CN101541713A - Novel condensed ring aromatic compound and organic light-emitting device having the same - Google Patents
Novel condensed ring aromatic compound and organic light-emitting device having the same Download PDFInfo
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Abstract
There are provided a condensed ring aromatic compound and an organic light-emitting device having an optical output with high efficiency and high luminance, and durability. An organic light-emitting device including: a pair of electrodes comprising an anode and a cathode of which at least one is transparent or translucent; and an organic compound layer disposed between the pair of electrodes, wherein the organic compound layer contains the condensed ring aromatic compound represented by the following formula [1]. In the formula, X1 to X16 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and each may be the same or different; adjacent groups combine with each other to form at least one ring in the group selected from X4 to X7; and adjacent groups combine with each other to form at least one ring in the group selected from X12 to X15.
Description
Technical field
The present invention relates to novel condensed ring aromatic compound and organic luminescent device with this compound.
Background technology
Organic luminescent device is to be used for the device that between anode and negative electrode clamping comprises the film of fluorescence organic compound.In addition, when by injecting the exciton that electronics and hole form the fluorescence organic compound from each electrode, and this exciton is when turning back to ground state, and organic luminescent device is luminous.
The organic light-emitting device latest developments are significant and its characteristic comprises, for example, and the high brightness under low impressed voltage, diversity, the high-speed response of emission wavelength and thin and light-weight luminescent device are provided.By these characteristic hints, it is possible that organic luminescent device is applied to various purposes.
Yet the organic luminescent device that has the light output of higher brightness or high conversion efficiency under existing conditions is essential.In addition, organic luminescent device still has many problems aspect weather resistance, for example because life-time service is caused changes in time and because the deterioration that oxygenated environment gas, moisture etc. cause.
Therefore, need to be used to realize having the organic light-emitting device material of high-luminous-efficiency and good durability in recent years always.
As being used for solution to the problems described above, proposed condensed ring aromatic compound as constituting the organic light-emitting device material.Japanese Patent Application Publication No.2001-102173, U.S. Patent Application Publication No.2004-0076853, Japanese Patent Application Publication No.2006-256979, Japanese Patent Application Publication No.H10-189247 and H09-241629 disclose and have used condensed ring aromatic compound as the example that constitutes the organic light-emitting device material.In addition, J.Org.Chem.64,1650-1656,1999 also disclose condensed ring aromatic compound.
Summary of the invention
Finished the present invention to solve aforesaid prior art problems.That is, the object of the present invention is to provide and be used for organic light-emitting device novel condensed ring aromatic compound.In addition, another object of the present invention is to provide the light output with high-level efficiency and high brightness and the organic luminescent device of weather resistance.
The inventor has carried out research to address the above problem, and the result has finished the present invention.That is, condensed ring aromatic compound of the present invention is represented by following general formula [1]:
X wherein
1-X
16Represent hydrogen atom, halogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted aryloxy, replacement or unsubstituted amino, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic independently of one another, and each other can be identical or different; Be selected from X
4-X
7Group in adjacent group be bonded to each other to form at least one ring; And be selected from X
12-X
15Group in adjacent group be bonded to each other to form at least one ring.
Novel condensed ring aromatic compound of the present invention has high-quantum efficiency.Therefore, according to the present invention, can provide the light output with high-level efficiency and high brightness and the organic luminescent device of weather resistance.
By the explanation of following exemplary with reference to accompanying drawing, further feature of the present invention will become clear.
Description of drawings
Fig. 1 is the sectional view that shows first embodiment in the organic luminescent device of the present invention.
Fig. 2 is the sectional view that shows second embodiment in the organic luminescent device of the present invention.
Fig. 3 is the sectional view that shows the 3rd embodiment in the organic luminescent device of the present invention.
Fig. 4 is the sectional view that shows the 4th embodiment in the organic luminescent device of the present invention.
Fig. 5 is the sectional view that shows the 5th embodiment in the organic luminescent device of the present invention.
Fig. 6 is the toluene solution (1 * 10 that shows exemplary compounds H-6
-5Mol/L) PL spectrum (excitation wavelength: figure 351nm).
Embodiment
Condensed ring aromatic compound of the present invention is elaborated.Condensed ring aromatic compound of the present invention is represented by following general formula [1]:
X wherein
1-X
16Represent hydrogen atom, halogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted aryloxy, replacement or unsubstituted amino, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic independently of one another, and each other can be identical or different; Be selected from X
4-X
7Group in adjacent group be bonded to each other to form at least one ring; And be selected from X
12-X
15Group in adjacent group be bonded to each other to form at least one ring.
And then condensed ring aromatic compound of the present invention is the condensed ring aromatic compound according to above-mentioned general formula [1], and it is represented by following general formula [2]:
R wherein
1-R
20Represent hydrogen atom, halogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted aryloxy, replacement or unsubstituted amino, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic independently of one another, and each other can be identical or different.
Below to respectively by the X in above-mentioned general formula [1] and [2]
1-X
16And R
1-R
20The substituent specific examples of expression describes, but is not limited to these substituting groups.
By X
1-X
16And R
1-R
20The example of the halogen atom of expression comprises fluorine, chlorine, bromine and iodine.
By X
1-X
16And R
1-R
20The example of the alkyl of expression comprises methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, the tertiary butyl, sec-butyl, n-pentyl, octyl group, 1-adamantyl, 2-adamantyl, benzyl and phenelyl.
By X
1-X
16And R
1-R
20The example of the alkoxyl group of expression comprises methoxyl group, oxyethyl group, propoxy-, 2-ethyl octyloxy and benzyloxy.
By X
1-X
16And R
1-R
20The example of the aryloxy of expression comprises phenoxy group, 4-tertiary butyl phenoxy group and thiophene oxy.
By X
1-X
16And R
1-R
20The example of the amino group of expression comprises N-methylamino, N-ethylamino, N, N-dimethylamino, N, N-diethylamino, N-methyl-N-ethylamino, N-benzylamino, N-methyl-N-benzylamino, N, N-dibenzyl amino, anilino, N, N-diphenyl amino, N, N-dinaphthyl amino, N, N-two fluorenyl amino, N-phenyl-N-tolyl amino, N, N-two (tolyl) amino, N-methyl-N-phenyl amino, N, N-two (p-methoxy-phenyl) is amino, N-
Base-N-phenyl amino, N, N-two
Base is amino, N-phenyl-N-(4-tert-butyl-phenyl) is amino, N-phenyl-N-(4-trifluoromethyl) is amino, N, N-two (4-tert-butyl-phenyl) is amino, N, N-two (3, the 5-3,5-dimethylphenyl) amino, N-(9,9-dimethyl-fluorenyl)-N-phenyl amino, N-(9,9-dimethyl-fluorenyl)-N-tolyl amino, N-(9,9-dimethyl-fluorenyl)-N-(3, the 5-3,5-dimethylphenyl) amino and N-(9,9-dimethyl-fluorenyl)-N-(2-naphthyl) amino.
By X
1-X
16And R
1-R
20The example of the aryl of expression comprises phenyl, naphthyl, pentalene base, indenyl, Azulene base, anthryl, pyrenyl, indacenyl base, acenaphthenyl, phenanthryl, phenalenyl base, fluoranthene base, acephenanthryl base, aceanthrenyl, benzo [9,10] phenanthryl, crycenyl base, naphthacenyl, perylene base, pentacenyl, xenyl, terphenyl and fluorenyl.
By X
1-X
16And R
1-R
20The example of the heterocyclic radical of expression comprises pyridyl, bipyridyl, pyrryl, oxazolyl, oxadiazole base, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, carbazyl, acridyl and phenanthroline base (phenanthoryl group).
The substituent example that abovementioned alkyl, aryl and heterocyclic radical can have comprises alkyl for example methyl, ethyl and propyl group; Aralkyl is benzyl for example; Aryl is phenyl and xenyl for example; Heterocyclic radical is pyridyl and pyrryl for example; Amino group is dimethylamino, diethylamino, dibenzyl amino, diphenyl amino, two (tolyl) amino and two (p-methoxy-phenyl) amino for example; Alkoxyl group is methoxyl group, oxyethyl group and propoxy-for example; Aryloxy is phenoxy group for example; Halogen atom is fluorine, chlorine, bromine and iodine for example; And cyano group.
By the condensed ring aromatic compound shown in general formula [1] and [2] can, for example, synthetic by the method shown in following synthetic route 1 and 2.
By the condensed ring aromatic compound of general formula [1] expression can, for example, by as shown in following synthetic route 1, using dibromo
Derivative and boric acid (boronic acid) derivative is synthetic as raw material, but synthetic method is not limited to this route 1.
Concrete grammar to synthetic route 1 describes.At first, pass through dibromo
Suzuki-Mi yaura-coupled reaction between derivative and the boric acid derivatives synthesize the dihydroxyl product (for example, Chem.Rev.1995,95,2457-2483).Other method comprises, for example, uses the Yamamoto method (for example, Bull.Chem.Soc.Jpn.51,2091,1978) of nickel catalyzator.Then, by derive two (triflate) product (ditriflateproduct) and carry out intramolecular cyclization (for example, J.Org.Chem.68,883-887,2003) of synthetic dihydroxyl product.Thus, can access the condensed ring aromatic compound of representing by general formula [1].
By the condensed ring aromatic compound of general formula [2] expression also can, for example, by as shown in following synthetic route 2, using dibromo
Derivative is synthetic as raw material.
Concrete grammar to synthetic route 2 describes.
As the R that various substituting groups is introduced in the general formula [2]
4-R
9Or R
14-R
19The time, synthetic route 2 is particularly useful.Specifically, with dibromo
Derivative is derived and is the Compound C R-1 as its ester products.Then, this ester products is hydrolyzed with derivative compound CR-2, and by process subsequently this Compound C R-2 is derived and to be Compound C R-3 as its acyl chlorides.And then this Compound C R-3 carried out intramolecular cyclization (for example, J.Am.Chem.Soc.105,7375,1983) with the ketone product of deriving thus.This ketone product is converted into diketone product (for example, Bull.Chem.Soc.Jpn.59,3311,1986).This diketone product is incorporated into R as intermediate and by two kinds of methods that Knoevenagel reaction (for example, Eur.J.Org.Chem.4185,2002) and Diels-Alder react (for example, J.Org.Chem.62,530,1997) with various substituting groups
4-R
9Or R
14-R
19
When as the luminescence center material, be used for the organic light-emitting device material and have the ideal high luminous quantum efficiency.
The compound of general formula [1] is by form the compound that condensed ring obtains in the compd A with high luminous quantum efficiency as follows.
Compd A is at toluene solution (1 * 10
-5Mol/L) show 0.91 high luminous quantum efficiency in.In mensuration, use fluoranthene compound and relatively calculate this luminous quantum efficiency in contrast.Should notice that fluoranthene has 0.35 luminous quantum efficiency (Handbook of Photochemistry, revises and expansion (1993) by the 2nd edition for Steven L, Murov.) in diluting soln.
Therefore, pass through the Pi-conjugated systems expansion of compd A is obtained the oscillator strength of raising, and therefore can expect further to improve luminous quantum efficiency by the compound of general formula [1] expression.
The inventor is for example by analog calculation, calculated the oscillator strength by the compound of compd A and exemplary compounds B-1 representative, thereby obtained being respectively 0.44 and 0.78 oscillator strength.
In this case, use the B3LYP method (to use three parameter hydridization methods (Three parameter hybrid the method) (J.Chem.Phys.98 of the Becke of Lee-Yang-Parr dependency, 5648 (1993))), promptly as the Gaussian 03package (Gaussian of Molecular Orbital Calculation program, Inc.) one of density function method is carried out this analog calculation.
And then, substituting group is introduced X in the general formula [1]
1-X
16In any one association that can suppress molecule self to reduce reducing of luminous efficiency.Like this, can expect that luminous efficiency further improves.Especially, when substituting group is introduced X
1, X
4, X
7, X
8, X
9, X
12, X
15Or X
16The time, because sterically hindered between the adjacent substituting group, this substituting group tends to be positioned on the vertical direction in plane with the compound of general formula [1], and reduces thus because the effect that the luminous efficiency that molecular association causes reduces is big.
Give the sterically hindered substituent example of molecule itself and comprise alkyl, alkoxyl group, aryloxy, amino, aryl and heterocyclic radical, and its preferred examples comprises amino, aryl and heterocyclic radical.
During as luminescent layer, it can be used as material of main part or guest materials with the compound of general formula [1] expression.Especially, during as the material of main part of luminescent layer, this compound preferably has the material of high glass-transition temperature with the compound of general formula [1] expression, and for this reason, preferred X
1-X
16Has substituting group.
Be used to improve the X of second-order transition temperature
1-X
16Substituent preferred embodiment comprise amino, aryl and heterocyclic radical.
In addition, the substituting group of introducing as the intermediate of synthetic method for the compound that uses general formula [1] expression comprises for example halogen atom.In this case, the active viewpoint from building-up reactions, preferred iodine, bromine and chlorine.
Compound as the organic light-emitting device material preferably has the high carrier injection efficiency.By helping current carrier to inject, can be under lower voltage driving element.The substituent preferred embodiment that is used to improve the current carrier injection efficiency and introduces comprises amino and heterocyclic radical.In this case, when amino is introduced as substituting group, the hole injection efficiency is improved.On the other hand, when heterocyclic radical was introduced, the electronics injection efficiency was improved.
The specific examples of the compound in the above-mentioned general formula [1] is as follows.But the present invention is not limited to these compounds.
Next, organic luminescent device of the present invention is elaborated.
Organic luminescent device of the present invention comprises: anode, negative electrode and be clipped in this anode and should the moon interpolar include the layer (organic compound layer) of organic compounds.And then in organic luminescent device of the present invention, the layer that includes organic compounds contains condensed ring aromatic compound of the present invention.
Organic luminescent device of the present invention can comprise being configured in as this anode of electrode pair and other organic compound layers between this negative electrode outside this organic compound layer.Other organic compound layers comprise for example hole injection layer, hole transmission layer, electronic barrier layer, hole blocking layer, electron transfer layer and electron injecting layer.
Followingly organic luminescent device of the present invention is elaborated with reference to accompanying drawing.
At first, the Reference numeral in the accompanying drawing is described.Reference numeral 1 expression base material; 2 is anode; 3 is luminescent layer; 4 is negative electrode; 5 is hole transmission layer; 6 is electron transfer layer; 7 is hole injection layer; 8 for being used for the hole/exciton barrier-layer of blocking hole and/or exciton; With 10,20,30,40,50 be organic luminescent device.
Fig. 1 is the sectional view that shows first embodiment in the organic luminescent device of the present invention.In the organic luminescent device 10 of Fig. 1, anode 2, luminescent layer 3 and negative electrode 4 are configured on the base material 1 successively.When this luminescent layer 3 comprised the organic compound that has cavity transmission ability, electron transport ability and luminescent properties simultaneously, this organic luminescent device 10 was useful.In addition, when this luminescent layer 3 comprised the mixture of the organic compound that has any characteristic in cavity transmission ability, electron transport ability and the luminescent properties separately, this organic luminescent device 10 also was useful.
Fig. 2 is the sectional view that shows second embodiment in the organic luminescent device of the present invention.In the organic luminescent device 20 of Fig. 2, on base material 1, dispose anode 2, hole transmission layer 5, electron transfer layer 6 and negative electrode 4 successively.When any luminous organic compound was used in combination with the organic compound that only has electronic transmission performance or hole transport performance in will having hole transport performance and electronic transmission performance, this organic luminescent device 20 was useful.In addition, in this organic luminescent device 20, this hole transmission layer 5 or this electron transfer layer 6 also play the effect of luminescent layer.
Fig. 3 is the sectional view that shows the 3rd embodiment in the organic luminescent device of the present invention.The organic luminescent device 30 of Fig. 3 is the organic luminescent devices that insert luminescent layer 3 in the organic luminescent device 20 of Fig. 2 between hole transmission layer 5 and electron transfer layer 6.This organic luminescent device 30 has carrier transport function and lighting function separated from one another, and can have the organic compound of each characteristic in hole transport performance, electronic transmission performance and the luminescent properties with suitable being used in combination.Therefore, the degree of freedom that material is selected extremely improves and can use the various organic compound with different emission wavelengths, makes the variation of luminous form and aspect become possibility thus.In addition, by current carrier or exciton are captured in the luminescent layer 3 at center effectively, also can be intended to make organic luminescent device 30 to improve luminous efficiency.
Fig. 4 is the sectional view that shows the 4th embodiment in the organic luminescent device of the present invention.The organic luminescent device 40 of Fig. 4 is the organic luminescent devices that dispose hole injection layer 7 in the organic luminescent device 30 of Fig. 3 between anode 2 and hole transmission layer 5.This organic luminescent device 40 improves adhesion or hole injection efficiency between anode 2 and the hole transmission layer 5 by disposing this hole injection layer 7, and effective to loss of voltage thus.
Fig. 5 is the sectional view that shows the 5th embodiment in the organic luminescent device of the present invention.The organic luminescent device 50 of Fig. 5 is to insert the organic luminescent device prevent hole or the exciton layer (hole/exciton barrier-layer 8) by entering negative electrode 4 sides in the organic luminescent device 30 of Fig. 3 between luminescent layer 3 and hole transmission layer 6.The organic compound that has high ionization potential by use is as this hole/exciton barrier-layer 8, and the luminous efficiency of this organic luminescent device 50 is improved.
But first to the 5th above-mentioned embodiment only has basic device architecture and uses the organic light-emitting device structure of condensed ring aromatic compound of the present invention to be not limited to these embodiments.Can adopt various layer structure, for example wherein insulation layer, bonding coat or interfering layer are configured in the layer structure at the interface between electrode and the organic layer, comprise two-layer layer structure with different ionization potentials with hole transmission layer wherein.
Condensed ring aromatic compound of the present invention can be used in any one embodiment in first to the 5th embodiment.In addition, when using condensed ring aromatic compound of the present invention, can use the simplification compound and can be used in combination multiple compound.
In addition, condensed ring aromatic compound of the present invention is included in the layer that includes organic compounds, for example, in any of the luminescent layer 3 in first to the 5th embodiment, hole transmission layer 5, electron transfer layer 6, hole injection layer 7 and hole/exciton barrier-layer 8.Preferably it is included in the luminescent layer 3.In addition, in these layers, can contain one or both or more kinds of condensed ring aromatic compound of the present invention.
1. electronics and the hole transmission in luminescent layer
2. the formation of the exciton of main body
3. the transmission of excitation energy between host molecule
4. excitation energy is transferred to object from main body
Energy transfer that needs in each process or light emission and various deactivation process competition ground take place.
Much less, in order to improve the organic light-emitting device luminous efficiency, improve the luminous quantum efficiency of luminescence center material itself.Yet, how can carry out between main body and the main body efficiently or the energy between the subject and object shifts and to have become significant problem.In addition, although the reason of the light emission deterioration that causes owing to energization it be not immediately clear, infer that its reason is with relevant by the environmental change of luminescence center material itself or the luminescent material that molecule causes around it at least.
At this, when main body that condensed ring aromatic compound of the present invention is used for luminescent layer or object, the luminous efficiency of device, the brightness of the light of device output and the weather resistance of device are improved.
When with condensed ring aromatic compound of the present invention during as organic light-emitting device luminescent layer material of the present invention, this luminescent layer can only be made up of condensed ring aromatic compound of the present invention.In addition, condensed ring aromatic compound of the present invention can be used as object (doping agent) material or material of main part.In addition, condensed ring aromatic compound of the present invention also can be used as the electric transmission layer material.
At this, when condensed ring aromatic compound of the present invention when the guest materials, the usage quantity of this compound is preferably 0.01wt%-20wt%, 0.1wt%-15wt% more preferably is based on material of main part.If in this scope, use condensed ring aromatic compound of the present invention, can suitably suppress the concentration quenching that overlaps each other and produce owing to guest materials in the luminescent layer.
When condensed ring aromatic compound of the present invention was used as guest materials, the energy gap of preferred material of main part was greater than the energy gap of guest materials.
Among the present invention, condensed ring aromatic compound of the present invention is especially as the material that constitutes luminescent layer, but also can use with for example conventional known low minute subclass and polymer class hole transport compound, luminophor or electric transmission compound if desired.
The hole transport examples for compounds comprises triarylamine derivative, phenylenediamine derivative, triazole derivative, oxadiazole derivative, imdazole derivatives, pyrazoline derivative, pyrazolone derivative, oxazole derivative, fluorenone derivatives, hydrazone derivative, stilbene derivative, phthalocyanine derivates, derivatives of porphyrin and poly-(vinylcarbazole), poly-(silicylene), poly-(thiophene) and other electric conductive polymers.
Except condensed ring aromatic compound of the present invention, the example of luminophor comprise naphthalene derivatives, phenanthrene derivative, fluorene derivatives, pyrene derivatives, tetracene derivative, coronene derivative,
Derivative perylene derivative, 9,10-diphenylanthrancene derivative, rubrene derivative etc., quinacridone derivative, acridone derivatives, coumarin derivatives, pyran derivate, Nile red, pyrazines derivatives, benzimidizole derivatives, benzothiazole derivant benzoxazole derivative, the stilbene derivative, organometallic complex (organic aluminium compound three (oxine closes) aluminium for example for example, organic beryllium complex) and for example poly-(phenylene vinylidene) derivative of polymer derivant, poly-(fluorenes) derivative, poly-(phenylene) derivative, poly-(inferior thienyl vinylidene) derivative and poly-(acetylene) derivative.
Electric transmission examples for compounds Bao Kuo oxadiazole derivative, oxazole derivative, thiazole derivative, thiadiazoles derivative, pyrazines derivatives, triazole derivative, pyrrolotriazine derivatives, perylene derivative, quinoline, quinoxaline derivatives, fluorenone derivatives, anthracyclinone derivatives, phenanthroline derivative and organometallic complex.
The example that constitutes the anodic material comprises metal simple-substance for example gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium and tungsten, or the alloy of these metal simple-substances, metal oxide is stannic oxide, zinc oxide, Indium sesquioxide, tin indium oxide (ITO) and indium zinc oxide for example.In addition, constitute the anodic material and comprise that also for example, electric conductive polymer is polyaniline, polypyrrole, Polythiophene and polyphenylene sulfide for example.These electrode materialss can use separately or with two or more be used in combination in them.In addition, anode can have the single or multiple lift structure.
The example that constitutes the material of negative electrode comprises metal simple-substance for example lithium, sodium, potassium, calcium, magnesium, aluminium, indium, ruthenium, titanium, manganese, yttrium, silver, lead, tin and chromium.Perhaps, the material that constitutes negative electrode comprises, for example, the alloy of two or more, for example lithium-indium, sodium-potassium, magnesium-Yin, aluminium-lithium, aluminium-magnesium or magnesium-indium alloy, and comprise for example tin indium oxide (ITO) of metal oxide.Can be separately or with in them two or more be used in combination these electrode materialss.In addition, negative electrode can have the single or multiple lift structure.
There is no particular restriction although be used for organic light-emitting device base material of the present invention, for example, uses for example for example glass, quartz and plastics sheet of metal base and ceramic base material and transparent substrate of translucent base material.
In addition, for example colour filter film, fluorescence color conversion colour filter film, dielectric reflections film can also be used for base material with the control illuminant colour.In addition, can also make this device by on base material, forming thin film transistor (TFT) and it being connected with device.
In addition, about taking out direction of light, can adopt these two kinds of bottom emission structure (from the structure of base material side-draw bright dipping) and top emission structure (taking out the structure of light from the opposite side of base material) from device.
Embodiment
By the following examples the present invention is further described particularly, but the present invention should not be limited to these embodiment.
＜embodiment 1〉[exemplary compounds H-6's is synthetic]
(1-1) synthetic intermediate compound 1-2's is synthetic
Reagent as follows and the solvent 300ml that packs into is reclaimed in the flask and under nitrogen gas stream and stirred 18 hours at 80 ℃.
Compound 1-1:5.0g (13.0mmol)
Methyl aceto acetate: 6.74g (51.8mmol)
Tripotassium phosphate: 16.5g (77.7mmol)
Acid chloride (II): 116mg (0.52mmol)
2-(di-t-butyl phosphino-)-2 '-methyl diphenyl: 324mg (1.04mmol)
Toluene: 100ml
Ethanol: 15ml
After reaction is finished, separate with the organic layer of water by adding toluene, and use dried over mgso, then solvent is distilled reaction mixture.By silica gel column chromatography (launch solvent: toluene/chloroform=1/1) with the products therefrom purifying to obtain 2.87g compound 1-2 (yield: 55%).
(1-2) synthetic intermediate compound 1-3's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and at 90 ℃ stirred 24 hours.
Compound 1-2:3.76g (89.6mmol)
Diox: 30ml
Lithium hydroxide monohydrate: 3.76g (89.6mmol)
Concentrated hydrochloric acid (20ml) added in this suspension and with the mixture that obtains lentamente at room temperature stirred 5 hours.Then, water (200ml) is added in this mixture also by the sedimentary crystal of filtering separation.Water, methyl alcohol and diethyl ether wash this crystal successively, then with this crystal heating and dry to obtain 2.87g compound 1-3 (yield: 93%) under high vacuum.
(1-3) synthetic intermediate compound 1-5's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and at 80 ℃ stirred 2 hours.
Compound 1-3:2.87g (6.36mmol)
Thionyl chloride: 50ml
Dimethyl formamide: 300 μ l
This suspension is under reduced pressure distilled, and in residue obtained, add methylene dichloride (50ml) and aluminum chloride successively (2.1g, 15.9mmol), and at room temperature with this mixture vigorous stirring 18 hours.Concentrated hydrochloric acid (180ml) is added in the suspension obtain, and with this mixture heating up and stirred 1 hour.As solvent filtrate is carried out the Soxhlet extraction by this suspension of filtering separation and use chloroform, and the extract that obtains is concentrated.(launch solvent: chloroform/ethyl acetate=15/1) extract is carried out purifying to obtain 1.2g compound 1-5 (yield: 61%) by silica gel column chromatography.
(1-4) synthetic intermediate compound 1-6's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and at 130 ℃ stirred 18 hours.
Compound 1-5:1.2g (3.89mmol)
Benzene selenic anhydride: 4.4g (8.56mmol)
Chlorobenzene: 60ml
This suspension is cooled to 100 ℃ and by filtering sedimentary but still hot crystal separation.With the crystal that obtains with hexane wash and dry to obtain 1.27g compound 1-6 (yield: 97%) under high vacuum.
(1-5) synthetic intermediate compound 1-8's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and under nitrogen gas stream stirred 18 hours at 80 ℃.
Compound 1-6:37mg (0.0046mmol)
Compound 1-7:40mg (0.0092mmol)
Ethanol: 2ml
Toluene: 0.4ml
6N-potassium hydroxide: 300 μ l
After reaction finishes, reaction mixture is placed with cool to room temperature and by filtering the crystal separation that obtains.Crystal is washed and crystal is dry to obtain 55mg compound 1-8 (yield: 99%) under high vacuum with methyl alcohol and IPE (isopropyl ether).
(1-6) exemplary compounds H-6's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and at 70 ℃ stirred 5 hours.
Compound 1-8:55mg (0.0485mmol)
Diazobenzene-2-carboxylic acid hydrochloride: 500mg (0.27mmol)
Propylene oxide: 0.5ml
Ethylene dichloride: 5ml
After reaction finishes, reaction mixture is placed with cool to room temperature and by filtering the crystal separation that obtains.With this crystal thorough washing, (launch solvent: hexane/chloroform=3/1) carry out purifying by silica gel column chromatography with diethyl ether-hexane then to obtain 33mg exemplary compounds H-6 (yield: 55%).
Physicals to the compound that obtains is measured and is estimated.
(molecular weight)
Confirm that by MALDI-TOF-MS (substance assistant laser desorpted/ionization time of flight mass spectrometry) this compound has 1229.79 M+ and therefore confirms it is exemplary compounds H-6.
(NMR)
Measure the structure of confirming this compound by NMR.
1H-NMR(CDCl3，400MHz)σ(ppm)：7.87-7.86(m，4H)，7.78-7.77(m，2H)，7.73(d，2H，J＝8.0Hz)，7.66(t，2H，J＝2.0Hz)，7.48-7.41(m，14H)，7.35(t，2H，J＝7.6Hz)，6.65(d，2H，J＝7.2Hz)，1.42(s，36H)，1.39(s，36H)
(characteristics of luminescence)
Emmission spectrum to the exemplary compounds H-6 of solution form is measured.Before emission spectrometry, use the toluene solution (1 * 10 of spectrophotometer " U-3010 " (making) earlier to exemplary compounds H-6 by HitachiHigh-Technologies Corporation
-5Mol/L) absorption spectrum is measured.After measuring absorption spectrum, use spectrophotofluorometer " F-4500 " (making) to measure the toluene solution (1 * 10 of exemplary compounds H-6 by Hitachi High-TechnologiesCorporation
-5Mol/L) emmission spectrum (PL spectrum).In this case, the result by absorption spectrometry is set in 351nm with excitation wavelength.Result as measuring obtains the PL spectrum shown in Fig. 6.Find that by the PL spectrum shown in Fig. 6 the maximum wavelength of exemplary compounds H-6 has respectively at the first peak and second peak of 469nm and 502nm, and this compound H-6 demonstrates good blue emission.
＜embodiment 2〉[exemplary compounds H-1's is synthetic]
(2-1) synthetic intermediate compound 1-10's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and under nitrogen gas stream stirred 0.5 hour at 80 ℃.
Compound 1-6:0.76g (2.26mmol)
Compound 1-9:0.8g (3.80mmol)
Ethanol: 18ml
Toluene: 2ml
6N-potassium hydroxide: 800ml
After reaction finishes, reaction mixture is placed with cool to room temperature and by filtering the crystal separation that obtains.This crystal is washed and dry to obtain 330mg compound 1-10 (yield: 21%) under high vacuum with methyl alcohol and IPE.
(2-2) exemplary compounds H-1's is synthetic
Reagent as follows and solvent packed into to reclaim in the flask and at 70 ℃ stirred 2 hours.
Compound 1-10:76mg (0.111mmol)
Diazobenzene-2-carboxylic acid hydrochloride: 82mg (0.444mmol)
Propylene oxide: 0.2ml
Ethylene dichloride: 4ml
After reaction finishes, reaction mixture is placed with cool to room temperature and by filtering the crystal separation that obtains.With this crystal thorough washing, (launch solvent: hexane/chloroform=3/1) carry out purifying by silica gel column chromatography with diethyl ether then to obtain 45mg exemplary compounds H-1 (yield: 51%).
Physicals to the compound that obtains is measured and is estimated.
(molecular weight)
Confirm that by MALDI-TOF-MS (substance assistant laser desorpted/ionization time of flight mass spectrometry) this compound has 780.04 M+ and therefore confirms it is exemplary compounds H-1.
(NMR)
Measure the structure of confirming this compound by NMR.
1H-NMR(CDCl3，400MHz)σ(ppm)：7.81(t，6H，J＝2.8Hz)，7.73-7.65(m，18H)，7.60-7.58(m，4H)，7.43-7.38(m，6H)，7.54(d，2H，J＝6.8Hz)，1.42(s，36H)，1.40(s，36H)
Below, each of exemplary compounds H-3, H-5, H-7 and I-1 can by with embodiment 1 in identical synthesis method synthetic.Specifically, with embodiment 1 in carry out that this is synthetic under the identical condition, difference is to use the dibromo that shows in the following table 1
Derivative and acetone derivatives replace compound 1-1 and the compound 1-7 among the embodiment 1 respectively.
Table 1
In addition, can synthesize each of exemplary compounds B-1, C-3, D-1, E-1, F-1, G-2, H-2, I-3 and J-2 by the method for synthetic route 1.Specifically, as the dibromo in the synthetic route 1
Derivative and boric acid derivatives use in the following table 2 corresponding to the shown compound of each derivative.
(embodiment 6) (organic light-emitting device manufacturing)
Organic luminescent device shown in the shop drawings 3 in this embodiment.At first, tin indium oxide (ITO) (anode 2) is gone up drawing having the thickness of 100nm at glass baseplate (base material 1), and make glass baseplate thus with ITO electrode.Secondly, make to be heated by resistive the layer that includes organic compounds and negative electrode are carried out vacuum evaporation to have on this glass baseplate of ITO electrode film forming continuously.Specifically, at first, use compound 2 shown below as the film of hole transmission layer 5 with formation thickness 20nm.Then, will as the compound shown below 3 of main body and as the exemplary compounds H-1 of object as luminescent layer 3 evaporations altogether so that the content of this exemplary compounds H-1 is 1 weight %, based on this compound 3.In this case, form luminescent layer 3 to have the thickness of 30nm.Then, be the film of 30nm as electron transfer layer to form thickness with compound shown below 4.Then, use KF, and use aluminium at last to form the film of thickness as 100nm with the film of formation thickness as 1nm.At this, KF and aluminium are as negative electrode 4 performance functions.
It should be noted that in film process the pressure in the vacuum chamber is set in 10
-5Pa.In addition, when making device, each electrode respect to one another formed have 3mm
2Area.As mentioned above, obtain organic luminescent device.
The organic light-emitting device physicals that obtains is measured and estimated.Specifically, by by Hewlett-Packard Development Company, the microammeter " 4140B " that L.P makes and measure the I-E characteristic and the emission brightness of this device by the luminance meter " BM 7 " that Topcon Corporation makes respectively.As a result, this organic luminescent device demonstrates 300cd/m under the impressed voltage of 4.0V
2Emission brightness and observe blue emission.In addition, affirmation with this device under nitrogen atmosphere at 30mA/cm
2Current density under keep and drive 100 hours by impressed voltage after demonstrate favorable durability.
Although describe the present invention with reference to exemplary, should understand and the invention is not restricted to disclosed exemplary.Thereby the scope of following claims should give the most wide in range explanation comprises that all these change and equivalent 26S Proteasome Structure and Function.
The application requires in view of the above their integral body to be hereby incorporated by in the rights and interests of the Japanese patent application No.2008-038298 of the Japanese patent application No.2007-096343 of submission on April 2nd, 2007 and submission on February 20th, 2008.
Claims (4)
1. by the condensed ring aromatic compound of following general formula [1] expression:
X wherein
1-X
16Represent hydrogen atom, halogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted aryloxy, replacement or unsubstituted amino, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic independently of one another, and each other can be identical or different; Be selected from X
4-X
7Group in adjacent group be bonded to each other to form at least one ring; And be selected from X
12-X
15Group in adjacent group be bonded to each other to form at least one ring.
2. condensed ring aromatic compound according to claim 1, it is represented by following general formula [2]:
R wherein
1-R
20Represent hydrogen atom, halogen atom, replacement or unsubstituted alkyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted aryloxy, replacement or unsubstituted amino, replacement or unsubstituted aryl or replacement or unsubstituted heterocyclic independently of one another, and each other can be identical or different.
3. organic luminescent device comprises:
The pair of electrodes that comprises anode and negative electrode, at least one in this anode and the negative electrode is transparent or semitransparent; With
Be configured in the organic compound layer between this counter electrode, wherein this organic compound layer contains condensed ring aromatic compound according to claim 1 and 2.
4. organic luminescent device according to claim 3, wherein this organic compound layer is a luminescent layer.
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| JP096343/2007 | 2007-04-02 | ||
| JP2007096343 | 2007-04-02 | ||
| JP038298/2008 | 2008-02-20 | ||
| JP2008038298 | 2008-02-20 | ||
| PCT/JP2008/056615 WO2008120806A1 (en) | 2007-04-02 | 2008-03-27 | Novel condensed ring aromatic compound and organic light-emitting device having the same |
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| US9005778B2 (en) | 2010-04-30 | 2015-04-14 | Canon Kabushiki Kaisha | Organic compound and organic light-emitting device including the same |
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