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

Abstract

The present invention relates to a compound and its application, and an organic electroluminescent device containing the compound, wherein the compound has a structure shown in Formula I. The parent core structure of the compound provided by the present invention adopts carbazole and naphthalene or naphthalene heterocycle to form a seven-membered nitrogen heterocycle through C-C and C-N bonds, and the structural unit can effectively improve the hole transport performance of the molecule while maintaining a higher molecular triplet energy level. When the compound of the present invention is used as an organic electroluminescent device, especially a light-emitting layer material, the carrier transport balance in the device can be effectively improved, thereby ensuring that the device obtains the excellent effects of high luminous efficiency and low starting voltage.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to a compound and application thereof, and an organic electroluminescence device containing the compound. Background Art

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

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

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

[0005] As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, life span, cost and other aspects.

[0006] Therefore, there is an urgent need in the art to develop an organic electroluminescent material that can improve the luminous efficiency of the device, reduce the driving voltage, and extend the service life. Summary of the invention

[0007] One of the purposes of the present invention is to provide a compound, which can be applied to an organic electroluminescent device to improve the device's luminous efficiency, reduce the driving voltage, and extend the service life.

[0008] To achieve this object, the present invention adopts the following technical solutions:

[0009] The present invention provides a compound having a structure shown in Formula I:

[0010]

[0011] The X 1 ~X 15 Independently selected from CR 1 or N, the R 1 independently selected from hydrogen or a combination of at least two of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 electron-rich heteroaryl, wherein R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring;

[0012] When the above R 1 When there is a substituent, the substituent is selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, C6-C30 condensed heteroaryl group, or a combination of at least two of them.

[0013] Preferably, the X 1 ~X 15 At least one of them is N; or preferably, the X 1 ~X 15 At least one of them is CR 1 , and the R 1 is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group, wherein R1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring;

[0014] Further preferably, the X 1 ~X 15 Independently selected from CR 1 or N, and X 1 ~X 15 1 to 3 of them are N; more preferably, the X 1 ~X 15 One or two of them are N;

[0015] More preferably, the X 1 ~X 15 Independently selected from CR 1 or N, the R 1 is independently selected from one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 electron-rich heteroaryl, wherein R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring;

[0016] Preferably, the R 1 independently selected from hydrogen or one of the following groups which are substituted or unsubstituted: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenylene, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimer indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl;

[0017] More preferably, the R 1 is hydrogen;

[0018] Preferably, the X 1 ~X 15 At least one of them is CR 1 , and the R 1 independently selected from hydrogen or substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, or R1 Independently selected from the formula *-L 1 -Ar 1 , the R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring;

[0019] The L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0020] Preferably, the R 1 At least one of the formula *-L 1 -Ar 1 .

[0021] Further preferably, the X 1 ~X 15 Independently selected from CR 1 , the R 1 are independently selected from hydrogen or selected from the formula *-L 1 -Ar 1 , and the R 1 At least one of the formula *-L 1 -Ar 1 , the R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring;

[0022] The L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0023] Preferably, the L 1 A single bond or one of the following groups which are substituted or unsubstituted: phenylene, naphthylene, biphenylene; when the above groups have substituents, the substituents are selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, C6-C30 condensed heteroaryl group, or a combination of at least two of them.

[0024] Still further preferably, the X 1 ~X15 Independently selected from CR 1 , the R 1 are independently selected from hydrogen or selected from the formula *-L 1 -Ar 1 , and the R 1 At least one of the formula *-L 1 -Ar 1 , the R 1 independently connected to the connected aromatic ring to form a ring or not; said L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 electron-rich heteroaryl groups;

[0025] Or, further preferably, the X 1 ~X 15 Independently selected from CR 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 ; said L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-deficient heteroaryl group; more preferably, Ar 1 It is selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups.

[0026] More preferably, the X 1 ~X 15 At least one of them is CR 1 , and the R 1 R is independently selected from hydrogen or substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, or R 1 Independently selected from the formula *-L 1 -Ar 1 , the R 1 independently connected to the connected aromatic ring to form a ring or not connected to form a ring, the L 1is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; and X 10 ~X 15 Independently selected from CR 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 ; Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-deficient heteroaryl group; preferably Ar 1 is selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups;

[0027] Still further preferably, the X 10 ~X 15 Independently selected from CR 1 , the R 1 are independently selected from hydrogen or selected from the formula *-L 1 -Ar 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 ;

[0028] Still further preferably, the X 1 ~X 9 Independently selected from CR 1 , and the R 1 All are hydrogen.

[0029] "Electron-deficient heteroaryl (also referred to as electron-deficient group)" in this specification refers to a group whose electron cloud density on the benzene ring is reduced after the group replaces the hydrogen on the benzene ring, and the Hammett value of such a group is usually greater than 0.6. The Hammett value refers to the characterization of the charge affinity of a specific group, which is a measure of an electron-withdrawing group (positive Hammett value) or an electron-donating group (negative Hammett value). The Hammett equation is described in more detail in Thomas H.Lowry and Katheleen Schueller Richardson, "Mechanism and Theory In Organic Chemistry', New York, 1987, pp. 143-151, which is cited herein as a reference. Such groups can be listed but are not limited to: triazine, pyrimidine, benzopyrimidine, benzopyridinyl, naphthyridine, phenanthroline, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, pyridazinyl, and the above-mentioned groups substituted with alkyl or aryl.

[0030] Further preferably, when the Ar 1 When Ar is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-deficient heteroaryl group, 1 Any one selected from the structures represented by the following formulae (3-1) to (3-4):

[0031]

[0032] In formula (3-1), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 Each independently selected from CR 2 or N atoms, and Z 1 , Z 2 , Z 3 , Z 4 and Z 5 At least one of them is a N atom,

[0033] In formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 Each independently selected from CR 2 or N atoms, and Z 6 , Z 7 , Z 8 , Z 9 , Z 10, Z 11 , Z 12 and Z 13 At least one of them is a N atom,

[0034] In formula (3-3), Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 Each independently selected from CR 2 or N atoms, and Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 At least one of them is a N atom,

[0035] In formula (3-4), Z 24 , Z 25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 Each independently selected from CR 2 or N atoms, and Z 24 , Z 25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 At least one of them is a N atom,

[0036] The R 2 One or a combination of at least two selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 condensed ring heteroaryl;

[0037] Where * represents the access bond of the group.

[0038] Preferably, the Ar 1 Having the structure shown in (3-1) or (3-2);

[0039] Preferably, in formula (3-1), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 At least two of them are N atoms;

[0040] Preferably, in formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 At least two of them are N atoms.

[0041] Preferably, the Ar 1 One of the following groups, substituted or unsubstituted, is selected from: pyridyl, quinolyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl;

[0042] Preferably, the Ar 1 One selected from the following substituted or unsubstituted groups: quinazolinyl, triazine, quinoxalinyl;

[0043] When the above-mentioned groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, and C6-C30 condensed heteroaryl group.

[0044] Preferably, the Ar 1 One selected from substituted or unsubstituted A1 to A14 groups:

[0045]

[0046] Where * represents the access bond of the group.

[0047] More preferably, the Ar 1 One selected from the group B1 to B19:

[0048]

[0049]

[0050] Where * represents the access bond of the group.

[0051] Preferably, the X 1 ~X 15 Independently selected from CR 1 , and the R 1 At least one of the formula *-L 1 -Ar 1 , the Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-rich heteroaryl group; more preferably, the Ar 1 One of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimerized indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl;

[0052] Further preferably, the X 1 ~X 15 Independently selected from CR 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 More preferably, the Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-rich heteroaryl group; more preferably, the Ar 1One of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimerized indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl;

[0053] More preferably, the X 1 ~X 15 Independently selected from CR 1 , the R 1 One or two of them are of the formula *-L 1 -Ar 1 , and the remaining R 1 are all hydrogen, and the Ar 1 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-rich heteroaryl group; more preferably, the Ar 1 One of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimerized indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl.

[0054] Still further preferably, the above L 1A single bond or one of the following groups which are substituted or unsubstituted: phenylene, naphthylene, biphenylene; when the above groups have substituents, the substituents are selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, C6-C30 condensed heteroaryl group, or a combination of at least two of them.

[0055] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0056] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0057] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0058] The atomic names described in the present invention include their corresponding isotopes. For example, hydrogen (H) includes 1 H (hydrogen or H), 2 H (deuterium or D), etc.; Carbon (C) includes 12 C. 13 C, etc.

[0059] In the present specification, 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.

[0060] Among the above-mentioned substituent groups, the C1-C20 chain alkyl group is preferably a C1-C10 chain alkyl group, and more preferably a C1-C6 chain alkyl group, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, n-pentyl, n-heptyl, n-nonyl, n-decyl, etc.

[0061] Among the above-mentioned substituent groups, the C3-C20 cycloalkyl group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0062] The substituted or unsubstituted C6-C30 aryl group is preferably a C6-C20 aryl group, and the aryl group is preferably 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.

[0063] The above-mentioned substituted or unsubstituted C3-C30 heteroaryl group is preferably a C4-C20 heteroaryl group, and the heteroaryl group is preferably a furyl group, a thienyl group, a pyrrolyl group, a benzofuranyl group, a benzothienyl group, an isobenzofuranyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazole group and derivatives thereof, wherein the carbazole derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolecarbazole.

[0064] Preferred structures of the compounds involved in the present invention include compounds represented by structures P1 to P108 below, but are not limited to these compounds:

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] A second object of the present invention is to provide an application of the compound described in the first object, wherein the compound is applied to organic electronic devices.

[0075] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or electronic paper, preferably an organic electroluminescent device.

[0076] Preferably, the compound is used as a host light-emitting layer material in the organic electroluminescent device.

[0077] The third object of the present invention is to provide an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one organic layer inserted between the first electrode and the second electrode, wherein the organic layer contains at least one compound described in one of the objects.

[0078] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer contains at least one compound described in one of the purposes.

[0079] Preferably, the compound is used as a host material of the light-emitting layer.

[0080] The specific reasons why the above compounds of the present invention have excellent performance as the main material of the light-emitting layer are not clear, but it is speculated that the reasons may be as follows:

[0081] The compound mother core structure of the present invention adopts carbazole and naphthalene or naphthalene heterocycle to form a seven-membered nitrogen heterocycle through CC and CN bonds. The structural unit can effectively improve the hole transport performance of the molecule while maintaining a higher molecular triplet energy level. At the same time, different electron-withdrawing structural units with electron transport capabilities are specifically designed and introduced at different positions of the mother core structural unit, thereby designing a new host material with different electron and hole transport capabilities to meet the material requirements of different structural devices.

[0082] The mother core structure of the compound of the present invention adopts carbazole and naphthalene or naphthalene heterocycle bonded by CC and CN bonds to form a seven-membered nitrogen heterocyclic mother core structure, and is combined with nitrogen substitution or different electron transport structural units and different connection modes between the two to achieve the best effect, so that the material can be applied to organic electroluminescent devices, especially when used as a main material, the luminous efficiency can be improved.

[0083] In addition, the preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, and it is suitable for mass production and expansion. DETAILED DESCRIPTION

[0084] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0085] The representative synthesis route of the compound of formula I of the present invention is as follows:

[0086]

[0087] Wherein, X1~X9, L1, Rr1 all have the same meanings as the symbols in Formula I; Pd(PPh3)4 represents tetrakis(triphenylphosphine)palladium, K2CO3 represents potassium carbonate, KOH represents potassium hydroxide, and KOAc represents potassium acetate.

[0088] More specifically, the following synthesis examples of the present invention exemplarily provide specific synthesis methods of representative compounds, and the solvents and reagents used in the following synthesis examples, various chemicals used in the present invention such as petroleum ether, ethyl acetate, sodium sulfate, toluene, xylene, tetrahydrofuran, dichloromethane, acetic acid, potassium phosphate, potassium acetate, potassium hydroxide, dimethyl sulfoxide and other basic chemical raw materials can be purchased or customized from the domestic chemical product market, for example, purchased from Sinopharm Group Reagent Company, Sigma-Aldrich Company, and J&K Reagent Company. In addition, those skilled in the art can also synthesize by known methods.

[0089] Synthesis Example 1: Synthesis of Compound P1

[0090]

[0091] In a 1000mL single-mouth bottle, add 103g (500mmol) 8-chloro-naphthyl-2-boric acid, 100g (500mmol) 2-nitrobromobenzene, 5.5g (5mmol) tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4), 210g (1500mmol) potassium carbonate (K2CO3), 500mL toluene, 100mL water, vacuum and replace nitrogen 3 times, heat the reaction to 90°C overnight, and stop the reaction after the reaction is complete. Cool to room temperature, separate the reaction solution, concentrate the organic phase, and separate by column chromatography (petroleum ether: ethyl acetate = 1:2) to obtain 92g of compound M1-1.

[0092] Theoretical M / Z value: 283; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 284.

[0093] In a 500mL single-mouth bottle, add 92g (320mmol) M1-1, 100mL triethyl phosphite, and 100mL xylene, heat to 140 degrees and react overnight. After the reaction is complete, stop the reaction. Cool to room temperature, remove xylene and excess triethyl phosphite under reduced pressure, and separate by column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain 67g compound M1-2.

[0094] Theoretical M / Z value: 251; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 252.

[0095] In a 500mL single-mouth bottle, add 67g (270mmol) M1-2, 76g (300mmol) bis(pinacolato) diboron, 3g (3mmol) tetrakis(triphenylphosphine) palladium (Pd(PPh3)4), 40g (405mmol) potassium acetate (KOAc), 300mL toluene, evacuate and replace nitrogen 3 times, heat the reaction to 90°C and react overnight, stop the reaction after the reaction is complete, cool to room temperature, wash the reaction solution with water, separate the liquid, concentrate the organic phase, separate by column chromatography (petroleum ether: ethyl acetate = 5:1), and obtain 70g compound M1-3.

[0096] In a 500mL single-mouth bottle, add 70g (200mmol) M1-3, 52g (200mmol) 1-fluoro-3-chloro-8-bromonaphthalene, 2,2g (2mmol) tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4), 83g (600mmol) potassium carbonate (K2CO3), 300mL toluene, 50mL water, vacuum and replace nitrogen 3 times, heat the reaction to 90°C overnight, and stop the reaction after the reaction is complete. Cool to room temperature, separate the reaction solution, concentrate the organic phase, and separate by column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 54g compound M1-4.

[0097] Theoretical M / Z value: 395; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 396.

[0098] In a 500mL single-mouth bottle, add 54g (136mmol) M1-4, 15.6g (270mmol) potassium hydroxide (KOH), and 200mL dimethyl sulfoxide (DMSO), heat to 150 degrees to react overnight, and stop the reaction after the reaction is complete. Cool to room temperature, remove dimethyl sulfoxide under reduced pressure, add 100mL toluene, wash with water to remove inorganic salts, concentrate the organic phase, and separate by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain 38g of compound M1-5.

[0099] Theoretical M / Z value: 375; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 376.

[0100] In a 500mL single-mouth bottle, add 38g (102mmol) M1-5, 38g (150mmol) bis(pinacolato) diboron, 2g (2mmol) tetrakis(triphenylphosphine) palladium (Pd(PPh3)4), 20g (200mmol) potassium acetate (KOAc), 300mL toluene, vacuum and replace nitrogen 3 times, heat the reaction to 90°C and react overnight, stop the reaction after the reaction is complete, cool to room temperature, wash the reaction solution with water, separate the liquid, concentrate the organic phase, separate by column chromatography (petroleum ether: ethyl acetate = 10:1), and obtain 41g compound M1-6.

[0101] In a 500mL single-mouth bottle, add 41g (85mmol) M1-6, 24g (85mmol) 2-chloro-4-phenylquinazoline, 1g (1mmol) tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4), 35g (255mmol) potassium carbonate (K2CO3), 300mL toluene, 50mL water, evacuate and replace with nitrogen 3 times, heat the reaction to 110°C and react overnight. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, boil with methanol, filter, and recrystallize from toluene to obtain 31g of compound P1.

[0102] Theoretical M / Z value: 545; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 546.

[0103] Synthesis Example 2: Synthesis of Compound P5

[0104]

[0105] The synthesis method of compound P5 is the same as that of P1, except that 2-(2-chlorophenyl)-4-phenylquinazoline is used to replace the 2-chloro-4-phenylquinazoline in P1.

[0106] Theoretical M / Z value: 621; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 622.

[0107] Synthesis Example 3: Synthesis of Compound P57

[0108]

[0109] The synthesis method of compound P57 is the same as that of P1, except that 1-fluoro-3-chloro-8-bromonaphthalene is replaced by 1-bromo-3-chloro-8-fluoronaphthalene, and 2-chloro-4-phenylquinazoline is replaced by 2-chloro-4,6-diphenyl-1,3,5-triazine. The theoretical M / Z value is 572; the measured M / Z value using a ZAB-HS mass spectrometer (manufactured by Micromass, UK) is 573.

[0110] Synthesis Example 4: Synthesis of Compound P84

[0111]

[0112] The synthesis method of compound M3-2 is the same as that of M1-5, except that 4-bromo-5-fluoro-7-chloroisoquinoline is used to replace 1-fluoro-3-chloro-8-bromonaphthalene. The theoretical M / Z value is 376; the measured M / Z value using a ZAB-HS mass spectrometer (manufactured by Micromass, UK) is 377.

[0113] In a 500mL three-necked flask, add 15.4g (40mmol) M3-2, 6.8g (40mmol) carbazole, 0.9g (1mmol) tri(dibenzylideneacetone)dipalladium (i.e. Pd2(dba)3), 0.5mL tri-tert-butylphosphine toluene solution (P(t-Bu)3, 50% by weight), 300mL toluene, 11.5g (120mmol) sodium tert-butoxide (NaOBu-t), evacuate and replace with nitrogen 3 times, heat the reaction to 120℃ and react for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, boil with methanol, filter, and recrystallize from toluene to obtain 10.5g compound P84.

[0114] Theoretical M / Z value: 507; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 508.

[0115] Synthesis Example 5: Synthesis of Compound P91

[0116]

[0117]

[0118] The synthesis method of compound M4-1 is the same as that of M1-1, except that 2-nitrobromobenzene is replaced by 2,4-dibromo-6-iodinitrobenzene. The theoretical M / Z value is 439; the measured M / Z value using a ZAB-HS mass spectrometer (manufactured by Micromass, UK) is 440.

[0119] In a 1000mL three-necked flask, add 167g (380mmol) M4-1, 127g (760mmol) carbazole, 5g (5mmol) tris (dibenzylideneacetone) dipalladium (i.e. Pd2 (dba) 3), 5mL tri-tert-butylphosphine toluene solution (P (t-Bu) 3, 50% weight ratio), 500mL toluene, 109g (120mmol) sodium tert-butoxide (NaOBu-t), vacuum and replace nitrogen 3 times, and heat the reaction to 120°C for 5h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, concentrate the organic phase, and column chromatograph the product (petroleum ether: ethyl acetate = 3:1) to obtain 142g compound M4-2.

[0120] Theoretical M / Z value: 613; measured M / Z value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 614.

[0121] The synthesis method of compound M4-3 and compound P91 is the same as that of M1-2 to M1-5, except that 1-fluoro-3-chloro-8-bromonaphthalene is replaced by 1-bromo-8-fluoro-2,6-naphthyridine, M / Z theoretical value: 673; M / Z measured value using ZAB-HS mass spectrometer (manufactured by Micromass, UK): 674.

[0122] Synthesis Example 6: Synthesis of Compound P25

[0123]

[0124] The synthesis method of compound P25 is the same as that of P1, except that 1-fluoro-3-chloro-8-bromonaphthalene is replaced by 1-fluoro-4-chloro-8-bromonaphthalene. The theoretical M / Z value is 545; the measured M / Z value using a ZAB-HS mass spectrometer (manufactured by Micromass, UK) is 546.

[0125] Synthesis Example 7: Synthesis of Compound P79

[0126]

[0127] The synthesis method of compound P79 is the same as that of P1, except that 2-nitrobromobenzene is replaced by 2-bromo-4-(9-carbazolyl)nitrobenzene, and 1-fluoro-3-chloro-8-bromonaphthalene is replaced by 1-fluoro-8-bromo-3-phenylisoquinoline. The theoretical M / Z value is 583; the measured M / Z value using a ZAB-HS mass spectrometer (manufactured by Micromass, UK) is 584.

[0128] Device Embodiment

[0129] Implementation

[0130] 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.

[0131] 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.

[0132] 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), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0133] 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.

[0134] 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).

[0135] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0136]

[0137]

[0138]

[0139]

[0140] 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.

[0141]

[0142] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit light of different wavelength spectra, and may also include a host material (Host). The light-emitting layer may be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors may be arranged in a plane according to a pixel pattern, or may be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they may be separated from each other or may be connected to each other. The light-emitting layer may also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0143] 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.

[0144] 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.

[0145]

[0146]

[0147]

[0148] D stands for deuterium.

[0149] 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.

[0150]

[0151]

[0152] 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.

[0153]

[0154] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described below; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0155]

[0156]

[0157] 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).

[0158] 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-65 listed below.

[0159]

[0160]

[0161]

[0162] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-65 described above, or one or more compounds of PH-1 to PH-46 described below; or a mixture of, but not limited to, one or more compounds of ET-1 to ET-65 and one or more compounds of PH-1 to PH-46.

[0163]

[0164]

[0165]

[0166] 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.

[0167] Device Example 1

[0168] This embodiment provides an organic electroluminescent device, and the specific preparation process is as follows:

[0169] 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;

[0170] Place the glass substrate with the anode in a vacuum chamber and evacuate to a vacuum of <1×10 -5 Pa, on the above anode layer film, 10nm of HT-4:HI-3 (97 / 3, w / w) mixture as a hole injection layer, 60nm of compound HT-4 as a hole transport layer, 5nm of compound HT-48 as an electron blocking layer; 40nm of compound P1:RPD-10 (100:3, w / w) binary mixture as a light-emitting layer; 5nm of ET-23 as a hole blocking layer, 25nm of compound ET-61:ET-57 (50 / 50, w / w) mixture as an electron transport layer, 1nm of LiF as an electron injection layer, and 150nm of metal aluminum as a 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.

[0171] The organic electroluminescent devices provided in Examples 2 to 7 are prepared in the same manner as in Device Example 1, except that the main material of the light-emitting layer is replaced by other compounds of the present invention as shown in Table 1 below instead of the compound P1 of the present invention.

[0172] The organic electroluminescent devices provided in Device Comparative Examples 1 and 2 are prepared by the same method as Device Example 1, except that the main material of the light-emitting layer is replaced by the compound P1 of the present invention with the compounds R-1 and R-2 in the prior art as shown in Table 1 below.

[0173] The structures of compounds R-1 and R-2 are shown below:

[0174]

[0175] Compound R-1 was synthesized with reference to patent KR1020200013600A, and compound R-2 was synthesized with reference to patent CN110526901A.

[0176] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0177] At the same brightness, a digital source meter (Keithley 2400) and a brightness meter (ST-86LA brightness meter, Beijing Normal University Optoelectronic Instrument Factory) were used to measure the current efficiency of the organic electroluminescent devices prepared in Examples 1-7 and Comparative Examples 1-2. Specifically, the device current was measured to be 10 mA / cm -2 When the current density is 0.0447 W / m, the ratio of the luminance of the organic electroluminescent device to the current density is the current efficiency. The test results are shown in Table 1.

[0178] Table 1:

[0179]

[0180]

[0181] It can be seen from the data in Table 1 that when the material scheme and preparation process of other functional layers in the structure of the organic electroluminescent device are exactly the same, compared with the comparative example, when the compound of the present invention is used as the main layer material of the organic electroluminescent device, the brightness of the device reaches 1000 cd / m 2 When the current efficiency is as high as 8.8cd / A, it is a main material with good performance.

[0182] The difference between the compound R-1 of comparative example 1 and the compound P25 in Example 6 is that the benzocarbazole and the naphthalene ring in the structure of the compound R-1 are not connected to form a macrocycle. When the compound R-1 is used as the main layer material of the organic electroluminescent device, the current efficiency of the device is 6.9 cd / A. The current efficiency of the device using the compound R-1 is worse than that of the device using P25, which may be related to the seven-membered nitrogen heterocyclic structural unit composed of the benzocarbazole and the naphthalene ring in the compound P25 having better hole transport performance.

[0183] The difference between the compound R-2 of Comparative Example 2 and the compound P79 in Example 7 is that the benzocarbazole and the naphthalene ring in the structure of the compound R-2 are not connected to form a macrocycle. When the compound R-2 is used as the main layer material of the organic electroluminescent device, the current efficiency of the device is 5.1 cd / A. The current efficiency of the device using the compound is worse than that of the device using the compound P79, which may be related to the seven-membered nitrogen heterocyclic structural unit composed of the benzocarbazole and the naphthalene ring in the compound P79 having better hole transport performance.

[0184] It can be seen that in the compounds provided by the present invention, the seven-membered nitrogen heterocyclic structure unit composed of carbazole and naphthalene or naphthalene heterocyclic ring, the number and position of nitrogen atoms substituted on the heterocyclic ring, the position of the electron transport unit on the macrocyclic ring, and the connection mode between the seven-membered nitrogen heterocyclic structure unit and the electron transport unit are important factors affecting the excellent performance of the compound when applied to organic electroluminescent devices.

[0185] The seven-membered nitrogen heterocyclic structural unit composed of benzocarbazole and naphthalene ring in the compound of the present invention has a higher molecular triplet energy level and better hole transport performance; by using this structural unit, in combination with different electron transport structural units, a new main body material with good carrier balance effect and better transport performance can be obtained.

[0186] The seven-membered nitrogen heterocyclic mother core structure formed by bonding benzocarbazole and naphthalene ring in the compound of the present invention is coordinated with the introduction of electron-withdrawing structural units on the naphthalene ring of the non-carbazole part, which can achieve the best effect, so that the material can be applied to organic electroluminescent devices, especially as a main material, to improve the luminous efficiency.

[0187] The above experimental data show that the novel organic material of the present invention is a main material with good performance as a light-emitting layer material of an organic electroluminescent device and has broad application prospects.

[0188] The present invention uses the above-mentioned embodiments to illustrate the compounds of the present invention and their application in OLED devices, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of 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 compound having a structure shown in Formula I: In Formula I, the X 1 ~X 15 Independently selected from CR 1 or N, the R 1 is independently selected from hydrogen or a combination of at least two of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, wherein R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring; When the above R 1 When there is a substituent, the substituent is selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, C6-C30 condensed heteroaryl group, or a combination of at least two of them.

2. The compound according to claim 1, wherein X 1 ~X 15 At least one of them is N; Alternatively, the X 1 ~X 15 At least one of them is CR 1 , and the R 1 is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group, wherein R 1 They may be independently connected to the aromatic ring to form a ring or may not be connected to form a ring.

3. The compound according to claim 1, wherein X 1 ~X 15 Independently selected from CR 1 or N, and X 1 ~X 15 1 to 3 of them are N.

4. The compound according to claim 3, wherein X 1 ~X 15 One or two of them are N.

5. The compound according to claim 1, wherein R 1 is independently selected from one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 electron-rich heteroaryl, wherein R 1 They may be independently connected to the aromatic ring to form a ring or may not be connected to form a ring.

6. The compound according to claim 1, wherein R 1 independently selected from hydrogen or one of the following groups which are substituted or unsubstituted: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenylene, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimer Indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl.

7. The compound according to claim 1, wherein R 1 For hydrogen.

8. The compound according to claim 1, wherein X 1 ~X 15 At least one of them is CR 1 , and the R 1 independently selected from hydrogen or substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 silyl, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, or R 1 Independently selected from the formula *-L 1 -Ar 1 , the R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring; The L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.

9. The compound according to claim 8, wherein R 1 At least one of the formula *-L 1 -Ar 1 .

10. The compound according to claim 1, wherein X 1 ~X 15 Independently selected from CR 1 , the R 1 are independently selected from hydrogen or selected from the formula *-L 1 -Ar 1 , and the R 1 At least one of the formula *-L 1 -Ar 1 , the R 1 Independently connected to the connected aromatic ring to form a ring or not connected to form a ring; The L 1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.

11. The compound according to claim 10, wherein L 1 A single bond or one of the following groups which are substituted or unsubstituted: phenylene, naphthylene, biphenylene; when the above groups have substituents, the substituents are selected from one of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, C6-C30 condensed heteroaryl group, or a combination of at least two of them.

12. The compound according to claim 10, wherein Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 electron-rich heteroaryl groups.

13. The compound according to claim 10, wherein X 1 ~X 15 Independently selected from CR 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 ; The Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups.

14. The compound according to claim 13, wherein Ar 1 It is selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups.

15. The compound according to claim 8, wherein X 10 ~X 15 Independently selected from CR 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 ; The Ar 1 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups.

16. The compound according to claim 15, wherein Ar 1 It is selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl groups.

17. The compound according to claim 15, wherein X 10 ~X 15 Independently selected from CR 1 , the R 1 are independently selected from hydrogen or selected from the formula *-L 1 -Ar 1 , and the R 1 One or two of them are of the formula *-L 1 -Ar 1 .

18. The compound according to claim 15 or 17, wherein X 1 ~X 9 Independently selected from CR 1 , and the R 1 All are hydrogen.

19. According to any one of claims 13-17, the compound wherein Ar 1 Any one selected from the structures represented by the following formulae (3-1) to (3-4): In formula (3-1), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 Each independently selected from CR 2 or N atoms, and Z 1 , Z 2 , Z 3 , Z 4 and Z 5 At least one of them is a N atom, In formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 Each independently selected from CR 2 or N atoms, and Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 At least one of them is a N atom, In formula (3-3), Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 Each independently selected from CR 2 or N atoms, and Z 14 , Z 15 , Z 16 , Z 17 , Z 18 , Z 19 , Z 20 , Z 21 , Z 22 and Z 23 At least one of them is a N atom, In formula (3-4), Z 24 , Z 25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 Each independently selected from CR 2 or N atoms, and Z 24 , Z 25 , Z 26 , Z 27 , Z 28 , Z 29 , Z 30 , Z 31 , Z 32 and Z 33 At least one of them is a N atom, The R 2 One or a combination of at least two selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 condensed ring heteroaryl; in, * represents the access key of the group.

20. The compound according to claim 19, wherein Ar 1 It has the structure shown in (3-1) or (3-2).

21. The compound according to claim 20, wherein in formula (3-1), Z 1 , Z 2 , Z 3 , Z 4 and Z 5 At least two of them are N atoms; In formula (3-2), Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 and Z 13 At least two of them are N atoms.

22. According to any one of claims 13-17, the compound wherein Ar 1 One of the following groups, substituted or unsubstituted, is selected from: pyridyl, quinolyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl; When the above-mentioned groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, and C6-C30 condensed heteroaryl group.

23. The compound according to claim 22, wherein Ar 1 One selected from the following substituted or unsubstituted groups: quinazolinyl, triazine, quinoxalinyl; When the above-mentioned groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, and C6-C30 condensed heteroaryl group.

24. According to any one of claims 13-17, the compound wherein Ar 1 One selected from substituted or unsubstituted A1 to A14 groups: in, * represents the access key of the group; When the above-mentioned groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, and C6-C30 condensed heteroaryl group.

25. According to any one of claims 13-17, the Ar 1 One selected from the group B1 to B19: in, * represents the access key of the group.

26. The compound according to claim 12, wherein Ar 1 When Ar is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 electron-rich heteroaryl group, 1 One of the following substituted or unsubstituted groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, terphenyl, triphenylene, quaterphenyl, fluorenyl, benzofluorenyl, indolofluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-indenofluorenyl, trans-indenofluorenyl, trimerized indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzodibenzofuranyl, fluorenylbenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzodibenzothienyl, fluorenylbenzothienyl, acridinyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, phenothiazinyl or phenoxazinyl; When the above-mentioned groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic group, C10-C30 condensed aromatic group, C3-C30 monocyclic heteroaryl group, and C6-C30 condensed heteroaryl group.

27. The compound according to claim 1, wherein the compound has the structure shown below:

28. Use of the compound according to any one of claims 1 to 27, wherein the use is as a functional material in an organic electronic device, wherein the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper.

29. Use of the compound according to claim 28 as a host material of a light-emitting layer in an organic electroluminescent device.

30. An organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound according to any one of claims 1 to 27.

31. The organic electroluminescent device according to claim 30, wherein the light-emitting functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is between the hole transport region and the electron transport region; wherein, The light-emitting layer contains the compound according to any one of claims 1 to 27.

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