CN109928960A - A kind of high exciton utilization rate small molecule material of non-aromatic amine and application - Google Patents
A kind of high exciton utilization rate small molecule material of non-aromatic amine and application Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 119
- 150000003384 small molecules Chemical class 0.000 title claims abstract description 103
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 96
- 150000001412 amines Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 5
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 10
- 150000004826 dibenzofurans Chemical class 0.000 abstract description 6
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005864 Sulphur Substances 0.000 abstract description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 121
- 239000004327 boric acid Substances 0.000 description 105
- 238000000921 elemental analysis Methods 0.000 description 60
- 239000000047 product Substances 0.000 description 59
- 239000002994 raw material Substances 0.000 description 59
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 48
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 47
- 229930192474 thiophene Natural products 0.000 description 24
- 229910001868 water Inorganic materials 0.000 description 23
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- COBWHQCRLCSRKO-UQQQWYQISA-N (z)-3-naphthalen-1-yl-2-[4-(4-phenylphenyl)-1,3-thiazol-2-yl]prop-2-enenitrile Chemical compound C=1C=CC2=CC=CC=C2C=1/C=C(/C#N)C(SC=1)=NC=1C(C=C1)=CC=C1C1=CC=CC=C1 COBWHQCRLCSRKO-UQQQWYQISA-N 0.000 description 4
- AAZYJKNISGEWEV-UHFFFAOYSA-N 2-chloro-4-phenylpyrimidine Chemical compound ClC1=NC=CC(C=2C=CC=CC=2)=N1 AAZYJKNISGEWEV-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 230000001052 transient effect Effects 0.000 description 4
- RDLQLVAVVVLVEW-UHFFFAOYSA-N 4-chloro-2-phenylpyrimidine Chemical compound ClC1=CC=NC(C=2C=CC=CC=2)=N1 RDLQLVAVVVLVEW-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000007725 thermal activation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000001075 voltammogram Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
The invention belongs to organic photoelectrical material field, a kind of high exciton utilization rate small molecule material of non-aromatic amine and application are disclosed.The high exciton utilization rate small molecule material of non-aromatic amine has general structure shown in formula (I), R in formula1、R2And R3For the donor monomer of sulphur xanthene, dibenzothiophenes or dibenzofuran derivative.Resulting materials structure of the present invention is single, molecular weight is clear, is free of conventional fragrant amine unit, is used for organic luminescent device luminescent layer, embodies the exciton utilization rate greatly improved.
Description
Technical field
The invention belongs to organic photoelectrical material fields, and in particular to a kind of non-aromatic high exciton utilization rate small molecule material of amine
Material and application.
Background technique
Organic Light Emitting Diode (OLED) device is due to characteristics such as its self-luminous, wide colour gamut, wide viewing angle, low energy consumption, flat
Plate is shown and solid light source field shows huge application prospect.Relative to polymer material, small molecule material is due to its conjunction
The advantages such as simple, molecular weight determination, stable structure at purification are more advantageous to the efficiency for improving organic electro-optic device, and have more
Add simple device preparation technology, to realize the commercial applications of Organic Light Emitting Diode.Thermal activation delayed fluorescence (TADF)
Material is due to intrinsic small single triplet state energy gap (Δ EST), its efficient reversed intersystem crossing (RISC) process in electroluminescent
Guarantee that it can efficiently utilize the unserviceable high concentration triplet excitons of conventional fluorescent material, to realize the height close to 100%
Internal quantum efficiency (IQE).At the same time, compared with the phosphor material using heavy metal atom, pure organic thermal activation delayed fluorescence
Organic Light Emitting Diode (TADF-OLED) has been realized in the similar high efficiency with phosphorescence Organic Light Emitting Diode (PH-OLED),
So that such material shows comparable application prospect.
To acceptor systems due to being advantageously implemented quick reversed intersystem crossing with lesser single triplet state break-up energy,
There is preferable carrier balance ability simultaneously, be conducive to realize effective bipolar transmission and good current-carrying in device application
Quantum balancing becomes the mainstream scheme of TADF design of material.However, reported at present be efficiently all based on to receptor TADF system
Aromatic amine donor compound or exciplex system containing aromatic amine unit.And based on the non-aromatic amine of unimolecule
High exciton utilization rate organic light emission system does not have been reported that so far.It is related to being more advantageous to the undoped height for realizing efficient stable device
Exciton utilization rate system is even more vacancy.
Summary of the invention
In place of the above shortcoming and defect of the existing technology, the primary purpose of the present invention is that providing a kind of non-aromatic
The fragrant high exciton utilization rate small molecule material of amine.
Another object of the present invention is to provide the above-mentioned non-aromatic high exciton utilization rate small molecule materials of amine in organic light
Application in electrical part.
The object of the invention is achieved through the following technical solutions:
A kind of high exciton utilization rate small molecule material of non-aromatic amine has the general structure as shown in following formula (I):
R in formula (I)1、R2And R3In at least one any one donor substituent group in following D1~D4, remaining is
Phenyl；
In formula, R4、R5And R6It is independently selected from S or O.
Preferably, the non-aromatic amine has shown in any one of following (1)~(60) to receptor type small molecule material
Structural formula:
The above-mentioned high exciton utilization rate small molecule material of non-aromatic amine can be prepared by Suzuki coupling reaction.
Application of the above-mentioned high exciton utilization rate small molecule material of non-aromatic amine in organic electro-optic device.
Preferably, the high exciton utilization rate small molecule material of the non-aromatic amine is as luminescent layer in organic electro-optic device
Application；The organic electro-optic device includes transparent substrate, and the transparent anode layer being formed on substrate, several organic hairs
Photosphere unit and cathode layer, the organic light emission layer unit include hole injection layer, hole transmission layer, one or more luminescent layers
And electron transfer layer, wherein luminescent layer includes the high exciton utilization rate small molecule of single or as mixed component non-aromatic amine
Material.
The high exciton utilization rate small molecule material of non-aromatic amine of the invention have the following advantages that and the utility model has the advantages that
It (1) is that donor and triphen yl pyrimidines spread out the present invention is based on sulphur xanthene, dibenzothiophenes, dibenzofuran derivative
Biology is that the small molecule material structure without conventional fragrant amine unit that receptor replaces is simple, molecular weight is determining, is easy to purify, electricity
Chemical stabilization and its easily studied structure-activity relationship；Organic film can be formed by vacuum evaporation or spin coating, and apply and including
In machine light emitting diode etc. organic electro-optic device.
(2) the non-aromatic high exciton utilization rate small molecule material of amine of the present invention is used for organic luminescent device luminescent layer, compares
In the exciton utilization rate of conventional fluorescent material 25%, the exciton utilization rate (> 80%) greatly improved is embodied, and part is presented
The property of thermal activation delayed fluorescence out.
(3) the non-aromatic high exciton utilization rate small molecule material of amine of the present invention can by change sulphur oxygen atom content and with
Coupling receptor unit bonding sites, the realization of the photochromic and efficiency of material is effectively regulated and controled, and meet organic photoelectric device
The needs of part.
Detailed description of the invention
Fig. 1 is suction of the high exciton utilization rate small molecule material of non-aromatic amine of resulting structures 1 in embodiment 1 under solution
Receipts, fluorescent emission and phosphorescence emission spectra figure.
Fig. 2 is the high exciton utilization rate small molecule material of non-aromatic amine of resulting structures 5 in embodiment 5 under pulverulence
Fluorescent emission and phosphorescence emission spectra figure.
Fig. 3 is the circulation of resulting structures 1 and the high exciton utilization rate small molecule material of the non-aromatic amine of structure 5 in embodiment
Voltammogram.
Fig. 4 be the high exciton utilization rate small molecule material of non-aromatic amine of resulting structures 1 in embodiment 1 thermogravimetric analysis and
Differential scanning calorimetry (embedded figure) curve graph.
Fig. 5 is the undoped film of the high exciton utilization rate small molecule material of non-aromatic amine of resulting structures 1 in embodiment 1
Under the conditions of transient lifetime test chart.
Fig. 6 is the undoped film of the high exciton utilization rate small molecule material of non-aromatic amine of resulting structures 5 in embodiment 5
Under the conditions of transient lifetime test chart；
Fig. 7 is obtained by the high exciton utilization rate small molecule material of non-aromatic amine based on structure 1 and structure 7 in embodiment 61
Current density-voltage-luminance graph of luminescent device.
Fig. 8 is obtained by the high exciton utilization rate small molecule material of non-aromatic amine based on structure 1 and structure 7 in embodiment 61
The electroluminescent light spectrogram of luminescent device
Fig. 9 is obtained by the high exciton utilization rate small molecule material of non-aromatic amine based on structure 5 and structure 7 in embodiment 61
Current density-voltage-luminance graph of luminescent device.
Figure 10 is the non-aromatic amine high exciton utilization rate small molecule material institute based on structure 5 and structure 7 in embodiment 61
Obtain the electroluminescent light spectrogram of luminescent device.
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.
Embodiment 1
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 1 is as follows:
Specific reaction step is as follows: by thianthrene -1- boric acid (3.84mmol, 1.00g), chloro- 4, the 6- diphenylpyrimidin of 2-
(4.22mmol, 1.13g), potassium phosphate (19.20mmol, 4.07g), tricyclohexyl phosphine (0.31mmol, 86mg), Pd2(dba)3
(0.192mmol, 176mg), Isosorbide-5-Nitrae-dioxane 100mL are sequentially added in reactor, after leading to nitrogen 15min, are added at 110 DEG C
Thermal response 18h.After reaction, it is restored to room temperature to system, is extracted with methylene chloride and saturated salt solution, recycle organic phase,
Vacuum distillation removes solvent.Crude product is petroleum ether/methylene chloride 5:1 by column chromatographic isolation and purification, eluant, eluent, obtains structure
1 product, yield 67%.1 molecular formula of structure: C28H18N2S2；Molecular weight: m/z:446.59；Elemental analysis result are as follows: C,
75.31；H,4.06；N,6.27；S,14.36.
It is absorption of the high exciton utilization rate small molecule material of the non-aromatic amine of the present embodiment resulting structures 1 under solution, glimmering
Light emitting and phosphorescence emission spectra figure are as shown in Figure 1；Cyclic voltammogram is as shown in Figure 3；Thermogravimetric analysis and differential scanning calorimetry
(embedded figure) test curve is as shown in Figure 4；Transient lifetime test chart under the conditions of undoped film is as shown in Figure 5.
Embodiment 2
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 2 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -4- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 2 product of structure, yield 67%.2 molecule of structure
Formula: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；S,
7.45。
Embodiment 3
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 3 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -1- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 3 product of structure, yield 67%.3 molecule of structure
Formula: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；S,
7.45。
Embodiment 4
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 4 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 4 product of structure, yield 67%.4 molecule of structure
Formula: C28H18N2O2；Molecular weight: m/z:414.46；Elemental analysis result are as follows: C, 81.14；H,4.38；N,6.76；O,7.72.
Embodiment 5
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 5 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that chloro- 4, the 6- diphenylpyrimidin of 2- is changed into
Chloro- 2, the 6- diphenylpyrimidin of the 4- of equivalent, other raw materials and step are same as structure 1.5 product of structure is finally obtained, yield is
67%.5 molecular formula of structure: C28H18N2S2；Molecular weight: m/z:446.59；Elemental analysis result are as follows: C, 75.31；H,4.06；N,
6.27；S,14.36.
Fluorescence of the high exciton utilization rate small molecule material of the non-aromatic amine of the present embodiment resulting structures 5 under pulverulence
Transmitting and phosphorescence emission spectra figure are as shown in Figure 2；Cyclic voltammogram is as shown in Figure 3；Transient lifetime under the conditions of undoped film
Test chart is as shown in Figure 6.
Embodiment 6
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 6 is as follows:
Specific reaction step is as follows: compared with structure 5, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -4- boric acid is disliked, other raw materials and step are same as structure 5.Finally obtain 6 product of structure, yield 67%.6 molecule of structure
Formula: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；S,
7.45。
Embodiment 7
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 7 is as follows:
Specific reaction step is as follows: compared with structure 5, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -1- boric acid is disliked, other raw materials and step are same as structure 5.Finally obtain 7 product of structure, yield 67%.7 molecule of structure
Formula: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；S,
7.45。
Embodiment 8
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 8 is as follows:
Specific reaction step is as follows: compared with structure 5, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 5.Finally obtain 8 product of structure, yield 67%.8 molecule of structure
Formula: C28H18N2O2；Molecular weight: m/z:414.46；Elemental analysis result are as follows: C, 81.14；H,4.38；N,6.76；O,7.72.
Embodiment 9
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 9 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that thianthrene -1- boric acid to be changed into the thiophene of equivalent
Anthracene -2- boric acid, other raw materials and step are same as structure 1.Finally obtain 9 product of structure, yield 67%.9 molecular formula of structure:
C28H18N2S2；Molecular weight: m/z:446.59；Elemental analysis result are as follows: C, 75.31；H,4.06；N,6.27；S,14.36.
Embodiment 10
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 10 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -3- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 10 product of structure, yield 67%.Structure 10 is divided
Minor: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；
S,7.45。
Embodiment 11
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 11 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 11 product of structure, yield 67%.Structure 11 is divided
Minor: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；
S,7.45。
Embodiment 12
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 12 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -2- boric acid is disliked, other raw materials and step are same as structure 1.Finally obtain 12 product of structure, yield 67%.Structure 12 is divided
Minor: C28H18N2O2；Molecular weight: m/z:414.46；Elemental analysis result are as follows: C, 81.14；H,4.38；N,6.76；O,7.72.
Embodiment 13
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 13 is as follows:
Specific reaction step is as follows: compared with structure 5, the difference is that thianthrene -1- boric acid to be changed into the thiophene of equivalent
Anthracene -2- boric acid, other raw materials and step are same as structure 5.Finally obtain 13 product of structure, yield 67%.13 molecule of structure
Formula: C28H18N2S2；Molecular weight: m/z:446.59；Elemental analysis result are as follows: C, 75.31；H,4.06；N,6.27；S,14.36.
Embodiment 14
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 14 is as follows:
Specific reaction step is as follows: compared with structure 13, the difference is that thianthrene -2- boric acid to be changed into the pheno of equivalent
Thiophene -3- boric acid is disliked, other raw materials and step are same as structure 13.Finally obtain 14 product of structure, yield 67%.Structure 14 is divided
Minor: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；
S,7.45。
Embodiment 15
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 15 is as follows:
Specific reaction step is as follows: compared with structure 13, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 13.Finally obtain 15 product of structure, yield 67%.Structure 15 is divided
Minor: C28H18N2OS；Molecular weight: m/z:430.53；Elemental analysis result are as follows: C, 78.12；H,4.21；N,6.51；O,3.72；
S,7.45。
Embodiment 16
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 16 is as follows:
Specific reaction step is as follows: compared with structure 13, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -2- boric acid is disliked, other raw materials and step are same as structure 13.Finally obtain 16 product of structure, yield 67%.Structure 16 is divided
Minor: C28H18N2O2；Molecular weight: m/z:414.46；Elemental analysis result are as follows: C, 81.14；H,4.38；N,6.76；O,7.72.
Embodiment 17
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 17 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -4- boric acid, other raw materials and step are same as structure 1.Finally obtain 17 product of structure, yield 73%.Structure
17 molecular formula: C28H18N2S；Molecular weight: m/z:414.53；Elemental analysis result are as follows: C, 81.13；H,4.38；N,6.76；S,
7.73。
Embodiment 18
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 18 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -4- boric acid, other raw materials and step are same as structure 1.Finally obtain 18 product of structure, yield 61%.Structure
18 molecular formula: C28H18N2O；Molecular weight: m/z:398.47；Elemental analysis result are as follows: C, 84.40；H,4.55；N,7.03；O,
4.02。
Embodiment 19
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 19 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -2- boric acid, other raw materials and step are same as structure 1.Finally obtain 19 product of structure, yield 73%.Structure
19 molecular formula: C28H18N2S；Molecular weight: m/z:414.53；Elemental analysis result are as follows: C, 81.13；H,4.38；N,6.76；S,
7.73。
Embodiment 20
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 20 is as follows:
Specific reaction step is as follows: compared with structure 1, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -2- boric acid, other raw materials and step are same as structure 1.Finally obtain 20 product of structure, yield 61%.Structure
20 molecular formula: C28H18N2O；Molecular weight: m/z:398.47；Elemental analysis result are as follows: C, 84.40；H,4.55；N,7.03；O,
4.02。
Embodiment 21
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 21 is as follows:
Specific reaction step is as follows: compared with structure 17, the difference is that chloro- 4, the 6- diphenylpyrimidin of 2- is changed into
Chloro- 2, the 6- diphenylpyrimidin of the 4- of equivalent, other raw materials and step are same as structure 17.Finally obtain 21 product of structure, yield
It is 73%.21 molecular formula of structure: C28H18N2S；Molecular weight: m/z:414.53；Elemental analysis result are as follows: C, 81.13；H,4.38；
N,6.76；S,7.73.
Embodiment 22
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 22 is as follows:
Specific reaction step is as follows: compared with structure 21, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzofurans -4- the boric acid of amount, other raw materials and step are same as structure 21.22 product of structure is finally obtained, yield is
61%.22 molecular formula of structure: C28H18N2O；Molecular weight: m/z:398.47；Elemental analysis result are as follows: C, 84.40；H,4.55；N,
7.03；O,4.02.
Embodiment 23
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 23 is as follows:
Specific reaction step is as follows: compared with structure 21, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzothiophenes -2- the boric acid of amount, other raw materials and step are same as structure 21.23 product of structure is finally obtained, yield is
73%.23 molecular formula of structure: C28H18N2S；Molecular weight: m/z:414.53；Elemental analysis result are as follows: C, 81.13；H,4.38；N,
6.76；S,7.73.
Embodiment 24
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 24 is as follows:
Specific reaction step is as follows: compared with structure 21, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzofurans -2- the boric acid of amount, other raw materials and step are same as structure 21.24 product of structure is finally obtained, yield is
61%.24 molecular formula of structure: C28H18N2O；Molecular weight: m/z:398.47；Elemental analysis result are as follows: C, 84.40；H,4.55；N,
7.03；O,4.02.
Embodiment 25
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 25 is as follows:
Specific reaction step is as follows: compared with structure 13, the difference is that 2,4- bis- chloro-6-phenyls -1,3,5-triazines
Change the chloro- 6- phenyl pyrimidine of 2,4- bis- of equivalent into, other raw materials and step are same as structure 13.Finally obtain the production of structure 61
Object, yield 67%.61 molecular formula of structure: C34H20N2S4；Molecular weight: m/z:584.79；Elemental analysis result are as follows: C, 69.83；
H,3.45；N,4.79；S,21.93.
Embodiment 26
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 26 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -4- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 26 product of structure, yield 59%.Structure 26 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 27
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 27 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -1- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 27 product of structure, yield 42%.Structure 27 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。。
Embodiment 28
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 28 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 28 product of structure, yield 59%.Structure 28 is divided
Minor: C34H20N2O4；Molecular weight: m/z:520.54；Elemental analysis result are as follows: C, 78.45；H,3.87；N,5.38；O,12.29.
Embodiment 29
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 29 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that the chloro- 6- phenyl pyrimidine of 4- bis- changes by 2
The chloro- 2- phenyl pyrimidine of 4,6- bis- of equivalent, other raw materials and step are same as structure 25.Finally obtain 29 product of structure, yield
It is 67%.29 molecular formula of structure: C34H20N2S4；Molecular weight: m/z:584.79；Elemental analysis result are as follows: C, 69.83；H,3.45；
N,4.79；S,21.93.
Embodiment 30
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 30 is as follows:
Specific reaction step is as follows: compared with structure 29, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -4- boric acid is disliked, other raw materials and step are same as structure 29.Finally obtain 30 product of structure, yield 59%.Structure 30 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 31
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 31 is as follows:
Specific reaction step is as follows: compared with structure 26, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -1- boric acid is disliked, other raw materials and step are same as structure 26.Finally obtain 31 product of structure, yield 42%.Structure 31 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 32
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 32 is as follows:
Specific reaction step is as follows: compared with structure 26, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 26.Finally obtain 32 product of structure, yield 59%.Structure 32 is divided
Minor: C34H20N2O4；Molecular weight: m/z:520.54；Elemental analysis result are as follows: C, 78.45；H,3.87；N,5.38；O,12.29.
Embodiment 33
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 33 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that thianthrene -1- boric acid to be changed into the thiophene of equivalent
Anthracene -2- boric acid, other raw materials and step are same as structure 25.Finally obtain 33 product of structure, yield 59%.33 molecule of structure
Formula: C34H20N2S4；Molecular weight: m/z:584.79；Elemental analysis result are as follows: C, 69.83；H,3.45；N,4.79；S,21.93.
Embodiment 34
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 34 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -3- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 34 product of structure, yield 73%.Structure 34 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 35
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 35 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 35 product of structure, yield 40%.Structure 35 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 36
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 36 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -2- boric acid is disliked, other raw materials and step are same as structure 25.Finally obtain 36 product of structure, yield 39%.Structure 36 is divided
Minor: C34H20N2O4；Molecular weight: m/z:520.54；Elemental analysis result are as follows: C, 78.45；H,3.87；N,5.38；O,
12.29。
Embodiment 37
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 37 is as follows:
Specific reaction step is as follows: compared with structure 33, the difference is that the chloro- 6- phenyl pyrimidine of 4- bis- changes by 2
The chloro- 2- phenyl pyrimidine of 4,6- bis- of equivalent, other raw materials and step are same as structure 33.Finally obtain 37 product of structure, yield
It is 67%.37 molecular formula of structure: C34H20N2S4；Molecular weight: m/z:584.79；Elemental analysis result are as follows: C, 69.83；H,3.45；
N,4.79；S,21.93.
Embodiment 38
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 38 is as follows:
Specific reaction step is as follows: compared with structure 37, the difference is that thianthrene -2- boric acid to be changed into the pheno of equivalent
Thiophene -3- boric acid is disliked, other raw materials and step are same as structure 37.Finally obtain 38 product of structure, yield 59%.Structure 38 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。
Embodiment 39
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 39 is as follows:
Specific reaction step is as follows: compared with structure 37, the difference is that thianthrene -2- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 37.Finally obtain 39 product of structure, yield 42%.Structure 39 is divided
Minor: C34H20N2O2S2；Molecular weight: m/z:552.67；Elemental analysis result be C, 73.89；H,3.65；N,5.07；O,5.79；
S,11.60。。
Embodiment 40
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 40 is as follows:
Specific reaction step is as follows: compared with structure 37, the difference is that changing thianthrene -2- boric acid the two of equivalent into
English -2- boric acid is disliked, other raw materials and step are same as structure 37.Finally obtain 40 product of structure, yield 59%.Structure 40 is divided
Minor: C34H20N2O4；Molecular weight: m/z:520.54；Elemental analysis result are as follows: C, 78.45；H,3.87；N,5.38；O,12.29.
Embodiment 41
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 41 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -4- boric acid, other raw materials and step are same as structure 25.Finally obtain 41 product of structure, yield 76%.Structure
41 molecular formula: C34H20N2S2；Molecular weight: m/z:520.67；Elemental analysis result are as follows: C, 78.43；H,3.87；N,5.38；S,
12.31。
Embodiment 42
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 42 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -4- boric acid, other raw materials and step are same as structure 25.Finally obtain 42 product of structure, yield 62%.Structure
42 molecular formula: C34H20N2O2；Molecular weight: m/z:488.55；Elemental analysis result are as follows: C, 83.59；H,4.13；N,5.73；O,
6.55。
Embodiment 43
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 43 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -2- boric acid, other raw materials and step are same as structure 25.Finally obtain 43 product of structure, yield 73%.Structure
43 molecular formula: C34H20N2S2；Molecular weight: m/z:520.67；Elemental analysis result are as follows: C, 78.43；H,3.87；N,5.38；S,
12.31。
Embodiment 44
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 44 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -2- boric acid, other raw materials and step are same as structure 25.Finally obtain 44 product of structure, yield 61%.Structure
44 molecular formula: C34H20N2O2；Molecular weight: m/z:488.55；Elemental analysis result are as follows: C, 83.59；H,4.13；N,5.73；O,
6.55。
Embodiment 45
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 45 is as follows:
Specific reaction step is as follows: compared with structure 41, the difference is that the chloro- 6- phenyl pyrimidine of 4- bis- changes by 2
The chloro- 2- phenyl pyrimidine of 4,6- bis- of equivalent, other raw materials and step are same as structure 41.Finally obtain 45 product of structure, yield
It is 76%.45 molecular formula of structure: C34H20N2S2；Molecular weight: m/z:520.67；Elemental analysis result are as follows: C, 78.43；H,3.87；
N,5.38；S,12.31.
Embodiment 46
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 46 is as follows:
Specific reaction step is as follows: compared with structure 45, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzofurans -4- the boric acid of amount, other raw materials and step are same as structure 45.46 product of structure is finally obtained, yield is
62%.46 molecular formula of structure: C34H20N2O2；Molecular weight: m/z:488.55；Elemental analysis result are as follows: C, 83.59；H,4.13；N,
5.73；O,6.55.
Embodiment 47
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 47 is as follows:
Specific reaction step is as follows: compared with structure 45, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzothiophenes -2- the boric acid of amount, other raw materials and step are same as structure 45.47 product of structure is finally obtained, yield is
73%.47 molecular formula of structure: C34H20N2S2；Molecular weight: m/z:520.67；Elemental analysis result are as follows: C, 78.43；H,3.87；N,
5.38；S,12.31.
Embodiment 48
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 48 is as follows:
Specific reaction step is as follows: compared with structure 45, working as the difference is that dibenzothiophenes -4- boric acid is changed into etc.
Dibenzofurans -2- the boric acid of amount, other raw materials and step are same as structure 45.48 product of structure is finally obtained, yield is
61%.48 molecular formula of structure: C34H20N2O2；Molecular weight: m/z:488.55；Elemental analysis result are as follows: C, 83.59；H,4.13；N,
5.73；O,6.55.
Embodiment 49
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 49 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that change Cyanuric Chloride into the 2 of equivalent, 4,
6- trichloropyrimidine, other raw materials and step are same as structure 25.Finally obtain 49 product of structure, yield 67%.Structure 49 is divided
Minor: C40H22N2S6；Molecular weight: m/z:722.99；Elemental analysis result are as follows: C, 66.45；H,3.07；N,3.87；S,26.61.
Embodiment 50
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 50 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -4- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 50 product of structure, yield 57%.Structure 50 is divided
Minor: C40H22N2O3S3；Molecular weight: m/z:674.81；Elemental analysis result are as follows: C, 71.20；H,3.29；N,4.15；O,
7.11；S,14.25.
Embodiment 51
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 51 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -1- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 51 product of structure, yield 56%.Structure 51 is divided
Minor: C40H22N2O3S3；Molecular weight: m/z:674.81；Elemental analysis result are as follows: C, 71.20；H,3.29；N,4.15；O,
7.11；S,14.25.
Embodiment 52
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 52 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 52 product of structure, yield 43%.Structure 52 is divided
Minor: C40H22N2O6；Molecular weight: m/z:626.62；Elemental analysis result are as follows: C, 76.67；H,3.54；N,4.47；O,15.32.
Embodiment 53
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 53 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that thianthrene -1- boric acid to be changed into the thiophene of equivalent
Anthracene -2- boric acid, other raw materials and step are same as structure 49.Finally obtain 53 product of structure, yield 67%.53 molecule of structure
Formula: C40H22N2S6；Molecular weight: m/z:722.99；Elemental analysis result are as follows: C, 66.45；H,3.07；N,3.87；S,26.61.
Embodiment 54
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 54 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 54 product of structure, yield 73%.Structure 54 is divided
Minor: C40H22N2O3S3；Molecular weight: m/z:674.81；Elemental analysis result are as follows: C, 71.20；H,3.29；N,4.15；O,
7.11；S,14.25.
Embodiment 55
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 55 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that thianthrene -1- boric acid to be changed into the pheno of equivalent
Thiophene -2- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 55 product of structure, yield 56%.Structure 55 is divided
Minor: C40H22N2O3S3；Molecular weight: m/z:674.81；Elemental analysis result are as follows: C, 71.20；H,3.29；N,4.15；O,
7.11；S,14.25.
Embodiment 56
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 56 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that changing thianthrene -1- boric acid the two of equivalent into
English -1- boric acid is disliked, other raw materials and step are same as structure 49.Finally obtain 56 product of structure, yield 43%.Structure 56 is divided
Minor: C40H22N2O6；Molecular weight: m/z:626.62；Elemental analysis result are as follows: C, 76.67；H,3.54；N,4.47；O,15.32.
Embodiment 57
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 57 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -4- boric acid, other raw materials and step are same as structure 49.Finally obtain 57 product of structure, yield 63%.Structure
57 molecular formula: C40H22N2S3；Molecular weight: m/z:626.81；Elemental analysis result are as follows: C, 76.65；H,3.54；N,4.47；S,
15.34。
Embodiment 58
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 58 is as follows:
Specific reaction step is as follows: compared with structure 25, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -4- boric acid, other raw materials and step are same as structure 25.Finally obtain 34 product of structure, yield 54%.Structure
34 molecular formula: C40H22N2O3；Molecular weight: m/z:578.63；Elemental analysis result are as follows: C, 83.03；H,3.83；N,4.84；O,
8.29。
Embodiment 59
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 59 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzothiophene -2- boric acid, other raw materials and step are same as structure 49.Finally obtain 59 product of structure, yield 63%.Structure
59 molecular formula: C40H22N2S3；Molecular weight: m/z:626.81；Elemental analysis result are as follows: C, 76.65；H,3.54；N,4.47；S,
15.34。
Embodiment 60
The high exciton utilization rate small molecule material reaction equation of the non-aromatic amine of the present embodiment structure 60 is as follows:
Specific reaction step is as follows: compared with structure 49, the difference is that changing thianthrene -1- boric acid the two of equivalent into
Benzofuran -2- boric acid, other raw materials and step are same as structure 49.Finally obtain 60 product of structure, yield 54%.Structure
60 molecular formula: C40H22N2O3；Molecular weight: m/z:578.63；Elemental analysis result are as follows: C, 83.03；H,3.83；N,4.84；O,
8.29。
Embodiment 61
A kind of Organic Light Emitting Diode device based on the high exciton utilization rate small molecule material of non-aromatic amine of the present embodiment
Part, specific stepped construction are as follows:
Glass substrate/ITO/ hole transmission layer/luminescent layer/electron transfer layer/LiF/Al.ITO is anode, with above-mentioned implementation
For the high exciton utilization rate small molecule material of non-aromatic amine in example as luminescent layer, which has lesser Δ EST, electronics
Transmission material is electron transfer layer, and LiF is as electron injecting layer, and Al is as cathode.
The preparation step of stepped construction luminescent device is as follows:
Acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol is successively used to surpass transparent electro-conductive glass
Sound is cleared up 15 minutes, to remove the dirt of substrate surface.80 degrees Celsius of drying in insulating box are then put into, it then will be after drying
Ito substrate is handled 3 minutes with oxygen plasma build-up of luminance equipment, is placed in vacuum chamber, in vacuum 1 × 10-5~9 × 10-4 Pa
Under the conditions of, withDeposition rate organic material layer is deposited on anode film, then luminescent layer is deposited, by 1-20 material and
Electron transport material is individually positioned in two evaporation sources, and the mixed proportion of the two is controlled by certain deposition rate.It
Afterwards again withDeposition rate be deposited LiF, withDeposition rate evaporating Al electrode, obtain organic hair of the present embodiment
Optical diode device.
Wherein using the high exciton utilization rate small molecule material of non-aromatic amine of 1 resulting structures 1 of embodiment as luminescent layer institute
OLED device CIE chromaticity coordinates value be (0.24,0.38), maximum external quantum efficiency be 6.31% and exciton utilization rate be~
84.1%, rate score (25%) is utilized significantly beyond can be obtained maximum exciton based on conventional fluorescent material.Basic characterization
Data are as shown in table 1:
Table 1
Table 2 is that the high exciton utilization rate small molecule material of non-aromatic amine of structure 1 has as light emitting host material
Necessary energy level, optical physics and thermodynamic behaviour.
Table 2
Photophore obtained by the high exciton utilization rate small molecule material of non-aromatic amine of the present embodiment based on structure 1 and structure 7
The Current density-voltage of part-luminance graph graph of relation and electroluminescent light spectrogram difference are as shown in Figure 7 and Figure 8.
Photophore obtained by the high exciton utilization rate small molecule material of non-aromatic amine of the present embodiment based on structure 5 and structure 7
The Current density-voltage of part-luminance graph graph of relation and electroluminescent light spectrogram difference are as shown in Figure 9 and Figure 10.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (4)
1. a kind of high exciton utilization rate small molecule material of non-aromatic amine, it is characterised in that the non-aromatic high exciton of amine utilizes
Rate small molecule material has the general structure as shown in following formula (I):
R in formula (I)1、R2And R3In at least one any one donor substituent group in following D1~D4, remaining is phenyl；
In formula, R4、R5And R6It is independently selected from S or O.
2. a kind of non-aromatic high exciton utilization rate small molecule material of amine according to claim 1, it is characterised in that described
Non-aromatic amine has structural formula shown in any one of following (1)~(60) to receptor type small molecule material:
3. high exciton utilization rate small molecule material the answering in organic electro-optic device of non-aromatic amine of any of claims 1 or 2
With.
4. the high exciton utilization rate small molecule material of non-aromatic amine is as luminescent layer in organic photoelectric device according to claim 3
Application in part, it is characterised in that: the organic electro-optic device includes transparent substrate, and the transparent anode being formed on substrate
Layer, several organic light emission layer units and cathode layer, the organic light emission layer unit include hole injection layer, hole transmission layer,
One or more luminescent layers and electron transfer layer, wherein luminescent layer includes that single or non-aromatic amine as mixed component is high
Exciton utilization rate small molecule material.
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