CN105837629B - The luminescent device of nitrogen-containing heterocycle phosphoric acid and its preparation method and application nitrogen-containing heterocycle phosphoric acid - Google Patents
The luminescent device of nitrogen-containing heterocycle phosphoric acid and its preparation method and application nitrogen-containing heterocycle phosphoric acid Download PDFInfo
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- CN105837629B CN105837629B CN201610124581.9A CN201610124581A CN105837629B CN 105837629 B CN105837629 B CN 105837629B CN 201610124581 A CN201610124581 A CN 201610124581A CN 105837629 B CN105837629 B CN 105837629B
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- phosphoric acid
- nitrogen
- containing heterocycle
- phenyl
- heterocycle phosphoric
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 29
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- -1 pyrimidine radicals Chemical class 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical class 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 10
- 238000005401 electroluminescence Methods 0.000 abstract description 6
- 238000010189 synthetic method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000033228 biological regulation Effects 0.000 abstract description 3
- 150000004696 coordination complex Chemical class 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 238000011105 stabilization Methods 0.000 abstract description 2
- 238000007385 chemical modification Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- MHRSWLYMKOJZKV-UHFFFAOYSA-N C(C=C1)=CC=C1[P]C1=NC=CC=C1 Chemical compound C(C=C1)=CC=C1[P]C1=NC=CC=C1 MHRSWLYMKOJZKV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- HXVQQJLKZNPFAS-UHFFFAOYSA-N OC=1C=C(C=CC1)C(C(=O)O)(C)P=O Chemical compound OC=1C=C(C=CC1)C(C(=O)O)(C)P=O HXVQQJLKZNPFAS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- NAVNIBXODTVAEF-UHFFFAOYSA-N boric acid;1,3-difluorobenzene Chemical compound OB(O)O.FC1=CC=CC(F)=C1 NAVNIBXODTVAEF-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000012374 esterification agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- SYBJZXZBVFWDAO-UHFFFAOYSA-N hydroxymethyl(phenyl)phosphinic acid Chemical class OCP(O)(=O)C1=CC=CC=C1 SYBJZXZBVFWDAO-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- CGNKSELPNJJTSM-UHFFFAOYSA-N phenylphosphonous acid Chemical compound OP(O)C1=CC=CC=C1 CGNKSELPNJJTSM-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- HOJLDGRYURJOJS-UHFFFAOYSA-N phosphoric acid;pyridine Chemical compound OP(O)(O)=O.C1=CC=NC=C1 HOJLDGRYURJOJS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
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- 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
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- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
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- C07F9/02—Phosphorus compounds
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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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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Abstract
Compound the present invention relates to one kind containing azepine cycli phosphate structure can be used as metal ligand and prepare luminous organic material.Compared to the phosphoric acid ligand for being widely studied report, other than this kind of novel azaheterocyclic phosphoric acid ligand that the invention is covered not only has many advantages, such as chemical property stabilization, is easily purified, and due to the introducing of the sub- phosphoric acid coordination structure of forceful electric power, it is capable of the luminescent color of Effective Regulation metal complex.By modifying the molecular structure of azepine ring substituents, the luminous position of complex can be adjusted in blue wavelength range, this provides convenience for the design production of display of organic electroluminescence and lighting source.Meanwhile the synthetic method of a series of new nitrogen-containing heterocycle phosphoric acid that the present invention introduces is simple, yield is higher, and the chemical modification for heterocycle is flexible.
Description
[technical field]
The present invention relates to technical field of organic synthesis, more particularly to a kind of nitrogen-containing heterocycle phosphoric acid and its preparation method and application
The luminescent device of the nitrogen-containing heterocycle phosphoric acid.
[background technique]
Organic phosphoric acid compound is a kind of important industrial chemicals, including phosphenylic acid (PPOA), phenyl-phosphonite
(BPA), diphenylphosphoric acid (DPA), 3- hydroxy phenyl phosphoroso- propionic acid (3-HPP), hydroxymethyl phenyl phosphinic acids (HMPPA) etc.,
With extensive chemical industry purposes.For example, PPOA can be used as the additive of unsaturated polyester (UP), polyurethane resin, them is made to generate resistance
Combustion property；It is added in nylon, the degree of polymerization can be improved；It can be added in lubricating oil as extreme pressure agent；Urging as carboxylic acid and alcohol esterification
Agent；When handling fiber, its flame retarding function can be improved；Also as organic synthesis raw material etc..HMPPA is environment friendly flame retardant, heat
Stability and oxidation stability are high, can prepare inflaming retarding copolymer.In synthesis chemistry, this kind of organic phosphoric acid structure is strong well
Ligand, can form stable phosphorescent complexes with various metals, can be used for preparing good phosphor material, solid state lighting,
Luminous organic material (OLED) etc. has broad application prospects.
[summary of the invention]
The purpose of the present invention is to provide the synthetic methods of a kind of nitrogen-containing heterocycle phosphoric acid, and it is efficient to can be used as assistant ligand preparation
Phosphorescent metal complex, such complex can be used as the centre of luminescence, be applied in organic electroluminescence device.
A kind of nitrogen-containing heterocycle phosphoric acid isAzacyclo-For substituted or non-substituted pyridyl group, pyrimidine radicals, pyrrole
Any one in piperazine base, imidazole radicals, triazol radical or triazine radical, R are substituted or non-substituted phenyl, pyridyl group, pyrimidine radicals
Or any one in triazine radical, the phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, imidazole radicals, triazol radical or triazine radical
Any position is replaced by the halogenated alkyl of halogen and/or C1-C6, and the quantity of substituent group is 0-4 on the phenyl；On the pyridyl group
The quantity of substituent group is 0-3, and substituent group quantity is 0-2 on the pyrimidine radicals.
Preferably, the halogen is any one in F, Cl, Br, I, and the halogenated alkyl is the substitution or more of single halogen
The halogenated alkyl for the C1-C6 that a identical or different halogen replaces.
Preferably, the azacyclo- is selected from:In
Any one.
One of preferably, the nitrogen-containing heterocycle phosphoric acid, have the following structure:
The present invention also provides a kind of preparation method of nitrogen-containing heterocycle phosphoric acid, nitrogen-containing heterocycle compound, n-BuLi and phenyl
Phosphorus dichloride reacts 24 hours in tetrahydrofuran, sodium hydrate aqueous solution is added after being passed through ozone, dilute hydrochloric acid, which neutralizes, to be produced
Object.
The present invention also provides a kind of luminescent devices using the nitrogen-containing heterocycle phosphoric acid comprising substrate, anode, hole pass
Defeated layer, organic luminous layer, electron transfer layer and cathode, the substrate are glass, and anode is indium tin oxygen, and cavitation layer uses TAPC material
Material, electron transfer layer are prepared using TmPyPB material.
Other than nitrogen-containing heterocycle phosphoric acid ligand of the present invention not only has many advantages, such as chemical property stabilization, is easily purified, and due to strong
The luminescent color of Effective Regulation metal complex is capable of in the introducing of electronics phosphoric acid coordination structure.By replacing on modification azacyclo-
The molecular structure of base can adjust the luminous position of complex in blue wavelength range, this is display of organic electroluminescence
And the design production of lighting source is provided convenience.Meanwhile synthetic method is simple, yield is higher, repairs for the chemistry of heterocycle
Decorations are flexible.
[Detailed description of the invention]
The complex of iridium Ir1-001 that Fig. 1 is phosphoric acid P-001 provided by the invention as assistant ligand and synthesizes is in room temperature condition
Under ultraviolet-visible absorption spectroscopy and photoluminescence spectra；
[specific embodiment]
The present invention is described in further detail with reference to the accompanying drawings and examples.Term as used in the present invention, unless
It is otherwise noted, the general meaning usually managed with those of ordinary skill in the art.
Nitrogen-containing heterocycle phosphoric acid of the invention has all used 2- bromopyridine, phenyl dichloro phosphorus etc. in the synthesis process, synthesis
Method is similar.Nitrogen-containing heterocycle compound, n-BuLi and phenyl dichloro phosphorus react 24 hours in tetrahydrofuran, are passed through ozone
After sodium hydrate aqueous solution is added, dilute hydrochloric acid neutralizes to obtain product.Below with a wherein embodiment, complex phosphoric acid P-001 is
Example illustrates the content of present invention, will be helpful to further understand the present invention by following embodiments, but do not limit of the invention
Content.
The synthetic method of phosphoric acid P-001 and the synthetic method of complex of iridium Ir1-001
2- bromopyridine (2.52g, 16mmol), n-BuLi (6.4mL, 2.5M, 16mmol) and phenyl dichloro phosphorus
(1.44g, 8mmol) is dissolved in 100mL tetrahydrofuran, and 0 degree is reacted 24 hours, cooling, and water, organic layer evaporating column chromatography is added
Obtain phenylpyridyl phosphorus (0.84g, yield 40%).Phenylpyridyl phosphorus (0.84g, 3mmol) is passed through ozone (1atm), one
Sodium hydrate aqueous solution (6N) is added after hour, continues to stir 10h.Dilute hydrochloric acid (1N) is added and is neutralized to pH 7, filters white
Solid P-001 (0.72g, yield: 90%).1H NMR(400MHz,D2O) δ 8.38 (d, J=4.8Hz, 1H), 7.87-7.71 (m,
2H),7.66–7.52(m,2H),7.43–7.26(m,4H).31P NMR(162MHz,D2O)δ19.42(s).ESI-MS:[M]
calcd for C11H9NNaO2P,241.03；With wherein another embodiment, complex phosphoric acid below found [M+H] 242.20.
It is illustrated for Ir1-001.
The synthetic method of complex Ir1-001
2- bromopyridine (4.17g, 26.39mmol), 2,4 difluorobenzene boric acid (5.00g, 31.66mmol), four triphenyl phosphorus
Palladium (0.91g, 0.79mmol) and sodium carbonate (6.36g, 60.00mmol) are dissolved in 100mL tetrahydrofuran, and 65 DEG C of reactions 24 are small
When, it is cooling, water is added and methylene chloride, organic layer evaporating column chromatograph to obtain main ligand (3.84g, yield 76.18%).Master is matched
Body (2.50g, 13.08mmol) and iridous chloride (2.30g, 6.23mmol) are dissolved in 15mL ethoxy ethanol, and 130 DEG C of mixture
12h is reacted, pyridine phosphoric acid (2.72g, 12.46mmol) and sodium carbonate (3.30g, 31.15mmol) is then added, continues 130 DEG C
Reaction is for 24 hours.System is cooling, and water and methylene chloride is added, and organic layer evaporating column chromatographs to obtain yellow solid Ir1-001 (1.06g, production
Rate: 21.5%).
1H NMR(400MHz,CDCl3, δ): 9.66 (d, J=5.5Hz, 1H), 8.38 (d, J=8.8Hz, 1H), 8.23 (d,
J=8.4Hz, 1H), 7.91 (t, J=5.8Hz, 1H), 7.81-7.73 (m, 4H), 7.42-7.31 (m, 5H), 7.23 (dd, J=
7.2,5.7Hz, 1H), 7.15 (td, J=7.5,3.0Hz, 2H), 6.79 (t, J=6.2Hz, 1H), 6.53-6.39 (m, 2H),
5.76 (dd, J=8.8,2.2Hz, 1H), 5.61 (dd, J=8.7,2.2Hz, 1H)31P NMR(400MHz,CDCl3,δ):
34.31ppm(s).EI,[M]calcd for C33H21F4IrN3O2P,790.72；found 790.00.
The preparation of organic electroluminescence device
For preparing organic electroluminescence device as luminescent material using Ir1-001 below, illustrate organic electroluminescence of the present invention
The preparation of luminescent device.
OLEDs device includes: substrate, anode, hole transmission layer, organic luminous layer, electron transfer layer and cathode.
Substrate is glass in element manufacturing of the invention, and anode material is indium tin oxygen (ITO)；Hole transmission layer uses 4,
[N, N- bis- (4- aminomethyl phenyl) aniline (TAPC), electron transport layer materials use 3,3'- (5'- (3- (pyridine-to 4'- cyclohexyl two
3- yl) phenyl)-[1,1':3', 1 "-triphenyl] -3,3 "-diyls) two pyridines (TmPyPB), with a thickness of 60nm, evaporation rate is
0.05nm/s；Cathode uses LiF/Al, and LiF is with a thickness of 1nm, and evaporation rate 0.01nm/s, Al are with a thickness of 100nm, vapor deposition speed
Rate is 0.2nm/s.Organic luminous layer uses doped structure, and material of main part is with 1,3- bis- (9H- carbazole -9- base) benzene (mCP), institute
The luminescent material of selection is Ir1-001.With a thickness of 40nm, evaporation rate 0.05nm/s, Ir1-001 mass fraction 8%.
Different materials structure in the present invention is as follows:
Using azepine cycli phosphate as the second cyclic metal complexes can effective synthesizing high lumineseent performance, different colours match
Object is closed, and shows good device performance, showing this kind of material in the fields such as display and illumination has practical application value.
Such phosphor material provided by the invention can be used as the emission layer that the centre of luminescence is applied to phosphorescent OLED s, by setting
Ligand or complex structure are counted, and is modified by the chemical substituents to the ligand, invention achieves regulations to cooperate
The purpose of object luminescent color.
Above-described is only embodiments of the present invention, it should be noted here that for those of ordinary skill in the art
For, without departing from the concept of the premise of the invention, improvement can also be made, but these belong to protection model of the invention
It encloses.
Claims (4)
1. a kind of nitrogen-containing heterocycle phosphoric acid, which is characterized in that the structure of the nitrogen-containing heterocycle phosphoric acid isAzacyclo-
For any one in substituted or non-substituted pyrimidine radicals, pyrazinyl, imidazole radicals, triazol radical or triazine radical, R is substitution or non-
Any one in substituted phenyl, pyridyl group, pyrimidine radicals or triazine radical, the phenyl, pyridyl group, pyrimidine radicals, pyrazinyl, miaow
Any position of oxazolyl, triazol radical or triazine radical is replaced by the halogenated alkyl of halogen and/or C1-C6, substituent group on the phenyl
Quantity be 0-4；The quantity of substituent group is 0-3 on the pyridyl group, and substituent group quantity is 0-2 on the pyrimidine radicals.
2. nitrogen-containing heterocycle phosphoric acid as described in claim 1, which is characterized in that the azacyclo- is selected from:In any one.
3. nitrogen-containing heterocycle phosphoric acid according to claim 1, which is characterized in that the nitrogen-containing heterocycle phosphoric acid has the following structure
One of:
4. a kind of method for preparing nitrogen-containing heterocycle phosphoric acid as described in any one of claims 1 to 3, which is characterized in that nitrogen-containing hetero
Cycle compound, n-BuLi and phenyl dichloro phosphorus react 24 hours in tetrahydrofuran, and sodium hydroxide is added after being passed through ozone
Aqueous solution, dilute hydrochloric acid neutralize to obtain product.
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| Title |
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| NEW CYCLOTRIPHOSPHAZENES WITH P-C BONDED ARYL OR HETEROARYL SUBSTITUENTS;TAILLEFER MARC，et al.;《Phosphorus Research Bulletin》;19991231;第10卷;第696-701页 |
| 新型铱配合物的合成和电致发光性能研究;朱玉成;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20111015;第B014-108页 |
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