CN117430566A - Compound and light-emitting device - Google Patents

Compound and light-emitting device Download PDF

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Publication number
CN117430566A
CN117430566A CN202311185593.9A CN202311185593A CN117430566A CN 117430566 A CN117430566 A CN 117430566A CN 202311185593 A CN202311185593 A CN 202311185593A CN 117430566 A CN117430566 A CN 117430566A
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independently selected
group
compound
synthesis
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陈少福
王煦
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Abstract

The invention provides a compound and a light-emitting device. The compound disclosed by the invention has the structure disclosed by the formula (1). The compound is formed by connecting substituted alkyl fluorene and nitrogen heterocycle, has the advantages of good optical, electrical and thermal stability, high luminous efficiency, low voltage, long service life and the like, can be used in a light-emitting device, and particularly can be used as a hole blocking layer material and an electron transport layer material, and has the possibility of being applied to AMOLED industry.

Description

Compound and light-emitting device
Technical Field
The present disclosure relates to the field of organic electroluminescent technology, and in particular, to an organic luminescent material suitable for use in a light emitting device, and more particularly, to a compound for connecting substituted alkylfluorene with nitrogen heterocycle and a light emitting device thereof.
Background
Currently, light emitting devices, which are a new generation of display technology, gain more and more attention in terms of display and illumination technologies, and have a very broad application prospect. However, the performance of light emitting devices, such as luminous efficiency, driving voltage, lifetime, etc., is still required to be continuously enhanced and improved, especially OLED devices, as compared with the market demands.
In general, the OLED device has a basic structure in which various organic functional material films with different functions are interposed between metal electrodes, like a sandwich structure, holes and electrons are injected from both electrodes under the driving of current, and after a certain distance, the holes and electrons are recombined in a light emitting layer and released in the form of light or heat, thereby generating light emission of the OLED. However, the organic functional material is a core component of the light emitting device, and thermal stability, photochemical stability, electrochemical stability, quantum yield, film formation stability, crystallinity, color saturation, and the like of the material are all main factors affecting the performance of the device.
Patent document 1 (CN 106132937 a) describesAnd the 9, 9-diphenyl fluorene is bonded to the triazine ring through a connector, and the compounds can be used as electron injection and transmission materials for light-emitting devices, so that the device voltage is high, and meanwhile, the efficiency and the service life are required to be further improved. Patent document 2 (CN 111433190 a) describes +.>The compounds in which cyclohexylfluorene is bonded to triazine ring via a linker are useful as host materials and electron transport materials for light emitting devices, and the device efficiency thereof is to be improved. Patent document 3 (CN 110615759B) describes +.>Adamantylfluorene is bonded to a triazine ring via a linker, and these compounds are used as an electron transport layer material in a light-emitting device, and further improvements in properties such as luminous efficiency and lifetime have been desired. Patent document 4 (CN 114763341 a) describes +.>The norbornyl fluorenyl group is bonded to an azacyclic ring via a linker, and these compounds are used as an electron transport layer material for a light-emitting device, and further improvement in material stability, luminous efficiency, lifetime, and other properties is required. Patent document 5 (KR 1020210156912A) describes +.>Compounds in which benzoheterocyclofluorenyl is bonded to an azacyclic ring via a linker, and which are used as electron transport layer materials for light-emitting devices, have high planarity and high sublimation temperatureThe stability is poor, and the luminous efficiency, the service life and other performances of the device are still to be further improved.
Disclosure of Invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide a high-performance light-emitting device and a novel material capable of realizing such a light-emitting device.
The present applicant has conducted intensive studies to achieve the above object, and as a result, has found that a high-performance light-emitting device can be obtained by using a compound represented by the following formula (1).
One of the purposes of the application is to provide a compound for connecting substituted alkyl fluorene and nitrogen heterocycle, which has the advantages of good film forming property, good photo, electric and thermal stability, high luminous efficiency, low voltage, long service life and the like, and can be used in a light-emitting device. In particular, as a hole blocking layer material and an electron transport layer material, there is a possibility of application to the AMOLED industry.
In order to achieve the above purpose, the present application adopts the following technical scheme:
a compound has a structural formula shown in a formula (1):
wherein X is independently selected from C (R 4 ) 2 、O、S、NR 5 ；
Wherein n is independently selected from 0 or an integer from 1 to 6, and when n=0, is not linked to form a ring; when n is more than or equal to 1, connecting to form a ring; when n is more than or equal to 2, each X is the same or different;
wherein X is 1 、X 2 、X 3 Independently selected from N or CR 6 And at least one is N;
R 1 、R 2 、R 3 is a substituent on each ring and is independently selected from deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxyA group, a C6-C60 aryloxy group, a C3-C40 alkylsilyl group, a C6-C60 arylsilyl group, a C1-C40 alkylboron group, a C6-C60 arylboron group, a C6-C60 arylphosphorus group, a C6-C60 monoarylphosphino group, a C6-C60 diarylphosphino group, or a C6-C60 arylamino group;
R 4 、R 5 、R 6 each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphido, C6-C60 monoarylphosphino, C6-C60 diarylphosphino, or C6-C60 arylamino;
l is selected from a single bond, or an aromatic group or a heteroaromatic group with 6-30 ring atoms which are substituted or unsubstituted;
wherein a, b, c are independently selected from integers from 0 to 8,
wherein Ar is 1 And Ar is a group 2 Independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the heteroatom in each said heteroaryl or heteroalkyl or heterocycloalkyl is independently selected from at least one heteroatom in O, S, N, se, si, ge;
the substitution is substituted by deuterium, F, cl, br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amino, C6-C12 aryl, cyano, isonitrile or phosphino, and the number of substitution of each substituent group is independently selected from one of single substitution to maximum number of substitution.
In some embodiments, a compound selected from structures represented by the following formulas (2), 3);
in some embodiments, in the formulas (1) - (3)Selected from the structures shown in the following formulas A-1 to A-8;
in some embodiments, wherein L is selected from a single bond and structures represented by formulas B-1 through B-18 below;
wherein R is a substituent, each R is independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphorus, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamino;
m is selected from integers from 0 to 4.
In some embodiments, each R is independently selected from deuterium or C1-C4 alkyl.
In some embodiments, wherein X 1 -X 3 Comprises at least two N;
R 1 、R 2 、R 3 each independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphorus, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamino;
R 6 selected from hydrogen, deuterium,Halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphido, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamino.
Wherein X is 1 -X 3 Two of them are N, and the other is CH or N, R 1 、R 2 、R 3 Each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphido, C6-C20 monoarylphosphino, C6-C20 diarylphosphino, or C6-C30 arylamino.
X 1 -X 3 Are all N; r is R 1 、R 2 、R 3 Each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C5-C12 heteroaryl, C1-C10 alkoxy, C6-C12 aryloxy, or C6-C12 arylamino.
In some embodiments, wherein X 1 -X 3 All N, a, b and c are all 0.
In some embodiments, wherein Ar 1 And Ar is a group 2 Each independently selected from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, t-butylphenyl, trideutero methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, phenanthryl, pyrenyl, and,Radical, carbazolyl radicalA pyridinyl group, a pyrimidinyl group, a 4-cyanophenyl group, a 3-cyanophenyl group, a benzophenanthryl group, or a combination of at least two of the foregoing.
As a compound in some embodiments, wherein the structure of formula (1) contains at least one deuterium atom.
As a compound in some embodiments, selected from, but not limited to, the following structures;
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it is also an object of the present invention to provide a light emitting device comprising the above compound, which comprises an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, at least one of the one or more organic layers comprising the compound.
The material is used as a material of at least one layer of a light-emitting layer, a hole blocking layer and an electron transport layer in an organic layer in a light-emitting device.
The material of the present application acts as a hole blocking layer material in a light emitting device.
The light emitting device of the present application may be an organic light emitting device or a quantum dot light emitting device. In some embodiments, when the light emitting device is an organic light emitting device, the compound may be used as a material of a light emitting layer, a hole blocking layer, or an electron transporting layer; when the light emitting device is a quantum dot light emitting device, the compound is used as a material of a hole blocking layer or an electron transporting layer.
In some embodiments the light emitting device is an organic electroluminescent device.
The material has the advantages of good film forming property, good optical, electrical and thermal stability, high luminous efficiency, low voltage, long service life and the like, and can be used in organic light-emitting devices. In particular, as a hole blocking layer material and an electron transport layer material, there is a possibility of application to the AMOLED industry.
Drawings
FIG. 1 is a schematic diagram of compound CPD 108 1 HNMR spectra.
Fig. 2 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
Detailed Description
A compound has a structural formula shown in a formula (1):
wherein X is independently selected from C (R 4 ) 2 、O、S、NR 5 ；
Wherein n is independently selected from 0 or an integer from 1 to 6, and when n=0, is not linked to form a ring; when n is more than or equal to 1, connecting to form a ring; when n is more than or equal to 2, each X is the same or different;
wherein X is 1 、X 2 、X 3 Independently selected from N or CR 6 And at least one is N;
R 1 、R 2 、R 3 each independently selected from deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 monoarylphosphino, C6-C60 diarylphosphino, or C6-C60 arylamino;
R 4 、R 5 、R 6 each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-a C60 aryl group, a C5-C60 heteroaryl group, a C1-C40 alkoxy group, a C6-C60 aryloxy group, a C3-C40 alkylsilyl group, a C6-C60 arylsilyl group, a C1-C40 alkylboryl group, a C6-C60 arylboryl group, a C6-C60 monoarylphosphinyl group, a C6-C60 diarylphosphino group or a C6-C60 arylamino group;
l is selected from a single bond, or an aromatic group or a heteroaromatic group with 6-30 ring atoms which are substituted or unsubstituted;
wherein a, b, c are independently selected from integers from 0 to 8, R 1 、R 2 、R 3 Is substituent on the corresponding ring, and when a, b and c are 0, the position on each corresponding ring is hydrogen without substituent;
wherein Ar is 1 And Ar is a group 2 Independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the heteroatom in the heteroaryl or heteroalkyl or heterocycloalkyl is selected from at least one heteroatom in O, S, N, se, si, ge;
the substitution is substituted by deuterium, F, cl, br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amino, C6-C12 aryl, cyano, isonitrile or phosphino, and the number of substitution of each substituent group is independently selected from one of single substitution to maximum number of substitution.
The examples are merely for the convenience of understanding the technical invention and should not be construed as a specific limitation of the present application.
The starting materials and solvents, etc., involved in the synthesis of the compounds herein are available from suppliers well known to those skilled in the art of Alfa, acros, etc.
Examples:
1. synthetic route for compound CPD 4
Synthesis of Compound CPD 4-3
Compound CPD 4-1 (50.00 g,186.88 mmol) and dry tetrahydrofuran (750 ml) were added to a 2000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, the system was then cooled to-78℃and then n-hexane solution of n-butyllithium (121.47 ml,242.95mmol, concentration 2 mol/L) was added dropwise, the internal temperature of the system was controlled to be not higher than-70℃for 1 hour, and stirring was maintained at-78℃for 1 hour. CPD 4-2 (33.02 g,261.63 mmol) was added in a final portion and stirring was continued for 1.5 hours at-78deg.C, and TLC (ethyl acetate: n-hexane=1:30 as developing agent) monitored for complete consumption of CPD 4-1 starting material, most of CPD 4-3 being formed. Adding deionized water dropwise to quench the reaction (300 ml), heating to room temperature, directly separating liquid, extracting aqueous phase once (500 ml) by ethyl acetate, merging organic phases, concentrating under reduced pressure at 65 ℃ for 1 hour to obtain pale yellow solid, loading the pale yellow solid on a chromatographic column silica gel sample stirring dry method, purifying by silica gel column chromatography (200-300 meshes of silica gel, ethyl acetate: n-hexane=1:30 is used as eluent), concentrating under reduced pressure at 65 ℃ for 1.5 hours after elution to obtain white solid which is CPD 4-3 (38.51 g, purity: 99.78%, yield: 65.45%), and carrying out mass spectrum: 315.15 (M+H).
Synthesis of Compound CPD 4-4
CPD 4-3 (37.00 g,117.52 mmol) and methylene chloride (370 ml) were added to a 1000ml three-necked round bottom flask, the system was cooled to 0℃and trifluoromethanesulfonic acid (35.27 g,235.03 mmol) was added dropwise over 15 minutes, the temperature was maintained and stirred for 30 minutes, and TLC (ethyl acetate: n-hexane=1:30 as developing agent) monitored the reaction and the consumption of CPD 4-3 as a starting material was completed. Adding deionized water dropwise into the system for quenching reaction (100 ml), separating liquid, loading the chromatographic column on the column by a silica gel stirring dry method, performing silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane=1:50 is used as eluent), and concentrating under reduced pressure at 65 ℃ for 2 hours after elution to obtain white solid CPD 4-4 (29.92 g, purity: 99.91%, yield: 85.76%), and mass spectrum: 297.12 (M+H).
Synthesis of Compound CPD 4-6
CPD 4-4 (35.00 g,117.91 mmol), CPD 4-5 (35.93 g,141.49 mmol), tris (dibenzylideneacetone) dipalladium (2.16 g,2.36 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (2.25 g,4.72 mmol), potassium acetate (23.14 g,235.82 mmol) and 1, 4-dioxane (350 ml) were added to a 1000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, and the system was heated to 100deg.C for 2 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane=1:10 as developing agent) and the consumption of the starting material CPD 4-4 was completed. Cooling to 60 ℃, concentrating under reduced pressure to remove the solvent, adding ethyl acetate (800 ml), washing with deionized water (300 ml x 3), separating, loading the chromatographic column on a silica gel column by a dry method, performing silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane=1:15 as eluent), eluting, concentrating under reduced pressure at 65 ℃ for 1 hour to obtain white solid CPD 4-6 (38.95 g, purity: 99.00%, yield: 85.06%), and mass spectrometry: 389.26 (M+H).
Synthesis of Compound CPD 4
CPD 4-7 (20.00 g,47.63 mmol), CPD 4-6 (19.42 g,50.01 mmol), bis (4-dimethylaminophenyl di-tert-butylphosphine) palladium dichloride (0.697 g,0.95 mmol), potassium carbonate (13.16 g,95.26 mmol), toluene (300 ml), ethanol (100 ml), deionized water (100 ml) were added to a 1000ml three port round bottom flask, the vacuum nitrogen was replaced three times, the system was then heated to 65℃for 2 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane=1:10 as the developing reagent) and the consumption of the starting material CPD 4-7 was completed. Cooled to room temperature, methanol (300 ml) was added thereto, and stirred at room temperature for 1 hour, whereby a large amount of solid was precipitated. Toluene (450 ml) is added, the system is heated to 100 ℃ for dissolution, then cooled to room temperature, 300-400 meshes of silica gel (50 g) is filtered once, methanol (450 ml) is added into filtrate at room temperature, stirring is carried out for 1 hour at room temperature, a white solid wet product is obtained through suction filtration, and 25.38g of white solid is obtained through drying at 80 ℃ for 1 hour; the above solid was added to a 100ml single neck round bottom flask, recrystallized once from toluene (254 ml) and methanol (127 ml), suction filtered and the filter cake dried in vacuo at 80℃for 5 hours to give CPD 4 (22.18 g, purity: 99.96%, yield: 72.11%) as a white solid. 22.18g of crude CPD 4 was purified by sublimation to give sublimated pure CPD 4 (17.96 g, purity: 99.97%, yield: 80.98%), mass spectrum: 646.22 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.35-8.33(m,1H),8.30-8.22(m,5H),8.13-8.11(m,1H),8.07(s,1H),8.04-8.00(m,4H),7.92-7.88(m,4H),7.82-7.79(m,1H),7.76-7.73(m,6H),7.69-7.61(m,2H),2.61-2.58(m,2H),2.36-2.30(m,2H),1.91-1.88(m,4H),1.20(s,6H).
2. Synthetic route to compound CPD 34
Synthesis of Compound CPD 34-2
The synthesis and purification method of the reference compound CPD 4-3 only needs to change the corresponding original material to obtain the target compound CPD 34-2 (35.12 g, purity: 99.81%, yield: 66.35%), mass spectrum: 355.12 (M+H).
Synthesis of Compound CPD 34-3
The synthesis and purification method of the reference compound CPD 4-4 only needs to change the corresponding original material to obtain the target compound CPD 34-3 (27.56 g, purity: 99.91%, yield: 84.36%), mass spectrum: 337.42 (M+H).
Synthesis of Compound CPD 34-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD 34-4 (29.64 g, purity: 99.87%, yield: 86.33%), mass spectrum: 429.02 (M+H).
Synthesis of Compound CPD 34
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD 34 (38.45 g, purity: 99.93%, yield: 74.12%). Sublimation purification of 38.45g of crude CPD 34 gave sublimated pure CPD 34 (31.68 g, purity: 99.94%, yield: 82.40%), mass Spectrometry: 610.32 (M+H). 1 HNMR(400MHz,CDCl 3 )δ8.12-8.04(m,2H),8.00(dd,J＝9.6,2.1Hz,1H),7.97-7.89(m,3H),7.79(dd,J＝6.7,1.1Hz,1H),7.73(d,J＝2.0Hz,1H),7.72-7.66(m,2H),7.60-7.55(m,2H),7.55-7.44(m,4H),7.44-7.37(m,3H),7.36-7.27(m,2H),2.38-2.33(m,2H),2.13-2.08(m,2H),1.71(t,J＝6.1Hz,4H),1.52-1.45(m,4H),1.43-1.33(m,6H).
3. Synthesis of Compound CPD 63
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD 63 (32.42 g, purity: 99.94%, yield: 76.32%). Sublimation purification of 32.42g of crude CPD 63 gave sublimated pure CPD 63 (26.02 g, purity: 99.94%, yield: 80.26%), mass spectrum: 570.22 (M+H).
1 H NMR(400MHz,CDCl 3 )δ8.12-8.04(m,4H),8.02(d,J＝7.7Hz,1H),7.97-7.91(m,2H),7.80-7.78(m,1H),7.72-7.64(m,3H),7.55-7.44(m,8H),7.36-7.27(m,2H),2.28-2.22(m,2H),2.02-1.97(m,2H),1.56-1.53(m,4H),1.21(s,6H).
4. Synthesis of Compound CPD 83
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD 83 (28.88 g, purity: 99.95%, yield: 75.00%). 28.88g of crude CPD 83 was purified by sublimation to give sublimated pure CPD 83 (22.80 g, purity: 99.95%, yield: 78.95%), mass spectrum: 570.22 (M+H).
1 H NMR(400MHz,CDCl 3 )δ8.20(t,J＝2.1Hz,1H),8.02(d,J＝7.9Hz,1H),7.90-7.85(m,4H),7.85-7.80(m,2H),7.79-7.77(m,2H),7.64-7.62(m,1H),7.57-7.53(m,1H),7.49-7.42(m,6H),7.36(s,1H),7.36-7.27(m,2H),2.28-2.22(m,2H),2.02-1.97(m,2H),1.56(t,J＝6.3Hz,4H),1.20(s,6H).
5. Synthesis of Compound CPD 90
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD 90 (29.06 g, purity: 99.93%, yield: 76.52%). Sublimation purification of 29.06g of CPD 90 crude product gave sublimated pure CPD 90 (22.56 g, purity: 99.94%, yield: 77.64%), mass Spectrometry: 660.00 (M+H).
1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.12-8.04(m,3H),8.02(d,J＝7.9Hz,1H),7.99-7.89(m,2H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.72(d,J＝2.2Hz,1H),7.67-7.59(m,2H),7.59-7.38(m,7H),7.36(s,1H),7.35-7.27(m,2H),2.28-2.22(m,2H),2.02-1.97(m,2H),1.56(t,J＝6.3Hz,4H),1.22(s,6H).
6. Synthesis of Compound CPD 108
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD 108 (25.11 g, purity: 99.97%, yield: 74.52%). Sublimation purification of 25.11g of crude CPD 108 gave sublimated pure CPD 108 (18.85 g, purity: 99.97%, yield: 75.07%), mass Spectrometry: 646.21 (M+H). 1 H NMR(400MHz,CDCl 3 )δ9.07(s,1H),8.83(d,J＝6.8Hz,5H),8.01(s,1H),7.94-7.91(m,2H),7.87-7.85(m,1H),7.82-7.80(m,1H),7.79-7.56(m,12H),7.41(t,J＝7.3Hz,1H),7.35(t,J＝7.2Hz,1H),1.96(m,2H),1.82(m,6H),1.25(s,6H).
7. Synthetic route to compound CPD 119
Synthesis of Compound CPD 119-3
CPD 119-1 (25.00 g,72.71 mmol), CPD 119-2 (21.97 g,94.53 mmol), tetrakis (triphenylphosphine) palladium (1.68 g,1.45 mmol), potassium carbonate (20.10 g,145.42 mmol), tetrahydrofuran (375 ml), deionized water (125 ml) were added to a 1000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, the system was then heated to 70℃for 4 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane=1:10 as developing agent) and the consumption of the starting CPD 119-1 was completed. Direct concentration to remove solvent, addition of dichloromethane (500 ml), washing with deionized water (150 ml x 3), separation, column chromatography on silica gel column by dry column chromatography (200-300 mesh silica gel, ethyl acetate: n-hexane=1:20 as eluent), concentration at 65 ℃ under reduced pressure for 1 hour after elution gave CPD 119-3 (29.97 g, purity: 99.32%, yield: 83.10%) as a white solid, mass spectrum: 496.20 (M+H).
Synthesis of Compound CPD 119
CPD 119-3 (25.00 g,50.40 mmol), CPD 4-6 (23.49 g,60.48 mmol), tris (dibenzylideneacetone) dipalladium (0.92 g,1.00 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.95 g,2.00 mmol), cesium carbonate (35.56 g,100.80 mmol), toluene (375 ml), ethanol (125 ml), deionized water (125 ml) were added to a 2000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, and then the system was heated to 90℃for 12 hours, and TLC (ethyl acetate: n-hexane=1:10 as developing agent) was monitored for complete consumption of CPD 119-3. Cooled to room temperature, methanol (300 ml) was added thereto, and stirred at room temperature for 1 hour, whereby a large amount of solid was precipitated. Toluene (500 ml) is added, the system is heated to 120 ℃ for heating and dissolving, then cooled to room temperature, 300-400 meshes of silica gel (60 g) is filtered once, methanol (200 ml) is added into filtrate at room temperature, stirring is carried out for 1 hour at room temperature, a white solid wet product is obtained through suction filtration, and 30.68g of white solid is obtained through drying at 100 ℃ for 1 hour; the above solid was added to a 1000ml single neck round bottom flask, recrystallized once from toluene (301 ml) and methanol (154 ml), suction filtered and the filter cake was dried in vacuo at 100℃for 12 hours to give CPD 119 (27.65 g, purity: 99.94%, yield: 76.00%) as a white solid. Sublimation purification of 27.65g of crude CPD 119 gave sublimated pure CPD 119 (22.55 g, purity: 99.94%, yield: 81.56%), mass spectrum: 722.32 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.12(t,J＝1.8Hz,1H),8.10-8.04(m,2H),8.02(d,J＝7.9Hz,1H),7.90-7.82(m,2H),7.81-7.75(m,2H),7.71(t,J＝2.2Hz,1H),7.65-7.63(m,1H),7.58-7.54(m,7H),7.52-7.46(m,4H),7.42(d,J＝1.9Hz,1H),7.41-7.36(m,3H),7.36-7.27(m,3H),2.28-2.22(m,2H),2.04-1.98(m,2H),1.58(t,J＝6.3Hz,4H),1.19(s,6H).
8. Synthetic route to compound CPD 128
Synthesis of Compound CPD 128-3
The synthesis and purification method of the reference compound CPD 119-3 only needs to change the corresponding original material to obtain the target compound CPD 128-3 (30.05 g, purity: 99.23%, yield: 82.78%), mass spectrum: 358.10 (M+H). Synthesis of Compound CPD 128-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD 128-4 (34.66 g, purity: 98.09%, yield: 85.74%), mass spectrum: 450.20 (M+H).
Synthesis of Compound CPD 128-6
The synthesis and purification method of the reference compound CPD 119-3 only needs to change the corresponding original material to obtain the target compound CPD 128-6 (28.41 g, purity: 99.52%, yield: 85.09%), mass spectrum: 448.14 (M+H).
Synthesis of Compound CPD 128
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 128 (16.01 g, purity: 99.93%, yield: 76.00%). Sublimation purification of 16.01g of crude CPD 128 gave sublimated pure CPD 128 (12.79 g, purity: 99.95%, yield: 79.89%), mass Spectrometry: 674.36 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.12-8.05(m,5H),8.02(d,J＝7.9Hz,1H),7.86-7.84(m,1H),7.81-7.75(m,3H),7.60-7.58(m,1H),7.55-7.44(m,7H),7.38-7.27(m,5H),2.40(s,6H),2.28-2.21(m,2H),2.03-1.96(m,2H),1.58(t,J＝6.3Hz,4H),1.19(s,6H).
9. Synthetic route to compound CPD 136
Synthesis of Compound CPD 136-2
The synthesis and purification method of the reference compound CPD 119-3 only needs to change the corresponding original material to obtain the target compound CPD 136-2 (45.61 g, purity: 99.46%, yield: 80.00%), mass spectrum: 510.13 (M+H).
Synthesis of Compound CPD 136
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 136 (27.13 g, purity: 99.95%, yield: 75.19%). Sublimation purification of 27.13g of crude CPD 136 gave sublimated pure CPD 136 (21.28 g, purity: 99.95%, yield: 78.44%), mass spectrum: 736.42 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.12-7.99(m,4H),7.90-7.83(m,2H),7.81-7.75(m,2H),7.71(t,J＝2.2Hz,1H),7.65-7.59(m,2H),7.58-7.53(m,4H),7.53-7.46(m,5H),7.45-7.41(m,2H),7.38-7.23(m,4H),2.26-2.21(m,2H),2.04-1.97(m,2H),1.58(t,J＝6.3Hz,4H),1.20(s,6H).
10. Synthetic route to compound CPD 160
Synthesis of Compound CPD 160-2
The synthesis and purification method of the reference compound CPD 4-3 only needs to change the corresponding original material to obtain the target compound CPD 160-2 (32.56 g, purity: 99.51%, yield: 66.85%), mass spectrum: 357.02 (M+H).
Synthesis of Compound CPD 160-3
The synthesis and purification method of the reference compound CPD 4-4 only needs to change the corresponding original material to obtain the target compound CPD 160-3 (28.02 g, purity: 99.90%, yield: 83.65%), mass spectrum: 339.14 (M+H).
Synthesis of Compound CPD 160-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD 160-4 (30.67 g, purity: 99.90%, yield: 86.23%), mass spectrum: 431.22 (M+H).
Synthesis of Compound CPD 160-6
The synthesis and purification method of the reference compound CPD 119-3 only needs to change the corresponding original material to obtain the target compound CPD 160-6 (28.06 g, purity: 99.42%, yield: 82.00%), mass spectrum: 420.32 (M+H).
Synthesis of Compound CPD 160
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 160 (22.96 g, purity: 99.96%, yield: 76.48%). 22.96g of crude CPD 160 was purified by sublimation to give sublimated pure CPD 160 (18.25 g, purity: 99.96%, yield: 79.49%), mass spectrum 688.32 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.12-8.04(m,4H),7.97-7.91(m,2H),7.81-7.75(m,2H),7.72 -7.64(m,3H),7.60-7.44(m,10H),7.38-7.28(m,4H),3.53-3.50(m,4H),2.39-2.34(m,2H),2.14-2.08(m,2H),1.69(t,J＝6.2Hz,4H),1.50-1.44(m,4H).
11. Synthetic route for compound CPD 179
Synthesis of Compound CPD 179-2
The synthesis and purification method of the reference compound CPD 119-3 only need to change the corresponding original material, so as to obtain the target compound CPD 179-2 (25.33 g, purity: 99.89%, yield: 82.96%), mass spectrum: 496.16 (M+H).
Synthesis of Compound CPD 179
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 179 (24.63 g, purity: 99.94%, yield: 73.56%). Sublimation purification of 24.63g of crude CPD 179 gave sublimated pure CPD 179 (20.82 g, purity: 99.96%, yield: 84.54%), mass Spectrometry 722.30 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.12-8.04(m,4H),8.02(d,J＝7.9Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.71(t,J＝2.2Hz,2H),7.65-7.62(m,1H),7.60-7.55(m,5H),7.53-7.45(m,8H),7.36(s,1H),7.36-7.28(m,3H),2.29-2.21(m,2H),2.01-1.96(m,2H),1.57(t,J＝6.3Hz,4H),1.20(s,6H).
12. Synthetic route for compound CPD 223
Synthesis of Compound CPD 223-3
Compound CPD 223-1 (50.00 g,177.60 mmol) and dry tetrahydrofuran (750 ml) were added to a 2000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, the system was cooled to-78deg.C, then n-hexane solution of n-butyllithium (97.68 ml,195.36mmol, concentration 2 mol/L) was added dropwise, the internal temperature of the system was controlled to be not higher than-70deg.C, after the dropwise addition was completed, and stirring was maintained at-78deg.C for 1 hour. CPD 223-2 (38.89 g,266.40 mmol) was slowly added dropwise, and after the addition was completed, the mixture was stirred for 1 hour at a natural temperature, and TLC (ethyl acetate: n-hexane=1:10 as developing agent) was used to monitor the consumption of CPD 223-1, and most of CPD 223-3 was produced. The system was quenched by dropping aqueous hydrochloric acid (2 mol/L,100 ml) to precipitate a large amount of solid, stirring at room temperature for 1 hour, suction-filtering to obtain a white solid, beating with n-hexane (100 ml) at room temperature for 1 hour, suction-filtering, and vacuum-drying the filter cake at 65℃for 3 hours to obtain CPD 223-3 (36.84 g, purity: 98.06%, yield: 84.16%) as a white solid, mass spectrum: 247.04 (M+H).
Synthesis of Compound CPD 223-4
The synthesis and purification method of the reference compound CPD 119-3 only needs to change the corresponding original material to obtain the target compound CPD 223-4 (27.80 g, purity: 99.54%, yield: 78.96%), mass spectrum: 434.26 (M+H).
Synthesis of Compound CPD 223
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 223 (23.30 g, purity: 99.96%, yield: 76.60%). Sublimation purification of 23.30g of CPD 223 crude product gave sublimated pure CPD 223 (18.64 g, purity: 99.96%, yield: 80.00%), mass Spectrometry 660.20 (M+H). 1 H NMR(400MHz,CDCl3)δ8.17(d,J＝2.7Hz,1H),8.12-8.03(m,6H),7.92 -7.85(m,2H),7.81-7.74(m,2H),7.68(dd,J＝7.8,2.1Hz,1H),7.58-7.44(m,8H),7.38 -7.28(m,3H),2.28-2.21(m,2H),2.00-1.96(m,2H),1.56(t,J＝6.3Hz,4H),1.21(s,6H).
13. Synthetic route to compound CPD 255
Synthesis of Compound CPD 255-3
According to the method for synthesizing and purifying the compound CPD 4, only the corresponding original materials are required to be changed, the reaction solvent is toluene and deionized water, and the reaction is carried out for 8 hours at 90 ℃ to obtain the target compound CPD 255-3 (18.24 g, purity: 99.67%, yield: 67.15%), and mass spectrum: 354.12 (M+H).
Synthesis of Compound CPD 255
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 255 (18.31 g, purity: 99.94%, yield: 74.52%). Sublimation purification of 18.31g of crude CPD 255 gave sublimated pure CPD 255 (14.85 g, purity: 99.96%, yield: 81.11%), mass spectrum 580.34 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.02(d,J＝7.8Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.65-7.63(m,1H),7.57-7.53(m,1H),7.49-7.46(m,1H),7.38-7.27(m,3H),2.27-2.21(m,2H),2.00-1.95(m,2H),1.54(t,J＝6.3Hz,4H),1.21(s,6H).
14. Synthetic route for compound CPD 262
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Synthesis of Compound CPD 262-1
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD 262-1 (20.33 g, purity: 99.75%, yield: 67.15%), mass spectrum: 446.22 (M+H).
Synthesis of Compound CPD 262-3
The synthesis and purification method of the reference compound CPD 4 only needs to change the corresponding original material to obtain the target compound CPD 262-3 (13.56 g, purity: 99.89%, yield: 78.06%), mass spectrum: 430.14 (M+H).
Synthesis of Compound CPD 262
The synthesis and purification method of the reference compound CPD 119 were carried out by changing the corresponding starting material to obtain the objective compound CPD 262 (14.36 g, purity: 99.96%, yield: 78.47%). Sublimation purification of 14.36g of crude CPD 262 gave sublimated pure CPD 262 (11.01 g, purity: 99.96%, yield: 76.68%), mass Spectrometry 656.34 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.02(d,J＝7.8Hz,1H),7.8-7.77(m,3H),7.71(t,J＝2.2Hz,1H),7.65-7.63(m,1H),7.60-7.52(m,3H),7.52-7.43(m,2H),7.36 -7.27(m,3H),2.26-2.21(m,2H),2.00-1.96(m,2H),1.57(t,J＝6.3Hz,4H),1.19(s,6H).
15. Synthetic route to compound CPD 266
Synthesis of Compound CPD 266-1
CPD 4-2 (50.00 g,396.20 mmol), anhydrous potassium carbonate (54.76 g,396.20 mmol) and heavy water (500 g) were added into a 1000ml three-necked round bottom flask, vacuum nitrogen was replaced three times, the system was closed for reaction, then the system was heated to 80℃for 48 hours, the reaction was monitored by GC-MS and hydrogen spectrum, and the consumption of the raw material CPD 4-2 was completed.
Cooled to room temperature, the organic phase was separated directly into dichloromethane (200 ml), a 300-400 mesh column was applied and suction filtered through silica gel (60 g), the filtrates were combined and concentrated under reduced pressure at 50℃for 3 hours to give CPD 266-1 (20.33 g, purity: 99.90%, deuteration of four D99%, yield: 80.74%) as a colorless liquid, mass spectrum: 131.12 (M+H).
Synthesis of Compound CPD 266-2
The synthesis and purification method of the reference compound CPD 4-3 only needs to change the corresponding original material to obtain the target compound CPD 266-2 (39.61 g, purity: 99.77%, yield: 64.71%), mass spectrum: 319.16 (M+H).
Synthesis of Compound CPD 266-3
The synthesis and purification method of the reference compound CPD 4-4 only needs to change the corresponding original material to obtain the target compound CPD 266-3 (28.42 g, purity: 99.90%, yield: 86.06%), mass spectrum: 301.02 (M+H).
Synthesis of Compound CPD 266-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD 266-4 (26.52 g, purity: 99.01%, yield: 81.33%), mass spectrum: 393.22 (M+H).
Synthesis of Compound CPD 266
The synthesis and purification method of the reference compound CPD 119-3 were carried out by changing the corresponding starting material to obtain the objective compound CPD 266 (24.50 g, purity: 99.97%, yield: 76.12%). Sublimation purification of 24.50g of crude CPD 266 gave sublimated pure CPD 266 (19.28 g, purity: 99.97%, yield: 78.70%), mass Spectrometry 650.24 (M+H). 1 H NMR(400MHz,CDCl 3 )δ8.21(t,J＝2.1Hz,1H),8.16(d,J＝7.7Hz,1H),8.12-8.04(m,4H),8.00-7.95(m,1H),7.86-7.75(m,3H),7.7 -7.64(m,2H),7.60 -7.44(m,12H),7.35-7.29(m,1H),2.22-2.12(m,4H),1.22(s,6H).
16. Synthetic route to compound CPD274
Synthesis of Compound CPD274-2
The synthesis and purification method of the reference compound CPD 4-3 only needs to change the corresponding original material to obtain the target compound CPD274-2 (36.41 g, purity: 99.52%, yield: 62.22%), mass spectrum: 327.16 (M+H).
Synthesis of Compound CPD274-3
The synthesis and purification method of the reference compound CPD 4-4 only need to change the corresponding original material, so as to obtain the target compound CPD274-3 (27.41 g, purity: 99.89%, yield: 83.45%), mass spectrum: 309.12 (M+H).
Synthesis of Compound CPD274-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD274-4 (32.41 g, purity: 98.89%, yield: 86.56%), mass spectrum: 401.26 (M+H).
Synthesis of Compound CPD 274-7
CPD 274-5 (25.00 g,57.43 mmol), CPD 274-6 (12.98 g,63.17 mmol), 1-bis (diphenylphosphine) dicyclopentadienyl iron palladium dichloride (0.841 g,1.15 mmol), potassium carbonate (15.87 g,114.86 mmol), toluene (375 ml), ethanol (125 ml), deionized water (125 ml) were added to a 1000ml three-necked round bottom flask, the vacuum nitrogen was replaced three times, the system was then heated to 60℃for 4 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane=1:10 as a developing agent) and the consumption of the starting material CPD 274-5 was completed. Cooled to room temperature, methanol (300 ml) was added thereto, and stirred at room temperature for 1 hour, whereby a large amount of solid was precipitated. Toluene (600 ml) is added, the system is heated to 100 ℃ for dissolution, then cooled to room temperature, 300-400 meshes of silica gel (60 g) is filtered once, methanol (450 ml) is added into filtrate at room temperature, stirring is carried out for 1 hour at room temperature, a white solid wet product is obtained through suction filtration, and 21.63g of white solid is obtained through drying at 80 ℃ for 1 hour; the above solid was added to a 500ml single neck round bottom flask, recrystallized once from tetrahydrofuran (130 ml) and methanol (130 ml), suction filtered and the filter cake dried in vacuo at 80℃for 8 hours to give CPD 274-7 (18.72 g, purity: 99.51%, yield: 75.12%) as a white solid, mass spectrum: 433.14 (M+H).
Synthesis of Compound CPD274
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD274 (15.69 g, purity: 99.95%, yield: 75.41%). Sublimation purification of 15.69g of crude CPD274 gave sublimated pure CPD274 (12.55 g, purity: 99.95%, yield 79.99%), mass Spectrometry 672.20 (M+H). 1 HNMR(400MHz,CDCl 3 )δ8.18(t,J＝2.2Hz,1H),8.11-8.04(m,4H),8.02(d,J＝7.9Hz,1H),7.93(d,J＝2.4Hz,1H),7.87-7.85(m,1H),7.80-7.77(m,2H),7.60-7.55(m,2H),7.55-7.43(m,8H),7.38-7.32(m,2H),7.32-7.27(m,2H),2.41(d,J＝1.0Hz,3H),2.35-2.31(m,2H),2.10-2.05(m,2H),1.61(t,J＝5.4Hz,4H),1.53-1.51(m,6H).
17. Synthetic route to compound CPD276
Synthesis of Compound CPD276-2
The synthesis and purification method of the reference compound CPD 4-3 only needs to change the corresponding original material to obtain the target compound CPD276-2 (32.0 g, purity: 99.63%, yield: 63.52%), mass spectrum: 370.12 (M+H).
Synthesis of Compound CPD276-3
The synthesis and purification method of the reference compound CPD 4-4 only needs to change the corresponding original material to obtain the target compound CPD276-3 (25.14 g, purity: 99.68%, yield: 82.63%), mass spectrum: 352.18 (M+H).
Synthesis of Compound CPD276-4
The synthesis and purification method of the reference compound CPD 4-6 only needs to change the corresponding original material to obtain the target compound CPD276-4 (26.84 g, purity: 98.53%, yield: 83.59%), mass spectrum: 444.26 (M+H).
Synthesis of Compound CPD276
The synthesis and purification method of the reference compound CPD 4 were carried out by changing the corresponding starting material to obtain the objective compound CPD276 (16.87 g, purity: 99.94%, yield: 73.52%). Sublimation purification of 16.87g of crude CPD276 gave sublimated pure CPD276 (13.26 g, purity: 99.95%, yield 78.61%), mass Spectrometry 715.32 (M+H). 1 HNMR(400MHz,CDCl 3 )δ8.18(t,J＝2.1Hz,1H),8.12-8.04(m,4H),8.02(d,J＝7.9Hz,1H),7.93(d,J＝2.4Hz,1H),7.87-7.85(m,1H),7.81-7.75(m,2H),7.62-7.41(m,10H),7.37-7.29(m,4H),2.54-2.49(m,4H),2.41(s,3H),2.39-2.34(m,2H),2.33(s,3H),2.14-2.08(m,2H),1.78(t,J＝6.2Hz,4H),1.57-1.52(m,4H).
Application example: fabrication of organic electroluminescent device
As shown in fig. 2, the organic electroluminescent device includes a glass substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4 (HTL 1), a second hole transport layer 5 (HTL 2), a light emitting layer 6, a hole blocking layer 7 (HBL), an electron transport layer 8 (ETL), and a cathode 9, which are stacked.
The preparation method of the organic electroluminescent device comprises the following steps:
ultrasonic cleaning glass substrate 1 with ITO (100 nm) transparent electrode (anode 2 and cathode 9) 50mm by 1.0mm in ethanol for 10 min, oven drying at 150deg.C, and processing with N 2 Plasma treatment for 30 minutes. The washed glass substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, a compound HATCN was deposited on the surface of the transparent electrode line so as to cover the transparent electrode line, to form a thin film (hole injection layer 3) having a film thickness of 5nm, then, a thin film having a film thickness of 60nm was deposited as HTL1 (first hole transport layer 4) by vapor deposition of HTM1, a thin film having a film thickness of 10nm was deposited as HTL2 (second hole transport layer 5) by vapor deposition of HTM2 on the thin film of HTM1, and then, a host material and a guest material (the weight ratio of host material to dopant material is 98%: 2%) were deposited on the thin film of HTM2 by co-vapor deposition to form a light-emitting layer 6 having a film thickness of 25 nm. A hole blocking layer 7 (HBL) with a film thickness of 5nm and an electron transport layer 8 with a film thickness of 350nm are sequentially formed on a light-emitting layer by adopting an evaporation method, wherein the material of the hole blocking layer is the compound or the contrast compound, and the material of the electron transport layer is the electron transport layer material ETL or the compound: liQ (weight ratio 1:1). Then, mg/Ag (100 nm, 1:9) was evaporated as cathode material using co-evaporation mode.
Evaluation:
the above devices were subjected to device performance testing, and in each of examples and comparative examples, a constant current power supply (Keithley 2400) was used, a constant current density was used to flow through the light emitting element, and the emission spectrum was tested using both spectroscopic radiation (CS 2000). At the same time, the current density is 10mA/cm 2 The device voltage value, efficiency and test luminance were measured for a time (LT95). The results are shown in Table 1 below:
table 1:
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as can be seen from the comparison of the data in the above tables, the application of the compounds of the present application to organic electroluminescent devices as hole blocking layer materials and electron transport layer materials shows superior performance in terms of driving voltage, luminous efficiency and device lifetime as compared with the comparison compounds.
The results show that the compound has the advantages of good optical, electrical and thermal stability, high luminous efficiency, low voltage, long service life and the like, and can be used in organic light-emitting devices. In particular, as a hole blocking layer material and an electron transport layer material, there is a possibility of application to the AMOLED industry.

Claims (16)

1. A compound has a structural formula shown in a formula (1):
wherein X is independently selected from C (R 4 ) 2 、O、S、NR 5 ；
Wherein n is independently selected from 0 or an integer from 1 to 6, and when n=0, is not linked to form a ring; when n is more than or equal to 1, connecting to form a ring; when n is more than or equal to 2, each X is the same or different;
wherein X is 1 、X 2 、X 3 Independently selected from N or CR 6 And at least one is N;
R 1 、R 2 、R 3 each independently selected from deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphido, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamino groups;
R 4 、R 5 、R 6 is a substituent on each ring and is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphorus, C6-C60 monoarylphosphine, C6-C60 diarylphosphine, and C6-C60 arylamine;
l is selected from a single bond, or an aromatic group or a heteroaromatic group with 6-30 ring atoms which are substituted or unsubstituted;
wherein a, b, c are independently selected from integers from 0 to 8,
wherein Ar is 1 And Ar is a group 2 Independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the heteroatom in the heteroaryl or heteroalkyl or heterocycloalkyl is selected from at least one heteroatom in O, S, N, se, si, ge;
the substitution is substituted by deuterium, F, cl, br, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted amino, C6-C12 aryl, cyano, isonitrile or phosphino, and the number of substitution of each substituent group is independently selected from one of single substitution to maximum number of substitution.
2. A compound according to claim 1, selected from one of structures represented by the following formulas (2) and (3);
3. a compound according to claim 2, wherein in said formulae (1) to (3)Selected from one of the structures represented by the following formulas A-1 to A-8;
4. a compound according to claim 1, wherein L in said formula (1) is selected from a single bond and one of structures represented by the following formulae B-1 to B-18;
wherein each R is independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphido, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamino, and m is selected from integers of 0 to 4.
5. A compound according to claim 4, wherein each R is independently selected from deuterium or C1-C4 alkyl.
6. According to claimA compound according to claim 3, wherein X 1 -X 3 Comprises at least two N, R 1 、R 2 、R 3 Each independently selected from deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphorus, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamino;
R 6 selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphorus, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamino.
7. A compound according to claim 6, wherein X 1 -X 3 Two of them are N, and the other is CH or N, R 1 、R 2 、R 3 Each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphido, C6-C20 monoarylphosphino, C6-C20 diarylphosphino, or C6-C30 arylamino.
8. A compound according to claim 7, wherein X 1 -X 3 Are all N; r is R 1 、R 2 、R 3 Each independently selected from deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C5-C12 heteroaryl, C1-C10 alkoxy, C6-C12 aryloxy, or C6-C12 arylamino.
9. A compound according to claim 8, wherein X 1 -X 3 All N, a, b and c are all 0.
10. A compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, t-butylphenyl, trideutero methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, phenanthryl, pyrenyl, and,A group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a 4-cyanophenyl group, a 3-cyanophenyl group, a benzophenanthryl group, or a combination of at least two of the foregoing.
11. A compound according to any one of claims 1 to 10, wherein formula (1) contains at least one deuterium atom.
12. A compound according to claim 1, selected from one of the following structures;
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13. a light-emitting device comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, at least one of the organic layers comprising the compound of any one of claims 1-12.
14. A light-emitting device according to claim 13, wherein the compound according to any one of claims 1 to 12 is used as a material in any one of a light-emitting layer, a hole-blocking layer, and an electron-transporting layer in an organic layer.
15. A light emitting device according to claim 14, the compound of any one of claims 1-12 being a hole blocking layer material.
16. A light emitting device according to any one of claims 13-15, which is an organic electroluminescent device.
CN202311185593.9A 2023-06-27 2023-09-14 Compound and light-emitting device Pending CN117430566A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110785401A (en) * 2017-06-14 2020-02-11 株式会社斗山 Organic compound and organic electroluminescent element comprising same
TW202120520A (en) * 2019-11-25 2021-06-01 大陸商廣東阿格蕾雅光電材料有限公司 A compound and its application
CN113717056A (en) * 2020-05-25 2021-11-30 广东阿格蕾雅光电材料有限公司 Compound and application thereof
CN115093332A (en) * 2021-07-01 2022-09-23 四川阿格瑞新材料有限公司 Spiro compound and application thereof
CN115322189A (en) * 2021-09-28 2022-11-11 四川阿格瑞新材料有限公司 Spiro compound and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110785401A (en) * 2017-06-14 2020-02-11 株式会社斗山 Organic compound and organic electroluminescent element comprising same
TW202120520A (en) * 2019-11-25 2021-06-01 大陸商廣東阿格蕾雅光電材料有限公司 A compound and its application
CN113717056A (en) * 2020-05-25 2021-11-30 广东阿格蕾雅光电材料有限公司 Compound and application thereof
CN115093332A (en) * 2021-07-01 2022-09-23 四川阿格瑞新材料有限公司 Spiro compound and application thereof
CN115322189A (en) * 2021-09-28 2022-11-11 四川阿格瑞新材料有限公司 Spiro compound and application thereof

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