Organic compound for luminescent device, application of organic compound and organic electroluminescent device

Abstract

The invention provides a polycyclic fused organic compound which is characterized in that the polycyclic fused organic compound has a structure represented by formula (1): # imgabs0 # Ar1 and Ar2 are aromatic groups respectively, and L1 and L2 are connecting bonds. The compound provided by the invention has excellent photoelectric efficiency as a functional material of an OLED device. The invention also provides an organic electroluminescent device and a display device.

Description

Technical Field

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

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and become a hot topic in the field. 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 OLED do not require additional backlight sources and have the advantages of bright colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a multi-layer 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] Common fluorescent emitters mainly emit light using singlet excitons generated when electrons and holes combine, 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 emitters. Their energy conversion efficiency can be increased by up to four times compared to traditional fluorescent emitters. 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 the emitter through energy transfer, which can also achieve higher luminescence efficiency.

[0005] Although products using OLED display technology have been commercialized, the device's lifespan, efficiency and other performance still need to be continuously improved to meet people's pursuit of higher quality. Therefore, the field is in urgent need of developing more types of organic materials for use in organic electroluminescent devices, so that the devices have higher luminous efficiency, lower driving voltage and longer service life. Summary of the invention

[0006] In view of the shortcomings of the prior art, one of the purposes of the present invention is to provide a polycyclic fused derivative with a naphthyl core fused to other heterocyclic structures, which has good photoelectric properties when applied to OLED devices. Specifically, the present invention provides a polycyclic fused organic compound, characterized in that it has a structure shown in formula (1):

[0007]

[0008] In formula (1), R 1 , R 2 , R 3 represents any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or substituted C1-C20 straight or branched alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C1-C20 alkoxy, unsubstituted or substituted C1-C20 alkylsilyl, unsubstituted or substituted C6-C60 arylamino, unsubstituted or substituted C3-C60 heteroarylamino, unsubstituted or substituted C6-C30 aryloxy, unsubstituted or substituted C3-C30 heteroaryloxy, unsubstituted or substituted C6-C60 aryl or C3-C60 heteroaryl;

[0009] a, b, c are each independently an integer from 0 to 4; when a is greater than 1, each R 1 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; when b is greater than 1, each R 2 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; when c is greater than 1, each R 3 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; R 1 , R 2 , R 3 Each is independently and optionally connected or unconnected to an adjacent group;

[0010] X and Z are each independently a single bond, O, S, or NR 4 , CR 5 R 6 ; Y is O or S; R 4 ~R 6 Each is independently selected from a substituted or unsubstituted C1-C20 straight or branched alkyl group, a C2-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; R 5 and R 6 optionally connected to form a ring,

[0011] Ar 1 and Ar 2Each independently represents one of hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 condensed ring aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 condensed ring heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino;

[0012] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 fused ring aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C3-C60 fused ring heteroaryl group;

[0013] The substitution in the above “substituted or unsubstituted” refers to substitution by at least one selected from halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, 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.

[0014] The expression of a ring structure crossed by “—” indicates that the connection site is at any position on the ring structure that can form a bond.

[0015] The compound of the present invention is fused with a phenyl five-membered nitrogen-containing heterocyclic ring and a benzo polycyclic heterocyclic ring at the 1, 2 and 7, 8 positions of the naphthyl group, respectively, to form a large conjugated nitrogen-containing and other heteroatom-containing mother core structure, which has a large planar structure and is conducive to the accumulation of molecules and the transmission of carriers. The preparation and application of the compound of the present invention to an organic electroluminescent device can reduce the voltage. At the same time, the compound contains nitrogen and other atoms with lone pairs of electrons such as O and S, so that the mother core structure has a higher proportion of n-π* transition in the singlet excited state, and the triplet excited state has a higher π-π* transition under the influence of the naphthyl group, so that the gap crossing rate from the singlet state to the triplet state is higher, so that more triplet excitons can be obtained. The preparation and application of the compound to the organic electroluminescent device can achieve high efficiency.

[0016] It should be noted that, unless otherwise defined below, the meanings of all technical terms and scientific terms used herein are intended to be the same as those generally understood by those skilled in the art. Reference to the technology used herein is intended to refer to the technology generally understood in the art, including those changes in technology or replacement of equivalent technology that are obvious to those skilled in the art. Although it is believed that the following terms are well understood by those skilled in the art, the following definitions are still set forth to better explain the present invention.

[0017] In this 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. When describing C1 to 30, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.

[0018] The terms "comprises," "comprising," "having," "containing," or "involving" and other variations thereof herein are inclusive or open-ended and do not exclude additional unrecited elements or method steps.

[0019] In the present invention, the expression of chemical elements, unless otherwise specified, generally includes the concept of isotopes with the same chemical properties. For example, the expression "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes 12 C. 13 C, etc., no further details.

[0020] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0021] As used herein, the terms "heterocyclyl", "heteroaryl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and / or triple bonds within the ring) cyclic group having at least one ring atom which is a heteroatom selected from N, O and S and the remaining ring atoms being C.

[0022] As used herein, the terms "(ylidene)aryl" and "aromatic ring" refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated π electron system. As used herein, the terms "(ylidene)heteroaryl" and "heteroaromatic ring" refer to a monocyclic, bicyclic or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably refers to an alkyl substituted with an aryl or heteroaryl group, wherein the aryl, heteroaryl and alkyl groups are as defined herein.

[0023] As used herein, the term "halo" or "halogen" group is defined to include F, Cl, Br, or I.

[0024] The term "substituted" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced by a selection from the indicated group, provided that the normal valence of the designated atom in the present context is not exceeded and the substitution forms a stable compound. Combinations of substituents and / or variables are permitted only if such combinations form stable compounds.

[0025] If substituents are described as being "independently selected" from a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.

[0026] As used herein, the term "one or more" means 1 or more than 1, such as 2, 3, 4, 5 or 10, where reasonable.

[0027] Unless otherwise indicated, as used herein, the point of attachment of a substituent may be from any suitable position of the substituent.

[0028] When a bond to a substituent is shown to pass through a bond connecting two atoms in a ring, then such substituent may be bonded to any ring atom in the substitutable ring.

[0029] The term "about" means within ±10% of the stated numerical value, preferably within ±5%, more preferably within ±2%.

[0030] In the structural formula disclosed in this specification, the expression of “—” crossing over a ring structure indicates that the connection site is at any position on the ring structure that can form a bond.

[0031] The above-mentioned C6-C60 aromatic ring and C3-C60 heteroaromatic ring in the present invention, unless otherwise specified, are aromatic groups satisfying the π conjugated system, including both monocyclic residues and condensed ring residues. The so-called monocyclic residue 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.; a fused ring residue refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but are fused to each other by sharing the ring edge, such as naphthyl, anthracenyl, phenanthryl, etc.; a monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; a fused heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or composed of at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0032] In the present specification, the substituted or unsubstituted C6-C60 aromatic ring is preferably a C6-C30 aromatic ring, and more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 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; 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 tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aromatic ring in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 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; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl.

[0033] In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 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; 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 tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 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; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[0034] In the present specification, the substituted or unsubstituted C3-C60 heteroaromatic ring is preferably a C3-C30 heteroaromatic ring, which can be a nitrogen-containing heteroaromatic group, an oxygen-containing heteroaromatic group, a sulfur-containing heteroaromatic group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridinyl , benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1, 1,2,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaromatic rings in the present invention include heteroaromatic rings of furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole.

[0035] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridine yl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidazinyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or / and fusion.

[0036] In the present invention, the aryl ether group and heteroaryl ether group include groups formed by the above-mentioned aryl group and heteroaryl group and oxygen. In the present invention, the aryl amino group and heteroaryl amino group include groups formed by replacing one or two H in the -NH2 group with the above-mentioned aryl group and heteroaryl group.

[0037] In this specification, the chain alkyl group includes both straight-chain and branched alkyl groups. Examples of the C1-C20 alkyl group include 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, trifluoromethyl, pentafluoroethyl, and 2,2,2-trifluoroethyl.

[0038] In the present specification, the C3-C20 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like.

[0039] The number of carbon atoms of the C2-C20 straight-chain or cyclic alkenyl group is preferably 2 to 10. Specific examples include vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0040] The number of carbon atoms in the C2-C20 straight-chain or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which these groups have substituents such as alkyl and alkoxy groups.

[0041] In the present specification, an alkoxy group refers to a group consisting of the above-mentioned chain alkyl group and oxygen, or a group consisting of the above-mentioned cycloalkyl group and oxygen.

[0042] Examples of C1-C20 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 which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy and isopentyloxy are preferred, and methoxy is more preferred.

[0043] In the present specification, examples of C1-C20 silyl groups include silyl groups substituted with the groups listed above for the C1-C20 alkyl groups, i.e., groups formed by replacing one, two or three hydrogen atoms on the silyl group with the above-mentioned chain alkyl or cycloalkyl groups. Specifically, groups include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0044] In addition, substitution at different sites of the mother core structure of the present invention is helpful to adjust the dipole moment of the molecule and the HOMO energy level and LUMO energy level of the compound of the present invention, thereby improving the electron injection and transmission capabilities of the compound, and using it in combination with materials of different functional layers to achieve carrier balance, adjust the position and width of the exciton recombination area, and at the same time, the molecular weight of the compound of the present invention is at a reasonable value, which can not only improve the Tg of the material, but also will not cause the evaporation temperature of the compound of the present invention to be too high, thereby affecting the thermal stability of the material, and can be applied to organic electroluminescent devices to achieve a long life. More specifically, as a preferred embodiment of the present invention, the compound represented by formula (1) has a structure represented by formula (2),

[0045]

[0046] In the above formula, X, Y, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 1 ,Ar 2 The definitions of a, b, and c are the same as those in formula (1).

[0047] As a further preferred embodiment of the present invention, the compound represented by formula (1) has a structure represented by formula (3),

[0048]

[0049] In the above formula, X, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 1 ,Ar 2 The definitions of a, b, and c are the same as those in formula (1).

[0050] As a preferred embodiment of the present invention, L 1 , L 2 Each is independently selected from a substituted or unsubstituted C6-C12 arylene group, a substituted or unsubstituted C3-C12 heteroarylene group, and the above-mentioned substituents are independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group;

[0051] Preferably, L 1 , L 2 Each is independently selected from a single bond or one or a combination of at least two of the following groups:

[0052]

[0053]

[0054] Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ;

[0055] R 11 , R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl;

[0056] More preferably, L 1 , L 2 Each is independently selected from a single bond or one of the following groups:

[0057]

[0058] The expression of “—” crossing over the ring structure indicates that the connection site is any position on the ring structure that can form a bond. A wavy line or an asterisk indicates the connection site. The substitution in the above “substituted or unsubstituted” refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexanyl, cyclopentanyl, and fluorenyl.

[0059] As a preferred embodiment of the present invention, Ar 1 and Ar 2 Each is independently selected from hydrogen or a substituted or unsubstituted one of the following groups:

[0060]

[0061]

[0062]

[0063] Among them, Ar d It is any one of substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and the substitution in the above "substituted or unsubstituted" means replacement by at least one selected from halogen, phenyl, cyano, methyl, cyclohexanyl, cyclopentanyl, and fluorenyl. The wavy line indicates the connection site.

[0064] As a preferred embodiment of the present invention, Ar 1 and Ar2 Each is independently selected from hydrogen or one of the following groups:

[0065]

[0066]

[0067] Among them, Ar d is a group selected from the following groups:

[0068]

[0069]

[0070] Wavy lines indicate junction sites.

[0071] As a preferred embodiment of the present invention, R 1 , R 2 , R 3 Each is independently selected from H, phenyl, and cyano; a, b, and c are all 0 or 1.

[0072] Furthermore, the general formula compound of the present invention is preferably the following specific compound, but the present invention is not limited to the specific compounds shown below:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] As another aspect of the present invention, there is also provided an application of the compound as described above in an organic electroluminescent device, specifically, preferably, the compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably, the compound is used in a red organic electroluminescent device.

[0092] More preferably, the compound of the present invention is used as a host material of the organic electroluminescent device, preferably as a red light host material.

[0093] In addition to organic electroluminescent devices, the compound of the present invention can be applied to 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 papers.

[0094] As another aspect of the present invention, an organic electroluminescent device is provided, comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, wherein the organic layer contains a compound represented by Formula 1 as described above, or contains a compound having a structure represented by at least one of A1 to A473 as described above.

[0095] Specifically, one embodiment of the present invention provides an organic electroluminescent device, including a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode sequentially formed on the substrate; the light-emitting functional layers include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is between the hole transport layer and the electron transport layer; wherein the light-emitting layer includes a main material and a doping material, the main material includes at least one compound represented by Formula 1 as described above, or a compound having a structure represented by at least one of A1 to A473 as described above.

[0096] In the organic electroluminescent device of the present invention, the technical solution of multiple luminescent host materials and / or multiple luminescent dyes can also be adopted in the luminescent layer. When multiple luminescent hosts are used, the luminescent host material may include a first compound and a second compound, and the first compound adopts at least one compound as shown in Formula 1 of the present invention, or a compound with a structure shown in at least one of A1 to A473 as described above. The second compound can be selected to match the energy level relationship, carrier transport performance, etc. of the first compound. Among them, the second compound may include a combination of one or more of the following PH-1 to PH-85, but is not limited to a combination of one or more of PH-1 to PH-85.

[0097] 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.

[0098] 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. DETAILED DESCRIPTION

[0099] The technical solution of the present invention is further described in more detail below. It should be understood by those skilled in the art that the specific implementation methods and examples are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0100] The process of obtaining the compound of the present invention is as follows:

[0101] The compound represented by formula (I) of 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 it by other known methods. A representative synthesis route of the compound represented by the general formula of the present invention is as follows:

[0102]

[0103] Description of organic EL elements

[0104] The OLED device structure of the present invention can be an existing device structure, generally speaking, including a first electrode and a second electrode, and an organic material layer located 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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).

[0109] 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 compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0110]

[0111]

[0112]

[0113] 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.

[0114]

[0115] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include 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.

[0116] 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.

[0117] Specifically, the host material in the light-emitting layer may include a single host compound or two host compounds, and the light-emitting dye in the light-emitting layer may include one type of dye compound or two types of dye compounds. When two host compounds are included, the energy level relationship and carrier transport performance of the two compounds can be matched, designed and selected according to requirements. When two types of dye compounds are included, the light-emitting wavelengths of the two compounds and the energy level relationship with the host material can be matched, designed and selected according to requirements.

[0118] In one aspect of the present invention, the host material of the light-emitting layer adopts the organic compound of the present invention.

[0119] Specifically, in the present invention, the main material of the light-emitting layer can only use the organic compound of the present invention as a single light-emitting main material. In addition, the light-emitting layer can also adopt a technical solution of multiple light-emitting main materials and / or multiple light-emitting dyes. When multiple light-emitting main bodies are used, the light-emitting main material may include a first compound and a second compound. The first compound uses at least one compound as shown in Formula 1 of the present invention, or a compound with a structure shown in at least one of A1 to A473 as described above. The second compound can be selected to match the energy level relationship, carrier transport performance, etc. of the first compound.

[0120] The second compound may include one or more combinations of the following PH-1 to PH-85, but is not limited to one or more combinations of the following PH-1 to PH-85.

[0121]

[0122]

[0123]

[0124]

[0125] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0126]

[0127]

[0128] Where D is deuterium.

[0129] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0130]

[0131]

[0132] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.

[0133]

[0134] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0135] 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.

[0136]

[0137]

[0138]

[0139]

[0140] 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.

[0141] Example

[0142] The organic compounds of the present invention were synthesized representatively, and applied together with corresponding comparative compounds in organic electroluminescent devices to test the device performance under the same conditions.

[0143] Synthesis Example

[0144] The specific preparation method of the above-mentioned new 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. It should be noted that obtaining the compound 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 compound proposed by the present invention. The compounds of the synthesis method not mentioned in the present invention are raw materials obtained from commercial channels, or are made by themselves according to known methods through these raw materials. The solvents and reagents used in the present invention, such as dichloromethane, petroleum ether, ethanol, tert-butylbenzene, boron tribromide, carbazole, diphenylamine, and other chemical reagents, can all be purchased from the domestic chemical product market, such as purchased from Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. The analysis and detection of the intermediates and compounds in the present invention uses an ABSCIEX mass spectrometer (4000QTRAP).

[0145] Synthesis example 1

[0146] Synthesis of Compound A1

[0147]

[0148] S1 (2-methoxy-7-naphthol) (20 g), S2 p-bromobenzylamine (24.5 g), ammonium persulfate (52.4 g), 2,2,6,6-tetramethylpiperidinoxide (36 g), and acetonitrile 250 mL were placed in a reaction vessel and heated to 50 ° C under nitrogen for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, washed with a saturated NaCl solution, extracted with EA, dried, and concentrated by vacuum distillation to remove the solvent. The crude product was separated by column chromatography to obtain A1-1 (24.6 g) as a white solid.

[0149] Under nitrogen protection, A1-1 (24.6 g) was dissolved in THF, cooled to 0°C, and NBS (16.6 g) was added in small batches. After the addition was completed, the temperature was kept at 0°C for 2 hours, and then the temperature was naturally returned to room temperature for overnight reaction. After the reaction was completed, water was added, and then extracted with EA. After collection and concentration, the crude product was separated by column chromatography to obtain a yellow product A1-2 (25 g).

[0150] In a three-necked flask, A1-2 (25 g), S32-fluoro-5-chlorophenylboronic acid (13.5 g), potassium carbonate (19.5 g) were added, followed by the solvent dioxane (250 mL) and water (40 mL). After nitrogen replacement, tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (0.77 g) was added, and the mixture was heated to 106°C and refluxed for 5 h. After the reaction was completed, the solvent was cooled and concentrated, and then extracted with DCM. After collection and concentration, A1-3 (22.4 g) was separated by column chromatography as a white solid.

[0151] A1-3 (22.4 g) was placed in a three-necked flask, and 250 mL of DCM solvent was added. Then, after nitrogen replacement, the temperature was lowered to 5-10°C and BBr3 (27.5 g) was slowly added dropwise. After the reaction was completed, the temperature was lowered to 0°C and water was added dropwise to quench the reaction. Then, DCM was used for extraction, and the organic phase was collected, concentrated, and purified by column chromatography to obtain A1-4 (19.4 g) as a white solid.

[0152] A1-4 (19.4 g) was added to a single-mouth bottle, followed by Cs2CO3 (40 g) and 200 mL of DMF solvent, and the mixture was heated to 120°C under nitrogen protection to react overnight. After the reaction was completed, a large amount of water was added to wash and filter to obtain a crude product, which was then boiled and washed twice with ethanol to obtain an off-white solid product A1-5 (15.3 g).

[0153] A1-5 (15.3 g) was placed in a single-mouth bottle, potassium acetate (12.2 g), diboronic acid pinacol ester (16.2 g), Sphos (0.7 g) and Pd2(dba)3 (0.78 g) were added, and the mixture was heated to 115°C and refluxed for 6 h under nitrogen protection. After the reaction was completed, the solvent was concentrated, DCM was added to dissolve, palladium and inorganic salts were removed by filtration with a silica gel short column, the mixture was collected and concentrated, ethanol was added to boil and wash, and the product A1-6 (15.8 g) was obtained after filtration.

[0154] A1-6 (15.8 g), S4 [2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine] (13.2 g), potassium carbonate (9.45 g), tetrakis(triphenylphosphine)palladium (0.8 g), 250 mL of dioxane and 25 mL of water were added to a 500 ml three-necked flask, and then the nitrogen was replaced by vacuum three times, and the temperature was raised to 105°C, and the reaction was allowed to proceed overnight. After the reaction was completed, a large amount of solid precipitated, and the heating was stopped. After cooling to room temperature, the solid was filtered, and the filtered solid was purified by silica gel column chromatography. The obtained crude product was recrystallized from xylene to obtain a white solid A1 (10.8 g. M / Z theoretical value: 642.206; ZAB-HS mass spectrometer (manufactured by Micromass, UK) measured value: 643.208 (M+1).

[0155] The synthesis method of the following compounds is the same as that of Synthesis Example 1, except that S1, S2, S3, and S4 are replaced by compounds in the following table in equal amounts.

[0156]

[0157]

[0158] The present invention exemplifies the specific synthesis methods of the above compounds. For the compounds for which the specific synthesis methods are not given in the following embodiments, they are also prepared by similar methods, and only the raw materials need to be replaced, which will not be described here. Alternatively, those skilled in the art can also prepare them by other methods in the prior art.

[0159] Device Embodiment

[0160] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0161] The above examples and comparative examples respectively provide organic electroluminescent devices, and the specific preparation methods are as follows:

[0162] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment to completely remove the water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0163] Place the glass substrate with ITO anode in a vacuum chamber and evacuate to <1×10 -5 Pa, vacuum thermally deposit 10nm of HT-4:HI-2 (97 / 3, w / w) mixture as hole injection layer on the above anode layer film in order; 60nm of compound HT-4 as hole transport layer; 5nm of compound HT-47 as electron blocking layer material of the device on the hole transport layer, with a total film thickness of 60nm; 40nm of main material: RPD-9 (100:3, w / w) binary mixture as light-emitting layer; 5nm of ET-17 as hole blocking layer of the device on the light-emitting layer; 25nm of compound ET-67:ET-57 (50 / 50, w / w) mixture as electron transport layer; 1nm of LiF as electron injection layer; 150nm of metal aluminum as cathode. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm / sec, and the evaporation rate of metal electrode is controlled at 1nm / sec.

[0164] According to the above preparation steps and testing methods, device examples 1 to 13 of the present invention and comparative device example 1 were completed. The main materials in examples 1 to 13 were the compounds of the present invention, and the main material in comparative device example 1 was the compound CP1 in the prior art.

[0165] According to the same preparation steps and testing methods as mentioned above, device Examples 14 to 27 of the present invention and comparative device Example 2 were completed, except that the main material in Examples 14 to 27 was a mixture of PH2: the compound of the present invention (50 / 50, w / w), and the main material in comparative device Example 2 was a mixture of PH2: the prior art compound CP1 (50 / 50, w / w).

[0166] The specific material selection scheme is detailed in Table 1 and Table 2. The structural formulas of the comparative compounds CP1 and CP2 are as follows:

[0167]

[0168] Among them, the synthesis methods of compounds CP1 and CP2 are detailed in patent application CN113045585A.

[0169] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0170] At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices prepared in the examples and comparative examples and the life of the devices were measured. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured to be 3000 cd / m 2The voltage at which the light is on is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the life test of LT97 is as follows: use a brightness meter at 10000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 9700cd / m 2 The time in hours.

[0171] The performance data of the organic electroluminescent devices prepared in the above device embodiments 1-13 and comparative example 1 are shown in Table 1 below. In order to better reflect the performance advantages of the present invention, the test data of comparative example 1 is set to 1, and the data in the following table are all ratios thereto.

[0172] Table 1:

[0173] Device Example Number Main material Brightness (cd / m2) Voltage efficiency life Comparative Example 1 CP1 3000 1 1 1 Example 1 A1 3000 0.94 1.18 1.76 Example 2 A6 3000 0.93 1.20 1.59 Example 3 A19 3000 0.92 1.22 1.90 Example 4 A48 3000 0.89 1.24 2.03 Example 5 A93 3000 0.91 1.23 2.21 Example 6 A132 3000 0.92 1.27 1.87 Example 7 A204 3000 0.91 1.25 1.79 Example 8 A233 3000 0.90 1.22 1.94 Example 9 A269 3000 0.88 1.24 1.55 Example 10 A282 3000 0.95 1.19 1.48 Embodiment 11 A318 3000 0.96 1.21 1.53 Example 12 A450 3000 0.91 1.26 1.49 Example 13 A458 3000 0.92 1.25 1.71 Embodiment 14 A473 3000 0.94 1.23 1.50

[0174] The performance data of the organic electroluminescent devices prepared in the above device embodiments 14-27 and comparative example 2 are shown in Table 2 below. In order to better reflect the performance advantages of the present invention, the test data of comparative example 2 is set to 1, and the data in the following table are all ratios thereto.

[0175] Table 2:

[0176]

[0177]

[0178] It can be seen from Table 1 and Table 2 above that, compared with the device prepared using the prior art compounds CP1-CP2, the organic electroluminescent device prepared using the compound of the present invention as the luminescent host material has a lower voltage and a longer life, and the luminous efficiency of the device is relatively higher. The inventor speculates that the possible reasons are as follows: Comparative Examples 1 and 2 use compounds CP1 and CP2 in the prior art. The parent core structure used in CP1 to CP2 is a 2,3-position fusion of benzofuran and 7,8-position oxadiazole, and the triplet energy level of the entire molecule is very low, which is very close to the triplet energy level of the dye in the light-emitting layer. In the excited state, after the main energy is transferred to the dye in the light-emitting layer, energy backtransfer is very likely to occur, resulting in reduced device efficiency. In addition, since the 4-membered fusion plane formed by the fusion of benzofuran 2,3-position and naphthyl is in the same direction, electrons are more easily enriched toward the center of the naphthyl, thereby making the electron cloud radius of the overall parent core structure smaller. Compared with the compound of the present invention, its electron injection and transport properties are poor. When it is used as the main material of the light-emitting layer, it is easy to cause carrier transport imbalance, causing the exciton recombination interface to deviate from the light-emitting layer, so the device performance is higher in voltage and shorter in life.

[0179] The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above-mentioned embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art can make various modifications and improvements. The attached claims summarize the scope of the present invention. The equivalent replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A polycyclic condensed organic compound, characterized in that: It is a structure shown in formula (1): In formula (1), R 1 , R 2 , R 3 represents any one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or substituted C1-C20 straight or branched alkyl, unsubstituted or substituted C2-C20 alkenyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C1-C20 alkoxy, unsubstituted or substituted C1-C20 alkylsilyl, unsubstituted or substituted C6-C60 arylamino, unsubstituted or substituted C3-C60 heteroarylamino, unsubstituted or substituted C6-C30 aryloxy, unsubstituted or substituted C3-C30 heteroaryloxy, unsubstituted or substituted C6-C60 aryl or C3-C60 heteroaryl; a, b, c are each independently an integer from 0 to 4; when a is greater than 1, each R 1 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; when b is greater than 1, each R 2 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; when c is greater than 1, each R 3 The substituents may be the same or different, and adjacent substituents may be connected to form a ring; R 1 , R 2 , R 3 Each is independently and optionally connected or unconnected to an adjacent group; X and Z are each independently a single bond, O, S, or NR 4 , CR 5 R 6 ; Y is O or S; R 4 ~R 6 Each is independently selected from a substituted or unsubstituted C1-C20 straight or branched alkyl group, a C2-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; R 5 and R 6 optionally connected to form a ring, Ar 1 and Ar 2 Each independently represents one of hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 condensed ring aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 condensed ring heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino; L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 fused ring aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C3-C60 fused ring heteroaryl group; The term "substituted or unsubstituted" as used herein means substituted by at least one selected from halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, 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. The expression of "—" crossing a ring structure indicates that the connection site is at any position on the ring structure that can form a bond.

2. The polycyclic fused organic compound according to claim 1, characterized in that: The compound represented by formula (1) has a structure represented by formula (2), In the above formula, X, Y, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 1 ,Ar 2 The definitions of a, b, and c are the same as those in formula (1).

3. The polycyclic fused organic compound according to claim 1, characterized in that: The compound represented by formula (1) has a structure represented by formula (3), In the above formula, X, R 1 , R 2 , R 3 , L 1 , L 2 ,Ar 1 ,Ar 2 The definitions of a, b, and c are the same as those in formula (1).

4. The polycyclic condensed organic compound according to claim 1, wherein L 1 , L 2 Each is independently selected from a substituted or unsubstituted C6-C12 arylene group, a substituted or unsubstituted C3-C12 heteroarylene group, and the above-mentioned substituents are independently selected from any one or a combination of at least two of a C1-C20 chain alkyl group, a C3-C20 cycloalkyl group, a C1-C20 alkoxy group, a C6-C30 aryl group or a C3-C30 heteroaryl group; Preferably, L 1 , L 2 Each is independently selected from a single bond or one or a combination of at least two of the following groups: Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 , R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl; More preferably, L 1 , L 2 Each is independently selected from a single bond or one of the following groups: The expression of "—" crossing the ring structure indicates that the connection site is any position on the ring structure that can form a bond. The wavy line or * asterisk indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexanyl, cyclopentanyl, and fluorenyl.

5. The polycyclic condensed organic compound according to claim 2, wherein: Ar 1 and Ar 2 Each is independently selected from hydrogen or a substituted or unsubstituted one of the following groups: Among them, Ar d It is any one of substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and the "substituted or unsubstituted" mentioned above means substituted by at least one selected from halogen, phenyl, cyano, methyl, cyclohexyl, cyclopentanyl and fluorenyl, and the wavy line indicates the connection site.

6. The polycyclic condensed organic compound according to claim 2, wherein: Ar 1 and Ar 2 Each is independently selected from hydrogen or one of the following groups: Among them, Ar d is a group selected from the following groups: Wavy lines indicate junction sites.

7. The polycyclic fused organic compound according to claim 1, characterized in that: R 1 , R 2 , R 3 Each is independently selected from H, phenyl, and cyano; a is 0 or 1; b is 0 or 1; and c is 0 or 1.

8. The polycyclic fused organic compound according to claim 1, characterized in that:

9. Use of the organic compound according to any one of claims 1 to 8 in an organic electronic device; Preferably, the organic electronic device comprises an organic electroluminescent device; Preferably, the application is application as a light-emitting layer material in an organic electroluminescent device.

10. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer inserted between the first electrode and the second electrode, characterized in that: The organic layer contains the organic compound according to any one of claims 1 to 8; Preferably, at least one of the organic layers is a light-emitting layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 8. Preferably, the light-emitting layer comprises a host material and a dye, and the host material comprises at least one organic compound according to any one of claims 1 to 8.

11. A display device, characterized in that: The display device comprises the organic electroluminescent device according to claim 10.

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