CN110872329A - Iridium complex and preparation method and application thereof - Google Patents
Iridium complex and preparation method and application thereof Download PDFInfo
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- CN110872329A CN110872329A CN201911060346.XA CN201911060346A CN110872329A CN 110872329 A CN110872329 A CN 110872329A CN 201911060346 A CN201911060346 A CN 201911060346A CN 110872329 A CN110872329 A CN 110872329A
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 100
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 238000010668 complexation reaction Methods 0.000 title description 2
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 22
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001555 benzenes Chemical class 0.000 claims abstract description 17
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 17
- 150000003222 pyridines Chemical class 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 11
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims abstract description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 9
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 125000004306 triazinyl group Chemical group 0.000 claims abstract description 9
- 150000001298 alcohols Chemical class 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 8
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 8
- 150000002790 naphthalenes Chemical class 0.000 claims abstract description 7
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims abstract description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 6
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims abstract 3
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims abstract 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 17
- -1 iridium halides Chemical class 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000003556 thioamides Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 150000001716 carbazoles Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 15
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 238000000859 sublimation Methods 0.000 abstract description 9
- 230000008022 sublimation Effects 0.000 abstract description 9
- 238000000746 purification Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract 1
- 239000000463 material Substances 0.000 description 38
- 101150115956 slc25a26 gene Proteins 0.000 description 15
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 150000002990 phenothiazines Chemical class 0.000 description 5
- 150000002991 phenoxazines Chemical class 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GVPOXQWXNHAESS-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]isoquinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC2=CC=CC=C12 GVPOXQWXNHAESS-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical class N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract
The invention discloses an iridium complex and a preparation method and application thereof. The iridium complex has the following structure:
wherein the C-segment coordinating group is selected from: phenyl, pyridyl, thienyl, pyrimidinyl; the N-segment coordinating group is selected from: pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, or pteridinyl; r1Selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives, naphthalene derivatives; r2Selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboAn quinoline derivative, a 9, 10-dihydroacridine derivative, a phenoxazine derivative, a phenothiazine derivative and an azole derivative. The iridium complex has the characteristics of high carrier transport capacity, simple synthesis, stable chemical property and easy sublimation and purification.
Description
Technical Field
The invention relates to the technical field of luminescent devices, in particular to an iridium complex and a preparation method and application thereof.
Background
Under the large background of increasing global energy demand and great ecological environment worries, governments of various countries continuously and vigorously develop sustainable energy-saving technologies and industries based on high technology. An Organic Light-emitting Diode (OLED), also called an Organic Light-emitting Diode, is a device for converting electric energy into Light energy by applying a voltage thereto. Since the Duncuo cloud of Kodak corporation published the OLED with low voltage starting, high efficiency and high brightness, small molecule organic thin film double-layer structure in 1987, the research of electroluminescent materials and devices has attracted great interest in the world science and technology field and the industry. The OLEDs are flat panel display technologies with low power consumption, wide viewing angle, large area, and soft screen implementation, and are widely considered to be capable of replacing displays such as liquid crystal LCDs and inorganic LEDs, and can be used for ideal display screens of mobile phones and color tvs, and show attractive prospects in solid state lighting and flat panel display.
The OLED device mainly comprises a transparent anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode. Wherein the properties of the light emitting material in the light emitting layer are of critical importance. In a metal complex luminescent system, electrons and holes are compounded to generate excitons, the ratio of singlet excitons to triplet excitons is 1:3, the singlet excitons are converted into the triplet excitons through intersystem crossing due to a heavy atom effect, and finally phosphorescence is emitted by radiation, so that the quantum efficiency can reach 100%. The phosphorescent iridium Ir (III) complex is the most potential OLED luminescent material due to the advantages of good thermal stability, short excited state life, easy adjustment of luminescent color, 100% internal quantum efficiency and the like.
Currently, the commercial green and red materials are iridium complexes. Cost control is crucial in OLED industrialization. The luminescent material, particularly the iridium complex, is key, if the room-temperature, rapid and efficient synthesis of the complex can be realized and the sublimation rate of the complex is improved, the production cost of the material and the device can be greatly reduced, and the method is very key for promoting the industrialization process of the material and the device. In addition, a quaternary ring structure generated by the auxiliary ligand and the iridium atom is not reported. A more serious problem commonly exists in the current devices: the hole mobility of the hole layer is much greater than the electron mobility of the electron layer, which can lead to carrier imbalance and reduced device efficiency. Therefore, if the developed iridium complex luminescent material has good carrier transmission capability, the carrier transmission can be balanced, the carrier composite region can be widened, the device efficiency can be improved, and the iridium complex luminescent material has important research significance for improving the performance of the device. In addition, the ease of synthesis, synthesis yield, and sublimation purification yield of the complex for practical materials are critical to reduce the manufacturing costs of materials and devices. Therefore, it is an urgent problem to provide a novel iridium complex luminescent material with simple synthesis, good carrier transport capability, and high synthesis and sublimation yield.
Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an iridium complex, and a preparation method and application thereof, and aims to solve the problem that the existing luminescent material has poor carrier transport capability.
The specific technical scheme of the invention is as follows:
an iridium complex, wherein the iridium complex has a structure as shown below:
wherein the C-segment coordinating group is selected from: phenyl, pyridyl, thienyl, pyrimidinyl;
the N-segment coordinating group is selected from: pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, pteridinyl;
R1selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives, naphthalene derivatives;
R2selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives, and azole derivatives.
The iridium complex, whereinR is1Selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives and naphthalene derivatives which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon groups and halogen elements;
the R is2Selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives and azole derivatives, which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon groups and halogen elements.
The iridium complex, wherein R is1Selected from:
the R is2Selected from:
the iridium complex, wherein the C-segment coordinating group is selected from: phenyl, pyridyl, thienyl and pyrimidyl which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon, halogen elements, cyano, aniline, carbazole and oxadiazole.
The iridium complex, wherein the C-segment coordinating group is selected from:
the iridium complex, wherein the N-segment coordinating group is selected from: pyridyl, pyrimidyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolyl, isoquinolyl, quinazolinyl or pteridinyl substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon group and halogen elements respectively.
The iridium complex, wherein the N-segment coordinating group is selected from:
the iridium complex, wherein the iridium complex is selected from the group consisting of:
a method for preparing the iridium complex, which comprises the following steps:
providing thioamide derivatives, main ligands containing nitrogen heterocycles, and iridium halides;
mixing the main ligand of the nitrogen-containing heterocycle with the iridium halide to obtain a halogen complex of iridium;
and mixing the iridium halogen complex with the thioamide derivative to obtain the iridium complex.
Use of an iridium complex as described above in the preparation of a light-emitting device.
Has the advantages that: the iridium complex has the characteristics of easy synthesis, good carrier transmission capability, stable chemical property, easy sublimation and purification and higher synthesis yield. Because the iridium complex contains nitrogen heterocycle, carbon-sulfur double bond, carbon-nitrogen double bond and other functional groups, the N-segment coordinated group, the C-segment coordinated group and R1、R2Specific substituent groups such as diphenylamine, carbazole and the like can be introduced, so that the comprehensive photoelectric property of the iridium complex can be effectively regulated and controlled, and convenience is provided for obtaining a high-efficiency organic electroluminescent device and application of the device in the fields of illumination and display.
Drawings
FIG. 1 is an electroluminescence spectrum of an iridium complex Samc 8 used in an organic electroluminescent device.
Fig. 2 is a graph of current density and luminance versus voltage for an organic electroluminescent device using the iridium complex Samc 8 according to the present invention.
Fig. 3 is a graph of the current efficiency and luminance of the iridium complex Samc 8 for an organic electroluminescent device provided by the present invention.
Detailed Description
The invention provides an iridium complex and a preparation method and application thereof, and the invention is further described in detail below in order to make the purpose, technical scheme and effect of the invention clearer and more clear. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Terms used in the present invention generally have meanings commonly understood by those of ordinary skill in the art, unless otherwise specified.
The invention provides an iridium complex, wherein the iridium complex has a structure shown as follows:
wherein the C-block coordinating group is selected from: phenyl, pyridyl, thienyl, pyrimidinyl;
the N-segment coordinating group is selected from: pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, pteridinyl;
R1selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives, naphthalene derivatives;
R2selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives, and azole derivatives.
The invention provides a novel iridium complex containing a nitrogen heterocyclic main ligand and a thioamide derivative auxiliary ligand. The iridium complex comprises nitrogen heterocyclic rings, carbon-sulfur double bonds, carbon-nitrogen double bonds and other functional groups, and meanwhile, the N-segment coordinated group, the C-segment coordinated group and the R1、R2All can introduce specific substituent groups, such as diphenylamine, carbazole and other groups, and can effectively improve the carrier transmission capability of the complex. Moreover, because the radius of the sulfur atom S is larger than that of oxygen, the sulfur atom S is easy to deform, and the electron donating capability of the nitrogen atom N is strong, the coordination capability of the sulfur and nitrogen atoms and the iridium atom is strong, so that the complex-forming reaction is easy to occur, the complex can be obtained by stirring at room temperature, and meanwhile, the complex synthesis and sublimation yield are also obviously improved.
In the structural formula of the iridium complex, the thioamide derivative is an auxiliary ligand of the iridium complex, and the auxiliary ligand comprises R1、R2Two radicals, R1Represents an alkane derivative, an ether derivative, a halogenated hydrocarbon derivative,Ketone derivatives, benzene derivatives, pyridine derivatives, naphthalene derivatives, and the like; r2Represents an alcohol derivative, an amine derivative, a benzene derivative, a pyridine derivative, a pyrimidine derivative, a diphenylamine derivative, a carbazole derivative, a carboline derivative, a 9, 10-dihydroacridine derivative, a phenoxazine derivative, a phenothiazine derivative, an azole derivative, or the like. In addition, R is1、R2Both groups may be substituted or unsubstituted, for example the alkane derivative may be a substituted or unsubstituted alkane derivative, or the alkane derivative includes both substituted and unsubstituted alkane derivatives. The substituted group refers to a group containing a substituent group, and the substituent group can be one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon, halogen elements, cyano, aniline, carbazole and oxadiazole. That is, the R1Selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives and naphthalene derivatives which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon groups and halogen elements; the R is2Selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives and azole derivatives, which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon groups and halogen elements. Further, "C1-C6" means that the number of carbon atoms in the substituent is 1 to 6.
Specifically, the R is1Selected from:
the R is2Selected from:
in the structural formula of the iridium complex of the invention,
the nitrogen heterocyclic main ligand of the iridium complex comprises a C-section coordinated group and an N-section coordinated group. The C-segment coordinating group is selected from: phenyl, pyridyl, thienyl, pyrimidinyl; the N-segment coordinating group is selected from: pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, or pteridinyl. It is noted that the phenyl group may be a substituted or substituted phenyl group, i.e. the phenyl group includes a substituted or substituted phenyl group, and similarly the pyridyl, thienyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, or pteridinyl groups may each be substituted or unsubstituted. The substituted group refers to a group containing a substituent group, and the substituent group can be one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon, halogen elements, cyano, aniline, carbazole and oxadiazole. That is, the C-block coordinating group is selected from: phenyl, pyridyl, thienyl and pyrimidyl which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon, halogen elements, cyano, aniline, carbazole and oxadiazole. The N-segment coordinating group is selected from: pyridyl, pyrimidyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolyl, isoquinolyl, quinazolinyl or pteridinyl substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon group and halogen elements respectively.
Specifically, the group coordinated by the C segment of the iridium complex is selected from:
specifically, the iridium complex, the N-segment coordinating group is selected from:
more specifically, the iridium complex has the following chemical structural formula:
the nitrogen heterocyclic ring, carbon-sulfur double bond, carbon-nitrogen double bond and other groups in the iridium complex molecule are good electron transmission groups, and a hole transmission group such as diphenylamine, carbazole and the like is introduced into thioamide, so that the luminescent material with bipolar property can be synthesized, and the photophysical properties of the luminescent material can be adjusted and controlled, thereby balancing the injection and transmission of holes and electrons, widening the recombination region of current carriers, improving the efficiency of devices and reducing the efficiency roll-off. For example, the device prepared by taking the iridium complex Samc 8 as a luminescence center in the invention has good device performance. And because the radius of the sulfur atom is larger than that of oxygen, the deformability is large, the electron-donating capability of the nitrogen atom is strong, the combination of the sulfur atom and the transition metal iridium is firmer, and the synthesis yield and the vacuum sublimation yield are higher. The synthesis yield of the iridium complex is generally higher than 80%, the vacuum sublimation rate is also higher than 70%, and the synthesis yield is far higher than that (< 70%) and vacuum sublimation rate (< 60%) of most iridium complexes at present, so that the iridium complex is very suitable for industrial production.
Further, the present invention also provides a preparation method of the iridium complex, wherein the preparation method comprises:
providing thioamide derivatives, main ligands containing nitrogen heterocycles, and iridium halides;
mixing the main ligand of the nitrogen-containing heterocycle with the iridium halide to obtain a halogen complex of iridium;
and mixing the iridium halogen complex with the thioamide derivative to obtain the iridium complex.
Specifically, the thioamide derivative of the present invention can be purchased commercially or prepared by the following method: will contain R1Isothiocyanate (R) substituted with substituent1The group definition is as described above), and the same substituted or non-substituted benzene, pyridine, pyrimidine, diphenylamine, bipyridine amine, carbazole, carboline, 9, 10-dihydro acridine, phenoxazine, phenothiazine, azole and the like react for two hours at low temperature in anhydrous THF under the action of n-butyl lithium and under the anaerobic condition to obtain the corresponding lithium salt THF solution of thioacetamide.
The iridium complexes according to the invention can be prepared, for example, by reacting the primary ligand with IrCl3Refluxing in an ethoxyethanol solution for 10 hours in a ratio of 2:1, cooling, adding water to separate out, and filtering to obtain an iridium chloro-bridged complex; then stirring the iridium complex with thioamide derivatives with twice equivalent weight for one hour at room temperature to obtain crude products of the iridium complex, carrying out column chromatography to obtain pure products, and further carrying out sublimation purification under the vacuum condition to obtain the luminescent material meeting the requirements of the preparation device.
The iridium complex has the advantages of simple preparation method, room-temperature reaction for dozens of minutes and high synthesis yield.
A light-emitting device, wherein the light-emitting device comprises the iridium complex as described above.
The invention also provides an application of the iridium complex in preparation of a light-emitting device. Wherein the light emitting device may be an organic electroluminescent device.
The iridium complex can be used for preparing an organic electroluminescent device, for example, the organic electroluminescent device comprises a substrate, an anode, a hole injection material, a hole transport layer, an organic luminescent layer, an electron transport layer, an electron injection material and a cathode. The substrate is glass, the anode is indium tin oxide, the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene HAT-CN, the hole layer is made of 4,4' -cyclohexyl bis [ N, N-bis (4-methylphenyl) aniline TAPC material, the electron transport layer is made of 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene TmPyPB, the electron injection material is LiF, and the cathode is metal Al; the organic light-emitting layer comprises a main material and a light-emitting material, wherein the main material is 4,4' -tri (9-carbazolyl) triphenylamine TCTA, and the light-emitting material is the iridium complex.
The present invention is described in further detail below with reference to specific examples and with reference to the data. It will be understood that this example is intended to illustrate the invention and not to limit the scope of the invention in any way. In the following examples, various procedures and methods not described in detail are conventional methods well known in the art.
Example 1
Preparation of lithium salt THF solution of assistant ligand isopropyl dianilino substituted thioamide
Diphenylamine and n-butyl lithium are reacted in THF solution at low temperature to extract hydrogen, and then reacted with isopropyl isothiocyanate to obtain lithium salt THF solution of isopropyl diphenylamine-thioamide
Directly used for the next step of complex synthesis reaction.
Other lithium thioamides in THF can be prepared using the above method:
example 2 preparation of an Iridium Complex according to the invention
The main ligands 1- (4- (trifluoromethyl) phenyl) isoquinoline and IrCl3Refluxing in an ethoxy ethanol solution for 10 hours in a ratio of 2:1, cooling and filtering to obtain an iridium chloro-bridge complex; then 10mmol (15.43g) of the chloro-bridged complex and 20mmol of lithium salt THF solution of isopropyl-diphenylaminothioamide were stirred in ethylene glycol dimethyl ether solution at room temperature for one hour to obtain crude iridium complex, and column chromatography gave 16.11g of pure Samc 8 (yield: 80%). And further 5g of Samc 8 were placed in a quartz tube at 10-5Heating, sublimating and purifying under the Pa vacuum condition to obtain 3.5g of luminescent material (sublimation rate is 70%) meeting the requirements of preparing devices. The reaction is shown below:
the obtained iridium complex Samc 8 is analyzed by nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum as follows:
1H NMR(400MHz,CDCl3)δ10.01(d,J＝6.42Hz,1H),8.95-8.74(m,3H),8.33-7.97(m,4H),7.90-7.71(m,6H),7.33(t,J＝7.82Hz,4H),7.21(d,J＝7.52Hz,4H),7.14(t,J＝7.39Hz,3H),7.06-7.01(m,1H),6.67(s,1H),6.27(s,1H),4.05(dt,J＝12.73,6.33Hz,1H),0.50(d,J＝6.34Hz,3H),-0.07(d,J＝6.39Hz,3H).
HRMS(ESI)m/z calcd for C48H36F6IrN4S[M+H]:1007.2188,found:1007.2184.
with reference to the above method, different primary ligands are selected:
with the lithium salt of thioamide prepared in example 1 in THF gave the following compound:
example 3 preparation of Iridium Complex Samc 8 organic electroluminescent device
The following description will be made of the preparation of the organic electroluminescent device of the present invention, taking Samc 8 as an example of the preparation of the organic electroluminescent device as the luminescent center of the luminescent layer. The structure of the OLEDs device includes: a substrate, an anode, a hole injection material, a hole transport layer, an organic light emitting layer, an electron transport layer, an electron injection material, and a cathode. The substrate is glass, the anode is indium tin oxide, the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene HAT-CN (5nm), and the evaporation rate is 0.05 nm/s; the hole layer adopts 4,4' -cyclohexyl di [ N, N-di (4-methylphenyl) aniline TAPC material (55nm), and the evaporation rate is 0.05 nm/s; the electron transport layer adopts 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene TmPyPB (55nm), and the evaporation rate is 0.05 nm/s; the electron injection material is LiF (1nm), and the evaporation rate is 0.01 nm/s; the cathode is metal Al (100nm), and the evaporation rate is 0.2 nm/s; the organic light-emitting layer is of a doped structure, the thickness of the organic light-emitting layer is 20nm, the organic light-emitting layer comprises a main material and a light-emitting material, the main material is 4,4' -tris (9-carbazolyl) triphenylamine TCTA, the light-emitting material is an iridium complex, and the mass fraction of the iridium complex is 8 wt%.
Several materials used in the present invention have the following structure:
the invention selects a new iridium complex Samc 8 as a luminescence center to prepare an organic electroluminescent device. Referring to fig. 1, fig. 2 and fig. 3 together, fig. 1 is an electroluminescence spectrum of Samc 8 provided by the present invention for an organic electroluminescent device, and fig. 2 and fig. 3 are graphs of photoelectric properties of Samc 8 provided by the present invention for an organic electroluminescent device. As shown in FIGS. 2 and 3, the organic electroluminescent device had a starting voltage of 3.6V and a maximum current efficiency of 10.5cd/A at 1000cd/m2The current efficiency can still be maintained at 8.6cd/a at luminance, showing a very small efficiency roll-off. Research on photophysical properties shows that the iridium complex luminescent material containing the nitrogen heterocyclic main ligand and the thioamide derivative auxiliary ligand has high device efficiency and has practical application value in the fields of display, illumination and the like.
The iridium complex Samc 1-7 and Samc 9-136 prepared in embodiment 2 of the invention can be prepared into an organic electroluminescent device by adopting the method, and has photoelectric properties similar to or superior to those of Samc 8.
The iridium complex provided by the invention can be used as a luminescent material to be applied to a luminescent layer of OLEDs, and the purpose of regulating and controlling the efficiency of a device is achieved by designing and optimizing the structure of a compound.
The iridium complex is a novel iridium complex containing a quaternary ring structure and taking nitrogen heterocycles as main ligands and thioamide derivatives as auxiliary ligands. Nitrogen heterocycle, carbon sulfur, carbon nitrogen, diphenylamine, carbazole and other groups in the iridium complex molecule are beneficial to improving the carrier transmission capability of the material and regulating and controlling the photophysical properties of the luminescent material, so that the injection and transmission of holes and electrons are balanced, the composite region of the carriers is widened, the device efficiency is improved, and the efficiency roll-off is reduced. The iridium complex has the advantages of novel structure, simple synthesis, stable chemical property, easy sublimation and purification, and excellent device performance, and provides convenience for obtaining an efficient organic electroluminescent device and application thereof in the fields of illumination and display.
While the foregoing is directed to embodiments of the present invention, it will be understood by those skilled in the art that various changes may be made without departing from the spirit and scope of the invention.
Claims (10)
1. An iridium complex, characterized in that the iridium complex has the structure shown below:
wherein the C-segment coordinating group is selected from: phenyl, pyridyl, thienyl, pyrimidinyl;
the N-segment coordinating group is selected from: pyridyl, pyrimidinyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, pteridinyl;
R1selected from: alkane derivatives, ether derivatives, halogenated hydrocarbon derivatives, ketone derivatives, benzene derivatives, pyridine derivatives, naphthalene derivatives;
R2selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives, and azole derivatives.
2. The iridium complex according to claim 1, wherein R is1Selected from: respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon group and halogen element, ether derivative, halogenated hydrocarbon derivative, ketone derivative, benzene derivative, pyridine derivative and naphthalene derivativeAn organism;
the R is2Selected from: alcohol derivatives, amine derivatives, benzene derivatives, pyridine derivatives, pyrimidine derivatives, diphenylamine derivatives, carbazole derivatives, carboline derivatives, 9, 10-dihydroacridine derivatives, phenoxazine derivatives, phenothiazine derivatives and azole derivatives, which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon groups and halogen elements.
3. The iridium complex according to claim 1, wherein R is1Selected from:
the R is2Selected from:
4. the iridium complex according to claim 1, wherein the group coordinated by the C segment is selected from: phenyl, pyridyl, thienyl and pyrimidyl which are respectively substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon, halogen elements, cyano, aniline, carbazole and oxadiazole.
5. The iridium complex according to claim 1, wherein the group coordinated by the C segment is selected from:
6. the iridium complex according to claim 1, wherein the N-block coordinating group is selected from: pyridyl, pyrimidyl, pyridazinyl, triazinyl, thiazolyl, imidazolyl, quinolyl, isoquinolyl, quinazolinyl or pteridinyl substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated hydrocarbon group and halogen elements respectively.
7. The iridium complex according to claim 1, wherein the N-block coordinating group is selected from:
8. the iridium complex according to claim 1, wherein the iridium complex is selected from the group consisting of:
9. a method for producing the iridium complex according to claim 1, comprising:
providing thioamide derivatives, main ligands containing nitrogen heterocycles, and iridium halides;
mixing the main ligand of the nitrogen-containing heterocycle with the iridium halide to obtain a halogen complex of iridium;
and mixing the iridium halogen complex with the thioamide derivative to obtain the iridium complex.
10. Use of an iridium complex as claimed in any one of claims 1 to 8 in the manufacture of a light-emitting device.
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Application publication date: 20200310 |