CN101835874A - Luminescent-element material and luminescent element - Google Patents

Luminescent-element material and luminescent element Download PDF

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CN101835874A
CN101835874A CN200880113149A CN200880113149A CN101835874A CN 101835874 A CN101835874 A CN 101835874A CN 200880113149 A CN200880113149 A CN 200880113149A CN 200880113149 A CN200880113149 A CN 200880113149A CN 101835874 A CN101835874 A CN 101835874A
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长尾和真
富永刚
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Idemitsu Kosan Co Ltd
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Toray Industries Inc
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Abstract

Disclosed is a light-emitting device material containing an anthracene compound represented by the general formula (1) below. This light-emitting device material enables a light-emitting device to have high efficiency and excellent durability. Also disclosed is a light-emitting device using such a light-emitting device material. In the formula below, R1-R16 may be the same as or different from each other and each represents a member selected from the group consisting of a hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an amino group, a silyl group and a ring structure formed together with an adjacent substituent, provided that one of R9-R16 is used for the linkage with A; R17-R20 may be the same as or different from each other and each represents a member selected from the group consisting of a hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an amino group and a silyl group; R21 represents a member selected from the group consisting of a hydrogen, a linear alkyl group, a cycloalkyl group, a heterocyclic group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an amino group, a silyl group and a ring structure formed together with an adjacent substituent; A represents an arylene group; n represents 1 or 2; and X represents an oxygen atom or a sulfur atom.

Description

Light emitting element material and luminous element
Technical field
The present invention relates to a kind ofly as the useful light emitting element material of fluorochrome and charge transport material and use its luminous element, described luminous element can be used for fields such as display element, flat-panel monitor, backlight, illumination, interior finish (interior), mark, billboard, Electrofax and optical signal generator.
Background technology
The research of organic film luminous element in recent years is more active, and described organic film luminous element is luminous when combining once more in by the organic luminophor of the two poles of the earth clamping from the anode injected holes from the negative electrode injected electrons.This luminous element is characterised in that, thin and under low driving voltage high brightness luminescent, and, receive much concern by selecting luminescent material can send polychromatic light.
Since the C.W.Tang of Eastman Kodak company etc. pointed out that organic film luminous element high brightness ground is luminous, a lot of research institutions were just carrying out this research.The exemplary configuration of the organic film luminous element that the research group of Kodak company proposes is, on ito glass substrate, set gradually the cavity conveying diamine compound, as three (oxine) aluminium (III) of luminescent layer and as the Mg:Ag (alloy) of negative electrode, under the driving voltage about 10V, can send 1,000cd/m 2Green (referring to non-patent literature 1).
In addition, the organic film luminous element can send the light of multiple color by use multiple fluorescent material in luminescent layer, and is therefore very in vogue to the practical research of indicating meter etc.The research of green luminescent material is the most deep in the three primary colors luminescent material, concentrates on studies to improve its characteristic over against red illuminating material and blue emitting material now.
One of problem of maximum in the organic film luminous element is to take into account the luminous efficiency and the weather resistance of element.Particularly for blue light emitting device, provide the blue emitting material of excellent in te pins of durability, element that reliability is high less.The technology of use styryl derivative (referring to patent documentation 1) is for example disclosed.In addition, also disclose and will be used for the example of blue light emitting device by the anthracene compound (referring to patent documentation 2～5) that diphenylene-oxide replaces, still, above-mentioned technology all can not fully be taken into account luminous efficiency and weather resistance.
No. 3086272 communique of [patent documentation 1] patent
[patent documentation 2] TOHKEMY 2005-314239 communique
[patent documentation 3] international specification sheets that discloses No. 05/113531
[patent documentation 4] TOHKEMY 2007-63501 communique
[patent documentation 5] TOHKEMY 2007-238500 communique
[non-patent literature 1] Applied Physics Letters (U.S.), 1987,51 volumes, No. 12,913～915 pages
Summary of the invention
The blue light emitting device of luminous efficiency height and excellent in te pins of durability can not be provided in the existing organic film luminous element as mentioned above.Therefore the object of the present invention is to provide a kind of light emitting element material and use its luminous element, described light emitting element material can obtain the blue light emitting device of luminous efficiency height and excellent in te pins of durability.
The present invention is the light emitting element material that contains the anthracene compound of general formula (1) expression.
Figure GPA00001113364200021
R 1～R 16Identical or different, respectively expression be selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms.Wherein, R 9～R 16In any be used for being connected with A.R 17～R 20Identical or different, expression is selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, reaches the group in the silyl respectively.R 21Expression be selected from hydrogen atom, straight chained alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms.A represents arylidene.N is 1 or 2.X is Sauerstoffatom or sulphur atom.
In addition, the present invention relates to a kind of luminous element, it is characterized in that, there is luminescent layer at least in described luminous element between anode and negative electrode, luminous by electric energy, and described luminous element contains the light emitting element material of general formula (1) expression.
The present invention can provide a kind of light emitting element material that can be used in luminous element etc. and thin film stability excellence.And, can obtain having the luminous element of high-luminous-efficiency and excellent durability.
Embodiment
The anthracene compound of general formula (1) expression that the present invention uses is described.
R 1～R 16Identical or different, respectively expression be selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms.Wherein, R 9～R 16In any be used for being connected with A.R 17～R 20Identical or different, expression is selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, reaches the group in the silyl respectively.R 21Expression be selected from hydrogen atom, straight chained alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms.A represents arylidene.N is 1 or 2.X is Sauerstoffatom or sulphur atom.
In the above-mentioned substituting group, so-called alkyl is represented for example representative examples of saturated aliphatic alkyl such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, the tertiary butyl, and they can have substituting group also can not have substituting group.The substituting group that appends when being substituted is not particularly limited, and can enumerate for example alkyl, aryl, heteroaryl etc., at this point, also is general in following record.In addition, the carbonatoms of alkyl is not particularly limited, but considers from easy acquisition and cost aspect, be generally more than 1 below 20, and more preferably be the scope below 8 more than 1, more preferably methyl, ethyl, sec.-propyl, sec-butyl, the tertiary butyl.
So-called cycloalkyl is represented for example saturated fat ring type alkyl such as cyclopropyl, cyclohexyl, norcamphyl, adamantyl, and they can have substituting group also can not have substituting group.The carbonatoms of moieties is not particularly limited, usually in the scope below 20 more than 3.
So-called straight chained alkyl is represented for example straight chain representative examples of saturated aliphatic alkyl such as methyl, ethyl, n-propyl, normal-butyl.The carbonatoms of moieties is not particularly limited, but considers from easy acquisition and cost aspect, usually in the scope below 8 more than 1.
So-called heterocyclic radical represents to have in the rings such as pyranoid ring, piperidine ring, cyclic amide for example the aliphatics ring of the atom outside the de-carbon, and they can have substituting group also can not have substituting group.The carbonatoms of heterocyclic radical is not particularly limited, usually in the scope below 20 more than 2.
So-called alkoxyl group represents that for example methoxyl group, oxyethyl group, propoxy-etc. are by the functional group of ehter bond and aliphatic alkyl bonding, and described aliphatic alkyl can have substituting group also can not have substituting group.The carbonatoms of alkoxyl group is not particularly limited, usually in the scope below 20 more than 1.
So-called alkyl sulfenyl, the group that is replaced by sulphur atom for the Sauerstoffatom of the ehter bond of alkoxyl group.The alkyl of alkyl sulfenyl can have substituting group also can not have substituting group.The carbonatoms of alkyl sulfenyl is not particularly limited, usually in the scope below 20 more than 1.
So-called aryl is represented for example aromatic hydrocarbyls such as phenyl, naphthyl, xenyl, phenanthryl, terphenyl.Aryl can not have replacement and can be substituted yet.The carbonatoms of aryl is not particularly limited, usually in the scope below 40 more than 6, more preferably in the scope below 12 more than 6.As aryl more preferably phenyl, naphthyl, xenyl.
So-called heteroaryl, have the ring-type aromatic series base of the one or more atoms outside the de-carbon in the rings such as expression furyl, thienyl, pyrryl, benzofuryl, benzothienyl, indyl, pyridyl, quinolyl, they can have substituting group also can not have substituting group.The carbonatoms of heteroaryl is not particularly limited, and is preferred usually in the scope below 30 more than 2.
Amino can have substituting group also can not have substituting group.Can enumerate for example aforesaid alkyl, cycloalkyl, aryl, heteroaryl etc. as substituting group.
So-called silyl represents that trimethyl silyl for example etc. has the functional group with the key of silicon atom bonding, and they can have substituting group also can not have substituting group.The carbonatoms of silyl is not particularly limited, and is preferred usually in the scope below 20 more than 3.In addition, the Siliciumatom number is preferred usually in the scope below 6 more than 1.
In addition, arbitrarily adjacent 2 substituting groups (R of general formula (1) for example 18With R 21) also bonding mutually, form conjugation or unconjugated condensed ring.Formation element as condensed ring can also contain the element that is selected from nitrogen, oxygen, sulphur, phosphorus and the silicon outside the de-carbon.In addition, condensed ring also can be further and other cyclic condensations.
So-called arylidene, divalence or trivalent group that expression phenylene, naphthylidene, biphenylene, phenanthrylene, inferior terphenyl (Terphenylene) etc. are derived and obtained by aromatic hydrocarbons, they can have substituting group also can not have substituting group.The carbonatoms of arylidene is not particularly limited, usually in the scope below 40 more than 6, more preferably in the scope below 12 more than 6.The divalent group (naphthylidene) of more preferably deriving the divalent group (phenylene) that obtains and deriving and obtain as arylidene by naphthyl by phenyl.
Above-mentioned group can have substituting group also can not have substituting group, and the position of substitution is not particularly limited when having substituting group.In addition, can have a plurality of substituting groups, can have a plurality of identical substituting groups this moment, also can have different substituting groups.
The anthracene compound of general formula of the present invention (1) expression, in molecule, have 1～2 that basic A is connected with the anthracene skeleton through connecting, for to aromatic diphenylene-oxide skeleton of electronics condensation (when X is Sauerstoffatom) or dibenzothiophene skeleton (when X is sulphur atom), can take into account thermotolerance and charge-transporting thus.And then, because the A of general formula (1) is an arylidene, thus stable film can be formed, can be long-term durability luminous.Wherein, consider obtaining and the synthetic easiness of raw material, more preferably A is phenylene or naphthylidene.
In the anthracene compound of general formula of the present invention (1) expression, A is connected with 9 (carbon potentials on the central rings) of anthracene skeleton, and from high fluorescent quantum yield and the viewpoint consideration of the thin film stability raising when making element, this is crucial.
In addition, can comprise above-mentioned diphenylene-oxide skeleton or dibenzothiophene skeleton respectively individually in the general formula (1), also can comprise both each one, when the X that contains general formula (1) is the diphenylene-oxide skeleton of Sauerstoffatom, can access higher luminous efficiency, so be preferred.In addition, the quantity of diphenylene-oxide skeleton or dibenzothiophene skeleton (n value) more preferably is 1.In addition, R 9～R 16In any be used for being connected with A, but from raw material obtaining and synthetic easiness aspect is considered, preferred R 9Be used for being connected with A.
In addition, the bonding position of above-mentioned diphenylene-oxide skeleton or dibenzothiophene skeleton and anthracene skeleton relation when being phenylene for general formula A, can in ortho position, a position, the contraposition any, but more preferably at a contraposition or a position bonding.Wherein, consider from the viewpoint that can form stabilizing films, particularly preferably in para-linkage.In addition, the bonding position of above-mentioned diphenylene-oxide skeleton or dibenzothiophene skeleton and anthracene skeleton relation when general formula A is naphthylidene is not particularly limited, but more preferably at 2 and 6 bondings of naphthylidene.
In addition, in the anthracene compound of general formula of the present invention (1) expression, R 21Be selected from hydrogen atom, straight chained alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl and and adjacent substituting group between the ring structure that forms, the viewpoint of the thin film stability during from the manufacturing element considers that this is crucial.Wherein, R 21More preferably be selected from hydrogen atom, straight chained alkyl, heterocyclic radical, aryl, heteroaryl, and and adjacent substituting group between the ring structure that forms, be preferably especially hydrogen atom, straight chained alkyl, aryl or and adjacent substituting group between the ring structure that forms.In addition, the substituting group of 10 (carbon potentials on the central rings) of anthracene skeleton is phenyl (R at this moment 21Be hydrogen atom), 2-xenyl (R 21Be hydrogen atom), 4-xenyl (R 21Be phenyl), to toluyl (R 21Be methyl) or betanaphthyl (R 21With adjacent substituent R 18Perhaps R 19The ring structure that forms) time, the thin film stability when making element improves effect and further increases, so be preferred.
As above-mentioned anthracene compound, be not particularly limited, specifically enumerate following example.
Figure GPA00001113364200071
Figure GPA00001113364200081
Figure GPA00001113364200101
Figure GPA00001113364200111
Figure GPA00001113364200121
Figure GPA00001113364200131
Figure GPA00001113364200141
Figure GPA00001113364200151
Figure GPA00001113364200161
The synthetic of the anthracene compound of general formula (1) expression can be used known method.In the anthracene skeleton, import the method for dibenzofuran group, for example can enumerate following method: in the presence of palladium or nickel catalyzator, make halo anthracene derivant and diphenylene-oxide metal complex or dibenzofuran group aryl (dibenzofuranylaryl) metal complex carry out the method for linked reaction, in the presence of palladium or nickel catalyzator, make anthryl metal complex and halogenated diphenyl benzofuran derivs carry out method of linked reaction etc., but be not limited thereto.
Next, describe the embodiment of luminous element of the present invention for example in detail.Luminous element of the present invention has anode, negative electrode and the organic layer between above-mentioned anode and negative electrode, and this organic layer contains luminescent layer at least, and this luminescent layer is luminous by electric energy.
Organic layer except that the structure that only is made of luminescent layer, can also enumerate 1) hole transporting layer/luminescent layer/electron supplying layer, and 2) luminescent layer/electron supplying layer, 3) laminate structures such as hole transporting layer/luminescent layer.In addition, above-mentioned each layer difference can be in individual layer, the multilayer any.When hole transporting layer and electron supplying layer are made of multilayer, the layer that will be connected side sometimes with electrode is called hole injection layer and electron injecting layer, but hole-injecting material is included in the hole transporting material in the following explanation, and the electronics injecting material is included in the electron transport materials.
In the luminous element of the present invention, organic layer is formed by the light emitting element material of the anthracene compound that contains general formula (1) expression.So-called light emitting element material for self luminous material and help in its luminous material any, is meant and luminous relevant compound, particularly is hole transporting material, luminescent material and electron transport materials etc.
Anthracene compound of the present invention can be used as hole transporting material and electron transport materials, but considers that it has high luminescent properties, more preferably as luminescent material.In addition, anthracene compound of the present invention sends high light at blue region, thus preferably use as blue emitting material, also can by with other luminescent materials combinations, the material of using as green～red light-emitting component or white-light luminescent component uses.White-light luminescent component can obtain by the material of laminated multiple different colors.Particularly, can enumerate 3 fit layer by layer systems of 2 fit layer by layer systems, blue emitting material, green luminescent material and the red illuminating material of blue emitting material and Yellow luminous material, light blue luminescent material and orange luminescence material.Because anthracene compound of the present invention preferably uses as blue emitting material, thus by with other different luminescent materials for example 2,3,5,6-1H, 4H-tetrahydrochysene-9-(2 '-benzothiazolyl) quinolizino-[9,9a, 1-gh] green luminescent material, 1,3 such as tonka bean camphor, 5,7-four (4-tert-butyl-phenyl)-8-phenyl-4,4-two fluoro-4-boron are mixed-3a, and 4a-diaza-red illuminating materials such as s-benzo two indenes carry out 3 and close layer by layer, can obtain white-light luminescent component.
The anode that the present invention uses, as long as be the material of injected hole in organic layer efficiently, be not particularly limited, but preferably use the bigger material of work function, can enumerate for example stannic oxide, Indium sesquioxide, indium zinc oxide, indium tin oxide target conductive metal oxides such as (ITO), perhaps metal such as gold and silver, chromium, inorganic conductive materials such as cupric iodide, cupric sulfide, electric conductive polymers such as Polythiophene, polypyrrole and polyaniline etc.Above-mentioned electrode materials can use separately, also various material layers can be closed or is mixed into to exercise and use.
Make luminous element luminous as long as anodic resistance can be supplied with sufficient electric current, but consider to be preferably low resistance from luminous element power consumption aspect.As long as for example be that the following ito substrate of 300 Ω/ then can be used as element electrode and carries out work, but owing to also can supply with substrate about 10 Ω/ at present, so especially preferably use the following low resistance thing of 100 Ω/.The thickness of ITO can be selected arbitrarily according to resistance value, how to use with the thickness between 100～300nm usually.
In addition, in order to keep the physical strength of luminous element, preferably on substrate, form luminous element.Substrate preferably uses glass substrates such as soda glass and non-alkali glass.As long as having enough thickness, the thickness of glass substrate keeps physical strength, therefore as long as for more than the 0.5mm.About the material of glass, because released ion is better less from glass, so be preferably non-alkali glass.Because implemented SiO 2Soda-lime glass (soda-lime glass) Deng barrier coat is also commercially available, so can also use this soda-lime glass.And then if anode can stably carry out work, then substrate also needn't be glass, for example also can form anode on plastic base.ITO film formation method is not defined as electronic beam method, sputtering method and chemical reaction method etc. especially.
The material that uses in the negative electrode that the present invention uses, as long as for can in organic layer, injecting the material of electronics efficiently, be not particularly limited, can enumerate platinum, gold and silver, copper, iron, tin, zinc, aluminium, indium, chromium, lithium, sodium, potassium, caesium, calcium and magnesium and their alloy etc. usually.In order to improve electron injection efficiency and to improve element characteristic, lithium, sodium, potassium, caesium, calcium, magnesium or the alloy that contains these low workfunction metal are effective.But above-mentioned low workfunction metal is scarcely stable in atmosphere usually.Therefore, can enumerate following method as preference: the lithium of the trace that mixes in organic layer and magnesium (film thickness gauge with vacuum evaporation is expressed as below the 1nm) obtain the method for the high electrode of stability.In addition, also can use lithium fluoride and so on inorganic salt.And then; for guard electrode, can enumerate following method: with metals such as platinum, gold and silver, copper, iron, tin, aluminium and indiums or use the organic high molecular compound such as inorganicss such as alloy, silicon-dioxide, titanium dioxide and silicon nitride, polyvinyl alcohol, polyvinyl chloride, hydro carbons macromolecular compound of these metals to carry out laminated as preference.The making method of above-mentioned electrode is not particularly limited as long as be the method that resistive heating, electron beam, sputter, ion plating and coating etc. can obtain conducting.
Hole transporting layer forms by following method: laminated or mix the method for one or more kinds of hole transporting materials or use hole transporting material and the method for the mixture of polymer binder.In addition, also can in hole transporting material, add iron(ic) chloride (III) and so on inorganic salt and form hole transporting layer.As long as hole transporting material is not particularly limited for following compound, and described compound can form the making necessary film of luminous element and can be from the anode injected hole, and can carry the hole.Preference is as 4,4 '-two (N-(3-aminomethyl phenyl)-N-phenyl amino) biphenyl, 4,4 '-two (N-(1-naphthyl)-N-phenyl amino) biphenyl, 4,4 '; 4 " triphenylamine derivatives such as-three (3-aminomethyl phenyl (phenyl) amino) triphenylamine, two carbazole derivative such as two (N-allyl group carbazoles) or two (N-alkyl carbazoles), pyrazoline derivative, stilbenes compound, hydrazone compounds, benzofuran derivative and thiophene derivant oxadiazole derivative, phthalocyanine derivates, heterogeneous ring compounds such as derivatives of porphyrin, side chain in the polymer class has above-mentioned monomeric polycarbonate and styrene derivatives, Polythiophene, polyaniline, poly-fluorenes, polyvinyl carbazole and polysilane etc.
Among the present invention, luminescent layer can be single or multiple lift, is formed by luminescent material (material of main part (host material), dopant material (dopant material)) respectively, and luminescent layer can be the mixture of material of main part and dopant material, can be material of main part only also, all can.That is, in the luminous element of the present invention, only material of main part or dopant material are luminous in each luminescent layer, also can material of main part and dopant material all luminous.Consider that from the luminous viewpoint of effectively utilizing electric energy and obtaining high color purity preferred luminescent layer is made of the mixing of material of main part and dopant material.In addition, material of main part and dopant material can also can all can for multiple combination for a kind of respectively.Dopant material can be contained in whole material of main parts, also can be contained in the part material of main part, all can.Dopant material can be laminated with material of main part, also can be scattered in the material of main part, all can.Dopant material can be regulated illuminant colour.Particularly, can obtain blue-light-emitting by making up with the dopant material that sends high light at blue region, the dopant material that sends high light at green～red area can obtain the luminous of green～redness too.The amount of dopant material causes the concentration frosting phenomenon when too much, therefore preferably use below the 20 weight % with respect to material of main part, more preferably below the 10 weight %.Adulterating method can adopt the common vapour deposition method with material of main part, also can mix back evaporation simultaneously in advance with material of main part.
Luminescent layer in the luminous element of the present invention contains the anthracene compound of general formula (1) expression.Though anthracene compound of the present invention can be used as dopant material and uses, because thin film stability and charge-transporting excellence, so preferably use as material of main part.When the anthracene compound that uses among the present invention is used as material of main part,, can obtain the higher and long-life luminous element of luminous efficiency by making up with the dopant material that sends high light at blue region.And then the anthracene compound that uses among the present invention is also preferred to be made up with the dopant material that sends high light at green～red area.
The ionization potential of the anthracene compound of general formula of the present invention (1) expression is not particularly limited, is preferably below the above 7.0eV of 4.5eV, and more preferably be below the above 6.4eV of 5.4eV.Need to prove, the absolute value of ionization potential is different because of measuring method sometimes, and ionization potential of the present invention is for using air atmosphere type ultraviolet electronic analysis device (AC-1, reason are ground machine (strain) system), the thickness of evaporation on ito glass substrate is measured the value that obtains as the film of 30nm～100nm.
The material of main part that the present invention uses is not limited to only a kind of for the anthracene compound of general formula of the present invention (1) expression, also can mix multiple anthracene compound of the present invention and use, perhaps more than one other material of main parts and anthracene compound of the present invention are mixed into enforcement usefulness.As can the blended material of main part, preferred use pyrene etc. has the compound and the derivative thereof of condensation aromatic ring, N, N '-dinaphthyl-N, N '-phenylbenzene-4,4 '-phenylbenzene-1, aromatic amine derivatives such as 1 '-diamines, with three (oxine) aluminium (III) (AluminumTris (8-quinolinate)) is metal chelating combination copper 8hydroxyquinolate (oxinoid) compound of representative, distyryl radical derivatives such as distyryl base benzene derivative, the tetraphenylbutadiene derivative, indene derivative, coumarin derivatives oxadiazole derivative, Pyrrolopyridine derivatives, purple cyclic ketones (perinone) derivative, cyclopentadiene derivant oxadiazole derivative, carbazole derivative, Pyrrolopyrrole derivatives, p-phenylene vinylene in the polymer class (polyphenylenevinylene) derivative, polyparaphenylene's derivative, poly-fluorene derivatives, the polyvinyl carbazole derivative, polythiofuran derivative.
Dopant material is not particularly limited, can enumerate naphthalene, anthracene, luxuriant and rich with fragrance, pyrene, benzo [9,10] luxuriant and rich with fragrance perylene, fluorenes, indenes etc. have the compound of condensation aromatic ring and derivative thereof (2-(benzothiazole-2-yl)-9 for example, 10-diphenylanthrancene and 5,6,11,12-tetraphenyl tetracene etc.), furans, the pyrroles, thiophene, thiophene is coughed up, 9-silicon heterofluorene (9-silafluorene), 9,9 '-spiral shell, two silicon heterofluorenes, thionaphthene, cumarone, indoles, dibenzothiophene, diphenylene-oxide, imidazopyridine, phenanthroline, pyrazine, 1, the 5-naphthyridine, quinoxaline, pyrrolopyridine, thioxanthenes etc. have the compound and the derivative thereof of heteroaryl ring, borane derivative, distyryl base benzene derivative, 4,4 '-two (2-(4-diphenyl amino phenyl) vinyl) biphenyl, 4, amino-benzene ethenyl derivatives such as 4 '-two (N-(Stilbene-4-yl)-N-phenyl amino) Stilbene, the aromatic series acetylene-derivative, the tetraphenylbutadiene derivative, stilbene derivative, aldazine (aldazine) derivative, the methylene pyrrole derivative, diketone pyrrolo-[3,4-c] pyrrole derivative, 2,3,5,6-1H, 4H-tetrahydrochysene-9-(2 '-benzothiazolyl) quinolizino-[9,9a, 1-gh] coumarin derivatives such as tonka bean camphor, imidazoles, thiazole, thiadiazoles, carbazole oxazole oxadiazole, oxazole derivatives such as triazole and metal complex thereof and with N, N '-phenylbenzene-N, N '-two (3-aminomethyl phenyl)-4,4 '-phenylbenzene-1,1 '-diamines are the aromatic amine derivative of representative etc.Wherein, use when having the substituent condensation aromatic nucleus of electronics acceptability derivative as doping agent, the thin film stability more remarkable effect that pyrene compound of the present invention had is so be preferred.Particularly, as particularly preferred doping agent, can enumerate with 1-(benzoxazole-2-yl)-3,8-two (4-aminomethyl phenyl) pyrene is the pyrene compound with benzothiazole (benzoazole) base of representative, and with (6-p-methylphenyl pyrene-1-yl)-two (2,4,6-trimethylphenyl) borine be representative have two
Figure GPA00001113364200211
The pyrene compound of base boryl (dimesitylboryl).
Among the present invention, so-called electron supplying layer is the layer that injects electronics and conveying electronic from negative electrode.Electron supplying layer preferred electron injection efficiency height and efficient are carried the electronics that is injected into well.Therefore electron supplying layer preferably is made of following substances: electron affinity is big, electronic migration is big and excellent in stability, be difficult for the impurity that generation forms trap when making and when using.But, when considering the conveying balance of hole and electronics, if electron supplying layer is mainly realized following function and is not promptly flowed with combining once more from the anodic hole and can stop effectively to cathode side, even then be made of the very not high material of electron transport ability, its effect that improves luminous efficiency also is equal to when being made of the high material of electron transport ability.Therefore, in the electron supplying layer of the present invention, also comprise the hole trapping layer that can efficient stops the hole to be moved well as the synonym thing.
The electron transport materials that electron supplying layer uses, be not particularly limited, can enumerate naphthalene, anthracene, pyrenes etc. have the compound and the derivative thereof of condensation aromatic ring, with 4,4 '-two (diphenylacetylene) biphenyl is the vinylbenzene base class aromatic nucleus derivative of representative; the perylene derivative, purple cyclic ketone derivative, coumarin derivatives, Naphthalamide derivatives, quinone derivative such as anthraquinone and diphenoquinone, the phosphine oxide derivative, carbazole derivative and indole derivatives, three (oxine) aluminium hydroxyquinoline complex compounds such as (III), reach hydroxyl azoles (Hydroxyazole) complex compounds such as Qiang base Ben Ji oxazole complex compound, the azomethine complex compound, tropolone metal complex and flavonol metal complex, owing to can reduce driving voltage, so containing, the preferred compound with heteroaryl ring structure that uses, described heteroaryl ring structure be selected from carbon, hydrogen, nitrogen, oxygen, silicon, element in the phosphorus, and has electronics acceptability nitrogen.
Electronics acceptability nitrogen among so-called the present invention, the nitrogen-atoms of formation multiple bond between expression and the adjacent atom.Because nitrogen-atoms has high electronegativity, so this multiple bond has the character of accepting electronics.Therefore, have the heteroaryl ring of electronics acceptability nitrogen, have high electron affinity, electron transport can be excellent, can reduce driving voltage of light-emitting by using it for electron supplying layer.Heteroaryl ring with electronics acceptability nitrogen, can enumerate for example pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, Mi Dingbing pyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole Huan, oxadiazole ring, triazole ring, thiazole ring, thiadiazoles ring, benzoxazole ring, benzothiazole ring, benzoglyoxaline ring, phenanthro-imidazole ring etc.
As above-mentioned compound with heteroaryl ring structure, can enumerate for example oligomerization pyridine derivate, quinoxaline derivativess and 1 such as benzimidizole derivatives, benzoxazole derivative, benzothiazole derivant, oxadiazole derivative, thiadiazoles derivative, triazole derivative, pyrazines derivatives, phenanthroline derivative, quinoxaline derivatives, quinoline, benzoquinoline derivative, dipyridyl and three pyridines as preferred compound, 5-naphthyridines derivativess etc. are as compound.Wherein, can consider the aspect from electron transport, (the imdazole derivatives such as the benzene of N-phenyl benzimidazolyl-2 radicals-yl) that preferred uses three, 1,3-two [(4-tert-butyl-phenyl) 1,3, derivative such as oxadiazole such as 4-oxadiazole base] Ben Deng, N-naphthyl-2,5-phenylbenzene-1,3, triazole derivatives such as 4-triazole, 2,9-dimethyl-4,7-biphenyl-1,10-phenanthrolene (Bathocuproin) and 1, phenanthroline derivatives such as 3-two (1,10-phenanthroline-9-yl) benzene, 2,2 '-two (benzo [h] quinoline-2-yl)-9,9 '-spiral shell, two fluorenes benzoquinoline derivatives such as (spirobifluorene), 2,5-two (6 '-(2 ', 2 "-bipyridyl))-1,1-dimethyl-3; 4-phenylbenzene thiophene such as coughs up at dipyridyl derivatives; 1; three pyridine derivates such as 3-two (4 '-(2,2 ': 6 ' 2 "-three pyridyl)) benzene, (1,8-(1 for two (1-naphthyl)-4-, the 5-naphthyridine)-and the 2-yl) naphthyridine derivative such as phenyl phosphine oxide.And, 1,3-two (1,10-phenanthroline-9-yl) benzene, 2,7-two (1,10-phenanthroline-9-yl) naphthalene, 1, phenanthroline dipolymers such as 3-two (2-phenyl-1,10-phenanthroline-9-yl) benzene, and 2,5-two (6 '-(2 '; 2 "-bipyridyl))-1,1-dimethyl-3,4-phenylbenzene thiophene such as cough up at the dipyridyl dipolymer, during with the luminescent layer combination of the anthracene compound that contains general formula (1) expression, luminous efficiency improves effect and enlarges markedly, and enumerates as more preferred example.
And then, because the thin film stability and the charge-transporting excellence of anthracene compound of the present invention, thus excellent characteristic can be obtained when using as material of main part, and owing to its charge-transporting height, so also preferably use as electron transport materials.
Above-mentioned electron transport materials can use separately, also above-mentioned electron transport materials more than 2 kinds can be mixed into enforcement usefulness, perhaps more than one other electron transport materials and above-mentioned electron transport materials is mixed into enforcement usefulness.In addition, can also be mixed into following substances and exercise to use: basic metal, contain the complex compound of complex compound, alkaline-earth metal, the inorganic salt that contain alkaline-earth metal, alkaline-earth metal and organism formation that alkali-metal inorganic salt, basic metal and organism form etc.The ionization potential of electron supplying layer is not particularly limited, is preferably below the above 8.0eV of 5.5eV, and more preferably be below the above 7.5eV of 5.7eV.
The formation method that constitutes above-mentioned each layer of luminous element is that resistive heating evaporation, electron beam evaporation plating, sputter, molecular layer are legal, coating method, ink jet method, print process, induced with laser thermal transfer etc., be not particularly limited, but consider element characteristic, usually preferred resistive heating evaporation or electron beam evaporation plating.
The thickness of organic layer also is subjected to the influence of the resistance value of luminophore, so do not do concrete qualification, can select between 1～1000nm.The thickness of luminescent layer, electron supplying layer and hole transporting layer is preferably respectively below the above 200nm of 1nm, more preferably below the above 100nm of 5nm.
Luminous element of the present invention has the function that converts electrical energy into light., mainly use galvanic current herein, but also can use pulsed current and alternating current as electric energy.Current value and magnitude of voltage are not particularly limited, but consider the power consumption and the life-span of element, and preferred selection can obtain the mode of high-high brightness with the low energy of trying one's best.
Luminous element of the present invention is preferably used as the indicating meter that shows with for example matrix and/or person's section shape (segment) mode.
In the matrix-style, the pixel that is used to show is with trellis and inlay two-dimensional approach such as shape and be configured, with the mode display text and the image of the set of pixel.The shape of pixel and size determine according to purposes.During for example the image of PC, monitor, TV and literal showed, can use usually on one side was quadrilateral pixels below the 300 μ m, in addition, and during for display panel and so on giant display, Yi Bian then use pixel as the mm magnitude.Pixel arrangement with same color during monochromatic the demonstration gets final product, and arranges red, green and blue pixel during colored the demonstration and shows.Its arrangement mode exists typical trilateral and stripe-shaped during colored the demonstration.The driving method of this matrix can for the line order drive and active matrix (active matrix) in any.Though luminous element was simple in structure during line drove in proper order, when considering acting characteristic, preferred sometimes active matrix.Driving method uses respectively according to purposes.
A so-called section shape mode is meant, forms pattern predetermined information is shown, the configuration by this pattern makes the regional luminous mode of really determining.For example can enumerate that the moment and temperature in digital display electronic watch and the thermometer represented, operating states such as audio equipment and electromagnetic cooker show and the panel demonstration of automobile etc.Matrix shows and section shape shows and can coexist in identical panel.
Luminous element of the present invention is preferably used as the backlight of various device etc.Backlight is mainly used in the visibility of can not the be own luminous display unit of raising, can be used for liquid crystal indicator, table, audio devices, car panel, display plate and mark etc.Luminous element of the present invention is particularly preferred for backlight that liquid crystal indicator uses, is especially wherein just carrying out the backlight that the PC of slimming research is used.By luminous element of the present invention, can provide and existing backlight thin in comparison and light-weight backlight.
Embodiment
Below provide embodiment the present invention is described, but the present invention is not limited to described embodiment.Need to prove that the numbering of compound is meant the numbering of record compound in the top chemical formula among following each embodiment.As described below about the evaluation method of structural analysis in addition.
1H-NMR: use superconduction FTNMREX-270 (NEC (strain) system), measure with chloroformic solution of deuteration.
HPLC purity: use high performance liquid chromatography LC-10 ((strain) Shimadzu Seisakusho Ltd. system) to measure with the 0.1g/L chloroformic solution.As the expansion solvent of post, use the mixing solutions of 0.1% phosphate aqueous solution and acetonitrile.
Synthesis example 1 (synthetic method of compound [1])
Under nitrogen gas stream, under 100 ℃ with 9-bromine anthracene 5.0g, phenyl-boron dihydroxide 3.6g, Tripotassium phosphate 12.4g, PdCl 2(dppf) CH 2Cl 2The mixing solutions heated and stirred of dimethyl formamide 120ml after the 480mg and the degassing 3 hours.In solution, inject 100ml water, filter precipitate.After water 50ml, methyl alcohol 50ml clean respectively with the solid that leaches, refining by silica gel column chromatography, vacuum-drying, obtaining 3.9g is the 9-phenylanthracene of white powder.
Then, under nitrogen gas stream, the mixing solutions with 9-phenylanthracene 3.9g and N-bromo-succinimide 3.0g and dimethyl formamide 150ml under room temperature stirred 5 hours.Inject 100ml water, filter the throw out of gained, behind the washed with methanol solid, obtain 4.6g 9-bromo-10-phenylanthracene.
Then, under nitrogen gas stream, under 100 ℃ with 9-bromo-10-phenylanthracene 2.0g, 4-[4-(4,4,5,5-tetramethyl--[1,3,2] two oxa-s borine-2-yl) phenyl] diphenylene-oxide 2.9g, Tripotassium phosphate 3.3g, PdCl 2(dppf) CH 2Cl 2The mixing solutions heated and stirred of dimethyl formamide 36ml after the 147mg and the degassing 4 hours.After being cooled to room temperature, filter the crystallization of gained.After cleaning with dimethyl formamide 10ml, water 30ml, ethanol 30ml successively, add 200ml toluene, under 140 ℃, make its dissolving.After being cooled to 100 ℃, use diatomite filtration.Evaporated filtrate adds 50ml methyl alcohol, filters.After the vacuum-drying, obtain the 2.4g white crystals.The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [1].
1H-NMR(CDCl 3(d＝ppm))：7.34-8.22(m，24H)。
Need to prove that this compound [1] is 1 * 10 -3After about 270 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.8% before sublimation purifying, is 99.9% behind sublimation purifying.
Synthesis example 2 (synthetic method of compound [2])
Except that using 4-aminomethyl phenyl boric acid to replace the phenyl-boron dihydroxide, synthetic according to the method identical with synthesis example 1, obtain white crystals.The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [2].
1H-NMR(CDCl 3(d＝ppm))：2.56(s，3H)，7.32-8.21(m，23H)。
Need to prove that this compound [2] is 1 * 10 -3After about 260 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.7% before sublimation purifying, is 99.8% behind sublimation purifying.
Synthesis example 3 (synthetic method of compound [17])
Except that using the 2-naphthalene boronic acids to replace the phenyl-boron dihydroxide, synthesize according to the method identical with synthesis example 1, obtain white crystals.The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [17].
1H-NMR(CDCl 3(d＝ppm))：7.31-8.23(m，26H)。
Need to prove that this compound [17] is 1 * 10 -3After about 270 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.8% before sublimation purifying, is 99.9% behind sublimation purifying.
Synthesis example 4 (synthetic method of compound [11])
Except that using 4-biphenyl boric acid to replace the phenyl-boron dihydroxide, synthesize according to the method identical with synthesis example 1, obtain white crystals.The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [11].
1H-NMR(CDCl 3(d＝ppm))：7.36-8.22(m，28H)。
Need to prove that this compound [11] is 1 * 10 -3After about 300 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.4% before sublimation purifying, is 99.9% behind sublimation purifying.
Synthesis example 5 (synthetic method of compound [13])
Under nitrogen gas stream, under the room temperature mixing solutions of the tetrahydrofuran (THF) 30ml after 9-bromine anthracene 3.3g, 2-biphenyl boric acid 3.0g, Potassium monofluoride 2.5g, tri-butyl phosphine a tetrafluoro borate 91mg, two (dibenzalacetone) palladium (0) 150mg and the degassing being stirred 20 hours.Use diatomite filtration solution.Evaporated filtrate, by the refining enriched material of silica gel column chromatography, vacuum-drying obtains 1.7g 9-biphenyl-2-base-anthracene.
Then, under nitrogen gas stream, the mixing solutions with 9-biphenyl-2-base-anthracene 1.7g and N-bromo-succinimide 993mg and dimethyl formamide 15ml under room temperature stirred 5 hours.Inject 20ml water, filter the throw out of gained, behind the washed with methanol solid, refining by silica gel column chromatography, vacuum-drying obtains 1.8g 9-biphenyl-2-base-10-bromine anthracene.
Then, under nitrogen gas stream, under 100 ℃ with 9-biphenyl-2-base-10-bromine anthracene 1.8g, 4-[4-(4,4,5,5-tetramethyl--[1,3,2] two oxa-s borine-2-yl) phenyl] diphenylene-oxide 1.8g, Tripotassium phosphate 2.0g, PdCl 2(dppf) CH 2Cl 2The mixing solutions heated and stirred of dimethyl formamide 26ml after the 145mg and the degassing 4 hours.After being cooled to room temperature, filter the crystallization of gained.After cleaning with 30ml water, 30ml ethanol successively, add toluene 200ml, under room temperature, make its dissolving, use diatomite filtration.Evaporated filtrate, refining by silica gel column chromatography, vacuum-drying obtains the 2.5g white crystals.The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [13].The gained powder 1The H-NMR analytical results is as follows, and the white crystals that can confirm above-mentioned gained is compound [13].
1H-NMR(CDCl 3(d＝ppm))：6.88-8.18(m，28H)。
Need to prove that this compound [13] is 1 * 10 -3After about 270 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.6% before sublimation purifying, is 99.6% behind sublimation purifying.
Synthesis example 6 (synthetic method of compound [79])
Under nitrogen gas stream, under the room temperature mixing solutions of the tetrahydrofuran (THF) 30ml after trifluoromethanesulfonic acid-6-bromo-2-naphthyl 5.3g, 4-diphenylene-oxide boric acid 3.2g, Potassium monofluoride 2.6g, tri-butyl phosphine a tetrafluoro borate 103mg, two (dibenzalacetone) palladium (0) 170mg and the degassing being stirred 9 hours.In solution, inject 30ml water, use the 30ml methylbenzene extraction.Clean organic layer 2 times with 30ml water, with using silica filler to filter after the dried over mgso.Evaporated filtrate thoroughly cleans the solid of gained with methyl alcohol, and vacuum-drying obtains 2.9g trifluoromethanesulfonic acid-6-diphenylene-oxide-4-base-naphthalene-2-base ester.
Then, under nitrogen gas stream, under 90 ℃ with trifluoromethanesulfonic acid-6-diphenylene-oxide-4-base-naphthalene-2-base ester 2.9g, connection boric acid pinacol ester 2.0g, jealous woman acid potassium 1.9g, PdCl 2(dppf) CH 2Cl 2The mixing solutions heated and stirred of dimethyl formamide 40ml after the 163mg and the degassing 3 hours.In solution, inject 50ml water, use the 40ml methylbenzene extraction.Clean 2 organic layers with 30ml water, with using diatomite filtration after the dried over mgso.Evaporated filtrate, refining by silica gel column chromatography, vacuum-drying obtains 1.7g 4-[6-(4,4,5,5-tetramethyl--[1,3,2] two oxa-s borine-2-yl) naphthalene-2-yl] diphenylene-oxide.
Then, remove use 4-[6-(4,4,5,5-tetramethyl--[1,3,2] naphthalene-2-yl two oxa-s borine-2-yl)] diphenylene-oxide replacement 4-[4-(4,4,5,5-tetramethyl--[1,3,2] phenyl two oxa-s borine-2-yl)] outside the diphenylene-oxide, synthesize according to the method identical with synthesis example 1, obtain faint yellow crystallization.The gained powder 1The H-NMR analytical results is as follows, and the faint yellow crystallization that can confirm above-mentioned gained is compound [79].
1H-NMR(CDCl 3(d＝ppm))：7.26-8.24(m，26H)。
Need to prove that this compound [79] is 1 * 10 -3After about 275 ℃ the use oil diffusion pump carries out sublimation purifying down, use under the pressure of Pa as light emitting element material.HPLC purity (measuring the area % at wavelength 254nm place) is 99.4% before sublimation purifying, is 99.5% behind sublimation purifying.
Embodiment 1
On the glass substrate (Asahi Glass (strain) system, 15 Ω/, electron beam evaporation plating thing) of 30 * 40mm, form the ITO conducting film of 30 * 13mm size as anode with the thickness of 150nm at the glass substrate middle body.To be formed with the anodic substrate and carry out ultrasonic cleaning 15 minutes, clean with ultrapure water afterwards with " Semico Clean (registered trademark) 56 " (Furuuchi chemistry (strain) system).Then carried out ultrasonic cleaning 15 minutes with Virahol, dipping made its drying in 15 minutes in hot methanol afterwards.Before being about to make element, this substrate to be carried out the UV-ozonize 1 hour, and be arranged in the vacuum deposition apparatus, the vacuum tightness that is vented in the device is 5 * 10 -5Below the Pa.By electrical resistance heating, at first making its thickness as hole-injecting material copper steam-plating phthalocyanine is 10nm, and making its thickness as hole transporting material evaporation 4,4 '-two (N-(1-naphthyl)-N-phenyl amino) biphenyl is 50nm.Then, it is 35nm that the evaporation luminescent material makes its thickness, is compound [1] as material of main part wherein, is the D-1 shown in the following formula as dopant material in addition, and to make the lacquer concentration of mixing be 5%.Afterwards, as electron transport materials, it is 20nm that the E-1 shown in the laminated following formula makes its thickness.To make its thickness be 0.5nm to the evaporation lithium fluoride on the organic layer of above formation, afterwards AM aluminum metallization make its thickness be 1000nm as negative electrode, make the square element of 5 * 5mm.Said herein thickness is the displayed value of crystal oscillation formula film thickness monitoring device.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency blue light of luminous efficiency 5.3lm/W.With this luminous element at 10mA/cm 2Continuous drive under the DC condition, the time of reducing by half of brightness as a result is 7500 hours.
Figure GPA00001113364200301
Embodiment 2～6
Except that using the described material of table 1, make luminous element similarly to Example 1 as the material of main part.Each embodiment the results are shown in table 1.
Comparative example 1
Except that using the H-1 shown in the following formula, make luminous element similarly to Example 1 as the material of main part.At 10mA/cm 2Following this luminous element of direct drive, the result sends the blue light of luminous efficiency 2.8lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the result reduces by half through brightness in 700 hours.
Figure GPA00001113364200302
Comparative example 2～6
Except that using the described material of table 1, make luminous element similarly to Example 1 as the material of main part.Each comparative example the results are shown in table 1.Need to prove that the H-2 in the table 1, H-3, H-4, H-5, H-6 are the compound that following formula is represented.
Figure GPA00001113364200311
Embodiment 7
Except that using the D-2 shown in the following formula to make doping content as dopant material is 5%, makes luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency bluish-green coloured light of luminous efficiency 4.5lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 4000 hours.
Figure GPA00001113364200321
Embodiment 8～20
Except that using the described material of table 2, make luminous element similarly to Example 1 as material of main part and the dopant material.Each embodiment the results are shown in table 2.Need to prove that the D-3 in the table 2, D-4, D-5, D-6 are the compound that following formula is represented.
Figure GPA00001113364200322
Embodiment 21
Except that using the E-2 shown in the following formula, make luminous element similarly to Example 1 as the electron transport materials.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency blue light of luminous efficiency 1.6lm/W.At 10mA/cm 2Following this luminous element of direct drive, the time of reducing by half of brightness as a result is 4000 hours.
Figure GPA00001113364200331
Comparative example 7
Except that using E-2, similarly make luminous element with comparative example 5 as the electron transport materials.At 10mA/cm 2Following this luminous element of direct drive, the result sends the blue light of luminous efficiency 0.6lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the result reduces by half through brightness in 2500 hours.
Embodiment 22～27
Except that using the material shown in the table 2, make luminous element similarly to Example 1 as the electron transport materials.Each embodiment the results are shown in table 2.Need to prove that the E-3 in the table 2, E-4, E-5, E-6, E-7 are the compound that following formula is represented.
Figure GPA00001113364200341
Embodiment 28
Except that not using the dopant material, make luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the blue light of luminous efficiency 1.2lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 3700 hours.
Embodiment 29
Except that using compound [17], make luminous element similarly to Example 28 as the material of main part.At 10mA/cm 2Following this luminous element of direct drive, the result sends the blue light of luminous efficiency 1.5lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 4100 hours.
Comparative example 8
Except that using H-6, make luminous element similarly to Example 28 as the material of main part.At 10mA/cm 2Following this luminous element of direct drive, the result sends the blue light of luminous efficiency 0.5lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the result reduces by half through brightness in 900 hours.
Embodiment 30
Except that using the D-7 shown in following to make doping content as dopant material is 2%, makes luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency green light of luminous efficiency 6.0lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 5800 hours.
Figure GPA00001113364200351
Embodiment 31
Except that using compound [17], make luminous element similarly to Example 30 as the material of main part.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency green light of luminous efficiency 5.7lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 6000 hours.
Embodiment 32
Except that using the D-8 shown in following to make doping content as dopant material is 5%, makes luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency green light of luminous efficiency 15.0lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 10000 hours.
Figure GPA00001113364200361
Embodiment 33
Except that use following shown in D-9 to make doping content as dopant material be 5%, make luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency green light of luminous efficiency 14.3lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 11000 hours.
Figure GPA00001113364200362
Embodiment 34
With thickness is 5nm evaporation luminescent material, making material of main part is that compound [1], dopant material are D-1 and to make doping content be 5%, then, it is that compound [1], dopant material are the D-10 shown in following and to make doping content be 1% that the luminescent material that further laminated thickness is 30nm makes material of main part, in addition makes luminous element similarly to Example 1.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency white light of luminous efficiency 7.0lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 6900 hours.
Embodiment 35
Except that using compound [17], similarly make luminous element with embodiment 34 as the material of main part.At 10mA/cm 2Following this luminous element of direct drive, the result sends the high efficiency white light of luminous efficiency 6.8lm/W.With this luminous element at 10mA/cm 2Carry out continuous drive under the DC condition, the time of reducing by half of brightness as a result is 6500 hours.
Embodiment 1～6 and comparative example 1～6 the results are summarized in table 1, embodiment 7～20 the results are summarized in table 2, embodiment 21～35 and comparative example 7～8 the results are summarized in table 3.
[table 1]
Table 1
Figure GPA00001113364200381
[table 2]
Table 2
Figure GPA00001113364200382
[table 3]
Table 3
Figure GPA00001113364200391
Embodiment 36
On the glass substrate (Asahi Glass (strain) system, 15 Ω/, electron beam evaporation plating thing) of 30 * 40mm, forming size at the glass substrate middle body with the thickness of 150nm is that the ITO conducting film of 30 * 13mm is as anode.To be formed with the anodic substrate and use acetone, " SemicoClean (registered trademark) 56 " (Furuuchi chemistry (strain) system) to carry out 15 minutes ultrasonic cleaning respectively, clean with ultrapure water afterwards.Next carry out 15 minutes ultrasonic cleaning with Virahol, dipping made its drying in 15 minutes in hot methanol then.Before being about to make element, this substrate to be carried out 1 hour UV-ozonize, and be arranged in the vacuum deposition apparatus, the vacuum tightness that is vented in the device is 5 * 10 -4Below the Pa.By electrical resistance heating, at first making its thickness as hole transporting material evaporation 4,4 '-two (N-(tolyl)-N-phenyl amino) biphenyl is 150nm.Then, be 35nm evaporation luminescent material with thickness, making material of main part is that compound [1], dopant material are D-1 and to make doping content be 5%.Then, as electron transport materials, it is 20nm that laminated E-1 makes its thickness.Herein, so-called thickness is the displayed value of crystal oscillation formula film thickness monitoring device.Then, will be on the Kovar alloy sheets of thick 50 μ m be provided with the mask of 16 250 μ m peristomes (residual width 50 μ m, be equivalent to 300 μ m spacings) by wet etching, carry out the mask exchange in a vacuum, make it perpendicular to the ITO striped, fixedly make mask and ito substrate driving fit from the back side with magnet.Then, behind the elements doped lithium, it is that 200nm makes 32 * 16 dot matrix elements that AM aluminum metallization makes its thickness in the 0.5nm organic layer.This element is carried out matrix driving, and the result can display text and is not had crosstalk (crosstalk).
Utilizability on the industry
The present invention can provide a kind of light emitting element material that can be used for light-emitting component etc., thin film stability excellence. According to the present invention, can obtain having the light-emitting component of high-luminous-efficiency and the durability of excellence. Light-emitting component of the present invention can be used in the fields such as display element, flat-panel monitor, backlight, illumination, upholstery, mark, billboard, Electrofax and optical signal generator.

Claims (7)

1. a light emitting element material is characterized in that, described light emitting element material contains the anthracene compound of general formula (1) expression,
Figure FPA00001113364100011
R 1～R 16Identical or different, respectively expression be selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms, wherein R 9～R 16In any be used for being connected with A; R 17～R 20Identical or different, expression is selected from hydrogen atom, alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, reaches the group in the silyl respectively; R 21Expression be selected from hydrogen atom, straight chained alkyl, cycloalkyl, heterocyclic radical, alkoxyl group, alkyl sulfenyl, aryl, heteroaryl, amino, silyl, and and adjacent substituting group between group in the ring structure that forms; A represents arylidene; N is 1 or 2; X is Sauerstoffatom or sulphur atom.
2. light emitting element material as claimed in claim 1 is characterized in that, A is phenylene or naphthylidene.
3. as claim 1 or 2 described light emitting element materials, it is characterized in that X is a Sauerstoffatom.
4. as each described light emitting element material in the claim 1～3, it is characterized in that A is at R 9The position on connect.
5. luminous element, there is luminescent layer at least in described luminous element between anode and negative electrode, luminous by electric energy, it is characterized in that, and described luminous element contains each described light emitting element material in the claim 1～4.
6. luminous element as claimed in claim 5 is characterized in that luminescent layer contains material of main part and dopant material, and the light emitting element material of general formula (1) expression is a material of main part.
7. luminous element as claimed in claim 6, it is characterized in that, between luminescent layer and negative electrode, there is electron supplying layer at least, electron supplying layer contains the compound with heteroaryl ring structure, and described heteroaryl ring structure contains electronics acceptability nitrogen and contains the element that is selected from carbon, hydrogen, nitrogen, oxygen, silicon, the phosphorus.
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