CN109503458A - A kind of preparation method and applications of blue light autonomous agent heat shock activating compound - Google Patents
A kind of preparation method and applications of blue light autonomous agent heat shock activating compound Download PDFInfo
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- CN109503458A CN109503458A CN201811421894.6A CN201811421894A CN109503458A CN 109503458 A CN109503458 A CN 109503458A CN 201811421894 A CN201811421894 A CN 201811421894A CN 109503458 A CN109503458 A CN 109503458A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 230000035939 shock Effects 0.000 title claims abstract description 16
- 230000003213 activating effect Effects 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000000463 material Substances 0.000 claims abstract description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 230000002093 peripheral effect Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 12
- 239000010410 layer Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- 235000002597 Solanum melongena Nutrition 0.000 claims description 4
- 244000061458 Solanum melongena Species 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 230000003111 delayed effect Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000012265 solid product Substances 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 3
- 239000012266 salt solution Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 239000000412 dendrimer Substances 0.000 abstract description 4
- 229920000736 dendritic polymer Polymers 0.000 abstract description 4
- 238000005538 encapsulation Methods 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010129 solution processing Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- MCPLVIGCWWTHFH-UHFFFAOYSA-M disodium;4-[4-[[4-(4-sulfoanilino)phenyl]-[4-(4-sulfonatophenyl)azaniumylidenecyclohexa-2,5-dien-1-ylidene]methyl]anilino]benzenesulfonate Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)O)=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-M 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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Abstract
The invention discloses a kind of preparation method and applications of blue light autonomous agent heat shock activating compound, the present invention has designed and synthesized a kind of fluorescent molecule, is the molecule by alkyl chain link as peripheral groups, introduces famous TADF blue emission core.The alkyl chain of introducing makes material be readily dissolved in the common organic solvent such as toluene, chloroform, chlorobenzene, influence of the peripheral object unit to the heat of autonomous transmission device, light, chemical property is had studied in detail simultaneously, the result shows that, the compound of introducing can effectively improve the thermal stability and carrier balance performance from main material, by using peripheral groups as emission layer, solution obtained handles undoped TADF OLEDs, and with very high device efficiency, (EQE=6.2%, current efficiency are 10.5 cd A‑1), and colour purity is stablized, the reason is that the balance of the electric charge transfer due to effective encapsulation and bipolar dendrimer to transmitting core.
Description
Technical field
The invention belongs to compound technicals, and in particular to a kind of preparation method of blue light autonomous agent heat shock activating compound
And its application.
Background technique
The present invention is that peripheral groups are introduced to famous TADF blue emission core by the molecule of two alkyl chain links, convenient
Ground design and synthesis, the alkyl chain of introducing make material be readily dissolved in the common organic solvent such as toluene, chloroform, chlorobenzene, while in detail
Have studied influence of the periphery object unit to the heat of autonomous transmission device, light, chemical property, the results showed that, the compound of introducing
The thermal stability and carrier balance performance from main material can be effectively improved, by using peripheral groups as emission layer, is made
Solution handle undoped TADF OLEDs there is very high device efficiency (EQE=6.2%, current efficiency 10.5cdA-1),
And colour purity is stablized, the reason is that since effective encapsulation of transmitting core and the balancing charge of bipolar dendrimer are shifted.
Organic Light Emitting Diode (OLEDs) simplifies the potentiality of easy processing due to it, at low cost, and production area is greatly and by pass
Note, the performance of solvent type Organic Light Emitting Diode is influenced strongly by the solubility of its ingredient, by efficient, stable small point
Sub- material has been used as the emission source of the Organic Light Emitting Diode of solution processing, but their dissolubility is poor, and crystallinity is strong.Mutually compared with
Under, alkyl chain decorating molecule can be readily formed the low film of uniform surface roughness, so being widely used as
Resolvability emissive material.In recent years, have become one using hot activation delayed fluorescence (TADF) to produce high performance OLED
The common method of kind, because being to pass through the pure single line emission that triplet capture obtains, energy by a return system crossover mechanism
Obtain 100% internal quantum.Soluble molecule TADF is created using this layout strategy, which provides one kind
By TADF technique transfers to the possible way of solution processing platform, in some reports, to for vacuum-deposited OLED
Small molecule be modified, be used further to dissolution process, if the pure films of these materials is used as the emission layer of OLED, due to
Quenching is concentrated, performance is usually very poor, this is because harmful quasi-molecule emits, erosion and other influences, therefore, these small point
Son, which must be entrained in suitable main body, could obtain high-quantum efficiency, and Lee et al. develops two kinds of soluble blue light TADF
Transmitter, external amount 13.8%, sub- efficiency are 20.0%, can be compared favourably with the blue light TADF device of vacuum processing.But
It is that preparing for doping device is increasingly complex, and heating consumers may influence the transmitting of energy and the stability of device, in order to
Main-objective hybrid system induction is avoided mutually to separate, after TADF material and master, object are combined into a molecule by Yang et al., instead
The undoped device of answering property solution processing can reach higher external quantum efficiency (EQE), close to after this, our groups
It develops and host's dendrimer is connected to by the alkyl chain chain that TADF core and three carbazole dendritic arbors form, simultaneously effective press down
The pique effect for having made exciton maintains the fluorescence of TADF core, has made great progress in terms of no main body TADF transmitter, but
Most of which is made of carbazole dendritic arbors, therefore, develops new dendritic arbors and system research surrounding body
Influence of the unit to autonomous transmission device physical property still has pending.
Summary of the invention
The present invention is that R group is introduced to famous TADF blue emission core by the molecule of an alkyl chain link, to set
Meter and synthesis, the alkyl chain of introducing make material be readily dissolved in the common organic solvent such as toluene, chloroform, chlorobenzene, while research in detail
Influence of the periphery object unit to the heat of autonomous transmission device, light, chemical property, the results showed that, the R group of introducing can be effective
Ground improves the thermal stability and carrier balance performance from main material, by using R group as emission layer, solution processing obtained
Undoped TADF OLEDs has very high device efficiency (EQE=6.2%, current efficiency 10.5cdA-1), and colour purity
Stablize, the reason is that since effective encapsulation of transmitting core and the balancing charge of bipolar dendrimer are shifted.
1, wherein the general structure of the molecule of the alkyl chain link is as follows:
(note: n=1,2,3,4...... in general structure).
2, the R in the general structure is selected from one or both of group as shown below:
3, a kind of method for preparing above-mentioned blue light autonomous agent heat shock activating compound, which comprises the following steps:
N2Under atmosphere, by hydroxyl luminous core molecule, in group Br-tb, KOH, TBAB the addition eggplant type bottle with bromo alkyl chain,
It is mixed that toluene is added, is warming up to 78 DEG C, is stirred at reflux reaction 12h, then cools to room temperature, with Rotary Evaporators by solvent
It removes, remaining crude product is dissolved in methylene chloride, is cleaned three times with saturated salt solution, the anhydrous MgSO of organic layer4It is dry
It is dry, finally product is purified with column chromatography method (silica gel, ethyl acetate/petroleum ether), obtains white solid product.
4, application of the above-mentioned blue light autonomous agent heat shock activating compound in electroluminescent field.
5, a kind of luminescent material, including hot activation delayed fluorescence material and organic functional material, the hot activation delay
Fluorescent material is above-mentioned one or more of blue light autonomous agent heat shock activating compound, and the organic functional material is hole
One of injection material, hole transport layer material, electron injecting layer material, electronic barrier layer, luminescent material, material of main part or
It is several.
The invention has the advantages that and the utility model has the advantages that
(1) R group introduced in the present invention can effectively improve thermal stability and carrier balance performance from main material, lead to
It crosses and uses R group as emission layer, solution obtained, which handles undoped TADF OLEDs, has very high device efficiency (EQE=
6.2%, current efficiency 10.5cdA-1), and colour purity is stablized.
(2) compound that synthesizes of the present invention has very high thermal decomposition temperature and glass transition temperature, assign compound with
Excellent thermal stability.
(3) compound that the present invention synthesizes has excellent charge injectability and transportation characterization.
Detailed description of the invention
(1) Fig. 1 is the photoluminescence spectra of tbCz-CO prepared by the present invention and poCz-CO；
(2) Fig. 2 is the transient state fluorescence decay figure of tbCz-CO prepared by the present invention and poCz-CO；
(3) Current density-voltage-brightness (J-V-L) relationship that Fig. 3 is tbCz-CO prepared by the present invention and poCz-CO is bent
Line.
Specific embodiment
The present invention provides a kind of compound and its application in organic electroluminescence device, the purpose of the present invention, technology
Scheme and effect are clearer, clear, and the present invention is described in more detail below, it should be understood that specific reality described herein
It applies case for explaining only the invention, is not intended to limit the present invention:
The synthesis of embodiment 1:tbCz-CO blue light molecular compound:
In N2Under atmosphere, by 0.58g OH-CO (1.0mmol), 1.33g Br-tb (3.0mmol), 0.56g KOH
(10mmol), 1.9g TBAB (6mmol) are added in eggplant type bottle, and addition 100ml toluene is mixed, are warming up to 78 DEG C, stir back
Stream reaction 12h, then cools to room temperature, is removed solvent with Rotary Evaporators, remaining crude product is dissolved in 100ml dichloro
It in methane, is cleaned three times with saturated salt solution (3 × 100ml), the anhydrous MgSO of organic layer4It is dry, finally use column chromatography method
(silica gel, ethyl acetate/petroleum ether) purifies product, obtains white solid product (0.9g, 70%).
(note: the TBAB mentioned in above-mentioned steps is tetrabutylammonium bromide).
The synthesis of embodiment 2:poCz-CO blue light molecular compound:
Note: wherein R ' is
In N2Under atmosphere, by 0.58g OH-CO (1.0mmol), 2.79g Br-po (3.0mmol), 0.56g KOH
(10mmol), 1.9g TBAB (6mmol) are added in eggplant type bottle, and addition 100ml toluene is mixed, are warming up to 78 DEG C, stir back
Stream reaction 12h, then cools to room temperature, removes solvent with Rotary Evaporators, remaining crude product is extracted with dichloromethane,
Finally product is purified with column chromatography method (silica gel, ethyl acetate/petroleum ether), obtain white solid product (1.2g,
69%).
The above description is merely a specific embodiment, but the protection scope invented is not limited thereto, any ripe
Know those skilled in the art in the technical scope disclosed by the present invention, any changes or substitutions that can be easily thought of, should all cover
Within the protection scope of invention.
Claims (8)
1. a kind of blue light autonomous agent heat shock activating compound, which is characterized in that contain transmitting core
2. a kind of blue light autonomous agent heat shock activating compound according to claim 1, feature are being: n in general structure
Represent carbon number amount, described carbon number amount at least one.
3. a kind of blue light autonomous agent heat shock activating compound according to claim 2, feature are being: peripheral R group choosing
From one of following group or a variety of:
4. a kind of method for preparing blue light autonomous agent heat shock activating compound, which comprises the following steps: in N2Under atmosphere,
By hydroxyl luminous core molecule OH-CO, the group Br-tb with bromo alkyl chain, KOH, TBAB are added in eggplant type bottle, are added
Toluene is mixed, is warming up to 78 DEG C, is stirred at reflux reaction 12h, then cools to room temperature, removed solvent with Rotary Evaporators
It goes, remaining crude product is dissolved in methylene chloride, cleaned three times with saturated salt solution, the anhydrous MgSO of organic layer4It is dry,
Finally purified with column chromatography method to product, obtains white solid product.
5. a kind of method for preparing blue light autonomous agent heat shock activating compound according to claim 4, which is characterized in that OH-
CO general structure are as follows:
6. a kind of method for preparing blue light autonomous agent heat shock activating compound according to claim 4, which is characterized in that Br-
Tb general structure are as follows:
；
TBAB is tetrabutylammonium bromide.
7. a kind of blue light autonomous agent heat shock activating compound according to claim 1, it is characterised in that: the compound is electroluminescent
Application in illumination field.
8. a kind of luminescent material, it is characterised in that: including hot activation delayed fluorescence material and organic functional material, the heat shock
Delayed fluorescence material living is one of blue light autonomous agent heat shock activating compound described in claim 1 or a variety of, and described has
Machine functional material is hole-injecting material, hole transport layer material, electron injecting layer material, electronic barrier layer, luminescent material, master
One of body material is a variety of.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229094A (en) * | 2019-07-01 | 2019-09-13 | 武汉华星光电半导体显示技术有限公司 | Electroluminescent material, the preparation method of electroluminescent material and luminescent device |
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| CN103740359A (en) * | 2013-12-27 | 2014-04-23 | 深圳市华星光电技术有限公司 | Thermal activation delayed fluorescence material, synthesis method thereof and OLED (Organic Light Emitting Diode) device using thermal activation delayed fluorescence material |
| CN108586318A (en) * | 2018-01-16 | 2018-09-28 | 东南大学 | A kind of hot activation delayed fluorescence material of solution processable and preparation method thereof |
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2018
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| CN110229094A (en) * | 2019-07-01 | 2019-09-13 | 武汉华星光电半导体显示技术有限公司 | Electroluminescent material, the preparation method of electroluminescent material and luminescent device |
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