CN101016248A - Organic electroluminescent material and application thereof - Google Patents
Organic electroluminescent material and application thereof Download PDFInfo
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Abstract
本发明涉及一种新型化合物和包含该化合物的有机电致发光器件。该化合物的结构通式如下所示，其中R1～R8独立选自氢原子、含C6－20的芳基或取代芳基、含C6－20的稠环芳基、含C4－20的杂环芳基或稠杂环芳基、含C1－30的烷基或取代烷基、含C1－30的烷氧基或取代的烷氧基、含C2－30的烷基氨基或取代的烷基氨基、含C1－30的烷硫基或取代烷硫基。本发明克服了目前常用的发光材料在色纯度、发光效率等方面存在的问题。本发明的材料可优先用作发光体，同时还可用作电子传输、空穴阻挡材料，利用本发明的材料制备的电致发光器件表现出高色纯度、高亮度、高效率的优越性能。
The present invention relates to a novel compound and an organic electroluminescent device comprising the compound. The general structural formula of the compound is as follows, wherein R 1 to R 8 are independently selected from hydrogen atoms, C6-20-containing aryl or substituted aryl, C6-20-containing fused ring aryl, C4-20-containing hetero Cyclic aryl or fused heterocyclic aryl, C1-30-containing alkyl or substituted alkyl, C1-30-containing alkoxy or substituted alkoxy, C2-30-containing alkylamino or substituted alkyl Amino, C1-30-containing alkylthio or substituted alkylthio. The invention overcomes the problems existing in the color purity, luminous efficiency and the like of commonly used luminous materials at present. The material of the invention can be preferentially used as a luminous body, and can also be used as an electron transport and hole blocking material at the same time. The electroluminescent device prepared by using the material of the invention shows superior performances of high color purity, high brightness and high efficiency.
Description
Technical field
The present invention relates to a kind of electroluminescent organic material, and the application in organic electroluminescence device, the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field belonged to.
Background technology
Organic electroluminescence device (hereinafter to be referred as organic EL) has a wide range of applications in various fields owing to have that thin, the full curing of ultralight, luminous, response speed are fast, good temp characteristic, can realize characteristic such as soft demonstration.
The research of organic EL starts from nineteen sixties.People (J.Chem.Phys.1963 such as Pope in 1963,38:2042～2043) studied the blue coloured electroluminous of anthracene single crystal sheet (10～20 μ m), restriction because of the thicker and employed electrode materials of anthracene single crystal luminescent layer (elargol and sodium chloride solution), the luminous trigger voltage of device is up to 400V, and efficient and brightness are all lower.Yet a frontier of luminous science and technology has been opened up in this discovery.Between two more than ten years after this, the progress of organic EL is slow.Until 1987, (Appl.Phys.Lett.1987,51:913～915) such as the C.W.Tang of Kodak just obtained the breakthrough with milestone significance.They adopt bilayer structure to do with oxine aluminium (Alq3) that luminescent layer, aromatic diamines are made hole transmission layer, ITO makes the bi-layer devices that anode, Mg: Ag (10: 1) alloy is made negative electrode, obtains higher quantum yield (1%) and luminous efficiency (1.5lm/W): high brightness (＞1000cd/m2) with than the low driving voltage (device of≤10V.This progress has been aroused the hope that organic EL is applied to panchromatic flat-panel monitor again, and the research of material and device becomes the focus of research rapidly.1988, people such as Adchi [J.Appl.Phys.1988,27 (2): L269～L271] released the multilayer sandwich type structural, have expanded the range of choice of organic EL Material greatly.
Through vicennial development, organic EL Material round Realization red, blue, green emitting, Application Areas has also expanded polymer and metal complex field to from small molecules.In theory, it is ripe that the organic electroluminescent technique of display has been tending towards, and some products come into the market, but in the commercialization process, still have many problems to need to be resolved hurrily.Especially for the various organic materialss of making device, its current carrier injects, transmission performance, material electroluminescence performance, work-ing life, purity of color, between each material and and each electrode between coupling etc., many problems are still unresolved.Simultaneously, material new, that performance is more excellent constantly is found and uses, and element manufacturing technology and device performance are being updated among the raising.
The basic structure of organic EL device comprises anode/hole injection and transport layer/organic luminous layer/electron injecting layer/negative electrode, now used organic EL device is mostly because driving voltage is higher, luminosity and efficient are lower, and the performance degradation of device get quite fast, so still be difficult to be applied to actual production.
Summary of the invention
The purpose of this invention is to provide and a kind ofly have excellent luminous efficiency and thermotolerance, the life-span is long and emission has excellent color purity novel electroluminescent material, and the organic electroluminescence device that adopts this material.
Have ring vinylbenzene of outer ethylene linkage constitutional features and derivative thereof and in luminescent material, use morely, also show luminescent properties preferably.But, in small molecule material, because the not high factor of its thermostability has limited its application in device.And polystyrene of using morely and derivative thereof also because polymer luminescent material itself has and is difficult to many defectives of overcoming at present, thereby also are difficult to well be used in actual production.After studying for a long period of time, the inventor has found to contain the X type compound of the outer ethylene linkage of a plurality of rings, has good carrier transmission performance and luminescent properties efficiently, has good thermal stability and easy advantages such as synthetic and purification simultaneously.Subsequently it is applied in the electroluminescent device, resulting device has higher purity of color and efficient.Just be based on this understanding, finishing the present invention.
The present invention proposes the compound that the following general formula of a kind of usefulness is represented:
In the said structure formula, R
1～R
8Can be a kind of in hydrogen atom, alkyl, iso-alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, trifluoromethyl or the heterocyclic substituent (furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles, carbazole, oxadiazole etc.).
In the said structure formula, R
1～R
8Can be identical or different.Be preferably hydrogen atom; Be preferably the aryl or the substituted aryl that contain C6-20, as phenyl, naphthyl, xenyl, p-terphenyl base, anthryl, dianthranide base, to tert-butyl-phenyl, 2,4-difluorophenyl, 4-(N, N-dimethyl amido) phenyl etc., wherein most preferred is phenyl, naphthyl, xenyl, anthryl; Be preferably the fused ring aryl that contains C6-20 such as pyrenyl, naphthacenyl, phenanthryl, benzo phenanthryl, benzanthrene, benzo pyrenyl, fluorenyl etc., wherein most preferred is pyrenyl, benzo anthryl, phenanthryl, fluorenyl, 9,10-dimethyl fluorenyl, 9,10-diethyl fluorenyl; Be preferably the heterocyclic aryl that contains C4-20 or fused heterocycle aryl such as pyridyl, quinolyl, benzothienyl, cumarone, indyl, benzimidazolyl-, benzothiazolyl etc., wherein most preferred is pyridyl, quinolyl, thienyl, pyrryl; Be preferably alkoxyl group or the alkoxyl group of replacement, the alkylamino of C2-30 or the alkylamino of replacement of the alkyl of C1-30 or substituted alkyl, C1-30, as methyl, trifluoromethyl, ethyl, sec.-propyl, the tertiary butyl, methoxyl group, oxyethyl group, isopropoxy, tertiary butyl oxygen base, N, N-dimethyl amido, N, N-diethyl amido, wherein most preferred is methyl, trifluoromethyl; Be preferably the alkylthio of C1-30 or substituted alkane sulphur base etc., as methylthio group, ethylmercapto group, sec.-propyl sulfenyl, tertiary butyl sulfenyl, wherein most preferred is methylthio group.
For clearer narration content of the present invention, the narration of following mask body but typical preferred structure in the type of compounds that is not limited to the present invention relates to:
Material of the present invention has the following advantages:
Electroluminescent organic material of the present invention can preferentially be used as twinkler, comprises separately as luminescent layer, perhaps as adulterated dyestuff and luminous, and also can be used as hole transport, electronics blocking material simultaneously.
Utilize the organic electroluminescence device of luminescent material preparation of the present invention can show high purity, high brightness, high efficiency high-performance.
Description of drawings
Fig. 1 is the mass spectrum of material C 48 of the present invention;
Fig. 2 is the electroluminescent graph of device OLED-1～OLED-3;
Embodiment
Preferred implementation: compound of the present invention mainly be adopt aryl aldehyde or aryl ketones and aryl dimethylphosphite derivatives reaction with and bromo derivative and boric acid carry out the SUZUKI linked reaction and prepare, used reaction is simply effective.
Most of raw material such as benzophenone, aryl bromide and boric acid etc. used among the present invention are the commercial goods, and intermediate main reference document (J.Org.Chem., 2003,68,839-853) synthetic.
The synthetic route of intermediate and invention compound is as follows:
Synthetic route:
R in the following formula, R ', R " be the substituent group R in the general formula compound of the present invention
1～R
8
Synthesizing of intermediate:
Intermediate 1,2,4,5-four (dimethylphosphite methylene radical) benzene (M1)
In the 50mL single port bottle of magnetic agitation and NaOH device for absorbing tail gas is housed, add 1,2,4,5-tetrabromo methylbenzene 10.6g (23.4mmol), trimethyl phosphite 16ml (140.4mmol), oil bath heat temperature raising to 160 ℃, back flow reaction 3h.Stopped reaction, the trimethyl phosphite that the water pump pressure reducing and steaming is excessive gets light yellow dope 11.4 grams, yield 86.6%.
Intermediate 21,2-two bromo-4,5-two (dimethylphosphite methylene radical) benzene (M2)
Process is synthetic with intermediate one, and just with raw material 1,2,4,5-tetrabromo methylbenzene changes 1 into, 2-two bromo-4,5-two (brooethyl) benzene.Light yellow dope, yield 90%.
Intermediate 31,4-two bromo-2,5-two (dimethylphosphite methylene radical) benzene (M3)
Process is synthetic with intermediate one, and just with raw material 1,2,4,5-tetrabromo methylbenzene changes 1 into, 4-two bromo-2,5-two (brooethyl) benzene.Light yellow solid, yield 94%.
Be the synthetic embodiment of compound of the present invention below:
Synthesizing of embodiment one Compound C 01
In the 250ml there-necked flask under the nitrogen protection that magnetic agitation is housed, add 2.5g (4.4mmol) M1, dimethylbenzene ketone 3.5g (19.4mmol), exsiccant THF100mL.In addition sodium hydride 1.6g (28.0mol) is scattered in the 15mL dry THF, under the magnetic agitation, slowly is added drop-wise in the reaction flask, drip and finish, slowly be warming up to backflow, continue back flow reaction 20h.Stopped reaction, cooling, careful in the system dropping methyl alcohol till do not have bubble and emit, add ethyl acetate and each 50mL of water, tell organic phase, water merges organic phase with ethyl acetate extraction, with anhydrous sodium sulfate drying, filter, rotation boils off solvent, and the gained solid is with the toluene recrystallization, get yellow powder 2.1 grams, yield 63.0%.
Product MS (m/e): 791; Ultimate analysis (C
62H
46): theoretical value C:94.14, H:5.86; Measured value C:C:94.02, H:5.97.
Synthesizing of embodiment two Compound C 03
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to 2-benzoyl naphthalene, gets yellow powder 1.8 grams, yield 70.4%.
Product MS (m/e): 991; Ultimate analysis (C
78H
54): theoretical value C:94.51, H:5.49; Measured value C:94.50, H:5.44.
Synthesizing of embodiment three Compound C 04
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to 4-benzoyl biphenyl, gets buff powder 1.5 grams, yield 55.6%.
Product MS (m/e): 1094; Ultimate analysis (C
86H
62): theoretical value C:94.30, H:5.70; Measured value C:94.38, H:5.58.
Embodiment Four Modernizations compound C06's is synthetic
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to acetylbenzene, and the gained solid gets pale yellow crystals 1.7 grams, yield 66.6% with toluene-ethyl alcohol recrystallization.
Product MS (m/e): 542; Ultimate analysis (C
42H
38): theoretical value C:92.94, H:7.06; Measured value C:92.88, H:7.00.
Synthesizing of embodiment five Compound C 09
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to the ethanoyl naphthalene, gets yellow crystals 2.2 grams, yield 69.7%.
Product MS (m/e): 742; Ultimate analysis (C
58H
46): theoretical value C:93.76, H:6.24; Measured value C:93.77, H:6.20.
Synthesizing of embodiment six Compound C 14
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to phenyl aldehyde, and the gained solid gets yellow crystals 2.7 grams, yield 86.1% with toluene-ethyl alcohol recrystallization.
Product MS (m/e): 486; Ultimate analysis (C
38H
30): theoretical value C:93.79, H:6.21; Measured value C:93.70, H:6.16.
Synthesizing of embodiment seven Compound C 15
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to the 2-naphthaldehyde, gets yellow solid 2.2 grams, yield 80.0%.
Product MS (m/e): 686; Ultimate analysis (C
54H
38): theoretical value C:94.42, H:5.58; Measured value C:94.42, H:5.56.
Synthesizing of embodiment eight Compound C 17
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to the 9-formaldehyde, gets yellow solid 2.0 grams, yield 76.8%.
Product MS (m/e): 886; Ultimate analysis (C
70H
46): theoretical value C:94.77, H:5.23; Measured value C:94.74, H:5.19.
Synthesizing of embodiment nine Compound C 19
Process is same as embodiment one, just raw material dimethylbenzene ketone is changed to 9, and 10-dimethyl-2-fluorenes formaldehyde gets yellow solid 1.3 grams, yield 79.9%.
Product MS (m/e): 951; Ultimate analysis (C
74H
62): theoretical value C:93.43, H:6.57; Measured value C:93.39, H:6.55.
Synthesizing of embodiment ten Compound C 20
(1) 1,2-two bromo-4, (2, the 2-diphenylethyllene-1-) benzene is synthetic for 5-two
Process is same as embodiment one, just intermediate M1 is changed to M2, gets pale yellow crystals 10.9 grams, yield 79.9%.
Product MS (m/e): 592; Ultimate analysis (C
34H
24Br
2): theoretical value C:68.94, H:4.08; Measured value C:68.90, H:4.00.
(2) Compound C 20 is synthetic
1.5g (2.5mmol) is gone up the dibromobenzene derivative that the step obtains; 0.9g (6.0mmol) vinylbenzene boric acid; 0.04g (0.25mmol) palladium chloride; 0.13g (0.5mmol) triphenylphosphine; 2.5g (18.0mmol) Anhydrous potassium carbonate and be that the solvent 32ml that toluene-alcohol-water of 3: 3: 2 is formed joins in the 100ml there-necked flask by volume ratio; under the nitrogen protection; reflux 5 hours; cooling; filter; tell water; the washing organic phase; anhydrous sodium sulfate drying; rotation boils off solvent; the gained solid gets yellow crystals 1.3 grams, yield 80.3% with the toluene recrystallization.
Product MS (m/e): 638; Ultimate analysis (C
50H
38): theoretical value C:94.00, H:6.00; Measured value C:93.88, H:6.07.
Synthesizing of embodiment 11 Compound C 21
Process is same as embodiment ten (2), just benzene feedstock ethene boric acid is changed to t-butyl styrene boric acid, gets yellow solid 1.7 grams, yield 70.5%.
Product MS (m/e): 751; Ultimate analysis (C
58H
54): theoretical value C:92.75, H:7.25; Measured value C:92.70, H:7.23.
Synthesizing of embodiment 12 Compound C 22
Process is same as embodiment ten, just in (1) raw material M2 is changed to M3, and benzophenone is changed to 9, and 10-dimethyl-2-fluorenes formaldehyde gets light yellow solid 1.3 grams, yield 75.5%.
Product MS (m/e): 719; Ultimate analysis (C
56H
46): theoretical value C:93.55, H:6.45; Measured value C:93.53, H:6.40.
Synthesizing of embodiment 13 Compound C 23
Process is same as embodiment ten, just in (1) raw material dimethylbenzene ketone is changed to 9, and 10-dimethyl-2-fluorenes formaldehyde gets light yellow solid 1.1 grams, yield 64.7%.
Product MS (m/e): 719; Ultimate analysis (C
56H
46): theoretical value C:93.55, H:6.45; Measured value C:93.53, H:6.40.
Embodiment ten Four Modernizations compound C24's is synthetic
Process is same as embodiment ten, just in (2) benzene feedstock ethene boric acid is changed to 9, and 10-dimethyl-2-fluorenes boric acid gets yellow solid 1.1 grams, yield 66.0%.
Product MS (m/e): 871; Ultimate analysis (C
68H
54): theoretical value C:93.75, H:6.25; Measured value C:93.77, H:6.23.
Synthesizing of embodiment 15 Compound C 25
Process is same as embodiment ten, just in (1) raw material dimethylbenzene ketone is changed to 2-benzoyl naphthalene, gets yellow solid 1.6 grams, yield 59.9%.
Product MS (m/e): 738; Ultimate analysis (C
58H
42): theoretical value C:94.27; H:5.73; Measured value C:94.16, H:5.68.
Synthesizing of embodiment 16 Compound C 26
Process is same as embodiment ten, just in (2) benzene feedstock boric acid is changed to the 2-naphthalene boronic acids, gets yellow solid 1.8 grams, yield 74.6%.
Product MS (m/e): 738; Ultimate analysis (C
58H
42): theoretical value C:94.27; H:5.73; Measured value C:94.16, H:5.68.
Synthesizing of embodiment 17 Compound C 27
Process is same as embodiment 15, just benzene feedstock boric acid is changed to the 2-naphthalene boronic acids, gets yellow solid 1.2 grams, yield 66.2%.
Product MS (m/e): 839; Ultimate analysis (C
74H
62): theoretical value C:94.47, H:5.53; Measured value C:94.44, H:5.50.
Synthesizing of embodiment 18 Compound C 29
Process is same as embodiment 12, and just with raw material 9,10-dimethyl-2-fluorenes formaldehyde is changed to the dimethylbenzene ketone, gets yellow crystals 1.5 grams, yield 80.3%.
Product MS (m/e): 638; Ultimate analysis (C
50H
38): theoretical value C:94.00, H:6.00; Measured value C:93.98, H:5.95
Synthesizing of embodiment 19 Compound C 30
Process is same as embodiment 12, just benzene feedstock boric acid is changed to the 2-naphthalene boronic acids, gets yellow crystals 2.0 grams, yield 72.3%.
Product MS (m/e): 738; Ultimate analysis (C
58H
42): theoretical value C:94.27, H:5.73; Measured value C:94.19, H:5.77
Synthesizing of embodiment 20 Compound C 33
Process is same as embodiment 12, just benzene feedstock boric acid is changed to tert.-butylbenzene boric acid, gets pale yellow crystals 1.7 grams, yield 65.8%.
Product MS (m/e): 751; Ultimate analysis (C
58H
54): theoretical value C:92.75, H:7.25; Measured value C:92.70, H:7.11.
Synthesizing of embodiment 21 Compound C 36
Process is same as embodiment 12, just the raw material benzophenone is changed to 2-benzoyl naphthalene, and phenylo boric acid is changed to the 2-naphthalene boronic acids, gets yellow solid 1.2 grams, yield 67.7%.
Product MS (m/e): 839; Ultimate analysis (C
66H
46): theoretical value C:94.47, H:5.53; Measured value C:94.35, H:5.49.
Synthesizing of embodiment 22 Compound C 41
Process is same as embodiment ten, just in (1) raw material M2 is changed to M3, in (2) benzene feedstock boric acid is changed to 9, and 10-dimethyl-2-fluorenes boric acid gets yellow solid 1.9 grams, yield 69.1%.
Product MS (m/e): 871; Ultimate analysis (C
68H
54): theoretical value C:93.75, H:6.25; Measured value C:93.65, H:6.22.
Synthesizing of embodiment 23 Compound C 42
Process is same as embodiment ten, just the raw material benzophenone is changed to 4-(N-carbazyl) phenyl aldehyde, gets light yellow solid 0.9 gram, yield 70.4%.
Product MS (m/e): 817; Ultimate analysis (C
62H
44N
2): theoretical value C:91.14, H:5.43, N:3.43; Measured value C:91.11, H:5.40, N:3.32
Be the Application Example of The compounds of this invention below:
The preferred implementation of fabricate devices:
The typical structure of OLED device is: substrate/anode/hole transmission layer (HTL)/organic luminous layer/electron transfer layer (ETL)/negative electrode.
Substrate is transparent, can be glass or flexible substrate, and flexible substrate adopts a kind of material in polyester, the polyimide compounds; Anode layer can adopt inorganic materials or organic conductive polymkeric substance, inorganic materials is generally the higher metals of work function such as metal oxides such as tin indium oxide (hereinafter to be referred as ITO), zinc oxide, zinc tin oxide or gold, copper, silver, the optimized ITO that is chosen as, organic conductive polymkeric substance are preferably a kind of material in Polythiophene/polyvinylbenzenesulfonic acid sodium (hereinafter to be referred as PEDOT:PSS), the polyaniline (hereinafter to be referred as PANI); Cathode layer generally adopts the alloy of the lower metal of work functions such as lithium, magnesium, calcium, strontium, aluminium, indium or they and copper, gold and silver, or the electrode layer that alternately forms of metal and metal fluoride, the present invention is preferably Mg:Ag alloy layer, Ag layer and LiF layer successively, Al layer successively; Hole transmission layer generally adopts the tri-arylamine group material, and the present invention is preferably N, N '-two-(1-naphthyl)-N, N '-phenylbenzene-1,1-xenyl-4,4-diamines (NPB); Electron transfer layer is generally a metal-organic complex, preferably closes gallium (III) (the following Alq that is called for short respectively as three (oxine) aluminium, three (oxine) gallium, (the adjacent amine phenol of salicylidene)-(oxine)
3, Gaq
3, Ga (Saph-q)), also can be the o-phenanthroline class, as 4,7-phenylbenzene-1,10-o-phenanthroline (hereinafter to be referred as Bphen) etc., organic luminous layer generally can adopt small molecule material, can doping fluorescent material or phosphorescent coloring, comprised the luminous organic material that the present invention proposes in the organic luminous layer of the present invention, it can be directly luminous, also can be used as dye adulterated luminously in corresponding material of main part, and preferred material of main part is Alq
3, Gaq
3, Ga (Saph-q), NPB.
Prepare a series of organic electroluminescence device of the present invention in accordance with the following methods:
(1) uses clean-out system, deionized water and organic solution to divide several steps to clean and have the anodic glass substrate;
(2) hole transmission layer of the method evaporation device by vacuum-evaporation;
(3) continue the luminescent layer that evaporation comprises red light material of the present invention again;
(4) electron transfer layer of continuation evaporation device;
(5) method by evaporation or sputter prepares metallic cathode again.
The preparation of embodiment 20 four device OLED-1～OLED-3
The preparation of OLED-1: sheet glass supersound process in commercial clean-out system that will be coated with the ITO transparency conducting layer, in deionized water, wash, at acetone: ultrasonic oil removing in the alcohol mixed solvent, under clean environment, be baked to and remove moisture content fully, with UV-light cleaning machine irradiation 10 minutes, and with low energy positively charged ion bundle bombarded surface.
The above-mentioned anodic glass substrate that has is placed in the vacuum chamber, be evacuated to 1 * 10
-4Pa continues evaporation NPB as hole transmission layer on above-mentioned anode tunic, evaporation speed is 0.1nm/s, and the evaporation thickness is 50nm;
On hole transmission layer, continue evaporation one deck and be doped with the luminescent layer of the NPB of Compound C 48 as device, Compound C 48 is 1: 100 with the evaporation speed ratio of NPB, and the doping content of Compound C 48 in NPB is 7wt%, the total speed of its evaporation is 0.1nm/s, and the evaporation total film thickness is 30nm;
Continue evaporation one deck Alq again
3Material is as the electron transfer layer of device, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 20nm;
At last, evaporation Mg:Ag alloy layer and Ag layer are as the cathode layer of device successively on above-mentioned electron transfer layer, and wherein the evaporation speed of Mg:Ag alloy layer is 2.5nm/s, and thickness is 100nm, and the evaporation speed of Ag layer is 0.3nm/s, and thickness is 100nm.
Preparing OLED-2 and OLED-3 according to the method described above, only is to have changed the doping content of Compound C 48 in NPB, and the performance of device sees table 1 for details:
Table 1:
| Device number | Device architecture is formed | Emission wavelength nm | Current density A/m 2 | Brightness cd/m2 | Efficient cd/A |
| OLED-1 | ITO/NPB (50nm)/NPB:7wt% Compound C 48 (30nm)/Alq 3(20nm)/MgAg:Ag | 476 | 500 | 1212 | 2.49 |
| OLED-2 | ITO/NPB (50nm)/NPB:12wt% Compound C 48 (30nm)/Alq 3(20nm)/MgAg:Ag | 480 | 500 | 1309 | 3.75 |
| OLED-3 | ITO/NPB (50nm)/NPB:20wt% Compound C 48 (30nm)/Alq 3(20nm)/MgAg:Ag | 480 | 500 | 1802 | 2.80 |
Although describe the present invention in conjunction with the preferred embodiments, but the present invention is not limited to the foregoing description and accompanying drawing, should be appreciated that under the guiding of the present invention's design, those skilled in the art can carry out various modifications and improvement, and claims have been summarized scope of the present invention.
Claims (7)
1, a kind of compound, general structure is as follows:
In the said structure formula, R
1～R
8Independently be selected from hydrogen atom, contain aryl or the substituted aryl of C6-20, the fused ring aryl that contains C6-20, the heterocyclic aryl that contains C4-20 or the alkylamino of the alkoxyl group of fused heterocycle aryl, the alkyl that contains C1-30 or substituted alkyl, the alkoxyl group that contains C1-30 or replacement, the alkylamino that contains C2-30 or replacement, the alkylthio that contains C1-30 or substituted alkane sulphur base.
2, compound according to claim 1 is characterized in that, wherein R
1～R
8Independently be preferably hydrogen atom respectively; Phenyl, naphthyl, xenyl, p-terphenyl base, anthryl, dianthranide base, to tert-butyl-phenyl, 2,4 difluorobenzene base, 4-(N, N-dimethyl amido) phenyl; Pyrenyl, naphthacenyl, phenanthryl, benzo phenanthryl, benzanthrene, benzo pyrenyl, 9,10-dimethyl fluorenyl, 9,10-diethyl fluorenyl; Pyridyl, quinolyl, benzothienyl, cumarone, indyl, benzimidazolyl-, benzothiazolyl, pyrryl; Methyl, trifluoromethyl, ethyl, sec.-propyl, the tertiary butyl, methoxyl group, oxyethyl group, isopropoxy, tertiary butyl oxygen base, N, N-dimethyl amido, N, N-diethyl amido; A kind of in methylthio group, ethylmercapto group, sec.-propyl sulfenyl, the tertiary butyl sulfenyl.
3, compound according to claim 1, the preferred construction formula is as follows:
4, a kind of organic electroluminescence device comprises first electrode and second electrode, and the organic function layer between two electrodes, it is characterized in that, the one deck at least in the organic function layer comprises the compound with following structural:
In the said structure formula, R
1～R
8Independently be selected from hydrogen atom, contain aryl or the substituted aryl of C6-20, the fused ring aryl that contains C6-20, the heterocyclic aryl that contains C4-20 or the alkylamino of the alkoxyl group of fused heterocycle aryl, the alkyl that contains C1-30 or substituted alkyl, the alkoxyl group that contains C1-30 or replacement, the alkylamino that contains C2-30 or replacement, the alkylthio that contains C1-30 or substituted alkane sulphur base.
5, organic electroluminescence device as claimed in claim 4 is characterized in that containing in the luminescent layer compound with following structural formula:
In the said structure formula, R
1～R
8Independently be selected from hydrogen atom, contain aryl or the substituted aryl of C6-20, the fused ring aryl that contains C6-20, the heterocyclic aryl that contains C4-20 or the alkylamino of the alkoxyl group of fused heterocycle aryl, the alkyl that contains C1-30 or substituted alkyl, the alkoxyl group that contains C1-30 or replacement, the alkylamino that contains C2-30 or replacement, the alkylthio that contains C1-30 or substituted alkane sulphur base.
6, organic electroluminescence device as claimed in claim 5 is characterized in that containing in the luminescent layer compound:
7, organic electroluminescence device as claimed in claim 4 is characterized in that containing in the electron transfer layer compound with following structural formula:
In the said structure formula, R
1～R
8Independently be selected from hydrogen atom, contain aryl or the substituted aryl of C6-20, the fused ring aryl that contains C6-20, the heterocyclic aryl that contains C4-20 or the alkylamino of the alkoxyl group of fused heterocycle aryl, the alkyl that contains C1-30 or substituted alkyl, the alkoxyl group that contains C1-30 or replacement, the alkylamino that contains C2-30 or replacement, the alkylthio that contains C1-30 or substituted alkane sulphur base.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2499969A (en) * | 2010-06-25 | 2013-09-11 | Cambridge Display Tech Ltd | Composition comprising an organic semiconducting material and a triplet-accepting material |
| CN103508836A (en) * | 2012-06-21 | 2014-01-15 | 昆山维信诺显示技术有限公司 | 6, 6-disubstituted-6-H-benzo[cd]pyrene derivative, and preparation method and applications thereof |
| US9142782B2 (en) | 2010-06-25 | 2015-09-22 | Cambridge Display Technology, Ltd. | Organic light-emitting material, device and method |
| US9738591B2 (en) | 2009-12-21 | 2017-08-22 | Ramiz Boulos | Antimicrobial compounds |
| CN115838365A (en) * | 2022-10-26 | 2023-03-24 | 扬州工业职业技术学院 | AIE type double D-pi-A structure fluorescent dye and construction method thereof |
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2006
- 2006-12-29 CN CN 200610167357 patent/CN101016248A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9738591B2 (en) | 2009-12-21 | 2017-08-22 | Ramiz Boulos | Antimicrobial compounds |
| US10696620B2 (en) | 2009-12-21 | 2020-06-30 | Boulos & Cooper Pharmaceuticals Pty Ltd | Antimicrobial compounds |
| GB2499969A (en) * | 2010-06-25 | 2013-09-11 | Cambridge Display Tech Ltd | Composition comprising an organic semiconducting material and a triplet-accepting material |
| US9142782B2 (en) | 2010-06-25 | 2015-09-22 | Cambridge Display Technology, Ltd. | Organic light-emitting material, device and method |
| US9773981B2 (en) | 2010-06-25 | 2017-09-26 | Cambridge Display Technology, Ltd. | Organic light-emitting device and method |
| US9812647B2 (en) | 2010-06-25 | 2017-11-07 | Cambridge Display Technology, Ltd. | Organic light-emitting device and method |
| CN103508836A (en) * | 2012-06-21 | 2014-01-15 | 昆山维信诺显示技术有限公司 | 6, 6-disubstituted-6-H-benzo[cd]pyrene derivative, and preparation method and applications thereof |
| CN103508836B (en) * | 2012-06-21 | 2016-02-10 | 昆山维信诺显示技术有限公司 | A kind of 6,6-is two replaces-6-H-benzo [cd] pyrene derivatives and preparation method thereof and application |
| CN115838365A (en) * | 2022-10-26 | 2023-03-24 | 扬州工业职业技术学院 | AIE type double D-pi-A structure fluorescent dye and construction method thereof |
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