A binuclear platinum complex and its use

Abstract

The application belongs to the technical field of luminescent materials, and particularly relates to a binuclear platinum complex and application thereof. The binuclear platinum complex has the structure shown in formula (1), and when used in an OLED, especially in a blue light emitting region, the binuclear platinum complex exhibits enhanced phosphorescence quantum yield, good luminescence stability, high luminescence efficiency, and is suitable for use as an emitter material in OLED application. The metal platinum complex of the application can obtain an organic electroluminescent device with deep blue phosphorescence and improved luminescence efficiency, and the luminescent device has good thermal stability. The binuclear platinum complex has the advantages of narrow emission spectrum, high stability and high efficiency by adjusting the structure of the ligand around the metal center and the structure of the substituent on the ligand to control the photophysical properties, and has wide application prospects in many fields such as OLED display and lighting.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of luminescent materials, and particularly relates to a binuclear platinum complex and application thereof. 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% luminance efficiency are used in various sizes of OLEDs, while no blue phosphorescent material has been commercialized so far, although blue fluorescent materials have only 25% luminance efficiency, and various 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 transition, 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 inhibit non-radiative transition of triplet excitons by using strong intermolecular interactions, and because of its dense molecular packing, it can reduce the quenching of triplet excitons by oxygen, water vapor, and the like, 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 shift of light 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 binuclear platinum complex and application thereof. When the binuclear platinum complex is used in OLEDs, especially in the blue 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 binuclear platinum complex. The binuclear platinum complex has good electroluminescent stability and excellent luminous efficiency.

[0007] The second object of the present application provides application of the binuclear platinum complex in an organic electroluminescent device.

[0008] A third object of the present application provides an organic electroluminescent device comprising the dinuclear platinum complex.

[0009] A fourth object of the present application provides a consumer product comprising the organic electroluminescent device.

[0010] To achieve the above object, the present application adopts the following technical solutions:

[0011] A dinuclear platinum complex, the general formula of the dinuclear platinum complex is shown in formula (I):

[0012]

[0013] wherein, ring A, ring B, ring C, ring D, ring E each independently represents a 5-membered carbon ring, a 5-membered heterocyclic ring, a 6-membered carbon ring or a 6-membered heterocyclic ring;

[0014] X 1 ~X 8 is a ring atom, each independently selected from C or N;

[0015] R 1 , R 2 , R 5 , R 6 , R 7 each represents mono-substitution or multi-substitution to saturated substitution, or no substitution;

[0016] R 3 , R 4 each independently represents mono-substitution or di-substitution;

[0017] L 1 , L 2 each independently selected from a single bond, or a divalent group;

[0018] R 1 ~R 7 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 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 silane group having C3-C 40 , an alkenyl group having C2-C 40alkenyl having C4to C10atoms, cycloalkenyl having C2to C10atoms, heteroalkenyl having C2to C10atoms, alkynyl having C6to C10atoms, aryl having C6to C10atoms, heteroaryl having C2to C10atoms, and combinations thereof, any two or more of which R 40 , R 40 , R 40 , R 60 , R 60 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 may optionally be joined or fused to form a substituted or unsubstituted ring.

[0019] Preferably, each of said ring A, ring E is a 5-membered heteroaromatic ring.

[0020] Preferably, each of said ring B, ring D is a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0021] Preferably, said ring C is a 5-membered heteroaromatic ring, a 6-membered aromatic ring, or a 6-membered heteroaromatic ring.

[0022] Preferably, said dinuclear platinum complex is selected from the group consisting of:

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032] R 1 to R 7 , L 1 , L 2 are defined the same as above for formula (I).

[0033] As a divalent linking functional group, the "divalent group" of the present application can be, as non-limiting examples, -0-, -S-, -(S=0)-, -(S02)-, -(CH2)-, -(C=0)-, -Se-, -(Se=0), -(Se02), -(NR 8 )-, -(PR 8 )-, -(P=OR 8 )-, -(CR 8 R 9 )- or -(SiR 8 R 9 )-, etc.

[0034] Further, the L 1 , L 2 are each independently selected from a single bond, O, S, S=0, S02, Se, NR 8 , PR 8 , R 8 P=0, CR 8 R 9 , C=0, SiR 8 R 9 , GeR 8 R 9 , BR 8 , or a group consisting of:

[0035]

[0036] wherein n is selected from 0, 1, 2 or 3;

[0037] R 8 , R 9 , R 10 , R 11 , R 12 are each independently selected from hydrogen or a 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 sulfide group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphine 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 heteroalkyl group having C2-C 40heteroene group, having C2 to C 40 The alkynyl group, having C6 to C6 60 aryl group, having C2~C 60 heteroaryl groups and their combinations; any two or more adjacent R groups 8 R 9 R 10 R 11 R 12 They can be optionally joined or circulated to form substituted or unsubstituted rings.

[0038] Furthermore, the L 1 L 2 Each is independently selected from single bond, O, S, S=O, SO2, C(CH3)2 or C=O.

[0039] Furthermore, the R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 Each is independently selected from hydrogen atoms, deuterium atoms, fluorine, nitrile groups, and R. A1 ~R A30 R B1 ~R B195 R C1 ~R C80 The group formed;

[0040] Among them, R A1 ~R A30 The structural formula shown is as follows:

[0041]

[0042] R B1 ~R B195 The structure shown is as follows:

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] R C1 ~R C80 The structure is shown as follows:

[0050]

[0051]

[0052] wherein each hydrogen atom in each substituent can be replaced with a deuterium atom.

[0053] Further, the R 8 , R 9 , R 10 , R 11 , R 12 each independently is selected from the group consisting of R A1 ~R A26 , R B1 ~R B185 , R C1 ~R C79 .

[0054] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 each independently is selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, isonitrile, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 .

[0055] In the substituted or unsubstituted ring formed by the adjacent groups binding to each other in the present application, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring. The condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocyclic ring, a condensed aromatic heterocyclic ring, or a combination thereof.

[0056] A 5-membered carbocyclic ring as described herein is a monocyclic and polycyclic ring system having 5 carbon atoms, a polycyclic ring is a ring system having two or more rings of which two carbons are common to two adjacent rings, e.g. a 5-membered carbocyclic ring can be cyclopentane, cyclopentene, indane, indene, etc. A 5-membered heterocyclic ring refers to a 5-membered carbocyclic ring comprising at least one heteroatom, the total number of heteroatoms and carbon atoms constituting the ring is 5, the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, phosphorus, boron, silicon or selenium, in many cases, oxygen, sulfur or nitrogen is the preferred heteroatom, as non-limiting examples of 5-membered heterocyclic rings there are: pyrazole, imidazole, oxazole, thiazole, triazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, benzimidazole, benzoxazole, benzotriazole, etc.

[0057] A 6-membered carbocyclic ring as described herein is a monocyclic and polycyclic ring system having 6 carbon atoms, as preferred, the 6-membered carbocyclic ring refers to an aryl group as described herein. A 6-membered heterocyclic ring refers to a ring system having a total number of heteroatoms and carbon atoms constituting the ring is 6, as preferred, the 6-membered heterocyclic ring refers to a 6-membered heteroaryl group, e.g. pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, pteridine, etc.

[0058] An "aryl" group according to the present application refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring can have two or more rings of which two carbons are common to two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g. the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclic and / or heteroaryl groups. Preferred aryl groups are aromatic groups containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 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, azulene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Additionally, the aryl group can be optionally substituted.

[0059] "Heteroaryl" in the sense of the present application means and includes both monocyclic aromatic groups and polycyclic aromatic ring systems comprising 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, for example the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocyclo, and / or heteroaryl. Heteropolycyclic aromatic ring systems can have from one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are heteroaryls containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryls 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, pteridine, xanthene, acridine, phenoxazine, phenothiazine, phenoxazine, benzofuro-pyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazylene, and nitrogen analogs thereof. Additionally, the heteroaryl groups can be optionally substituted.

[0060] Alkyl in the sense of the present application preferably contains from 1 to 40 carbon atoms and straight-chain alkyl or branched alkyl groups, in which the individual hydrogen atoms or -CH2- groups can also be replaced by substituents, and alkenyl or alkynyl groups contain at least two carbon atoms. 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.

[0061] Alkyl is preferably alkyl having 1 to 40 carbon atoms and is considered to mean methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, 2-methylbutyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, pentafluoroethyl, and the like.

[0062] Heteroalkyl is preferably heteroalkyl having 1 to 40 carbon atoms and is considered to mean alkyl groups in which an individual hydrogen atom or -CH2- group is replaced by an oxygen, sulfur, halogen atom, and is considered to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, and is considered to mean methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-buthylthio, isobutylthio, sec-buthylthio, tert-buthylthio, 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, ethynoxy, ethynylthio, propynoxy, propynylthio, butynoxy, butynylthio, pentynoxy, pentynylthio, hexynoxy, hexynylthio.

[0063] Generally, the cycloalkyl, cycloalkenyl groups according to the present 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 a deuterium atom, a halogen atom or a nitrile group.

[0064] The alkenyl or alkynyl groups according to the present application preferably have 2 to 40 carbon atoms and are considered to mean alkenyl or alkynyl groups in which an individual hydrogen atom can be replaced, and are considered to mean ethenyl, propenyl, butenyl, isobutenyl, phenylethenyl, diphenylethenyl, ethynyl, propynyl, butynyl, phenylbutynyl; furthermore, one or more hydrogen atoms can also be replaced by a deuterium atom, a halogen atom or a nitrile group.

[0065] The aryl or heteroaryl groups according to the present application are considered to mean, in particular, groups derived from phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluoranthenyl, picenyl, azulenyl, and the like. fluorenyl, spirobifluorenyl, dihydrouenyl, triphenylenyl, dihydropyranyl, tetrahydropyranyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, cis- or trans-indolocarbazolyl, triindenylyl, isotriindenylyl, spirotrindenylyl, spiroisotriindenylyl, 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-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperylenyl, pyrazinyl, phenoxazinyl, phenoxazinyl, phenothiazinyl, fluorubinyl, 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.

[0066] "Acyl" in the sense of the present application means a substituted carbonyl group (COR).

[0067] "Ester" in the sense of the present application means a substituted oxycarbonyl group (-OCOR or CO2R).

[0068] "Ether" in the sense of the present application means a -OR group.

[0069] "Sulfur group" or "sulfide" as described herein are used interchangeably and mean a -SR group.

[0070] "Sulfinyl" in the sense of the present application means a -SOR group.

[0071] "Sulfonyl" in the sense of the present application means a -SO2R group.

[0072] "Phosphino" in the sense of the present application means a -PR3 group, where each R can be the same or different.

[0073] "Silyl" in the sense of the present application means a -SiR3 group, where each R can be the same or different.

[0074] Each R described above is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.

[0075] "Aryloxy" used in the present application means R'O - where R' is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy groups are phenoxy, naphthoxy, biphenyloxy, and the like.

[0076] "Alkylsilyl" used in the present application means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of alkylsilyl groups are trimethylsilyl, triethylsilyl, and the like. "Arylsilyl" means a silyl group substituted with an aryl group having 6 to 60 carbon atoms.

[0077] "Arylphosphino" used in the present application means a diarylphosphino group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylphosphino groups are diphenylphosphino, di(4-trimethylsilylphenyl)phosphino, and the like. "Aryloxyphosphino" means a diarylphosphino group in which the phosphorus atom is oxidized to the highest valence state.

[0078] "Arylboryl" used in the present application means a diarylboryl group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylboryl groups are diphenylboryl, di(2,4,6-trimethylphenyl)boryl, and the like. "Alkylboryl" means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of alkylboryl groups are di-tert-butylboryl, diisobutylboryl, and the like.

[0079] "Halogen", "halo", "halo atom", "halogen atom" are used interchangeably and mean fluorine, chlorine, bromine, or iodine.

[0080] 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.

[0081] 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.

[0082] In one instance, the term substitution includes a combination of two to four listed groups.

[0083] 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.

[0084] According to an embodiment of the present invention, the binuclear platinum complex is selected from the group consisting of:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] Some or all of the hydrogen atoms in the above structures can be replaced by deuterium atoms;

[0105] R A1 , R A20 , R B1 , R B107 , R B186 , R C1 The structures are as described above.

[0106] Use of an organic electroluminescent material as described in an organic electroluminescent device.

[0107] The organic electroluminescent device of the present application can achieve blue light with high luminous efficiency.

[0108] 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 dinuclear platinum complex of formula (I).

[0109] The organic layer of the present application can be an emissive layer and the dinuclear platinum complex as described herein can be an emissive dopant or a non-emissive dopant.

[0110] Further, the organic layer can further comprise a host material and a dopant, wherein the dopant comprises a dinuclear platinum complex of formula (I).

[0111] The organic electroluminescent material can be a sensitizer; wherein the device can further comprise an acceptor, a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0112] The organic electroluminescent device of the present application can further comprise an emission region comprising a compound as disclosed in the above compound section of the present disclosure.

[0113] Further, the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dithiophene, dithiophene, fluorene, dithiophene, 5,9-dioxo-13b-boron naphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dithiophene, aza-dithiophene, aza-dithiophene, and aza-(5,9-dioxo-13b-boron naphtho[3,2,1-de]anthracene) or a group derived from a combination of these systems.

[0114] Preferably, the host material is selected from the group consisting of the following structures:

[0115]

[0116]

[0117] Materials described herein as useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein 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. The materials described or referenced below are non-limiting examples from among the many that exist in the art and that can be used in combination with the compounds disclosed herein. One of ordinary skill in the art can readily identify other materials that are suitable for use in combination with the compounds disclosed herein.

[0118] The mass ratio of the host material to the dopant material is 99:1 to 1:99.

[0119] Preferably, the mass ratio of the host material to the dopant material is 98:2 to 50:50.

[0120] Further, the mass ratio of the host material to the dopant material is 98:2 to 90:10.

[0121] 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.

[0122] According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have found that the incorporation of these ligands unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and increases the luminous efficiency of the device.

[0123] 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:

[0124] a cleaning step of cleaning the ITO-equipped glass substrate using a cleaning agent, deionized water, an organic solvent, or the like;

[0125] 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;

[0126] a step of forming a hole transport layer by vacuum deposition of a hole transport layer-forming material on the aforementioned hole injection layer;

[0127] 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;

[0128] 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;

[0129] 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.

[0130] A consumer product comprising the organic electroluminescent device described.

[0131] 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.

[0132] Compared with the prior art, the present application has the following advantages:

[0133] (1) The dinuclear platinum 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 OLEDs, especially in blue light emitting regions. The dinuclear platinum complex of the present application can be used to obtain an organic electroluminescent device with blue phosphorescence and improved light emission efficiency, and the light emission device has good thermal stability. 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 blue phosphorescence and improved light emission efficiency.

[0134] (2) The dinuclear platinum complex of the present application can regulate its photophysical properties by adjusting the structure of the ligand around the metal center and regulating the structure of the substituent on the ligand, and has the advantages of narrow emission spectrum, high stability and high efficiency, and has wide application prospects in the fields of OLED display and lighting lamps. BRIEF DESCRIPTION OF DRAWINGS

[0135] 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 following embodiment or prior art description will be briefly introduced. Obviously, the drawings in the following description are only some embodiments of the present application, and those skilled in the art can also obtain other drawings according to these drawings without creative labor.

[0136] 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, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 can be manufactured by sequentially depositing the described layers.

[0137] Figure 2 A schematic diagram of an organic light emitting device 200 is shown. The drawings are not necessarily drawn to scale. The device 200 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 200 is an example of the device 100 with an additional hole blocking layer 107, and can be manufactured by the same method as the device 100.

[0138] Figure 3An organic light-emitting device 300 schematic showing two light-emitting layers. The device includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a first light-emitting layer 1061, an electron transport layer 108, a charge generation layer 1022, a hole injection layer 103, a hole transport layer 104, a second light-emitting layer 1063, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer 111. The device 300 can be prepared by sequentially depositing the described layers. Because the most common OLED device has one light-emitting layer, while the device 300 has a first light-emitting layer and a second light-emitting layer, the light-emitting peak shapes 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 300, similar materials to those described with respect to the device 100 can be used. Figure 3 One example of how some layers can be added from the structure of the device 100 is provided. DETAILED DESCRIPTION

[0139] 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, 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 belong to the scope protected by the present application.

[0140] In the present application, "EQE" refers to the external quantum efficiency of the element, that is, the ratio of the number of photons emitted by the element to the number of electrons injected into the element.

[0141] The organic electroluminescent device described in the present application includes at least one organic layer, which is disposed between the anode and the cathode and is electrically connected with the anode and the cathode. Figure 1 An organic light-emitting device 100 schematic is shown. The illustration is 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, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) or light refractive layer 111. The device 100 can be fabricated by sequentially depositing the described layers.

[0142] Figure 2 An organic light-emitting device 200 schematic is shown, which is an example of adding a hole blocking layer 107 on the basis of the structure of the device 100.

[0143] Figure 3An organic light emitting device 300 containing two light emitting layers is shown schematically. The device includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a first light emitting layer 1061, an electron transport layer 108, a charge generation layer 1022, a hole injection layer 103, a hole transport layer 104, a second light emitting layer 1063, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) or light refractive layer 111. The device 300 can be prepared by sequentially depositing the described layers. While the most common OLED devices have one light emitting layer of a single color or have three light emitting layers of the three primary colors, the device 300 has two light emitting layers of the same color or different colors. Similar materials to those described with respect to device 100 can be used in the corresponding layers of device 300. Figure 3 One example of how some layers can be added from the structures of devices 100 and 200 is provided.

[0144] Figure 1 Figure 2 Figure 3 The simple layered structure illustrated in Figure 1 , Figure 2 , and Figure 3 is provided as a non-limiting example, and it should be understood that embodiments of the present application can be used in connection with a wide 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 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. As an example, in the examples provided herein, many layers are described as including a single material, but it will be understood that combinations of materials, such as mixtures of matrix and dopant, or more generally mixtures, can be used. Furthermore, 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 300, the hole transport layer 104 transports holes and injects holes into the light emitting layer 1061, and can be described as a hole transport layer or an electron blocking layer. In one embodiment, an OLED can be described as having an organic layer disposed between a cathode and an anode. This organic layer can include a single layer, or can further include a plurality of layers of different organic materials as described in Figure 1 , Figure 2 , and Figure 3 . Figure 1 Figure 2 Figure 3

[0145] Structures and materials not specifically described can also be used, such as PLEDs including polymeric materials. As another example, OLEDs having a single organic layer or multiple stacks can be used. OLED structures can depart from the simple layered structure illustrated in Figure 1 , Figure 2 , and Figure 3 . For example, the substrate can include an angled reflective surface to improve light coupling. Figure 1 Figure 2 Figure 3 ​​​​​​​​

[0146] 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 application of one or more layers by sublimation with the aid of a carrier gas, wherein the materials are applied at a pressure in the range from 10 -5 The materials are applied at a pressure of between 10

[0147] Devices fabricated in accordance with embodiments of the application can further optionally include a barrier layer. The barrier layer can function to protect the electrod and organic layer from the environment surrounding the device. The barrier layer can be deposited on the substrate, on the electrode, on the organic layer, or on any other portion of the device, including on the edge portions of the substrate. The barrier layer can be deposited by any appropriate technique, including but not limited to thermal evaporation, sputtering, laser ablation, chemical vapor deposition, and molecular beam deposition. The barrier layer can be composed of materials including but not limited to metals, metalloids, and inorganic compounds. The barrier layer can be composed of a single material, or of a composite material including two or more materials. The barrier layer can be composed of an inorganic material, an organic material, or both. The barrier layer can be composed of a mixture of polymeric and non-polymeric materials. In order to be considered a mixture, the aforementioned polymeric and non-polymeric materials composing 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 be in the range from 95 / 5 to 5 / 95. In one example, the mixture of polymeric and non-polymeric materials composing the barrier layer consists essentially of polymeric silicon and inorganic silicon.

[0148] In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or completely deuterated. Thus, any specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (such as (but not limited to) alkyl, aryl, cycloalkyl, heteroaryl, and the like) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.

[0149] 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 employ the materials and structures.

[0150] Further, organic devices such as organic transistors can use the materials and structures.

[0151] 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.

[0152] In order to more clearly illustrate the present application, the technical solutions of the present application are described below in combination with some specific examples:

[0153] In the examples of the present application, the performance detection conditions of the electroluminescent device prepared are as follows:

[0154] Chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0155] Current-voltage: tested using a digital source meter Keithley 2420;

[0156] Power efficiency: tested using a NEWPORT 1931-C;

[0157] Luminance: tested using a luminance meter Minolta Cs-1000A.

[0158] Example 1

[0159] The preparation method of the metal complex P2 includes the following steps:

[0160] First step: preparation of compound Int-1

[0161]

[0162] Under nitrogen protection, 25.0 mmol of S1 was dissolved in 60 mL of DMSO, cooled to 0℃, 37.5 mmol of 60% oil-dispersed sodium hydride was added in batches, stirred for 30 minutes, then 30.0 mmol of S2 was added, the temperature was raised to room temperature, and the reaction was stirred for 15 hours. The reaction liquid was poured into 200 mL of ice water, filtered, the filter cake was washed with water, and the solid was separated and purified with a silica gel column to obtain the intermediate Int-1, a yellow solid, yield: 83%.

[0163] Second step: preparation of compound Int-2

[0164]

[0165] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 60 mL of DMF, and then 48.0 mmol of S3, 60.0 mmol of anhydrous potassium carbonate, 3.0 mmol of cuprous iodide and 6.0 mmol of N,N-dimethylglycine were added, and the temperature was raised to 120 °C, and the reaction was stirred for 12 hours, and then the temperature was lowered to room temperature, and the reaction solution was poured into 200 mL of water, and then filtered, and the filter cake was washed with water, and dried, and then separated and purified by silica gel column to obtain yellow solid Int-2, yield: 80%.

[0166] Third step: preparation of compound P2

[0167]

[0168] Under nitrogen protection, 15.0 mmol of Int-2 was dissolved in 50 mL of acetonitrile and 50 mL of chloroform, and then 31.0 mmol of Pt(COD)Cl2 and 150.0 mmol of sodium carbonate were added, and the temperature was raised to reflux, and the reaction was stirred for 2 days, and then the temperature was lowered to room temperature, and the reaction solution was poured into 500 mL of water, and then the organic phase was separated, and the aqueous phase was extracted with chloroform, and then the organic phase was collected, washed with water, dried, filtered, and the filtrate was concentrated under reduced pressure, and then dried, and then separated and purified by silica gel column to obtain compound P2, black blue solid, yield 42%. HRMS (MALDI-TOF): calculated value: 1047.12, measured value: 1047.12 [M + ].

[0169] Example 2

[0170] The preparation method of metal complex P23 comprises the following steps:

[0171] First step: preparation of compound Int-3

[0172]

[0173] Referring to the synthesis method of Example 1, second step, only S3 in Example 1, second step was replaced by S4 to prepare compound Int-3, yellow solid, yield 86%.

[0174] Third step: preparation of compound Int-4

[0175]

[0176] Under nitrogen protection, 10.0 mmol of Int-3 was dissolved in 50 mL of DMSO, and then 24.0 mmol of S5 (diphenyl iodonium triflate), 0.4 mmol of anhydrous copper acetate were added, and the temperature was raised to 120 °C, and the reaction was stirred for 10 hours, and then the temperature was lowered to room temperature, and the reaction solution was poured into 150 mL of ice water, and then filtered, and the filter cake was washed with water and ethanol to obtain yellow solid Int-4, yield: 58%.

[0177] Fourth step: preparation of compound P23

[0178]

[0179] Under nitrogen protection, 15.0 mmol of Int-4 was dissolved in 200 mL of DMF, 31.0 mmol of Pt(COD)Cl2 and 150.0 mmol of sodium acetate were added, and the reaction was stirred to reflux for 15 hours, cooled to room temperature, concentrated to dryness under reduced pressure, dissolved in dichloromethane, the organic phase was collected and washed with water, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column separation to obtain compound P23, a dark green solid, with a yield of 23%. HRMS (MALDI-TOF): calculated value: 1099.14, found value: 1099.15 [M + ]。

[0180] Example 3

[0181] The preparation method of metal complex P53 comprises the following steps:

[0182] First step: preparation of compound Int-5

[0183]

[0184] Under nitrogen protection, 25.0 mmol of S6 (prepared according to the synthesis method of Reference Example 1) was dissolved in 60 mL of 1-methylpyrrolidin-2-one, 50.0 mmol of anhydrous potassium carbonate and 25.0 mmol of S7 were added, and the reaction was stirred to reflux for 15 hours, cooled to room temperature, and the reaction solution was poured into 250 mL of water, extracted with dichloromethane, the organic phase was collected and washed with water, dried, filtered, and the filtrate was concentrated to dryness and purified by silica gel column separation to obtain intermediate Int-5, a yellow solid, with a yield of 75%.

[0185] Second step: preparation of compound Int-6

[0186]

[0187] Under nitrogen protection, 20.0 mmol of Int-5 was dissolved in 60 mL of 1-methylpyrrolidin-2-one, 50.0 mmol of anhydrous potassium carbonate and 25.0 mmol of S8 were added, and the reaction was stirred to reflux for 15 hours, cooled to room temperature, and the reaction solution was poured into 250 mL of water, filtered, the filter cake was washed with water and ethanol, and purified by silica gel column separation to obtain intermediate Int-6, a yellow solid, with a yield of 56%.

[0188] Third step: preparation of compound P53

[0189]

[0190] Under nitrogen protection, 15.0 mmol of Int-6 was dissolved in 50 mL of acetonitrile and 50 mL of chloroform, 31.0 mmol of Pt(COD)Cl2 and 150.0 mmol of sodium carbonate were added, and the reaction was stirred to reflux for 2 days, and then cooled to room temperature. The reaction solution was poured into 500 mL of water, and the organic phase was separated. The aqueous phase was extracted with chloroform, and the organic phase was collected, washed with water, dried, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound P53, a black solid, in a yield of 38%. HRMS (MALDI-TOF): calculated value: 1074.13, found value: 1074.13 [M + ]。

[0191] Example 4

[0192] Preparation of metal complex P320, comprising the following steps:

[0193] First step: preparation of compound Int-7

[0194]

[0195] Under nitrogen protection, 20.0 mmol of S9 was dissolved in 50 mL of DMF, and the temperature was lowered to 0°C. Then 24.0 mmol of 60% sodium hydride oil dispersion was added in batches, and the reaction was stirred for 1 hour. Then 22.0 mmol of S10 was added, and the temperature was raised to room temperature. The reaction was stirred for 15 hours. The reaction solution was poured into 200 mL of ice water, and then filtered. The filter cake was washed with water and ethanol, and the solid was purified by silica gel column chromatography to obtain compound Int-7, a yellow solid, in a yield of 93%.

[0196] Second step: preparation of compound Int-8

[0197]

[0198] Under nitrogen protection, 20.0 mmol of Int-7 was dissolved in 80 mL of dichloromethane, and the temperature was lowered to 0°C. Then 60.0 mmol of boron tribromide was added dropwise, and the reaction was stirred for 5 hours. Then 100 mL of saturated sodium bicarbonate aqueous solution was added, and the organic phase was separated, dried, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound Int-8, a yellow solid, in a yield of 95%.

[0199] Third step: preparation of compound Int-9

[0200]

[0201] Under nitrogen protection, 20.0 mmol of Int-8 was dissolved in 80 mL of DMF, 0.1 mol of anhydrous potassium carbonate and 60.0 mmol of S11 were added, and the temperature was raised to 110°C, and the reaction was stirred for 15 hours, and then the temperature was lowered to room temperature, the reaction solution was poured into 250 mL of water, filtered, the filter cake was washed with water and ethanol, and separated and purified by silica gel column to obtain intermediate Int-9, yellow solid, yield: 71%.

[0202] Fourth step: preparation of compound P320

[0203]

[0204] Referring to the synthesis method of Example 3 third step, only compound Int-6 in Example 3 third step was replaced by Int-9, compound P320 was prepared, yield: 40%, HRMS (MALDI-TOF): calculated value: 988.09, measured value: 988.09 [M + ].

[0205] Examples 5 to 339

[0206] Referring to the synthesis method similar to the above examples, the following compounds were prepared:

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] Fabrication of organic electroluminescent devices

[0240] An OLED element 200, such as Figure 2 As shown, the OLED element in this embodiment is a top-emitting element, including a substrate 101, an anode 102 disposed on 101, a hole injection layer 103 disposed on 102, a hole transport layer 104 disposed on 103, an electron blocking layer 105 disposed on 104, an organic light-emitting layer 106 disposed on 105, a hole blocking layer 107 disposed on 106, an electron transport layer 108 disposed on 107, an electron injection layer 109 disposed on 108, a cathode 110 disposed on 109, and a capping layer 111 on 110. The fabrication method of the OLED element is as follows:

[0241] The patterned ITO electrode glass substrate was treated in a cleaning agent for 30 minutes, rinsed in deionized water, treated in an acetone / ethanol mixed solvent for 30 minutes, baked to dryness in a clean environment, irradiated by a UV light cleaning machine for 10 minutes, and the surface was bombarded by a low-energy cation beam.

[0242] The treated ITO glass substrate was placed in a vacuum chamber, vacuumed to less than 1 x 10 -5 Pa, and silver was evaporated as an anode on the ITO film, with an evaporation film thickness of Compound HATCN was continuously evaporated as a hole injection layer, with an evaporation film thickness of HTM was continuously evaporated as a hole transport layer on the hole injection layer film, with an evaporation film thickness of

[0243] BPrime was evaporated as an electron blocking layer on the hole transport layer, with an evaporation film thickness of

[0244] The metal complex of the present application and PH025 were evaporated as an organic light-emitting layer of the device on the electron blocking layer, wherein PH025 is a host material and the metal complex of the present application is a dopant material, with a doping concentration of 3%, and an evaporation film thickness of

[0245] Compound DPO was continuously evaporated as a hole blocking layer of the device on the organic light-emitting layer, with an evaporation film thickness of

[0246] LiQ and ET218 were continuously evaporated as an electron transport layer of the device on the hole blocking layer, wherein LiQ is 50% of the mass of ET218, with an evaporation film thickness of

[0247] LiF was continuously evaporated as an electron injection layer of the device on the electron transport layer, with an evaporation film thickness of

[0248] Metallic magnesium and silver were evaporated as a cathode layer of the device on the electron injection layer, wherein the mass ratio of magnesium and silver is 1:10, with an evaporation film thickness of

[0249] Finally, compound HTM was evaporated as a capping layer on the cathode layer, with an evaporation film thickness of The organic electroluminescent element of the present application was fabricated, as shown in FIG. 2 of the attached drawing. Figure 2 The device 200.

[0250] Comparative Example 1

[0251] A comparative element 1 was produced in the same manner as the above-described organic electroluminescent device, except that the compound shown by BD011 was used instead of the metal complex of the above-described organic electroluminescent device.

[0252] The structural formulas of the aforementioned HATCN, HTM, BPrime, PH025, BD011, DPO, ET218 are shown below:

[0253]

[0254]

[0255] Examples 340 to 679

[0256] An organic electroluminescent element was produced in the same manner as the above-described organic electroluminescent device, except that the metal complex contained in the organic electroluminescent material of the present application was used instead of the metal complex of the above-described organic electroluminescent device, and the driving voltage and current efficiency of the light-emitting element and the lifetime of the element were measured using a digital source meter and a luminance meter. 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 element reached 10 mA / cm 2 was measured, i.e., the driving voltage, and the luminance at that time was also measured; the ratio of the luminance to the current density was the current efficiency; the LT95% lifetime test was performed as follows: using a luminance meter, the luminance of the organic electroluminescent element was measured while maintaining a constant current at 1000 cd / m 2 , and the time until the luminance decreased to 950 cd / m 2 was measured, in hours; some of the results are summarized in Table 2, and the data are normalized relative to the comparative element 1.

[0257] Table 2

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] As can be seen from Table 2, the organic electroluminescent element prepared from the dinuclear platinum complex of the application has lower driving voltage, higher efficiency and excellent lifetime compared with the comparative element 1, and is an excellent organic electroluminescent material in performance.

[0268] The metal complex BD011 of the comparative element 1 is different from the dinuclear platinum complex of the application in that two platinum atoms are introduced into the monoligand molecule of the dinuclear platinum complex of the application, and the metal-to-ligand charge transfer (MLCT) is multiplied, thus the efficiency is high and the lifetime is prolonged. The metal complex BD011 utilizes the conjugation effect of boron-nitrogen or boron-oxygen to realize TADF effect and MLCT, which reduces the MLCT efficiency, and the phosphorescent lifetime of the complex is increased, thus the driving voltage is high and the efficiency is low, which indicates that the dinuclear platinum complex of the application is more advantageous in performance such as luminescent efficiency and lifetime.

[0269] The above merely represents a representative example of the specific implementation of the application, but the protection scope of the application is not limited thereto, any person skilled in the art can easily think of changes or replacements within the technical range disclosed by the application, which should be covered within the protection scope of the application. Therefore, the protection scope of the application should be subject to the protection scope of the claims.

Claims

1. A dinuclear platinum complex, characterized in that, The dinuclear platinum complex is selected from the group consisting of: R A1 , R A20 , R B1 , R B107 , R B186 , R C1 The structures of R A1 , R A20 , R B1 , R B107 , R B186 , R C1 are shown below.

2. An organic electroluminescent device, characterized by comprising The organic electroluminescence device comprises an anode, a cathode and at least one organic layer disposed between the anode and the cathode, and the organic layer comprises the dinuclear platinum complex of claim 1.

3. The organic electroluminescence device according to claim 2, wherein The organic layer further comprises a host material and a dopant material, and the dopant material comprises the dinuclear platinum complex of claim 1; and the host material is selected from the group consisting of triphenylene, carbazole, indolocarbazole, dithiophene, dithiophene, fluorene, dithiophene, 5,9-dioxo-13b-boron naphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dithiophene, aza-dithiophene, aza-dithiophene and aza-(5,9-dioxo-13b-boron naphtho[3,2,1-de]anthracene) or a group derived from a combination of these systems.

4. The organic electroluminescence device according to claim 3, wherein The host material is selected from the group consisting of the following structures: 5.The organic electroluminescence device according to claim 3 or 4, characterized by The mass ratio of the host material and the dopant material is 99:1 to 1:99.

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