Polycyclic aromatic compound and application thereof

Abstract

The invention provides a polycyclic aromatic compound and application thereof, the polycyclic aromatic compound has a structure as shown in formula (1), rings A, B, C, D, E and F are independently selected from one of substituted or unsubstituted C6-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings, and at least one of Z1 and Z3 has a structure as shown in formula (a). The polycyclic aromatic compound provided by the invention has good stability and steric configuration, can realize relatively high luminous efficiency by utilizing triplet excitons, has excellent carrier transport efficiency, effectively avoids molecular aggregation, can be used as a material of a luminescent layer for an organic electroluminescent device, can effectively prolong the service life of the device, and has good application prospects in the field of organic electroluminescent devices. The luminous efficiency is improved. # imgabs0 #

Description

Technical Field

[0001] The invention relates to a polycyclic aromatic compound, belonging to the technical field of organic luminescent materials. The invention also relates to the application of the compound in an organic electroluminescent device and an organic electroluminescent device using the compound. Background Art

[0002] OLED (Organic Light-Emitting Diode) refers to an organic semiconductor that is made of an extremely thin organic material coating and a glass substrate and emits light when current passes through it. As a new generation of display technology, OLED has better display performance than LCD, with the advantages of self-luminescence, good display effect, low power consumption, high flexibility and ultra-thinness. It is widely used in the screens of smart phones, automotive electronics, smart wearable devices, VR devices and other products.

[0003] There are three main OLED light-emitting materials: blue, red, and green. Together, they determine the performance and lifespan of OLED self-luminescence. Among them, although blue light-emitting materials can emit brighter light, their luminous efficiency is lower and their lifespan is shorter than that of red and green light-emitting materials. Today, red and green OLED phosphorescent materials have been mass-produced and applied on OLED screens. However, blue OLED phosphorescent materials have always had defects in terms of color purity and service life, so blue fluorescent materials are still commonly used in commercial OLED products.

[0004] In 2016, Professor Takuji Hatakeyama of Japan proposed a TADF (Thermally Activated Delayed Fluorescence) material design strategy based on BN resonance (Adv. Mater. 2016, 28, 2777-2781). This type of material is composed of boron atoms, nitrogen atoms and multiple benzene rings, presenting a rigid polycyclic aromatic hydrocarbon structure with a high fluorescence quantum yield. In particular, compared with traditional blue fluorescent dyes, its spectrum is narrower and its color purity is higher, which has obvious advantages. However, due to its particularly planar rigid structure, it is easy to cause molecular accumulation and exciton annihilation, resulting in serious efficiency roll-off. Therefore, this type of organic electroluminescent material still has a lot of room for improvement in terms of luminescent performance, and the industry is in urgent need of developing new luminescent material systems to meet commercial needs. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides a polycyclic aromatic compound. In the structure of this series of compounds, a large steric hindrance group substituted with an ortho-aryl group is added to the ortho position of the benzene ring connected to the N atom. On the one hand, this structure is beneficial to inhibiting molecular stacking and exciton annihilation; on the other hand, the presence of the large steric hindrance group inhibits the vibration of the molecular excited state, significantly narrows the half-peak width of the material, improves the color purity of the blue light material, and is beneficial to improving the device efficiency.

[0006] Based on this purpose, the present invention adopts the following technical solutions:

[0007] In the first aspect, the present invention provides a novel organic compound based on a BN structure, the structure of which is shown in the general formula (1):

[0008]

[0009] In formula (1), Ring A, Ring B, Ring C, and Ring D are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring, an unsubstituted or R'-substituted C3-C60 heteroaromatic ring, and two adjacent R's are not connected or connected to form a ring by a chemical bond;

[0010] Z1, Z2, and Z3 are each independently selected from CR 1 or N, R 1 each independently selected from one of hydrogen, deuterium, halogen, unsubstituted or R"-substituted C1-C20 chain 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 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, wherein the two adjacent R 1 They are not connected or connected to form a ring through chemical bonds, and at least one of Z1 and Z3 is a structure represented by formula (a);

[0011] In formula (a), "—*" represents the connection site of ring E and Z1 or / and Z3, and the connection site is adjacent to the connection site of ring F on ring E;

[0012] In formula (a), Ring E and Ring F are each independently selected from an unsubstituted or R"' substituted C6-C60 aromatic ring, an unsubstituted or R"' substituted C3-C60 heteroaromatic ring, the two adjacent R"'s are not connected or connected by a chemical bond to form a ring; and Ring E and Ring F may be fused by a single bond, O, S, NR1 or CR2R3, and the R2 and R3 are not connected or connected to form a ring;

[0013] R1, R2, and R3 are each independently selected from hydrogen, deuterium, unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C6-C60 aryloxy, and unsubstituted or R"-substituted C3-C60 heteroaryl;

[0014] The R', R", and R'" are each independently selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0015] 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.

[0016] 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.

[0017] 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.

[0018] In the present specification, “each independently” means that when there are multiple subjects, they may be the same as or different from each other.

[0019] 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.

[0020] 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.

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

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

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] The C6 to C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0028] The C3~C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0029] The C2 to C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0030] In the present invention, the substituted or unsubstituted C6-C60 aryl group includes a monocyclic aryl group and a condensed aryl group, preferably a C6-C30 aryl group, and more preferably a C6-C20 aryl group. The so-called monocyclic aryl group 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 group includes 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group 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. A condensed aryl group 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.

[0031] 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. A 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. A 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.

[0032] 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.

[0033] 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.

[0034] In the present specification, the substituted or unsubstituted C1~C20 alkoxy group is preferably a substituted or unsubstituted C1~C10 alkoxy group. Examples of C1~C10 alkoxy groups 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 them, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0035] In the present specification, as the substituted or unsubstituted C1~C20 alkylsilyl group, as the substituted or unsubstituted C1~C10 alkylsilyl group, examples of the C1~C10 alkylsilyl group can be a silyl group substituted by the groups listed in the above-mentioned C1~C10 alkyl groups, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like groups.

[0036] 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.

[0037] 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.

[0038] Further, in formula (1), the ring A and the ring B have the structure shown in formula (b) or formula (c), the ring C and the ring D have the structure shown in formula (d), and "—*" represents the connection site:

[0039]

[0040] Among them, the dotted lines represent the fused bonds of the groups;

[0041] Y is selected from O, S, NR 2 or CR 3 R 4 ;

[0042] The R 2 , R 3 , R 4 are independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R 3 With R 4 Not connected or connected into rings by chemical bonds;

[0043] R 2 , R 3 , R 4 The substituents are each independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl;

[0044] U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 Each independently is CR5 or N, R 5 Each is independently selected from one or a combination of hydrogen, deuterium, halogen, cyano, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; two adjacent R 5 They are not connected to each other or are connected to form a ring through chemical bonds.

[0045] Furthermore, the compound of the present invention has a structure as shown in formula (2-1) or formula (2-2):

[0046]

[0047] In formula (2-1) and (2-2), Y, U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 The definition range is the same as that in formula (b), (c), and (d);

[0048] U 1’ , U 2’ , U 3’ , U 4’ The definition of U 1 , U 2 , U 3 , U 4 The definition scope is the same.

[0049] In the above formulas (2-1) and (2-2), it is preferred that Y is selected from O or S;

[0050] and / or, the U 1 , U 2 , U 3 and U 4 There is at most one N, the U 5 , U 6 , U 7 and U 8 At most one of them is N;

[0051] and / or, 9 , U10 , U 11 , U 12 , U 13 Each independently is CR 5 ;

[0052] More preferably, the U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of hydrogen, deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryloxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl; two adjacent R 5 are not connected or connected to form a ring through chemical bonds; More preferably, the U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of two of hydrogen, deuterium, fluorine, methyl, ethyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 2,2,5,5-tetramethylcyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, naphthyl, pyridyl, diphenylamino; most preferably, U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of two of hydrogen, methyl, tert-butyl, cyclopentyl, cyclohexyl, 2,2,5,5-tetramethylcyclohexyl, cyclooctyl, phenyl and naphthyl.

[0053] Furthermore, in formula (1), formula (2-1), and formula (2-2), one of Z1 and Z3 is a structure shown in formula (a), and the other of Z1 and Z3 is selected from CR 1 , while Z2 is selected from CR 1 , the R 1 One or a combination of two selected from hydrogen, deuterium, C1-C10 chain alkyl, C3-C10 cycloalkyl, and C6-C30 aryl;

[0054] Preferably, the above R 1is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, naphthyl or biphenyl; more preferably, the above R 1 is selected from hydrogen, methyl, ethyl, or tert-butyl.

[0055] Furthermore, in formula (1), formula (2-1), and formula (2-2), the formula (a) has a structure shown in formula (3-1) or formula (3-2):

[0056]

[0057] Wherein, X1, X2, X3, X4, X5, X6, X7, X8, and X9 are each independently selected from CR 6 or N, R 6 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of two of them, and two adjacent R 6 They are not connected or connected to form a loop;

[0058] Z is selected from a single bond, O, S or CR2R3, and R2 and R3 are each independently selected from hydrogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

[0059] Preferably, in formula (3-1), X4 and X5 are each independently selected from CR 6 , R 6 Each independently selected from C1 to C20 chain alkyl, and the two R 6 Not connected or connected in a loop.

[0060] Still more preferably, in formula (3-1) and formula (3-2), X6 and X8 are each independently selected from CR 6 , R 6 Each is independently selected from one or a combination of two of hydrogen, deuterium, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl;

[0061] Preferably, X6 and X8 are each independently selected from CR 6 , R 6Each is independently selected from tert-butyl, 2,2,5,5-tetramethylcyclohexyl, adamantyl or phenyl.

[0062] Preferably, in the above general formula, the ring C and the ring D are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring, and two adjacent R's are not connected or connected to form a ring through a chemical bond;

[0063] More preferably, the ring C and the ring D are each independently selected from an unsubstituted or R'-substituted benzene ring, and two adjacent R's are not connected or are connected to form a ring through a chemical bond; further preferably, the substituent R' on the ring C and the ring D is selected from one or a combination of two of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl;

[0064] More preferably, the substituent R' on the ring C and the ring D is selected from one or a combination of two of deuterium, methyl, ethyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 2,2,5,5-tetramethylcyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, biphenyl, dibenzofuran, and dibenzothiophene, and two adjacent R's are not connected or are connected to form a ring through a chemical bond.

[0065] More preferably, ring C or ring D has 1 or 2 substituent groups R', respectively.

[0066] As preferred structures of the compounds of the present invention, the following specific compounds M1-M306 can be cited, but are not limited to these compounds:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In a second aspect, the present invention provides a use of the polycyclic aromatic compound as described in the first aspect, wherein the polycyclic aromatic compound is applied to an organic electronic device.

[0089] Preferably, the organic electronic device includes 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 electronic paper, and an organic electroluminescent device is further preferred.

[0090] Preferably, the polycyclic aromatic compound is used as a light-emitting layer material in an organic electroluminescent device. More preferably, the polycyclic aromatic compound is used as a light-emitting dye of a light-emitting layer in an organic electroluminescent device.

[0091] In a third aspect, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and at least one organic layer arranged between the first electrode and the second electrode; the organic layer comprises at least one polycyclic aromatic compound as described in the first aspect, preferably comprises at least one polycyclic aromatic compound with a structure shown in M1-M306.

[0092] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one polycyclic aromatic compound as described in the first aspect, and further preferably includes at least one polycyclic aromatic compound with a structure shown as M1-M306.

[0093] Preferably, the light-emitting layer includes a host material and a dye, and the dye includes at least one polycyclic aromatic compound as described in the first aspect, and further preferably includes at least one polycyclic aromatic compound with a structure shown as M1-M306.

[0094] The polycyclic aromatic compound provided by the present invention has excellent luminescent properties. When used in an organic electroluminescent device, it can provide triplet excitons to achieve higher luminescent efficiency. At the same time, based on its excellent carrier transport efficiency, it is suitable for use as a dye of a luminescent layer.

[0095] Preferably, the polycyclic aromatic compound acts as a sensitizer of the light-emitting layer, and works together with the host material and the dye to achieve a good light-emitting effect.

[0096] Preferably, the organic layer further comprises any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, or a combination of at least two thereof.

[0097] In a preferred technical solution, an organic electroluminescent device (OLED device) includes a first electrode, a second electrode, and an organic layer between the electrodes. The organic layer can be divided into multiple regions, for example, a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one polycyclic aromatic compound as described in the first aspect, and further preferably contains at least one polycyclic aromatic compound having a structure shown in M1-M306.

[0098] In a preferred technical solution, the organic electroluminescent device includes a substrate, and a first electrode, a plurality of light-emitting functional layers (organic layers) and a second electrode sequentially arranged on the substrate; the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer sequentially arranged, and the hole injection layer is in contact with the first electrode. The organic layer (preferably the light-emitting layer) contains at least one polycyclic aromatic compound as described in the first aspect, and further preferably contains at least one polycyclic aromatic compound having a structure shown in M1-M306.

[0099] In a preferred technical solution, a substrate can be used below the first electrode or above the second electrode. The substrate is glass or polymer material with excellent mechanical strength, thermal stability, water resistance and transparency. In addition, a thin film transistor (TFT) can also be provided on the substrate used as a display.

[0100] 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.

[0101] The organic layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer can be an organic small molecule, an organic macromolecule or a polymer, and a combination thereof.

[0102] 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.

[0103] 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.

[0104]

[0105]

[0106]

[0107] 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.

[0108]

[0109] 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.

[0110] 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.

[0111] 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.

[0112]

[0113]

[0114] In one aspect of the present invention, the barrier layer around the light-emitting layer can be selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0115]

[0116]

[0117]

[0118]

[0119] 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.

[0120] 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).

[0121] 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.

[0122]

[0123]

[0124]

[0125]

[0126] 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.

[0127] 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, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0128] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0129] Compared with the prior art, the present invention has the following beneficial effects:

[0130] The polycyclic aromatic compound provided by the present invention has a specific molecular structure shown in formula (1). By designing the BN mother core structure and introducing the structure shown in formula (a) at least one of the adjacent positions of the N atom of the mother core, namely Z1 and Z3, the polycyclic aromatic compound has excellent photoelectric properties. On the one hand, it is beneficial to suppress the vibration of the molecular excited state, narrow the half-peak width of the material, and improve the color purity of the blue light material; on the other hand, the existence of this structure suppresses molecular stacking and exciton annihilation, which is beneficial to improve the efficiency of the device. The polycyclic aromatic compound has good stability and spatial configuration, can use triplet excitons to achieve higher luminous efficiency, has excellent carrier transport characteristics, and effectively avoids molecular aggregation, which has an improving effect on the stability and efficiency of the device. The preparation process of the polycyclic aromatic compound is simple and easy, the raw materials are easy to obtain, and it is suitable for mass production and amplification. It is used as a material for the light-emitting layer in an organic electroluminescent device, so that the device can achieve a high-quality blue light luminescence effect, and effectively prolong the life of the device and improve the luminous efficiency. DETAILED DESCRIPTION

[0131] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0132] The polycyclic aromatic compounds provided by the present invention can be obtained by known methods, for example, by known organic synthesis methods. An exemplary synthesis route is given below, but those skilled in the art can also obtain the polycyclic aromatic compounds by other known methods.

[0133] In a specific embodiment, the polycyclic aromatic compound can be prepared by the following synthetic route:

[0134]

[0135] Wherein, ring A, ring B, ring C, ring D, Z1, Z2, and Z3 have the same limited range as in formula (1); Hal 1 Hal 2 Hal 3 Each is independently a halogen, more preferably Cl or Br.

[0136] In one embodiment, the representative synthesis route of the polycyclic aromatic compound is as follows:

[0137]

[0138] Among them, U 1 , U 2 , U 3 , U 4 , U 5 , U6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 , U 1’ , U 2’ , U 3’ , U 4’ , Y has the same definition as above; Pd(dppf)Cl2 is 1,1'-bis(diphenylphosphinoferrocene)palladium dichloride, NaOtBu is sodium tert-butoxide, Pd2(dba)3 is tri(dibenzylideneacetone)dipalladium, P-tBu3 is tri-tert-butylphosphine, tBu-Li is tert-butyllithium, and NEt(i-Pr)2 is N,N-diisopropylethylamine.

[0139] It should be noted that obtaining the polycyclic aromatic compounds is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art may also select other methods or routes to obtain the polycyclic aromatic compounds proposed in the present invention. The compounds for which the synthesis method is not mentioned in the present invention are all raw materials obtained from commercial channels, or are prepared by these raw materials according to known methods.

[0140] The solvents and reagents used in the present invention can all be purchased from the chemical product market.

[0141] The specific preparation method of the polycyclic aromatic compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0142] The structural analysis of the intermediates and compounds in the present invention was performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0143] Synthesis Example 1: Synthesis of M5

[0144]

[0145] Synthesis of intermediate A1:

[0146] Intermediate A1 was prepared according to the above synthetic route and was a commercially customized raw material provided by Puyang Huicheng.

[0147] The molecular ion mass determined by mass spectrometry was: 488.02 (theoretical value: 488.07).

[0148] Synthesis of intermediate M5-1:

[0149] At room temperature, bis(4-tert-butylphenyl)amine (20.0 g), A1 (34.8 g), Pd2(dba)3 (3.3 g), tri-tert-butylphosphine (1.4 g), sodium tert-butoxide (13.7 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated, extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and subjected to column chromatography (PE:DCM=10:1, v:v) to obtain a crude product, which was slurried with ethanol to obtain 40.2 g of a white solid with a yield of 81.9%.

[0150] The molecular ion mass determined by mass spectrometry was: 689.34 (theoretical value: 689.36).

[0151] Synthesis of intermediate M5-2:

[0152] At room temperature, M5-1 (20.0 g), bis(4-tert-butylphenyl)amine (8.2 g), Pd2(dba)3 (1.3 g), tri-tert-butylphosphine (0.6 g), sodium tert-butoxide (5.6 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated, and column chromatography (PE:DCM=10:1, v:v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 23.2 g of a white solid with a yield of 85.6%.

[0153] The molecular ion mass determined by mass spectrometry was: 934.52 (theoretical value: 934.59).

[0154] Synthesis of compound M5:

[0155] At room temperature, M5-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and heated for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.6 g of yellow solid, with a yield of 18.5%.

[0156] The molecular ion mass determined by mass spectrometry was: 908.60 (theoretical value: 908.62).

[0157] Synthesis Example 2: Synthesis of M39

[0158]

[0159] Synthesis of intermediate B1:

[0160] Intermediate B1 was prepared according to the above synthetic route and was a commercially customized raw material provided by Puyang Huicheng.

[0161] The molecular ion mass determined by mass spectrometry was: 653.42 (theoretical value: 653.50).

[0162] Synthesis of intermediate M5-1:

[0163] At room temperature, bis(4-tert-butylphenyl)amine (20.0 g), A1 (34.8 g), Pd2(dba)3 (3.3 g), tri-tert-butylphosphine (1.4 g), sodium tert-butoxide (13.7 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated, extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and subjected to column chromatography (PE:DCM=10:1, v:v) to obtain a crude product, which was slurried with ethanol to obtain 40.2 g of a white solid with a yield of 81.9%.

[0164] The molecular ion mass determined by mass spectrometry was: 689.34 (theoretical value: 689.36).

[0165] Synthesis of intermediate M39-2:

[0166] At room temperature, M5-1 (20.0 g), B1 (18.9 g), Pd2 (dba) 3 (1.3 g), tri-tert-butyl phosphine (0.6 g), sodium tert-butoxide (5.6 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 32.4 g of a white solid with a yield of 85.5%.

[0167] The molecular ion mass determined by mass spectrometry was: 1307.82 (theoretical value: 1307.88).

[0168] Synthesis of compound M39:

[0169] At room temperature, M39-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and continued to heat for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.2 g of yellow solid, with a yield of 16.4%.

[0170] The molecular ion mass determined by mass spectrometry was: 1280.82 (theoretical value: 1280.90).

[0171] Synthesis Example 3: Synthesis of M68

[0172]

[0173] Synthesis of intermediate M68-1:

[0174] At room temperature, M68-0 (20.0 g), A1 (7.4 g), Pd2 (dba) 3 (2.6 g), tri-tert-butyl phosphine (1.1 g), sodium tert-butoxide (10.8 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 35.7 g of a white solid with a yield of 83.2%.

[0175] The molecular ion mass determined by mass spectrometry was: 765.34 (theoretical value: 765.39).

[0176] Synthesis of intermediate M68-2:

[0177] At room temperature, M68-1 (20.0 g), B2 (12.8 g), Pd2 (dba) 3 (1.2 g), tri-tert-butyl phosphine (0.5 g), sodium tert-butoxide (5.0 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and subjected to column chromatography (PE: DCM = 10: 1, v: v) to obtain a crude product, and ethanol was added to slurry to obtain 24.2 g of a white solid with a yield of 87.1%.

[0178] The molecular ion mass determined by mass spectrometry was: 1066.52 (theoretical value: 1066.60).

[0179] Synthesis of compound M68:

[0180] At room temperature, M68-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and heated for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.6 g of yellow solid, with a yield of 18.4%.

[0181] The molecular ion mass determined by mass spectrometry was: 1040.60 (theoretical value: 1040.62).

[0182] Synthesis Example 4: Synthesis of M128

[0183]

[0184] Synthesis of intermediate M128-1:

[0185] At room temperature, B2 (20.0 g), A1 (29.1 g), Pd2 (dba) 3 (2.7 g), tri-tert-butyl phosphine (1.2 g), sodium tert-butoxide (11.4 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and subjected to column chromatography (PE: DCM = 10: 1, v: v) to obtain a crude product, and ethanol was added to slurry to obtain 35.7 g of a white solid with a yield of 80.7%.

[0186] The molecular ion mass determined by mass spectrometry was: 745.34 (theoretical value: 745.33).

[0187] Synthesis of intermediate M128-2:

[0188] At room temperature, M128-1 (20.0 g), B1 (17.5 g), Pd2 (dba) 3 (1.2 g), tri-tert-butyl phosphine (0.5 g), sodium tert-butoxide (5.2 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 30.4 g of a white solid with a yield of 83.2%.

[0189] The molecular ion mass determined by mass spectrometry was: 1363.79 (theoretical value: 1363.85).

[0190] Synthesis of compound M128:

[0191] At room temperature, M128-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and heated for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.9 g of yellow solid, with a yield of 19.9%.

[0192] The molecular ion mass determined by mass spectrometry was: 1336.82 (theoretical value: 1336.87).

[0193] Synthesis Example 5: Synthesis of M155

[0194]

[0195] Synthesis of intermediate A2:

[0196] Intermediate A2 was prepared according to the above synthetic route and was a commercially customized raw material provided by Puyang Huicheng.

[0197] The molecular ion mass determined by mass spectrometry was: 576.03 (theoretical value: 576.06).

[0198] Synthesis of intermediate M155-1:

[0199] At room temperature, bis(4-tert-butylphenyl)amine (20.0 g), A2 (35.7 g), Pd2(dba)3 (3.3 g), tri-tert-butylphosphine (1.4 g), sodium tert-butoxide (13.7 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100°C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated, extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and subjected to column chromatography (PE:DCM=10:1, v:v) to obtain a crude product, which was slurried with ethanol to obtain 42.5 g of a white solid with a yield of 85.1%.

[0200] The molecular ion mass determined by mass spectrometry was: 701.25 (theoretical value: 701.32).

[0201] Synthesis of intermediate M155-2:

[0202] At room temperature, M155-1 (20.0 g), B3 (9.2 g), Pd2 (dba) 3 (1.3 g), tri-tert-butyl phosphine (0.6 g), sodium tert-butoxide (5.5 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 24.2 g of a white solid with a yield of 86.1%.

[0203] The molecular ion mass determined by mass spectrometry was: 986.51 (theoretical value: 986.55).

[0204] Synthesis of compound M155:

[0205] At room temperature, M155-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and continued to heat for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.5 g of yellow solid, with a yield of 18.0%.

[0206] The molecular ion mass determined by mass spectrometry was: 960.54 (theoretical value: 960.58).

[0207] Synthesis Example 6: Synthesis of M174

[0208]

[0209] Synthesis of intermediate B4:

[0210] Intermediate B4 was prepared according to the above synthetic route and was a commercially customized raw material provided by Puyang Huicheng.

[0211] The molecular ion mass determined by mass spectrometry was: 545.39 (theoretical value: 545.40).

[0212] Synthesis of intermediate M174-1:

[0213] At room temperature, B3 (20.0 g), A1 (30.5 g), Pd2 (dba) 3 (2.9 g), tri-tert-butyl phosphine (1.3 g), sodium tert-butoxide (12.0 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 40.1 g of a white solid with a yield of 88.2%.

[0214] The molecular ion mass determined by mass spectrometry was: 729.28 (theoretical value: 729.35).

[0215] Synthesis of intermediate M174-2:

[0216] At room temperature, M174-1 (20.0 g), B4 (14.9 g), Pd2 (dba) 3 (1.3 g), tri-tert-butyl phosphine (0.6 g), sodium tert-butoxide (5.3 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 28.4 g of a white solid with a yield of 83.7%.

[0217] The molecular ion mass determined by mass spectrometry is: 1238.72 (theoretical value: 1238.78).

[0218] Synthesis of compound M174:

[0219] At room temperature, M174-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and heated for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.7 g of yellow solid, with a yield of 18.9%.

[0220] The molecular ion mass determined by mass spectrometry was: 1212.73 (theoretical value: 1212.80).

[0221] Synthesis Example 7: Synthesis of M243

[0222]

[0223] Synthesis of intermediate B5:

[0224] Intermediate B5 was prepared according to the above synthetic route and was a commercially customized raw material provided by Puyang Huicheng.

[0225] The molecular ion mass determined by mass spectrometry was: 526.31 (theoretical value: 526.33).

[0226] Synthesis of intermediate A3:

[0227] Intermediate A3 was prepared according to the above synthetic route, and was a commercially customized raw material provided by Puyang Huicheng.

[0228] Molecular ion mass determined by mass spectrometry: 486.02 (theoretical value: 486.05)

[0229] Synthesis of intermediate M243-1:

[0230] At room temperature, M243-0 (20.0 g), A3 (34.7 g), Pd2 (dba) 3 (3.3 g), tri-tert-butyl phosphine (1.4 g), sodium tert-butoxide (13.7 g), and toluene (500 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 40.2 g of a white solid with a yield of 82.1%.

[0231] The molecular ion mass determined by mass spectrometry was: 687.32 (theoretical value: 687.34).

[0232] Synthesis of intermediate M243-2:

[0233] At room temperature, M243-1 (20.0 g), B5 (15.3 g), Pd2 (dba) 3 (1.3 g), tri-tert-butyl phosphine (0.6 g), sodium tert-butoxide (5.6 g), and toluene (400 mL) were added to a 1L single-mouth bottle, replaced with nitrogen three times, and heated to 100 ° C for overnight reaction. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, and the organic phase was dried and concentrated and column chromatography (PE: DCM = 10: 1, v: v) was performed to obtain a crude product, and ethanol was added to slurry to obtain 29.4 g of a white solid with a yield of 85.9%.

[0234] The molecular ion mass determined by mass spectrometry was: 1177.68 (theoretical value: 1177.70).

[0235] Synthesis of compound M243:

[0236] At room temperature, M243-2 (20.0 g) was dissolved in 120 mL of xylene. After nitrogen replacement three times, the reaction system was cooled to -20 ° C, and then tert-butyl lithium (30 mL, 1.6 M) was added, and stirring was continued at low temperature for 30 minutes. Then the temperature was gradually raised to 60 ° C and heated for 2 hours. Finally, the temperature of the reaction system was lowered to -20 ° C again, and boron tribromide (7 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (24 mL) was added. Finally, the reaction system was heated to 120 ° C and reacted for 8 hours. After the reaction was cooled to room temperature, the organic phase was decompressed and dried. Dichloromethane (200 mL) was extracted three times, the organic phases were combined, dried over anhydrous sodium sulfate, the organic phase was mixed with silica gel and concentrated, and the crude product was obtained by column chromatography (PE: DCM = 20: 1, v: v), and then recrystallized to obtain 3.2 g of yellow solid, with a yield of 16.4%.

[0237] The molecular ion mass determined by mass spectrometry was: 1151.68 (theoretical value: 1151.72).

[0238] Theoretical calculation:

[0239] The calculations described in the present invention were completed using the Gaussian16 program.

[0240] Optimize the ground state structure of the molecule at the B3LYP / 6-31G* calculation level.

[0241] The energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the molecule in the ground state were calculated using the B3LYP / 6-31G* method, and the UV-visible absorption spectrum of the molecule was obtained using the B3LYP / 6-31G* method in the SMD solvent model (toluene).

[0242] The structure of the lowest singlet excited state of the molecule was optimized using the B3LYP / 6-31G* method. The energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the molecule in the excited state were calculated using the B3LYP / 6-31G* method. The maximum fluorescence emission wavelength of the molecule was obtained using the B3LYP / 6-31G* method in the SMD solvent model (toluene). See Table 1 for details.

[0243] Table 1:

[0244] Compound HOMO / eV LUMO / eV <![CDATA[S1 / eV]]> <![CDATA[T1 / eV]]> λ / nm <![CDATA[ΔE ST / eV]]> M5 -4.54 -1.37 2.68 2.19 463 0.49 M68 -4.56 -1.38 2.67 2.20 464 0.47 D1 -4.56 -1.29 2.56 2.12 484 0.44 D2 -5.85 -3.14 2.33 1.81 532 0.52 D3 -4.55 -1.37 2.67 2.18 464 0.49

[0245]

[0246] As can be seen from Table 1 above, among the compounds prepared and applied in the present invention, the emission wavelengths of the compounds M5 and M68 of the present invention are located in the blue light region, while the comparative compounds D1 and D2 are obviously red-shifted, and D2 has even reached the green light region, and can only be used as a green light dye. The T1 energy levels of the four compounds are similar and relatively low, which can effectively prevent triplet quenching. In addition, the rigid large steric hindrance groups are introduced in the embodiments M5 and M68, which increase the molecular rigidity and inhibit the molecular stacking, and can further improve the life of the related devices.

[0247] Device Example 1

[0248] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode (Al) arranged in sequence. The preparation method of the organic electroluminescent device is as follows:

[0249] (1) a glass substrate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent, 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] (2) Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, vacuum evaporating a mixture of compound HT-4:HI-3 (97 / 3, w / w) on the above anode layer as a hole injection layer, the evaporation rate is 0.1 nm / s, and the evaporation film thickness is 10 nm;

[0251] (3) vacuum evaporating compound HT-4 on the hole injection layer as a hole transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 60 nm;

[0252] (4) vacuum evaporating compound HT-14 on the hole transport layer as an electron blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0253] (5) vacuum evaporating a light-emitting layer on the electron blocking layer, wherein the light-emitting layer includes a binary mixture of a main material BFH-4 and a dye (the polycyclic aromatic compound M5 provided by the present invention), BFH-4:M5 (100:3, w / w), with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 20 nm;

[0254] (6) vacuum evaporating compound ET-23 on the light-emitting layer as a hole blocking layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 5 nm;

[0255] (7) vacuum evaporating a mixture of compounds ET-69:ET-57 (50 / 50, w / w) on the hole blocking layer as an electron transport layer, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0256] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer at a rate of 0.1 nm / s and a thickness of 1 nm;

[0257] (9) Vacuum-evaporating an Al layer with a thickness of 150 nm on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0258] Device Examples 2-12, Device Comparative Example 1

[0259] An organic electroluminescent device, which differs from device embodiment 1 only in that the dyes of the light-emitting layer are the compounds shown in Table 2; other layers, thicknesses, materials and preparation methods are the same as those of device embodiment 1.

[0260] In device comparative example 1, the following prior art compound D3 is used as the dye of the light-emitting layer, and the specific structural formula is as follows:

[0261]

[0262] Device performance test:

[0263] (1) Luminescence peak and half-peak width: at 10 mA / cm 2 Tested under current density;

[0264] (2) LT97 life: Use a brightness meter at 40mA / cm2 The initial brightness value of the device under the current density is measured by maintaining a constant current and measuring the time for the device brightness to drop to 97% of the initial brightness, in hours; the LT97 life test value of the device comparative example 1 is recorded as 1.0, and the ratio of the LT97 life test value of other devices to the LT97 life test value of the device comparative example 1 is calculated;

[0265] (3) External quantum efficiency: The external quantum efficiency (EQE, %) of the device was measured using the integrating sphere method.

[0266] The test results are shown in Table 2.

[0267] Table 2:

[0268]

[0269]

[0270] Combined with the data in Table 2, it can be seen that the polycyclic aromatic compounds provided by the present invention, as dyes for the light-emitting layer of an organic electroluminescent device, can significantly extend the life of the device, significantly improve the luminous efficiency, and the device has more excellent stability and efficiency.

[0271] Compared with compound D3, the compounds of the present invention choose to replace the more rigid aromatic and heteroaromatic steric groups at the ortho position of the N atom. This scheme enhances the rigidity of the molecule and can inhibit the vibration of the molecular excited state and the annihilation of excitons, thereby having higher color purity, efficiency and longer life.

[0272] In summary, the present invention uses a special design of the molecular structure to make the polycyclic aromatic compound as the dye of the light-emitting layer, which can significantly prolong the device life, improve the device luminescence efficiency, and optimize the device luminescence performance.

[0273] 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. A polycyclic aromatic compound having a structure as shown in formula (1): In formula (1), Ring A, Ring B, Ring C, and Ring D are each independently selected from an unsubstituted or R'-substituted C6-C60 aromatic ring, an unsubstituted or R'-substituted C3-C60 heteroaromatic ring, and two adjacent R's are not connected or connected to form a ring by a chemical bond; Z1, Z2, and Z3 are each independently selected from CR 1 or N, R 1 each independently selected from one of hydrogen, deuterium, halogen, unsubstituted or R"-substituted C1-C20 chain 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 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, wherein the two adjacent R 1 They are not connected or connected to form a ring through chemical bonds, and at least one of Z1 and Z3 is a structure represented by formula (a); In formula (a), "—*" represents the connection site between ring E and Z1 or / and Z3, and the connection site is adjacent to the connection site of ring F on ring E; In formula (a), Ring E and Ring F are each independently selected from an unsubstituted or R"' substituted C6-C60 aromatic ring, an unsubstituted or R"' substituted C3-C60 heteroaromatic ring, the two adjacent R"'s are not connected or connected by a chemical bond to form a ring; and Ring E and Ring F may be fused by a single bond, O, S, NR1 or CR2R3, and the R2 and R3 are not connected or connected to form a ring; R1, R2, and R3 are each independently selected from one of hydrogen, deuterium, unsubstituted or R"-substituted C1-C20 chain alkyl, unsubstituted or R"-substituted C3-C20 cycloalkyl, unsubstituted or R"-substituted C6-C30 arylamino, unsubstituted or R"-substituted C6-C60 aryl, unsubstituted or R"-substituted C6-C60 aryloxy, and unsubstituted or R"-substituted C3-C60 heteroaryl; The R', R", and R'" are each independently selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The polycyclic aromatic compound according to claim 1, characterized in that The ring A and the ring B have a structure as shown in formula (b) or formula (c), and the ring C and the ring D have a structure as shown in formula (d), and "—*" represents a connection site: Among them, the dotted lines represent the fused bonds of the groups; Y is selected from O, S, NR 2 or CR 3 R 4 ; The R 2 , R 3 , R 4 are independently selected from one of hydrogen, deuterium, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R 3 With R 4 Not connected or connected into rings by chemical bonds; R 2 , R 3 , R 4 The substituents are each independently selected from one or a combination of two of deuterium, halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 Each independently is CR 5 or N, R 5 Each is independently selected from one or a combination of hydrogen, deuterium, halogen, cyano, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; two adjacent R 5 They are not connected or connected to form a ring through chemical bonds.

3. The polycyclic aromatic compound according to claim 2, characterized in that Having a structure as shown in formula (2-1) or formula (2-2): In formula (2-1) and (2-2), Y, U 1 , U 2 , U 3 , U 4 , U 5 , U 6 , U 7 , U 8 , U 9 , U 10 , U 11 , U 12 , U 13 The definition range is the same as that in formula (b), (c), and (d); U 1’ , U 2’ , U 3’ , U 4’ The definition of U 1 , U 2 , U 3 , U 4 The definition scope is the same.

4. The polycyclic aromatic compound according to claim 2, characterized in that Said Y is selected from O or S; and / or, the U 1 , U 2 , U 3 and U 4 There is at most one N, the U 5 , U 6 , U 7 and U 8 At most one of them is N; and / or, 9 , U 10 , U 11 , U 12 , U 13 Each independently is CR 5 ; Preferably, the U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of hydrogen, deuterium, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryloxy, C6-C60 arylamino, C6-C60 aryl, C3-C60 heteroaryl; two adjacent R 5 They are not connected to each other or connected to form a ring through chemical bonds; More preferably, the U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of two of hydrogen, deuterium, fluorine, methyl, ethyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 2,2,5,5-tetramethylcyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, naphthyl, pyridyl, and diphenylamino; Most preferably, the U 2 , U 3 , U 6 , U 7 Each independently is CR 5 , R 5 Each is independently selected from one or a combination of two of hydrogen, methyl, tert-butyl, cyclopentyl, cyclohexyl, 2,2,5,5-tetramethylcyclohexyl, cyclooctyl, phenyl and naphthyl.

5. The polycyclic aromatic compound according to claim 1 or 3, characterized in that: One of Z1 and Z3 is a structure shown in formula (a), and the other of Z1 and Z3 is selected from CR 1 , while Z2 is selected from CR 1 , the R 1 One or a combination of two selected from hydrogen, deuterium, C1-C10 chain alkyl, C3-C10 cycloalkyl, and C6-C30 aryl; Preferably, the above R 1 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, naphthyl or biphenyl; More preferably, the above R 1 is selected from hydrogen, methyl, ethyl, or tert-butyl.

6. The polycyclic aromatic compound according to claim 1 or 5, characterized in that The formula (a) has a structure shown in formula (3-1) or formula (3-2): Wherein, X1, X2, X3, X4, X5, X6, X7, X8, and X9 are each independently selected from CR 6 or N, R 6 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 linear alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylamino, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl, or a combination of two of them, and two adjacent R 6 They are not connected or connected to form a loop; Z is selected from a single bond, O, S or CR2R3, and R2 and R3 are each independently selected from hydrogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl.

7. The polycyclic aromatic compound according to claim 6, characterized in that in, In formula (3-1) and formula (3-2), X6 and X8 are each independently selected from CR 6 , R 6 Each is independently selected from one or a combination of two of hydrogen, deuterium, C1-C20 chain alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C6-C60 aryl, and C3-C60 heteroaryl; Preferably, X6 and X8 are each independently selected from CR 6 , R 6 Each is independently selected from tert-butyl, 2,2,5,5-tetramethylcyclohexyl, adamantyl or phenyl.

8. The polycyclic aromatic compound according to claim 1, characterized in that The ring C and ring D are each independently selected from unsubstituted or R'-substituted C6-C60 aromatic rings, and two adjacent R's are not connected or connected to form a ring through a chemical bond; Preferably, the ring C and the ring D are each independently selected from an unsubstituted or R'-substituted benzene ring, and two adjacent R's are not connected or connected to form a ring through a chemical bond; More preferably, the substituent R' on the ring C and the ring D is selected from one or a combination of two of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, the substituent R' on the ring C and the ring D is selected from one or a combination of two of deuterium, methyl, ethyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 2,2,5,5-tetramethylcyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, phenyl, biphenyl, dibenzofuran, and dibenzothiophene, and two adjacent R's are not connected or are connected to form a ring through a chemical bond.

9. The polycyclic aromatic compound according to claim 1, having the structure shown below:

10. Use of the organic compound according to any one of claims 1 to 9, 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; The organic compound is used as a light-emitting layer material in an organic electroluminescent device, preferably as a light-emitting dye in the light-emitting layer.

11. 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 9; 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 9; 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, and 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 9.

12. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 11.

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