Metal platinum complex and use thereof

Abstract

The application belongs to the technical field of luminescent materials, and particularly relates to a metal platinum complex and application thereof. The structure of the metal platinum complex is shown in formula (1). When the metal platinum complex is used in an OLED, especially in a blue light emitting area, the metal platinum complex exhibits enhanced phosphorescence quantum yield, good luminescence stability, high luminescence efficiency, and is suitable for being used as an emitter material in OLED application. The metal platinum complex can obtain an organic electroluminescent device with deep blue phosphorescence and improved luminescence efficiency, and the luminescent device has good thermal stability. The metal platinum complex can regulate the photophysical properties by adjusting the structure of the ligand around the metal center and the structure of the substituent on the ligand, has the advantages of narrow emission spectrum, high stability and high efficiency, 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 metal 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 adapted to emit 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 inhibit 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 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-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 platinum complex and application thereof. When the metal 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 metal platinum complex. The metal platinum complex has good electroluminescent stability and excellent luminous efficiency.

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

[0008] A third object of the present application provides an organic electroluminescent device, comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal 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 metal platinum complex, having a structure as shown in formula (1):

[0012]

[0013] wherein ring A is a 5-membered heterocycle;

[0014] ring C, ring D, and ring E are each independently selected from a 5-membered carbocycle, a 5-membered heterocycle, a 6-membered carbocycle, or a 6-membered heterocycle;

[0015] V 1 , V 2 , V 3 , V 4 are each independently selected from C or N;

[0016] X 1 , X 2 , X 3 are each independently selected from CR 1 or N;

[0017] R 2 , R 3 , R 4 each independently represent mono-substitution or multi-substitution to a saturated substitution, or no substitution;

[0018] L 1 , L 2 are each independently selected from a single bond, O, S, S=O, SO2, Se, NR 5 , PR 5 , R 5 P=O, CR 5 R 6 ,

[0019] C=O, SiR 5 R 6 , GeR 5 R 6 , or BR 5 ;

[0020] R 1 , R 2 , R3 4 5 6 at each occurrence is independently selected from hydrogen or is 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 sulfido group, a selenoalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, a linear alkyl group having Ci to C 40 , a linear heteroalkyl group having Ci to C 40 , a branched or cyclic alkyl group having C3 to C 40 , an alkoxy group having Ci to C 40 , an arylalkyl group having C6 to C 60 , an aryloxy group having C6 to C 60 , an arylamine group having C6 to C 60 , a silyl group having C3 to C 40 , an alkenyl group having C2 to C 40 , a cycloalkenyl group having C4 to C 40 , a heteroalkenyl group having C2 to C 40 , an alkynyl group having C2 to C 40 , an aryl group having C6 to C 60 , a heteroaryl group having C2 to C 60 and combinations thereof, any two or more adjacent R 1 2 3 4 5 6 may optionally be joined or fused to form a substituted or unsubstituted ring.

[0021] Preferably, the metal platinum complex is selected from the group consisting of:

[0022]

[0023]

[0024] wherein V 2 , V 3 , V 4 , L 1 , L 2 , R 1 to R 4 , ring A, ring C, ring D and ring E are defined the same as in formula (I).

[0025] ​​​​​​​​In the substituted or unsubstituted ring formed by the adjacent groups binding to each other in the present application, the "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The condensed ring refers to a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocyclic ring, a condensed aromatic heterocyclic ring or a combination thereof.

[0026] The 5-membered carbon ring in the present application refers to a monocyclic and polycyclic system having 5 carbon atoms, and the polycyclic ring refers to a ring having two or more rings in which two carbons are shared by two adjacent rings, for example, the 5-membered carbon ring can be cyclopentane, cyclopentene, 2,3-dihydroindene, indene, etc. The 5-membered heterocyclic ring refers to a 5-membered carbon ring containing at least one heteroatom, and the total number of heteroatoms and carbon atoms constituting the ring is 5, and the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, phosphorus, boron, silicon or selenium, and in many cases, oxygen, sulfur or nitrogen is the preferred heteroatom, and non-limiting examples of the 5-membered heterocyclic ring include: pyrazole, imidazole, oxazole, thiazole, triazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, benzimidazole, benzoxazole, benzotriazole, etc.

[0027] The 6-membered carbon ring in the present application refers to a monocyclic and polycyclic system having 6 carbon atoms, and as preferred, the 6-membered carbon ring refers to the aryl group in the present application. The 6-membered heterocyclic ring refers to a ring system in which the total number of heteroatoms and carbon atoms is 6, and as preferred, the 6-membered heterocyclic ring refers to a 6-membered heteroaryl group, for example: pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phthalazine, pteridine, etc.

[0028] Preferably, the ring C is a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0029] Preferably, the ring D, the ring E are each independently selected from a 5-membered heteroaromatic ring, a 6-membered aromatic ring or a 6-membered heteroaromatic ring.

[0030] Further, the metal platinum complex is selected from the group consisting of:

[0031]

[0032]

[0033]

[0034] wherein, V 1 ~V 4 , L 1 , L 2 , R 2 ~R 4 , X 1 ~X 3 , the definitions of the ring A, the ring C are the same as those in formula (I).

[0035] Y is independently selected from N, P, P=O, and CR. 9 SiR 9 or GeR 9 ;

[0036] Z is independently selected from single bonds, O, S, and NR. 10 PR 10 R 10 P = O, CR 10 R 11 SiR 10 R 11 BR 10 S=O, SO2, C=O, AsR 10 R 10 As = O, GeR 10 R 11 Or without Z, or a group consisting of the following groups:

[0037]

[0038]

[0039] Where n is selected from 0, 1, 2 or 3;

[0040] R 7 R 8 Each can be used independently to represent monosubstituted or polysubstituted to saturated substituted, or unsubstituted;

[0041] R 7 R 8 R 9 R 10 R 11 R 12 Each is independently selected from hydrogen or from the group consisting of: deuterium, halogen atom, nitrile group, acyl group, carboxylic acid group, ether, ester group, isonitrile group, thio group, selenyl group, sulfinyl group, sulfonyl group, phosphine 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 40The 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 7 R 8 R 9 R 10 R 11 R 12 They can be optionally joined or circulated to form substituted or unsubstituted rings.

[0042] Preferably, Y is N.

[0043] Preferably, the L 1 L 1 Each is independently selected from single bonds, O, S, S=O, SO2, CR 5 R 6 C=O or SiR 5 R 6 .

[0044] Preferably, each of Z is independently selected from O, S, S=O, SO2, and CR. 9 R 10 C=O, SiR 9 R 10 or NR 11 .

[0045] Preferably, 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, deuterium, fluorine, and nitrile groups, and has a C1 to C2 group. 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 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.

[0046] Furthermore, the R 1 R2 3 4 5 6 7 8 9 10 11 12 each independently selected from the group consisting of a hydrogen atom, a deuterium atom, fluorine, a nitrile group, R A1 A30 B1 B195 C1 C80

[0047] wherein R A1 A30 are represented by the following structural formulae:

[0048]

[0049]

[0050] R B1 B195 are represented by the following structural formulae:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] R C1 C80 are represented by the following structural formulae:

[0057]

[0058]

[0059]

[0060] wherein each hydrogen atom in each substituent can be replaced with a deuterium atom.

[0061] Further, R 5 6 9 10 ​​​​​​​​​​​​​​​​​​​​​​, R 11 each independently is selected from the group consisting of R A1 ~R A26 , R B1 ~R B185 , R C1 ~R C79 .

[0062] Further, each R 1 , R 2 , R 3 , R 4 , R 7 , R 8 is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, isonitrile, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 ; R 2 , R 3 , R 4 , R 7 , R 8 each represents mono- or polysubstitution to saturated substitution or no substitution, and any two or more adjacent substituents can optionally be joined or fused to form a substituted or unsubstituted ring.

[0063] Still further, each L 1 , L 1 is independently selected from a single bond, O, S, or CR 5 R 6 .

[0064] Still further, each Z is independently selected from O, S, CR 9 R 10 , or NR 11 .

[0065] Still further, each R 5 , R 6 , R 9 , R 10 , R 11 is independently selected from the group consisting of R A1 , R A10 , R B1 , R C1 .

[0066] Still further, each R 1 , R 2 , R 3 , R 4 , R 7 , R 8each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ~R A30 , R B1 ~R B195 , R C1 ~R C80 consisting of hydrogen, deuterium, fluorine, nitrile, R 2 , R 3 , R 4 , R 7 , R 8 each independently represents mono- or polysubstitution to saturated substitution or no substitution.

[0067] "Aryl" according to the present application means and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic can have two or more rings in which two carbons 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 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, naphthyl, anthracenyl, azulenyl, phenanthrenyl, fluorenyl, pyrenyl, perylenyl, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenyl and naphthyl. Additionally, the aryl group can be optionally substituted.

[0068] "Heteroaryl" in the sense of the present invention 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, benzoseleophene, 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, benzoseleophenopyridine, and seleophenodipyridine, 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.

[0069] Alkyl in the sense of the present invention contains from 1 to 40 carbon atoms, and straight-chain alkyl or branched alkyl groups, alkenyl or alkynyl groups, in which the individual hydrogen atoms or -CH2- groups can also be replaced, contain at least two carbon atoms, as non-limiting examples, alkyl, alkenyl or alkynyl groups are preferably understood to mean methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-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.

[0070] The preferred alkoxy group has 1 to 40 carbon atoms and is considered to be alkoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy, and 2,2,2-trifluoroethoxy.

[0071] Heteroalkyl groups are preferably alkyl groups having 1 to 40 carbon atoms, referring to groups in which a single hydrogen atom or -CH2- group is replaced by an oxygen, sulfur, or halogen atom. These are considered to be alkoxy, alkathio, fluorinated alkoxy, fluorinated alkathio, particularly methyl thio, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethyl thio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio. Trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butenthio, butenoxy, penenoxy, penenthio, cyclopentenoxy, cyclopententhio, hexenoxy, hexenthio, cyclohexenoxy, cyclohexenthio, acetylenoxy, acetylenthio, propylenoxy, propylenthio, butylenoxy, butylenthio, penylenoxy, penylenthio, hexylenoxy, hexylenthio.

[0072] Generally, the cycloalkyl and cycloalkenyl groups according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, or cycloheptenyl, wherein one or more -CH2- groups can be replaced by the above groups; in addition, one or more hydrogen atoms can be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0073] The alkenyl or ynyl group according to the invention has 2 to 40 carbon atoms, and wherein individual hydrogen atoms may be substituted, preferably vinyl, propenyl, butenyl, isobutenyl, styrene, stilbene, acetylenyl, propynyl, butynyl, or phenylacetylenyl; furthermore, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0074] According to the invention, aryl or heteroaryl groups, in particular, refer to groups derived from substances such as phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, pyrene, etc. 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.

[0075] As used herein, "acyl" means a substituted carbonyl group (COR).

[0076] As used herein, "ester" means a substituted oxycarbonyl group (-OCOR or CO2R).

[0077] As used herein, "ether" means a -OR group.

[0078] As used herein, "sulfide" or "sulfide" are used interchangeably and mean a -SR group.

[0079] As used herein, "sulfenyl" refers to a -SOR group.

[0080] As used herein, "sulfonyl" refers to a -SO2R group.

[0081] As used herein, "phosphino" refers to a -PR3 group, where each R can be the same or different.

[0082] As used herein, "silyl" refers to a -SiR3 group, where each R can be the same or different.

[0083] Each R described above is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.

[0084] As used herein, aryloxy refers to R'O - As used herein, aryloxy refers to R'O

[0085] As used herein, alkylsilyl refers to a silyl group substituted with an alkyl group having a carbon number of 1 to 40, and the carbon number constituting the alkylsilyl group is at least 3. As non-limiting examples of alkylsilyl, there are trimethylsilyl, triethylsilyl, and the like. Arylsilyl refers to a silyl group substituted with an aryl group having a carbon number of 6 to 60.

[0086] As used herein, arylphosphino refers to a diarylphosphino group substituted with an aryl group having a carbon number of 6 to 60. As non-limiting examples of arylphosphino, there are diphenylphosphino, di(4-trimethylsilylphenyl)phosphino, and the like. Aryloxyphosphino refers to a diarylphosphino group in which the phosphorus atom is oxidized to the highest valence state.

[0087] As used herein, arylboron refers to a diarylboron group substituted with an aryl group having a carbon number of 6 to 60. As non-limiting examples of arylboron, there are diphenylboron, di(2,4,6-trimethylphenyl)boron, and the like. Alkylboron refers to a dialkylboron group substituted with an alkyl group having a carbon number of 1 to 40. As non-limiting examples of alkylboron, there are di-t-butylboron, di-isobutylboron, and the like.

[0088] As used herein, "halo", "halogen", "halogen atom", and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, or iodine.

[0089] 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.

[0090] 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.

[0091] In one instance, the term substitution includes a combination of two to four listed groups.

[0092] 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.

[0093] According to an embodiment of the present invention, the platinum metal complex is selected from the group consisting of:

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] wherein some or all of the hydrogen atoms in each structure can be replaced by deuterium atoms. Use of one of the metal platinum complexes in an organic electroluminescent device.

[0117] The organic electroluminescent device of the present application can achieve blue light with high luminous efficiency.

[0118] 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 platinum complex of formula (I).

[0119] The organic layer of the present application can be an emissive layer and the metal platinum complex as described herein can be an emissive dopant or a non-emissive dopant.

[0120] Further, the organic layer can further comprise a host material and a dopant, wherein the dopant comprises a metal platinum complex of formula (I).

[0121] The metal platinum complex can be a sensitizer; wherein the device can further comprise an acceptor, a fluorescent emitter, a delayed fluorescent emitter, and combinations thereof.

[0122] The organic electroluminescent device of the present disclosure can further comprise an emission region comprising a compound as disclosed in the above compound section of the present disclosure.

[0123] 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.

[0124] The mass ratio of the host material to the dopant material is 99:1 to 1:99.

[0125] Preferably, the mass ratio of the host material to the dopant material is 99:1 to 50:50.

[0126] More preferably, the mass ratio of the host material to the dopant material is 98:2 to 90:10.

[0127] 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. 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. Those skilled in the art will be able to assess whether a material is suitable based on its performance in conjunction with the compounds disclosed herein and the underlying principles described herein.

[0128] 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.

[0129] According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have found that the introduction of these ligands unexpectedly narrows the emission spectrum, reduces the sublimation temperature, and increases the luminous efficiency of the device.

[0130] As the production method of the organic electroluminescent device of the present application, the following production method can be cited, but is not limited thereto, and various changes can be made by those skilled in the art based on the technical common sense in the art. The aforementioned production method includes the following steps:

[0131] a cleaning step of cleaning the ITO-equipped glass substrate using a cleaning agent, deionized water, an organic solvent, or the like;

[0132] 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;

[0133] a step of forming a hole transport layer by vacuum deposition of a hole transport layer-forming material on the aforementioned hole injection layer;

[0134] 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;

[0135] 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;

[0136] 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.

[0137] A consumer product including the aforementioned organic electroluminescent device.

[0138] 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 interior or exterior illumination and / or signaling, a heads-up display, a full or partial 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 micro display 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.

[0139] Compared with the prior art, the present application has the following advantages:

[0140] (1) The metal 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 metal platinum complex of the present application can obtain an organic electroluminescent device with blue phosphorescence and improved light emission efficiency, and the light emitting device has good thermal stability, the consumer product of the organic light emitting device of the present application can obtain electronic equipment with blue phosphorescence and improved light emission efficiency by containing the organic electroluminescent device of the present application;

[0141] (2) The metal 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, has the advantages of narrow emission spectrum, high stability and high efficiency, and has wide application prospects in many fields of OLED display and lighting lamps. BRIEF DESCRIPTION OF DRAWINGS

[0142] 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 description of the embodiments or the prior art 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 also obtain other drawings according to these drawings without creative labor.

[0143] Figure 1 A schematic diagram of an organic light emitting device 100 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, 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.

[0144] Figure 2 A schematic diagram of an organic light emitting device 200 is shown. The illustration is 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, 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 omitting the hole blocking layer 107, and can be fabricated by the fabrication method of the device 100.

[0145] Figure 3An organic light-emitting device 300 showing two light-emitting layers is schematically illustrated. 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

[0146] 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 below in detail. 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.

[0147] 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.

[0148] The organic electroluminescent device described in the present application includes at least one organic layer, which is disposed between and electrically connected to an anode and a cathode. Figure 1 An organic light-emitting device 100 is schematically illustrated. 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 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. The device 100 can be fabricated by sequentially depositing the described layers.

[0149] Figure 2An organic light emitting device 200 containing two light emitting layers is shown schematically. The device includes a substrate 201, an anode 202, a hole injection layer 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. While the most common OLED devices have one light emitting layer of a single color or three light emitting layers of the three primary colors, the device 200 has two light emitting layers of the same color. Similar materials to those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 One example of how some layers can be added from the structure of device 100 is provided.

[0150] Figure 1 and Figure 2 The simple layered structure illustrated in FIGS. 1-3 is provided as a non-limiting example, and it should be understood that embodiments of the 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. In the examples provided herein, many of the layers are described as including a single material, but it will be understood that combinations of materials can be used, e.g., mixing a matrix and a dopant, or more generally, a mixture. 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, the hole transport layer 204 transports holes and injects holes into the light emitting layer 205, 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 FIGS. 1-3, for example. The organic materials can be deposited as a single film or as multiple films. Figure 1 and Figure 2 multiple layers of different organic materials as described in FIGS. 1-3.

[0151] PLEDs including polymeric materials can also be used, for example. As another example, OLEDs having a single organic layer or multiple stacks can be used. The OLED structure can depart from the simple layered structure illustrated in FIGS. 1-3. For example, the substrate can include an angled reflective surface to improve light coupling. Figure 1 and Figure 2 PLEDs including polymeric materials can also be used, for example. As another example, OLEDs having a single organic layer or multiple stacks can be used. The OLED structure can depart from the simple layered structure illustrated in FIGS. 1-3. For example, the substrate can include an angled reflective surface to improve light coupling.

[0152] 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 material is applied at a pressure of 10 -5 between 10"3and 1 bar. 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 process, such as screen printing, flexographic printing, offset printing, light-induced thermal imaging, thermal transfer printing, inkjet printing or nozzle printing, to produce one or more layers. 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.

[0153] Devices made in accordance with embodiments of the application can further optionally include a barrier layer. One use of a barrier layer is to protect the electrodes and organic layers from being damaged by 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, beside the substrate, 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.

[0154] 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, 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.

[0155] 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.

[0156] Further, organic devices such as organic transistors can use the materials and structures.

[0157] 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.

[0158] 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:

[0159] In the examples of the present application, the performance detection conditions of the electroluminescent device prepared are as follows:

[0160] Chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0161] Current-voltage: tested using a digital source meter Keithley 2420;

[0162] Power efficiency: tested using a NEWPORT 1931-C;

[0163] Luminance: tested using a luminance meter Minolta Cs-1000A.

[0164] Example 1

[0165] The preparation method of the metal complex P1 includes the following steps:

[0166] First step: preparation of compound Int-1

[0167]

[0168] 20.0 mmol of S1 was dispersed in 100 mL of dry toluene, 24.0 mmol of 1,2-diphenylethylenediamine, 24.0 mmol of p-toluenesulfonic acid, 2.0 mmol of anhydrous magnesium sulfate and 20 g of molecular sieves were added, and the reaction was stirred at reflux for 24 hours. The temperature was lowered to room temperature, and the mixture was filtered. The filtrate was concentrated under reduced pressure to dryness, 150 mL of dry toluene was added, and 200.0 mmol of manganese dioxide was added. The reaction was stirred at reflux for 24 hours. The temperature was lowered to room temperature, and the mixture was filtered. The filtrate was concentrated under reduced pressure to dryness, and was purified by silica gel column separation to obtain compound Int-1, a yellow solid, with a yield of 78%.

[0169] Second step: preparation of compound Int-2

[0170]

[0171] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 150 mL of acetone, 24.0 mmol of methyl iodide was added dropwise, the reaction was stirred at room temperature for 3 days, about 20 mL of residual liquid was concentrated under reduced pressure, 100 mL of ethyl acetate was added, filtered, the filter cake was washed with ethyl acetate, the obtained solid was dissolved in 150 mL of methanol and 15 mL of water, 40.0 mmol of ammonium hexafluorophosphate was added, the reaction was stirred at room temperature for 15 hours, a small amount of residual water was concentrated under reduced pressure, 50 mL of water was added, filtered, the filter cake was washed with water, dried, and compound Int-2 was obtained, yellow solid, yield 52%.

[0172] Third step: preparation of compound P1

[0173]

[0174] Under nitrogen protection, 15.0 mmol of Int-2 was dispersed in 150 mL of DMF, 16.5 mmol of Pt(COD)Cl2 and 45.0 mmol of anhydrous potassium acetate were added, the reaction was stirred to reflux for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, dissolved in dichloromethane, filtered, and the filtrate was concentrated to dryness under reduced pressure, and purified by silica gel column separation to obtain compound P1, yellow solid, yield: 38%. MS (MALDI-TOF): 659.16 [M + ]。

[0175] Example 2

[0176] The preparation method of metal complex P31 comprises the following steps:

[0177] First step: preparation of compound Int-4

[0178]

[0179] Under nitrogen protection, 20.0 mmol of Int-3 (prepared according to the synthesis method of reference example 1) was dissolved in 80 mL of DMF, 30.0 mmol of S3, 3.0 mmol of cuprous iodide, 60.0 mmol of anhydrous cesium carbonate and 6.0 mmol of N,N-dimethylglycine were added, the temperature was raised to 150°C, the reaction was stirred for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, 80 mL of dichloromethane was added and stirred to dissolve, filtered, the filtrate was concentrated to dryness, and purified by silica gel column separation to obtain intermediate Int-4, yellow solid, yield: 90%.

[0180] Second step: preparation of compound P31

[0181]

[0182] Under nitrogen protection, 15.0 mmol of Int-4 was dissolved in 100 mL of acetic acid, 16.5 mmol of K2PtCl4 and 1.5 mmol of tetrabutylammonium bromide were added, and the reaction was stirred to reflux for 48 hours, cooled to room temperature, concentrated to dryness under reduced pressure, dissolved in dichloromethane, filtered, and the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column separation to obtain compound P31, yellow solid, yield: 56%. MS (MALDI-TOF): 745.18 [M + ]。

[0183] Example 3

[0184] The preparation method of metal complex P188 comprises the following steps:

[0185] First step: preparation of compound Int-5

[0186]

[0187] Under nitrogen protection, 20.0 mmol of S4 was dispersed in 100 mL of dry toluene, 24.0 mmol of S5, 24.0 mmol of p-toluenesulfonic acid, 2.0 mmol of anhydrous magnesium sulfate and 20 g of molecular sieves were added, and the reaction was stirred to reflux for 24 hours, cooled to room temperature, filtered, and the filtrate was concentrated to dryness under reduced pressure, 150 mL of dry toluene was added, 0.1 mol of manganese dioxide was added, the reaction was stirred to reflux for 24 hours, cooled to room temperature, filtered, and the filtrate was concentrated to dryness under reduced pressure and purified by silica gel column separation to obtain compound Int-5, white solid, yield 84%.

[0188] Second step: preparation of compound Int-6

[0189]

[0190] Referring to the synthesis method of the first step of Example 2, only Int-3 of the first step of Example 2 was replaced by Int-5, compound Int-6 was prepared, yellow solid, yield 88%.

[0191] Third step: preparation of compound P188

[0192]

[0193] Referring to the synthesis method of the second step of Example 2, only Int-4 of the second step of Example 2 was replaced by Int-6, compound P188 was prepared, yellow solid, yield: 54%. MS (MALDI-TOF): 670.15 [M + ]。

[0194] Example 4

[0195] The method for preparing the metal complex P339 comprises the following steps:

[0196] First step: preparation of compound Int-7

[0197]

[0198] Under nitrogen protection, 24.0 mmol of 3-methoxybromobenzene was dissolved in 100 mL of dry xylene, cooled to -78°C, and 28.5 mmol of 2.5M n-butyllithium n-hexane solution was added dropwise, stirred for 30 minutes, then 29.0 mmol of boron tribromide was added dropwise, stirred for 1 hour, 20.0 mmol of S6 dissolved in 20 mL of triethylamine was added dropwise, stirred for 1 hour, warmed to reflux and stirred for 24 hours, cooled to room temperature, concentrated under reduced pressure, and dried with silica gel column separation and purification to obtain compound Int-7, white solid, yield 74%.

[0199] Second step: preparation of compound Int-8

[0200]

[0201] Under nitrogen protection, 20.0 mmol of Int-7 was dissolved in 100 mL of dichloromethane, cooled to 0°C, and 24.0 mmol of boron tribromide was added dropwise, stirred for 1 hour, 50 mL of saturated aqueous ethylenediaminetetraacetic acid disodium salt solution was added, the organic phase was separated, dried, filtered, and the filtrate was concentrated under reduced pressure and dried with silica gel column separation and purification to obtain compound Int-8, yellow solid, yield 94%.

[0202] Third step: preparation of compound Int-9

[0203]

[0204] Under nitrogen protection, 20.0 mmol of Int-8 and 22.0 mmol of S7 were dissolved in 60 mL of DMF, 30.0 mmol of anhydrous cesium carbonate was added, warmed to 120°C, stirred for 15 hours, cooled to room temperature, the reaction liquid was poured into 150 mL of water, filtered, the filter cake was washed with water and ethanol, and purified with a silica gel column to obtain compound Int-9, yellow solid, yield 82%.

[0205] Fourth step: preparation of compound P339

[0206]

[0207] Referring to the synthetic method of Example 2, Step 2, only replacing Int-4 of Example 2, Step 2 with Int-9, Compound P339 was prepared in yield of 35% as a yellow solid. MS (MALDI-TOF): 736.19 [M+H] + .

[0208] Examples 5 to 383

[0209] The following compounds were prepared according to synthetic methods analogous to the above examples:

[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]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] Application Example 1

[0247] Fabrication of organic electroluminescent devices

[0248] 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 layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 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 fabrication method of the element is as follows:

[0249] The patterned ITO electrode glass substrate is 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 is bombarded by a low-energy cation beam.

[0250] The treated ITO glass substrate is placed in a vacuum chamber, vacuumed to less than 1 x 10 -5 Pa, and silver is evaporated as an anode on the ITO film, with an evaporation film thickness of The compound HATCN is continuously evaporated as a hole injection layer, with an evaporation film thickness of The HTM is continuously evaporated as a hole transport layer on the hole injection layer film, with an evaporation film thickness of

[0251] BPrime is evaporated as an electron blocking layer on the hole transport layer, with an evaporation film thickness of

[0252] The metal complex of the present application and PH022 are evaporated as an organic light-emitting layer of the device on the electron blocking layer, wherein PH022 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

[0253] The compound DPO is continuously evaporated as a hole blocking layer of the device on the organic light-emitting layer, with an evaporation film thickness of

[0254] LiQ and ET318 are continuously evaporated as an electron transport layer of the device on the hole blocking layer, wherein LiQ is 50% of the mass of ET318, with an evaporation film thickness of

[0255] LiF is continuously evaporated as an electron injection layer of the device on the electron transport layer, with an evaporation film thickness of

[0256] Metallic magnesium and silver are 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

[0257] Finally, the compound HTM is evaporated as a capping layer on the cathode layer, with an evaporation film thickness of The organic electroluminescent element of the present application is manufactured, as shown in FIG. 1, as a device 100. Figure 1 Comparative Example 1

[0258]

[0259] ​The metal complex of the present invention shown in Application Example 1 was replaced with the compound shown in BD015, and the other steps were the same as described above to prepare the comparative element 1.

[0260] The structural formulas of HATCN, HTM, BPrime, PH022, BD015, DPO, and ET318 mentioned above are shown below:

[0261]

[0262]

[0263] Application Example 2

[0264] Fabrication of organic electroluminescent devices

[0265] 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 layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 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, an electron transport layer 108 disposed on the organic light-emitting layer 106, 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 OLED element in this embodiment omits the hole blocking layer 107. In the corresponding layers of the element 200, materials similar to those described with respect to the element 100 can be used. The element 200 of the present invention can be manufactured with reference to the manufacturing method of the element 100 in Application Example 1.

[0266] Application Example 3

[0267] Fabrication of organic electroluminescent devices

[0268] Figure 3 A schematic diagram of an organic light-emitting device 300 with two light-emitting layers is shown. 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 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 fabricated by sequentially depositing the described layers. Because most common OLED devices have one light-emitting layer, and device 300 has a first light-emitting layer and a second light-emitting layer, the emission peaks of the first and second light-emitting layers can be overlapping, cross-overlapping, or non-overlapping. Materials similar to those described with respect to device 100 can be used in the corresponding layers of device 300.Figure 3 Provide an example of how to add layers from the structure of device 100.

[0269] The organic electroluminescent element manufactured above was used to measure its driving voltage, current efficiency, and lifetime using a digital source meter and luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the current density of the organic electroluminescent element was measured when it reached 10mA / cm². 2 The voltage at that time is the driving voltage, and the brightness at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the LT95% lifespan test is as follows: using a luminance meter at 5000 cd / m² 2 At a constant current under the given brightness, the brightness decay of the organic electroluminescent element was measured to be 4750 cd / m². 2 The time is in hours, and some of the results are summarized in Table 1. *The data is normalized compared to Comparative Example 1.

[0270] Table 1

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281] As can be seen from Table 1, compared with the comparative element 1, the organic electroluminescent element prepared by the metal complex of the present invention has a lower driving voltage, higher efficiency and longer lifespan, and is a high-performance organic electroluminescent material.

[0282] The above merely represents a representative example of a specific implementation 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 by the present application, which should be encompassed within the scope of protection of the present application. Therefore, the scope of protection of the present application should be subject to the scope of protection of the claims.

Claims

1. A platinum metal complex, characterized in that, The structures of the platinum metal complexes belong to the following group: 。 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 platinum complex of claim 1.

3. The organic electroluminescent device according to claim 2, characterized in that, The organic layer comprises a host material and a dopant material, wherein the dopant material comprises the platinum metal complex as described in claim 1.

4. The organic electroluminescent device according to claim 3, characterized in that, The main 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).

5. The organic electroluminescent device according to claim 3 or 4, characterized in that, The mass ratio of the main material to the doped material is 99:1 to 1:99.

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