CN115304491B - Hole organic electroluminescent compound and preparation method and application thereof - Google Patents

Hole organic electroluminescent compound and preparation method and application thereof Download PDF

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CN115304491B
CN115304491B CN202211067801.0A CN202211067801A CN115304491B CN 115304491 B CN115304491 B CN 115304491B CN 202211067801 A CN202211067801 A CN 202211067801A CN 115304491 B CN115304491 B CN 115304491B
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mmol
added
hole
organic electroluminescent
general formula
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CN115304491A (en
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汪康
贾宇
赵贺
孟范贵
杨冰
王勇壮
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses a hole organic electroluminescent compound, belongs to the technical field of luminescent materials, and provides an indene hole transport material as a mother nucleus, wherein the general structural formula of the indene hole transport material is shown in an instruction book. Wherein the indene parent nucleus reduces the symmetry of the molecule, increases the conformational isomer of the molecule, and inhibits the aggregation of the molecule so as to improve the hole mobility. Meanwhile, the amine units have lower ionization potential, better electron donating property and higher hole mobility, and the molecular weight is increased, so that the molecules are not easy to crystallize and aggregate, and the material has higher photo-thermal stability. After the hole transport material is used for an organic electroluminescent device, the device with improved luminous efficiency, low driving voltage and longer service life is obtained.

Description

Hole organic electroluminescent compound and preparation method and application thereof
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to a hole organic electroluminescent compound, a preparation method and application thereof.
Background
An organic electroluminescent diode (hereinafter referred to as OLED) is an important electroluminescent device, and is used for active light emission without a backlight source, and has the advantages of high luminous efficiency, large visual angle, fast response speed, large temperature adaptation range, small energy consumption, lighter weight, thinner weight, flexible display, and the like, and has great application prospects, thereby attracting attention of numerous researchers.
In such an organic light emitting diode, when a voltage is applied between an anode and a cathode, holes from the anode and electrons from the cathode are injected into the organic material layer. The generated excitons generate light having a specific wavelength when they migrate to the ground state. It has the following structure: an anode, a cathode, and an organic material layer interposed therebetween. In order to improve efficiency and stability of the organic EL element, the organic material layer includes a plurality of layers having different materials, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emitting layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Among them, a layer having a hole transporting function such as a hole injection layer, a hole transport layer, an electron blocking layer, etc. can change hole transport efficiency, light emitting efficiency, lifetime, etc. of holes to a light emitting layer, and has a great influence on performance data of an electronic device.
The life of the existing organic EL devices is not ideal, and thus, how to develop a device having excellent current efficiency and low driving voltage, and long service life is a technical problem that those skilled in the art have been urgent to solve.
Disclosure of Invention
In view of the above, the invention provides a hole organic electroluminescent compound, a preparation method thereof and application thereof in preparing devices.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the structural general formula of the hole organic electroluminescent compound is shown as the general formula I:
in formula I, X is selected from: a single bond, O, S, siR, se, CR or NR, R being a substituted or unsubstituted C6-C24 aryl group, or R in NR being linked to Cy2 to form an aliphatic ring;
l1 and L2 are each independently selected from a C4-C20 aromatic or heteroaromatic ring, or a C1-C20 alkyl, C1-C20 heteroalkyl, C6-C30 aryl or C6-C30 heteroaryl substituted C4-C20 aromatic or heteroaromatic ring wherein the heteroatom is any one of oxygen, nitrogen, sulfur;
ar1-Ar8 are each independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl, or substituted or unsubstituted C3-C20 cycloalkyl wherein the heteroatom is any of oxygen, nitrogen, sulfur;
cy1-Cy2 are each independently selected from a C4-C30 aromatic or heteroaromatic ring, or a C1-C20 alkyl, C1-C20 heteroalkyl, C6-C30 aryl or C6-C30 heteroaryl substituted C4-C30 aromatic or heteroaromatic ring wherein the heteroatom is any one of oxygen, nitrogen, sulfur;
n1-n4 represent 0 or 1, respectively, and 1.ltoreq.n1+n2+n3+n4.ltoreq.4.
Further, the L1 and L2 are independently selected from C4-C10 aromatic rings or heteroaromatic rings, or C1-C10 alkyl, C1-C10 heteroalkyl, C6-C20 aryl or C6-C20 heteroaryl substituted C4-C10 aromatic rings or heteroaromatic rings, wherein the heteroatom is any one of oxygen, nitrogen and sulfur.
Further, ar1 to Ar8 mentioned above are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, or a substituted or unsubstituted C3-C10 cycloalkyl group, wherein the heteroatom is any one of oxygen, nitrogen, and sulfur.
Further, the above Cy1-Cy2 are each independently selected from the group consisting of C4-C6 aromatic or heteroaromatic rings, or C1-C10 alkyl, C1-C10 heteroalkyl, C6-C20 aryl or C6-C20 heteroaryl substituted C4-C6 aromatic or heteroaromatic rings wherein the heteroatom is any one of oxygen, nitrogen, sulfur.
Further, n1+n2+n3+n4=1, and the structural general formula of the hole organic electroluminescent compound is shown as a general formula a-1, a general formula a-2 or a general formula a-3:
or, n1+n2+n3+n4=2, and the structural general formula of the hole organic electroluminescent compound is shown as a general formula b-1, a general formula b-2, a general formula b-3 or a general formula b-4:
or, n1+n2+n3+n4=3 or 4, and the structural general formula of the hole organic electroluminescent compound is shown as the general formula c-1, the general formula c-2, the general formula c-3 or the general formula d-1:
preferably, the hole-type organic electroluminescent compound is selected from any one of compounds represented by the following structural formulae:
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the invention also provides a preparation method of the hole organic electroluminescent compound,
n1+n2+n3+n4=1, comprising the steps of:
intermediate a3 is obtained by a Suzuki reaction between intermediate a1 and intermediate a2, intermediate a5 is obtained by a Suzuki reaction between intermediate a3 and intermediate a4, intermediate a7 is obtained by a Grignard reaction between intermediate a5 and lithium reagent of intermediate a6, and a series of compounds shown in the general formula a-2 is obtained by a dehydrative cyclization reaction of intermediate a 7;
or, intermediate b2 is obtained by a Suzuki reaction between intermediate a1 and intermediate b1, intermediate b4 is obtained by a Suzuki reaction between intermediate b2 and intermediate b3, intermediate b6 is obtained by a Grignard reaction between intermediate b4 and lithium reagent of intermediate b5, and a series of compounds shown in the general formula a-1 is obtained by a dehydrative cyclization reaction of intermediate b 6;
or, intermediate a1 and intermediate b1 can obtain intermediate b2 through a suzuki reaction, intermediate b2 and intermediate c1 can obtain intermediate c2 through a suzuki reaction, intermediate c2 and intermediate c3 can obtain intermediate c4 through a grignard reaction by a lithium reagent, intermediate c4 can obtain intermediate c5 through a dehydrative cyclization reaction, and intermediate c5 and intermediate c6 can obtain a series of compounds shown in a general formula a-3 through a buhelde-hart reaction;
the synthetic route is as follows:
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or, n1+n2+n3+n4=2, comprising the steps of:
intermediate d2 is obtained by the reaction of intermediate a1 and intermediate d1 through bell wood, intermediate d4 is obtained by the reaction of intermediate d2 and intermediate d3 through bell wood, intermediate d6 is obtained by the reaction of intermediate d4 and lithium reagent of intermediate d5 through a lattice reaction, and a series of compounds shown in the general formula b-1 is obtained by the dehydration cyclization reaction of intermediate d 6;
or, intermediate a1 and intermediate d1 are subjected to a bell-wood reaction to obtain an intermediate d2, intermediate d2 and intermediate e1 are subjected to a bell-wood reaction to obtain an intermediate e2, intermediate e2 and a lithium reagent of intermediate e3 are subjected to a lattice reaction to obtain an intermediate e4, intermediate e4 is subjected to a dehydration cyclization reaction to obtain a general formula e5, and intermediate e5 and intermediate e6 are subjected to a Buch Walder-Hartmann reaction to obtain a series of compounds shown in a general formula b-3;
or the synthesis process of the series of compounds shown in the general formula b-2 is the same as that of the series of compounds shown in the general formula b-3;
or, intermediate a1 and intermediate f1 are subjected to a bell-wood reaction to obtain intermediate f2, intermediate f2 and intermediate g1 are subjected to a bell-wood reaction to obtain intermediate g2, intermediate g2 and lithium reagent of intermediate g3 are subjected to a lattice reaction to obtain intermediate g4, intermediate g4 is subjected to a dehydrative cyclization reaction to obtain intermediate g5, intermediate g5 and intermediate g6 are subjected to a Buchwald-Hattv reaction to obtain intermediate g7, and intermediate g7 and intermediate g8 are subjected to a Buchwald-Hattv reaction to obtain a series of compounds shown in the general formula b 4; the synthetic route is as follows:
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or, n1+n2+n3+n4=3 or 4, comprising the steps of:
intermediate a1 and intermediate h1 react through a bell wood to obtain intermediate h2, intermediate h2 reacts with intermediate h3 to obtain intermediate h4, intermediate h4 reacts with a lithium reagent of intermediate h5 in a format to obtain intermediate h6, intermediate h6 reacts through a dehydrative cyclization reaction to obtain intermediate h7, and intermediate h7 reacts with intermediate h8 through a Buch Walder-Hartmann reaction to obtain a series of compounds shown in a general formula c-1;
or, intermediate a1 and intermediate h1 are reacted through a bell wood reaction to obtain intermediate h2, intermediate h2 and intermediate h3 are reacted to obtain intermediate h4, intermediate h4 and lithium reagent of intermediate i1 are reacted through a format reaction to obtain intermediate i2, intermediate i2 is reacted through a dehydration cyclization reaction to obtain intermediate i3, intermediate i3 and intermediate i4 are reacted through a Buchnolde-Hastech reaction to obtain intermediate i5 through a reaction dynamics regulation, and intermediate i5 and intermediate i6 are reacted through a Buchnolde-Hastech reaction to obtain a series of compounds shown in a general formula d-1;
or, the synthetic route of the series compounds shown in the general formula c-2 and the general formula c-3 is the same as that of the general formula d-1;
the synthetic route is as follows:
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the borate compounds such as intermediate a2 and the like involved in the above synthetic routes can be obtained through the corresponding halogenated compounds through the hystero Pu Pengji reaction, the corresponding halogenated compounds can also be obtained through the browald-hattery reaction, and the related methods are common practice in the industry and are also described in great numbers in the present disclosure, so that the details of the disclosure are omitted herein.
The invention also provides an application of the hole organic electroluminescent compound prepared by the hole organic electroluminescent compound or the method in preparation of an organic electroluminescent device.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a hole transport material with indene as a mother nucleus. Wherein the indene parent nucleus reduces the symmetry of the molecule, increases the conformational isomer of the molecule, and inhibits the aggregation of the molecule so as to improve the hole mobility. Meanwhile, the amine units have lower ionization potential, better electron donating property and higher hole mobility, and the molecular weight is increased, so that the molecules are not easy to crystallize and aggregate, and the material has higher photo-thermal stability. After the hole transport material is used for an organic electroluminescent device, the device with improved luminous efficiency, low driving voltage and longer service life is obtained.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a hole-class organic electroluminescent compound of example 1;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of a hole-class organic electroluminescent compound of example 2;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of a hole-class organic electroluminescent compound of example 3;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the hole-class organic electroluminescent compound of example 4;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the hole-class organic electroluminescent compound of example 5;
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the hole-class organic electroluminescent compound of example 6;
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of a hole-class organic electroluminescent compound of example 7;
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Intermediate a1 (62 mmol), intermediate b1 (68 mmol), K 2 CO 3 (123 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 ( 0.6 mmol), heating to 85deg.C, stirring for 2h, cooling to room temperature, separating, collecting organic phase, drying over anhydrous sodium sulfate, stirring with silica gel, spin-drying, and performing column chromatography (DCM: pe=1: 3) Intermediate c1 (14.17 g, yield: 95%) was obtained )
Intermediate c1 (58 mmol), intermediate d1 (64 mmol), cs 2 CO 3 (116 mmol) was placed in a three-necked flask, 150mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.6 mmol) and X-PhOS (3 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e1 (31.76 g, yield: 91%).
Intermediate f1 (58 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (58 mmol) was added dropwise, stirring was performed for 2h, intermediate e1 (53 mmol) was added, and the mixture was stirred at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g1 (34.85 g, yield: 87%).
Intermediate g1 (46 mmol) was added to a single vial, 100mL of DCM was added, MSA (231 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave the target molecule M1 (27.49 g, yield: 81%). 1 H NMR(400MHz,)δ7.63(m,8H),7.52(m,20H),7.34(m,5H),7.27(m,6H).
Example 2
Intermediate a2 (41 mmol), intermediate b2 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 (0.4 mmol) was warmed to 85 ℃, stirred for 2h, cooled to room temperature, the organic phase was collected, dried over anhydrous sodium sulfate, taken up in silica gel, and column chromatography (DCM: pe=1:3) after spin-drying gave intermediate c2 (19.98 g, yield: 87%).
Intermediate c2 (36 mmol), intermediate d2 (39 mmol), cs 2 CO 3 (71 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.35 mmol) and X-PhOS (0.71 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e2 (18.04 g, yield: 83%).
Intermediate f2 (33 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (32.8 mmol) was added dropwise, stirring was performed for 2h, intermediate e2 (30 mmol) was added, and the mixture was stirred at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g2 (20.12 g, yield: 88.5%).
Intermediate g2 (26 mmol) was added to a single vial, 100mL of DCM was added, MSA (132 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave the target molecule M11 (14.81 g, yield: 77%). 1 H NMR(400MHz,)δ:9.00(s,2H),8.92(s,1H),7.59(m,7H),7.51(d,8H),7.47(m,5H),7.43(d,2H),7.38(d,4H),7.28(m,5H),7.23(s,1H),7.20(d,2H).
Example 3
Intermediate a3 (41 mmol), intermediate b3 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 Heating to 85deg.C, stirring for 2 hr, cooling to room temperature, separating, collecting organic phase, drying over anhydrous sodium sulfate, mixing with silica gel, and performing column chromatography (DCM: PE=1:3) after spin-drying to obtain intermediate c3 (21.90 g, yield: 89%)
Intermediate c3 (37 mmol), intermediate d3 (40 mmol), cs 2 CO 3 (73 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.4 mmol) and X-PhOS (0.7 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e3 (21.20 g, yield: 89%).
Intermediate f3 (36 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (36 mmol) was added dropwise, stirring was performed for 2h, intermediate e3 (33 mmol) was added, and the mixture was stirred at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g3 (20.20 g, yield: 69%).
Intermediate g3 (23 mmol) was added to a single vial, 100mL of DCM was added, MSA (113 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave the target molecule M226 (16.19 g, 81% yield). 1 HNMR(400MHz,)δ9.01(s,2H),8.92(s,1H),8.12(d,1H),7.90(d,1H),7.83(d,1H),7.76(d,2H),7.73(d,1H),7.69(d,1H),7.64(d,2H),7.59(d,2H),7.55(d,1H),7.49(d,3H),7.46(m,6H),7.42(d,2H),7.38(m,5H),7.34(d,1H),7.30(d,2H),7.25(m,3H),7.06(d,1H),1.61(s,3H),1.56(s,3H).
Example 4
Intermediate a4 (41 mmol), intermediate b4 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 ( 0.4 mmol), heating to 85deg.C, stirring for 2h, cooling to room temperature, separating, collecting organic phase, drying over anhydrous sodium sulfate, stirring with silica gel, spin-drying, and performing column chromatography (DCM: pe=1: 3) Intermediate c4 (8.98 g, yield: 91%) was obtained )
Intermediate c4 (37 mmol), intermediate d4 (41 mmol), cs 2 CO 3 (74 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.37 mmol) and X-PhOS (0.74 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting organic phase, extracting the aqueous phase with DCM for three times, mixing the organic phases, adding anhydrous sodium sulfate, and dryingSpin-drying and column chromatography (DCM: pe=1:1) gave intermediate e4 (10.88, yield: 88.5%).
Intermediate f4 (33 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (33 mmol) was added dropwise, stirring was performed for 2h, intermediate e4 (30 mmol) was added, and stirring was performed at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g4 (11.95, yield: 76.5%).
Intermediate g4 (23 mmol) was added to a single vial, 100mL of DCM was added, MSA (115 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave intermediate h4 (9.95, yield: 86%).
Add intermediate h4 (20 mmol), intermediate i4 (22 mmol), t-BuONa (40 mmol) to a three-necked flask, add 100mL of anhydrous toluene, take a breath three times, add Pd 2 (dba) 3 (0.2mmol),P(t-Bu) 3 (0.2 mmol) was heated to 110℃and stirred for 10h. Cooled to room temperature, purified water was added and stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and the target molecule M32 by column chromatography (14.07, yield: 85%). 1 H NMR(400MHz,)δ:8.00(s,1H),7.94(d,1H),7.91(d,1H),7.87(d,1H),7.76(d,1H),7.72(m,3H),7.58(m,4H),7.54(s,5H),7.51(d,2H),7.48(m,5H),7.38(m,8H),7.30(d,1H),7.29(d,2H),7.25(s,1H),7.23(t,1H),7.17(d,1H),7.13(d,1H),1.62(s,3H),1.57(s,3H).
Example 5
Intermediate a5 (41 mmol), intermediate b5 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 ( 0.4 mmol), heating to 85deg.C, stirring for 2h, cooling to room temperature, separating, collecting organic phase, drying over anhydrous sodium sulfate, stirring with silica gel, spin-drying, and performing column chromatography (DCM: pe=1: 3) Intermediate c5 (19.06 g, yield: 83%) was obtained )
Intermediate c5 (34 mmol), intermediate d5 (37 mmol), cs 2 CO 3 (68 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.34 mmol) and X-PhOS (0.68 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e5 (28.10 g, yield: 86%).
Intermediate f5 (32 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (32 mmol) was added dropwise, stirring was performed for 2h, intermediate e5 (28 mmol) was added, and the mixture was stirred at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g5 (24.05 g, yield: 77%).
Intermediate g5 (22 mmol) was added to a single vial, 100mL of DCM was added, MSA (110 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave the target molecule M245 (17.6 g, yield: 73%). 1 H NMR(400MHz,)δ:8.42(d,2H),7.76(m,3H),7.66(d,3H),7.61(m,12H),7.52(d,3H),7.47(t,2H),7.46(m,6H),7.42(s,2H),7.39(m,9H),7.30(d,4H),7.23(s,2H),7.22(s,1H),7.07(d,1H),7.05(d,4H),1.46(s,6H).
Example 6
Intermediate a6 (41 mmol), intermediate b6 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 (0.4 mmol) was warmed to 85 ℃, stirred for 2h, cooled to room temperature, the organic phase was collected, dried over anhydrous sodium sulfate, stirred with silica gel, and column chromatographed after spin-drying (DCM: pe=1:3) to give intermediate c6 (8.98 g, yield: 91%).
Intermediate c6 (37 mmol), intermediate d6 (41 mmol), cs 2 CO 3 (74 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.37 mmol) and X-PhOS (0.75 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e6 (17.81 g, yield: 80%).
Intermediate f6 (33 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium (33 mmol) was added dropwise, stirring was performed for 2h, intermediate e6 (30 mmol) was added, and the mixture was stirred at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g6 (19.92 g, yield: 84%).
Intermediate g6 (25 mmol) was added to a single vial, 100mL of DCM was added, MSA (127 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave intermediate h6 (15.83 g, yield: 82%).
Add intermediate h6 (20 mmol), intermediate i6 (22 mmol), t-BuONa40 mmol to a three-necked flask, add anhydrous toluene 100mL, take a breath three times, add Pd 2 (dba) 3 (0.20mmol),P(t-Bu) 3 (0.40 mmol), the temperature was raised to 110℃and stirred for 10h. Cooled to room temperature, purified water was added and stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and the target molecule M242 by column chromatography (14.48 g, yield: 66%). 1 H NMR(400MHz,)δ8.19(d,4H),8.05(d,4H),7.70(m,4H),7.66(m,3H),7.59(m,7H),7.54(m,3H),7.46(d,4H),7.43(d,6H),7.39(m,2H),7.37(m,4H),7.35(d,3H),7.31(d,1H),7.27(t,4H),7.20(d,2H),7.15(s,1H),7.07(d,1H),6.97(d,1H),1.61(s,3H),1.56(s,3H).
Example 7
Intermediate a7 (41 mmol), intermediate b7 (45 mmol), K 2 CO 3 (82 mmol) was placed in a three-necked flask, 100mL of THF and 50mL of purified water were added, the mixture was purged three times, and Pd (PPh) 3 ) 4 (0.4 mmol) was warmed to 85 ℃, stirred for 2h, cooled to room temperature, the organic phase was collected, dried over anhydrous sodium sulfate, taken up in silica gel, and column chromatography (DCM: pe=1:3) after spin-drying gave intermediate c7 (8.98 g, yield: 91%).
Intermediate c7 (37 mmol), intermediate d7 (41 mmol), cs 2 CO 3 (74 mmol) was placed in a three-necked flask, 100mL of anhydrous dioxane was added, the air was changed three times, and Pd was added 2 (dba) 3 (0.37 mmol) and X-PhOS (0.74 mmol), heating to 120deg.C, stirring for 10h, cooling to room temperature, adding purified water, stirring for 30min, separating, collecting the organic phase, adding DCM to the aqueous phase for three times, combining the organic phases, adding anhydrous sodium sulfate for drying, spin-drying, and column chromatography (DCM: PE=1:1) to give intermediate e7 (8.87 g, yield: 85%).
Intermediate f7 (35 mmol) was added to a three-necked flask, 100mL of anhydrous tetrahydrofuran was added, the temperature was lowered to-78 ℃, butyllithium was added dropwise, stirring was performed for 2h, intermediate e7 (31 mmol) was added, and stirring was performed at room temperature for 10h. Dilute hydrochloric acid was added, stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatographed (DCM: pe=1:1) to give intermediate g7 (12.53 yield: 80%).
Intermediate g7 (24 mmol) was added to a single vial, 100mL of DCM was added, MSA (119 mmol) was added, stirred at room temperature for 2h, water was added, stirred for 30min, the organic phase was collected, the aqueous phase was extracted 3 times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave intermediate h7 (9.81 g, yield: 84%).
Add intermediate h7 (20 mmol), intermediate i7 (22 mmol), t-BuONa (40 mmol) to a three-necked flask, add 100mL of anhydrous toluene, take a breath three times, add Pd 2 (dba) 3 (0.2mmol),P(t-Bu) 3 (0.2 mmol) was heated to 110℃and stirred for 10h. Cooled to room temperature, purified water was added and stirred for 30min, the organic phase was separated, the aqueous phase was extracted 3 times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography gave intermediate j7 (yield: 88%).
Adding the intermediate j7 (17 mmol), the intermediate k7 (19 mmol) and t-BuONa into a three-mouth bottle, adding 100mL of anhydrous toluene, ventilating for three times, and adding Pd 2 (dba) 3 (0.2mmol),P(t-Bu) 3 (0.2 mmol) was heated to 110℃and stirred for 10h. Cooling to room temperature, adding purified water, stirring for 30min, separating, collecting organic phase, extracting water phase with ethyl acetate for 3 times, mixing organic phases, drying with anhydrous sodium sulfate, and performing column chromatography to obtain target molecule M242 (14.38 g, yield: 79%). 1 H NMR(400MHz,)δ:8.69(d,2H),8.67(m,1H),8.26(d,2H),7.95(d,1H),7.91(m,3H),7.86(d,2H),7.81(d,1H),7.59(m,6H),7.55(d,1H),7.54(m,4H),7.45(m,8H),7.39(m,8H),7.33(d,1H),7.30(m,2H),7.23(s,1H),7.19(m,2H),7.13(d,5H),7.04(d,4H).
The synthesis methods of other compounds are the same as those of the above examples, and are not described in detail herein, and mass spectra, molecular formulas and yields of other synthesis examples are shown in table 1 below:
TABLE 1
Chemical combinationArticle (B) Molecular formula Mass spectrum calculated value Mass spectrometry test values Yield (%)
Compound M3 C57H39N 737.95 737.69 80.5
Compound M7 C63H45N3 844.07 844.22 65.94
Compound M14 C61H41N3 816.02 816.34 61.08
Compound M19 C55H37N3 739.92 739.76 80.49
Compound M25 C63H43N 814.04 814.22 79.72
Compound M30 C64H45N 828.07 828.26 58.83
Compound M36 C62H47N 806.07 806.18 74.88
Compound M38 C62H47N 806.07 805.87 66.38
Compound M40 C66H47N 854.11 854.33 73.61
Compound M44 C64H45N3 856.09 856.28 62.38
Compound M50 C61H45N 792.04 791.91 71.75
Compound M57 C65H46N2 855.10 855.33 67.1
Compound M64 C62H41NO 816.02 816.19 70.86
Compound M70 C63H41NO 828.03 827.79 71.78
Compound M75 C62H40N2O 829.02 829.26 80.09
Compound M85 C63H41NO 828.03 828.15 57.6
Compound M96 C62H47N 806.07 806.24 72.71
Compound M105 C65H46N2 855.10 855.43 72.95
Compound M113 C63H51NSi 850.19 850.34 58.31
Compound M120 C67H49N 868.14 868.37 74.47
Compound M130 C66H47NO 870.11 869.26 58.37
Compound M146 C66H47NO 870.11 870.28 73.84
Compound M155 C61H51N 834.12 834.36 73.4
Compound M163 C61H47N3 822.07 822.18 62.04
Compound M177 C68H52N2 897.18 897.39 66.53
Compound M186 C68H52N2 897.18 896.92 80.93
Compound M201 C66H48N2 869.12 869.35 68
Compound M210 C75H52N2 981.28 981.06 70.6
Device example 1: manufacture of organic electroluminescent devices containing Compound M1
a. ITO anode: washing an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, washing by ultrasonic waves for 30min, repeatedly washing by distilled water for 2 times, washing by ultrasonic waves for 10min, transferring into a spin dryer for spin drying after washing, baking for 2 hours at 220 ℃ by a vacuum oven, and cooling after baking is finished, so that the glass substrate can be used. The substrate is used as an anode, a vapor deposition device process is performed by using a vapor deposition machine, and other functional layers are sequentially vapor deposited on the substrate.
b. HIL (hole injection layer): to be used forThe chemical formulas of the compounds M1 and P-dopant provided in the above examples are shown below. The evaporation rate ratio of the compound M1 and the P-dock of the above example was 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used forThe compound M1 provided in the above example was vacuum-evaporated as a hole transport layer on top of the hole injection layer at 130 nm.
d. Light-emitting auxiliary layer: to be used forVacuum evaporating 10nm EBL-1 as a light-emitting auxiliary layer on the hole transport layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer toThe Host material (Host) and the Dopant material (Dopant) having a thickness of 20nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 98:2.
f. HBL (hole blocking layer): to be used forIs used as a hole blocking layer, and HB-1 of 5nm is vacuum deposited on the upper surface of the light-emitting layer.
g. ETL (electric)Sub-transport layer): to be used forAnd vacuum evaporating ET-1 as an electron transport layer on the hole blocking layer.
h. EIL (electron injection layer): to be used forThe vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used forThe vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used forCPL-1 having a thickness of 70nm was vacuum deposited on the cathode as a light extraction layer. And packaging the evaporated substrate. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The structural formula of the used materials is shown in the following figure:
device example 2-device example 35 referring to the above method, the compounds M1 used in device example 1 were replaced with the compounds M11, M226, M32, M245, M242, M3, M7, M14, M19, M25, M30, M36, M38, M40, M44, M50, M57, M64, M70, M75, M85, M96, M105, M113, M120, M130, M146, M155, M163, M177, M186, M201, M210, respectively, as hole transport layers, to prepare corresponding organic electroluminescent devices.
Device comparative example 1: this comparative example provides an organic electroluminescent device whose fabrication method is the only difference from device example 1 in that the organic electroluminescent device was fabricated by vapor deposition using the existing comparative compound a, b, c, d instead of the hole transport layer (compound M1) in device example 1 described above, respectively, to fabricate device comparative examples 1 to 4. Wherein, the chemical structural formula of the comparative compound a, b, c, d is as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 35 and device comparative examples 1 to 4 were characterized in terms of driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits), and the test results are shown in table 2 below:
TABLE 2
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From the above table, it can be seen that: compared with the organic electroluminescent device prepared by using the comparative compound as the hole transport layer, the organic electroluminescent device prepared by using the organic electroluminescent compound as the hole transport layer has lower starting voltage, and the luminous efficiency and the service life are obviously improved.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.

Claims (4)

1. The hole organic electroluminescent compound is characterized in that the structural general formula of the hole organic electroluminescent compound is shown as the general formula I:
in formula I, X is selected from: a single bond, O, CR or NR, R being an aryl group of C6;
l1, L2 are each independently selected from C6 aryl or C6 heteroaryl, wherein the heteroatom is nitrogen;
ar1-Ar8 are each independently selected from C6-C30 aryl or C6-C30 heteroaryl, wherein the heteroatom is any one of oxygen, nitrogen, sulfur;
cy1-Cy2 are each independently selected from C6 aryl;
n1-n4 represent 0 or 1, respectively, and n1+n2+n3+n4=1 or n1+n2+n3+n4=2.
2. The hole-type organic electroluminescent compound according to claim 1, wherein the structural formula of the hole-type organic electroluminescent compound is represented by general formula a-1, general formula a-2 or general formula a-3:
or, n1+n2+n3+n4=2, and the structural general formula of the hole organic electroluminescent compound is shown as a general formula b-1, a general formula b-2, a general formula b-3 or a general formula b-4:
3. a hole-type organic electroluminescent compound, wherein the hole-type organic electroluminescent compound is selected from any one of the compounds represented by the following structural formulas:
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4. use of a hole class organic electroluminescent compound as claimed in any one of claims 1 to 3 in the preparation of an organic electroluminescent device.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112480115A (en) * 2020-11-30 2021-03-12 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound containing nitrogen heterocycle and preparation method and application thereof
CN113307770A (en) * 2021-05-21 2021-08-27 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material and preparation method and application thereof
CN114716330A (en) * 2022-04-27 2022-07-08 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material, preparation method and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112480115A (en) * 2020-11-30 2021-03-12 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound containing nitrogen heterocycle and preparation method and application thereof
CN113307770A (en) * 2021-05-21 2021-08-27 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material and preparation method and application thereof
CN114716330A (en) * 2022-04-27 2022-07-08 吉林奥来德光电材料股份有限公司 Luminescent auxiliary material, preparation method and application thereof

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