CN105722826A - Novel organic compound, and organic electroluminescent element and electronic device comprising same - Google Patents
Novel organic compound, and organic electroluminescent element and electronic device comprising same Download PDFInfo
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Abstract
Provided are an organic compound represented by chemical formula 1 in the specification (see image in the specification) and an organic electroluminescent element comprising the same.
Description
Technical field
The organic electroluminescence device (ORGANICELECTROLUMINESCENTELEMENT) the present invention relates to novel organic compound, comprising it and electronic equipment.
Background technology
Generally, organic electronic device refers to and utilizes hole and electronics to need to carry out the device that electric charge exchanges between electrode with Organic substance.Such as, Organic substance electronic device is organic transistor, organic solar batteries, organic organic photoconductor (OPC), organic luminescent device etc., for driving element, above-mentioned Organic substance electronic device all needs luminescent material, electronics to inject or transmission material, hole injection or transmission material.
In organic electronic device, luminescent material is the most important material of the performances such as efficiency and the life-span of decision device luminescence.The requirement of this luminescent material had following several characteristic: the fluorescent quantum yield under solid state wants the mobility in big, electronics and hole to want high, should be not easily decomposed when carrying out vacuum evaporation, should form uniform thin film, to stablize.
The material being used as organic matter layer in organic electronic device can be divided into luminescent material, hole-injecting material, hole mobile material, electron transport material, electron injection material etc. by function.When only using a kind of material as luminescent material, due to can there are the following problems: because of the interaction of molecule, maximum emission wavelength moves to long wavelength and causes that color purity reduces, or cause that efficiency reduces because of decay of luminescence effect, therefore, in order to improve color purity and luminous efficiency, as luminescent material, main body/adulterant class can be used.If a small amount of adulterant that the matrix with formation luminescent layer compares band gap narrow is mixed into luminescent layer, then the exciton generated at luminescent layer moves to adulterant, thus sending high efficiency light, now, the wavelength of main body moves along with the wavelength of adulterant.That is, the kind according to the adulterant used, can obtain the luminescence of desirable wavelength.
Utilize the electroluminescent device of the pyrene compound replaced by diphenylamine derivatives disclosed in the US granted patent publication the US5153073rd, but, decline due to blue color purity, dark green is presented under most cases, when producing blue-light-emitting once in a while, the shortcoming that there is effect and luminance-reduction.
As blue light-emitting substances, central part has a diphenylanthracene structure and end is substituted with aryl disclosed in the US granted patent the 7053255th blue light-emitting compound and the organic electroluminescence device utilizing it, but, there is luminous efficiency and the low insufficient problem of brightness in above-mentioned organic electroluminescence device.
And, the aromatic amine derivative that substituted or unsubstituted hexichol amido is directly replaced by pyrene compound disclosed in No. WO2005/108348A1, but, owing to having aryl or alkyl pyrene ring is direct substitution, therefore have that to present be not the emission wavelength of the pure blue problem that moves the dark green light to long wavelength.
On the other hand, in US granted patent publication the 7233019th, Korean Patent Laid the 2006-0006760th, Korean granted patent the 10-0852328th, Korean granted patent the 10-0874472nd, utilize the organic electroluminescence device of anthracene and the pyrene compound being replaced disclosed in Korean Patent Laid 2011-0121147, but, owing to blue color purity is low, and it is difficult to navy blue (deepblue), and, owing to the color purity according to driving time reduces, therefore emission wavelength moves to long wavelength side, so that luminous efficiency increases, but, this also cannot meet embodiment pure blue, thus, there is the problem being difficult to be applicable to technicolour full color display.
As it has been described above, so far but without the exploitation fully realized material for organic electroluminescent device stable, that efficiency is high, color purity is good.Therefore, in the art, in addition it is also necessary to the material that continual exploitation is new.
Summary of the invention
Technical problem
One example of the present invention is provided with organic electroluminescence devices, especially, it is provided that be applicable to novel tetrahydro that alkene acridine (tetrahydrophenalenoacridine) class organic compound non-of organic electroluminescence device.
Another example of the present invention provides and comprises above-mentioned tetrahydrochysene that alkene acridine organic compound non-, so that the organic electroluminescence device that long-life, high brightness, efficiency and color purity improve.
Another example of the present invention provides the electronic equipment being suitable for above-mentioned organic electroluminescence device.
The means of solution problem
One example of the present invention provides the organic compound represented by formula 1 below.
Chemical formula 1
In above-mentioned chemical formula 1, Ar1 and Ar2 be separately substituted or unsubstituted phenyl, replacement or unsubstituted pyridine radicals, replacement or unsubstituted pyrimidine radicals, replacement or unsubstituted triazine radical and substituted or unsubstituted naphthyl, when above-mentioned Ar1 and Ar2 is replaced, when above-mentioned Ar1 and Ar2 is replaced, substituent group can comprise choosing free hydrogen, deuterium (D), halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, replacement or in the group of unsubstituted C1～C10 alkoxyl, phenyl, pyridine radicals and pyrimidine radicals composition at least one, above-mentioned Ar1 and Ar2 closes, by tying mutually, the cycloalkyl forming C3～C5, can be formed using with above-mentioned Ar1 and the Ar2 carbon atom the combined helical structure as spiro-atom, R1, R2, R3 and R4 are separately hydrogen, deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C40 alkyl, C5～C40 aryl, C4～C40 heteroaryl, C3～C40 cycloalkyl or C3～C40 Heterocyclylalkyl, when above-mentioned R1, R2, R3 and R4 are replaced, substituent group comprises choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, replacement or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition group at least one, L is singly-bound, substituted or unsubstituted C5～C40 arlydene or C4～C40 heteroarylidene, when above-mentioned L is replaced, substituent group can be choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, replacement or at least one in the group of unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition, Z is non-existent, singly-bound, Si (CH3)2, bivalence amido, the alkylidene of substituted or unsubstituted C1～C5 or the alkylene group of substituted or unsubstituted C2～C5, when above-mentioned Z is replaced, substituent group comprises the free C1～C40 alkyl of choosing, C5～C40 aryl, at least one in the group of C4～C40 heteroaryl and C3～C40 cycloalkyl composition, in the non-existent situation of above-mentioned Z, R5 and R6 can be separately substituted or unsubstituted C1～C40 alkyl, substituted or unsubstituted C2～C40 thiazolinyl, substituted or unsubstituted C5～C40 aryl, substituted or unsubstituted C6～C40 aralkyl, substituted or unsubstituted C5～C40 heteroaryl, substituted or unsubstituted C3～C40 cycloalkyl or substituted or unsubstituted C3～C40 Heterocyclylalkyl, when above-mentioned R5 and R6 is replaced, substituent group comprises the free deuterium of choosing, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, by the substituted or unsubstituted phenyl of the alkyl of C1～C10, by the substituted or unsubstituted pyridine radicals of the alkyl of C1～C10 (pyridyl), by the substituted or unsubstituted pyridine of the alkyl of C1～C10 (pyridinyl), by the substituted or unsubstituted naphthyl of the alkyl of C1～C10, by the substituted or unsubstituted dibenzofuran group of the alkyl of C1～C10, by the alkyl of C1～C10 substituted or unsubstituted dibenzothiophenes base and by least one in the group of the substituted or unsubstituted anthryl composition of the alkyl of C1～C10, depositing in case at above-mentioned Z, R5 and R6 is separately substituted or unsubstituted C1～C40 alkylidene, C2～C40 the alkylene group replaced by the alkyl of C1～C10, C5～C40 the arlydene replaced by the alkyl of C1～C10, C6～C40 the arylmethylene alkyl replaced by the alkyl of C1～C10, C5～C40 the heteroarylidene replaced by the alkyl of C1～C10, C3～C40 ring the alkylidene replaced by the alkyl of C1～C10, or the C3～C40 heterocycloalkylene group replaced by the alkyl of C1～C10, when above-mentioned R5 and R6 is replaced, substituent group comprises the free deuterium of choosing, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, phenyl, the phenyl replaced by the alkyl of C1～C10, the pyridine radicals (pyridyl) replaced by the alkyl of C1～C10, the pyridine (pyridinyl) that the alkyl of C1～C10 replaces, the naphthyl replaced by the alkyl of C1～C10, the dibenzofuran group replaced by the alkyl of C1～C10, at least kind in the group of the dibenzothiophenes base replaced by the alkyl of C1～C10 and the anthryl replaced by the alkyl of C1～C10 composition, carbon atom or hetero atom in above-mentioned R5 or R6 are combined by adjacent pyrene structure and connector X, and together can be formed by C1～C40 alkyl with the nitrogen-atoms and above-mentioned connector X being combined with above-mentioned R5 or R6, the five-membered ring of C5～C40 aryl and the substituted or unsubstituted fusion of C5～C40 heteroaryl or condensation or hexatomic ring, above-mentioned connector X selects in free N (Y1) and C (Y2) (Y3) group formed, now, Y1, Y2 and Y3 is each independently selected from by hydrogen atom, in the group of C1～C10 alkyl and C5～C10 aryl composition, above-mentioned hetero atom；Or the hetero atom being contained in above-mentioned heteroaryl, above-mentioned assorted alkyl, above-mentioned heteroarylidene and above-mentioned assorted alkylidene comprises at least one in the group selecting free N, O, S, Se and Si composition.
Another example of the present invention provides following organic electroluminescence device: accompany the organic thin film layer formed by one or more layers at least including luminescent layer between negative electrode and anode, at least one of which in above-mentioned organic thin film layer individually contains the one in organic compound, or containing the two or more combination in organic compound.
Another example of the present invention provides the electronic equipment including above-mentioned organic electroluminescence device.
The effect of invention
The above-mentioned organic electroluminescence device utilizing above-mentioned organic compound can realize high-luminous-efficiency, high brightness, high color purity and the luminescent lifetime significantly improved.
Accompanying drawing explanation
Fig. 1 is proton nmr spectra (1H-NMR) measurement result of compound 1 prepared in an embodiment.
Fig. 2 is differential scanning calorimeter (DSC) measurement result of compound 1 prepared in an embodiment.
Fig. 3 is thermogravimetric analyzer (TGA) measurement result of compound 1 prepared in an embodiment.
Fig. 4 is ultraviolet (UV) absorption spectrum of compound 1 prepared in an embodiment.
Fig. 5 is luminescence generated by light (PL, the PhotoLuminescence) curve chart of compound 1 prepared in an embodiment.
Detailed description of the invention
The present invention is described in detail below.
The present invention can be carried out numerous variations, and the present invention can be implemented in every way, by multiple examples (or embodiment) to being described in detail herein.But, it is not used to limit the specifically disclosed mode to the present invention, and is interpreted as it thought including being included in the present invention and all changes of technical scope, equivalent technical solutions and sub.
The term used in this manual is merely to illustrate particular instance (or aspect (aspect)) (or embodiment), and is not intended to limit the present invention.If not having obvious difference in the literal meaning, then odd number expression way includes plural number expression way.In this application, "～include～" or the term such as "～formed～" for specifying the existence of described in the description feature, numeral, step, action, structural element, components or groups thereof, it is thus understood that do not get rid of other features one or more or numeral, step, action, structural element, the existence of components or groups thereof or additional function in advance.
If without other definition, the meaning of all terms here used including technology or scientific terminology is equivalent in meaning with what general technical staff of the technical field of the invention was generally understood that.Should be interpreted that on the word of normally used term defined in dictionary and correlation technique expressed equivalent in meaning, if not explicitly defining in this application, then should be not desirable with the meaning on surface or exceedingly explain.
In this manual, organic compound refers to the compound being used in organic electroluminescence device, the scope of the organic compound of the present invention be not limited to its be necessary for can be luminous compound, its scope of application is also not limited to organic luminous layer, and all can be used in any layer constituting the organic electroluminescence device such as electric charge injection layer and charge transport layer.
And, consider that the present invention is all suitable in the situation of organic electroluminescence device and the device for solar power generation, term " organic compound " in this specification and " optical device " with on dictionary or define unrelated routinely, but for including above-mentioned term and selected term.
In this manual, " substituted or unsubstituted " in situation about stating, if without other definition, then situation about being replaced refers to following situation: be selected from by D, F, CF3、OCH3, halogen, itrile group, nitro, the alkyl of C1～C40, the thiazolinyl of C2～C40, the alkoxyl of C1～C40, the amino of C1～C40, silylation, the cycloalkyl of C3～C40, the Heterocyclylalkyl of C3～C40, the aryl of C6～C40 and C5～C40 heteroaryl composition group at least kind substituent group replace.
In this manual, if without other definition, then alkyl all includes straight chain and attachment.
In an example of the present invention, it is provided that the organic compound represented by formula 1 below.
Chemical formula 1
In above-mentioned chemical formula 1, Ar1 and Ar2 is separately substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical and substituted or unsubstituted naphthyl, when above-mentioned Ar1 and Ar2 is replaced, substituent group can comprise choosing free hydrogen, deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, phenyl, pyridine radicals and pyrimidine radicals composition group at least one, above-mentioned Ar1 and Ar2 forms the cycloalkyl of C3～C5 by combining, can be formed using with above-mentioned Ar1 and the Ar2 carbon atom the combined helical structure as spiro-atom, R1, R2, R3 and R4 are separately hydrogen, deuterium, halogen, CN, Si (CH3)3、CF3, the substituted or unsubstituted C1～C40 alkyl of nitro, C5～C40 aryl, C4～C40 heteroaryl, C3～C40 cycloalkyl or C3～C40 Heterocyclylalkyl, when above-mentioned R1, R2, R3 and R4 are replaced, substituent group comprises choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition group at least one, L be singly-bound, replacement or unsubstituted C5～C40 arlydene or C4～C40 heteroarylidene, when above-mentioned L is replaced, substituent group can be choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition group at least one, Z is non-existent, singly-bound, Si (CH3)2, bivalence amido, the alkylidene of substituted or unsubstituted C1～C5 or the alkylene group of substituted or unsubstituted C2～C5, when above-mentioned Z is replaced, substituent group comprises the free C1～C40 alkyl of choosing, C5～C40 aryl, at least one in the group of C4～C40 heteroaryl and C3～C40 cycloalkyl composition, in the non-existent situation of above-mentioned Z, R5 and R6 can be separately substituted or unsubstituted C1～C40 alkyl, substituted or unsubstituted C2～C40 thiazolinyl, substituted or unsubstituted C5～C40 aryl, substituted or unsubstituted C6～C40 aralkyl, substituted or unsubstituted C5～C40 heteroaryl, substituted or unsubstituted C3～C40 cycloalkyl or replacement or unsubstituted C3～C40 Heterocyclylalkyl, when above-mentioned R5 and R6 is replaced, substituent group comprises the free deuterium of choosing, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, by the substituted or unsubstituted phenyl of the alkyl of C1～C10, by the substituted or unsubstituted pyridine radicals of the alkyl of C1～C10 (pyridyl), by the substituted or unsubstituted pyridine of the alkyl of C1～C10 (pyridinyl), by the substituted or unsubstituted naphthyl of the alkyl of C1～C10, that replaced by the alkyl of C1～C10 or unsubstituted dibenzofuran group, by the alkyl of C1～C10 substituted or unsubstituted dibenzothiophenes base and replaced by the alkyl of C1～C10 or at least one in the group of unsubstituted anthryl composition, depositing in case at above-mentioned Z, R5 and R6 is separately substituted or unsubstituted C1～C40 alkylidene, C2～C40 the alkylene group replaced by the alkyl of C1～C10, C5～C40 the arlydene replaced by the alkyl of C1～C10, C6～C40 the arylmethylene alkyl replaced by the alkyl of C1～C10, C5～C40 the heteroarylidene replaced by the alkyl of C1～C10, C3～C40 ring the alkylidene replaced by the alkyl of C1～C10 or the C3～C40 heterocycloalkylene group replaced by the alkyl of C1～C10, when above-mentioned R5 and R6 is replaced, substituent group comprises the free deuterium of choosing, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, phenyl, the phenyl replaced by the alkyl of C1～C10, the pyridine radicals (pyridyl) replaced by the alkyl of C1～C10, the pyridine (pyridinyl) replaced by the alkyl of C1～C10, the naphthyl replaced by the alkyl of C1～C10, the dibenzofuran group replaced by the alkyl of C1～C10, at least one in the group of the dibenzothiophenes base replaced by the alkyl of C1～C10 and the anthryl replaced by the alkyl of C1～C10 composition, carbon atom or hetero atom in above-mentioned R5 or R6 are combined by adjacent pyrene structure and connector X, and together can be formed by C1～C40 alkyl with the nitrogen-atoms and above-mentioned connector X being combined with above-mentioned R5 or R6, the five-membered ring of C5～C40 aryl and the substituted or unsubstituted fusion of C5～C40 heteroaryl or condensation or hexatomic ring, above-mentioned connector X selects in free N (Y1) and C (Y2) (Y3) group formed, now, Y1, Y2 and Y3 is each independently selected from by hydrogen atom, in the group of C1～C10 alkyl and C5～C10 aryl composition, above-mentioned hetero atom or be contained in above-mentioned heteroaryl, above-mentioned assorted alkyl, the hetero atom of above-mentioned heteroarylidene and above-mentioned assorted alkylidene comprises the free N of choosing, O, S, at least one in the group of Se and Si composition.
The organic compound represented due to above-mentioned chemical formula 1 is used in organic electroluminescence device, can to realize having the organic electroluminescence device of good luminous efficiency, luminosity, color purity and luminescent lifetime characteristic, or can be used as being used in the optical compounds of solar power generation optical device.
The organic compound represented by above-mentioned chemical formula 1 can as the various organic film purposes between the first electrode and above-mentioned second electrode such as the electron transfer layer (ETM) of organic electroluminescence device, luminescent layer (EML), hole transmission layer (HTM), many-sided material used, therefore, the above-mentioned organic compound represented by chemical formula 1 has the improvement as increased the performances such as efficiency and minimizing driving voltage and the maximized function as organic electroluminescence device (OLED) material.
According to an example, above-mentioned chemical formula 1 organic compound represented is characterised by, above-mentioned R1 select free hydrogen atom, C1～C10 alkyl, C3～C10 cycloalkyl,
In the group of composition, above-mentioned X1Selecting in free N (Y1) and C (Y2) (Y3) group formed, now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and C5～C10 aryl composition, above-mentioned X1Select in free N (Y1) and C (Y2) (Y3) group formed, now, Y1, Y2 and Y3 are each independently selected from the group being made up of hydrogen atom, C1～C10 alkyl and C5～C10 aryl, R7 and R8 separately selects free hydrogen, deuterium, halogen, CN, CF3, nitro, the alkyl of C1～C20 straight or branched, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, list (C1～C1 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (C1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition group in, n and m is the integer of 1 to 5.
Above-mentioned R2, R3 and R4 are separately hydrogen or substituted or unsubstituted C1～C10 alkyl, and above-mentioned Z is absent from, above-mentioned R5 and R6 can be each independently selected from by hydrogen atom, C1～C10 alkyl,
In the group of composition, above-mentioned X1Selecting in the group that free O, S, N (Y1) and C (Y2) (Y3) form, now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and C5～C10 aryl composition, above-mentioned RaAnd RbSeparately choosing free hydrogen, deuterium, halogen, CN ,-OH, CF3, nitro, the alkyl of C1～C20 straight or branched, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, single (C1～C1 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (C1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl, and in the group of C3～C10 Heterocyclylalkyl composition, k and l is the integer of 1 to 4, or, above-mentioned R5, Z, R6 and being combined with and above-mentioned R5, Z, the nitrogen-atoms of R6 can form choosing freely
Fusion ring in the group of composition.
Above-mentioned X1Select free O, S, N, Se, Si (alkyl of C1～C10)2, N (Y1), C (Y2) (Y3), C (Y2) (Y3)-C (Y2) (Y3), in the group that C (Y2)=C (Y3) and Si (Y2) (Y3) forms, now, Y1, Y2 and Y3 separately selects free hydrogen atom, C1～C10 alkyl, C5～C10 aryl, C5～C10 heteroaryl, in the group of C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition, or, Y2 and Y3 can by the formation C5～C10 aryl that combines with adjacent base, C5～C10 heteroaryl, C3～C10 cycloalkyl or C3～C10 Heterocyclylalkyl, above-mentioned P is CH2Or by one or two substituted or unsubstituted carbon atom of C1～C10 alkyl, above-mentioned RaAnd RbSeparately choosing free hydrogen, deuterium, halogen, CN ,-OH, CF3, nitro, C1～C20 straight or branched alkyl, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, single (C1～C1 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (CC1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, in the group of C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition, k and l is the integer of 1 to 4, or, when above-mentioned Z is absent from and carbon atom in above-mentioned R5 or R6 or hetero atom are combined by adjacent pyrene structure and connector X, above-mentioned R5, R6 and above-mentioned connector X can form fusion (fused) or condensation (condensed) ring of formula 2 below.
Chemical formula 2
In above-mentioned chemical formula 2, X and RaAs defined in above-mentioned content, R9 can be substituted or unsubstituted C1～C40 alkyl, substituted or unsubstituted C2～C40 thiazolinyl, substituted or unsubstituted C5～C40 aryl, substituted or unsubstituted C6～C40 aralkyl, substituted or unsubstituted C5～C40 heteroaryl, substituted or unsubstituted C3～C40 cycloalkyl or substituted or unsubstituted C3～C40 Heterocyclylalkyl, and two carbon that above-mentioned two binding site is adjacent with in the pyrene structure in above-mentioned chemical formula 1 are connected and form fusion or the hexatomic ring of condensation.
According to another example, the organic compound represented by above-mentioned chemical formula 1 is characterised by, Ar1 and Ar2 is separately substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and substituted or unsubstituted naphthyl, when above-mentioned Ar1 and Ar2 is replaced, substituent group can comprise choosing free deuterium, halogen, CN, Si (CH3)3、CF3, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C1～C10 alkoxyl and phenyl composition group at least one, above-mentioned R1 be substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, the alkyl of substituted or unsubstituted C1～C10, substituted or unsubstituted 9, the cycloalkyl of 9-dimethyl fluorenyl or substituted or unsubstituted C3～C10, when above-mentioned R1 is replaced, substituent group is deuterium or Si (CH3)3, above-mentioned R2, R3, R4 are separately the alkyl of hydrogen or C1～C10, and above-mentioned L is singly-bound or phenylene, or, above-mentioned R5, Z, R6 and be combined with the nitrogen-atoms of above-mentioned R5, Z, R6 and can form choosing freely
Fusion ring in the group of composition, above-mentioned X1Select free O, S, N, Se, Si (alkyl of C1～C10)2, in the group that forms of N (Y1), C (Y2) (Y3), C (Y2) (Y3)-C (Y2) (Y3) and Si (Y2) (Y3), now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and phenyl composition, and above-mentioned P is CH2, or one or two substituted or unsubstituted carbon atom of C1～C10 alkyl, above-mentioned RaAnd RbIt is each independently hydrogen or phenyl, or, when above-mentioned Z is absent from and carbon atom in above-mentioned R5 or R6 or hetero atom are combined by adjacent pyrene structure and connector X, above-mentioned R5, R6 and above-mentioned connector X can form fusion or the condensed ring of formula 3 below.
Chemical formula 3
In above-mentioned chemical formula 3, X is by the substituted or unsubstituted carbon atom of one or two phenyl, and R10 is by the substituted or unsubstituted phenyl of the alkyl of C1～C10, RaFor hydrogen or C1～C20 straight or branched alkyl, two carbon that the binding site of above-mentioned two is adjacent with in the pyrene structure in above-mentioned chemical formula 1 are connected and fetch the hexatomic ring forming fusion or condensation.
Above-mentioned organic compound can have any one chemical constitution in compound 1 to the compound 185 represented in following first table group.
First table group
Can refer to the reaction equation of following synthesis example, or utilize the synthetic method that therefrom can substantially predict, synthesize the organic compound represented by above-mentioned chemical formula 1 comprising above-claimed cpd 1 to compound 185.To multiple reaction equations with reference to following synthesis example of the specific example of the synthetic route of above-claimed cpd.Above-claimed cpd 1 to compound 185 is suitable for being used in the organic membrane of organic electroluminescence device, is especially suitable for being used in hole transmission layer, hole injection layer or luminescent layer.
The available organic compound represented by above-mentioned chemical formula 1 forms above-mentioned organic film by solution process (solubleprocess).
In one example, above-mentioned chemical formula 1 organic compound represented can be used as above-mentioned luminescent layer material, specifically, can be used as blue-fluorescence dopant.
The structure of above-mentioned organic electroluminescence device is very various.The more than one layer in the group selecting free hole injection layer, hole transmission layer, hole blocking layer, electronic barrier layer, electron transfer layer and electron injecting layer composition is may also include between above-mentioned first electrode and the second electrode.
In more detail, in an example of above-mentioned organic electroluminescence device, above-mentioned organic electroluminescence device can have the structure being made up of the first electrode/hole injection layer/luminescent layer/electron transfer layer/electron injecting layer/the second electrode, or, above-mentioned organic electroluminescence device can have the structure being made up of the first electrode/hole injection layer/hole transmission layer/luminescent layer/electron transfer layer/electron injecting layer/the second electrode pole, or, above-mentioned organic electroluminescence device can have the structure of the first electrode/hole injection layer/hole transmission layer/luminescent layer/hole blocking layer/electron transfer layer/electron injecting layer/the second electrode.
Now, more than one in above-mentioned hole transmission layer, hole injection layer and luminescent layer can include the organic compound that represented by above-mentioned chemical formula 1.
The luminescent layer of above-mentioned organic electroluminescence device can comprise containing red, green, blue or white phosphorescence or fluorescent dopants.Wherein, above-mentioned phosphorescent dopant can be organo-metallic compound, and above-mentioned organo-metallic compound comprises more than one the element in the group selecting free iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm) to form.Further, above-mentioned chemical formula 1 it is fluorescent dopants that the compound represented can also use in luminescent layer.
Hereinafter, the preparation method of above-mentioned organic electroluminescence device is understood.
First, utilize vapour deposition method or sputtering method etc. to form the first electrode material with high work function, form the first electrode on substrate top.Above-mentioned first electrode can be anode (Anode).Wherein it is preferred to, the substrate being used in conventional organic electroluminescence device is adopted as substrate, this substrate is mechanical strength, heat stability, the transparency, surface smoothness, the glass substrate that advisability and water proofing property is good or transparent plastic substrate.As the first electrode material, use tin indium oxide (ITO) that transparent and electrically conductive is good, indium zinc oxide (IZO), stannum oxide (SnO2), zinc oxide (ZnO) etc..
Then, may utilize the multiple methods such as vacuum vapour deposition, spin-coating method, casting, LB (LangmuirBlodgett) method, form hole injection layer (HIL) at above-mentioned first electrode upper.
When utilizing vacuum vapour deposition to form hole injection layer, its evaporation condition compound because of the material as hole injection layer, the structure of the hole injection layer as purpose and thermal characteristics etc. and different, it is, however, preferable that generally evaporation temperature be 100 DEG C to 500 DEG C, vacuum be 10-5Torr to 10-3Torr, evaporation rate areExtremelyFilm thickness is generallySuitable selection is carried out to the scope of 1 μm.
When utilizing spin-coating method to form hole injection layer, its coating condition compound because of the material as hole injection layer, the structure of the hole injection layer as purpose and thermal characteristics for etc. and different, but, preferably, after the coating speed of about 2000rpm to 5000rp, coating, the heat treatment temperature for removing solvent carries out suitable selection at about 80 DEG C to the temperature range of 200 DEG C.
Above-mentioned hole injection layer material can be the compound represented by above-mentioned chemical formula 1.
Or, such as, as above-mentioned hole injection layer material, following known hole injecting material can be used: specially permit the phthalocyanine compounds such as C.I. Pigment Blue 15 disclosed in No. 4356429 or at " advanced material (AdvancedMaterial) in the U.S., 6, p.677 (1994) " in record as the 4 of star burst type amine derivative class, 4 ', 4 "-three (carbazole-9-base) triphenylamine (TCTA), 4, 4 ', 4 '-three (N-3-methylphenyl-N-phenyl amino) triphenylamine (m-MTDATA), 1, 3, 5-tri-[4-(3-aminomethyl phenyl-phenyl amino) phenyl] benzene (m-MTDAPB), 4, 4 ', 4 " three (N-(2-naphthyl)-N-phenyl amino) triphenylamine (2-TNATA:4, 4', 4 "-tris (N-(2-naphtyl)-N-phenylamino) triphenylamine)), as the polyaniline/DBSA (Pani/DBSA:Polyaniline/Dodecylbenzenesulfonicacid) with deliquescent conducting polymer, or poly-(3, 4-ethene dioxythiophene)/poly-(4-styrene sulfonic acid) (PEDOT/PSS:Poly (3, 4-ethylenedioxythiophene)/Poly (4-styrenesulfonate)), polyaniline/camphorsulfonic acid (PANI/CSA:Polyaniline/Camphorsulfonicacid), or polyaniline/poly-(4-styrene sulfonic acid) (PANI/PSS:Polyaniline/Poly (4-styrenesulfonate)) etc..
The thickness of above-mentioned hole injection layer is aboutExtremelyPreferably, the thickness of above-mentioned hole injection layer can beExtremelyThis is because, above-mentioned hole injection layer thickness less thanWhen, hole-injection characteristics is likely to decrease, above-mentioned hole injection layer thickness more thanWhen, driving voltage likely rises.
Unlike this, available vacuum gas-phase vapour deposition method forms above-mentioned hole injection layer.Concrete evaporation condition is different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.Such as, N can be used, N-pair-[4-(two-p-Tolylamino) phenyl]-N, N-diphenyl xenyl-4,4-diamidogen (DNTPD, N, N-bis-[4-(di-m-tolylamino) phenyl]-N, N-diphenylbiphenyl-4,4-diamine) etc..
Then, may utilize the multiple methods such as vacuum vapour deposition, spin-coating method, casting, LB (LangmuirBlodgett) method, form hole injection layer (HIL) on above-mentioned hole injection layer top.When utilizing vacuum vapour deposition and spin-coating method forms hole transmission layer, its evaporation condition and coating condition are different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.
Above-mentioned hole transmission layer material can comprise the compound represented by chemical formula 1 as above.Or, such as, following known hole transporting material can be used: there is carbazole derivates, the N such as N-phenyl carbazole, polyvinylcarbazole, N '-bis-(3-aminomethyl phenyl)-N, N '-diphenyl-[1,1-xenyl]-4,4 '-ethylenediamine (TPD), N, N '-two (naphthalene-1-base)-N, N ' the conventional amine derivative etc. of the aromatic condensation ring such as-diphenylbenzidine (α-NPD).The thickness of above-mentioned hole transmission layer is aboutExtremelyPreferably, the thickness of above-mentioned hole transmission layer can beExtremelyAbove-mentioned hole transmission layer thickness less thanWhen, hole transporting properties is likely to decrease, above-mentioned hole transmission layer thickness more thanWhen, driving voltage likely rises.
Then, may utilize the multiple methods such as vacuum vapour deposition, spin-coating method, casting, LB (LangmuirBlodgett) method, form luminescent layer (EML) on above-mentioned hole transmission layer top.When utilizing vacuum vapour deposition and spin-coating method forms luminescent layer, its evaporation condition and coating condition are different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.
Above-mentioned luminescent layer can comprise the compound represented by chemical formula 1 as above.Now, above-mentioned chemical formula 1 compound represented can be used along with applicable and known material of main part, or, can use together with known dopant material.
The compound represented by above-mentioned chemical formula 1 can also be used alone.When material of main part, following compound can be used: such as, three (oxine) aluminum (Alq3, tris (8-hydroxy-quinolatealuminium)), 4,4 '-N, N '-two carbazoles-xenyl (CBP), or poly-(n-VCz) (PVK) etc..
When dopant material, as fluorescent dopants, the IDE102 that can buy can be used in Idemitsu Kosen Co., Ltd. of Japan (Idemitsu company), IDE105 and can at Lin Yuan Co., Ltd. (HayashibaraCo., Ltd.) C545T etc. bought, as phosphorescent dopants, red phosphorescent adulterant PtOEP can be used, the RD61 of UDC company, green phosphorescent adulterant three (2-phenylpyridine) closes iridium (III) (Ir (PPy) 3:PPy=2-phenylpyridine), as blue phosphorescent adulterant double, two (4, 6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium (F2Irpic), the red phosphorescent adulterant RD61 etc. of UDC company.And, as phosphorescent dopants, it is also possible to use N-acridone methylquinoline (MQD, N-methylquinacridone), coumarin (Coumarine) derivant etc..
Although without particular limitation of doping content, generally, with the main body of 100 weight portions for benchmark, the content of above-mentioned adulterant is 0.01～15 weight portion.The thickness of above-mentioned luminescent layer can be aboutExtremelyPreferably, the thickness of above-mentioned luminescent layer can beExtremely
This is because, above-mentioned luminescent layer thickness less thanWhen, the characteristics of luminescence is likely to decrease, above-mentioned luminescent layer thickness more thanWhen, driving voltage likely rises.
In luminescent layer, when by used along to luminophor and phosphorescent dopants, in order to prevent the phenomenon spread to triplet exciton or both hole and electron transport layer, the methods such as available vacuum vapour deposition, spin-coating method, casting, LB method, form hole blocking layer (HBL) on above-mentioned luminescent layer top.When utilizing vacuum vapour deposition and spin-coating method forms hole blocking layer, its condition is different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.As using and known hole barrier materials, can enumerate, oxadiazoles derivant or triazole derivative, phenanthroline derivant, bromocresol purple sodium salt (BCP) etc..
The thickness of above-mentioned hole blocking layer can be aboutExtremelyPreferably, the thickness of above-mentioned hole blocking layer can beExtremelyThis is because, above-mentioned hole blocking layer thickness less thanWhen, hole-blocking characteristics can decline, above-mentioned hole blocking layer thickness more thanWhen, driving voltage likely rises.Above-mentioned hole blocking layer is omissible.
Then, the multiple methods such as vacuum vapour deposition, spin-coating method, casting are utilized to form electron transfer layer (ETL).
When utilizing vacuum vapour deposition and spin-coating method forms electron transfer layer, its condition is different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.Above-mentioned electron transport layer materials plays the effect stably transmitted from electron injection electrode (Cathode) injected electrons, as above-mentioned electron transport layer materials, quinoline can be used, especially, it is possible to use three (oxine) aluminum (Alq3), the known material such as TAZ, Balq, PBD.
The thickness of above-mentioned electron transfer layer can be aboutExtremelyPreferably, the thickness of above-mentioned electron transfer layer can beExtremelyThis is because, above-mentioned electron transfer layer thickness less thanWhen, electron transport property likely declines, above-mentioned electron transfer layer thickness more thanWhen, driving voltage likely rises.
Further, can portion's stacking electron injecting layer (EIL) on the electron transport layer, above-mentioned electron injecting layer (EIL) is the material with the function being easily injected into electronics from negative electrode, but without particular limitation of its material.
As electron injecting layer, available following known material: lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li2O), Barium monoxide (BaO) etc. form the material of electron injecting layer.The evaporation condition of above-mentioned electron injecting layer is different because of the compound of use, but, generally, select in the condition and range almost identical with the condition forming hole injection layer.
The thickness of above-mentioned electron injecting layer can be aboutExtremelyPreferably, the thickness of above-mentioned electron injecting layer can beExtremelyThis is because, above-mentioned electron injecting layer thickness less thanWhen, Electron Injection Characteristics is likely to decrease, above-mentioned electron injecting layer thickness more thanWhen, driving voltage likely rises.
Finally, the available method such as vacuum vapour deposition or sputtering method, form the second electrode on electron injecting layer top.
Above-mentioned second electrode can be used as negative electrode (Cathode).As the metal forming above-mentioned second electrode, can use and there is the metal of low work function, alloy, conductive compound and their mixture.Specifically, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-Yin (Mg-Ag) etc. can be enumerated.Further, in order to obtain positive surface light-emitting device, it is possible to use adopt the transmission-type negative electrode of tin indium oxide, indium zinc oxide.
Hereinafter, illustrate reaction example and comparative example in detail, but, the invention is not limited in following synthesis example and embodiment.In following reaction example, in the way of the numbering of the end product at midbody compound adds sequence number, carry out labelling.Such as, represent compound 1 with compound 1, represent the midbody compound of above-claimed cpd with midbody compound [1-1] etc..In this manual, the numbering of compound is represented with the numbering of chemical formula.Such as, the compound represented by chemical formula 1 is represented with compound 1.
Reaction example 1: the synthesis of compound 1
The preparation of midbody compound [1-2]
Under nitrogen atmosphere, to the 1 of 30.0g in the reaction flask of 500mL, 6-dibromo pyrene (83.3mmol), the compound [1-1] (83.3mmol) of 10.0g, Hydro-Giene (Water Science). (CuI) g (83.3mmol) of 15.9, the potassium carbonate (183.3mmol) of 25.3g add the diphenyl ether of 150mL, and with 180 DEG C of heating temperatures and stir 33 hours.After question response terminates, being cooled to room temperature, after adding the methanol of 200mL, stirring is filtration under diminished pressure also, after adding the acetone of 150mL and the distilled water stirring of 500mL, and filtration under diminished pressure.Utilize silica gel column chromatography that solid is easily separated purification and obtain the bright yellow solid midbody compound [1-2] (8%) of 3.2g.
The preparation of midbody compound [1-4]
Under nitrogen atmosphere, the compound [1-2] (6.7mmol) of 3.2g is dissolved in the oxolane of 30mL by the reaction flask of 500mL, at ambient temperature, the compound [1-3] (1.0MinTHF) (6.7mmol) of 6.7mL it is slowly added dropwise.After stirring 13 hours, add the NH of 100mL4Cl aqueous solution terminates reaction, and utilize ethyl acetate to extract, utilize anhydrous magnesium sulfate to dry, filter, and after concentrating under reduced pressure filtrate, utilize silica gel column chromatography to be easily separated purification and obtain bright yellow solid midbody compound [1-4] 1.1g (29%) of 1.1g.
The preparation of midbody compound [1-5]
Under nitrogen atmosphere, compound [1-4] 1.1g (1.9mmol) of 1.1g is dissolved in the toluene of 10mL by the reaction flask at 500mL, adds the polyphosphoric acid stirring of 20g, and drips the methanesulfonic acid (3.9mmol) of 0.4g.After question response terminates, add the oxolane of 70mL respectively and after methanol stirs 1 hour, extract by ethyl acetate, dry with anhydrous magnesium sulfate, filter, and after concentrating under reduced pressure filtrate, utilize silica gel column chromatography that solid is easily separated purification and obtain the bright yellow solid midbody compound [1-5] (38%) of 0.4g.
The preparation of midbody compound [1-7]
Under nitrogen atmosphere, in the reaction flask of 250mL, to the compound [1-5] (0.7mmol) of 0.4g, the compound [1-6] (2.2mmol) of 0.5g, the Hydro-Giene (Water Science). (CuI) (0.4mmol) of 0.1g, 0.2g potassium carbonate (1.5mmol) add the diphenyl ether of 50mL, with 180 DEG C of heating temperatures and stir 18 hours.After question response terminates, after adding the methanol of 100mL, stirring is filtration under diminished pressure also, after adding the acetone of 50mL and the distilled water stirring of 200mL, carries out filtration under diminished pressure.Utilize silica gel column chromatography that solid is easily separated purification and obtain the bright yellow solid midbody compound [1-7] (57%) of 0.3g.
The preparation of compound 1
In the reaction flask of 100mL to the compound [1-7] (4.2mmol) of 2.6g, the compound [1-8] (4.7mmol) of 0.8g, the sodium tert-butoxide (8.5mmol) of 0.8g, three (dibenzalacetone) two palladium (0) (Tris (dibenzylideneacetone) dipalladium (0)) (0.2mmol) of 0.2g, 0.1g tri-butyl phosphine (0.4mmol) add the toluene of 50mL, return stirring 3 hours.After question response terminates, with dichloromethane extraction, utilize anhydrous magnesium sulfate to dry, filter, after concentrating under reduced pressure filtrate, utilize silica gel column chromatography to be easily separated purification and obtain the yellow solid compound 1 (45%) of 1.3g.
1HNMR(300MHz,THF-d8): δ 8.27 (d, 1H), 8.19 (d, 1H), 8.10 (d, 1H), 8.01～7.98 (q, 2H), 7.88 (s, 1H), 7.85～7.81 (q, 2H), 7.48～7.46 (t, 1H), 7.21～7.20 (t, 5H), 7.19～7.09 (m, 6H), 7.07 (d, 4H), 6.95～6.93 (m, 6H), 6.91～6.90 (d, 1H), 6.75～6.73 (t, 2H), 6.60～6.58 (t, 3H)
MS/FAB:701(M+)
Fig. 1 is the nuclear magnetic resonance hydrogen spectruming determining result of prepared above-claimed cpd 1.
Fig. 2 is the differential scanning calorimeter measurement result of prepared above-claimed cpd 1.
Fig. 3 is the thermogravimetric analyzer measurement result of prepared above-claimed cpd 1.
Fig. 4 is the ultra-violet absorption spectrum of prepared above-claimed cpd 1.
Fig. 5 is the luminescence generated by light curve chart of prepared above-claimed cpd 1.
Reaction example 2: the synthesis of compound [158]
The preparation of midbody compound [158-1]
Under nitrogen atmosphere, to the 2 of 30.0g in the reaction flask of 500mL, 7-dibromo pyrene (83.3mmol), the compound [1-1] (83.3mmol) of 10.0g, the Hydro-Giene (Water Science). (83.3mmol) of 15.9g, 25.3g potassium carbonate (183.3mmol) add the diphenyl ether of 100mL, with 180 DEG C heating and stir 30 hours.After question response terminates, it is cooled to room temperature, after adding the methanol of 300mL, stirring filtration under diminished pressure, then after adding the acetone of 250mL and the distilled water stirring of 500mL, carry out filtration under diminished pressure.Utilize silica gel column chromatography that solid is easily separated purification and obtain the bright yellow solid midbody compound [158-1] (14%) of 5.6g.
The preparation of midbody compound [158-2]
Under nitrogen atmosphere, in the reaction flask of 500mL, 5.6g compound [158-1] (11.7mmol) is dissolved in the oxolane of 50mL, at ambient temperature, is slowly added dropwise compound [1-3] (1.0MinTHF) 11.7mL (11.7mmol).After stirring 15 hours, add the NH of 150mL4Cl aqueous solution terminates reaction, utilizes ethyl acetate to extract, dries with anhydrous magnesium sulfate, filters, and after concentrating under reduced pressure filtrate, utilizes silica gel column chromatography separation purification to obtain the bright yellow solid midbody compound [158-2] (37%) of 2.4g.
The preparation of midbody compound [158-3]
Under nitrogen atmosphere, in the reaction flask of 500mL, the compound [158-2] (4.3mmol) of 2.4g is dissolved in the toluene of 30mL, adds the polyphosphoric acid stirring of 30g, and drip the methanesulfonic acid (8.6mmol) of 0.8g.After question response terminates, add the oxolane of 100mL respectively and after methanol stirs 1 hour, ethyl acetate is utilized to extract, dry with anhydrous magnesium sulfate, filter, after concentrating under reduced pressure filtrate, utilize silica gel column chromatography to be easily separated purification and obtain the bright yellow solid midbody compound [158-3] (41%) of 1.0g.
The preparation of midbody compound [158-4]
Under nitrogen atmosphere, in the reaction flask of 250mL to the compound [158-3] (1.8mmol) of 1.0g, the compound [1-6] (5.3mmol) of 1.1g, the Hydro-Giene (Water Science). (0.9mmol) of 0.2g, 0.5g potassium carbonate (3.5mmol) add the diphenyl ether of 70mL, with 180 DEG C heating and stir 14 hours.After question response terminates, after adding the methanol of 110mL, stir and carry out filtration under diminished pressure, then after adding the acetone of 50mL and the distilled water stirring of 200mL, carry out filtration under diminished pressure.Utilize silica gel column chromatography that solid is easily separated purification and obtain the bright yellow solid midbody compound [158-4] (49%) of 0.5g.
The preparation of compound [158]
In the reaction flask of 250mL to the compound [158-4] (8.7mmol) of 5.3g, the compound [1-8] (10.4mmol) of 1.8g, 1.7g put into sodium tert-butoxide (17.3mmol), three (dibenzalacetone) two palladium (0) (0.5mmol) of 0.5g, 0.2g tri-butyl phosphine (0.9mmol) add the toluene of 70mL, and return stirring 4 hours.After question response terminates, utilize dichloromethane extraction, dry with anhydrous magnesium sulfate, filter, after concentrating under reduced pressure filtrate, utilize silica gel column chromatography to be easily separated purification and obtain the yellow solid compound [158] (55%) of 3.3g.
1HNMR (300MHz, THF-d8): δ 8.22 (d, 1H), 8.18 (d, 1H), 8.08 (d, 1H), 7.99～7.96 (q, 2H), 7.84～7.78 (q, 2H), 7.76 (s, 1H), 7.45～7.43 (t, 1H), 7.41 (s, 1H), 7.19～7.15 (t, 4H), 7.13～7.02 (m, 10H), 6.91～6.86 (m, 7H), 6.70～6.66 (t, 2H), 6.58～6.56 (t, 3H)
MS/FAB:701(M+)
Comparative example 1
The compound a represented by below formula a is used as Day-Glo blue main body, the compound b represented by below formula b is used as blue-fluorescence dopant, by 4, 4 ', 4 " three (N-(2-naphthyl)-N-phenyl amino) triphenylamine is used as hole injection layer material, by N, N'-bis-(naphthalene-1-base)-N, N'-diphenylbenzidine is used as hole transmission layer material, it is prepared for the organic luminescent device being structured with: tin indium oxide/4, 4 ', 4 " three (N-(2-naphthyl)-N-phenyl amino) triphenylamine (80nm)/N, N '-two (naphthalene-1-base)-N, N '-diphenylbenzidine (30nm)/compound a+compound b (30nm)/tri-(oxine) aluminum (30nm)/lithium fluoride (1nm)/aluminum (100nm).
15 Ω/cm by healthy and free from worry (corning) company2 Indium tin oxid glass substrate is cut into the size of 50mm × 50mm × 0.7mm, and carries out ultrasonic waves for cleaning respectively in acetone isopropanol and pure substance after 15 minutes, carries out using anode after UV ozone is cleaned 30 minutes.By on aforesaid substrate top to vacuum moulding machine, form the hole injection layer that thickness is 80nm.N, N'-bis-(naphthalene-1-base)-N, N'-diphenylbenzidine is carried out vacuum evaporation by above-mentioned hole injection layer top, defines the hole transmission layer that thickness is 30nm.By compound b (doping 5%) vacuum moulding machine that the compound a to being represented by chemical formula a on above-mentioned hole transmission layer top and chemical formula b represent, define the luminescent layer that thickness is 30nm.Then, by successively lithium fluoride 1nm (electron injecting layer) and aluminum 100nm (negative electrode) being carried out vacuum evaporation on above-mentioned electron transfer layer top, define such as the first table group] shown in organic luminescent device.Above-mentioned organic luminescent device is called and compares sample 1.
Embodiment 1 to embodiment 20
In above-mentioned comparative example 1, as luminescent layer fluorescent dopants compound, the compound 3 in above-mentioned first table group respectively, compound 7, compound 15, compound 22, compound 28, compound 35, compound 43, compound 56, compound 58, compound 88, compound 95, compound 101, compound 113, compound 117, compound 121, compound 133, compound 145, compound 153, compound 156 and compound 164 replace compound b to utilize, in addition, it is prepared for that there are tin indium oxide/4 with the method identical with above-mentioned comparative example 1, 4 ', 4 " three (N-(2-naphthyl)-N-phenyl amino) triphenylamine (80nm)/N, N '-two (naphthalene-1-base)-N, N '-diphenylbenzidine (30nm)/[compound a+blue-fluorescence dopant compound 3, compound 7, compound 15, compound 22, compound 28, compound 35, compound 43, compound 56, compound 58, compound 88, compound 95, compound 101, compound 113, compound 117, compound 121, compound 133, compound 145, compound 153, compound 156 and compound 164 (5%)] organic luminescent device of structure of (30nm)/tri-(oxine) aluminum (30nm)/lithium fluoride (1nm)/aluminum (100nm).Above-mentioned organic luminescent device is called sample 1 to sample 20.
Assessment example 1: compare the characteristics of luminescence assessment of sample 1 and sample 1～sample 20
For comparing sample 1 and sample 1～sample 20, utilizing Keithleysourcemeter " 2400 ", Konica Minolta (KONIKAMINOLTA) " CS-2000 ", with 10mA/cm2For benchmark, respectively luminosity, luminous efficiency, luminescence peak being estimated, its result is shown in following second table group.Above-mentioned multiple sample illustrates blue-light-emitting peak value under 448nm～461nm scope.
Second table group
As shown in above-mentioned second table group, relative to comparing sample 1, sample 1 to sample 20 presents the characteristics of luminescence obtaining improving.
Assessment example 2: compare the life characteristic assessment of sample 1 and sample 1～sample 20
For comparing sample 1 and sample 1～sample 20, utilizing the LTS-1004AC biometrics device of ENCtechnology company, with 700nit for benchmark, the time of 97% of respectively life-span being reached is measured, and its result represents in following 3rd table group.
3rd table group
As shown in above-mentioned 3rd table group, relative to comparing sample 1, the presenting of sample 1 to sample 20 obtains the life characteristic improved.
In the above description, although eliminate the known technology of routine, but, those of ordinary skill in the art can easily speculate, reasoning and realize the known technology of this routine.
Claims (13)
1. an organic compound, it is characterised in that represented by formula 1 below,
Chemical formula 1
In above-mentioned chemical formula 1,
Ar1 and Ar2 is separately substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical and substituted or unsubstituted naphthyl, when above-mentioned Ar1 and Ar2 is replaced, substituent group can comprise choosing free hydrogen, deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, phenyl, pyridine radicals and pyrimidine radicals composition group at least one,
Above-mentioned Ar1 and Ar2 forms the cycloalkyl of C3～C5 by combining, it is possible to formed using with above-mentioned Ar1 and the Ar2 carbon atom the combined helical structure as spiro-atom,
R1, R2, R3 and R4 are separately hydrogen, deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C40 alkyl, C5～C40 aryl, C4～C40 heteroaryl, C3～C40 cycloalkyl or C3～C40 Heterocyclylalkyl, when above-mentioned R1, R2, R3 and R4 are replaced, substituent group comprises choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition group at least one,
L is singly-bound, substituted or unsubstituted C5～C40 arlydene or C4～C40 heteroarylidene, and when above-mentioned L is replaced, substituent group can be choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl and substituted or unsubstituted C1～C10 alkoxyl composition group at least one,
Z is non-existent, singly-bound, Si (CH3)2, bivalence amido, the alkylidene of substituted or unsubstituted C1～C5 or substituted or unsubstituted C2～C5 alkylene group, when above-mentioned Z is replaced, substituent group comprises at least one in the group selecting free C1～C40 alkyl, C5～C40 aryl, C4～C40 heteroaryl and C3～C40 cycloalkyl composition
In the non-existent situation of above-mentioned Z, R5 and R6 can be separately substituted or unsubstituted C1～C40 alkyl, substituted or unsubstituted C2～C40 thiazolinyl, substituted or unsubstituted C5～C40 aryl, substituted or unsubstituted C6～C40 aralkyl, substituted or unsubstituted C5～C40 heteroaryl, substituted or unsubstituted C3～C40 cycloalkyl or substituted or unsubstituted C3～C40 Heterocyclylalkyl, when above-mentioned R5 and R6 is replaced, substituent group comprises choosing free deuterium, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, by the substituted or unsubstituted phenyl of the alkyl of C1～C10, by the substituted or unsubstituted pyridine radicals of the alkyl of C1～C10, by the substituted or unsubstituted pyridine of the alkyl of C1～C10, by the substituted or unsubstituted naphthyl of the alkyl of C1～C10, by the substituted or unsubstituted dibenzofuran group of the alkyl of C1～C10, by the alkyl of C1～C10 substituted or unsubstituted dibenzothiophenes base and by least one in the group of the substituted or unsubstituted anthryl composition of the alkyl of C1～C10,
Deposit in case at above-mentioned Z, R5 and R6 is separately substituted or unsubstituted C1～C40 alkylidene, C2～C40 the alkylene group replaced by the alkyl of C1～C10, C5～C40 the arlydene replaced by the alkyl of C1～C10, C6～C40 the arylmethylene alkyl replaced by the alkyl of C1～C10, C5～C40 the heteroarylidene replaced by the alkyl of C1～C10, C3～C40 ring the alkylidene replaced by the alkyl of C1～C10 or the C3～C40 heterocycloalkylene group replaced by the alkyl of C1～C10, when above-mentioned R5 and R6 is replaced, substituent group comprises the free deuterium of choosing, halogen, CN, Si (CH3)3、CF3, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C3～C10 cycloalkyl, substituted or unsubstituted C1～C10 alkoxyl, phenyl, the phenyl replaced by the alkyl of C1～C10, the pyridine radicals replaced by the alkyl of C1～C10, the pyridine replaced by the alkyl of C1～C10, the naphthyl replaced by the alkyl of C1～C10, the dibenzofuran group replaced by the alkyl of C1～C10, the dibenzothiophenes base replaced by the alkyl of C1～C10 and replaced by the alkyl of C1～C10 anthryl composition group at least one
Carbon atom or hetero atom in above-mentioned R5 or R6 are combined by adjacent pyrene structure and connector X, and together can be formed by the five-membered ring of C1～C40 alkyl, C5～C40 aryl and the substituted or unsubstituted fusion of C5～C40 heteroaryl or condensation or hexatomic ring with the nitrogen-atoms and above-mentioned connector X that are combined with above-mentioned R5 or R6
Above-mentioned connector X selects in free N (Y1) and C (Y2) (Y3) group formed, and now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and C5～C10 aryl composition,
Above-mentioned hetero atom or be contained in the hetero atom of above-mentioned heteroaryl, above-mentioned assorted alkyl, above-mentioned heteroarylidene and above-mentioned assorted alkylidene and comprise at least one in the group selecting free N, O, S, Se and Si to form.
2. organic compound according to claim 1, it is characterised in that
Above-mentioned R1 select free hydrogen atom, C1～C10 alkyl, C3～C10 cycloalkyl,
In the group of composition,
Above-mentioned X1Selecting in free N (Y1) and C (Y2) (Y3) group formed, now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and C5～C10 aryl composition,
R7 and R8 separately selects free hydrogen, deuterium, halogen, CN, CF3, nitro, C1～C20 straight or branched alkyl, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, list (C1～C10 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (C1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition group in, n and m is the integer of 1 to 5
Above-mentioned R2, R3 and R4 are separately hydrogen or substituted or unsubstituted C1～C10 alkyl,
Above-mentioned Z is absent from, above-mentioned R5 and R6 can separately select free hydrogen atom, C1～C10 alkyl,
In the group of composition,
Above-mentioned X1Selecting in the group that free O, S, N (Y1) and C (Y2) (Y3) form, now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and C5～C10 aryl composition,
Above-mentioned RaAnd RbSeparately choosing free hydrogen, deuterium, halogen, CN ,-OH, CF3, nitro, C1～C20 straight or branched alkyl, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, list (C1～C10 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (C1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition group in, k and l is the integer of 1 to 4
Or, above-mentioned R5, Z, R6 and be combined with the nitrogen-atoms of above-mentioned R5, Z, R6 and can form choosing freely
Fusion ring in the group of composition,
Above-mentioned X1Select free O, S, N, Se, Si (alkyl of C1～C10)2, in the group that forms of N (Y1), C (Y2) (Y3), C (Y2) (Y3)-C (Y2) (Y3), C (Y2)=C (Y3) and Si (Y2) (Y3), now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition, or, Y2 and Y3 can combine with adjacent base and form C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl or C3～C10 Heterocyclylalkyl
Above-mentioned P is CH2Or by one or two substituted or unsubstituted carbon atom of C1～C10 alkyl,
Above-mentioned RaAnd RbSeparately choosing free hydrogen, deuterium, halogen, CN ,-OH, CF3, nitro, C1～C20 straight or branched alkyl, C1～C10 haloalkyl, C1～C10 hydroxyalkyl, C1～C10 alkoxyl, amino, C1～C10 alkylamino, two (C1～C10 alkyl) amino, C5～C10 virtue amino, two (C5～C10 aryl) amino, list (C1～C10 alkyl) silicyl, two (C1～C10 alkyl) silicyl, three (C1～C10 alkyl) silicyl, C5～C10 aryl, C5～C10 heteroaryl, C3～C10 cycloalkyl and C3～C10 Heterocyclylalkyl composition group in, k and l is the integer of 1 to 4
Or, when above-mentioned Z is absent from and carbon atom in above-mentioned R5 or R6 or hetero atom are combined by adjacent pyrene structure and connector X, above-mentioned R5, R6 and above-mentioned connector X can form fusion or the condensed ring of formula 2 below,
Chemical formula 2
In above-mentioned chemical formula 2,
X and RaAs defined in above-mentioned content,
R9 can be substituted or unsubstituted C1～C40 alkyl, substituted or unsubstituted C2～C40 thiazolinyl, substituted or unsubstituted C5～C40 aryl, substituted or unsubstituted C6～C40 aralkyl, substituted or unsubstituted C5～C40 heteroaryl, substituted or unsubstituted C3～C40 cycloalkyl or substituted or unsubstituted C3～C40 Heterocyclylalkyl
Two carbon that the binding site of above-mentioned two is adjacent with in the pyrene structure in above-mentioned chemical formula 1 are connected and fetch the hexatomic ring forming fusion or condensation.
3. organic compound according to claim 2, it is characterised in that
Ar1 and Ar2 is separately substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, substituted or unsubstituted pyrimidine radicals and substituted or unsubstituted naphthyl, when above-mentioned Ar1 and Ar2 is replaced, substituent group can comprise choosing free deuterium, halogen, CN, Si (CH3)3、CF3, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C1～C10 alkoxyl and phenyl composition group at least one,
Above-mentioned R1 be substituted or unsubstituted phenyl, substituted or unsubstituted pyridine radicals, the alkyl of substituted or unsubstituted C1～C10, substituted or unsubstituted 9, the cycloalkyl of 9-dimethyl fluorenyl or substituted or unsubstituted C3～C10, when above-mentioned R1 is replaced, substituent group is deuterium or Si (CH3)3,
Above-mentioned R2, R3, R4 are separately the alkyl of hydrogen or C1～C10,
Above-mentioned L is singly-bound or phenylene,
Or, above-mentioned R5, Z, R6 and be combined with the nitrogen-atoms of above-mentioned R5, Z, R6 and can form choosing freely
Fusion ring in the group of composition,
Above-mentioned X1Select free O, S, N, Se, Si (alkyl of C1～C10)2, in the group that forms of N (Y1), C (Y2) (Y3), C (Y2) (Y3)-C (Y2) (Y3) and Si (Y2) (Y3), now, Y1, Y2 and Y3 separately select in the group of free hydrogen atom, C1～C10 alkyl and phenyl composition
Above-mentioned P is CH2Or by one or two substituted or unsubstituted carbon atom of C1～C10 alkyl,
Above-mentioned RaAnd RbIt is separately hydrogen or phenyl,
Or, when above-mentioned Z is absent from and carbon atom in above-mentioned R5 or R6 or hetero atom are combined by adjacent pyrene structure and connector X, above-mentioned R5, R6 and above-mentioned connector X can form fusion or the condensed ring of formula 3 below,
Chemical formula 3
In above-mentioned chemical formula 3,
X is by the substituted or unsubstituted carbon atom of one or two phenyl,
R10 is by the substituted or unsubstituted phenyl of the alkyl of C1～C10,
RaFor hydrogen or C1～C20 straight or branched alkyl,
Two carbon that the binding site of above-mentioned two is adjacent with in the pyrene structure in above-mentioned chemical formula 1 are connected and fetch the hexatomic ring forming fusion or condensation.
4. organic compound according to claim 1, it is characterised in that above-mentioned organic compound is the one in following compound 1 to compound 185,
5. organic compound according to claim 1, it is characterised in that above-mentioned organic compound uses with the purposes of luminescent layer material in material for organic electroluminescent device.
6. organic compound according to claim 1, it is characterised in that above-mentioned luminescent layer material is blue-fluorescence dopant.
7. an organic electroluminescence device, it is characterised in that
The organic thin film layer formed by one or more layers at least including luminescent layer is accompanied between negative electrode and anode,
At least one of which in above-mentioned organic thin film layer individually contains the one in the organic compound according to any one of claim 1 to 6, or containing the two or more combination in the organic compound according to any one of claim 1 to 6.
8. organic electroluminescence device according to claim 7, it is characterised in that utilize above-mentioned organic compound to form above-mentioned organic thin film layer by solution process.
9. organic electroluminescence device according to claim 7, it is characterised in that comprise above-mentioned organic compound as luminescent layer material.
10. organic electroluminescence device according to claim 9, it is characterised in that above-mentioned luminescent layer material is blue-fluorescence dopant.
11. organic electroluminescence device according to claim 7, it is characterized in that, above-mentioned organic electroluminescence device has the structure stacked gradually by anode, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode.
12. an electronic equipment, it is characterised in that include the organic electroluminescence device described in claim 7.
13. electronic equipment according to claim 12, it is characterized in that, above-mentioned electronic equipment is organic integrated circuits, organic field effect tube, OTFT, organic light-emitting transistor, organic solar batteries, organic optical detector, organophotoreceptorswith, organic electroluminescence quenching device, light-emitting electrochemical cell, organic laser diode or organic electroluminescence device.
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| WO2018128470A1 (en) * | 2017-01-05 | 2018-07-12 | 머티어리얼사이언스 주식회사 | Organic electroluminescent element |
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