CN117417379A - Metal complex, organic electroluminescent element comprising same, and consumer product - Google Patents

Metal complex, organic electroluminescent element comprising same, and consumer product Download PDF

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Publication number
CN117417379A
CN117417379A CN202311358155.8A CN202311358155A CN117417379A CN 117417379 A CN117417379 A CN 117417379A CN 202311358155 A CN202311358155 A CN 202311358155A CN 117417379 A CN117417379 A CN 117417379A
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substituted
unsubstituted
metal complex
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layer
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张嫣然
赵利杰
乔法杰
刘友玲
曹建华
唐怡杰
张昊
宋小东
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to a metal complex, an organic electroluminescent element containing the metal complex and a consumer product, wherein the metal complex can be used as a luminescent material to obtain a green phosphorescent material with high luminous efficiency, and the prepared luminescent material has good thermal stability; the organic electroluminescent element disclosed by the invention emits green phosphorescence and has the advantages of narrow emission spectrum, high stability and high efficiency; by incorporating the organic electroluminescent element of the present invention in an electronic device, a consumer product which emits green light and has high luminous efficiency can be obtained.

Description

Metal complex, organic electroluminescent element comprising same, and consumer product
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex, an organic electroluminescent element containing the metal complex and a consumer product.
Background
Currently, optoelectronic devices utilizing organic materials are becoming increasingly popular, and many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.
OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting.
One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color. In particular, these standards require saturated red, green and blue pixels. Alternatively, the OLED may be designed to emit white light. In conventional liquid crystal displays, the emission from a white backlight is filtered using an absorbing filter to produce red, green and blue emissions. The same technique can also be used for OLEDs. The white OLED may be a single light emitting layer (EML) device or a stacked structure. The CIE coordinates, which are well known in the art, can be used to measure color, and the luminescent materials in the prior art have poor luminescence stability and low luminescence efficiency.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a metal complex exhibiting enhanced phosphorescent quantum yield when used in an OLED, particularly in a green emission region, an organic electroluminescent element comprising the same, and a consumer product.
The first object of the present invention is to provide a metal complex which is stable in electroluminescence and high in luminous efficiency.
A second object of the present invention is to provide an organic electroluminescent element made of the metal complex.
A third object of the present invention is to provide a consumer product made of said organic electroluminescent element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a metal complex comprising a ligand of formula (LA):
wherein,
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 each independently selected from N or CR 4 And at least one is N;
R 1 selected from substituted or unsubstituted C 1 ～C 40 Chain alkyl, substituted or unsubstituted C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 1 ～C 40 Heteroalkyl, substituted or unsubstituted C 3 ～C 40 Heterocycloalkyl, substituted or unsubstituted C 6 ～C 60 Aralkyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 5 ～C 40 Cycloalkenyl, substituted or unsubstituted C 3 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, or a group consisting of the foregoing;
R 2 、R 3 、R 4 is selected identically or differently at each occurrence from the group consisting of hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, amino, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino groups; any two or more adjacent substituents may optionally be joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring;
the metal complex is formed by coordination of a ligand shown in a formula (LA) and metal M through a dotted line;
the metal complex also comprises other ligands, and the ligand shown in the formula (LA) is connected with the other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand;
the metal M is selected from one of Os, ir, pd, pt, cu, ag and Au, preferably, the metal M is selected from one of Ir, pd or Pt.
Further, the formula (LA) includes one of the following LAI to LAXVIII:
wherein R is 1 ～R 3 、X 1 ～X 8 The meaning of (A) is as defined for formula (LA).
Further, the metal complex has the chemical formula of M (LA) p (LB) q (LC) j LB, LC are bidentate ligands, p is 1, 2 or 3, q is 0, 1 or 2, j is 0, 1 or 2, and p+q+j is equal to the oxidation state of the metal M; preferably, LB is selected from one of the following structures:
Wherein Y is 1 ～Y 16 Each independently selected from N or CR 10 ，T 1 Selected from BR 12 、NR 13 、PR 14 、O、S、Se、C＝O、S＝O、SO 2 、CR 12 R 13 、SiR 12 R 13 And GeR 12 R 13 One of R 12 And R is 13 Can be optionally joined or fused to form a ring; t (T) 2 Selected from N, B, siR 12 P or p=o;
each R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 Each independently selected from hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino groups; and optionally joined or condensed between any two or more adjacent substituentsTogether forming a substituted or unsubstituted five-, six-or polycyclic ring.
The LC is as follows:
wherein R is 0 、R a 、R b 、R c 、R d 、R e 、R f Each independently selected from hydrogen, deuterium, fluorine, nitrile, substituted or unsubstituted C 1 ～C 40 Chain alkyl, substituted or unsubstituted C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 1 ～C 40 Heteroalkyl, substituted or unsubstituted C 3 ～C 40 Heterocycloalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, or a group consisting of the foregoing; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring.
Regarding the oxidation state of the metal M, when M is Ir, the oxidation valence of Ir may be 3, and when M is Pt, the oxidation valence of Pt may be 2.
"halogen", "halogen atom", "halo" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine or iodine.
"acyl" in the sense of the present invention refers to a substituted carbonyl group (COR).
"ester or ester group" in the sense of the present invention means a substituted oxycarbonyl group (-OCOR or CO) 2 R)。
An "ether OR ether group" in the sense of the present invention refers to an-OR group.
"thio" or "thioether" as described herein is used interchangeably and refers to an-SR group.
"sulfinyl" in the sense of the present invention means a-SOR group.
"sulfonyl" in the sense of the present invention"means-SO 2 An R group.
"phosphino" in the sense of the present invention means-PR 3 A group, wherein each R may be the same or different.
"silane group" in the sense of the present invention means-SiR 3 A group, wherein each R may be the same or different.
Each of the foregoing R is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.
"alkyl", "alkenyl" or "alkynyl" in the sense of the present invention are preferably taken to mean the following radicals: 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" in the sense of the present invention is preferably an alkoxy group having 1 to 40 carbon atoms, which is understood to mean 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-trifluoroethoxy.
In general, "cycloalkyl", "cycloalkenyl" according to the present invention refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are cycloalkyl groups having 3 to 15 ring carbon atoms, which may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, bicyclo [ 3.1.1:1]Heptyl, spiro [4.5 ]]Decyl, spiro [5.5 ]]Undecyl, adamantyl, and the like, wherein one or more of-CH 2 The group may be replaced by O, S or N; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
"heteroalkyl" or "heterocycloalkyl" in the sense of the present invention means alkyl or cycloalkyl, respectively, preferably having 1 to 40 carbon atoms, meaning hydrogen atom or-CH alone 2 -groups which may be substituted by oxygen, sulphur, halogen atoms, nitrogen, phosphorus, boron, silicon or selenium, preferably groups substituted by oxygen, sulphur or nitrogen. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.
"heteroalkenyl" or "heterocycloalkenyl" in the sense of the present invention means alkenyl or cycloalkenyl in which at least one carbon atom has been replaced with a heteroatom. Optionally, the at least one heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon or selenium, preferably oxygen, sulfur or nitrogen. Preferred alkenyl and cycloalkenyl groups are those containing from 3 to 15 carbon atoms. In addition, the heteroalkenyl, heterocyclenyl groups may be optionally substituted.
"aralkyl" or "arylalkyl" in the sense of the present invention is used interchangeably and refers to an alkyl group substituted with an aryl group. In addition, aralkyl groups may be optionally substituted.
"aryl" according to the present invention refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring may have two or more rings in common in which two carbons are two adjoining rings (the rings being "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenylene, tetraphenylene, naphthyl, anthracenyl, phenalenyl, phenanthrenyl, fluorenyl, pyrenyl, perylenyl, Radicals and azulene radicals, preferably phenyl, biphenyl, triphenylene, fluorenyl and naphthyl. In addition, aryl groups may be optionally substituted.
"heteroaryl" in the sense of the present invention refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems which include at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases oxygen, sulfur or nitrogen are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjoining rings (the rings being "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. The heteropolycyclic aromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoselenophenyl, carbazolyl, indolocarbazolyl, pyridylindolyl, pyrrolodipyridyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, oxazolyl, dioxazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, oxathiazinyl, oxadiazolyl, indolyl, benzimidazolyl, indazolyl, oxazinyl, and the like benzoxazolyl, benzisoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phthalazinyl, pteridinyl, xanthene (xanthene) yl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, benzofuranopyridinyl, furandipyridyl, benzothiophenopyridinyl, thienodipyridinyl, benzoselenophenopyridinyl, selenophenodipyridinyl, 1, 2-azaboryl, 1, 3-azaboryl, 1, 4-azaboryl, borazine and aza analogues thereof, dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridinyl, triazinyl, benzimidazolyl, 1, 2-azaboryl, 1, 3-azaboryl, 1, 4-azaboryl, borazaynyl and the aza analogues thereof are preferred. In addition, heteroaryl groups may be optionally substituted.
In many cases, the typical substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphine groups.
As used herein, "combination" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
In one example, the term substitution includes a combination of two to four of the listed groups.
In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms other than hydrogen or deuterium, or combinations comprising up to forty atoms other than hydrogen or deuterium, or combinations comprising up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.
Further, said R 1 、R 2 、R 3 、R 4 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 Each occurrence is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of groups;
wherein R is A1 ～R A55 The structural formula is as follows:
R B1 ～R B45 the structural formula is as follows:
R C1 ～R C295 the structural formula is as follows:
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further, the metal M is selected from one of Ir, pd or Pt.
Further, M is Ir.
Further, the chemical formula of the metal complex is Ir (LA) (LB) 2 、Ir(LA) 2 (LB)、Ir(LA) 3 Or Ir (LA) 2 (LC); wherein, LB is selected from the group consisting of LB 1-LB 432, and the concrete structure of LB 1-LB 432 is as follows:
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further, the LC is selected from the group consisting of structures shown by LC1 to LC60, and specific structures of LC1 to LC60 are as follows:
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further, the formula (LA) includes one of LA1 to LA248, and specific structures of LA1 to LA248 are as follows:
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wherein the hydrogen atoms in the structural formula may be partially or wholly substituted with deuterium atoms.
Further, the chemical formula of the metal complex is Ir (LAi) (LBj) 2 、Ir(LAi) 2 (LBj)、Ir(LAi) 3 Or Ir (LAi) 2 (LCt) wherein i is an integer of 1 to 248, j is an integer of 1 to 432, and t is an integer of 1 to 60;
the structures of LA1 to LA248, LB1 to LB432, and LC1 to LC60 are as described above.
The organic electroluminescent material of the present invention comprises one or more of the metal complexes of the present invention. The organic electroluminescent material of the present invention may be formed of only one or more of the metal complexes of the present invention, or may contain other materials than the metal complexes of the present invention.
By incorporating the metal complex of the present invention in the organic electroluminescent material of the present invention, an organic electroluminescent material having a high luminous efficiency in which electroluminescence is green emission can be obtained. In addition, the organic electroluminescent material provided by the invention is an organic electroluminescent material with good thermal stability.
An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, the organic layer comprising the metal complex.
Further, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer;
the light-emitting layer further comprises a host material and a doping material, wherein the host material comprises the following chemical groups: triphenylene, carbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, azatriphenylene, azacarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, and azadibenzoselenophenyl, or a group consisting of the foregoing.
Wherein any substituents in the host material are non-fused substituents independently selected from the group consisting of: c (C) n H 2n+1 、OC n H 2n+1 、OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 )、CH＝CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 1 、Ar 1 -Ar 2 、C n H 2n -Ar 1 Or no substituent, wherein n is an integer from 1 to 10; and wherein Ar is 1 With Ar 2 Independently selected from the group consisting of: phenyl, biphenyl, naphthyl, triphenylene, carbazolyl, and heteroaromatic analogs thereof.
Further, the doping material comprises the metal complex of the present invention.
In the organic electroluminescent element of the present invention, one of the layers may be a layer containing the metal complex of the present invention, or two or more layers may contain the metal complex of the present invention.
The organic layer may be a light emitting layer and the metal complex as described herein may be an emissive doping material or a non-emissive doping material.
The doping material is 1-100% of the mass of the main body material.
Furthermore, the metal complex is used as a doping material, and the doping material accounts for 1-50% of the mass of the main body material.
Furthermore, the metal complex is used as a doping material, and the doping material accounts for 1-10% of the mass of the main body material.
A consumer product made from the organic electroluminescent element.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Compared with the prior art, the invention has the beneficial effects that:
according to the metal complex, the boron-nitrogen heterocycle is introduced to form a large-steric-hindrance structural ligand, so that energy loss between pyridine and aryl caused by free conjugated rotation of single bonds is effectively prevented, and quantum efficiency is improved. The material has good thermal stability, the conjugated area is increased, the molecular film forming and exciton transmission performance is improved, the sublimation temperature of the material is reduced, and the material can be used as a luminescent material to obtain a green phosphorescent material with high luminous efficiency; by incorporating the organic electroluminescent element of the present invention, an electronic device can obtain a consumer product having a narrow emission spectrum, high stability and high efficiency.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a schematic view of an organic electroluminescent device according to the present invention;
FIG. 2 is a schematic view of an inverted organic electroluminescent element according to the present invention;
reference numerals
110-substrate, 115-anode layer, 120-hole injection layer, 125-hole transport layer, 130-electron blocking layer, 135-organic light emitting layer, 140-hole blocking layer, 145-electron transport layer, 150-electron injection layer, 155-protective layer, 160-cathode layer, 162-first conductive layer, 164-second conductive layer, 170-capping layer.
Detailed Description
In the organic electroluminescent element of the present invention, the constitution of the layers other than the layer containing the metal complex of the present invention is not limited at all, and the constitution of the other layers of the organic electroluminescent element can be determined by a person skilled in the art as required according to the technical knowledge in the art.
In fig. 1, an anode layer 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an organic light emitting layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode layer 160, and an encapsulation layer 170 are sequentially disposed on a substrate 110. The metal complex of the present invention is contained in the aforementioned organic light-emitting layer. When the organic electroluminescent device of the present invention is connected to an external power source and is applied with a voltage, the metal complex in the organic luminescent layer 135 is electroluminescent, and the wavelength of the emitted light ranges from 520 to 650nm. The cathode layer 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device may be manufactured by depositing the layers in sequence.
Included in fig. 2 are a substrate 110, a cathode layer 160, an organic light emitting layer 135, a hole transport layer 125, and an anode layer 115. The device may be manufactured by depositing the layers sequentially. Because the most common OLED configuration has a cathode disposed above the anode, and the present device has a cathode layer 160 disposed below the anode layer 115, the present device may be referred to as an inverted type. Materials similar to those described for the present device may be used in the corresponding layers of the present device. Fig. 2 provides an example of how some layers may be omitted from the structure of the fig. 1 device.
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 may 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. Functional OLEDs may be implemented by combining the various layers described in different ways based on design, performance, and cost factors, or several layers may be omitted entirely. 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 is understood that combinations of materials may be used, such as mixtures of host and dopant materials, or more generally, mixtures. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in fig. 2, the hole transport layer 125 transports holes and injects holes into the organic light emitting layer 135, 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, an OLED with 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, wherein at 10 -5 At a pressure of between mbar and 1 barThe material is applied. A particular example of this method is the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include producing one or more layers, for example, by spin coating, or by means of any desired printing method, such as screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a 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, vapors and/or gases, etc. The barrier layer may be deposited on the substrate, electrode, under the substrate, electrode, or beside the substrate, electrode, or on any other portion of the device, including the edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by a variety of known chemical vapor deposition techniques and may comprise a composition having a single phase as well as a composition 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 to 5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.
In any of the above mentioned compounds used in each layer of the above mentioned OLED device, 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 (e.g., without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.
The materials and structures described herein may 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, such materials and structures may be used for organic devices such as organic transistors.
These methods are generally known to those of ordinary skill in the art and they can be applied to organic electroluminescent devices comprising the compounds according to the present invention without inventive effort.
According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have found 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 is not limited to the following, and may be variously modified by those skilled in the art based on the common general knowledge in the art. The preparation method comprises the following steps:
and (3) cleaning: cleaning the glass substrate with ITO by using cleaning agents, deionized water, organic solvents and the like;
a step of forming a hole injection layer: forming a hole injection layer containing the metal complex of the present invention on the substrate by vapor deposition of a hole injection layer forming material containing the metal complex of the present invention on the anode layer by vacuum vapor deposition;
a step 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 vapor deposition 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 transport layer to form a cathode layer.
In the embodiment of the invention, the performance detection conditions of the prepared electroluminescent device are as follows:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
Metal complex: ir (LAi) (LBj) 2 Wherein i is an integer of 1 to 248 and j is an integer of 1 to 432, comprising the steps of;
the first step: preparation of triflate salt of bis-LBj iridium complex:
10.0mmol of compound LBj and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and the filter cake is washed by water and ethanol and dried in vacuum to obtain yellow solid, the obtained yellow solid is dissolved in 100mL of dichloromethane and 10mL of methanol, 5.0mmol of silver triflate is added, the mixture is stirred for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain the triflate of the compound bis-LBj iridium complex.
And a second step of: metal complexes Ir (LAi) (LBj) 2 Is prepared from
4.8mmol of compound LAi and 2.3mmol of triflate of the compound bis-LBj iridium complex prepared in the first step are dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and eluted by methylene dichloride-normal hexane to obtain a metal complex Ir (LAi) (LBj) 2 The above-mentioned LA1 to LA248 and LB1 to LB432 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) (LBj) 2 Is prepared by the general preparation method of Ir (LA 17) (LB 105) only as a metal complex 2 Is illustrated in more detail by the preparation examples:
the first step: preparation of Compound Int-1
10.0g of compound LB105 and 9.5g of IrCl 3 ·3H 2 O is dispersed in 150mL of ethylene glycol diethyl ether and 50mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and filter cakes are washed with water and ethanol and dried in vacuum to obtain 14.8g of yellow solid, the obtained yellow solid is dissolved in 250mL of dichloromethane and 25mL of methanol, 6.5g of silver triflate is added, the mixture is stirred and reacted for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain a compound Int-1, and the yield is: 83%.
And a second step of: ir (LA 17) (LB 105) metal complex 2 Is prepared from
4.8mmol of Compound LA17 and 2.3mmol of intermediate Int-1 were dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF under nitrogenUnder the protection, heating to 100 ℃, stirring and reacting for 7 days, cooling to room temperature, concentrating under reduced pressure, separating and purifying by a silica gel column, eluting with dichloromethane-normal hexane to obtain a metal complex Ir (LA 17) (LB 105) 2 Yellow solid, yield: 46%, HRMS (TOF): m/z=992.4166 [ m+h ]] + 。
Example 2
Metal complex: ir (LAi) 2 The general preparation method of (LBj), wherein i is an integer of 1 to 248 and j is an integer of 1 to 432, comprises the steps of;
the first step: preparation of triflate salt of bis-LAi iridium complex:
referring to the synthesis of the first step of example 1, the intermediate compound bis-LAi iridium complex triflate was prepared by substituting only LBj in the first step of example 1 with LAi.
And a second step of: metal complex: ir (LAi) 2 Preparation of (LBj)
Referring to the synthesis method of the second step of example 1, only LAi in the second step of example 1 was replaced with LBj, and the triflate of the compound bis-LBj iridium complex was replaced with the triflate of the compound bis-LAi iridium complex, to prepare and obtain a metal complex Ir (LAi) 2 (LBj)。
The above-mentioned LA1 to LA248 and LB1 to LB432 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) 2 General preparation of (LBj) Ir (LA 149) alone as a metal complex 2 The preparation of (LB 90) is described in more detail;
the first step: preparation of Compound Int-2
10.0mmol of compound LA149 and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and the filter cake is washed with water and ethanol and dried in vacuum to obtain yellow solid, the obtained yellow solid is dissolved in 50mL of dichloromethane and 5mL of methanol, 20.0mmol of silver triflate is added, the mixture is stirred for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain a compound Int-2, the yellow solid is obtained in a yield: 81%.
And a second step of: ir metal complex (LA 149) 2 Preparation of (LB 90)
5.0mmol of compound LB90 and 2.5mmol of intermediate Int-2 are dispersed in 15mL of ethylene glycol diethyl ether and 15mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, the reaction solution is poured into 250mL of ice water, extracted by methylene dichloride, an organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and separated and purified by a silica gel column, and methylene dichloride-n-hexane is eluted to obtain a metal complex Ir (LA 149) 2 (LB 90), dark yellow solid, yield: 45%, HRMS (TOF): m/z=1091.4359 [ m+h ]] + 。
Example 3
Ir metal complex (LAi) 3 Wherein i is an integer of 1 to 248, comprising the steps of:
the first step: preparation of LAi iridium chloro bridge complex:
9.5mmol of compound LAi and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, and the mixture is heated and refluxed for reaction for 24 hours under the protection of nitrogenAnd cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain the LAi iridium chloride bridge complex.
And a second step of: preparing a metal complex: ir (LAi) 3 ，
5.0mmol of the LAi iridium chloride bridge complex prepared in the first step, 10.0mmol of silver triflate and 12.0mmol of LAi are dispersed in 20mL of ethylene glycol diethyl ether, and under the protection of nitrogen, the mixture is heated, refluxed and stirred for reaction for 24 hours, cooled to room temperature, filtered, and the filter cake is dissolved by methylene dichloride and separated and purified by a silica gel column to obtain a metal complex Ir (LAi) 3 。
The above-mentioned LA1 to LA248 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) 3 Is prepared by the general preparation method of Ir (LA 145) only as a metal complex 3 Is illustrated in more detail by way of example;
the first step: preparation of Compound Int-3
9.5mmol of compound LA145 and 4.5mmol of IrCl 3 ·3H 2 Dispersing O in 60mL of ethylene glycol diethyl ether and 20mL of water, heating and refluxing under the protection of nitrogen for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain a compound Int-3 as a yellow solid, wherein the yield is: 74%.
And a second step of: ir metal complex (LA 145) 3 Is prepared from
5.0mmol of Int-3 prepared in the first step, 10.0mmol of silver triflate and 12.0mmol of LA145 were dispersed in 20mL of ethylene glycol monoethyl ether under nitrogenUnder the protection, heating, refluxing and stirring for reaction for 24 hours, cooling to room temperature, filtering, dissolving a filter cake with dichloromethane, and separating and purifying by a silica gel column to obtain a metal complex Ir (LA 145) 3 Yellow solid, yield: 38%, HRMS (TOF): m/z=1478.6535 [ m+h ]] + 。
Example 4
Ir metal complex (LAi) 2 The general preparation method of (LCt), wherein i is an integer of 1 to 248 and t is an integer of 1 to 60, comprises the steps of:
the first step: preparation of LAi iridium chloro bridge complex:
9.5mmol of compound LAi and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, and under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and filter cakes are washed with water and ethanol and dried in vacuum to obtain the LAi iridium chloride bridge complex.
And a second step of: preparing a metal complex: ir (LAi) 2 (LCt)，
5.0mmol of the LAi iridium chloride bridge complex prepared in the first step, 20.0mmol of LCt and 50.0mmol of anhydrous sodium carbonate are dispersed in 40mL of acetonitrile and 40mL of chloroform, the mixture is heated, refluxed and stirred for reaction for 24 hours under the protection of nitrogen, cooled to room temperature, the reaction solution is poured into ice water, an organic phase is separated, the aqueous phase is extracted by methylene dichloride, the organic phase is dried and filtered, the filtrate is concentrated under reduced pressure to dryness, and the metal complex Ir (LAi) is obtained by separation and purification by a silica gel column 2 (LCt)。
The above-mentioned LA1 to LA248 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) 2 (LCt) general preparation method with only the metal complex Ir (LA 197) 2 The preparation of (LC 4) is described in more detailA fine description;
the first step: preparation of Compound Int-4
9.5mmol of compound LA197 and 4.5mmol of IrCl 3 ·3H 2 Dispersing O in 60mL of ethylene glycol diethyl ether and 20mL of water, heating and refluxing under the protection of nitrogen for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and vacuum drying to obtain a compound Int-4 as a red solid, wherein the yield is: 76%.
And a second step of: ir metal complex (LA 197) 2 (LC 4) preparation
5.0mmol of Int-4 prepared in the first step, 20.0mmol of LC4 and 50.0mmol of anhydrous sodium carbonate are dispersed in 40mL of acetonitrile and 40mL of chloroform, the mixture is heated, refluxed and stirred for reaction for 24 hours under the protection of nitrogen, cooled to room temperature, the reaction solution is poured into ice water, an organic phase is separated, the aqueous phase is extracted by methylene dichloride, the organic phase is dried and filtered, the filtrate is concentrated and dried under reduced pressure, and the metal complex Ir (LA 197) is obtained by separation and purification by a silica gel column 2 (LC 4), red solid, 52% yield, HRMS (TOF): m/z=1041.5616 [ m+h ]] + 。
Example 5
Preparation of an organic electroluminescent element:
(1) Ultrasonic treating the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, flushing in deionized water, ultrasonic treating in an acetone/ethanol mixed solvent for 30 minutes, baking in a clean environment until the glass substrate is completely dried, irradiating for 10 minutes by an ultraviolet cleaning machine, and bombarding the surface by a low-energy cation beam;
(2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, continuing to vapor-deposit the compound HATCN as a hole injection layer on the anode layer filmThe thickness of the vapor deposition film isContinuously evaporating HTM as hole transport layer on the hole injection layer film to obtain an evaporating film with a thickness of +.>
(3) Evaporating EBM as electron blocking layer on the hole transport layer to obtain an evaporation film with a thickness of
(4) An organic light-emitting layer is deposited on the electron blocking layer, wherein the light-emitting layer contains H1 as a main material and 5% by mass of the metal complex prepared by the method of the invention as a doping material, and the thickness of the deposited film is
(5) Evaporating an electron transport layer of LiQ and ETM as elements on the organic light-emitting layer, wherein LiQ is 50% of ETM by mass, and the film thickness of the evaporated film is
(6) Continuously evaporating a LiF layer on the light-emitting layer to form an electron injection layer of the device, wherein the film thickness of the evaporated film is
(7) Depositing metal aluminum as a cathode layer of the device on the electron injection layer to form a deposited film having a thickness of
Comparative example 1
Comparative element 1 was produced in the same manner as in example 5 except that the metal complex in example 5 was replaced with the compound shown by GD-1.
The structural formulas of HATCN, HTM, EBM, H, liQ, GD-1 and ETM are as follows:
in the same manner as in example 5, an organic electroluminescent device was fabricated using the metal complex of the present invention as a dopant material for an organic light-emitting layer, and the structure and performance data thereof are summarized in Table 1, and only the metal complexes Ir (LA 1 to LA 169) (LB 105) were used as follows 2 For representative example, the data is normalized compared to the comparison element 1.
TABLE 1
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As can be seen from table 1, the metal complex of the present invention is a material for a light-emitting layer, which has a low driving voltage compared to the comparative element 1, particularly has a significantly improved external quantum efficiency and LT95% lifetime compared to the comparative element 1, and thus has a great advantage in that the metal complex of the present invention is a material for a light-emitting layer having excellent properties.
The properties of only a portion of the metal complexes are shown in Table 1 above, and the inventors have conducted the above-described experiments on other metal complexes, and the results are substantially consistent and not listed herein because of limited space.
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 will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. A metal complex comprising a ligand of formula (LA):
wherein,
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 each independently selected from N or CR 4 And at least one is N;
R 1 selected from substituted or unsubstituted C 1 ～C 40 Chain alkyl, substituted or unsubstituted C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 1 ～C 40 Heteroalkyl, substituted or unsubstituted C 3 ～C 40 Heterocycloalkyl, substituted or unsubstituted C 6 ～C 60 Aralkyl, substituted or unsubstituted C 2 ～C 40 Alkenyl, substituted or unsubstituted C 5 ～C 40 Cycloalkenyl, substituted or unsubstituted C 3 ～C 40 Heteroalkenyl, substituted or unsubstituted C 2 ～C 40 Alkynyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, or a group consisting of the foregoing;
R 2 、R 3 、R 4 is selected identically or differently at each occurrence from the group consisting of hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, amino, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino groups; any two or more adjacent substituents may optionally be joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring;
the metal complex is formed by coordination of a ligand shown in a formula (LA) and metal M through a dotted line;
the metal complex also comprises other ligands, and the ligand shown in the formula (LA) is connected with the other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand;
The metal M is selected from one of Os, ir, pd, pt, cu, ag and Au, preferably, the metal M is selected from one of Ir, pd or Pt.
2. The metal complex of claim 1, wherein the formula (LA) comprises one of the following structures LAI-LAXVIII:
wherein R is 1 ～R 3 、X 1 ～X 8 The meaning of (A) is as defined for formula (LA).
3. The metal complex of claim 1 or 2, wherein the metal complex has the formula M (LA) p (LB) q (LC) j LB and LC are bidentate ligands, p is 1, 2 or 3, q is 0, 1 or 2, j is 0, 1 or 2, and p+q+j is equal to the oxidation state of the metal M, LB is selected from one of the following structures:
wherein Y is 1 ～Y 16 Each independently selected from N or CR 10 ，T 1 Selected from BR 12 、NR 13 、PR 14 、O、S、Se、C＝O、S＝O、SO 2 、CR 12 R 13 、SiR 12 R 13 And GeR 12 R 13 One of R 12 And R is 13 Can be optionally joined or fused to form a ring; t (T) 2 Selected from N, B, siR 12 P or p=o;
R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 each independently selected from hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino groups; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring;
LC is:
wherein R is 0 、R a 、R b 、R c 、R d 、R e 、R f Each independently selected from hydrogen, deuterium, fluorine, nitrile, substituted or unsubstituted C 1 ～C 40 Chain alkyl, substituted or unsubstituted C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 1 ～C 40 Heteroalkyl, substituted or unsubstituted C 3 ～C 40 Heterocycloalkyl, substituted or unsubstituted C 3 ～C 40 Silyl, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl, or a group consisting of the foregoing; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring.
4. A metal complex according to any one of claims 1 to 3, wherein R 1 、R 2 、R 3 、R 4 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 Each occurrence is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of groups;
wherein R is A1 ～R A55 The structural formula is as follows:
R B1 ～R B45 the structural formula is as follows:
R C1 ～R C295 the structural formula is as follows:
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5. a metal complex according to any one of claims 1 to 3, wherein the metal complex has the formula Ir (LA) (LB) 2 、Ir(LA) 2 (LB)、Ir(LA) 3 Or Ir (LA) 2 (LC), wherein LB is selected from the group consisting of LB 1-LB 432, and the specific structure of LB 1-LB 432 is as follows:
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the LC is selected from the group consisting of structures shown as LC 1-LC 60, and the specific structures of the LC 1-LC 60 are as follows:
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6. The metal complex of any one of claims 1-5, wherein formula (LA) comprises one of LA 1-LA 248, and LA 1-LA 248 has the following specific structure:
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wherein hydrogen atoms in the structure may be partially or fully substituted with deuterium atoms.
7. The metal complex according to claim 5 or 6, wherein the metal complex has a chemical formula of Ir (LAi) (LBj) 2 、Ir(LAi) 2 (LBj)、Ir(LAi) 3 Or Ir (LAi) 2 (LCt) wherein i is an integer of 1 to 248, j is an integer of 1 to 432, and t is an integer of 1 to 60;
LA1 to LA248 are the structures shown in claim 6; LB1 to LB432 and LC1 to LC60 are the structures shown in claim 5.
8. An organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 7.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; wherein, the luminescent layer also comprises a host material and a doping material, and the host material comprises the following chemical groups: triphenylene, carbazolyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, azatriphenylene, azacarbazolyl, azadibenzothiophenyl, azadibenzofuranyl, and azadibenzoselenophenyl, or a group consisting of the foregoing;
The doping material comprises the metal complex according to any one of claims 1 to 7;
the doping material is 1-100% of the mass of the main body material.
10. A consumer product made from the organic electroluminescent element of claim 8 or 9.
CN202311358155.8A 2023-10-19 2023-10-19 Metal complex, organic electroluminescent element comprising same, and consumer product Pending CN117417379A (en)

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