CN114835699A - Anthracene furan compound, intermediate, organic electroluminescent device and display device - Google Patents

Anthracene furan compound, intermediate, organic electroluminescent device and display device Download PDF

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CN114835699A
CN114835699A CN202210646471.4A CN202210646471A CN114835699A CN 114835699 A CN114835699 A CN 114835699A CN 202210646471 A CN202210646471 A CN 202210646471A CN 114835699 A CN114835699 A CN 114835699A
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王占奇
李志强
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Fuyang Sineva Material Technology Co Ltd
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Abstract

The invention provides an anthracenopyran compound, an intermediate, an organic electroluminescent device and a display device. The anthracenopyran compound comprises a group shown as a formula BH-A1 and a group shown as a formula BH-A; the anthracofuran compound is obtained by fusing a group shown in a formula BH-A1 with two adjacent carbon atoms on a ring A and/or a ring B in the group shown in the formula BH-A; the intermediate is used for preparing the anthracofuran compound. The anthrafuran compound provided by the invention can be used as a main material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.

Description

Anthracene furan compound, intermediate, organic electroluminescent device and display device
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an anthracenopyran compound, an intermediate, an organic electroluminescent device and a display device.
Background
The organic electroluminescent device is prepared by depositing one or more layers of organic materials between two metal electrodes through spin coating or vacuum evaporation, and a classic three-layer organic electroluminescent device comprises a hole transport layer, a light emitting layer and an electron transport layer. Holes generated by the anode are combined in the light emitting layer through the hole transport layer and electrons generated by the cathode through the electron transport layer to form excitons, and then light is emitted. The organic electroluminescent device can be adjusted to emit various desired lights by changing the material of the light emitting layer as desired.
As a novel display technology, the organic electroluminescent device has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
Since the invention at the end of the 20 th century and the 80 th era, organic electroluminescent devices have been used in industry, such as screens of cameras and mobile phones, but the current OLED devices have limited wider application due to low efficiency, short service life and other factors, especially large screen displays, and therefore, the efficiency of the devices needs to be improved. One of the important factors for the restriction is the performance of the organic electroluminescent material in the organic electroluminescent device. Therefore, there is a need to develop stable and efficient organic electroluminescent materials to improve the current efficiency and lifetime of OLED devices.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an anthracofuran compound, an intermediate, an organic electroluminescent device and a display device. The anthrafuran compound provided by the invention can be used as a main material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has lower driving voltage, higher current efficiency and longer service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the invention provides an anthracofuran compound, which is obtained by fusing at least one group represented by the formula BH-A1 with any two adjacent carbon atoms on ring A and/or ring B in a group represented by the formula BH-A;
Figure BDA0003684294180000011
wherein denotes the site of fusion of a group of formula BH-A1; the opposite side indicates the condensed sites of hydrogen atoms or groups of the formula BH-A;
Ar 101 and Ar 102 Each independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;
Ar 101 and Ar 102 Wherein the substituted substituents are independently selected from at least one of-D, C1-C10 alkyl, C1-C6 alkoxy or C6-C15 aryl;
the hydrogen atom in the anthracofuran compound can be substituted by at least one of-D, -F, -CN, C1-C10 alkyl, C1-C6 alkoxy or C6-C15 aryl;
the anthrafurans contain at least two heteroatoms in the heteroaryl group.
In the heteroaryl group, the heteroatom is Ar 101 And/or Ar 102 In the case of heteroaryl, the heteroatom in the heteroaryl group, and the heteroatom (O atom) in the anthracofuran group obtained by fusing the group of formula BH-A1 with any two adjacent carbon atoms of ring A and/or ring B in the group of formula BH-A.
According to the invention, by designing the structure of the anthrafuran compound, and further fusing the group shown in the formula BH-A1 with two adjacent carbon atoms on the ring A and/or the ring B of the group shown in the formula BH-A, the obtained anthrafuran compound with a specific structure can be used as a main body material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has high current efficiency and long service life.
According to the invention, the anthrabenzofuran group is used as a mother nucleus structure, so that the fluorescence quantum efficiency is higher, the number of heteroatoms in the anthrafuran compound is limited, the number of the heteroatoms in the anthrafuran compound is more, and when the anthrafuran compound provided by the invention is used as a main material of a light emitting layer, the energy can be smoothly transferred between the anthrafuran compound and a doping material, so that an OLED light emitting device has higher current efficiency and longer service life.
In the present invention, Ar 101 And Ar 102 Each independently selected from a substituted or unsubstituted aryl group of C6 to C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40), and a substituted or unsubstituted heteroaryl group of C12 to C20 (for example, C12, C14, C16, C18, or C20).
Ar 101 And Ar 102 The substituted substituents in (1) are each independently at least one selected from the group consisting of-D, C1 to C10 alkyl groups (e.g., methyl, ethyl, propyl, tert-butyl, cyclopentyl, tert-butyl, adamantyl, etc.), C1 to C6 alkoxy groups (e.g., methoxy, ethoxy, propoxy, hexyloxy, etc.), and C6 to C15 aryl groups (e.g., phenyl, naphthyl, fluorenyl, etc.).
The hydrogen atom in the anthracofuran compound may be substituted with at least one of a-D, -F, -CN, C1-C10 alkyl group (for example, methyl, ethyl, propyl, tert-butyl, cyclopentyl, tert-butyl, adamantyl, etc.), a C1-C6 alkoxy group (for example, methoxy, ethoxy, propoxy, hexyloxy, etc.), or a C6-C15 aryl group (for example, phenyl, naphthyl, fluorenyl, etc.).
The following is a preferred technical solution of the present invention, but not a limitation to the technical solution provided by the present invention, and the object and advantageous effects of the present invention can be better achieved and achieved by the following preferred technical solution.
In a preferred embodiment of the present invention, the anthrafuran compound is selected from any one of the following anthrafurans compounds 1 to 27:
Figure BDA0003684294180000021
Figure BDA0003684294180000031
wherein in the anthracenopyran compounds 1-6, Ar is 101 And Ar 102 Having the same protective range as above, and Ar 101 And Ar 102 At least one is selected from substituted or unsubstituted C12-C20 heteroaryl;
in the anthracenopyran compounds 7-27, Ar 101 And Ar 102 Having the same protection ranges as described above.
In the present invention, when the anthrafuran compound is obtained by fusing 1 group represented by the formula BH-A1 with two adjacent carbon atoms on ring A and/or ring B in the group represented by the formula BH-A, Ar 101 And Ar 102 At least one is selected from substituted or unsubstituted C12-C20 heteroaryl; if the anthrafurans are obtained by fusing 2 groups of the formula BH-A1 with two adjacent carbon atoms of ring A and/or ring B in a group of the formula BH-A, then the pair of Ar groups 101 And Ar 102 The choice of (a) is not further limited. Accordingly, it is understood that the anthrafuran compound provided by the present invention contains at least 2 hetero atoms in the molecule.
In a preferred embodiment of the present invention, the aryl group having C6 to C40 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, and benzonaphthofluorenyl.
Preferably, the C12-C20 heteroaryl is selected from any one of dibenzofuran, dibenzothiophene, dinaphthofuran and dinaphthothiophene.
Preferably, Ar 101 And Ar 102 Each independently selected from any one of the following groups substituted unsubstituted: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl.
Said, Ar 101 And Ar 102 Wherein each of said substituted substituents is independently selected from at least one of-D, methyl, ethyl, t-butyl, adamantyl, hexyloxy, methoxy, isopropoxy, phenyl or naphthyl.
Preferably, the hydrogen atom in the anthrafuran compound may be substituted with at least one of-D, methyl, ethyl, t-butyl, adamantyl, hexyloxy, methoxy, isopropoxy, phenyl, or naphthyl.
In a preferred embodiment of the present invention, the anthrafuran compound is selected from any one of the following compounds:
Figure BDA0003684294180000032
Figure BDA0003684294180000041
Figure BDA0003684294180000051
Figure BDA0003684294180000061
Figure BDA0003684294180000071
Figure BDA0003684294180000081
Figure BDA0003684294180000091
Figure BDA0003684294180000101
Figure BDA0003684294180000111
preferably, the anthracenopyran compound is selected from any one of the following compounds 1-10 or compounds D1-D10:
Figure BDA0003684294180000112
Figure BDA0003684294180000121
in a second aspect, the present invention provides an intermediate selected from any one of the following compounds:
Figure BDA0003684294180000122
the intermediate is used for preparing the anthracenopyran compound of the first aspect.
Preferably, the intermediate is selected from any one of the following compounds:
Figure BDA0003684294180000123
in a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising the anthrafurans compound according to the first aspect.
Preferably, the organic thin film layer includes a light-emitting layer, and a material of the light-emitting layer includes the anthrafuran-based compound according to the first aspect.
Preferably, the organic thin film layer further includes a hole layer including a hole transport layer, a hole injection layer, and an electron blocking layer.
As a preferred technical solution of the present invention, the material of the hole layer is selected from a compound having a structure shown in formula I or a deuterated composition, wherein the deuterated composition comprises at least two compounds each having a structure shown in formula I;
Figure BDA0003684294180000131
wherein Ar is 11 、Ar 12 、Ar 21 、Ar 22 Ar is independently selected from substituted or unsubstituted aryl of C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40) and substituted or unsubstituted heteroaryl of C12-C20 (for example, C12, C14, C16, C18 or C20);
Ar 11 、Ar 12 may be connected by a single bond, Ar 21 、Ar 22 Can be connected by a single bond; ar, Ar 12 Can be connected by a single bond, Ar 11 Can be connected by a single bond, Ar 21 Can be connected by a single bond, Ar 22 Can be connected by a single bond;
n is selected from 0 or 1;
Ar 11 、Ar 12 、Ar 21 、Ar 22 the substituents for Ar are independently at least one selected from the group consisting of C1-C12 (for example, C1, C2, C4, C6, C8, C10, C12, etc.) alkyl, C1-C12 (for example, C1, C2, C4, C6, C8, C10, C12, etc.) alkoxy, and C6-C12 aryl (for example, phenyl, naphthyl, etc.);
the compound of formula I meets at least one of the following conditions:
(1) the compound of the formula I does not contain deuterium atom;
(2)Ar 11 、Ar 12 、Ar 21 、Ar 22 or the hydrogen atoms of at least one of the substituted substituents in Ar are all substituted by deuterium atoms;
(3)Ar 11 、Ar 12 、Ar 21 、Ar 22 or at least one of the hydrogen atoms of Ar is entirely substituted by a deuterium atom;
the deuterated composition comprises a compound of formula I meeting the condition (2) or (3).
In a preferred embodiment of the present invention, Ar is selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenylenyl, fluorenyl, benzofluorenyl;
the substituted substituent is at least one selected from methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl or naphthyl.
Preferably, Ar is 11 、Ar 12 、Ar 21 、Ar 22 Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, triphenylene, fluoranthenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl;
the substituted substituents are each independently selected from at least one of methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or naphthyl.
As a preferred embodiment of the present invention, the compound of formula I is selected from any one of the following substituted or unsubstituted compounds:
Figure BDA0003684294180000141
Figure BDA0003684294180000151
Figure BDA0003684294180000161
Figure BDA0003684294180000171
Figure BDA0003684294180000181
Figure BDA0003684294180000191
Figure BDA0003684294180000201
Figure BDA0003684294180000211
Figure BDA0003684294180000221
Figure BDA0003684294180000231
Figure BDA0003684294180000241
the substitution means that hydrogen atoms in the above compounds are partially or completely substituted by deuterium atoms; preferably, the compound of formula I is selected from any one of the following compounds:
Figure BDA0003684294180000242
Figure BDA0003684294180000251
in the invention, the anthrafuran compound is used as a main material of the light-emitting layer, and the light-emitting layer material also comprises a compound with a structure shown in a formula II and/or a compound with a structure shown in a formula III:
Figure BDA0003684294180000252
wherein Ar is 21 、Ar 22 Each independently selected from a substituted or unsubstituted C6-C20 (for example, C6, C8, C10, C12, C16, C20, etc.) aryl group, a substituted or unsubstituted C3-C20 (for example, C3, C6, C8, C10, C12, C16, C20, etc.) heteroaryl group;
R 21 、R 22 and R 23 Each independently selected from hydrogen, C1-C12 (for example, C1, C2, C4, C6, C8, C10, C12, etc.) straight chain or branched chain alkyl, C6-C12 (for example, C6, C8, C10, C12, etc.) cycloalkyl;
Ar 21 、Ar 22 wherein the substituted substituents are independently selected from C1-C5 (for example, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) straight-chain or branched alkyl groups or C6-C12 (for example, phenyl, biphenyl, naphthyl, etc.) aryl groups;
Ar 31 、Ar 32 、Ar 33 and Ar 34 Each independentlyAny one selected from substituted or unsubstituted aryl groups of C6 to C22 (for example, C6, C8, C10, C16, C18, or C22), and substituted or unsubstituted heteroaryl groups of C12 to C40 (for example, C12, C18, C20, C24, C30, C36, or C40);
R 31 any one selected from phenyl, naphthyl or biphenyl;
a is selected from 0 or 1;
Ar 31 、Ar 32 、Ar 33 、Ar 34 the substituted substituents in (1) are each independently selected from a C1-C5 linear or branched alkyl group (for example, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) or a C6-C12 (for example, C6, C8, C10, C12, etc.) aryl group.
As a preferred embodiment of the present invention, Ar is 21 、Ar 22 Each independently selected from
Figure BDA0003684294180000261
Figure BDA0003684294180000262
Figure BDA0003684294180000263
Any one of them.
Preferably, said R is 21 、R 22 And R 23 Each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.
Preferably, Ar is 31 、Ar 32 、Ar 33 And Ar 34 Each independently selected from
Figure BDA0003684294180000264
Figure BDA0003684294180000265
Any one or a combination of at least two of them.
As a preferred embodiment of the present invention, the compound having the structure shown in formula II is selected from any one of the following compounds:
Figure BDA0003684294180000266
Figure BDA0003684294180000271
as a preferred embodiment of the present invention, the compound having the structure shown in formula III is selected from any one of the following compounds:
Figure BDA0003684294180000272
Figure BDA0003684294180000281
in a fourth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device according to the third aspect.
Compared with the prior art, the invention has the following beneficial effects:
according to the invention, by designing the structure of the anthrafuran compound, and further fusing the group shown in the formula BH-A1 with two adjacent carbon atoms on the ring A and/or the ring B of the group shown in the formula BH-A, the obtained anthrafuran compound with a specific structure can be used as a main body material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has higher current efficiency and longer service life.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation of example 1
The preparation embodiment provides an intermediate M2, and the preparation method thereof is as follows:
Figure BDA0003684294180000282
(1) synthesis of intermediate M2-1
Under the protection of nitrogen, 40mL of toluene, 20mL of ethanol and 10mL of water are added into a 250mL three-necked flask, 2-bromo-1-hydroxyanthracene (2.73g) is added, and then o-chlorobenzeneboronic acid (1.56g) and K are added 3 PO 4 (4.24g) and tetrakistriphenylphosphine palladium (0.23g), the mixture was refluxed for 12 hours while slowly raising the temperature, the temperature was lowered, water was added for liquid separation, the organic layer was washed with water, magnesium sulfate and a small amount of silica gel were added for drying, the magnesium sulfate and the silica gel were removed by filtration, the solvent was removed under reduced pressure, and the obtained solid was crystallized twice with ethanol to give intermediate M2-1(2.6 g).
Performing mass spectrometry detection on the intermediate M2-1: the mass to charge ratio (m/z) was found to be 304.07.
(2) Synthesis of intermediate M2-2
Under nitrogen protection, 100mL of DMF, intermediate M2-1(3.00g), potassium carbonate (1.38g), cuprous iodide (0.1g) and cuprous oxide (0.1g) were added to a 500mL three-necked flask, the mixture was heated to reflux reaction for 20 hours, the temperature was reduced to room temperature, water and ethyl acetate were added, liquid separation was performed after filtration, the organic layer was washed with water and then concentrated to dryness, silica gel column chromatography was performed, and petroleum ether and ethyl acetate were eluted at a volume ratio of 20:1 to obtain intermediate M2-2(1.7 g).
Mass spectrometric detection of intermediate M2-2: the mass to charge ratio (m/z) was found to be 268.09.
(3) Synthesis of intermediate M2
Under the protection of nitrogen, 100mL of DMF and an intermediate M2-2(2.7g) are added into a 500mL three-necked flask, a DMF solution (20mL) containing NBS (3.6g) is added dropwise at the temperature of 20-25 ℃, after the addition is finished, the mixture is stirred and reacted at the temperature of 20-25 ℃ for 4 hours, water is added, the obtained solid is filtered, and after the solid is dried, silica gel column chromatography separation is carried out, petroleum ether is eluted, and the intermediate M2(1.1g) is obtained, wherein the yield is 25.8%.
Mass spectrometric detection of intermediate M2: the peak with the largest measured mass-to-charge ratio (m/z) intensity was 425.91, intensity 100%; the other two peaks were 423.91 and 427.91, respectively, with an intensity of about 50%.
The intermediate M2 was subjected to nuclear magnetic resonance and 1H-NMR (Bruker, Switzerland, Avance II 400MHz NMR spectrometer, CDCl3) was determined to be Δ 8.39(d, 2H), Δ 8.11(M, 1H), Δ 7.99(M, 1H), Δ 7.67(d, 1H), Δ 7.63(M, 1H), Δ 7.59 to 7.52(M, 2H), Δ 7.38(M, 1H), Δ 7.30(M, 1H).
Preparation of example 2
The preparation embodiment provides an intermediate M3, and the preparation method thereof is as follows:
Figure BDA0003684294180000291
(1) synthesis of intermediate M3-1
Referring to the synthesis method of intermediate M2-1, except for replacing 2-bromo-1-hydroxyanthracene with an equivalent amount of 1-bromo-2-hydroxyanthracene and under the same conditions as in preparation example 1, intermediate M3-1 was obtained.
Mass spectrometry detection of intermediate M3-1: the mass to charge ratio (m/z) was found to be 304.07.
(2) Synthesis of intermediate M3-2
With reference to the synthesis method of intermediate M2-2, intermediate M3-2 was obtained except that intermediate M2-1 was replaced with an equivalent amount of intermediate M3-1 and the other conditions were the same as those in preparation example 1.
Mass spectrometric detection of intermediate M3-2: the mass to charge ratio (m/z) was found to be 268.09.
(3) Synthesis of intermediate M3
The procedure of synthesis of intermediate M2 was followed except that intermediate M2-2 was replaced with an equivalent amount of intermediate M3-2 and the other conditions were the same as in preparation example 1 to give intermediate M3(0.89g) in a 20.9% yield.
Mass spectrometric detection of intermediate M3: the peak with the largest measured mass-to-charge ratio (m/z) intensity was 425.91, intensity 100%; the other two peaks were 423.91 and 427.91, respectively, and the intensity was about 50%.
Performing nuclear magnetic detection on the intermediate M3 to obtain 1 H-NMR (Bruk Switzerland)Erco, Avance II 400MHz NMR spectrometer, CDCl 3 ):δ8.41～8.35(m，2H)，δ8.09(m，1H)，δ8.05(d，1H)，δ7.97(m，1H)，δ7.68～7.52(m，3H)，δ7.37(m，1H)，δ7.30(m，1H)。
Preparation of example 3
The present preparation example provides another preparation method of intermediate M2-2, which is as follows:
Figure BDA0003684294180000292
(1) synthesis of M2-1-A
Referring to the synthesis method of intermediate M2-1, except that o-chlorobenzoic acid was replaced with an equal amount of o-fluorobenzoic acid and the other conditions were the same as in preparation example 1, M2-1-a was obtained.
Mass spectrometry detection of intermediate M2-1-A: the mass to charge ratio (m/z) was found to be 288.10.
(2) Synthesis of M2-2
Under the protection of nitrogen, 200mL of DMF, intermediate M2-1-A (3.0g), potassium carbonate (1.4g), cuprous iodide (0.1g) and cuprous oxide (0.1g) were added to a 500mL three-necked flask, the mixture was heated to reflux for reaction for 32h, the temperature was reduced to room temperature, water and ethyl acetate were added for liquid separation, the organic layer was concentrated to dryness, silica gel column chromatography was performed, and petroleum ether/ethyl acetate ratio of 20:1 (volume ratio) was eluted to give intermediate M2-2(1.9 g).
Mass spectrometric detection of intermediate M2-2: the mass to charge ratio (m/z) was found to be 268.09.
Preparation of example 4
The present preparation example provides another preparation method of intermediate M3-2, which is as follows:
Figure BDA0003684294180000301
(1) synthesis of M3-1-A
Referring to the synthesis method of intermediate M3-1, except for replacing o-chlorobenzoic acid with an equal amount of o-fluorobenzoic acid, the other conditions were the same as in preparation example 2, yielding M3-1-a.
Mass spectrometry detection of intermediate M3-1-A: the mass to charge ratio (m/z) was found to be 288.10.
(2) Synthesis of M3-2
Under the protection of nitrogen, 200mL of DMF, intermediate M3-1-A (3.0g), potassium carbonate (1.4g), cuprous iodide (0.1g) and cuprous oxide (0.1g) were added to a 500mL three-necked flask, the mixture was heated to reflux for reaction for 32h, the temperature was reduced to room temperature, water and ethyl acetate were added for liquid separation, the organic layer was concentrated to dryness, silica gel column chromatography was performed, and petroleum ether/ethyl acetate ratio of 20:1 (volume ratio) was eluted to obtain intermediate M3-2(2.0 g).
Mass spectrometric detection of intermediate M3-2: the mass to charge ratio (m/z) was found to be 268.09.
Preparation of example 5
The preparation embodiment provides an intermediate MDI, and the preparation method comprises the following steps:
Figure BDA0003684294180000302
(1) synthesis of intermediate MD1-1
Under nitrogen protection, 150mL of toluene, 130mL of ethanol and 30mL of water were added to a 500mL three-necked flask, 3, 7-dibromoanthracene-2, 6-diol (3.68g) was added, o-chlorobenzeneboronic acid (3.2g), K3PO4(8.5g) and tetratriphenylphosphine palladium (0.5g) were further added, the mixture was slowly heated to reflux reaction for 12 hours, the temperature was lowered to room temperature, water was added for liquid separation, the organic layer was washed with water, magnesium sulfate and a small amount of silica gel were added for drying, the magnesium sulfate and the silica gel were removed by filtration, the solvent was removed under reduced pressure, and the obtained solid was crystallized twice with a mixed solvent of ethanol and toluene to give an intermediate 1-1(3.5 g).
And (3) performing mass spectrum detection on the intermediate MD 1-1: the mass to charge ratio (m/z) was found to be 430.05.
(2) Synthesis of intermediate MD1-2
Under the protection of nitrogen, 200mL of DMF, intermediate MD1-1(4.31g), potassium carbonate (2.8g), cuprous iodide (0.2g) and cuprous oxide (0.2g) are added into a 500mL three-necked flask, the temperature is raised to reflux reaction for 40h, the temperature is reduced, water and ethyl acetate are added for separating, an organic layer is concentrated to be dry, silica gel column chromatography is carried out, and petroleum ether and ethyl acetate are eluted at a volume ratio of 20:1 to obtain intermediate MD1-2(2.6 g).
Mass spectrometry detection of intermediate MD 1-2: the mass to charge ratio (m/z) was found to be 358.10.
(3) Synthesis of intermediate MD1
Under the protection of nitrogen, 150mL of DMF and an intermediate MD1-2(3.6g) are added into a 500mL three-necked flask, a DMF solution (20mL) containing NBS (3.6g) is added dropwise at the temperature of 20-25 ℃, the mixture is stirred and reacted for 4 hours at the temperature of 20-25 ℃, water is added, the obtained solid is filtered, and after the solid is dried, silica gel column chromatography is carried out, petroleum ether is eluted to obtain an intermediate MD1(0.92g), and the yield is 17.8%.
Mass spectrometric detection of intermediate MD 1: the peak with the largest measured mass-to-charge ratio (m/z) intensity was 515.92, intensity 100%; the other two peaks are 513.92 and 517.92, respectively, with an intensity of about 50%.
Performing nuclear magnetic detection on the intermediate MD1 to obtain 1 H-NMR (Bruker, Switzerland, Avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl) 3 ):δ8.40(s，2H)，δ8.25(s，2H)，δ7.99(m，2H)，δ7.50(m，2H)，δ7.37(m，2H)，δ7.31(m，2H)。
Preparation of example 6
The preparation embodiment provides an intermediate MD2, and the preparation method thereof is as follows:
Figure BDA0003684294180000311
(1) synthesis of intermediate MD2-1
Referring to the synthesis of intermediate MD1-1, the only difference was that 3, 7-dibromoanthracene-2, 6-diol was replaced with equal amounts of 1, 5-dibromoanthracene-2, 6-diol to give intermediate MD 2-1.
And (3) performing mass spectrum detection on the intermediate MD 2-1: the mass to charge ratio (m/z) was found to be 430.05.
(2) Synthesis of intermediate MD2-2
Referring to the synthesis method of intermediate MD1-2, the only difference was that intermediate MD1-1 was replaced with intermediate MD2-1 in equal amounts to give intermediate MD 2-2.
Mass spectrometry detection of intermediate MD 2-2: the mass to charge ratio (m/z) was found to be 358.10.
(3) Synthesis of intermediate MD2
The synthesis of intermediate MD1 was referenced, except that intermediate MD1-2 was replaced with an equivalent amount of intermediate MD2-2 to give intermediate MD2(0.95g) in 18.4% yield.
Mass spectrometric detection of intermediate MD 2: the peak with the largest measured mass-to-charge ratio (m/z) intensity was 515.92, intensity 100%; the other two peaks are 513.92 and 517.92, respectively, with an intensity of about 50%.
Performing nuclear magnetic detection on the intermediate MD2 to obtain 1 H-NMR (Bruker, Switzerland, Avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl) 3 ):δ8.41(d，2H)，δ8.07(d，2H)，δ7.99(m，2H)，δ7.51(m，2H)，δ7.37(m，2H)，δ7.31(m，2H)。
Preparation of example 7
The preparation example provides another preparation method of the intermediate MD1-2, which comprises the following steps:
Figure BDA0003684294180000321
(1) synthesis of MD1-1-A
Referring to the synthesis method of intermediate MD1-1, the only difference is that o-chlorobenzoic acid is replaced with o-fluorobenzoic acid in equal amount to give MD 1-1-a.
Performing mass spectrum detection on the intermediate MD 1-1-A: the mass to charge ratio (m/z) was found to be 398.11.
(2) Synthesis of MD1-2
Under the protection of nitrogen, 220mL of DMF, an intermediate MD1-1-1A (4.31g), potassium carbonate (2.8g), cuprous iodide (0.2g) and cuprous oxide (0.2g) are added into a 500mL three-necked flask, the mixture is heated to reflux for reaction for 60 hours, the temperature is reduced to room temperature, water and ethyl acetate are added for liquid separation, an organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, and petroleum ether and ethyl acetate are eluted at a volume ratio of 20:1 to obtain an intermediate MD1-2(2.2 g).
Mass spectrometry detection of intermediate MD 1-2: the mass to charge ratio (m/z) was measured to be 358.10.
Preparation of example 8
The present preparation example provides another preparation method of intermediate MD2-2, which is as follows:
Figure BDA0003684294180000322
(1) synthesis of MD2-1-A
Referring to the synthesis method of intermediate MD2-1, the only difference is that o-chlorobenzoic acid is replaced with o-fluorobenzoic acid in equal amount to give MD 2-1-a.
And (3) performing mass spectrum detection on the intermediate MD 2-1-A: the mass to charge ratio (m/z) was found to be 398.11.
(2) Synthesis of MD2-2
Under the protection of nitrogen, 220mL of DMF, an intermediate MD2-1-A (4.31g), potassium carbonate (2.8g), cuprous iodide (0.2g) and cuprous oxide (0.2g) are added into a 500mL three-necked bottle, the temperature is raised to reflux reaction for 60h, the temperature is reduced to room temperature, water and ethyl acetate are added for liquid separation, an organic layer is concentrated to be dry, silica gel column chromatography separation is carried out, and petroleum ether and ethyl acetate are eluted at a volume ratio of 20:1 to obtain an intermediate MD2-2(1.9 g).
Mass spectrometry detection of intermediate MD 2-2: the mass to charge ratio (m/z) was found to be 358.10.
Synthesis example 1
The present synthesis example provides a compound 1, the preparation method of which is as follows:
Figure BDA0003684294180000323
80mL of toluene, 30mL of ethanol, and 20mL of water were added to a 250mL three-necked flask under nitrogen atmosphere, and intermediate M1(4.26g) and dibenzo [ b, d ] were added thereto]Furan-3-boronic acid (4.3g), Na 2 CO 3 (3.0g) and tetrakistriphenylphosphine palladium (0.23g), slowly heating to reflux reaction for 8h, cooling to room temperature, adding water for separating liquid, washing organic layer with water, adding magnesium sulfate and a small amount of silica gel for drying, filtering to remove sulfuric acidAfter magnesium and silica gel, the solvent was removed under reduced pressure, and the obtained solid was crystallized from a mixed solvent of ethanol and toluene to obtain compound 1(4.9 g).
Mass spectrometric detection of compound 1: the mass to charge ratio (m/z) was measured to be 600.17.
Elemental analysis was performed on compound 1, theoretical value: c, 87.98%; h, 4.03%; o, 7.99%, found: c, 87.92%; h,4.02 percent.
Synthesis example 2
The present synthesis example provides a compound 2, the preparation method of which is as follows:
(1) synthesis of Compound 2-1
Figure BDA0003684294180000331
Under nitrogen protection, 80mL of toluene, 30mL of ethanol, and 20mL of water were added to a 250mL three-necked flask, and the intermediate (4.73g) represented by M1-A was added to the flask, followed by addition of dibenzo [ b, d ]]Furan-3-boronic acid (2.1g), Na 2 CO 3 (1.5g) and tetrakistriphenylphosphine palladium (0.115g), slowly heating to 60 ℃ for reaction for 8h, cooling to room temperature, adding water for separating liquid, washing an organic layer with water, adding magnesium sulfate and a small amount of silica gel for drying, filtering to remove the magnesium sulfate and the silica gel, removing the solvent under reduced pressure, carrying out column chromatography separation on the obtained solid silica gel, and eluting with petroleum ether to obtain a compound 2-1(4.3 g).
Mass spectrometric detection of Compound 2-1: the two peaks with the largest measured mass-to-charge ratio (m/z) were 512.04, 514.04, respectively, and were of substantially the same intensity, establishing the structure as shown by 2-1.
(2) Synthesis of Compound 2
Figure BDA0003684294180000332
Referring to the synthesis method of compound 2-1, the only difference is that compound M1-a is replaced with compound 2-1 in equivalent amount, dibenzo [ b, d ] furan-3-boronic acid is replaced with biphenyl boronic acid in equivalent amount, and the reaction conditions are reflux reaction for 8h to obtain compound 2.
Mass spectrometric detection of compound 2: the mass to charge ratio (m/z) was found to be 586.19.
Synthesis example 3
This synthetic example 3 provides a compound 3, the preparation method of which is as follows:
Figure BDA0003684294180000333
referring to the synthesis of compound 2, the only difference is that biphenyl boronic acid is replaced with an equivalent amount of 2-naphthalene boronic acid to compound 3.
Mass spectrometric detection of compound 3: the mass to charge ratio (m/z) was found to be 560.18.
Synthesis example 4
This synthetic example provides a compound 4, the preparation method of which is as follows:
Figure BDA0003684294180000341
referring to the synthesis method of compound 2, the only difference is that compound 4 is obtained by replacing diphenylboronic acid with deuterated 2-naphthoic acid in an equivalent amount.
Mass spectrometric detection of compound 4: the mass to charge ratio (m/z) was found to be 567.22.
Synthesis example 5
This synthetic example provides a compound 5, the preparation method of which is as follows:
(1) synthesis of Compound 5-1
Figure BDA0003684294180000342
Under nitrogen protection, 80mL of toluene, 30mL of ethanol, and 20mL of water were added to a 250mL three-necked flask, and the intermediate (4.26g) represented by M2 was added, followed by addition of dibenzo [ b, d ]]Furan-3-boronic acid (2.1g), Na 2 CO 3 (1.5g) and tetratriphenylphosphine palladium (0.08g), slowly heating to 70 ℃, carrying out reflux reaction for 8h, and then heating to reflux reactionAfter 4h, the temperature is reduced to room temperature, water is added for liquid separation, the organic layer is washed by water, magnesium sulfate and a small amount of silica gel are added for drying, the magnesium sulfate and the silica gel are removed by filtration, the solvent is removed under reduced pressure, the obtained solid silica gel is subjected to column chromatography separation, and petroleum ether elution to obtain the compound 5-1(1.1g) with the yield of 21%.
Mass spectrometric detection of Compound 5-1: the two peaks with the largest measured mass-to-charge ratio (m/z) were 512.04, 514.04, respectively, and were of substantially the same intensity, confirming the structure as shown in 5-1.
The intermediate 5-1 was subjected to nuclear magnetic resonance and 1H-NMR (Bruker, Switzerland, Avance II 400MHz nuclear magnetic resonance spectrometer, CDCl3) was measured, and δ 8.36(m, 1H), δ 8.21(m, 1H), δ 8.09(d, 1H), δ 8.02(d, 1H), δ 8.00(m, 2H), δ 7.76(d, 1H), δ 7.65(m, 1H), δ 7.59 to 7.50(m, 4H), δ 7.46(d, 1H), δ 7.37(m, 2H), δ 7.30(m, 2H) was measured.
(2) Synthesis of Compound 5
Figure BDA0003684294180000343
Referring to the synthesis of compound 3, the only difference is that compound 5 is obtained by replacing intermediate 2-1 with an equivalent amount of intermediate 5-1.
Mass spectrometric detection of compound 5: the mass to charge ratio (m/z) was found to be 560.18.
Synthesis example 6
This synthetic example provides a compound 6, the preparation method of which is as follows:
Figure BDA0003684294180000351
referring to the synthesis of compound 3, the only difference was that intermediate 2-1 was replaced with an equivalent amount of intermediate 5-1 and 2-naphthalene boronic acid was replaced with an equivalent amount of biphenyl-3-boronic acid to give compound 6.
Mass spectrometric detection of compound 6: the mass to charge ratio (m/z) was found to be 586.19.
Synthesis example 7
This synthetic example provides a compound 7, the preparation method of which is as follows:
(1) synthesis of Compound 7-1
Figure BDA0003684294180000352
With reference to the synthesis of compound 5-1, the only difference was that intermediate M2 was replaced with an equivalent amount of intermediate M3 to afford compound 7-1(1.2 g).
Mass spectrometric detection of Compound 7-1: the two peaks with the largest measured mass-to-charge ratio (m/z) were 512.04, 514.04, respectively, and were of substantially the same intensity, establishing the structure as shown by 7-1.
Nuclear magnetic detection is carried out on the intermediate 7-1, and the result is obtained 1 H-NMR (Bruker, Switzerland, Avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl) 3 ):δ8.35(m，1H)，δ8.11(m，1H)，δ8.06(d，1H)，δ8.04(d，1H)，δ7.99(d，1H)，δ7.95(m，2H)，δ7.76(d，1H)，δ7.62(m，1H)，δ7.58～7.52(m，4H)，δ7.37(m，2H)，δ7.28(m，2H)。
(2) Synthesis of Compound 7
Figure BDA0003684294180000353
With reference to the synthesis of compound 3, the only difference is that intermediate 2-1 is replaced with an equivalent amount of intermediate 7-1 and 2-naphthaleneboronic acid is replaced with an equivalent amount of intermediate
Figure BDA0003684294180000361
Compound 7 is obtained.
Mass spectrometric detection of compound 7: the mass to charge ratio (m/z) was found to be 636.21.
Synthesis example 8
This synthetic example provides a compound 8, the preparation method of which is as follows:
Figure BDA0003684294180000362
with reference to the synthesis of compound 3, the only difference is that intermediate 2-1 is replaced with an equivalent amount of intermediate 7-1 and 2-naphthaleneboronic acid is replaced with an equivalent amount of intermediate
Figure BDA0003684294180000363
Compound 8 is obtained.
Mass spectrometric detection of compound 8: the mass to charge ratio (m/z) was found to be 626.22.
Synthesis example 9
This synthetic example provides a compound 9, the preparation method of which is as follows:
(1) synthesis of Compound 9-1
Figure BDA0003684294180000364
Reference is made to the synthesis of compound 2-1, the only difference being dibenzo [ b, d ]]With equivalent amounts of furan-3-boronic acid substituted
Figure BDA0003684294180000365
Compound 9-1 is obtained.
Mass spectrometric detection of Compound 9-1: the two peaks with the largest measured mass-to-charge ratio (m/z) were 562.06, 564.05, respectively, and were of substantially the same intensity, confirming the structure as shown in 9-1.
(2) Synthesis of Compound 9
Figure BDA0003684294180000371
Referring to the synthesis of compound 3, the only difference is that compound 9 is obtained by replacing intermediate 2-1 with an equivalent amount of intermediate 9-1.
Mass spectrometric detection of compound 9: a mass to charge ratio (m/z) of 610.19 was measured.
Synthesis example 10
This synthetic example provides a compound 10, the preparation method of which is as follows:
Figure BDA0003684294180000372
referring to the synthesis of compound 3, the only difference was that intermediate 2-1 was replaced with an equivalent amount of intermediate 9-1 and naphthalene boronic acid was replaced with an equivalent amount of phenylboronic acid to give compound 10.
Mass spectrometric detection of compound 10: the mass to charge ratio (m/z) was measured to be 560.18.
Synthesis example 11
The synthesis example provides a compound D1, and the preparation method thereof is as follows:
Figure BDA0003684294180000373
80mL of toluene, 50mL of ethanol, and 20mL of water were added to a 250mL three-necked flask under nitrogen atmosphere, and the intermediate (5.16g) shown in MD1 was added, followed by further addition of phenylboronic acid (2.5g) and Na 2 CO 3 (3.0g) and tetrakistriphenylphosphine palladium (0.23g), the mixture was gradually heated to reflux reaction for 8 hours, the temperature was reduced to room temperature, water was added to separate the reaction solution, the organic layer was washed with water, magnesium sulfate and a small amount of silica gel were added to dry the mixture, the magnesium sulfate and the silica gel were removed by filtration, the solvent was removed under reduced pressure, and the obtained solid was crystallized from a mixed solvent of ethanol and toluene to give compound D1(4.7 g).
Mass spectrometric detection of compound D1: the mass to charge ratio (m/z) was found to be 510.16.
Elemental analysis was performed on compound D1, theoretical value: c, 89.39%; h, 4.34%; o, 6.27%, found: c, 89.37%; h,4.33 percent.
Synthesis example 12
The synthesis example provides a compound D2, and the preparation method thereof is as follows:
Figure BDA0003684294180000381
referring to the synthesis method of compound D1, the only difference was that compound D2 was obtained by replacing phenylboronic acid with 2-naphthylboronic acid in an equivalent amount.
Mass spectrometric detection of compound D2: a mass to charge ratio (m/z) of 610.19 was measured.
Synthesis example 12
The synthesis example provides a compound D3, and the preparation method thereof is as follows:
(1) synthesis of Compound D3-1
Figure BDA0003684294180000382
Under nitrogen protection, a 250mL three-necked flask was charged with 80mL of toluene, 40mL of ethanol, and 20mL of water, followed by addition of intermediate (5.16g) shown in MD1-A, further addition of phenylboronic acid (1.7g) and Na 2 CO 3 (1.5g) and tetrakistriphenylphosphine palladium (0.115g), slowly heating to 60 ℃ for reaction for 2h, then heating to 80 ℃ for reaction for 6h, cooling to room temperature, adding water for liquid separation, washing an organic layer with water, adding magnesium sulfate and a small amount of silica gel for drying, filtering to remove magnesium sulfate and silica gel, removing the solvent under reduced pressure, carrying out column chromatography separation on the obtained solid silica gel, and eluting with petroleum ether to obtain a compound D3-1(3.9 g).
Mass spectrometric detection of Compound D3-1: the two peaks with the largest measured mass-to-charge ratio (m/z) were 562.06, 564.05, respectively, and were of substantially the same intensity, determined to be of structure D3-1.
(2) Synthesis of Compound D3
Figure BDA0003684294180000383
With reference to the synthesis of compound D3-1, the only difference was that intermediate MD1 was replaced with an equivalent amount of intermediate D3-1, and
Figure BDA0003684294180000384
by substitution with equal amounts of substances
Figure BDA0003684294180000385
And isThe reaction conditions were reflux reaction for 8h to afford compound D3.
Mass spectrometric detection of compound D3: a mass to charge ratio (m/z) of 610.19 was measured.
Synthesis example 14
The synthesis example provides a compound D4, and the preparation method thereof is as follows:
Figure BDA0003684294180000391
with reference to the synthesis of compound D3, the only difference is that
Figure BDA0003684294180000392
By substitution with equal amounts of substances
Figure BDA0003684294180000393
Compound D4 was obtained.
Mass spectrometric detection of compound D4: the mass to charge ratio (m/z) was found to be 650.19.
Synthesis example 15
The synthesis example provides a compound D5, and the preparation method thereof is as follows:
Figure BDA0003684294180000394
with reference to the synthesis of compound D3, the only difference is that
Figure BDA0003684294180000395
By substitution with equal amounts of substances
Figure BDA0003684294180000396
Compound D5 was obtained.
Mass spectrometric detection of compound D5: the mass to charge ratio (m/z) was found to be 676.24.
Synthesis example 16
The synthesis example provides a compound D6, and the preparation method thereof is as follows:
Figure BDA0003684294180000397
with reference to the synthesis of compound D1, the only difference is that phenylboronic acid is replaced by an equivalent amount of substance
Figure BDA0003684294180000401
Compound D6 was obtained.
Mass spectrometric detection of compound D6: the mass to charge ratio (m/z) was found to be 624.28.
Synthesis example 17
The synthesis example provides a compound D7, and the preparation method thereof is as follows:
Figure BDA0003684294180000402
referring to the synthesis method of compound D1, the only difference was that compound D7 was obtained by replacing intermediate MD1 with an equivalent amount of intermediate MD2 and replacing phenylboronic acid with an equivalent amount of 2-naphthylboronic acid.
Mass spectrometric detection of compound D7: a mass to charge ratio (m/z) of 610.19 was measured.
Synthesis example 18
The synthesis example provides a compound D8, and the preparation method thereof is as follows:
Figure BDA0003684294180000403
referring to the synthesis method of compound D1, the only difference was that compound D8 was obtained by replacing intermediate MD1 with an equivalent amount of intermediate MD2 and replacing phenylboronic acid with an equivalent amount of 1-naphthylboronic acid.
Mass spectrometric detection of compound D8: a mass to charge ratio (m/z) of 610.19 was measured.
Synthetic example 19
The synthesis example provides a compound D9, and the preparation method thereof is as follows:
(1) synthesis of Compound D9-1
Figure BDA0003684294180000404
Referring to the synthesis method of compound D3-1, the only difference was that intermediate MD1 was replaced with an equivalent amount of intermediate MD2 and phenylboronic acid was replaced with an equivalent amount of 2-naphthylboronic acid to give compound D9-1.
Mass spectrometric detection of Compound D9-1: the two peaks with the largest measured mass-to-charge ratio (m/z), 562.06, 564.05, and substantially identical intensities, were determined to be of the structure D9-1.
(2) Synthesis of Compound 9
Figure BDA0003684294180000411
With reference to the synthesis of compound D3, the only difference was that compound D9 was obtained by replacing intermediate D3-1 with an equivalent amount of intermediate D9-1.
Mass spectrometric detection of compound D9: a mass to charge ratio (m/z) of 610.19 was measured.
Synthesis example 20
The synthesis example provides a compound D10, and the preparation method thereof is as follows:
Figure BDA0003684294180000412
with reference to the synthesis of compound D3, the only difference was that intermediate D3-1 was replaced with an equivalent amount of intermediate D9-1 and 1-naphthalene boronic acid was replaced with an equivalent amount of intermediate D9-1
Figure BDA0003684294180000413
Compound D10 was obtained.
Mass spectrometric detection of compound D10: the mass to charge ratio (m/z) was found to be 636.21.
The specific structures of several materials used in the following application examples are as follows:
Figure BDA0003684294180000414
the synthesis method of H3 is as follows:
Figure BDA0003684294180000421
referring to the synthesis method of compound 1, the only difference was that intermediate M1 was replaced with an equivalent amount of intermediate M3, and dibenzo [ b, d ] furan-3-boronic acid was replaced with an equivalent amount of 2-naphthaleneboronic acid, to give compound H3.
Mass spectrometric detection of compound H3: the mass to charge ratio (m/z) was found to be 520.18.
Application example 1
The application example provides an organic electroluminescent device, and the structure of the organic electroluminescent device is as follows: HI-2 (5%) (20nm)/HTL (50nm)/HTSP3(20 nm)/BH: BD-1 (5%) (30nm)/TPBI (30nm)/Al (150 nm);
the preparation method of the organic electroluminescent device comprises the following steps:
placing each layer of material in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～1×10 -6 Pa, and sequentially performing vacuum evaporation on the cleaned ITO substrate. Wherein HTL: HI-2 (5%) (20nm) means that in this device HTL and HI-2 were co-evaporated in a volume ratio of 95:5 to form a hole injection layer having a thickness of 20 nm. BH: BD-1 (5%) (30nm) means that BH and BD-1 are mixed at 95:5 was co-evaporated to form a light-emitting layer having a thickness of 30 nm.
In the application example, the HTL material is a mixture of D4-HTSP1 and D8-HTSP1, and the two different compounds are respectively placed in different evaporation sources, and the evaporation rates of the two compounds are controlled by controlling the temperatures of the evaporation sources to obtain a mixture with a desired volume ratio, which is used as the HTL of the device.
BH is a blue light host material, and in the application example, BH is a compound 1.
In the device provided by the application example, HI-2 (5%) (20nm) is a hole injection layer, HTL (50nm) is a hole transport layer, and HTSP3(20nm) is an electron blocking layer. In this application example, a mixture of D4-HTSP1 and D8-HTSP1 was used as both the hole injection material and the hole transport material in this device, and the volume ratio of the two was 5: 5.
Application examples 2 to 8
Application examples 2 to 8 each provide an organic electroluminescent device, which is different from application example 1 only in that BH material is different (specific composition is as described in table 1 below), and other preparation steps are the same as application example 1.
Comparative application examples 1 to 4
Comparative application examples 1 to 4 each provide an organic electroluminescent device, which is different from application example 1 only in the BH material (specifically, as described in table 1 below), and the other preparation steps are the same as application example 1.
Performance testing
The test method comprises the following steps: testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance, wherein the test items comprise the brightness, the driving voltage, the current efficiency and LT80 of an organic electroluminescent device; wherein LT80 refers to maintaining the initial brightness of the device at 1000cd/m 2 The current density of the transistor is not changed, and the efficiency of the device is reduced to 1000cd/m of the initial brightness 2 The time required for 80% of the corresponding efficiency.
The specific test results are shown in table 1 below:
TABLE 1
Figure BDA0003684294180000422
Figure BDA0003684294180000431
As can be seen from the contents in table 1, the structure of the anthrafuran compound is designed, and the group represented by formula BH-a1 is fused with two adjacent carbon atoms on ring a and/or ring B in the group represented by formula BH-a, and the anthrafuran compound is controlled to have at least two heteroatoms, so that the anthrafuran compound is used as a host material of a light-emitting layer of an OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency, and a longer lifetime.
Compounds 1 to 4 of application examples 1 to 4, having
Figure BDA0003684294180000432
(dotted line indicates the attachment site of the substituent, the same below) the parent core structure, the efficiency and lifetime of the device are significantly improved.
Application examples 5 and 6 use the compounds 5 to 6 as host materials for light-emitting layers, and the compounds 5 to 6 each have
Figure BDA0003684294180000433
The service life of the organic electroluminescent device prepared by the mother core structure is short, but the driving voltage of the organic electroluminescent device is obviously reduced, and the current efficiency of the organic electroluminescent device is improved.
Application examples 7 to 8 Using Compounds 7 to 8 as host materials for light-emitting layers, Compounds 7 to 8 all had
Figure BDA0003684294180000434
The voltage and the service life of the mother core structure and the organic electroluminescent device are obviously improved.
Application examples 9 to 10 in which compounds 9 to 10 were used as host materials for light-emitting layers, the compounds 9 to 10 contained
Figure BDA0003684294180000435
The organic electroluminescent device has improved voltage, efficiency and service life, especially has improved service life.
Compared with application examples 1 to 10, if the anthrafuran compound has only one heteroatom (comparative examples 1 to 4), the organic electroluminescent device prepared has higher driving voltage, lower current efficiency and shorter service life.
Application example 11
The application example provides an organic electroluminescent device, and the structure of the organic electroluminescent device is as follows: HI-2 (5%) (20nm)/HTL (50nm)/HTSP3(20 nm)/BH: BD-1 (5%) (30nm)/TPBI (30nm)/Al (150 nm);
the preparation method of the organic electroluminescent device comprises the following steps:
placing each layer of material in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～1×10 -6 Pa, and sequentially performing vacuum evaporation on the cleaned ITO substrate. Wherein HTL: HI-2 (5%) (20nm) means that in this device HTL and HI-2 were co-evaporated in a volume ratio of 95:5 to form a hole injection layer having a thickness of 20 nm. BH: BD-1 (5%) (30nm) means that BH and BD-1 are mixed at 95:5 was co-evaporated to form a light-emitting layer having a thickness of 30 nm.
In the application example, the HTL material is D8-HTSP 2.
BH is a blue light host material, and in the application example, BH is a compound 1.
In the device provided by the application example, HI-2 (5%) (20nm) is a hole injection layer, HTL (50nm) is a hole transport layer, and HTSP3(20nm) is an electron blocking layer.
Application examples 12 to 13
Application examples 12 to 13 each provide an organic electroluminescent device, which is different from application example 11 only in that BH material is different (specifically, as described in table 2 below), and other preparation steps are the same as application example 11.
Comparative application examples 5 to 6
Comparative application examples 5 to 6 each provide an organic electroluminescent device, which is different from application example 11 only in the BH material (specifically, as described in table 2 below), and the other preparation steps are the same as application example 11.
Performance testing
The test method comprises the following steps: testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance, wherein the test items comprise the brightness, the driving voltage, the current efficiency and LT80 of an organic electroluminescent device; wherein LT80 refers to maintaining the initial brightness of the device at 1000cd/m 2 The current density of the transistor is not changed, and the efficiency of the device is reduced to 1000cd/m of the initial brightness 2 The time required for 80% of the corresponding efficiency.
The specific test results are shown in table 2 below:
TABLE 2
Figure BDA0003684294180000441
From the contents of table 2, the organic electroluminescent device prepared by using the anthrafuran compound having a specific structure as the host material of the light-emitting layer and D8-HTSP2 as the hole material (application examples 11 to 13) according to the present invention has high current efficiency and long lifetime.
Application example 14
The application example provides an organic electroluminescent device, and the structure of the organic electroluminescent device is as follows: HI-2 (5%) (20nm)/HTL (50nm)/HTSP3(20 nm)/BH: BD-4 (5%) (30nm)/TPBI (30nm)/Al (150 nm);
the preparation method of the organic electroluminescent device comprises the following steps:
placing each layer of material in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～1×10 -6 Pa, and sequentially performing vacuum evaporation on the cleaned ITO substrate. Wherein HTL: HI-2 (5%) (20nm) means that in this device HTL and HI-2 were co-evaporated in a volume ratio of 95:5 to form a hole injection layer having a thickness of 20 nm. BH: BD-4 (5%) (30nm) means that BH and BD-4 are mixed at 95:5 was co-evaporated to form a light-emitting layer having a thickness of 30 nm.
In the application example, the HTL material is a mixture of D4-HTSP1 and D8-HTSP1, and the two different compounds are respectively placed in different evaporation sources, and the evaporation rates of the two compounds are controlled by controlling the temperatures of the evaporation sources to obtain a mixture with a desired volume ratio, which is used as the HTL of the device.
BH is blue light main body material, and in the application example, BH is compound D1.
In the device provided by the application example, HI-2 (5%) (20nm) is a hole injection layer, HTL (50nm) is a hole transport layer, and HTSP3(20nm) is an electron blocking layer. In this application example, a mixture of D4-HTSP1 and D8-HTSP1 was used as both the hole injection material and the hole transport material in this device, and the volume ratio of the two was 5: 5.
Application examples 15 to 23
Application examples 15-23 differ from application example 14 only in that the BH materials are different (specifically, as described in table 3 below), and other preparation steps are the same as in application example 14.
Comparative application examples 7 to 8
Comparative application examples 7-8 differ from application example 14 only in the BH materials (specific compositions are as described in table 3 below), and other preparation steps are the same as application example 14.
Performance test
The test method comprises the following steps: testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance, wherein the test items comprise the brightness, the driving voltage, the current efficiency and LT80 of an organic electroluminescent device; wherein LT80 refers to maintaining the initial brightness of the device at 1000cd/m 2 The current density of the transistor is not changed, and the efficiency of the device is reduced to 1000cd/m of the initial brightness 2 The time required for 80% of the corresponding efficiency.
The specific test results are shown in table 3 below:
TABLE 3
Figure BDA0003684294180000451
As can be seen from the content in table 3, the structure of the anthrafuran compound is designed, and the group represented by formula BH-a1 is fused with two adjacent carbon atoms on ring a and/or ring B in the group represented by formula BH-a, and the anthrafuran compound is controlled to have at least two heteroatoms, so that the anthrafuran compound is used as the host material of the light-emitting layer of the OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency, and a longer lifetime.
Application examples 20 to 23 use the compounds D7 to D10 as host materials for light-emitting layers, and the compounds D7 to D10 contain
Figure BDA0003684294180000452
The service life of the organic electroluminescent device provided by the mother core structure is short, butThe driving voltage of the organic electroluminescent device is obviously reduced, and the current efficiency of the organic electroluminescent device is obviously improved.
The applicant states that the present invention is illustrated by the detailed process flow of the present invention through the above examples, but the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (10)

1. An anthracofuran compound, which is obtained by fusing at least one group represented by the formula BH-A1 with any two adjacent carbon atoms on the ring A and/or the ring B in the group represented by the formula BH-A;
Figure FDA0003684294170000011
wherein denotes the site of fusion of a group of formula BH-A1; the opposite side indicates the condensed sites of hydrogen atoms or groups of the formula BH-A;
Ar 101 and Ar 102 Each independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;
Ar 101 and Ar 102 Wherein the substituted substituents are independently selected from at least one of-D, C1-C10 alkyl, C1-C6 alkoxy or C6-C15 aryl;
the hydrogen atom in the anthracofuran compound can be substituted by at least one of-D, -F, -CN, C1-C10 alkyl, C1-C6 alkoxy or C6-C15 aryl;
the anthracenopyran compound contains at least two heteroatoms in the heteroaryl group.
2. The anthrafuran compound of claim 1, wherein the anthrafuran compound is selected from any one of the following anthrafurans compounds 1 to 27:
Figure FDA0003684294170000012
Figure FDA0003684294170000021
wherein in the anthracenopyran compounds 1-6, Ar is 101 And Ar 102 Has the same protective scope as claim 1, and Ar 101 And Ar 102 At least one is selected from substituted or unsubstituted C12-C20 heteroaryl;
in the anthracenopyran compounds 7-27, Ar 101 And Ar 102 Having the same protective scope as claimed in claim 1.
3. The anthrafuran compound of claim 1 or 2, wherein the C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, or benzonaphthofluorenyl;
preferably, the C12-C20 heteroaryl is selected from any one of dibenzofuran, dibenzothiophene, dinaphthofuran and dinaphthothiophene;
preferably, Ar 101 And Ar 102 Each independently selected from any one of the following groups substituted unsubstituted: phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, dibenzofuranyl, fluorenyl;
of said, Ar 101 And Ar 102 Substituted as described in (1)The substituents are independently selected from at least one of-D, methyl, ethyl, tert-butyl, adamantyl, hexyloxy, methoxy, isopropoxy, phenyl or naphthyl;
preferably, the hydrogen atom in the anthrafuran compound may be substituted with at least one of-D, methyl, ethyl, t-butyl, adamantyl, hexyloxy, methoxy, isopropoxy, phenyl, or naphthyl.
4. The anthrafurans compound according to any one of claims 1 to 3, wherein the anthrafurans compound is selected from any one of the following compounds:
Figure FDA0003684294170000022
Figure FDA0003684294170000031
Figure FDA0003684294170000041
Figure FDA0003684294170000051
Figure FDA0003684294170000061
Figure FDA0003684294170000071
Figure FDA0003684294170000081
Figure FDA0003684294170000091
5. an intermediate, characterized in that the intermediate is selected from any one of the following compounds:
Figure FDA0003684294170000092
the intermediate is used for preparing the anthracenopuran compound as described in any one of claims 1 to 4.
6. An organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising the anthrafuran-based compound according to any one of claims 1 to 4;
preferably, the organic thin film layer includes a light-emitting layer whose material includes the anthrafuran-based compound according to any one of claims 1 to 4;
preferably, the organic thin film layer further includes a hole layer including a hole transport layer, a hole injection layer, and an electron blocking layer.
7. The organic electroluminescent device according to claim 6, wherein the material of the hole layer is selected from a compound having a structure represented by formula I or a deuterated composition comprising at least two compounds each having a structure represented by formula I;
Figure FDA0003684294170000101
wherein Ar is 11 、Ar 12 、Ar 21 、Ar 22 Ar is independently selected from substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C20 heteroaryl;
Ar 11 、Ar 12 may be connected by a single bond, Ar 21 、Ar 22 Can be connected by a single bond; ar, Ar 12 Can be connected by a single bond, Ar 11 Can be connected by a single bond, Ar 21 Can be connected by a single bond, Ar 22 Can be connected by a single bond;
n is selected from 0 or 1;
Ar 11 、Ar 12 、Ar 21 、Ar 22 and the substituted substituent groups in Ar are respectively and independently selected from at least one of C1-C12 alkyl, C1-C12 alkoxy and C6-C12 aryl;
the compound of formula I meets at least one of the following conditions:
(1) the compound of the formula I does not contain deuterium atom;
(2)Ar 11 、Ar 12 、Ar 21 、Ar 22 or the hydrogen atoms of at least one of the substituted substituents in Ar are all substituted by deuterium atoms;
(3)Ar 11 、Ar 12 、Ar 21 、Ar 22 or at least one of the hydrogen atoms of Ar is entirely substituted by a deuterium atom;
the deuterated composition comprises a compound of formula I meeting the condition (2) or (3).
8. The organic electroluminescent device according to claim 7, wherein Ar is selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenylenyl, fluorenyl, benzofluorenyl;
the substituted substituent is selected from at least one of methyl, ethyl, tertiary butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl or naphthyl;
preferably, Ar is 11 、Ar 12 、Ar 21 、Ar 22 Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, triphenylene, fluoranthenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiophenyl;
the substituted substituents are each independently selected from at least one of methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or naphthyl.
9. The organic electroluminescent device according to claim 7 or 8, wherein the compound of formula I is selected from any one of the following substituted or unsubstituted compounds:
Figure FDA0003684294170000111
Figure FDA0003684294170000121
Figure FDA0003684294170000131
Figure FDA0003684294170000141
Figure FDA0003684294170000151
Figure FDA0003684294170000161
Figure FDA0003684294170000171
Figure FDA0003684294170000181
Figure FDA0003684294170000191
Figure FDA0003684294170000201
Figure FDA0003684294170000211
the substitution means that hydrogen atoms in the above compounds are partially or completely substituted with deuterium atoms.
10. A display device characterized in that the display device comprises the organic electroluminescent device according to any one of claims 6 to 9.
CN202210646471.4A 2022-06-08 2022-06-08 Anthracene furan compound, intermediate, organic electroluminescent device and display device Pending CN114835699A (en)

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