CN113045585A - Organic fused ring compound and preparation method and application thereof - Google Patents

Organic fused ring compound and preparation method and application thereof Download PDF

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CN113045585A
CN113045585A CN202110281282.7A CN202110281282A CN113045585A CN 113045585 A CN113045585 A CN 113045585A CN 202110281282 A CN202110281282 A CN 202110281282A CN 113045585 A CN113045585 A CN 113045585A
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王辉
王猛
魏忠义
仲维明
段伟伟
李龙
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic fused ring compound, which has a structure shown in formula 1:
Figure DDA0002978530150000011
wherein X and Y are selected from O or N, and the number of N is 1; r1 represents unsubstituted, mono-, di-or trisubstituted; r2 and R3 are unsubstituted, mono-or di-substituted; ar (Ar)1，Ar2Each independently represents a single substituent.

Description

Organic fused ring compound and preparation method and application thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic fused ring compound and a preparation method and application thereof.
Background
An Organic Light Emitting Device (OLED) is generally composed of a cathode, an anode, and organic layers interposed between the cathode and the anode, that is, the device is composed of a transparent ITO anode, a hole injection layer (ETL), a Hole Transport Layer (HTL), a light Emitting Layer (EL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode, and 1 to 2 organic layers may be omitted as needed. The OLED has the action mechanism that voltage is formed between two electrodes, electrons are injected from a cathode on one side, holes are injected from an anode on the other side, the electrons and the holes are recombined in a light-emitting layer to form an excited state, the excited state is excited to return to a stable ground state, and the device emits light.
The inherent properties of organic materials, such as flexibility, can make them well suited for particular applications, such as fabrication on flexible substrates. Organic opto-electronic devices include organic light emitting devices, organic phototransistors, organic photovoltaic cells, organic photodetectors, and the like, for which the properties of the organic material may be advantageous over conventional materials, e.g., the wavelength at which the organic emissive layer emits light can generally be readily tuned with appropriate dopants, the organic film will emit light when a voltage is applied to the device, and the organic light emitting devices may also be used in flat panel displays, lighting, backlighting, and the like. Accordingly, organic light emitting devices have been widely researched, developed, and used in various fields.
At present, the materials of organic light-emitting devices mainly have the technical problem of short service life, and the materials have low luminous efficiency, low power efficiency and high driving voltage, so that the use cost of the materials is increased, and the later use of the materials has great obstacles to the development of the market.
Therefore, the development of a new organic fused ring compound to prepare an organic electroluminescent device with low driving voltage, high luminous efficiency and long service life is a technical problem which needs to be solved by the people in the field.
Disclosure of Invention
In view of the above, the present invention provides an organic fused ring compound having advantages of high light emitting efficiency, low driving voltage, and long lifetime.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic fused ring compound having a structure represented by formula 1:
Figure BDA0002978530140000021
wherein X and Y are selected from O or N, and the number of N is 1;
r1 represents unsubstituted, mono-, di-or trisubstituted; r2 and R3 are unsubstituted, mono-or di-substituted; ar (Ar)1，Ar2Each independently represents a single substituent.
Preferably, R1, R2 and R3 are at least one of substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C4-C12 aromatic heterocyclic groups.
Preferably, the C1-C8 alkyl is C1-C8 straight-chain alkyl or branched-chain alkyl;
the C3-C15 cycloalkyl is any one of monocycloalkyl, polycycloalkyl and spiro alkyl;
the C6-C18 aryl group is a monocyclic group or a polycyclic group, and the polycyclic group has a plurality of rings in which two carbons are common to two adjoining rings, wherein at least one of the rings is an aromatic ring, and the other rings are at least one of cycloalkyl, cycloalkenyl, aryl, heteroaryl;
the C4-C12 aromatic heterocyclic group is any one of furan, thiophene and pyridine.
Preferably, the carbon atom of the C3-C15 cycloalkyl is substituted by at least one heteroatom, and the heteroatom is at least one of N, O, S, Si, Se and Ge.
Preferably, the C1-C8 alkyl is one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl;
the C3-C15 cycloalkyl is any one of cyclopropyl, cyclopentyl, cyclohexyl and adamantylamine; the heteroatom is at least one of N, O, S;
the C6-C18 aryl is any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene and pyrene.
Preferably, Ar is1Independently represent a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-60 membered aromatic heterocyclic group;
Ar2as shown in formula II or formula III; a first host material when formula II and a second host material when formula III;
Figure BDA0002978530140000031
wherein the content of the first and second substances,
Figure BDA0002978530140000032
is a radical junction;
l1 and L2 each independently represent any one of a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, and a substituted or unsubstituted (C3-C30) cycloalkylene group;
wherein Ar is3，Ar4Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or unsubstituted mono or di (C1-C30) alkylamino, substituted or unsubstituted mono or di (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
Ar5represents a substituted or unsubstituted 3-30 membered heteroaryl group.
Preferably, Ar is5Is a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substitutedOr any one of unsubstituted triazinyl and substituted or unsubstituted pyrimidyl.
Preferably, the organic fused ring compound includes compounds represented by the following C-1-001 to C-2-104:
Figure BDA0002978530140000041
Figure BDA0002978530140000051
Figure BDA0002978530140000061
Figure BDA0002978530140000071
Figure BDA0002978530140000081
Figure BDA0002978530140000091
Figure BDA0002978530140000101
a method for preparing a fused ring compound comprising the steps of:
1) under the protection of inert gas, mixing the compound A, the compound B, an alkaline substance and a mixed solvent I of toluene, ethanol and water, adding a catalyst, and then carrying out heating reaction;
2) after the reaction is finished, carrying out suction filtration, washing, drying, column chromatography and rotary evaporation and concentration to obtain an organic fused ring compound C shown in the formula I;
the synthetic route is as follows:
Figure BDA0002978530140000111
wherein Ar is3Is one of the halogen groups;
X，Y，R1，R2，R3，Ar1，Ar2and X, Y, R1, R2, R3, Ar of claim 71，Ar2。
Preferably, the catalyst selected is tetrakis (triphenylphosphine) palladium, and the molar ratio of tetrakis (triphenylphosphine) palladium to compound a is (0.005-0.05): 1;
the alkaline substance is potassium carbonate or sodium carbonate; the molar ratio of the compound A to the alkaline substance is 1 (1.2-2.0);
the molar ratio of the compound A to the compound B is 1 (1.1-1.5);
the heating reaction temperature is 70-90 ℃, and the reaction time is 20-30 h;
the solvent I is a mixed solvent of toluene, ethanol and water, and the volume ratio of the toluene, the ethanol and the water is 2:1: 1;
the ratio of the compound A to the solvent is 50mmol (350-400) mL;
the detergent is one or a mixture of water, absolute ethyl alcohol and petroleum ether;
the drying temperature is 70-80 ℃, and the drying time is more than or equal to 8 hours;
the column chromatography uses the mixture of dichloromethane and petroleum ether as a solvent and adopts silica gel column chromatography.
The condensed ring compound prepared by the preparation method is applied to the preparation of organic electroluminescent devices.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1: preparation of luminescent Compound C-1-005
Under the protection of nitrogen, weighing and placing compound A-1-005(27.04mmol, 10.0g), B-1-005(32.45mmol, 14.32g) and potassium carbonate (40.56mmol, 5.6g) into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solid is separated out, so that the bridging ligand C-1-005(10.1g, the yield is 51.1%) in yellow powder is obtained.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 4, purifying the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000121
the detection analysis of the obtained compound C-1-005 showed the following results:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 730.26; the test value was 730.87.
Elemental analysis:
the calculated values are: c: 87.10 percent; h: 4.69 percent; n: 3.83 percent; o: 4.38 percent;
the test values are: c: 87.11 percent; h: 4.68 percent; n: 3.84 percent; o: 4.37 percent;
as can be seen from the above test results, example 1 produces a compound of C-1-005 structure with high purity.
Example 2: preparation of luminescent Compound C-1-027
Under the protection of nitrogen, compound A-1-027(27.04mmol, 10.0g), B-1-027(32.45mmol, 13.93g) and potassium carbonate (40.56mmol, 5.6g) were weighed out and placed in a reaction system, a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water was added, under the protection of nitrogen, tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) was added, and under the protection of nitrogen, the mixture was heated under reflux at 80 ℃ for 24 hours. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solid is separated out, so that the bridging ligand C-1-027(10.21g, the yield is 52.53%) is obtained in a yellow powder shape.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 3, purifying the eluent by using the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000131
the compound C-1-027 obtained was analyzed by detection, and the results were as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 718.23; the test value was 718.81.
Elemental analysis:
the calculated values are: c: 85.22 percent; h: 4.21 percent; n: 3.90 percent; o: 6.68 percent;
the test values are: c: 85.23 percent; h: 4.22 percent; n: 3.91 percent; o: 6.65 percent;
as can be seen from the above test results, example 2 prepared a compound of C-1-027 structure with high purity.
Example 3: preparation of luminescent Compound C-1-039
Under the protection of nitrogen, weighing the compound A-1-039(27.04mmol, 10.0g), B-1-039(32.45mmol, 16.08g) and potassium carbonate (40.56mmol, 5.6g), putting into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solid is separated out, so that the bridging ligand C-1-039(11.11g, the yield is 52.34%) in yellow powder is obtained.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 5, purifying the eluent by using the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000141
the detection analysis of the compound C-1-039 showed the following results:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 718.23; the test value was 718.81.
Elemental analysis:
the calculated values are: c: 84.16 percent; h: 4.11 percent; n: 3.57 percent; o: 4.08 percent; s: 4.08 percent;
the test values are: c: 84.17 percent; h: 4.12 percent; n: 3.55 percent; o: 4.09%; s: 4.07 percent;
as can be seen from the above test results, example 3 produces a compound of C-1-039 structure of high purity.
Example 4: preparation of luminescent Compound C-1-057
Under the protection of nitrogen, weighing the compound A-1-057(23.83mmol, 10.0g), B-1-057(28.58mmol, 14.73g) and potassium carbonate (35.74mmol, 4.9g) into the reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.024mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solid is separated out, so that the bridging ligand C-1-057(12.1g, the yield is 59.42%) is obtained in a yellow powder shape.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 2, purifying the eluent by using the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000151
the detection and analysis of the compound C-1-057 are as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 854.29; the test value was 855.01.
Elemental analysis:
the calculated values are: c: 88.50 percent; h: 4.48 percent; n: 3.28 percent; o: 3.74 percent;
the test values are: c: 88.51 percent; h: 4.47%; n: 3.29 percent; o: 3.73 percent;
as can be seen from the above test results, example 4 prepared a compound of C-1-057 structure with high purity.
Example 5: preparation of luminescent Compound C-2-003
Under the protection of nitrogen, weighing the compound A-2-003(27.04mmol, 10.0g), the compound B-2-003(32.45mmol, 13.09g) and the potassium carbonate (40.56mmol, 5.6g), putting the mixture into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture was cooled to 25 ℃ to precipitate, the precipitate was filtered, washed with water, absolute ethanol, and petroleum ether in this order, dried, and then subjected to silica gel column chromatography using dichloromethane as a solvent, and the filtrate was concentrated to precipitate a solid, thereby obtaining a bridging ligand C-2-003(9.71g, yield 51.8%) in the form of a yellow powder.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 4, purifying the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000161
the detection analysis of the obtained compound C-2-003 showed the following results:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 692.22; the test value was 692.78.
Elemental analysis:
the calculated values are: c: 83.22 percent; h: 4.07 percent; n: 8.09%; o: 4.62 percent;
the test values are: c: 83.21 percent; h: 4.06 percent; n: 8.10 percent; o: 4.63 percent;
as can be seen from the above test results, example 5 was prepared to obtain a compound of C-2-003 structure at high purity.
Example 6: preparation of luminescent Compound C-2-010
Under the protection of nitrogen, weighing the compound A-2-010(27.04mmol, 10.0g), B-2-010(32.45mmol, 11.46g) and potassium carbonate (40.56mmol, 5.6g) into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture was cooled to 25 ℃ to precipitate, the precipitate was filtered, washed with water, absolute ethanol, and petroleum ether in this order, dried, and subjected to silica gel column chromatography using dichloromethane as a solvent, and the filtrate was concentrated to precipitate a solid, thereby obtaining a bridging ligand C010(14.52g, yield 53.68%) in the form of yellow powder.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 6, purifying the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000171
the compound C-2-010 was subjected to detection analysis, and the results were as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 642.21; the test value was 642.72.
Elemental analysis:
the calculated values are: c: 82.23 percent; h: 4.08 percent; n: 8.72 percent; o: 4.98 percent;
the test values are: c: 82.24 percent; h: 4.09%; n: 8.71 percent; o: 4.97 percent;
as can be seen from the above test results, example 6 produces a compound of C-2-010 structure with high purity.
Example 7: preparation of luminescent Compound C-2-021
Under the protection of nitrogen, weighing the compound A-2-021(27.04mmol, 10.0g), the compound B-2-021(32.45mmol, 13.54g) and the potassium carbonate (40.56mmol, 5.6g), putting the mixture into a reaction system, adding a mixed solution of 200mL of methylbenzene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solids are separated out, so that the bridging ligand C-2-021(12.3g, the yield is 64.36%) is obtained in yellow powder.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 3, purifying the eluent by using the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000181
the compound C-2-021 is detected and analyzed, and the result is as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 706.20; the test value was 706.76.
Elemental analysis:
the calculated values are: c: 81.75 percent; h: 3.71 percent; n: 7.93 percent; o: 6.79 percent;
the test values are: c: 81.73 percent; h: 3.72 percent; n: 7.92 percent; o: 6.81 percent; as can be seen from the above test results, example 7 produces a compound having a C-2-021 structure with high purity.
Example 8: preparation of luminescent Compound C-2-050
Under the protection of nitrogen, weighing the compound A-2-050(27.04mmol, 10.0g), B-2-050(32.45mmol, 19g) and potassium carbonate (40.56mmol, 5.6g), putting into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.027mmol, 0.3g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solid is separated out, so that the bridging ligand C-2-050(14.1g, the yield is 59.59%) in yellow powder is obtained.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 4, purifying the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000191
the compound C-2-050 thus obtained was subjected to detection analysis, and the results were as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 874.24; the test value was 875.02.
Elemental analysis:
the calculated values are: c: 82.36 percent; h: 3.92 percent; n: 6.40 percent; o: 3.66 percent; s: 3.66 percent;
the test values are: c: 82.35 percent; h: 3.93 percent; n: 6.41 percent; o: 3.67 percent; s: 3.64 percent;
as can be seen from the above test results, example 8 produces a compound of the structure C-2-050 with high purity.
Example 9: preparation of luminescent Compound C-2-080
Under the protection of nitrogen, weighing the compound A-2-080(21.28mmol, 10.0g), B-2-080(25.54mmol, 16.32g) and potassium carbonate (31.92mmol, 4.4g), putting the compound A-2-080, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.21mmol, 0.24g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solids are separated out, so that the bridging ligand C-2-080(13.1g, the yield is 60.05%) is obtained in a yellow powder shape.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 6, purifying the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000201
the detection analysis of the compound C-2-080 showed the following results:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 1024.29; the test value was 1025.20.
Elemental analysis:
the calculated values are: c: 84.35 percent; h: 3.93 percent; n: 5.47%; o: 3.12 percent; s: 3.13 percent;
the test values are: c: 84.36 percent; h: 3.94 percent; n: 5.48 percent; o: 3.10 percent; s: 3.11 percent;
as can be seen from the above test results, example 9 produces a compound of C-2-080 structure with high purity.
Example 10: preparation of luminescent Compound C-2-101
Under the protection of nitrogen, weighing the compound A-2-101(21.14mmol, 10.0g), the compound B-2-101(25.37mmol, 13.18g) and the potassium carbonate (31.17mmol, 4.4g) into a reaction system, adding a mixed solution of 200mL of toluene, 100mL of ethanol and 100mL of purified water, adding tetrakis (triphenylphosphine) palladium (0.22mmol, 0.24g) under the protection of nitrogen, and heating and refluxing at 80 ℃ for 24 hours under the protection of nitrogen. Then, the mixture is cooled to 25 ℃, precipitates are separated out, the precipitates are filtered, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried, then, dichloromethane is used as a solvent for silica gel column chromatography, and the filtrate is concentrated until solids are separated out, so that the bridging ligand C-2-101(13.25g, the yield is 68.71%) is obtained in a yellow powder shape.
Wherein, the conditions of the silica gel column chromatography are as follows: selecting dichloromethane and petroleum ether as a solvent, weighing 500g of silica gel (200-300 meshes) as an adsorbent, adding petroleum ether, fully stirring until the mixture is uniform, pouring the mixture into a column, and adding a mixture after the silica gel is settled, wherein the developing agent is dichloromethane: petroleum ether is 1: and 2, purifying the eluent by using the eluent.
The reaction route of the preparation process is as follows:
Figure BDA0002978530140000211
the detection analysis of the compound C-2-101 is carried out, and the results are as follows:
HPLC purity: is more than 99 percent.
Mass spectrometry test: a theoretical value of 911.29; the test value was 911.02.
Elemental analysis:
the calculated values are: c: 82.97 percent; h: 4.09%; n: 7.68 percent; o: 5.26 percent;
the test values are: c: 82.98 percent; h: 4.10 percent; n: 7.67 percent; o: 5.25 percent;
as can be seen from the above test results, example 10 produced a compound of C-2-101 structure with high purity.
Example 11
The preparation process is carried out according to the above examples, compound a and compound B are respectively replaced by compounds corresponding to the corresponding ligand structures in the target product, and the amounts of the materials are adjusted according to the corresponding stoichiometric ratio, thereby obtaining the compounds of groups 1 to 24, see table 1 below. The detection analysis of each product was carried out according to the detection method in example 1, and the result was shown to be a luminescent compound of the corresponding structure.
TABLE 1 products from group 1 to group 24
Figure BDA0002978530140000212
Figure BDA0002978530140000221
Example 12 preparation of organic electroluminescent device (OLED) Using luminescent Compound
The structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/EML/HBL/ETL/EIL/cathode a, ITO anode: coating with a thickness of
Figure BDA0002978530140000222
The ITO (indium tin oxide) glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30min, then repeatedly cleaned for 2 times by distilled water, ultrasonically cleaned for 10min, after the cleaning is finished, ultrasonically cleaned by methanol, acetone and isopropanol in sequence (each time for 5min), dried, then transferred into a plasma cleaning machine for cleaning for 5min, and then sent into an evaporation machine, and other functional layers are sequentially evaporated on the substrate by taking the substrate as an anode.
b. HIL (hole injection layer): a hole injection layer was formed by evaporation of 2-TNATA (N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenylbenzene-1, 4-diamine) at 60 nm.
c. HTL (hole transport layer): NPB (i.e., N '-diphenyl-N, N' - (1-naphthyl) -1, 1 '-biphenyl-4, 4' -diamine) was evaporated to 60nm to form a hole transport layer.
d. EML (light-emitting layer):
the light emitting layer includes a host and a dopant. The body includes a plurality of body materials. The plurality of matrix materials includes a first matrix material and a second matrix material. The first host material may be composed of Ar alone2A compound represented by the formula II or at least one compound represented by Ar2Is a compound represented by formula II, and may further include conventional materials included in organic electroluminescent materials. The second host material may consist of only Ar2A compound represented by the formula IIIOr may consist of at least one of Ar2Is a compound represented by formula III, and may further include conventional materials included in organic electroluminescent materials.
C-1-003 is selected as a first host compound, C-2-006 is selected as a second host compound, and the weight ratio of the first host compound to the second host compound is 50: 50.
The dopant contained in the organic electroluminescent device is a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device is an ortho-metallized iridium complex. The dopant material used was a phosphorescent compound as shown in European patent application 07102949.0, and the dopant concentration of the dopant compound in the light-emitting layer was less than 20 wt% relative to the host compound, and the light-emitting layer was formed by vapor deposition of a mixture of the dopant compound and the host compound at a weight ratio of 90:10 and 30 nm.
Figure BDA0002978530140000231
e. HBL (hole blocking layer): a hole blocking layer was formed by evaporation of BALq 10 nm.
f. ETL (electron transport layer): alq 340 nm was evaporated to form an electron transport layer.
g. EIL (electron injection layer): and evaporating LiF by 0.2nm to form an electron injection layer.
h. Cathode: and evaporating Al for 150nm to form a cathode, thus obtaining the OLED device.
Example 13
With reference to the above method, OLED device groups 1-10 having different luminescent compounds were prepared by replacing luminescent compounds C-1-003 with C-1-005, C-1-009, C-1-013, C-1-017, C-1-028, C-1-034, C-1-041, C-1-043, and C-1-050, respectively, and replacing second host C-2-006 with C-2-008, C-2-009, C-2-010, C-2-036, C-2-048, C-2-050, C-2-054, C-2-058, and C-2-063, respectively.
Comparative example 1
An OLED device was prepared as in example 11, except that the host material in the light-emitting layer was replaced with the compound RH-1 shown in the following figure:
Figure BDA0002978530140000232
comparative examples 2 to 10
OLEDs were manufactured in the same manner as in device example 1, except that only the second host compound shown in table 2 was used instead of two hosts.
The OLED devices obtained in device examples 35-44 and comparative examples 1-10 were tested for emission performance, and driving voltage, emission lifetime, and emission efficiency were measured using a KEITHLEY model 2400 measuring unit and a CS-2000 spectral radiance luminance meter. The test results are shown in Table 2.
Table 2 luminescence property test results
(luminance value of 5000 cd/m)2)
Figure BDA0002978530140000241
Figure BDA0002978530140000251
Example 14
Referring to the above method, the light emitting compound is replaced with C-1-057, C-1-059, C-1-061, C-1-063, C-1-070, C-1-072, C-1-075, C-1-077, C-1-080, respectively, and the second host is replaced with C-2-066, C-2-069, C-2-070, C-2-071, C-2-074, C-2-075, C-2-087, C-2-090, C-2-099, C-2-105, respectively, while the dopant material is changed to the phosphorescent compound shown in the following figure, the dopant concentration of the dopant compound in the light emitting layer is less than about 20 wt% with respect to the host compound, the light-emitting layer is formed by vapor deposition of a mixture of the materials with the weight ratio of 90:10 and the thickness of 30 nm.
Figure BDA0002978530140000252
Groups 1 to 10 of OLED devices having different light-emitting compounds are thus prepared, respectively.
Comparative example 1
An OLED device was prepared as in device example 34, except that the host material in the light-emitting layer was replaced with the compound 4, 4'-N, N' -biphenyl dicarbazole ("CBP");
comparative examples 2 to 11
An OLED was manufactured in the same manner as in device example 1, except that only the second host compound shown in table 3 was used instead of two hosts.
The OLED devices obtained from the device groups 1-10 and the comparative examples 2-11 were tested for luminescence performance, and driving voltage, luminescence lifetime, and luminescence efficiency were measured using a KEITHLEY 2400-type measuring unit and a CS-2000 spectroradiometer. The test results are shown in Table 3.
Table 3 luminescence property test results
(luminance value of 5000 cd/m)2)
Figure BDA0002978530140000261
Figure BDA0002978530140000271
From the test results, the organic fused ring compound shown in the chemical formula 1 provided by the invention can effectively reduce the driving voltage of an OLED device, and improve the luminous efficiency and the service life.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (10)

1. An organic fused ring compound, wherein the structure of the organic fused ring compound is shown as formula 1:
Figure FDA0002978530130000011
wherein X and Y are selected from O or N, and the number of N is 1;
r1 represents unsubstituted, mono-, di-or trisubstituted; r2 and R3 are unsubstituted, mono-or di-substituted; ar (Ar)1，Ar2Each independently represents a single substituent.
2. The organic fused ring compound according to claim 1, wherein each of R1, R2, and R3 is at least one of a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C3 to C15 cycloalkyl group, a substituted or unsubstituted C6 to C18 aryl group, and a substituted or unsubstituted C4 to C12 aromatic heterocyclic group.
3. An organic fused ring compound according to claim 2, wherein the C1-C8 alkyl is a C1-C8 straight-chain or branched-chain alkyl group;
the C3-C15 cycloalkyl is any one of monocyclic alkyl, polycyclic alkyl or spiro alkyl;
the C6-C18 aryl group is a monocyclic group or a polycyclic group, the polycyclic group is a polycyclic group shared by two adjoining rings, at least one of the rings is an aromatic ring, and the other rings are at least one of cycloalkyl, cycloalkenyl, aryl or heteroaryl;
the C4-C12 aromatic heterocyclic group is any one of furan, thiophene or pyridine.
4. An organic fused ring compound according to claim 3, wherein at least one of the carbon atoms of the C3-C15 cycloalkyl group is substituted with a heteroatom, and the heteroatom is at least one of N, O, S, Si, Se or Ge.
5. The organic fused ring compound of claim 2, wherein the C1-C8 alkyl group is one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl;
the C3-C15 cycloalkyl is any one of cyclopropyl, cyclopentyl, cyclohexyl or adamantylamine, and at least one carbon atom is substituted by a heteroatom, wherein the heteroatom is at least one of N, O, S;
the C6-C18 aryl is any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene or pyrene.
6. An organic fused ring compound according to claim 5, wherein Ar is Ar1Independently represent a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-60 membered aromatic heterocyclic group;
Ar2as shown in formula II or formula III;
Figure FDA0002978530130000021
wherein the content of the first and second substances,
Figure FDA0002978530130000022
is a radical junction;
l1 and L2 each independently represent any one of a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-to 30-membered) heteroarylene group, and a substituted or unsubstituted (C3-C30) cycloalkylene group;
wherein Ar is3，Ar4Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or unsubstituted mono or di (C1-C30) alkylamino, substituted or unsubstituted mono or di (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
Ar5represents a substituted or unsubstituted 3-30 membered heteroaryl group.
7. An organic fused ring compound according to claim 6, wherein Ar is Ar5Is any one of substituted or unsubstituted quinazoline group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted triazinyl group and substituted or unsubstituted pyrimidyl group.
8. The method of claim 7, comprising the steps of:
1) under the protection of inert gas, mixing the compound A, the compound B, an alkaline substance and a solvent I, adding a catalyst, and then carrying out heating reaction;
wherein the solvent I is a mixed solvent of methanol, ethanol and water;
the alkaline substance is potassium carbonate or sodium carbonate;
2) after the reaction is finished, carrying out suction filtration, washing, drying, column chromatography and rotary evaporation and concentration to obtain an organic fused ring compound C shown in the formula I;
the synthetic route is as follows:
Figure FDA0002978530130000031
wherein Ar is3Is one of the halogen groups;
X，Y，R1，R2，R3，Ar1，Ar2and X, Y, R1, R2, R3, Ar of claim 71，Ar2。
9. The method for preparing the condensed-cyclic compound according to claim 8, wherein the catalyst is tetrakis (triphenylphosphine) palladium, and the molar ratio of tetrakis (triphenylphosphine) palladium to compound a is (0.005-0.05): 1;
the molar ratio of the compound A to the compound B is 1 (1.1-1.5);
the molar ratio of the compound A to the alkaline substance is 1 (1.2-2.0);
the heating reaction temperature is 70-90 ℃, and the reaction time is 20-30 h;
the volume ratio of toluene, ethanol and water in the solvent I is 2:1: 1;
the ratio of the compound A to the solvent I is 50mmol (350-400) mL;
the detergent is one or a mixture of water, absolute ethyl alcohol and petroleum ether;
the drying temperature is 70-80 ℃, and the drying time is more than or equal to 8 hours;
the column chromatography uses the mixture of dichloromethane and petroleum ether as a solvent and adopts silica gel column chromatography.
10. Use of the condensed cyclic compound obtained by the preparation method according to any one of claims 8 to 9 for preparing an organic electroluminescent device.
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KR20180041480A (en) * 2016-10-14 2018-04-24 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof

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US11814404B2 (en) 2020-07-20 2023-11-14 Annexon, Inc. Inhibitors of complement factors and uses thereof
WO2023137166A1 (en) * 2022-01-14 2023-07-20 Annexon, Inc. Inhibitors of complement factors and uses thereof
WO2023241137A1 (en) * 2022-06-13 2023-12-21 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent apparatus, and electronic device
WO2023241136A1 (en) * 2022-06-13 2023-12-21 陕西莱特光电材料股份有限公司 Heterocyclic compound, organic electroluminescent apparatus, and electronic device
CN115819351A (en) * 2022-12-22 2023-03-21 吉林奥来德光电材料股份有限公司 Organic fused ring compound and preparation method and application thereof

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