CN116284151A - Metal complex, organic electroluminescent element comprising same, and consumer product - Google Patents
Metal complex, organic electroluminescent element comprising same, and consumer product Download PDFInfo
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- CN116284151A CN116284151A CN202310297359.9A CN202310297359A CN116284151A CN 116284151 A CN116284151 A CN 116284151A CN 202310297359 A CN202310297359 A CN 202310297359A CN 116284151 A CN116284151 A CN 116284151A
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- metal complex
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- organic electroluminescent
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 69
- 239000000463 material Substances 0.000 claims abstract description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- -1 phosphino groups Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
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- 125000003636 chemical group Chemical group 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 230000000903 blocking effect Effects 0.000 description 6
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- 238000001704 evaporation Methods 0.000 description 6
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- 239000001301 oxygen Substances 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 5
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- 239000010703 silicon Chemical group 0.000 description 5
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 125000005981 pentynyl group Chemical group 0.000 description 1
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- 229950000688 phenothiazine Drugs 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic 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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- 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
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- 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
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- 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
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- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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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
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 W is selected from O, S or NR 7 ；
X 1 、X 2 、X 3 、X 4 Each independently selected from N or CR 8
R 1 ～R 8 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; r is R 5 Is one ofOr multiple to saturated substitution, R 6 One or two, and 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;
m and n are each independently selected from 0, 1 or 2, and m+n is not less than 2;
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 structures LAI to LAIV:
wherein R is 1 ～R 6 、W、X 1 ～X 4 The meanings of m and n are the same as defined above.
Further, the metal complex has the chemical formula of M (LA) p (LB) q LB is a bidentate ligand, p is 1,2 or 3, q is 0, 1 or 2, and p+q 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; 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, cycloalkenyl groups are cycloalkyl groups containing 3 to 15 ring carbon atoms, and may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptylCycloheptenyl, bicyclo [3.1.1]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, naphthalene, anthracene, pa, phenanthrene, fluorene, pyrene, perylene,
And azulenes, preferably phenyl, biphenyl, triphenylene, fluorene and naphthalene. 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 dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene (xanthone), acridine, phenazine, phenothiazine, phenoxazine, benzofuranpyridine, furanbipyridine, benzothiophenopyridine, thienodipyridine, benzoselenophenopyridine, selenophenodipyridine, 1, 2-azaborane, 1, 3-azaborane, 1, 4-azaborane, borazine, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborane, 1, 3-azaborane, 1, 4-azaborane, borazine, and 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 5 、R 6 、R 7 、R 8 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:
further, the chemical formula of the metal complex is Ir (LA) (LB) 2 、Ir(LA) 2 (LB), or Ir (LA) 3 The method comprises the steps of carrying out a first treatment on the surface of the 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:
further, M is selected from one of Ir, pd or Pt.
Further, the formula (LA) includes one of LA1 to LA208, and the specific structure of LA1 to LA208 is as follows:
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) or Ir (LAi) 3 Wherein i is an integer of 1 to 208, and j is an integer of 1 to 432;
the structures of LA1 to LA208 and LB1 to LB432 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 further comprises a host material, wherein the host material comprises the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, nitrogen triphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, and azadibenzoselenophene.
Wherein any substituents in the host 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: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
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 dopant or a non-emissive dopant.
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, pyridine, quinoline or isoquinoline is connected with a seven-membered ring containing hetero atoms such as O or S and the like and the hetero rings above to form a large-steric-hindrance structural ligand, so that energy loss caused by conjugated free rotation of single bonds between the pyridine and aryl 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, 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 the 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- 5 The material is applied at a pressure between mbar and 1 bar. 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 208 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 LA1 to LA208 and LB1 to LB432 are 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 2) (LB 105) only as a metal complex 2 Is illustrated in more detail by the preparation examples:
the first step: preparation of Compound Iht-1
10.0g of compound LB105 and 9.5g of IrCl 3 ·3H 2 Dispersing O in 150mL of ethylene glycol diethyl ether and 50mL of water, heating and refluxing under nitrogen protection for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, vacuum drying to obtain 14.8g of yellow solid, dissolving the obtained yellow solid in the following conditionTo 250mL of methylene chloride and 25mL of methanol, 6.5g of silver triflate was added, and the mixture was stirred and reacted for 24 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure to give compound Iht-1, yield: 83%.
And a second step of: ir (LA 2) metal complex (LB 105) 2 Is prepared from
4.8mmol of compound LA2 and 2.3mmol of intermediate Int-1 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 (LA 2) (LB 105) 2 Dark yellow solid, yield: 49%, HRMS (TOF): m/z=846.3664 [ m+h ]] + 。
Example 2
Metal complex: ir (LAi) 2 The general preparation method of (LBj), wherein i is an integer of 1 to 208 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 of the second step of example 1, only LAi in the second step of example 1 was replaced with LBj, and the compound bis LBj iridium complex was replaced with triflateThe metal complex Ir (LAi) is prepared by changing the metal complex into the trifluoro methanesulfonate of the compound bis LAi iridium complex 2 (LBj)。
The LA1 to LA208 and LB1 to LB432 are as defined above.
Reference is made to the above metal complexes: ir (LAi) 2 General preparation of (LBj) Ir (LA 30) 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 LA30 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: 86%.
And a second step of: ir metal complex (LA 30) 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 30) 2 (LB 90), dark yellow solid, yield: 48%, HRMS (TOF): m/z=917.3298 [ m+h ]] + 。
Example 3
Ir metal complex (LAi) 3 Wherein i is an integer of 1 to 208, 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 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) 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 LA1 to LA208 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 161) 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 LA161 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,heating and refluxing 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 with the yield: 76%.
A second part: ir metal complex (LA 161) 3 Is prepared from
5.0mmol of Int-3 prepared in the first step, 10.0mmol of silver triflate and 12.0mmol of LA161 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 a filter cake is dissolved by methylene dichloride, and separated and purified by a silica gel column to obtain a metal complex Ir (LA 161) 3 Yellow solid, yield: 42%, HRMS (TOF): m/z=1022.3621 [ m+h ]] + 。
Example 4
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 1×10 -5 ～9×10 -3 Pa, continuing to deposit a compound HATCN as a hole injection layer on the anode layer film, the thickness of the deposited film being
Continuously 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 body and 3% by mass of the metal complex prepared by the method of the invention is used 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 4 except that the metal complex in example 4 was replaced with the compound shown by GD-1.
Comparative example 2
Comparative element 2 was produced in the same manner as in example 4 except that the metal complex in example 4 was replaced with the compound shown by GD-2.
The structural formulas of HATCN, HTM, EBM, H, liQ, GD-1, GD-2 and ETM are as follows:
the present product was used in the same manner as in example 4The structure and performance data of the organic electroluminescent element produced by using the metal complex of the invention as a dopant material for the organic light-emitting layer are summarized in Table 1, and the complex Ir (LA 1 to LA 208) (LB 105) is used alone 2 For example, the data is normalized compared to the comparison element 1.
TABLE 1
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 large advantage in that the driving voltage is low compared to comparative example 1, particularly, the external quantum efficiency and LT95% lifetime are remarkably improved compared to comparative example 1 and comparative example 2, as a doping material for a light emitting layer.
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 W is selected from O, S or NR 7 ；
X 1 、X 2 、X 3 、X 4 Each independently selected from N or CR 8 ；
R 1 ～R 8 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; r is R 5 Is one or more to saturated substitution, R 6 One or two, and 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;
m and n are each independently selected from 0, 1 or 2, and m+n is not less than 2;
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-LAIV:
wherein R is 1 ～R 6 、W、X 1 ～X 4 The meanings of m and n are 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 LB is a bidentate ligand, p is 1,2 or 3, q is 0, 1 or 2, and p+q 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.
4. A metal complex according to any one of claims 1 to 3, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 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:
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) or Ir (LA) 3 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:
6. the metal complex of any one of claims 1-5, wherein formula (LA) comprises one of LA 1-LA 208, and LA 1-LA 208 has the following specific structure:
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) or Ir (LAi) 3 Where i is an integer from 1 to 208 and j is an integer from 1 to 432.
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 of claim 8, wherein the organic layer further comprises a host material comprising the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, and azadibenzoselenophene.
10. A consumer product made from the organic electroluminescent element of claim 8 or 9.
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