WO2018113782A1 - 金属有机配合物、高聚物、混合物、组合物及有机电子器件 - Google Patents
金属有机配合物、高聚物、混合物、组合物及有机电子器件 Download PDFInfo
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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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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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Images
Classifications
-
- 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
一种金属有机配合物,具有通式M(L)n(L1)m(1),其中,M(L)n选自通式(2)及(3)中的一种,M为金属原子;L为单阴离子单齿螯合配体;L1为其他配体;式(A)和式(B)分别独立选自双键、具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基中的一种,且通式(3)中的式(A)和式(B)中的最多一个为双键;Ar3选自具有2个~20个碳原子的芳香族、具有2个~20个碳原子的杂芳香族及具有2个~20个碳原子的非芳香族环系中的一种;-X-为单键,或者,X为二桥联基;n为1~3的任一整数;m为0~4的任一整数;o为0~2的任一整数。
Description
本发明涉及有机电子器件领域,尤其涉及一种金属有机配合物、高聚物、混合物、组合物及有机电子器件。
在平板显示器和照明应用中,有机发光二极管(OLEDs)具有低成本、轻重量、低工作电压、高亮度、颜色可调性、宽视角、易装配到挠性基底上以及低能量消耗的优势,因而成为最有发展潜力的显示技术。为了提高有机发光二极管的发光效率,各种基于荧光和磷光发光材料体系已被开发出来。使用荧光材料的有机发光二极管,具有较高可靠性,但在电场激发下其内部电致发光量子效率被限制为25%。与此相反,因为激子的单重激发态和三重激发态的分支比为1:3,使用磷光材料的有机发光二极管几乎可以取得100%的内部发光量子效率。对于小分子OLED来说,通过掺杂重金属中心来有效地获取三重态激发,这提高了自旋轨道偶合并由此系间窜越到三重态。
基于金属铱(III)的配合物是广泛用于高效率OLEDs的一类材料,具有较高的效率和稳定性。Baldo等人报道了使用fac-三(2-苯基吡啶)铱(III)[Ir(ppy)3]作为磷光发光材料,4,4’-N,N’-二咔唑-联苯(4,4’-N,N’-diarbazole-biphenyl)(CBP)为基质材料的高量子效率的OLED(Appl.Phys.Lett.1999,75,4)。磷光发光材料的另一实例是天蓝色配合物双[2-(4’,6’-二氟苯基)吡啶-N,C2]-吡甲酸铱(III)(FIrpic),其掺杂到高三重态能量基质中时表现出在大约溶液中60%和在固体膜中几乎100%的极高光致发光量子效率(Appl.Phys.Lett.2001,79,2082)。尽管基于2-苯基吡啶及其衍生物的铱(III)体系已经大量用于制备OLEDs,但含有带有这些配体的其它金属中心的磷光发光材料的仍未充分研究。
尽管对磷光发光材料,特别是具有重金属中心的金属配合物的兴趣与日俱增,大多数努力仍集中于使用铱(III)、铂(II)、铜(I)和镣(II)。其它金属中心极少被关注。不同于已知表现出高效发光性质的等电子铂(II)配位化合物,发光的金(III)配合物的实例极少报道,这可能源自金(III)金属中心所具有的低能量d-d配位场(LF)的存在和金(III)金属中心的亲电性。一种提高金(III)配合物的发光效率的方式是引入强σ-给体配体,如Yam等人最早发现并合成的稳定的金(III)芳基化合物,甚至在室温下也表现出令人感兴趣的光致发光性质(J.Chem.Soc.,Dalton Trans.1993,1001)。另一令人感兴趣的给体是炔基。尽管已经大量研究了金(I)炔基配合物的发光性质,但金(III)炔基的化学基本上被忽略了,除了一个例外:6-芐基-2,2‘-联吡啶的炔基金(III)化合物的合成(J.Chem.Soc.Dalton Trans.1999,2823),但其发光性能仍未经研究过。Yam等人公开了使用各种强σ-给体炔基配体的一系列双-环金属化炔基金(III)化合物的合成,其中所有化合物在各种介质中在室温和低温下都表现出很强的发光特性(J.Am.Chem.Soc.2007,129,4350)。此外,用这些发光的金(III)化合物作为磷光掺杂剂材料制备的OLEDs外部量子效率达5.5%。这些发光金(III)化合物含有一个三齿配体和至少一个配位到金(III)金属中心上的强σ-给体基团。此后,Yam等人相继报道了金属化炔基金(III)配合物的一类新型磷光材料(J.Am.Chem.Soc.2010,132,14273)。
经过优化的蒸镀型OLED达到11.5%的EQE和37.4cd A-1的电流效率。这表明炔基金(III)配合物是有希望的发光材料。但是该类化合物的稳定性较低。
发明内容:
基于此,提供一种稳定性较高的金属有机配合物。
此外,还提供了一种高聚物、混合物、组合物及有机电子器件。
一种金属有机配合物,具有通式M(L)n(L1)m(1),其中,M(L)n选自如下通式中的一种:
M为金属原子;
L为单阴离子单齿螯合配体;
L1为双齿螯合配体或三齿螯合配体;
分别独立选自双键、具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种,且通式(3)中,中的最多一个为双键;
Ar3选自具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种;
R选自氢、氘、卤素原子、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种,其中,一个或多个R既可以彼此键合形成脂族环系或芳族环系,又可以与通式2或3键合形成脂族环系或芳族环系;
-X-为单键,或者,X为二桥联基;
n为1~3的任一整数;
m为0~4的任一整数;
o为0~2的任一整数。
一种高聚物,包括重复单元,重复单元的结构式包含上述的金属有机配合物的结构式。
一种混合物,包括上述的金属有机配合物及上述的高聚物中的一种和有机功能材料。
一种组合物,包括上述的金属有机配合物、上述的高聚物及上述的混合物中的一种,和有机溶剂。
一种有机电子器件,包括功能层,功能层的材料包括上述的金属有机配合物、上述的高聚物、上述的混合物及上述的组合物中的一种。
本发明的一个或多个实施例的细节在下面的附图和描述中提出。本发明的其它特征、目的和优点将从说明书、附图以及权利要求书变得明显。
图1为实施例1、3、4及5制得的金属有机配合物的光致发光光谱图。
为了便于理解本发明,下面将参照相关附图对本发明进行更全面的描述。附图中给出了本发明的较佳的实施例。但是,本发明可以以许多不同的形式来实现,并不限于本文所描述的实施例。相反地,提供这些实施例的目的是使对本发明的公开内容的理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体地实施例的目的,不是旨在于限制本发明。
一实施方式的金属有机配合物,具有如下通式:
M(L)n(L1)m(通式1);
其中,M为金属原子;L为单阴离子单齿螯合配体;L1为双齿螯合配体或三齿螯合配体;n为1~3的任一整数;m为0~4的任一整数。
进一步地,金属有机配合物的分结构M(L)n选自如下通式中的一种:
其中,
M为金属原子;
分别独立选自双键、具有2个~20个碳原子的芳基、具有2个~20个碳原
子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种,且通式(3)中,中的最多一个为双键;
Ar3选自具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种;
R选自氢、氘、卤素原子、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种,其中,一个或多个R既可以彼此键合形成脂族环系或芳族环系,又可以与通式2或3键合形成脂族环系或芳族环系;
-X-为单键,或者,X为二桥联基;
n为1~3的任一整数;
m为0~4的任一整数;
o为0~2的任一整数。
进一步地,M为过渡族金属原子。再进一步地,M选自铱、金、铂、镣、铑、锇、铼、镍、铜、银、锌、钨及钯中的一种。更进一步地,M选自金、铂及钯中的一种。具体地,M为金。金的化学性质稳定,且具有显著的重原子效应,能够使金属有机配合物得到高的发光效率。
在其中一个实施例中,o为1。此时,M直接与N相连。在另一个实施例中,o为0。
进一步地,及Ar3分别独立选自具有5个~20个环原子的芳族环基及具有5个~20个环原子的杂芳族环基中的一种。进一步地,及Ar3分别选自具有5个~18个环原子的芳族环基及具有5个~18个环原子的杂芳族环基中的一种。更进一步地,及Ar3分别独立选自具有5个~12个环原子的芳族环基及具有5个~18个环原子的杂芳族环基中的一种。
其中,芳族基团(芳基)指至少包含一个芳环的烃基,包括单环基团和多环的环***。杂芳族基团(杂芳基)指包含至少一个杂芳环的烃基(含有杂原子),杂芳环的烃基包括单环基团和多环的环***。这些多环的环可以具有两个或多个环,其中两个碳原子被两个相邻的环共用,即稠环。多环的这些环种,至少一个环种是芳族或杂芳族。其中,芳香族环基或杂芳香族环基中的芳香基或杂芳香基可以被短的非芳族单元间断。其中,非芳族单元为小于10%的非氢原子。进一步地,非芳族单元为小于5%的非氢原子。例如,非芳族单元为碳原子、氮原子或氧原子。因此,像9,9'-螺二芴、9,9-二芳基芴、三芳胺及二芳基醚等环系,同样认为是
芳香族环系。
具体地,芳族基团选自苯、苯的衍生物、萘、萘的衍生物、蒽、蒽的衍生物、菲、菲的衍生物、二萘嵌苯、二萘嵌苯的衍生物、并四苯、并四苯的衍生物、芘、芘的衍生物、苯并芘、苯并芘的衍生物、三亚苯、三亚苯的衍生物、苊、苊的衍生物、芴及芴的衍生物中的一种。
具体地,杂芳族基团选自呋喃、呋喃的衍生物、苯并呋喃、苯并呋喃的衍生物、噻吩、噻吩的衍生物、苯并噻吩、苯并噻吩的衍生物、吡咯、吡咯的衍生物、吡唑、吡唑的衍生物、***、***的衍生物、咪唑、咪唑的衍生物、噁唑、噁唑的衍生物、噁二唑、噁二唑的衍生物、噻唑、噻唑的衍生物、四唑、四唑的衍生物、吲哚、吲哚的衍生物、咔唑、咔唑的衍生物、吡咯并咪唑、吡咯并咪唑的衍生物、吡咯并吡咯、吡咯并吡咯的衍生物、噻吩并吡咯、噻吩并吡咯的衍生物、噻吩并噻吩、噻吩并噻吩的衍生物、呋喃并吡咯、呋喃并吡咯的衍生物、呋喃并呋喃、呋喃并呋喃的衍生物、噻吩并呋喃、噻吩并呋喃的衍生物、苯并异噁唑、苯并异噁唑的衍生物、苯并异噻唑、苯并异噻唑的衍生物、苯并咪唑、苯并咪唑的衍生物、吡啶、吡啶的衍生物、吡嗪、吡嗪的衍生物、哒嗪、哒嗪的衍生物、嘧啶、嘧啶的衍生物、三嗪、三嗪的衍生物、喹啉、喹啉的衍生物、异喹啉、异喹啉的衍生物、邻二氮萘、邻二氮萘的衍生物、喹喔啉、喹喔啉的衍生物、菲啶、菲啶的衍生物、伯啶、伯啶的衍生物、喹唑啉、喹唑啉的衍生物、喹唑啉酮及喹唑啉酮的衍生物中的一种。
在其中一个实施例中,及Ar3分别独立选自未被取代的具有5~20个环原子的非芳香族环基及被R0取代的具有5~20个环原子的非芳香族环基中的一种,以提高金属有机配合物的三线态能级,以便获得绿光发光体或蓝光发光体。
其中,非芳香族环基的环中至少包含2个碳原子。进一步地,非芳香族环基的环中包含2个~6个碳原子。非芳香族环基的环可以为饱和的环和部分饱和的环。非芳香族环基包括未被取代的非芳香族环基和被R取代的非芳香族环基。
R0包含杂原子。进一步地,R0包含Si、N、P、O、S及Ge中的至少一种。更进一步地,R0包含Si、N、P、O及S中的至少一种。例如,R0可以为类环己基或类哌啶体系的基团,也可以为类环辛二烯环状体系的基团。
具体地,R0选自C1~C10烷基、C1~C10烷氧基、C2~C10芳基及C2~C10杂芳基中的一种。其中,C1~C10烷基选自甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、2-甲基丁基、正戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟甲基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基及辛炔基中的一种。
其中,C1~C10烷氧基选自甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基及2-甲基丁氧基中的一种。
其中,C2~C10芳基及C2~C10杂芳基既能够进一步被上述R0取代,又能够与芳香环或杂
芳香环连接。
具体地,C2~C10芳基或C2~C10杂芳基选自苯、萘、蒽、嵌二萘、二氢芘、屈、茈、萤蒽、丁省、戊省、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、硫芴、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩恶嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、恶唑、苯并恶唑、萘并恶唑、蒽并恶唑、菲并恶唑、异恶唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、二氮蒽、1,5-二氮杂萘、氮咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-恶二唑、1,2,4-恶二唑、1,2,5-恶二唑、1,3,4-恶二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑。1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、中氮茚及苯并噻二唑中的一种。
需要说明的是,芳香环基和杂芳族环基不限于为上述基团,还可以选自亚联苯基、亚三联苯、芴、螺二芴、二氢菲、四氢芘及茚并芴(顺式或反式)中的一种。
其中,
A1、A2、A3、A4、A5、A6、A7、A8分别独立选自CR3及N中的一种;
Y1选自CR4R5、SiR4R5、NR3、C(=O)、S及O中的一种;
R3、R4及R5分别选自H、D、具有1个~20个碳原子的直链烷基、具有1个~20个碳原子的烷氧基、具有1个~20个碳原子的硫代烷氧基、具有3个~20个碳原子的支链烷基、具有3个~20个碳原子的环状的烷基、具有3个~20个碳原子的烷氧基、具有3个~20个碳原子的硫代烷氧基、具有3个~20个碳原子的甲硅烷基、具有1个~20个碳原子的取代的酮基、具有2个~20个碳原子的烷氧基羰基、具有7个~20个碳原子的芳氧基羰基、氰基(-CN)、氨基甲酰基(-C(=O)NH2)、卤甲酰基(-C(=O)-X,其中X代表卤素原子)、甲酰基(-C(=O)-H)、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、CF3、Cl、Br、F、可交联的基团、具有5个~40个环原子的芳基、具有5个~40个环原子的杂芳基、具有5个~40个环原子的芳氧基及具有5个~40个环原子的杂芳氧基中的至少一种。其中,R3、R4及R5之间能够键合成脂族环基或芳族环基,同时R3、R4及R5本身也能够分别键合成脂族环基或芳族环基。可交联的基团是指含有不饱和键如烯基、炔基等官能团。
更进一步地,分别独立选自环芳香烃基、芳香杂环基及含有2个~10个环结构的基团中的一种。其中,环芳香烃基选自苯基、联苯基、三苯基、苯并基、萘基、蒽基、
非那烯基、菲基、芴基、芘基、屈基、苝基及薁基中的一种;芳香杂环基选自二苯并噻吩基、二苯并呋喃基、呋喃基、噻吩基、苯并呋喃基、苯并噻吩基、咔唑基、吡唑基、咪唑基、三氮唑基、异恶唑基、噻唑基、恶二唑基、恶***基、二恶唑基、噻二唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、恶嗪基、恶噻嗪基、恶二嗪基、吲哚基、苯并咪唑基、吲唑基、吲哚嗪基、苯并恶唑基、苯异恶唑基、苯并噻唑基、喹啉基、异喹啉基、邻二氮(杂)萘基、喹唑啉基、喹喔啉基、萘基、酞基、蝶啶基、氧杂蒽基、吖啶基、吩嗪基、吩噻嗪基、吩恶嗪基、二苯并硒吩基、苯并硒吩基、苯并呋喃吡啶基、吲哚咔唑基、吡啶吲哚基、吡咯二吡啶基、呋喃二吡啶基、苯并噻吩吡啶基、噻吩吡啶基、苯并硒吩吡啶基及硒吩二吡啶基中的一种;含有2个~10个环结构的基团选自环芳香烃基及芳香杂环基中的一种,且环结构连接在一起,或者环结构通过氧原子、氮原子、硫原子、硅原子、磷原子、硼原子、链结构单元及脂肪环基团中的至少一种连接在一起。
在其中一个实施例中,X为非芳香族的桥联基。进一步地,X选自具有0个~10个碳原子的直链烷烃基、具有0个~10个碳原子的支链烷烃基、具有0个~10个碳原子的直链烯烃基、具有0个~10个碳原子的支链烯烃基、具有0个~10个碳原子的烷烃醚基、O、S、S=O、SO2、N(R)、B(R)、Si(R)2、Ge(R)2、P(R)、P(=O)R、P(R)3、Sn(R)2、C(R)2、C=O、C=S、C=Se、C=N(R)2、C=C(R)2、包含5个~20个碳原子的芳香环基及包含4个~20个碳原子的杂芳香族环基中的一种。其中,R分别独立选自氢、氘、卤素原子、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的烷烃芳香环基、具有1个~20个碳原子的烷烃杂芳香族环基及具有1个~20个碳原子的烷烃非芳香族环基中的一种。
再进一步地,X选自具有0个~5个碳原子的直链烷烃基、具有0个~5个碳原子的支链烷烃基、具有0个~5个碳原子的直链烯烃基、具有0个~5个碳原子的支链烯烃基、具有0个~5
个碳原子的烷烃醚基、包含5个~15个碳原子的芳香环基及包含4个~15个碳原子的杂芳香族环基中的一种。
更进一步地,X选自具有0个~2个碳原子的直链烷烃基、具有0个~2个碳原子的支链烷烃基、具有0个~2个碳原子的直链烯烃基、具有0个~2个碳原子的支链烯烃基、具有0个~2个碳原子的烷烃醚基、包含5个~10个碳原子的芳香环基及包含4个~10个碳原子的杂芳香族环基中的一种。
具体地,X选自如下结构式中的一种:
其中,R6、R7、R8及R9分别独立选自氢、氘、卤素原子、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种,其中,R6、R7、R8及R9可以分别自身或彼此键合形成脂族环系或芳族环系,又可以分别与通式
2或3键合形成脂族环系或芳族环系。
更具体地,X选自如下结构中的一种:
在其中一个实施例中,M(L)n包含如下分结构式中的一种:
其中,#表示与通式(3)中的Ar3或M相连的位置;-Z1-、-Z2-及-Z3-分别独立选自单键、-N(R)-、-C(R)2-、-Si(R)2-、-O-、-S-、-C=N(R)-、-C=C(R)2-及-P(R)-中的一种;
分别独立选自具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种。
进一步地,M(L)n包含如下分结构式中的一种:
其中,,#表示与通式(3)中的Ar3或M相连的位置;-Z1-、-Z2-及-Z3-分别独立选自单键、-N(R)-、-C(R)2-、-Si(R)2-、-O-、-S-、-C=N(R)-、-C=C(R)2-及-P(R)-中的一种。
具体地,M(L)n包含如下分结构式中的一种:
其中,#表示与通式(3)中的Ar3或M相连的位置;上述分结构式能够进一步被取代。
在其中一个实施例中,o为1,Ar3与M之间通过σ-键相连,Ar3为负离子单齿的强σ-给体配体。
在其中一个实施例中,Ar3选自苯、萘、蒽、芘、菲、芴、咔唑、咪唑及苯并咪唑中的一种。
进一步地,金属有机配合物选自如下通式中的一种:
其中,
X71~X73分别选自氮原子、氧原子及碳原子中的一种。进一步地,X71~X73中至少一个为氮原子;
R16~R21分别选自氢、氘、卤素原子、CN、NO2、CF3、B(OR2)2、Si(R2)3、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链
烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的烷烃硫醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种;
L为单阴离子单齿螯合配体,与上述的M(L)n中L的定义相同。。
在其中一个实施例中,上述金属有机配合物便于得到热激发延迟荧光TADF或者所谓的SingletHarvesting特性。按照Adachi et al.,Nature Vol 492,234,(2012)中公开的热激发延迟荧光TADF材料的原理,当金属有机化合物的ΔE(S1-T1)足够小时,该有机化合物的三线态激子可以通过反向内部转换到单线态激子,从而实现高效发光。
具体地,金属有机配合物的ΔE(S1-T1)≤0.30eV。进一步地,金属有机配合物的ΔE(S1-T1)≤0.25eV。再进一步地,金属有机配合物的ΔE(S1-T1)≤0.20eV。更进一步地,金属有机配合物的ΔE(S1-T1)≤0.10eV。其中,ΔE(S1-T1)为单线态能级S1和三线态能级T1的差。
需要说明的是,HOMO、LUMO、S1和T1的绝对值取决于所用的测量方法或计算方法,甚至对于相同的方法,不同评价的方法,例如在CV曲线上起始点和峰点可给出不同的HOMO/LUMO值。因此,合理有意义的比较应该用相同的测量方法和相同的评价方法进行。在本实施例中,HOMO、LUMO、S1和T1的值是基于Time-dependent DFT的模拟,但不影响其他测量或计算方法的应用。
具体地,金属有机配合物选自如下结构中的一种:
在其中一个实施例中,金属有机配合物为发光材料,金属有机配合物的发光波长为300nm~1000nm。进一步地,金属有机配合物的发光波长为350nm~900nm。更进一步地,金属有机配合物的发光波长为400nm~800nm。其中,发光是指光致发光或电致发光。进一步地,金属有机配合物的光致发光效率≥30%。再进一步地,金属有机配合物的光致发光效率≥40%。
再进一步地,金属有机配合物的光致发光效率≥50%。更进一步地,金属有机配合物的光致发光效率≥60%。
在另一个实施例中,金属有机配合物为不发光材料。
一实施方式的高聚物,包括重复单元,重复单元的结构式包含上述的金属有机配合物的结构式。在本实施例中,高聚物是非共轭高聚物,例如,通式(1)所示的金属有机配合物的结构单元在高聚物的侧链上。在另一个的实施例中,高聚物为共轭高聚物。
上述金属有机配合物或高聚物在有机电子器件的应用。其中,有机电子器件选自有机发光二极管(OLED)、有机光伏电池(OPV)、有机发光电池(OLEEC)、有机场效应管(OFET)、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)中的一种。进一步地,有机电子器件为OLED。具体地,将上述金属有机配合物用于OLED器件的发光层中。
一实施方式的混合物,包括金属有机配合物及高聚物中的一种,和有机功能材料。
其中,有机功能材料选自空穴注入材料(HIM)、空穴传输材料(HTM)、电子传输材料(ETM)、电子注入材料(EIM)、电子阻挡材料(EBM)、空穴阻挡材料(HBM)、有机基质材料(Host)、单重态发光体(荧光发光体)、热激活延迟荧光发光材料(TADF)、三重态发光体(磷光发光体)及有机染料中的一种。进一步地,有机功能材料选自发光金属有机配合物和有机染料中的一种。具体地,有机功能材料还可以为WO2010135519A1,US20090134784A1和WO 2011110277A1中公开的有机功能材料。
有机功能材料可以是小分子或高聚物材料。本文所述的小分子是指非聚合物、非低聚物、非树枝状聚合物及非共混物的分子,小分子中没有重复结构。其中,小分子的摩尔质量≤3000克/摩尔。进一步地,小分子的摩尔质量≤2000克/摩尔。更进一步地,小分子的摩尔质量≤1500克/摩尔。
高聚物(Polymer)包含均聚物(homopolymer),共聚物(copolymer),镶嵌共聚物(block copolymer)。另外在本申请中,高聚物也包含树状物(dendrimer),有关树状物的合成及应用请参见Dendrimers and Dendrons,Wiley-VCH Verlag GmbH&Co.KGaA,2002,Ed.George R.Newkome,Charles N.Moorefield,Fritz Vogtle中的介绍。
共轭高聚物(conjugated polymer)是高聚物的一种。共轭高聚物的主链(backbone)主要是由碳原子的sp2杂化轨道构成。例如:聚乙炔(polyacetylene)和poly(phenylene vinylene),其主链上的碳原子的也可以被其他非碳原子取代,而且当主链上的碳原子的sp2杂化被一些自然的缺陷打断时,仍然被认为是共轭高聚物。另外在本申请中,共轭高聚物的主链上也可以包含有芳基胺(aryl amine)、芳基磷化氢(aryl phosphine)及其他杂环芳烃(heteroarmotics)、金属有机络合物(organometallic complexes)等。
在其中一个实施例中,混合物包括金属有机配合物和有机功能材料,金属有机配合物的质量百分含量为0.01%~30%。进一步地,金属有机配合物的质量百分含量为0.1%~20%。再进一步地,金属有机配合物的质量百分含量为0.2%~15%。更进一步地,金属有机配合物的质量百分含量为2%~15%。
在其中一个实施例中,混合物包括金属有机配合物及高聚物中的一种,和三重态基质材
料。其中,金属有机配合物作为磷光发光体,金属有机配合物的重量百分比≤30wt%;进一步地,金属有机配合物的重量百分比≤20wt%;更进一步地,金属有机配合物的重量百分比≤15wt%。
在另一个实施例中,混合物包括金属有机配合物及高聚物中的一种、三重态基质材料和三重态发光体。
在另一个实施例中,混合物包括金属有机配合物及高聚物中的一种,和热激活延迟荧光发光材料(TADF)。
下面对三重态基质材料,三重态发光体和TADF材料作一些较详细的描述(但不限于此)。
1、三重态基质材料(TripletHost):
任何金属配合物或有机化合物都可以作为三重态基质材料的基质,只要其三重态能量比发光体的能量更高,特别是比三重态发光体(磷光发光体)的能量更高。
具体地,三重态基质材料的金属配合物具有如下通式:
其中,M为金属;(Y3-Y4)为二齿配体;Y3和Y4分别独立地选自C、N、O、P及S中的一种;L为辅助配体;m为整数,m的值从1到M的最大配位数;m+n是M的最大配位数。
在其中一个实施例中,M选自Cu、Au、Ir及Pt中的一种。
进一步地,三重态基质材料的金属配合物具有如下通式:
其中,(O-N)为两齿配体,金属与O原子和N原子配位。
其中,可作为三重态基质材料的有机化合物为包含有环芳香烃基的化合物或包含有芳香杂环基的化合物。其中,包含有环芳香烃基的化合物包括:苯、联苯、三苯基、苯并及芴;包含有芳香杂环基的化合物包括:二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚咔唑、吡啶吲哚、吡咯二吡啶、吡唑、咪唑、***类、恶唑、噻唑、恶二唑、恶***、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪类、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、恶唑、二苯并恶唑、苯异恶唑、苯并噻唑、喹啉、异喹啉、邻二氮杂萘、喹唑啉、喹喔啉、萘、酞、蝶啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩恶嗪、苯并呋喃吡啶、呋喃并吡啶、苯并噻吩吡啶、噻吩吡啶、苯并硒吩吡啶及硒吩苯并二吡啶。
此外,可作为三重态基质材料的有机化合物还可以为包含有2环~10环结构的基团,例如:环芳香烃基团或芳香杂环基团。其中,每个基团之间直接连接,或通过氧原子、氮原子、
硫原子、硅原子、磷原子、硼原子、链结构单元及脂肪环基团中的至少一个连接。进一步地,每个芳香基团(Ar)被氢、烷基、烷氧基、氨基、烯基、炔基、芳烷基、杂烷基、芳基及杂芳基中的一种所取代。
在其中一个实施例中,三重态基质材料的有机化合物包含以下基团中的至少一个:
其中,n为0~20的任一整数;X1-X8分别选自CR1和N中的一种;X9选自CR1R2和NR1中的一种;R1-R7分别独立地选自氢、烷基、烷氧基、氨基、烯、炔、芳烷基、杂烷基、芳基及杂芳基中的一种。
具体地,三重态基质材料选自如下结构中的一种:
2、三重态发光体(Triplet Emitter)
三重态发光体也称磷光发光体。三重态发光体为含有通式M(L)n的金属配合物。其中,M为金属元素,L为有机配体,L通过一个或多个位置键接或配位连接到M上;n为大于1的整数,优选地,n选自1、2、3、4、5及6中的一个。
进一步地,金属配合物通过一个或多个位置联接到聚合物上。具体地,金属配合物通过有机配体联接到聚合物上。
进一步地,M选自过渡金属元素、镧系元素及锕系元素中的一种。优选地,M选自Ir、Pt、Pd、Au、Rh、Ru、Os、Sm、Eu、Gd、Tb、Dy、Re、Cu及Ag中的一种。更优选地,M选自Os、Ir、Ru、Rh、Cu、Au及Pt中的一种。
其中,三重态发光体包含有螯合配体,即配体。配体通过至少两个结合点与金属配位。进一步地,三重态发光体包含有2个~3个的双齿配体或多齿配体。螯合配体有利于提高金属配合物的稳定性。
有机配体选自苯基吡啶衍生物、7,8-苯并喹啉衍生物、2(2-噻吩基)吡啶衍生物、2(1-萘基)吡啶衍生物及2苯基喹啉衍生物中的一种。进一步地,有机配体都可被取代,例如被含氟或三氟甲基取代。辅助配体选自乙酸丙酮和苦味酸中的一种。
具体地,三重态发光体的金属配合物具有如下通式:
其中,M为金属。优选地,M选自过渡金属元素、镧系元素及锕系元素中的一种;
Ar1为环状基团,其中,Ar1至少包含有一个施主原子,即有一孤对电子的原子,如氮或磷,通过施主原子使环状基团与金属配位连接;
Ar2为环状基团,其中,Ar2至少包含有一个C原子,通过C原子使环状基团与金属连接;
Ar1和Ar2由共价键联接在一起;Ar1和Ar2可各自携带一个或多个取代基团,Ar1和Ar2也可再通过取代基团联接在一起;
L为辅助配体。优选地,L为双齿螯合配体。更优选地,L为单阴离子双齿螯合配体;
m为1~3中的任一整数。优选地,m为2或3。更优选地,m为3;
n是0~2中的任一整数。优选地,n为0或1。更优选地,n为0。
其中,三重态发光体的材料及其应用可以为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.Nature 403,(2000),750-753、US 20090061681 A1、US 20090061681 A1、Adachi et al.Appl.Phys.Lett.78(2001),1622-1624、J.Kido et al.Appl.Phys.Lett.65(1994),2124、Kido et al.Chem.Lett.657,1990、US 2007/0252517 A1、Johnson et al.,JACS 105,1983,1795、Wrighton,JACS 96,1974,998、Ma et al.,Synth.Metals 94,1998,245、US 6824895、US 7029766、US 6835469、US 6830828、US 20010053462 A1、WO 2007095118 A1、US 2012004407A1、WO 2012007088A1、WO2012007087A1、WO 2012007086A1、US 2008027220A1、WO 2011157339A1、CN 102282150A及WO 2009118087A1中公开的三重态发光体的材料及其应用。
具体地,三重态发光体选自如下结构中的一种:
3、热激活延迟荧光发光材料(TADF):
传统有机荧光材料只能利用电激发形成25%的单线态激子发光,有机电子器件的内量子效率较低(最高为25%)。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间穿越,可以有效利用电激发形成的单线态激子和三线态激子发光,使有机电子器件的内量子效率达到100%。但磷光材料昂贵,材料稳定性差,器件效率滚降严重等问题限制了其在OLED中的应用。热激活延迟荧光发光材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(ΔEst),三线态激子可以通过反系间穿越转变成单线态激子发光。因此,可以充分利用电激发下形成的单线态激子和三线态激子,使有机电子器件内量子效率可达到100%。
TADF需要具有较小的单线态-三线态能级差(ΔEst)。其中,TADF的ΔEst<0.3eV。进一步地,TADF的ΔEst<0.2eV。再进一步地,TADF的ΔEst<0.1eV。更进一步地,TADF的ΔEst<0.05eV。
在其中一个实施例中,TADF可以为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.Commun.,48,2012,11392、Adachi,et.al.Nature Photonics,6,2012,253、Adachi,et.al.Nature,492,2012,234、Adachi,et.al.J.Am.Chem.Soc,134,2012,14706、Adachi,et.al.Angew.Chem.Int.Ed,51,2012,11311、Adachi,et.al.Chem.Commun.,48,2012,9580、Adachi,et.al.Chem.Commun.,48,2013,10385、Adachi,et.al.Adv.Mater.,25,2013,3319、Adachi,et.al.Adv.Mater.,25,2013,3707、Adachi,et.al.Chem.Mater.,25,2013,3038、Adachi,et.al.Chem.Mater.,25,2013,3766、Adachi,et.al.J.Mater.Chem.C.,1,2013,4599及Adachi,et.al.J.Phys.Chem.A.,117,2013,5607中公开的TADF。
具体地,TADF选自如下结构中的一种:
在其中一个实施例中,金属有机配合物用于蒸镀性OLED器件。其中,金属有机配合物的摩尔质量≤1000g/mol;进一步地,金属有机配合物的摩尔质量≤900g/mol;再进一步地,金属有机配合物的摩尔质量≤850g/mol;再进一步地,金属有机配合物的摩尔质量≤800g/mol;更进一步地,金属有机配合物的摩尔质量≤700g/mol。
在另一个实施例中,金属有机配合物用于印刷OLED器件。其中,金属有机配合物的摩尔质量≥700g/mol;进一步地,金属有机配合物的摩尔质量≥800g/mol;再进一步地,金属有机配合物的摩尔质量≥900g/mol;再进一步地,金属有机配合物的摩尔质量≥1000g/mol;更进一步地,金属有机配合物的摩尔质量≥1100g/mol。
其中,当金属有机配合物用于印刷OLED器件时,在25℃下,金属有机配合物在甲苯中的溶解度≥5mg/mL;进一步地,金属有机配合物在甲苯中的溶解度≥8mg/mL;金属有机配合物在甲苯中的溶解度≥10mg/mL。
一实施方式的组合物包括上述金属有机配合物、上述聚合物及上述混合物中的一种,和有机溶剂。
在其中一个实施例中,当组合物作为印刷油墨时,组合物可以为溶液,也可以为悬浮液。粘度和表面张力是组合物的重要参数。合适的组合物的表面张力参数适合于特定的基板和特定的印刷方法。
其中,当组合物作为印刷油墨时,在工作温度或在25℃下,组合物的表面张力为
19dyne/cm~50dyne/cm。进一步地,组合物的表面张力为22dyne/cm~35dyne/cm。更进一步地,组合物的表面张力为25dyne/cm~33dyne/cm。
在另一个实施例中,当组合物用于喷墨印刷时,在工作温度或25℃下,组合物的粘度为1cps~100cps。进一步地,组合物的粘度为1cps~50cps。再进一步地,组合物的粘度为1.5cps~20cps。更进一步地,组合物的粘度为4.0cps~20cps。
粘度可以通过很多方法调节,例如,通过选取溶剂和调节组合物中功能材料的浓度来调节粘度。其中,上述组合物可以根据印刷方法来适当调节组合物的粘度。当上述组合物包括金属有机配合物、有机功能材料和有机溶剂,或包括高聚物、有机功能材料和有机溶剂时,有机功能材料的质量百分含量为0.3%~30%。进一步地,有机功能材料的质量百分含量为0.5%~20%。再进一步地,有机功能材料的质量百分含量为0.5%~15%。更进一步地,有机功能材料的质量百分含量为0.5%~10%。更进一步地,有机功能材料的质量百分含量为1%~5%。
其中,有机溶剂包括第一溶剂,第一溶剂包括芳族溶剂、杂芳族溶剂、酮溶剂、醚溶剂及酯溶剂中的至少一种。进一步地,芳族溶剂选自脂肪族链取代的芳族溶剂和环取代的芳族溶剂中的一种。
具体地,芳族溶剂选自对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二甲苯、间二甲苯、对二甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、1-甲氧基萘、环己基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、1,3-二丙氧基苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、N-甲基二苯胺、4-异丙基联苯、1,1-二氯二苯甲烷、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘及二苄醚中的一种。
具体地,杂芳族溶剂选自2-苯基吡啶、3-苯基吡啶及4-(3-苯基丙基)吡啶中的一种。
具体地,酮溶剂选自1-四氢萘酮、2-四氢萘酮、2-(苯基环氧)四氢萘酮、6-(甲氧基)四氢萘酮、苯乙酮、苯丙酮、二苯甲酮、4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮、异佛尔酮、2,6,8-三甲基-4-壬酮、葑酮、2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、佛尔酮及二正戊基酮中的一种。
具体地,醚溶剂选自3-苯氧基甲苯、丁氧基苯、苄基丁基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本***、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚、戊醚c己醚、二辛醚、乙二醇二丁醚、二乙二醇二***、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚及四乙二醇二甲醚中的一种。
酯溶剂选自辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯及油酸烷酯中的一种。
进一步地,第一溶剂包括脂肪族酮和脂肪族醚中的至少一种。其中,脂肪族酮选自2-壬
酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、佛尔酮及二正戊基酮中的至少一种;脂肪族醚选自戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二***、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚及四乙二醇二甲醚中的至少一种。
在另一个实施例中,有机溶剂还包括第二溶剂,第二溶剂包括甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷及茚中的至少一种。
上述组合物作为涂料或印刷油墨时,能够应用于制备有机电子器件。进一步地,上述组合物通过打印或涂布的方法制备有机电子器件。
其中,打印或涂布的方法选自但不限于喷墨打印、喷印(Nozzle Printing)、活版印刷、丝网印刷、浸涂、旋转涂布、刮刀涂布、辊筒印花、扭转辊印刷、平版印刷、柔版印刷、轮转印刷、喷涂、刷涂、移印、喷印刷(Nozzle printing)及狭缝型挤压式涂布中的一种。进一步地,打印或涂布的方法选自喷墨印刷、狭缝型挤压式涂布、喷印刷及凹版印刷中的一种。
在其中一个实施例中,上述组合物还包括添加剂,添加剂选自表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂及粘接剂中的至少一种。添加剂用于调节组合物的粘度、成膜性能及附着性等。
其中,关于打印技术及对溶液的相关要求,如溶剂及浓度,粘度等详细信息,请参见Helmut Kipphan主编的《印刷媒体手册:技术和生产方法》(Handbook of Print Media:Technologies and Production Methods),ISBN 3-540-67326-1。
一实施方式的有机电子器件,包括功能层,功能层的材料包括上述的金属有机配合物及上述的高聚物中的一种。进一步地,有机电子器件包括阴极、阳极及位于阴极和阳极之间的功能层,功能层的材料包括上述金属有机配合物和上述高聚物中的一种。
其中,有机电子器件选自有机发光二极管(OLED)、有机光伏电池(OPV)、有机发光电池(OLEEC)、有机场效应管(OFET)、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管(Organic Plasmon Emitting Diode)中的一种。进一步地,有机电子器件为电致发光器件。更进一步地,有机电子器件为OLED,其中,OLED包括基片、阳极、发光层及阴极。
其中,基片可以是不透明的或透明的。透明的基片可以用来制造一个透明的发光元器件。基片可以为Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606中公开的基片。基片可以是刚性的或弹性的。进一步地,基片选自塑料、金属、半导体晶片及玻璃中的一种。具体地,基片有一个平滑的表面。更具体地,基片的表面无缺陷。
在其中一个实施例中,基片是柔性的,基片为聚合物薄膜或塑料。其中,基片的玻璃化温度Tg为150℃以上。进一步地,基片的玻璃化温度Tg为200℃以上。再进一步地,基片的玻璃化温度Tg为250℃以上。更进一步地,基片的玻璃化温度Tg为300℃以上。具体地,柔性的基片为聚对苯二甲酸乙二醇酯(PET)或聚乙二醇(2,6-萘)(PEN)。
其中,阳极包括导电金属、金属氧化物及导电聚合物中的一种。阳极能够容易地注入空穴到空穴注入层(HIL)、空穴传输层(HTL)或发光层中。在一个的实施例中,阳极的功函数和发光层中的发光体HOMO能级之间能级差绝对值,或阳极的功函数和作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV。进一步地,阳极的功函数和发光层中的发光体HOMO能级之间能级差绝对值,或阳极的功函数和作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于小于0.3eV。更进一步地,阳极的功函数和发光层中的发光体HOMO能级之间能级差绝对值,或阳极的功函数和作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于小于0.2eV。
其中,阳极材料包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。阳极材料可以使用技术沉积的方法获取,如物理气相沉积法,包括射频磁控溅射、真空热蒸发及电子束(e-beam)等。
在其中一个实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备有机电子器件。
其中,阴极包括导电金属及金属氧化物中的一种,阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在其中一个的实施例中,阴极的功函数和发光层中发光体LUMO能级差的绝对值,或阴极的功函数与作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV。进一步地,阴极的功函数和发光层中发光体LUMO能级差的绝对值,或阴极的功函数与作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.3eV。更进一步地,阴极的功函数和发光层中发光体LUMO能级差的绝对值,或阴极的功函数与作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.2eV。
一般地,可用作OLED的阴极的材料都可作为有机电子器件的阴极材料。阴极材料选自Al、Au、Ag、Ca、Ba、Mg、LiF/Al、Mg/Ag合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt及ITO中的一种。阴极材料可以采用物理气相沉积法制备。其中,物理气相沉积法包括射频磁控溅射,真空热蒸发及电子束(e-beam)等。
进一步地,OLED还包括其他功能层,其他功能层选自空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)及空穴阻挡层(HBL)中的一种。
在其中一个实施例中,有机电子器件包括发光层,发光层包括上述的金属有机配合物和高聚物中的一种。其中,发光层通过真空蒸镀或溶液加工的方法制备而成。
其中,当有机电子器件为发光器件时,有机电子器件的发光波长为300nm~1000nm。进一步地,有机电子器件的发光波长为350nm~900nm。更进一步地,有机电子器件的发光波长为400nm~800nm。
上述有机电子器件可应用于电子设备中。其中,电子设备包括显示设备、照明设备、光源及传感器等。
具体实施例部分:
实施例1
本实施例的金属有机配合物Au-1的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)金属有机配合物Au-1的合成
在充满氮气的气氛中,于一个100mL的三口烧瓶中称取氢化钠(60wt%in mineral oil,17mg,0.43mmol),用己烷清洗,通过倾滤除去上面澄清部分。向其中加入脱水THF(20mL),接着加入咔唑(72mg,0.43mmol)在室温下搅拌。反应开始时为悬浊液,经过1小时左右后投入前驱物A(198mg,0.43mmol),变成橙色的溶液。再在室温下搅拌一天,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,通过适量加入己烷进行重结晶,得到红色粉末的化合物Au-1,产率50%。
实施例2
本实施例的金属有机配合物Au-2的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)金属有机配合物Au-2的合成
在充满氮气的气氛中,于一个100mL的三口烧瓶中称取氢化钠(60wt%in mineral oil,17mg,0.43mmol),用己烷清洗,通过倾滤除去上面澄清部分。向其中加入脱水THF(20mL),接着加入二苯胺(73mg,0.43mmol)在室温下搅拌。反应开始时为悬浊液,经过1小时左右后投入前驱物A(198mg,0.43mmol),变成红色的溶液。再在60℃下搅拌一天,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,通
过适量加入己烷进行重结晶,得到红色粉末的化合物Au-2,产率35%。
实施例3
本实施例的金属有机配合物Au-3的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)金属有机配合物Au-3的合成
在一个干燥的双口瓶里放置4-溴代三苯胺(139g,0.43mmol),镁片(1032mg,43mmol),抽真空充氮气循环三次,然后加入15mL脱水THF,加入少量碘以引发格氏反应,以60℃回流4小时,制备格氏试剂,并将其直接使用。在另一反应瓶放置前驱物A(198mg,0.43mmol)和15mL脱水THF,用注射器滴加上述制备的格氏试剂。滴加后,在室温下搅拌1小时,然后加热至60℃反应一天,反应液变绿色,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,通过适量加入己烷进行重结晶,得到黄色粉末的化合物Au-3,产率10%。
实施例4
本实施例的金属有机配合物Au-4的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)金属有机配合物Au-4的合成
在充满氮气的气氛中,于一个100mL的三口烧瓶中称取氢化钠(60wt%in mineral oil,17mg,0.43mmol),用己烷清洗,通过倾滤除去上面澄清部分。向其中加入脱水THF(20mL),接着加入3,6-二叔丁基咔唑(120mg,0.43mmol)在室温下搅拌。反应开始时为悬浊液,经过1小时左右后投入前驱物A(198mg,0.43mmol),变成橙色的溶液。再在室温下搅拌一天,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,通过适量加入己烷进行重结晶,得到红色粉末的化合物Au-4,产率60%。
实施例5
本实施例的金属有机配合物Au-5的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)中间体B的合成
首先把对甲基苯基磺酰氯(7.6g,40mmol)与3,7-二溴咔唑(9.75g,30mmol)在氢氧化钾(2.24g,40mmol)在100mL丙酮并且在室温下反应3个小时。然后减压蒸馏除去溶剂,将所得固体溶于二氯甲烷(100mL),并通过硅胶短柱纯化。然后把生成的白色固体(9.54g,20mmol)与咔唑(8.35g,50mmol),磷酸钾(20.2g,100mmol),碘化亚铜(1g,5mmol),1,4-二氨基环己烷(1mL,5mmol),在150mL的1,4-二氧六环(20mL),在氮气下回流130℃反应24h,冷却到室温,向反应溶液中加水,用二氯甲烷萃取,有机相水洗最后用无水硫酸镁干燥,浓缩,然后过柱纯化,然后再把得到白色固体(1.956g,3mmol),加入氢氧化钠(2g,50mmol),在比例为50:20:20THF:MeOH:H2O下加热80℃搅拌24小时,得白色固
体,产率35%。
(3)金属有机配合物Au-5的合成
在充满氮气的气氛中,于一个100mL的三口烧瓶中称取氢化钠(60wt%in mineral oil,17mg,0.43mmol),用己烷清洗,通过倾滤除去上面澄清部分。向其中加入脱水THF(20mL),接着加入中间体B(214mg,0.43mmol)在室温下搅拌。反应开始时为悬浊液,经过1小时左右后投入前驱物A(198mg,0.43mmol),变成橙色的溶液。再在室温下搅拌一天,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,通过适量加入己烷进行重结晶,得到黄色粉末的化合物Au-5,产率35%。
实施例6
本实施例的金属有机配合物Au-6的合成步骤如下:
(1)前驱物A的合成
参照文献J.Am.Chem.Soc.2007,129,4350公开的方法合成前驱物A,产率为45%。
(2)金属有机配合物Au-6的合成
在充满氮气的气氛中,于一个100mL的三口烧瓶中称取氢化钠(60wt%in mineral oil,17mg,0.43mmol),用己烷清洗,通过倾滤除去上面澄清部分。向其中加入脱水THF(20mL),接着加入苯并吲哚(51mg,0.43mmol)在室温下搅拌。反应开始时为悬浊液,经过1小时左右后投入前驱物A(198mg,0.43mmol),变成橙色的溶液。再在室温下搅拌一天,然后减压蒸馏除去溶剂,将所得固体溶于三氯甲烷(100mL),使之通过氧化铝短柱。将馏分减压浓缩,
通过适量加入己烷进行重结晶,得到黃色粉末的化合物Au-6,产率43%。
测试:
1、金属有机配合物的能量结构的测定
实施例1~6得到的金属有机配合物Au-1、Au-2、Au-3、Au-4、Au-5及Au-6的能级可通过量子计算得到,比如利用TD-DFT(含时密度泛函理论)通过Gaussian03W(Gaussian Inc.),具体的模拟方法可参见WO2011141110。首先用半经验方法“Ground State/Hartree-Fock/Default Spin/LanL2MB”(Charge 0/Spin Singlet)来优化分子几何结构,然后有机分子的能量结构由TD-DFT(含时密度泛函理论)方法算得“TD-SCF/DFT/Default Spin/B3PW91/gen geom=connectivity pseudo=lanl2”(Charge 0/Spin Singlet)。HOMO和LUMO能级按照下面的校准公式计算,S1和T1直接使用。
HOMO(eV)=((HOMO(Gaussian)×27.212)-0.9899)/1.1206
LUMO(eV)=((LUMO(Gaussian)×27.212)-2.0041)/1.385
其中HOMO(G)和LUMO(G)是Gaussian 03W的直接计算结果,单位为Hartree。结果如表1所示:
表1实施例1~6得到的金属有机配合物的能量结构
材料 | HOMO[eV] | LUMO[eV] | T1[eV] | S1[eV] |
Au-1 | -5.18 | -3.18 | 1.87 | 1.89 |
Au-2 | -5.06 | -3.00 | 1.88 | 2.01 |
Au-3 | -5.19 | -2.90 | 2.41 | 2.44 |
Au-4 | -5.11 | -3.13 | 1.85 | 1.87 |
Au-5 | -5.25 | -3.39 | 1.79 | 1.80 |
Au-6 | -5.70 | -3.28 | 2.31 | 2.60 |
2、金属有机配合物的光物理性质的检测
将实施例1、3、4及5得到的金属有机配合物进行光致发光(PL)光谱检测,结果如图1所示。
从图1可以看出,Au-1、Au-3、Au-4和Au-5的固体的光致发光光谱中,所有咔唑类金(III)配合物的发射光谱最大峰皆位于500nm至700nm之间,说明此类型的配合物适合用于黄光和红光的电子器件。
3、OLED器件的检测
分别采用实施例1~6得到的金属有机配合物制备OLED器件,具体步骤如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、HTL(60nm),EML(45nm),ETL(35nm):在高真空(1×10-6毫巴,mbar)中分别将实施例1~6得到的金属有机配合物热蒸镀到功能层中;
c、阴极:LiF/Al(1nm/150nm)在高真空(1×10-6毫巴)中热蒸镀而成;
d、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
通过实施例1~6得到的金属有机配合物制备的OLED器件分别具有如下结构:
OLED器件1:ITO/NPD(60nm)/15%Au-1:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极;
OLED器件2:ITO/NPD(60nm)/15%Au-2:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极;
OLED器件3:ITO/NPD(60nm)/15%Au-3:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极;
OLED器件4:ITO/NPD(60nm)/15%Au-4:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极;
OLED器件5:ITO/NPD(60nm)/15%Au-5:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极;
OLED器件6:ITO/NPD(60nm)/15%Au-6:mCP(45nm)/TPBi(35nm)/LiF(1nm)/Al(150nm)/阴极。
测试:
OLED器件1~6的电流电压亮度(JVL)特性通过表征设备来表征,同时记录重要的参数如效率及外部量子效率。
经测试,OLED器件1~6的最大外部量子效率分别为10.2%,7.6%,8.8%,9.8%,6.4%,2.4%。
进一步的优化,如器件结构的优化,HTM,ETM及主体材料的组合优化,将进一步提高OLED器件的性能,特别是效率,驱动电压及寿命。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (16)
- 一种金属有机配合物,具有通式M(L)n(L1)m(1),其中,M(L)n选自如下通式中的一种:M为金属原子;L为单阴离子单齿螯合配体;L1选自双齿螯合配体和三齿螯合配体中的一种;分别独立选自双键、具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种,且通式(3)中,中的最多一个为双键;Ar3选自具有2个~20个碳原子的芳基、具有2个~20个碳原子的杂芳基、具有2个~20个碳原子的非芳香族环基、被R取代的具有2个~20个碳原子的芳基、被R取代的具有2个~20个碳原子的杂芳基及被R取代的具有2个~20个碳原子的非芳香族环基中的一种;R选自氢、氘、卤素原子、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种;-X-为单键,或者,X为二桥联基;n为1~3的任一整数;m为0~4的任一整数;o为0~2的任一整数。
- 根据权利要求1所述的金属有机配合物,其特征在于,所述M选自铱、金、铂、镣、铑、锇、铼、镍、铜、银、锌、钨及钯中的一种。
- 其中,A1、A2、A3、A4、A5、A6、A7及A8分别独立选自CR3及N中的一种;Y1选自CR4R5、SiR4R5、NR3、C(=O)、S及O中的一种;R3、R4及R5分别独立选自H、D、具有1个~20个碳原子的直链烷基、具有1个~20个碳原子的烷氧基、具有1个~20个碳原子的硫代烷氧基、具有3个~20个碳原子的支链烷基、具有3个~20个碳原子的环状的烷基、具有3个~20个碳原子的烷氧基、具有3个~20个碳原子的硫代烷氧基、具有3个~20个碳原子的甲硅烷基、具有1个~20个碳原子的取代的酮基、具有2个~20个碳原子的烷氧基羰基、具有7个~20个碳原子的芳氧基羰基、氰基、氨基甲酰基、卤甲酰基、甲酰基、异氰基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基、羟基、硝基、CF3、Cl、Br、F、可交联的基团、具有5个~40个环原子的芳基、具有5个~40个环原子的杂芳基、具有5个~40个环原子的芳氧基及具有5个~40个环原子的杂芳氧基中的至少一种。
- 根据权利要求1~2任意一项所述的金属有机配合物,其特征在于,所述o为1,Ar3为负离子单齿的强σ-给体配体。
- 根据权利要求1~2任意一项所述的金属有机配合物,其特征在于,所述Ar3选自苯、萘、蒽、芘、菲、芴、咔唑、咪唑及苯并咪唑中的一种。
- 根据权利要求1~2任意一项所述的金属有机配合物,其特征在于,所述金属有机配合物选自如下通式中的一种:其中,X71~X73分别选自氮原子、氧原子及碳原子中的一种;R16~R21分别选自氢、氘、卤素原子、CN、NO2、CF3、B(OR2)2、Si(R2)3、具有1个~20个碳原子的直链烷烃基、具有1个~20个碳原子的支链烷烃基、具有1个~20个碳原子的直链烯烃基、具有1个~20个碳原子的支链烯烃基、具有1个~20个碳原子的烷烃醚基、具有1个~20个碳原子的烷烃硫醚基、具有1个~20个碳原子的芳基、具有1个~20个碳原子的杂芳基及具有1个~20个碳原子的非芳香族环基中的一种;L为单阴离子单齿螯合配体。
- 一种高聚物,包括重复单元,所述重复单元的结构式包含权利要求1~10任意一项所述的金属有机配合物的结构式。
- 一种混合物,包括权利要求1~10任意一项所述的金属有机配合物及权利要求11所述的高聚物中的一种和有机功能材料。
- 根据权利要求12所述的混合物,其特征在于,所述有机功能材料选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、有机基质材料、单重态发光体、热激活延迟荧光发光材料、三重态发光体及有机染料中的一种。
- 一种组合物,包括权利要求1~10任意一项所述的金属有机配合物、权利要求11所述的高聚物及权利要求12~13任意一项所述的混合物中的一种,和有机溶剂。
- 一种有机电子器件,包括功能层,所述功能层的材料包括权利要求1~10任意一项所述的金属有机配合物、权利要求11所述的高聚物、权利要求12~13任一项所述混合物及权利要求14所述的组合物中的一种。
- 根据权利要求15所述的有机电子器件,其特征在于,所述有机电子器件选自有机发光二极管、有机光伏电池、有机发光电池、有机场效应管、有机发光场效应管、有机激光器、有机自旋电子器件、有机传感器及有机等离激元发射二极管中的一种。
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