CN106206996A - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
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- CN106206996A CN106206996A CN201510210700.8A CN201510210700A CN106206996A CN 106206996 A CN106206996 A CN 106206996A CN 201510210700 A CN201510210700 A CN 201510210700A CN 106206996 A CN106206996 A CN 106206996A
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Abstract
The invention discloses a kind of organic electroluminescence device, including luminescent layer, the material of main part of described luminescent layer is thermal activation delayed fluorescence material, guest materials is thermal activation delayed fluorescence material, wherein, the energy gap of material of main part is more than the photic absorption spectrum of the energy gap of guest materials, the electroluminescent spectrum of material of main part and guest materials after normalization, and the difference of the wavelength that peak value is corresponding is within 50nm.
Description
Technical field
The invention belongs to organic electroluminescence device field, be specifically related to a kind of luminescent layer and use the organic electroluminescence device of thermal activation delayed fluorescence material.
Background technology
During the electroluminescent of organic electroluminescence device, rely primarily on luminous organic material electron transition from excited state to ground state and produce luminescence.At room temperature, returning to, from Triplet Excited State, the luminescence that the electron transition of ground state produces atomic weak, its energy overwhelming majority lost in the form of heat, luminous mainly by the electron transition generation of singlet excited state to ground state, referred to as electroluminescent fluorescent.Due to probability is singlet excited state three times of Triplet Excited State generation, the energy being therefore equivalent to 75% is not applied to luminescence.Make full use of this energy, the luminous efficiency of organic electroluminescence device will be effectively improved.
In order to make full use of the energy of luminescent layer material of main part Triplet Excited State, people are it is proposed that cross multiple way.Such as research and develop efficient phosphorescence dopant dye and be doped in material of main part, the triplet energy state making material of main part is effectively transferred to phosphorescence dopant dye, then phosphorescence dopant dye produces phosphorescence luminescence, so that the energy of luminescent layer material of main part Triplet Excited State is utilized effectively.The organic electroluminescence device efficiency that the method is obtained is high, but materials synthesis needs the precious metal such as iridium, platinum, expensive.Still an alternative is that the intersystem crossing character utilizing lanthanide series compound, i.e. utilize intramolecular energy to shift the 4f energy level of the Triplet energy transfer of luminescent layer material of main part to lanthanide metal ion, then luminescence etc., but obtained device efficiency is low at present.
Thermal activation delayed fluorescence (TADF, Thermal active
Delay fluorescent) it is the most popular a kind of scheme utilizing triplet excitons energy.Such as, Adachi reports thermal activation delayed fluorescence material in its article, as it is shown in figure 1, the triplet (T of such material1) and singletstate energy level (S1)Difference (Δ EST) less, then triplet energy state can be transferred to singletstate energy level, and fluorescent radiation is luminous.Patent CN 102709485 A mentions, improves device efficiency by doped with fluorescent dyes in heat lag fluorescent host.In order to carry high energy transmission combined efficiency further.Adachi etc. are at article Nature
communications 2014“High-efficiency organic light-emitting diodes
With fluorescent emitters " in, propose to use a kind of broad stopband body-dopant TADF material as auxiliary dyestuff scheme.But during charge recombination, part energy direct combination is in main body, and singletstate energy is passed to dyestuff by main body.Another part is compound on auxiliary dyestuff.Article report structure, can not fully effective utilization directly at the energy that main body is compound.Using normal body material, energy gap is big, and required driving voltage is high simultaneously.
Summary of the invention
High for above-mentioned device drive voltage and transmit insufficient problem, present invention further propose that the luminescent layer of OLED uses thermal activation delayed fluorescence material (TADF material) as material of main part the TADF material that adulterates as guest materials (fluorescence radiation dyestuff) scheme.Electric charge compound energy produced in main body and dyestuff can be made full use of further.
The organic electroluminescence device of the present invention, including luminescent layer, the material of main part of described luminescent layer is thermal activation delayed fluorescence material, guest materials is thermal activation delayed fluorescence material, wherein, the energy gap of material of main part is more than the photic absorption spectrum of the energy gap of guest materials, the electroluminescent spectrum of material of main part and guest materials after normalization, and the difference of the wavelength that peak value is corresponding is within 50 nm.
Preferably, described organic electroluminescence device, including the anode stacked gradually, hole injection layer, hole transmission layer, described luminescent layer, electron transfer layer and negative electrode.
Preferably, the mass percent that described guest materials is shared in luminescent layer is less than 10%.
Preferably, the triplet of described thermal activation delayed fluorescence material and energy gap < 0.3 eV of singletstate.
It is highly preferred that the triplet of described thermal activation delayed fluorescence material and energy gap < 0.15 eV of singletstate.
Preferably, the lumo energy of described thermal activation delayed fluorescence material is distributed on the different groups in its molecular structure from HOMO energy level.
Preferably, described thermal activation delayed fluorescence material is the material that there is charge transfer transition, there is donor groups unit and acceptor groups unit in thermal activation delayed fluorescence material simultaneously,
The group that described donor groups unit is a donor groups or plural donor groups connects and composes；
The group that described acceptor groups unit is an acceptor groups or plural acceptor groups connects and composes；
Described donor groups is selected from indolocarbazole base, carbazyl, dicarbazyl, triphenylamine base, phenazinyl, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one group substituted indolocarbazole base, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted carbazyl of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted dicarbazyl of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted triphenylamine base of group, or C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted phenazinyl of group；
Described acceptor groups is selected from naphthyl, anthryl, phenanthryl, pyrenyl, triazine radical, benzimidazolyl, cyano group, pyridine radicals, sulfuryl, phenanthro-imidazole radicals, aphthothiazoles base, benzothiazolyl, di azoly, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted naphthyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted anthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted phenanthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyrenyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted triazine radical of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzimidazolyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyridine radicals of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted sulfuryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one group substituted phenanthro-imidazole radicals；C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one group substituted aphthothiazoles base, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzothiazolyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted di azoly of group；
Wherein, one or more described donor groups unit and one or more described acceptor groups unit are directly connected to form thermal activation delayed fluorescence material；Or, one or more described donor groups unit and one or more described acceptor groups unit are connected formation thermal activation delayed fluorescence material respectively with linking group, and described linking group is for having sterically hindered group.
Preferably, one or both donor groups unit and one or both acceptor groups unit are connected formation thermal activation delayed fluorescence material respectively with linking group, or one or both acceptor groups unit are directly connected to form thermal activation delayed fluorescence material with one or both donor groups unit.
Preferably, described linking group is selected from Spirofluorene-based, phenyl, xenyl, C1-6Substituted Spirofluorene-based, the C of at least one of which of alkyl or phenyl1-6The substituted phenyl of at least one of which of alkyl or phenyl or C1-6The substituted xenyl of at least one of which of alkyl or phenyl.
Preferably, described donor groups is selected from following group:
,,,,,,,,,,,,,,, or。
Preferably, described acceptor groups is selected from following group:
,,,,,,,,Or。
Preferably, described thermal activation delayed fluorescence material is the compound with following structure:
,
1-1
,
1-2
,
1-3
,
1-4
,
1-5
,
1-6
,
1-7
,
1-8
,
1-9
,
1-10
,
1-11
,
1-12
,
1-13
,
1-14
,
1-15
,
1-16
,
2-1
,
2-2
,
2-3
,
2-4
,
2-5
,
2-6
,
2-7
,
2-8
,
2-9
,
2-10
,
2-11
,
2-12
,
2-13
,
2-14
,
2-15
,
2-16
,
3-1
,
3-2
,
3-3
,
3-4
,
3-5
,
3-6
,
3-7
,
3-8
,
3-9
,
3-10
,
3-11
3-12 。
The present invention can reach techniques below effect:
In the present invention, thermal activation delayed fluorescence material (TADF) is as material of main part (light emitting host) and guest materials (luminescent dye).The triplet of such material is less with singletstate energy level difference.And delayed fluorescence is as dyestuff, can triplet state and singletstate energy be used again simultaneously.Low-work voltage, high efficiency luminescent device can be obtained based on this.
Accompanying drawing explanation
Fig. 1 is the transmission of thermal activation delayed fluorescence material energy and radioluminescence schematic diagram
Fig. 2 is the OLED structure schematic diagram of the present invention；
Fig. 3 is the energy transmission schematic diagram of OLED luminescent layer in prior art；
Fig. 4 is thermal activation delayed fluorescence material (TADF) the energy transmission schematic diagram as light emitting host material and guest materials.
Detailed description of the invention
The invention will be further described with specific embodiment below in conjunction with the accompanying drawings, so that those skilled in the art can be better understood from the present invention and can be practiced, but illustrated embodiment is not as a limitation of the invention.
As in figure 2 it is shown, the organic electroluminescence device of the present invention includes: stack gradually the anode 2 of deposition, hole injection layer (HIL) 3, hole transmission layer (HTL) 4, luminescent layer (EML) 5, electron transfer layer (ETL) 6, electron injecting layer (EIL) 7 and negative electrode (Al) 8 on substrate 1.To have etched the ITO electro-conductive glass substrate of special pattern as substrate in experiment, substrate is placed in the deionized water containing cleanout fluid ultrasonic waves for cleaning, wash temperature is about 60 DEG C, then with infrared baking lamp, the substrate cleaned is dried, put in evaporation chamber and be deposited with hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode successively.During evaporation, chamber pressure is less than 5.0 × 10-3Wherein first organic layer is deposited with 100nm thickness MTDATA:4%F4TCNQ as hole injection layer, is then deposited with the NPB of 20 nm thickness as hole transmission layer, is deposited with organic luminous layer afterwards, after be deposited with 30nm thickness A lq3As electron transfer layer.It is deposited with the LiF of 1 nm as electron injecting layer, is finally deposited with the metal Al of 150 nm as negative electrode.
In the present invention, luminescent layer 5 uses thermal activation delayed fluorescence material (TADF material) as material of main part the TADF material that adulterates as guest materials (i.e. fluorescence radiation dyestuff).
In prior art, the luminescent layer of OLED is the material doped dyestuff of conventional body, and the triplet of conventional body material and singletstate energy level difference are relatively big, and therefore the triplet excitons energy of 75% is all wasted.As it is shown on figure 3, conventional body material doped dyestuff energy transfer process is as follows: the singletstate energy level (S1 of material of main partH) energy pass to the singletstate energy level (S1 of phosphorescent coloringD), the triplet (T1 of material of main partH) energy pass to the triplet (T1 of phosphorescent coloringD), because the life-span of triplet excitons be greater than the singlet exciton life-span, so the transmission range of triplet excitons is greater than singlet exciton transmission range.Triplet state enters the transport layer of OLED, can cause energy loss.
And the luminescent layer of OLED of the present invention uses TADF material as main body and object (also known as dyestuff).The triplet of thermal activation delayed fluorescence material and singletstate energy level difference (Δ EST) less (Δ EST<0.3
EV, preferably smaller than 0.15 eV), triplet excitons T1 the most no matter material of main part producesH, or triplet excitons T1 of dye moleculeD, all energy respectively can be passed to singletstate S1HAnd S1D.Thus it is eventually transformed into the radiation transistion luminescence of dyestuff, exciton energy has been carried out abundant application.
Wherein the energy gap of material of main part is more than the energy gap of guest materials, and the luminescence peak of material of main part substantially overlapping with the absworption peak of guest materials (after normalization, the difference of the wavelength that peak value is corresponding is within 50 nm for the photic absorption spectrum of the electroluminescent spectrum of material of main part and guest materials).On material of main part, singlet exciton shifts to the energy of object singletstate, main by Forster energy branch mode.I.e. based on the dipole-dipole mechanism between electron donor and electron acceptor molecule.If wanting energy transmission fully, the luminescent spectrum of material of main part is needed to overlap as far as possible with the absorption spectrum of guest materials.And triplet excitons is mainly shifted by Dexter energy on host material.The transfer of Dexter energy is carried out by electron exchange between electron donor and electron acceptor molecule, is the energy transfer process of a kind of short distance.Dexter mechanism has only to the electron cloud of donor and acceptor molecule pair and effectively overlaps, no matter so singletstate is to singletstate, or triplet state to shift to the energy of triplet state be all to allow.
The singletstate of thermal activation delayed fluorescence material and triplet state energy gap (Δ E in the present inventionST) < 0.3 eV, preferably smaller than 0.15 eV.
Specifically, the thermal activation delayed fluorescence material as material of main part in the present invention is following material:
The material that triplet state is less with singletstate energy gap, needs the HOMO track of corresponding molecule to separate with LUMO track.Such material is typically containing donor groups unit and acceptor groups unit.
Heretofore described thermal activation delayed fluorescence material is the material that there is charge transfer transition, there is donor groups unit and acceptor groups unit in thermal activation delayed fluorescence material simultaneously.Wherein, the group that donor groups unit is a donor groups or plural donor groups connects and composes；The group that acceptor groups unit is an acceptor groups or plural acceptor groups connects and composes；
Concrete, the structure of material of main part can be donor-connection-acceptor or the structure etc. for donor-acceptor-donor.
Donor groups is selected from indolocarbazole base, carbazyl, and two connect carbazyl, triphenylamine base, phenazinyl, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one group substituted indolocarbazole base, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted carbazyl of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted dibenzofuran group of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted triphenylamine base of group, or C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted phenazinyl of group；
Acceptor groups is selected from naphthyl, anthryl, phenanthryl, pyrenyl, triazine radical, benzimidazolyl, cyano group, pyridine radicals, sulfuryl, phenanthro-imidazole radicals, aphthothiazoles base, benzothiazolyl, di azoly, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted naphthyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted anthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted phenanthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyrenyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted triazine radical of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzimidazolyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyridine radicals of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted sulfuryl of group, more than one group substituted phenanthro-imidazole radicals in the alkyl of C1-6, methoxyl group, ethyoxyl, phenyl or pyridine radicals；C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one group substituted aphthothiazoles base, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzothiazolyl of group or C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted di azoly of group；
Wherein, one or more described donor groups unit and one or more described acceptor groups unit are directly connected to form thermal activation delayed fluorescence material；Or, one or more described donor groups unit and one or more described acceptor groups unit are connected formation thermal activation delayed fluorescence material respectively with linking group, and described linking group is for having sterically hindered group.
Above-mentioned linking group is preferably selected from Spirofluorene-based, phenyl, xenyl, C1-6Substituted Spirofluorene-based, the C of at least one of which of alkyl or phenyl1-6The substituted phenyl of at least one of which of alkyl or phenyl or C1-6The substituted xenyl of at least one of which of alkyl or phenyl.
Donor groups is preferably selected from following structure:
,,,,,,,,,,,,,,, or。
Acceptor groups is preferably selected from following structure:
,,,,,,,,Or。
Specifically, thermal activation delayed fluorescence material is selected from the compound with following structure:
1-1(Chem. Commun.,
2012,48,9580-9582)
1-2 (Angew. Chem.
Int. Ed., 2012,51,11311-11315)
1-3(Chem. Commun.
2012,48,11392-11394)
1-4(J. Mater.
Chem. C, 2013,1,4599-4604)
1-5(J. Mater.
Chem. C, 2013,1,4599-4604)
1-6 (Phys. Chem. Chem.
Phys., 2013, 15, 15850)
1-7(Δ EST=0.11, utilize Gaussian
03/TD-DFT calculates)
1-8(Δ EST=0.14, utilize Gaussian
03/TD-DFT calculates)
1-9 (Nature, 2012,492,234)
1-10 (Nature, 2012,492,234)
1-11(Nature, 2012,492,234)
1-12 (Nature, 2012,492,234)
1-13 (Nature, 2012,492,234)
1-14(Nature, 2012,492,234)
1-15(Δ EST=0.21, utilize Gaussian
03/TD-DFT calculates)
1-16
2-1(Δ EST=0.15, utilize Gaussian
03/TD-DFT calculates)
2-2(Δ EST=0.04, utilize Gaussian
03/TD-DFT calculates)
2-3
2-4 (J. AM. Chem. Soc.
2012, 134, 14706-14709)
2-5 (J. AM. Chem. Soc.
2012, 134, 14706-14709)
2-6(Chem. Mater.,
2013,25 (18), pp 3,766 3771)
2-7(Δ EST=0.07, utilize Gaussian
03/TD-DFT calculates)
2-8(Δ EST=0.16, utilizes Gaussian
03/TD-DFT calculates)
2-9(Δ EST=0.09, utilize Gaussian
03/TD-DFT calculates)
2-10(PRL, 2013,110,247401)
2-11(Δ EST=0.06, utilizes Gaussian
03/TD-DFT calculates)
2-12(Appl. Phys.
Lett., 2012,101,093306)
2-13(Phys. Chem. Chem.
Phys. 2013,15,15850)
2-14((J. Mater.
Chem. C, 2013,1,4599-4604)
2-15 (J. Mater.
Chem. C, 2013,1,4599-4604)
,
2-16
,
3-1 (CC, DOI:
10.1039/c3cc47130f)
3-2 (CC, DOI:
10.1039/c3cc47130f)
The Δ E of 3-3(CT stateST=0.03, localized modes singletstate and triplet state energy extreme difference are at 1.1 eV simultaneously, utilize Gaussian
03/TD-DFT calculates)
The Δ E of 3-4(CT stateST=0.05, localized modes singletstate and triplet state energy extreme difference are at 1.2 eV simultaneously, utilize Gaussian
03/TD-DFT calculates)
The Δ E of 3-5(CT stateST=0.01, localized modes singletstate and triplet state energy extreme difference utilize Gaussian at 1.4 eV simultaneously
03/TD-DFT calculates)
3-6 (AFM,
DOI: 10.1002/adfm.201301750)
,
3-7
,
3-8
,
3-9
,
3-10
,
3-11
3-12 。
The synthesis of related compound in the application:
1, the synthesis of compound 1-7
Synthesis 1-7a,
3.34 g carbazole, 3.22 g 3,6-dibromo carbazole, 0.5 g CuI,
0.5g phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 mlDMF, and heating reflux reaction 48 hours, are poured into water reactant liquor subsequently under nitrogen atmosphere, and decompression sucking filtration obtains solid.Solid chromatographic column isolated 1-7a, productivity is 30%.
Mass spectrometric data: ESI-MS m/z:
498 [M+H]+, elementary analysis: C36H23N3:
C:86.90, H:4.66, N:8.44.
Synthesis 1-7b,
3.11 g tribromo-benzenes, 2.48 g are to methylbenzene phenyl-sulfhydrate, and 6 g potassium carbonate, 1 g Hydro-Giene (Water Science). joins in 100 ml round-bottomed flasks, adds the DMF of 50 ml, and under nitrogen atmosphere, 100 DEG C are heated 24 hours.Being poured into water by reactant liquor subsequently, decompression sucking filtration obtains solid.Solid chromatographic column isolated 1-7b, productivity is 60%.
Mass spectrometric data: ESI-MS m/z:
401 [M+H]+, elementary analysis: C20H17BrS, C:59.85, H:4.27.
Synthesis 1-7c,
Under ice-water bath, the 1-7b being dissolved in 30 ml is slowly dropped in the dichloromethane solution of 1 g mCPBA, is maintained in ice-water bath and adds, following reaction 12h.Solid chromatographic column isolated 1-7c, productivity is 99%.
Mass spectrometric data: ESI-MS m/z:
465 [M+H]+, elementary analysis: C20H17BrO4S2, C:86.90, H:4.66, N:8.44.
Synthesis 1-7,
4.97 g 1-7a, 4.63 g
1-7b, 0.5 g CuI, 0.5 g phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 ml DMF, and heating reflux reaction 48 hours, are poured into water reactant liquor subsequently under nitrogen atmosphere, and decompression sucking filtration obtains solid.Solid chromatographic column isolated 1-7, productivity is 60%.
Mass spectrometric data: ESI-MS m/z:
882 [M+H]+, elementary analysis: C56H39N3O4S2, C 76.25, H
4.46, N 4.76.
2, the synthesis of compound 1-4
The synthesis reference 1-7 of 1-4, material detection data: mass spectrometric data: ESI-MS m/z:
717 [M+H]+, elementary analysis C44H32N2O4S2, C:73.72, H:4.50, N:3.91.
3, the synthesis of compound 1-8
4.52 g 1-8a, 3 g 1-8b and 0.05g tetra-triphenylphosphine palladium catalyst, and 5.4g potassium carbonate, join in round-bottomed flask, adds 30 ml toluene and 20 ml water and 5 ml ethanol, reacts 48h at 85 DEG C.Reaction end dichloromethane extracts, and obtains organic layer, then separates by chromatographic column, obtains 1-8, and productivity is 65%.
Mass spectrometric data: ESI-MS m/z:
640 [M+H]+, elementary analysis: C45H29N5, C:84.48, H:4.57, N:10.95.
4, the synthesis of compound 2-1
2.43 g 2-1a join in the super dry DMF solution of 0.24 g NaH (30 ml), 30 mins are stirred at room temperature, are then added drop-wise in above-mentioned solution by the DMF solution of 2.54 g 2-1b, heat 100 degree to stir 1 hour, during cooling is fallen back, cross filter solid, separate by chromatographic column.Obtain 2-1.
Mass spectrometric data: ESI-MS m/z:
701 [M+H]+, elementary analysis: C48H32N2O2S, C:82.26, H:4.60, N:4.0.
5, the synthesis of compound 2-2
The synthesis of compound 2-2 sees 2-1, and method is essentially identical with compound 2-1, and difference is to change 2-1a into bigeminy carbazole.
Mass spectrometric data: ESI-MS m/z:
879 [M+H]+, elementary analysis: C60H38N4O2S, C:81.98, H:4.36, N:6.37.
6, the synthesis of compound 2-7
Synthesis 2-7a,
2.25 g 2,4-bis-chloro-6-benzene triazine, bromobenzeneboronic acid between 2 g, 0.05 g tetra-triphenylphosphine palladium catalyst, and 5.4 g potassium carbonate, join in round-bottomed flask, add 30 ml toluene and 20 ml water and 5 ml ethanol, at 85 DEG C, react 48 h.Reaction end dichloromethane extracts, and obtains organic layer, then separates by chromatographic column, obtains 2-7a, and productivity is 58%.
Mass spectrometric data: ESI-MS m/z:
466 [M+H]+, elementary analysis: C21H13Br2N3, C:53.99, H:2.80, N:8.99.
Synthesis 2-7,
4.65 g 2-7a, 3.66 g azophenlyene, 0.5 g CuI, 0.5
G phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 ml DMF, under nitrogen atmosphere heating reflux reaction 48 hours, subsequently reactant liquor is poured into water, decompression sucking filtration obtains solid, and solid chromatographic column isolated 2-7, productivity is 48%.
Mass spectrometric data: ESI-MS m/z:
672 [M+H]+. elementary analysis: C45H29N5O2, C:80.46, H:4.35, N:4.76.
7, the synthesis of compound 2-8
Synthesis 2-8a,
2.25 g 2,4-bis-chloro-6-benzene triazine, 2 g to bromobenzeneboronic acid, 0.05 g tetra-triphenylphosphine palladium catalyst, and 5.4 g potassium carbonate, join in round-bottomed flask, add 30 ml toluene and 20 ml water and 5 ml ethanol, at 85 DEG C, react 48 h.Reaction end dichloromethane extracts, and obtains organic layer, then separates by chromatographic column, obtains 2-8a, and productivity is 55%.
Mass spectrometric data: ESI-MS m/z:
466 [M+H]+, elementary analysis: C21H13Br2N3, C:53.99, H:2.80, N:8.99.
Synthesis 2-8,
4.65 g 2-8a, 3.66 g azophenlyene, 0.5 g CuI, 0.5
G phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 ml DMF, under nitrogen atmosphere heating reflux reaction 48 hours, subsequently reactant liquor is poured into water, decompression sucking filtration obtains solid, and solid chromatographic column isolated 2-8, productivity is 56%.
Mass spectrometric data: ESI-MS m/z:
640 [M+H]+, elementary analysis: C45H29N5, C:84.48, H:4.57, N:10.95.
8, the synthesis of compound 2-9
The synthesis of 2-9 sees 2-7, and difference is to use different donor groups instead., the carbazole of selection replaces azophenlyene.4.65 g 2-8a, 3.0 g carbazoles, 0.5 g CuI, 0.5
G phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 ml DMF, under nitrogen atmosphere heating reflux reaction 48 hours, subsequently reactant liquor is poured into water, decompression sucking filtration obtains solid, and solid chromatographic column isolated 2-9, productivity is 50%.
Mass spectrometric data: ESI-MS m/z:
640 [M+H]+, elementary analysis: C45H29N5, C:84.48, H:4.57, N:10.95.
9, the synthesis of compound 2-11
Synthesis 2-11,
3.32 g Phenylindole carbazoles, 2.67g 2-chloro-4,6-hexichol triazine, 0.5g CuI, 0.5 g phenanthrene quinoline and 5.2 g potassium carbonate join in 100 ml round-bottomed flasks, add 60 ml DMF, under nitrogen atmosphere heating reflux reaction 48 hours, being poured into water by reactant liquor subsequently, decompression sucking filtration obtains solid.Solid chromatographic column isolated 2-7, productivity is 48%.
Mass spectrometric data: ESI-MS m/z:
564 [M+H]+, elementary analysis: C39H25N5, C:83.10, H:4.47, N:12.43.
10, the synthesis of compound 3-3
Synthesis 3-3a,
3 ml pyridines join in the mixed solution of o-phenylenediamine (0.6 g) and thionyl chloride (5ml), stir 10 hours at a temperature of 60 degree, extract with dichloromethane, then clean with substantial amounts of water, obtain solid.
Mass spectrometric data: ESI-MS m/z:
205。
Synthesis 3-3b,
2.25 g 3-3a, 2 g phenylboric acids, 0.05 g tetra-triphenylphosphine palladium catalyst, and 5.4 g potassium carbonate, join in round-bottomed flask, add 30 ml toluene and 20 ml water and 5 ml ethanol, at 85 DEG C, react 48 h.Reaction end dichloromethane extracts, and obtains organic layer, then separates by chromatographic column, obtains 3-3a, and productivity is 58%.
Mass spectrometric data: ESI-MS m/z:
246 [M+H]+。
Synthesis 3-3,
2.46 g 3-3b, 2.39 g 4-boric acid triphenylamine, 0.05 g tetra-triphenylphosphine palladium catalyst, and 5.4 g potassium carbonate, join in round-bottomed flask, adding 30 ml toluene and 20 ml water and 5 ml ethanol, react 48h at 85 DEG C, reaction end dichloromethane extracts, obtain organic layer, then separating by chromatographic column, obtain 3-3, productivity is 58%.
Mass spectrometric data: ESI-MS m/z:
456 [M+H]+, elementary analysis: C30H21N3S, C:79.09, H:4.65, N:9.22.
11, the synthesis of compound 3-4
The synthesis of compound 3-4 sees compound 3-3, and step is essentially identical, and difference is that acceptor groups uses the substituted benzothiazole of thiophene.
Mass spectrometric data: ESI-MS m/z:
462 [M+H]+, elementary analysis: C28H19N3S2:
C:72.86, H:4.15, N:9.10.
12, the synthesis of compound 3-5
The synthesis of compound 3-5 sees compound 3-3, and step is essentially identical, and difference is: acceptor groups uses the substituted aphthothiazoles of thiophene.
Mass spectrometric data: ESI-MS m/z:
512 [M+H]+, elementary analysis: C32H21N3S2:
C:75.12, H:4.15, N:8.21.
In the organic electroluminescence device of the present invention, anode can use inorganic material or organic conductive polymer.Inorganic material is generally the metal that the work functions such as metal-oxide or gold, copper, silver such as tin indium oxide (ITO), zinc oxide (ZnO), indium zinc oxide (IZO) are higher, preferably ITO；Organic conductive polymer is preferably the one in polythiophene/polyvinylbenzenesulfonic acid sodium (hereinafter referred to as PEDOT/PSS), polyaniline (hereinafter referred to as PANI).
Negative electrode typically uses the relatively low metal of the work functions such as lithium, magnesium, calcium, strontium, aluminum, indium or they and copper, the alloy of gold, silver, or the electrode layer that metal is alternatively formed with metal fluoride.In the present invention, negative electrode is preferably LiF layer and the Al layer (LiF layer is in outside) of stacking.
The material of hole transmission layer can be selected from arylamine class and branch polymer class low molecule material, preferably NPB.
Fluorescent dye is preferably the material such as Coumarins (such as DMQA, C545T) or double pyran (such as DCJTB, DCM) compound.
The material of electron transfer layer can use organometallic complex (such as Alq3、Gaq3, BAlq or Ga(Saph-q)) or other be usually used in the material of electron transfer layer, as aromatic condensed ring class (as pentacene) or o-phenanthroline class (such as Bphen, BCP) compound.
The organic electroluminescence device of the present invention also can have hole injection layer between anode and hole transmission layer, the material of described hole injection layer such as can use 4,4 ', 4 ' '-three (3-aminomethyl phenyl aniline) triphenylamine doping F4TCNQ, or use C.I. Pigment Blue 15 (CuPc), can be maybe metal oxide-type, such as molybdenum oxide.
For convenience, abbreviation and the full name of some organic materials related in this specification are listed as follows:
In following comparative example and embodiment, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer, cathode construction keep constant, and only luminescent layer part uses different luminescence system.
Comparative example 1,
Conventional body doping conventional fluorescent dyestuff is used to make luminescent layer,
The organic electroluminescence device structure of this comparative example is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/Alq3:1%rubrene(30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
The i.e. luminescent layer of this comparative example uses common fluorescent materials A lq3Doing material of main part, rubrene is entrained in material of main part (accounting for the 1% of luminescent layer quality) as guest materials (luminescent dye).
Comparative example 2
Use independent TADF material as luminescent layer,
The organic electroluminescence device structure of this comparative example is as follows:
ITO/MTDATA:4%F4TCNQ (100nm)/NPB (20nm)/host (compound 2-16) (30nm)/Alq3 (30nm)/LiF (1nm)/Al (150nm)
Comparative example 3
Use TADF material as light emitting host, use a kind of common fluorescent material rubrene as dyestuff.
The organic electroluminescence device structure of the present embodiment is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
HOST (compound 1-16): 1%rubrene (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
The i.e. luminescent layer of the present embodiment uses TADF material to be material of main part HOST (compound 1-16), uses common fluorescent material rubrene to be entrained in material of main part (accounting for the 1% of luminescent layer quality) as luminescent dye.
Embodiment 1
Use TADF material HOST (compound 1-16) as light emitting host, the another kind of TADF material Dopant (compound 2-16) of doping as dyestuff (accounting for the 3% of luminescent layer quality), the two.The wherein energy gap of light emitting host HOST (compound 1-16) energy gap more than dyestuff Dopant (compound 2-16), and the luminescence peak of material of main part substantially overlapping with the absworption peak of guest materials (after normalization, the difference of the wavelength that peak value is corresponding is within 50 nm for the photic absorption spectrum of the electroluminescent spectrum of material of main part and guest materials).
The organic electroluminescence device structure of the present embodiment is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
HOST(1-16):1% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
The experimental data of above-mentioned comparative example and embodiment is as shown in the table:
Because relating to when embodiment color not quite identical, so cannot simply be contrasted from current efficiency, under our focusing on comparative's external quantum efficiency and different brightness, the variation tendency of external quantum efficiency.And the driving voltage of correspondence under 1000nits, to select the device of optimum performance.
By comparative example above it can be seen that 1) conventional fluorescent system doped with fluorescent dyes, corresponding relatively low external quantum efficiency, mainly it is limited to singletstate 25% ratio and limits.2) use TADF material separately as luminescent layer, although under low-light level, the higher external quantum efficiency of correspondence, but along with the increase of brightness, efficiency declines very fast.3) using TADF material doped fluorescent dye scheme, compare and obtain higher quantum efficiency, efficiency increases along with brightness simultaneously, reduces the most serious.4) use TADF material doped TADF dyestuff scheme, compare quantum efficiency the highest, and efficiency decline phenomenon is the most obvious.
By above-mentioned contrast it can be seen that use common light emitting host forbidden band width, required driving voltage is high, efficient.And using TADF material as main body and dyestuff, efficiency is high and follows brightness rising, and efficiency declines inconspicuous.
Embodiment 2 carries out comparative study to the ratio of two kinds of TADF materials further to embodiment 6.This series embodiment agent structure is similar to Example 1, effectively regulates simply by the concentration of two kinds of material of main parts.
Embodiment 2
Use TADF material Host (1-16) as light emitting host, use 50% concentration (accounting for the 50% of luminescent layer quality) Dopant (2-16) as luminescent dye
The organic electroluminescence device structure of the present embodiment is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
Host(1-16):50% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
Embodiment 3
The organic electroluminescence device structure of the present embodiment is as follows:
Use TADF material Host (1-16) as light emitting host, use 30% concentration Dopant (2-16) as luminescent dye
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
Host(1-16):30% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
Embodiment 4
The organic electroluminescence device structure of the present embodiment is as follows:
Use TADF material Host (1-16) as light emitting host, use 10% concentration Dopant (2-16) as luminescent dye
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
Host(1-16):10% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
Embodiment 5
Use TADF material Host (1-16) as light emitting host, use 5% concentration Dopant (2-16) as luminescent dye
The organic electroluminescence device structure of the present embodiment is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
Host(1-16):5% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
Embodiment 6
Use TADF material Host (1-16) as light emitting host, use 1% concentration Dopant (2-16) as luminescent dye
The organic electroluminescence device structure of the present embodiment is as follows:
ITO/MTDATA:4%F4TCNQ(100nm)/NPB(20nm)/
Host(1-16):1% Dopant(2-16) (30nm)/Alq3(30nm)/LiF(1nm)/Al(150nm)
The experimental data of above-mentioned comparative example 1 and embodiment 2-6 is as shown in the table:
Emphasis is by external quantum efficiency size and the variation tendency of external quantum efficiency under the different brightness of contrast.And the driving voltage of correspondence under 1000nits, to select the device of optimum performance.
By above-described embodiment it can be seen that when TADF material is as dyestuff in this system, concentration has higher efficiency, relatively low driving voltage when less than 10% relatively, and shields body efficiency and decline inconspicuous.
Embodiment 7
The structure of the present embodiment is similar to Example 1, differing only in luminescent layer uses different material of main parts different, wherein, after normalization, the difference of the wavelength that peak value is corresponding is within 50 nm for the photic absorption spectrum of the electroluminescent spectrum of material of main part (compound 1-12,2-10,2-12) and guest materials (compound 2-16).
Embodiment described above is only the preferred embodiment lifted by absolutely proving the present invention, and protection scope of the present invention is not limited to this.The equivalent that those skilled in the art are made on the basis of the present invention substitutes or conversion, all within protection scope of the present invention.Protection scope of the present invention is as the criterion with claims.
Claims (12)
1. an organic electroluminescence device, including luminescent layer, it is characterized in that, the material of main part of described luminescent layer is thermal activation delayed fluorescence material, guest materials is thermal activation delayed fluorescence material, and wherein, the energy gap of material of main part is more than the energy gap of guest materials, after normalization, the difference of the wavelength that peak value is corresponding is within 50 nm for the photic absorption spectrum of the electroluminescent spectrum of material of main part and guest materials.
Organic electroluminescence device the most according to claim 1, it is characterised in that include anode, hole injection layer, hole transmission layer, described luminescent layer, electron transfer layer and the negative electrode stacked gradually.
Organic electroluminescence device the most according to claim 1, it is characterised in that described guest materials mass percent shared by luminescent layer is less than 10%.
4. according to the organic electroluminescence device described in any one of claim 1 ~ 3, it is characterised in that the triplet of described thermal activation delayed fluorescence material and energy gap < 0.3 eV of singletstate.
5. according to the organic electroluminescence device described in any one of claim 4, it is characterised in that the triplet of described thermal activation delayed fluorescence material and energy gap < 0.15 eV of singletstate.
Organic electroluminescence device the most according to claim 4, it is characterised in that the lumo energy of described thermal activation delayed fluorescence material is distributed on the different groups in its molecular structure from HOMO energy level.
Organic electroluminescence device the most according to claim 6, it is characterised in that described thermal activation delayed fluorescence material is the material that there is charge transfer transition, there is donor groups unit and acceptor groups unit in thermal activation delayed fluorescence material simultaneously,
The group that described donor groups unit is a donor groups or plural donor groups connects and composes；
The group that described acceptor groups unit is an acceptor groups or plural acceptor groups connects and composes；
Described donor groups is selected from indolocarbazole base, carbazyl, dicarbazyl, triphenylamine base, phenazinyl, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one group substituted indolocarbazole base, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted carbazyl of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted dicarbazyl of group, C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted triphenylamine base of group, or C1-6Alkyl, methoxyl group, ethyoxyl or phenyl in more than one the substituted phenazinyl of group；
Described acceptor groups is selected from naphthyl, anthryl, phenanthryl, pyrenyl, triazine radical, benzimidazolyl, cyano group, pyridine radicals, sulfuryl, phenanthro-imidazole radicals, aphthothiazoles base, benzothiazolyl, di azoly, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted naphthyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted anthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted phenanthryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyrenyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted triazine radical of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzimidazolyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted pyridine radicals of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted sulfuryl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one group substituted phenanthro-imidazole radicals；C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one group substituted aphthothiazoles base, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted benzothiazolyl of group, C1-6Alkyl, methoxyl group, ethyoxyl, phenyl or pyridine radicals in more than one the substituted di azoly of group；
Wherein, one or more described donor groups unit and one or more described acceptor groups unit are directly connected to form thermal activation delayed fluorescence material；Or, one or more described donor groups unit and one or more described acceptor groups unit are connected formation thermal activation delayed fluorescence material respectively with linking group, and described linking group is for having sterically hindered group.
Organic electroluminescence device the most according to claim 7, it is characterized in that, one or both donor groups unit and one or both acceptor groups unit are connected formation thermal activation delayed fluorescence material respectively with linking group, or one or both acceptor groups unit are directly connected to form thermal activation delayed fluorescence material with one or both donor groups unit.
Organic electroluminescence device the most according to claim 7, it is characterised in that described linking group is selected from Spirofluorene-based, phenyl, xenyl, C1-6Substituted Spirofluorene-based, the C of at least one of which of alkyl or phenyl1-6The substituted phenyl of at least one of which of alkyl or phenyl or C1-6The substituted xenyl of at least one of which of alkyl or phenyl.
Organic electroluminescence device the most according to claim 7, it is characterised in that described donor groups is selected from following group:
,,,,,,
,
,,
,,,,
,, or。
11. organic electroluminescence devices according to claim 7, it is characterised in that described acceptor groups is selected from following group:
,
,
,,,
,
,
,
Or。
12. organic electroluminescence device according to claim 7, it is characterised in that described thermal activation delayed fluorescence material is the compound with following structure:
,
1-1
,
1-2
,
1-3
,
1-4
,
1-5
,
1-6
,
1-7
,
1-8
,
1-9
,
1-10
,
1-11
,
1-12
,
1-13
,
1-14
,
1-15
,
1-16
,
2-1
,
2-2
,
2-3
,
2-4
,
2-5
,
2-6
,
2-7
,
2-8
,
2-9
,
2-10
,
2-11
,
2-12
,
2-13
,
2-14
,
2-15
,
2-16
,
3-1
,
3-2
,
3-3
,
3-4
,
3-5
,
3-6
,
3-7
,
3-8
,
3-9
,
3-10
,
3-11
3-12 。
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Application publication date: 20161207 |