阅读说明：本技术 一种金属配合物、有机电致发光元件及消费型产品 (Metal complex, organic electroluminescent element and consumer product ) 是由 赵雷 韩洪波 曹建华 唐怡杰 刘殿君 边坤 郭文龙 何连贞 于 2021-08-26 设计创作，主要内容包括：本发明涉及一种金属配合物、有机电致发光元件及消费型产品,本发明所述的金属配合物用作发光材料能够获得发光效率高的绿色至红色磷光材料,且制备的发光材料的热稳定性好,本发明制备的有机电致发光元件发绿色至红色磷光且发光效率高,热稳定性好；本发明的电子设备通过含有本发明的有机电致发光元件,从而能够获得电致发光为绿色至红色磷光且发光效率提高的消费型产品。(The invention relates to a metal complex, an organic electroluminescent element and a consumer product, the metal complex is used as a luminescent material to obtain a green to red phosphorescent material with high luminous efficiency, and the prepared luminescent material has good thermal stability; the electronic device of the present invention contains the organic electroluminescent element of the present invention, and thus a consumer product having green to red phosphorescence as electroluminescence and improved luminous efficiency can be obtained.)

1. A metal complex comprising a ligand of formula LA:

wherein R is^x、R¹～R¹³Selected, identically or differently on each occurrence, from the group consisting of hydrogen, deuterium, a halogen atom, an alkanyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carboxylic acid group, an ether, an ester, a nitrile, an isonitrile, a thio group, a sulfinyl group, a sulfonyl group, and a phosphino group; and any two or more adjacent substituents are optionally joined or fused together to form a five-, six-or polycyclic ring;

R⁰identically or differently on each occurrence is selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkanyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, and a nitrile group;

R¹1,2 or 3;

the ligand LA is coordinated through a metal M to form a five-membered chelate ring;

m is capable of coordinating to other ligands; and the ligand LA can be linked to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

and M is selected from one of Os, Ir, Pd, Pt, Cu, Ag and Au.

2. The metal complex of claim 1, wherein LA is selected from one of the following structures:

wherein each symbol has the same meaning as in claim 1.

3. The metal complex of claim 1 or 2, wherein the metal complex has the formula m (la)_p(LB)_q(LC)_rWherein LB and LC are bidentate ligands, p is 1,2 or 3, q is 0, 1 or 2, r is 0, 1 or 2, and p + q + r is the oxidation state of the metal M, each of LB and LC being selected from one of the following structures:

wherein, Y¹～Y¹³Each independently selected from N or CR, T¹Selected from BR¹⁴、NR¹⁵、PR¹⁶、O、S、Se、C＝O、S＝O、SO₂、CR¹⁴R¹⁵、SiR¹⁴R¹⁵And GeR¹⁴R¹⁵One of (1), R¹⁴And R¹⁵May be optionally joined or fused to form a ring;

each R, R¹⁴、R¹⁵、R¹⁶Each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkanyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carboxylic acid group, an ether, an ester, a nitrile, an isonitrile, a thio group, a sulfinyl group, a sulfonyl group, and a phosphino group; and any two or more adjacent substituents are optionally joined or fused together to formForming five-membered rings, six-membered rings or multiple rings.

4. A metal complex as claimed in any one of claims 1 to 3 wherein R, R is present^x、R⁰、R¹～R¹⁶Each independently selected from the group consisting of hydrogen atom, deuterium atom, R^A1～R^A56、R^B1～R^B45、R^C1～R^C295A group of compounds;

wherein R is^A1～R^A56The structural formula is as follows:

R^B1～R^B45the structural formula is as follows:

R^C1～R^C295the structural formula is as follows:

。

5. the metal complex according to any one of claims 1 to 4, wherein the metal complex has a chemical formula of Ir (LA) (LB)₂、Ir(LA)₂(LB)、Ir(LA)₂(LC) or Ir (LA)₃Wherein LB is selected from a group consisting of LB 1-LB 432, and the concrete structures of LB 1-LB 432 are as follows:

LC is selected from a group consisting of LC 1-LC 56, and the specific structural formula is as follows:

6. the metal complex as claimed in any one of claims 1 to 5, wherein the formula (LA) is selected from one of LA 1-LA 188, and LA 1-LA 188 have the following specific structures:

。

7. the metal complex according to any one of claims 1 to 6, wherein the metal complex is Ir (LAi)₂(LBj)、Ir(LAi)(LBj)₂、Ir(LAi)₂(LCt) or Ir (LAi)₃；

Wherein i is an integer of 1 to 188, j is an integer of 1 to 432, t is an integer of 1 to 56, and LA1 to LA188, LB1 to LB432, and LC1 to LC56 have the same meanings as in claims 1 to 6.

8. An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 7.

9. The organic electroluminescent element as claimed in claim 8, wherein the organic layer further comprises a host material, the host material consisting essentially of the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, nitrotriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, and azadibenzoselenophene.

10. A consumer product made from the organic electroluminescent element as claimed in claim 8 or 9.

Technical Field

The invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex, an organic electroluminescent element and a consumer product.

Background

Currently, optoelectronic devices utilizing organic materials are becoming increasingly popular, and many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them more suitable for particular applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials.

OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for applications such as flat panel displays, lighting and backlighting.

One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color. In particular, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, an absorptive filter is used to filter the emission from a white backlight to produce red, green, and blue emissions. The same technique can also be used for OLEDs. The white OLED may be a single emission layer (EML) device or a stacked structure. The color can be measured using CIE coordinates well known in the art, and the luminescent material in the prior art has poor luminous stability and low luminous efficiency.

The present invention has been made in view of the above circumstances.

Disclosure of Invention

In order to solve the above problems of the prior art, the present invention provides a metal complex exhibiting enhanced phosphorescence quantum yield when used in an OLED, particularly in green to red emission regions, and an organic electroluminescent device and consumer products containing the same.

The first purpose of the invention is to provide a metal complex which has stable electroluminescence and high luminous efficiency.

In a second object of the present invention, there is provided an organic electroluminescent element containing the metal complex.

According to a third aspect of the present invention, there is provided a consumer product made from the organic electroluminescent device.

In order to achieve the purpose, the invention adopts the following technical scheme:

a metal complex comprising a ligand of formula LA:

wherein R is^x、R¹～R¹³Selected, identically or differently on each occurrence, from the group consisting of hydrogen, deuterium, a halogen atom, an alkanyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carboxylic acid group, an ether, an ester, a nitrile, an isonitrile, a thio group, a sulfinyl group, a sulfonyl group, and a phosphino group; and any two or more adjacent substituents are optionally joined or fused together to form a five-, six-or polycyclic ring;

R⁰identical at each occurrence orVariously selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkanyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group and a nitrile group;

R¹1,2 or 3;

the ligand LA is coordinated through a metal M to form a five-membered chelate ring;

m is capable of coordinating to other ligands; and the ligand LA can be linked to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

and M is selected from one of Os, Ir, Pd, Pt, Cu, Ag and Au.

Further, the LA is selected from one of the following structures:

wherein the symbols used have the meaning as defined above.

Further, the chemical formula of the metal complex is M (LA)_p(LB)_q(LC)_rWherein LB and LC are bidentate ligands, p is 1,2 or 3, q is 0, 1 or 2, r is 0, 1 or 2, and p + q + r is the oxidation state of the metal M, each of LB and LC being selected from one of the following structures:

wherein, Y¹～Y¹³Each independently selected from N or CR, T¹Selected from BR¹⁴、NR¹⁵、PR¹⁶、O、S、Se、C＝O、S＝O、SO₂、CR¹⁴R¹⁵、SiR¹⁴R¹⁵And GeR¹⁴R¹⁵One of (1), R¹⁴And R¹⁵May be optionally joined or fused to form a ring;

each R, R¹⁴、R¹⁵、R¹⁶Each independently selected from hydrogen, deuterium, a halogen atom, alkanyl, cycloalkyl, heteroalkyl,Heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphino; and any two or more adjacent substituents are optionally joined or fused together to form a five-, six-or polycyclic ring.

Further, R, R¹⁴、R¹⁵、R¹⁶Each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkanyl, cycloalkyl, heteroalkyl, silyl, aryl, heteroaryl.

"halogen", "halogen atom", "halo" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine or iodine.

"acyl" in the sense of the present invention means a substituted carbonyl group (COR).

"ester" in the sense of the present invention means a substituted oxycarbonyl group (-OCOR or CO)₂R)。

"Ether" in the sense of the present invention means an-OR group.

The "thio" or "thioether" groups described herein are used interchangeably and refer to the-SR group.

"sulfinyl" in the sense of the present invention means the-SOR group.

"Sulfonyl" in the sense of the present invention means-SO₂And R group.

"Phosphino" in the sense of the present invention means-PR₃Groups, wherein each R may be the same or different.

"silyl" in the sense of the present invention means-SiR₃Groups, wherein each R may be the same or different.

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

"alkyl", "alkenyl" or "alkynyl" in the sense of the present invention is preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

"alkoxy" in the sense of the present invention is preferably an alkoxy having 1 to 40 carbon atoms, and is taken to mean methoxy, 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.

In general, "cycloalkyl", "cycloalkenyl" according to the invention refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are those containing from 3 to 15 ring carbon atoms and may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, bicyclo [3.1.1]Heptyl, spiro [4.5 ]]Decyl, spiro [5.5 ]]Undecyl, adamantyl, and the like, wherein one or more-CH₂The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.

"Heteroalkyl" or "heterocycloalkyl" in the sense of the present invention means alkyl or cycloalkyl, respectively, preferably alkyl or cycloalkyl having 1 to 40 carbon atoms, meaning hydrogen or-CH, respectively₂Groups which may be substituted by oxygen, sulfur, halogen atoms, nitrogen, phosphorus, boron, silicon or selenium, preferably groups substituted by oxygen, sulfur or nitrogen. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.

"heteroalkenyl" or "heterocycloalkenyl" in the sense of the present invention refers to an alkenyl or cycloalkenyl group wherein at least one carbon atom is replaced by a heteroatom. Optionally, the at least one heteroatom is selected from oxygen, sulphur, nitrogen, phosphorus, boron, silicon or selenium, preferably oxygen, sulphur or nitrogen. Preferred alkenyl, cycloalkenyl groups are those containing from 3 to 15 carbon atoms. In addition, heteroalkenyl, heterocycloalkenyl may be optionally substituted.

"aralkyl" or "arylalkyl" in the sense of the present invention are used interchangeably and refer to an alkyl group substituted with an aryl group. In addition, the aralkyl group may be optionally substituted.

The "aryl" according to the invention refers to and includes monocyclic aromatic hydrocarbon radicals and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbyl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. Preferred aryl groups are those having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and 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, phenalene, phenanthrene, fluorene, pyrene, perylene, and the like,And azulenes, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted.

"heteroaryl" in the sense of the present invention means monocyclic aromatic radicals 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 with 5 or 6 ring atoms, and rings may have one to six heteroatoms. A heteropolycyclic system can have two or more rings in which two atoms are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles and/or heteroaryls. The heterocyclic aromatic ring system may have one to six heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothienopyridine, and selenenopyridine, preferably dibenzothiophene, and benzothiophene, Dibenzofurans, dibenzoselenophenes, carbazoles, indolocarbazoles, imidazoles, pyridines, triazines, benzimidazoles, 1, 2-azaborines, 1, 3-azaborines, 1, 4-azaborines, borazines, and aza analogs thereof. In addition, the heteroaryl group may be optionally substituted.

In many cases, typical substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphino.

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

In one example, the term substituted includes combinations of two to four of the listed groups.

In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are those containing up to fifty atoms other than hydrogen or deuterium, or those containing up to forty atoms other than hydrogen or deuterium, or those containing up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.

Further, the R, R⁰、R^x、R¹～R¹⁶Each independently selected from the group consisting of hydrogen atom, deuterium atom, R^A1～R^A56、R^B1～R^B45、R^C1～R^C295A group of compounds;

wherein R is^A1～R^A56The structural formula is as follows:

R^B1～R^B45the structural formula is as follows:

R^C1～R^C295the structural formula is as follows:

further, the chemical formula of the metal complex is Ir (LA) (LB)₂、Ir(LA)₂(LB)、Ir(LA)₂(LC)、Ir(LA)₃Wherein LB is selected from LB 1-LB 432, and the concrete structure of LB 1-LB 432 is as follows:

the LC is mainly selected from a group consisting of LC 1-LC 56, and the specific structural formulas of LC 1-LC 56 are as follows:

further, R in the formula (LA)^x、R¹～R¹³Identically or differently on each occurrence is selected from the group consisting of hydrogen, deuterium, alkanyl, cycloalkyl, heteroalkyl, heterocycloalkyl, silyl, nitrile; and any two or more adjacent substituents are optionally joined or fused together to form a five-, six-or polycyclic ring;

R⁰identically or differently on each occurrence is selected from the group consisting of hydrogen, deuterium, alkanyl, cycloalkyl, heteroalkyl, heterocycloalkyl, silyl, and nitrile;

R¹1,2 or 3;

the ligand LA is coordinated through a metal M to form a five-membered chelate ring;

m is capable of coordinating to other ligands; and the ligand LA can be linked to other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;

and M is selected from one of Ir, Pd or Pt.

Further, the formula (LA) is mainly selected from one of LA 1-LA 188, and the specific structures of LA 1-LA 188 are as follows:

further, the chemical formula of the metal complex is Ir (LAi)₂(LBj)、Ir(LAi)(LBj)₂、Ir(LAi)₂(LCt) or Ir (LAi)₃；

Wherein i is an integer of 1 to 188, j is an integer of 1 to 432, t is an integer of 1 to 56, and LA1 to LA188, LB1 to LB432, and LC1 to LC56 are the same as defined above.

The organic electroluminescent material of the present invention includes one or more of the metal complexes of the present invention. The organic electroluminescent material of the present invention may be formed of only one or more of the metal complexes of the present invention, or may contain other materials than the metal complexes of the present invention.

By including the metal complex of the present invention in the organic electroluminescent material of the present invention, an organic electroluminescent material which emits green, yellow or red light and has high luminous efficiency can be obtained. In addition, the organic electroluminescent material of the present invention is an organic electroluminescent material having good thermal stability.

The invention also provides an organic electroluminescent element which comprises a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises the metal complex.

Further, the organic layer further comprises a host material, the host material mainly comprising a group consisting of the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran and azadibenzoselenophene, indolocarbazole, 5, 9-dioxa-13 b-boronaphtho [3,2,1-de ] anthracene, azaindolocarbazole, and aza- (5, 9-dioxa-13 b-boronaphtho [3,2,1-de ] anthracene).

Wherein any substituent in the host is a non-fused substituent independently selected from the group consisting of: c_nH_2n+1、OC_nH_2n+1、OAr¹、N(C_nH_2n+1)₂、N(Ar¹)(Ar²)、CH＝CH-C_nH_2n+1、C≡CC_nH_2n+1、Ar¹、Ar¹-Ar²、C_nH_2n-Ar¹Or no substituent, wherein n is an integer of 1-10; and wherein Ar¹And Ar²Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

In the organic electroluminescent element of the present invention, one of the layers may contain the metal complex of the present invention, or two or more layers may contain the metal complex of the present invention.

The organic layer may be an emissive layer and the metal complex as described herein may be an emissive dopant or a non-emissive dopant.

The invention also provides a consumer product made of the organic electroluminescent element.

The consumer product according to the invention may be one of the following products: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior lighting and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet computer, a phablet, a Personal Digital Assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay at a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall containing multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.

Compared with the prior art, the invention has the beneficial effects that:

the metal complex can be used as a luminescent material to obtain a green to red phosphorescent material with high luminous efficiency, and the prepared luminescent material has good thermal stability; the electronic device of the present invention contains the organic electroluminescent element of the present invention, and thus a consumer product having green to red phosphorescence as electroluminescence and improved luminous efficiency can be obtained.

Drawings

In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.

FIG. 1 is a schematic view of an organic electroluminescent element according to the present invention;

FIG. 2 is a schematic view of an inverted organic electroluminescent device according to the present invention;

reference numerals

110-substrate, 115-anode layer, 120-hole injection layer, 125-hole transport layer, 130-electron blocking layer, 135-organic light emitting layer, 140-hole blocking layer, 145-electron transport layer, 150-electron injection layer, 155-protective layer, 160-cathode layer, 162-first conductive layer, 164-second conductive layer, 170-encapsulation layer.

Detailed Description

In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.

In the organic electroluminescent element of the present invention, the constitution of the layer other than the layer containing the metal complex of the present invention is not limited at all, and a person skilled in the art can determine the constitution of other layers of the organic electroluminescent element as necessary based on the general knowledge of the art in the field.

In fig. 1, an anode layer 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an organic light emitting layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode layer 160, and an encapsulation layer 170 are sequentially disposed on a substrate 110. The organic light-emitting layer contains the metal complex of the present invention. When the organic electroluminescent device is connected with an external power supply and voltage is applied, the metal complex in the organic light-emitting layer 135 emits light in an electroluminescent manner, and the wavelength range of the emitted light is 520-650 nm. Cathode layer 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device can be manufactured by depositing the layers in sequence.

Fig. 2 includes substrate 110, cathode 160, organic light emitting layer 135, hole transport layer 125, and anode layer 115. The device can be manufactured by depositing the layers in sequence. Because the most common OLED configuration has a cathode disposed over the anode, and the present device has a cathode layer 160 disposed under the anode layer 115, the present device may be referred to as inverted. Materials similar to those described for the present device may be used in the corresponding layers of the present device. Fig. 2 provides an example of how some layers may be omitted from the structure of the device of fig. 1.

The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be realized by combining the various layers described in different ways, or several layers may be omitted altogether, based on design, performance and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as mixtures of a host and a dopant, or more generally, mixtures. Also, the layer may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in fig. 2, the hole transport layer 125 transports holes and injects holes into the organic light emitting layer 135, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.

Structures and materials not specifically described, such as PLEDs comprising polymeric materials, may also be used. As another example, OLEDs having a single organic layer or multiple stacks may be used. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve optical coupling.

Any of the layers of the various embodiments may be deposited by any suitable method, unless otherwise specified. For organic layers, preferred methods include thermal evaporation, organic vapor deposition methods, or application of one or more layers by means of carrier gas sublimation, where at 10^-5The material is applied at a pressure between mbar and 1 bar. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured. Other suitable deposition methods include, for example, by spin coating, or by any desired methodPrinting methods such as screen printing, flexographic printing, offset printing, photo-induced thermal imaging, thermal transfer printing, ink jet printing, or nozzle printing to produce one or more layers. Soluble compounds, for example, are obtained by appropriate substitution of the metal complexes provided herein. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.

Devices fabricated according to embodiments of the present invention may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapor, and/or gases, among others. The barrier layer may be deposited on, under, or beside the substrate, electrode, or any other portion of the device, including the edges. The barrier layer may comprise 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 may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer comprises a mixture of polymeric and non-polymeric materials. To be considered a mixture, the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same conditions and/or at the same time. The weight ratio of polymeric material to non-polymeric material may be in the range of 95/5-5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric and inorganic silicon.

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

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 may use the materials and structures. Further, organic devices such as organic transistors may use the materials and structures.

These methods are generally known to those skilled in the art and they can be applied without inventive effort to organic electroluminescent devices comprising the compounds according to the invention.

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

The method for producing the organic electroluminescent element of the present invention includes the following methods, but is not limited thereto, and those skilled in the art can variously change the method according to the general knowledge in the art.

The preparation method comprises the following steps:

a cleaning procedure: cleaning the glass substrate with the ITO by using a cleaning agent, deionized water, an organic solvent and the like;

step of forming a hole injection layer: a hole injection layer forming material containing the metal complex of the present invention is vapor-deposited on the anode layer by vacuum vapor deposition, thereby forming a hole injection layer containing the metal complex of the present invention on the substrate;

step (2) of forming a hole transport layer: forming a hole transport layer on the hole injection layer by vacuum evaporation;

a step of forming an organic light-emitting layer: forming an organic light-emitting layer containing the metal complex of the present invention on the hole transport layer by vacuum evaporation of an organic light-emitting layer-forming material containing the material of the present invention on the hole transport layer;

a step of forming an electron transport layer: forming an electron transport layer containing the metal complex of the present invention on the organic light-emitting layer by vacuum evaporation of an electron transport layer forming material containing the metal complex of the present invention on the organic light-emitting layer;

a step of forming a cathode layer: a cathode forming material is vapor-deposited, sputtered, or spin-coated on the electron transporting layer to form a cathode layer.

In the embodiment of the invention, the performance detection conditions of the prepared electroluminescent device are as follows:

luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;

current density and lighting voltage: testing using a digital source table Keithley 2420;

power efficiency: tested using NEWPORT 1931-C.

Example 1

Metal complex Ir (LA39) (LB105)₂The preparation of (1):

the first step is as follows: preparation of Compound Int-1

10.0mmol of 1, 3-diphenyl-1, 3-propanedione (CAS:120-46-7) is dissolved in 50mL of acetonitrile, 10.0mmol of o-bromobenzaldehyde (CAS:6630-33-7) and 1.0mmol of piperidine are added, the mixture is refluxed for 12 hours under the protection of nitrogen, cooled to room temperature, concentrated and dried under reduced pressure, and separated and purified by a silica gel column to obtain a compound Int-1 as a yellow solid with the yield of 67%.

The second step is that: preparation of Compound Int-2

Dissolving 10.0mmol of Int-1 in 40mL of dichloromethane, cooling to-78 ℃ with liquid nitrogen under the protection of nitrogen, adding 35.0mL of 0.4M aqueous solution of cerium chloride hydrate in methanol, adding 21.0mmol of sodium borohydride solid, stirring for reaction for 30 minutes, heating to room temperature for reaction for 1 hour, adding 30mL of 0.5M dilute aqueous solution of hydrochloric acid, extracting with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, drying, and separating and purifying with a silica gel column to obtain the compound Int-2, namely a white solid with the yield of 91%.

The third step: preparation of Compound Int-3

Dissolving 25.3mmol of intermediate Int-2 in 60mL of dry chlorobenzene, adding 4.8g of polyphosphoric acid, heating to 130 ℃ under the protection of nitrogen, stirring for reacting for 24 hours, cooling to room temperature, adding 150mL of ice water, extracting with dichloromethane, collecting an organic phase, drying, filtering, and separating and purifying a filtrate by using a silica gel column to obtain a compound Int-3, namely a white solid with the yield of 30%.

The fourth step: preparation of Compound Int-4

20.0mmol of intermediate Int-3 was dissolved in 60mL of DMF, and 24.0mmol of pinacol diboride, 30.0mmol of anhydrous potassium acetate and 0.2mmol of PdCl₂(dppf) catalyst, under the protection of nitrogen, heating to 90 ℃, stirring for reaction for 14 hours, cooling to room temperature, adding 150mL of ice water, extracting with ethyl acetate, collecting an organic phase, drying, filtering, and separating and purifying a filtrate by using a silica gel column to obtain a compound Int-4, wherein the yield is 89% and the colorless oily substance is obtained.

The fifth step: preparation of Compound Int-5

12.0mmol of intermediate Int-4 is dissolved in 40mL of toluene, 20mL of ethanol and 20mL of water, 10.0mmol of 2-bromo-4- (methyl-d 3) -pyridine (CAS:1185311-65-2), 30.0mmol of anhydrous potassium carbonate and 0.01mmol of Pd132 catalyst are added, the mixture is heated under reflux and stirred for 12 hours under the protection of nitrogen, the mixture is cooled to room temperature, 100mL of water is added for dilution, extraction is carried out with ethyl acetate, an organic phase is collected, dried and filtered, and a filtrate is separated and purified by a silica gel column to obtain compound Int-5 which is yellow solid with the yield of 87%.

And a sixth step: preparation of compound LA39

Dissolving 10.0mmol of intermediate Int-5 in 50mL of deuterium-methanol, adding 30.0mmol of sodium methoxide, heating under reflux and stirring for reaction for 2 days under the protection of nitrogen, cooling to room temperature, concentrating under reduced pressure to dryness, adding 100mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, and separating and purifying a filtrate by using a silica gel column to obtain a compound LA39 as a yellow solid with the yield of 100%.

The seventh step: preparation of Compound Int-6

10.0g of the compound LB105 and 9.5g of IrCl₃·3H₂Dispersing O in 150mL of ethylene glycol ethyl ether and 50mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and drying in vacuum to obtain 14.8g of yellow solid, dissolving the obtained yellow solid in 250mL of dichloromethane and 25mL of methanol, adding 6.5g of silver trifluoromethanesulfonate, stirring for reaction for 24 hours, filtering, and concentrating and drying the filtrate under reduced pressure to obtain a compound Int-6 with the yield of 83%.

Eighth step: compound Ir (LA39) (LB105)₂Preparation of

4.7mmol of compound LA39 and 2.3mmol of intermediate Int-6 were dispersed in 50mL of ethylene glycol ethyl ether and 50mL of DMF, and the reaction was stirred at 100 ℃ for 7 days under nitrogen protection, and cooledCooling to room temperature, concentrating under reduced pressure, drying, separating and purifying with silica gel column, eluting with dichloromethane-n-hexane to obtain compound Ir (LA39) (LB105)₂Brown solid, yield 38%.

Example 2

Metal complex Ir (LA56) (LB105)₂The preparation of (1):

the first step is as follows: preparation of Compound Int-7

Compound Int-7 was prepared in 86% yield by substituting 2-bromopyridine for only 2-bromo-4- (methyl-d 3) -pyridine of the fifth step of example 1, according to the synthesis of the fifth step of example 1.

The second step is that: preparation of compound LA56

Dispersing 10.0mmol of compound Int-7 and 32.0mmol of NBS in 250mL of carbon tetrachloride, adding 0.1mmol of AIBN, heating under reflux and stirring for 5 hours under the protection of nitrogen, cooling to room temperature, filtering, washing filtrate with saturated aqueous sodium bisulfite solution, washing with water, drying organic phase, concentrating under reduced pressure, dissolving residue with 100mL of benzene, dropwise adding 27mL of 2M trimethylaluminum toluene solution, heating to 50 ℃, stirring for 8 hours, cooling to room temperature, adding 50mL of saturated aqueous ammonium chloride solution, extracting with toluene, washing organic phase with saturated salt water, washing with water, collecting organic phase, drying, concentrating under reduced pressure, separating and purifying with silica gel column to obtain compound LA56, yellow solid with yield of 55%.

The third step: compound Ir (LA56) (LB105)₂Preparation of

5.0mmol of the compound LA56 and 2.5mmol of the seventh step of example 1Dispersing the prepared intermediate Int-6 in 50mL of ethylene glycol ethyl ether and 50mL of DMF, heating to 100 ℃ under the protection of nitrogen, stirring for reaction for 7 days, cooling to room temperature, concentrating under reduced pressure to dryness, separating and purifying by using a silica gel column, eluting by dichloromethane-n-hexane to obtain a compound Ir (LA56) (LB105)₂Brown solid, yield 42%.

Example 3

With reference to a similar synthetic procedure as in example 1 and example 2 above, a LA ligand was prepared: LA 1-LA 38, LA 40-LA 55 and LA 57-LA 96.

Example 4

Metal complex Ir (LA111) (LB105)₂The preparation of (1):

the first step is as follows: preparation of Compound Int-8

15.0mmol of 2- (methyl-d 3) -1, 3-indandione and 15.1mmol of (2-methoxyphenyl) phenylmethanol (CAS:22788-49-4) were dispersed in 150mL of toluene, 5.0mmol of p-toluenesulfonic acid was added, the reaction was stirred at an elevated temperature under reflux for 24 hours, and the water of reaction was removed by a water separator, cooled to room temperature, added with 50mL of a saturated aqueous potassium carbonate solution, extracted with ethyl acetate, dried under reduced pressure, concentrated and dried, and separated and purified by a silica gel column to give compound Int-8 as a white solid with a yield of 75%.

The second step is that: preparation of Compound Int-9

Dispersing 25.0mmol of lithium aluminum hydride in 80mL of dry THF, cooling to 0 ℃ under the protection of nitrogen, dropwise adding 10.0mmol of Int-8 solution in THF, heating to room temperature, stirring for 5 hours, cooling to 0 ℃, dropwise adding 5mL of 25% sodium hydroxide aqueous solution and 1mL of water, filtering, washing a filter cake with ethyl acetate, collecting a filtrate, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-9 which is colorless oily matter with the yield of 86%.

The third step: preparation of Compound Int-10

Mixing 5.0mL of polyphosphoric acid and 50mL of dried chlorobenzene, dropwise adding 10.0mmol of Int-9 solution dissolved in chlorobenzene under the protection of nitrogen, heating, refluxing, stirring, reacting for 20 hours, cooling to room temperature, pouring the reaction solution into 200mL of saturated sodium bicarbonate aqueous solution, separating an organic phase, extracting an aqueous phase with ethyl acetate, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-10 which is colorless oily matter with the yield of 38%.

The fourth step: preparation of Compound Int-11

Dissolving 10.0mmol of Int-10 in 80mL of dry dichloromethane, cooling to-5 ℃ under the protection of nitrogen, dropwise adding a solution of 15.0mmol of boron tribromide dissolved in dichloromethane, stirring for reacting for 2 hours, heating to room temperature, adding 150mL of saturated aqueous sodium bicarbonate solution, separating an organic phase, extracting an aqueous phase with dichloromethane, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-11 which is colorless oily matter with the yield of 98%.

The fifth step: preparation of Compound Int-12

Dissolving 10.0mmol of Int-11 in 80mL of dry dichloromethane, adding 20.0mmol of pyridine, cooling to 0 ℃ under the protection of nitrogen, dropwise adding 12.0mmol of trifluoromethanesulfonic anhydride, stirring for 2 hours for reaction, raising the temperature to room temperature, adding 50mL of 1N dilute hydrochloric acid aqueous solution, separating an organic phase, extracting an aqueous phase with dichloromethane, combining and drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-12 as colorless oily substance with the yield of 88%.

And a sixth step: preparation of Compound Int-13

10.0mmol of Int-12 are dissolved in 50mL of DMF and 12.0mmol of pinacol diboron, 15.0mmol of anhydrous potassium acetate and 0.1mmol of PdCl₂(dppf) DCM catalyst, under the protection of nitrogen, heating to 100 ℃ and stirring for reaction for 10 hours, cooling to room temperature, adding 150mL of water, extracting with ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound Int-13 as a colorless oily substance with the yield of 87%.

The seventh step: preparation of Compound Int-14

Referring to the first step synthesis of example 2, compound Int-14 was prepared as a yellow solid in 88% yield by replacing Int-13 with Int-4 only in the first step of example 2.

Eighth step: preparation of compound LA111

Referring to the synthesis procedure of the sixth step of example 1, only Int-5 of the sixth step of example 1 was replaced with Int-14 to prepare compound LA111 as a yellow solid with a yield of 100%.

The ninth step: compound Ir (LA111) (LB105)₂Preparation of

5.0mmolCompound LA111 and 2.5mmol of intermediate Int-6 prepared in the seventh step of example 1 were dispersed in 50mL of ethylene glycol ethyl ether and 50mL of DMF, heated to 100 ℃ under nitrogen protection, stirred for reaction for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by silica gel column, eluted with dichloromethane-n-hexane to give compound Ir (LA111) (LB105)₂Brown solid, yield 36%.

Example 5

With reference to a similar synthetic method as in examples 1 to 4 above, a LA ligand was prepared: LA 97-LA 110, LA 112-LA 188.

Example 6

Metal complex Ir (LA37)₂Preparation of (LB 105):

the first step is as follows: preparation of Compound Int-15

Referring to the preparation method of the seventh step of example 1, compound Int-15 is prepared in a yield of 82% as a yellow solid by replacing only LB105 of the seventh step of example 1 with LA37, changing the mass usage of the compound according to the molar amount, and adjusting other experimental parameters according to actual needs.

The second step is that: metal complex Ir (LA37)₂Preparation of (LB105)

Dispersing 5.0mmol of compound LB105 and 2.5mmol of intermediate Int-15 in 50mL of ethylene glycol ethyl ether and 50mL of DMF, heating to 100 ℃ under the protection of nitrogen, stirring for reaction for 7 days, cooling to room temperature, concentrating under reduced pressure, separating and purifying by using a silica gel column, eluting with dichloromethane-petroleum ether to obtain compound Ir (LA37)₂(LB105), brown solid, yield 28%.

Example 7

With reference to the synthesis procedures of examples 1-6, compounds of formula Ir (LAi) or (LBj) were prepared₂And Ir (LAi))₂(LBj) wherein i is an integer of 1 to 188, j is an integer of 1 to 432, and LA1 to LA188 and LB1 to LB432 are as defined above.

Example 8

Metal complex Ir (LA1)₃The preparation of (1):

the first step is as follows: preparation of Compound Int-16

10.0mmol of the compound LA1 and 5.0mmol of IrCl₃·3H₂Dispersing O in 90mL of ethylene glycol ethyl ether and 30mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and drying in vacuum to obtain a compound Int-16, namely a brown solid, wherein the yield is 58%.

The second step is that: compound Ir (LA1)₃Preparation of

5.0mmol of Int-16 prepared in the first step, 10.0mmol of silver trifluoromethanesulfonate and 12.0mmol of LA1 dispersed in 20mL of ethylene glycol ethyl ether, heating under reflux and stirring for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, dissolving a filter cake with dichloromethane, and separating and purifying by a silica gel column to obtain a compound Ir (LA1)₃Dark yellow solid, yield 47%.

Example 9

With reference to the synthesis procedure of example 8, with appropriate adjustment of the experimental parameters and conditions, the metal complex Ir (LAi) was prepared₃I is an integer of 1 to 188, wherein LA1 to LA188 are as defined above.

Example 10

Compound Ir (LA125)₂Preparation of (LC 7):

the first step is as follows: preparation of Compound Int-17

Referring to the preparation method of the first step of example 8, only LA1 of the first step of example 8 was replaced by LA125, the mass amount of the compound was changed according to the molar amount, and other experimental parameters were adjusted according to actual needs to prepare compound Int-17 as a yellow solid with a yield of 55%.

The second step is that: compound Ir (LA125)₂Preparation of (LC7)

5.0mmol of Int-17 prepared in the first step, 50.0mmol of anhydrous potassium carbonate and 15.0mmol of LC7 dispersed in 40mL of ethylene glycol ethyl ether, heating under reflux and stirring for 24 hours under the protection of nitrogen, cooling to room temperature, pouring the reaction solution into 150mL of ice water, extracting with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying with a silica gel column to obtain a compound Ir (LA125)₂(LC7), yellow solid, yield 54%.

Example 11

With reference to the synthesis of example 10, preparation of Ir (LAi)₂(LCt) wherein i is an integer of 1 to 188, t is an integer of 1 to 56, and LA1 to LA188 and LC1 to LC56 are as defined above.

EXAMPLE 12 preparation of organic electroluminescent element

The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.

Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10^-5～9×10^-3Pa, continuously and respectively evaporating HATCN compound as hole injection layer on the anode layer film to obtain a film thicknessContinuously depositing HTM on the hole injection layer film to form a hole transport layer, wherein the deposition film has a thickness of

Depositing EBM as an electron blocking layer on the hole transport layer to a thickness of

An organic light-emitting layer is evaporated on the electron blocking layer, the light-emitting layer contains H1 as a main body and 5% of the metal complex prepared by the invention as a doping material by mass, and the thickness of the evaporated film is

Depositing an electron transport layer of LiQ and ETM as elements on the organic light-emitting layer, wherein LiQ is 60% of ETM mass, and the deposition film thickness is

Continuously evaporating a layer of LiF on the luminescent layer to form an electron injection layer of the device, wherein the thickness of the evaporated film is

Finally, metal aluminum is evaporated on the electron injection layer to form a cathode layer of the device, and the thickness of the evaporated layer is set to

Comparative example 1

A comparative element 1 was produced in the same manner as in example 12 except that the compound shown in GD-1 was used in place of the metal complex in example 12.

The structural formulas of the HATCN, HTM, EBM, H1, LiQ, GD-1 and ETM are shown as follows:

in the same manner as in example 12, an organic electroluminescent element was produced using the metal complex of the present invention as a doping material for an organic light-emitting layer, and the structure and performance data thereof are summarized in table 1, in which the data are normalized with respect to the comparative example.

TABLE 1

As can be seen from table 1, the metal complex of the present invention as a doping material of the light emitting layer has a lower driving voltage compared to comparative example 1, especially has a significant advantage in external quantum efficiency compared to comparative example 1, and the LT 95% lifetime of the device is very desirable.

The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.