Pyrene-containing B-N material and application thereof

Abstract

The invention provides a compound and application thereof, the compound has a structure as shown in formula (1), a ring A, a ring D and a ring E are independently selected from one of substituted or unsubstituted C3-C60 heteroaromatic rings and substituted or unsubstituted C6-C60 aromatic rings, and at least one of the ring A, the ring D and the ring E has a structure as shown in formula (a). When the compound is used in an organic electroluminescent device, especially used as a luminescent dye material, the carrier transmission efficiency can be effectively improved, and the service life of the device can be prolonged. # imgabs0 #

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, in particular to an organic green light dye and application thereof, and also to an organic electroluminescence 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 by energy transfer, which can also achieve higher luminescence efficiency. Especially in the field of blue luminescence, which has always been difficult to effectively improve luminescence efficiency, it has a very broad application prospect.

[0005] Under the condition of electrical excitation, organic electroluminescent devices will produce 25% singlet and 75% triplet excitons. Traditional fluorescent materials can only use 25% of singlet excitons due to spin prohibition, so the external quantum efficiency is limited to less than 5%. Almost all triplet excitons can only be lost in the form of heat. In order to improve the efficiency of organic electroluminescent devices, triplet excitons must be fully utilized.

[0006] To this end, researchers have proposed many methods, the most notable of which is the use of phosphorescent materials. Phosphorescent materials introduce heavy atoms and have a spin-orbit coupling effect, which can fully utilize 75% of triplet excitons and achieve 100% internal quantum efficiency. However, phosphorescent materials use rare heavy metals, which makes the materials expensive and not conducive to cost control. If fluorescent devices can make good use of triplet excitons, this problem can be solved well. Researchers have proposed a method to improve the efficiency of fluorescent devices by quenching triplet excitons to produce singlet excitons in fluorescent devices, but the maximum external quantum efficiency that this method can theoretically achieve is only 62.5%, which is much lower than that of phosphorescent materials. Therefore, it is very necessary to find new technologies to make full use of the triplet energy levels of fluorescent materials to improve the luminescence efficiency. Summary of the invention

[0007] Through in-depth research, the researchers of the present invention discovered a new molecular design scheme, which resulted in a compound with more balanced luminous efficiency and lifespan characteristics.

[0008] Specifically, the present invention provides an organic compound having a structure shown in formula (1),

[0009]

[0010] In formula (1), Y and Y' are independently one of O, S, Se, N-Ar1, C(R1)(R2), Si(R3)(R4);

[0011] Ar1 is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0012] R1, R2, R3, and R4 are each independently selected from one of the following substituted or unsubstituted groups: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl; R1 and R2 are not connected or connected to form a ring, and R3 and R4 are not connected or connected to form a ring;

[0013] Ar1, R1, R2, R3, and R4 are each independently not connected to the adjacent ring A, ring D, or ring E, or Ar1, R1, R2, R3, and R4 are each independently connected to the adjacent ring A, ring D, or ring E through a CC single bond to form a ring structure;

[0014] In formula (1), ring A, ring D, and ring E are each independently selected from a substituted or unsubstituted C3-C60 heteroaromatic ring, or a substituted or unsubstituted C6-C60 aromatic ring, and at least one of ring A, ring D, and ring E is a structure represented by the following formula (a), wherein formula (a) is fused to the parent nucleus of formula (1) through one of rings F, ring G, or ring H to form a ring;

[0015]

[0016] In formula (a), Ring F, Ring G, and Ring H are each independently selected from a substituted or unsubstituted C3-C54 heteroaromatic ring, or a substituted or unsubstituted C6-C54 aromatic ring;

[0017] X 11 , X 12 , X 13 Each is independently one of O, S, N-Ar11, C(R11)(R12), Si(R13)(R14), and a, b, c are each independently 0 or 1;

[0018] When a is 0, it means X 11 The position is a CC single bond, that is, ring F and ring H are connected by a five-membered ring fusion. When b is 0, it represents X 12 The position is a CC single bond, which means that ring H and ring G are connected by a five-membered ring fusion. When c is 0, it represents X 13 The position is a CC single bond, which means that ring G and ring F are connected by a five-membered ring fusion;

[0019] Ar11 is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;

[0020] R11, R12, R13, and R14 are each independently selected from one of the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; R11 and R12 are not connected or connected to form a ring, and R13 and R14 are not connected or connected to form a ring;

[0021] The substituents substituted in the above-mentioned ring A, ring D, ring E, ring F, ring G, and ring H are each independently selected from halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C3-C60 heteroarylamino, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C3-C60 heteroaryloxy R' is selected from the group consisting of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds;

[0022] When substituents are independently present on the above-mentioned Ar1, Ar11, R1, R2, R3, R4, R11, R12, R13, and R14, the substituents are independently selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0023] 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.

[0024] 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, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0025] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0026] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0027] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes thereof. For example, the expression "hydrogen (H)" includes its isotopes. 1 H (hydrogen or H), 2 The concept of H (deuterium or D); carbon (C) includes 12 C. 13 C, etc., no further details.

[0028] 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.

[0029] In the present specification, examples of halogen include fluorine, chlorine, bromine, iodine and the like.

[0030] In the present invention, unless otherwise specified, aryl and heteroaryl include both single ring and condensed ring.

[0031] In the present invention, the C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0032] The C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0033] The C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0034] The C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0035] The C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] The C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0037] The C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0038] 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.

[0039] 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.

[0040] Specific examples of arylene groups in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of aryl groups. The number of carbon atoms in arylene groups includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc. Specific examples of heteroarylene groups in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of heteroaryl groups.

[0041] The aryloxy group in the present invention includes a monovalent group composed of the above-mentioned aryl group and heteroaryl group and oxygen.

[0042] In the present invention, arylamino represents a group formed by substituting one or two aryl groups for hydrogen on amino, wherein the connection point of the arylamino can be connected to the aryl group in the arylamino or to N in the arylamino, and the exemplary carbon number and specific group of the aryl group in the arylamino are the same as described above.

[0043] Examples of the C6-C30 arylamino group mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0044] Examples of the C3-C30 heteroarylamino group mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] In the present specification, the C2-C10 alkenyl group is a hydrocarbon group containing at least one C=C double bond, and illustratively includes but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl and the like.

[0050] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0051] Furthermore, at least one of ring A and ring D has a structure represented by formula (a); preferably, one and only one of ring A and ring D has a structure represented by formula (a).

[0052] Furthermore, Y and Y' are each independently one of O, S, Se, and N-Ar1; preferably, Y and Y' are each independently N-Ar1.

[0053] Furthermore, in formula (1), at least one of the substituents of ring E is a substituted or unsubstituted pyrenyl group;

[0054] In formula (a), ring F, ring G and ring H are each independently selected from a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C6-C30 aromatic ring.

[0055] Furthermore, in formula (1), ring E is a structure represented by formula (b):

[0056]

[0057] X 1 , X 2 , X 3 Each independently selected from CR 1 or N, the R 1 Each is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R" substituted C2~C20 alkenyl, unsubstituted or R" substituted C1~C20 straight or branched alkyl, unsubstituted or R" substituted C3~C20 cycloalkyl, unsubstituted or R" substituted C2~C20 alkenyl, unsubstituted or R" substituted C1~C20 alkoxy, unsubstituted or R" substituted C1~C20 alkylsilyl, unsubstituted or R" substituted C1~C20 alkylamino, unsubstituted or R" substituted C6~C30 arylamino, unsubstituted or R" substituted C3~C30 heteroarylamino, unsubstituted or R" substituted C6~C30 aryloxy, unsubstituted or R" substituted C3~C30 heteroaryloxy, unsubstituted or R" substituted C6~C60 aryl, and unsubstituted or R" substituted C3~C60 heteroaryl;

[0058] R" is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R"s are not connected or are connected to form a ring by chemical bonds; the R" is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

[0059] Furthermore, the compound of the present invention has a structure as shown in formula (2):

[0060]

[0061] In formula (2), the definitions of Y, Y', ring A, and ring D are the same as those in formula (1);

[0062] X 1 , X 2 , X 3 The definition of is the same as that in formula (b);

[0063] And X 1 , X 2 , X 3 At least one of them is CR 1 , and the R 1 is unsubstituted or R"-substituted pyrenyl;

[0064] Preferably, X 1 , X 2 , X 3 Each independently selected from CR 1 , the R 1 Each is independently selected from hydrogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C3-C60 heteroaryl; and X 1 , X 2 , X 3 At least one CR 1 R 1 is unsubstituted or R"-substituted pyrenyl;

[0065] R" is selected from one or a combination of two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;

[0066] More preferably, X 1 , X 2 , X 3 There is only one CR 1 R 1 is unsubstituted or R"-substituted pyrenyl;

[0067] Continue to preferably, X 1 , X 2 , X 3 There is only one CR 1 R 1 is unsubstituted or R"-substituted pyrenyl, X 1 , X 2 , X 3 The other two CR 1 R 1 is H;

[0068] More preferably, X 2 CR 1 , the R 1 is unsubstituted or R"-substituted pyrenyl;

[0069] Most preferably, X 2 CR 1 , the R 1 is unsubstituted or R"-substituted pyrenyl, X 1 , X 3 All are CH.

[0070] Furthermore, in formula (a), ring F, ring G, and ring H are structures represented by formula (c):

[0071]

[0072] In formula (c), X 4 , X 5 , X 6 Each independently selected from CR 2 or N, the R 2Each is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R"' substituted C2~C20 alkenyl, unsubstituted or R"' substituted C1~C20 straight or branched alkyl, unsubstituted or R"' substituted C3~C20 cycloalkyl, unsubstituted or R"' substituted C1~C20 alkoxy, unsubstituted or R"' substituted C1~C20 alkylsilyl, unsubstituted or R"' substituted C1~C20 alkylamino, unsubstituted or R"' substituted C6~C30 arylamino, unsubstituted or R"' substituted C3~C30 heteroarylamino, unsubstituted or R"' substituted C6~C30 aryloxy, unsubstituted or R"' substituted C3~C30 heteroaryloxy, unsubstituted or R"' substituted C6~C60 aryl, and unsubstituted or R"' substituted C3~C60 heteroaryl;

[0073] R'' is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R''s are not connected or are connected to form a ring by chemical bonds; the R'' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

[0074] Furthermore, formula (a) is a structure shown in the following formula (a-1):

[0075]

[0076] Wherein, a and b represent the fusion positions with the parent core of formula (1);

[0077] X 11 , X 12 , X 13 , a, b, c are the same as those in formula (a);

[0078] X 4 , X 5 , X 6 The definition of is the same as that in formula (c), X 4’ , X 5’ , X 6’ Definition and X 4 , X 5 , X 6 The definition of is the same as;

[0079] Preferably, X 11 , X 12 , X 13At least two of them are CC single bonds;

[0080] More preferably, formula (a) is a structure as shown in the following formula (a-2):

[0081]

[0082] X 12 One selected from CC single bond, O, S, N-Ar11, C(R11)(R12), Si(R13)(R14).

[0083] Furthermore, in formula (1), one of ring A and ring D has a structure represented by formula (a), and the other has a structure represented by the following formula (e) or the following formula (d):

[0084]

[0085] In formula (e), Y 1 , Y 2 , Y 3 , Y 4 Each independently selected from CR 3 or N, R 3 Each is independently selected from one of hydrogen, halogen, unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C2-C20 alkenyl, unsubstituted or R"" substituted C1-C20 alkoxy, unsubstituted or R"" substituted C1-C20 alkylsilyl, unsubstituted or R"" substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"" substituted C6-C30 arylamino, unsubstituted or R"" substituted C3-C30 heteroarylamino, unsubstituted or R"" substituted C6-C30 aryloxy, unsubstituted or R"" substituted C3-C30 heteroaryloxy, unsubstituted or R"" substituted C6-C60 aryl, and unsubstituted or R' substituted C3-C60 heteroaryl;

[0086] In formula (d), X is selected from O, S, NR 4 or CR 5 R 6 , where R 4 , R 5 , R 6 Each is independently selected from one of unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C6-C60 aryl, and unsubstituted or R"" substituted C3-C60 heteroaryl;

[0087] Ring I is selected from a substituted or unsubstituted C6-C58 aromatic ring, a substituted or unsubstituted C3-C58 heteroaromatic ring;

[0088] The substituents substituted in ring I are each independently selected from halogen, unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C2-C20 alkenyl, unsubstituted or R"" substituted C1-C20 alkoxy, unsubstituted or R"" substituted C1-C20 alkylsilyl, unsubstituted or R"" substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"" substituted C6-C30 arylamino, unsubstituted or R"" substituted C3-C30 heteroarylamino, unsubstituted or R"" substituted C6-C30 aryloxy, unsubstituted or R"" substituted C3-C30 heteroaryloxy, unsubstituted or R"" substituted C6-C60 aryl, unsubstituted or R"" substituted C3-C60 heteroaryl;

[0089] R"" is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R"" are not connected or connected to form a ring by chemical bonds;

[0090] More preferably, in formula (1), one of ring A and ring D has a structure represented by formula (a), and the other has a structure represented by formula (e).

[0091] Furthermore, in formula (2), X 1 , X 2 , X 3 At least one of them is CR 1 , and the R 1 One of the following structures selected from pyrenyl or R" substituted, "*—" represents the connection site:

[0092]

[0093] R" is selected from one or a combination of two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;

[0094] Preferably, R" is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl and carbazolyl.

[0095] As preferred structures of the compounds of the present invention, the following specific compounds S1-S126 can be cited, but are not limited to these compounds:

[0096]

[0097]

[0098]

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[0110] The above-mentioned compound of the present invention has excellent luminescent properties, can provide triplet excitons to achieve higher luminescent efficiency, and is suitable for use as a luminescent dye, especially as a green luminescent dye, based on its excellent carrier transfer efficiency. Of course, since the compound of the present invention can also be used as a sensitizer together with the host material and the dye to achieve a good luminescent layer. The devices used include but are not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper, preferably organic electroluminescent devices.

[0111] As a low triplet energy level fragment, pyrene is beneficial to lowering the triplet energy level of the molecule and has a significant effect on improving the device life. The a-type structure can increase molecular conjugation, adjust the light color to green, and is beneficial to the carrier transfer balance, thereby improving device efficiency.

[0112] The present invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains at least one compound described in the present invention.

[0113] The structure of the organic electroluminescent device of the present invention is consistent with that of the existing devices, for example, it includes an anode layer, multiple light-emitting functional layers and a cathode layer; the multiple light-emitting functional layers at least include a light-emitting layer, wherein the light-emitting layer contains the above-mentioned organic compound of the present invention.

[0114] 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.

[0115] 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.

[0116] The OLED device prepared by using the compound of the present invention has high luminous efficiency and better service life, especially can adjust the light color of red light dye to achieve the light color required for mass production, and can meet the requirements of current panel and display manufacturers for high-performance materials. DETAILED DESCRIPTION

[0117] In order to enable those skilled in the art to better understand the present invention, the present invention is further described in detail below in conjunction with specific implementation modes.

[0118] The compounds of the synthesis methods not mentioned in the present invention are all raw materials obtained through commercial channels. The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, toluene, anhydrous sodium sulfate, carbazole, benzimidazole and other chemical reagents, can be purchased from the domestic chemical product market, such as Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. In addition, those skilled in the art can also synthesize by known methods.

[0119] The analysis and detection of the intermediates and compounds in the present invention were performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0120] The synthesis method of the compound of the present invention is briefly described below.

[0121] Synthesis Example 1: Synthesis of S1

[0122]

[0123] Synthesis of intermediate M1-1

[0124] At room temperature, raw material 1 (50 g, 273.26 mmol), raw material 2 (83.99 g, 300.58 mmol), cesium tricarbonate (133.55 g, 409.88 mmol), DMF (500 ml) as solvent were added to a 1L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100°C overnight. After the reaction solution was cooled, water (500 ml) was added to precipitate a white solid, and stirred for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 101 g of white solid M1-1. The molecular ion mass determined by mass spectrometry is: 441.17 (theoretical value: 441.14).

[0125] Synthesis of intermediate M1-2

[0126] At room temperature, add raw material M1-1 (50g, 113.02mmol), raw material 3 (43.45g, 113.02mmol), cesium carbonate (55.24g, 169.53mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 63.5g of white solid M1-2. The molecular ion mass determined by mass spectrometry is: 805.32 (theoretical value: 805.30).

[0127] Synthesis of intermediate M1-3

[0128] At room temperature, raw material M1-2 (15 g, 18.59 mmol), raw material 4 (5.49 g, 22.31 mmol), tetrakis(triphenylphosphine)palladium (0.64 g, 0.56 mmol), potassium carbonate (3.85 g, 27.89 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 12.3 g of a white solid. The molecular ion mass determined by mass spectrometry was 971.41 (theoretical value: 971.40).

[0129] Synthesis of final product S1

[0130] At room temperature, add M1-3 (12g, 12.34mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (10.02ml, 16.04mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.38ml, 24.67mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.46ml, 37.01mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.5 g of a red solid. The molecular ion mass determined by mass spectrometry was 945.44 (theoretical value: 945.43).

[0131] Synthesis Example 2: Synthesis of S2

[0132]

[0133] Synthesis of intermediate M2-1

[0134] At room temperature, add raw material M1-1 (15g, 33.91mmol), raw material 5 (13.04g, 33.91mmol), cesium carbonate (16.57g, 50.86mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 17.5g of white solid M2-1. The molecular ion mass determined by mass spectrometry is: 805.31 (theoretical value: 805.30).

[0135] Synthesis of intermediate M2-2

[0136] At room temperature, raw material M2-1 (17 g, 21.07 mmol), raw material 4 (6.22 g, 25.28 mmol), tetrakis(triphenylphosphine)palladium (0.73 g, 0.63 mmol), potassium carbonate (4.37 g, 31.60 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 15.7 g of a white solid. The molecular ion mass determined by mass spectrometry was 971.42 (theoretical value: 971.40).

[0137] Synthesis of final product S2

[0138] At room temperature, add M2-2 (12g, 12.34mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (10.02ml, 16.04mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.38ml, 24.67mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.46ml, 37.01mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.7 g of a red solid. The molecular ion mass determined by mass spectrometry was 945.44 (theoretical value: 945.43).

[0139] Synthesis Example 3: Synthesis of S3

[0140]

[0141] Synthesis of intermediate M3-1

[0142] At room temperature, add raw material M1-1 (15g, 33.91mmol), raw material 6 (14.94g, 33.91mmol), cesium carbonate (16.57g, 50.86mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 21.3g of white solid M3-1. The molecular ion mass determined by mass spectrometry is: 861.38 (theoretical value: 861.36).

[0143] Synthesis of intermediate M3-2

[0144] At room temperature, raw material M3-1 (21 g, 24.33 mmol), raw material 4 (7.19 g, 29.20 mmol), tetrakis(triphenylphosphine)palladium (0.84 g, 0.73 mmol), potassium carbonate (5.04 g, 36.50 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 18.3 g of a white solid. The molecular ion mass determined by mass spectrometry was 1027.47 (theoretical value: 1027.46).

[0145] Synthesis of final product S3

[0146] At room temperature, add M3-2 (16.00 g, 15.55 mmol) and xylene (100 ml) to a 500 ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (12.64 ml, 20.22 mmol, 1.6 M) to the system at -70 ° C, stir at room temperature for 5 min, heat to 60 ° C and react for 2 h, the system changes from anhydrous clear to dark red. Add boron tribromide (3.00 ml, 31.00 mmol, 2.60 g / ml) to the system at -40 ° C, stir at low temperature for 10 min, the system changes from dark red transparent to red turbid. Then add N, N-diisopropylethylamine (8.15 ml, 46.66 mmol, 0.74 g / ml) at -40 ° C, heat to 120 ° C and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 3.5 g of a red solid. The molecular ion mass determined by mass spectrometry was 1001.52 (theoretical value: 1001.50).

[0147] Synthesis Example 4: Synthesis of S10

[0148]

[0149] Synthesis of intermediate M4-1

[0150] At room temperature, add raw material M1-1 (15g, 33.91mmol), raw material 7 (16.09g, 33.91mmol), cesium carbonate (16.57g, 50.86mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 21.3g of white solid M4-1. The molecular ion mass determined by mass spectrometry is: 895.32 (theoretical value: 895.31).

[0151] Synthesis of intermediate M4-2

[0152] At room temperature, raw material M4-1 (20 g, 22.30 mmol), raw material 4 (6.58 g, 26.76 mmol), tetrakis(triphenylphosphine)palladium (0.77 g, 0.67 mmol), potassium carbonate (4.61 g, 33.37 mmol), 1,4-dioxane (300 ml) and water (30 ml) were added to a 1000 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 16.60 g of a white solid. The molecular ion mass determined by mass spectrometry was 1061.47 (theoretical value: 1061.46).

[0153] Synthesis of final product S10

[0154] At room temperature, add M4-2 (16g, 15.06mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (18.82ml, 30.11mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.90ml, 30.11mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (7.89ml, 45.17mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.3 g of a red solid. The molecular ion mass determined by mass spectrometry was 1035.45 (theoretical value: 1035.44).

[0155] Synthesis Example 5: Synthesis of S53

[0156]

[0157] Synthesis of intermediate M5-1

[0158] At room temperature, raw material 8 (50 g, 219.85 mmol), raw material 2 (67.57 g, 241.83 mmol), cesium carbonate (107.44 g, 329.77 mmol), DMF (500 ml) as solvent were added to a 1 L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. After the reaction solution was cooled, water (500 ml) was added to precipitate a white solid, and stirred for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 95 g of white solid M5-1. The molecular ion mass determined by mass spectrometry is: 485.11 (theoretical value: 485.09).

[0159] Synthesis of intermediate M5-2

[0160] At room temperature, add raw material M5-1 (50g, 102.7mmol), raw material 9 (38.87g, 102.7mmol), cesium carbonate (50.19g, 154.05mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 65.3g of white solid M5-2. The molecular ion mass determined by mass spectrometry is: 843.21 (theoretical value: 843.20).

[0161] Synthesis of intermediate M5-3

[0162] At room temperature, raw material M5-2 (15 g, 17.57 mmol), raw material 4 (5.24 g, 21.29 mmol), tetrakis(triphenylphosphine)palladium (0.62 g, 0.53 mmol), potassium carbonate (3.68 g, 26.62 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 8.5 g of a white solid. The molecular ion mass determined by mass spectrometry was 965.36 (theoretical value: 965.35).

[0163] Synthesis of final product S53

[0164] At room temperature, add M5-3 (8.5g, 8.79mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (7.14ml, 11.43mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (1.69ml, 17.59mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (4.61ml, 26.38mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.1 g of a red solid. The molecular ion mass determined by mass spectrometry was 939.39 (theoretical value: 939.38).

[0165] Synthesis Example 6: Synthesis of S56

[0166]

[0167] Synthesis of intermediate M6-1

[0168] At room temperature, add raw material M5-1 (15 g, 30.81 mmol), raw material 10 (11.66 g, 30.81 mmol), cesium carbonate (15.06 g, 46.22 mmol), DMF (200 ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 18.2 g of white solid M6-1. The molecular ion mass determined by mass spectrometry is: 843.22 (theoretical value: 843.20).

[0169] Synthesis of intermediate M6-2

[0170] At room temperature, raw material M6-1 (18 g, 21.29 mmol), raw material 4 (6.29 g, 25.55 mmol), tetrakis(triphenylphosphine)palladium (0.74 g, 0.64 mmol), potassium carbonate (4.41 g, 31.94 mmol), 1,4-dioxane (300 ml) and water (30 ml) were added to a 1000 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 11.3 g of a white solid. The molecular ion mass determined by mass spectrometry was 965.36 (theoretical value: 965.35).

[0171] Synthesis of final product S56

[0172] At room temperature, add M6-2 (12g, 12.41mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (10.09ml, 16.14mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.39ml, 24.83mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.50ml, 37.24mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 3.2 g of a red solid. The molecular ion mass determined by mass spectrometry was 939.41 (theoretical value: 939.38).

[0173] Synthesis Example 7: Synthesis of S62

[0174]

[0175] Synthesis of intermediate M7-1

[0176] At room temperature, add raw material M5-1 (15 g, 30.81 mmol), raw material 11 (10.61 g, 30.81 mmol), cesium carbonate (15.06 g, 46.22 mmol), DMF (200 ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 17.5 g of white solid M7-1. The molecular ion mass determined by mass spectrometry is: 809.20 (theoretical value: 809.18).

[0177] Synthesis of intermediate M7-2

[0178] At room temperature, raw material M7-1 (17 g, 20.96 mmol), raw material 4 (6.19 g, 25.15 mmol), tetrakis(triphenylphosphine)palladium (0.73 g, 0.63 mmol), potassium carbonate (4.34 g, 31.43 mmol), 1,4-dioxane (300 ml) and water (30 ml) were added to a 1000 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 12.3 g of a white solid. The molecular ion mass determined by mass spectrometry was 931.34 (theoretical value: 931.33).

[0179] Synthesis of final product S62

[0180] At room temperature, add M7-2 (12g, 12.87mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (10.46ml, 16.73mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.48ml, 25.74mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.74ml, 38.60mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.7 g of a red solid. The molecular ion mass determined by mass spectrometry was 905.38 (theoretical value: 905.36).

[0181] Synthesis Example 8: Synthesis of S103

[0182]

[0183] Synthesis of intermediate M8-1

[0184] At room temperature, raw material 8 (50 g, 219.85 mmol), raw material 2 (67.57 g, 241.83 mmol), cesium carbonate (107.44 g, 329.77 mmol), DMF (500 ml) as solvent were added to a 1 L single-mouth bottle, nitrogen was replaced three times, and the reaction was carried out at 100 ° C overnight. After the reaction solution was cooled, water (500 ml) was added to precipitate a white solid, and stirred for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 85 g of white solid M8-1. The molecular ion mass determined by mass spectrometry is: 485.12 (theoretical value: 485.09).

[0185] Synthesis of intermediate M8-2

[0186] At room temperature, add raw material M8-1 (15 g, 30.81 mmol), raw material 12 (10.12 g, 30.81 mmol), cesium carbonate (15.06 g, 46.22 mmol), DMF (200 ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110°C overnight. After the reaction solution is cooled, add water (500 ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 19.3 g of white solid M8-2. The molecular ion mass determined by mass spectrometry is: 793.20 (theoretical value: 793.19).

[0187] Synthesis of intermediate M8-3

[0188] At room temperature, raw material M8-2 (18 g, 22.64 mmol), raw material 13 (6.68 g, 27.16 mmol), tetrakis(triphenylphosphine)palladium (0.78 g, 0.68 mmol), potassium carbonate (4.69 g, 33.95 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel and concentrated, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 11.1 g of a white solid. The molecular ion mass determined by mass spectrometry was 915.35 (theoretical value: 915.34).

[0189] Synthesis of final product S103

[0190] At room temperature, add M8-3 (11g, 12.00mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (9.75ml, 15.60mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.31ml, 24.00mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.29ml, 36.00mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.9 g of a red solid. The molecular ion mass determined by mass spectrometry was 889.37 (theoretical value: 889.36).

[0191] Synthesis Example 9: Synthesis of S108

[0192]

[0193] Synthesis of intermediate M9-1

[0194] At room temperature, raw material M8-2 (16 g, 21.02 mmol), raw material 13 (5.94 g, 24.14 mmol), tetrakis(triphenylphosphine)palladium (0.70 g, 0.60 mmol), potassium carbonate (4.17 g, 30.18 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 12.6 g of a white solid. The molecular ion mass determined by mass spectrometry was 915.36 (theoretical value: 915.34).

[0195] Synthesis of final product S108

[0196] At room temperature, add M9-2 (11g, 12mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (9.75ml, 15.60mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.31ml, 24.0mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.29ml, 36.0mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 3.0 g of a red solid. The molecular ion mass determined by mass spectrometry was 889.37 (theoretical value: 889.36).

[0197] Synthesis Example 10: Synthesis of S111

[0198]

[0199] Synthesis of intermediate M10-1

[0200] At room temperature, add raw material M8-1 (15g, 30.81mmol), raw material 11 (10.61g, 30.81mmol), cesium carbonate (15.06g, 46.22mmol), DMF (200ml) as solvent to a 1L single-mouth bottle, replace nitrogen three times, and react at 110℃ overnight. After the reaction solution is cooled, add water (500ml) to precipitate a white solid, and stir for 30 minutes. Filter, dissolve the filter cake in dichloromethane, perform rapid column chromatography, concentrate, and wash with ethanol to obtain 18.6g of white solid M10-1. The molecular ion mass determined by mass spectrometry is: 809.19 (theoretical value: 809.18).

[0201] Synthesis of intermediate M10-2

[0202] At room temperature, raw material M10-1 (16 g, 19.72 mmol), raw material 10 (5.82 g, 23.67 mmol), tetrakis(triphenylphosphine)palladium (0.68 g, 0.59 mmol), potassium carbonate (4.09 g, 29.59 mmol), 1,4-dioxane (150 ml) and water (30 ml) were added to a 250 ml single-mouth bottle as solvent, nitrogen was replaced three times, and the reaction was carried out at 100°C for 4 hours. The mixture was cooled to room temperature, 40 ml of water was added, and dichloromethane (30 ml) was extracted three times. The organic phase was mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 10.7 g of a white solid. The molecular ion mass determined by mass spectrometry was: 931.34 (theoretical value: 931.33).

[0203] Synthesis of final product S111

[0204] At room temperature, add M10-2 (11g, 11.77mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (9.56ml, 15.30mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (2.27ml, 23.54mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (6.17ml, 35.31mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 2.1 g of a red solid. The molecular ion mass determined by mass spectrometry was 905.37 (theoretical value: 905.36).

[0205] Synthesis Example 11: Synthesis of S124

[0206]

[0207] Synthesis of intermediate M11-1

[0208] At room temperature, raw material 12 (15 g, 66.40 mmol), raw material 13 (12.36 g, 73.04 mmol), Pd2dba3 (1.22 g, 1.33 mmol), s-Phos (1.09 g, 2.66 mmol), sodium tert-butoxide (9.57 g, 99.60 mmol) and toluene (100 ml) were added to a 1L single-mouth bottle, and nitrogen was replaced three times. The reaction was carried out at 100°C overnight. After the reaction solution was cooled, it was dissolved in dichloromethane and subjected to rapid column chromatography, concentrated, and washed with ethanol to obtain 15.2 g of white solid M11-1. The molecular ion mass determined by mass spectrometry was 313.05 (theoretical value: 313.04).

[0209] Synthesis of intermediate M11-2

[0210] At room temperature, raw material M11-1 (15.2 g, 48.38 mmol), raw material 14 (17.58 g, 53.21 mmol), Pd132 (1.03 g, 1.45 mmol), sodium tert-butoxide (6.97 g, 72.56 mmol), and toluene (100 ml) were added to a 250 ml single-mouth bottle, and the mixture was reacted at 100 ° C overnight, cooled to room temperature, and the organic phase was dissolved in dichloromethane and mixed with silica gel for concentration, column chromatography (PE: DCM = 20: 1), and toluene / ethanol recrystallization was performed to obtain 13.1 g of a white solid. The molecular ion mass determined by mass spectrometry analysis was 605.18 (theoretical value: 605.17).

[0211] Synthesis of final product S124

[0212] At room temperature, add M11-2 (13g, 21.38mmol) and xylene (100ml) to a 500ml three-necked flask, replace nitrogen 3 times, add tert-butyl lithium n-hexane solution (26.72ml, 42.75mmol, 1.6M) to the system at -70℃, stir at room temperature for 5min, heat to 60℃ and react for 2h, the system changes from anhydrous clear to dark red. Add boron tribromide (4.12ml, 42.75mmol, 2.60g / ml) to the system at -40℃, stir at low temperature for 10min, the system changes from dark red transparent to red turbid. Then add N,N-diisopropylethylamine (11.2ml, 64.13mmol, 0.74g / ml) at -40℃, heat to 120℃ and react overnight. The system was cooled to room temperature, dichloromethane (200 ml) was added to dissolve, the mixture was concentrated by silica gel, column chromatography (PE: DCM = 20:1), and the crude product was recrystallized twice from toluene / ethanol to obtain 1.2 g of a red solid. The molecular ion mass determined by mass spectrometry was 581.22 (theoretical value: 581.21).

[0213] The synthesis method of S125 and S126 is the same as that of S124

[0214]

[0215] Implementation

[0216] 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.

[0217] 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.

[0218] The first electrode can be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like and any combination thereof can be used.

[0219] 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.

[0220] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) of a single-layer structure, 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 multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0221] 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, wherein the aromatic amine derivatives include the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0222]

[0223]

[0224]

[0225] 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.

[0226]

[0227] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra and a host material (Host). The light-emitting layer can 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 can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0228] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0229]

[0230] In one aspect of the present invention, the light-emitting layer adopts the technology of combining phosphorescence sensitized luminescence and thermally activated sensitized fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above PH-1 to PH-85.

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] 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.

[0237] The OLED organic 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 multi-layer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0238] 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.

[0239]

[0240]

[0241]

[0242]

[0243] 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.

[0244] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li 2 O、Cs 2 CO 3 , BaO, Na, Li, Ca, Mg, Yb.

[0245] Device Example 1:

[0246] The device structure is shown below:

[0247] ITO(150nm) / HI-2(10nm) / HT-2(40nm) / BFH-3:S1(30nm, 5%wt) / ET-59(25nm) / LiF(0.5nm) / Al(150nm).

[0248] The preparation process of organic electroluminescent device is as follows:

[0249] A glass plate coated with a transparent conductive layer of ITO (thickness 150 nm) 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 until the water was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0250] Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 , HI-2 and HT-2 were vacuum-deposited on the above-mentioned anode layer as a hole injection layer and a hole transport layer, respectively, with a deposition rate of 0.1 nm / s and a deposition film thickness of 10 nm and 40 nm, respectively;

[0251] Compound HT-40 was vacuum-deposited on the hole transport layer as an electron blocking layer, with a total film thickness of 5 nm;

[0252] Vacuum evaporate "BFH-3: S1 (30nm, 5%wt)" on the hole transport layer as the light-emitting layer of the organic electroluminescent device, the evaporation rate is 0.1nm / s, and the total evaporation film thickness is 30nm; "5%wt" refers to the doping ratio of the green dye, that is, the weight ratio of the main material to S1 is 95:5;

[0253] Compound ET-23 was vacuum-deposited on the light-emitting layer as a hole blocking layer, with a total film thickness of 5 nm;

[0254] ET-59 was vacuum-deposited on the light-emitting layer as the electron transport layer of the organic electroluminescent device, with a deposition rate of 0.1 nm / s and a total deposition film thickness of 20 nm;

[0255] 0.5 nm of LiF as an electron injection layer and 150 nm of Al as a cathode were vacuum-deposited on the electron transport layer.

[0256] The manufacturing process of device examples 2-13 and comparative examples 1-3 is the same as that of device example 1, except that the dyes are replaced with R-1, R-2, and R-3.

[0257]

[0258] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0259] At the same brightness, a digital source meter and a brightness meter were used to measure the driving voltage and current efficiency of the organic electroluminescent devices prepared in Examples 1-10 and Comparative Examples 1-3. 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 that time is the driving voltage; the external quantum efficiency is measured with an integrating sphere;

[0260] The test method for LT95 life is as follows: Use a luminance meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 950cd / m 2 The time, in h;

[0261] The LT95 life test value of comparative example 1 is recorded as 1, and the LT95 life of each device embodiment and other comparative examples is the ratio of the respective LT95 life test value to the test value of comparative example 1 (relative life); the test results are shown in Table 1:

[0262] Table 1

[0263]

[0264]

[0265] In the compounds of Examples 1-10, in the structure of formula a, the benzene rings on the carbazole are bonded to each other, which increases the conjugation of the molecule, enhances the rigidity of the molecule, promotes the transmission of carriers, reduces the energy loss caused by molecular vibration, and improves the luminous efficiency. The pyrene substituent is introduced into the structure to balance the carrier transmission, so that the carriers can be better recombined on the dye. Thereby improving the material stability, improving the stability of the device operation, reducing the operating voltage, and improving the EQE.

[0266] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compounds and their applications, and the organic electroluminescent devices containing the same, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that Having the structure shown in formula (1), In formula (1), Y and Y' are independently one of O, S, Se, N-Ar1, C(R1)(R2), Si(R3)(R4); Ar1 is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; R1, R2, R3, and R4 are each independently selected from one of the following substituted or unsubstituted groups: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl; R1 and R2 are not connected or connected to form a ring, and R3 and R4 are not connected or connected to form a ring; Ar1, R1, R2, R3, and R4 are each independently not connected to the adjacent ring A, ring D, or ring E, or Ar1, R1, R2, R3, and R4 are each independently connected to the adjacent ring A, ring D, or ring E through a CC single bond to form a ring structure; In formula (1), ring A, ring D, and ring E are each independently selected from a substituted or unsubstituted C3-C60 heteroaromatic ring, or a substituted or unsubstituted C6-C60 aromatic ring, and at least one of ring A, ring D, and ring E is a structure represented by the following formula (a), wherein formula (a) is fused to the parent nucleus of formula (1) through one of rings F, ring G, or ring H to form a ring; In formula (a), Ring F, Ring G, and Ring H are each independently selected from a substituted or unsubstituted C3-C54 heteroaromatic ring, or a substituted or unsubstituted C6-C54 aromatic ring; X 11 , X 12 , X 13 Each is independently one of O, S, N-Ar11, C(R11)(R12), Si(R13)(R14), and a, b, c are each independently 0 or 1; When a is 0, it means X 11 The position is a CC single bond, that is, ring F and ring H are connected by a five-membered ring fusion. When b is 0, it represents X 12 The position is a CC single bond, which means that ring H and ring G are connected by a five-membered ring fusion. When c is 0, it represents X 13 The position is a CC single bond, which means that ring G and ring F are connected by a five-membered ring fusion; Ar11 is selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; R11, R12, R13, and R14 are each independently selected from one of the following substituted or unsubstituted groups: C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; R11 and R12 are not connected or connected to form a ring, and R13 and R14 are not connected or connected to form a ring; The substituents substituted in the above-mentioned ring A, ring D, ring E, ring F, ring G, and ring H are each independently selected from halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C20 straight or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C1-C20 alkylamino, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C3-C60 heteroarylamino, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C3-C60 heteroaryloxy R' is selected from the group consisting of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryloxy, C3-C60 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R's are not connected or are connected to form a ring by chemical bonds; the R' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds; When substituents are independently present on the above-mentioned Ar1, Ar11, R1, R2, R3, R4, R11, R12, R13, and R14, the substituents are independently selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that At least one of ring A and ring D has a structure represented by formula (a); Preferably, one and only one of ring A and ring D has a structure represented by formula (a).

3. The organic compound according to claim 1, characterized in that Y and Y' are independently one of O, S, Se, and N-Ar1; Preferably, Y and Y' are each independently N-Ar1.

4. The organic compound according to claim 1, characterized in that In formula (1), at least one of the substituents of ring E is a substituted or unsubstituted pyrenyl group; In formula (a), ring F, ring G and ring H are each independently selected from a substituted or unsubstituted C3-C30 heteroaromatic ring and a substituted or unsubstituted C6-C30 aromatic ring.

5. The organic compound according to claim 1, characterized in that Ring E is a structure represented by formula (b): X1, X2, and X3 are each independently selected from CR1 or N, and R1 is each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C2-C20 alkenyl, unsubstituted or R"-substituted C1-C20 alkoxy, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C1-C20 alkylamino, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C3-C30 heteroarylamino, unsubstituted or R"-substituted C6-C30 aryloxy, unsubstituted or R"-substituted C3-C30 heteroaryloxy, unsubstituted or R"-substituted C6-C60 aryl, and unsubstituted or R"-substituted C3-C60 heteroaryl; R" is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R"s are not connected or are connected to form a ring by chemical bonds; the R" is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

6. The organic compound according to claim 5, characterized in that It has the structure shown in formula (2): In formula (2), the definitions of Y, Y', ring A, and ring D are the same as those in formula (1); X1, X2, and X3 are defined the same as in formula (b); At least one of X1, X2, and X3 is CR1, and R1 is an unsubstituted or R"-substituted pyrene group; Preferably, X1, X2, and X3 are each independently selected from CR1, and R1 is each independently selected from one of hydrogen, unsubstituted or R"-substituted C1-C20 straight or branched alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C1-C20 alkylsilyl, unsubstituted or R"-substituted C6-C60 aryl, and unsubstituted or R"-substituted C3-C60 heteroaryl; and R1 in at least one CR1 among X1, X2, and X3 is unsubstituted or R"-substituted pyrenyl; R" is selected from one or a combination of two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; More preferably, among X1, X2, and X3, only one R1 in CR1 is unsubstituted or R"-substituted pyrene; Still preferably, only one R1 in CR1 among X1, X2, and X3 is unsubstituted or R″-substituted pyrene, and the R1 in the other two CR1 among X1, X2, and X3 is H; More preferably, X2 is CR1, and R1 is unsubstituted or R"-substituted pyrenyl; Most preferably, X2 is CR1, R1 is unsubstituted or R"-substituted pyrene, and X1 and X3 are both CH.

7. The organic compound according to claim 1, characterized in that In formula (a), ring F, ring G, and ring H are structures represented by formula (c): In formula (c), X4, X5, and X6 are each independently selected from CR2 or N, and R2 is each independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R"' substituted C2-C20 alkenyl, unsubstituted or R"' substituted C1-C20 straight or branched alkyl, unsubstituted or R"' substituted C3-C20 cycloalkyl, unsubstituted or R"' substituted C1-C20 alkoxy, unsubstituted or R"' substituted C1-C2 0 alkylsilyl, unsubstituted or R"' substituted C1-C20 alkylamino, unsubstituted or R"' substituted C6-C30 arylamino, unsubstituted or R"' substituted C3-C30 heteroarylamino, unsubstituted or R"' substituted C6-C30 aryloxy, unsubstituted or R"' substituted C3-C30 heteroaryloxy, unsubstituted or R"' substituted C6-C60 aryl, unsubstituted or R"' substituted C3-C60 heteroaryl; R'' is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R''s are not connected or are connected to form a ring by chemical bonds; the R'' is not connected to adjacent ring structures or is connected to form a ring by chemical bonds.

8. The organic compound according to claim 7, characterized in that Formula (a) is a structure shown in the following formula (a-1): Wherein, a and b represent the fusion positions with the parent core of formula (1); X 11 , X 12 , X 13 , a, b, c are the same as those in formula (a); X4, X5, and X6 have the same definitions as those in formula (c). 4’ , X 5’ , X 6’ The definition of is the same as that of X4, X5, and X6; Preferably, X 11 , X 12 , X 13 At least two of them are CC single bonds; More preferably, formula (a) is a structure shown in the following formula (a-2): X 12 One selected from CC single bond, O, S, N-Ar11, C(R11)(R12), Si(R13)(R14).

9. The organic compound according to claim 1, characterized in that In formula (1), one of ring A and ring D has a structure represented by formula (a), and the other has a structure represented by the following formula (e) or (d): In formula (e), Y 1 , Y 2 , Y 3 , Y 4 Each is independently selected from CR3 or N, and R3 is independently selected from hydrogen, halogen, unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C2-C20 alkenyl, unsubstituted or R"" substituted C1-C20 alkoxy, unsubstituted or R"" substituted C1-C20 alkylsilyl, unsubstituted or R"" substituted C1-C20 One of C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"" substituted C6-C30 arylamino, unsubstituted or R"" substituted C3-C30 heteroarylamino, unsubstituted or R"" substituted C6-C30 aryloxy, unsubstituted or R"" substituted C3-C30 heteroaryloxy, unsubstituted or R"" substituted C6-C60 aryl, and unsubstituted or R' substituted C3-C60 heteroaryl; In formula (d), X is selected from O, S, NR4 or CR5R6, wherein R4, R5, and R6 are each independently selected from one of unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C6-C60 aryl, and unsubstituted or R"" substituted C3-C60 heteroaryl; Ring I is selected from a substituted or unsubstituted C6-C58 aromatic ring, a substituted or unsubstituted C3-C58 heteroaromatic ring; The substituents substituted in ring I are each independently selected from halogen, unsubstituted or R"" substituted C1-C20 straight or branched alkyl, unsubstituted or R"" substituted C3-C20 cycloalkyl, unsubstituted or R"" substituted C2-C20 alkenyl, unsubstituted or R"" substituted C1-C20 alkoxy, unsubstituted or R"" substituted C1-C20 alkylsilyl, unsubstituted or R"" substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R"" substituted C6-C30 arylamino, unsubstituted or R"" substituted C3-C30 heteroarylamino, unsubstituted or R"" substituted C6-C30 aryloxy, unsubstituted or R"" substituted C3-C30 heteroaryloxy, unsubstituted or R"" substituted C6-C60 aryl, unsubstituted or R"" substituted C3-C60 heteroaryl; R"" is selected from one or a combination of two of halogen, cyano, nitro, hydroxyl, amino, C2-C20 alkenyl, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R"" are not connected or connected to form a ring by chemical bonds; Preferably, in formula (1), one of ring A and ring D has a structure represented by formula (a), and the other has a structure represented by formula (e).

10. The organic compound according to claim 6, characterized in that In formula (2), at least one of X1, X2, and X3 is CR1, and R1 is selected from one of the following structures substituted with pyrenyl or R", and "*—" represents a connection site: R" is selected from one or a combination of two of halogen, cyano, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; Preferably, R" is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, trifluoromethyl, cyano, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, furanyl, benzofuranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl and carbazolyl.

11. The organic compound according to claim 1, characterized in that It has the following structure:

12. Use of the organic compound according to any one of claims 1 to 11, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device is selected from 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; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in the light-emitting layer.

13. 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 contains the organic compound according to any one of claims 1 to 11; Preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the organic compound described in any one of claims 1 to 11; More preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the light-emitting layer includes a host material and a dye, and the dye includes at least one organic compound described in any one of claims 1 to 11.

14. A display device, characterized in that: The display device comprises the organic electroluminescent device as claimed in claim 13.

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