CN110963989A - Compound with xanthene as core and application thereof - Google Patents

Compound with xanthene as core and application thereof Download PDF

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CN110963989A
CN110963989A CN201811159110.7A CN201811159110A CN110963989A CN 110963989 A CN110963989 A CN 110963989A CN 201811159110 A CN201811159110 A CN 201811159110A CN 110963989 A CN110963989 A CN 110963989A
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李崇
谢丹丹
叶中华
王芳
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound taking xanthene as a core and application thereof, belonging to the technical field of semiconductors, wherein the structure of the compound taking xanthene as the core is shown as a general formula (1):
Figure DDA0001819611570000011
the invention also provides application of the compound taking the xanthene as the core. The compound takes the xanthene as a core, has high carrier mobility and good carrier balance capability, and simultaneously has high glass transition temperature, high molecular thermal stability and proper HOMO and LUMO energy levels. The compound is used as a light-emitting layerThe host material can generate a triplet-triplet coupling effect, so that the utilization rate of the triplet is effectively improved; the device structure based on the compound can effectively improve the efficiency and the service life of an OLED device.

Description

Compound with xanthene as core and application thereof
Technical Field
The invention relates to a compound taking xanthene as a core and application thereof, belonging to the technical field of semiconductors.
Background
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, the OLED photoelectric functional material needs to be continuously researched and innovated, and an OLED functional material with higher performance is created.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
Currently, the efficiency and lifetime of blue light devices, especially deep blue light devices, are a problem in OLED research, and especially the difference between the lifetime of blue light devices and the lifetimes of green and red light devices is large. The main reason is that on one hand, the driving of the blue light device is larger than high, and the material is easy to generate membrane phase separation under the action of heat; in addition, since the energy of blue light is high, the stability of the material is lowered, and the material is easily decomposed. The blue light material mainly comprises fluorescence and phosphorescence, and although the blue phosphorescence material has high device efficiency, the blue phosphorescence material has the characteristics of high material cost, poor service life and the like, so that the blue light material is restricted to be applied to devices. Currently, the mainstream device manufacturers use fluorescent materials for blue light devices, and although the efficiency of the fluorescent materials is low, the service life of the fluorescent materials is long. The traditional fluorescent material cannot emit light due to the influence of spin forbidden resistance, and the theoretical limit of external quantum efficiency of the device is 5%; and the TTA material, including TTA host and TTA doping material, can utilize triplet-triplet coupling effect to raise the theoretical limit value of external quantum efficiency of the device to 12.5%. Therefore, the development of high-efficiency and high-stability blue-light TTA host materials is an important direction in the field of blue-light devices.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
An object of the present invention is to provide a compound having a xanthene core. The compound takes the xanthene as a core, has higher glass transition temperature and molecular thermal stability, also has proper HOMO and carrier mobility, and is beneficial to reducing the driving voltage of the device and prolonging the service life of the device.
The technical scheme for solving the technical problems is as follows: a compound taking xanthene as a core has a structure shown as a general formula (1):
Figure BDA0001819611550000021
in the general formula (1), Z represents a nitrogen atom or C-R;
l represents a single bond, substituted or unsubstituted C6-C30One of an arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
r, which is identical or different at each occurrence, is hydrogen, halogen, cyano, C1-C20Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
Ar1、Ar2each independently represents substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
wherein the substituents of the substitutable group are optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, in the general formula (1), at least one of Z's is a nitrogen atom.
Further, in the general formula (1), Ar is1、Ar2And R independently represents a structure represented by a general formula (2), a general formula (3), a general formula (4) or a general formula (5);
Figure BDA0001819611550000031
wherein the symbols and indices used have the meanings given above,
in the general formulae (2) and (3), X is1、X2、X3Each independently represents a single bond, an oxygen atom, a sulfur atom, -C (R)4)(R5)-、-Si(R6)(R7)-、
Figure BDA0001819611550000032
or-N (R)8) -one of the above; and X1、X2Not simultaneously represent a single bond; wherein R is4And R5、R6And R7Can be bonded to each other to form a ring;
R1～R3each independently represents a hydrogen atom, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; r1～R3The connection mode with the general formula (2) or the general formula (3) is single bond substitution connection or ring-merging connection;
z, which is the same or different at each occurrence, is represented by a nitrogen atom or C-H; z at the connecting site with other groups represents a carbon atom;
in the general formula (4) and the general formula (5), X represents a nitrogen atom or C-R9；
The R is4～R8Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the R is9Represented by hydrogen atom, cyano group, halogen, C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C30Aryl of (a), substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, two or more adjacent R9Can be bonded to each other to form a ring;
wherein said substitutable group is optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
Further, in the general formula (2) or the general formula (3), R is1～R3Independently represent a hydrogen atom, a structure represented by general formula (6), general formula (7) or general formula (8);
Figure BDA0001819611550000041
said Y is1、Y2、Y3Each independently represents an oxygen atom, a sulfur atom, -C (R)10)(R11)-、-Si(R12)(R13)-、
Figure BDA0001819611550000042
or-N (R)14) -one of the above; wherein R is10And R11、R12And R13Can be bonded to each other to form a ring;
wherein represents a site of formula (6), formula (7) or formula (8) in parallel ring-connection with formula (2) or formula (3);
the Y represents a nitrogen atom or C-H;
the R is10～R14Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
Further, the L represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted benzothiophenylene group;
ar is1、Ar2Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted naphthyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted isobenzothiophenyl and substituted or unsubstituted isoquinolyl;
the R is4～R8、R10～R14Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, biphenylyl, naphthyridinyl or pyridyl;
the R, R9Each independently represents a hydrogen atom, a cyano group, a fluorine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group;
the substituent of the substitutable group is one or more selected from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, naphthyridinyl or pyridyl.
Further, the structure of the general formula (1) is specifically represented by any one of the following structures:
Figure BDA0001819611550000051
Figure BDA0001819611550000061
Figure BDA0001819611550000071
Figure BDA0001819611550000081
Figure BDA0001819611550000091
Figure BDA0001819611550000101
Figure BDA0001819611550000111
the second objective of the present invention is to provide an organic electroluminescent device. The compound has good application effect and good industrialization prospect in OLED light-emitting devices.
The technical scheme for solving the technical problems is as follows: at least one functional layer of the organic electroluminescent device contains the compound taking xanthene as the core.
On the basis of the technical scheme, the invention can be further improved as follows.
The light-emitting layer further includes a light-emitting layer, and the host material of the light-emitting layer is the above-described xanthene-based compound.
It is a further object of the present invention to provide an illumination or display device. The organic electroluminescent device can be applied to display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a lighting or display element comprising an organic electroluminescent device as described above.
The invention has the beneficial effects that:
1. the compound takes the xanthene as a core, and due to the introduction of double bonds, the hole mobility of the material is effectively improved, and the hole mobility and the electron mobility are more matched. When the compound is used as a host material and matched with a blue fluorescent material, the compound area of the current carrier can be far away from one side of the hole transport layer/the electron blocking layer. On one hand, the carrier recombination region of the device can be improved, and the quenching probability of triplet excitons is reduced; in addition, the accumulation of holes in the hole transport layer/the electron blocking layer can be effectively prevented, and the service life of the device is prolonged.
2. The compound has higher glass transition temperature and molecular thermal stability, effectively ensures the stability of the material, and prevents the phase separation of material films and the decomposition of the material when the device works for a long time. Meanwhile, the material has proper HOMO and LUMO energy levels and carrier mobility, can be well matched with EB and ET materials in device energy level, and reduces the driving voltage of the device.
3. The compound has higher S1 singlet state energy level, T1 is more than or equal to 0.5S1, and the compound has good TTA effect, can fully utilize triplet state energy, and improves the external quantum efficiency of devices.
Drawings
FIG. 1 is a schematic diagram of a device structure to which the compound of the present invention is applied, wherein the components represented by the respective reference numerals are as follows:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer, 5, electron blocking layer, 6, luminescent layer, 7, electron transport layer, 8, electron injection layer, 9, cathode reflecting electrode layer.
Detailed Description
Synthesis of intermediate B:
Figure BDA0001819611550000121
under the protection of nitrogen, adding the raw material A and a proper amount of toluene, then adding carbon tetrachloride and triphenylphosphine, heating and refluxing for reaction for 18-24 hours, then cooling to room temperature, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate B; the molar ratio of the raw material A to carbon tetrachloride is 1: 1-1: 2, the molar ratio of the raw material A to triphenyl phosphine is 1: 0.01-1: 0.1, and 60-80ml of toluene is added into 0.01mol of the raw material A as the toluene solvent.
Synthesis of intermediate F:
Figure BDA0001819611550000122
(1) under the protection of nitrogen, adding raw materials C and Ar2Adding mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, and adding triphenylphosphine and dichlorotriphenylphosphine palladiumHeating and refluxing at 80-120 ℃ for reaction for 15-20 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain an intermediate D; the raw materials C and Ar2The molar ratio of-Br is 1: 1.05-1: 1.0, the molar ratio of the raw material C to the triphenyl phosphine is 1: 0.001-1: 0.01, the molar ratio of the raw material C to the dichlorotriphenyl phosphine palladium is 1: 0.001-1: 0.01, and the dosage of the mixed solvent is 0.01mol, and 150ml of 100-150ml of mixed solvent is added into the raw material C.
(2) Under the protection of nitrogen, adding an intermediate D and Br-L-Br, then adding a mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, then adding triphenylphosphine and palladium dichlorotriphenylphosphate, heating and refluxing at 85-120 ℃ for 20-24 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain an intermediate E; the molar ratio of the intermediate D to Br-L-Br is 1: 1.05-1: 1.0, the molar ratio of the intermediate D to triphenylphosphine is 1: 0.001-1: 0.01, the molar ratio of the intermediate D to dichlorotriphenylphosphine palladium is 1: 0.001-1: 0.01, and the dosage of the mixed solvent is that 100-150ml of mixed solvent is added into 0.01mol of the intermediate D.
(3) Weighing the intermediate E, dissolving the intermediate E in tetrahydrofuran under the nitrogen atmosphere, cooling to-78 ℃, slowly dropping a cyclohexane solution containing n-butyllithium, and stirring for 30 minutes under heat preservation; slowly dripping tetrahydrofuran solution containing trimethyl borate, slowly heating to room temperature after dripping, and reacting for 10 hours under heat preservation; after the reaction is finished, cooling to 0 ℃, slowly dripping distilled water, stirring for 1 hour after no gas is generated, and then heating to room temperature; extracting with ethyl acetate, washing with saturated saline solution, drying with anhydrous magnesium sulfate, distilling under reduced pressure, and recrystallizing the obtained solid with mixed solution of toluene and ethanol to obtain intermediate F; the molar ratio of the intermediate E to the n-butyllithium is 1 (1-2), the molar ratio of the intermediate E to the trimethyl borate is 1 (3-6), and the dosage ratio of the intermediate E to the THF is 1g (20-30 ml).
Synthesis of intermediate G:
Figure BDA0001819611550000131
adding the intermediate B and the intermediate F under the protection of nitrogen, then adding a mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, then adding triphenylphosphine and dichlorotriphenylphosphine palladium, heating and refluxing at 80-130 ℃ for reaction for 15-20 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain an intermediate G; the molar ratio of the intermediate B to the intermediate F is 1: 1.05-1: 1.0, the molar ratio of the intermediate B to triphenylphosphine is 1: 0.001-1: 0.01, the molar ratio of the intermediate B to dichlorotriphenylphosphine palladium is 1: 0.001-1: 0.01, and the amount of the mixed solvent is that 100-150ml of mixed solvent is added into 0.01mol of the intermediate B.
Synthesis of a final product:
Figure BDA0001819611550000132
under the protection of nitrogen, adding the intermediate G and the raw material H, then adding a mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, then adding triphenylphosphine and dichlorotriphenylphosphine palladium, heating and refluxing at 85-130 ℃ for 20-24 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain a target product; the molar ratio of the intermediate G to the raw material H is 1: 1.05-1: 1.0, the molar ratio of the intermediate G to the triphenyl phosphine is 1: 0.001-1: 0.01, the molar ratio of the intermediate G to the dichlorotriphenyl phosphine palladium is 1: 0.001-1: 0.01, and the amount of the mixed solvent is that 100-150ml of mixed solvent is added into 0.01mol of the intermediate G.
The starting materials and intermediates involved in the preparation of the compounds of synthesis examples 1-21 are shown in Table 1, and reference is made to the above procedures for the preparation of the intermediates involved.
TABLE 1
Figure BDA0001819611550000141
Figure BDA0001819611550000151
Figure BDA0001819611550000161
Example 1: preparation of Compound 1
Figure BDA0001819611550000162
To a 200ml three-necked flask, 0.01mol of intermediate C-1, 0.011mol of 1-bromonaphthalene, 0.03mol of potassium carbonate, and 1X 10 mol of potassium carbonate were added under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine, then 120ml of toluene: ethanol: the mixture of water and water at 1:1:1 was heated at 80-125 ℃ under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to obtain intermediate D-1.
To a 200ml three-necked flask, 0.01mol of intermediate D-1, 0.011mol of p-dibromobenzene, 0.03mol of potassium carbonate, and 1X 10 mol were added under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine, then 120ml of toluene: ethanol: water-1: 1:1 mixed solution, heated at 85-130 ℃ under reflux for 24 hours, and the reaction was observed by TLC until completion. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to afford intermediate E-1.
Weighing 0.01mol of intermediate E-1 under the nitrogen atmosphere, dissolving in 45ml of tetrahydrofuran, cooling to-78 ℃, slowly dripping a cyclohexane solution containing 0.02mol of n-butyllithium, and keeping the temperature and stirring for 30 minutes after dripping is finished; slowly dripping tetrahydrofuran solution containing 0.035mol trimethyl borate, after dripping, slowly heating to room temperature, and reacting for 10 hours under the condition of heat preservation; the reaction is finishedThen, cooling to 0 ℃, slowly dripping distilled water, stirring for 1.5 hours after no gas is generated, and then heating to room temperature; the reaction mixture was extracted with 150ml of ethyl acetate, the extract was washed three times with 150ml of saturated brine, finally dried over anhydrous magnesium sulfate, the solution was distilled under reduced pressure, and the obtained solid was dissolved in 300ml of VToluene：VEthanolThe mixture was recrystallized at a ratio of 3:1 to give intermediate F-1.
Figure BDA0001819611550000171
To a 200ml three-necked flask, 0.01mol of intermediate B-1, 0.011mol of intermediate F-1, 0.03mol of potassium carbonate, and 1X 10 mol were added under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine and then 120ml of VToluene:VEthanol:VWater (W)The mixture was heated at 80-120 ℃ under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to afford intermediate G-1.
Figure BDA0001819611550000172
In a 200ml three-necked flask, 0.01mol of intermediate G-1, 0.011mol of raw material H-1, 0.03mol of potassium carbonate, and 1X 10 mol of potassium carbonate were placed under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine and then 120ml of VToluene:VEthanol:VWater (W)The mixture was heated at 85-130 ℃ under reflux for 15-22 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to obtain the target product compound 1 with purity of 99.1% and yield of 75.8%.
Elemental analysis Structure (molecular formula C)50H32O): theoretical value: c, 92.56; h, 4.97; o, 2.47; test values are: c, 92.55; h, 4.96; o, 2.44.
ESI-MS(m/z)(M+): theoretical value is 648.25, found 648.23.
Example 2: preparation of Compound 26
Figure BDA0001819611550000173
Prepared according to the synthesis method of the compound 1, except that the intermediate G-2 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)46H30O): theoretical value: c, 92.28; h, 5.05; o, 2.67; test values are: c, 92.27; h, 5.05; o, 2.65.
ESI-MS(m/z)(M+): theoretical value is 598.23, found 598.21.
Example 3: preparation of Compound 21
Figure BDA0001819611550000181
Prepared according to the synthesis method of the compound 1, except that the intermediate G-3 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)56H34O2): theoretical value: c, 91.03; h, 4.64; o, 4.33; test values are: c, 91.02; h,4.65O, 4.35.
ESI-MS(m/z)(M+): theoretical value is 738.26, found 738.25.
Example 4: preparation of Compound 27
Figure BDA0001819611550000182
Prepared according to the synthesis method of the compound 1, except that the intermediate G-4 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)52H34O): theoretical value: c, 92.55; h, 5.08; o, 2.37; test values are: c, 92.55; h, 5.06; o, 2.39.
ESI-MS(m/z)(M+): theoretical value is 674.26, found 674.28.
Example 5: preparation of Compound 18
Figure BDA0001819611550000183
Prepared according to the synthesis method of the compound 1, except that the intermediate G-5 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)45H29NO): theoretical value: c, 90.12; h, 4.87; n, 2.34; o, 2.67; test values are: c, 90.11; h, 4.86; n, 2.35; o, 2.65.
ESI-MS(m/z)(M+): theoretical value is 599.22, found 599.20.
Example 6: preparation of Compound 150
Figure BDA0001819611550000191
Prepared according to the synthesis method of the compound 1, except that the intermediate G-6 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)42H26N2O): theoretical value: c, 87.78; h, 4.56; n, 4.87; o, 2.78; test values are: c, 87.77; h, 4.55; n, 4.85; o, 2.79.
ESI-MS(m/z)(M+): theoretical value is 574.20, found 574.22.
Example 7: preparation of Compound 20
Figure BDA0001819611550000192
Prepared according to the synthesis method of the compound 1, except that the intermediate G-7 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)48H29FO2): theoretical value: c, 87.78; h, 4.45; f, 2.89; o, 4.87; test values are: c, 87.76; h, 4.46; f, 2.91; and O, 4.86. ESI-MS (M/z) (M)+): theoretical value is 656.22, found 656.23.
Example 8: preparation of Compound 29
Figure BDA0001819611550000193
Prepared according to the synthesis method of the compound 1, except that the intermediate G-8 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)50H35NO2): theoretical value: c, 88.08; h, 5.17; n, 2.05; o, 4.69; test values are: c, 88.06; h, 5.16; n, 2.03; and O, 4.68.
ESI-MS(m/z)(M+): theoretical value is 681.27, found 681.26.
Example 9: preparation of Compound 28
Figure BDA0001819611550000201
Prepared according to the synthesis method of the compound 1, except that the intermediate G-9 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)54H35NO): theoretical value: c, 90.85; h, 4.94; n, 1.96; o, 2.24; test values are: c, 90.84; h, 4.93; n, 1.98; o, 2.26.
ESI-MS(m/z)(M+): theoretical value is 713.27, found 713.25.
Example 10: preparation of Compound 32
Figure BDA0001819611550000202
The compound is prepared according to the synthetic method of the compound 1, except that the intermediate G-10 is used for replacing the intermediate G-1, the raw material H-8 is used for replacing the raw material H-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)47H29N3O): theoretical value: c, 86.61; h, 4.49; n, 6.45; o, 2.45; test values are: c, 86.62; h, 4.48; n, 6.46; o, 2.43. ESI-MS (M/z) (M)+): theoretical value is 651.23, found 651.25.
Example 11: preparation of Compound 37
Figure BDA0001819611550000211
Prepared according to the synthesis method of the compound 1, except that the intermediate G-11 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)50H32O): theoretical value: c, 92.56; h, 4.97; o, 2.47; test values are: c, 92.55; h, 4.96; o, 2.48.
ESI-MS(m/z)(M+): theoretical value is 648.25, found 648.27.
Example 12: preparation of Compound 87
Figure BDA0001819611550000212
Prepared according to the synthesis method of the compound 1, except that the intermediate G-12 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)51H37NO): theoretical value: c, 90.10; h, 5.49; n, 2.06; o, 2.35; test values are: c, 90.11; h, 5.50; n, 2.04; o, 2.36.
ESI-MS(m/z)(M+): theoretical value is 679.29, found 679.26.
Example 13: preparation of Compound 110
Figure BDA0001819611550000213
Prepared according to the synthesis method of the compound 1, except that the intermediate G-13 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)58H39NO): theoretical value: c, 90.95; h, 5.13; n, 1.83; o, 2.09;
test values are: c, 90.93; h, 5.12; n, 1.81; and O, 2.07. ESI-MS (M/z) (M)+): theoretical value is 765.30, found 765.28.
Example 14: preparation of Compound 153
Figure BDA0001819611550000221
Prepared according to the synthesis method of the compound 1, except that the intermediate G-14 is used for replacing the intermediate G-1, the raw material H-2 is used for replacing the raw material H-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)52H32O): theoretical value: c, 92.83; h, 4.79; o, 2.38; test values are: c, 92.81; h, 4.78; o, 2.39.
ESI-MS(m/z)(M+): theoretical value is 672.25, found 672.23.
Example 15: preparation of Compound 135
Figure BDA0001819611550000222
Prepared according to the synthesis method of the compound 1, except that the intermediate G-15 is used for replacing the intermediate G-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)48H30N2O): theoretical value: c, 88.59; h, 4.65; n, 4.30; o, 2.46; test values are: c, 88.58; h, 4.66; n, 4.32; o, 2.45.
ESI-MS(m/z)(M+): theoretical value of650.24, found 650.25.
Example 16: preparation of Compound 154
Figure BDA0001819611550000223
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate G-1 was replaced with the intermediate G-16 and the raw material H-1 was replaced with the raw material H-9, and the purity of the obtained objective product was 98.8% and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)48H30N2O): theoretical value: c, 88.59; h, 4.65; n, 4.30; o, 2.46; test values are: c, 88.57; h, 4.66; n, 4.32; and O, 5.28. ESI-MS (M/z) (M)+): theoretical value is 650.24, found 650.23.
Example 17: preparation of Compound 157
Figure BDA0001819611550000231
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate G-1 was replaced with the intermediate G-17 and the raw material H-1 was replaced with the raw material H-3, and the purity of the obtained objective product was 98.8% and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)56H36O): theoretical value: c, 92.79; h, 5.01; o, 2.21; test values are: c, 92.78; h, 5.03; o, 2.20.
ESI-MS(m/z)(M+): theoretical value is 724.28, found 724.26.
Example 18: preparation of Compound 160
Figure BDA0001819611550000232
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate G-1 was replaced with the intermediate G-18 and the raw material H-1 was replaced with the raw material H-4, and the purity of the obtained objective product was 98.8% and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)45H27N3O): theory of the inventionThe value: c, 86.38; h, 4.35; n, 6.72; o, 2.56; test values are: c, 86.36; h, 4.35; n, 6.70; o, 2.55. ESI-MS (M/z) (M)+): theoretical value is 625.22, found 625.24.
Example 19: preparation of Compound 163
Figure BDA0001819611550000241
The compound was prepared according to the synthetic method of the compound 1 except that the intermediate G-1 was replaced with the intermediate G-19 and the raw material H-1 was replaced with the raw material H-5, and the purity of the obtained objective product was 98.8% and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)50H30O2): theoretical value: c, 90.61; h, 4.56; o, 4.83; test values are: c, 90.60; h, 4.55; and O, 4.85.
ESI-MS(m/z)(M+): theoretical value is 662.22, found 662.23.
Example 20: preparation of Compound 166
Figure BDA0001819611550000242
The compound is prepared according to the synthesis method of the compound 1, except that the intermediate G-20 is used for replacing the intermediate G-1, the raw material H-6 is used for replacing the raw material H-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)50H30O2): theoretical value: c, 90.61; h, 4.56; o, 4.83; test values are: c, 90.60; h, 4.55; and O, 4.85.
ESI-MS(m/z)(M+): theoretical value is 662.22, found 662.20.
Example 21: preparation of Compound 181
Figure BDA0001819611550000243
Prepared according to the synthesis method of the compound 1, except that the intermediate G-21 is used for replacing the intermediate G-1, the raw material H-7 is used for replacing the raw material H-1, the purity of the obtained target product is 98.8 percent, and the yield is 75.1 percent.
Elemental analysis Structure (molecular formula C)56H32O3): theoretical value: c, 89.34; h, 4.28; o, 6.38; test values are: c, 89.35; h, 4.26; and O, 6.36.
ESI-MS(m/z)(M+): theoretical value is 752.24, found 752.22.
Example 22: preparation of Compound 14
Figure BDA0001819611550000251
A250 ml three-necked flask was prepared, and 0.01mol of the reactant 1, 0.012mol of the reactant 2, 0.03mol of sodium tert-butoxide, and 1X 10 in an atmosphere of nitrogen gas were added-4mol Pd2(dba)3，1×10-4Heating and refluxing the mol of tri-tert-butylphosphine and 150ml of toluene at 80 ℃ for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate 1.
Figure BDA0001819611550000252
To a 200ml three-necked flask, 0.01mol of intermediate 1, 0.011mol of p-dibromobenzene, 0.03mol of potassium carbonate, and 1X 10 under a nitrogen atmosphere were added-4mol Pd(PPh3)Cl2And 1X 10-4The triphenyl phosphine is added in mol, and then 120mlV is addedToluene:VEthanol:VWater (W)The mixture was heated at 85-130 ℃ under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to afford intermediate 2.
Weighing 0.01mol of intermediate 2 under the nitrogen atmosphere, dissolving the intermediate 2 in 45ml of tetrahydrofuran, cooling to-78 ℃, slowly dripping a cyclohexane solution containing 0.02mol of n-butyllithium, and keeping the temperature and stirring for 30 minutes after dripping is finished; the tetrahydrofuran containing 0.035mol trimethyl borate is slowly drippedAfter the solution is dropwise added, slowly heating to room temperature, and reacting for 10 hours under the condition of heat preservation; after the reaction is finished, cooling to 0 ℃, slowly dripping distilled water, stirring for 1.5 hours after no gas is generated, and then heating to room temperature; the reaction mixture was extracted with 150ml of ethyl acetate, the extract was washed with 150ml of saturated brine three times, finally dried over anhydrous magnesium sulfate, the solution was distilled under reduced pressure, and the obtained solid was used 300mlVToluene:VEthanolThe mixture at 3:1 was recrystallized to give intermediate 3.
Figure BDA0001819611550000253
To a 200ml three-necked flask, 0.01mol of intermediate B-1, 0.011mol of intermediate 3, 0.03mol of potassium carbonate, and 1X 10 mol were charged under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine and then 120ml of VToluene:VEthanol:VWater (W)The mixture was heated at 80-120 ℃ under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was purified by silica gel column (dichloromethane: mixed solvent of petroleum ether ═ 1:5 as eluent) to give intermediate G-22.
Figure BDA0001819611550000261
In a 200ml three-necked flask, 0.01mol of intermediate G-22, 0.011mol of raw material H-1, 0.03mol of potassium carbonate, and 1X 10 mol of potassium carbonate were placed under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine and then 120ml of VToluene:VEthanol:VWater (W)The mixture was heated at 80-120 ℃ under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was passed through a silica gel column (V)Methylene dichloride:VPetroleum etherMixed solvent of 1:5 as eluent) to obtain compound 14, and the target product is obtainedThe purity of the product was 98.8%, and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)52H33NO): theoretical value: c, 90.80; h, 4.48; (ii) a N, 2.04; o, 2.33; test values are: c, 90.81; h, 4.46; n, 2.05; o, 2.35.
ESI-MS(m/z)(M+): theoretical value is 687.26, found 687.25.
Example 23: preparation of Compound 183
Figure BDA0001819611550000262
Prepared according to the synthetic method of compound 14, except that intermediate G-23 was used instead of intermediate G-22, the purity of the obtained target product was 98.8%, and the yield was 75.1%.
Elemental analysis Structure (molecular formula C)58H35NO2): theoretical value: c, 89.55; h, 4.54; (ii) a N, 1.80; o, 4.11; test values are: c, 89.56; h, 4.55; n, 1.82; and O, 4.13.
ESI-MS(m/z)(M+): theoretical value is 777.27, found 777.25.
Example 24: preparation of Compound 200
Figure BDA0001819611550000271
Prepared according to the synthetic method of compound 14, except that intermediate G-24 is used instead of intermediate G-22, the purity of the obtained target product is 98.8%, and the yield is 75.1%.
Elemental analysis Structure (molecular formula C)58H43NO): theoretical value: c, 90.47; h, 5.63; (ii) a N, 1.82; o, 2.08; test values are: c, 90.45; h, 5.62; n, 1.80; o, 2.05.
ESI-MS(m/z)(M+): theoretical value is 769.33, found 769.31.
Example 25: preparation of Compound 185
Figure BDA0001819611550000272
Prepared according to the synthetic method of compound 14, except that intermediate G-25 is used instead of intermediate G-22, the purity of the obtained target product is 98.8%, and the yield is 75.1%.
Elemental analysis Structure (molecular formula C)55H37NO): theoretical value: c, 90.75; h, 5.12; (ii) a N, 1.92; o, 2.20; test values are: c, 90.76; h, 5.14; n, 1.94; o, 2.23.
ESI-MS(m/z)(M+): theoretical value is 727.29, found 727.28.
The organic compound of the present invention is used in a light-emitting device as a host material of a light-emitting layer. The thermal properties, the HOMO/LUMO energy levels and the cyclic voltammetric characteristics of the compounds of the invention and CBP were measured, respectively, and the results are shown in Table 2.
TABLE 2
Figure BDA0001819611550000273
Figure BDA0001819611550000281
Note: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in a vacuum environment and the test values were absolute values. The LUMO energy level is the absolute value of the energy at the longest wavelength (Eg) of the ultraviolet absorption spectrum of a material minus the HOMO energy level. The cyclic voltammetry test adopts CS350H electrochemical workstation of Costet instruments Co., Ltd, tetrabutyl hexafluorophosphate is used as electrolyte and is dissolved into dichloromethane solution; the scanning speed is 100 mv/s.
As can be seen from the data in the table, compared with the conventional blue light host material CBP, the compound of the invention has good glass transition temperature and decomposition temperature; and has good reversible redox characteristics. The material is used as a main material of the luminous layer, and can inhibit crystallization and film phase separation of the material; meanwhile, the decomposition of the material under high brightness can be inhibited, and the service life of the device is prolonged. In addition, the compound has a lower HOMO energy level relative to CBP, so that injection of current carriers is facilitated, the driving voltage of the device is effectively reduced, and the power efficiency of the device is improved.
To further illustrate the excellent characteristics of the material of the present invention with respect to CBP, the singlet energy level, the triplet energy level, the carrier mobility and the material bond energy stability of the material were tested, and the detailed results are shown in table 3 below:
TABLE 3
Figure BDA0001819611550000291
Note: testing the singlet state energy level and the triplet state energy level in a film state by adopting an FLS980 instrument of Edinburgh; the carrier mobility is tested by adopting a flight time method; the bond energy is the bond energy of the weakest bond of the material, and is calculated by simulation by using B3LYP/6-31G of Gaussian 16.
As can be seen from table 3, the S1 energy level of the material of the present invention is lower than that of CBP, and the host material transits from the ground state to the first excited state (singlet state) due to the recombination of carriers on the host material, so that the lower singlet state energy level can effectively reduce the device driving voltage. The TTA effect is that two triplet excitons generate a singlet exciton through coupling, and the closer the T1/S1 is to 0.5, the better the TTA effect is; therefore, compared with CBP, the structure of the application is closer to 0.5 in T1/S1, the TTA effect can be increased, and the device efficiency is improved. The difference of hole and electron mobility of the material is about 2 orders of magnitude, and CBP is close to 4 orders of magnitude; therefore, the material disclosed by the invention can be used as a main material to effectively improve the electron-hole recombination rate and improve the device efficiency. Furthermore, the bond energy of the weakest bond of the material is superior to that of CBP, so that the stability of the material can be effectively ensured, and the service life of the device can be prolonged.
To further illustrate the advantages of the material of the present invention as a host material, the fluorescence quantum efficiency of the doped thin film can be tested for comparison, and the specific test results are shown in table 4.
TABLE 4
Figure BDA0001819611550000301
Figure BDA0001819611550000311
Note that: the film is subjected to double-source co-evaporation by adopting vacuum evaporation equipment, wherein the mass percent of 96:4 is the mass percent of the film and the vacuum evaporation equipment; the absolute fluorescence quantum efficiency was tested using the Edinburgh FLS980 in combination with an integrating sphere.
The OLED device is manufactured, the driving voltage, the efficiency and the service life of the OLED device are tested, and the material is comprehensively evaluated.
Preparation of the organic electroluminescent device of the present invention
The effect of the compound synthesized according to the present invention as a host material for a light emitting layer in a device is explained in detail by device examples 1 to 25 and device comparative example 1 below. Device examples 2 to 25 and device comparative example 1 compared with device example 1, the manufacturing process of the devices was completely the same, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept the same, except that the host material of the light emitting layer was changed, the structural composition of the devices obtained in each example is shown in table 5, and the test results of the obtained devices are shown in table 6.
Device example 1
Cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 30 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes; drying the ITO glass substrate, placing the ITO glass substrate in a vacuum cavity until the vacuum degree is less than 1 multiplied by 10-6Torr, evaporating a mixture of HT1 and P1 with the film thickness of 10nm on the ITO anode layer 2, the mass ratio of HT1 and P1 is 97:3, and the layer is a hole injection layer 3; next, 50nm thick HT1 was evaporated to form a hole transport layer 4; then evaporating EB1 with the thickness of 20nm, wherein the layer is used as an electron blocking layer 5; further, a light emitting layer 6 of 25nm is evaporated, whereinThe light-emitting layer comprises a host material compound 1 and an object doping material BD-1, the mass percent of the doping material is 5%, and the rate is controlled by a film thickness meter according to the mass percent of the host material and the doping dye; further evaporating ET1 and Liq with the thickness of 40nm on the light-emitting layer 6, wherein the mass ratio of ET1 to Liq is 1:1, and the organic material of the layer is used as an electron transport layer 7; vacuum evaporating LiF with the thickness of 1nm on the electron transport layer 7, wherein the layer is an electron injection layer 8; on the electron injection layer 8, a cathode Al (80nm) was vacuum-evaporated, which was a cathode electrode layer 9. The specific prior art material structure referred to in example 1 is shown below:
Figure BDA0001819611550000321
device examples 2-25 and device comparative example 1 were fabricated in exactly the same manner as device example 1, except that the host material of the light-emitting layer was changed. Device examples 1-25 and device comparative example 1 the device structures are shown in table 5 below:
TABLE 5
Figure BDA0001819611550000322
Figure BDA0001819611550000331
Figure BDA0001819611550000341
After the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the driving voltage, external quantum efficiency, and lifetime of the device were measured.
TABLE 6
Device numbering Drive voltage (V) External quantum efficiency (%) LT95 Life (H)
Comparative device example 1 5.1 4.48 15
Device example 1 4.02 7.20 112
Device example 2 4.21 7.08 118
Device example 3 4.23 6.91 109
Device example 4 4.15 7.25 98
Device example 5 4.30 6.98 99
Device example 6 3.98 7.34 107
Device example 7 4.25 7.22 115
Device example 8 4.18 7.30 108
Device example 9 4.11 7.51 116
Device example 10 3.99 7.31 119
Device example 11 4.08 7.56 107
Device example 12 4.25 7.53 108
Device example 13 4.27 7.48 110
Device example 14 4.22 7.29 112
Device example 15 4.09 7.24 103
Device example 16 3.99 7.56 119
Device example 17 3.98 7.59 120
Device example 18 4.01 7.56 121
Device example 19 4.02 7.47 130
Device example 20 4.07 7.48 128
Device example 21 3.99 7.52 122
Device example 22 4.00 7.23 127
Device example 23 4.08 7.40 129
Device example 24 4.09 7.48 126
Device example 25 4.07 7.37 131
The driving voltage and external quantum efficiency are that the current density of the device is 20mA/cm2A test value for the case; LT95 refers to a current density of 20mA/cm2The time taken for the luminance of the device to decay to 95% in the case; the life test System is an OLED device life tester developed by LTD and having model number of EAS-62C.
From the results of table 6, it can be seen that the compound of the present invention can be applied to the fabrication of an OLED light emitting device, and compared to comparative example 1, the driving voltage is effectively reduced at the same current density; meanwhile, the external quantum efficiency and the service life of the device are greatly improved.
Furthermore, the efficiency of the OLED device prepared by the material of the invention is stable when the OLED device works at low temperature and high temperature, and the results of external quantum efficiency tests of device examples 1, 2, 4, 6, 9, 11, 14, 18 and 23 and device comparative example 1 at the temperature range of-10 to 80 ℃ are shown in Table 7.
TABLE 7
Figure BDA0001819611550000361
As can be seen from the data in table 7, device examples 1, 2, 4, 6, 9, 11, 14, 18 and 23, in which the material of the present invention was used in combination with the known material, had very stable device efficiency and less influence of temperature, compared to device comparative example 1.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (9)

1. A xanthene-centered compound, characterized in that the structure of the compound is shown in general formula (1):
Figure FDA0001819611540000011
in the general formula (1), Z represents a nitrogen atom or C-R;
l represents a single bond, substituted or unsubstituted C6-C30One of an arylene group, a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
r, which is identical or different at each occurrence, is hydrogen, halogen, cyano, C1-C20Alkyl, substituted or unsubstituted C6-C30Aryl radicals, containing one or more hetero atomsOne of a substituted or unsubstituted 5-30 membered heteroaryl;
Ar1、Ar2each independently represents substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
wherein the substituents of the substitutable group are optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
2. The xanthene-based compound according to claim 1, wherein at least one of the Z's in the general formula (1) represents a nitrogen atom.
3. The xanthene-core compound according to claim 1, wherein in formula (1), Ar is Ar1、Ar2And R independently represents a structure represented by a general formula (2), a general formula (3), a general formula (4) or a general formula (5);
Figure FDA0001819611540000021
wherein the symbols and indices used have the meanings given in claim 1,
in the general formulae (2) and (3), X is1、X2、X3Each independently represents a single bond, an oxygen atom, a sulfur atom, -C (R)4)(R5)-、-Si(R6)(R7)-、
Figure FDA0001819611540000022
or-N (R)8) -one of the above; and X1、X2Not simultaneously represent a single bond; wherein R is4And R5、R6And R7Can be bonded to each other to form a ring;
R1～R3each independently represents a hydrogen atom, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; r1～R3The connection mode with the general formula (2) or the general formula (3) is single bond substitution connection or ring-merging connection;
z, which is the same or different at each occurrence, is represented by a nitrogen atom or C-H; z at the connecting site with other groups represents a carbon atom;
in the general formula (4) and the general formula (5), X represents a nitrogen atom or C-R9；
The R is4～R8Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the R is9Represented by hydrogen atom, cyano group, halogen, C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C30Aryl of (a), substituted or unsubstituted 5-to 30-membered heteroaryl containing one or more heteroatoms, two or more adjacent R9Can be bonded to each other to form a ring;
wherein said substitutable group is optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
4. The xanthene-based compound according to claim 3, wherein R in formula (2) or formula (3)1～R3Independently represent a hydrogen atom, a structure represented by general formula (6), general formula (7) or general formula (8);
Figure FDA0001819611540000031
said Y is1、Y2、Y3Each independently represents an oxygen atom, a sulfur atom, -C (R)10)(R11)-、-Si(R12)(R13)-、
Figure FDA0001819611540000032
or-N (R)14) -one of the above; wherein R is10And R11、R12And R13Can be bonded to each other to form a ring;
wherein represents a site of formula (6), formula (7) or formula (8) in parallel ring-connection with formula (2) or formula (3);
the Y represents a nitrogen atom or C-H;
the R is10～R14Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-C20Alkyl of (C)6-C30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
5. The xanthene-based compound according to claim 4, wherein in the general formula (1), L represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted benzothienylene group;
ar is1、Ar2Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substitutedOr one of unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted isobenzofuranyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted isobenzothiophenyl, and substituted or unsubstituted isoquinolyl;
the R is4～R8、R10～R14Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl, biphenylyl, naphthyridinyl or pyridyl;
the R, R9Each independently represents a hydrogen atom, a cyano group, a fluorine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group;
the substituent of the substitutable group is one or more selected from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, naphthyridinyl or pyridyl.
6. The xanthene-core compound according to claim 1, wherein the structure of the general formula (1) is specifically represented by any one of the following structures:
Figure FDA0001819611540000041
Figure FDA0001819611540000051
Figure FDA0001819611540000061
Figure FDA0001819611540000071
Figure FDA0001819611540000081
Figure FDA0001819611540000091
Figure FDA0001819611540000101
7. an organic electroluminescent element, characterized in that at least one functional layer of the organic electroluminescent element contains a xanthene-based compound according to any of claims 1 to 6.
8. An organic electroluminescent device according to claim 7, comprising a light-emitting layer, wherein the host material of the light-emitting layer is the xanthene-based compound according to any one of claims 1 to 6.
9. A lighting or display element comprising an organic electroluminescent device as claimed in any one of claims 7 to 8.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010866A (en) * 2020-09-07 2020-12-01 京东方科技集团股份有限公司 Dioxin compound and preparation method and application thereof
CN114213377A (en) * 2021-12-10 2022-03-22 上海钥熠电子科技有限公司 Anthracene-based fluorescent light-emitting main body material and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112010866A (en) * 2020-09-07 2020-12-01 京东方科技集团股份有限公司 Dioxin compound and preparation method and application thereof
CN114213377A (en) * 2021-12-10 2022-03-22 上海钥熠电子科技有限公司 Anthracene-based fluorescent light-emitting main body material and application thereof

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