Naphthalene benzo five-membered heterocyclic compound for organic electroluminescent device, application of naphthalene benzo five-membered heterocyclic compound and organic electroluminescent device

Abstract

The present invention provides a naphthalene benzo five-membered heterocyclic compound which is a compound for an organic electroluminescent device, characterized by comprising a compound having a structure represented by formula (1) # imgabs0. The compound according to the present invention can be used in a light-emitting layer in an organic EL device, is simple to prepare, can improve and balance the transport of carriers in the device, and has excellent light-emitting properties. The voltage of the device is reduced; the luminous efficiency is improved; and the service life is prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound used for an organic electroluminescent device, and also to an organic electroluminescent device. 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.

[0006] Therefore, there is an urgent need to develop organic electroluminescent devices with higher performance in this field, and further development of organic electroluminescent materials that can provide better photoelectric performance, especially electron blocking materials, is the direction in which the industry is constantly striving to make breakthroughs. Summary of the invention

[0007] In view of the shortcomings of the prior art, one of the purposes of the present invention is to provide a compound that can be used as a main material of the light-emitting layer in an organic electronic device, and the electronic device using the compound has high luminous efficiency and low starting voltage, and the life span is greatly improved. To achieve this purpose, the inventors have devoted themselves to research and developed the following technical solutions to complete the present invention.

[0008] Specifically, the present invention provides a naphthylbenzo five-membered heterocyclic compound, characterized in that it is a compound represented by the structure of formula (1):

[0009]

[0010] In formula (1), X is CR a R b , O or S, R a , R b Each independently represents one of a substituted or unsubstituted C1-C30 alkyl group, a C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group;

[0011] L is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0012] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted -NR 4 R 5 One of;

[0013] Among them, R 4 , R 5 Each independently represents one of a substituted or unsubstituted C1-C30 alkyl group, a C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group;

[0014] R 1 is selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; n is an integer of 0 to 6; when R 1 When there are multiple R 1 Same or different, adjacent R 1 Optionally fused to form a ring or not fused to form a ring;

[0015] R 2, R 3 Each is independently selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silanyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer from 0 to 4, p is an integer from 0 to 3; when R 2 When there are multiple R 2 Same or different, adjacent R 2 Optionally fused to form a ring or not fused to form a ring, when R 3 When there are multiple R 3 Same or different, adjacent R 3 Optionally fused to form a ring or not; provided that adjacent R 2 The fused ring between the adjacent R 3 The fusion rings between them do not occur simultaneously.

[0016] The substituents in the above-mentioned substituted or unsubstituted groups are each independently selected from one or a combination of at least two of 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 a ring structure crossed out by “—” indicates that the connection site is at any bonding position on the ring structure.

[0017] The compound of the present invention can effectively reduce the driving voltage of the device when used as the main material of the light-emitting layer, improve the device luminous efficiency, and according to the comparative test in the embodiment, it is believed that it also contributes to the improvement of the life characteristics. The reason is not clear, and it is speculated that it may be the following reasons: the compound of the present invention adopts the structural group (referred to as large heterocycle) of naphthoxybenzo five-membered heterocycle by naphthyl bridging-L-Ar, and the naphthyl is connected on the inner side of the large heterocyclic structure, that is, the naphthyl is connected to the naphthalene in the large heterocyclic structure, so that the electron cloud of the large heterocyclic ring and the electron cloud of the naphthyl can be effectively overlapped and the electron cloud distribution radius is increased, and the molecular planarity of the large heterocyclic ring itself is better, and the injection and transmission ability of the electron can be effectively enhanced, and an electron injection transmission channel is formed, and the HOMO energy level and LUMO energy level of the compound of the present invention can be adjusted at different positions of the naphthyl, and then the compound preparation can be applied to the organic electroluminescent device to achieve the purpose of reducing the device voltage. After the large heterocycle is bridged with the naphthyl group, the conjugation of the molecule increases, the triplet energy level is low, and the excited state is conducive to energy transfer. After the compound is prepared and applied to the organic electroluminescent device, the energy transfer efficiency can be improved to achieve the purpose of improving efficiency. More importantly, the naphthyl group is double substituted, so that the stacking arrangement radius of the entire molecule is larger, which helps to arrange the molecules more regularly and orderly when prepared into a solid film. After the compound is prepared and applied to the organic electroluminescent device, the light extraction efficiency is effectively improved, thereby improving the overall luminous efficiency of the device. The heteroatom X is introduced into the large heterocycle of the compound of the present invention, and the five-membered heterocycle is fused with phenyl and naphthyl on the outside of the molecule, which can reduce the ratio of n-π* transitions due to the lone pair of electrons of the heteroatom X in the triplet state, thereby improving the inter-gap crossing rate and the life of the triplet exciton. 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 the compound preparation can be applied to the organic electroluminescent device to achieve a long life.

[0018] It should be noted that in this specification, the expression of Ca to Cb means 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. For example, C1 to C10 means C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, indicating that the intermediate numbers are also recorded in the present invention.

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

[0021] In this specification, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed rings. The so-called monocyclic aryl refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; condensed ring aryl refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but condensed to each other by sharing the ring edge, such as naphthyl, anthracenyl, etc.; 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 other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; condensed ring heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0022] 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.

[0023] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0024] 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.

[0025] In this specification, the term alkyl includes the concept of cycloalkyl, and if the emphasis is on chain alkyl, cycloalkyl is not included. Examples of C1-C30 alkyl include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, etc. The C1-C30 alkyl is preferably a C1-C12 alkyl, more preferably a C1-C10 alkyl, and more preferably a C1-C6 alkyl.

[0026] In the present specification, the cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

[0027] In the present specification, examples of C1-C30 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, and methoxy is more preferred.

[0028] In the present specification, examples of C1-C30 silyl groups include silyl groups substituted with the groups listed in the above C1-C30 alkyl groups, specifically including methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

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

[0030] More specifically, as the above-mentioned R group, preferably 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, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, naphthyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, tripolyphenyl, quaternaryl, fluorenyl , spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyrrolyl, imidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthrozolyl, 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, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of the above two groups. But not limited to these groups.

[0031] 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.

[0032] In a preferred embodiment of the present invention, the compound of the present invention has a structure shown in formula (2) or formula (3):

[0033]

[0034]

[0035] In the formula, R 1 , R 2 , R 3 , Ar, L, and X have the same meanings as in formula (1). 2 or R 3 When there are multiple adjacent R 2 There is no fusion ring between adjacent R 3 There is no fusion ring between them.

[0036] In a preferred embodiment of the present invention, L is selected from one of the following substituted or unsubstituted groups,

[0037]

[0038] Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; 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;

[0039] The expression of a ring structure with “—” crossing it indicates that the connection site is any position on the ring structure that can form a bond; a wavy line indicates a connection site, and the substitution in the above “substituted or unsubstituted” means being substituted by at least one selected from halogen, phenyl, cyano, methyl, cyclohexyl, cyclopentyl, and fluorenyl;

[0040] Preferably, L is selected from a single bond or one of the following groups:

[0041]

[0042] In a preferred embodiment of the present invention, Ar is one selected from the following groups,

[0043]

[0044] Among them, Ar 5 and Ar 6 Each is independently selected from one of the following substituted or unsubstituted groups:

[0045]

[0046]

[0047]

[0048]

[0049] The wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexane, and adamantane.

[0050] In a preferred embodiment of the present invention, R 1 , R 2 , R 3 Each is independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C1-C10 chain alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, m, n, p are preferably 0 or 1, and the substituents in the above substituted or unsubstituted groups are independently selected from one or a combination of two of halogen, carboxyl, nitro, cyano, amino, hydroxyl, and thiol;

[0051] Preferably R 1 , R 2 , R 3 Each is independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, and cyano.

[0052] In a preferred embodiment of the present invention, X is CR a R b , O or S, R a , R b Each independently represents one of H, methyl, ethyl, isopropyl, tert-butyl, and phenyl; preferably, X is O or S; more preferably, X is O.

[0053] In a preferred embodiment of the present invention, L is a single bond or a phenylene group, m, n, and p are all 0, and Ar is the following group, wherein Ar 5 and Ar 6The meaning is the same as above.

[0054]

[0055] As more specific examples of the present invention, the following specific compounds can be cited: However, the present invention is not limited to the specific compounds shown below:

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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, characterized in that 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 A204 as described above.

[0068] Specifically, an embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and a first electrode, a plurality of light-emitting functional layers and a second electrode sequentially formed on the substrate; the light-emitting functional layers comprise a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is provided between the hole transport layer and the electron transport layer; wherein the light-emitting layer comprises a main material and a doping material, the main material comprises 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 A204 as described above.

[0069] 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 A204 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.

[0070] 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.

[0071] 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

[0072] 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 embodiments are only used to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0073] Method for obtaining the compound of the present invention

[0074] The preferred compounds of the present invention can be obtained by common chemical synthesis reactions. Taking general formula (2) as an example,

[0075] If X is O, the synthetic pathway is as follows:

[0076]

[0077] If X is S, the synthesis path is as follows:

[0078]

[0079] More specifically, the following synthesis examples of the present invention illustratively provide specific synthesis methods of representative compounds, and the solvents and reagents used in the following synthesis examples can all be purchased or customized from the domestic chemical product market. In addition, those skilled in the art can also synthesize by known methods.

[0080] Organic electroluminescent device of the present invention

[0081] Furthermore, the structure of the organic electroluminescent device of the present invention is a well-known structure, which is characterized in that the above-mentioned compound of the present invention is used in the light-emitting layer. The compound of the present invention can be used alone as a main material or in combination with other materials to form a light-emitting layer of multiple main materials.

[0082] According to the basic principle and usage habits, the compound of the present invention can also be used for electron transport layer, electron injection layer, hole transport layer and hole injection layer. The organic electroluminescent device is described in detail below.

[0083] OLED includes a first electrode, a second electrode, and an organic material layer between the electrodes. The organic material can be divided into multiple regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0084] In a specific embodiment, a substrate may 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) may also be provided on the substrate used as a display.

[0085] 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.

[0086] 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.

[0087] 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).

[0088] 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.

[0089]

[0090]

[0091]

[0092] 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.

[0093]

[0094] 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.

[0095] 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.

[0096] 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.

[0097] In one aspect of the present invention, the host material of the light-emitting layer adopts the organic compound of the present invention.

[0098] 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, and 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 A204 as described above. The second compound can be selected to match the energy level relationship, carrier transport performance, etc. of the first compound.

[0099] 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.

[0100]

[0101]

[0102]

[0103]

[0104] 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.

[0105]

[0106]

[0107] Where D is deuterium.

[0108] 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.

[0109]

[0110] 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.

[0111]

[0112]

[0113] 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).

[0114] 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.

[0115]

[0116]

[0117]

[0118] 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.

[0119] Example

[0120] 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.

[0121] The following synthesis examples of the present invention illustratively provide specific synthesis methods for representative compounds. The solvents and reagents, intermediates, ethyl acetate, methanol, ethanol and other chemical reagents used in the following synthesis examples can all be purchased or customized from the domestic chemical product market.

[0122] Synthesis example 1

[0123] Synthesis of Compound A1

[0124]

[0125] S1 (2-methoxyphenylboronic acid) (15 g), S2 (1-bromo-2-fluoro-4-chloronaphthalene) (25 g), potassium carbonate (27.6 g) were added to a three-necked flask, and solvent dioxane (300 mL) and water (40 mL) were added, and then tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (1.15 g) was added after nitrogen replacement, and the temperature was raised to reflux for overnight reaction. After the reaction was completed, the solvent was concentrated, DCM was added to dissolve and extract, the organic phase was collected, and then purified and separated by silica gel column to obtain A1-1 (23.7 g) as a white solid.

[0126] A1-1 (23.7 g) was placed in a three-necked flask, and 250 mL of DCM solvent was added. After nitrogen replacement, the temperature was lowered to 5-10 ° C and BBr3 (30.7 g) was slowly added dropwise. After the addition, the temperature was naturally returned to room temperature to react for 2 hours. After the reaction was completed, the temperature was lowered to 0 ° C and water was added dropwise to quench the reaction, and then extracted with DCM, the organic phase was collected and concentrated, and purified by column chromatography to obtain A1-2 (19.1 g) as a white solid.

[0127] A1-2 (19.1 g) was added to a single-mouth bottle, followed by Cs2CO3 (46 g) and 200 mL of DMF solvent, and the mixture was heated to 120°C under nitrogen protection and reacted 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 a white solid product A1-3 (14.5 g).

[0128] Under nitrogen protection, A1-3 (14.5 g), pinacol diboron (17.5 g), potassium acetate (16.9 g) were dissolved in dioxane (300 mL), Pd2(dba)3 (1.2 g) and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.1 g) were added, and the mixture was heated to reflux for 7 h under nitrogen protection. After concentration, the mixture was dissolved in DCM and purified by silica gel column chromatography to obtain A1-4 (17 g) as a white solid.

[0129] In a three-necked flask, add A1-4 (17 g), S3 2-bromo-5-chloronaphthalene (11.8 g), and potassium carbonate (13.6 g) to a single-necked flask, then add solvent dioxane (200 mL) and water (20 mL), and add tetrakis(triphenylphosphine)palladium Pd(PPh3)4 (0.57 g) after nitrogen replacement, and heat to 105°C to reflux for 6 hours. A large amount of solid precipitates in the system, which is filtered after cooling, and rinsed with water and ethanol, and dried to obtain A1-5 (14.7 g) as a light yellow solid.

[0130] A1-5 (14.7 g), biboronic acid pinacol ester (11.9 g), potassium acetate (11.4 g) were added to a three-necked flask, and 150 mL of dioxane solvent was added. Then, after nitrogen replacement, Pd2(dba)3 (0.73 g) and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.77 g) were added, and the temperature was raised to reflux for overnight reaction. After the reaction was completed, the solvent was filtered and concentrated, dissolved in DCM, and purified by silica gel column to obtain A1-6 (16 g) as a white solid.

[0131] A1-6 (16 g), S4 [2-chloro-4,6-diphenyl-1,3,5-triazine] (9 g), potassium carbonate (9.3 g), tetrakis (triphenylphosphine) palladium (0.39 g), 150 mL of dioxane and 20 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 106 ° C. The reaction was allowed to proceed overnight. After the reaction was completed, the heating was stopped, and the mixture was cooled to room temperature and filtered. The filtered solid was purified by silica gel column chromatography, and the obtained crude product was recrystallized from xylene to obtain a white solid A1 (9.3 g. M / Z theoretical value: 575.200; ZAB-HS mass spectrometer (manufactured by Micromass, UK) measured value: 576.203 (M+1).

[0132] The synthesis methods of the following synthesis examples are the same as those of Synthesis Example 1, except that S1, S2, S3, and S4 are replaced by compounds in the following table in equal amounts.

[0133]

[0134] 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.

[0135] Device Embodiment

[0136] Examples 1 to 11 and Comparative Examples 1 to 3

[0137] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0138] 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;

[0139] 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, and the total film thickness of the main material: RPD-7 (100:3, w / w) binary mixture with a total film thickness of 60nm:40nm is deposited as the light-emitting layer; 5nm of ET-17 is vacuum evaporated on the light-emitting layer as the hole blocking layer of the device; 25nm of compound ET-69:ET-57 (50 / 50, w / w) mixture as the electron transport layer; 1nm of LiF as the electron injection layer; 150nm of metal aluminum as the cathode. The total evaporation rate of all organic layers and LiF is controlled at 0.1nm / sec, and the evaporation rate of the metal electrode is controlled at 1nm / sec.

[0140] According to the above preparation steps and testing methods, device examples 1 to 11 of the present invention and comparative device examples 1 to 3 were completed. The main materials in examples 1 to 11 were the compounds of the present invention, and the main materials in comparative device examples 1-3 were the compounds CP1-CP3 in the prior art.

[0141] According to the same preparation steps and testing methods as mentioned above, device Examples 9 to 16 of the present invention, comparative device Example 4 and comparative device Example 5 were completed, except that the main material in Examples 9 to 16 was a mixture of PH2: the compound of the present invention (50 / 50, w / w), the main material in comparative device Example 4 was a mixture of PH2: the prior art compound CP4 (50 / 50, w / w), and the main material in comparative device Example 5 was a mixture of PH2: the prior art compound CP5 (50 / 50, w / w).

[0142] The specific material selection scheme is detailed in Table 1 and Table 2. The structural formulas of the comparative compounds CP1-CP5 are as follows:

[0143]

[0144] Among them, the compound CP1 is detailed in patent application KR1020200070462A, the synthesis method of compound CP2 is detailed in patent application CN115725292A, the synthesis method of compound CP3 is detailed in patent application KR1020210139185A, the synthesis method of compound CP4 is detailed in patent application WO2022231319A1, and the synthesis method of compound CP5 is detailed in patent application WO2012073541A1.

[0145] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0146] 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 2 The 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.

[0147] The performance data of the organic electroluminescent devices prepared in the above device embodiments and comparative embodiments 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.

[0148] Table 1:

[0149]

[0150]

[0151] The performance data of the organic electroluminescent devices prepared in the above device embodiments 12-21 and comparative embodiments 4-5 are shown in Table 2 below. In order to better reflect the performance advantages of the present invention, the test data of comparative embodiment 4 is set to 1, and the data in the following table are all ratios thereto.

[0152] Table 2:

[0153] Device Example Number First main material Second main material Brightness (cd / m2) Voltage efficiency life Comparative Example 4 PH2 CP4 3000 1 1 1 Comparative Example 5 PH2 CP5 3000 0.98 0.99 1.14 Example 12 PH2 A118 3000 0.93 1.09 1.26 Example 13 PH2 A131 3000 0.90 1.17 1.30 Embodiment 14 PH2 A137 3000 0.94 1.21 1.24 Embodiment 15 PH2 A139 3000 0.92 1.19 1.29 Example 16 PH2 A149 3000 0.97 1.11 1.52 Embodiment 17 PH2 A152 3000 0.95 1.08 1.84 Embodiment 18 PH2 A166 3000 0.94 1.13 1.61 Embodiment 19 PH2 A185 3000 0.96 1.22 1.73 Embodiment 20 PH2 A203 3000 0.95 1.16 2.11 Embodiment 21 PH2 A204 3000 0.93 1.20 1.55

[0154] As can be seen from Table 1 and Table 2 above, compared with the device prepared by using the prior art compound CP1-CP5, the organic electroluminescent device prepared by using the compound of the present invention as the main material of the light-emitting device has a lower voltage, a higher lifespan, and the luminous efficiency of the device is relatively higher. The inventor speculates that the reasons are as follows: Comparative Examples 1 to Comparative Examples 5 respectively use the compounds CP1-CP5 in the prior art, and the oxygen atom of furan in the naphthobenzofuran parent nucleus structure in CP1 is connected to the 1 position of naphthalene to form a ring, and the 1 position of naphthalene is larger than the 2 position electron density. Compared with the present invention, the electron cloud of the parent nucleus in CP1 will deviate from the center of the parent nucleus molecule, reducing the electron injection ability, and at the same time, it is not conducive to the transmission of electrons to the triazine group. When it is used as the main material of the light-emitting layer, the carrier transmission is unbalanced, and the exciton composite interface deviates from the light-emitting layer, so the device performance is worse. In CP2 and CP4, the naphthobenzofuran parent nucleus is bridged with the naphthyl group by the outer benzene ring of naphthalene, so that the dipole moment of the molecule is too large, which is unfavorable for the arrangement of the molecule and the planarity variation, and has a strong impact on the transmission performance of the electron, and easily leads to the generation of polaron, and the light extraction efficiency is low when it is prepared into thin film devices at the same time. And the T1 of the phenanthroline naphthothiophene parent nucleus of CP3 is too low, and when used as the host material, the triplet energy is easily caused to be transmitted back to the guest, thereby causing the roll-off of efficiency and life span. In addition, the benzocarbazole group and the naphthyl bridged used in CP5, compared to the compounds of the present invention, naphthobenzofuran or naphthiophene are used and the naphthyl bridged, and its HOMO energy level is deeper, and the phenyl group on N on carbazole and the parent nucleus group have a larger angle, which affects the planarity of the whole molecule, and when it is used for the red light host material in the light-emitting layer of OLED, it is unfavorable for the injection and transmission of holes, and the formation efficiency of excitons is low, so that the overall device performance is deteriorated.

[0155] The above experimental data show that the novel organic material of the present invention is an organic light-emitting functional material with good performance as an electron blocking material for an organic electroluminescent device and has broad application prospects.

[0156] The applicant declares that 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. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various 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 naphthylbenzo five-membered heterocyclic compound, characterized in that: It is a compound represented by the formula (1): In formula (1), X is CR a R b , O or S, R a , R b Each independently represents one of a substituted or unsubstituted C1-C30 alkyl group, a C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; L is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted -NR 4 R 5 One of; Among them, R 4 , R 5 Each independently represents one of a substituted or unsubstituted C1-C30 alkyl group, a C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; R 1 is selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; n is an integer of 0 to 6; when R 1 When there are multiple R 1 Same or different, adjacent R 1 Optionally fused to form a ring or not fused to form a ring; R 2 , R 3 Each is independently selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silanyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer from 0 to 4, p is an integer from 0 to 3; when R 2 When there are multiple R 2 Same or different, adjacent R 2 Optionally fused to form a ring or not fused to form a ring, when R 3 When there are multiple R 3 Same or different, adjacent R 3 Optionally fused to form a ring or not; provided that adjacent R 2 The fused ring between the adjacent R 3 The fusion rings between them do not occur simultaneously. The substituents in the above-mentioned substituted or unsubstituted groups are each independently selected from the group consisting of 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, or a combination of at least two of the following groups; the expression of a ring structure crossed out by "—" indicates that the connection site is at any bonding position on the ring structure.

2. The naphthoxybenzo five-membered heterocyclic compound according to claim 1, characterized in that Having the structure shown in formula (2) or formula (3): In the formula, R 1 , R 2 , R 3 , Ar, L, and X have the same meanings as in formula (1). 2 or R 3 When there are multiple adjacent R 2 There is no fusion ring between adjacent R 3 There is no fusion ring between them.

3. The naphthylbenzo five-membered heterocyclic compound according to claim 1, characterized in that L is selected from one of the following substituted or unsubstituted groups, Y 1 Each independently selected from O, S, NR 11 or CR 12 R 13 ; R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; 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; 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 indicates the connection site, and the substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexane, cyclopentane, and fluorenyl; Preferably, L is selected from a single bond or one of the following groups:

4. The naphthoxybenzo five-membered heterocyclic compound according to claim 1, characterized in that Ar is one selected from the following groups, Among them, Ar 5 and Ar 6 Each is independently selected from one of the following substituted or unsubstituted groups: The wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclohexane, and adamantane.

5. The naphthylbenzo five-membered heterocyclic compound according to claim 1, characterized in that R 1 , R 2 , R 3 Each is independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C1-C10 chain alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, m, n, p are preferably 0 or 1, and the substituents in the above substituted or unsubstituted groups are independently selected from one or a combination of two of halogen, carboxyl, nitro, cyano, amino, hydroxyl, and thiol; Preferably R 1 , R 2 , R 3 Each is independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, and cyano.

6. The naphthoxybenzo five-membered heterocyclic compound according to claim 1, characterized in that: X is CR a R b , O or S, R a , R b Each independently represents one of H, methyl, ethyl, isopropyl, tert-butyl, and phenyl; preferably, X is O or S; more preferably, X is O.

7. The naphthoxybenzo five-membered heterocyclic compound according to any one of claims 1 to 6, characterized in that L is a single bond or phenylene, m, n, and p are all 0, and Ar is the following group, wherein Ar 5 and Ar 6 The meaning is the same as in claim 4.

8. The naphthoxybenzo five-membered heterocyclic compound according to claim 1, characterized in that: The formula (1) has any one of the following structures:

9. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises the naphthylbenzo five-membered heterocyclic compound according to any one of claims 1 to 8. 10 . A host material for a light-emitting layer of an organic electroluminescent device, comprising one of the naphthoxybenzo five-membered heterocyclic compounds according to claim 1 .

11. Use of the naphthylbenzo five-membered heterocyclic compound according to any one of claims 1 to 8 as a functional material in an organic electronic device, wherein the organic electronic device comprises: Organic electroluminescent device, optical sensor, solar cell, lighting element, organic thin film transistor, organic field effect transistor, organic thin film solar cell, information tag, electronic artificial skin sheet, sheet-type scanner or electronic paper. 12 . The use according to claim 11 , which is used as a host material for a light-emitting layer.

13. A display device comprising the organic electroluminescent device according to claim 9.

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