WO2018113782A1 - Complexe organométallique, polymère, mélange, composition et dispositif électronique organique - Google Patents

Complexe organométallique, polymère, mélange, composition et dispositif électronique organique Download PDF

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WO2018113782A1
WO2018113782A1 PCT/CN2017/118063 CN2017118063W WO2018113782A1 WO 2018113782 A1 WO2018113782 A1 WO 2018113782A1 CN 2017118063 W CN2017118063 W CN 2017118063W WO 2018113782 A1 WO2018113782 A1 WO 2018113782A1
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carbon atoms
organic
metal
organic complex
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潘君友
梁志明
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广州华睿光电材料有限公司
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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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/12—Gold compounds
    • 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

Definitions

  • the present invention relates to the field of organic electronic devices, and more particularly to a metal organic complex, a high polymer, a mixture, a composition, and an organic electronic device.
  • organic light-emitting diodes In flat panel display and lighting applications, organic light-emitting diodes (OLEDs) have the advantages of low cost, light weight, low operating voltage, high brightness, color adjustability, wide viewing angle, easy assembly to flexible substrates, and low energy consumption. Therefore, it has become the most promising display technology.
  • OLEDs organic light-emitting diodes
  • various systems based on fluorescent and phosphorescent materials have been developed.
  • An organic light-emitting diode using a fluorescent material has high reliability, but its internal electroluminescence quantum efficiency is limited to 25% under electric field excitation.
  • the branch ratio of the singlet excited state and the triplet excited state of the excitons is 1:3, an organic light emitting diode using a phosphorescent material can achieve an internal luminescence quantum efficiency of almost 100%.
  • the triplet excitation is effectively obtained by doping the center of the heavy metal, which improves the spin-orbital merging and thus the inter-system transition to the triplet state.
  • Metal ruthenium (III)-based complexes are a class of materials widely used in high-efficiency OLEDs with high efficiency and stability. Baldo et al. reported the use of fac-tris(2-phenylpyridine)ruthenium(III)[Ir(ppy) 3 ] as a phosphorescent material, 4,4'-N,N'-dicarbazole-biphenyl (4 , 4'-N, N'-diarbazole-biphenyl) (CBP) is a high quantum efficiency OLED of matrix material (Appl. Phys. Lett. 1999, 75, 4).
  • a phosphorescent luminescent material is the sky blue complex bis[2-(4',6'-difluorophenyl)pyridine-N,C 2 ]-pyridinium ruthenium (III) (FIrpic), which is doped to The high triplet energy matrix exhibits an extremely high photoluminescence quantum efficiency of approximately 60% in solution and almost 100% in solid film (Appl. Phys. Lett. 2001, 79, 2082).
  • ruthenium (III) systems based on 2-phenylpyridine and its derivatives have been used in large quantities for the preparation of OLEDs, phosphorescent luminescent materials containing other metal centers with these ligands have not been fully investigated.
  • One way to improve the luminous efficiency of gold (III) complexes is to introduce strong ⁇ -donor ligands, such as the stable gold (III) aryl compounds first discovered and synthesized by Yam et al., even at room temperature.
  • ⁇ -donor ligands such as the stable gold (III) aryl compounds first discovered and synthesized by Yam et al., even at room temperature.
  • Another interesting donor is an alkynyl group.
  • the luminescent properties of the gold (I) alkynyl complex have been extensively studied, the chemistry of the gold (III) alkynyl group has been largely ignored, with one exception: the 6-benzyl-2,2'-bipyridine alkyne
  • the synthesis of the compound of the fund (III) J. Chem. Soc. Dalton Trans.
  • a high polymer, a mixture, a composition, and an organic electronic device are also provided.
  • a metal organic complex having the general formula M(L) n (L 1 ) m (1), wherein M(L) n is selected from one of the following formulae:
  • M is a metal atom
  • L is a monoanionic monodentate chelating ligand
  • L 1 is a bidentate chelate ligand or a tridentate chelate ligand
  • An aryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms substituted by R, and a non-aromatic ring group having 2 to 20 carbon atoms substituted by R One, and in the formula (3), At most one of them is a double bond;
  • Ar 3 is selected from the group consisting of an aryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a non-aromatic ring group having 2 to 20 carbon atoms, and having 2 substituted by R
  • aryl group having 2 to 20 carbon atoms a heteroaryl group having 2 to 20 carbon atoms substituted by R, and a non-aromatic ring group of 2 to 20 carbon atoms substituted by R;
  • R is selected from the group consisting of hydrogen, hydrazine, a halogen atom, a linear alkane group having 1 to 20 carbon atoms, a branched alkane group having 1 to 20 carbon atoms, and a linear olefin having 1 to 20 carbon atoms. a branched olefin group having 1 to 20 carbon atoms, an alkane ether group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, and having 1 to 20 carbon atoms.
  • heteroaryl group and one of non-aromatic ring groups having 1 to 20 carbon atoms wherein one or more R groups may be bonded to each other to form an aliphatic ring system or an aromatic ring system, or Formula 2 or 3 bonding to form an aliphatic ring system or an aromatic ring system;
  • -X- is a single bond, or X is a two bridging group
  • n is any integer from 1 to 3;
  • n is any integer from 0 to 4.
  • o is any integer from 0 to 2.
  • a high polymer comprising a repeating unit, the structural formula of the repeating unit comprising the structural formula of the above metal organic complex.
  • a mixture comprising the above metal organic complex and one of the above polymers and an organic functional material.
  • a composition comprising the above metal organic complex, the above-mentioned high polymer, and one of the above mixtures, and an organic solvent.
  • An organic electronic device comprising a functional layer, and the material of the functional layer comprises one of the above metal organic complex, the above-mentioned high polymer, the above mixture, and the above composition.
  • M is a metal atom
  • L is a monoanionic monodentate chelate ligand
  • L 1 is a bidentate chelate ligand or a tridentate chelate ligand
  • n is any integer from 1 to 3
  • m is 0 to 4 Any integer.
  • substructure M(L) n of the metal organic complex is selected from one of the following formulas:
  • M is a metal atom
  • An aryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms substituted by R, and a non-aromatic ring group having 2 to 20 carbon atoms substituted by R One, and in the formula (3), At most one of them is a double bond;
  • Ar 3 is selected from the group consisting of an aryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a non-aromatic ring group having 2 to 20 carbon atoms, and having 2 substituted by R
  • aryl group having 2 to 20 carbon atoms a heteroaryl group having 2 to 20 carbon atoms substituted by R, and a non-aromatic ring group of 2 to 20 carbon atoms substituted by R;
  • R is selected from the group consisting of hydrogen, hydrazine, a halogen atom, a linear alkane group having 1 to 20 carbon atoms, a branched alkane group having 1 to 20 carbon atoms, and a linear olefin having 1 to 20 carbon atoms. a branched olefin group having 1 to 20 carbon atoms, an alkane ether group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, and having 1 to 20 carbon atoms.
  • heteroaryl group and one of non-aromatic ring groups having 1 to 20 carbon atoms wherein one or more R groups may be bonded to each other to form an aliphatic ring system or an aromatic ring system, or Formula 2 or 3 bonding to form an aliphatic ring system or an aromatic ring system;
  • -X- is a single bond, or X is a two bridging group
  • n is any integer from 1 to 3;
  • n is any integer from 0 to 4.
  • o is any integer from 0 to 2.
  • M is a transition metal atom. Still further, M is selected from the group consisting of ruthenium, gold, platinum, rhodium, ruthenium, osmium, iridium, nickel, copper, silver, zinc, tungsten, and palladium. Further, M is selected from one of gold, platinum, and palladium. Specifically, M is gold. Gold is chemically stable and has a significant heavy atomic effect, enabling metal organic complexes to achieve high luminous efficiency.
  • o is one. At this time, M is directly connected to N. In another embodiment, o is zero.
  • Ar 3 are each independently selected from one of an aromatic ring group having 5 to 20 ring atoms and a heteroaromatic ring group having 5 to 20 ring atoms. Further, And Ar 3 is each selected from the group consisting of an aromatic cyclic group having 5 to 18 ring atoms and a heteroaromatic ring group having 5 to 18 ring atoms. go a step further, And Ar 3 are each independently selected from one of an aromatic ring group having 5 to 12 ring atoms and a heteroaromatic ring group having 5 to 18 ring atoms.
  • the aromatic group means a hydrocarbon group containing at least one aromatic ring, and includes a monocyclic group and a polycyclic ring system.
  • the heteroaromatic group refers to a hydrocarbon group (containing a hetero atom) containing at least one heteroaromatic ring, and the hydrocarbon group of the heteroaromatic ring includes a monocyclic group and a polycyclic ring system.
  • These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, a fused ring.
  • These ring species of polycyclic ring, at least one ring species are aromatic or heteroaromatic.
  • an aromatic group or a heteroaryl group in an aromatic ring group or a heteroaromatic ring group may be interrupted by a short non-aromatic unit.
  • the non-aromatic unit is less than 10% of a non-hydrogen atom. Further, the non-aromatic unit is less than 5% of a non-hydrogen atom.
  • the non-aromatic unit is a carbon atom, a nitrogen atom or an oxygen atom. Therefore, ring systems such as 9,9'-spirobifluorene, 9,9-diarylsulfonium, triarylamine and diaryl ether are also considered to be Aromatic ring system.
  • the aromatic group is selected from the group consisting of benzene, a derivative of benzene, a derivative of naphthalene, naphthalene, a derivative of ruthenium, osmium, a derivative of phenanthrene, phenanthrene, a perylene, a derivative of perylene, Derivatives of tetracene and tetracene, derivatives of ruthenium and osmium, derivatives of benzopyrene, benzopyrene, derivatives of triphenylene, triphenylene, derivatives of ruthenium and osmium, derivatives of ruthenium and osmium One of them.
  • the heteroaromatic group is selected from the group consisting of furan, a derivative of furan, a derivative of benzofuran, benzofuran, a derivative of thiophene, thiophene, a derivative of benzothiophene, benzothiophene, pyrrole, pyrrole Derivatives, derivatives of pyrazoles, pyrazoles, derivatives of triazoles, triazoles, imidazoles, derivatives of imidazoles, derivatives of oxazoles, oxazoles, oxadiazoles, derivatives of oxadiazoles, thiazoles, Derivatives of thiazole, derivatives of tetrazole, tetrazole, derivatives of ruthenium and osmium, derivatives of oxazole, oxazole, pyrroloimidazole, derivatives of pyrroloimidazole, pyrrolopyrrole, pyrrolopyrrole
  • Ar 3 are each independently selected from the group consisting of an unsubstituted non-aromatic ring group having 5 to 20 ring atoms and a non-aromatic ring group having 5 to 20 ring atoms substituted by R 0 to improve The triplet level of the metal organic complex to obtain a green or blue light emitter.
  • the ring of the non-aromatic ring group contains at least two carbon atoms. Further, the ring of the non-aromatic ring group contains 2 to 6 carbon atoms.
  • the ring of the non-aromatic ring group may be a saturated ring and a partially saturated ring.
  • the non-aromatic ring group includes an unsubstituted non-aromatic ring group and a non-aromatic ring group substituted with R.
  • R 0 contains a hetero atom. Further, R 0 includes at least one of Si, N, P, O, S, and Ge. Further, R 0 contains at least one of Si, N, P, O, and S.
  • R 0 may be a group of a cyclohexyl- or piperidine-like system, or a group of a cyclooctadiene-like ring system.
  • R 0 is selected from one of a C 1 - C 10 alkyl group, a C 1 - C 10 alkoxy group, a C 2 - C 10 aryl group, and a C 2 - C 10 heteroaryl group.
  • C 1 -C 10 alkyl is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, 2 -methylbutyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoromethyl, 2, 2,2-Trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, One of cycloocten
  • the C 1 -C 10 alkoxy group is selected from the group consisting of methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and One of 2-methylbutoxy groups.
  • the C 2 -C 10 aryl group and the C 2 -C 10 heteroaryl group can be further substituted by the above R 0 and can be bonded to an aromatic ring or a heteroaromatic ring.
  • the C 2 -C 10 aryl group or the C 2 -C 10 heteroaryl group is selected from the group consisting of benzene, naphthalene, anthracene, anthracene, anthracene, fluorene, fluorene, fluorene, butyl, pentane, benzo. ⁇ , furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, thiopurine, pyrrole, hydrazine, isoindole, carbazole, pyridine, quinoline, iso Quinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, Carbazole, imidazole, benzimidazole,
  • aromatic ring group and the heteroaromatic ring group are not limited to the above groups, and may also be selected from the group consisting of a biphenylylene group, a linoleylene, an anthracene, a spirobifluorene, a dihydrophenanthrene, a tetrahydroanthracene and an anthracene.
  • ⁇ cis or trans
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 are each independently selected from one of CR 3 and N;
  • R 3 , R 4 and R 5 can bond to an aliphatic ring group or an aromatic ring group, and R 3 , R 4 and R 5 themselves can also bond to an aliphatic ring group or an aromatic ring group, respectively.
  • the crosslinkable group means a functional group containing an unsaturated bond such as an alkenyl group or an alkynyl group.
  • cycloaromatic hydrocarbon group is selected from the group consisting of phenyl, biphenyl, triphenyl, benzo, naphthyl, anthryl, phenalkenyl, phenanthryl, anthracenyl, fluorenyl, fluorenyl, fluorenyl and fluorenyl
  • aromatic heterocyclic groups selected from the group consisting of dibenzothiophenyl, dibenzofuranyl, furyl, thienyl, benzofuranyl, benzothienyl, oxazolyl, pyrazolyl, imidazolyl, Triazolyl, isoxazolyl, thiazolyl, oxadiazolyl, oxatriazole, oxazolyl, thiadiazol
  • the ring structure is bonded together by at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group.
  • each It can be further substituted with at least one of an anthracene, an alkyl group, an alkoxy group, an amino group, an alkene group, an alkyne group, an aralkyl group, a heteroalkyl group, an aryl group, and a heteroaryl group.
  • Ar 3 are each selected from one of the following groups:
  • R is independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a linear alkane group having 1 to 20 carbon atoms, a branched alkane group having 1 to 20 carbon atoms, and having 1 to 20 carbon atoms.
  • X is selected from a linear alkane group having 0 to 5 carbon atoms, a branched alkane group having 0 to 5 carbon atoms, a linear olefin group having 0 to 5 carbon atoms, and a branched olefin group of 0 to 5 carbon atoms, having 0 to 5
  • a linear alkane ether group of a carbon atom an aromatic ring group of 5 to 15 carbon atoms, and a heteroaromatic ring group of 4 to 15 carbon atoms.
  • X is selected from a linear alkane group having 0 to 2 carbon atoms, a branched alkane group having 0 to 2 carbon atoms, a linear olefin group having 0 to 2 carbon atoms, and having a branched olefin group of 0 to 2 carbon atoms, an alkane ether group having 0 to 2 carbon atoms, an aromatic ring group having 5 to 10 carbon atoms, and a heteroaromatic group containing 4 to 10 carbon atoms One of the group of ring groups.
  • X is selected from one of the following structural formulas:
  • R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a linear alkane group having 1 to 20 carbon atoms, and a branched alkane having 1 to 20 carbon atoms.
  • a linear olefin group having 1 to 20 carbon atoms a branched olefin group having 1 to 20 carbon atoms, an alkane ether group having 1 to 20 carbon atoms, having 1 to 20 carbon atoms
  • the aliphatic ring system or the aromatic ring system may be bonded to each other or to each other, or may be bonded to the formula 2 or 3, respectively, to form an aliphatic ring system or an aromatic ring system.
  • X is selected from one of the following structures:
  • M(L) n comprises one of the following substructures:
  • # represents a position connected to Ar 3 or M in the general formula (3);
  • M(L) n includes one of the following substructures:
  • M(L) n includes one of the following substructures:
  • # represents a position connected to Ar 3 or M in the formula (3); the above substructure formula can be further substituted.
  • o is 1, Ar 3 and M are connected by a ⁇ -bond, and Ar 3 is a strong sigma-donor ligand of a negative ion monodentate.
  • Ar 3 is selected from the group consisting of benzene, naphthalene, anthracene, anthracene, phenanthrene, anthracene, oxazole, imidazole, and benzimidazole.
  • metal organic complex is selected from one of the following formulae:
  • X 71 to X 73 are each selected from the group consisting of a nitrogen atom, an oxygen atom, and a carbon atom. Further, at least one of X 71 to X 73 is a nitrogen atom;
  • R 16 to R 21 are each selected from the group consisting of hydrogen, hydrazine, a halogen atom, CN, NO 2 , CF 3 , B(OR 2 ) 2 , Si(R 2 ) 3 , and a linear alkane group having 1 to 20 carbon atoms.
  • a branched alkane group having 1 to 20 carbon atoms a linear olefin group having 1 to 20 carbon atoms, a branched olefin group having 1 to 20 carbon atoms, having 1 to 20 carbon atoms
  • L is a monoanionic monodentate chelating ligand, which has the same definition as L in the above M(L) n . .
  • the above metal-organic complex facilitates obtaining thermally excited delayed fluorescent TADF or so-called Singlet Harvesting characteristics.
  • thermally excited delayed fluorescent TADF material disclosed in Adachi et al., Nature Vol 492, 234, (2012), when the ⁇ E(S1-T1) of the metal organic compound is sufficiently small, the triplet excitons of the organic compound can pass the opposite Converts internally to singlet excitons for efficient illumination.
  • ⁇ E(S1-T1) of the metal organic complex is ⁇ 0.30 eV. Further, the metal organic complex has ⁇ E(S1-T1) ⁇ 0.25 eV. Still further, the metal organic complex has ⁇ E(S1-T1) ⁇ 0.20 eV. Further, ⁇ E(S1-T1) ⁇ 0.10 eV of the metal organic complex.
  • ⁇ E(S1-T1) is the difference between the singlet energy level S1 and the triplet energy level T1.
  • the absolute values of HOMO, LUMO, S1 and T1 depend on the measurement method or calculation method used. Even for the same method, different evaluation methods, for example, the starting point and the peak point on the CV curve can be given differently. HOMO/LUMO value. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method.
  • the values of HOMO, LUMO, S1, and T1 are based on Time-dependent DFT simulations, but do not affect the application of other measurement or calculation methods.
  • the metal organic complex is selected from one of the following structures:
  • the metal organic complex is a luminescent material, and the metal organic complex has an emission wavelength of 300 nm to 1000 nm. Further, the metal organic complex has an emission wavelength of 350 nm to 900 nm. Further, the metal organic complex has an emission wavelength of 400 nm to 800 nm.
  • luminescence refers to photoluminescence or electroluminescence.
  • the photoluminescence efficiency of the metal organic complex is ⁇ 30%. Still further, the photoluminescence efficiency of the metal organic complex is ⁇ 40%. Still further, the photoluminescence efficiency of the metal organic complex is ⁇ 50%. Further, the photoluminescence efficiency of the metal organic complex is ⁇ 60%.
  • the metal organic complex is a non-luminescent material.
  • the high polymer of one embodiment includes a repeating unit, and the structural formula of the repeating unit includes the structural formula of the above metal organic complex.
  • the high polymer is a non-conjugated high polymer, and for example, the structural unit of the metal organic complex represented by the general formula (1) is on the side chain of the high polymer.
  • the high polymer is a conjugated high polymer.
  • the use of the above metal organic complexes or polymers in organic electronic devices is selected from the group consisting of an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, and an organic spintronic device.
  • OLED organic light emitting diode
  • OLED organic photovoltaic cell
  • OFET organic field effect transistor
  • OLED organic light emitting field effect transistor
  • a mixture of an embodiment comprising one of a metal organic complex and a high polymer, and an organic functional material.
  • the organic functional material is selected from the group consisting of a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injecting material (EIM), an electron blocking material (EBM), and a hole blocking material (HBM).
  • HIM hole injection material
  • HTM hole transport material
  • ETM electron transport material
  • EIM electron injecting material
  • EBM electron blocking material
  • HBM hole blocking material
  • the organic functional material is selected from one of a luminescent metal organic complex and an organic dye.
  • the organic functional material may also be an organic functional material as disclosed in WO2010135519A1, US20090134784A1 and WO2011110277A1.
  • the organic functional material may be a small molecule or a high polymer material.
  • Small molecules as used herein refer to molecules that are non-polymeric, non-oligomer, non-dendritic, and non-blend, with no repeating structures in small molecules. Among them, the molar mass of the small molecule is ⁇ 3000 g/mol. Further, the molar mass of the small molecule is ⁇ 2000 g/mol. Further, the molar mass of the small molecule is ⁇ 1500 g/mol.
  • the polymer comprises a homopolymer, a copolymer, and a block copolymer. Also in this application, the high polymer also contains dendrimers.
  • dendrimers For the synthesis and application of dendrimers, see Dendrimers and Dendrons, Wiley-VCH Verlag GmbH & Co. KGaA, 2002, Ed. George R. Newkome, Charles Introduction to N. Moorefield, Fritz Vogtle.
  • a conjugated polymer is a type of high polymer.
  • the backbone of the conjugated polymer is mainly composed of sp 2 hybrid orbitals of carbon atoms.
  • the carbon atoms in the main chain can also be substituted by other non-carbon atoms, and the sp 2 hybridization of carbon atoms in the main chain is interrupted by some natural defects.
  • the conjugated polymer may also contain an aryl amine, an aryl phosphine, and other heteroarmotics, metal organic complexes in the main chain. (organometallic complexes) and so on.
  • the mixture comprises a metal organic complex and an organic functional material, and the metal organic complex has a mass percentage of 0.01% to 30%. Further, the metal organic complex has a mass percentage of 0.1% to 20%. Further, the metal organic complex has a mass percentage of 0.2% to 15%. Further, the metal organic complex has a mass percentage of 2% to 15%.
  • the mixture comprises one of a metal organic complex and a high polymer, and a triplet matrix material material.
  • the metal organic complex as the phosphorescent emitter, the weight percentage of the metal organic complex ⁇ 30 wt%; further, the weight percentage of the metal organic complex ⁇ 20 wt%; further, the weight percentage of the metal organic complex ⁇ 15 wt% .
  • the mixture includes one of a metal organic complex and a high polymer, a triplet matrix material, and a triplet emitter.
  • the mixture comprises one of a metal organic complex and a high polymer, and a thermally activated delayed fluorescent luminescent material (TADF).
  • TADF thermally activated delayed fluorescent luminescent material
  • triplet matrix material the triplet emitter and the TADF material (but is not limited thereto).
  • Any metal complex or organic compound can be used as a matrix for the triplet matrix material as long as its triplet energy is higher than that of the illuminant, especially higher than that of the triplet emitter (phosphorescent emitter).
  • the metal complex of the triplet matrix material has the following general formula:
  • M is a metal
  • (Y 3 -Y 4 ) is a bidentate ligand
  • Y 3 and Y 4 are each independently selected from one of C, N, O, P and S
  • L is an auxiliary ligand
  • the value of m has a maximum coordination number from 1 to M
  • m+n is the maximum coordination number of M.
  • M is selected from the group consisting of Cu, Au, Ir, and Pt.
  • metal complex of the triplet matrix material has the following general formula:
  • (O-N) is a bidentate ligand, and the metal is coordinated to the O atom and the N atom.
  • the organic compound which can be used as the triplet matrix material is a compound containing a cyclic aromatic hydrocarbon group or a compound containing an aromatic heterocyclic group.
  • the compound containing a cyclic aromatic hydrocarbon group includes: benzene, biphenyl, triphenyl, benzo and anthracene; and the compound containing an aromatic heterocyclic group includes: dibenzothiophene, dibenzofuran, dibenzoselenophene , furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, carbazole, pyridinium, pyrrole dipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, dioxin Oxazole, triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine,
  • the organic compound which can be used as the triplet matrix material may also be a group containing a 2-ring to 10-ring structure, for example, a cyclic aromatic hydrocarbon group or an aromatic heterocyclic group. Wherein each group is directly connected, or through an oxygen atom, a nitrogen atom, At least one of a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group is bonded.
  • each aromatic group (Ar) is substituted with one of hydrogen, an alkyl group, an alkoxy group, an amino group, an alkenyl group, an alkynyl group, an aralkyl group, a heteroalkyl group, an aryl group, and a heteroaryl group.
  • the organic compound of the triplet matrix material comprises at least one of the following groups:
  • n is any integer from 0 to 20;
  • X 1 -X 8 are each selected from one of CR 1 and N;
  • X 9 is selected from one of CR 1 R 2 and NR 1 ;
  • R 1 - R 7 Each is independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl.
  • the triplet matrix material is selected from one of the following structures:
  • Triplet emitters are also known as phosphorescent emitters.
  • the triplet emitter is a metal complex containing the formula M(L)n. Wherein M is a metal element, L is an organic ligand, and L is bonded to M through one or more position linkages or coordination; n is an integer greater than 1, preferably n is selected from 1, 2, 3, 4 One of 5, 6 and 6.
  • the metal complex is coupled to the polymer through one or more locations. Specifically, the metal complex is coupled to the polymer via an organic ligand.
  • M is selected from one of a transition metal element, a lanthanoid element, and a lanthanoid element.
  • M is selected from one of Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu, and Ag. More preferably, M is selected from one of Os, Ir, Ru, Rh, Cu, Au, and Pt.
  • the triplet emitter contains a chelating ligand, that is, a ligand.
  • the ligand is coordinated to the metal by at least two bonding sites.
  • the triplet emitter comprises 2 to 3 bidentate ligands or polydentate ligands. Chelating ligands are beneficial for increasing the stability of metal complexes.
  • the organic ligand is selected from the group consisting of a phenylpyridine derivative, a 7,8-benzoquinoline derivative, a 2(2-thienyl)pyridine derivative, a 2(1-naphthyl)pyridine derivative, and a 2-phenylquinoline derivative. One of them. Further, the organic ligands may all be substituted, for example by fluorine or trifluoromethyl.
  • the ancillary ligand is selected from one of acetic acid acetone and picric acid.
  • the metal complex of the triplet emitter has the following general formula:
  • M is a metal.
  • M is selected from one of a transition metal element, a lanthanoid element, and a lanthanide element;
  • Ar 1 is a cyclic group, wherein Ar 1 contains at least one donor atom, that is, an atom having a lone pair of electrons, such as nitrogen or phosphorus, and the cyclic group is coordinated to the metal through a donor atom;
  • Ar 2 is a cyclic group, wherein Ar 2 contains at least one C atom, and the cyclic group is bonded to the metal through a C atom;
  • Ar 1 and Ar 2 are bonded together by a covalent bond;
  • Ar 1 and Ar 2 each may carry one or more substituent groups, and Ar 1 and Ar 2 may be further coupled together by a substituent group;
  • L is an ancillary ligand.
  • L is a bidentate chelate ligand. More preferably, L is a monoanionic bidentate chelate ligand;
  • n is any integer from 1 to 3.
  • m is 2 or 3. More preferably, m is 3;
  • n is any integer from 0 to 2.
  • n is 0 or 1. More preferably, n is zero.
  • the material of the triplet illuminant and its use can be WO 200070655, WO 200141512, WO 200202714, WO 200215645, EP 1191613, EP 1191612, EP 1191614, WO 2005033244, WO 2005019373, US 2005/0258742, WO 2009146770, WO 2010015307, WO 2010031485, WO 2010054731, WO 2010054728, WO 2010086089, WO 2010099852, WO 2010102709, US 20070087219 A1, US 20090061681 A1, US 20010053462 A1, Baldo, Thompson et al.
  • the triplet emitter is selected from one of the following structures:
  • TDF Thermally activated delayed fluorescent luminescent material
  • the thermally activated delayed fluorescent luminescent material is a third generation organic luminescent material developed after organic fluorescent materials and organic phosphorescent materials.
  • Such materials generally have a small singlet-triplet energy level difference ( ⁇ Est), and triplet excitons can be converted into singlet exciton luminescence by anti-intersystem crossing. Therefore, the singlet excitons and triplet excitons formed under electrical excitation can be fully utilized, so that the quantum efficiency in the organic electronic device can reach 100%.
  • ⁇ Est singlet-triplet energy level difference
  • TADF needs to have a small singlet-triplet energy level difference ( ⁇ Est).
  • ⁇ Est of the TADF is ⁇ 0.3 eV.
  • ⁇ Est of the TADF is ⁇ 0.2 eV.
  • ⁇ Est of the TADF is ⁇ 0.1 eV.
  • ⁇ Est of the TADF is ⁇ 0.05 eV.
  • the TADF may be CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et. al. Adv. Mater., 21, 2009, 4802, Adachi, et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et. al. Appl. Phys. Lett., 101 , 2012, 093306, Adachi, et.al. Chem.
  • the TADF is selected from one of the following structures:
  • the metal organic complex is used in an evaporated OLED device.
  • the molar mass of the metal organic complex is ⁇ 1000 g/mol; further, the molar mass of the metal organic complex is ⁇ 900 g/mol; further, the molar mass of the metal organic complex is ⁇ 850 g/mol; further, the metal The molar mass of the organic complex is ⁇ 800 g/mol; further, the molar mass of the metal organic complex is ⁇ 700 g/mol.
  • a metal organic complex is used to print an OLED device.
  • the molar mass of the metal organic complex is ⁇ 700 g/mol; further, the molar mass of the metal organic complex is ⁇ 800 g/mol; further, the molar mass of the metal organic complex is ⁇ 900 g/mol; further, the metal The molar mass of the organic complex is ⁇ 1000 g/mol; further, the molar mass of the metal organic complex is ⁇ 1100 g/mol.
  • the solubility of the metal organic complex in toluene is ⁇ 5 mg/mL at 25 ° C; further, the solubility of the metal organic complex in toluene is ⁇ 8 mg / mL; The solubility of the metal organic complex in toluene is ⁇ 10 mg/mL.
  • composition of one embodiment includes one of the above metal organic complex, the above polymer, and the above mixture, and an organic solvent.
  • the composition when used as a printing ink, the composition may be a solution or a suspension. Viscosity and surface tension are important parameters of the composition. The surface tension parameters of suitable compositions are suitable for the particular substrate and the particular printing process.
  • the surface tension of the composition is at an operating temperature or at 25 ° C. 19dyne/cm to 50dyne/cm. Further, the composition has a surface tension of 22 dyne/cm to 35 dyne/cm. Further, the surface tension of the composition is from 25 dyne/cm to 33 dyne/cm.
  • the viscosity of the composition when the composition is used in ink jet printing, is from 1 cps to 100 cps at an operating temperature or 25 °C. Further, the viscosity of the composition is from 1 cps to 50 cps. Still further, the viscosity of the composition is from 1.5 cps to 20 cps. Further, the viscosity of the composition is from 4.0 cps to 20 cps.
  • Viscosity can be adjusted by a number of methods, for example, by selecting a solvent and adjusting the concentration of the functional material in the composition.
  • the above composition can appropriately adjust the viscosity of the composition according to the printing method.
  • the organic functional material has a mass percentage of 0.3% to 30%. Further, the organic functional material has a mass percentage of 0.5% to 20%. Further, the organic functional material has a mass percentage of 0.5% to 15%. Further, the organic functional material has a mass percentage of 0.5% to 10%. Further, the organic functional material has a mass percentage of 1% to 5%.
  • the organic solvent includes a first solvent
  • the first solvent includes at least one of an aromatic solvent, a heteroaromatic solvent, a ketone solvent, an ether solvent, and an ester solvent.
  • the aromatic solvent is selected from one of an aliphatic chain-substituted aromatic solvent and a ring-substituted aromatic solvent.
  • the aromatic solvent is selected from the group consisting of p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, and p-methyl Propylene, dipentylbenzene, trimerene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4- Tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropyl, pen
  • the heteroaromatic solvent is selected from one of 2-phenylpyridine, 3-phenylpyridine, and 4-(3-phenylpropyl)pyridine.
  • the ketone solvent is selected from the group consisting of 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(methoxy)tetralone, acetophenone, Phenylacetone, benzophenone, 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methyl Propiophenone, isophorone, 2,6,8-trimethyl-4-indanone, anthrone, 2-nonanone, 3-fluorenone, 5-nonanone, 2-nonanone, 2,5- One of adipone, phorone and di-n-pentyl ketone.
  • the ether solvent is selected from the group consisting of 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1 ,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-B Basic diethyl ether, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, Dibenzyl ether, 4-tert-butyl anisole, trans-p-propenyl anisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenyl
  • the ester solvent is selected from the group consisting of alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkanolactone and oil.
  • alkyl octanoate alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkanolactone and oil.
  • One of the acid alkyl esters One of the acid alkyl esters.
  • the first solvent includes at least one of an aliphatic ketone and an aliphatic ether.
  • the aliphatic ketone is selected from 2- ⁇ Ketone, 3-fluorenone, 5-fluorenone, 2-nonanone, 2,5-hexanedione, 2,6,8-trimethyl-4-indanone, phorone and di-n-pentanone At least one;
  • the aliphatic ether is selected from the group consisting of pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, three At least one of ethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
  • the organic solvent further includes a second solvent
  • the second solvent includes methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, and benzene.
  • Ether morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxy Toluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl At least one of sulfone, tetrahydronaphthalene, decalin and hydrazine.
  • the above composition When the above composition is used as a coating or printing ink, it can be applied to the preparation of an organic electronic device. Further, the above composition is prepared by a method of printing or coating an organic electronic device.
  • the printing or coating method is selected from, but not limited to, inkjet printing, Nozzle Printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, torsion roller printing, One of lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, nozzle printing (Nozzle printing), and slit type extrusion coating. Further, the printing or coating method is selected from one of inkjet printing, slit type extrusion coating, jet printing, and gravure printing.
  • the above composition further comprises an additive selected from at least one of a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobic agent, and a binder.
  • the additive is used to adjust the viscosity, film forming properties, adhesion, and the like of the composition.
  • An organic electronic device includes a functional layer, and the material of the functional layer includes one of the above-described metal organic complex and the above-mentioned high polymer. Further, the organic electronic device comprises a cathode, an anode and a functional layer between the cathode and the anode, and the material of the functional layer comprises one of the above metal organic complex and the above high polymer.
  • the organic electronic device is selected from the group consisting of an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, and an organic spintronic device.
  • OLED organic light emitting diode
  • OLED organic photovoltaic cell
  • OEEC organic light emitting cell
  • OFET organic field effect transistor
  • an organic light emitting field effect transistor an organic laser
  • an organic spintronic device One of an organic sensor and an organic plasmon emitting diode (Organic Plasmon Emitting Diode).
  • the organic electronic device is an electroluminescent device.
  • the organic electronic device is an OLED, wherein the OLED comprises a substrate, an anode, a light emitting layer and a cathode.
  • the substrate may be opaque or transparent.
  • a transparent substrate can be used to make a transparent light-emitting component.
  • the substrate may be a substrate as disclosed in Bulovic et al. Nature 1996, 380, p29, and Gu et al, Appl. Phys. Lett. 1996, 68, p2606.
  • the substrate can be rigid or elastic.
  • the substrate is selected from the group consisting of plastics, metals, semiconductor wafers, and glass.
  • the substrate has a smooth surface. More specifically, the surface of the substrate is free from defects.
  • the substrate is flexible and the substrate is a polymeric film or plastic.
  • the glass transition temperature Tg of the substrate is 150 ° C or higher.
  • the glass transition temperature Tg of the substrate is 200 ° C or higher.
  • the glass transition temperature Tg of the substrate is 250 ° C or higher.
  • the substrate has a glass transition temperature Tg of 300 ° C or more.
  • the flexible substrate is polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).
  • the anode comprises one of a conductive metal, a metal oxide and a conductive polymer.
  • the anode can easily inject holes into a hole injection layer (HIL), a hole transport layer (HTL), or a light-emitting layer.
  • HIL hole injection layer
  • HTL hole transport layer
  • the absolute value of the difference between the HOMO level or the valence band level is less than 0.5 eV.
  • the absolute value of the difference in the valence band energy level is less than less than 0.3 eV.
  • the work function of the anode and the absolute value of the energy level difference between the HOMO levels of the illuminants in the luminescent layer, or the work function of the anode and the HOMO energy of the p-type semiconductor material as HIL or HTL or electron blocking layer (EBL) The absolute value of the difference of the level or valence band level is less than less than 0.2 eV.
  • the anode material includes, but not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like.
  • the anode material can be obtained by a method of technical deposition, such as physical vapor deposition, including RF magnetron sputtering, vacuum thermal evaporation, and electron beam (e-beam).
  • the anode is patterned.
  • Patterned ITO conductive substrates are commercially available and can be used to make organic electronic devices.
  • the cathode comprises one of a conductive metal and a metal oxide, and the cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer.
  • the work function of the cathode and the absolute value of the LUMO energy level difference of the illuminant in the luminescent layer, or the work function of the cathode and the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer The absolute value of the difference between the LUMO level or the conduction band level of the (HBL) n-type semiconductor material is less than 0.5 eV.
  • the work function of the cathode and the absolute value of the LUMO energy level difference of the illuminant in the luminescent layer or the work function of the cathode and n as an electron injection layer (EIL) or an electron transport layer (ETL) or a hole blocking layer (HBL)
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the absolute value of the difference between the LUMO level or the conduction band level of the type semiconductor material is less than 0.3 eV.
  • the work function of the cathode and the absolute value of the LUMO energy level difference of the illuminant in the luminescent layer or the work function of the cathode and the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL)
  • EIL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • cathode materials for organic electronic devices.
  • the cathode material is one selected from the group consisting of Al, Au, Ag, Ca, Ba, Mg, LiF/Al, Mg/Ag alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO.
  • the cathode material can be prepared by physical vapor deposition. Among them, the physical vapor deposition method includes radio frequency magnetron sputtering, vacuum thermal evaporation, and electron beam (e-beam).
  • the OLED further includes other functional layers selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), and an electron transport layer (ETL). And one of a hole blocking layer (HBL).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • ETL electron injection layer
  • ETL electron transport layer
  • HBL hole blocking layer
  • the organic electronic device includes a light-emitting layer comprising one of the above-described metal organic complexes and high polymers.
  • the luminescent layer is prepared by vacuum evaporation or solution processing.
  • the organic electronic device when the organic electronic device is a light emitting device, the organic electronic device has an emission wavelength of 300 nm to 1000 nm. Further, the organic electronic device has an emission wavelength of 350 nm to 900 nm. Further, the organic electronic device has an emission wavelength of 400 nm to 800 nm.
  • the above organic electronic device can be applied to an electronic device.
  • the electronic device includes a display device, a lighting device, a light source, a sensor, and the like.
  • the synthetic steps of the metal organic complex Au-1 of the present embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the synthetic steps of the metal organic complex Au-2 of this embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the synthetic steps of the metal organic complex Au-3 of the present embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the synthetic steps of the metal organic complex Au-4 of this embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the synthetic steps of the metal organic complex Au-5 of the present embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the synthetic steps of the metal organic complex Au-6 of this embodiment are as follows:
  • Precursor A was synthesized by the method disclosed in J. Am. Chem. Soc. 2007, 129, 4350 in a yield of 45%.
  • the energy levels of the metal organic complexes Au-1, Au-2, Au-3, Au-4, Au-5, and Au-6 obtained in Examples 1 to 6 can be obtained by quantum calculation, for example, using TD-DFT (including Time-Frequency Functional Theory) By Gaussian03W (Gaussian Inc.), the specific simulation method can be found in WO2011141110.
  • TD-DFT Time-Frequency Functional Theory
  • Gaussian03W Gaussian Inc.
  • HOMO(eV) ((HOMO(Gaussian) ⁇ 27.212)-0.9899)/1.1206
  • HOMO(G) and LUMO(G) are direct calculation results of Gaussian 03W, and the unit is Hartree.
  • the results are shown in Table 1:
  • the OLED device was prepared by using the metal organic complexes obtained in Examples 1 to 6, respectively, and the specific steps are as follows:
  • a, cleaning of the conductive glass substrate when used for the first time, can be washed with a variety of solvents, such as chloroform, ketone, isopropyl alcohol, and then UV ozone plasma treatment;
  • cathode LiF / Al (1nm / 150nm) in a high vacuum (1 ⁇ 10 -6 mbar) in the thermal evaporation;
  • the device is encapsulated in a nitrogen glove box with an ultraviolet curable resin.
  • the OLED devices prepared by the metal organic complexes obtained in Examples 1 to 6 each have the following structure:
  • OLED device 1 ITO/NPD (60 nm) / 15% Au-1: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode;
  • OLED device 2 ITO/NPD (60 nm) / 15% Au-2: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode;
  • OLED device 3 ITO/NPD (60 nm) / 15% Au-3: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode;
  • OLED device 4 ITO/NPD (60 nm) / 15% Au-4: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode;
  • OLED device 5 ITO/NPD (60 nm) / 15% Au-5: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode;
  • OLED device 6 ITO/NPD (60 nm) / 15% Au-6: mCP (45 nm) / TPBi (35 nm) / LiF (1 nm) / Al (150 nm) / cathode.
  • the current-voltage luminance (JVL) characteristics of OLED devices 1 through 6 are characterized by characterization equipment while recording important parameters such as efficiency and external quantum efficiency.
  • the maximum external quantum efficiencies of the OLED devices 1 to 6 were tested to be 10.2%, 7.6%, 8.8%, 9.8%, 6.4%, and 2.4%, respectively.

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Abstract

L'invention concerne un complexe organométalique de formule générale M(L)n(L1)m(1), dans laquelle M(L) n est sélectionné parmi l'une des formules générales (2) et (3), et M est un atome de métal; L est un ligand de chélate monodenté monoanionique; L1 est un autre ligand; les formules (A) et (B) sont chacune indépendamment sélectionnées parmi une liaison double, un groupe aryle de 2 à 20 atomes de carbone, un groupe hétéroaryle de 2 à 20 atomes de carbone, et un groupe cyclique non aromatique de 2 à 20 atomes de carbone, et au plus l'une des formules (A) et (B) dans la formule générale (3) est une double liaison; Ar3 est sélectionné parmi l'un des systèmes cycliques aromatiques de 2 à 20 atomes de carbone, des systèmes cycliques hétéroaromatiques de 2 à 20 atomes de carbone, et des systèmes cycliques non aromatiques de 2 à 20 atomes de carbone; -X- est une liaison simple, ou, X est un groupe de pontage secondaire; n est tout nombre entier de 1 à 3; m est un nombre entier de 0 à 4; et o est tout nombre entier de 0 à 2.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022237348A1 (fr) * 2021-05-10 2022-11-17 The University Of Hong Kong Composés d'or (iii) luminescents ayant des propriétés de fluorescence retardée activée thermiquement (tadf) et de phosphorescence retardée stimulée thermiquement (tsdp) pour des dispositifs électroluminescents organiques et leur préparation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003084973A1 (fr) * 2002-03-26 2003-10-16 Sumitomo Chemical Company, Limited Complexes metalliques et dispositifs electroluminescents organiques
CN101128507A (zh) * 2004-12-28 2008-02-20 住友化学株式会社 高分子化合物及使用该高分子化合物的元件

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003084973A1 (fr) * 2002-03-26 2003-10-16 Sumitomo Chemical Company, Limited Complexes metalliques et dispositifs electroluminescents organiques
CN101128507A (zh) * 2004-12-28 2008-02-20 住友化学株式会社 高分子化合物及使用该高分子化合物的元件

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TO, WAI-PONG ET AL.: "Highly Luminescent Pincer Gold(III) Aryl Emitters: Thermally Activated Delayed Fluorescence and Solution-Processed OLEDs", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 56, no. 45, 5 October 2017 (2017-10-05) - 6 November 2017 (2017-11-06), pages 14036 - 14041, XP055606288, ISSN: 1433-7851, DOI: 10.1002/anie.201707193 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022237348A1 (fr) * 2021-05-10 2022-11-17 The University Of Hong Kong Composés d'or (iii) luminescents ayant des propriétés de fluorescence retardée activée thermiquement (tadf) et de phosphorescence retardée stimulée thermiquement (tsdp) pour des dispositifs électroluminescents organiques et leur préparation

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