CN104471022A - Organic light-emitting compound comprising acridine derivatives, and organic light-emitting device comprising same - Google Patents
Organic light-emitting compound comprising acridine derivatives, and organic light-emitting device comprising same Download PDFInfo
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Abstract
The organic light-emitting compound comprising acridine derivatives according to the present invention adjusts the charge balance in an organic material layer by means of comprising an appropriate balance between the acridine derivatives and a cyclic compound, thereby achieving excellent luminance, power efficiency, heat resistance, charge transport performance, and charge injection performance to thus increase color purity and luminous efficiency. Therefore, the organic light-emitting compound of the present invention can be used as a light-emitting material for an organic light-emitting device in order to exhibit low driving voltage and high luminance and luminous efficiency for an organic light-emitting device, thus enabling the maximized performance and improved lifespan of a full-color organic panel.
Description
Technical field
The present invention relates to the organic luminescent compounds comprising acridine derivatives and the organic illuminating element comprising this organic luminescent compounds.
Background technology
Recently, can with the emissive type organic illuminating element of low voltage drive, with the liquid-crystal display (LCD of the main flow as flat panel displaying element, liquid crystal display) compare, field angle, contrast gradient etc. are excellent and without the need to backlight, thus can realize lightweight, slimming, also favourable and color reproduction range is wide in power consumption, therefore, receive much concern as display element of future generation.
In general, organic illuminating element has in negative electrode (electron injection electrode) and anode (hole injecting electrode) and the structure comprising organic matter layer between above-mentioned two electrodes.Now, organic matter layer is except comprising luminescent layer (EML, light emitting layer) outside, hole injection layer (HIL can be comprised, hole injection layer), hole transmission layer (HTL, hole transport layer), electron transfer layer (ETL, electron transport layer), or electron injecting layer (EIL, electron injection layer), electronic barrier layer (EBL can be comprised further from the characteristics of luminescence of luminescent layer, electron blocking layer) or hole blocking layer (HBL, holeb locking layer).
If apply electric field to the organic illuminating element of this structure, then hole from anode inject and electronics inject from negative electrode, and hole and electronics reconfigure (recombination) at luminescent layer after respectively through hole transmission layer and electron transfer layer and form luminescent excitons (electron-hole pair, exitons).The luminescent excitons formed returns ground state (ground states) and gives out light.
Luminophore can divide into blueness, green, red light emitting substance and the yellow thoroughly realized needed for better self colour and the Yellow luminous material of Zhu according to illuminant colour.In addition, in order to improve efficiency and the stability of luminance, also to adulterate luminescent pigment (doping agent) at luminescent layer (main body).Its principle is as follows: if mix a small amount of doping agent at luminescent layer, then the electron-hole pair produced in main body transfers to doping agent and sends high-level efficiency light, and wherein, its band gap of described doping agent is less than the main body of main composition luminescent layer and luminous efficiency is excellent.Now, because the wavelength of main body moves to the wave band of doping agent, the light of desired wavelength can thus be obtained according to the kind of utilized doping agent.
As the luminophore of luminescent layer being used in organic illuminating element, there will be a known multiple compounds up to now, but when make use of the organic illuminating element of luminophore known up to now, due to high driving voltage, low efficiency and short work-ing life, thus have any problem in practical more.Therefore, continue the effort having carried out a kind of organic illuminating element of exploitation, described organic illuminating element utilization has the material of the excellent characteristics of luminescence thus has the advantages such as low voltage drive, high brightness and long life.
Summary of the invention
Technical problem
In order to solve problem as above, the present invention its object is to provide a kind of organic luminescent compounds that improve the novelty of purity of color, luminous efficiency, brightness, power-efficient and thermotolerance etc.
In addition, the present invention its object is to provide a kind of and comprises above-claimed cpd and low driving voltage and high-luminous-efficiency and high brightness be shown and thoroughly can realize the organic illuminating element of long life.
To deal with problems scheme
In order to achieve the above object, the invention provides a kind of organic luminescent compounds comprising acridine derivatives, this organic luminescent compounds represents with following chemical formula 1:
Chemical formula 1
In above-mentioned formula,
X is substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen-atoms of acridine can not combine in No. 3 positions of heteroaryl class part,
R1 to R17 is separately hydrogen; Heavy hydrogen; With the alkyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the thiazolinyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkynyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkoxyl group of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the aryloxy of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-30 of nitro; With the aryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-36 of nitro; Or with the heteroaryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-36 of nitro, optionally, in above-mentioned R1 to R17 adjacent group can be combined with each other and form saturated or unsaturated carbocyclic.
In addition, the invention provides and a kind ofly prepare the method comprising the organic luminescent compounds of acridine derivatives represented with chemical formula 1, the method is characterized in that, comprises the step that following chemical formula 1-1 and chemical formula 1-2 is reacted:
Chemical formula 1-1
Chemical formula 1-2
Above-mentioned X and R1 to R17 with define at chemical formula 1 identical.
In addition, the invention provides a kind of organic illuminating element, it comprises the compound that represents using above-mentioned chemical formula 1 as luminophore at organic matter layer.
Invention effect
Organic luminescent compounds of the present invention regulates the charge balance in organic matter layer by the suitable mediation of acridine derivatives and ring compound, thus brightness, power-efficient, thermotolerance, charge transport properties and charge injection excellent property and purity of color and luminous efficiency can be improved, thus can be applicable in the functional layer material of organic illuminating element and the main body of luminescent layer or doping agent more than one.Therefore, the organic illuminating element comprising compound of the present invention illustrates low driving voltage and high brightness and high-luminous-efficiency, the performance of the organic panel of full color can be made thus to maximize and can extend the work-ing life of the organic panel of full color.
Accompanying drawing explanation
Fig. 1 schematically illustrates the section of the OLED according to one embodiment of the invention.
What Fig. 2 illustrated the organic electroluminescent LED of the principle of luminosity had based on organic light emission phenomenon can be with (band) figure.
Nomenclature
10-substrate, 11-anode, 12-hole injection layer, 13-hole transport layer, 14-luminescent layer, 15-electron transfer layer, 16-negative electrode.
Embodiment
With the compound of the present invention that following chemical formula 1 represents, it is characterized in that, acridine part (moiety) and aryl class or heteroaryl class part are directly connected in the nitrogen-atoms of acridine:
Chemical formula 1
In above-mentioned formula,
X is substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen-atoms of acridine can not combine in No. 3 positions of heteroaryl class part,
R1 to R17 is separately hydrogen; Heavy hydrogen; With the alkyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the thiazolinyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkynyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkoxyl group of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the aryloxy of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-30 of nitro; With the aryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-36 of nitro; Or with the heteroaryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-36 of nitro, optionally, in above-mentioned R1 to R17 adjacent group can be combined with each other and form saturated or unsaturated carbocyclic.
When above-mentioned R1 to R10 is replaced by heavy hydrogen respectively, at least 20% can by heavy-hydrogenated in R1 to R10, preferably at least 40% by heavy-hydrogenated, and more preferably at least 50% by heavy-hydrogenated.
In addition, in above-claimed cpd, the aryl class be directly connected with the nitrogen-atoms of acridine part (moiety) or heteroaryl class part are when being replaced by heavy hydrogen, and preferably at least 50% by heavy-hydrogenated.
In addition, the substituting group of above-mentioned X and R1 to R17 preferably separately replaced with the substituting group of more than a kind be selected from the group that is made up of the aryl amine of the alkoxyl group of the heteroaryl of the aryl of the Heterocyclylalkyl of the cycloalkyl of the alkoxyl group of the alkyl of heavy hydrogen, halogen, itrile group, nitro, C1-30, C1-30, C3-30, C3-30, C6-30, C5-30, C1-30, the aryloxy of C6-30 and C6-30, but be not limited thereto, adjacent group can be combined with each other and form saturated or unsaturated carbocyclic.
In the present invention, the preference of the compound represented with above-mentioned chemical formula 1 is as follows:
According to the compound of chemical formula 1 of the present invention, its acridine part and aryl class or heteroaryl class part are directly connected in the nitrogen-atoms of acridine, thus regulate the charge balance in organic matter layer by the suitable mediation of acridine derivatives and ring compound.Thus, brightness, power-efficient, thermotolerance, charge transport properties and charge injection excellent property and can improve purity of color and luminous efficiency, thus can be applicable in the functional layer material of organic illuminating element and the main body of luminescent layer or doping agent more than one.
Therefore, if be suitable for compound of the present invention on organic illuminating element, then the characteristics such as the driving voltage of luminous element and luminous efficiency can be improved.
In addition, the invention provides and a kind ofly prepare the method comprising the organic luminescent compounds of acridine derivatives represented with chemical formula 1, the method is characterized in that, comprises the step that following chemical formula 1-1 and chemical formula 1-2 is reacted:
Chemical formula 1-1
Chemical formula 1-2
Above-mentioned X is identical with R1 to R17 with the X defined at chemical formula 1 with R1 to R17.
As a concrete example, the compound according to chemical formula 1 of the present invention can be prepared according to according to the method for following reaction formula 1.
Reaction formula 1
In above-mentioned reaction formula 1, X is identical with the X defined at chemical formula 1, and each R is corresponding with R1 and R2 of chemical formula 1-1 respectively.
In addition, the invention provides a kind of organic illuminating element, it comprises the compound that represents using above-mentioned chemical formula 1 and as luminophore at organic matter layer.Now, compound of the present invention can be used alone or use together with known organic luminescent compounds.
In addition, organic illuminating element of the present invention comprises the organic matter layer of more than 1 layer, and this organic matter layer contains the compound represented with above-mentioned chemical formula 1, and the preparation method that the following describes above-mentioned organic illuminating element is as follows.
Above-mentioned organic illuminating element can comprise more than 1 in the organic matter layers such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL) between anode (anode) and negative electrode (cathod).
First, at substrate top evaporation, there is the positive electrode material of high work function and form anode.Now, aforesaid substrate can be used in the substrate that common organic illuminating element uses, and especially preferably uses glass substrate or transparent plastic substrate that physical strength, thermostability, transparency, surface flatness, handling easiness and water-repellancy are excellent.In addition, as positive electrode material, the tin indium oxide (ITO) that transparent and electrically conductive can be used excellent, indium zinc oxide (IZO), stannic oxide (SnO2), zinc oxide (ZnO) etc.Above-mentioned positive electrode material can utilize common anodic formation method to carry out evaporation, specifically, vapour deposition method or sputtering method can be utilized to carry out evaporation.
Thereafter, utilize as vacuum vapour deposition, spin-coating method, teeming practice, Langmuir-Blodgett (Langmuir-Blodgett, LB) method such as method can form hole injection layer material on above-mentioned positive electrode top, and the uniform film quality and not easily produce pin hole (pin hole) angularly of being easy to get calmly, preferably utilize vacuum vapour deposition and formed.When forming hole injection layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is with being used as the compound of material of hole injection layer, the structure of desired hole injection layer and thermal property etc. and different, but in general, preferably 50-500 DEG C evaporation temperature, 10-8 to 10-3 holder (torr) vacuum tightness, 0.01 to
the evaporation rate of/sec and
suitably select to the layer thicknesses of 5 μm.
Above-mentioned hole injection layer material, be not particularly limited, can by United States Patent (USP) the 4th, 356, phthalocyanine compound or the TCTA (4 as star burst sulfonamide derivatives class such as the CuPc disclosed in No. 429, 4 ＇, 4 "-three (N-carbazyl) triphenylamine), m-MTDATA (4, 4 ＇, 4 "-three (3-MethYlphenylamino) triphenylamine), m-MTDAPB (4, 4 ＇, 4 "-three (3-MethYlphenylamino) phenoxy group benzene), HI-406 (N1, N1 ＇-(xenyl-4, 4 ＇-two bases) two (N1-(naphthyl-1-base)-N4, N4-diphenyl benzene-1, 4-diamines) etc. be used as hole injection layer material.
Then, utilize as the methods such as vacuum vapour deposition, spin-coating method, teeming practice, LB method can form hole transmission layer material on above-mentioned hole injection layer top, and be easy to get calmly uniform film quality and not easily produce pin hole angularly, preferably utilize vacuum vapour deposition and formed.When forming hole transmission layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.
In addition, above-mentioned hole transmission layer material, is not particularly limited, and it can select and use arbitrarily in the common known material being used in hole transmission layer.Specifically, above-mentioned hole transmission layer material can use carbazole derivative and the N such as N-phenyl carbazole, Polyvinyl carbazole, N ＇-bis-(3-aminomethyl phenyl)-N, N ＇-phenylbenzene-[1,1-xenyl]-4,4 ＇-diamines (TPD), N, N ＇-two (naphthyl-1-base)-N, N ＇-diphenylbenzidine (α-NPD) etc. have the common sulfonamide derivatives etc. of aromatic fused ring.
Thereafter, utilize as the methods such as vacuum vapour deposition, spin-coating method, teeming practice, LB method can form luminescent layer material on above-mentioned hole transmission layer top, and be easy to get calmly uniform film quality and not easily produce pin hole angularly, preferably utilize vacuum vapour deposition and formed.When forming luminescent layer when utilizing above-mentioned vacuum vapour deposition, although its evaporation condition is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.In addition, with regard to above-mentioned emitting layer material, the compound represented of the present invention can be used as main body or doping agent with chemical formula 1.
When the compound will represented with above-mentioned chemical formula 1 is used as light emitting host, phosphorescence or fluorescent dopants can be used together and forms luminescent layer.Now, IDE102 or IDE105 or BD142 (two (3,4-3,5-dimethylphenyl)-N6, N12-bis-sym-trimethylbenzene base of N6, N12-that can buy in Co., Ltd.'s bright dipping (Idemitsu company) can be used as fluorescent dopants
(chrysene)-6,12-diamines), can using green phosphorescent doping agent Ir (ppy) 3 (three (2-phenylpyridine) iridium), F2Irpic (two (4 as blue phosphorescent doping agent as phosphorescent dopants, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (III)), the red phosphorescent doping agent RD61 etc. of UDC (Universal Display Corporation, the U.S.) company jointly carries out vacuum evaporation (doping) and uses.With regard to the doping content of doping agent, although be not particularly limited, the doping agent of 0.01 to 15 weight part that 100 weight part main bodys are preferably adulterated.When the content of doping agent is less than 0.01 weight part, there is the problem that can not normally develop the color because dopant dose is not enough, when the content of doping agent is more than 15 weight part, there is the problem that efficiency sharply declines because of concentration quenching effect.
In addition, when being used on luminescent layer together with phosphorescent dopants, in order to prevent the phenomenon that triplet exciton or hole are spread to electron transfer layer, preferably by vacuum vapour deposition or spin-coating method, further stacked hole suppresses material (HBL).Now, although the hole inhibitory substance that can use is not particularly limited, can selects arbitrarily in the known material being used as hole suppression material and utilize.Such as, hole described in oxadiazoles (oxadiazole) derivative or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11-329734 (A1) can be enumerated and suppress material etc., as its representative, Balq (two (8-hydroxy-2-methylquinoline-N1 can be used, O8)-biphenylyloxy aluminium), phenanthroline (phenanthrolines) compounds (such as: UDC company bathocuproine (Bathocuproine, BCP)) etc.
Form electron transfer layer on the luminescent layer top formed as described above, and now utilize the methods such as vacuum vapour deposition, spin-coating method, teeming practice to form above-mentioned electron transfer layer, especially preferably utilize vacuum vapour deposition and formed.
Above-mentioned electron transport layer materials transmits the function from electron injection electrode institute injected electrons with playing stably, its kind is not particularly limited, such as, can quinoline be used, especially can use three (oxine) aluminium (Alq3) or ET4 (6,6 ＇-(3,4-bis-sym-trimethylbenzene base-1,1-dimethyl-1H-thiophene coughs up-2,5-bis-bases) two-2,2 ＇-dipyridyl).In addition, portion stackedly can have material and the electron injecting layer (EIL) of the function easily making electronics inject from negative electrode on the electron transport layer, as electron injecting layer material, the materials such as LiF (lithium fluoride), NaCl (sodium-chlor), CsF (cesium fluoride), Li2O (Lithium Oxide 98min), BaO (barium oxide) can be utilized.
In addition, although the evaporation condition of above-mentioned electron transfer layer is different with used compound, in general, preferably select in the condition and range almost identical with forming hole injection layer.
Thereafter, electron injecting layer material can be formed on above-mentioned electron transfer layer top, now, common electron injecting layer material is formed above-mentioned electron transfer layer by methods such as vacuum vapour deposition, spin-coating method, teeming practices, especially forms above-mentioned electron transfer layer preferably by vacuum vapour deposition.
Finally, the method such as vacuum vapour deposition or sputter (sputtering) method is utilized to form negative electrode formation metal on electron injecting layer top and be used as negative electrode.Here, there is the metal of low work function, alloy, electric conductivity compound and their mixture and can be used as negative electrode formation metal.As object lesson, there are lithium (Li), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-Yin (Mg-Ag) etc.In addition, in order to obtain top emitting element, the transmission-type negative electrode employing ITO, IZO can also be utilized.
Organic illuminating element of the present invention can be not only have anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, the organic illuminating element of electron injecting layer, cathode construction, and the organic luminous element structure of various structures can be had, also can form the middle layer of 1 layer or 2 layers as required further.
As mentioned above, the thickness of each organic matter layer formed according to the present invention can regulate according to required degree, and described thickness is preferably 10 to 1,000nm, is more preferably 20 to 150nm.
In addition, the present invention can regulate the thickness of organic matter layer due to the organic matter layer comprising the compound represented with above-mentioned chemical formula 1 with molecular unit, therefore, has surface uniform and the preeminent advantage of morphological stability.
Organic luminescent compounds of the present invention, purity of color and luminous efficiency can be improved due to brightness, power-efficient, thermotolerance, charge transport properties and charge injection excellent property, thus be used as the luminophore of organic illuminating element and low driving voltage and high brightness and high-luminous-efficiency are shown, the performance of the organic panel of full color can be made thus to maximize and the work-ing life of the organic panel of full color can be extended.
Below, in order to contribute to understanding the present invention, preferred embodiment is shown, and following embodiment just illustrates the present invention, scope of the present invention also be can't help following embodiment and limited.
Embodiment 1: the synthesis of compound 1
By 9,9-dimethyl-9,10-acridan (9,9-dimethyl-9,10-dihydroacridine) 5g, 4-bromine diphenylene-oxide (4-bromodibenzo [b, d] furan) 7.1g, t-BuONa (sodium tert-butoxide) 3.5g, Pd
2(dba)
3(three (dibenzalacetone) two palladium) 0.9g, (t-Bu)
3p (tri-butyl phosphine) 1.2ml has carried out return stirring after dissolving in 100ml toluene.After reaction terminates, distilled water and ethanol (EA) is utilized to carry out extracting and carry out post purification and obtain compound 1.(productive rate is 61%)
m/z：375.16(100.0％)、376.17(29.5％)、377.17(4.4％)
Embodiment 2: the synthesis of compound 2
After bromo-for 2-N-phenylaniline (2-bromo-N-phenylaniline) 10g is dissolved in 100ml THF (tetrahydrofuran (THF)), temperature of reaction is reduced to-78 DEG C, drips the 2.5M BuLi (butyllithium) of 20ml lentamente and stirred 1 hour.Benzophenone (Benzophenone) 11g to be dissolved in 100ml THF (tetrahydrofuran (THF)) and after dripping lentamente, temperature be increased to room temperature and stirred 12 hours.After reaction terminates, distilled water and MC (methylene dichloride) will be utilized to carry out extracting and carry out filtration under diminished pressure and the solid obtained after utilizing anhydrous magnesium sulfate and removing water, after directly dissolving in 100ml acetic acid (Acetic acid) without purifying further, dripping 7ml sulfuric acid and also having carried out return stirring.After reaction terminates, distilled water and MC (methylene dichloride) is utilized to carry out extracting and carry out post purification to generated solid and obtain 7.1g I2.(productive rate 53%)
7g I2,4-bromine diphenylene-oxide (4-bromodibenzo [b, d] furan) 6.5g, t-BuONa (sodium tert-butoxide) 3g, Pd2 (dba) 3 of above-mentioned steps (three (dibenzalacetone) two palladium) 0.7g, (t-Bu) 3P (tri-butyl phosphine) 1ml have been carried out return stirring after dissolving in 150ml toluene.After reaction terminates, distilled water and EA (ethanol) is utilized to carry out extracting and carry out post purification and obtain compound.(productive rate 67%)
m/z：499.19(100.0％)、500.20(40.3％)、501.20(8.1％)、502.20(1.1％)
Embodiment 3: the synthesis of compound 3
Except reacting except replacing benzophenone (Benzophenone) with 9-Fluorenone (9H-fluoren-9-one), obtain following compound 3 with the method identical with the synthetic method of compound 2.
m/z：497.18(100.0％)、498.18(40.3％)、499.18(8.1％)、500.19(1.1％)
Embodiment 4: the synthesis of compound 4
Except reacting except replacing benzophenone (Benzophenone) with two (pyridin-3-yl) ketone (di (pyridin-3-yl) methanone), obtain following compound 4 with the method identical with the synthetic method of compound 2.
m/z：501.18(100.0％)、502.19(38.2％)、503.19(7.3％)、502.18(1.1％)
Embodiment 5: the synthesis of compound 5
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace bromine diphenylene-oxide (bromodibenzo [b, d] furan) (247.09), 4-bromine diphenylene-oxide (4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 5 with the method identical with the synthetic method of compound 1.
m/z：375.16(100.0％)、376.17(29.5％)、377.17(4.4％)
Embodiment 6: the synthesis of compound 6
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace 4-bromine diphenylene-oxide (4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 6 with the method identical with the synthetic method of compound 2.
m/z：499.19(100.0％)、500.20(40.3％)、501.20(8.1％)、502.20(1.1％)
Embodiment 7: the synthesis of compound 7
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 7 with the method identical with the synthetic method of compound 3.
m/z：497.18(100.0％)、498.18(40.3％)、499.18(8.1％)、500.19(1.1％)
Embodiment 8: the synthesis of compound 8
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 8 with the method identical with the synthetic method of compound 4.
m/z：501.18(100.0％)、502.19(38.2％)、503.19(7.3％)、502.18(1.1％)
Embodiment 9: the synthesis of compound 9
After bromo-for 2-N-phenylaniline (2-bromo-N-phenylaniline) 10g is dissolved in 100ml THF (tetrahydrofuran (THF)), temperature of reaction is reduced to-78 DEG C, drips the 2.5M BuLi (butyllithium) of 20ml lentamente and stirred 1 hour.Two (4-chloro-phenyl-) ketone (bis (4-chlorophenyl) methanone) 15.2g to be dissolved in 150ml THF (tetrahydrofuran (THF)) and after dripping lentamente, temperature is increased to room temperature and stirred 12 hours.After reaction terminates, distilled water and MC (methylene dichloride) will be utilized to carry out extracting and carry out filtration under diminished pressure and the solid obtained after utilizing anhydrous magnesium sulfate and removing water, after directly dissolving in 150ml acetic acid (Acetic acid) without purifying further, dripping 10ml sulfuric acid and having carried out return stirring.After reaction terminates, distilled water and MC (methylene dichloride) is utilized to carry out extracting and carry out post purification to generated solid and obtain 10g I3.(productive rate 62%)
9g I3,4-bromine diphenylene-oxide (4-bromodibenzo [b, d] furan) 6.65g, t-BuONa (sodium tert-butoxide) 3.2g, Pd2 (dba) 3 of above-mentioned steps (three (dibenzalacetone) two palladium) 0.8g, (t-Bu) 3P (tri-butyl phosphine) 1.1ml have been carried out return stirring after dissolving in 200ml toluene.After reaction terminates, distilled water and EA (ethanol) is utilized to carry out extracting and carry out post purification and obtain 11g I3-1.(productive rate 59%)
The 10g I3-1 of above-mentioned steps, pentanoic (diphenylamine) 6.85g, t-BuONa (sodium tert-butoxide) 2.5g, Pd2 (dba) 3 (three (dibenzalacetone) two palladium) 0.6g, (t-Bu) 3P (tri-butyl phosphine) 1.6ml have been carried out return stirring after dissolving in 200ml toluene.After reaction terminates, distilled water and EA (ethanol) is utilized to carry out extracting and carry out post purification and obtain 98g compound.(productive rate 55%)
m/z：833.34(100.0％)、834.34(67.1％)、835.35(21.8％)、836.35(4.8％)
Embodiment 10: the synthesis of compound 10
Except reacting except replacing pentanoic (diphenylamine) with 9H-carbazole (9H-carbazole), obtain following compound 10 with the method identical with the synthetic method of compound 9.
m/z：829.31(100.0％)、830.31(67.1％)、831.32(21.7％)、832.32(4.8％)
Embodiment 11: the synthesis of compound 11
Except with 2, the chloro-9-Fluorenone (2 of 7-bis-, 7-dichloro-9H-fluoren-9-one) replace two (4-chloro-phenyl-) ketone (bis (4-chlorophenyl) methanone) and outside reacting, obtain following compound 11 with the method identical with the synthetic method of compound 9.
m/z：831.32(100.0％)、832.33(66.5％)、833.33(22.7％)、834.34(4.7％)、832.32(1.1％)
Embodiment 12: the synthesis of compound 12
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 12 with the method identical with the synthetic method of compound 9.
m/z：833.34(100.0％)、834.34(67.1％)、835.35(21.8％)、836.35(4.8％)
Embodiment 13: the synthesis of compound 13
Except reacting except replacing pentanoic (diphenylamine) with 9H-carbazole (9H-carbazole), obtain following compound 13 with the method identical with the synthetic method of compound 12.
m/z：829.31(100.0％)、830.31(67.1％)、831.32(21.7％)、832.32(4.8％)
Embodiment 14: the synthesis of compound 14
Except with 1-bromine diphenylene-oxide (1-bromodibenzo [b, d] furan) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 14 with the method identical with the synthetic method of compound 11.
m/z：831.32(100.0％)、832.33(66.5％)、833.33(22.7％)、834.34(4.7％)、832.32(1.1％)
Embodiment 15: the synthesis of compound 15
By 9,9-dimethyl-9,10-acridan (9,9-dimethyl-9,10-dihydroacridine) 5g, 4-bromine dibenzothiophene (4-bromodibenzo [b, d] thiophene) 6.9g, t-BuONa (sodium tert-butoxide) 3.5g, Pd2 (dba) 3 (three (dibenzalacetone) two palladium) 0.9g, (t-Bu) 3P (tri-butyl phosphine) 1.2ml have carried out return stirring after dissolving in 100ml toluene.After reaction terminates, distilled water and EA (ethanol) is utilized to carry out extracting and carry out post purification and obtain compound 15.(yield rate 61%)
m/z：391.14(100.0％)、392.14(30.4％)、393.14(4.9％)、393.15(4.2％)、394.14(1.3％)
Embodiment 16: the synthesis of compound 16
Except with 4-bromine dibenzothiophene (4-bromodibenzo [b, d] thiophene) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 16 with the method identical with the synthetic method of compound 2.
m/z：515.17(100.0％)、516.17(41.2％)、517.18(7.9％)、517.17(5.0％)、518.17(1.9％)、518.18
Embodiment 17: the synthesis of compound 17
Except with 4-bromine dibenzothiophene (4-bromodibenzo [b, d] thiophene) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 17 with the method identical with the synthetic method of compound 3.
m/z：513.16(100.0％)、514.16(40.3％)、515.16(8.4％)、515.15(4.5％)、516.15(1.8％)、514.15(1.2％)、516.17(1.0％)
Embodiment 18: the synthesis of compound 18
Except with 9,9-dimethyl-2-bromine fluorenes (2-bromo-9,9-dimethyl-9H-fluorene) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 18 with the method identical with the synthetic method of compound 4.
Embodiment 19: the synthesis of compound 19
Except with 9,9-dimethyl-2-bromine fluorenes (2-bromo-9,9-dimethyl-9H-fluorene) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 19 with the method identical with the synthetic method of compound 2.
m/z：525.25(100.0％)、526.25(43.6％)、527.25(9.3％)、528.26(1.3％)
Embodiment 20: the synthesis of compound 20
Except with 9,9-dimethyl-2-bromine fluorenes (2-bromo-9,9-dimethyl-9H-fluorene) replace 4-4-bromine diphenylene-oxide (4-4-bromodibenzo [b, d] furan) and outside reacting, obtain following compound 20 with the method identical with the synthetic method of compound 4.
Make use of the manufacture of the organic illuminating element of main body
Prepare the organic illuminating element that structure is identical with Fig. 1.Specifically, utilize distilled water ultrasonic cleaning to be coated with thickness to be
the glass substrate of indium tin oxide (ITO) film.After distilled water cleaning terminates, Virahol, acetone, methyl alcohol equal solvent is utilized to carry out ultrasonic cleaning and have carried out drying, be delivered to plasma cleaner afterwards and utilize oxygen plasma to carry out cleaning in 5 minutes to aforesaid substrate, utilizing thermovacuum evaporator (thermalevaporator) thickness that portion has made as hole injection layer to be on an ito substrate afterwards
2-TNATA (4,4', 4 "-three [2-naphthylphenyl amino] triphenylamine) film and as the thickness of hole transport layer be
nPB (N, N'-phenylbenzene-N, N'-bis-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines) film.
Then, the main substance 7%Ir (ppy) 3 (three (2-phenylpyridines) close iridium) of the embodiment 1 to 20 synthesized by above-described embodiment is carried out adulterating and made thickness and be
film.Then, the thickness made as electron transfer layer is
tPBi (1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene) film after, make thickness be
liF film and thickness be
aluminium (Al) film and glove box sealing (Encapsulation) this element, made organic illuminating element thus.
Make use of the manufacture of the organic illuminating element of hole transmission layer
Utilize distilled water ultrasonic cleaning to be coated with thickness to be
the glass substrate of indium tin oxide (ITO) film.After distilled water cleaning terminates, Virahol, acetone, methyl alcohol equal solvent is utilized to carry out ultrasonic cleaning and have carried out drying, be delivered to plasma cleaner afterwards and utilize oxygen plasma to carry out cleaning in 5 minutes to aforesaid substrate, utilizing thermovacuum evaporator (thermal evaporator) thickness that portion has made as hole injection layer to be on an ito substrate afterwards
2-TNATA film and as hole transport layer, thickness is
, compound film synthesized by above-described embodiment 1 to 20.Then, mCP (9,9'-(1,3-phenyl) two-9H-carbazole) is carried out adulterating with 7%Ir (ppy) 3 and made thickness and be
film.Then, the thickness made as electron transfer layer is
tPBi film after, make thickness be
liF film and thickness be
aluminium (Al) film and glove box sealing (Encapsulation) this element, made organic illuminating element thus.
Comparative example: the manufacture that make use of the organic illuminating element of hole transmission layer
Except the hole transmission layer of above-described embodiment and luminescent layer main body, organic illuminating element has been made in the same way except being used as by NPB and mCP.
The performance evaluation of organic illuminating element
Keithley 2400 source measuring unit (Keithley 2400source measurement unit) is utilized to apply voltage and inject electronics and hole, and brightness when utilizing Konica Minolta (Konica Minolta) spectroradio luminance meter (CS-2000) and determine light outgoing, thus measure the performance that executed alive current density and brightness be have rated to the organic illuminating element of embodiment and comparative example under atmospheric conditions, the results are shown in table 1.
Table 1
As shown in Table 1, can confirm to employ in its brightness of organic illuminating element of the embodiment 21 to 32 of the compound synthesized by embodiments of the invention 1 to 11, efficiency and current density all excellent than the organic illuminating element of comparative example.
Industrial utilizability
Organic luminescent compounds of the present invention regulates the charge balance in organic matter layer by the suitable mediation of acridine derivatives and ring compound, thus brightness, power-efficient, thermotolerance, charge transport properties and charge injection excellent property and purity of color and luminous efficiency can be improved, thus can be applicable in the functional layer material of organic illuminating element and the main body of luminescent layer or doping agent more than one.Therefore, the organic illuminating element comprising compound of the present invention illustrates low driving voltage and high brightness and high-luminous-efficiency, the performance of the organic panel of full color can be made thus to maximize and can extend the work-ing life of the organic panel of full color.
Claims (11)
1. comprise an organic luminescent compounds for acridine derivatives, represent with following chemical formula 1:
Chemical formula 1
In above-mentioned formula,
X is substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen-atoms of acridine can not combine in No. 3 positions of heteroaryl class part,
R1 to R17 is separately hydrogen; Heavy hydrogen; With the alkyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the thiazolinyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkynyl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-30 of nitro; With the alkoxyl group of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C1-30 of nitro; With the aryloxy of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-30 of nitro; With the aryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C6-36 of nitro; Or with the heteroaryl of heavy hydrogen, halogen, amino, itrile group, the substituted or unsubstituted C2-36 of nitro, optionally, in above-mentioned R1 to R17 adjacent group can be combined with each other and form saturated or unsaturated carbocyclic.
2. the organic luminescent compounds comprising acridine derivatives according to claim 1, is characterized in that,
The compound of above-mentioned chemical formula 1 is when being replaced by heavy hydrogen, and at least 20% by heavy-hydrogenated.
3. the organic luminescent compounds comprising acridine derivatives according to claim 1, is characterized in that,
The aryl class be directly connected with the nitrogen-atoms of above-mentioned acridine part (moiety) or heteroaryl class part are when being replaced by heavy hydrogen, and at least 50% by heavy-hydrogenated.
4. the organic luminescent compounds comprising acridine derivatives according to claim 1, is characterized in that,
Described organic luminescent compounds is to represent one of in following each chemical formula, and described each chemical formula is
5. prepare the method comprising the organic luminescent compounds of acridine derivatives represented with chemical formula 1, it is characterized in that,
Comprise the step that following chemical formula 1-1 and chemical formula 1-2 is reacted:
Chemical formula 1-1
Chemical formula 1-2
Above-mentioned X and R1 to R17 with define at chemical formula 1 identical.
6. the method comprising the organic luminescent compounds of acridine derivatives that represents with chemical formula 1 of preparation according to claim 1, is characterized in that,
Above-mentioned preparation method is one of in the preparation method represented with following reaction formula 1:
Reaction formula 1
In above-mentioned reaction formula 1, X is identical with the X defined at chemical formula 1, and each R is corresponding with R1 and R2 of chemical formula 1-1 respectively.
7. an organic illuminating element, it comprises anode (anode), negative electrode (cathode) and the organic matter layer of more than 1 layer between two electrodes containing compound described in claim 1.
8. organic illuminating element according to claim 7, is characterized in that,
Above-mentioned organic matter layer is selected from more than in the group that is made up of hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer.
9. organic illuminating element according to claim 8, is characterized in that,
Above-mentioned hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer have the thickness of 10 to 1,000nm respectively.
10. organic illuminating element according to claim 7, is characterized in that,
Above-mentioned organic matter layer contains compound according to claim 1 and it can be used as light emitting host or doping agent.
11. organic illuminating elements according to claim 10, is characterized in that,
Above-mentioned doping agent adds the amount of 0.01 to 15 weight part for 100 weight part main bodys.
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| KR1020130087572A KR102169273B1 (en) | 2012-07-26 | 2013-07-24 | Organic electroluminescent compound comprising acridine derivative and organic electroluminescent device comprising same |
| PCT/KR2013/006669 WO2014017844A1 (en) | 2012-07-26 | 2013-07-25 | Organic light-emitting compound comprising acridine derivatives, and organic light-emitting device comprising same |
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| KR20140015202A (en) | 2014-02-06 |
| KR102169273B1 (en) | 2020-10-23 |
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