CN114773366A - Carbonyl-fused boron-nitrogen derivative and preparation method and application thereof - Google Patents
Carbonyl-fused boron-nitrogen derivative and preparation method and application thereof Download PDFInfo
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- CN114773366A CN114773366A CN202210284023.4A CN202210284023A CN114773366A CN 114773366 A CN114773366 A CN 114773366A CN 202210284023 A CN202210284023 A CN 202210284023A CN 114773366 A CN114773366 A CN 114773366A
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- Prior art keywords
- compound
- boron
- nitrogen
- carbonyl
- formula
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- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical class [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 19
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 10
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 10
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
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- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
The invention belongs to the field of light-emitting devices, and relates to a carbonyl-fused boron-nitrogen derivative, and a preparation method and application thereof. The invention provides a preparation method of a novel carbonyl fused boron-nitrogen derivative B/N/C ═ O, and the preparation method is applied to an organic electroluminescent device to obtain excellent effect; the system expands a molecular library of TADF materials, promotes the application of organic light-emitting diodes with high efficiency, high color purity and low efficiency roll-off, and provides a certain foundation for designing a thermal activation delayed fluorescence OLED (organic light-emitting diode) material which is closer to the commercial requirement in the future.
Description
Technical Field
The invention belongs to the field of luminescent devices, and relates to a carbonyl fused boron-nitrogen derivative, a preparation method and application thereof, in particular to an organic electroluminescent device.
Background
Organic light emitting diodes are widely applied to the fields of flexible screen display, daily illumination and the like, and research on developing organic light emitting materials with higher color purity and reduction degree is very important for enhancing display technologies such as high definition and ultrathin.
As a third generation organic light emitting material, a Thermally Activated Delayed Fluorescence (TADF) material is a current research hotspot due to its advantages of low cost, high efficiency, and the like. Thermally activated delayed fluorescence materials are often obtained by designing twisted donor-acceptor fragments to achieve smaller singlet triplet band gaps Δ ESTBut this inevitably leads to an increase in molecular relaxation, resulting in poor color purity. The molecular design strategy of multiple resonance proposed in recent years provides an effective solution for developing devices with higher radiative transition rate, smaller half-peak width and higher color purity. Through years of research, three types of molecular structures are mainly developed in the current multiple resonance system, namely DABNA-1(5,9-diphenyl-5,9-diaza-13 b-boranophtho [3,2,1-de ]]anthracene) as parent nucleus, QAO (quinolino [3,2, 1-de)]acridine-5,9-dione) as mother nucleus, 2a (5,9-dioxa-13 b-boranopho [3,2, 1-de)]anthracene) is the boron-oxygen molecular structure of the mother nucleus. Among them, the boron oxygen system is usually designed as the molecular acceptor fragment, the nitrogen carbonyl system is gradually cooled down due to the obvious extension of half-peak width in the device, and the research of multiple resonance is mainly based on the molecular structure of the BN system as the core at present. Although the BN molecular system has been developed over many years to achieve higher EQE (external quantum efficiency) and narrower FWHM (full width at half maximum), it faces the problem of severe efficiency roll-off, hindering the commercialization thereof. Although the introduction of a proper sensitizer can effectively improve the utilization rate of triplet excitons and reduce roll-off, the selection of matched sensitizers, fine control of device structures and the like are inevitable problems. Thus increasing the reverse intersystem crossing rate k by enhancing the self-Selected Orbital Coupling (SOC) of the moleculeRISCIt would be a strategy full of great potential for reducing molecular roll-off.
Disclosure of Invention
The present invention aims to provide a carbonyl-fused boron-nitrogen derivative, a preparation method and applications thereof, which can obtain excellent devices with high efficiency, high color purity and low efficiency roll-off and with commercial application potential.
According to the technical scheme, the carbonyl-condensed boron-nitrogen derivative is condensed with a carbonyl group which influences the cloud distribution of HOMO and LUMO energy level electrons on the basis of a boron-nitrogen structure.
Further, the boron nitrogen derivative has a structure shown as follows:
wherein X is selected from oxygen, sulfur, selenium, fluorenyl, silicon base or diphenyl;
R1-R6independently selected from hydrogen, cyano, methyl, tert-butyl, diphenylamine, 3, 6-di-tert-butyldiphenylamine, carbazolyl, 3, 6-di-tert-butylcarbazolyl, phenothiazinyl, phenoxazinyl, triazinyl, fluorenone, or 9,9' -spirobifluorenyl.
The second aspect of the present invention provides a method for producing the above carbonyl-fused boron nitrogen derivative, comprising the steps of,
s1: under the action of a palladium catalyst and alkali, carrying out coupling reaction on a compound I and a compound shown in a formula (7) to obtain a compound II, wherein the structural formula of the compound I is shown as a formula (5), (6), (12) or (13), and the structural formula of the compound II is shown as a formula (8), (9), (14) or (15);
s2: under the action of organic lithium, boron tribromide and N, N-diisopropylethylamine, carrying out boronization cyclization reaction on the compound II to generate a boron-nitrogen compound; the structure of the boron-nitrogen compound is shown as a formula (10), (11), (16) or (17);
s3: under the action of 2, 3-dichloro-5, 6-dicyanobenzoquinone, a methylene group of the boron nitrogen compound is oxidized to obtain a carbonyl condensed boron nitrogen derivative;
wherein X1And X2Selected from fluorine, chlorine, bromine or iodine; x is selected from oxygen, sulfur, selenium, fluorenyl,A diphenyl group; r is1-R6As defined in claim 2.
Further, in the step S1, the coupling reaction is carried out in the organic solvent I, the reaction temperature is 100 ℃ and 120 ℃, and the reaction time is 10-20 h; preferably, the reaction temperature is 110 ℃ and the reaction time is 12 h.
Further, the organic solvent I is selected from toluene, tetrahydrofuran, 1, 4-dioxane or dimethyl sulfoxide solvent.
Further, in the step S1, a catalyst ligand is further added before the coupling reaction, and the catalyst ligand is tBu3P (tri-tert-butylphosphine), tBu3P-HBF4(tri-tert-butylphosphine tetrafluoroborate), S-phos (2-dicyclohexyl-2 ',6' -dimethoxy biphenyl) or X-phos (2-dicyclohexyl-2 ',4',6' -triisopropyl biphenyl), wherein the molar ratio of the catalyst ligand to the palladium catalyst is 1-10: 1.
further, the palladium catalyst is Pd (dba)2(bis (dibenzylacetyl) palladium), Pd2(dba)3(tris (dibenzylideneacetone) dipalladium) or Pd (OAc)2(palladium acetate), wherein the base is sodium tert-butoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate or cesium carbonate.
Further, in the step S1,
when the structural formula of the compound I is shown as the formula (5) or (6), the molar ratio of the palladium catalyst, the alkali, the compound I and the compound shown as the formula (7) is 0.02-0.1: 1-4: 1-3: 1;
when the structural formula of the compound I is shown as the formula (12) or (13), the molar ratio of the palladium catalyst, the alkali, the compound I and the compound shown as the formula (7) is 0.04-0.1: 2-12: 1: 1-3.
Further, the specific operation of step S2 is as follows: under the protective atmosphere, adding anhydrous tert-butyl benzene solvent or mesitylene solvent into the compound II, adding organic lithium at the temperature of-50 to-30 ℃, and reacting for 0.8 to 2 hours at the temperature of 50 to 70 ℃; boron tribromide is added at the temperature of minus 50 to minus 30 ℃, and the reaction is carried out for 0.8 to 2 hours at the room temperature (25 +/-5 ℃); adding N, N-diisopropylethylamine at the temperature of about 0 ℃ in ice bath, and reacting at the temperature of 120-140 ℃ for 10-20h to obtain the boron-nitrogen compound.
Further, the protective atmosphere is nitrogen, argon or helium.
Further, the organic lithium is tert-butyl lithium or n-butyl lithium.
Further, in the step S2, the molar ratio of the organolithium, the boron tribromide, the N, N-diisopropylethylamine and the compound II is 1 to 10: 1-10: 1-10: 1.
further, in order to improve the solubility, in step S3, the oxidation reaction is performed in a mixed solvent of the organic solvent II and water.
Further, the organic solvent II is dichloromethane and/or 1, 4-dioxane.
Further, the step S3 is performed under a protective atmosphere.
Further, in the step S3, the molar ratio of the 2, 3-dichloro-5, 6-dicyanobenzoquinone to the boron nitrogen compound is 5 to 20: 1.
in a third aspect, the present invention provides the use of the carbonyl-fused boron nitrogen derivative described above in an organic electroluminescent device.
The invention provides a preparation method of a novel carbonyl-condensed boron-nitrogen derivative and application of the novel carbonyl-condensed boron-nitrogen derivative in an organic electroluminescent device based on excellent photoelectric property of a B/N system and the combination of the carbonyl with the potential of improving the self-selected track coupling SOC. Through ingenious route design, the methylene in the traditional boron-nitrogen structure can be oxidized, a novel carbonyl-fused boron-nitrogen derivative is synthesized, the combination of a B/N system and an N/C (O) system can be effectively realized, a novel B/N/C (O) system is formed, and the prepared photoelectric device can also realize the aims of high efficiency, high color purity and low efficiency roll-off. The results show that the introduction of carbonyl in BNOCZ not only enhances SOC of S1 (first singlet) and T2 (second triplet), but also improves kRISC(3×106s-1) Meanwhile, the smaller half-peak width of the device is ensured. Finally BNOCZ achieves ultra pure green luminescence with low efficiency roll-off at maximum electroluminescent efficiency of 25.1% (CIEy ═ 0.70).
Compared with the prior art, the technical scheme of the invention has the following advantages: a preparation method of a novel carbonyl-condensed boron-nitrogen derivative B/N/C ═ O is provided, and the preparation method is applied to an organic electroluminescent device to obtain excellent effects. The system expands a molecular library of TADF materials, promotes the application of organic light-emitting diodes with high efficiency, high color purity and low efficiency roll-off, and provides a certain foundation for designing a thermal activation delayed fluorescence OLED (organic light-emitting diode) material which is closer to the commercial requirement in the future.
Drawings
Fig. 1 is a schematic view of the structure of an organic electroluminescent device in an experimental example.
Description of reference numerals: 1-glass substrate, 2-hole transport layer, 3-electron barrier layer, 4-luminescent layer, 5-electron transport layer and 6-cathode layer.
Detailed Description
The present invention is further described below in conjunction with the drawings and the embodiments so that those skilled in the art can better understand the present invention and can carry out the present invention, but the embodiments are not to be construed as limiting the present invention.
Example 1: synthesis of 10, 13-di-tert-butyl-15 b-aza-8 b-borabenzo [ j ] fluorene [1,9-ab ] perylene-5-one (BNOCZ)
1. The synthetic route is as follows:
2. synthesis of intermediate 2a
Starting material 9, 10-dihydroacridine (1.01g,5.60mmol), 1a (2.80g,6.1mmol), Pd (dba)2(161mg,0.28mmol), sodium t-butoxide (tBuONa, 1.40g,14.6mmol) was added to a 100mL two-necked flask, replacing N2After protection, toluene (15mL) was added, nitrogen was further purged three times, and tri-tert-butylphosphine (tBu) was added3P, 0.50mL,0.80mmol), reflux reaction at 110 ℃ for 12h, TLC (thin layer chromatography) showed disappearance of starting material 1a, quenching with water, DCM (dichloromethane) extractionDrying, spin-drying, PE (petroleum ether): DCM ═ 10:1 column chromatography gave white solid 2a (1.98g, 62%).
And (3) product characterization:1H NMR(400MHz,CDCl3):δ8.27(d,J＝1.9Hz,2H),7.78–7.72(m,2H),7.70–7.66(m,1H),7.59(dd,J＝8.6,2.0Hz,2H),7.28–7.24(m,2H),7.23–7.14(m,4H),7.01(t,J＝7.4Hz,2H),6.39(d,J＝8.2Hz,2H),4.37(s,2H),1.57(s,19H).13C NMR(101MHz,CDCl3):δ143.14,140.89,140.11,139.12,138.42,135.78,133.11,130.72,129.22,128.83,127.06,123.75,123.48,121.13,120.94,116.42,113.21,109.42,34.78,32.04,32.01,31.61.MALDI-TOF:Calculated:568.26,Found:568.03.
3. synthesis of intermediate 3a
Starting material 2a (5.70g,10.0mmol) was charged into a 100mL two-necked flask, and N was replaced2After the protection, anhydrous tert-butyl benzene (30mL) was added, nitrogen gas was purged three times, tert-butyl lithium (15.6mL,1.6M,25.0mmol) was added at-40 ℃ and the mixture was reacted at 60 ℃ for 2 hours while moving away from the low temperature bath. Boron tribromide (2.4mL,25.0mmol) was added slowly at-40 ℃ and the reaction was allowed to proceed for 1h at room temperature. N, N-diisopropylethylamine (3.5mL,25.0mmol) was added under ice-cooling and reacted overnight at 130 ℃. Sampling TLC showed disappearance of starting material 2a and formation of new spots, quenching with aqueous PBS, DCM extraction, drying, spin drying, PE column chromatography to give yellow solid 3a (1.36g, 25%).
And (3) product characterization:1H NMR(400MHz,CDCl3)δ:8.84(d,J＝1.9Hz,1H),8.64(dd,J＝7.5,1.6Hz,1H),8.44(d,J＝1.8Hz,1H),8.35(d,J＝8.8Hz,1H),8.26(d,J＝2.1Hz,1H),8.16(dd,J＝7.5,1.4Hz,1H),7.81–7.72(m,2H),7.71–7.62(m,2H),7.49(dd,J＝7.3,1.5Hz,1H),7.42(t,J＝7.3Hz,1H),7.35(dd,J＝5.8,3.4Hz,1H),7.16(dd,J＝5.9,3.4Hz,2H),3.83(s,2H),1.62(s,9H),1.52(s,9H).13C NMR(101MHz,CDCl3):δ145.06,144.84,144.75,144.41,141.84,141.19,138.25,133.60,133.05,131.84,31.32,131.24,129.61,127.31,127.01,126.18,124.29,124.00,123.52,121.97,120.40,120.32,117.18,13.96,111.28,106.48,55.40,36.54,35.18,34.79,32.25,31.86,27.64,0.01.MALDI-TOF:Calculated:542.29,Found:542.17.
3. synthesis of BNOCZ
Material 3a (1.08g,2.0mmol) was charged into a 100mL two-necked flask, dissolved by addition of dichloromethane (80mL) under ice-cooling, and then 1, 4-dioxane (40mL) and water (10mL) were added, followed by slow addition of 2, 3-dichloro-5, 6-dicyanobenzoquinone (3.09g,13.6 mmol). The reaction was carried out overnight at room temperature, TLC showed disappearance of starting material 3a and formation of new spots, quenched with water, extracted with DCM, dried, spun dried, column chromatographed at PE: DCM ═ 2:1 to remove most of the impurities, and column chromatographed at PE: DCM ═ 45:1 to give BNOCZ430mg as a tan product in 39% yield.
And (3) product characterization:1H NMR(400MHz,CDCl3):δ8.96(dd,J＝7.3,1.8Hz,1H),8.77–8.72(m,2H),8.53–8.47(m,2H),8.38–8.32(m,2H),8.28(d,J＝2.1Hz,1H),8.22(d,J＝8.6Hz,1H),7.80(d,J＝7.2Hz,2H),7.71–7.65(m,2H),7.58(ddd,J＝8.7,7.0,1.7Hz,1H),7.42(ddd,J＝7.9,7.0,1.0Hz,1H),1.63(s,9H),.53(s,9H).13CNMR(101MHz,CDCl3):δ180.13,143.72,141.94,141.49,141.03,132.06,131.39,31.22,127.22,127.16,124.86,123.79,123.49,121.11,113.82,50.92,0.01.MALDI-TOF:Calculated:556.27,Found:556.11.
example 2: synthesis of BNOAC
1. Synthetic route
2. Synthesis of intermediate 1b
Starting materials 9, 10-dihydroacridine (1.01g,5.60mmol), 2-chloro-1, 3-dibromobenzene (0.73g,2.60mmol), Pd (dba)2(322mg,0.60mmol), sodium t-butoxide (2.80g,29mmol) was added to a 100mL two-necked flask, substituting N2After protection, toluene (15mL) was added, nitrogen was purged three times, tri-tert-butylphosphine (0.50mL,0.80mmol) was added, the mixture was refluxed at 110 ℃ for 12h, TLC showed disappearance of 2-chloro-1, 3-dibromobenzene as a starting material, water was added to quench, DCM was extracted, dried, and spin dried, and PE: DCM ═ 10:1 column chromatography gave white solid 1b (0.58g, 48%).
And (3) product characterization:1H NMR(400MHz,CDCl3):δ7.73(dd,J＝8.5,7.1Hz,1H),7.64–7.60(m,2H),7.17(dq,J＝7.4,1.2Hz,4H),7.06–6.99(m,4H),6.90(td,J＝7.4,1.2Hz,4H),6.23(dd,J＝8.2,1.2Hz,4H),4.26(s,4H).13C NMR(101MHz,CDCl3):δ143.72,142.48,140.89,140.85,134.69,133.70,132.98,131.48,128.82,128.55,126.99,126.79,121.15,121.12,121.06,120.85,113.94,113.30,31.98,31.68.MALDI-TOF:Calculated:470.15,Found:470.30.
3. synthesis of intermediate 2b
Raw material 1b (4.71g,10.0mmol) was charged into a 100mL two-necked flask, and N was replaced2After the protection, anhydrous tert-butyl benzene (30mL) was added, nitrogen gas was purged three times, tert-butyl lithium (15.6mL,1.60M,25.0mmol) was added at-40 ℃ and the mixture was reacted at 60 ℃ for 2 hours while moving away from the low temperature bath. Boron tribromide (2.40mL,25.0mmol) was added slowly at-40 ℃ and the reaction was allowed to proceed for 1h at room temperature. N, N-diisopropylethylamine (3.50mL,25.0mmol) was added under ice-cooling and reacted at 130 ℃ overnight. TLC showed disappearance of starting material 1b and formation of a new spot, quenching with aqueous PBS, extraction with DCM, drying, spin drying, and PE column chromatography to give 2b as a yellow solid (840mg, 19%).
And (3) product characterization:1H NMR(400MHz,CDCl3):δ8.38(dt,J＝7.5,1.3Hz,2H),7.68–7.62(m,4H),7.58(dd,J＝9.2,7.0Hz,1H),7.53(dt,J＝7.3,1.4Hz,2H),7.39(ddd,J＝5.2,3.6,1.0Hz,2H),7.35(t,J＝7.4Hz,2H),7.17–7.12(m,4H),4.20(d,J＝16.4Hz,2H),4.03(d,J＝16.5Hz,2H).13C NMR(101MHz,CDCl3):δ144.86,143.40,141.28,132.64,130.94,130.01,129.85,128.08,126.62,126.29,124.44,122.61,119.43,110.36,77.34,77.03,76.71,33.94,0.01.MALDI-TOF:Calculated:444.18,Found:444.37.
4. synthesis of BNOAC
Starting material 2b (88mg,0.2mmol) was charged into a 100mL two-necked flask, dissolved by addition of dichloromethane (80mL) under ice-cooling, added 1, 4-dioxane (40mL) and water (10mL) and added 2, 3-dichloro-5, 6-dicyanobenzoquinone (618mg,3.72mmol) slowly. The reaction was carried out overnight at room temperature, TLC showed disappearance of starting material 2b and formation of new spots, quenched with water, extracted with DCM, dried, spun dried, column chromatographed at PE: DCM ═ 2:1 to remove most of the impurities, and column chromatographed at PE: DCM ═ 45:1 to give the tan product BNOAC10mg in 11% yield.
And (3) product characterization:1H NMR(400MHz,CDCl3):δ8.73(dd,J＝7.7,1.7Hz,2H),8.61(dd,J＝7.2,1.7Hz,2H),8.47(dd,J＝8.0,1.7Hz,2H),8.12(d,J＝8.5Hz,2H),7.88(d,J＝8.3Hz,2H),7.66(td,J＝7.8,2.4Hz,3H),7.58(ddd,J＝8.7,7.0,1.7Hz,2H),7.47–7.41(m,2H).13C NMR(101MHz,CDCl3):δ179.91,145.75,145.42,144.67,143.72,142.47,142.25,141.85,138.28,131.98,131.87,130.76,129.57,127.12,127.04,126.70,124.73,124.32,124.05,123.47,123.08,121.38,120.90,117.42,114.00,109.81,35.25,34.85,32.21,31.82,0.01.MALDI-TOF:Calculated:472.14,Found:472.36.
example 3: BNOD2Synthesis of (2)
1. Synthetic route
2. Synthesis of intermediate 2c
A100 mL two-necked flask was charged with 9, 10-dihydroacridine (145mg,0.80mmol), 1c (800mg,0.87mmol), Pd as a starting material2(dba)3(41mg,0.04mmol), sodium t-butoxide (230mg,24mmol), substitution of N2After protection, DMF (15mL) was added, followed by addition of tri-tert-butylphosphine (120mg,0.41mmol), followed by three additional nitrogen purging, reflux reaction at 110 ℃ for 12h, TLC sampling indicated disappearance of the starting 9, 10-dihydroacridine, quenching with water, DCM extraction, drying over anhydrous sodium sulfate, spin-drying, and PE: DCM-10: 1 column chromatography gave white solid 2c (433mg, 52%).
And (3) product characterization: 1H NMR (400MHz, CDCl3): δ 7.79(d, J ═ 2.2Hz,2H), 7.73-7.69 (m,2H),7.62(dd, J ═ 6.4,3.1Hz,1H),7.20(td, J ═ 6.0,5.6,1.7Hz,12H),7.06(d, J ═ 8.6Hz,3H), 7.03-6.98 (m,9H),6.92(td, J ═ 7.3,1.2Hz,2H),6.25(dd, J ═ 8.2,1.1Hz,2H),4.30(s,2H),1.29(s,36H).13C NMR (101MHz, CDCl3 δ 145.94,144.21,141.21,140.81,140.18,138.04,137.93,137.48,135.70,133.42,130.68,130.24,129.31,128.86,127.06,125.85,125.74,124.25,122.26,122.17,121.17,120.92,118.38,113.12,110.86,34.17,31.46.MALDI, 23: cut: 1014.54: 18 TOF: 1014.59.
3. Intermediate BND2Synthesis of (2)
Feed 2c (5.08g,5.0mmol) was charged into a 100mL two-necked flask, and N was replaced2After the protection, anhydrous tert-butyl benzene (30mL) was added, nitrogen gas was purged three times, tert-butyl lithium (7.80mL,1.6M,12.5mmol) was added at-40 ℃ and the mixture was reacted at 60 ℃ for 2 hours while moving away from the low temperature bath. Boron tribromide (1.20mL,12.5mmol) was added slowly at-40 ℃ and the reaction was carried out at room temperature for 1 h. N, N-diisopropylethylamine (1.80mL,12.5mmol) was added under ice-bath and reacted overnight at 170 ℃. Sampling TLC to show that the raw material 2b disappears and new spots are generated, adding PBS aqueous solution for quenching, DCM for extraction, drying, spin-drying, performing PE column chromatography to obtain yellow solid BND2(1.14g,23％)。
And (3) product characterization: 1H NMR (400MHz, CD2Cl2) δ:8.53(d, J ═ 2.1Hz,1H),8.36(d, J ═ 9.0Hz,1H), 8.25-8.22 (m,1H),8.17(dd, J ═ 6.2,2.7Hz,1H),8.10(d, J ═ 2.1Hz,1H),7.89(d, J ═ 2.3Hz,1H), 7.83-7.80 (m,2H),7.67(dd, J ═ 5.9,3.6Hz,1H),7.52(d, J ═ 7.3Hz,1H),7.43(d, J ═ 1.8Hz,1H),7.38(dd, J ═ 8.9,2.4, 1H), 7.34H, 1H, 7.19H, 7.9H, 7.6H), 7.8H, 7.9H, 7.19H, 7.9H, 7.6H, 7.13H, 7.9H, 7.6H, 7.7.6H, 7.6H, 7.13H, 7.6H, 7.7.7.6H, 7.6H, 7.8H, 7.6 (d, 7.8H, 7.6H, 7.8H, 7.9H, 7.6H, 7.9H, 7.6H, 13H, 7.9H, 7.6H, 7.9H, 7H, 7.6H, 7H, 7.6H, 7H, 7.6H, 7H, 7.6H, 13H, 7.6H, 7H, 3H, 7H, 7.6H, 7H, 3H, 13H, 3H, 7H, 3H, 13H, 3H, 7H, 3H, 13H, 7H, 7.9H, 7H, 3H, 7H, 13H, 3H, 13H, CD2Cl2), delta 145.99,145.63,145.30,145.13,144.81,144.64,142.99,142.98,142.30,141.20,140.29,136.32,132.89,131.97,130.66,130.26,129.89,128.09,127.73,126.65,126.22,126.07,126.03,124.63,124.56,122.91,122.51,121.72,119.55,117.28,115.15,112.30,106.65,34.13,34.10,31.19,29.69, MALDI-TOF, scaled: 988.56, Found:988.56.
4、BNOD2Synthesis of (2)
BND raw material2(396mg,0.40mmol) was charged into a 100mL two-necked flask, and dissolved in dichloromethane (20mL) under ice bath in an oxygen atmosphere of 1atm, followed by addition of 1, 4-dioxane (10mL) and water (2.50mL), followed by slow addition of 2, 3-dichloro-5, 6-dicyanobenzoquinone (618mg,2.72 mmol). Reacting at room temperature overnight, TLC shows that the raw material BND2 disappears and new spots are generated, adding water for quenching, DCM for extraction, drying by anhydrous sodium sulfate, spin-drying, carrying out column chromatography on PE: DCM (2: 1) to remove most impurities, and carrying out column chromatography on PE: DCM (45: 1) to obtain a brownish red product BNOD2120mg, yield 30%.
And (3) product characterization: 1H NMR (400MHz, CD2Cl2): δ 8.51-8.47 (m,2H), 8.39-8.32 (m,2H), 8.25-8.15 (m,2H),8.11(d, J ═ 2.0Hz,1H), 8.06-8.00 (m,1H),7.84(d, J ═ 2.3Hz,1H),7.67(H, J ═ 5.8,4.7Hz,2H), 7.50-7.43 (m,1H), 7.37-7.27 (m,11H),7.12(d, J ═ 8.6Hz,4H),7.05(d, J ═ 8.7Hz,4H), 1.33-1.30 (m,36H), 13 (mr, 101MHz, CD2Cl2, 179.23,145.90,145.53,145.34,145.15,144.55,143.53,143.44,141.98,141.35,140.06,136.16,131.95,131.80,130.34,130.14,127.81,126.70,126.63,126.13,124.99,124.55,124.23,123.98,123.53,123.20,123.11,122.79,122.69,122.10,121.64,120.82,116.99,115.15,114.00,109.65, δ, 179.23,145.90,145.53,145.34,145.15,144.55,143.53,143.44,141.98,141.35,140.06,136.16,131.95,131.80,130.34,130.14,127.81,126.70,126.63,126.13,124.99,124.55,124.23,123.98,123.53,123.20,123.11,122.79,122.69,122.10,121.64,120.82,116.99,115.15,114.00,109.65, 15.31, 19, 21, 26, 21, 7,3, 7,3, 7,3, 7,3, 8, 3, 8, 3, 8, 3, 8, 3, 8, 3, etc. H.
Test examples
Preparation and performance evaluation of organic electroluminescent device with example 1 as fluorescent doped dye
A glass plate with an Indium Tin Oxide (ITO) transparent electrode was used as a substrate, and the substrate was striped and 3mm in width. After the glass substrate was washed with isopropyl alcohol, surface treatment was performed by ozone ultraviolet rays. Vacuum deposition of each layer was performed on the cleaned substrate by vacuum deposition to produce a light-emitting area 9mm as shown in FIG. 1 in a cross-sectional view2The organic electroluminescent device of (1).
First, the glass substrate is introduced into a vacuum evaporation tank and reduced in pressure to 1X 10-4Pa. Then, on the glass substrate shown in fig. 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, and an electron transport layer 5 were formed in this order as organic compound layers, and then a cathode layer 6 was formed. 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline vacuum-evaporated in a film thickness of 30nm](TAPC) and 10nm thick film vacuum deposition of 4,4 '-three (carbazole-9-base) triphenylamine (TCTA) as the hole transport layer 2, with 10nm thick film vacuum deposition of 1, 3-two-9-carbazolylbenzene (mCP) as the electron barrier layer 3, with 20nm thick film vacuum deposition of 94:6 (mass%) of 2- (9,9' -spirobi [ fluorene)]-3-yl) -4, 6-diphenyl-1, 3, 5-triazine (SF3TRZ) 3,3'- [5' - [3- (3-pyridyl) phenyl) which was vacuum-evaporated with a film thickness of 40nm as the light-emitting layer 4 with BNOCZ synthesized in practical example 1 of the present invention][1,1':3', 1' -terphenyl]-3,3 "-diyl]Bipyridine (TmPyPb) was used as the electron transport layer 5. Wherein each organic material is formed into a film by means of resistance heating. Heating the compound to vacuum-evaporate at a film forming rate of 0.3-0.5 nm. Finally, a metal mask is disposed so as to be orthogonal to the ITO stripes, thereby forming a film cathode 6. The cathode layer 6 has a two-layer structure formed by vacuum-depositing lithium fluoride and aluminum in film thicknesses of 1nm and 100nm, respectively. Each film thickness was measured by a stylus film thickness measuring instrument (DEKTAK). Further, the device was sealed in a glove box under a nitrogen atmosphere containing water and oxygen at a concentration of 1ppm or less. The sealing was carried out by using a vitreous sealing cap and the above film-forming substrate epoxy ultraviolet curable resin (manufactured by Nagase ChemteX Corporation).
The prepared organic electroluminescent device was subjected to direct current application, evaluated for light emission performance using a Spectrascan PR650 luminance meter, and measured for current-voltage characteristics using a computer-controlled Keithley 2400 digital source meter. As the light emission characteristics, CIE color coordinate values and maximum luminance (cd/m) were measured under the change of applied DC voltage2) External quantum efficiency (%), power efficiency (lm/W). The measurement values of the fabricated devices were (0.222,0.703), 11100cd/m224.1% and 71.3 lm/W.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. This need not be, nor should it be exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.
Claims (10)
1. A carbonyl-fused boron-nitrogen derivative characterized in that a carbonyl group which affects the HOMO and LUMO level electron cloud distribution thereof is fused on the basis of a boron-nitrogen structure.
2. A carbonyl-fused boron nitrogen derivative according to claim 1, wherein the boron nitrogen derivative has the structure shown below:
wherein X is selected from oxygen, sulfur, selenium, fluorenyl or diphenyl;
R1-R6independently selected from hydrogen, cyano, methyl, tert-butyl, diphenylamine, 3, 6-di-tert-butyldiphenylamine, carbazolyl, 3, 6-di-tert-butylcarbazolyl, phenothiazinyl, phenoxazinyl, triazinyl, fluorenone, or 9,9' -spirobifluorenyl.
3. The method of producing a carbonyl-fused boron-nitrogen derivative according to claim 2, comprising the steps of,
s1: under the action of a palladium catalyst and alkali, carrying out coupling reaction on a compound I and a compound shown in a formula (7) to obtain a compound II, wherein the structural formula of the compound I is shown as a formula (5), (6), (12) or (13), and the structural formula of the compound II is shown as a formula (8), (9), (14) or (15);
s2: under the action of organic lithium, boron tribromide and N, N-diisopropylethylamine, carrying out boronization cyclization reaction on the compound II to generate a boron-nitrogen compound; the structure of the boron-nitrogen compound is shown as a formula (10), (11), (16) or (17);
s3: under the action of 2, 3-dichloro-5, 6-dicyanobenzoquinone, oxidizing a methylene group of the boron nitrogen compound to obtain a carbonyl condensed boron nitrogen derivative;
wherein, X1And X2Selected from fluorine, chlorine, bromine or iodine; x is selected from oxygen, sulfur, selenium, fluorenyl and diphenyl; r is1-R6As defined in claim 2.
4. The method as claimed in claim 3, wherein in step S1, the coupling reaction is carried out in the organic solvent I at a temperature of 100-120 ℃ for a reaction time of 10-20 h.
5. The production method according to claim 3 or 4, wherein in the step S1,
when the structural formula of the compound I is shown as the formula (5) or (6), the molar ratio of the palladium catalyst, the alkali, the compound I and the compound shown as the formula (7) is 0.02-0.1: 1-4: 1-3: 1;
when the structural formula of the compound I is shown as the formula (12) or (13), the molar ratio of the palladium catalyst, the alkali, the compound I and the compound shown as the formula (7) is 0.04-0.1: 2-12: 1: 1-3.
6. The method according to claim 3, wherein the step S2 is specifically performed by: under the protective atmosphere, adding tert-butyl benzene or mesitylene into the compound II, adding organic lithium at the temperature of-50 to-30 ℃, and reacting for 0.8 to 2 hours at the temperature of 50 to 70 ℃; boron tribromide is added at the temperature of-50 to-30 ℃ and the reaction is carried out for 0.8 to 2 hours at room temperature; adding N, N-diisopropylethylamine under an ice bath condition, and reacting at the temperature of 120-140 ℃ for 10-20h to obtain the boron-nitrogen compound.
7. The method according to claim 3 or 6, wherein in step S2, the molar ratio of the organolithium, boron tribromide, N-diisopropylethylamine and compound II is 1-10: 1-10: 1-10: 1.
8. the method according to claim 3, wherein in the step S3, the oxidation reaction is carried out in a mixed solvent of an organic solvent II and water.
9. The method according to claim 3 or 8, wherein in step S3, the molar ratio of 2, 3-dichloro-5, 6-dicyanobenzoquinone to the boron nitrogen compound is 5 to 20: 1.
10. use of a carbonyl-fused boron nitrogen derivative as claimed in claim 1 or 2 in an organic electroluminescent device.
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| CN115433217A (en) * | 2022-08-12 | 2022-12-06 | 苏州大学 | Carbonyl-fused boron-nitrogen derivative and preparation method and application thereof |
| WO2023035820A1 (en) * | 2021-09-13 | 2023-03-16 | 广东阿格蕾雅光电材料有限公司 | B-n-containing organic electroluminescent material and use thereof in electroluminescent device |
| WO2023179092A1 (en) * | 2022-03-22 | 2023-09-28 | 苏州大学 | Carbonyl-fused boron-nitrogen derivative, and preparation method therefor and use thereof |
| CN117683055A (en) * | 2022-08-26 | 2024-03-12 | 江苏三月科技股份有限公司 | Boron-containing organic compound containing diphenyl substituted naphthopyrrole structure and organic electroluminescent device thereof |
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| CN112480154A (en) * | 2020-11-26 | 2021-03-12 | 深圳大学 | Chiral thermal activation delayed fluorescent material and circular polarization electroluminescent device thereof |
| CN114149458A (en) * | 2021-11-29 | 2022-03-08 | 苏州大学 | B/N organic electroluminescent material and preparation method and application thereof |
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| CN112480154A (en) * | 2020-11-26 | 2021-03-12 | 深圳大学 | Chiral thermal activation delayed fluorescent material and circular polarization electroluminescent device thereof |
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| WO2023179092A1 (en) * | 2022-03-22 | 2023-09-28 | 苏州大学 | Carbonyl-fused boron-nitrogen derivative, and preparation method therefor and use thereof |
| CN115433217A (en) * | 2022-08-12 | 2022-12-06 | 苏州大学 | Carbonyl-fused boron-nitrogen derivative and preparation method and application thereof |
| CN115433217B (en) * | 2022-08-12 | 2023-08-25 | 苏州大学 | Carbazole-fused boron-nitrogen derivative and preparation method and application thereof |
| WO2024031919A1 (en) * | 2022-08-12 | 2024-02-15 | 苏州大学 | Carbazole fused boron-nitrogen derivative, preparation method therefor, and use thereof |
| CN117683055A (en) * | 2022-08-26 | 2024-03-12 | 江苏三月科技股份有限公司 | Boron-containing organic compound containing diphenyl substituted naphthopyrrole structure and organic electroluminescent device thereof |
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