invention has height
Stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
Preferred embodiment of the invention described in detail above.It should be appreciated that the ordinary skill of this area is without wound
The property made work just can make many modifications and variations according to the design of the present invention.Therefore, all technical staff in the art
Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Scheme, all should be in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of heterocyclic organic electroluminescent compounds, it is characterised in that be the compound with following structural formula I：
Wherein, Ar1And Ar2Independently selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted C3-C30
Heteroaryl；
L is selected from substitution or unsubstituted C6-C30 aryl.
2. heterocyclic organic electroluminescent compounds as claimed in claim 1, it is characterised in that Ar1And Ar2Independently selected from
Phenyl, xenyl, naphthyl, above aryl are further replaced by C1-C10 alkyl.
3. heterocyclic organic electroluminescent compounds as claimed in claim 1, it is characterised in that L is selected from biphenyl and phenyl.
4. heterocyclic organic electroluminescent compounds as claimed in claim 1, it is characterised in that it is following structural 1-22
Compound：
。
5. a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer includes luminescent layer, hole
It is at least one layer of in implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, in the organic layer at least
There is one layer containing the heterocyclic organic electroluminescent compounds as described in structural formula I.
6. organic electroluminescence device as claimed in claim 4, it is characterised in that the heterocyclic as described in structural formula I is organic
Layer where electroluminescent compounds is luminescent layer.
7. organic electroluminescence device as claimed in claim 4, it is characterised in that the heterocyclic as described in structural formula I is organic
Electroluminescent compounds are structural formula 1-22 compound.
8. organic electroluminescence device as claimed in claim 4, it is characterised in that the heterocyclic as described in structural formula I is organic
Electroluminescent compounds can be used alone, and can also be used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 4, it is characterised in that the heterocyclic as described in structural formula I is organic
A kind of compound therein is used alone in electroluminescent compounds, or uses the two or more compounds in structural formula I simultaneously.
10. organic electroluminescence device as claimed in claim 4, it is characterised in that the organic electroluminescence device is organic
The gross thickness of layer is 1-1000nm.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590770A (en) * | 2019-08-22 | 2019-12-20 | 武汉尚赛光电科技有限公司 | Triazolopyridine-based organic electroluminescent material and organic electroluminescent device |
| KR20200126198A (en) * | 2019-04-29 | 2020-11-06 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015099450A1 (en) * | 2013-12-27 | 2015-07-02 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| CN106632325A (en) * | 2017-01-25 | 2017-05-10 | 上海道亦化工科技有限公司 | Azacycle-containing compound and organic electroluminescence device thereof |
-
2017
- 2017-08-09 CN CN201710677387.8A patent/CN107266438A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015099450A1 (en) * | 2013-12-27 | 2015-07-02 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
| CN106632325A (en) * | 2017-01-25 | 2017-05-10 | 上海道亦化工科技有限公司 | Azacycle-containing compound and organic electroluminescence device thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200126198A (en) * | 2019-04-29 | 2020-11-06 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| KR102521449B1 (en) | 2019-04-29 | 2023-04-12 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN110590770A (en) * | 2019-08-22 | 2019-12-20 | 武汉尚赛光电科技有限公司 | Triazolopyridine-based organic electroluminescent material and organic electroluminescent device |
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Application publication date: 20171020 |