CN107879984A - One kind buries in oblivion organic blue light small molecule and its application of mechanism based on triplet state-triplet state - Google Patents
One kind buries in oblivion organic blue light small molecule and its application of mechanism based on triplet state-triplet state Download PDFInfo
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- CN107879984A CN107879984A CN201711154506.8A CN201711154506A CN107879984A CN 107879984 A CN107879984 A CN 107879984A CN 201711154506 A CN201711154506 A CN 201711154506A CN 107879984 A CN107879984 A CN 107879984A
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- 0 CC(c1c(*2c3ccc(**)cc3)c(C=C(C3)C3(*)C=C3)c3c(C=C3)c1C=C*3N)=C2c1ccc*(N)c1 Chemical compound CC(c1c(*2c3ccc(**)cc3)c(C=C(C3)C3(*)C=C3)c3c(C=C3)c1C=C*3N)=C2c1ccc*(N)c1 0.000 description 3
- AFETWUDWZMASMB-UHFFFAOYSA-N CC(C)(C)C1C=CC(NO)=CC1 Chemical compound CC(C)(C)C1C=CC(NO)=CC1 AFETWUDWZMASMB-UHFFFAOYSA-N 0.000 description 1
- GSTNQAOWVWJLIH-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c1nc(c(ccc(Br)c2)c2c2c3ccc(Br)c2)c3[n]1-c1ccccc1 Chemical compound CC(C)(C)c(cc1)ccc1-c1nc(c(ccc(Br)c2)c2c2c3ccc(Br)c2)c3[n]1-c1ccccc1 GSTNQAOWVWJLIH-UHFFFAOYSA-N 0.000 description 1
- NQWGCNBJYHVHPZ-UHFFFAOYSA-N O=C(C1C(c2ccccc22)=C=CCC1)C2=O Chemical compound O=C(C1C(c2ccccc22)=C=CCC1)C2=O NQWGCNBJYHVHPZ-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
One kind buries in oblivion the blue-fluorescence small molecule of phenanthro- imidazoles-anthracene derivant of mechanism and its application in high efficiency non-doping electric electroluminescence device is prepared based on triplet state-triplet state, belongs to technical field of organic electroluminescence.It is prepared more particularly to preparing phenanthro- imidazoles raw material from phenanthrenequione one kettle way and being connected phenanthro- imidazoles with anthracene using Suzuki couplings.Phenanthro- imidazoles is connected with anthryl group by suitable mode, is effectively buried in oblivion by triplet state-triplet state using Triplet exciton, and introduces cyano group enhancing intermolecular interaction, is further improved triplet state-triplet state and is buried in oblivion efficiency, lifts device overall performance.Undoped blue-light device is 1000cd m in brightness in the present invention‑2When external quantum efficiency be 9.44%, efficiency roll-off is small, and cut-in voltage is low, realizes high efficiency under high illumination, is the blue-light device leading level in the world.The compound of the present invention is significant for filling up the undoped blue-light device of current high efficiency this blank, there is important application prospect in total colouring and white-light illuminating.
Description
Technical field
The invention belongs to technical field of organic electroluminescence, and in particular to one kind buries in oblivion mechanism based on triplet state-triplet state
Phenanthro- imidazoles-anthracene derivant blue-fluorescence small molecule and its application in the undoped OLEDs devices of high efficiency are prepared.
Background technology
Kodak doctor Deng Qingyun in 1987 et al. (Organic electroluminescent diodes,
C.W.Tang and S.A.VanSlyke, Appl.Phys.Lett., 1987,51 913-915.) invented it is efficient organic
Membrane electro luminescent device, the research boom of OLEDs materials and device is started in worldwide.In the last thirty years,
OLEDs fast developments simultaneously have corresponding commercialized products application in display and illumination.But this field still has a lot
Yet unresolved issue hinders OLEDs further commercialization.In OLEDs devices, singlet and triplet excitons generation ratio
Example is 1：3, traditional organic fluorescence small molecule can only utilize 25% singlet exciton, be left 75% as triplet excitons due to jump
Move and prohibit, cause device efficiency relatively low.Metal complex phosphor material based on iridium (Ir) or platinum (Pt), can allow spin forbidden
Triplet state is directly luminous, realizes that 100% exciton utilizes.Popular thermal activation delayed fluorescence (TADF) material (Highly recently
efficient organic light-emitting diodes from delayed fluorescence”,H.Uoyama,
K.Goushi, K.Shizu, H.Nomura, C.Adachi, Nature, 2012,492,234-240), in the feelings without noble metal
Under condition, by rational MOLECULE DESIGN, singlet and poor (the Δ E of triplet are reducedST), realize triplet state has to singlet
(RISC) is passed through between the inverse system of effect, can also reach the purpose that exciton 100% utilizes.But either metal complex phosphorescence
Material or TADF materials, all deposit the problem of device efficiency decay is serious under high illumination.Due to triplet state to singlet spin
Prohibit, for metal complex phosphor material, the speed of triplet state radiation transistion to singlet ground state is very slow；For TADF
For material, the speed that singlet excited state is traversed between triplet state inverse system is very slow.This all can cause the life-span of triplet state very
It is long.In device practical work process, as current density increases, the triplet excitons of generation have little time rapid radiation transistion
To singlet excited state is traversed between ground state or inverse system, a large amount of accumulations of triplet excitons in device are caused, so that can be each
The non-radiative interaction of kind is buried in oblivion, and is caused efficiency roll-off serious under high brightness, is unfavorable for the practical application of material.And it is exactly
Because triplet state is very slow to singlet spin reversal rate, metal complex phosphor material and TADF materials are required for being doped to conjunction
Triplet state Quenching caused by alleviate self assemble among suitable parent.This just needs to select suitable fertile material and essence
Thin regulation and control doping concentration, can make device architecture become complex, increase practical application cost.Blue light is in total colouring and in vain
It is essential in optical illumination, and metal complex phosphor material and TADF materials have respective limitation in blue emission is realized
Property.Therefore, exploitation can keep efficient organic fluorescence small molecule material meaning under high illumination suitable for undoped device
Great, to OLEDs technologies, further popularization has important impetus.
It is the machine that one singlet of generation is mutually collided based on two triplet excitons that triplet state-triplet state (TTA), which is buried in oblivion,
System, triplet excitons effectively can be converted into singlet and be used for lighting, and caused by triplet excitons excessive concentration can be overcome
Efficiency roll-off problem, because triplet excitons concentration is bigger in theory, the probability that two triplet excitons are mutually collided
It is bigger, it is also more effective using triplet excitons by TTA mechanism.Phenanthro- imidazoles and anthracene are all the blue light lifes of high-luminous-efficiency
Color group, and can be transferred through TTA mechanism and effectively utilize triplet excitons.Phenanthro- imidazoles is connected with anthracene by rational method,
And strengthen intermolecular interaction by introducing cyano group (CN), TTA efficiency is further improved, so as to reach the whole of lifting device
Body performance.
The content of the invention
It is an object of the invention to provide a kind of organic blue light small molecule of high efficiency for being applied to undoped device, this kind of material
Material can realize effective utilization of triplet excitons by effective TTA mechanism, and can realize high efficiency under high illumination, overcome
Metal complex phosphor material and TADF materials have to the shortcomings of device efficiency decay is serious under doping and high brightness.
A further object of the present invention in provide above-mentioned material as luminescent layer in undoped Nan dian Yao s devices are prepared
Application.
A kind of organic blue light small molecule for being based on phenanthro- imidazoles-anthracene derivant of the present invention, its structural formula such as P1n
Or shown in P2n：
Wherein Ar represents the aromatic group shown in following structural formula：
Preferably, above-mentioned organic blue light small molecule based on phenanthro- imidazoles-anthracene derivant, its structural formula such as P1-P8One of
It is shown：
Above-mentioned organic blue light small molecule based on phenanthro- imidazoles-anthracene derivant, it is to prepare phenanthrene from phenanthrenequione one kettle way
And imidazoles raw material and phenanthro- imidazoles is connected with anthracene be prepared using Suzuki couplings.
A kind of organic electroluminescence device prepared based on above-mentioned organic blue light small molecule, by glass substrate, ito anode,
Hole transmission layer, luminescent layer, electron transfer layer and negative electrode composition, it is characterised in that：Luminescent layer at least contains a kind of institute of the present invention
The organic blue light small molecule stated.
The present invention principle be：Phenanthro- imidazoles and anthracene are efficient blue light chromophores, and can be effectively sharp by TTA mechanism
With triplet excitons, the exciton for breaking through traditional singlet production rate of organic fluorescence small molecule 25% counts.TTA mechanism is to be based on two
Individual triplet state collision one singlet of generation, in certain triplet state concentration range, triplet state concentration is higher, and TTA is more effective, because
This can remain to keep under high illumination high device efficiency, and can be used for undoped device, be advantageous to simplify device architecture, drop
Low element manufacturing cost, overcoming metal complex phosphor material and TADF materials, serious efficiency roll-off is asked under high illumination
Topic.In addition, the introducing of cyano group can strengthen intermolecular interaction, be advantageous to improve TTA efficiency, it is non-so as to further be lifted
Adulterate the overall performance of device.Finally, by suitable chemical synthesis process, can have phenanthro- imidazoles multiple different anti-
Site is answered, is advantageously implemented the variation of material structure.
Organic the blue light small molecule emitter material and organic electroluminescence device of the present invention has the following advantages that and beneficial to effect
Fruit：
(1) the single determination of organic fluorescence small molecule structure of the invention, synthesis is simple, purification facility, is easy to research structure
With property relationship, be advantageous to industrial amplification production.
(2) organic fluorescence small molecule of the invention has good heat endurance, and evaporated film is smooth homogeneous, without obvious phase point
From suitable for the undoped OLEDs devices based on evaporation coating technique.
(3) organic fluorescence small molecule of the invention has higher HOMO energy levels and relatively low lumo energy, is advantageous to carry
Flow the injection and transmission of quantum balancing.
(4) undoped Nan dian Yao s device efficiencies prepared by organic fluorescence small molecule of the invention roll-off small, cut-in voltage
It is low, higher device efficiency is shown under high illumination.For the blue-light device leading level in the world.The compound of the present invention is for filling out
It is significant to mend the undoped blue-light device of current high efficiency this blank, has important application in total colouring and white-light illuminating
Prospect.
Brief description of the drawings
Fig. 1 is P1 differential calorimetry curve, fusing point (Tm) it is 344 DEG C, phase in version or glass transition are not observed
Temperature；
Fig. 2 is P1 thermogravimetric curve, glass transition temperature (Tg) it is 483 DEG C；
Fig. 3 is solvation emission spectrum.Compound shows as localized modes transmitting, does not occur obvious solvation effect, lights
Main peak is from the 434nm red shifts in non-polar solven n-hexane to the 446nm in polar solvent acetonitrile；
Fig. 4 is the Absorption and emission spectra of undoped evaporated film.Absorption spectrum main peak position is located at respectively：265nm、
326nm, 365nm, 381nm and 404nm；Emission spectrum main peak position is located at 463nm；
Fig. 5 is Current density-voltage-brightness curve of non-adulterated EL part, device energy normal work；It is most light
Spend 57787cd m-2, cut-in voltage 3.0V；
Fig. 6 is the external quantum efficiency curve of non-adulterated EL part, and maximum external quantum efficiency is 9.44%.Illustration：
Electroluminescent spectrum under 7V driving voltages, spectrum main peak are located at 470nm；
Fig. 7 is electroluminescent spectrum of the non-adulterated EL part under different voltages, and spectrum main peak is located at 470nm,
Electroluminescent spectrum is very stable under different driving voltage.
Embodiment
Embodiment 1
The present embodiment P1Preparation, including following preparation process：
M1Synthesis：M1It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by 9,10- dibromoanthracenes (5mmol,
1.67g), 4- cyanophenylboronic acids (5mmol, 735mg), tetra-triphenylphosphine palladium (0.1mmol, 115mg) be dissolved in 40mL toluene and
20mL wet chemical (2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, with two
Chloromethanes extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=3：1, volume ratio) obtain it is yellowish
Green solid (710mg, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 357.87, theoretical value
357.02。
M2Synthesis：M2Prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g), 4-
Bromobenzaldehyde (20mmol, 3.68g), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g) are dissolved in 150mL ice
In acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into 100mL frozen water, moment
There are a large amount of Precipitations.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1, volume ratio)
To white brown solid (8.05g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 448.67, theoretical value
448.06。
M3Synthesis：M3It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M2(5mmol, 2.24g), join boric acid
Pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloride
Palladium (0.1mmol, 73mg) is dissolved in 60mL dioxane, and 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates,
Extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain
White brown solid (1.48g, yield：60%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 497.03, theoretical value
496.23。
P1Synthesis：P1It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M3
(5mmol, 2.48g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (2.26g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 648.11, theoretical value
647.24.Elementary analysis (%) C48H29N3:Theoretical value C 89.00, H 4.51, N 6.49；Test value C 89.03, H 4.49,
N 6.48。
Embodiment 2
The present embodiment P2Preparation, including following preparation process：
M4Synthesis：M4Prepared by one kettle way.It is right by 9,10- phenanthrenequione (20mmol, 4.16g) in 250mL round-bottomed flasks
Tert-butyl benzene formaldehyde (20mmol, 3.34mL), 4- bromanilines (100mmol, 17.20g), ammonium acetate (80mmol, 6.16g) dissolving
In 150mL glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into 100mL ice
In water, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1,
Volume ratio) obtain white brown solid (9.05g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 505.08,
Theoretical value 504.12.
M5Synthesis：M5It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M4(5mmol, 2.52g), join boric acid
Pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloride
Palladium (0.1mmol, 73mg) is dissolved in 60mL dioxane, and 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates,
Extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain
White brown solid (1.65g, yield：60%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 552.93, theoretical value
552.29。
P2Synthesis：P2It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M5
(5mmol, 2.76g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (2.46g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 704.22, theoretical value
703.30.Elementary analysis (%) C48H29N3:Theoretical value C 88.73, H 5.30, N 5.97；Test value C 88.75, H 5.29,
N 5.96
Embodiment 3
The present embodiment P3Preparation, including following preparation process：
M6Synthesis：M6Prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g), 4-
Bromobenzaldehyde (20mmol, 3.68g), 4- bromanilines (100mmol, 17.20g), ammonium acetate (80mmol, 6.16g) are dissolved in
In 150mL glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into 100mL frozen water
In, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1, body
Product ratio) obtain white brown solid (9.47g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 526.54, reason
It is 525.97 by value.
M7Synthesis：M7It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M6(5mmol, 2.63g), join boric acid
Pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloride
Palladium (0.1mmol, 73mg) is dissolved in 60mL dioxane, and 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates,
Extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain
White brown solid (1.25g, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 623.77, theoretical value
622.32。
P3Synthesis：P3It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M7
(5mmol, 3.11g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (3.23g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 925.08, theoretical value
924.33.Elementary analysis (%) C48H29N3:Theoretical value C 89.59, H 4.36, N 6.06；Test value C 89.61, H 4.34,
N 6.05
Embodiment 4
The present embodiment P4Preparation, including following preparation process：
M8Synthesis：M8Prepared by one kettle way.In 250mL round-bottomed flasks, by 2,7- dibromos phenanthrenequione (20mmol,
7.28g), p-t-Butylbenzaldehyde (20mmol, 3.34mL), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g)
It is dissolved in 150mL glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into
In 100mL frozen water, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane
Alkane=1：1, volume ratio) obtain white brown solid (10.48g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value
For 583.15, theoretical value 582.03.
M9Synthesis：M9It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M8(5mmol, 2.91g), join boric acid
Pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloride
Palladium (0.1mmol, 73mg) is dissolved in 60mL dioxane, and 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates,
Extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain
White brown solid (1.36g, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 678.92, theoretical value
678.38。
P4Synthesis：P4It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M9
(5mmol, 3.39g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (3.43g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 981.43, theoretical value
980.39.Elementary analysis (%) C48H29N3:Theoretical value C 89.36, H 4.93, N 5.71；Test value C 89.33, H 4.95,
N 5.72
Embodiment 5
The present embodiment P5Preparation, including following preparation process：
M10Synthesis：M8Prepared by one kettle way.In 250mL round-bottomed flasks, by 3,6- dibromos phenanthrenequione (20mmol,
7.28g), p-t-Butylbenzaldehyde (20mmol, 3.34mL), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g)
It is dissolved in 150mL glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into
In 100mL frozen water, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane
Alkane=1：1, volume ratio) obtain white brown solid (10.48g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value
For 583.74, theoretical value 582.03.
M11Synthesis：M11It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M10(5mmol, 2.91g), join boron
Sour pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloro
Change palladium (0.1mmol, 73mg) and be dissolved in 60mL dioxane, 90 DEG C are stirred at reflux 24 hours under nitrogen protection.Reaction terminates
Afterwards, extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio)
Obtain white brown solid (1.36g, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 679.21, theoretical value
For 678.38.
P5Synthesis：P5It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M11
(5mmol, 3.39g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (3.43g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 981.24, theoretical value
980.39.Elementary analysis (%) C48H29N3:Theoretical value C 89.36, H 4.93, N 5.71；Test value C 89.37, H 4.93,
N 5.70
Embodiment 6
The present embodiment P6Preparation, including following preparation process：
M12Synthesis：M12Prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g),
3-bromobenzaldehyde (20mmol, 3.68g), aniline (100mmol, 9.5mL), ammonium acetate (80mmol, 6.16g) are dissolved in 150mL
In glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into 100mL frozen water, wink
Between have a large amount of Precipitations.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1, volume ratio)
Obtain white brown solid (8.05g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 449.39, theoretical value
For 448.06.
M13It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M12(5mmol, 2.24g), join boric acid pinacol
Ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] palladium chloride
(0.1mmol, 73mg) is dissolved in 60mL dioxane, and 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, use
Dichloromethane extracts, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain it is white
Brown solid (1.48g, yield：60%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 497.37, theoretical value
496.23。
P6Synthesis：P6It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M13(5mmol, 1.78g), M1
(5mmol, 2.48g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (2.26g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 647,91, theoretical value
647.24.Elementary analysis (%) C48H29N3:Theoretical value C 89.00, H 4.51, N 6.49；Test value C 89.03, H 4.50,
N 6.47
Embodiment 7
The present embodiment P7Preparation, including following preparation process：
M14Synthesis：M14Prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g),
P-t-Butylbenzaldehyde (20mmol, 3.34mL), m-bromoaniline (100mmol, 17.20g), ammonium acetate (80mmol, 6.16g) are molten
Solution in 150mL glacial acetic acid, protect lower 120 DEG C and be stirred at reflux 4 hours by nitrogen.After reaction terminates, reaction system is poured into 100mL
In frozen water, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：
1, volume ratio) obtain white brown solid (9.05g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is
505.29 theoretical value 504.12.
M15Synthesis：M15It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M14(5mmol, 2.52g), join boron
Sour pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloro
Change palladium (0.1mmol, 73mg) and be dissolved in 60mL dioxane, 90 DEG C are stirred at reflux 24 hours under nitrogen protection.Reaction terminates
Afterwards, extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio)
Obtain white brown solid (1.65g, yield：60%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 553.06, theoretical value
For 552.29.
P7Synthesis：P7It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M15
(5mmol, 2.76g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (2.46g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 704.63, theoretical value
703.30.Elementary analysis (%) C48H29N3:Theoretical value C 88.73, H 5.30, N 5.97；Test value C 88.71, H 5.31,
N 5.98
Embodiment 8
The present embodiment P8Preparation, including following preparation process：
M16Synthesis：M16Prepared by one kettle way.In 250mL round-bottomed flasks, by 9,10- phenanthrenequione (20mmol, 4.16g),
3-bromobenzaldehyde (20mmol, 3.68g), m-bromoaniline (100mmol, 17.20g), ammonium acetate (80mmol, 6.16g) are dissolved in
In 150mL glacial acetic acid, nitrogen is protected lower 120 DEG C and is stirred at reflux 4 hours.After reaction terminates, reaction system is poured into 100mL frozen water
In, there are a large amount of Precipitations moment.Filter, gained solid is used column chromatography into purification (petroleum ether：Dichloromethane=1：1, body
Product ratio) obtain white brown solid (9.47g, yield：90%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 526.73, reason
It is 525.97 by value.
M17Synthesis：M17It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M16(5mmol, 2.63g), join boron
Sour pinacol ester (10mmol, 2.54g), potassium acetate (15mmol, 1.47g), [1,1'- double (diphenylphosphino) ferrocene] dichloro
Change palladium (0.1mmol, 73mg) and be dissolved in 60mL dioxane, 90 DEG C are stirred at reflux 24 hours under nitrogen protection.Reaction terminates
Afterwards, extracted with dichloromethane, rotary evaporation concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio)
Obtain white brown solid (1.25g, yield：40%).Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 623.55, theoretical value
For 622.32.
P8Synthesis：P8It is coupled and is prepared by Suzuki.In 100mL round-bottomed flasks, by M1(5mmol, 1.78g), M17
(5mmol, 3.11g), tetra-triphenylphosphine palladium (0.1mmol, 115mg) are dissolved in 40mL toluene and 20mL wet chemical
(2.0mol L-1), 90 DEG C are stirred at reflux 24 hours under nitrogen protection.After reaction terminates, extracted with dichloromethane, rotary evaporation
Concentrated extract, column chromatography for separation (petroleum ether：Dichloromethane=1：2, volume ratio) obtain light green solid (3.23g, yield：
70%).Product is further proposed by distilling.Mass spectrum MALDI-TOF (m/z) [M+]：Test value is 925.36, theoretical value
924.33.Elementary analysis (%) C48H29N3:Theoretical value C 89.59, H 4.36, N 6.06；Test value C 89.57, H 4.35,
N 6.08
Embodiment 9
A kind of undoped organic electroluminescence device, organic blue light small molecule using molecular structure as P1 is luminescent layer material
Material, the structure of the organic electroluminescence device are as follows：
ITO/HATCN(6nm)/TAPC(25nm)/TCTA(15nm)/EML(20nm)/TPBI(40nm)/LiF(1nm)/Al
(120nm).Wherein EML is the undoped luminescent layer using P1 as luminescent material
Device fabrication process is as follows：By transparent electro-conductive glass in deionized water：Soaked two hours in alcohol mixeding liquid,
Use dust-free paper wiped clean again, then with deionized water be cleaned by ultrasonic one time, finally successively with isopropanol-acetone-toluene-
Acetone-isopropanol is cleaned by ultrasonic three times repeatedly.Before preparing device, ito glass substrate is dried up with nitrogen, it is smelly in ultraviolet
Half an hour is irradiated under oxygen, is subsequently placed in evaporation cavity, is evacuated to 5 × 10-4Pa, steamed successively on above-mentioned ito glass substrate
The material needed for device is plated, obtains organic electroluminescence device.It is described in detail below：Wherein HATCN is hole injection layer, thickness
For 6nm, evaporation rate is 0.1A s-1；TAPC is hole transmission layer, and thickness 25nm, evaporation rate is 0.3A s-1；TCTA is
Cushion, thickness 15nm, evaporation rate are 0.3A s-1；Light emitting layer thickness is 20nm, and evaporation rate is 0.3A s-1；TPBI
For electron transfer layer, thickness 40nm, evaporation rate is 0.4A s-1；LiF is electron injecting layer, thickness 1nm, evaporation rate
For 0.1A s-1；Al is negative electrode, and thickness 120nm, just beginning evaporation rate is slightly slow, is 0.7A s-1, as Al thickness degree increases
Add, when Al thickness degree is to 20nm, can gradually increase Al layer evaporation rates, be 2A s-1。
The present embodiment is with P1Current density-voltage-brightness of the undoped organic electroluminescence device of emitting layer material
Electroluminescence spectrum under curve, current efficiency-brightness curve figure and different voltages, respectively as shown in Fig. 5, Fig. 6 and Fig. 7.Gained device
The photoelectric properties of part are as shown in table 1.
Table 1：The results of property of the undoped Nan dian Yao s devices of embodiment 9
The structural formula of material therefor is as follows in the organic electroluminescence device of the present embodiment：
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (4)
1. one kind buries in oblivion organic blue light small molecule of mechanism based on triplet state-triplet state, its structural formula is as shown in P1n or P2n：
Wherein Ar represents the aromatic group shown in following structural formula,
2. a kind of organic blue light small molecule for burying in oblivion mechanism based on triplet state-triplet state as claimed in claim 1, its structure
Formula such as P1-P8One of shown in：
3. prepared by organic blue light small molecule that one kind described in claim 1 or 2 buries in oblivion mechanism based on triplet state-triplet state
Application in undoped Nan dian Yao s devices.
4. it is as claimed in claim 3 a kind of based on triplet state-triplet state bury in oblivion organic blue light small molecule of mechanism prepare it is non-
The application in Nan dian Yao s devices is adulterated, the OLEDs devices are by glass substrate, ito anode, hole transmission layer, luminescent layer, electricity
Sub- transport layer and negative electrode composition；It is characterized in that：Luminescent layer is at least based on phenanthrene containing one kind described in a kind of claim 1 or 2
And organic blue light small molecule of imidazoles-anthracene derivant.
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