CN109336926A - A class of multifunctional organic light-emitting materials based on triphenylphosphine oxide and carbazole derivatives - Google Patents
A class of multifunctional organic light-emitting materials based on triphenylphosphine oxide and carbazole derivatives Download PDFInfo
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- CN109336926A CN109336926A CN201811238586.XA CN201811238586A CN109336926A CN 109336926 A CN109336926 A CN 109336926A CN 201811238586 A CN201811238586 A CN 201811238586A CN 109336926 A CN109336926 A CN 109336926A
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- triphenylphosphine oxide
- organic material
- luminous organic
- carbazole derivates
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 title description 6
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 239000011368 organic material Substances 0.000 claims abstract description 21
- 238000000295 emission spectrum Methods 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- -1 M10 compound Chemical class 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 9
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 8
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 claims description 7
- 230000002776 aggregation Effects 0.000 claims description 5
- 238000004220 aggregation Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKRDLYQFJLVRPR-UHFFFAOYSA-N 10H-phenoxazine piperazine Chemical compound N1CCNCC1.C1=CC=CC=2OC3=CC=CC=C3NC12 OKRDLYQFJLVRPR-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract description 5
- 238000006467 substitution reaction Methods 0.000 abstract description 5
- 230000033228 biological regulation Effects 0.000 abstract description 4
- 238000013461 design Methods 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 238000005859 coupling reaction Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000010129 solution processing Methods 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- SCHRRICRQNJJKN-UHFFFAOYSA-N P.[O] Chemical group P.[O] SCHRRICRQNJJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000000873 masking effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PKHKPLVXRYPWPO-UHFFFAOYSA-N 1-bromo-3-[(3-bromophenyl)-phenylphosphoryl]benzene Chemical class BrC1=CC=CC(P(=O)(C=2C=CC=CC=2)C=2C=C(Br)C=CC=2)=C1 PKHKPLVXRYPWPO-UHFFFAOYSA-N 0.000 description 2
- URGNHDJCYWEAKG-UHFFFAOYSA-N 1-bromo-4-[(4-bromophenyl)-phenylphosphoryl]benzene Chemical class C1=CC(Br)=CC=C1P(=O)(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 URGNHDJCYWEAKG-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- UKOVIQFHGOCRSA-UHFFFAOYSA-N [O].C1(=CC=CC=C1)P Chemical compound [O].C1(=CC=CC=C1)P UKOVIQFHGOCRSA-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
- C07F9/65335—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6544—Six-membered rings
- C07F9/6547—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
Present invention discloses one kind multi-functional luminous organic material based on triphenylphosphine oxide and carbazole derivates, the technical program is using carbazole derivates as electron donor unit, triphenylphosphine oxide obtains the luminous organic material of excellent combination property as electron acceptor unit, by different the position of substitution and different substituent group come the optical physics of regulating compound and other performances.Six kinds of compounds have been synthesized by mature Suzuki and Buchwald-Harting coupling reaction, have there is preferable dissolubility in common organic solvent；Occurs the phenomenon that increasing with the property of solvent pole, the red shift of the emission spectra of compound to some extent；With the variation of solvent strength, the chromaticity coordinate of part of compounds has successively been transitioned into white light from blue light.The present invention realizes the regulation of compound spectra by cleverly MOLECULE DESIGN, and compound all has good thermodynamic stability and dissolubility, can be applied to the preparation of the electroluminescent device of solution processing.
Description
Technical field
The present invention relates to one kind multi-functional luminous organic material based on triphenylphosphine oxide and carbazole derivates, belongs to photoelectricity
Functional organic material technical field.
Background technique
The origin of Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED) will trace back to last century
The eighties, U.S.'s Kodak Company in 1987 have obtained the OLED with low-voltage and high brightness using organic semiconducting materials, have made
Obtain the visual field that organic luminescent device gradually enters into the public.Hereafter, related fields also becomes the hot spot of all circles' research.Organic light emission
The material component part indispensable as OLED, characteristic have far-reaching influence for OLED device performance.By long-term
The type of research and development, luminescent material is more and more diversified, wherein triphenylphosphine oxide due to its special structure and properties and
It attracts attention.Due to phosphorus atoms self property, five covalent bonds can be formed, so phosphine oxygen functional group is easily and other groups
Connection is formed using it as the derivative of core.Since oxygen atom has very strong electronegativity, this just makes the polarization of phosphine oxide structure height
And there is by force electron-withdrawing.The triphenylphosphine oxide unit that electrophilic phosphine oxygen groups connection phenyl ring is formed also has stronger suction
Electro and triphenylphosphine oxide has outstanding electron transport ability, high triplet and unique tetrahedron space structure
Type；And carbazole derivates group possesses outstanding luminous efficiency, wide energy gap, good carrier transmission performance and is easy to carry out
The features such as modification of molecular structure.
Based on this, by access have stronger electron characteristic carbazole derivates group, can be formed molecular structure compared with
The D-A type compound of distortion, and by different substituent group and different the position of substitution come the electronics knot of Effective Regulation compound
Structure, and then control the optical physics and other characteristics of compound.
Summary of the invention
It is an object of the invention to: in view of the defects existing in the prior art, using triphenylphosphine oxide as electron-withdrawing group,
The multi-functional luminous organic material of different topology structure that carbazole derivates are processed as electron donating group synthesis of soluble liquid.And it studies
The influence of different electron donating groups and the position of substitution to material emission performance.
It is a kind of based on triphenylphosphine oxide and carbazole derivates that the purpose of the invention will be achieved through the following technical solutions:
Multi-functional luminous organic material, have the following structure Formulas I:
Wherein, L1、L2、L3In the meta position and contraposition connection of phenyl ring；L1、L2、L3For hydrogen atom, ethyl carbazole, phenthazine or
Phenoxazine.
Preferably, structural formula I has chemical structure shown in following general formula J1-J4:
Wherein L is ethyl carbazole, phenthazine or phenoxazine.
Preferably, the L chemical structure in J1-J4 structural formula is one of molecular formula shown in H1-H3:
Preferably, the structure I is selected from any of following compounds M1-M18:
Preferably, the decomposition temperature of the M1-18 compound is 251 DEG C -286 DEG C.
Preferably, maximum emission wavelength range of the M1-M18 compound in toluene solution is 400-460nm.
Preferably, there is Two peak emission phenomenon in the toluene solution of various concentration in M7, M8, M9 and M10 compound
And chromaticity coordinate with the reduction of concentration successively from dark blue light to white light transition.
Preferably, the M1-M28 compound has resolvability in organic solvent, and as the polarity of solvent increases,
There is red shift in fluorescence emission spectrum.
Preferably, M1, M2, M7, M8, M9 and M10 compound all has aggregation-induced emission characteristic.
Preferably, the energy gap of M1, M2, M7, M8, M9 and M10 compound be respectively 3.42eV, 3.40eV, 3.25eV,
3.06eV, 3.27eV and 3.28eV.
The advantages of technical solution of the present invention is mainly reflected in: the technical program is using carbazole derivates as electron donor list
Member, triphenylphosphine oxide is as electron acceptor unit, by different the position of substitution and different substituent group come the light of regulating compound
Physics and other performances, it is desirable to obtain the multi-functional luminous organic material of solution processable type of excellent combination property.Therefore pass through
Mature Suzuki and Buchwald-Harting coupling reaction synthesizes six kinds of compounds of f, this six kinds of compounds are all common
There is preferable dissolubility in organic solvent；Occur increasing with the property of solvent pole to some extent, the transmitting light of compound
The phenomenon that composing red shift；With the variation of solvent strength, the chromaticity coordinate of part of compounds has successively been transitioned into white light from blue light；Six
Kind compound all has aggregation-induced emission effect.Speculate accordingly, possesses compound (the hereafter compound M1- of this class formation
M18) all there is the above characteristic.In conclusion the present invention realizes the regulation of compound spectra by cleverly MOLECULE DESIGN, and
And the compound all has good thermodynamic stability and dissolubility, can be applied to the electroluminescent device of solution processing
Preparation.
Detailed description of the invention
Fig. 1 is the thermomechanical curve of M1, M2, M7, M8, M9 and M10 compound in the present invention, specially the curve graph of DSC.
Fig. 2 is the thermomechanical curve of M1, M2, M7, M8, M9 and M10 compound in the present invention, specially the curve graph of TGA.
Fig. 3 be in the present invention M1, M2, M7, M8, M9 and M10 compound in toluene solution (10-5Mol/L in) it is ultraviolet-can
See absorption spectrum.
Fig. 4 be in the present invention compound respectively in different solvents (10-3Mol/L) toluene (TOL), methylene chloride (DGM),
Tetrahydrofuran (THE), the normalization PL spectrum in ethyl acetate (EA) and n,N-Dimethylformamide (DMF).
Fig. 5 is that normalized compound is in 2- methyltetrahydrofuran solution in the present invention, the antenna effect spectrum of 77k
Figure.
Fig. 6 is normalization PL spectrum of the compound in the toluene solution of various concentration in the present invention.
Fig. 7 is the I/I of compound in the present invention0About fwIt is figure (I0For strong light of the corresponding compound in THF solvent
Degree).
Fig. 8 is cyclic voltammetry curve of the compound in anhydrous acetonitrile in the present invention.
Specific embodiment
The purpose of the present invention, advantage and feature, by by the non-limitative illustration of preferred embodiment below carry out diagram and
It explains.These embodiments are only the prominent examples using technical solution of the present invention, it is all take equivalent replacement or equivalent transformation and
The technical solution of formation, all falls within the scope of protection of present invention.
Present invention discloses one kind multi-functional luminous organic material based on triphenylphosphine oxide and carbazole derivates has such as
Flowering structure Formulas I:
Wherein, L1、L2、L3In the meta position and contraposition connection of phenyl ring；L1、L2、L3For hydrogen atom, ethyl carbazole, phenthazine or
Phenoxazine.
Structural formula I has chemical structure shown in following general formula J1-J4:
Wherein L is ethyl carbazole, phenthazine or phenoxazine.
L chemical structure in J1-J2 structural formula is one of molecular formula shown in H1-H3:
The structure I is selected from any of following compounds M1-M18:
The decomposition temperature of M1, M2, M7, M8, M9 and M10 compound is 251 DEG C -286 DEG C, has good thermostabilization
Property.Maximum emission wavelength range of M1, M2, M7, M8, M9 and M10 compound in toluene solution is 400-480nm.Institute
State M1, M2, M7, M8, M9 and M10 compound has resolvability in organic solvent, and as the polarity of solvent increases, fluorescence
There is red shift in emission spectrum.There is Two peak emission in the toluene solution of various concentration in M7, M8, M9 and M10 compound
Phenomenon and chromaticity coordinate are with the reduction of concentration successively from dark blue light to white light transition.M1, M2, M7, M8, M9 and M10 chemical combination
Object all has aggregation-induced emission characteristic.The energy gap of M1, M2, M7, M8, M9 and M10 compound be respectively 3.42eV,
3.40eV, 3.25eV, 3.06eV, 3.27eV and 3.28eV.
Raw material used in the present embodiment is commercially available compound, does not do any purification processes using preceding, passes through ability
The synthesis of method known to domain, but these embodiments are not intended to limit the present invention.
Embodiment 1:
Bis- (3- bromophenyl) phenyl phosphine oxides: tetrahydrofuran (350mL) is steamed by 1,3- dibromobenzene (14g, 60mmol) and again
Be added in bottle with two necks, under -78 DEG C of nitrogen environment, be added dropwise n-BuLi (1.6M hexane solution, 57mmol,
35.58mL).Reaction is kept two hours at low temperature, and phenylphosphonic dichloride (30mmol, 2.7mL) then is added, and removes low temperature dress
It sets, is stirred overnight.With 15mL methanol quenching reaction, reaction substrate is extracted with dichloromethane, and anhydrous sodium sulfate is dry.Rotary evaporation
Fall all solvents, hydrogen peroxide and each 120mL of methylene chloride is added, continues to be stirred at room temperature overnight.Organic layer saturation food
Salt water is separated and is washed.It is dry, admix silica white.It (petroleum ether: ethyl acetate=3: 1) is obtained by the filtering of column layer
0.69g target product, puts it into refrigerator freezing.(yield: 53%).1H NMR (400MHz, CDCl3, ppm) and δ 7.85-7.78
(d, 2H), 7.72-7.50 (m, 9H) 7.40-7.32 (d, 2H).GC-MS m/z: theoretical value: 436, experiment value: 436.58.
Bis- (4- bromophenyl) phenyl phosphine oxides: tetrahydrofuran (350mL) is steamed by Isosorbide-5-Nitrae-dibromobenzene (14g, 60mmol) and again
Be added in bottle with two necks, under -78 DEG C of nitrogen environment, be added dropwise n-BuLi (1.6M hexane solution, 57mmol,
35.58mL).Reaction is kept two hours at low temperature, and phenylphosphonic dichloride (30mmol, 2.7mL) then is added, and removes low temperature dress
It sets, is stirred overnight.With 15mL methanol quenching reaction, reaction substrate is extracted with dichloromethane, and anhydrous sodium sulfate is dry.Rotary evaporation
Fall all solvents, hydrogen peroxide and each 120mL of methylene chloride is added, continues to be stirred at room temperature overnight.Organic layer saturation food
Salt water is separated and is washed.It is dry, admix silica white.It (petroleum ether: ethyl acetate=3: 1) is obtained by the filtering of column layer
0.72g target product, puts it into refrigerator freezing.(yield: 55%).1H NMR (400MHz, CDCl3, ppm) and δ 7.65-7.56
(m, 6H), 7.56-7.45 (m, 7H).GC-MS m/z: theoretical value: 436, experiment value: 436.58.
M1: will be bis- (3- bromophenyl) phenyl phosphine oxide (5mmol, 2.18g), 3- boric acid -9- ethyl -9H- carbazole (5mmol,
1.195g) and reaction kettle, sealing is added in catalyst.It vacuumizes, inflated with nitrogen is three times.The potassium carbonate and toluene solution of deoxygenation is added,
90 DEG C of reactions are overnight.After reaction, substrate is extracted with dichloromethane three times, and revolving removes solvent.(stone is filtered by chromatographic column
Oily ether: ethyl acetate=3: 1) 0.9g yellow solid M-EtCz-Br (yield: 50%) and 0.36g yellow target product M1 is obtained.1H
NMR (400MHz, DMSO, ppm) δ 8.47-8.42 (d, 2H), 8.19-8.07 (m, 4H), 8.04-7.96 (d, 2H), 7.83-
7.75 (d, 2H), 7.68-7.51 (m, 13H), 7.43-7.36 (d, 2H), 7.15-7.08 (d, 2H), 4.40-4.30 (d, 2H),
1.25-1.18 (t, 3H).GC-MS m/z: theoretical value: 664, experiment value: 664.559.
M2: will be bis- (4- bromophenyl) phenyl phosphine oxide (5mmol, 2.18g), 3- boric acid -9- ethyl -9H- carbazole (5mmol,
1.195g) and reaction kettle, sealing is added in catalyst.It vacuumizes, inflated with nitrogen (is heated when pumping with hair dryer) three times.Deoxygenation is added
Potassium carbonate and toluene solution, 90 ° reaction overnight.After reaction, substrate is extracted with dichloromethane three times, and revolving removes molten
Agent.By chromatographic column filtering (petroleum ether: ethyl acetate=3: 1) obtain 0.9g yellow solid P-EtCz-Br (yield: 50%) and
0.36g yellow target product M2.1HNMR (400MHz, DMSO, ppm) δ 8.60-8.53 (d, 2H), 8.27-8.20 (d, 2H),
8.02-7.93 (m, 4H), 7.85-7.56 (m, 15H), 7.50-7.41 (d, 2H), 7.26-7.16 (d, 2H), 4.55-4.30 (d,
2H), 1.37-1.26 (t, 3H).GC-MS m/z: theoretical value: 664, experiment value: 663.558.
M7: by M-EtCz-Br (1mmol, 0.55g), phenthazine (1.1mmol, 0.218g) and potassium tert-butoxide (1.1mmol,
It 0.123g) is placed in reaction kettle, vacuumizes, inflated with nitrogen is primary；Reaction kettle is coated with masking foil again, catalysis is taken under the conditions of being protected from light
Agent is immediately placed in reaction kettle, and sealing, vacuum nitrogen gas is three times.The steamed toluene solution of 100mL weight is measured, is injected in
Reaction kettle.It is reacted for 24 hours at 110 DEG C.After reaction, substrate is extracted with dichloromethane three times, and revolving removes solvent.Pass through layer
Analysis column filtering (petroleum ether: ethyl acetate=3: 1) obtains 0.3g yellow-brown solid target product (yield: 50%).1HNMR
(400MHz, DMSO, ppm) δ 8.50-8.3 (s, 1H), 8.23-8.13 (s, 1H), 8.06-7.94 (d, 2H), 7.80-7.37 (m,
17H), 7.20-7.12 (s, 1H), 7.09-7.03 (s, 1H), 6.89-6.77 (t, 3H), 6.34-6.27 (d, 2H), 4.40-
4.30 (d, 2H), 1.25-1.18 (t, 3H).GC-MS m/z: theoretical value: 668, experiment value: 668.470.
M8: by M-EtCz-Br (0.7mmol, 0.385g), phenoxazine (0.8mol, 0.146g) and potassium tert-butoxide
(0.8mol, 0.09g) is placed in reaction kettle, is vacuumized, and inflated with nitrogen is primary；Reaction kettle is coated with masking foil again, is protected from light condition
Under take catalyst to be immediately placed in reaction kettle, seal, vacuum nitrogen gas is three times.The steamed toluene solution of 100mL weight is measured, it will
It is injected in reaction kettle.It is reacted for 24 hours at 110 DEG C.After reaction, substrate is extracted with dichloromethane three times, and revolving removes molten
Agent.By chromatographic column filtering (petroleum ether: ethyl acetate=3: 1) obtain 0.33g yellow-brown solid target product (yield:
72%).1H NMR (400MHz, DMSO, ppm) δ 8.46-8.38 (s, 1H), 8.23-8.13 (s, 1H), 8.06-7.94 (d,
2H), 7.91-7.53 (m, 15H), 7.22-7.16 (s, 1H), 6.73-6.50 (m, 6H), 5.88-5.80 (d, 2H), 4.40-
4.30 (d, 2H), 1.25-1.18 (t, 3H).GC-MS m/z: theoretical value: 652, experiment value: 651.279.
M9: by P-EtCz-Br (0.7mmol, 0.385g), phenthazine (0.8mmol, 0.195g) and potassium tert-butoxide
(0.8mol, 0.09g) is placed in reaction kettle, is vacuumized, and inflated with nitrogen is primary；Reaction kettle is coated with masking foil again, is protected from light condition
Under take catalyst to be immediately placed in reaction kettle, seal, vacuum nitrogen gas is three times.The steamed toluene solution of 100mL weight is measured, it will
It is injected in reaction kettle.It is reacted for 24 hours at 110 DEG C.After reaction, substrate is extracted with dichloromethane three times, and revolving removes molten
Agent.(petroleum ether: ethyl acetate=3: 0.3g yellow-brown solid target product (yield: 65%) 1) is obtained by chromatographic column filtering.1H
NMR (400MHz, DMSO, ppm) δ 8.58-8.49 (s, 1H), 8.27-8.17 (s, 1H), 7.99-7.87 (d, 2H), 7.82-
7.51 (m, 12H), 7.50-7.40 (s, 1H), 7.37-7.25 (m, 4H), 7.24-7.14 (t, 3H), 7.13-7.04 (d, 2H),
6.96-6.86 (d, 2H), 4.51-4.31 (d, 2H), 1.34-1.26 (t, 3H).GC-MS m/z: theoretical value: 668, experiment value:
668.528。
M10: by P-EtCz-Br (1mmol, 0.55g), phenoxazine (1.1mmol, 0.2g) and potassium tert-butoxide (1.1mol,
It 0.123g) is placed in reaction kettle, vacuumizes, inflated with nitrogen is primary；Reaction kettle is coated with masking foil again, catalysis is taken under the conditions of being protected from light
Agent is immediately placed in reaction kettle, and sealing, vacuum nitrogen gas is three times.The steamed toluene solution of 100mL weight is measured, is injected in
Reaction kettle.It is reacted for 24 hours at 110 DEG C.After reaction, substrate is extracted with dichloromethane three times, and revolving removes solvent.Pass through layer
Analysis column filtering (petroleum ether: ethyl acetate=3: 1) obtains 0.41g yellow-brown solid target product (yield: 63%).1H NMR
(400MHz, DMSO, ppm) δ 8.61-8.51 (s, 1H), 8.29-8.17 (s, 1H), 8.03-7.88 (d, 2H), 8.03-7.52
(m, 16H), 7.49-7.38 (s, 1H), 7.25-7.12 (s, 1H), 6.79-6.56 (m, 6H), 5.98-5.85 (d, 2H), 4.51-
4.33 (d, 2H), 1.33-1.25 (t, 3H).GC-MS m/z: theoretical value: 652, experiment value: 652.539.
As a result it characterizes:
Hot property
Fig. 1 and Fig. 2 is respectively DSC the and TGA curve of compound M1, M2, M7, M8, M9 and M10, is tested, is obtained by DSC
To the glass transition temperature (T of six kinds of compoundsg) it is respectively 98 DEG C, 92 DEG C, 142 DEG C, 153 DEG C, 90 DEG C and 98 DEG C.
Fig. 2 is the TGA curve of M1, M2, M7, M8, M9 and M10, equally, point of six kinds of compounds in 5% mass loss
Solve temperature (Td) it is respectively 268 DEG C, 251 DEG C, 263 DEG C, 278 DEG C, 284 DEG C and 286 DEG C；The result shows that newly synthesized four kinds of changes
Closing object has preferable thermal stability.
Photophysical property
Fig. 3 illustrates the Photophysical Behaviors of compound M1, M2, M7, M8, M9 and M10, and it is molten in toluene to test them respectively
UV absorption and fluorescent emission map in liquid (10-6mol/L).Absorption peak there are two six kinds of compounds are equal in toluene solution,
The absorption peak of 290nm or so is the n- π * transition of carbazole derivates group；And the corresponding absorption peak of 310-350nm wavelength is electronics
Intramolecular electron transfer (IntramolecularCharge Transfer, the ICT) peak value of donor to electron acceptor.According to six
Ultra-violet absorption spectrum of the kind compound in toluene solution, can calculate the energy gap of compound M1, M2, M7, M8, M9 and M10
Respectively 3.42,3.40,3.25,3.06,3.27 and 3.28eV.It can be seen that, part of compounds has from fluorescent emission map
Apparent Two peak emission phenomenon, this may be related with the polarity of solvent and concentration.
Fig. 4 is fluorescent emission map of the compound in opposed polarity solvent, and Fig. 4 is to have surveyed M1 in different solvents
(10-3mol/L) toluene (TOL), methylene chloride (DGM), tetrahydrofuran (THF), ethyl acetate (EA) and N, N- dimethyl formyl
Emission spectrum in amine (DMF), such as Fig. 4 are arrived from the lesser toluene solution of polarity (absorption peak 450nm, half-peak breadth 79nm)
The biggish n,N-Dimethylformamide solution of polarity (absorption peak 488nm, half-peak breadth 86nm), the emission spectrum of compound M1
There is apparent red shift；Other five kinds of compounds also have similar solvatochromic phenomenon.This is because compound is spread out with carbazole
Biology is donor monomer, and triphenylphosphine oxide constitutes D-A type molecule by receptor unit, they have Intramolecular electron transfer spy
Property.With the increase of solution polarity, vibration relaxation enhancing, excited level reduces, therefore wavelength becomes larger, and intuitively shows as wavelength
There is red shift with the increase of solution polarity.
Fig. 5 is six kinds of compounds phosphorescence spectrum figure at low temperature, in particular to compound in methyltetrahydrofuran solution
In antenna effect spectrum, according to energy peak position at the arrow of spectrogram calculate separately out available compound M1, M2,
The triplet of M7, M8, M9 and M10 are respectively 2.71eV, 2.67eV, 2.51,2.74eV, 2.53 and 2.74eV.Compare and
Speech, four kinds of compounds after the triplet of both compounds of M1 and M2 is higher than, this may be the confession due to ethyl carbazole
Electronic capability is better than phenthazine or phenoxazine.
Fluorescent emission map and compound of six kinds of compounds under various concentration have been surveyed respectively in various concentration solvent
In chromaticity coordinate.Fig. 6 is fluorescent emission map of the compound in various concentration toluene solution, as shown in fig. 6, with concentration
Successively decrease, the fluorescent emission map of compound M10 becomes Two peak emission from unimodal, consistent with ultraviolet and solvation result above；
And also there is variation in its chromaticity coordinate with the change of solvent strength.
When solvent strength is 10-2mol/L, the chromaticity coordinate of compound is (0.18,0.29), and day blue emission is presented；
And when solution concentration is decremented to 10-6mol/L, the chromaticity coordinate of compound is (0.29,0.25), close to white light emission.Thus
As it can be seen that solvent strength has a certain impact for the fluorescent emission of compound.
In order to determine whether compound has AIE characteristic, it is dissolved into good solvent (tetrahydrofuran) and poor solvent
In the mixed solution of (water), fluorescent emission intensity of the compound at different moisture content (fw=0%~90%) is had detected.
Fig. 7 is the tendency chart of I/I0 (I0 is emissive porwer of the compound in pure tetrahydrofuran solution) and water content (fw).Such as Fig. 7 institute
Show, when water content is 0%~60%, the fluorescent emission intensity of compound is very weak；And when water content increases to 80%, it is glimmering
Increasing sharply occurs in light emitting intensity, and when water content further increases, the fluorescent emission intensity of compound occurs a degree of
Weaken, this may be since water content is completely dissolved compound not very much, and luminous intensity has reduction by a small margin.Always
It, with being incremented by for water content, the phenomenon that all compounds all show fluorescence enhancement, this result shows that, this six kinds of chemical combination
Object all has AIE characteristic.
Electrochemical properties
The chemical property of six kinds of compounds M1, M2, M7, M8, M9 and M10, Fig. 8 are determined by cyclic voltammetry (CV)
The cyclic voltammetry curve for being compound in anhydrous acetonitrile.Fig. 8 illustrates six kinds of compounds in anhydrous acetonitrile solvent
Redox curve.By the initial oxidation potential and reduction potential of compound, the HOMO energy level of six kinds of compounds can be calculated
It is respectively as follows: -5.54eV, -5.58eV, -5.29V, -5.31eV, -5.50V and -5.29eV.Lumo energy is respectively as follows :-
2.02eV, -2.07eV, -2.07eV, -2.10eV, -2.13eV and -2.17eV.
This invention address that synthesizing a kind of multi-functional luminous organic material based on triphenylphosphine oxide and carbazole derivates.By
In phosphorus atoms self property, five covalent bonds can be formed, thus phosphine oxygen functional group easily connected with other groups to be formed with
It is the derivative of core.Since oxygen atom has very strong electronegativity, this just makes the polarization of phosphine oxide structure height and has strong
It is electron-withdrawing.The triphenylphosphine oxide unit that electrophilic phosphine oxygen groups connection phenyl ring is formed also has stronger electron-withdrawing and three
Phenylphosphine oxygen has outstanding electron transport ability, high triplet and unique tetrahedron steric configuration；And carbazole spreads out
Biological group possesses outstanding luminous efficiency, wide energy gap, good carrier transmission performance and is easy to carry out molecular structure
The features such as modification.Based on this, the technical program using carbazole derivates as electron donor unit, triphenylphosphine oxide as electronics by
Body unit has obtained the organic fluorescence small molecule with AIE characteristic by reasonable MOLECULE DESIGN.And pass through the position of substitution
Variation with substituent group effectively controls the Photophysical Behaviors of luminescent material, and enriches the synthesis of existing D-A type luminescent material
System, obtains the multi-functional luminous organic material of the solution processable of excellent combination property, thus by mature Suzuki and
Buchwald-Harting coupling reaction has synthesized six kinds of compounds of M1, M2, M7, M8, M9 and M10, this six kinds of compounds all exist
There is preferable dissolubility in common organic solvent；Occur increasing with the polarity of solvent to some extent, compound
The phenomenon that red shift of the emission spectra；With the variation of solvent strength, the chromaticity coordinate of part of compounds is successively transitioned into from blue light
White light；Six kinds of compounds all have aggregation-induced emission effect.
These results suggest that the present invention realizes the regulation of compound spectra, and describedization by cleverly MOLECULE DESIGN
Closing object all has good thermodynamic stability and dissolubility, can be applied to the preparation of the electroluminescent device of solution processing.
Still there are many embodiment, all technical sides formed using equivalents or equivalent transformation by the present invention
Case is within the scope of the present invention.
Claims (10)
1. a kind of multi-functional luminous organic material based on triphenylphosphine oxide and carbazole derivates, it is characterised in that: have as follows
Structural formula I:
Wherein, L1、L2、L3In the meta position and contraposition connection of phenyl ring；L1、L2、L3For hydrogen atom, ethyl carbazole, phenthazine or phenoxazine
Piperazine.
2. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 1,
It is characterized by:
Structural formula I has chemical structure shown in following general formula J1-J4:
Wherein L is ethyl carbazole, phenthazine or phenoxazine.
3. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 2,
It is characterized by: the L chemical structure in J1-J4 structural formula is one of molecular formula shown in H1-H3:
4. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 1,
It is characterized by: the structure I is selected from any of following compounds M1-M18:
5. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 4,
It is characterized by: the decomposition temperature of the M1-18 compound is 251 DEG C -286 DEG C.
6. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 4,
It is characterized by: maximum emission wavelength range of the M1-M18 compound in toluene solution is 400-460nm.
7. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 4,
It is characterized by: there is Two peak emission phenomenon and color in the toluene solution of various concentration in M7, M8, M9 and M10 compound
Reduction of the coordinate with concentration is spent successively from dark blue light to white light transition.
8. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 4,
It is characterized by: the M1-M28 compound has resolvability in organic solvent, and as the polarity of solvent increases, fluorescence
There is red shift in emission spectrum.
9. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 4,
It is characterized by: M1, M2, M7, M8, M9 and M10 compound all has aggregation-induced emission characteristic.
10. multi-functional luminous organic material of the one kind based on triphenylphosphine oxide and carbazole derivates according to claim 9,
It is characterized by: the energy gap of M1, M2, M7, M8, M9 and M10 compound be respectively 3.42eV, 3.40eV, 3.25eV,
3.06eV, 3.27eV and 3.28eV.
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