CN113637473B - Host material and organic electroluminescent device comprising same - Google Patents

Host material and organic electroluminescent device comprising same Download PDF

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CN113637473B
CN113637473B CN202111206962.9A CN202111206962A CN113637473B CN 113637473 B CN113637473 B CN 113637473B CN 202111206962 A CN202111206962 A CN 202111206962A CN 113637473 B CN113637473 B CN 113637473B
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host
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CN113637473A (en
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赵晓宇
王鹏
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

The present invention provides a host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 and the second host compound is represented by formula 2:
Figure 147946DEST_PATH_IMAGE002
formula 1

Description

Host material and organic electroluminescent device comprising same
Technical Field
The present invention relates to a host material, and more particularly, to a host material and an organic electroluminescent device including the same.
Background
An Organic Light-Emitting Diode (OLED for short). The light emitting device has a feature of being thin and capable of emitting light with high luminance at a low driving voltage and emitting light in multiple colors by selecting a light emitting material, and thus attracts attention.
Organic electroluminescent devices convert electrical energy into light by applying a voltage across the device. In general, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (including a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. Materials constituting the organic layer may be classified into a hole injection material, a hole transport material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, a hole blocking material, and the like according to the function of the material. When a bias is applied to the device, holes are injected from the anode into the light-emitting layer and electrons are injected from the cathode into the light-emitting layer. The holes and electrons meet to form excitons, which recombine to emit light. Of which the influence of the light-emitting layer on the performance of the organic light-emitting device is most critical. The light emitting layer material is required to have characteristics of high quantum efficiency, high electron mobility, high hole mobility, and the like, and the light emitting layer material may use a combination of a host material and a dopant material to improve color purity, light emitting efficiency, and stability. In order to obtain an organic light emitting device with characteristics of higher efficiency, longer service life, and the like, it is important to select an appropriate matching combination of a host material and a dopant material. Japanese patent application laid-open No. 2001-23777 discloses an organic electroluminescent device comprising a nitrogen-containing 5-membered heteroaryl group condensed on an intermediate benzene ring compound of a phenanthrene skeleton as a host material. The organic electroluminescent device comprising the above compound disclosed in the reference has excellent color purity characteristics of blue. However, the above-mentioned japanese patent still needs improvement in terms of driving voltage, current efficiency, and driving life.
Therefore, there is a need to develop a novel host material.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a main body material with high luminous efficiency and an organic electroluminescent device comprising the main body material.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the present invention provides a host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 and the second host compound is represented by formula 2:
Figure 655209DEST_PATH_IMAGE001
formula 1
Wherein R1 is selected from the following structures:
Figure 634666DEST_PATH_IMAGE002
X1，Y1each independently selected from CR3R4、NR、O、S、S(=O)、S(=O)2Or SiR3R4；
Z1、Z2、Z3、Z4Are identical or different from each other and are each independently selected from CR5Or an N atom;
R2、R3、R4、R5the aryl group is the same or different from each other, and is independently selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof, or is bonded with adjacent atoms to form a ring;
Ar1is an aryl group of C6-C60 or a heteroaryl group of C5-C60;
Figure 257146DEST_PATH_IMAGE003
formula 2
When X is present2,Y2Each independently selected from C, NR8O, S, and X2，Y2When at least one of them is a C atom,
R6、R7and R8The groups are the same or different from each other, and each of them is independently selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof, or is bonded with adjacent atoms to form a ring;
L1represents a single bond, a substituted or unsubstituted arylene group having C6-C40, a substituted or unsubstituted heteroarylene group having C5-C40;
the group A is selected from CN, F, carbonyl, carboxyl, nitro or selected from the following groups, or the combination of the groups;
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Figure 342094DEST_PATH_IMAGE005
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Figure 873493DEST_PATH_IMAGE011
Figure 469559DEST_PATH_IMAGE012
wherein R is9、R10、R11And R12Independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or combinations thereof;
when X is present2,Y2Each independently selected from N, O, S and X2，Y2When at least one of them is an N atom, L1Is substituted or unsubstituted arylene of C6-C40, substituted or unsubstituted heteroarylene of C5-C40, and the heteroatoms are not all nitrogen atoms;
the group A is selected from one or more of hydrogen, CN, F, carbonyl, carboxyl, nitro or the combination of the hydrogen, the CN, the F, the carbonyl, the carboxyl and the nitro, and at least one is not hydrogen.
Preferably, wherein the compound represented by formula i is selected from the group consisting of:
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Figure 439101DEST_PATH_IMAGE014
Figure 539781DEST_PATH_IMAGE015
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Figure 999710DEST_PATH_IMAGE068
Figure 892711DEST_PATH_IMAGE069
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Figure 171148DEST_PATH_IMAGE101
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preferably, wherein the compound represented by formula 2 is selected from the group consisting of:
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Figure 813799DEST_PATH_IMAGE107
Figure 964026DEST_PATH_IMAGE108
Figure 979256DEST_PATH_IMAGE109
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the invention also provides an organic electroluminescent device, which comprises a cathode layer, an anode layer and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the light emitting layer contains the host material.
Preferably, wherein the light emitting layer further comprises a dopant, wherein the mass ratio of the host material to the dopant is 1:99-99: 1.
preferably, wherein the mass ratio of the first host compound to the second host compound in the host material is 1: 9-9: 1.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.
The carbazole derivative represented by formula 1 according to the present disclosure has a high triplet level and has a good hole transport ability, the derivative compound based on phenanthrothiazole, oxazole, furan, thiophene, etc. represented by formula 2 inherently has high electronegativity and negative electron groups, and the compounds represented by both formulas have rigid characteristics due to a structure in which carbazole, phenanthrene and oxazole, or phenanthrene and thiazole, or phenanthrene and furan, or phenanthrene and thiophene, etc. are condensed, so that the two derivatives of the present invention promote charge transition between molecules. In addition, the derivatives such as the carbazole phenothiazine and the like and the derivatives such as phenanthrene and oxazole, phenanthrene and thiazole, phenanthrene and furan, phenanthrene and thiophene and the like have good planarity, so that the intermolecular stacking of the two kinds of the derivatives can be enhanced, the horizontal molecular orientation can be realized more easily, and the rapid electron current characteristic can be realized. An organic electroluminescent device having high efficiency and long life can be realized.
In formula 2 above, formula 2 is represented by any one of the following formulae 2-1 to 2-12:
Figure 574851DEST_PATH_IMAGE200
Figure 242592DEST_PATH_IMAGE202
Figure 458941DEST_PATH_IMAGE204
Figure 45780DEST_PATH_IMAGE206
wherein the content of the first and second substances,
L1is a substituted or unsubstituted arylene group having C6-C40, a substituted or unsubstituted heteroarylene group having C5-C40, and the heteroatoms are not all nitrogen atoms.
R6、R13And R14The same or different from each other, and each of them is independently selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof, or is bonded to an adjacent atom to form a ring.
Z5、Z6、Z7Identical or different, independently selected from CR5Or an N atom.
Ar2、Ar3、Ar4The same or different, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof, or are bonded to adjacent atoms to form a ring。
Group A1、A2、A3Identical or different, independently selected from hydrogen, deuterium, CN, F, carbonyl, carboxyl, NO2And at least one is not hydrogen or deuterium. The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and the organic functional layer contains the host material.
Preferably, the organic functional layer is a light-emitting layer, and the light-emitting layer further contains a dopant.
More preferably, the mass ratio of the host material to the dopant is 1:99 to 99: 1.
The invention also provides application of the main body material in an organic electroluminescent device.
Preferably, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode deposited in sequence, and the organic compound is used as a host material of the light emitting layer.
Preferably, the organic light emitting device comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode, wherein the organic functional layers contain the one or more compounds.
The organic electroluminescent device comprises a plurality of main body materials with a general formula 1 and a general formula 2 as light-emitting layers, and the light-emitting device comprises a substrate, a first electrode, an organic layer, a second electrode and a covering layer.
The organic layer of the present invention may include a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer as the structure of the organic layer. The organic layer of the light-emitting device can be formed by a single-layer structure, or can be formed by a multi-layer structure formed by laminating a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer; meanwhile, the organic layer may further include one or more layers, for example, the hole transport layer may include a first hole transport layer and a second hole transport layer. In the light-emitting device of the present invention, any material known in the art for the layer may be used for the other layers except that the light-emitting layer contains the plurality of host materials of the present invention.
In the light-emitting device of the present invention, any substrate used in a typical organic light-emitting device can be used as the substrate material. The substrate can be sodium glass or alkali-free glass or a transparent flexible substrate, can also be a substrate made of opaque materials such as silicon or stainless steel, and can also be a flexible polyimide film. Different substrate materials have different properties and different application directions. The hole transport layer of the present invention can be formed by a method of stacking or mixing one or two or more kinds of hole transport materials, or a method of using a mixture of a hole transport material and a polymer binder. Since the hole transport material needs to transport holes from the positive electrode efficiently between electrodes to which an electric field is applied, it is desirable that the hole transport material has high hole injection efficiency and can transport injected holes efficiently. Therefore, a hole transport material is required to have an appropriate ionization potential, an appropriate energy level, and a large hole mobility, to be excellent in material stability, and to be less likely to generate impurities that become traps during manufacturing and use. The substance satisfying such conditions is not particularly limited, and examples thereof include carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, phthalocyanine compounds, hexacarbonitrile hexaazatriphenylene compounds, quinacridone compounds, perylene derivatives, anthraquinone compounds, F4-TCNQ, polyaniline, polythiophene, and polyvinylcarbazole, but are not limited thereto.
As the light emitting layer material of the present invention, in addition to containing a plurality of host materials provided by the present invention, a dopant material (also referred to as a guest material) may also be used, and a plurality of dopant materials may be contained. The compound represented by the general formula (1) may be contained as a first host compound of the plurality of host materials, and the compound represented by the general formula (2) may be contained as a second host compound of the plurality of host materials. The mass ratio of the first host compound to the second host compound is about 1:99 to about 99: 1. preferably about 10: 90 to about 90: 10. more preferably about 30: 70 to 70: 30. even more preferably about 40: 60 to about 60: 40. and more preferably about 50: 50. when the light-emitting layer contains two or more materials, a layer may be formed by mixed evaporation, or layers may be simultaneously and separately co-evaporated. In addition, the light-emitting layer can be a single light-emitting layer or a composite light-emitting layer which is overlapped together in the transverse direction or the longitudinal direction. The dopant may be a fluorescent material or a phosphorescent material. The amount of the dopant is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, even more preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.
The fluorescent dopant material that can be used in the present invention may include: fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, and the like, but are not limited thereto. Phosphorescent dopant materials useful in the present invention may include: heavy metal complexes, phosphorescent rare earth metal complexes, and the like, but are not limited thereto. Examples of the heavy metal complex include iridium complexes, platinum complexes, osmium complexes, and the like; examples of the rare earth metal complex include, but are not limited to, terbium complexes and europium complexes. As the electron transport material of the present invention, a material having good electron mobility and suitable HOMO and LUMO energy levels are preferable. Electron transport materials that can be used in the present invention include: metal complexes, oxathiazole derivatives, oxazole derivatives, triazole derivatives, azabenzene derivatives, phenanthroline derivatives, diazene derivatives, silicon-containing heterocycles, boron-containing heterocycles, cyano compounds, quinoline derivatives, benzimidazole derivatives, and the like, but are not limited thereto.
As electron beam of the inventionThe material is preferably a substance having an ability to transport electrons, and has an effect of injecting electrons from the cathode, and has an excellent ability to form a thin film. Electron injection materials that can be used as the present invention include: alkali metal compounds such as lithium oxide, lithium fluoride, lithium 8-hydroxyquinoline, lithium boron oxide, cesium carbonate, cesium 8-hydroxyquinoline, potassium silicate, calcium fluoride, calcium oxide, magnesium fluoride, magnesium oxide; a fluorenone; nitrogen-containing five-membered ring derivatives, for example, oxazole derivatives, oxadiazole derivatives, imidazole derivatives; a metal complex; anthraquinone dimethane, diphenoquinone, anthrone derivatives, and the like, but are not limited thereto, and these compounds may be used alone or in combination with other materials. As the cathode material of the present invention, a material having a low work function is preferable in order to easily inject electrons into the organic layer. Cathode materials useful in the present invention include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, aluminum, silver, tin, lead, or alloys thereof; and multilayer materials, e.g. LiF/Al or LiO2and/Al, but not limited thereto.
When the organic layer materials of the present invention are used, they may be formed into a single layer structure by film formation alone, or may be mixed with other materials to form a single layer structure, or may be formed into a single layer laminated structure by film formation alone, a single layer laminated structure by film mixing, a single layer formed by film formation alone, and a single layer laminated structure by film mixing, but not limited thereto. The organic electroluminescent device according to the present invention can be manufactured by sequentially laminating the above-described structures. The production method may employ a known method such as a dry film formation method or a wet film formation method. Specific examples of the dry film formation method include a vacuum deposition method, a sputtering method, a plasma method, an ion plating method, and the like. Specific examples of the wet film formation method include various coating methods such as a spin coating method, a dipping method, a casting method, and an ink jet method, but are not limited thereto. The organic light-emitting device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like.
Examples
The synthesis of the compound represented by formula 1 or formula 2 above can be carried out using known methods. For example, a cross-coupling reaction of a transition metal such as nickel or palladium is used. Other synthesis methods are C-C, C-N coupling reactions using transition metals such as magnesium or zinc. The above reaction is limited to mild reaction conditions, superior selectivity of various functional groups, and the like, and Suzuki and Buchwald reactions are preferred.
The host material compounds of the present invention are illustrated by the following examples, but are not limited to the compounds and synthetic methods illustrated by these examples.
The initial raw materials and the solvent of the invention are purchased from Chinese medicine, and some common products such as OLED intermediates and the like are purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. are available from sigma-Aldrich.
1H-NMR data were determined using a JEOL (400MHz) nuclear magnetic resonance apparatus; HPLC data were determined using a Shimadzu LC-20AD HPLC.
Example 1
Synthesis of Compound 1
Figure 534530DEST_PATH_IMAGE208
26.9 g (240 mmol) of potassium tert-butoxide, 648 mg (1 mmol) of [1, 3-bis (2, 6-di-isopropylphenyl) -4, 5-dihydroimidazol-2-ylidene ] chloro ] [ 3-phenylallyl ] palladium (II) catalyst, 39.8 g (100mmol) of compound 1-A, 35.5 g (110 mmol) of compound 1-B and 1000mL of ethylene glycol dimethyl ether (DME) were charged into a reaction vessel under an argon atmosphere, and stirred under heating at 80 ℃ for 15 hours. The reaction mixture was cooled to room temperature, 500ml of water was added, filtered and the crude product was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 45.5 g of compound 1, 99.6% purity by HPLC, 71% yield.
1 HNMR(DMSO)：δ8.28 (d，1H)，8.11(d，1H),7.98(d，1H),7.82(d，1H), 7.75（m,1H）,7.69(m,3H),7.62(m,2H),7.58(m,1H),7.57(m，1H), 7.55(d，3H), 7.54(d,1H),7.40(d,1H),7.39(m,1H),7.37(d,2H),7.31(m,1H),7.21(s,1H),7.14(d,1H),7.01(m,2H),6.96(d,1H).
Example 2
Synthesis of Compound 41
Figure 379864DEST_PATH_IMAGE210
The procedure was repeated in the same manner as in example 1 except that the starting materials were replaced with Compound 41-A and Compound 41-B.
1HNMR(DMSO)：δ8.54 (d，1H)，7.99(d，1H),7.96(d，1H),7.94(d，1H), 7.90(d,1H),7.78(d,1H),7.69(s，1H), 7.65(d，1H), 7.62(m,1H),
7.61(m,1H),7.58(m,1H),7.55(m,2H),7.53(m,1H),7.50(d,2H),7.47(m,1H),7.38(m,1H),7.28(m,1H),7.27(d,1H),7.21(s,1H),7.17(d,1H),7.14(d,1H),7.01(m,2H),6.96(m,1H)，1.75(s,6H).
Example 3
Synthesis of Compound 87
Figure 372091DEST_PATH_IMAGE212
Same as example 1 except that the starting materials were changed to 87-A and 87-B
1HNMR(DMSO)：δ8.28 (d，2H),8.11(d,2H),8.03(d，1H),7.82(d，1H), 7.76(d,1H),7.75(m,2H),7.69(m,3H),7.62(m,2H),7.58(m,1H),7.55(m,2H),7.50(d,2H),7.49(s,1H),7.42(s,1H),7.40(s,1H),7.27(d,1H)，7.21(s,1H),
7.18(m,1H),7.17(d,1H),7.14(d,1H),7.01(m,2H),6.96(d,1H).
Example 4
Synthesis of Compound 139
Figure 333094DEST_PATH_IMAGE214
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to compound 139-A and compound 139-B.
1 HNMR(DMSO)：δ8.51(d,1H),8.43 (d，2H),8.17(s，1H),8.11(d,1H),8.08(s，1H),7.98(d,1H),7.97(d,2H),7.88(d,1H),7.85(s,1H),7.72(m,1H),7.69(s,1H),7.67(m,1H),7.62(m,2H),7.55(m,1H),7.53(m,1H),7.50(d,2H),7.27(s,1H),
7.21(s,1H),7.17(d,1H),7.14(d,1H),7.01(m,2H),6.96(d,1H)，1.75(s,6H).
Example 5
Synthesis of Compound 160
Figure 918927DEST_PATH_IMAGE216
The reaction was conducted in the same manner as in example 1 except that the starting materials were replaced with Compound 160-A and Compound 160-B.
1HNMR(DMSO)：δ8.54(d,1H),8.30(d，1H),8.19(d，1H),8.13(d，1H),7.47(s,6H),
7.99(d,1H), 7.96(d,1H), 7.94(d,1H), 7.89(d,1H), 7.69(s,1H), 7.62(m,4H), 7.61(m,1H), 7.58(m,3H), 7.55(m,1H), 7.53(m,1H), 7.50(m,5H), 7.27(s,1H),
7.21(s,1H), 7.20(m,1H), 7.18(d,1H), 7.17(d,1H),7.14(d,1H),7.01(m,2H),
6.96(d,1H).
Example 6
Synthesis of Compound 194
Figure 521947DEST_PATH_IMAGE218
The procedure was repeated in the same manner as in example 1 except that the starting materials were changed to Compound 194-A and Compound 194-B.
1HNMR(DMSO)：δ8.55(d,1H),8.51(d，1H),8.45(d，1H),8.43(d,1H),8.32(d,1H),
7.93(d,1H),7.88(d,1H),7.72(m.1H),7.70(m,1H),7.69(s,1H),7.67(m,1H),7.62(m,2H),7.58(m,1H),7.56(m,1H),7.55(m,1H),7.50(d,2H), 7.27(s,1H),
7.21(s,1H), 7.20(m,1H), 7.18(d,1H), 7.17(d,1H),7.14(d,1H),7.01(m,2H),
6.96(d,1H).
Example 7
Synthesis of Compound 238
Figure 368680DEST_PATH_IMAGE220
The procedure was as in example 1 except that the starting materials were replaced with the compounds 238-A and 238-B.
1 HNMR(DMSO)：δ8.54 (d，1H),8.00（d,1H）,7.99(d,1H),7.96(d,1H),7.94(d,1H),7.90(d,1H),7.68(m,1H),7.62(m,2H),7.61(m,1H),7.57(m,1H),7.55(m,2H),7.53(m,1H),7.38(m，1H),7.28(m，1H),7.27(d,1H),7.21(m,1H),7.20(d,1H),7.18(d,2H),7.16(d,1H),6.97(m,1H),6.92(s,1H),6.68(m,1H),1.69(s,6H).
Example 8
Synthesis of Compound 288
Figure 77748DEST_PATH_IMAGE222
The procedure of example 1 was repeated, except that the starting materials were changed to 288-A and 288-B.
1 HNMR(DMSO)：δ8.28(d,2H),8.11(d,2H),8.03(d,1H),7.94(d，1H),7.86(d，1H),7.78(d,1H),7.75(m,2H),7.69(m,2H),7.68(m,1H),7.62(m,2H),7.55(m,2H), 7.50(d,2H),7.40(s,1H),7.27(d,1H),7.21(m,1H),7.20(d,1H),7.18(d,2H),
7.16(d,1H),6.97(m,1H),6.91(s,1H),6.68(s,1H).
Example 9
Synthesis of Compound 322
Figure 9932DEST_PATH_IMAGE224
The procedure of example 1 was repeated, except that the starting materials were changed to 322-A and 322-B.
1 HNMR(DMSO)：δ8.51(d,1H),8.43(d，1H),8.17(s，1H),8.11(d,1H),8.08(s,1H),
7.98(d,3H),7.88(d,1H),7.85(d,1H),7.72(m,1H),7.67(m,1H),7.62(m,2H),
7.58(m,1H),7.55(d,2H),7.53(m,1H),7.50(d,2H),7.48(m,1H),7.37(d,2H),7.21(m,1H),7.20(d,1H),7.16(d,1H),6.97(m,1H),6.91(s,1H),6.68(s,1H),1.75(s,6H)..
Example 10
Synthesis of Compound 454
Figure 947801DEST_PATH_IMAGE226
The procedure of example 1 was repeated, except that the starting materials were changed to 454-A and 454-B.
1 HNMR(DMSO)：δ8.51(d，1H),8.43(d，1H),8.18(s,1H),8.11(d,1H),8.01(s,1H), 7.90(d,1H),7.88(d,1H),7.74(d,1H),7.72(m,1H),7.68(d,1H),7.67(m,1H),7.62(m,2H),7.58(m,1H),7.55(d,3H),7.50(d,2H),7.38(m,1H),7.37(d,2H),7.28(m,1H),7.24(s,1H),7.19(m,1H),7.17(d,1H),7.14(d,1H),6.95(m,1H),1.69(s,12H)..
Example 11
Synthesis of Compound E-1
Figure 727669DEST_PATH_IMAGE228
Under an argon atmosphere, compound E-1-A (37.3g, 100mmol), E-1-B (27.5g, 110mmol), palladium bis (dibenzylideneacetone) (1.15g, 2mmol), tri-tert-butylphosphine tetrafluoroborate (1.16g, 4mmol), 1.5M cesium carbonate (200mL, 300mmol), and 800mL o-xylene were added to a reaction vessel and heated under reflux for 20 hours. After completion of the reaction, the mixture was cooled to room temperature, a solid precipitated, filtered, and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to obtain 35.9g of compound E-1 in a yield of 72% and a HPLC purity of 99.3%.
1HNMR(DMSO)：δ9.27(s，1H),8.52 (d，1H), 8.36(d，4H),8.18 (d,2H), 8.15(d,1H),8.12(d,1H),7.92 (d,1H),7.82 (d,1H),7.75(d,1H),7.65(m,2H), 7.62(m,1H),7.50(m,6H)
Example 12
Synthesis of Compound E-69
Figure 968158DEST_PATH_IMAGE230
The procedure of example 11 was repeated, except that the starting materials were changed to the compounds E-69-A and E-69-B.
1 HNMR(DMSO)：δ9.27 (s，1H), 8.52 (d，1H), 8.36(d，1H),8.33(d,1H), 8.15(d,1H),8.03(d,1H),7.98(d,1H),7.92(d,1H),7.82(d,3H),7.81(d,1H),7.76(s,1H),7.75(d,1H),7.59(s,1H),7.54(d,1H),7.50(m,3H),7.48(m,3H),7.39(m,1H),7.31(m,1H).
Example 13
Synthesis of Compound E-169
Figure 777851DEST_PATH_IMAGE231
The procedure was repeated in the same manner as in example 11 except that the starting materials were replaced with the compound E-169-A and the compound E-169-B.
1 HNMR(DMSO)：δ9.83 (s，1H), 8.71 (d，1H), 8.56(d,1H),8.11(d,3H),
8.08(d,1H),8.03(d,1H),7.94(s,2H),7.84(d,2H),7.82(d,1H),7.75(d,1H),7.69(m,2H),7.62(m,2H),7.59(m,1H),7.53(m,2H),7.50(d,2H),7.32(m,2H),6.80(s,1H).
Example 14
Synthesis of Compound E-191
Figure 129198DEST_PATH_IMAGE233
The procedure of example 11 was repeated, except that the starting materials were replaced with the compounds E-191-A and E-191-B.
1 HNMR(DMSO)：δ9.27(s，1H), 9.24(d,1H),8.87(s,1H),8.70(d,1H),8.68
(s,1H),8.53(s,1H),8.42(d,1H),8.37(d,1H),8.35(d,1H),8.11(d,1H),8.04(d,1H),7.92(d,1H),7.84(d,1H),7.82(d,1H),7.75(d,1H),7.57(m,1H).
Example 15
Synthesis of Compound E-204
Figure 324424DEST_PATH_IMAGE234
The procedure of example 11 was repeated, except that the starting materials were replaced with the compounds E-204-A and E-204-B.
1 HNMR(DMSO)：δ9.27(s,1H),8.37 (d,1H), 8.35(d,1H),8.18(d,1H),8.11
(m,2H),7.98(d,1H),7.92(d,1H),7.82(d,1H),7.78(s,1H),7.75(d,1H),7.65(m,2H),7.62(m,1H),7.54(d,1H),7.39(m,1H),7.31(m,1H).
Example 16
Synthesis of Compound E-261
Figure 63710DEST_PATH_IMAGE235
The procedure of example 11 was repeated, except that the starting materials were changed to E-261-A and E-261-B.
1 HNMR(DMSO)：δ9.27(s,1H),8.37 (d,1H), 8.35(d,1H),8.28(d,2H),8.11
(d,1H),7.94(s,1H),7.92(d,1H),7.82(d,1H),7.75(d,3H),7.73(m,1H),7.62
(s,1H),7.60(d,2H),7.51(m,2H),7.50(m,3H),7.49(m,2H),7.48(m,2H),7.46(m,2H),7.41(s,2H),7.38(d,2H).
Example 17
Synthesis of Compound E-288
Figure 970486DEST_PATH_IMAGE236
The procedure of example 11 was repeated, except that the starting materials were changed to E-288-A and E-288-B.
1HNMR(DMSO)：δ9.27(s，1H),8.98 (d，1H), 8.65(s，1H),8.37 (d,1H), 8.35(d,1H),8.18(d,2H),8.11(d,1H),7.92(d,2H),7.90(d,1H),7.82(d,1H), 7.75(d,1H),7.70(d,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H).
Example 18
Synthesis of Compound E-328
Figure 890DEST_PATH_IMAGE237
The procedure of example 11 was repeated, except that the starting material E-328-A was changed to E-328-B.
1HNMR(DMSO)：δ9.27(s，1H),8.37 (d，1H), 8.35(d，1H),8.18(d,2H), 8.11(d,1H),8.09(d,1H),8.06 (d,1H),7.99(d,1H),7.82(d,1H),7.75(d,1H),
7.65(m,2H),7.63(m,1H), 7.62(m,1H),7.60(m,1H),7.55(s,1H),7.51(d,2H),
7.46(m,2H),7.41(s,1H),7.38(d,1H).
Example 19
Synthesis of Compound E-379
Figure DEST_PATH_IMAGE239
The procedure of example 11 was repeated, except that the starting materials were changed to the compounds E-379-A and E-379-B.
1HNMR(DMSO)：δ9.27(s，1H),8.37 (d，1H), 8.35(d，1H),8.28（d，2H），8.03(d,1H), 7.98(d,1H),7.92(d,1H),7.82 (d,2H),7.76 (d,2H),7.62(s,1H), 7.54(d,1H),7.51(d,2H),7.50(m,3H),7.48(m,2H)，7.46(m,2H),7.41(s,1H),
7.39(m,1H),7.38(d,2H),7.31(m,1H).
Example 20
Synthesis of Compound E-403
Figure 535777DEST_PATH_IMAGE240
The procedure of example 11 was repeated, except that the starting materials were replaced with the compounds E-403-A and E-403-B.
1HNMR(DMSO)：δ9.27(s，1H),8.55(d,1H),8.37 (d，1H), 8.35(d，1H),
8.18(d,2H), 8.11(d,1H),7.94(d,1H),7.92(d,1H),7.85(s,1H),7.82
(d,1H),7.75 (d,1H),7.65(m,2H),7.62(m,3H),7.51(s.1H),7.50(d,2H),
7.35(m,1H),7.16(m,1H).
Device embodiments
Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples of the present invention are as follows:
Figure 531169DEST_PATH_IMAGE242
example 21
The basic structural model of the device is as follows: ITO/HAT-CN (10 nm)/TAPC (40 nm)/TCTA (10 nm)/EML (40nm)/ETL (30nm)/LiF (1nm)/Al (80nm), wherein the composition of EML: the main material of the invention: RD (Ir complex) = 98: 2.
the manufacturing method of the organic photoelectric device comprises the following steps:
(1) carrying out ultrasonic cleaning on a transparent anode Indium Tin Oxide (ITO)20(10 omega/sq) glass substrate by using acetone, ethanol and distilled water in sequence, and then treating for 15 minutes by using ozone plasma;
(2) after an ITO substrate is arranged on a substrate fixer of vacuum vapor deposition equipment, the system pressure is controlled to be 10-6Sequentially evaporating HAT-CN with the thickness of 10nm, TAPC with the thickness of 40nm and TCTA with the thickness of 10nm on the ITO substrate;
(3) evaporating a light emitting layer (EML) with the thickness of 40nm (wherein the compound 1 and the compound E-1 of the invention are evaporated at the rate of 4: 6, and the mass ratio of the host material to the RD-1 is 98: 2),
(4) an Electron Transport Layer (ETL) material was evaporated to a thickness of 30 nm.
(5) Evaporating LiF with the thickness of 1nm as an electron injection layer;
(6) and finally, evaporating Al with the thickness of 80nm as a cathode, and packaging the device by using a glass packaging cover.
The device test results are shown in table 1.
Example 22
The same devices as those in example 21 were fabricated and evaluated except that the EML material was changed to compounds 5 and E-10, and the test results are shown in Table 1.
Example 23
The same devices as those in example 21 were evaluated except that the EML materials were Compound 11 and E-37, and the test results are shown in Table 1.
Example 24
The same devices as those in example 21 were evaluated except that the EML materials were compound 19 and E-50, and the test results are shown in Table 1.
Example 25
The same devices as those in example 21 were evaluated except that the EML materials were compound 24 and E-65, and the test results are shown in Table 1.
Example 26
The same devices as those in example 21 were evaluated except that the EML materials were compound 29 and E-77, and the test results are shown in Table 1.
Example 27
The same devices as those in example 21 were evaluated except that the EML materials were compound 38 and E-99, and the test results are shown in Table 1.
Example 28
The same devices as those in example 21 were evaluated except that the EML materials were Compound 43 and E-112, and the test results are shown in Table 1.
Example 29
The same devices as those in example 21 were evaluated except that the EML materials were compound 46 and E-135, and the test results are shown in Table 1.
Example 30
The same devices as those in example 21 were evaluated except that the EML materials were compound 54 and E-154, and the test results are shown in Table 1.
Comparative example 1
The same devices as those in example 21 were evaluated except that the EML material was CBP compound, and the test results are shown in table 1.
Comparative example 2
The same devices as those prepared in example 21 were evaluated except that the EML material was the compounds Ref-1 and Ref-2, and the test results are shown in Table 1.
Table 1 shows the results of the performance test of the devices in the examples of the present invention and the comparative examples.
TABLE 1
Figure 190821DEST_PATH_IMAGE244
The device structure of the invention is consistent except that the luminescent layer is different, based on the device performance of the comparative example 1 and the comparative example 2 as reference, the current efficiency of the device after the host material is applied to the luminescent layer is obviously improved, and the service life of the device is also improved. In conclusion, the main body material prepared by the invention has a great application value in organic light emitting diodes.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (6)

1. A host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 and the second host compound is represented by formula 2:
Figure FDA0003371913660000011
wherein R is1Selected from the following structures:
Figure FDA0003371913660000012
X1，Y1each independently selected from CR3R4、O、S、S(＝O)、S(＝O)2Or SiR3R4；
Z1、Z2、Z3、Z4Are identical or different from each other and are each independently selected from CR5Or an N atom;
R2、R3、R4、R5the same or different, each independently selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or combinations thereof;
Ar1is aryl of C6-C60 or heteroaryl of C5-C60;
Figure FDA0003371913660000013
X2,Y2each independently selected from C, NR8O, S, and X2，Y2At least one of them is a C atom,
R6、R7and R8The same or different from each other, and each is independently selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
L1represents a single bond, substituted or unsubstitutedArylene of C6-C40, substituted or unsubstituted heteroarylene of C5-C40;
the group A is selected from CN, F, carbonyl, carboxyl, nitro or selected from the following groups, or the combination of the groups;
Figure FDA0003371913660000014
Figure FDA0003371913660000021
wherein R is9、R10、R11And R12Independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or combinations thereof;
or, X2,Y2Each independently selected from N, O, S and X2，Y2In which at least one is an N atom, L1Is substituted or unsubstituted arylene of C6-C40, substituted or unsubstituted heteroarylene of C5-C40, and the heteroatoms are not all nitrogen atoms; the group A is selected from one or more of hydrogen, CN, F, carbonyl, carboxyl, nitro or the combination of the hydrogen, the CN, the F, the carbonyl, the carboxyl and the nitro, and at least one is not hydrogen.
2. The host material of claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
Figure FDA0003371913660000031
Figure FDA0003371913660000041
Figure FDA0003371913660000051
Figure FDA0003371913660000061
Figure FDA0003371913660000071
Figure FDA0003371913660000081
Figure FDA0003371913660000091
Figure FDA0003371913660000101
Figure FDA0003371913660000111
Figure FDA0003371913660000121
Figure FDA0003371913660000131
Figure FDA0003371913660000141
Figure FDA0003371913660000151
Figure FDA0003371913660000161
Figure FDA0003371913660000171
Figure FDA0003371913660000181
Figure FDA0003371913660000191
Figure FDA0003371913660000201
Figure FDA0003371913660000211
3. the host material of claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
Figure FDA0003371913660000212
Figure FDA0003371913660000221
Figure FDA0003371913660000231
Figure FDA0003371913660000241
Figure FDA0003371913660000251
Figure FDA0003371913660000261
Figure FDA0003371913660000271
Figure FDA0003371913660000281
Figure FDA0003371913660000291
Figure FDA0003371913660000301
Figure FDA0003371913660000311
Figure FDA0003371913660000321
Figure FDA0003371913660000331
Figure FDA0003371913660000341
Figure FDA0003371913660000351
Figure FDA0003371913660000361
wherein R is7Selected from hydrogen, deuterium, cyano, halogen, alkoxy, alkylthio, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or combinations thereof.
4. An organic electroluminescent device comprising a cathode layer, an anode layer and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer, and the light-emitting layer contains the host material according to any one of claims 1 to 3.
5. The organic electroluminescent device according to claim 4, wherein the light-emitting layer further comprises a dopant, wherein the mass ratio of the host material to the dopant is 1:99-99: 1.
6. the organic electroluminescent device according to claim 4, wherein the mass ratio of the first host compound to the second host compound in the host material is 1:99-99: 1.
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