CN112341500A - Iridium complex with main ligand containing carbazolyl and application - Google Patents
Iridium complex with main ligand containing carbazolyl and application Download PDFInfo
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- CN112341500A CN112341500A CN202011260197.4A CN202011260197A CN112341500A CN 112341500 A CN112341500 A CN 112341500A CN 202011260197 A CN202011260197 A CN 202011260197A CN 112341500 A CN112341500 A CN 112341500A
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 51
- 239000003446 ligand Substances 0.000 title abstract description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 31
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 150000008282 halocarbons Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000011941 photocatalyst Substances 0.000 claims description 2
- 239000000523 sample Substances 0.000 claims description 2
- 125000004149 thio group Chemical group *S* 0.000 claims description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 6
- 230000005281 excited state Effects 0.000 abstract description 5
- 238000005286 illumination Methods 0.000 abstract description 2
- 238000005424 photoluminescence Methods 0.000 abstract description 2
- 238000006862 quantum yield reaction Methods 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 17
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 12
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 150000002503 iridium Chemical class 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000001816 cooling Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 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 3
- 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 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- -1 carbazolyl pyridyl Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000007787 solid Substances 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- VCDOOGZTWDOHEB-UHFFFAOYSA-N 1-bromo-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Br)=CC=C2 VCDOOGZTWDOHEB-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- FDAJIIRNXYZSJQ-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3NC1=2)[Ir] Chemical compound C1(=CC=CC=2C3=CC=CC=C3NC1=2)[Ir] FDAJIIRNXYZSJQ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- VJASJHNHBZQZAK-UHFFFAOYSA-N [N].C1=CC=C2C3=CC=CC=C3NC2=C1 Chemical group [N].C1=CC=C2C3=CC=CC=C3NC2=C1 VJASJHNHBZQZAK-UHFFFAOYSA-N 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B01J35/39—
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention belongs to the technical field of electroluminescent materials, and relates to a novel iridium complex with a main ligand containing carbazolyl, wherein pyridine and derivatives thereof are introduced into a carbazole 1 position in the structure to realize steric hindrance, so that the free relaxation of a benzene ring at the carbazole 9 position is limited, and the non-radiative transition process of molecules can be inhibited. The iridium complex has high photoluminescence quantum yield and short excited state life. The device prepared by the iridium complex has excellent performance, high external quantum efficiency, low starting voltage and low efficiency roll-off, and has potential application value in the field of OLED illumination and display.
Description
Technical Field
The invention relates to the technical field of organic light-emitting devices (OLED), in particular to an iridium complex with a main ligand containing carbazolyl and application thereof as a luminescent material in an organic light-emitting device.
Background
High performance phosphorescent emitters for Organic Light Emitting Diodes (OLEDs) have evolved rapidly over the past few decades. Particularly, oled based on iridium (III) complex attracts people's attention due to its excellent quantum efficiency, short tristate excited state lifetime, excellent coordination ability and adjustable color gamut. This has the advantage that intersystem crossing of singlet excited states is accelerated to strongly emissive triplet excited states due to the strong spin-orbit coupling caused by the heavy iridium atoms, so that singlet and triplet excitons can be trapped simultaneously. Therefore, the Ir (III) complex can break the selection rule of quantum mechanics and theoretically achieve the maximum Internal Quantum Efficiency (IQE) up to 100% compared to 25% of fluorescence oled. However, to meet the needs of display and lighting applications, low turn-on voltages (<2.8V), high External Quantum Efficiency (EQE) and low efficiency roll-off are still necessary.
Carbazole (Cz) derivatives have good hole injection and hole transport properties, and thus are widely used in hole transport and host materials of organic light emitting devices. Of course, complexes of carbazole moieties with high hole mobility in combination with Ir (III) have proven to be a good choice for high efficiency vacuum evaporation OLEDs. The carbazolyl iridium complex structure reported previously is not limited by free relaxation of the group attached to the carbazole nitrogen, which increases the nonradiative transition rate of the molecule and is not favorable for the luminescence process. It is clear that the use of carbazolyl pyridyl Ir (III) complexes as phosphorescent emitters still has the potential to improve device performance.
Disclosure of Invention
Aiming at the defects of the prior art, the invention designs a novel iridium complex with a main ligand containing carbazolyl, applies the material to an organic electroluminescent device and provides a novel high-efficiency luminescent material for an OLED device.
The specific technical scheme of the invention is as follows:
an iridium complex with a main ligand containing carbazolyl has the following structural general formula:
wherein R is1-R4The same or different, are independently selected from the group consisting of hydrogen, deuterium, halogen, halogenated hydrocarbon groups, alkyl groups, cycloalkyl groups, heteroalkyl groups, alkoxy groups, aryloxy groups, amino groups, silyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, deuterated alkyl groups, deuterated cycloalkyl groups, deuterated heteroalkyl groups, deuterated alkoxy groups, deuterated aryloxy groups, deuterated silyl groups, deuterated aryl groups, deuterated heteroaryl groups, acyl groups, carbonyl groups, carboxylic acids, esters, nitriles, thio groups, and combinations thereof;
wherein R is1Independently represent mono-, di-, tri-, tetra-or unsubstituted, R1When it represents di-, tri-or tetra-substitution, each substituent may be the same or different;
wherein R is2Independently represent mono-, di-, tri-, tetra-, penta-or unsubstituted, R2When the substituent is a double substituent, a triple substituent, a tetra substituent or a penta substituent, the substituents are the same or different;
wherein R is3Independently represent mono-, di-, tri-, tetra-or unsubstituted, R3When it represents di-, tri-or tetra-substitution, each substituent may be the same or different;
wherein R is4Independently represent mono-, di-substituted or unsubstituted, and when R4 represents di-substituted, each substituent is the same or different;
wherein R is5-R7The same or different, are independently selected from the group consisting of hydrogen, deuterium, halogenated hydrocarbon groups, alkyl groups, cycloalkyl groups, heteroalkyl groups, alkoxy groups, aryloxy groups, silyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, deuterated alkyl groups, deuterated cycloalkyl groups, deuterated heteroalkyl groups, deuterated alkoxy groups, deuterated aryloxy groups, deuterated silyl groups, deuterated aryl groups, deuterated heteroaryl groups.
Preferably, R1-R4 in the general formula of the iridium complex are the same or different and are selected from hydrogen, halogen, halogenated hydrocarbon groups, alkyl groups, silane groups, deuterium, deuterated alkyl groups, heteroalkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, aryl groups, heteroaryl groups and nitrile groups.
Preferably, R5-R7 in the general formula of the iridium complex are the same or different and are selected from alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, deuterated alkyl, deuterated cycloalkyl, deuterated heteroalkyl, deuterated aryl and deuterated heteroaryl.
Further preferably, in the general formula of the iridium complex, the R1 and R2 are selected from the following groups:
further preferably, in the general formula of the iridium complex, the R3 and R4 are selected from the following groups:
further preferably, in the general formula of the iridium complex, the R5 and R6 are selected from the following groups:
further preferably, in the general formula of the iridium complex, R7 is selected from hydrogen, methyl and deuteromethyl. Preferably, the iridium complex is selected from the following structures:
the iridium complexes of the invention may be prepared by conventional methods, for example by reacting a primary ligand with IrCl3Refluxing in a mixed solution of ethoxyethanol and water for 20 hours in a ratio of 2:1, cooling and filtering to obtain an iridium chloro-bridge complex; then refluxing the iridium chlorine-bridge complex and the beta-diketone auxiliary ligand with the corresponding structure in ethoxyethanol for 24 hours to obtain a crude product of the iridium complex, performing column chromatography to obtain a pure product, and further performing sublimation purification under a vacuum condition to obtain the luminescent material meeting the requirements of the preparation device.
The invention also aims to provide application of the iridium complex as a luminescent material in preparation of organic electroluminescent devices, photocatalysts and optical probes.
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 (ITO), 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 di [ N, N-di (4-methylphenyl) aniline TAPC material, the electron transport layer is made of 1,3, 5-tri [ (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' -tris (9-carbazolyl) triphenylamine TCTA, and the light-emitting material is the iridium complex.
The invention has the beneficial effects that: the iridium complex molecular carbazolyl provided by the invention is beneficial to regulating and controlling the luminescent color of the material, can effectively regulate and control the electron transmission performance, increases the stability of the material, improves the efficiency of a device, and reduces the efficiency roll-off. The iridium complex has high photoluminescence quantum yield and short excited state life. The device prepared by the iridium complex has excellent performance, high external quantum efficiency, low starting voltage and low efficiency roll-off, and has potential application value in the field of OLED illumination and display.
Drawings
FIG. 1 shows thermograms of the iridium complexes AG02, AG26 and AG50 of the present invention (FIG. 1a is a TGA chart, and FIG. 1b is a DSC chart).
Fig. 2 shows several functional material structures used in the fabrication of devices according to the present invention.
Detailed Description
Terms used in the present invention generally have meanings commonly understood by those of ordinary skill in the art, unless otherwise specified. 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 the iridium complex AG02 according to the invention
Preparation of compound L1-1 in the above route: 1-bromo-9H-carbazole (3.00g, 12.24mmol), iodobenzene (3.00g, 14.71mmo), K2CO3(2.53g, 18.36mmol) and DMPU (10 drops) were introduced into a sealed pressure-resistant tube and reacted by heating at 200 ℃ for 18 hours. After cooling to ambient temperature, the mixture was filtered and washed with dichloromethane. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (pure PE eluent) to obtain 3.50g of compound L1-1 (yield 89%).
Preparation of compound L1-2 in the above route: n-BuLi (4.78mL,12.00mmol,2.50M in hexanes) was added dropwise to a solution of L1-1(3.50g,10.90mmol,1.00equiv.) in anhydrous tetrahydrofuran (60mL) to give a pale yellow solution at-78 ℃. After stirring for 1h, trimethyl borate (1.70g,16.35mmol,1.50equiv.) was added. The resulting solution was stirred at-78 ℃ for 40 minutes, allowed to warm to room temperature overnight. Water (60mL) was then added to the solution and the pH adjusted to 7 with dilute HCl. The organic layer was extracted with dichloromethane and concentrated under reduced pressure to give a white solid compound L1-2, which was used in the next reaction without further purification.
Preparation of the master ligand L1 in the above route: pd (dppf) was added under a nitrogen atmosphere2Cl2(0.16g,0.21mmol), 2-bromopyridine (0.55g,3.48mmol), Compound L1-2(1.00g,3.48mmol), K2CO3(0.72g,5.22mmol) was added to a mixed solvent of tetrahydrofuran (20 ml) and water (10 ml), followed by heating under reflux for 12 hours. After the reaction was completed, the reaction mixture was treated with water and extracted with ethyl acetate, and purified by silica gel column chromatography (PE/EA ═ 5/1, v/v) to obtain a white solid ligand with a yield of 40%.1H NMR(400MHz,CDCl3)δ8.27(dd,J＝4.8,0.7Hz,1H),8.24(dd,J＝7.7,1.1Hz,1H),8.18(d,J＝7.7Hz,1H),7.55(dd,J＝7.4,1.1Hz,1H),7.43–7.36(m,2H),7.30(dd,J＝12.2,5.1Hz,2H),7.27(d,J＝1.8Hz,1H),7.25–7.22(m,1H),7.14–7.04(m,6H),6.90(ddd,J＝7.5,4.9,1.0Hz,1H).13C NMR(101MHz,CDCl3)δ157.07,148.63,142.27,139.05,137.80,134.79,128.66,128.52,127.30,126.54,126.14,125.44,125.23,124.50,123.28,120.79,120.50,120.24,120.09,119.97,110.12,77.35,77.03,76.71.HRMS(MALDI-TOF,m/z):[M]+calcd for C23H16N2,320.131；found,321.105.
Preparation of the chloro-bridged compound C1: iridium trichloride (IrCl)3·3H2O, 0.28g,0.78mmol) and L1(0.50g,1.56mmol) were dissolved in 40mL of a mixture of ethylene glycol ethyl ether and water (volume ratio: 3:1) at 130 ℃ under a nitrogen atmosphereAnd refluxed for 20 hours. After cooling, a yellow precipitate was precipitated, filtered, and washed with water, ethanol, and petroleum ether in this order to obtain the product C1 with a yield of 96%.
Preparation of iridium complex AG 02: compound C1(0.09mmol) and the ancillary ligand salt (tBuacacNA) (0.04g,0.19mmol) were dissolved in 2-ethoxyethanol (15mL) and stirred at 110 ℃ under a nitrogen atmosphere for 24 h. After cooling to room temperature, the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (PE/EA ═ 10/1, v/v) to give the product as a yellow solid in 40% yield.1H NMR(500MHz,CD2Cl2)δ8.37(d,J＝4.3Hz,2H),7.94(d,J＝7.1Hz,2H),7.63–7.52(m,6H),7.44(dd,J＝15.6,7.7Hz,8H),7.34(d,J＝6.5Hz,4H),7.25(d,J＝7.7Hz,4H),6.95(s,2H),6.13(d,J＝7.5Hz,2H),5.65(s,1H),1.04(s,18H).13C NMR(126MHz,CD2Cl2)δ194.58,166.13,153.46,147.64,142.45,142.14,139.52,135.09,130.33,129.58,126.86,126.41,125.81,125.43,124.64,122.23,121.57,121.03,119.99,119.84,118.66,110.63,89.82,53.89,53.67,53.46,53.24,53.02,41.09,28.00.HRMS(MALDI-TOF,m/z):[M]+calcd for C57H49IrN4O2,1014.348；found,1014.801。
Example 2 preparation of the iridium complex AG26 according to the invention
Similarly, with reference to the synthetic scheme of example 1 above, an iridium complex AG26 can be prepared, following a certain mass ratio, replacing the corresponding starting materials.1H NMR(500MHz,CD2Cl2)δ8.52(d,J＝5.9Hz,2H),7.96(d,J＝7.6Hz,2H),7.71(s,2H),7.62(d,J＝8.2Hz,4H),7.57–7.49(m,5H),7.36(dd,J＝8.8,5.5Hz,6H),7.28(t,J＝7.3Hz,3H),7.14(d,J＝5.8Hz,2H),6.09(d,J＝7.9Hz,2H),5.68(s,1H),1.04(s,18H).13C NMR(126MHz,CD2Cl2)δ195.19,167.47,154.22,148.29,142.16,141.94,140.02,137.36,137.09,129.96,128.91,126.85,126.57,125.51,125.09,122.01,121.37,121.32,118.85,118.00,115.58,110.79,90.14,53.88,53.67,53.45,53.23,53.02,41.15,27.96.HRMS(MALDI-TOF,m/z):[M]+calcd for C59H47F6IrN4O2,1050.323；found,1050.666。
Example 3 preparation of the iridium complex AG50 according to the invention
Similarly, referring to the synthesis schemes of the above examples 1 and 2, an iridium complex AG50 can be prepared by following a certain mass ratio instead of the corresponding raw material.1H NMR(500MHz,CD2Cl2)δ8.32(d,J＝5.4Hz,2H),7.94(d,J＝7.5Hz,2H),7.70–7.58(m,7H),7.45(d,J＝7.8Hz,6H),7.29(ddd,J＝23.4,15.4,7.3Hz,7H),7.06(d,J＝5.2Hz,2H),6.10(d,J＝7.8Hz,2H),5.66(s,1H),1.06(s,18H),0.25(s,18H).13C NMR(126MHz,CD2Cl2)δ194.39,164.77,153.59,150.11,146.12,142.48,142.21,139.15,130.76,129.64,127.08,126.93,126.19,124.91,124.69,124.62,121.67,121.16,119.65,118.67,110.75,89.75,53.88,53.67,53.45,53.24,53.02,41.13,28.03,-1.69.HRMS(MALDI-TOF,m/z):[M]+calcd for C63H65IrN4O2Si2,1058.424；found,1059.346。
The thermograms of the iridium complexes AG02, AG26 and AG50 are shown in figure 1. (FIG. 1a is a TGA chart, and FIG. 1b is a DSC chart).
Example 4 preparation of Iridium Complex AG02 organic electroluminescent device
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 (50nm), and the evaporation rate is 0.05 nm/s; the electron transport layer adopts 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene TmPyPb (50nm), 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 40nm, the organic light-emitting layer comprises a main material and a light-emitting material, the main material is 4,4' -tri (9-carbazolyl) triphenylamine TCTA, the light-emitting material is an iridium complex AG02, and the mass fraction of the iridium complex is 8 wt%. The HAT-CN, TAPC, TCTA and TmPyPb functional material has the structure shown in figure 1. The properties of the organic electroluminescent device thus obtained are shown in Table 1.
Example 5 preparation of Iridium Complex AG26 organic electroluminescent device
Referring to the method of example 4, the luminescent material iridium complex AG26 was used to prepare organic electroluminescent devices, and the device properties are shown in Table 1.
Example 6 preparation of Iridium Complex AG50 organic electroluminescent device
Referring to the method of example 4, the light-emitting material iridium complex AG50 organic electroluminescent device used has the device properties shown in Table 1.
TABLE 1 Performance parameters of devices made from the iridium complexes AG02, AG26, AG50 of the present invention
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 invention achieves the purpose of regulating and controlling the efficiency and the service life of a device by designing and optimizing the structure of a compound. As can be seen from the results in Table 1, the iridium complex of the present invention is excellent in device performance.
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 (9)
1. An iridium complex is characterized by the following structural general formula:
wherein R is1-R4The same or different, are independently selected from the group consisting of hydrogen, deuterium, halogen, halogenated hydrocarbon groups, alkyl groups, cycloalkyl groups, heteroalkyl groups, alkoxy groups, aryloxy groups, amino groups, silyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, deuterated alkyl groups, deuterated cycloalkyl groups, deuterated heteroalkyl groups, deuterated alkoxy groups, deuterated aryloxy groups, deuterated silyl groups, deuterated aryl groups, deuterated heteroaryl groups, acyl groups, carbonyl groups, carboxylic acids, esters, nitriles, thio groups, and combinations thereof;
wherein R is1Independently represent mono-, di-, tri-, tetra-or unsubstituted, R1When it represents di-, tri-or tetra-substitution, each substituent may be the same or different;
wherein R is2Independently represent mono-, di-, tri-, tetra-, penta-or unsubstituted, R2When the substituent is a double substituent, a triple substituent, a tetra substituent or a penta substituent, the substituents are the same or different;
wherein R is3Independently represent mono-, di-, tri-, tetra-or unsubstituted, R3When it represents di-, tri-or tetra-substitution, each substituent may be the same or different;
wherein R is4Independently represent mono-, di-or unsubstituted, R4When the substituent is disubstituted, the substituents may be the same or different;
wherein R is5-R7The same or different, are independently selected from the group consisting of hydrogen, deuterium, halogenated hydrocarbon groups, alkyl groups, cycloalkyl groups, heteroalkyl groups, alkoxy groups, aryloxy groups, silyl groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, deuterated alkyl groups, deuterated cycloalkyl groups, deuterated heteroalkyl groups, deuterated alkoxy groups, deuterated aryloxy groups, deuterated silyl groups, deuterated aryl groups, deuterated heteroaryl groups.
2. The iridium complex of claim 1A compound of formula (I), wherein R1-R4The same or different, are independently selected from the group consisting of hydrogen, halogen, halogenated hydrocarbon groups, alkyl groups, silane groups, deuterium, deuterated alkyl groups, heteroalkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, aryl groups, heteroaryl groups, and nitrile groups.
3. The iridium complex according to claim 1, wherein R is5-R7The same or different, are independently selected from alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, deuterated alkyl, deuterated cycloalkyl, deuterated heteroalkyl, deuterated aryl, deuterated heteroaryl.
4. The iridium complex according to claim 2, wherein R is1，R2Independently selected from the group consisting of:
5. the iridium complex according to claim 2, wherein R is3，R4Independently selected from the group consisting of:
6. the iridium complex according to claim 3, wherein R is5，R6Independently selected from the group consisting of:
7. the iridium complex according to claim 3, wherein R is7Independently selected from hydrogen, methyl, deuteromethyl.
8. The iridium complex according to claim 1, wherein the iridium complex is selected from the following structures:
9. use of an iridium complex as claimed in any one of claims 1 to 8 as a luminescent material in the preparation of organic electroluminescent devices, photocatalysts and optical probes.
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| CN114920783A (en) * | 2022-06-29 | 2022-08-19 | 北京云基科技有限公司 | Luminescent material and application thereof |
| CN115260201A (en) * | 2022-07-12 | 2022-11-01 | 马鞍山南大高新技术研究院有限公司 | Iridium complex based on nitrogen heterocyclic aromatic ring modified indolo [3,2,1-jk ] carbazole main ligand and application thereof |
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