Metal complex and use thereof

Abstract

The present application relates to a kind of metal platinum complex and its application, when the metal platinum complex is used in OLED, especially when it is used in blue light emitting area, it exhibits enhanced phosphorescence quantum yield, good light stability, high luminous efficiency, and applicable as emitter material in OLED application, the metal platinum complex of the present application can obtain the organic electroluminescence device that electroluminescence is deep red phosphorescence and luminous efficiency is improved, and the thermal stability of light emitting device is good;The metal platinum complex of the present application controls its photo-physical properties by adjusting the structure of ligand around metal center and regulating the structure of substituent group on ligand, has the advantages of narrow emission spectrum, high stability and high efficiency, and has wide application prospect in many fields of OLED display and lighting lamp.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of luminescent materials, and particularly relates to a metal complex and application thereof in OLEDs. BACKGROUND

[0002] OLEDs (Organic Light Emitting Diodes) utilize organic thin films that emit light when a voltage is applied to the device. OLEDs are becoming an increasingly popular technology for use in applications such as flat panel displays, lighting, and backlights.

[0003] One application of phosphorescent emitting molecules is full color displays. Industry standards for such displays require pixels suitable for emitting specific colors. Specifically, these standards require saturated red, green, and blue pixels. Currently, red and green phosphorescent materials with 100% luminous efficiency are used in OLEDs of all sizes, while no blue phosphorescent material has been commercialized to date, although blue fluorescent materials have a luminous efficiency of only 25%, and a variety of blue light materials have been widely researched and developed, such as inorganic fluorescent powder, metal complexes, and thermally activated delayed fluorescence materials. However, there are many dissipation pathways for triplet excitons of phosphorescent materials, such as non-radiative transitions, delayed fluorescence, triplet-triplet annihilation, and quenching by oxygen and water vapor, which seriously affect the improvement of phosphorescent performance. With the discovery that crystal engineering can effectively suppress non-radiative transitions of triplet excitons using strong intermolecular interactions, and because of its dense molecular packing, it can reduce the quenching of triplet excitons by oxygen, water vapor, and other substances, it is an effective way to achieve high-efficiency room-temperature phosphorescence. However, under the crystal aggregate state, intermolecular π-π stacking easily leads to triplet-triplet annihilation, which dissipates a large number of triplet excitons and affects the improvement of phosphorescent efficiency; and π-π stacking increases the intermolecular conjugation, resulting in red-shifted emission, making it difficult to achieve blue phosphorescence. How to construct long-lived and high-efficiency blue phosphorescence is one of the challenges in the field of organic phosphorescent materials.

[0004] In view of the above reasons, the present application is proposed. SUMMARY

[0005] In order to solve the above problems existing in the prior art, the present application provides a metal complex and application thereof. When the metal complex is used in OLEDs, especially in the red light emitting region, it exhibits enhanced phosphorescent quantum yield, and is suitable for use as an emitter material in OLED applications.

[0006] The first object of the present application provides a metal complex. The metal complex has good electroluminescent stability and excellent luminous efficiency.

[0007] The second object of the present application provides application of the metal complex in organic electroluminescent devices.

[0008] A third object of the present application provides a consumer product comprising the metal complex.

[0009] In order to achieve the above object, the present application adopts the following technical solutions:

[0010] A metal complex, the general formula of which is formula (I):

[0011]

[0012] wherein, each of ring B, ring C, and ring D is a 5-membered carbon ring, a 5-membered heterocyclic ring, a 6-membered carbon ring, or a 6-membered heterocyclic ring;

[0013] X 1 ~ X 4 are each independently selected from C or N;

[0014] X 5 , X 6 , X 7 are each independently selected from CR 5 or N;

[0015] R 1 , R 2 , R 3 , R 4 each represent mono-substitution or multi-substitution to a saturated substitution, or no substitution;

[0016] L 1 , L 2 are each independently selected from a single bond, O, S, S=O, SO2, Se, NR 6 , PR 6 , R 6 P=O, CR 6 R 7 , C=O, SiR 6 R 7 , GeR 6 R 7 , or BR 8 ;

[0017] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from hydrogen or selected from the group consisting of deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfur group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphine group, a linear alkyl group having C1-C 40 , a linear alkyl group having C1-C 40straight chain heteroalkyl, having C3-C20, preferably C3-C10, more preferably C3-C6, even more preferably C3-C4, most preferably C3-C4; 40 branched or cyclic alkyl, having C1-C20, preferably C1-C10, more preferably C1-C6, even more preferably C1-C4, most preferably C1-C4; 40 alkoxy, having C1-C20, preferably C1-C10, more preferably C1-C6, even more preferably C1-C4, most preferably C1-C4; 60 arylalkyl, having C6-C20, preferably C6-C10, more preferably C6-C6, even more preferably C6-C4, most preferably C6-C4; 60 aryloxy, having C6-C20, preferably C6-C10, more preferably C6-C6, even more preferably C6-C4, most preferably C6-C4; 60 aromatic amine, having C6-C20, preferably C6-C10, more preferably C6-C6, even more preferably C6-C4, most preferably C6-C4; 40 silyl, having C2-C20, preferably C2-C10, more preferably C2-C6, even more preferably C2-C4, most preferably C2-C4; 40 alkenyl, having C4-C20, preferably C4-C10, more preferably C4-C6, even more preferably C4-C4, most preferably C4-C4; 40 cycloalkenyl, having C4-C20, preferably C4-C10, more preferably C4-C6, even more preferably C4-C4, most preferably C4-C4; 40 heteroalkenyl, having C2-C20, preferably C2-C10, more preferably C2-C6, even more preferably C2-C4, most preferably C2-C4; 40 alkynyl, having C2-C20, preferably C2-C10, more preferably C2-C6, even more preferably C2-C4, most preferably C2-C4; 60 aryl, having C6-C20, preferably C6-C10, more preferably C6-C6, even more preferably C6-C4, most preferably C6-C4; 60 heteroaryl, having C2-C20, preferably C2-C10, more preferably C2-C6, even more preferably C2-C4, most preferably C2-C4; and combinations thereof, any two or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 may optionally be joined or fused to form a substituted or unsubstituted ring.

[0018] Preferably, the rings B, C, D are 5-membered heteroaromatic rings, 6-membered aromatic or heteroaromatic rings.

[0019] Preferably, the metal complex is selected from the group consisting of:

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026] wherein X 1 , X 7 , L 1 , L 2 , R 1 , R 4 are defined as in formula (I);

[0027] G is independently selected from O, S, S=O, SO2, Se, NR 9 , PR 9, R 9 P = O, CR 9 R 10 , C=O, SiR 9 R 10 , GeR 9 R 10 , or BR 11 ;

[0028] X 8 ~ X 11 are each independently selected from CR 1 or N;

[0029] R 9 , R 10 , R 11 are each independently selected from hydrogen or from the group consisting of deuterium, a halogen atom, a nitrile group, an acyl group, a carboxylic acid, an ether, an ester group, an isonitrile group, a sulfido group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a linear alkyl group having C1-C 40 , a linear heteroalkyl group having C1-C 40 , a branched or cyclic alkyl group having C3-C 40 , an alkoxy group having C1-C 40 , an arylalkyl group having C6-C 60 , an aryloxy group having C6-C 60 , an arylamine group having C6-C 60 , a silyl group having C3-C 40 , an alkenyl group having C2-C 40 , a cycloalkenyl group having C4-C 40 , a heteroalkenyl group having C2-C 40 , an alkynyl group having C2-C 40 , an aryl group having C6-C 60 , a heteroaryl group having C2-C 60 , and combinations thereof, any two or more adjacent R 9 , R 10 , R 11 may optionally be joined or fused to form a substituted or unsubstituted ring.

[0030] Preferably, the X 8 ~ X 11 are each independently selected from CR 1 .

[0031] Preferably, the L 1 , L 2 are each independently selected from a single bond, O, S;

[0032] The G are each independently selected from O or S;

[0033] The R1 ~R 5 Each is independently selected from hydrogen or from the group consisting of: deuterium, halogen atom, nitrile group, having C1 to C2 groups. 40 Straight-chain alkyl groups, having C1 to C2 40 Straight-chain heteroalkyl groups, having C3 to C4 40 Branched or cyclic alkyl groups, having C1 to C2... 40 Alkyl groups, having C6 to C6 60 arylalkyl groups, having C6 to C6 60 aryloxy groups, having C6 to C6 60 Aromatic amino groups, having C3 to C4 40 Silyl groups, having C2 to C3 40 Alkenyl groups, having C4 to C5 40 Cycloalkenyl groups, having C2 to C3 40 heteroene group, having C2 to C 40 The alkynyl group, having C6 to C6 60 aryl group, having C2~C 60 heteroaryl compounds and their combinations.

[0034] Preferably, the R 6 R 7 R 8 R 9 R 10 R 11 Each is independently selected from hydrogen, deuterium, and has C1 to C2 atoms. 40 Straight-chain alkyl groups, having C1 to C2 40 Straight-chain heteroalkyl groups, having C3 to C4 40 Branched or cyclic alkyl groups, having C6 to C6 carbon atoms. 60 arylalkyl groups, having C6 to C6 60 Aromatic amino groups, having C3 to C4 40 Silyl groups, having C6 to C6 60 aryl group, having C2~C 60 heteroaryl compounds and their combinations.

[0035] Furthermore, the R 1 ~R 11 Each is independently selected from hydrogen atoms, deuterium atoms, fluorine, nitrile groups, and R. A1 ~R A55 R B1 ~R B45 R C1 ~R C295 The group formed;

[0036] Among them, R A1 ~R A55 The structure is as follows:

[0037]

[0038]

[0039] R B1 ~R B45 The structural formula is as follows:

[0040]

[0041]

[0042] R C1 ~R C295 The structural formula is as follows:

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050] wherein each hydrogen atom in each substituent can be replaced with a deuterium atom.

[0051] Further, the R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 ~R A55 , R B1 ~R B45 , R C1 ~R C295

[0052] ​"Aryl" according to the present invention means both monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic can have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is an aromatic hydrocarbon group, for example the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic and / or heteroaryl. Preferred aryl groups are aryl groups containing from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms. Especially preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, pyrene, chrysene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Additionally, the aryl group can be optionally substituted.

[0053] "Heteroaryl" according to the present invention means both monocyclic aromatic groups and polycyclic aromatic ring systems that 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. Monocyclic heteroaromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the ring can have from one to six heteroatoms. Heteropolycyclic systems can have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), where at least one of the rings is a heteroaryl group, for example the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic and / or heteroaryl. The heteropolycyclic aromatic ring systems can have from one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are heteroaryl groups 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, pyrrolo-dipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indooxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, phenanthroline, xanthene, acridine, phenoxazine, phenothiazine, phenoxazine, benzofuropyridine, furopyridine, benzothienopyridine, thienopyridine, benzoselenopyridine and selenopyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazylene and nitrogen heteroanalogues thereof. Additionally, the heteroaryl group can be optionally substituted.

[0054] Alkyl groups according to the meaning of the application contain 1 to 40 carbon atoms and in which individual hydrogen atoms or -CH2- groups can also be replaced by substituents, and alkenyl or alkynyl groups contain at least two carbon atoms, and as non-limiting examples, alkyl, alkenyl or alkynyl groups are preferably understood to mean 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.

[0055] Alkoxy groups preferably have 1 to 40 carbon atoms and are understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.

[0056] Heteroalkyl groups preferably have 1 to 40 carbon atoms and are understood to mean groups in which individual hydrogen atoms or -CH2- groups are replaced by oxygen, sulfur, halogen atoms and are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.

[0057] Generally, cycloalkyl, cycloalkenyl groups according to the application can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, in which one or more -CH2- groups can be replaced by the above-mentioned groups; furthermore, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0058] Alkyl or alkenyl or alkynyl according to the application has 1 to 40 carbon atoms, and wherein one or more hydrogen atoms can be replaced by deuterium atoms, halogen atoms or nitrile groups.

[0059] Aryl or heteroaryl according to the application, in particular a radical derived from phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, pyrenyl, fluoranthenyl, naphthacene, pentaphene, benzopyrenyl, biphenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, triphenylenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, cis- or trans-indolocarbazolyl, triindene, iso-triindene, spiro-triindene, spiro-iso-triindene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenoxazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazimidazolyl, quinoximidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenoxazinyl, phenoxazinyl, fluoranthenyl, naphthidinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a radical derived from a combination of these systems.

[0060] "Acyl" in the sense of the present application means a substituted carbonyl group (COR).

[0061] "Ester" in the sense of the present application means a substituted oxycarbonyl group (-OCOR or CO2R).

[0062] "Ether" in the sense of the present application means a -OR group.

[0063] "Sulfanyl" or "sulfide" as described herein are used interchangeably and mean a -SR group.

[0064] "Sulfinyl" in the sense of the present application means a -SOR group.

[0065] "Sulfonyl" in the sense of the present application means a -SO2R group.

[0066] "Phosphine" in the sense of the present application means a -PR3 group, where each R can be the same or different.

[0067] "Silyl" in the sense of the present application means a -SiR3 group, where each R can be the same or different.

[0068] Each R described above is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.

[0069] "Aryloxy" as used in the present application means R'O - wherein R' represents an aromatic group having a carbon number of from 6 to 60. Non-limiting examples of such aryloxy groups include phenoxy, naphthoxy, biphenyloxy, and the like.

[0070] "Alkylsilyl" as used in the present application means a silyl group substituted with an alkyl group having a carbon number of from 1 to 40, and the carbon number of the alkylsilyl group is at least 3. Non-limiting examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, and the like. "Arylsilyl" means a silyl group substituted with an aromatic group having a carbon number of from 6 to 60.

[0071] "Arylphosphine" as used in the present application means a diarylphosphine group substituted with an aromatic group having a carbon number of from 6 to 60. Non-limiting examples of arylphosphine groups include diphenylphosphine, di(4-trimethylsilylphenyl)phosphine, and the like. "Aryloxyphosphine" means a diarylphosphine group in which the phosphorus atom is oxidized to the highest valence state.

[0072] "Arylboryl" as used in the present application means a diarylboryl group substituted with an aromatic group having a carbon number of from 6 to 60. Non-limiting examples of arylboryl groups include diphenylboryl, di(2,4,6-trimethylphenyl)boryl, and the like. "Alkylboryl" means a dialkylboryl group substituted with an alkyl group having a carbon number of from 1 to 40. Non-limiting examples of alkylboryl groups include di-tert-butylboryl, diisobutylboryl, and the like.

[0073] In this invention, the terms "halogen", "halogen", "halogen atom", and "halogen group" are used interchangeably and refer to fluorine, chlorine, bromine, or iodine.

[0074] As used herein, “combination of” or “group” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl groups can be combined to form haloalkyl substituents, such as trifluoromethyl; and halogen, alkyl and aryl groups can be combined to form haloaralkyl groups.

[0075] In this invention, the term "substituted or unsubstituted" refers to a group selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40 Alkyl, C2-C 40 alkenyl, C2-C 40 Alkyne group, C1-C 40 Alkoxy, C3-C 40 cycloalkyl, C3-C 40 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Aryl sulfide groups and C2-C 60 One or more substituents in the heteroaryl group are substituted or unsubstituted, or are substituted or unsubstituted by substituents formed by linking two or more substituents of the substituents exemplified above.

[0076] In one instance, the term substitution includes a combination of two to four listed groups.

[0077] In another example, the term substitution comprises a combination of two or three groups. In yet another example, the term substitution comprises a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms that are not hydrogen or deuterium, or combinations containing up to forty atoms that are not hydrogen or deuterium, or combinations containing up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will comprise up to twenty atoms that are not hydrogen or deuterium.

[0078] In this invention, the term "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle formed by the combination of adjacent groups. A condensed ring refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle, or a combination thereof.

[0079] According to an embodiment of the present invention, the metal complex is selected from the group consisting of:

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] Part or all of the hydrogen atoms in the above structures can be replaced with deuterium.

[0099] Use of the organic electroluminescent material in an organic electroluminescent device.

[0100] The organic electroluminescent device of the present application can obtain red light or deep red light with high luminous efficiency.

[0101] An organic electroluminescent device comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex of formula (I).

[0102] The organic layer of the present application can be an emissive layer and the metal complex as described herein can be an emissive dopant or a non-emissive dopant.

[0103] Further, the organic layer can further comprise a host material and a dopant, wherein the dopant comprises a metal complex of formula (I).

[0104] The organic electroluminescent material described can be a sensitizer; wherein the device can further comprise an acceptor, a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0105] The organic electroluminescent device described can further comprise an emissive region comprising the above compound as disclosed in the present application.

[0106] Further, the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dithiophene, dithiophene, fluorene, dithiophene, 5,9-dioxo-13b-boron naphthacene [3,2,1-de] anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dithiophene, aza-dithiophene, aza-dithiophene, and aza-(5,9-dioxo-13b-boron naphthacene [3,2,1-de] anthracene) or a group derived from a combination of these systems.

[0107] Preferably, the host material is selected from the group consisting of the following structures:

[0108]

[0109]

[0110] The mass ratio of the host material and the dopant is 99:1 to 1:99.

[0111] Further, the mass ratio of the host material and the dopant is 99:1 to 80:20.

[0112] Materials described herein as useful for particular layers in an organic light emitting device can be used in combination with a wide variety of other materials present in devices. For example, the emissive dopants disclosed herein can be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that can be present. Materials described or referenced below are non-limiting examples from among a wide variety of materials that can be employed in combination with the compounds disclosed herein. One of ordinary skill in the art can readily identify additional materials and / or variants of a material that are suitable for use in combination with the compounds disclosed herein.

[0113] These methods are generally known to those of ordinary skill in the art and they can apply them without inventive skill to organic electroluminescent devices comprising a compound according to the present application.

[0114] According to one embodiment, novel ligands for metal complexes are disclosed. It has been found that the incorporation of these ligands unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and increases the luminous efficiency of the device.

[0115] As the method for manufacturing the organic electroluminescent device of the present application, the following manufacturing method can be exemplified, but is not limited thereto, and various changes can be made by those skilled in the art based on common technical knowledge in the art. The aforementioned manufacturing method includes the following steps:

[0116] a cleaning step of cleaning the ITO-equipped glass substrate using a cleaning agent, deionized water, an organic solvent, or the like;

[0117] a step of forming a hole injection layer by vacuum deposition of a hole injection layer-forming material containing the organic electroluminescent material of the present application on the aforementioned anode layer, thereby forming a hole injection layer containing the organic electroluminescent material of the present application on the aforementioned substrate;

[0118] a step of forming a hole transport layer by vacuum deposition of a hole transport layer-forming material on the aforementioned hole injection layer;

[0119] a step of forming an organic light-emitting layer by vacuum deposition of an organic light-emitting layer-forming material containing the material of the present application on the aforementioned hole transport layer, thereby forming an organic light-emitting layer containing the organic electroluminescent material of the present application on the aforementioned hole transport layer;

[0120] a step of forming an electron transport layer by vacuum deposition of an electron transport layer-forming material containing the organic electroluminescent material of the present application on the aforementioned organic light-emitting layer, thereby forming an electron transport layer containing the organic electroluminescent material of the present application on the aforementioned organic light-emitting layer;

[0121] a step of forming a cathode layer by evaporation, sputtering, or spin coating of a cathode-forming material on the aforementioned electron transport layer, thereby forming a cathode layer.

[0122] A consumer product comprising the organic electroluminescent device described.

[0123] The consumer product of the present application can be one of the following: a flat panel display, a computer monitor, a medical monitor, a television, a signboard, a lamp for internal or external illumination and / or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising a plurality of displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

[0124] Compared with the prior art, the present application has the following advantages:

[0125] (1) The metal complex of the present application exhibits enhanced phosphorescence quantum yield, good light emission stability, high light emission efficiency, and is suitable for use as an emitter material in OLED applications when used in OLED, especially in the red light emission region. The metal complex of the present application can obtain an organic electroluminescent device with red phosphorescence and improved light emission efficiency, and the thermal stability of the light emitting device is good. The consumer product of the organic light emitting device of the present application contains the organic electroluminescent device of the present application, thereby obtaining an electronic device with red phosphorescence and improved light emission efficiency.

[0126] (2) The metal complex of the present application can control its photophysical properties by adjusting the structure of the ligand around the metal center and controlling the structure of the substituent on the ligand, and has the advantages of narrow emission spectrum, high stability and high efficiency, and has a wide application prospect in the fields of OLED display and lighting lamps. BRIEF DESCRIPTION OF DRAWINGS

[0127] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the prior art, the drawings needed in the embodiments or prior art description will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application, and those skilled in the art can obtain other drawings according to these drawings without creative labor.

[0128] Figure 1 A schematic diagram of an organic light emitting device 100 is shown. The drawings are not necessarily drawn to scale. The device 100 can include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 can be fabricated by sequentially depositing the described layers.

[0129] Figure 2An organic light emitting device 200 is shown schematically that exhibits two light emitting layers. The device comprises a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 can be prepared by sequentially depositing the described layers. Since the most common OLED device has one light emitting layer, while the device 200 has a first light emitting layer and a second light emitting layer, the light emission peak shape of the first light emitting layer and the second light emitting layer can be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, similar materials to those described with respect to the device 100 can be used. Figure 2 One example of how to add some layers from the structure of the device 100 is provided. DETAILED DESCRIPTION

[0130] In order to make the objects, technical solutions and advantages of the present application clearer, the technical solutions of the present application will be described in detail below. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by a person of ordinary skill in the art without creative work fall within the scope of protection of the present application.

[0131] In the present application, "EQE" refers to the external quantum efficiency of the element, i.e. the ratio of the number of photons emitted by the element to the number of electrons injected into the element.

[0132] The organic electroluminescent device described in the present application comprises at least one organic layer, which is disposed between an anode and a cathode and is electrically connected with the anode and the cathode. Figure 1 An organic light emitting device 100 is shown schematically. Figure 2 An organic light emitting device 200 is shown schematically that exhibits two light emitting layers. Since the most common OLED device has one single color light emitting layer or has three light emitting layers of three primary colors, while the device 200 has two light emitting layers of the same light color or two light emitting layers of different light colors.

[0133] Figure 1 and Figure 2The simple layered structure illustrated in the middle is provided as a non-limiting example, and it should be understood that embodiments of the application can be used in combination with a variety of other structures. The particular materials and structures described are exemplary in nature and other materials and structures can be used. Functional OLEDs can be achieved by combining a variety of the various layers described in different ways, or layers can be omitted altogether, based on design, performance, and cost factors. Other layers not specifically described can also be included. Materials other than those specifically described can be employed. Although many of the examples provided herein describe various layers as having a single material, it will be understood that combinations of materials, such as a mixture of materials, or a mixture of a material and a dopant, or more generally a mixture, can be used. Also, the layers can have various sub-layers. The names given to the various layers in this document are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into emissive layer 205, and can be described as a hole transport layer or a electron blocking layer. In one embodiment, an OLED can be described as having a single organic layer comprising a mixture of materials, a plurality of organic layers, or a plurality of stacked layers. Figure 1 and Figure 2 a plurality of layers of different organic materials as described below.

[0134] Structures and materials other than those specifically described can also be used. For example, a PLED including a polymeric material can be used. As another example, an OLED having a single organic layer or a plurality of stacked layers can be used. The OLED structure can depart from the simple layered structure illustrated in the middle of Figure 1 and Figure 2 . For example, the substrate can include an angled reflective surface to improve light coupling.

[0135] Unless otherwise specified, any of the layers of the various embodiments can be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, organic vapor phase deposition methods, or sublimation by means of a carrier gas, wherein the material is applied at a pressure of 10 -5 millitorr to 1 bar, preferably 0.2 to 1 bar, and the material is deposited on the substrate in a thin layer. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include, for example, by spin-coating, or by means of any desired printing method, such as screen printing, flexographic printing, offset printing, light-induced thermal imaging, thermal transfer, inkjet printing, or nozzle printing, one or more layers are produced. Soluble compounds, for example, are obtained by suitable substitution. These methods are also particularly suitable for oligomers, dendrimers, and polymers. It is also possible to use hybrid methods, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.

[0136] The device fabricated according to the embodiments of the present application can further optionally include a barrier layer. One use 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 can be deposited on the substrate, on the electrodes, under the substrate, under the electrodes, beside the substrate, beside the electrodes, or on any other part of the device, including on the edges. The barrier layer can include a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques, and can include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials can be used for the barrier layer. The barrier layer can incorporate inorganic or organic compounds, or both. Preferably, the barrier layer includes a mixture of polymeric and non-polymeric materials. In order to be considered a mixture, the aforementioned polymeric and non-polymeric materials making 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 can range from 95 / 5 to 5 / 95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

[0137] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, etc., can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes, such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, etc., can also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0138] The materials and structures described herein can be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors can use the materials and structures.

[0139] Further, organic devices such as organic transistors can use the materials and structures.

[0140] In the following examples of the present application, the conventional preparation methods are used unless otherwise specified. The raw materials used are commercially available unless otherwise specified. The percentages are mass percentages unless otherwise specified.

[0141] In order to more clearly illustrate the present application, the technical solutions of the present application are described below in conjunction with some specific examples:

[0142] In the embodiments of the present application, the performance detection conditions of the electroluminescent device prepared are as follows:

[0143] Color coordinates: tested using a spectrometer Photo Research PR-715;

[0144] Current-voltage: tested using digital source meter Keithley 2420;

[0145] Power efficiency: tested using NEWPORT 1931-C;

[0146] Luminance: tested using luminance meter Minolta Cs-1000A.

[0147] Example 1

[0148] The method for preparing the metal complex P1 comprises the following steps:

[0149] First step: preparation of compound Int-1

[0150]

[0151] Under nitrogen protection, 25.0 mmol of sub-1 was dissolved in 80 mL of 2-methyltetrahydrofuran, 50.0 mmol of sub-2, 2.5 mmol of 2,2-bipyridine, 1.25 mmol of palladium trifluoroacetate and 0.25 mol of trifluoroacetic acid were added, the temperature was raised to 80°C, the reaction was stirred for 24 hours, and then the temperature was reduced to room temperature. 50 mL of ethyl acetate and 50 mL of saturated aqueous sodium bicarbonate solution were added and stirred to dissolve, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated and dried, and then purified by silica gel column separation to obtain intermediate Int-1, a white solid, with a yield of 82%.

[0152] Second step: preparation of compound Int-2

[0153]

[0154] Under nitrogen protection, 20.0 mmol of Int-1 was dispersed in 50 mL of phosphorus oxychloride, the temperature was raised to 50°C, the reaction was stirred for 12 hours, and then concentrated and dried under reduced pressure. The black residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and saturated brine, the organic phase was dried, filtered, and the filtrate was concentrated and dried under reduced pressure, and then purified by silica gel column separation to obtain Int-2, a yellow solid, with a yield of 87%.

[0155] Third step: preparation of compound Int-3

[0156]

[0157] Under nitrogen protection, 22.0 mmol of sub-3 was dissolved in 60 mL of DMF, cooled to 0 °C, 30.0 mmol of 60% sodium hydride was added in batches, and the reaction was stirred for 1 h. Then 20.0 mmol of Int-2 was added, and the reaction was stirred for 1 h. The temperature was increased to 50 °C, and the reaction was stirred for 15 h. The reaction was cooled to room temperature, and the reaction solution was poured into 150 mL of ice water. The filter cake was washed with water and ethanol, and the gray solid was separated and purified by silica gel column to obtain Int-3, a yellow solid, in a yield of 89%.

[0158] Fourth step: preparation of compound P1

[0159]

[0160] Under nitrogen protection, 15.0 mmol of Int-3 was dissolved in 100 mL of acetic acid, and 16.5 mmol of K2PtCl4 and 1.5 mmol of tetrabutylammonium bromide were added. The reaction was stirred and heated to reflux for 15 h. The reaction was cooled to room temperature, and the reaction solution was concentrated under reduced pressure. Dichloromethane was added for extraction, and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column to obtain compound P1, a red solid, in a yield of 67%. HRMS (MALDI-TOF): calculated value: 880.3105, measured value: 881.3197.

[0161] Example 2

[0162] The preparation method of metal complex P2 comprises the following steps:

[0163] First step: preparation of compound Int-4

[0164]

[0165] Under nitrogen protection, 25.0 mmol of sub-4 was dissolved in 60 mL of acetonitrile and 30 mL of water, and 50.0 mmol of anhydrous potassium carbonate and 5.0 mmol of tetrabutylammonium bromide were added. Then 30.0 mmol of sub-5 and 0.01 mmol of Pd132 were added, and the reaction was heated to reflux and stirred for 15 h. The reaction was cooled to room temperature, and 50 mL of ethyl acetate and 50 mL of water were added for stirring and dissolution. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was collected, washed with saturated brine, dried, filtered, and concentrated under reduced pressure. The residue was separated and purified by silica gel column to obtain intermediate Int-4, a yellow solid, in a yield of 76%.

[0166] Second step: preparation of compound Int-5

[0167]

[0168] Int-4 and 20.0 mmol of sub-6 were dissolved in 60 mL of xylene, 30.0 mmol of sodium tert-butoxide, 2.0 mmol of copper iodide, 2.0 mmol of Pd2(dba)3 and 5.0 mmol of 10% tri-tert-butylphosphine in toluene were added, the temperature was raised to 110 °C and the reaction was stirred for 15 hours, it was allowed to cool down to room temperature, 50 mL of ice water were added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phases were combined and dried, filtered and the filtrate was concentrated under reduced pressure and dried, the solid was purified by column separation on silica gel to obtain Int-5 as a yellow solid in 87% yield.

[0169] Third step: preparation of compound P2

[0170]

[0171] Int-5 was dissolved in 100 mL of acetic acid under nitrogen, 16.5 mmol of K2PtCl4 and 1.5 mmol of tetrabutylammonium bromide were added, the temperature was raised to reflux and the reaction was stirred for 15 hours, it was allowed to cool down to room temperature, it was concentrated under reduced pressure, dichloromethane was added, it was filtered and the filtrate was concentrated under reduced pressure and dried, it was purified by column separation on silica gel to obtain compound P2 as a red solid in 58% yield. HRMS (MALDI-TOF): calculated 830.2948, found 831.3034.

[0172] Example 3

[0173] The method for preparing the metal complex P3 comprises the following steps:

[0174] First step: preparation of compound Int-6

[0175]

[0176] Int-5 was dissolved in 100 mL of acetic acid under nitrogen, 16.5 mmol of K2PtCl4 and 1.5 mmol of tetrabutylammonium bromide were added, the temperature was raised to reflux and the reaction was stirred for 15 hours, it was allowed to cool down to room temperature, it was concentrated under reduced pressure, dichloromethane was added, it was filtered and the filtrate was concentrated under reduced pressure and dried, it was purified by column separation on silica gel to obtain compound P2 as a red solid in 58% yield. HRMS (MALDI-TOF): calculated 830.2948, found 831.3034.

[0177] Second step: preparation of compound Int-7

[0178]

[0179] Compound Int-7 was prepared according to the procedure described in Step 2 of Example 1, by replacing Int-1 in Step 2 of Example 1 with Int-6, as a yellow solid in 88% yield.

[0180] Step 3: Preparation of compound Int-8

[0181]

[0182] Under nitrogen, 22.0 mmol of Int-7 and 20.0 mmol of sub-6 were dissolved in 60 mL of DMF, 40.0 mmol of anhydrous cesium carbonate was added, the temperature was raised to 125 °C, the reaction was stirred for 10 hours, it was allowed to cool to room temperature, 150 mL of ice water was added, it was filtered, the filter cake was washed with water and ethanol, and the solid was purified by silica gel column to obtain Int-8 as a yellow solid in 82% yield.

[0183] Step 4: Preparation of compound P3

[0184]

[0185] Compound P3 was prepared according to the procedure described in Step 4 of Example 1, by replacing Int-3 in Step 4 of Example 1 with Int-8, as a red solid in 78% yield, HRMS (MALDI-TOF): calculated 858.2356, found 859.2448.

[0186] Example 4

[0187] The following compounds were prepared according to the similar synthetic procedures described in Example 1 to Example 3 above:

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] Fabrication of organic electroluminescent devices

[0207] An OLED element 100, such as Figure 1 As shown, the OLED element in this embodiment is a top-emitting element, including a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light-emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light-emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, a cathode 110 disposed on the electron injection layer 109, and a capping layer 111 above the cathode. The method for fabricating an OLED element without the hole blocking layer 107 is as follows:

[0208] The glass substrate with patterned ITO electrodes was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0209] The prepared ITO glass substrate was placed in a vacuum chamber and evacuated to a vacuum level of less than 1 × 10⁻⁶. -5 Pa, metallic silver is deposited as the anode on the above ITO film, and the film thickness is [missing value]. Continue by depositing the compound HATCN as a hole injection layer, with a film thickness of [missing information]. HTM is then deposited onto the aforementioned hole injection layer to form a hole transport layer, with a deposition thickness of [missing information].

[0210] RPrime is evaporated on the hole transport layer as an electron blocking layer, and the film thickness is

[0211] The metal complex of the present application and RH022 are evaporated on the electron blocking layer as the organic light emitting layer of the device, wherein RH022 is the host material and the metal complex of the present application is the dopant material, the doping concentration is 5%, and the film thickness is

[0212] LiQ and ET318 are further evaporated on the light emitting layer as the electron transport layer of the device, wherein LiQ is 50% of the mass of ET318, and the film thickness is

[0213] LiF is further evaporated on the electron transport layer as the electron injection layer of the device, and the film thickness is

[0214] Metal magnesium and silver are evaporated on the electron injection layer as the cathode layer of the device, wherein the mass ratio of magnesium and silver is 1:9, and the film thickness is

[0215] Finally, compound HTM is evaporated on the cathode layer as the capping layer, and the film thickness is

[0216] The organic light emitting device 200 with two light emitting layers according to the above method, as shown in Figure 2 includes a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213.

[0217] Comparative Example 1

[0218] Comparative Element 1 is prepared by using the compound shown in RD025 instead of the metal complex of the organic electroluminescent device, and other steps are the same as above.

[0219] The structural formulas of the aforementioned HATCN, HTM, RPrime, RH022, RD025, and ET318 are shown as follows:

[0220]

[0221] Example 5

[0222]

[0223] An organic electroluminescent device was produced in the same manner as described above, using the metal complex of the present application instead of the metal complex of the above organic electroluminescent device, and the driving voltage and current efficiency of the light-emitting element were measured using a digital source meter and a luminance meter, and the lifetime of the element was measured. Specifically, the voltage was increased at a rate of 0.1 V per second, and the voltage at which the current density of the organic electroluminescent device reached 10 mA / cm 2 was measured as the driving voltage, and the luminance at that time was measured; the ratio of the luminance to the current density was the current efficiency; and the LT98% lifetime was measured as follows: the luminance of the organic electroluminescent device was measured while maintaining a constant current at 1000 cd / m 2 , and the time until the luminance decreased to 980 cd / m 2 was measured in hours, and some of the results are summarized in Table 1. The data are normalized with respect to Comparative Element 1 (the data in parentheses).

[0224] Table 1

[0225]

[0226] As can be seen from Table 1, the organic electroluminescent device produced using the metal complex of the present application has a lower driving voltage, a higher external quantum emission efficiency, and a narrower half-peak width, and has a good color purity, compared to Comparative Element 1, and is an excellent organic electroluminescent material.

[0227] The metal complex RD025 of Comparative Element 1 differs from the metal complex of the present application in that the ligand of the metal complex of the present application has a cyclic monomolecule as a mother nucleus, and the separation of the HOMO and LUMO of the ligand is achieved by a single bond of carbazole or carbolin, and various different substituent groups are introduced to increase the steric hindrance and improve the stability, and at the same time, the degree of relaxation of the excited state is reduced. In contrast, the metal complex RD025 coordinates with isoquinoline and 1,3-diketone, and the planar conjugation is weak, and energy is lost due to the rotation of the ligand, and the stability of the metal complex is low, and therefore, the driving voltage is high, the efficiency is low, the emission peak is wide, and the LT98% lifetime of the element is not as excellent as the element using the metal complex of the present application as a dopant material for the light-emitting layer.

[0228] The above description is merely representative examples of specific implementations of the present application, but the scope of protection of the present application is not limited thereto, and any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed in the present application, and all of them should be included in the scope of protection of the present application. Therefore, the scope of protection of the present application should be based on the scope of protection of the claims.

Claims

1. A metal complex, characterized in that, The metal complex is selected from the group consisting of the following structures: 、 、 。 2. An organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and at least one organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex of claim 1.

3. The organic electroluminescent device according to claim 2, characterized in that, The organic layer further includes a host material and a dopant material, wherein the dopant material includes the metal complex of claim 1; the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, fluorene, dibenzoselenene, 5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenene, and aza-(5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene).

4. The organic electroluminescent device according to claim 3, characterized in that, The main material is selected from the group consisting of the following structures: 。 5. The organic electroluminescent device according to claim 3, characterized in that, The mass ratio of the main material to the doped material is 1:99 to 99:1.

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