CN104650041A - Fluorine-containing phenanthroimidazole derivative, synthetic method and application thereof - Google Patents
Fluorine-containing phenanthroimidazole derivative, synthetic method and application thereof Download PDFInfo
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- CN104650041A CN104650041A CN201310589113.5A CN201310589113A CN104650041A CN 104650041 A CN104650041 A CN 104650041A CN 201310589113 A CN201310589113 A CN 201310589113A CN 104650041 A CN104650041 A CN 104650041A
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- PRGFQVUSXRPNOG-PLNGDYQASA-N CC(/C=C\C(C(F)(F)F)=C)=C Chemical compound CC(/C=C\C(C(F)(F)F)=C)=C PRGFQVUSXRPNOG-PLNGDYQASA-N 0.000 description 1
- 0 CCc1cc(-c2c(C)c(c(cccc3)c3c3ccccc33)c3[n]2-c2ccc(*)cc2)cc(CC)c1 Chemical compound CCc1cc(-c2c(C)c(c(cccc3)c3c3ccccc33)c3[n]2-c2ccc(*)cc2)cc(CC)c1 0.000 description 1
- LLYXUFQXCNIGDG-UHFFFAOYSA-N CCc1cccc(C=O)c1 Chemical compound CCc1cccc(C=O)c1 LLYXUFQXCNIGDG-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N O=C(c1ccccc1-c1c2cccc1)C2=O Chemical compound O=C(c1ccccc1-c1c2cccc1)C2=O YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
The invention provides a fluorine-containing phenanthroimidazole derivative, a synthetic method and an application thereof. In particularly, the invention provides a compound represented as the formula I, wherein the R is defined as the specification. The compound can be used for preparing a luminescent material or preparing an electroluminescent device, is high in stability, performance and efficiency, and is especially used for preparing the electroluminescent device emitting a red light, a green light, a blue light and a yellow light.
Description
Technical field
The invention belongs to electroluminescent organic material and light emitting device field, be specifically related to phenanthro-imidazole derivative and preparation method thereof, and the organic electroluminescence device of this series material.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide, resolving power advantages of higher, becomes the focus of the area researches such as material, information, physics.Different according to principle of luminosity, electroluminescent organic material is divided into fluorescent material and the large class of phosphor material two.Compared with fluorescent material, phosphor material can utilize triplet state and singlet excitons, and internal quantum efficiency can reach 100% in theory.Therefore, phosphor material is utilized to be a kind of important means obtaining high efficiency organic electroluminescence device.
In order to obtain higher electrophosphorescence efficiency, usually heavy metal phosphor material being doped in material of main part and reducing concentration quenching and triplet state-triplet state annihilation.Desirable material of main part must meet following requirements: the triplet (E of (1) material of main part
t) be greater than guest triplets energy level; (2) there is good carrier transmission performance; (3) there is good thermostability and morphological stability.At present, ruddiness and yellow phosphor device have obtained gratifying luminous efficiency.And blue emitting phosphor device is little efficiently, simultaneously major cause lacks the charge transport properties and high triplet (E that have had
t) material of main part.
Some research groups developed a series of bipolar host material with excellent charge transport properties in recent years, achieved good device performance, along with the increase efficiency decay of current density is very little.But all also there is certain defect in these materials, the triplet (E that such as HOMO/LUMO is improper or low
t) more high performance blue-light device cannot be obtained.
The triplet of ruddiness and green glow guest materials is lower, and its material of main part such as PFO, PVK, PFB etc. have made great progress, and device has met business-like requirement.But due to the triplet that blue light object is as high in FIrPic has, above material of main part cannot meet the demand of blue light electro phosphorescent device.
In sum, this area still lacks a kind of charge transport properties of having had and high triplet (E
t), be suitable for the material of main part preparing multiple color device, particularly blue light emitting device.
Summary of the invention
The object of this invention is to provide a kind of charge transport properties of having had and high triplet (E
t), be suitable for the material of main part preparing red, green, blue, Huang Si kind color device.
A first aspect of the present invention, provides a kind of as shown in the formula the compound shown in I:
Wherein, described R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
In another preference, described R is selected from lower group: the aryl of substituted or unsubstituted C12-C30, the heteroaryl of substituted or unsubstituted C6-C30.
In another preference, described R is selected from lower group: the aryl of substituted or unsubstituted C12-C30, the heteroaryl of substituted or unsubstituted C6-C30; Wherein, in described aryl or heteroaryl, there are at least 2 six-membered ring structures.
In another preference, described R is selected from lower group: the aryl of substituted or unsubstituted C12-C30, the heteroaryl of substituted or unsubstituted C6-C30; Wherein, in described aryl or heteroaryl, there are at least 3 six-membered ring structures.
In another preference, described R is selected from lower group: the aryl of substituted or unsubstituted C12-C30, the heteroaryl of substituted or unsubstituted C6-C30; Wherein, in described aryl or heteroaryl, there are at least 3 benzene ring structures.
In another preference, described R is selected from lower group: triphenylamine base, N-phenyl carbazole base.
In another preference, the triplet >=2.8eV of described compound, preferably >=3eV.
A second aspect of the present invention, provide a kind of method for making of compound as described in the first aspect of the invention, described method comprises step:
In inert solvent, react with formula II compound and formula III compound, obtain formula I.
Wherein, described formula III compound is selected from lower group: R-B (OH)
2, R-B (OCCH
3cH
3)
2.
X is selected from lower group: H, F, Cl, Br, I;
R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
Preferably, described X is selected from lower group: Cl, Br.
In another preference, described reaction is carried out under catalyzer and/or alkali exist.
In another preference, described catalyzer is palladium catalyst, is preferably selected from lower group: tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride, or its combination.
In another preference, described alkali comprises: sodium carbonate, salt of wormwood, cesium carbonate, Potassium ethanoate, potassiumphosphate, sodium hydroxide, potassium hydroxide, Potassium monofluoride, or its combination.
In another preference, the mol ratio of described formula II compound and formula III compound is 1:2 ~ 1:3.
In another preference, described inert solvent is selected from lower group: water, ethanol, glycol dimethyl ether, toluene, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, or its combination.
In another preference, described method is bag step also:
In inert solvent, use formula II ' a compound, formula II ' b compound with
reaction, obtains formula II ' compound;
Above-mentioned various in, X ' is selected from lower group: H, F, Cl, Br, I; And X ' and X may be the same or different.
In another preference, described inert solvent is selected from lower group: acetic acid, acetic anhydride, or its combination.
In another preference, described reaction is carried out under acetic acid and/or ammonium acetate exist.
In another preference, described method also comprises step: in inert solvent, uses formula II ' compound and X
2reaction, obtains formula II compound.
A third aspect of the present invention, provides a kind of purposes of compound as described in the first aspect of the invention, and described compound is for the preparation of electroluminescent material, or described compound is for the preparation of electroluminescent device.
In another preference, described electroluminescent device is Phosphorescent adulterated EL part.
A fourth aspect of the present invention, provides a kind of electroluminescent material, and described electroluminescent material comprises compound as described in the first aspect of the invention, or described electroluminescent material prepares with compound as described in the first aspect of the invention.
In another preference, described material also comprises guest materials.
In another preference, described guest materials is Ir (PPy)
3, FIrPic, Ir (f-ppy)
2(acac), Ir (ppy)
2pc, Ir (piq)
3, Ir (mppy)
3or its combination.
In another preference, described formula I and the mass ratio of guest materials are 50-99:1-10.
In another preference, described electroluminescent material is blue light material.
In another preference, described electroluminescent material is green light material.
In another preference, described electroluminescent material is yellow light material.
In another preference, described electroluminescent material is red light material.
A fifth aspect of the present invention, provides a kind of electroluminescent device, and described device comprises:
(1) substrate;
(2) nesa coating on substrate is positioned at;
(5) luminescent layer; With
(8) negative electrode on electron injecting layer is positioned at;
And described luminescent layer comprises compound as described in the first aspect of the invention, or described luminescent layer prepares with compound as described in the first aspect of the invention.
In another preference, described electroluminescent device is blue-light device.
In another preference, described electroluminescent device is green device.
In another preference, described electroluminescent device is gold-tinted device.
In another preference, described electroluminescent device is red device.
In another preference, described luminescent layer comprises the electroluminescent material described in fourth aspect present invention.
In another preference, described device also comprises:
(3) hole injection layer on nesa coating is positioned at;
(4) hole transmission layer on hole injection layer is positioned at;
(6) electron transfer layer on luminescent layer is positioned at;
(7) electron injecting layer on electron transfer layer is positioned at;
And
Described luminescent layer is between described hole transmission layer and described electron transfer layer;
Described negative electrode is positioned on described electron injecting layer.
In another preference, described device comprises the one or more features being selected from lower group:
The material of described hole injection layer comprises 4,4 ', 4 '-three (carbazole-9-base) triphenylamine; And/or
The material of described hole transmission layer comprises 4,4 '-two (9-carbazole) biphenyl; And/or
The material of described electron transfer layer comprises 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene; And/or
Described electron injecting layer comprises the material being selected from lower group: LiF, MoO
3, WO
3, or its combination.
In another preference, described substrate is glass and/or transparent plastics.
In another preference, the material of described nesa coating is tin indium oxide.
In another preference, the material of described negative electrode is Al.
In another preference, described device also comprises the one or more features being selected from lower group:
The thickness of described hole injection layer (3) is 10-30nm; And/or
The thickness of described hole transmission layer (4) is 15-35nm; And/or
Described luminescent layer (5) thickness is 10-30nm; And/or
Described electron transfer layer (6) thickness is 25-40nm; And/or
The thickness of described electron injecting layer (5) is 0.5-2nm.
A sixth aspect of the present invention, provide a kind of preparation method of the device as described in fifth aspect present invention, described method comprises step:
The substrate that one has a nesa coating is provided, and described nesa coating has hole injection layer and hole transmission layer successively;
Described emitting layer material is deposited on described hole transmission layer, forms luminescent layer;
Make described luminescent layer forms described electron transfer layer, electron injecting layer and negative electrode successively, obtain described device.
In another preference, described luminescent layer is deposited by evaporation mode.
In another preference, described method comprises step:
I substrate that () provides one to have a nesa coating;
(ii) material of described hole injection layer is deposited on described nesa coating, form hole injection layer;
(iii) material of described hole transmission layer is deposited on described hole injection layer, form hole transmission layer;
(iv) material of described luminescent layer is deposited on described hole transmission layer, form luminescent layer;
V () makes the material of described electron transfer layer deposit on described luminescent layer, form electron transfer layer;
(vi) material of described electron injecting layer is deposited on described electron transfer layer, form electron injecting layer;
(vii) material of described negative electrode is deposited on described electron injecting layer, form negative electrode.
Should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the present invention and can combining mutually between specifically described each technical characteristic in below (eg embodiment), thus form new or preferred technical scheme.As space is limited, tiredly no longer one by one to state at this.
Accompanying drawing explanation
Fig. 1 is the present invention and the Phosphorescent doping type EL device structure schematic diagram of imidazole derivative;
Fig. 2 is low temperature (77K) phosphorescence spectrum of compound obtained in embodiment 1,2;
Fig. 3 is Ir (PPy) in embodiment 3,4
3the electroluminescence spectrum of doped body material devices.
Embodiment
The present inventor, through long-term and deep research, have unexpectedly discovered that a class has the compound such as formula structure shown in I.Described compound triplet is high, may be used for preparing electroluminescent device, especially can prepare the material that luminescent spectrum wave band is blue light, has a good application prospect in monochrome, total colouring and illumination white light parts.
Term
Term " electroluminescent organic material " refers to polymer or the Small molecule organic materials that can send light under electric field action.Especially, in the present invention, described electroluminescent organic material is Small molecule organic materials.
Term " C6 ~ C30 aryl " refers to the aryl with 6 ~ 30 carbon atoms, comprises monocycle, two rings, polyaromatic, such as phenyl, naphthyl, or similar group.
Term " C1 ~ C30 aryl " refers to the aryl with 1 ~ 30 carbon atom, comprises monocycle, two rings, polyaromatic, such as pyridyl, quinolyl, or similar group.
Term " replacement " refers to that the one or more hydrogen atoms on group are selected from the substituting group replacement of lower group: C1 ~ C4 alkyl, C3 ~ C6 cycloalkyl, halogen, phenyl; Wherein, described phenyl comprises unsubstituted phenyl or has 1-3 substituent substituted-phenyl, and described substituting group is selected from: halogen, C1-C4 alkyl.
Term " halogen " refers to F, Cl, Br and I.
Compound title is abridged:
Material of main part
In phosphorescent OLED device, in order to avoid or reduce concentration quenching and triplet state-triplet state annihilation effect, cause the reduction of phosphorescence quantum yield, so phosphorescent devices adopts the phosphor material of luminescence to be entrained in material of main part and forms object structure usually.In addition, material of main part also plays the effects such as transferring charge.
Luminescent device requires that material of main part triplet is higher than doping triplet, blue light material then has triplet the highest in four kinds of colors, therefore can as the material of main part of ruddiness, green glow, gold-tinted as the material of blue light main body, Blue-light emitting host material general requirement triplet is greater than 2.8eV, by differing materials be doping can realize different colours luminescence, as FirPic doping realizes blue-light-emitting, Ir (ppy)
2pc doping realizes Yellow luminous, Ir (piq)
3doping realizes emitting red light etc.
Guest materials
In the phosphorescent OLED device of Subjective and Objective structure, luminous phosphor material is called guest materials.Usually, guest materials is some transition metal complexes, as the title complex of the metals such as Ir, Os, Pt, Cu.
Formula I
The invention provides a kind of as shown in the formula the compound shown in I:
Wherein, described R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
In another preference, described R is selected from lower group: the aryl of substituted or unsubstituted C12-C30, the heteroaryl of substituted or unsubstituted C6-C30.
In another preference, described R is selected from lower group: triphenylamine base, N-phenyl carbazole base.
Described compound can be prepared by the following method:
In inert solvent, react with formula II compound and formula III compound, obtain formula I.
Wherein, described formula III compound is selected from lower group: R-B (OH)
2, R-B (OCCH
3cH
3)
2.
X is selected from lower group: H, F, Cl, Br, I;
R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
Preferably, described X is selected from lower group: Cl, Br.
In another preference, described reaction is carried out under catalyzer and/or alkali exist.
In another preference, described catalyzer is palladium catalyst, is preferably selected from lower group: tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride, or its combination.
In another preference, described alkali comprises: sodium carbonate, salt of wormwood, cesium carbonate, Potassium ethanoate, potassiumphosphate, sodium hydroxide, potassium hydroxide, Potassium monofluoride, or its combination.
In another preference, the mol ratio of described formula II compound and formula III compound is 1:2 ~ 1:3.
In another preference, described inert solvent is selected from lower group: water, ethanol, glycol dimethyl ether, toluene, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, or its combination.
Wherein, raw material II can be prepared by the following method:
In inert solvent, use formula II ' a compound, formula II ' b compound with
reaction, obtains formula II ' compound;
Above-mentioned various in, X ' is selected from lower group: H, F, Cl, Br, I; And X ' and X may be the same or different.
In another preference, described inert solvent is selected from lower group: acetic acid, acetic anhydride, or its combination.
In another preference, described reaction is carried out under acetic acid and/or ammonium acetate exist.
In another preference, described method also comprises step: in inert solvent, uses formula II ' compound and X
2reaction, obtains formula II compound.
Described compound may be used for preparing electroluminescent material, or electroluminescent device.
Electroluminescent material
The invention provides one and there is ambipolar phenanthro-imidazole derivative, can be applied to and have in the organic electrophosphorescenpolymer doping type luminescent device of stratiform doping type structure, as the material of main part of luminescent layer.
Generally speaking, the design of material of main part should meet the following conditions: singlet and the triplet excitons energy of material of main part can be transferred to guest materials effectively, the quenching effect of the exciton energy of main object is very little simultaneously, namely the emmission spectrum of main body and the absorption spectrum of object have larger overlap, are also energy match; Material of main part should have good carrier mobility character.
Compound of the present invention owing to can adulterate from different phosphorescent guest material, therefore can prepare the multiple light section transmittings such as Red, yellow, green, blue, purple.In addition, because it has high triplet energy level (> 3.0eV), be suitable as the material of main part of the blue light guest materials of high triplet energy level, panchromatic and illumination white light parts in all have a good application prospect.
Electroluminescent material of the present invention comprises compound as described in the first aspect of the invention, or described electroluminescent material prepares with compound as described in the first aspect of the invention.
Described material optionally can also comprise guest materials, as heavy metal phosphor material etc.In the present invention, preferred guest materials comprises (but being not limited to): Ir (PPy)
3, FIrPic, Ir (f-ppy)
2(acac), Ir (ppy)
2pc, Ir (piq)
3, Ir (mppy)
3, or its combination.
In another preference, described formula I and the mass ratio of guest materials are 50-99:1-10.
Electroluminescent device
Phenanthro-imidazole derivative of the present invention can use as the material of main part of luminescent layer in organic phosphorescent electroluminescence device, to prepare electroluminescent device.
Particularly, described device comprises:
(1) substrate;
(2) nesa coating on substrate is positioned at;
(5) containing compound as described in the first aspect of the invention, or with luminescent layer prepared by compound as described in the first aspect of the invention; With
(8) negative electrode on electron injecting layer is positioned at;
Preferably, device of the present invention can also comprise other assemblies or coating, and e.g., a kind of preferred electroluminescent device of the present invention comprises:
(1) substrate;
(2) nesa coating on substrate is positioned at;
(3) hole injection layer on nesa coating is positioned at;
(4) hole transmission layer on hole injection layer is positioned at;
(5) luminescent layer on hole transmission layer is positioned at;
(6) electron transfer layer on luminescent layer is positioned at;
(7) electron injecting layer on electron transfer layer is positioned at; With
(8) negative electrode on electron injecting layer is positioned at;
And described luminescent layer comprises compound as described in the first aspect of the invention, or described luminescent layer prepares with compound as described in the first aspect of the invention.
In another preference, described luminescent layer can be compound described in first aspect present invention and guest materials, as common electroluminescent materials formed such as heavy metallic salts, such as formula I and Ir (PPy)
3the electroluminescent material etc. of common formation.
The material of other layers such as described nesa coating, hole injection layer, hole transmission layer is not limit, and can be chosen according to actual needs, preferably, in described device by those skilled in the art:
Described hole injection layer can comprise 4,4 ', 4 '-three (carbazole-9-base) triphenylamine; And/or
Described hole transmission layer can comprise 4,4 '-two (9-carbazole) biphenyl; And/or
Described electron transfer layer can comprise 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene; And/or
Described electron injecting layer can comprise the material being selected from lower group: LiF, MoO
3, WO
3, or its combination.
Described each layer thickness is not particularly limited, and can be adjusted according to practical situation.In a preference of the present invention, in described device, the thickness of each layer is as follows:
The thickness of described hole injection layer (3) is 10-30nm; And/or
The thickness of described hole transmission layer (4) is 15-35nm; And/or
Described luminescent layer (5) thickness is 10-30nm; And/or
Described electron transfer layer (6) thickness is 25-40nm; And/or
The thickness of described electron injecting layer (5) is 0.5-2nm.
A kind of preferred structure of described electroluminescent device is stratiform doping type structure, as shown in Figure 1, be followed successively by substrate (1), nesa coating (2), hole injection layer (3), hole transmission layer (4), luminescent layer (5), hole blocking layer (6), electron transfer layer (7), electron injecting layer (8), negative electrode (9) by substrate to negative electrode, it is characterized in that: luminescent layer (5) adopts phenanthro-imidazole derivative bipolar host material Doping Phosphorus photon Ir (PPy)
3.
In above-mentioned Phosphorescent doping type electroluminescent device:
Hole injection layer (3) material is preferably 4,4 ', 4 '-three (carbazole-9-base) triphenylamine, and its thickness is preferably 10-30nm;
Hole transmission layer (4) material is preferably 4,4 '-two (9-carbazole) biphenyl, and its thickness is preferably 15-35nm;
Luminescent layer (5) material of main part, guest materials mass ratio are preferably 1 ~ 10:90, and light emitting layer thickness is preferably 10-30nm;
Electron transfer layer (7) material is preferably 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene, and its thickness is preferably 25-40nm;
Electron injecting layer (8) material is preferably LiF, MoO
3, WO
3deng, its thickness is preferably 0.5-2nm; Negative electrode (9) material is preferably aluminium, and silver, calcium, magnesium etc., its thickness is preferably 100-200nm.
Major advantage of the present invention
The present invention has obtained the material of main part that a class has very high triplet (>=2.8eV), and described material of main part can adulterate with multiple guest materials, thus prepares the luminescent device of different colours.Especially, material of the present invention can also adulterate by blue light guest materials, prepares blue light emitting device.
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.The experimental technique of unreceipted actual conditions in the following example, usually conveniently condition, or according to the condition that manufacturer advises.Unless otherwise indicated, otherwise per-cent and number calculate by mol.
Embodiment 1:2-(4,4 "-two (azoles bases)-(1,1 ': 3 ', 1 "-terphenyl)-1-(synthesis of 4-(trifluoromethyl) phenanthro-imidazoles (DCzBPI)
In the present embodiment, 2-(4,4 "-two (azoles bases)-(1,1 ': 3 ', 1 "-terphenyl)-1-(structural formula of 4-(trifluoromethyl) phenanthro-imidazoles is:
Above-mentioned 2-(4,4 "-two (azoles bases)-(1,1 ': 3 ', 1 "-terphenyl) (Preparation Method of 4-(trifluoromethyl) phenanthro-imidazoles comprises the steps:-1-
Step 1: synthetic intermediate 1:2-(3,5-dibromo phenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles (Br
2bPI):
In the 500mL there-necked flask that stirring, thermometer, gas access equipment are housed, pass into argon gas 10min, add p-trifluoromethylaniline 100 parts, phenanthrenequione 20 parts, 3 successively, 5-dibromo benzaldehyde 20 parts and ammonium acetate 85 parts are dissolved in the acetic acid of 200 parts, raised temperature to 125 DEG C reaction 12h, cooling, filter, filtrate evaporate to dryness obtains crude product, and crude product adopts column chromatography silica gel to cross post and is separated, and purifies and obtains intermediate 1 (Br
2bPI): 2-(3,5-dibromo phenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles.
Above-mentioned intermediate 1 is analyzed: nuclear-magnetism:
1h NMR (400MHz, CDCl
3): δ 8.85 (d, 1H, J=8.08Hz), 8.81 (d, 1H, J=8.22Hz), 8.73 (d, 1H, J=8.21Hz), 7.97 (d, 2H, J=8.31Hz), 7.79 (t, 1H, J=8.14Hz), 7.73-7.65 (m, 4H), 7.60-7.56 (m, 3H), 7.38-7.32 (m, 1H), 7.18 (d, 1H, J=8.44Hz); Mass spectrum: (M
+): 595.8,594.1; Ultimate analysis: C56.13, H2.92, N4.27, calculated value: C56.40, H2.54, N4.70.
Step 2: target compound 2-(4,4 "-two (azoles bases)-(1,1 ': 3 ', 1 "-terphenyl)-1-(preparation (DCzBPI) of 4-(trifluoromethyl) phenanthro-imidazoles
In the there-necked flask that magnetic stirring apparatus is housed, the intermediate 1:2-(3 that 3 parts of steps 1 are synthesized, 5-dibromo phenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles, 7.5 parts of 4-(9-carbazyl) phenylo boric acids, 8 parts 20% tetraethyl-oxyammonia and 0.2 part of four triphenyl phosphorus palladium be dissolved in the toluene of 100 deals, at 105 DEG C of reaction 24h under argon shield, remove solvent, cross post to be separated, purification obtains target compound 2-(4, 4 "-two (azoles bases)-(1, 1 ': 3 ', 1 "-terphenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles.
Above-mentioned target compound is analyzed:
Nuclear-magnetism:
1h NMR (400MHz, CDCl
3): δ 8.98 (d, 1H, J=8.21Hz), 8.84 (d; 1H, J=8.20Hz), 8.76 (d; 1H, J=8.21Hz), 8.18 (d; 4H, J=7.82Hz), 8.05 (d; 2H, J=8.21Hz), 7.97 (s; H), 7.79 (t, 1H; J=8.14Hz), 7.86-7.79 (m, 5H); 7.73-7.67 (m, 4H), 7.59 (t; 1H, J=7.78Hz), 7.51-7.44 (m; 8H), 7.39-7.30 (m, 6H);
13cNMR (100MHz, CDCl
3): δ 150.1,142.4,141.3,140.8,139.3,137.9,137.6,132.4,132.1,131.2,130.1,129.6,128.6,128.5,128.0,127.6,127.5,127.4,127.3,127.1,126.7,127.6,126.1,125.4,125.0,124.5,123.6,132.3,123.0,122.6,122.3,120.8,120.4,120.2,109.8.Anal. theoretical value: C
64h
43f
3n
4: C, 83.46; H, 4.27; N, 6.08. experimental value: C, 83.01; H, 4.30; N, 5.99.
Above-mentioned phenanthro-imidazole derivative bipolar host material DCzBPI can be applied in Phosphorescent doping type electroluminescent device.Low temperature (77K) phosphorescence spectrum measuring method obtains target compound 2-(4; 4 "-two (azoles bases)-(1,1 ': 3 ', 1 "-terphenyl) (4-(trifluoromethyl) phenanthro-imidazoles triplet is 3.09eV (Fig. 2) to-1-.
Embodiment 2:2-(4,4 "-two (pentanoic)-(1,1 ': 3 ', 1 "-terphenyl)-1-(preparation of 4-(trifluoromethyl) phenanthro-imidazoles (DTPABPI)
In the present embodiment, 2-(4,4 "-two (pentanoic)-(1,1 ': 3 ', 1 "-terphenyl)-1-(structural formula of 4-(trifluoromethyl) phenanthro-imidazoles is:
Above-mentioned 2-(4,4 "-two (pentanoic)-(1,1 ': 3 ', 1 "-terphenyl) (Preparation Method of 4-(trifluoromethyl) phenanthro-imidazoles comprises the steps:-1-
Step 1: target compound 2-(4,4 "-two (pentanoic)-(1,1 ': 3 ', 1 "-terphenyl)-1-(preparation (DTPABPI) of 4-(trifluoromethyl) phenanthro-imidazoles
In the there-necked flask that magnetic stirring apparatus is housed, by the intermediate 1:2-(3 that step 1 in 1 part of embodiment 1 is synthesized, 5-dibromo phenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles, 2.5 parts of 4-boric acid triphenylamines, 4 parts 20% tetraethyl-oxyammonia and 0.1 part of four triphenyl phosphorus palladium be dissolved in the toluene of 50 deals, at 105 DEG C of reaction 24h under argon shield, remove solvent, cross post to be separated, purification obtains target compound 2-(4, 4 "-two (pentanoic)-(1, 1 ': 3 ', 1 "-terphenyl)-1-(4-(trifluoromethyl) phenanthro-imidazoles.
Above-mentioned target compound 2b is analyzed:
1h NMR (400MHz, CDCl
3): δ 8.91 (d, 1H, J=7.43Hz), 8.80 (d, 1H, J=8.17Hz), 8.73 (d, 1H, J=7.43Hz), 7.92 (d, 2H, J=7.40Hz), 7.75-7.55 (m, 8H), 7.31-7.06 (m, 31H).
13c NMR (100MHz, CDCl
3): δ 150.7,147.6,142.4,141.3,137.8134.2,132.1,131.8,130.7,130.0,129.6,129.5,129.3,128.4,127.8,127,5,127.4,127.3,127.1,126.5,126.2,125.9,125.7,125.2,124.9,124.5,124.4,123.8,123.1,123.0,122.9,122.7,122.2,120.7.Anal. theoretical value: C
64h
43f
3n
4: C, 83.10; H, 4.69; N, 6.06. experimental value: C, 82.88; H, 4.67; N, 5.99.
Above-mentioned phenanthro-imidazole derivative bipolar host material DTPABPI can be applied in Phosphorescent doping type electroluminescent device.Low temperature (77K) phosphorescence spectrum measuring method obtains target compound 2-(4; 4 "-two (pentanoic)-(1,1 ': 3 ', 1 "-terphenyl) (4-(trifluoromethyl) phenanthro-imidazoles (DTPABPI) triplet is 3.04eV (Fig. 2) to-1-.
The preparation of embodiment 3:DCzBPI Phosphorescent doping type electroluminescent device
Above-mentioned phenanthro-imidazole derivative bipolar host material DCzBPI can be applied in Phosphorescent doping type electroluminescent device.This electroluminescent device is stratiform doping type structure, as shown in Figure 1, comprises substrate successively and is followed successively by substrate 1, nesa coating 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5 to negative electrode, electron transfer layer 6, electron injecting layer 7 and negative electrode 8.Wherein, substrate 1 selects glass or transparent plastics; It is that the tin indium oxide (ITO) of 20 Ω/sq is as anode that nesa coating 2 selects face to hinder; After being cleaned by substrate, glow discharge under high purity oxygen atmosphere (plasma) processes 10min, under a high vacuum (3 ~ 2 × 10
-4pa) under, on nesa coating 2 evaporation one deck 20nm thick 4,4 ', 4 '-three (carbazole-9-base) triphenylamine is as hole injection layer 3, then continue on hole injection layer 3 evaporation one deck 24nm thick 4,4 '-two (9-carbazole) biphenyl is as hole transmission layer 4, then the luminescent layer 5 that evaporation one deck 20nm is thick on hole transmission layer 4, luminescent layer 5 adopts in the present embodiment 1 and prepares phenanthro-imidazole derivative bipolar host material DCzBPI and complex of iridium Ir (PPy)
3and FIrPic, its mass ratio is 100:X, wherein X=6; Thick 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene of evaporation one deck 30nm is continued afterwards as electron transfer layer 6 on luminescent layer 5; Then on luminescent layer 6, deposit electron injecting layer 7, electron injecting layer 7 selects LiF, and its thickness is 1nm; Finally deposition cathode 8 on electron injecting layer 7, negative electrode 8 selects Al, and its thickness is 100nm.
In the preparation process of above-mentioned Phosphorescent doping type electroluminescent device, the thickness of film adopts miniature thickness tester to measure it, measures luminosity with luminance meter, and all organic materialss and LiF and metal A l adopt the mode of vacuum evaporation film forming.
When applying suitable external voltage to above-mentioned Phosphorescent doping type electroluminescent device, the performance recording this electro-phosphorescent luminescent device is as shown in table 1.
The preparation of embodiment 4:DTPABPI Phosphorescent doping type electroluminescent device
Substantially identical with the step in embodiment 3, difference is, replaces DCzBPI with the phenanthro-imidazole derivative bipolar host material DTPABPI prepared in embodiment 2.
In above-described embodiment 3-4, the performance of Phosphorescent doping type electroluminescent device is as shown in table 1 below:
Table 1: the performance table of organic electroluminescence device in embodiment 3-4
As can be seen from above-mentioned table 1, fluorine-containing phenanthro-imidazole derivative DTPABPI and DCzBPI is all suitable as the material of main part of the luminescent layer in phosphorescent OLED device.When adopting Ir (PPy) respectively
3during with FIrPic as guest materials, realize the green emission of electroluminescent spectrum peak value at 512 ± 3nm and the blue emission (emmission spectrum is by PR705 testing of equipment) of 476 ± 5nm.Therefore, phenanthro-imidazole derivative bipolar host material derivative of the present invention can be applied in monochrome, total colouring and illumination white light parts.
The all documents mentioned in the present invention are quoted as a reference all in this application, are just quoted separately as a reference as each section of document.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read above-mentioned teachings of the present invention, these equivalent form of values fall within the application's appended claims limited range equally.
Claims (10)
1. one kind as shown in the formula the compound shown in I:
Wherein, described R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
2. the method for making of compound as claimed in claim 1, is characterized in that, comprise step:
In inert solvent, react with formula II compound and formula III compound, obtain formula I; Wherein, described formula III compound is selected from lower group: R-B (OH)
2, R-B (OCCH
3cH
3)
2;
X is selected from lower group: H, F, Cl, Br, I;
R is selected from lower group: the aryl of substituted or unsubstituted C6-C30, the heteroaryl of substituted or unsubstituted C1-C30.
3. method for making as claimed in claim 2, it is characterized in that, described method is bag step also:
In inert solvent, use formula II ' a compound, formula II ' b compound with
reaction, obtains formula II ' compound;
Above-mentioned various in, X ' is selected from lower group: H, F, Cl, Br, I; And X ' and X may be the same or different.
4. the purposes of compound as claimed in claim 1, it is characterized in that, described compound is for the preparation of electroluminescent material, or described compound is for the preparation of electroluminescent device.
5. an electroluminescent material, is characterized in that, described electroluminescent material comprises compound as claimed in claim 1, or prepared by described electroluminescent material compound as claimed in claim 1.
6. material as claimed in claim 5, it is characterized in that, described material also comprises guest materials.
7. an electroluminescent device, is characterized in that, described device comprises:
(1) substrate;
(2) nesa coating on substrate is positioned at;
(5) luminescent layer; With
(8) negative electrode on electron injecting layer is positioned at;
And described luminescent layer comprises compound as claimed in claim 1, or prepared by described luminescent layer compound as claimed in claim 1.
8. electroluminescent device as claimed in claim 7, it is characterized in that, described device also comprises:
(3) hole injection layer on nesa coating is positioned at;
(4) hole transmission layer on hole injection layer is positioned at;
(6) electron transfer layer on luminescent layer is positioned at;
(7) electron injecting layer on electron transfer layer is positioned at;
And
Described luminescent layer is between described hole transmission layer and described electron transfer layer;
Described negative electrode is positioned on described electron injecting layer.
9. device as claimed in claim 7, it is characterized in that, described device comprises the one or more features being selected from lower group:
The material of described hole injection layer comprises 4,4 ', 4 '-three (carbazole-9-base) triphenylamine; And/or
The material of described hole transmission layer comprises 4,4 '-two (9-carbazole) biphenyl; And/or
The material of described electron transfer layer comprises 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene; And/or
Described electron injecting layer comprises the material being selected from lower group: LiF, MoO
3, WO
3, or its combination.
10. the preparation method of device as claimed in claim 7, is characterized in that, comprise step:
The substrate that one has a nesa coating is provided, and described nesa coating has hole injection layer and hole transmission layer successively;
Described emitting layer material is deposited on described hole transmission layer, forms luminescent layer;
Make described luminescent layer forms described electron transfer layer, electron injecting layer and negative electrode successively, obtain described device.
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| CN113135902A (en) * | 2021-03-26 | 2021-07-20 | 广州万物物联科技有限公司 | Red light micromolecule based on carbazole phenanthroimidazole and preparation method thereof |
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