An anthracene compound, an intermediate, an anthracene mixture, an organic electroluminescence device, and a display device

Abstract

The application provides an anthracene compound, an intermediate, an anthracene mixture, an organic electroluminescent device and a display device. The anthracene compound has a structure as shown in formula (I) or formula (II). In the application, through the design of the structural formula of the anthracene compound, an anthracene compound and an anthracene mixture with a specific structure are obtained, and when the anthracene compound or the anthracene mixture is used as a main body material of a light-emitting layer, an organic electroluminescent device prepared has a lower driving voltage, a higher current efficiency and a longer service life.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic electroluminescent materials, and particularly relates to an anthracene compound, an intermediate, an anthracene mixture, an organic electroluminescent device and a display device. BACKGROUND

[0002] Electroluminescence, also known as electric field luminescence, for short, EL, is a luminescence phenomenon that a solid directly converts electric energy into light energy under the action of an electric field generated by a voltage applied to two electrodes. The electroluminescence of an organic material belongs to injection type composite luminescence, and the organic electroluminescent material can be divided into hole injection layer (HIL), hole transport layer (HTL), light-emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL) and other materials according to different functions in an organic electroluminescent (OLED) device and different device structures.

[0003] At present, the organic electroluminescence (OLED) has become a mainstream display technology, and accordingly various new OLED materials have also been developed. As a blue light host material of a light-emitting layer, the current main compound is obtained by substituting the 9,10 position of anthracene with an aromatic group, wherein the aromatic group mainly includes benzene, naphthalene, anthracene, dibenzofuran, dibenzothiophene, benzo-dibenzofuran, benzo-dibenzothiophene and the like.

[0004] However, various performances thereof still need to be improved, especially in terms of efficiency, service life, voltage and the like. In order to meet the higher requirements of people for OLED devices, more types and higher performance blue light host materials need to be developed in the field. SUMMARY

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide an anthracene compound, an intermediate, an anthracene mixture, an organic electroluminescent device and a display device. The organic electroluminescent device prepared by using the anthracene compound with a specific structure has good comprehensive performance.

[0006] To achieve this purpose, the present application adopts the following technical solutions:

[0007] In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first aspect, the present application provides an anthracene compound, which has a structure as shown in formula (I) or formula (II):

[0008]

[0009] In the anthracene compounds of formula (I) and formula (II), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group;

[0010] X is selected from O, S or In a first

[0011] R 11 , R 12 is selected from any one of substituted or unsubstituted C1-C6 linear or branched alkyl, substituted or unsubstituted phenyl, R 11 , R 12 is not connected or connected into a ring by a chemical bond;

[0012] The rings A and B in the anthracene compounds of formula (I) and formula (II) each include four sp2 hybridized carbon atoms, and the four sp2 hybridized carbon atoms in the rings A and B and the adjacent benzene rings are fused;

[0013] The rings A and B in the anthracene compounds of formula (I) and formula (II) can each independently exist or not exist;

[0014] Ar1, Ar2, R 11 , R 12 The substituted substituents in the above-mentioned substituted groups are each independently selected from at least one of -F, -CN, -D, C1-C12 branched or branched alkyl, C2-C8 alkenyl, C1-C6 alkoxy or C6-C40 aryl;

[0015] a in the anthracene compounds of formula (I) and formula (II) is each independently selected from an integer from 0 to 4;

[0016] b in the anthracene compounds of formula (I) and formula (II) is each independently selected from an integer from 0 to 8.

[0017] In the present application, by designing the position of the Ar2 substituent, it is in the meta position (formula (I)) or in the ortho position (formula (II)) with the position of another substituent on the benzene ring (the benzene ring directly connected with Ar2), thereby obtaining an anthracene compound with a specific structure. With the anthracene compound with a specific structure as a raw material, the organic electroluminescent device prepared has good comprehensive performance, has a lower driving voltage, has a higher current efficiency, and has a longer service life.

[0018] In the present application, Ar1 and Ar2 in the anthracene compounds of formula (I) and formula (II) are each independently selected from substituted or unsubstituted C6-C40 aryl (for example, it can be C6, C8, C10, C15, C20, C35, C38 or C40, etc.), and further, Ar1 and Ar2 in the anthracene compounds of formula (I) and formula (II) are each independently selected from substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrobenzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl.

[0019] R 11 , R12 selected from substituted or unsubstituted C1-C6 linear or branched alkyl, for example, can be methyl, ethyl, propyl, n-butyl, isobutyl, n-pentyl, isopentyl, neopentyl, and the like.

[0020] Ar1, Ar2, R 11 , R 12 each of the substituents in the substituents described in Ar1, Ar2, X, R

[0021] Further, the C1-C12 branched or branched alkyl is selected from methyl, ethyl, propyl, or butyl; the C1-C12 alkoxy is selected from methoxy, ethoxy, propoxy, or butoxy; and the C6-C40 aryl is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrobenzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzindenofluorenyl, naphthofluorenyl, or benzonaphthofluorenyl.

[0022] It should be noted that in the present application, "the four sp2 hybridized carbon atoms in ring A and ring B in the anthracene compounds of formula (I) and formula (II) are fused with adjacent benzene rings" means that the four sp2 hybridized carbon atoms in ring A and ring B are fused with adjacent benzene rings to form a naphthalene ring.

[0023] Ring A and ring B in the anthracene compounds of formula (I) and formula (II) can each independently exist or not exist.

[0024] The following are preferred technical solutions of the present application, but not as a limitation on the technical solutions provided by the present application, through the following preferred technical solutions, the purpose and beneficial effects of the present application can be better achieved and realized.

[0025] As a preferred technical solution of the present application, b in the anthracene compounds of formula (I) and formula (II) is 8, and the anthracene compounds have a structure as shown in formula (I-a) or formula (II-a):

[0026]

[0027] In formula (I-a), Ar1, Ar2, X, R11 , R 12 , ring A, ring B and a each independently have the same defined range as formula (I);

[0028] Ar1, Ar2, X, R 11 , R 12 , ring A, ring B and a each independently have the same defined range as formula (II).

[0029] As a preferred technical solution of the present application, the anthracene compound having the structure as shown in formula (I) or formula (II) each independently meets at least one of the following conditions:

[0030] (1) all hydrogen atoms on Ar1 in formula (I) or formula (II) are replaced by deuterium atoms;

[0031] (2) all hydrogen atoms on Ar2 in formula (I) or formula (II) are replaced by deuterium atoms;

[0032] (3) a in formula (I) or formula (II) is 4;

[0033] (4) b in formula (I) or formula (II) is 8.

[0034] Preferably, the anthracene compound having the structure as shown in formula (I) or formula (II) each independently meets conditions (1) to (4).

[0035] As a preferred technical solution of the present application, Ar1 is selected from any one of the following groups:

[0036]

[0037] wherein the short line represents the connecting site of the group.

[0038] Preferably, Ar2 is selected from any one of the following groups:

[0039]

[0040] wherein the short line represents the connecting site of the group.

[0041] Preferably, R 11 , R 12 each independently is selected from methyl, ethyl or phenyl.

[0042] As a preferred technical solution of the present application, the anthracene compound having the structure as shown in formula (I) is selected from any one of the following anthracene compounds 1 to 276, anthracene compounds 1S to 276S:

[0043] The structural formula of the anthracene compounds 1-276 is shown as follows:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S. The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S.

[0058] It should be noted that the anthracene compound 1S-276S is formed by replacing O at the X position in the anthracene compound 1-276 with S, for example, the anthracene compound 1 has a structure shown in formula (I) The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S. The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S. The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S. The anthracene compound 1S-276S has a structure shown in formula (I) and is formed by replacing O at the X position in the anthracene compound 1-276 with S.

[0059] Preferably, the anthracene compound having a structure shown in formula (II) is selected from any one of the following anthracene compounds II-1-II-276, anthracene compounds II-1S-II-276S.

[0060] The anthracene compound II-1~II-276 has a structure formula that the substituent at the corresponding Ar2 in anthracene compounds 1~276 with the structure formula (I) is replaced to the corresponding Ar2 in anthracene compounds with the structure formula (II) to form the anthracene compound II-1~II-276.

[0061] The anthracene compound II-1S~II-276S has a structure formula that the substituent at the corresponding Ar2 in anthracene compounds 1S~276S with the structure formula (I) is replaced to the corresponding Ar2 in anthracene compounds with the structure formula (II) to form the anthracene compound II-1S~II-276S.

[0062] It should be noted that the structure formula of the anthracene compound II-1~II-276 is that the substituent at the corresponding Ar2 in anthracene compounds 1~276 with the structure formula (I) (the position relationship with another substituent on the benzene ring is meta) is replaced to the corresponding Ar2 in anthracene compounds with the structure formula (II) (the position relationship with another substituent on the benzene ring is ortho), and the selection and position of other substituents are the same as those of the corresponding anthracene compounds 1-276, to form the anthracene compound II-1~II-276, for example, the structure formula of the anthracene compound 1 is and the structure formula of the anthracene compound II-1 is For another example, the structure formula of the anthracene compound 217 is and the structure formula of the anthracene compound II-217 is As can be seen from the above examples, the anthracene compound 1 and the anthracene compound II-1, and the anthracene compound 217 and the anthracene compound II-217, only the substitution position of the biphenyl group connected to the dibenzofuran is changed, that is, only the substituent (phenyl) at Ar2 is changed in position, and the selection and position of other substituents are not changed.

[0063] The structure formula of the anthracene compound II-1S~II-276S is that the substituent at the corresponding Ar2 in anthracene compounds 1S~276S with the structure formula (I) (the position relationship with another substituent on the benzene ring is meta) is replaced to the corresponding Ar2 in anthracene compounds with the structure formula (II) (the position relationship with another substituent on the benzene ring is ortho) to form the anthracene compound II-1S~II-276S. That is, the structure formula of the anthracene compound II-1S~II-276S is that O or in the corresponding X position of the anthracene compound II-1~II-276 with the structure formula (II) is replaced to S to form the anthracene compound II-1S~II-276S. For example, the structure formula of the anthracene compound II-1 is and the structure formula of the anthracene compound II-1S is For example, the anthracene compound II-217 has the structural formula The anthracene compound II-217S has the structural formula

[0064] In the present application, the synthesis of the anthracene compound can be carried out by C-C coupling reactions known in the art, such as suzuki coupling reaction, Negishi reaction, to link the fragments of the compound of the present application together to prepare the compound of the present application.

[0065] In a second aspect, the present application provides an intermediate, which has the structure as shown in formula (I-Y) or formula (II-Y):

[0066]

[0067] wherein Ar1, Ar2, X, R 11 , R 12 , ring A, ring B, a and b each independently have the same defined range as in formula (I) or formula (II);

[0068] Y in formula (I-Y) and formula (II-Y) represents Br or I;

[0069] The intermediate of formula (I-Y) is used for preparing the anthracene compound of formula (I) as described in the first aspect.

[0070] The intermediate of formula (II-Y) is used for preparing the anthracene compound of formula (II) as described in the first aspect.

[0071] Preferably, the intermediate of formula (I-Y) or formula (II-Y) is selected from any one of the following intermediates:

[0072]

[0073] In a third aspect, the present application provides an anthracene mixture, which comprises at least two anthracene compounds as described in the first aspect.

[0074] Preferably, the anthracene mixture comprises the anthracene compound of formula (I) which does not meet any one of conditions (1) to (4) and / or the anthracene compound of formula (II) which does not meet any one of conditions (1) to (4).

[0075] Further, the anthracene mixture includes the anthracene compound of formula (I) not satisfying any one of conditions (1) to (4) and / or the anthracene compound of formula (II) not satisfying any one of conditions (1) to (4), and the anthracene mixture includes the anthracene compound of formula (I) satisfying any one of conditions (1) to (4) and / or the anthracene compound of formula (II) satisfying any one of conditions (1) to (4). That is, the anthracene mixture includes the anthracene compound of formula (I) and / or the anthracene compound of formula (II) not containing deuterium atom, and the anthracene mixture includes the anthracene compound of formula (I) and / or the anthracene compound of formula (II) containing deuterium atom.

[0076] Preferably, the volume ratio of the anthracene compound not containing deuterium atom to the anthracene compound containing deuterium atom is 1:10 to 10:1, for example, 1:10, 3:10, 7:10, 1:1, 3:1, 5:1, 7:1 or 10:1, etc. The anthracene compound not containing deuterium atom refers to the anthracene compound of formula (I) not satisfying any one of conditions (1) to (4) and / or the anthracene compound of formula (II) not satisfying any one of conditions (1) to (4); the anthracene compound containing deuterium atom refers to the anthracene compound of formula (I) satisfying any one of conditions (1) to (4) and / or the anthracene compound of formula (II) satisfying any one of conditions (1) to (4).

[0077] In a fourth aspect, the present application provides an organic electroluminescent device, which comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer.

[0078] The material of the organic thin film layer comprises the anthracene compound according to the first aspect and / or the anthracene mixture according to the third aspect.

[0079] As a preferred technical solution of the present application, the material of the organic thin film layer further comprises a compound having a structure as shown in formula (III):

[0080]

[0081] wherein, Ar 21 , Ar 22 each independently is selected from any one of substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;

[0082] R 21 , R 22 and R 23 each independently is selected from any one of hydrogen, C1-C12 linear or branched alkyl, C6-C12 cycloalkyl;

[0083] Ar21 , Ar 22 each of the substituents of the substitution described in Ar

[0084] Preferably, Ar 21 , Ar 22 each is independently selected from any one of the group consisting of

[0085] Preferably, R1, R2and R3each is independently selected from any one of the group consisting of hydrogen, methyl, ethyl, propyl, n-butyl, i-butyl, sec-butyl, t-butyl, cyclohexyl or adamantyl.

[0086] Preferably, the compound having the structure as shown in formula (III) is selected from any one of the following compounds:

[0087]

[0088]

[0089] Preferably, the material of the organic thin film layer further comprises a compound having the structure as shown in formula (IV):

[0090]

[0091] wherein Ar 31 , Ar 32 , Ar 33 and Ar 34 each is independently selected from any one of the group consisting of substituted or unsubstituted C6-C22 aryl, substituted or unsubstituted C12-C40 heteroaryl;

[0092] R 31 is selected from any one of the group consisting of phenyl, naphthyl or biphenyl;

[0093] a is selected from 0 or 1 ;

[0094] Ar 31 , Ar 32 , Ar 33 , Ar 34 each of the substituents of the substitution described in Ar

[0095] Preferably, Ar 31 , Ar 32 , Ar 33 and Ar 34 each is independently selected from or a combination of at least two of any one of the above.

[0096] Preferably, the compound having the structure as shown in formula (IV) is selected from any one of the following compounds:

[0097]

[0098] In a fifth aspect, the present application provides a display device comprising the organic electroluminescent device according to the fourth aspect.

[0099] Compared with the prior art, the present application has the following beneficial effects:

[0100] The present application designs the structural formula of anthracene compound, obtains anthracene compound and anthracene mixture with specific structure, and uses the anthracene compound or the anthracene mixture as the main material of the light-emitting layer, so that the prepared organic electroluminescent device has low driving voltage, high current efficiency and long service life. DETAILED DESCRIPTION

[0101] In order to facilitate the understanding of the present application, the present application is illustrated as follows. It should be understood by those skilled in the art that the examples are only to help understand the present application, and should not be regarded as specific limitations of the present application.

[0102] The preparation method of the anthracene compound having the structure as shown in formula (I) or formula (II) in the present application is as follows:

[0103] Preparation method of the anthracene compound having the structure of formula (I)

[0104]

[0105] Preparation method of the anthracene compound having the structure as shown in formula (II)

[0106]

[0107] In the above preparation method, Ar1, Ar2, X, R 11 , R 12 , ring A, ring B, a and b each independently have the same defined range as in formula (I) or formula (II);

[0108] Y represents Br or I.

[0109] Synthetic example 1

[0110] This example provides an anthracene compound 1, and the specific structural formula is as follows:

[0111]

[0112] The preparation method of the anthracene compound 1 provided by the embodiment is as follows:

[0113] (1) Synthesis of intermediate 1-1

[0114]

[0115] Under the protection of argon, 100 mL of dry tetrahydrofuran, 3.2 g of the compound shown in formula 1-0 (0.01 mol) were added into a 250 mL three-necked flask, and the temperature was lowered to-78°C. Then 6.25 mL of butyllithium with a concentration of 1.6 M (0.01 mol) was added dropwise. After the dropwise addition was completed, the temperature was kept at-78°C for 30 min. Then 1,2-dibromoethane (5 g) was added, and the temperature was slowly raised to room temperature. Water and ethyl acetate were added for liquid separation. After the organic layer was washed with water, it was dried with magnesium sulfate. After the magnesium sulfate was filtered off, the product was separated by silica gel column chromatography and eluted with petroleum ether to obtain 2.7 g of the intermediate shown in formula 1-1.

[0116] Mass spectrometry was performed on the intermediate shown in formula 1-1, and the two peaks with the largest mass-to-charge ratio (m / z) were 398.03 and 400.03, which determined that the molecular formula of the product was C 24 H 15 BrO;

[0117] H-NMR detection was performed on the intermediate shown in formula 1-1. 1 H-NMR (Switzerland Bruker Company, Avance II 400 MHz nuclear magnetic resonance spectrometer, CDCl3): δ 8.13 (m, 1H), δ 8.07 (m, 1H), δ 8.00 (m, 1H), δ 7.95 (m, 1H), δ 7.78-7.66 (m, 3H), δ 7.59 (m, 2H), δ 7.55-7.36 (m, 5H), δ 7.10 (m, 1H).

[0118] (1') Synthesis of intermediate 1-1I

[0119]

[0120] The synthesis method of the intermediate 1-1I is the same as that of the intermediate 1-1, except that 1,2-dibromoethane is replaced by an equal amount of iodine.

[0121] The characterization data of the intermediate shown in 1-1I are as follows:

[0122] Mass spectrometry was performed on the synthesized intermediate shown in 1-1I, and the mass-to-charge ratio (m / z) of the intermediate was 446.02, which determined that the molecular formula of the product was C 24 H 15 IO.

[0123] (2) The synthesis reaction formula of the anthracene compound 1 is as follows:

[0124]

[0125] The preparation method of anthracene compound 1 comprises the following steps: under the protection of nitrogen, 100 mL of toluene, 30 mL of ethanol, 20 mL of water, 3.99 g (0.01 mol) of the intermediate shown in 1-1, 2.98 g (0.01 mol) of 9-phenylanthracene-10-boronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetrakis triphenylphosphine palladium are added into a 250 mL three-necked flask, the reaction is slowly warmed to reflux for 12 h, then the reaction is completed, the temperature is lowered to room temperature, water is added for liquid separation, the organic layer is washed with water, then the organic layer is dried with magnesium sulfate, the magnesium sulfate is removed by filtration, the solvent is removed under reduced pressure, and the obtained solid is separated by silica gel column chromatography, and the obtained anthracene compound 1 (4.3 g) is eluted with petroleum ether.

[0126] The mass spectrometry detection result shows that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 1 is 572.21.

[0127] Meanwhile, the embodiment provides another preparation method (2') of the anthracene compound 1, which is different from the preparation method of the anthracene compound 1 in that the intermediate shown in 1-1 is replaced by the intermediate shown in 1-1I in an equal amount, and other conditions refer to the preparation method.

[0128] Synthesis Example 2

[0129] The embodiment provides an anthracene compound 2, and the specific structural formula is shown in the following formula:

[0130]

[0131] The preparation method of the anthracene compound 2 provided in the embodiment is as follows:

[0132] (1) Synthesis of intermediate 2-1 or 2-1I

[0133]

[0134] The synthesis methods of the intermediates 2-1 and 2-1I are the same as those of the intermediates 1-1 and 1-1I in the synthesis example 1, and the only difference is that the compound shown in formula 1-0 is replaced by the compound shown in formula 2-0, and other conditions refer to the synthesis methods of the intermediates 1-1 and 1-1I in the synthesis example 1.

[0135] The mass spectrometry detection is performed on the intermediate 2-1, and the two peaks with the largest mass-to-charge ratio (m / z) are 448.05 and 450.04, and it is determined that the molecular formula of the product is C 28 H 17 BrO;

[0136] NMR detection was performed on intermediate 2-1: 1 H-NMR (Switzerland Bruker Company, Avance II 400MHz nuclear magnetic resonance spectrometer, CDCl3): δ 8.23 (m, 1H), δ 8.12-7.96 (m, 5H), δ 7.90 (m, 1H), δ 7.74-7.56 (m, 5H), δ 7.54 (m, 1H), δ 7.50 (m, 1H), δ 7.45-7.35 (m, 2H), δ 7.09 (m, 1H).

[0137] Mass spectrometry was performed on intermediate 2-1I: the mass-to-charge ratio (m / z) was 496.03, and the molecular formula of the product was determined to be C 28 H 17 IO;

[0138] The synthesis reaction formula of anthracene compound 2 is as follows:

[0139]

[0140] The preparation method of anthracene compound 2 is the same as that of anthracene compound 1 in synthesis example 1, except that the intermediate 1-1 is replaced by an equal amount of intermediate 2-1, and other conditions refer to example 1 step (2).

[0141] The mass spectrometry result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 2 is 622.23.

[0142] Meanwhile, the present example provides another preparation method (2') of anthracene compound 2, which is different from the above preparation method (2) of anthracene compound 2 only in that the intermediate shown as 2-1 is replaced by an equal amount of intermediate shown as 2-1I, and other conditions are the same as the above preparation method.

[0143] Synthesis example 3

[0144] The present example provides an anthracene compound 6, and the specific structural formula is as follows:

[0145]

[0146] The preparation method of anthracene compound 6 provided in the present example is as follows:

[0147] (1) Synthesis of intermediate 6-1

[0148]

[0149] Into a 250 mL three-necked flask, 100 mL of toluene, 30 mL of ethanol, 20 mL of water were added, followed by the addition of 3.26 g (0.01 mol) of 4,6-dibromodibenzo[b,d]furan, 2.88 g (0.01 mol) of the boronic acid compound shown in Formula 6-0, 2.12 g (0.02 mol) of sodium carbonate, and 0.115 g (0.0001 mol) of tetrakis(triphenylphosphine)palladium, and the mixture was slowly warmed to reflux for 12 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the organic layer was washed with water, dried over magnesium sulfate, filtered to remove the magnesium sulfate, and the solvent was removed under reduced pressure. The obtained solid was separated by silica gel column chromatography using petroleum ether as the eluent to obtain 2.1 g of the intermediate shown in Formula 6-1.

[0150] The intermediate shown in Formula 6-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were 488.04 and 490.04, which confirmed that the molecular formula of the product was C 30 H 17 BrO2;

[0151] The intermediate shown in Formula 6-1 was subjected to H-NMR detection: 1H-NMR (Switzerland Bruker Company, Avance II 400 MHz nuclear magnetic resonance spectrometer, CDCl3): δ 8.19 (m, 1H), δ 8.06 (m, 1H), δ 8.04-7.95 (m, 3H), δ 7.88 (m, 1H), δ 7.76 (d, 1H), δ 7.71 (m, 1H), δ 7.64-7.50 (m, 5H), δ 7.45-7.27 (m, 3H), δ 7.09 (m, 1H).

[0152] (2) The synthesis reaction formula of anthracene compound 6 is as follows:

[0153]

[0154] The preparation method of anthracene compound 6 is the same as that of anthracene compound 1 in Synthesis Example 1, except that the intermediate 1-1 is replaced by an equivalent amount of intermediate 6-1, and the other conditions are referred to those in Example 1 step (2).

[0155] The mass spectrometry detection result confirmed that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 6 was 662.22.

[0156] Synthesis Example 4

[0157] This example provides an anthracene compound 21, and the preparation method is as follows:

[0158]

[0159] The preparation method of anthracene compound 21 provided in the embodiment is the same as that of synthetic example 1, except that 9-phenyl anthracene-10-boric acid in step (2) is replaced by 9-(1-naphthyl)-10-anthracene boric acid with equal amount of substance, and other conditions refer to synthetic example 1.

[0160] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 1 is 622.23.

[0161] Synthetic example 5

[0162] The embodiment provides an anthracene compound 22, and a preparation method thereof is as follows:

[0163]

[0164] The preparation method of anthracene compound 22 provided in the embodiment is the same as that of synthetic example 2, except that 9-phenyl anthracene-10-boric acid in step (2) is replaced by 9-(1-naphthyl)-10-anthracene boric acid with equal amount of substance, and other conditions refer to synthetic example 1.

[0165] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 22 is 672.25.

[0166] Synthetic example 6

[0167] The embodiment provides an anthracene compound 61, and a preparation method thereof is as follows:

[0168]

[0169] The preparation method of anthracene compound 61 provided in the embodiment is the same as that of synthetic example 1, except that 9-phenyl anthracene-10-boric acid in step (2) is replaced by 10-(4-biphenyl)-9-anthracene boric acid with equal amount of substance, and other conditions refer to synthetic example 1.

[0170] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 61 is 648.25.

[0171] Synthetic example 7

[0172] The embodiment provides an anthracene compound 66, and a preparation method thereof is as follows:

[0173]

[0174] The preparation method of anthracene compound 66 provided in the embodiment is the same as that of synthetic example 2, except that 9-phenylanthracene-10-boronic acid in step (2) is replaced by 10-(4-biphenyl)-9-anthracene boronic acid with equal amount of substance, and other conditions refer to synthetic example 1.

[0175] The mass spectrometry result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 66 is 738.26.

[0176] Synthetic example 8

[0177] The embodiment provides an anthracene compound 169, and a preparation method thereof is as follows:

[0178]

[0179] The preparation method of anthracene compound 169 provided in the embodiment is the same as that of synthetic example 1, except that is replaced by with equal amount of substance in step (2), and other conditions refer to synthetic example 1.

[0180] The mass spectrometry result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 169 is 724.28.

[0181] Synthetic example 9

[0182] The embodiment provides an anthracene compound 185, and a preparation method thereof is as follows:

[0183]

[0184] The preparation method of anthracene compound 185 provided in the embodiment is the same as that of synthetic example 1, except that is replaced by with equal amount of substance in step (2), and other conditions refer to synthetic example 1.

[0185] The mass spectrometry result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 185 is 662.22.

[0186] Synthetic example 10

[0187] The embodiment provides an anthracene compound II-1, and a specific structural formula is as follows:

[0188]

[0189] The preparation method of anthracene compound II-1 provided in the embodiment is as follows:

[0190] (1) Synthesis of intermediate II-1-1

[0191]

[0192] The synthesis method of intermediate II-1-1 is the same as that of intermediate 1-1 in synthesis example 1, except that the compound shown in formula 1-0 is replaced by the compound shown in formula II-1-0, and other conditions are the same as those in synthesis example 1.

[0193] The intermediate shown in formula II-1-1 is subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) are 398.03 and 400.03, and the molecular formula of the product is determined to be C 24 H 15 BrO;

[0194] The intermediate shown in formula II-1-1 is subjected to nuclear magnetic detection: 1H-NMR (Switzerland Bruker Company, Avance Ⅱ 400MHz nuclear magnetic resonance spectrometer, CDCl3): δ 8.09 (m, 1H), δ 8.03 (m, 1H), δ 8.01 (m, 2H), δ 7.90 (m, 1H), δ 7.80 (m, 2H), δ 7.61 (m, 2H), δ 7.53 (m, 1H), δ 7.39 (m, 2H), δ 7.34 (m, 2H), δ 7.10 (m, 1H).

[0195] (2) The synthesis reaction formula of anthracene compound II-1 is as follows:

[0196]

[0197] The preparation method of anthracene compound II-1 is the same as that of anthracene compound 1 in synthesis example 1, except that intermediate 1-1 is replaced by intermediate II-1-1, and other conditions refer to synthesis example 1.

[0198] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound II-1 is 572.21.

[0199] Synthesis example 11

[0200] This example provides an anthracene compound II-6, and the specific structural formula is as follows:

[0201]

[0202] The preparation method of anthracene compound II-1 provided in this example is as follows:

[0203] (1) Synthesis of intermediate II-6-1

[0204]

[0205] The synthesis method of intermediate II-6-1 is the same as that of intermediate 6-1 in synthesis example 3, except that the compound shown as formula 6-0 is replaced by the compound shown as formula II-6-0, and other conditions are the same as those in synthesis example 1.

[0206] The intermediate shown as formula II-6-1 is subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) are 488.04 and 490.04, and the molecular formula of the product is determined to be C 30 H 17 BrO2;

[0207] (2) The synthesis reaction formula of anthracene compound II-6 is as follows:

[0208]

[0209] The preparation method of anthracene compound II-6 is the same as that of anthracene compound 6 in synthesis example 3, except that intermediate 6-1 is replaced by intermediate II-6-1, and other conditions are referred to synthesis example 3.

[0210] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound II-6 is 662.22.

[0211] Synthesis example 12

[0212] This example provides an anthracene compound 1S, and the specific structural formula is as follows:

[0213]

[0214] The preparation method of anthracene compound 1S provided in this example is as follows:

[0215] (1) Synthesis of intermediate 1S-1

[0216]

[0217] The synthesis method of intermediate 1S-1 is the same as that of intermediate 1-1 in synthesis example 1, except that the compound shown as formula 1-0 is replaced by the compound shown as formula 1S-0, and other conditions are the same as those in synthesis example 1.

[0218] The intermediate shown as formula 1S-1 is subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) are 416.01 and 414.01, and the molecular formula of the product is determined to be C 24 H 15 BrS;

[0219] (2) The synthesis reaction formula of anthracene compound 1S is as follows:

[0220]

[0221] The preparation method of anthracene compound 1S is the same as that of anthracene compound 1 in synthesis example 1, except that intermediate 1-1 is replaced by intermediate 1S-1, and other conditions are the same as those in synthesis example 1.

[0222] Mass spectrometry results determine that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 1S is 588.19.

[0223] Synthesis example 13

[0224] This example provides an anthracene compound 21S, and the preparation reaction formula is as follows:

[0225]

[0226] The preparation method of anthracene compound 21S provided in this example is the same as that in synthesis example 4, except that intermediate 1-1 is replaced by intermediate 1S-1, and other conditions refer to synthesis example 1.

[0227] Mass spectrometry results determine that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 21S is 638.21.

[0228] Synthesis example 14

[0229] This example provides an anthracene compound 257, and the specific structural formula is as follows:

[0230]

[0231] The preparation method of anthracene compound 257 provided in this example is as follows:

[0232] (1) Synthesis of intermediate 257-1

[0233]

[0234] The synthesis method of intermediate 257-1 is the same as that of anthracene compound 1 in synthesis example 1, except that intermediate 1-1 is replaced by Other conditions are the same as those in synthesis example 1.

[0235] Mass spectrometry is performed on the intermediate represented by formula 257-1: the mass-to-charge ratio (m / z) is 470.17.

[0236] (2) Synthesis of intermediate 257-2

[0237]

[0238] The synthesis method of intermediate 257-2 is the same as that of intermediate 1-1 in synthesis example 1, except that the compound shown in formula 1-0 is replaced by intermediate 257-1, and other conditions are the same as those in synthesis example 1.

[0239] The intermediate shown in formula 257-2 is subjected to mass spectrometry detection: the two peaks with the largest mass-to-charge ratio (m / z) are 550.08 and 548.08, and the molecular formula of the product is determined to be: C 36 H 21 BrO.

[0240] (3) The synthesis reaction formula of anthracene compound 257 is as follows:

[0241]

[0242] The synthesis method of anthracene compound 257 is the same as that of anthracene compound 1 in synthesis example 1, except that intermediate 1-1 is replaced by intermediate 257.2, and other conditions refer to synthesis example 1.

[0243] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 257 is 622.23.

[0244] Synthesis example 15

[0245] This example provides an anthracene compound 201, and the preparation method is as follows:

[0246]

[0247] The preparation method of anthracene compound 201 provided in this example is the same as that of synthesis example 1, except that the 9-phenyl anthracene-10-boric acid in step (2) is replaced by an equal amount of Other conditions refer to synthesis example 1.

[0248] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 201 is 580.26.

[0249] Synthesis example 16

[0250] This example provides an anthracene compound 209, and the preparation method is as follows:

[0251]

[0252] The preparation method of anthracene compound 209 provided in this example is the same as that of synthesis example 1, except that the 9-phenyl anthracene-10-boric acid in step (2) is replaced by an equal amount of Other conditions refer to synthesis example 1.

[0253] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 209 is 577.25.

[0254] Synthesis Example 17

[0255] This example provides an anthracene compound 197, and the specific structural formula is as shown below:

[0256]

[0257] The preparation method of the anthracene compound 197 provided in this example is as follows:

[0258] (1) Synthesis of intermediate 197-1

[0259]

[0260] The synthesis method of the intermediate 197-1 is the same as that of the intermediate 6-1 in the synthesis example 3, except that the compound shown in formula 6-0 is replaced by an equal amount of 9-(2-naphthyl)-10-anthracene boronic acid, and other conditions are the same as those in the synthesis example 3. 4,6-dibromodibenzo[b,d]furan is replaced by an equal amount of 9-(2-naphthyl)-10-anthracene boronic acid. Other conditions are the same as those in the synthesis example 3.

[0261] Mass spectrometry is performed on the intermediate shown in formula 197-1: the two peaks with the largest mass-to-charge ratio (m / z) are 424.08 and 426.08, and it is determined that the molecular formula of the product is C 27 H 21 Br.

[0262] (2) The synthesis reaction formula of the anthracene compound 197 is as follows:

[0263]

[0264] The preparation method of the anthracene compound 197 provided in this example is the same as that of the anthracene compound 1 in the synthesis example 1, except that 9-phenylanthracene-10-boronic acid is replaced by an equal amount of 9-(2-naphthyl)-10-anthracene boronic acid, the intermediate 1-1 is replaced by the intermediate 197-1, and other conditions are the same as those in the synthesis example 1.

[0265] The mass spectrometry detection result determines that the mass-to-charge ratio (m / z) of the synthesized anthracene compound 197 is 648.28.

[0266] The anthracene compound 197 was detected by H-NMR: 1H-NMR (Switzerland Bruker Company, Avance Ⅱ 400MHz nuclear magnetic resonance spectrometer, CDCl3): δ 8.20 (m, 4H), δ 8.12-8.03 (m, 2H), δ 8.02-7.95 (m, 4H), δ 7.77 (m, 2H), δ 7.72-7.35 (m, 18H), δ 1.70 (s, 6H).

[0267] It should be noted that other anthracene compounds not listed in the present application which require protection and do not have specific synthesis steps can be prepared by combining the above examples with common knowledge in the art.

[0268] The following organic electroluminescent device provided in the present application is used in

[0269] The specific structure of the compound used in the following device example is as follows:

[0270]

[0271] The preparation method of BH-2 is as follows:

[0272]

[0273] The preparation method of BH-2 is the same as that of anthracene compound 1 in synthesis example 1, except that the intermediate 1-1 is replaced by Other conditions are the same as those in synthesis example 1.

[0274] The mass spectrometry result determines that the mass-to-charge ratio (m / z) of the synthesized BH-2 is 572.21.

[0275] Device example 1-19

[0276] Device example 1-19 respectively provides an organic electroluminescent device, and the structure of the organic electroluminescent device is ITO / HIL02 (100 nm) / HT6601 (40 nm) light-emitting layer (30 nm): BD-1 (3%) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm);

[0277] The preparation method of the above organic electroluminescent device is as follows:

[0278] (1) The glass substrate coated with ITO transparent conductive layer (as anode) is treated by ultrasonic in cleaning agent, then washed in deionized water, then ultrasonic deoiled in acetone and ethanol mixed solvent, then dried completely in clean environment, then washed by ultraviolet light and ozone, and then the surface is bombarded by low-energy cation beam to improve the property of ITO surface and improve the binding ability with hole injection layer;

[0279] (2) The glass substrate is placed in a vacuum chamber, and vacuumed to 1 x 10 -5 ~ 1 x 10 -4 Pa, HIL02 is vacuum-deposited on the anode as a hole injection layer, the deposition rate is 0.01 nm / s, and the deposition film thickness is 100 nm;

[0280] (3) HT6601 is vacuum-deposited on the hole injection layer as a hole transport layer, the deposition rate is 0.01 nm / s, and the deposition film thickness is 40 nm;

[0281] (4) The light-emitting layer is vacuum-deposited on the hole transport layer, the deposition rate is 0.01 nm / s, the total deposition film thickness is 30 nm, the light-emitting layer host material is at least one of the anthracene compounds provided in Synthesis Example 1-17 of the present application (see Table 1 for details), and the doping material is BD-1 (3%), wherein 3% refers to the doping ratio of the doping material, i.e., the volume ratio of the light-emitting layer host material to the doping material is 100:3;

[0282] (5) TPBI is vacuum-deposited on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device, the deposition rate is 0.01 nm / s, and the total deposition film thickness is 30 nm;

[0283] (6) 0.5 nm of LiF and 150 nm of Al are vacuum-deposited on the electron transport layer as an electron injection layer and a cathode, thereby obtaining the organic electroluminescent device.

[0284] Device Comparative Example 1-2

[0285] Device Comparative Example 1-2 respectively provides an organic electroluminescent device, and the structure of the organic electroluminescent device is ITO / HIL02 (100 nm) / HT6601 (40 nm) light-emitting layer (30 nm): BD-1 (3%) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0286] The difference from Device Example 1 is only that the light-emitting layer host material is different (see Table 1 for details), and the other structures, materials, and preparation methods are the same as those of Device Example 1.

[0287] Performance test:

[0288] The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang is used to test the driving voltage, current efficiency, and life LT90 of the organic electroluminescent device provided above; wherein, LT90 refers to the time required for the luminance to drop to 90% of the original luminance while keeping the current density unchanged at the initial luminance of 2000 nit, and the specific test results are shown in Table 1:

[0289] Table 1

[0290]

[0291] It should be noted that the numbers in Table 1 represent the code of anthracene compounds, for example, the luminescent layer host material in device example 1 is "1", which represents "anthracene compound 1", the luminescent layer host material in device example 12 is "II-1", which represents "anthracene compound II-1", and so on.

[0292] From the content of Table 1, it can be seen that by using the anthracene compounds with specific structural formula in the present application as the host material of the luminescent layer, the service life of the organic electroluminescent device prepared thereby is longer, especially by using anthracene compound 1, anthracene compound 2, anthracene compound 3, anthracene compound 4, anthracene compound 61 or anthracene compound 169 provided by the present application as the luminescent layer host material, the service life of the organic electroluminescent device prepared thereby is ≥400h, and in particular, by using anthracene compound 169 as the luminescent layer host material, the service life of the organic electroluminescent device prepared thereby is as high as 600h.

[0293] By using the specific anthracene compounds provided by the present application as the host material of the luminescent layer, the driving voltage of the organic electroluminescent device prepared thereby is lower, especially by using anthracene compound 6, anthracene compound 66, anthracene compound II-6 provided by the present application as the luminescent layer host material, the driving voltage of the organic electroluminescent device prepared thereby is significantly reduced, which is presumably due to the fact that these three compounds contain two dibenzofuran units. The voltage advantage is more obvious for the organic electroluminescent device prepared from anthracene compound 185 which also contains 2 dibenzofuran units in the structure. The difference between anthracene compound 185 and anthracene compound 6, anthracene compound 66, anthracene compound II-6 is that, corresponding to general formula (I) / general formula (II), in anthracene compound 185, Ar1 is selected from dibenzofuranyl; in anthracene compound 6, anthracene compound 66, anthracene compound II-6, Ar2 is selected from dibenzofuranyl, thus resulting in this difference.

[0294] From the data of device example 17 compared with device example 1 and the data of device example 18 compared with device example 5, it can be seen that by using anthracene compounds containing deuterium atoms as the luminescent layer host material, the driving voltage of the organic electroluminescent device prepared thereby is lower and the service life is longer.

[0295] Device examples 20-25

[0296] Device Examples 20-25 are respectively an organic electroluminescent device, the structure of which is ITO / HIL02(100 nm) / HT6601(40 nm) light-emitting layer(30 nm):BD-2(3%) / TPBI(30 nm) / LiF(0.5 nm) / Al(150 nm);

[0297] The difference between Device Example 1 is only that the light-emitting layer host material is different (see Table 2 for details), and the doping material BD-1 is replaced by BD-2, and the other structures, materials and preparation methods are the same as those of Device Example 1;

[0298] When the light-emitting layer host material is more than two substances, different host materials are placed in different evaporation sources, and the evaporation rates of different host materials are controlled so that mixtures of different volume ratios are used as light-emitting layer host materials in organic electroluminescent devices.

[0299] Performance test:

[0300] The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used to test the driving voltage, current efficiency and lifetime LT90 of the organic electroluminescent devices provided above; wherein, LT90 refers to the time required for the luminance to drop to 90% of the original luminance while keeping the current density unchanged at the initial luminance of 2000 nit, and the specific test results are shown in Table 2:

[0301] Table 2

[0302]

[0303] It should be noted that in the data of the light-emitting layer host material column in Device Examples 20-25 in Table 2, the number on the left side of the equal sign represents the serial number of the anthracene compound, and the number on the right side of the equal sign represents the volume ratio of different anthracene compounds, for example, in Device Example 20, the data in the light-emitting layer host material column is "1:2=5:5", which means that the light-emitting layer host material in Device Example 20 is composed of anthracene compound 1 and anthracene compound 2 in a volume ratio of 5:5; if the data in the light-emitting layer host material column has only one data, it represents the serial number of the anthracene compound, for example, in Device Example 23, the data in the light-emitting layer host material column is "1", which means that the light-emitting layer host material in Device Example 23 is anthracene compound 1.

[0304] From the data in Table 2, it can be seen that compared with using a single anthracene compound as the light-emitting layer host material (Device Examples 23-24), the organic electroluminescent device prepared by using an anthracene compound mixture containing multiple anthracene compounds as the light-emitting layer host material (Device Example 22) has lower driving voltage, higher current efficiency and longer service life.

[0305] As can be seen from the data in Table 2, when the anthracene mixture containing a plurality of anthracene compounds is used as the host material of the light-emitting layer, if at least one of the anthracene compounds in the anthracene mixture contains deuterium atoms, the comprehensive performance of the prepared organic electroluminescent device is relatively excellent, and the anthracene compound without deuterium atoms is relatively simple to prepare and has a lower cost, so when the host material of the light-emitting layer is a combination of the anthracene compound without deuterium atoms and the anthracene compound containing deuterium atoms, the prepared OLED device has a lower cost.

[0306] In summary, by designing the structural formula of the anthracene compound, the anthracene compound and the anthracene mixture with a specific structure are obtained, and when the anthracene compound or the anthracene mixture is used as the host material of the light-emitting layer, the prepared organic electroluminescent device has a lower driving voltage, a higher current efficiency and a longer service life.

[0307] The applicant declares that the anthracene organic compound, the electroluminescent device and the display device of the present application are illustrated by the above-mentioned embodiments, but the present application is not limited to the above-mentioned embodiments, that is, it does not mean that the present application must rely on the above-mentioned embodiments to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific modes, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. An anthracene compound, characterized by, The anthracene compound has a structure as shown in formula (I) or formula (II): In the anthracene compound of formula (I) and formula (II), Ar1 is selected from any one of the following groups: In the anthracene compound of formula (I) and formula (II), the short line represents the connection site of the group; Ar2 is selected from any one of the following groups: In the anthracene compound of formula (I) and formula (II), the short line represents the connection site of the group; X is selected from O, S or R 11 , R 12 are each independently selected from methyl, ethyl or phenyl; In the anthracene compound of formula (I) and formula (II), ring A and ring B each include four sp2 hybridized carbon atoms, and the four sp2 hybridized carbon atoms in the ring A and ring B are fused with the adjacent benzene ring; In the anthracene compound of formula (I) and formula (II), ring A can exist or not exist, and ring B does not exist; In the anthracene compound of formula (I) and formula (II), a is independently selected from an integer from 0 to 4; In the anthracene compound of formula (I) and formula (II), b is independently selected from an integer from 0 to 8.

2. The anthracene compound according to claim 1, characterized by In the anthracene compound of formula (I) and formula (II), b is 8, and the anthracene compound has a structure as shown in formula (I-a) or formula (II-a): In the anthracene compound of formula (I-a), Ar1, Ar2, X, ring A, ring B and a each independently have the same defined range as formula (I); In the anthracene compound of formula (II-a), Ar1, Ar2, X, ring A, ring B and a each independently have the same defined range as formula (II).

3. The anthracene compound according to claim 1, characterized by The anthracene compound having a structure as shown in formula (I) or formula (II) each independently meets at least one of the following conditions: (1) All hydrogen atoms on Ar1 in formula (I) or formula (II) are replaced by deuterium atoms; (2) All hydrogen atoms on Ar2 in formula (I) or formula (II) are replaced by deuterium atoms; (3) a in formula (I) or formula (II) is 4; (4) b in formula (I) or formula (II) is 8.

4. The anthracene compound according to claim 3, characterized by The anthracene compound having a structure as shown in formula (I) or formula (II) each independently meets conditions (1) to (4).

5. The anthracene compound according to claim 1, characterized by The anthracene compound having a structure as shown in formula (I) is selected from any one of anthracene compounds 1-264, anthracene compounds 1S-264S; The structure of the anthracene compound 1-264 is as follows: The structural formula of the anthracene compound 1S-264S is O or S at the corresponding X position in the anthracene compounds 1-264 shown in the structure of formula (I) is replaced by S to form the anthracene compounds 1S-264S.

6. The anthracene compound according to claim 5, characterized by The anthracene compound having a structure as shown in formula (II) is selected from any one of anthracene compounds II-1- II-264, anthracene compounds II-1S- II-264S; The structure of the anthracene compound II-1- II-264 is that the substituent at the corresponding Ar2 in the anthracene compound 1-264 having a structure as shown in formula (I) is replaced at the corresponding Ar2 of the anthracene compound having a structure as shown in formula (II), thereby forming the anthracene compound II-1- II-264; The structure of the anthracene compound II-1S- II-264S is that the substituent at the corresponding Ar2 in the anthracene compound 1S-264S having a structure as shown in formula (I) is replaced at the corresponding Ar2 of the anthracene compound having a structure as shown in formula (II), thereby forming the anthracene compound II-1S- II-264S.

7. An intermediate characterized by, The intermediate is selected from any one of the following intermediates: The intermediate is used for preparing the anthracene compound of formula (I) or formula (II) as claimed in any one of claims 1-6.

8. An anthracene mixture, characterized in that, The anthracene mixture comprises at least two anthracene compounds as claimed in any one of claims 1-6.

9. Anthracene mixture according to claim 8, characterized in that The anthracene mixture comprises the anthracene compound of formula (I) not meeting any one of conditions (1)-(4) and / or the anthracene compound of formula (II) not meeting any one of conditions (1)-(4).

10. An organic electroluminescent device, characterized by comprising The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer; The material of the organic thin film layer comprises the anthracene compound as claimed in any one of claims 1-6 and / or the anthracene mixture as claimed in claim 8 or 9.

11. The organic electroluminescent device according to claim 10, characterized in that The material of the organic thin film layer further comprises a compound having a structure as shown in formula (III): wherein Ar 21 , Ar 22 each independently is selected from any one of substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl; R 21 , R 22 , and R 23 are each independently selected from any one of hydrogen, C1-C12straight chain or branched chain alkyl, C6-C12cycloalkyl; Ar 21 , Ar 22 each of the substituents of the substituents described in Ar is independently selected from the group consisting of deuterium, C1-C5 straight chain or branched alkyl, or C6-C12 aryl.

12. The organic electroluminescent device according to claim 11, characterized in that, Ar 21 Ar 22 each independently is selected from any one of.

13. The organic electroluminescent device according to claim 11, wherein Each of R1, R2 and R3 is independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.

14. The organic electroluminescent device according to claim 11, wherein The compound having a structure as shown in formula (III) is selected from any one of the following compounds:

15. The organic electroluminescent device according to claim 11, wherein The material of the organic thin film layer further comprises a compound having a structure as shown in formula (IV): wherein Ar 31 , Ar 32 , Ar 33 , and Ar 34 are each independently selected from any one of substituted or unsubstituted C6to C22aryl, substituted or unsubstituted C12to C40heteroaryl; R 31 is selected from any one of phenyl, naphthyl or biphenyl; a is selected from 0 or 1; Ar 31 , Ar 32 , Ar 33 , Ar 34 each of the substituents described in Ar is independently selected from deuterium, C1-C5straight chain or branched alkyl, or C6-C12aryl.

16. The organic electroluminescent device according to claim 15, characterized in that Ar 31 , Ar 32 , Ar 33 , and Ar 34 are each independently selected from the group consisting of any one or a combination of at least two.

17. The organic electroluminescent device according to claim 15, wherein The compound having a structure as shown in formula (IV) is selected from any one of the following compounds:

18. A display device comprising: The display device comprises the organic electroluminescent device as claimed in any one of claims 10-17.

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