A compound and its application, and an organic electroluminescent device containing the same

Abstract

The present invention relates to a general formula compound and its application, wherein the compound has a structure shown in the following formula. The compound provided by the present invention preferably adopts an alkyl-substituted aryl-substituted carbazole structure at the ortho position of the cyano group on the benzene ring of the parent core general formula (1), which can increase the molecular rigidity while improving the degree of distortion of the molecular structure, thereby promoting the blue shift of the luminescence of the compound of the present invention, and improving the luminescence efficiency, and can improve the carrier transport performance of the compound. When the compound of the present invention is used as an organic electroluminescent device, especially a light-emitting layer material, it can ensure that the device obtains the excellent effects of high luminescence efficiency and low starting voltage.

Description

Technical Field

[0001] The invention relates to a general compound, specifically a thermal excitation sensitized fluorescent material, belonging to the technical field of organic light-emitting materials. The invention also relates to the application of the compound in an organic electroluminescent device. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates. Beautiful and cool optoelectronic products can be designed and produced according to demand, gaining unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a thin film structure containing a variety of organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] People have developed a variety of organic materials, combined with various unique device structures, which can improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device attenuation. For quantum mechanical reasons, common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and voids combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously use triplet excitons and singlet excitons to emit light, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize luminescent bodies through energy transfer, which can also achieve higher luminescence efficiency.

[0005] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, life span, cost, etc. Through careful thinking and continuous experiments, the researchers of the present invention have discovered an ingenious molecular design scheme, which is described in detail below. Surprisingly, the compounds disclosed in the present invention are very suitable for application in OLED and improve the performance of the device. Summary of the invention

[0006] In order to solve the above problems in the prior art, the present invention provides a new class of compounds for organic electroluminescent devices to meet the requirements for the photoelectric performance and operating voltage of OLED devices.

[0007] The present invention provides a compound of general formula, whose structure is shown in formula (1):

[0008]

[0009] In formula (1), R is selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C18 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino; preferably, R is hydrogen.

[0010] In formula (1), D 1 -D 4 They are independently the structures shown in formula (2):

[0011]

[0012] In formula (2), X 1 -X 8 Each independently selected from N or CR 1 , R 1 is independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, and the adjacent R 1 They are connected to form a ring or not; * represents the access bond position of the group;

[0013] And D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3):

[0014]

[0015] In formula (3), X 9 -X 12 Independently selected from N or CR 2 , R 2 Independently selected from one of hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C18 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino; * represents the access bond position of the group;

[0016] When there is a substituent on each of the above-mentioned groups, the substituent is independently selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0017] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0018] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, in the present specification, "each independently" generally means that when there are multiple subjects, they can be the same or different.

[0019] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0020] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen (H)" also includes isotopes with the same chemical properties. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0021] In the present specification, examples of halogen include fluorine, chlorine, bromine, and iodine.

[0022] In the present invention, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed ring forms.

[0023] In the present invention, the substituted or unsubstituted C6-C60 aryl includes a monocyclic aryl and a condensed aryl, preferably a C6-C30 aryl, and more preferably a C6-C20 aryl. The so-called monocyclic aryl refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as: phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed aryl refers to a molecule containing at least two aromatic rings, and the aromatic rings are not independent of each other but share two adjacent carbon atoms to condense each other. For example, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylene, pyrenyl, peryl, The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthacenyl group is selected from 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirobifluorene and benzofluorenyl.

[0024] The C3-C60 heteroaryl mentioned in the present invention includes monocyclic heteroaryl and condensed ring heteroaryl, preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and more preferably C5-C12 heteroaryl. Monocyclic heteroaryl refers to a molecule containing at least one heteroaryl. When the molecule contains one heteroaryl and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl include furanyl, thienyl, pyrrolyl, pyridyl, etc. Condensed ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms and are fused to each other. Examples of fused ring heteroaryl groups include benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl and the like.

[0025] Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl groups. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl groups.

[0026] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0027] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0028] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.

[0029] The chain alkyl mentioned in the present invention, unless otherwise specified, includes straight chain alkyl and branched chain alkyl. Specifically, the substituted or unsubstituted C1-C30 chain alkyl is preferably a substituted or unsubstituted C1-C16 chain alkyl, and more preferably a substituted or unsubstituted C1-C10 chain alkyl. The substituted or unsubstituted C1-C10 chain alkyl includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0030] In the present invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein the monocycloalkyl group refers to an alkyl group containing a single cyclic structure; the polycycloalkyl group refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on the ring; the C3-C20 cycloalkyl group can be exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0031] In the present specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of the C1-C10 alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0032] In the present specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, examples of the C1-C10 silyl group can be a silyl group substituted by the groups listed in the above-mentioned C1 to C10 alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like groups.

[0033] Preferably, the D 1 -D 4 In the structure of formula (2) represented by 2 to 4 of 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3);

[0034] More preferably, the D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 is the structure shown in formula (3); or, D 1 -D 4 In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 is the structure shown in formula (3); or, D 1 -D4 In the structure of formula (2) represented by the four 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

[0035] More preferably, the D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by the other two, X 1 -X 8 At least one of them is CR 1 , and the R 1 is selected from hydrogen, methyl or tert-butyl;

[0036] Or, D 1 -D 4 In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by another one of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 is selected from hydrogen, methyl or tert-butyl;

[0037] Or, D 1 -D 4 In the structure of formula (2) represented by the four 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

[0038] Further preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 One or two of them are CR 1 , and the R 1 The structure is shown in formula (3);

[0039] More preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is the structure shown in formula (3); or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 It is the structure shown in formula (3).

[0040] More preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl;

[0041] Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, and substituted or unsubstituted C1-C12 chain alkyl.

[0042] Most preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 are all hydrogen; further, X 9-X 12 All CR 2 , and the R 2 All are hydrogen;

[0043] Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 are all hydrogen; further, X 9 -X 12 All CR 2 , and the R 2 All are hydrogen.

[0044] Further, in formula (1), R is hydrogen. Further, in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 to 4 of 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

[0045] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3);

[0046] Or, D 1 -D 4 In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3);

[0047] Or, D 1 -D 4 In the structure of formula (2) represented by the four1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3);

[0048] Preferably, D 1 and D 3 In the structure of formula (2) represented by one of 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 2 and D 4 In the structure of formula (2) represented by one of 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

[0049] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by the other two, X 1 -X 8 Each independently selected from N or CR 1 , R 1’ are independently selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C18 cycloalkyl, and the adjacent R 1’ Connected to form a ring or not connected to form a ring, X 1 -X 8 Where 0 or 1 is N; preferably, X 1 -X 8 Each independently selected from CR 1’ , R 1 is independently selected from one of hydrogen, methyl, and tert-butyl; more preferably, D 1 -D 4 The other two represented by formula (2) are selected from one of the following structures:

[0050]

[0051] Or, D 1 -D 4In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by another one of the above, X 1 -X 8 Each independently selected from N or CR 1 ', R 1 ' is independently selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C18 cycloalkyl, and the adjacent R 1 ' are connected to form a ring or not, X 1 -X 8 Where 0 or 1 is N; preferably, X 1 -X 8 Each independently selected from CR 1 ', R 1’ is independently selected from one of hydrogen, methyl, and tert-butyl; more preferably, D 1 -D 4 The other one of the formula (2) is selected from one of the following structures:

[0052]

[0053] Or, D 1 -D 4 In the structure of formula (2) represented by the four 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

[0054] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 One or two of them are CR 1 , and the R 1 The structure is shown in formula (3);

[0055] Preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 The structure is shown in formula (3);

[0056] Or preferably, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 It is the structure shown in formula (3).

[0057] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl;

[0058] Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, and substituted or unsubstituted C1-C12 chain alkyl.

[0059] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 are all hydrogen; further, X 9 -X 12 All CR 2 , and the R 2 All are hydrogen;

[0060] Or, D 1 -D 4In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 are all hydrogen; further, X 9 -X 12 All CR 2 , and the R 2 All are hydrogen.

[0061] Furthermore, in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 Each independently selected from CR 1 , X 1 -X 8 Selected R 1 At least one R 1 The structure is shown in formula (3), and at the same time, other X 1 -X 8 The selected R 1 For hydrogen.

[0062] Further preferably, the D 1 -D 4 At least one of the structures of formula (2) represented by is selected from the substituent groups shown below:

[0063]

[0064] As preferred structures of the compounds of the present invention, the following specific compounds S1 to S70 can be cited, but are not limited to these compounds:

[0065]

[0066]

[0067]

[0068]

[0069] As another aspect of the present invention, there is also provided an application of the compound as described above in an organic electroluminescent device. Specifically, it is preferably used as a light-emitting layer material in an organic electroluminescent device, and more preferably used as a material in the light-emitting layer in the organic electroluminescent device, and specifically can be used as a luminescent dye.

[0070] As another aspect of the present invention, an organic electroluminescent device is provided, comprising a first electrode, a second electrode and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer contains the compound of the general formula (1) as described above, or contains the compounds having the structures shown in S1 to S69 as shown above.

[0071] Specifically, one embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode sequentially formed on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is provided between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound of the general formula (1) as described above, or contains a compound of the structures shown in S1 to S69 as shown above.

[0072] The present invention further discloses a display screen or a display panel, wherein the organic electroluminescent device as described above is adopted in the display screen or the display panel; preferably, the display screen or the display panel is an OLED display.

[0073] The present invention also discloses an electronic device, wherein the electronic device has a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device as described above.

[0074] The OLED device prepared by using the compound of the present invention has a low starting voltage and a better service life, and can meet the requirements of current panel manufacturing companies for high-performance materials.

[0075] The specific reasons why the above compounds of the present invention have excellent performance as light-emitting layer materials are not yet clear, but it is speculated that the reasons may be as follows:

[0076] 1. The compounds of the present invention preferably adopt an alkyl-substituted aryl-substituted carbazole structure at the ortho position of the cyano group on the benzene ring of the parent core general formula (1), which can increase the rigidity of the molecule and improve the degree of distortion of the molecular structure, thereby promoting the blue shift of the luminescence of the compounds of the present invention and improving the luminescence efficiency, which is conducive to the application of such materials in deep blue light OLED devices;

[0077] 2. The compounds of the present invention can improve the carrier transport performance of the compounds by introducing the most preferred alkyl-substituted aromatic group of the structure of formula (3) connected to the general formula (1) connected to the parent core, which is beneficial to reduce the voltage of the device when such materials are used in OLED devices. DETAILED DESCRIPTION

[0078] Synthesis Example 1: Synthesis of S1

[0079]

[0080] Synthesis of intermediate S1-1:

[0081] At room temperature, 3-bromocarbazole (20 g, 81.27 mmol), 2-methylphenylboronic acid (12.15 g, 89.19 mmol), potassium carbonate (22.46 g, 162.53 mmol), 120 ml of dioxane, 30 ml of water were added to a 1000 ml flask, nitrogen was replaced three times, tetrakistriphenylphosphine palladium (1.88 g, 1.63 mmol) was added, nitrogen was replaced again, stirred and heated to reflux, and the reaction was allowed to proceed overnight. The reaction system was cooled, the reaction solution was filtered through 100-200 mesh silica gel, the solvent was dried, and silica gel was mixed with a sample column for chromatography to obtain 18.4 g of a white solid. The molecular weight determined by mass spectrometry was 257.34 (theoretical value: 257.34).

[0082] Synthesis of S1:

[0083] Add 2,3,5,6-tetrafluorobenzonitrile (2.0 g, 11.42 mmol), S1-1 (12.93 g, 50.26 mmol), cesium carbonate (13.22 g, 68.54 mmol) to a 500 ml three-necked flask and dissolve in 100 ml DMF. Replace with nitrogen three times and protect. Heat to 80 °C and react for 16 h.

[0084] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 6.51g of yellow solid. Molecular mass determined by mass spectrometry: 1124.40 (theoretical value: 1124.40).

[0085] Synthesis Example 2: Synthesis of S2

[0086]

[0087] Synthesis of intermediate S2-1:

[0088] Add 2,3,5,6-tetrafluorobenzonitrile (2.0 g, 11.42 mmol), S1-1 (3.23 g, 12.57 mmol), cesium carbonate (3.31 g, 17.14 mmol) to a 100 ml three-necked flask and dissolve in 30 ml DMF. Replace with nitrogen three times and protect. Heat to 80°C and react for 16 hours.

[0089] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 3.51g of yellow solid. Molecular mass determined by mass spectrometry: 412.12 (theoretical value: 412.12).

[0090] Synthesis of S2:

[0091] S2-1 (3 g, 7.27 mmol), carbazole (4.38 g, 26.19 mmol), cesium carbonate (10.67 g, 32.73 mmol) were added to a 100 ml three-necked flask and dissolved in 50 ml DMF. Nitrogen was replaced three times and protected. The temperature was raised to 80°C and the reaction was carried out for 16 hours.

[0092] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 6.67g of yellow solid. Molecular mass determined by mass spectrometry: 854.03 (theoretical value: 854.03).

[0093] Synthesis Example 3: Synthesis of S3

[0094]

[0095] Synthesis of intermediate S3-1:

[0096] Add 2,3,5,6-tetrafluorobenzonitrile (2.0 g, 11.42 mmol), S1-1 (6.46 g, 35.14 mmol), cesium carbonate (6.62 g, 34.28 mmol) to a 250 ml three-necked flask and dissolve in 60 ml DMF. Replace with nitrogen three times and protect. Heat to 80 °C and react for 16 h.

[0097] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 5.87g of yellow solid. Molecular mass determined by mass spectrometry: 649.23 (theoretical value: 649.23).

[0098] Synthesis of S3:

[0099] S2-1 (5 g, 7.27 mmol), carbazole (3.22 g, 19.24 mmol), cesium carbonate (9.42 g, 30 mmol) were added to a 250 ml three-necked flask and dissolved in 50 ml DMF. Nitrogen was replaced three times and protected. The temperature was raised to 80°C and the reaction was carried out for 16 hours.

[0100] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 7.69g of yellow solid. Molecular mass determined by mass spectrometry: 943.37 (theoretical value: 943.37).

[0101] Synthesis of S1:

[0102] Add 2,3,5,6-tetrafluorobenzonitrile (2.0 g, 11.42 mmol), S1-1 (12.93 g, 50.26 mmol), cesium carbonate (13.22 g, 68.54 mmol) to a 500 ml three-necked flask and dissolve in 100 ml DMF. Replace with nitrogen three times and protect. Heat to 80 °C and react for 16 h.

[0103] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 6.51g of yellow solid. Molecular mass determined by mass spectrometry: 1124.40 (theoretical value: 1124.40).

[0104] Synthesis Example 4: Synthesis of S4

[0105]

[0106] Synthesis of intermediate S4-1:

[0107] Add 2,3,5,6-tetrafluorobenzonitrile (4.08 g, 23.32 mmol), S1-1 (20 g, 77.72 mmol), cesium carbonate (37.98 g, 116.58 mmol) to a 1000 ml three-necked flask and dissolve in 200 ml DMF. Replace with nitrogen three times and protect. Heat to 80°C and react for 16 hours.

[0108] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 56.92g of yellow solid. Molecular mass determined by mass spectrometry: 887.07 (theoretical value: 887.07).

[0109] Synthesis of S4:

[0110] S4-1 (40 g, 45.09 mmol), carbazole (7.54 g, 45.09 mmol), cesium carbonate (22.04 g, 67.64 mmol) were added to a 1000 ml three-necked flask and dissolved in 50 ml DMF. Nitrogen was replaced three times and protected. The temperature was raised to 80°C and the reaction was carried out for 16 hours.

[0111] Stop the reaction, inject the reaction solution into water, add a certain amount of ammonium chloride solid, stir, solid precipitates, filter, column chromatography, recrystallize, and obtain 41.81g of yellow solid. Molecular mass determined by mass spectrometry: 1034.28 (theoretical value: 1034.28).

[0112] Synthesis Example 5: Synthesis of S9

[0113] The synthesis method is the same as that of S1, except that the reactant 3-bromocarbazole is replaced by 3-bromo-6-methylcarbazole. The molecular mass determined by mass spectrometry is: 1180.51 (theoretical value: 1180.51)

[0114] Synthesis Example 6: Synthesis of S11

[0115] The synthesis method is the same as that of S1, except that the reactant 3-bromocarbazole is replaced by 3-bromo-6-tert-butylcarbazole. The molecular mass determined by mass spectrometry is: 1348.84 (theoretical value: 1348.84)

[0116] Synthesis Example 7: Synthesis of S27

[0117]

[0118] Synthesis of intermediate S27-1: The synthesis method is the same as that of S1-1, except that 2-methylphenylboronic acid in the raw material is replaced by 2,6-dimethylphenylboronic acid. Molecular mass determined by mass spectrometry: 271.14 (theoretical value: 971.40).

[0119] Synthesis of S27: The synthesis method is the same as that of S3, except that the raw material S1-1 is replaced by S27-1. Molecular mass determined by mass spectrometry: 971.40 (theoretical value: 971.40).

[0120] Synthesis Example 8: Synthesis of S49

[0121]

[0122] Synthesis of intermediate S49-1: At room temperature, in a 1000 ml flask, add 3,6-dibromocarbazole (20 g, 61.54 mmol), 2-methylphenylboronic acid (16.73 g, 123.08 mmol), potassium carbonate (34.02 g, 246.15 mmol), 120 ml of dioxane, 30 ml of water, replace nitrogen three times, add tetrakistriphenylphosphine palladium (1.42 g, 1.23 mmol), replace nitrogen again, stir and heat to reflux, and react overnight. Cool the reaction system, filter the reaction solution with 100-200 mesh silica gel, spin dry the solvent, and silica gel column chromatography to obtain 17.6 g of white solid. Molecular mass determined by mass spectrometry: 347.46 (theoretical value: 347.46).

[0123] Synthesis of S49: The synthesis method is the same as that of S1, except that the raw material S1-1 is replaced by S49-1. The molecular mass determined by mass spectrometry is: 1483.65 (theoretical value: 1483.65).

[0124] Device Embodiment

[0125] Implementation

[0126] OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0127] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0128] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0129] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0130] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0131] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0132]

[0133]

[0134]

[0135]

[0136] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0137]

[0138] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0139] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0140] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0141]

[0142]

[0143]

[0144]

[0145] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0146] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0147] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0148]

[0149]

[0150]

[0151] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0152] The device may further include an electron injection layer located between the electron transport layer and the cathode. Materials for the electron injection layer include, but are not limited to, one or more combinations of the following.

[0153] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0154] Computational Chemistry:

[0155] The present invention uses Gaussian03 to perform quantum chemical calculations on the compounds, and uses a time-dependent density functional method to perform theoretical calculations on the compounds of the present invention and the comparative compounds listed in Table 1, respectively. The calculation results are shown in Table 1. The structural formulas of comparative compounds C1, C2, C3 and C4 are as follows.

[0156]

[0157] Among them, C1 is detailed in patent application CN110914378A, C2 is detailed in patent application WO2019002175A, and C4 is detailed in patent application US20190181353A.

[0158] Table 1:

[0159]

[0160]

[0161] The fluorescence emission wavelength of the material is related to the first singlet energy level. The higher the energy level, the shorter the fluorescence emission wavelength of the material, and the bluer the emission. From the calculation results of Table 1, it can be seen that the example compound of the present invention has a higher singlet energy than the compound of Comparative Example 1 and the compound of Comparative Example 2. It can be expected that its emission wavelength is shorter and more suitable as a light-emitting material for a blue light OLED device. This may be due to: (1) Compared with compound C1, the ortho position of the substituted aromatic group on the carbazole ortho to the cyano group in the compound of the present invention is substituted by an alkyl group, which reduces the degree of conjugation of the molecule; (2) Compared with compound C2, the compound of the present invention contains four carbazole groups, the structure is more distorted, and the angle between carbazole and the middle benzene ring is larger, so the degree of conjugation is smaller, and the emission is more blue; (3) Compared with compound C3, the phenyl group on the carbazole of the compound of the present invention has an alkyl substituent at the ortho position, which is beneficial to reduce the degree of conjugation of carbazole, increase the excited state energy level, and make the light color blue shift.

[0162] Device Example:

[0163] The manufacturing process of device embodiment 1 is as follows:

[0164] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment to completely remove the water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0165] Place the glass substrate with the anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5 Pa, vacuum thermally evaporate 10nm of HT-4:HI-3 (97 / 3, w / w) mixture as hole injection layer, 60nm of compound HT-4 as hole transport layer, 5nm of compound HT-51 as electron blocking layer; 40nm of compound PH54:S1 (100:40, w / w) binary mixture as light emitting layer; 5nm of PH-28 as hole blocking layer, 25nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as electron transport layer, 1nm of LiF as electron injection layer, and 150nm of metal aluminum as cathode on the above anode layer film in order. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm / sec, and the evaporation rate of metal electrode is controlled at 1nm / sec.

[0166] The preparation process of device examples 2-19 and comparative examples 1-3 is the same as that of device example 1, except that S1 in the light-emitting layer is replaced with the compounds listed in Table 2.

[0167] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0168] At the same brightness, the driving voltage and external quantum efficiency EQE of the organic electroluminescent device prepared from the compound and the comparative material were measured using a digital source meter, a brightness meter and a PR650. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 1000 cd / m 2 The voltage at this time is the driving voltage.

[0169] The properties of the organic electroluminescent devices prepared in the above Examples 1-19 and Comparative Examples 1-3 are shown in Table 2 below.

[0170] Table 2:

[0171]

[0172] As can be seen from Table 2, when the compound of the present invention is used as a dye, the wavelength of the luminescent peak position is shorter than that of the comparative example compound, showing excellent device performance. This may be due to the smaller degree of molecular conjugation. At the same time, the luminous efficiency is slightly improved, which may be due to the stronger rigidity of the compound of the present invention. These are conducive to the practical application of the compound of the present invention.

[0173] Embodiment 20

[0174] The device was prepared according to the method described in Example 1, vacuum evaporating 10 nm of a mixture of HT-4:HI-3 (97 / 3, w / w) as a hole injection layer, 60 nm of compound HT-4 as a hole transport layer, and 5 nm of compound HT-51 as an electron blocking layer;

[0175] Vacuum evaporation of "PH-54:S1:BFD-16 (100:40:1, w / w / w) (40 nm)" on the hole transport layer as the light-emitting layer of the organic electroluminescent device;

[0176] On the light-emitting layer, 5nm of ET-23 was vacuum-deposited as a hole blocking layer, 25nm of a mixture of compounds ET-69:ET-57 (50 / 50, w / w) was used as an electron transport layer, 1nm of LiF was used as an electron injection layer, and 150nm of metal aluminum was used as a cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1nm / sec, and the evaporation rate of the metal electrode was controlled at 1nm / sec.

[0177] Examples 21-26

[0178] The difference from Example 20 is that S1 is replaced with the structures listed in Table 3 in sequence.

[0179] Comparative Examples 4-5

[0180] The only difference from Example 20 is that S1 is replaced by C1 and C3.

[0181] Table 3:

[0182]

[0183] It can be seen from Table 3 that when the compound of the present invention is used as a sensitizer, the wavelength corresponding to the luminescence peak is shorter and the efficiency is higher than that of the comparative example compound. This may be because the emission spectrum of the compound of the present invention itself is blue, so the energy can be completely transferred to the dye, while the wavelength of the luminescence peak position of the comparative compound is longer, and the energy transfer to the dye is incomplete, so the luminescence is reddish and the efficiency is lower.

[0184] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A compound of the general formula, whose structure is shown in the general formula (1): In formula (1), R is selected from hydrogen; in formula (1), D 1 -D 4 They are independently the structures shown in formula (2): In formula (2), X 1 -X 8 Each independently selected from CR 1 , R 1 are independently selected from hydrogen, C1-C12 chain alkyl, C3-C18 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and the adjacent R 1 They are connected to form a ring or not; * represents the access bond position of the group; At least one R 1 The structure is shown in formula (3): In formula (3), X 9 -X 12 Independently selected from CR 2 , the R 2 Independently selected from one of hydrogen, C1-C12 chain alkyl, and C6-C30 aryl; * represents the access bond position of the group; When there is a substituent on each of the above groups, the substituent is independently selected from one or a combination of at least two of a C1-C20 alkyl group, a C3-C20 cycloalkyl group, a C6-C60 aryl group, and a C3-C60 heteroaryl group.

2. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 to 4 of 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

3. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3); Or, D 1 -D 4 In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3); Or, D 1 -D 4 In the structure of formula (2) represented by the four 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

4. The compound of the general formula according to claim 3, D 1 and D 3 In the structure of formula (2) represented by one of 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 2 and D 4 In the structure of formula (2) represented by one of 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

5. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by 2 of the above, X 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by the other two, X 1 -X 8 Each independently selected from CR 1’ , R 1’ independently selected from hydrogen, C1-C12 chain alkyl, C3-C18 cycloalkyl, adjacent R 1’ Connected to form a ring or not connected to form a ring, X 1 -X 8 Where 0 or 1 is N.

6. The compound of the general formula according to claim 5, X 1 -X 8 Each independently selected from CR 1’ , R 1’ Independently selected from one of hydrogen, methyl and tert-butyl.

7. The compound of the general formula according to claim 5, D 1 -D 4 The other two represented by formula (2) are selected from one of the following structures: Or, D 1 -D 4 In the structure of formula (2) represented by the three 1 -X 8 At least one of them is CR 1 , and the R 1 The structure is shown in formula (3), and D 1 -D 4 In the structure of formula (2) represented by another one of the above, X 1 -X 8 Each independently selected from N or CR 1’ , R 1’ are independently selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C18 cycloalkyl, and the adjacent R 1’ Connected to form a ring or not connected to form a ring, X 1 -X 8 Where 0 or 1 is N.

8. The compound of the general formula according to claim 7, X 1 -X 8 Each independently selected from CR 1’ , R 1’ Independently selected from one of hydrogen, methyl and tert-butyl.

9. The compound of the general formula according to claim 7, D 1 -D 4 The other one of the formula (2) is selected from one of the following structures: Or, D 1 -D 4 In the structure of formula (2) represented by the four 1 -X 8 At least one of them is CR 1 , and the R 1 It is the structure shown in formula (3).

10. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 One or two of them are CR 1 , and the R 1 It is the structure shown in formula (3).

11. The compound of the general formula according to claim 10, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 The structure is shown in formula (3); Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 It is the structure shown in formula (3).

12. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl; Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 Selected from hydrogen, and substituted or unsubstituted C1-C12 chain alkyl.

13. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 All are hydrogen; Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and X 10 -X 12 All CR 2 , and the R 2 All are hydrogen.

14. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 3 CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C12 chain alkyl, and X 9 -X 12 All CR 2 , and the R 2 All are hydrogen; Or, D 1 -D 4 In the structure of formula (2) represented by at least one of 3 and X 6 All CR 1 , and the R 1 is a structure shown in formula (3), and in formula (3), X 9 CR 2 , and the R 2 is selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and X 9 -X 12 All CR 2 , and the R 2 All are hydrogen.

15. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 In the structure of formula (2) represented by at least one of 1 -X 8 Each independently selected from CR 1 , X 1 -X 8 Selected R 1 At least one R 1 The structure is shown in formula (3), and at the same time, other X 1 -X 8 The selected R 1 For hydrogen.

16. The compound of the general formula according to claim 1, wherein in formula (1), D 1 -D 4 At least one of the structures of formula (2) represented by is selected from the substituent groups shown below:

17. The compound according to claim 1, which has the structure shown below:

18. Use of the compound according to any one of claims 1 to 17, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper.

19. Use of the compound according to claim 18 as a light-emitting layer material in an organic electroluminescent device, as a light-emitting dye of the light-emitting layer.

20. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, wherein the hole transport region is formed on the first electrode, the second electrode is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein, The light-emitting layer contains the compound according to any one of claims 1 to 17.

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