CN114874191A - Organic luminescent material and preparation method and application thereof - Google Patents

Organic luminescent material and preparation method and application thereof Download PDF

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CN114874191A
CN114874191A CN202210588300.0A CN202210588300A CN114874191A CN 114874191 A CN114874191 A CN 114874191A CN 202210588300 A CN202210588300 A CN 202210588300A CN 114874191 A CN114874191 A CN 114874191A
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emitting material
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王辉
陈剑锋
罗红凯
尹健
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The organic luminescent material provided by the invention has a structural general formula shown in the specification, is highly stable in a film state due to the existence of a polycyclic ring, is favorable for intermolecular charge transition capacity, and has a high photo-thermal stability due to the fact that a substituent is connected to the R position of a compound structural formula, the molecular weight is increased, and the intermolecular is not easy to crystallize and aggregate. Therefore, using the organic light emitting material of the present invention as a host in a light emitting layer, the efficiency and lifetime of the organic light emitting material of the present invention are significantly improved compared to conventional organic electroluminescent compounds. In particular, the organic light emitting material of the present invention shows properties more suitable for the current high resolution demand trend by maintaining high efficiency at high luminance and having a remarkably improved lifetime.

Description

Organic luminescent material and preparation method and application thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic luminescent material and a preparation method and application thereof.
Background
The organic electroluminescent device has the characteristics of self luminescence, wide viewing angle, high contrast, short response time, low driving voltage and the like, can realize a full-color OLED display through three organic electroluminescent materials (red, green and blue), is a latest generation flat panel display technology, can be used for a flat panel display and an illumination light source, and is put into the market in batch at present. Illumination sources will also be industrialized due to their absolute advantages. Electroluminescent devices have an all-solid-state structure, and organic electroluminescent materials are the core and foundation of the device. The development of new materials is a source power for promoting continuous progress of an electroluminescence technology, and the original material preparation and device optimization are also research hotspots of the current organic electroluminescence industry.
Therefore, the research and development of an organic luminescent material with good film forming property, high efficiency, low driving voltage, long service life and low cost, and a preparation method and application thereof are technical problems to be solved by the technical personnel in the field.
Disclosure of Invention
In view of the above, the present invention provides an organic light emitting material, and a preparation method and an application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic light-emitting material, wherein the structural general formula of the organic light-emitting material is shown as a general formula I:
Figure BDA0003664020610000021
wherein R is selected from-L- (A) n or-CX 1 X 2 ；
L is selected from a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 3-to 30-membered heteroarylene group, or a substituted or unsubstituted C3-C30 cycloalkylene group;
a is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, or-NX 3 X 4 ；
X 1 To X 4 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted fused ring of C6-C30, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl; or, linked to an adjacent substituent to form one or more rings;
n is selected from 1 or 2, and when n is selected from 2, each A may be the same or different.
Further, the C3 to C30 cycloalkyl group is any of a monocyclic alkyl group, a polycyclic alkyl group and a spiro alkyl group, and carbon atoms of the substituted C3 to C30 cycloalkyl groups may be substituted with at least one hetero atom; the heteroatom is at least one of N, O, S, Si, Se and Ge;
the C6-C30 aryl is monocyclic or polycyclic; the polycyclic group has two carbons that are common to two adjoining rings, wherein at least one of the rings is an aromatic ring and the other ring is at least one of cycloalkyl, cycloalkenyl, aryl, heteroaryl.
Further, the above aryl groups are monocyclic aryl groups and polycyclic aryl groups; the polycyclic aryl group has two or more rings in which two carbons are common to two adjoining rings, at least one of the rings being an aryl group, and the other rings being selected from the group consisting of a cycloalkyl group, a cycloalkenyl group, an aryl group, and a heteroaryl group in combination of one or more.
Further, the heteroaryl group is any one of furan, thiophene, pyridine, and triazine.
Further, the alkyl group having 1 to 30 carbon atoms is selected from any one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl;
the cycloalkyl groups include monocyclic, polycyclic, spiro alkyl groups; the cycloalkyl group is preferably a C3-C30 cycloalkyl group, more specifically including cyclopropyl, cyclopentyl, cyclohexyl, adamantyl;
the heterocycloalkyl group is a cycloalkyl group containing at least one heteroatom, preferably a heterocycloalkyl group containing 3 to 7 ring atoms including at least one of the heteroatoms, and including cyclic amines, more specifically including morpholinyl, piperidinyl, pyrrolidinyl, tetrahydrofuran, tetrahydropyran, the heteroatoms being selected from one or a combination of N, O, S, P, B, Si, Se, Ge; the above-mentioned heteroatoms are preferably N, O, S in combination of one or more.
Further, the C6-C30 aryl group is selected from any one of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene and pyrene.
It is to be noted that the above-mentioned "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted, that is, a position at which the substituent may be substituted, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
Further, the above R is selected from any one of the following groups:
Figure BDA0003664020610000041
further, the organic light emitting material is selected from any one of compounds represented by the following structural formula:
Figure BDA0003664020610000051
Figure BDA0003664020610000061
Figure BDA0003664020610000071
Figure BDA0003664020610000081
Figure BDA0003664020610000091
Figure BDA0003664020610000101
Figure BDA0003664020610000111
Figure BDA0003664020610000121
the invention also provides a preparation method of the organic luminescent material, which comprises the following steps:
(1) under the protection of nitrogen, adding 4, 5-dibromo-9, 9-dimethyl-9H-fluorene, 3-chloronaphthalene-1, 8-diyl diboronic acid, potassium carbonate, tetrakis (triphenylphosphine) palladium, toluene, ethanol and water into a reaction vessel, reacting, cooling, and performing suction filtration to obtain a compound B1-1;
(2) under the protection of nitrogen, adding a compound B1-1, 2-chloroaniline and sodium tert-butoxide into a reaction vessel, and adding toluene and a catalyst Pd 2 (dba) 3 And P (t-Bu) 3 Refluxing, cooling, adding water, stirring, standing for layering, separating liquid, passing the organic phase through a silica gel funnel, rotating the organic phase filtrate until no liquid flows out, and performing column chromatography to obtain a compound B1-2;
(3) adding a compound B1-2 and potassium carbonate into a reaction container under the protection of nitrogen, then adding DMA, then adding palladium acetate and tri-tert-butylphosphine, heating for reaction, cooling to room temperature after the reaction is stopped, adding DCM extraction reaction liquid, concentrating, and purifying by column chromatography to obtain a compound B1;
(4) under the protection of nitrogen, adding a compound B1, 2-bromo-4, 6-diphenyl-1, 3, 5-triazine and sodium tert-butoxide into a reaction vessel, adding toluene and a catalyst Pd 2 (dba) 3 And P (t-Bu) 3 Refluxing, cooling, adding water, stirring, standing for layering, separating liquid, enabling the organic phase to pass through a silica gel funnel, enabling the organic phase filtrate to be rotated until no liquid flows out, adding petroleum ether, stirring, performing suction filtration, leaching a filter cake with the petroleum ether, and drying the filter cake in vacuum to obtain the organic luminescent material shown in the general formula I;
the synthetic route of the organic luminescent material shown as the general formula I is as follows:
Figure BDA0003664020610000131
further, in the step (1), the above 4, 5-dibromo-9, 9-dimethyl-9H-fluorene, 3-chloronaphthalene-1, 8-diylboronic acid, potassium carbonate, tetrakis (triphenylphosphine) palladium, toluene, ethanol and water were used in a ratio of 142.02mmol:284mmol:426mmol:2.84mmol:600ml:300 ml.
Further, in the step (1), the reaction temperature is 90 ℃, the reaction time is 12 hours, and then the reaction solution is cooled to 25 ℃.
Further, in the step (2), the above-mentioned compound B1-1, 2-chloroAniline, sodium tert-butoxide, toluene and catalyst Pd 2 (dba) 3 、P(t-Bu) 3 The ratio of the amount of water to water was 113.36mmol, 56.68mmol, 340.08mmol, 200mL, 2.27mmol, 4.53mmol, 200 mL.
Further, in the step (2), the reflux temperature is 110 ℃, the reflux time is 15 hours, and then the temperature is cooled to 25 ℃.
Further, in the step (3), the above-mentioned compound B1-2, potassium carbonate, DMA, palladium acetate and tri-tert-butylphosphine were used in a ratio of 67.57mmol, 202.72mmol, 300mL, 2.03mmol and 2.7 mmol.
Further, in the step (3), the heating temperature was 170 ℃ and the reaction time was 12 hours.
Further, in the step (4), the above-mentioned compound B1, 2-bromo-4, 6-diphenyl-1, 3, 5-triazine, sodium tert-butoxide, toluene, and a catalyst Pd 2 (dba) 3 、P(t-Bu) 3 The ratio of the amount of water to the amount of water was 24.54mmol, 73.62mmol, 150mL, 0.49mmol, 0.98mmol, 250 mL.
Further, in the step (4), the reflux temperature is 110 ℃, the reflux time is 18h, and then the temperature is cooled to 25 ℃.
The invention also provides an application of the organic luminescent material prepared by the method and the organic luminescent material prepared by the method in preparing an organic electroluminescent device.
Further, the organic electroluminescent device comprises a first electrode, an organic electroluminescent material layer and a second electrode which are sequentially evaporated; wherein the organic electroluminescent material layer comprises the organic luminescent material.
Further, the organic electroluminescent material layer includes a light emitting layer; wherein the light-emitting layer includes a dopant material and the organic light-emitting material.
Furthermore, the mass ratio of the organic luminescent material to the doping material is (90-99.5): 0.5-10).
Further, the organic electroluminescent material layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
The invention has the beneficial effects that: the organic luminescent material provided by the invention has the advantages that the polycyclic ring is highly stable in a film state, the intermolecular charge transition capability is facilitated, meanwhile, the R position in the compound structural formula is connected with a substituent, the molecular weight is increased, the intermolecular crystallization and aggregation are not easy, and the material has higher photo-thermal stability.
Therefore, using the organic light emitting material of the present invention as a host in a light emitting layer, the efficiency and lifetime of the organic light emitting material of the present invention are significantly improved compared to conventional organic electroluminescent compounds. In particular, the organic light emitting material of the present disclosure shows properties more suitable for the current high resolution demand trend by maintaining high efficiency at high luminance and having a significantly improved lifetime.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the present invention. 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.
Synthesis of intermediate B1
Figure BDA0003664020610000151
Under the protection of nitrogen, 4, 5-dibromo-9, 9-dimethyl-9H-fluorene (142.02mmol, 50g), 3-chloronaphthalene-1, 8-diyl diboronic acid (284mmol, 71g), potassium carbonate (426mmol, 58.88g), tetrakis (triphenylphosphine) palladium (2.84mmol, 3.28g), toluene 600ml, ethanol 300ml, water 300ml, and under the protection of nitrogen, reacting at 90 ℃ for 12H, then cooling to 25 ℃, and performing suction filtration to obtain B1-1(40g, 79.82%) with the HPLC purity of more than 99.6%.
B1-1(113.36mmol, 40g), 2-chloroaniline (56.68mmol, 7.23g), sodium tert-butoxide (340.08mmol, 32.68g) are weighed into a reaction system under the protection of nitrogen, 200mL of toluene, catalysts Pd2(dba)3(2.27mmol, 1.3g) and (50%) P (t-Bu)3(4.53mmol, 0.92g) under the protection of nitrogen are added, the mixture is refluxed at 110 ℃ for 15h under the protection of nitrogen, then the mixture is cooled to 25 ℃, 200mL of purified water is added, the mixture is stirred for 30min, then the mixture is kept stand and separated, an organic phase passes through a 50g silica gel funnel, the filtrate of the organic phase is rotated until no liquid flows out, and column chromatography is carried out to obtain the compound shown as formula B1-2(32.5g, the yield is 64.58%) with the HPLC purity of more than 99.5%.
Compound B1-2(30g, 67.57mmol), potassium carbonate (28.02g, 202.72mmol) were weighed under nitrogen protection, DMA (300mL) was added to the reaction system, followed by palladium acetate (2.03mmol, 0.455g), tri-tert-butylphosphine (2.7mmol, 0.5g) and heated to 170 ℃ for 12 hours, the system was cooled to room temperature after the reaction was stopped, DCM was added to extract the reaction solution, concentrated, and purified by column chromatography to give compound B1(11.2g, yield: 40.67%) with an HPLC purity of more than 99.3%.
Example 1: preparation of Compound H1
Figure BDA0003664020610000161
Weighing the compound B1(24.54mmol, 10g), 2-bromo-4, 6-diphenyl-1, 3, 5-triazine (24.54mmol, 7.66g) and sodium tert-butoxide (73.62mmol, 7.08g) into a reaction system under the protection of nitrogen, adding 150ml of toluene, and adding a catalyst Pd under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 ℃ for 18H under the protection of nitrogen, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, filtering, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H1(12.6g, with a yield of 80.38%) with an HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 638.24 test value is 638.75. Elemental analysis: calculated values are C: 86.49 percent; h: 4.73%; n: 8.77 percent; the test value is C: 86.50%; h: 4.74 percent; n: 8.75 percent; nuclear magnetic data: 1 H-NMR(500MHz，Chloroform-d)δ8.48–8.45(m，1H)，8.45–8.44(m，1H)，8.44–8.42(m，1H)，8.42(d，J＝1.5Hz，1H)，8.18–8.14(m，2H)，8.13(t，J＝1.5Hz，1H)，8.12(t，J＝1.5Hz，2H)，7.77(dd，J＝7.5，1.6Hz，1H)，7.67(d，J＝7.5Hz，1H)，7.66–7.63(m，1H)，7.58(dd，J＝7.4，1.6Hz，1H)，7.55–7.51(m，2H)，7.51–7.49(m，5H)，7.48(d，J＝7.5Hz，1H)，7.40(d，J＝3.1Hz，1H)，7.39(s，1H)，1.80(s，3H)，1.77(s，3H).
example 2: preparation of Compound H2
Figure BDA0003664020610000171
Weighing the compound B1(24.54mmol, 10g), 2-bromo-4-naphthalene-6-phenyl-1, 3, 5-triazine (24.54mmol, 8.89g) and sodium tert-butoxide (73.62mmol, 7.08g) into a reaction system under the protection of nitrogen, adding 150ml of toluene and adding a catalyst Pd under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 ℃ for 18H under the protection of nitrogen, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, filtering, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H2(13.1g, the yield is 77.5%) with the HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 688.26 test value is 688.81. Elemental analysis: calculated values are C: 87.18 percent; h: 4.68 percent; n: 8.13 percent; the test value is C: 87.18 percent; h: 4.69 percent; n: 8.12 percent; nuclear magnetic data: 1 H-NMR(500MHz，Chloroform-d)δ8.49(dd，J＝4.3，2.1Hz，1H)，8.48–8.46(m，1H)，8.45(dd，J＝6.3，1.5Hz，2H)，8.38(dd，J＝7.3，1.6Hz，1H)，8.17(dd，J＝7.5，1.6Hz，2H)，8.15–8.12(m，1H)，8.12–8.07(m，2H)，7.99(dt，J＝7.2，1.4Hz，2H)，7.76(dd，J＝7.3，1.6Hz，2H)，7.68(d，J＝7.5Hz，1H)，7.67–7.64(m，1H)，7.62(dd，J＝7.5，1.6Hz，1H)，7.58(dd，J＝7.5，1.7Hz，1H)，7.54(dd，J＝7.4，1.4Hz，1H)，7.51(d，J＝3.2Hz，1H)，7.50–7.48(m，2H)，7.48–7.44(m，2H)，7.37(dd，J＝7.4，1.7Hz，1H)，7.32(d，J＝1.5Hz，1H)，1.80(s，3H)，1.77(s，3H).
example 3: preparation of Compound H7
Figure BDA0003664020610000181
Weighing the formula B1(24.54mmol, 10g), 2- (4-bromophenyl-), 4, 6-diphenyl-1, 3, 5-triazine (24.54mmol, 9.63g) and sodium tert-butoxide (73.62mmol, 7.08g) into a reaction system under the protection of nitrogen, adding 150ml of toluene and adding a catalyst Pd under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g) and refluxing at 110 ℃ for 18H under the protection of nitrogen, then cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, carrying out suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H7(14.1g, with the yield of 80.38%) with the HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 714.27 test value is 714.85. Elemental analysis: calculated values are C: 87.37 percent; h: 4.79 percent; n: 7.84 percent; the test value is C: 87.38 percent; h: 4.78 percent; n: 7.84 percent; nuclear magnetic data: 1 H-NMR(500MHz，Chloroform-d)δ8.38(d，J＝1.2Hz，2H)，8.36(s，4H)，8.32(d，J＝1.7Hz，2H)，8.31(d，J＝1.7Hz，1H)，8.18–8.15(m，2H)，8.15–8.14(m，2H)，8.13(d，J＝1.4Hz，1H)，8.09(d，J＝1.4Hz，1H)，8.02(dt，J＝7.5，1.5Hz，1H)，7.74(dd，J＝7.3，1.6Hz，1H)，7.65(d，J＝1.7Hz，1H)，7.64–7.61(m，1H)，7.58(dd，J＝7.5，1.7Hz，1H)，7.55–7.51(m，2H)，7.51(s，1H)，7.50(s，2H)，7.48(d，J＝7.5Hz，1H)，7.39(td，J＝7.4，1.6Hz，1H)，7.33(td，J＝7.4，1.6Hz，1H)，1.80(s，3H)，1.77(s，3H).
example 4: preparation of Compound H8
Figure BDA0003664020610000191
Weighing the formula B1(24.54mmol, 10g), 2- (4-bromophenyl-), 4-naphthyl-6-phenyl-1, 3, 5-triazine (24.54mmol, 10.76g) and sodium tert-butoxide (73.62mmol, 7.08g) into a reaction system under the protection of nitrogen, adding 150ml of toluene and adding a catalyst Pd under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 ℃ for 18H under the protection of nitrogen, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, filtering, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H8(14.3g, 76.18% yield) with the HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 764.29 test value is 764.91. Elemental analysis: calculated values are C: 87.93%; h: 4.74 percent; n: 7.32 percent; the test value is C: 87.94 percent; h: 4.75 percent; n: 7.30 percent; nuclear magnetic data: 1 H-NMR(500MHz，Chloroform-d)δ8.42–8.36(m，3H)，8.36(d，J＝1.9Hz，2H)，8.35–8.31(m，2H)，8.18–8.14(m，2H)，8.13(d，J＝1.5Hz，2H)，8.12(s，2H)，8.11–8.07(m，2H)，7.74(dd，J＝7.3，1.6Hz，2H)，7.67–7.63(m，2H)，7.63–7.61(m，1H)，7.61–7.55(m，1H)，7.55–7.52(m，2H)，7.52–7.48(m，4H)，7.46(d，J＝7.5Hz，1H)，7.38(td，J＝7.4，1.6Hz，1H)，7.31(td，J＝7.4，1.6Hz，1H)，1.80(s，3H)，1.77(s，3H).
example 5: preparation of Compound H29
Figure BDA0003664020610000201
Weighing 1(24.54mmol, 10g), (24.54mmol, 6.09g) and sodium tert-butoxide (73.62mmol, 7.08g) of the formula B under the protection of nitrogen, adding 150ml of toluene and Pd as a catalyst under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g) under nitrogenRefluxing for 18H at 110 ℃, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, spinning the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H29(11.5g, with the yield of 81.54%) with the HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 574.24 test value is 574.71. Elemental analysis: calculated values are C: 89.86 percent; h: 5.26 percent; n: 4.87 percent; the test value is C: 89.87 percent; h: 5.27 percent; n: 4.85 percent; nuclear magnetic data: 1 H-NMR(500MHz，Chloroform-d)δ8.16(dd，J＝7.4，1.6Hz，1H)，8.12(dd，J＝7.5，1.5Hz，1H)，7.96(d，J＝1.4Hz，1H)，7.94(dt，J＝7.5，1.5Hz，1H)，7.87(dd，J＝7.5，1.5Hz，1H)，7.74(dd，J＝7.4，1.6Hz，1H)，7.64–7.61(m，1H)，7.60(s，1H)，7.59–7.55(m，1H)，7.54–7.51(m，1H)，7.50(d，J＝7.5Hz，1H)，7.46(t，J＝7.4Hz，1H)，7.36(td，J＝7.4，1.6Hz，2H)，7.28(s，1H)，7.27(s，1H)，7.25(d，J＝1.9Hz，1H)，7.23(d，J＝7.5Hz，1H)，7.10(t，J＝1.8Hz，2H)，7.08(d，J＝2.0Hz，2H)，7.01(dd，J＝4.8，2.7Hz，1H)，7.00–6.97(m，1H)，1.80(s，3H)，1.76(s，3H).
example 6: preparation of Compound H30
Figure BDA0003664020610000211
Weighing the formula B1(24.54mmol, 10g), (24.54mmol, 7.96g) and sodium tert-butoxide (73.62mmol, 7.08g) into the reaction system under the protection of nitrogen, adding 150ml of toluene and Pd as a catalyst under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 deg.C for 18h under nitrogen protection, cooling to 25 deg.C, adding 250mL purified water, stirring for 30min, standing for layering, separating, passing organic phase through 50g silica gel funnel, rotating organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, vacuum filtering, leaching filter cake with petroleum ether, filtering, and filtering to obtain filtrateThe filter cake was dried in vacuo to afford the compound of formula H30(12.8g, 80.15% yield) with an HPLC purity of greater than 99.5%.
Mass spectrum: the calculated value is; 650.27 test value is 650.80. Elemental analysis: calculated values are C: 90.43 percent; h: 5.27 percent; n: 4.30 percent; the test value is C: 90.42 percent; h: 5.26 percent; n: 4.32 percent; nuclear magnetic data: 1 HNMR(500MHz，Chloroform-d)δ8.17(dd，J＝7.4，1.6Hz，1H)，8.12(dd，J＝7.5，1.5Hz，1H)，7.99(d，J＝1.5Hz，1H)，7.95(dt，J＝7.5，1.5Hz，1H)，7.89(dd，J＝7.5，1.6Hz，1H)，7.75(dd，J＝7.4，1.6Hz，1H)，7.65–7.61(m，1H)，7.61–7.59(m，1H)，7.58(q，J＝1.6Hz，1H)，7.56(d，J＝1.6Hz，1H)，7.55–7.53(m，1H)，7.53–7.51(m，1H)，7.49(d，J＝7.0Hz，1H)，7.47(d，J＝2.9Hz，1H)，7.46(s，0H)，7.40–7.33(m，1H)，7.33–7.30(m，1H)，7.29(dd，J＝3.8，1.7Hz，2H)，7.28–7.25(m，3H)，7.13–7.05(m，2H)，7.00(tt，J＝7.5，2.0Hz，1H)，1.80(s，3H)，1.77(s，3H).
example 7: preparation of Compound H60
Figure BDA0003664020610000221
Weighing 1(24.54mmol, 10g), 2- (4-bromophenyl) -4-phenylquinazoline (24.54mmol, 8.86g) and sodium tert-butoxide (73.62mmol, 7.08g) of the formula B into a reaction system under the protection of nitrogen, adding 150ml of toluene and adding Pd as a catalyst under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 ℃ for 18H under the protection of nitrogen, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, filtering, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula H60(12.5g, yield 74.06%) with HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 687.26 test value is 687.82. Elemental analysis: meterThe calculated value is C: 89.06 percent; h: 4.84 percent; n: 6.11 percent; the test value is C: 89.06 percent; h: 4.85 percent; n: 6.10 percent; nuclear magnetic data: 1 HNMR(500MHz，Chloroform-d)δ8.32(d，J＝1.6Hz，1H)，8.31(d，J＝1.6Hz，1H)，8.24(dd，J＝7.4，1.5Hz，1H)，8.20(d，J＝1.5Hz，1H)，8.19(d，J＝1.7Hz，1H)，8.15(dd，J＝5.0，1.8Hz，1H)，8.14–8.11(m，1H)，8.07(d，J＝1.5Hz，1H)，8.01(q，J＝1.6Hz，1H)，8.00(q，J＝1.6Hz，1H)，7.86(td，J＝7.5，1.5Hz，1H)，7.74(dd，J＝7.3，1.7Hz，1H)，7.70(t，J＝2.1Hz，1H)，7.68(d，J＝2.1Hz，1H)，7.66–7.63(m，1H)，7.62(td，J＝4.1，2.3Hz，2H)，7.57(dd，J＝7.4，1.6Hz，1H)，7.54–7.52(m，1H)，7.52–7.49(m，1H)，7.49–7.47(m，1H)，7.46–7.44(m，1H)，7.44–7.38(m，1H)，7.37(dd，J＝7.4，1.6Hz，1H)，7.33(dd，J＝7.4，1.7Hz，1H)，1.80(s，3H)，1.76(s，3H).
example 8: preparation of Compound H63
Figure BDA0003664020610000231
Weighing the formula B1(24.54mmol, 10g), 2-bromo-4-phenylquinazoline (24.54mmol, 7g) and sodium tert-butoxide (73.62mmol, 7.08g) in a nitrogen protection system, adding 150ml toluene, and adding Pd as a catalyst under the protection of nitrogen 2 (dba) 3 (0.49mmol, 0.28g) and (50%) P (t-Bu) 3 (0.98mmol, 0.19g), refluxing at 110 ℃ for 18H under the protection of nitrogen, cooling to 25 ℃, adding 250mL of purified water, stirring for 30min, standing for layering, separating, passing the organic phase through a silica gel funnel of 50g, rotating the organic phase filtrate until no liquid flows out, adding petroleum ether, stirring for 20min, filtering, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound H63(11g, yield 73.28%) with HPLC purity of more than 99.5%.
Mass spectrum: the calculated value is; 611.23 test value is 611.73. Elemental analysis: calculated values are C: 88.35 percent; h: 4.78 percent; n: 6.87 percent; the test value is C: 88.36 percent; h: 4.78 percent; n: 6.86 percent; nuclear magnetic data: 1 HNMR(500MHz，Chloroform-d)δ8.40–8.34(m，1H)，8.29(dd，J＝7.5，1.6Hz，1H)，8.23(d，J＝1.5Hz，1H)，8.14(t，J＝2.0Hz，1H)，8.12(t，J＝1.3Hz，1H)，8.06(dd，J＝7.5，1.7Hz，1H)，7.98(dt，J＝7.5，1.5Hz，1H)，7.88(td，J＝7.5，1.5Hz，1H)，7.79(d，J＝1.9Hz，1H)，7.77(d，J＝1.9Hz，1H)，7.74(dd，J＝7.5，1.6Hz，1H)，7.64(dd，J＝2.5，1.6Hz，1H)，7.62(dd，J＝2.5，1.6Hz，1H)，7.61–7.58(m，1H)，7.57(dd，J＝7.5，1.6Hz，1H)，7.54–7.49(m，2H)，7.49–7.45(m，3H)，7.45–7.40(m，1H)，7.40–7.37(m，1H)，7.37–7.33(m，1H)，1.80(s，3H)，1.76(s，3H).
other examples test data are shown in Table 1
TABLE 1
Examples Compound (I) Mass spectrometry Elemental analysis
Example 9 Compound H70 648.79 C:90.71；H:4.97；N:4.32
Example 10 Compound H72 535.63 C:87.45；H:4.70；N:7.84
Example 11 Compound H74 488.63 C:90.95；H:6.19；N:2.87
Example 12 Compound H75 649.77 C:90.57；H:4.81；N:2.16；O:2.46
Example 13 Compound H76 665.84 C:88.39；H:4.69；N:2.10；S:4.82
Example 14 Compound H77 675.85 C:92.41；H:5.52；N:2.07
Example 15 Compound H110 756.91 C:84.10；H:4.26；N:7.40；S:4.24
Example 16 Compound H111 667.81 C:84.53；H:4.38；N:6.29；S:4.80
Example 17 Compound H112 717.87 C:85.33；H:4.35；N:5.85；S:4.47
Example 18 Compound H120 533.65 C:92.28；H:5.10；N:2.62
Example 19 Compound H121 583.71 C:92.59；H:5.01；N:2.40
Example 20 Compound H123 559.69 C:92.27；H:5.22；N:2.50
The embodiment provides an organic electroluminescent device, which comprises a first electrode, and a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer and a second electrode which are sequentially arranged on the first electrode. Wherein the first electrode is an ITO anode; the second electrode is a cathode; a light-emitting layer was prepared from the organic electroluminescent compound H1 prepared in example 1 and the dopant material E.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
an ITO anode: coating with a thickness of
Figure BDA0003664020610000251
Cleaning the ITO (indium tin oxide) glass substrate in distilled water for 2 times, ultrasonically cleaning for 30min, repeatedly cleaning with distilled water for 2 times, ultrasonically cleaning for 10min, and ultrasonically cleaning with methanol, acetone and isopropanol in sequence after the cleaning is finishedAnd (4) washing by waves (5 min for each time), drying, and then transferring to a plasma cleaning machine for washing for 5min to obtain the ITO anode.
HIL (hole injection layer): in the evaporator, 2-TNATA (N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine) is vacuum evaporated on the ITO anode
Figure BDA0003664020610000252
A hole injection layer is formed.
HTL (hole transport layer): then, NPB (i.e., N '-diphenyl-N, N' - (1-naphthyl) -1, 1 '-biphenyl-4, 4' -diamine) was vacuum-evaporated on the hole injection layer
Figure BDA0003664020610000253
A hole transport layer is formed.
EML (light-emitting layer): a mixed material of a host material and a dopant material E of the compound H1 obtained in example 1 was vacuum-deposited on the hole transport layer as a light-emitting layer, wherein the weight ratio of the host material to the dopant material was 90:10, and the thickness was set to be 90:10
Figure BDA0003664020610000254
Wherein the structural formula of the doping material E is as follows;
Figure BDA0003664020610000255
HBL (hole blocking layer): on the luminescent layer, bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BALq) was vacuum evaporated
Figure BDA0003664020610000256
And forming a hole blocking layer.
ETL (electron transport layer): vacuum evaporation of 8-hydroxyquinoline aluminum (Alq3) onto the hole-blocking layer
Figure BDA0003664020610000257
An electron transport layer is formed.
EIL (electron injection layer): vacuum evaporation on the electron transport layer
Figure BDA0003664020610000258
An electron injection layer is formed.
Cathode: vapor plating Al1 on the electron injection layer
Figure BDA0003664020610000259
And forming a cathode to obtain the organic electroluminescent device.
Referring to the organic electroluminescent device and the method for manufacturing the same provided in example 1, organic electroluminescent compounds H2, H7, H8, H29, H30, H60, H63, H70, H72, H74, H75, H76, H77, H110, H111, H112, H120, H121, and H123 were selected instead of the organic electroluminescent compound H1 provided in example 1, and evaporation of a host material was performed to prepare an organic electroluminescent device of a corresponding compound.
Comparative example: referring to the organic electroluminescent device and the method for manufacturing the same provided in example 1, host materials P49, P51, P57, P58, P87, P88, C1, and C2 were used instead of organic electroluminescent compound H1, and evaporation of the host material was performed to prepare organic electroluminescent devices of the corresponding compounds, that is, comparative examples 1 to 8. Wherein, the structural formula of the main material RH is as follows:
Figure BDA0003664020610000261
performance detection
The organic electroluminescent devices obtained in examples 1 to 26 and comparative examples 1 to 8 described above were characterized in terms of driving voltage, luminous efficiency and lifetime at 6000(nits) luminance, and the test results are shown in table 2 below.
TABLE 2
Figure BDA0003664020610000262
Figure BDA0003664020610000271
Figure BDA0003664020610000281
As can be seen from table 2, compared with comparative examples 1 to 8, the driving voltage of the organic electroluminescent devices provided in examples 1 to 20 of the present invention is 3.2V to 3.9V, which is significantly lower than that of comparative examples 1 to 8, and the luminous efficiency is higher than that of comparative examples 1 to 8, and the lifetime is much longer than that of comparative examples, so that it can be seen that the organic electroluminescent devices prepared using the organic electroluminescent compounds provided in the present invention as the luminescent layer material have significantly reduced driving voltage, significantly improved luminous efficiency, and significantly improved lifetime, compared with the organic electroluminescent devices prepared using the comparative compound RH as the luminescent layer material.
The above description is for simplicity of explanation, and the application of the present invention is not limited to the above examples, and it is obvious to those skilled in the art that modifications and variations can be made within the scope of the above description, and all such modifications and variations are intended to fall within the scope of the claims. In the following description, the scope of the present disclosure is not limited to the embodiments described in the embodiments. The scope of the present invention must be interpreted within the scope of the following claims, and all techniques that are equivalent to the scope of the present invention are included in the scope of the claims.

Claims (10)

1. An organic light-emitting material is characterized in that the structural general formula of the organic light-emitting material is shown as a general formula I:
Figure FDA0003664020600000011
wherein R is selected from-L- (A) n or-CX 1 X 2 ；
L is selected from a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted 3-to 30-membered heteroarylene group, or a substituted or unsubstituted C3-C30 cycloalkylene group;
a is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, or-NX 3 X 4 ；
X 1 To X 4 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted fused ring of C6-C30, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl; or, linked to an adjacent substituent to form one or more rings;
n is selected from 1 or 2, and when n is selected from 2, each A may be the same or different.
2. The organic light-emitting material of claim 1, wherein the C3-C30 cycloalkyl is any one of monocycloalkyl, polycycloalkyl and spiroalkyl, and carbon atoms of the substituted C3-C30 cycloalkyl can be substituted by at least one heteroatom; the heteroatom is at least one of N, O, S, Si, Se and Ge;
the C6-C30 aryl is monocyclic group or polycyclic group; the polycyclic group has multiple rings with two carbons common to two adjoining rings, wherein at least one ring is aromatic and the others are at least one of cycloalkyl, cycloalkenyl, aryl, heteroaryl.
3. A method for preparing the organic light emitting material as claimed in claim 1 or 2, comprising the steps of:
(1) under the protection of nitrogen, adding 4, 5-dibromo-9, 9-dimethyl-9H-fluorene, 3-chloronaphthalene-1, 8-diyl diboronic acid, potassium carbonate, tetrakis (triphenylphosphine) palladium, toluene, ethanol and water into a reaction vessel, reacting, cooling and carrying out suction filtration to obtain a compound B1-1;
(2) under the protection of nitrogen, adding a compound B1-1, 2-chloroaniline and sodium tert-butoxide into a reaction vessel, and adding toluene and a catalyst Pd 2 (dba) 3 And P (t-Bu) 3 Refluxing, cooling, adding water, stirring, standing for layering, separating liquid, passing the organic phase through a silica gel funnel, rotating the organic phase filtrate until no liquid flows out, and performing column chromatography to obtain a compound B1-2;
(3) adding a compound B1-2 and potassium carbonate into a reaction container under the protection of nitrogen, then adding DMA, then adding palladium acetate and tri-tert-butylphosphine, heating for reaction, cooling to room temperature after the reaction is stopped, adding DCM extraction reaction liquid, concentrating, and purifying by column chromatography to obtain a compound B1;
(4) under the protection of nitrogen, adding a compound B1, 2-bromo-4, 6-diphenyl-1, 3, 5-triazine and sodium tert-butoxide into a reaction vessel, adding toluene and a catalyst Pd 2 (dba) 3 And P (t-Bu) 3 Refluxing, cooling, adding water, stirring, standing for layering, separating liquid, enabling the organic phase to pass through a silica gel funnel, enabling the organic phase filtrate to be rotated until no liquid flows out, adding petroleum ether, stirring, performing suction filtration, leaching a filter cake with the petroleum ether, and drying the filter cake in vacuum to obtain the organic luminescent material shown in the general formula I;
the synthetic route of the organic luminescent material shown as the general formula I is as follows:
Figure FDA0003664020600000031
4. the method according to claim 3, wherein in the step (1), the ratio of the 4, 5-dibromo-9, 9-dimethyl-9H-fluorene, the 3-chloronaphthalene-1, 8-diyl diboronic acid, the potassium carbonate, the tetrakis (triphenylphosphine) palladium, the toluene, the ethanol, and the water is 142.02mmol, 284mmol, 426mmol, 2.84mmol, 600ml, 300 ml.
5. The method according to claim 3, wherein in the step (1), the reaction temperature is 90 ℃ and the reaction time is 12h, and then the mixture is cooled to 25 ℃.
6. The method of claim 3The preparation method of the organic luminescent material is characterized in that in the step (2), the compound B1-1, 2-chloroaniline, sodium tert-butoxide, toluene and a catalyst Pd are used 2 (dba) 3 、P(t-Bu) 3 The ratio of the amount of water to water was 113.36mmol, 56.68mmol, 340.08mmol, 200mL, 2.27mmol, 4.53mmol, 200 mL.
7. The method according to claim 3, wherein in the step (2), the reflux temperature is 110 ℃, the reflux time is 15h, and then the mixture is cooled to 25 ℃.
8. The method for preparing an organic light-emitting material according to claim 3, wherein in the step (3), the compound B1-2, the potassium carbonate, the DMA, the palladium acetate and the tri-tert-butylphosphine are used in a ratio of 67.57mmol, 202.72mmol, 300mL, 2.03mmol and 2.7 mmol.
9. The method according to claim 3, wherein in the step (4), the compound B1, 2-bromo-4, 6-diphenyl-1, 3, 5-triazine, sodium tert-butoxide, toluene and Pd as a catalyst are added 2 (dba) 3 、P(t-Bu) 3 The ratio of the amount of water to the amount of water was 24.54mmol, 73.62mmol, 150mL, 0.49mmol, 0.98mmol, 250 mL.
10. Use of an organic light-emitting material according to claim 1 or 2 and an organic light-emitting material prepared by a method according to any one of claims 3 to 9 for the preparation of an organic electroluminescent device.
CN202210588300.0A 2022-05-26 2022-05-26 Organic luminescent material and preparation method and application thereof Withdrawn CN114874191A (en)

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