CN101558030A - Condensed ring aromatic compound for organic light-emitting device and organic light-emitting device having the same - Google Patents

Abstract

Provided are a condensed ring aromatic compound for an organic light-emitting device, and an organic light-emitting device having optical output with high efficiency and high luminescence and having durability. An organic light-emitting device including an anode and a cathode, and a layer made of an organic compound interposed between the anode and the cathode, wherein at least one layer of the layers made of the organic compound contains a condensed ring aromatic compound shown in the following general formula [1]: wherein R1 to R16 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 may be the same or different.

Description

Condensed ring aromatic compound for organic light-emitting device and organic luminescent device with it

Technical field

The present invention relates to condensed ring aromatic compound for organic light-emitting device and organic luminescent device with this condensed ring aromatic compound.

Background technology

Organic luminescent device is to have the device that is clipped in the film between anode and the negative electrode that contains the fluorescence organic compound.Charged electronics and hole (positive hole) from each electrode make that the exciton of fluorescence compound is produced, and when this exciton returned ground state, organic luminescent device was luminous thus.

The recent development of organic luminescent device is remarkable, and the example of its characteristic be included in low apply variation, the high-speed response of high brightness voltage under, emission wavelength and can form approach and lightweight luminescent device.According to these characteristics, show that organic luminescent device can be used for purposes widely.

But, under present situation, require more high brightness or the more luminous power of high conversion efficiency.In addition, consider from the viewpoint of weather resistance, still exist many problems for example since life-time service through the time variation or contain the deterioration that the atmosphere gas of oxygen and moisture causes.

When considering to be applied to full-color display etc., need have for example blue, green and red luminous of excellent color purity, but can not approve fully and solve these problems.Therefore, need be used to realize having good color purity, the organic light-emitting device material of high-luminous-efficiency and gratifying weather resistance.

As solution to the problems described above, advised condensed ring aromatic compound is used for the organic light-emitting device composition material.As the example that condensed ring aromatic compound is used for the organic light-emitting device composition 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.H10-189248 and Japanese Patent Application Publication No.H09-241629 are disclosed.But, do not disclose condensed ring aromatic compound of the present invention or contain the organic luminescent device of this compound as composition material.In addition, J.Org.Chem.64,1650-1656,1999 also disclose condensed ring aromatic compound.

Summary of the invention

Make the present invention for solving the aforementioned problems in the prior.That is, the purpose of this invention is to provide condensed ring aromatic compound for organic light-emitting device.Another object of the present invention provides light output with high-level efficiency and high brightness and the organic luminescent device with weather resistance.

In order to address the above problem, the present inventor studies, and they have finished the present invention as a result.That is,, provide condensed ring aromatic compound for organic light-emitting device by following general formula [1] expression according to the present invention.

In the formula, R ₁～R ₁₆Represent by 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, and they can be identical or different.

Condensed ring aromatic compound of the present invention has high-quantum efficiency, and therefore, can provide light output with high-level efficiency and high brightness and the organic luminescent device with weather resistance according to the present invention.

Description of drawings

Fig. 1 is the sectional view of explanation according to organic luminescent device first embodiment of the present invention.

Fig. 2 is the sectional view of explanation according to organic luminescent device second embodiment of the present invention.

Fig. 3 is the sectional view of explanation according to organic luminescent device the 3rd embodiment of the present invention.

Fig. 4 is the sectional view of explanation according to organic luminescent device the 4th embodiment of the present invention.

Fig. 5 is the sectional view of explanation according to organic luminescent device the 5th embodiment of the present invention.

Fig. 6 is the toluene solution (1 * 10 of illustrated example compd A-1 ^-5Mol/l) PL spectrum (excitation wavelength: figure 340nm).

Fig. 7 is the toluene solution (1 * 10 of illustrated example Compound C-6 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Fig. 8 is the toluene solution (1 * 10 of illustrated example compound G-14 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Fig. 9 is the toluene solution (1 * 10 of illustrated example compound G-19 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Figure 10 is the toluene solution (1 * 10 of illustrated example compound G-18 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Figure 11 is the toluene solution (1 * 10 of illustrated example compound G-22 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Figure 12 is the toluene solution (1 * 10 of illustrated example compound G-20 ^-5Mol/l) PL spectrum (excitation wavelength: figure 355nm).

Embodiment

At first describe condensed ring aromatic compound of the present invention in detail.Condensed ring aromatic compound for organic light-emitting device of the present invention is represented by following general formula [1]:

In formula [1], R ₁～R ₁₆Represent by 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, and they can be identical or different.

R in the top general formula [1] below is shown ₁～R ₁₆The substituent object lesson of expression.But example is not limited to them.

By R ₁～R ₁₆The example of the halogen atom of expression comprises fluorine, chlorine, bromine and iodine.

By R ₁～R ₁₆The 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 styroyl.

By R ₁～R ₁₆The example of the alkoxyl group of expression comprises methoxyl group, oxyethyl group, propoxy-, 2-ethyl-octyloxy and benzyloxy.

By R ₁～R ₁₆The examples of aryloxy of expression comprises phenoxy group, 4-tertiary butyl phenoxy group and thiophene oxy.

By R ₁～R ₁₆The 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 (methyl-phenoxide base) 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 R ₁～R ₁₆The example of aryl of expression comprise phenyl, naphthyl, pentalene base, indenyl, Azulene base, anthryl, pyrenyl, indacenyl base, acenaphthenyl, phenanthryl, phenalenyl base, fluoranthene base, vinegar phenanthrene (acephenanthryl) base, aceanthrenyl, benzo [9,10] phenanthryl,

Base, naphthacenyl, perylene base, pentacenyl, xenyl, terphenyl and fluorenyl.

By R ₁～R ₁₆The example of the aryl of expression also comprises the substituting group from following compound deriving.

Above-claimed cpd can have halogen atom, alkyl is methyl, ethyl, sec.-propyl, the tertiary butyl for example, alkoxyl group is methoxyl group, oxyethyl group, propoxy-for example, aryloxy is phenoxy group, 4-tertiary butyl phenoxy group for example, amino group is N for example, N-diphenyl amino, N, N-dinaphthyl amino, aryl be for example pyridyl and pyrryl of phenyl, naphthyl or heterocyclic radical for example.

By R ₁～R ₁₆The example of the heterocyclic radical of expression comprises pyridyl, pyrryl, oxazolyl, oxadiazole base, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, carbazyl, acridyl and phenanthrolyl base.

By R ₁～R ₁₆The substituent example that can contain in alkyl, aryl and the heterocyclic radical of expression 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 (methyl-phenoxide base) 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.

Can synthesize the condensed ring aromatic compound of representing by general formula [1] by the method shown in for example following synthetic route 1 or 2 or 3.

Synthetic route 1

Use dibromo

Derivative and 2-hydroxy phenyl boric acid derivatives or bromine chloroiodobenzone derivative can synthesize the condensed ring aromatic compound of general formula [1] expression as raw material, and for example, as shown in following synthetic route 1, still, synthetic method is not limited to this.

Concrete grammar to synthetic route 1 is illustrated.At first, pass through dibromo

The suzuki-miyaura coupled reaction of derivative and 2-hydroxy phenyl boric acid derivatives synthesize the dihydroxyl form (for example, Chem.Rev.1995,95,2457-2483).As other method, for example, also enumerate the Yamamoto method (for example, Bull.Chem.Soc.Jpn.51,2091,1978) of using nickel catalyzator.Synthetic dihydroxyl form is developed become two trifluoromethanesulfonic acid ester-formins, and carry out intramolecular cyclization reaction (for example, J.Org.Chem.68,883-887,2003) in form in two triflate.Thus, can obtain condensed ring aromatic compound by general formula [1] expression.

Synthetic route 2

Use dibromo Derivative and bromine chloroiodobenzone derivative can synthesize the condensed ring aromatic compound of being represented by general formula [1] as raw material, for example, and as shown in following synthetic route 2.

Concrete grammar to synthetic route 2 is illustrated.

Synthetic route 2 is the synthetic methods through dichloro-thing form, and dichloro-thing form is the compound that produces in the 3rd step in above-mentioned synthesis step.This route is for the R from general formula [1] simply and easily ₄～R ₇Perhaps R ₁₂～R ₁₅It is particularly useful to introduce various substituent situations.Particularly, with dibromo

Derivative develops into two tetramethyl ethylene ketone thing forms (for example, J.Org.Chem.65,164,2000).Carry out the suzuki-miyaura coupled reaction with bromine chloroiodobenzone derivative then, and then carry out cyclisation (for example, J.Org.Chem.68,883-887 with the technology similar to intramolecular cyclization reaction in the said synthesis route 1,2003), develop into dichloro-thing form thus.

Below the example that uses this dichloro-thing form to introduce various substituent synthetic methods as intermediate is described.

For example, these examples comprise coupled reaction for example suzuki-miyaura coupled reaction (J.Am.Chem.Soc.120,9722,1998), Still reaction (Macromolecules.18,321,1985) and Heck reaction (J.Org.Chem.46,1067,1981).

Synthetic route 3

Use dibromo Derivative also can synthesize the condensed ring aromatic compound of being represented by general formula [1] as raw material, for example, and as shown in following synthetic route 3.

Concrete grammar to synthetic route 3 is illustrated.

Synthetic route 3 is for the R from general formula [1] simply and easily ₄～R ₇Perhaps R ₁₂～R ₁₅It is particularly useful to introduce various substituent situations.Particularly, with dibromo

Derivative develops into the Compound C R-1 of ester-formin.Be hydrolyzed on ester-formin then developing into Compound C R-2, and experience step subsequently, developing then becomes Compound C R-3 as acyl chlorides.In addition, by intramolecular cyclization (for example, J.Am.Chem.Soc.105,7375,1983), Compound C R-3 is developed into the ketone form.This ketone formal transformation is become diketone form (for example, Bull.Chem.Soc.Jpn.59,3311,1986).Use this diketone form as intermediate, after two steps through Knoevenagel reaction (for example, Eur.J.Org.Chem.4185,2002) and Diels-Alder reaction (for example, J.Org.Che.62,530,1997), from R ₄～R ₇Perhaps R ₁₂～R ₁₅Introduce various substituting groups.

In order to improve the organic light-emitting device luminous efficiency, usually, wish that the luminous quantum efficiency of luminescence center material itself is big.

R in the general formula [1] ₁～R ₁₆The compound that all is hydrogen atom has high luminous quantum efficiency in dilute solution, as shown in Example 1.Therefore, when the compound of general formula [1] is used as the organic light-emitting device material, can expect to increase the luminous efficiency of device.

In addition, by substituting group being introduced the R in the general formula [1] ₁～R ₁₆, can reduce the reduction of the luminous efficiency that molecular association causes.Especially and since because of adjacent substituent sterically hindered substituting group easily with the vertical direction in plane of the compound of general formula [1] expression on locate, to R ₁, R ₄, R ₇, R ₈, R ₉, R ₁₂, R ₁₅, R ₁₆Introduce substituting group and have big influence for the reduction that reduces the luminous efficiency that causes by molecular association.

Bring sterically hindered substituent example to comprise alkyl, alkoxyl group, aryloxy, amino group, aryl and heterocyclic radical to molecule itself.Preferred example comprises amino group, aryl and heterocyclic radical.

In addition, when the compound of general formula [1] expression was used as luminescent layer, this compound can be used for any of material of main part and guest materials.Especially, when the compound of general formula [1] expression during as the material of main part in the luminescent layer, this material preferably has high glass-transition temperature, and therefore, this compound is preferably at R ₁～R ₁₆The place has substituting group.

The substituent example that is used to improve second-order transition temperature preferably includes amino group, aryl and heterocyclic radical.

The intermediate in this synthesis step of substituent example will introduce as to(for) the compound that uses general formula [1] expression is a halogen atom.In this case, the level of activity from building-up reactions is considered, preferred iodine, bromine and chlorine.

Compound as the organic luminescent device material preferably has the high carrier injection.Improving the current carrier injection makes device with low voltage drive.Substituent example to be introduced is preferably amino group and heterocyclic radical in order preferably to have the high carrier injection.Usually, when amino group is introduced as substituting group, the hole injection is improved.And when introducing heterocyclic radical, the electronics injection is improved.

To convert at the emission wavelength in rare solvent in the situation of cie color coordinate, the not replacement form of condensed ring aromatic compound of the present invention shows the blueness with preferred color of choice purity.Therefore, extend into the illuminant colour that this substituent introducing that does not replace form can be converted to long wavelength side from blueness with pi-conjugated.Be used to extend pi-conjugated substituent example and comprise amino group, aryl and heterocyclic radical.

The object lesson of the compound in the above-mentioned general formula [1] is as follows.But the invention is not restricted to these examples.

Then organic luminescent device of the present invention is described in detail.

Organic luminescent device of the present invention comprises anode and negative electrode, and insert between this anode and this negative electrode by organic compound make the layer.In the organic luminescent device of the present invention, the layer of being made by organic compound contains condensed ring aromatic compound of the present invention.

Except above-mentioned by organic compound make the layer, organic luminescent device of the present invention can have other organic compound layer.The example of other organic compound layer comprises hole transmission layer, hole injection layer, electronic barrier layer, hole blocking layer, electron transfer layer and electron injecting layer.

Hereinafter, with reference to accompanying drawing, organic luminescent device of the present invention is elaborated.

Reference numeral in the accompanying drawing at first is described.

Reference numeral 1 expression substrate, Reference numeral 2 expression anodes, Reference numeral 3 expression luminescent layers, Reference numeral 4 expression negative electrodes, Reference numeral 5 expression hole transmission layers, Reference numeral 6 expression electron transfer layers, Reference numeral 7 expression hole injection layers, Reference numeral 8 expression hole and/or exciton barrier-layers; Represent organic luminescent device respectively with Reference numeral 10,20,30,40,50 and 60.

Fig. 1 is the sectional view of explanation according to organic light-emitting device first embodiment of the present invention.In the organic luminescent device 10 in Fig. 1, anode 2, luminescent layer 3 and negative electrode 4 are successively set on the substrate 1.This organic luminescent device 10 is useful when having cavity transmission ability, electron transport ability and the whole organic compound of luminescent properties characteristic and form at luminescent layer 3.It is also useful when in addition, the organic compound of any characteristic of organic luminescent device 10 when have cavity transmission ability, electron transport ability and luminescent properties characteristic by mixing in is formed luminescent layer 3.

Fig. 2 is the sectional view of explanation according to organic light-emitting device second embodiment of the present invention.In the organic luminescent device 20 among Fig. 2, on substrate 1, set gradually anode 2, hole transmission layer 5, electron transfer layer 6 and negative electrode 4.It is useful when a kind of luminous organic compound of this organic luminescent device 20 in will having hole transport performance and electronic transmission performance is used in combination with the organic compound that only has electronic transmission performance or only have a hole transport performance.In addition, in organic luminescent device 20, hole transmission layer 5 or electron transfer layer 6 also play the effect of luminescent layer.

Fig. 3 is the sectional view of explanation according to organic light-emitting device the 3rd embodiment of the present invention.Come organic luminescent device 30 in the pie graph 3 by inserting luminescent layer 3 between hole transmission layer in the organic luminescent device in Fig. 2 20 5 and the electron transfer layer 6.In this organic luminescent device 30, the carrier transport function is separated with lighting function, can have for example organic compound of hole transport performance, electronic transmission performance and luminescent properties of individual features with suitable being used in combination.Therefore, greatly increased the handiness that material is selected, and can use the various organic compound with different emission wavelengths, therefore it can make luminous tone variation.In addition, thus by making organic luminescent device 30 on luminous efficiency, be expected raising in the luminescent layer 3 that effectively current carrier or exciton is blocked in central authorities.

Fig. 4 is the sectional view of explanation according to organic light-emitting device the 4th embodiment of the present invention.By being set between anode in the organic luminescent device in Fig. 3 30 2 and the hole transmission layer 5, hole injection layer 7 comes organic luminescent device 40 in the pie graph 4.It is effectively that 40 pairs of this organic luminescent devices have low voltage, because be provided with hole injection layer 7, improves adhesion or hole injection efficiency between anode 2 and the hole transmission layer 5 thus.

Fig. 5 is the sectional view of explanation according to organic light-emitting device the 5th embodiment of the present invention.Come organic luminescent device 50 in the pie graph 5 by between luminescent layer 3 and electron transfer layer 6, insert suppressing hole or exciton by layer (hole/exciton barrier-layer 8) that arrives negative electrode 4 sides.The organic compound that has high ionization potential by use improves the luminous efficiency of organic luminous layer 50 as hole/exciton barrier-layer 8.

But above-mentioned first～the 5th embodiment is very basic device architecture just, and uses the organic light-emitting device structure of condensed ring aromatic compound of the present invention to be not limited to these structures.For example, insulation layer, bonding coat or interfering layer can be arranged on the interface of organic layer and electrode, and can form hole transmission layer by the various layer structure that the bilayer with different ionization potentials is formed.

Condensed ring aromatic compound of the present invention can be used in any of above-mentioned first～the 5th embodiment.When using condensed ring aromatic compound of the present invention, can use the simplification compound, perhaps can be used in combination multiple compound.

At the random layer of making by organic compound, for example, in the luminescent layer 3 in first～the 5th embodiment, hole transmission layer 5, electron transfer layer 6, hole injection layer 7 and the hole/exciton barrier-layer 8, contain condensed ring aromatic compound of the present invention.Preferably in luminescent layer 3, contain condensed ring aromatic compound.The condensed ring aromatic compound of the present invention that in these layers, contains can for one or both or more kinds of.

Luminescent layer 3 is preferably formed by subject and object.Herein, when luminescent layer 3 is formed by the subject and object with carrier transmission performance, reach luminous main process and comprise following step.

1. the transmission in electronics and hole in the luminescent layer

2. the generation of the exciton of main body

3. excitation energy transmission in the host molecule

4. the excitation energy from the main body to the object shifts

Energy transfer required in each step and luminous takes place with various deactivation process competitions ground.

In order to improve the organic light-emitting device luminous efficiency, need not superfluous words, the luminous quantum efficiency of luminescence center material itself is increased.But, how to carry out between main body and the main body effectively or the energy between the subject and object to shift be big factor.At present, the reason of the luminous deterioration that causes owing to energising is not clear, still, it is believed that to relate to luminescence center material itself or because the environmental change of the luminescent material that molecule causes around it at least.

When condensed ring aromatic compound of the present invention is used for main body or object, the luminous efficiency of device, be improved by the luminance brightness of device output and the weather resistance of device.

When being used in of the present invention organic luminescent device as the material of luminescent layer condensed ring aromatic compound of the present invention, can only form luminescent layer by 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.

Herein, when condensed ring aromatic compound of the present invention was used as guest materials, the amount of use was preferably 0.01 weight %～20 weight % based on material of main part, more preferably 0.1 weight %～15 weight %.Use condensed ring aromatic compound of the present invention can suitably suppress the overlapping concentration quenching that causes by each object in the luminescent layer in this scope.

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 object.

In the present invention, especially, condensed ring aromatic compound of the present invention can use conventional known lower molecular weight and polymkeric substance hole transport compound, luminophor, electric transmission compound etc. as required together as the composition material of luminescent layer.

The example of hole transport compound comprises triarylamine derivative, phenylenediamine derivative, triazole derivative, oxadiazole derivative, imdazole derivatives, pyrazoline derivative, pyrazolone derivative, oxazole derivative, Fluorenone (fluorenone) derivative, hydrazone derivative, stilbene derivative, phthalocyanine derivates, derivatives of porphyrin, poly-(vinylcarbazole), poly-(silylene), poly-(thiophene) and other electric conductive polymer.

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, the rubrene derivative, quinacridone derivative, acridone derivatives, coumarin derivatives, pyran derivate, Nile red, pyrazines derivatives, benzimidizole derivatives, benzothiazole derivant benzoxazole derivative, stilbene derivative, and organometallic complex (for example, organic aluminium compound is three (oxine closes) aluminium and organic beryllium complex for example) 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.

Example 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 the organometallic complex of electric transmission compound.

Form the anodic examples of material and comprise metal simple-substance for example gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium and tungsten, perhaps for example stannic oxide, zinc oxide, Indium sesquioxide, tin indium oxide (ITO) and indium zinc oxide of their alloy and metal oxide.In addition, other example comprises electric conductive polymer for example polyaniline, polypyrrole, Polythiophene and polyphenylene sulfide.Can use these electrode substances separately, perhaps can be used in combination multiple these materials.In addition, anode can be formed by single layer structure, perhaps can be formed by multilayered structure.

The examples of material of forming 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, other example comprises multiple alloy for example lithium-indium, sodium-potassium, magnesium-Yin, aluminium-lithium, aluminium-magnesium and magnesium-indium.In addition, example comprises for example tin indium oxide (ITO) of metal oxide.These electrode substances can use separately, perhaps multiple these combinations of substances can be used.In addition, negative electrode can be formed by single layer structure, perhaps can be formed by multilayered structure.

The substrate that uses in the organic luminescent device of the present invention is not particularly limited, and uses translucent substrate for example metal substrate and ceramic substrate, and transparency carrier for example glass, quartz and plastics sheet.

Also can wait and control colour developing light by colour filter film, fluorescence color conversion colour filter film, the dielectric reflections film that use is used for substrate.In addition, can on substrate, prepare thin film transistor (TFT) and connecting and fabricate devices.

According to taking out direction of light, two kinds of structures can be arranged: bottom emission structure (taking out the structure of light from substrate-side) and top emission structure (taking out the structure of light from the opposition side of substrate) by device.

(embodiment)

Hereinafter, the present invention is illustrated more specifically that still, the present invention is not limited to these embodiment with reference to embodiment.

＜embodiment 1〉(example compound A-1's is synthetic)

(1-1) synthetic intermediate compound 1-3's is synthetic

Compound 1-1 compound 1-2 compound 1-3

In the recovery flask with following reactant and solvent dress 300ml, and under nitrogen gas stream, stirred 8 hours down at 60 ℃.

Compound 1-1:1.3g (4.05mmol)

Compound 1-2:1.22g (8.90mmol)

Four (triphenyl phosphine) palladium (0): 519mg (0.45mmol)

Toluene: 100ml

Ethanol: 50ml

2M-aqueous sodium carbonate: 20ml

After reaction is finished, add ethyl acetate and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/1) purify, obtain the compound 1-3 (productive rate 78%) of 1.3g by silica gel column chromatography.

(1-2) synthetic intermediate 1-4's is synthetic

Compound 1-3 compound 1-4

Following reactants, solvent etc. packed into reclaim in the flask, and under-20 ℃, in cooling bath, stirred 30 minutes.

Compound 1-3:1.3g (3.15mmol)

Chloroform: 100ml

Triethylamine: 2ml

Then, to the trifluoromethanesulfanhydride anhydride that wherein slowly drips 1.58ml (9.45mmol), and at room temperature stirred 6 hours.After reaction is finished, add ethyl acetate and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/2) purify, obtain the compound 1-4 of 1.74g (productive rate 82%) with silica gel column chromatography.

(1-3) example compound A-1's is synthetic

Compound 1-4 example compound A-1

Following reactants, solvent etc. packed into reclaim in the flask, and under nitrogen gas stream, stirred 8 hours down at 80 ℃.

Compound 1-4:270mg (0.4mmol)

LiCl：100mg(2.4mmol)

1,8-diazabicyclo [5.4.0] 7-undecylene: 146mg (0.96mmol)

Two (triphenyl phosphine) palladium chloride (II): 40mg (0.04mmol)

Dimethyl formamide: 50ml

After reaction is finished, add ethyl acetate and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/3) purify, obtain the example compound A-1 of 72mg (productive rate 48%) with silica gel column chromatography.

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 376.4, and differentiated example compound A-1.

(NMR)

Structure to this example compound A-1 is confirmed with NMR mensuration.

¹H-NMR(THF-d8，400MHz)σ(ppm)：9.36(s，2H)，8.80(d，2H，J＝8.0Hz)，8.18-8.16(m，2H)，8.07(d，2H，J＝8.0Hz)，7.97-7.95(m，2H)，7.82(m，2H)，7.38(m，4H)

(fusing point)

Confirmed that with difference formula scanning calorimeter (DSC) fusing point of example compound A-1 is 378 ℃.

(characteristics of luminescence)

Measured the luminescent spectrum of example compound A-1 under solution state.In order to measure luminescent spectrum, measured the toluene solution (1 * 10 of example compound A-1 in advance with spectrophotometer U-3010 (by Hitachi, Ltd. makes) ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, use spectrophotometer F-4500 (by Hitachi, Ltd makes) to measure the toluene solution (1 * 10 of example compound A-1 ^-5Mol/l) luminescent spectrum.Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 340nm.As measurement result, obtain the PL spectrum shown in Fig. 6.According to the PL spectrum shown in Fig. 6, the first peak and second peak of the maximum emission wavelength of example compound A-1 are respectively 436nm and 461nm, and find to demonstrate preferred blue-light-emitting.

Measured example compound A-1 in toluene solution (1 * 10 ^-5Mol/l) quantum yield, result demonstrate high value for example 0.91.In addition, in the mensuration of quantum yield, be convenient to contrast use fluoranthene as a comparison control compound come evaluation.Quantum yield in the dilute solution of fluoranthene is 0.35 (Steven L, Murov., Handbook of Phtochemistry, SecondEdition, Revised and Exapanded, (1993)).

＜embodiment 2〉(example compound C-6's is synthetic)

With the synthetic example compound C-6 of synthetic method similarly to Example 1.Particularly, except compound 1-2 being changed into compound 1-5, with embodiment 1 in synthesize under the same condition.

Compound 1-1 compound 1-5 example compound C-6

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 488.6, and differentiated example compound C-6.

(NMR)

Structure to this example compound C-6 is confirmed with NMR mensuration.

¹H-NMR(CDCl ₃，400MHz)σ(ppm)：9.15(s，2H)，8.69(d，2H，J＝8.0Hz)，8.08-8.01(m，6H)，7.87-7.83(m，2H)，7.52-7.48(m，2H)，1.54(s，18H)

(fusing point)

Confirmed that with difference formula scanning calorimeter the fusing point of example compound C-6 is 459 ℃.

(characteristics of luminescence)

Measured the toluene solution (1 * 10 of example compound C-6 under the solution state ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, measure the toluene solution (1 * 10 of example compound C-6 ^-5Mol/l) luminescent spectrum (PL spectrum).Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 355nm.As measurement result, obtain the PL spectrum shown in Fig. 7.According to the PL spectrum shown in Fig. 7, the first peak of the maximum emission wavelength of example compound C-6 and second peak are respectively 446nm and 472nm, and find to demonstrate preferred blue-light-emitting.

＜embodiment 3〉(example compound G-14 and G-19's is synthetic)

(3-1) synthetic intermediate compound 1-6's is synthetic

Compound 1-1 compound 1-6

Following reactants and solvent are packed in the recovery flask of 300ml, and under nitrogen gas stream, stirred 8 hours down at 80 ℃.

Compound 1-1:2.5g (6.48mmol)

4,4,5,5-tetramethyl--1,3,2-dioxane pentaborane: 5.63ml (38.8mmol)

[1, two (diphenylphosphino) propane of 3-] Nickel Chloride II): 325mg (0.65mmol)

Toluene: 100ml

Triethylamine: 30ml

After reaction is finished, temperature is cooled to room temperature, adds water to it then.Add aqueous ammonium chloride solution in addition and stirred 3 hours.Then, add ethyl acetate and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene) purify, obtain the compound 1-6 of 2.1g (productive rate 68%) with silica gel column chromatography.

(3-2) synthetic intermediate compound 1-8's is synthetic

Compound 1-6 compound 1-7 compound 1-8

In the recovery flask with following reactants and solvent dress 300ml, and under nitrogen gas stream, stirred 4 hours down at 80 ℃.

Compound 1-6:2.0g (4.16mmol)

Compound 1-7:2.7g (8.5mmol)

Four (triphenyl phosphine) palladium (0): 485mg (0.42mmol)

Toluene: 100ml

Ethanol: 50ml

2M-aqueous sodium carbonate: 20ml

After reaction is finished, add toluene and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/9) purify, obtain the compound 1-8 of 1.81g (productive rate 72%) with silica gel column chromatography.

(3-3) synthetic intermediate compound 1-9's is synthetic

Compound 1-8 compound 1-9

Following reactants and solvent packed into reclaim in the flask, and under nitrogen gas stream, stirred 8 hours down at 100 ℃.

Compound 1-8:1.5g (2.47mmol)

LiCl：636mg(15.0mmol)

1,8-diazabicyclo [5.4.0] 7-undecylene: 943mg (6.20mmol)

Two (triphenyl phosphine) palladium chloride (II): 40mg (0.24mmol)

Dimethyl formamide: 150ml

After reaction is finished, add water to it and also at room temperature stirred 1 hour.Affirmation has orange throw out in reaction soln, filters then, and water, methyl alcohol and acetone wash filtrate.Filtrate is dry and obtain the compound 1-9 of 1.1g (productive rate 51%).

To the compound that obtains, measured molecular weight.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 445.3, and differentiated compound 1-9.

(3-4) example compound G-14 and G-19's is synthetic

Following reactants and solvent packed into reclaim in the flask, and under nitrogen gas stream, stirred 8 hours down at 80 ℃.

Compound 1-9:500mg (1.12mmol)

Compound 1-10:100mg (2.4mmol)

Acid chloride (II): 75mg (0.33mmol)

2-dicyclohexyl phosphino--2 ', 6 '-dimethoxy-biphenyl: 410mg (0.99mmol)

Tripotassium phosphate: 713mg (3.36mmol)

Toluene: 50ml

After reaction is finished, add toluene and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/3) purify, obtain the example compound G-14 of 209mg (productive rate 32%) and the example compound G-19 of 97mg (productive rate 18%) with silica gel column chromatography.

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) each M+ is 584.7 and 480.6, and differentiated example compound G-14 and G-19.

(NMR)

Measure the structure of having confirmed example compound G-14 with NMR.

¹H-NMR(CDCl ₃，400MHz)σ(ppm)：9.22(s，2H)，8.74(d，2H，J＝9.6Hz)，8.19(d，2H，J＝9.2Hz)，8.03(d，2H，J＝8.2Hz)，7.88(dd，2H，J＝8.4Hz，J＝8.2Hz)，7.78(d，2H，J＝0.96Hz)，7.27-7.20(m，8H)，2.18(s，12H)。

Also measure the structure of having confirmed example compound G-19 with NMR.

¹H-NMR(CDCl ₃，400MHz)σ(ppm)：9.10(s，2H)，9.08(s，2H)，8.63(d，2H，J＝9.6Hz)，8.14(d，1H，J＝7.2Hz)，8.01-8.06(m，1H)，7.99(dd，1H，J＝7.2Hz，J＝11.2Hz)，7.95-7.92(m，1H)，7.84-7.76(m，2H)，7.46-7.42(m，2H)，7.26-7.18(m，4H)，2.19(s，6H)

(characteristics of luminescence)

With with embodiment 1 in same mode carry out the mensuration of the characteristics of luminescence.

Measured the toluene solution (1 * 10 of example compound G-14 and G-19 under the solution state ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, measure the toluene solution (1 * 10 of example compound G-14 and G-19 ^-5Mol/l) luminescent spectrum (PL spectrum).Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 340nm.As measurement result, obtain the PL spectrum shown in Fig. 7.According to the PL spectrum shown in Fig. 7, the first peak of the maximum emission wavelength of example compound G-14 and second peak are respectively 444nm and 470nm, and find to demonstrate blue-light-emitting, and the first peak of the maximum emission wavelength of example compound G-19 and second peak are respectively 440nm and 467nm, and find to demonstrate blue-light-emitting.

＜embodiment 4〉(example compound G-18's is synthetic)

With the synthetic example compound G-18 of synthetic method similarly to Example 3.Particularly, except compound 1-10 being changed into the compound 1-11 among the embodiment 1, with embodiment 3 in synthesize under the same condition.

Compound 1-9 compound 1-11 example compound G-18

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 656.8, and differentiated example compound G-18.

(NMR)

Measure the structure of having confirmed this compound with NMR.

¹H-NMR(CDCl ₃，600MHz)σ(ppm)：9.34(s，2H)，8.82(d，2H，J＝5.8Hz)，8.30(d，2H，J＝6.3Hz)，8.06(d，2H，J＝5.8Hz)，7.93-7.86(m，8H)，7.62(d，2H，J＝7.1Hz)，7.51(d，2H，J＝7.1Hz)，7.46-7.39(m，6H)，2.40(s，6H)

(characteristics of luminescence)

With with embodiment 1 in same mode carry out the mensuration of the characteristics of luminescence.

Measured the toluene solution (1 * 10 of example compound G-18 under the solution state ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, measure the toluene solution (1 * 10 of example compound G-18 ^-5Mol/l) luminescent spectrum (PL spectrum).Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 355nm.As measurement result, obtain the PL spectrum shown in Fig. 7.According to the PL spectrum shown in Fig. 7, the first peak of the maximum emission wavelength of example compound G-18 and second peak are respectively 442nm and 469nm, and find to demonstrate preferred blue-light-emitting.

＜embodiment 5〉(example compound G-22's is synthetic)

(5-1) synthetic intermediate compound 1-12's is synthetic

Compound 1-1 compound 1-12

Following reactants and solvent are packed in the recovery flask of 300ml, and under nitrogen gas stream, stirred 18 hours down 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 '-methoxyl biphenyl: 324mg (1.04mmol)

Toluene: 100ml

Ethanol: 15ml

After reaction is finished, add toluene and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/chloroform=1/1) purify, obtain the compound 1-12 of 2.87g (productive rate 55%) with silica gel column chromatography.

(5-2) synthetic intermediate compound 1-13's is synthetic

Compound 1-12 compound 1-13

Following reactants and solvent packed into reclaim in the flask, and stirred 24 hours down at 90 ℃.

Compound 1-12:3.76g (89.6mmol)

Diox: 30ml

One hydronium(ion) oxidation lithium: 3.76g (89.6mmol)

(20ml) adds to this suspension gradually with concentrated hydrochloric acid, and at room temperature stirs this mixture 5 hours.Then, add water (200ml) and pass through filtration to it sedimentary crystal separation.Water, methyl alcohol and diethyl ether clean this crystal and carry out drying with the high vacuum heating successively, obtain the compound 1-13 of 2.87g (productive rate 93%).

(5-3) synthetic intermediate compound 1-15's is synthetic

Compound 1-13 compound 1-14 compound 1-15

Following reactants and solvent packed into reclaim in the flask, and stirred 2 hours down at 80 ℃.

Compound 1-13:2.87g (6.36mmol)

Thionyl chloride: 50ml

Dimethyl formamide: 300 μ l

Under reduced pressure this suspension is distilled, and (2.1g 15.9mmol) adds residue successively, and this mixture of vigorous stirring 18 hours at room temperature with methylene dichloride (50ml) and aluminum chloride.(180ml) adds to this suspension with concentrated hydrochloric acid, and stirs 1 hour under heating.By this suspension of filtering separation, and use chloroform this filtrate to be carried out the Soxhlet extraction to concentrate the material of extraction as solvent.(launch solvent: chloroform/ethyl acetate=15/1) purify, and obtain the compound 1-15 of 1.2g (productive rate 61%) with silica gel column chromatography.

(5-4) synthetic intermediate compound 1-16's is synthetic

Compound 1-15 compound 1-16

Following reactants and solvent packed into reclaim in the flask, and stirred 18 hours down at 130 ℃.

Compound 1-15:1.2g (3.89mmol)

Benzene selenic anhydride: 4.4g (8.56mmol)

Chlorobenzene: 60ml

This suspension is cooled to 100 ℃, and by filtering sedimentary crystal separation.The crystal that obtains cleans with hexane, carries out drying under high vacuum, obtains the compound 1-16 of 1.27g (productive rate 97%).

(5-5) synthetic intermediate compound 1-18's is synthetic

Compound 1-17

Compound 1-16 compound 1-18

Following reactants and solvent packed into reclaim in the flask, and under nitrogen gas stream, stirred 18 hours down at 80 ℃.

Compound 1-16:37mg (0.0046mmol)

Compound 1-17:40mg (0.0092mmol)

Ethanol: 2ml

Toluene: 0.4ml

6N-potassium hydroxide: 300 μ l

After reaction is finished, crystal placed be cooled to room temperature and separate by filtration.Clean this crystal and under high vacuum, carry out drying with methyl alcohol and IPE successively, obtain the compound 1-18 of 55mg (productive rate 99%).

(5-6) example compound G-22's is synthetic

Compound 1-18 example compound G-22

Pack into following reactants, solvent and acetylene gas in the autoclave and seal, and stirred 24 hours down at 190 ℃.

Compound 1-18:200mg (0.176mmol)

Ethylene dichloride: 4ml

After reaction is finished, crystal placed be cooled to room temperature and separate by filtration.Fully clean this crystal with hexane/toluene=2/1.(launch solvent: hexane/chloroform=4/1) purify, obtain the example compound G-22 of 0.14g (productive rate 70%) with silica gel column chromatography.

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 1129.68, and differentiated example compound G-22.

(NMR)

Measure the structure of having confirmed this example compound G-22 by NMR.

¹H-NMR(CDCl ₃，400MHz)σ(ppm)：8.01(s，2H)，7.80(d，2H，J＝8.0Hz)，7.80(t，2H，J＝2.0Hz)，7.57(t，2H，J＝2.0Hz)，8.18-8.16(m，2H)，8.07(t，2H，J＝2.0Hz)，7.54(d，4H，J＝2.0Hz)，7.53(d，4H，J＝2.0Hz)，7.40-7.32(m，4H)，1.42(s，36H)，1.40(s，36H)

(characteristics of luminescence)

With with embodiment 1 in same mode carry out the mensuration of the characteristics of luminescence.

Measured the toluene solution (1 * 10 of example compound G-22 under the solution state ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, measure the toluene solution (1 * 10 of example compound G-22 ^-5Mol/l) luminescent spectrum (PL spectrum).Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 355nm.As measurement result, obtain the PL spectrum shown in Figure 11.According to the PL spectrum shown in Figure 11, the first peak of the maximum emission wavelength of example compound G-22 and second peak are respectively 458nm and 486nm, and find to demonstrate preferred blue-light-emitting.

＜embodiment 6〉(example compound G-24's is synthetic)

Compound 1-19 example compound G-24

Following reactants and solvent packed into reclaim in the flask, and under nitrogen atmosphere, stirring 1 hour under 150 ℃.

Compound 1-19:500mg (0.603mmol)

LiCl：76mg(1.81mmol)

1,8-diazabicyclo [5.4.0] 7-undecylene: 918mg (6.03mmol)

Acid chloride: 13.5mg (0.0603mmol)

2-dicyclohexyl phosphino--2 ', 6 '-dimethoxy-biphenyl: 56.8mg (0.133mmol)

Dimethyl formamide: 30ml

After reaction is finished, add ethyl acetate and water, on sal epsom, carry out drying, then solvent is distilled to separate organic layer.(launch solvent: toluene/heptane=1/2) purify, obtain the example compound G-24 of 32mg (productive rate 10%) with silica gel column chromatography.

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 528.6, and differentiated example compound G-24.

＜embodiment 7〉(example compound G-20's is synthetic)

(7-1) compound 1-20's is synthetic

With 20.0g (87.6mmol)

, 46.7g (350mmol) aluminum chloride and 400ml methylene dichloride pack in the there-necked flask of 500ml, and when stirring, under-78 ℃, splashing into 55.6g (438mmol) oxalyl chloride under the nitrogen atmosphere, and then stirred this mixture 30 minutes, and temperature of reaction is risen to room temperature through 2 hours.When stirring, reaction mixture is poured in the frozen water of 4L, and filtered out the solid of generation, and make solid dispersed and clean with the methyl alcohol of 100ml.Solid is filtered and carries out drying and obtain 21.5g (productive rate: compound 1-20 (orange powder) 87%) under heating under vacuum.

(7-2) compound 1-22's is synthetic

2.01g (7.10mmol) compound 1-20,1.50g (7.13mmol) compound 1-21 and 100ml ethanol are packed in the 200ml there-necked flask, and when stirring, under nitrogen atmosphere, at room temperature splash into the 25ml aqueous solution that has dissolved 4.00g potassium hydroxide.Then with mixture heating up to 75 ℃ and stirred 1 hour 30 minutes.With the solid of reaction solution cooling and filtering-depositing, carry out dry to obtain 3.08g (productive rate: compound 1-22 (green powder) 95%).

(7-3) compound 1-23's is synthetic

With 2 of 3.00g (6.58mmol) compound 1-22,4.97g (54mmol), 5-norbornadiene and 40ml diacetyl oxide are packed in the 200ml there-necked flask, and this mixture is heated to 90 ℃ under nitrogen atmosphere, and stir 18 hours.Reaction mixture is cooled to room temperature and solvent is under reduced pressure distilled, (launch solvent: the mixture of toluene and heptane) the purification residue is to obtain 1.58g (productive rate: compound 1-23 (yellow powder) 53%) to use silica gel chromatography then.

(7-4) compound 1-24's is synthetic

1.00g (2.20mmol) compound 1-23,1.06g (7.92mmol) aluminum chloride and 50ml methylene dichloride are packed in the 100ml there-necked flask, and when stirring, under-78 ℃ temperature, splashing into 1.11g (8.80mmol) oxalyl chloride under the nitrogen atmosphere, then with mixture restir 30 minutes, and through 2 hours temperature of reaction is risen to room temperature.When stirring, reaction mixture is poured in the frozen water of 1L, and filtered out the solid of generation, and make solid dispersed and clean with the methyl alcohol of 30ml.Solid is filtered and carries out drying to obtain 0.894g (productive rate: compound 1-24 (orange powder) 80%) under heating under vacuum.

(7-5) compound 1-26's is synthetic

0.890g (1.75mmol) compound 1-24,0.855g (1.97mmol) compound 1-25,100ml ethanol and 10ml toluene are packed in the 200ml there-necked flask, when stirring, under nitrogen atmosphere, at room temperature splash into the 5ml aqueous solution that has dissolved 1.11g potassium hydroxide.Then with mixture heating up to 75 ℃ and stirred 2 hours 30 minutes.The cooling reaction solution also filters precipitated solid and carries out drying to obtain 0.49g (productive rate: compound 1-26 (green powder) 31%).

(7-6) example compound G-20's is synthetic

With 0.49g (0.541mmol) compound 1-26,4.97g (54mmol) 2,5-norbornadiene and 40ml diacetyl oxide are packed in the 200ml there-necked flask, and under nitrogen atmosphere with mixture heating up to 90 ℃, and stirred 18 hours.Reaction mixture is cooled to room temperature also under reduced pressure solvent is distilled, residue is purified with silica gel chromatography (launch solvent: then the mixture of toluene and heptane) to obtain 0.17g (productive rate: example compound G-20 (yellow powder) 35%).

To the compound that obtains, measure and estimated its physicals.

(molecular weight)

Confirmed that with MALDI-TOF-MS (substance assistant laser desorpted ionized-flight time mass spectrum) M+ is 905.5, and differentiated example compound G-20.

(NMR)

Measure the structure of having confirmed this example compound G-20 with NMR.

¹H-NMR(CDCl ₃，400MHz)σ(ppm)：8.35(s，1H)，8.00(s，1H)，7.81(dd，2H，J＝8.4Hz，J＝10.4Hz)，7.76-7.73(m，3H)，7.69-7.64(m，5H)，7.56-7.50(m，8H)，7.45-7.30(m，7H)，7.22(d，1H，J＝7.2Hz)，1.42(s，18H)，1.40(s，18H)

(characteristics of luminescence)

With with embodiment 1 in same mode carry out the mensuration of the characteristics of luminescence.

Measured the toluene solution (1 * 10 of example compound G-20 under the solution state ^-5Mol/l) absorption spectrum.After measuring absorption spectrum, measure the toluene solution (1 * 10 of example compound G-20 ^-5Mol/l) luminescent spectrum (PL spectrum).Herein, as the measurement result of absorption spectrum, excitation wavelength is defined as 355nm.As measurement result, obtain the PL spectrum shown in Figure 12.According to the PL spectrum shown in Figure 12, the first peak of the maximum emission wavelength of example compound G-20 and second peak are respectively 456nm and 482nm, and find to demonstrate preferred blue-light-emitting.

With embodiment 1 in can synthesize example compound B-2, C-12, D-1, E-8, F-6, G-1, G-2, G-7, G-10, G-40, G-41 and H-2 under the same condition, the compound shown in the table 1 that illustrates below using and 2 replaces the compound 1-1 and 1-2 among the embodiment 1.

(table 1)

(table 2)

＜embodiment 8〉(organic light-emitting device preparation)

In the present embodiment, the organic luminescent device shown in preparation Fig. 3.At first, go up the sheet glass that tin indium oxide (ITO) (anode 2) patterning is had the ITO electrode with preparation with the 100nm thickness at glass substrate (substrate 1).Then, have on the sheet glass of ITO electrode at this, the vacuum moulding machine by resistive heating will form film continuously by layer and the negative electrode that organic compound is made.Particularly, at first, the following compound that illustrates 2 formation had the film of 20nm thickness as hole transmission layer 5.Then, as luminescent layer 3, make the content of example compound A-1 be 1 weight % as main body and example compound A-1 as the object codeposition the following compound that illustrates 3 based on compound 3.Herein, the film thickness with luminescent layer 3 is set in 30nm.Then, as electron transfer layer, the following compound that illustrates 4 is formed the film of thickness 30nm.Then KF is formed film and the last film that aluminium is formed 100nm thickness of thickness 1nm.Herein, KF and Al play the effect of negative electrode 4.

Compound 2 compounds 3

Compound 4

In addition, when forming film, the pressure in the vacuum chamber is set in 10 ^-5Pa.In addition, for fabricate devices, the electrode relative area is made as 3mm ²Obtain organic luminescent device like this, as mentioned above.

By measuring its performance the organic luminescent device that obtains is estimated.Particularly, use the micro ampere table 4140B that makes by Hewlett-Packard Co. to measure the I-E characteristic of device, use the BM7 that makes by Topcon Corporation to measure the luminance brightness of device.The result observes under the voltage applying of 4.0V has 360cd/m ²The blue-light-emitting of luminance brightness.When at driving element under such condition so that under the nitrogen atmosphere current density remain on 30mA/cm ²With apply voltage in the time of 100 hours, initial brightness is from 800cd/m ²Change to 740cd/m ²According to the above, can think the organic luminescent device of having realized having favourable luminous efficiency and excellent weather resistance.

＜embodiment 9〉(organic light-emitting device preparation)

With similarly to Example 8 device preparation method the device of example compound C-6 is estimated.Particularly, with embodiment 8 in fabricate devices under the same condition, except in embodiment 8, changing example compound A-1 into example compound C-6.

The result observes under the voltage applying of 4.0V has 810cd/m ²The blue-light-emitting of luminance brightness.Current density remains on 30mA/cm under the nitrogen atmosphere when making at driving element under such condition ²With apply voltage in the time of 100 hours, initial brightness is from 1250cd/m ²Change to 1000cd/m ²According to the above, can think the organic luminescent device of having realized having favourable luminous efficiency and excellent weather resistance.

＜embodiment 10〉(organic light-emitting device preparation)

With similarly to Example 8 device preparation method the device of example compound G-14 is estimated.Particularly, with embodiment 8 in fabricate devices under the same condition, except in embodiment 8, changing example compound A-1 into example compound G-14.

The result observes under the voltage applying of 4.0V has 950cd/m ²The blue-light-emitting of luminance brightness.Current density remains on 30mA/cm under the nitrogen atmosphere when making at driving element under such condition ²With apply voltage in the time of 100 hours, initial brightness is from 1320cd/m ²Change to 1210cd/m ²According to the above, can think the organic luminescent device of having realized having favourable luminous efficiency and excellent weather resistance.

＜embodiment 11〉(organic light-emitting device preparation)

With similarly to Example 8 device preparation method the device of example compound G-18 is estimated.Particularly, with embodiment 8 in fabricate devices under the same condition, except in embodiment 8, changing example compound A-1 into example compound G-18.

The result observes under the voltage applying of 4.0V has 1250cd/m ²The blue-light-emitting of luminance brightness.Current density remains on 30mA/cm under the nitrogen atmosphere when making at driving element under such condition ²With apply voltage in the time of 100 hours, initial brightness is from 1500cd/m ²Change to 1400cd/m ²According to the above, can think the organic luminescent device of having realized having favourable luminous efficiency and excellent weather resistance.

＜embodiment 12〉(organic light-emitting device preparation)

With similarly to Example 8 device preparation method the device of example compound G-20 is estimated.Particularly, with embodiment 8 in fabricate devices under the same condition, except in embodiment 8, changing example compound A-1 into example compound G-20.

The result observes under the voltage applying of 4.0V has 1340cd/m ²The blue-light-emitting of luminance brightness.Current density remains on 30mA/cm under the nitrogen atmosphere when making at driving element under such condition ²With apply voltage in the time of 100 hours, initial brightness is from 1480cd/m ²Change to 1320cd/m ²According to the above, can think the organic luminescent device of having realized having favourable luminous efficiency and excellent weather resistance.

The rights and interests of the Japanese patent application No.2007-096343 that this application requires to submit on April 2nd, 2007, the No.2008-038299 that submits on February 30th, 2008 are drawn it in full in this article thus and are reference.

Claims (3)

1. by the condensed ring aromatic compound for organic light-emitting device of following general formula [1] expression:

R wherein ₁～R 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 can be identical or different.

2. organic luminescent device, it comprise anode and negative electrode and insert this anode and this negative electrode between the layer of making by organic compound, wherein should contain condensed ring aromatic compound according to claim 1 by the layer that organic compound is made.

3. organic luminescent device according to claim 2, wherein this layer of being made by organic compound that contains condensed ring aromatic compound is a luminescent layer.

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