CN114591372A - Metal complex and application thereof - Google Patents

Metal complex and application thereof Download PDF

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CN114591372A
CN114591372A CN202210186319.2A CN202210186319A CN114591372A CN 114591372 A CN114591372 A CN 114591372A CN 202210186319 A CN202210186319 A CN 202210186319A CN 114591372 A CN114591372 A CN 114591372A
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metal complex
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CN114591372B (en
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曹建华
冯静
郭文龙
边坤
唐怡杰
邸庆童
刘赛赛
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Shanghai 800 Million Spacetime Advanced Material Co ltd
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    • C—CHEMISTRY; METALLURGY
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to a metal complex and application thereof. The metal complex is a novel carbazole, carboline or azacarbazole ligand and can be used as an electrophosphorescent luminescent material, and the metal complex is red in electroluminescence, high in luminous efficiency, good in thermal stability, easy to prepare, easy to sublimate and purify and wide in market prospect.

Description

Metal complex and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent display, in particular to a metal complex and application thereof.
Background
Organic electroluminescent diodes (OLEDs), which use organic thin films, emit light when a voltage is applied across the positive and negative electrodes of the device. OLEDs are becoming increasingly attractive as technology in flat panel displays, lighting and backlighting applications.
One application of phosphorescent emissive molecules is in full color displays, and industry standards for such displays require pixels adapted to emit a specific color. In particular, these standards require saturated red, green and blue pixels, which can be measured using CIE coordinates well known in the art.
An example of a red emissive molecule is bis (1-phenylisoquinoline) iridium acetylacetonate, denoted Ir (piq)2(acac) having the structure:
Figure BDA0003523591580000011
in this structural formula and the following structural formulae, the coordinate bond of metallic iridium to nitrogen is depicted as a straight line.
At present, the red phosphorescent material still has the problems of low luminescence quantum efficiency and poor color purity. The main reason for this is that red light comes from the transition between energy levels with narrow energy gaps, while the heavy metal complex with narrow forbidden band has a certain difficulty in ligand design, and secondly, the red light material system has strong pi-pi bond interaction, and the ligands have strong charge transfer characteristics, so that more radiationless relaxation channels exist in the narrow band gap, which aggravates the quenching of the phosphor and reduces the quantum yield of the red light system. Therefore, designing and synthesizing metal complexes with excellent comprehensive performance becomes an important subject of organic electroluminescent material research.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a metal complex and application thereof, and a luminescent material prepared by using the metal complex has good stability, and the metal complex is a red-light phosphorescent material with excellent luminescent property.
In a first aspect of the present invention, there is provided a metal complex, wherein the metal complex has the formula: m (L)A)x(LC)y(ii) a Wherein the content of the first and second substances,
m is a metal atom having an atomic weight greater than 40;
x represents an integer of 1, 2 or 3; y represents an integer of 0 or 1; and x + y is equal to the oxidation state of metal M;
LAcomprises the following steps:
Figure BDA0003523591580000021
wherein the content of the first and second substances,
X1、X2、X3、X4、X5、X6、X7each independently represents CR0Or N;
y is selected from N, B, SiR1P or P ═ O;
at W1、W2、W3、W4Any two adjacent groups in the above formula (1) or (2),
Figure BDA0003523591580000022
g is selected from O, S, CR2R3、NR4、SiR2R3Or GeR2R3(ii) a Z independently represent CR which may be the same or different5Or N, and ^ LACorresponding adjacent group W in (1)1And W2、W2And W3Or W3And W4；
R0、R1、R2、R3、R4、R5Each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, an alkenyl group, a cycloalkenyl group, an isoalkenyl group, an alkynyl group, an aryl group, a heterocyclic group, and a heterocyclic group,One or more of heteroaryl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfur group, sulfonyl, sulfinyl, phosphino and phosphino; any adjacent substituents are optionally joined or fused to form a polycyclic ring, preferably a five-membered or six-membered ring;
LCcomprises the following steps:
Figure BDA0003523591580000023
wherein the content of the first and second substances,
R6、R7、R8each independently selected from one or more of a hydrogen atom, a deuterium atom, a halogen atom, an alkane group, a cycloalkyl group, a heteroalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silane group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, and a heterocyclic aryl group; and R is6、R7、R8Optionally joined or fused to form a polycyclic ring, preferably a five-membered or six-membered ring;
the dotted line represents ligand LAOr LCCoordination or bonding to the metal M.
Preferably, the metal M is selected from Ir or Pt.
Preferably, L isAOne or more selected from the following structures:
Figure BDA0003523591580000024
Figure BDA0003523591580000031
wherein X1、X2、X3、X4、X5、X6、X7Each independently represents CR0Or N;
y is selected from N, B, SiR1P or P ═ O; g is selected from O, S, CR2R3、NR4、SiR2R3Or GeR2R3；
R0、R1、R2、R3、R4、R5Each independently selected from one or more of hydrogen atom, deuterium atom, halogen atom, alkyl group, cycloalkyl group, heteroalkyl group, heterocycloalkyl group, aralkyl group, alkoxy group, aryloxy group, amino group, alkenyl group, cycloalkenyl group, isoalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfonyl group, sulfinyl group, phosphino group; any adjacent substituents are optionally joined or fused to form a multi-membered ring, preferably a five-or six-membered ring.
Preferably, L isASelected from the group consisting of the following structural formulas:
Figure BDA0003523591580000032
Figure BDA0003523591580000041
Figure BDA0003523591580000051
wherein, T1Selected from single bond, O, S, C (CH)3)2、NR4Or Si (CH)3)2；
G、R0、R4、R5Have the same meanings as defined above.
Preferably, X is1、X2、X3、X4、X5、X6、X7Each independently represents CR0Or N; y is selected from N or B; g is selected from O, S, CR2R3Or NR4；
R0、R2、R3、R4、R5、R6、R7、R8Each independently selected from hydrogen atom, deuterium atom, RA1-RA55、RB1-RB45、RC1-RC295A group of compounds; wherein the content of the first and second substances,
RA1-RA55the structural formula is as follows:
Figure BDA0003523591580000052
Figure BDA0003523591580000061
RB1-RB45the structural formula is as follows:
Figure BDA0003523591580000062
Figure BDA0003523591580000071
RC1-RC295the structural formula is as follows:
Figure BDA0003523591580000072
Figure BDA0003523591580000081
Figure BDA0003523591580000091
Figure BDA0003523591580000101
Figure BDA0003523591580000111
Figure BDA0003523591580000121
preferably, L isAOne selected from formula LA 1-formula LA225, formula LA 1-formula LA225 has the following specific structure:
Figure BDA0003523591580000122
Figure BDA0003523591580000131
Figure BDA0003523591580000141
Figure BDA0003523591580000151
Figure BDA0003523591580000161
preferably, Lc is selected from one of formula LC 1-formula LC40, and the specific structure of formula LC 1-formula LC40 is as follows:
Figure BDA0003523591580000171
preferably, the metal complex has a formula of Ir (LAi)3、Ir(LAi)2(LCw) or Pt (LAi) (LCw); wherein i is an integer of 1 to 225, and w is an integer of 1 to 40;
preferably, the metal complex has the formula Ir (LAi)3Or Ir (LAi)2(LCw)。
"halo", "halogen atom" or "halide" in the sense of the present invention includes fluorine, bromine and iodine.
Alkyl in the sense of the present invention covers both straight-chain and branched alkyl radicals, the preferred alkyl radicals being those containing from 1 to 40 carbon atoms and in which a single hydrogen atom or-CH2Alkyl radicals which may also be substituted include, in particular, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
Alkoxy, preferably alkoxy having 1 to 40 carbon atoms, is to be understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2,2, 2-trifluoroethoxy.
Heteroalkyl is preferably alkyl having 1 to 40 carbon atoms, meaning that the individual hydrogen atoms or-CH2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propyneThio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present2The radicals may be replaced by alkyl or alkoxy radicals as defined above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Alkynyl in the sense of the present invention encompasses straight-chain and branched alkynyl groups, preferably alkynyl is alkynyl having 2 to 40 carbon atoms.
Alkenyl in the sense of the present invention comprises straight-chain and branched alkenyl groups, preferably alkenyl is alkenyl having 2 to 40 carbon atoms.
"aralkyl" or "arylalkyl" in the sense of the present invention are used interchangeably and comprise alkyl groups having an aromatic group as a substituent, in addition, aralkyl groups may be optionally substituted.
An aryl or aromatic group in the sense of the present invention contains from 5 to 60 carbon atoms and a heteroaryl group in the sense of the present invention contains from 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl groups herein encompass monocyclic groups and polycyclic ring systems. Polycyclic rings can have two carbons that are two contiguous rings or two or more rings in common, referred to as "fused," where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls.
The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl groups may be optionally substituted with one or more substituents selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, cyclic amino, silane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
As described herein, "substituted" means that a substituent other than hydrogen is bonded to the relevant position, e.g., carbon. Thus, for example, at R0When monosubstituted, then one R0Must not be hydrogen. Similarly, at R0When disubstituted, then two R0Must not be hydrogen. Similarly, at R0When unsubstituted, R0Hydrogen for all available locations.
It is understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be as if it is a fragment, such as phenyl, phenylene, naphthyl, dibenzofuranyl, either as it is a whole molecule or as if it is written as if it is an entire molecule. These different ways of naming the substituents or connecting the fragments are considered to be equivalent.
The second object of the present invention is to provide the use of the metal complex described above for the preparation of organic electroluminescent elements or organic electroluminescent materials.
A third object of the present invention is to provide an organic electroluminescent device, which comprises a substrate, an anode, a cathode, a capping layer, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex.
In some embodiments, the organic layer may be an emissive layer and the compound as described herein may be an emissive dopant or a non-emissive dopant.
In some embodiments, the organic layer may further comprise a host, wherein the host comprises at least one selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5, 9-dioxa-13 b-boranaphtho [3,2,1-de]Anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene and aza- (5, 9-diaza-13 b-boranaphtho [3,2, 1-de)]Anthracene), wherein any substituents in the host group are independentA non-fused substituent selected from the group consisting of: cnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、NAr1Ar2、CH＝CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1Or no substituent, wherein n is an integer of 1-10; and wherein Ar1And Ar2Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
Preferably, the host material contained in the organic layer is selected from the group consisting of:
Figure BDA0003523591580000191
and combinations thereof.
In some embodiments, the organic layer may further comprise a host and a dopant, wherein the dopant comprises a metal complex disclosed herein.
In some embodiments, a metal complex as described herein may be a sensitizer; wherein the device may further comprise a receptor; and wherein the receptor may be selected from the group consisting of: fluorescent emitters, delayed fluorescent emitters, and combinations thereof.
In yet another aspect, the OLEDs disclosed herein can further comprise an emissive region containing a compound as disclosed in the compounds section above as disclosed herein.
Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. Fig. 1 shows a schematic diagram of an organic electroluminescent device 100. The illustrations are not necessarily drawn to scale. The organic electroluminescent device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic diagram of an inverted organic electroluminescent device 200. The organic electroluminescent device 200 includes a substrate 201, a cathode 202, an emission layer 203, a hole transport layer 204, and an anode 205. The organic electroluminescent device 200 may be prepared by sequentially depositing the described layers. Because the most common OLED devices have a cathode disposed over an anode, while the organic electroluminescent device 200 has a cathode 202 disposed under an anode 205, the organic electroluminescent device 200 may be referred to as an "inverted" organic light emitting device. In the corresponding layer of the organic electroluminescent device 200, materials similar to those described with respect to the organic electroluminescent device 100 may be used. Fig. 2 provides one example of how some layers may be omitted from the structure of the organic electroluminescent device 100.
The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be realized by combining the various layers described in different ways, or several layers may be omitted altogether, based on design, performance and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as mixtures of a host and a dopant, or more generally, mixtures. Also, the layer may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in the organic electroluminescent device 200, the hole transport layer 204 transports holes and injects holes into the light emitting layer 203, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.
Structures and materials not specifically described, such as PLEDs comprising polymeric materials, may also be used. As another example, OLEDs having a single organic layer or multiple stacks may be used. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve optical coupling.
Any of the layers of the various embodiments may be deposited by any suitable method, unless otherwise specified. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or application of one or more layers by means of carrier gas sublimation, where at 10-5The material is applied at a pressure between mbar and 1 bar. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured. Other suitable deposition methods include creating one or more layers, for example by spin coating, or by any desired printing method, such as screen printing, flexographic printing, lithography, photo-induced thermal imaging, thermal transfer, ink jet printing, or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
Devices fabricated according to embodiments of the present invention may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapor, and/or gas, among others. The barrier layer may be deposited on or under the substrate, electrode, or beside the substrate, electrode, or on any other part of the device, including the edge. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer comprises a mixture of polymeric and non-polymeric materials. To be considered a mixture, the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same conditions and/or at the same time. The weight ratio of polymeric material to non-polymeric material may be in the range of 95/5-5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric and inorganic silicon.
In any of the above-mentioned compounds used in each layer of the above-described OLED devices, the hydrogen atoms may be partially or fully deuterated. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be non-deuterated, partially-deuterated, and fully-deuterated forms thereof.
The materials and structures described herein can be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. Further, organic devices such as organic transistors may use the materials and structures.
In some embodiments, the organic layer comprises an emissive layer and the metal complex is an emissive material.
In some embodiments, the organic layer further comprises a host material.
In some embodiments, the organic layer further comprises at least two host materials.
Materials described herein as suitable for use in a particular layer in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. The materials described or referenced below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of ordinary skill in the art can readily review the literature to identify other materials that can be used in combination.
A fourth object of the present invention is to provide a consumer product comprising an OLED, wherein the OLED comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex described above.
In some embodiments, the consumer product may be one of the following: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior lighting and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet computer, a phablet, a Personal Digital Assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay at a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall containing multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.
Preparation methods are generally known to those skilled in the art, and they can apply them to organic electroluminescent elements comprising the metal complexes according to the invention without inventive effort.
According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have discovered that the introduction of these ligands unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and increases the luminous efficiency of the device.
The method for producing the organic electroluminescent element of the present invention includes the following methods, but is not limited thereto, and those skilled in the art can variously change the method according to the general knowledge in the art. The preparation method comprises the following steps:
a cleaning procedure: cleaning the glass substrate with the ITO by using a cleaning agent, deionized water, an organic solvent and the like;
step of forming a hole injection layer: a hole injection layer forming material containing the metal complex of the present invention is vapor-deposited on the anode layer by vacuum vapor deposition, thereby forming a hole injection layer containing the metal complex of the present invention on the substrate;
step (2) of forming a hole transport layer: forming a hole transport layer on the hole injection layer by vacuum evaporation;
a step of forming an organic light-emitting layer: forming an organic light-emitting layer containing the metal complex of the present invention on the hole transport layer by vacuum evaporation of an organic light-emitting layer-forming material containing the material of the present invention on the hole transport layer;
a step of forming an electron transport layer: forming an electron transport layer containing the metal complex of the present invention on the organic light-emitting layer by vacuum evaporation of an electron transport layer forming material containing the metal complex of the present invention on the organic light-emitting layer;
a step of forming a cathode layer: a cathode forming material is vapor-deposited, sputtered, or spin-coated on the electron transporting layer to form a cathode layer.
Compared with the prior art, the invention has the beneficial effects that:
the metal complex is a novel carbazole, carboline or azacarbazole ligand, can be used as an electrophosphorescent luminescent material, is red in electroluminescence, has high luminous efficiency, and simultaneously has good thermal stability, easy preparation and sublimation purification, and has very wide market prospect.
Drawings
FIG. 1 is a schematic view of an organic electroluminescent device 100 according to the present invention;
in fig. 1, 101 denotes a substrate, 102 denotes an anode layer, 103 denotes a hole injection layer, 104 denotes a hole transport layer, 105 denotes an electron blocking layer, 106 denotes a light emitting layer, 107 denotes a hole blocking layer, 108 denotes an electron transport layer, 109 denotes an electron injection layer, 110 denotes a cathode layer, and 111 denotes a CPL layer.
FIG. 2 is a schematic view of an inverted organic electroluminescent device 200 according to the present invention;
in fig. 2, 201 denotes a substrate, 202 denotes a cathode, 203 denotes a light-emitting layer, 204 denotes a hole-transporting layer, and 205 denotes an anode.
FIG. 3 is a perspective view of the compound of example 3.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are available from published commercial sources unless otherwise specified, and the percentages are by mass unless otherwise specified. The series of novel metal complexes provided by the present invention, all reactions being carried out under well-known suitable conditions, some involving simple organic preparations, for example the preparation of phenylboronic acid derivatives, can be synthesized by skilled operative skills and are not described in detail herein.
Example 1
Compound Ir (LA1)2Preparation of (LC 16):
metal complex Ir (LA1)2(LC16) a method for preparing comprising the steps of:
the first step is as follows: preparation of compound LA1
Figure BDA0003523591580000221
Dissolving 20.0mmol of carbazole in 100mL of dry THF, cooling to 0 ℃ under the protection of nitrogen, adding 24.0mmol of 65% sodium hydride in batches, stirring for reaction for 30 minutes, dropwise adding a solution of 20.0mmol of 1-chloroisoquinoline dissolved in THF, heating to room temperature, stirring for reaction for 12 hours, adding 50mL of saturated aqueous ammonium chloride solution, separating out an organic phase, extracting an aqueous phase with ethyl acetate, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the filtrate by using a silica gel column to obtain a compound LA1, a yellow solid, and the yield: 87%, GC-MS: 294.12[M]+，1HNMR(δ、CDCl3)：8.29～8.27(1H,d)；8.15～8.12(3H,m)；7.97～7.95(3H,m)；7.65～7.61(1H,m)；7.56～7.52(1H,t)；7.48～7.44(2H,m)；7.35～7.31(2H,m)；7.25～7.23(1H,m)。
the second step is that: preparation of Compound Int-1
Figure BDA0003523591580000222
10.0mmol of the compound LA1 and 5.0mmol of IrCl3·3H2Dispersing O in 30mL of ethylene glycol ethyl ether and 10mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain a compound Int-1, namely a red solid, wherein the yield is as follows: 72 percent.
The third step: compound Ir (LA1)2Preparation of (LC16)
Figure BDA0003523591580000231
Dispersing 5.0mmol of compound Int-1 and 15.0mmol of LC16 and 25.0mmol of anhydrous potassium carbonate in 40mL of acetonitrile and 40mL of chloroform, heating under reflux for 24 hours under nitrogen protection, cooling to room temperature, pouring the reaction solution into water, extracting with dichloromethane, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying the residue with silica gel column to obtain compound Ir (LA1)2(LC16), red solid, yield: 52%, HRMS: 1018.3782[ M ]]+，1HNMR(δ、CDCl3)：9.38～9.37(2H,d)；8.56～8.54(2H,m)；8.46～8.43(2H,m)；8.15～8.09(4H,m)；8.05～7.96(6H,m)；7.76～7.62(8H,m)；7.43～7.39(2H,m)；5.13(1H,s)；1.68～1.51(4H,m)；1.29～1.05(10H,m)；0.67(6H,s)；0.63(6H,s)。
Example 2
Compound Ir (LA26)2Preparation of (LC 4):
metal complex Ir (LA26)2(LC4) preparation method, comprising the following stepsThe method comprises the following steps:
the first step is as follows: preparation of Compound Int-2
Figure BDA0003523591580000232
5.0mmol of the compound LA26 and 2.5mmol of IrCl3·3H2Dispersing O in 24mL of ethylene glycol ethyl ether and 8mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain a compound Int-2, namely a red solid, wherein the yield is as follows: 59 percent.
The second step is that: compound Ir (LA26)2Preparation of (LC4)
Figure BDA0003523591580000233
Dispersing 5.0mmol of compound Int-2 and 15.0mmol of LC4 and 25.0mmol of anhydrous sodium carbonate in 40ml of acetonitrile and 40ml of chloroform, heating under reflux for 24 hours under nitrogen protection, cooling to room temperature, pouring the reaction solution into water, extracting with dichloromethane, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying the residue with silica gel column to obtain compound Ir (LA26)2(LC4), red solid, yield: 55%, HRMS: 1046.4095[ M ]]+，1HNMR(δ、CDCl3)：8.87～8.85(2H,m)；8.72～8.70(2H,d)；8.51～8.49(2H,m)；8.24～8.20(2H,m)；7.99～7.78(10H,m)；7.38～7.36(2H,d)；7.09～7.07(2H,d)；5.21(1H,s)；2.68～2.61(1H,m)；2.54(6H,s)；2.43(6H,s)；1.73～1.63(3H,m)；1.49～1.38(2H,m)；1.29～1.09(4H,m)；0.79(6H,m)；0.74(6H,m)。
Example 3
With reference to the preparation methods of example 1 and example 2, compounds were prepared: ir (LA1)2(LC4), the structure of the compound is shown in figure 3.
Example 4
Referring to the preparation methods of example 1 and example 2, compounds were prepared: ir (LAi)2(LCw), i is an integer from 1 to 225, w is an integer from 1 to 40.
Example 5
Compound Ir (LA1)3The preparation of (1):
Figure BDA0003523591580000241
5.0mmol of Ir prepared in example 4 (LA1)2(LC1) and 20.0mmol of LA1 dispersed in 50mL of glycerol, heated to 180 ℃ under nitrogen protection, stirred and reacted for 10 hours, cooled to room temperature, added dropwise to 100mL of 1N diluted hydrochloric acid, filtered, the filter cake washed with water and ethanol, and separated and purified by a silica gel column to obtain a compound Ir (LA1)3Reddish brown solid, yield: 44%, HRMS: 1072.2847[ M ]]+，1HNMR(δ、CDCl3)：9.25～9.23(1H,d)；8.58～8.56(1H,m)；8.36～8.34(1H,m)；8.26～8.24(1H,m)；8.15～8.10(2H,m)；7.96～7.91(2H,m)；7.85～7.83(1H,d)；7.75～7.71(2H,m)；7.64～7.59(1H,m)；7.51～7.49(1H,m)。
Example 6
With reference to the preparation of example 5, the compound was prepared: ir (LAi)3And i is an integer of 1 to 225.
Example 7
The embodiment provides an OLED device, as shown in fig. 1, and a method for manufacturing the OLED device includes the following steps:
(1) carrying out ultrasonic treatment on the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, washing the glass substrate in deionized water, carrying out ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baking the glass substrate in a clean environment until the glass substrate is completely dried, irradiating the glass substrate for 10 minutes by using an ultraviolet light cleaning machine, and bombarding the surface by using low-energy cation beams;
(2) placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5-9×10-3Pa, evaporating aluminum on the ITO film to form an anode layer with a thickness of
Figure BDA0003523591580000242
Continue to divide intoDepositing HI01 as hole injection layer to obtain a film thickness of
Figure BDA0003523591580000243
Continuously depositing HTM on the hole injection layer film to form a hole transport layer, wherein the deposition film has a thickness of
Figure BDA0003523591580000244
(3) Continuously evaporating a layer of compound RP on the hole transport layer as an electron blocking layer, wherein the thickness of the evaporated film is
Figure BDA0003523591580000245
(4) Continuously evaporating a layer of the metal complex and TDC of the invention on the electron barrier layer to be used as a light emitting layer of the device, wherein the TDC is a main material and the metal complex of the invention is a doping material, the doping concentration of the metal complex of the invention is 3 percent, and the thickness of the evaporated film is
Figure BDA0003523591580000246
(5) Evaporating a layer of LiQ and ET materials on the luminescent layer to be used as an electron transport layer of the device, wherein the mass ratio of LiQ to ET is 3:2, and the thickness of the evaporated film is
Figure BDA0003523591580000247
Finally, a magnesium/silver alloy layer is sequentially evaporated on the electron transport layer to be used as a cathode layer of the device, wherein the mass ratio of the magnesium/silver alloy layer is 3:7, and the thickness of the evaporated film is
Figure BDA0003523591580000248
Comparative example 1
A comparative device EL-1 was produced in the same manner as in example 7 except that the metal complex doped material of the present invention was replaced with RD-A.
Comparative example 2
A comparative device EL-2 was produced in the same manner as in example 7 except that the metal complex doped material of the present invention was replaced with RD-B.
The specific structure of the materials used in example 7 and comparative examples 1 and 2 is shown below:
Figure BDA0003523591580000251
test examples
Devices EL-3 to EL-20 were fabricated by the method of example 7 using the different metal complexes prepared in accordance with the present invention as doping materials, and the data were normalized with EL-1 as a reference,
the roll-off ratio was calculated as follows:
roll-off ratio [1- (at a current density of 50 mA/cm)2Lower efficiency/maximum luminous efficiency)]X100%, the results are shown in Table 1.
TABLE 1
Figure BDA0003523591580000252
The metal complex of the present invention is used as a doping material of a light emitting layer, and devices EL-3 to EL-20 have a lower driving voltage and an improved light emitting efficiency than comparative devices EL-1 and EL-2, and have an initial current density of 50mA/cm2Under the condition, the LT 95% lifetime attenuation of the device is obviously improved, and a more gentle attenuation curve is shown from the data of the roll-off ratio.
The above experiments were also carried out on the metal complexes prepared in the other examples, and the results were substantially consistent and, due to the limited space, are not listed.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. A metal complex of the formula: m (L)A)x(LC)y(ii) a Wherein the content of the first and second substances,
m is a metal atom having an atomic weight greater than 40;
x represents an integer of 1, 2 or 3; y represents an integer of 0 or 1; and x + y is equal to the oxidation state of metal M;
LAcomprises the following steps:
Figure FDA0003523591570000011
wherein the content of the first and second substances,
X1、X2、X3、X4、X5、X6、X7each independently represents CR0Or N;
y is selected from N, B, SiR1P or P ═ O;
at W1、W2、W3、W4Any two adjacent groups in the above formula (1) or (2),
Figure FDA0003523591570000012
g is selected from O, S, CR2R3、NR4、SiR2R3Or GeR2R3(ii) a Z independently represent CR which may be the same or different5Or N, and ^ LACorresponding adjacent group W in (1)1And W2、W2And W3Or W3And W4；
R0、R1、R2、R3、R4、R5Each independently selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, alkyl group, cycloalkyl group, heteroalkyl group, heterocycloalkyl group, aralkyl group, alkoxy group, aryloxy group, amino group, alkenyl group, cycloalkenyl group, isoalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfonyl group, sulfinyl group, phosphine groupOne or more of a group, a phosphonoxy group; any adjacent substituents are optionally joined or fused to form a polycyclic ring, preferably a five-membered or six-membered ring;
LCcomprises the following steps:
Figure FDA0003523591570000021
wherein the content of the first and second substances,
R6、R7、R8each independently selected from one or more of a hydrogen atom, a deuterium atom, a halogen atom, an alkane group, a cycloalkyl group, a heteroalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silane group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, and a heterocyclic aryl group; and R is6、R7、R8Optionally joined or fused to form a polycyclic ring, preferably a five-membered ring or a six-membered ring;
the dotted line represents ligand LAOr LCCoordination or bonding to the metal M.
2. A metal complex according to claim 1, wherein the metal M is selected from Ir or Pt.
3. The metal complex of claim 1, wherein L isAOne or more selected from the following structures:
Figure FDA0003523591570000022
Figure FDA0003523591570000031
wherein X1、X2、X3、X4、X5、X6、X7Each independently represents CR0Or N;
y is selected from N, B, SiR1P or P ═ O; g is selectedFrom O, S, CR2R3、NR4、SiR2R3Or GeR2R3；
R0、R1、R2、R3、R4、R5Each independently selected from one or more of hydrogen atom, deuterium atom, halogen atom, alkyl group, cycloalkyl group, heteroalkyl group, heterocycloalkyl group, aralkyl group, alkoxy group, aryloxy group, amino group, alkenyl group, cycloalkenyl group, isoalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfonyl group, sulfinyl group, phosphino group; any adjacent substituents are optionally joined or fused to form a multi-membered ring, preferably a five-membered ring or a six-membered ring.
4. The metal complex of any one of claims 1 to 3, wherein L isASelected from the group consisting of the following structural formulas:
Figure FDA0003523591570000041
Figure FDA0003523591570000051
wherein, T1Selected from single bond, O, S, C (CH)3)2、NR4Or Si (CH)3)2；
G、R0、R4、R5Have the same meaning as defined in claim 1.
5. A metal complex according to any one of claims 1 to 4, wherein X is1、X2、X3、X4、X5、X6、X7Each independently represents CR0Or N; y is selected from N or B; g is selected from O, S, CR2R3Or NR4；
R0、R2、R3、R4、R5、R6、R7、R8Each independently selected from the group consisting of hydrogen atom, deuterium atom, RA1-RA55、RB1-RB45、RC1-RC295A group of compounds; wherein the content of the first and second substances,
RA1-RA55the structural formula is as follows:
Figure FDA0003523591570000052
Figure FDA0003523591570000061
RB1-RB45the structural formula is as follows:
Figure FDA0003523591570000062
Figure FDA0003523591570000071
RC1-RC295the structural formula is as follows:
Figure FDA0003523591570000072
Figure FDA0003523591570000081
Figure FDA0003523591570000091
Figure FDA0003523591570000101
Figure FDA0003523591570000111
Figure FDA0003523591570000121
Figure FDA0003523591570000131
6. a metal complex according to any one of claims 1 to 5, wherein L isAOne selected from formula LA 1-formula LA225, formula LA 1-formula LA225 has the following specific structure:
Figure FDA0003523591570000132
Figure FDA0003523591570000141
Figure FDA0003523591570000151
Figure FDA0003523591570000161
Figure FDA0003523591570000171
Figure FDA0003523591570000181
7. the metal complex as claimed in any one of claims 1 to 6, wherein Lc is selected from one of the formulas LC 1-LC 40, and the specific structure of formula LC 1-LC 40 is as follows:
Figure FDA0003523591570000191
8. the metal complex of any one of claims 1-7, wherein the metal complex has the formula Ir (LAi)3、Ir(LAi)2(LCw) or Pt (LAi) (LCw); wherein i is an integer of 1 to 225, and w is an integer of 1 to 40;
preferably, the metal complex has the formula Ir (LAi)3Or Ir (LAi)2(LCw)。
9. An organic electroluminescent element comprising a substrate, an anode, a cathode, a capping layer, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of any one of claims 1 to 8.
10. A consumer product comprising an OLED, characterized in that the OLED comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex according to any one of claims 1-8.
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