Organic electroluminescent device having high performance and compound thereof

Abstract

The present disclosure relates to an organic compound represented by formula O comprising an aza-spiro group, an electron transport material, and an organic electroluminescent device. The compound, as an electron transport material, is used in an organic electroluminescent device, and exhibits good electroluminescent performance.

Description

High-performance organic electroluminescent device and compound thereof Technical Field

[0001] The present disclosure relates to the technical field of luminescent materials, and in particular to an organic compound containing an azaspirocyclic group, an electron transport material, and an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) refer to the phenomenon in which organic electroluminescent materials emit light when electrically excited. As the latest display technology compared to traditional LCD displays, OLEDs offer advantages such as self-luminescence, wide viewing angles, low power consumption, full black display, and full color, and possess broad commercial application potential. In recent years, organic electroluminescent materials have made remarkable progress. Following the commercialization of flexible OLED devices, relevant research institutions and companies have been conducting research in this area. While research on organic electroluminescent materials has yielded significant results, there are still some pressing challenges to be addressed in the commercialization of OLEDs.

[0003] Driven by an electric field, holes are injected from the anode and gradually transferred to the EML via the HOMO energy levels of functional layers such as the HIL and HTL. Simultaneously, electrons are injected from the cathode and gradually transferred to the EML via the LUMO energy levels of functional layers such as the EIL and ETL. Holes and electrons recombine in the EML to produce excitons. When the excitons return from the excited state to the ground state, energy is emitted as light. Therefore, balancing the injection and recombination of holes and electrons is a key research topic for achieving excellent luminous efficiency in OLEDs.

[0004] Organic electroluminescent devices are carrier-injecting devices, and the efficiency of carrier recombination affects device efficiency. To achieve efficient carrier recombination in the luminescent layer and prevent exciton diffusion into surrounding functional layers, the functional layers adjacent to the luminescent layer must have a high T1 energy level. Therefore, developing electron transport materials with suitable T1 energy levels to effectively improve device efficiency is particularly important.

[0005] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, this can easily lead to an imbalance in the number of electrons and holes in the light-emitting layer, resulting in low device efficiency. Therefore, the development of electron transport materials with high electron mobility is extremely important.

[0006] In addition, since OLED devices generate Joule heat when voltage is applied, the organic material is prone to crystallization, affecting the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials.

[0007] Electron transport materials are electron-deficient in their molecular structure and possess strong electron-withdrawing groups. This imparts a certain degree of polarity to these materials, making them more susceptible to crystallization than hole transport materials. This can lead to poor film-forming properties and even pore blockage during film formation, hindering mass production of OLED devices. Therefore, crystallization performance is an important consideration in the development and design of electron transport materials.

[0008] In short, electron transport materials with excellent transport performance should have the following characteristics:

[0009] 1. Appropriate HOMO and LUMO energy levels. A lower LUMO energy level facilitates electron injection from the cathode, reducing the device's turn-on voltage. A lower HOMO energy level can more effectively confine hole carriers in the light-emitting layer, thereby increasing the recombination efficiency of holes and electrons.

[0010] 2. Higher triplet energy level. Since triplet excitons have a longer lifetime and a larger diffusion distance, the higher triplet energy level of electron transport materials can prevent triplet excitons from diffusing from the light-emitting layer to the electron transport layer, thereby improving the efficiency of the device.

[0011] 3. Higher electron mobility. Mobility affects the driving voltage of the device. Low electron mobility will increase the driving voltage of the device, thereby reducing the power efficiency of the device. In addition, if the driving voltage of the device is too high, it will also have a significant impact on the stability of the device.

[0012] 4. It can form a good amorphous film to avoid performance degradation caused by crystallization.

[0013] The efficiency and lifespan of currently available electron transport materials need to be improved, so developing stable and efficient electron transport materials to improve device efficiency and extend device life has very important practical application value.

[0014] Summary of the Invention

[0015] The inventors of the present disclosure designed an organic small molecule material containing an azaspirocyclic group, and used it as an electron transport material in an organic electroluminescent device, showing good electroluminescent performance.

[0016] Specifically, in the first aspect of the present disclosure, there is provided a compound represented by formula O, or a stereoisomer or tautomer of the compound,

[0017] in:

[0018] X 1 、X 2 、X3 、X 4 are each independently selected from CH, N, and X 1 、X 2 、X 3 、X 4 At least one of them is N, X 3 、X 4 Not all N at the same time;

[0019] X 5 、X 6 、X 7 are each independently selected from CH, N, and X 6 、X 7 Not all N at the same time;

[0020] A1 ring and A2 ring are each independently selected from C6-C12 aromatic rings;

[0021] Y is selected from -O-, -S-, -CR a R b -;

[0022] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0023] Preferably, R a 、R b are each independently selected from hydrogen, methyl;

[0024] Preferably, Y is selected from -O-, -S-, -CH2-,

[0025] More preferably, Y is selected from -O-, -S-;

[0026] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0027] L 1 、L 2 are each independently selected from a direct bond, a C6-C18 arylene group, and the C6-C18 arylene group is optionally substituted by 1 R L replaced by;

[0028] R L Selected from benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl;

[0029] R 1 、R 2Each is independently selected from diazaphenanthrenyl, 6-membered nitrogen-containing heteroaryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, and the diazaphenanthrenyl, 6-membered nitrogen-containing heteroaryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl are each independently optionally substituted by 1-2 R R replaced by;

[0030] R R Selected from C6-C18 aryl and fluorenyl, wherein the C6-C18 aryl and fluorenyl are each independently optionally substituted with 1-3 (preferably 1-2, more preferably 2) C1-C6 alkyl groups;

[0031] R 3 、R 4 Each is independently selected from hydrogen, C1-C6 alkyl;

[0032] Preferably, R 3 、R 4 For hydrogen.

[0033] In some embodiments, the A1 ring and the A2 ring are each independently selected from a benzene ring and a naphthalene ring.

[0034] In some embodiments, the A1 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring.

[0035] In some embodiments, the A1 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring.

[0036] In some embodiments, the A2 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring.

[0037] In some embodiments, the A2 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring.

[0038] In some embodiments, Selected from:

[0039] Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the right.

[0040] In some embodiments, Selected from:

[0041] Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the right.

[0042] In some embodiments, Selected from: Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the left.

[0043] In some embodiments, Selected from:

[0044] Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the left.

[0045] In some embodiments, L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and a biphenylene group, and the phenylene group, the naphthalene group, and the biphenylene group are each independently optionally substituted by one R L replaced.

[0046] In some embodiments, L 1 , L 2 are independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by one R L replaced.

[0047] In some embodiments, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected.

[0048] In some embodiments, R L Selected from benzoxazolyl and benzothiazolyl.

[0049] In some embodiments, R L It is benzoxazolyl.

[0050] In some embodiments, R L Selected from

[0051] In some embodiments, L 1 、L 2 Each independently selected from:

[0052] Direct keys, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected.

[0053] In some embodiments, R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 R R replaced.

[0054] In some embodiments, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced.

[0055] In some embodiments, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced.

[0056] In some embodiments, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced.

[0057] In some embodiments, R R Selected from phenyl, biphenyl, naphthyl, fluorenyl, and said phenyl, biphenyl, naphthyl, and fluorenyl are each independently and optionally substituted by two C1-C6 alkyl groups.

[0058] In some embodiments, R R Selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by two C1-C6 alkyl groups.

[0059] In some embodiments, R R It is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted by two methyl groups.

[0060] In some embodiments, R R Selected from

[0061] In some embodiments, R 1 、R 2 Each independently selected from:

[0062] In some embodiments, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0063] In the second aspect of the present disclosure, there is provided a compound represented by Formula I, or a stereoisomer or tautomer of the compound,

[0064] in:

[0065] X 1 、X 2 、X 3 、X 4 are each independently selected from CH, N, and X 1 、X 2 、X 3 、X 4 At least one of them is N, X 3 、X 4 Not all N at the same time;

[0066] Preferably, X 1 、X 2 、X 3 、X 4 are each independently selected from CH, N, and X 1 、X 2 、X 3 、X 4 There are two N, X 3 、X 4 Not all N at the same time;

[0067] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0068] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0069] More preferably, Selected from:

[0070] Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0071] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0072] A1 ring is selected from benzene ring and naphthalene ring;

[0073] Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0074] More preferably, the A1 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0075] A2 ring is selected from benzene ring and naphthalene ring;

[0076] Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0077] More preferably, the A2 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0078] Y is selected from -O-, -S-, -CR a R b -;

[0079] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0080] Preferably, R a 、Rb are each independently selected from hydrogen, methyl;

[0081] Preferably, Y is selected from -O-, -S-, -CH2-,

[0082] More preferably, Y is selected from -O-, -S-;

[0083] L 1 、L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and a biphenylene group, and the phenylene group, the naphthalene group, and the biphenylene group are each independently optionally substituted by one R L replaced by;

[0084] Preferably, L 1 、L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0085] More preferably, L 1 、L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0086] R L Selected from benzoxazolyl and benzothiazolyl;

[0087] Preferably, R L is benzoxazolyl;

[0088] More preferably, R L for

[0089] Most preferably, L 1 、L 2 Each independently selected from a direct bond,

[0090] Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0091] R 1 、R 2Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0092] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0093] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0094] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0095] R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein each of the phenyl, biphenyl, naphthyl, and fluorenyl groups is independently optionally substituted with two C1-C6 alkyl groups;

[0096] Preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0097] More preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0098] Most preferably, R R Selected from

[0099] Most preferably, R 1 、R 2 Each independently selected from:

[0100] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0101] R 3 、R 4 Each is independently selected from hydrogen, C1-C6 alkyl;

[0102] Preferably, R 3 、R 4 For hydrogen.

[0103] In the third aspect of the present disclosure, there is provided a compound represented by formula I-1, or a stereoisomer or tautomer of the compound,

[0104] in:

[0105] A1 ring is selected from benzene ring and naphthalene ring;

[0106] Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0107] More preferably, the A1 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0108] A2 ring is selected from benzene ring and naphthalene ring;

[0109] Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0110] More preferably, the A2 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0111] Y is selected from -O-, -S-, -CR a R b -;

[0112] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0113] Preferably, Ra 、R b are each independently selected from hydrogen, methyl;

[0114] Preferably, Y is selected from -O-, -S-, -CH2-,

[0115] More preferably, Y is selected from -O-, -S-;

[0116] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0117] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0118] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0119] L 1 、L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and a biphenylene group, and the phenylene group, the naphthalene group, and the biphenylene group are each independently optionally substituted by one R L replaced by;

[0120] Preferably, L 1 、L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0121] More preferably, L 1 、L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0122] R L Selected from benzoxazolyl and benzothiazolyl;

[0123] Preferably, R L is benzoxazolyl;

[0124] More preferably, R L for

[0125] Most preferably, L 1 、L 2 Each independently selected from a direct bond,

[0126] Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0127] R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0128] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0129] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0130] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0131] R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein each of the phenyl, biphenyl, naphthyl, and fluorenyl groups is independently optionally substituted with two C1-C6 alkyl groups;

[0132] Preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0133] More preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0134] Most preferably, R R Selected from

[0135] Most preferably, R 1 、R 2 Each independently selected from:

[0136] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0137] In a fourth aspect of the present disclosure, there is provided a compound represented by formula I-2, or a stereoisomer or tautomer of the compound,

[0138] in:

[0139] A1 ring is selected from benzene ring and naphthalene ring;

[0140] Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0141] More preferably, the A1 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0142] A2 ring is selected from benzene ring and naphthalene ring;

[0143] Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0144] More preferably, the A2 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0145] Y is selected from -O-, -S-, -CRa R b -;

[0146] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0147] Preferably, R a 、R b are each independently selected from hydrogen, methyl;

[0148] Preferably, Y is selected from -O-, -S-, -CH2-,

[0149] More preferably, Y is selected from -O-, -S-;

[0150] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0151] Preferably, n1 is 0 and n2 is 1;

[0152] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0153] Preferably, Selected from Among them, the carbon atom No. 1 is connected to the central spiro carbon atom, and the carbon atom No. 2 is connected to the carbon atom of the aromatic ring on the left;

[0154] L 1 , L 2 are each independently selected from a direct bond, a phenylene group;

[0155] Preferably, L 1 , L 2 is a direct key;

[0156] R 1 、R 2 are each independently selected from diazophanol, and the diazophanol is optionally substituted by 1-2 (preferably 2) R R Replaced by R R is phenyl;

[0157] Preferably, R 1 、R 2 are each independently selected from diazaphenanthroline;

[0158] More preferably, R 1 、R 2 Each independently selected from:

[0159] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0160] In a fifth aspect of the present disclosure, there is provided a compound represented by formula I-3, or a stereoisomer or tautomer of the compound,

[0161] in:

[0162] A1 ring is selected from benzene ring and naphthalene ring;

[0163] Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0164] More preferably, the A1 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0165] A2 ring is selected from benzene ring and naphthalene ring;

[0166] Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0167] More preferably, the A2 ring is Among them, the No. 1 C atom is fused to the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused to the carbon atom far from Y on the middle six-membered ring;

[0168] Y is selected from -O-, -S-, -CR a R b -;

[0169] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0170] Preferably, R a 、R b are each independently selected from hydrogen, methyl;

[0171] Preferably, Y is selected from -O-, -S-, -CH2-,

[0172] More preferably, Y is selected from -O-, -S-;

[0173] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0174] Preferably, n1 is 0 and n2 is 1;

[0175] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0176] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0177] L 1 、L 2 are each independently selected from a direct bond, a phenylene group;

[0178] Preferably, L 1 、L 2 is a direct key;

[0179] R 1 、R 2 are each independently selected from diazophanol, and the diazophanol is optionally substituted by 1-2 (preferably 2) R R Replaced by R R is phenyl;

[0180] Preferably, R 1 、R 2 are each independently selected from diazaphenanthroline;

[0181] More preferably, R 1 、R 2 Each independently selected from:

[0182] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0183] In a sixth aspect of the present disclosure, there is provided a compound represented by Formula II, or a stereoisomer or tautomer of the compound,

[0184] X 2 、X 3are each independently selected from CH, N, and X 2 、X 3 At least one of them is N;

[0185] X 5 、X 6 are each independently selected from CH, N, and X 5 、X 6 At least one of them is N;

[0186] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0187] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0188] More preferably, Selected from:

[0189] Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0190] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0191] More preferably, Selected from:

[0192] Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0193] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0194] Preferably, ring A1 and ring A2 are benzene rings;

[0195] Y is selected from -O-, -S-, -CR a R b -;

[0196] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0197] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0198] More preferably, R a 、R b is methyl;

[0199] Preferably, Y is selected from -O-, -S-,

[0200] More preferably, Y is selected from -O-, -S-;

[0201] L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by one R L replaced by;

[0202] Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0203] More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L replaced by;

[0204] R L Selected from benzoxazolyl, benzothiazolyl;

[0205] Preferably, R L is benzoxazolyl;

[0206] More preferably, R L Selected from

[0207] Most preferably, L 1 , L 2 Each independently selected from:

[0208] Direct keys, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0209] R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0210] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0211] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0212] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0213] R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein each of the phenyl, biphenyl, naphthyl, and fluorenyl groups is independently optionally substituted with two C1-C6 alkyl groups;

[0214] Preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0215] More preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0216] Most preferably, R R Selected from

[0217] Most preferably, R 1 、R 2 Each independently selected from:

[0218] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0219] R 3 、R 4 Each is independently selected from hydrogen, C1-C6 alkyl;

[0220] Preferably, R 3 、R 4 For hydrogen.

[0221] In a seventh aspect of the present disclosure, there is provided a compound represented by formula II-1, or a stereoisomer or tautomer of the compound,

[0222] in:

[0223] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0224] Preferably, ring A1 and ring A2 are benzene rings;

[0225] Y is selected from -O-, -S-, -CR a R b -;

[0226] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0227] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0228] More preferably, R a 、R b is methyl;

[0229] Preferably, Y is selected from -O-, -S-,

[0230] More preferably, Y is selected from -O-, -S-;

[0231] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0232] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0233] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0234] L 1 、L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Replaced by R L is benzoxazolyl;

[0235] Preferably, L 1 、L 2 Each independently selected from a direct bond,

[0236] R 1 、R 2 Each is independently selected from phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0237] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, triazinyl, benzoxazolyl, and the pyridinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0238] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridyl, s-triazinyl, benzoxazolyl, and the pyridyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0239] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0240] R R is selected from phenyl, biphenyl, and fluorenyl, wherein the phenyl, biphenyl, and fluorenyl are each independently optionally substituted with two C1-C6 alkyl groups;

[0241] Preferably, R R is selected from phenyl, biphenyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0242] More preferably, R R is selected from phenyl, biphenyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0243] Most preferably, R R Selected from

[0244] Most preferably, R 1 、R 2 Each independently selected from:

[0245] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0246] In an eighth aspect of the present disclosure, there is provided a compound represented by formula II-2, or a stereoisomer or tautomer of the compound,

[0247] in:

[0248] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0249] Preferably, ring A1 and ring A2 are benzene rings;

[0250] Y is selected from -O-, -S-, -CR a R b -;

[0251] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0252] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0253] More preferably, R a 、R b is methyl;

[0254] Preferably, Y is selected from -O-, -S-,

[0255] More preferably, Y is selected from -O-, -S-;

[0256] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0257] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0258] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0259] L 1 、L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Replaced by R L is benzoxazolyl;

[0260] Preferably, L 1 、L 2 Each independently selected from a direct bond,

[0261] R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0262] Preferably, R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0263] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0264] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced by;

[0265] R R is selected from phenyl, biphenyl, and fluorenyl, wherein the phenyl, biphenyl, and fluorenyl are each independently optionally substituted with two C1-C6 alkyl groups;

[0266] Preferably, R R is selected from phenyl, biphenyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0267] More preferably, R R is selected from phenyl, biphenyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0268] Most preferably, R R Selected from

[0269] Most preferably, R 1 、R 2 Each independently selected from:

[0270] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0271] In the ninth aspect of the present disclosure, there is provided a compound represented by formula II-3, or a stereoisomer or tautomer of the compound,

[0272] in:

[0273] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0274] Preferably, ring A1 and ring A2 are benzene rings;

[0275] Y is selected from -O-, -S-, -CR a R b -;

[0276] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0277] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0278] More preferably, R a 、R b is methyl;

[0279] Preferably, Y is selected from -O-, -S-,

[0280] More preferably, Y is selected from -O-, -S-;

[0281] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0282] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0283] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0284] L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Replaced by R L is benzoxazolyl;

[0285] Preferably, L 1 , L 2 Each independently selected from a direct bond,

[0286] R 1 、R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0287] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyrimidinyl, triazinyl, benzoxazolyl, and the pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0288] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0289] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced by;

[0290] R R is selected from phenyl and fluorenyl, wherein the phenyl and fluorenyl are each independently optionally substituted with two C1-C6 alkyl groups;

[0291] Preferably, R R is selected from phenyl and fluorenyl, wherein the fluorenyl is optionally substituted by two C1-C6 alkyl groups;

[0292] More preferably, R R is selected from phenyl and fluorenyl, wherein the fluorenyl is optionally substituted by 2 methyl groups;

[0293] Most preferably, R R Selected from

[0294] Most preferably, R 1 、R 2 Each independently selected from:

[0295] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0296] In the tenth aspect of the present disclosure, there is provided a compound represented by formula II-4, or a stereoisomer or tautomer of the compound,

[0297] in:

[0298] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0299] Preferably, ring A1 and ring A2 are benzene rings;

[0300] Y is selected from -O-, -S-, -CR a R b -;

[0301] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0302] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0303] More preferably, R a 、R b is methyl;

[0304] Preferably, Y is selected from -O-, -S-,

[0305] More preferably, Y is selected from -O-, -S-;

[0306] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0307] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0308] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0309] L 1 、L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by one R L replaced by;

[0310] Preferably, L 1 、L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0311] More preferably, L 1 、L 2 Each independently selected from a direct bond, and Optionally replaced by 1 R L replaced by;

[0312] R L Selected from benzoxazolyl and benzothiazolyl;

[0313] Preferably, R L is benzoxazolyl;

[0314] More preferably, R L for

[0315] Most preferably, L 1 , L 2 Each independently selected from a direct bond, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0316] R 1 、R 2 Each is independently selected from phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0317] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, triazinyl, benzoxazolyl, and the pyridinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0318] More preferably, R 1 、R 2 Each is independently selected from o-phenanthroline, pyridyl, s-triazinyl, benzoxazolyl, and the pyridyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0319] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced by;

[0320] R R is selected from phenyl and biphenyl, wherein the phenyl and biphenyl are each independently optionally substituted with two C1-C6 alkyl groups;

[0321] Preferably, R R Selected from phenyl, biphenyl;

[0322] More preferably, R R Selected from

[0323] Most preferably, R 1 、R 2 Each independently selected from:

[0324] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0325] In the eleventh aspect of the present disclosure, there is provided a compound represented by formula II-5, or a stereoisomer or tautomer of the compound,

[0326] in:

[0327] A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring;

[0328] Preferably, ring A1 and ring A2 are benzene rings;

[0329] Y is selected from -O-, -S-, -CR a R b -;

[0330] R a 、R b Each is independently selected from hydrogen, C1-C6 alkyl;

[0331] Preferably, R a 、R b Each independently selected from C1-C6 alkyl;

[0332] More preferably, R a 、R b is methyl;

[0333] Preferably, Y is selected from -O-, -S-,

[0334] More preferably, Y is selected from -O-, -S-;

[0335] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0336] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right;

[0337] Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the carbon atom of the aromatic ring on the left;

[0338] L 1、L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by one R L replaced by;

[0339] Preferably, L 1 、L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0340] More preferably, L 1 、L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L replaced by;

[0341] R L Selected from benzoxazolyl and benzothiazolyl;

[0342] Preferably, R L is benzoxazolyl;

[0343] More preferably, R L Selected from

[0344] Most preferably, L 1 、L 2 Each independently selected from:

[0345] Direct keys, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0346] R 1 、R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0347] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyrimidinyl, triazinyl, benzoxazolyl, and the pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0348] More preferably, R 1 、R 2Each is independently selected from o-phenanthroline, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by;

[0349] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced by;

[0350] R R is selected from phenyl, biphenyl, and naphthyl, wherein the phenyl, biphenyl, and naphthyl are each independently optionally substituted with two C1-C6 alkyl groups;

[0351] Preferably, R R Selected from phenyl, biphenyl, naphthyl;

[0352] More preferably, R R Selected from

[0353] Most preferably, R 1 、R 2 Each independently selected from:

[0354] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0355] In the twelfth aspect of the present disclosure, there is provided a compound represented by formula Oc-1, formula Oc-2 or formula Oc-3, or a stereoisomer or tautomer of the compound,

[0356] in:

[0357] Y is selected from O, S;

[0358] n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time;

[0359] L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and a biphenylene group, and the phenylene group, the naphthalene group, and the biphenylene group are each independently optionally substituted by one R L replaced by;

[0360] Preferably, L1 、L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by;

[0361] More preferably, L 1 、L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0362] R L Selected from benzoxazolyl and benzothiazolyl;

[0363] Preferably, R L is benzoxazolyl;

[0364] More preferably, R L Selected from

[0365] Most preferably, L 1 、L 2 Each independently selected from:

[0366] Direct keys, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected;

[0367] R 1 、R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 R R replaced by;

[0368] Preferably, R 1 、R 2 Each is independently selected from diazophanol, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by;

[0369] More preferably, R 1 、R 2Each is independently selected from o-phenanthroline, pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by;

[0370] More preferably, R 1 、R 2 Each independently selected from and Each independently optionally substituted by 1-2 R R replaced by;

[0371] R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein each of the phenyl, biphenyl, naphthyl, and fluorenyl groups is independently optionally substituted with two C1-C6 alkyl groups;

[0372] Preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two C1-C6 alkyl groups;

[0373] More preferably, R R is selected from phenyl, biphenyl, naphthyl, and fluorenyl, wherein the fluorenyl is optionally substituted with two methyl groups;

[0374] Most preferably, R R Selected from

[0375] Most preferably, R 1 、R 2 Each independently selected from:

[0376] Most preferably, R 1 -L 1 -、R 2 -L 2 - are each independently selected from:

[0377] Unless otherwise specified, the above groups and substituents have the common meanings in the field of organic chemistry.

[0378] Throughout this disclosure, substituents of the compounds disclosed herein are disclosed by group class or range. It is specifically noted that the present invention includes each independent subcombination of the individual members of these group classes and ranges. For example, the term "C1-C6 alkyl" specifically refers to the independently disclosed methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl groups.

[0379] In this disclosure, unless otherwise explicitly stated, the description “…are independently selected from” used throughout this document may mean that in different groups, the specific options expressed by the same or different symbols do not affect each other, or that in the same group, the specific options expressed by the same or different symbols do not affect each other.

[0380] In the present disclosure, the term "C1-C6 alkyl" refers to an alkyl group having 1 to 6 carbon atoms, preferably a "C1-C4 alkyl group", more preferably a "C1-C3 alkyl group", and most preferably a "C1-C2 alkyl group". Examples of "C1-C6 alkyl" include, but are not limited to, methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, tert-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl), and the like. Examples of "C1-C4 alkyl" include, but are not limited to, methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, tert-butyl), and the like. Examples of "C1-C3 alkyl" include, but are not limited to, methyl, ethyl, propyl (e.g., n-propyl, isopropyl), and the like. Examples of "C1-C2 alkyl" include, but are not limited to, methyl and ethyl.

[0381] In the present disclosure, the terms "aryl" and "aromatic ring" are used interchangeably and refer to a carbon ring in which all carbon atoms have conjugated p orbitals, such as phenyl and naphthyl. Two or more rings may be connected by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc. For example, "C6-C12 aryl / ring" may be phenyl / ring, naphthyl / ring, biphenyl / ring, and "C6-C18 aryl / ring" may be phenyl / ring, naphthyl / ring, biphenyl / ring, terphenyl / ring, anthracenyl / ring, phenanthrenyl / ring, etc.

[0382] In the present disclosure, the term "arylene group" refers to a divalent group obtained by losing one hydrogen atom from any of the above-mentioned aromatic groups or two hydrogen atoms from the above-mentioned aromatic rings. For example, a "C6-C12 arylene group" can be a phenylene group, a naphthalene group, or a biphenylene group. A "C6-C18 aryl group" can be a phenylene group, a naphthalene group, a biphenylene group, a terphenylene group, an anthracene group, a phenanthracene group, and the like.

[0383] In the present disclosure, heteroatom refers to N, O, S or P.

[0384] In this disclosure, the terms "heteroaryl" and "heteroaromatic ring" are used interchangeably and refer to aromatic 5- or 6-membered monocyclic groups, 8-, 9- or 10-membered bicyclic groups, and 11- to 14-membered tricyclic or higher ring groups having at least one heteroatom (N, O, S or P) in at least one ring, the heteroatom-containing ring optionally further having 1, 2 or 3 heteroatoms selected from N, O, S or P. Heteroaryl groups or heteroaromatic rings that are bicyclic, tricyclic or higher require a bicyclic, tricyclic or higher ring structure to form an aromatic system. The heteroaryl group or heteroaromatic ring may be attached at any available nitrogen or carbon atom of any ring.

[0385] Exemplary monocyclic heteroaryl groups or monocyclic heteroaromatic rings include, but are not limited to, pyrrolyl / ring, pyrazolyl / ring, imidazolyl / ring, oxazolyl / ring, isoxazolyl / ring, thiazolyl / ring, thiadiazolyl / ring, isothiazolyl / ring, furanyl / ring, thienyl / ring, oxadiazolyl / ring, pyridinyl / ring, pyrazinyl / ring, pyrimidinyl / ring, pyridazinyl / ring, triazinyl / ring, triazolyl / ring, pyridazinyl / ring, 2-pyridone, and the like.

[0386] Exemplary bicyclic heteroaryl groups include, but are not limited to, indolyl, 5-azaindolyl, pyrrolo[2,3-d]pyrimidinyl, 5,6-diazaindolyl, 6-azaindolyl, 7-azaindolyl, pyrazolo[3,4-b]pyridinyl, pyrrolo[2,3-c]pyridazinyl, thieno[2,3-d]imidazolyl, thieno[2,3-d]imidazolyl, pyrazolo[3,4-c]pyridinyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, benzothienyl, quinolinyl, isoquinolinyl, benzofuranyl, indolizinyl, quinoxalinyl, pyrrolopyrimidinyl, furopyridinyl, isoindolyl, and the like.

[0387] In the present disclosure, the term "heteroarylene group" refers to a divalent group obtained by losing one hydrogen atom from any of the above heteroaryl groups or by losing two hydrogen atoms from the above heteroaryl ring.

[0388] In the present disclosure, for example, "the pyridyl, pyrimidyl, triazinyl, benzoxazolyl are each independently optionally substituted with 1-2 R R substituted by", wherein "each independently" means that the substituents of pyridyl, pyrimidinyl, triazinyl and benzoxazolyl do not affect each other and may be the same or different; "optionally" means that the pyridyl, pyrimidinyl, triazinyl and benzoxazolyl may be substituted by a substituent or may not be substituted; and when the pyridyl, pyrimidinyl, triazinyl and benzoxazolyl are each independently substituted by more than one (i.e., two) R R When substituted, selected from R R The two substituents may be the same or different. For other similar definitions in this disclosure, please refer to the above content for understanding.

[0389] In the present disclosure, Represents the A1 ring and the middle six-membered ring Condensed, Represents the A2 ring and the middle six-membered ring Condensed, Represents a substituent In the ring The substitution position on is not fixed, and it can be understood by those skilled in the art that At a certain position such as X 1 When the position is replaced, X 1 It cannot be N, but CH, and in fact the position of the hydrogen atom in "CH" will be The remaining similar definitions in this disclosure are understood with reference to the foregoing.

[0390] In one aspect of the present disclosure, an electron transport material is provided, which comprises the aforementioned compound, or a stereoisomer or tautomer of the compound.

[0391] In another aspect of the present disclosure, an organic electroluminescent device is provided, which includes an electron transport layer, wherein the material of the electron transport layer includes the aforementioned compound, or a stereoisomer or tautomer of the compound.

[0392] In some embodiments, the organic electroluminescent device includes a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a second electrode stacked in sequence, and the material of the electron transport layer contains the aforementioned compound, or a stereoisomer or tautomer of the compound.

[0393] In the present disclosure, an exemplary organic electroluminescent device is provided, as shown in FIG1 , comprising 1: a substrate, 2: a first electrode, 3: a hole injection layer, 4: a hole transport layer, 5: an electron blocking layer, 6: a light-emitting layer, 7: a hole blocking layer, 8: an electron transport layer, 9: an electron injection layer, and 10: a second electrode, which are stacked in sequence.

[0394] In this disclosure, as examples, the first electrode can be a transparent oxide such as ITO or IZO, or a composite electrode formed of ITO / Ag / ITO, Ag / IZO, CNT / ITO, or CNT / IZO. The second electrode can be a silver-magnesium composite electrode or an Al electrode. The electroluminescent device also includes a substrate 1 disposed on the side of the first electrode 2 facing away from the second electrode 10. Substrate 1 can be made of a transparent rigid or flexible material, such as glass or polyimide, enabling both rigid and flexible substrate displays.

[0395] The electroluminescent device further comprises a hole injection layer, a hole transport layer, an electron blocking layer and a light emitting layer which are sequentially stacked and arranged on the side of the anode close to the hole blocking layer; and an electron injection layer which is arranged on the side of the electron transport layer away from the hole blocking layer.

[0396] The hole injection layer can be an inorganic oxide, such as oxides of metals such as molybdenum, titanium, vanadium, rhenium, ruthenium, chromium, zirconium, hafnium, tantalum, silver, tungsten, and manganese, or it can be a dopant of a strong electron-withdrawing system, such as F4TCNQ, HAT-CN, etc., or the hole transport material can be P-type doped. The thickness of the hole injection layer can be 5nm to 30nm.

[0397] The material of the hole transport layer has good hole transport properties and can be an aromatic amine or carbazole material, such as NPB, TPD, BAFLP, DFLDPBi, etc. The thickness of the hole transport layer can be 300 nm to 100 nm.

[0398] The electron blocking layer, i.e., the luminescent auxiliary layer, has hole transport properties and can be a red luminescent auxiliary layer, a green luminescent auxiliary layer, or a blue luminescent auxiliary layer. The material of the luminescent auxiliary layer can be an aromatic amine or carbazole material, such as CBP, PCzPA, etc. The thickness of the electron blocking layer can be 5nm to 50nm.

[0399] The light-emitting layer can be a phosphorescent host and a red phosphorescent dopant, a phosphorescent host and a green phosphorescent dopant, or a fluorescent host and a fluorescent dopant. The host material of the light-emitting layer can include one material or a mixture of two or more materials. The host material of the blue light-emitting layer can be selected from anthracene derivatives ADN, MADN, etc., and the guest material can be a pyrene derivative, a fluorene derivative, a perylene derivative, a styrylamine derivative, a metal complex, etc., such as TBPe, BDAVBi, DPAVBi, FIrpic, etc. The host material of the green light-emitting layer can be selected from coumarin dyes, quinacridone copper, etc. Derivatives of the type, polycyclic aromatic hydrocarbons, diamine anthracene derivatives, carbazole derivatives, such as DMQA, BA-NPB, Alq3, etc., the guest material can be a metal complex, such as Ir(ppy)3, Ir(ppy)2(acac), etc.; the red light-emitting host material can be selected from DCM series materials, such as DCM, DCJTB, DCJTI, etc., the guest material can be a metal complex, such as Ir(piq)2(acac), PtOEP, Ir(btp)2(acac), etc., and the thickness of the light-emitting layer can be 20nm to 100nm.

[0400] The thickness of the hole blocking layer can be 5nm to 100nm, and the thickness of the electron transport layer can be 20nm to 100nm. The hole blocking layer and the electron transport layer independently include aromatic heterocyclic compounds, such as imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, benzimidazolephenanthridine derivatives, and oxazine derivatives such as pyrimidine derivatives and triazine derivatives, as well as quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives and other compounds containing nitrogen-containing six-membered ring structures, and may also include compounds having phosphine oxide-based substituents on the heterocyclic ring, such as: OXD-7, TAZ, p-EtTAZ), BPhen, BCP, the electron transport material disclosed in the present invention, etc.

[0401] The thickness of the electron injection layer may be 1 nm to 10 nm, and the material of the electron injection layer includes alkali metals or metals, such as LiF, Yb, Mg, Ca, or compounds thereof.

[0402] As shown in the embodiment of Figure 1, the structure of the light-emitting device is: substrate / first electrode (ITO) / hole injection layer (5nm) / hole transport layer (30nm) / electron blocking layer (10nm) / light-emitting layer (20nm) / hole blocking layer (10nm) / electron transport layer (40nm) / electron injection layer (1nm) / second electrode (100nm).

[0403] In another aspect of the present disclosure, an electronic device is provided, which includes the aforementioned organic electroluminescent device. Beneficial effects

[0404] 1. The present disclosure provides an electron transport material comprising an azaspirocyclic group and some electron-withdrawing groups, and applies the material to an organic electroluminescent device to improve the performance of the light-emitting device. In the structure of the electron transport material, the benzoxazole group has a high electron affinity, which gives it excellent electron conduction properties; at the same time, in the process of designing the molecular structure, a variety of electron-withdrawing groups are selected, which have a low LUMO energy level and can effectively transport electrons to the light-emitting layer, thereby increasing the recombination probability of electrons and holes in the light-emitting layer, and the device exhibits high luminous efficiency; the spirocyclic group has an orthogonal spatial configuration, which can reduce the van der Waals force between molecules and help prevent the crystallization of the electron transport material; at the same time, the structure is made relatively rigid, so that the compound has a high glass transition temperature, which improves the film-forming property and thermal stability of the compound.

[0405] 2. The present disclosure provides an electron transport material comprising an electron-withdrawing group and an azaspiro group, and the material is applied to an organic electroluminescent device. In the structure of the electron transport material, the selected multiple electron-withdrawing groups have high electron affinity, so that it has excellent electron conduction characteristics, can effectively transport electrons to the light-emitting layer, increase the recombination probability of electrons and holes in the light-emitting layer, and the device exhibits high luminous efficiency; the azaspiro group has an orthogonal spatial stereo configuration, which can reduce the van der Waals force between molecules and help prevent the crystallization of the electron transport material; at the same time, the structure has a relatively rigid structure that gives the compound a higher glass transition temperature, improves the film-forming property and thermal stability of the compound, and further improves the luminous life and operational stability of the organic electroluminescent device.

[0406] 3. The present disclosure provides an electron transport material comprising an azaspirocyclic group and some electron-withdrawing groups, and applies the material to an organic electroluminescent device to improve the performance of the light-emitting device. In the structure of the electron transport material, the azaphenanthrene group, the benzoxazole group, and the azine group all have high electron affinity, which gives them excellent electron conduction properties. At the same time, in the process of designing the molecular structure, some West Point groups are selected, which have a low LUMO energy level and can effectively transport electrons to the light-emitting layer, thereby increasing the recombination probability of electrons and holes in the light-emitting layer, and the device exhibits high luminous efficiency. The spirocyclic group has an orthogonal spatial configuration, which can reduce the van der Waals force between molecules and help prevent the crystallization of the electron transport material. At the same time, the structure is made relatively rigid, so that the compound has a higher glass transition temperature, which improves the film-forming property and thermal stability of the compound. These material properties have significantly improved the material's use process and the performance of the device.

[0407] 4. The present disclosure provides a material containing an azaspirocyclic group of sp3 hybridized carbon atoms. The sp3 hybridized carbon atoms have an orthorhombic configuration and a large steric hindrance, which can reduce the van der Waals force between molecules and inhibit the crystallization phenomenon of the material film. The material is used as an electron transport material and applied to organic electroluminescent devices in order to achieve excellent device performance. In the structure of the electron transport material, the various electron-withdrawing groups selected have a high electron affinity, which makes it have excellent electron conduction characteristics, can effectively transport electrons to the light-emitting layer, and increase the recombination probability of electrons and holes in the light-emitting layer. The device exhibits high luminous efficiency; at the same time, the structure has a relatively rigid structure, which makes the compound have a higher glass transition temperature, improves the film-forming property and thermal stability of the compound, and further improves the luminous life and operational stability of the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0408] Figure 1 shows an exemplary device structure of an experimental example of the present disclosure, wherein: 1: substrate, 2: first electrode, 3: hole injection layer, 4: hole transport layer, 5: electron blocking layer, 6: light-emitting layer, 7: hole blocking layer, 8: electron transport layer, 9: electron injection layer, 10: second electrode. DETAILED DESCRIPTION

[0409] The present disclosure is further explained below with reference to specific embodiments, but these embodiments should not be construed as limiting the present disclosure in any way.

[0410] Example: Preparation and physicochemical properties of compounds

[0411] 1. Preparation of Compounds

[0412] The present disclosure prepared the following compound:

[0413] For example, the following disclosure provides methods for synthesizing some compounds. Those skilled in the art can refer to the following methods to prepare other compounds. Wherein, raw materials not otherwise specified can be commercially obtained. Synthesis of intermediates:

[0414] Synthesis of intermediate M1: In a round-bottom flask, 7-bromo-9H-indolo[1,2-b]pyrazin-9-one (5 g, 19.3 mmol) and phenol (2.18 g, 23.2 mmol) were heated to reflux and stirred for 12 h in a mixed solution of trifluoromethanesulfonic acid (6 g) and toluene (60 ml). The reaction was confirmed by thin layer chromatography (TLC) and terminated after the addition of water. The organic layer was extracted with dichloromethane and filtered under reduced pressure. The mixture was subjected to column purification and recrystallization to obtain intermediate compound M1 (5.20 g, yield: 65%). 1 H NMR (500MHz, Chloroform) δ8.58 (s, 1H), 8.54 (s, 1H), 8.21 (s, 1H), 7.57 (d, J = 5.0Hz, 2H), 7.31 (s, 2H), 7.18 (m, 4H), 7.00 (s, 2H).

[0415] Synthesis of intermediate M2: The synthesis of intermediate M2 is similar to that of intermediate M1, except that the benzene ring is replaced by thiophenol to obtain intermediate M2. 1 H NMR (500MHz, Chloroform) δ8.58(s,1H),8.54(s,1H),8.21(s,1H),7.69(s,2H),7.57(d,J=5.0Hz,2H),7.33(s,1H),7.03(d,J=10.0Hz,4H).

[0416] Synthesis of intermediate M3: The synthesis of intermediate M3 is similar to that of intermediate M1, except that 7-bromo-9H-indolo[1,2-b]pyrazin-9-one is replaced by 2-bromo-9H-indolo[1,2-b]pyrazin-9-one to obtain intermediate M3. 1 H NMR (500MHz, Chloroform) δ8.63 (s, 1H), 8.18 (s, 1H), 7.47 (d, J = 5.0Hz, 2H), 7.31 (s, 3H), 7.18 (m, 4H), 7.00 (s, 2H).

[0417] Synthesis of intermediate M4: The synthesis of intermediate M4 is similar to that of intermediate M1, except that 7-bromo-9H-indolo[1,2-b]pyrazin-9-one is replaced by 3-bromo-9H-cyclopenta[1,2-c:4,3-c']bipyridin-9-one to obtain intermediate M4. 1 H NMR (500MHz, Chloroform) δ8.95(s,1H),8.63(s,1H),8.54(s,1H),8.15(s,1H),7.56(s,1H),7.31(s,2H),7.18(m,4H),7.00(s,2H).

[0418] Synthesis of intermediate M5: The synthesis of intermediate M5 is similar to that of intermediate M1, except that 7-bromo-9H-indolo[1,2-b]pyrazin-9-one is replaced by 3-bromo-5H-cyclopenta[2,1-c:3,4-c']bipyridin-5-one to obtain intermediate M5. 1 H NMR (500MHz, Chloroform) δ9.24(s,1H),8.68(s,1H),8.20(s,1H),7.94(s,1H),7.31(s,2H),7.18(m,4H),7.06(s,1H),7.00(s,2H).

[0419] Synthesis of intermediate M6: The synthesis of intermediate M6 is similar to that of intermediate M1, except that 7-bromo-9H-indolo[1,2-b]pyrazin-9-one is replaced by 3-bromo-5H-cyclopenta[2,1-c:3,4-c']bipyridin-5-one and the benzene ring is replaced by thiophenol to obtain intermediate M6. 1 H NMR (500MHz, Chloroform) δ9.24(s,1H),8.67(s,1H),8.20(s,1H),8.02(s,1H),7.69(s,2H),7.33(s,1H),7.08-6.96(m,5H).

[0420] Synthesis of intermediate M7: The synthesis of intermediate M7 is similar to that of intermediate M1, except that 7-bromo-9H-indolo[1,2-b]pyrazin-9-one is replaced with 3,7-dibromo-5H-cyclopentadieno[2,1-c:3,4-c']dipyridin-5-one to obtain intermediate M7. 1 H NMR (500MHz, Chloroform) δ8.67 (s, 1H), 7.94 (s, 1H), 7.31 (s, 1H), 7.18 (d, J = 15.0Hz, 2H), 7.00 (s, 1H).

[0421] Synthesis of compounds:

[0422] Synthesis of Compound 1: M1 (5 g, 12.14 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline (3.80 g, 12.5 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), potassium carbonate (2.76 g, 20 mmol), and THF / H2O (60 mL / 12 mL) were added to a 200 mL pressure bottle. Under argon, the mixture was heated to 100°C and pressurized for 12 h. After the reaction, the mixture was cooled to room temperature, resulting in the precipitation of a large amount of solid. The reaction mixture was filtered, the filtered solid washed with ethanol (100 mL), and dried to obtain a white powder (4.66 g, 9.10 mmol). Yield: 75%. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.63(s,1H),8.58(s,1H),8.53(m,2H),8.49-8 .36(m,3H),7.88(s,1H),7.57(d,J=10.0Hz,2H),7.33(m,3H),7.18(m,4H),7.00(s,2H).

[0423] Synthesis of compound 2: The synthesis of compound 2 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline to obtain compound 2. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.62-8.49(m,3H),8.45(d,J=3.2Hz,2H),8.26(s,1 H),8.03(s,1H),7.80(s,1H),7.58(m,2H),7.31(s,2H),7.19(t,J=7.5Hz,5H),7.00(s,2H).

[0424] Synthesis of compound 3: The synthesis of compound 3 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline to obtain compound 3. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.63-8.27(m,7H),8.03(s,1H),7.88(s, 1H),7.70(s,1H),7.64-7.50(m,3H),7.33(m,3H),7.25-7.12(m,5H),7.00(s,2H).

[0425] Synthesis of compound 4: The synthesis of compound 4 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline to obtain compound 4. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.63-8.48(m,3H),8.45(d,J=1.0Hz,2H),8 .26(s,1H),8.03(s,1H),7.80(s,1H),7.57(m,2H),7.38-7.12(m,11H),7.00(s,2H).

[0426] Synthesis of compound 5: The synthesis of compound 5 is similar to that of compound 1, except that M1 is replaced by M2 to obtain compound 5. 1 H NMR(500MHz,Chloroform)δ8.80(s,1H),8.63(s,1H),8.58(s,1H),8.53(d,J=15.0Hz,2H),8.48-8.35( m,3H),7.88(s,1H),7.69(s,2H),7.57(d,J=10.0Hz,2H),7.34(d,J=5.0Hz,3H),7.03(d,J=10.0Hz,4H).

[0427] Synthesis of compound 6: The synthesis of compound 6 is similar to that of compound 4, except that M1 is replaced by M2 to obtain compound 6. 1 H NMR (500MHz, Chloroform) δ8.80 (s, 1H), 8.63-8.48 (m, 3H), 8.45 (d, J = 2.5Hz, 2H), 8.26 (s, 1H), 8.03 (s, 1H), 7. 80(s,1H),7.69(s,2H),7.58(d,J=15.0Hz,2H),7.33(s,2H),7.25(s,4H),7.19(s,1H),7.03(d,J=10.0Hz,4H).

[0428] Synthesis of compound 7: The synthesis of compound 7 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-triazine to obtain compound 7. 1 H NMR(500MHz,Chloroform)δ8.58(s,1H),8.53(d,J=15.0Hz,2H),8.36(s,4H),8.03( s,1H),7.90(s,1H),7.50(s,6H),7.31(s,2H),7.18(d,J=15.0Hz,4H),7.00(s,2H).

[0429] Synthesis of compound 8: The synthesis of compound 8 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine to obtain compound 8. 1 H NMR (500MHz, Chloroform) δ8.65-8.47(m,3H),8.36(s,4H),8.03(s,1H),7.96(s,2H),7.50(s,6H),7.38-7.11(m,9H),7.00(s,2H).

[0430] Synthesis of compound 9: The synthesis of compound 9 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2-([1,1'-diphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine to obtain compound 9. 1 H NMR(500MHz,Chloroform)δ8.62-8.47(m,3H),8.37(d,J=10.0Hz,3H),8.29(s,1H),8.03(s,1 H),7.96(s,2H),7.72(m,3H),7.61(s,1H),7.55-7.36(m,6H),7.35-7.12(m,9H),7.00(s,2H).

[0431] Synthesis of compound 10: The synthesis of compound 10 is similar to that of compound 1, except that M1 is replaced by M3, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2-([1,1'-diphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine to obtain compound 10. 1 H NMR(500MHz,Chloroform)δ8.73(s,1H),8.56-8.44(m,3H),8.36(s,2H),8.18(s,1H), 7.96(s,2H),7.74(d,J=5.0Hz,3H),7.56-7.39(m,8H),7.38-7.13(m,9H),7.00(s,2H).

[0432] Synthesis of intermediate M8: 7-bromo-9H-indolo[1,2-b]pyrazol-9-one (2.08 g, 8 mmol) and 2-([1,1'-diphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-1,3,5-triazine (4.6 g, 9 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), potassium carbonate (2.76 g, 20 mmol) and THF / H2O (60 mL / 12 mL) were added to a 200 mL pressure bottle and heated to 100 ° C under argon protection and pressurized for 12 h. After the reaction was completed, the mixture was cooled to room temperature, and a large amount of solid precipitated. The reaction solution was filtered, and the filtered solid was washed with ethanol (100 mL) and dried to obtain a yellow powdery solid (3.25 g, 5.76 mmol). Yield: 72%. 1 H NMR(500MHz,Chloroform)δ8.83-8.66(m,3H),8.43-8.30(m,4H),8.02(s,1H),7.96( s,2H),7.72(d,3H),7.59(d,2H),7.54-7.36(m,6H),7.25(s,1H),7.25-7.21(m,1H).

[0433] Synthesis of compound 11: 1-Bromo-2-(2-isopropylphenyl-2-yl)benzene (1.65 g, 6 mmol) was dissolved in 30 mL of anhydrous tetrahydrofuran and added to a two-necked flask under argon protection. The mixture was cooled to -78°C and stirred for 10 min. n-Butyl lithium (1.6 mol / L, THF, 4.5 mL) was slowly added dropwise with a syringe and stirred at -78°C for 1 h. Then, M8 (2.82 g, 5 mmol) was weighed and dissolved in anhydrous tetrahydrofuran and added to the flask. The mixture was warmed to room temperature and stirred under argon protection for 24 h. A small amount of deionized water was added to quench the reaction and the reaction was monitored by TLC thin plate until the reaction was complete. The reaction solution was spin-dried, mixed, and separated by silica gel chromatography to obtain a solid powder product (2.04 g, 2.75 mmol) with a yield of 55%. 1 H NMR(500MHz,Chloroform)δ8.64-8.47(m,3H),8.37(d,J=10.0Hz,3H),8.29(s,1H),8.03(s,1H ),7.96(s,2H),7.72(m,3H),7.61(s,1H),7.57-7.35(m,10H),7.31-7.10(m,7H),1.69(s,6H).

[0434] Synthesis of compound 12: The synthesis of compound 12 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole to obtain compound 12. 1 H NMR (500MHz, Chloroform) δ8.62-8.46 (m, 3H), 8.16 (d, J = 6.8Hz, 2H), 8.03 (s ,1H),7.72(m,3H),7.61(s,1H),7.35(m,4H),7.26-7.12(m,5H),7.00(s,2H).

[0435] Synthesis of compound 13: The synthesis of compound 13 is similar to that of compound 1, except that 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,2'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenyl)dibenzo[d]oxazole to obtain compound 13. 1 HNMR(500MHz,Chloroform)δ8.62-8.46(m,3H),8.33(s,1H),8.24(s,2H),8.03(s,1H),7.74(s,4H),7.35(m,6H),7.25-7.12(m,5H),7.00(s,2H).

[0436] Synthesis of compound 14: The synthesis of compound 14 is similar to that of compound 1, except that M1 is replaced by M3, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,10-phenanthroline is replaced by 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)benzo[d]oxazole to obtain compound 14. 1 H NMR(500MHz,Chloroform)δ8.52(d,J=20.0Hz,2H),8.45(s,1H),8.25(s,1H),8.18(s,1H),7. 74(s,3H),7.47(d,J=5.0Hz,2H),7.35(d,J=35.0Hz,5H),7.18(d,J=15.0Hz,4H),7.00(s,2H).

[0437] Synthesis of compound 15: The synthesis of compound 15 is similar to that of compound 1, except that M1 is replaced by M4, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline to obtain compound 15. 1 H NMR(500MHz,Chloroform)δ8.97(d,J=20.0Hz,2H),8.80(d,J=4.0Hz,2H),8.71(s,1H),8.63(s,1H), 8.53(s,1H),8.45(s,1H),7.82(s,1H),7.57(d,J=5.0Hz,3H),7.31(s,2H),7.18(m,4H),7.00(s,2H).

[0438] Synthesis of compound 16: The synthesis of compound 16 is similar to that of compound 1, except that M1 is replaced by M5, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline to obtain compound 16. 1 H NMR(500MHz,Chloroform)δ9.25(d,J=7.2Hz,2H),8.99(s,1H),8.79(d,J=5.3Hz,2H),8.45(s,1H),8.18( d,J=20.0Hz,2H),7.82(s,1H),7.57(d,J=5.0Hz,2H),7.31(s,2H),7.18(m,4H),7.06(s,1H),7.00(s,2H).

[0439] Synthesis of compound 17: The synthesis of compound 17 is similar to that of compound 1, except that M1 is replaced by M4, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline to obtain compound 17. 1H NMR(500MHz,Chloroform)δ8.95(s,1H),8.80(s,1H),8.63(s,1H),8.52-8.38(m,4H),8.34(d,J=10.0Hz ,2H),8.26(s,1H),7.80(s,1H),7.70(s,1H),7.65-7.49(m,4H),7.31(s,2H),7.18(m,4H),7.00(s,2H).

[0440] Synthesis of compound 18: The synthesis of compound 18 is similar to that of compound 1, except that M1 is replaced by M5, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline to obtain compound 18. 1 H NMR (500MHz, Chloroform) δ9.24 (s, 1H), 9.18 (s, 1H), 8.80 (s, 1H), 8.69 (s, 2H), 8.46 (d, J = 5. 8Hz,2H),8.23(m,2H),7.98(s,1H),7.80(s,1H),7.58(m,2H),7.40-7.11(m,8H),7.03(m,3H).

[0441] Synthesis of compound 19: The synthesis of compound 19 is similar to that of compound 1, except that M1 is replaced by M5, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-triazine to obtain compound 19. 1 H NMR (500MHz, Chloroform) δ9.29(s,1H),9.24(s,1H),8.36(s,4H),8.18(m,2H),7.50(s,6H),7.31(s,2H),7.18(m,4H),7.06(s,1H),7.00(s,2H).

[0442] Synthesis of compound 20: The synthesis of compound 20 is similar to that of compound 1, except that M1 is replaced by M4, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,4-bis([1,1'-diphenyl]-4-yl)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine to obtain compound 20. 1 H NMR (500MHz, Chloroform) δ8.95(s,1H),8.63(s,1H),8.49(s,1H),8.35(s,2H),7.96(s,5H),7.75(s,4H),7.66-7.12(m,19H),7.00(s,2H).

[0443] Synthesis of compound 21: The synthesis of compound 21 is similar to that of compound 1, except that M1 is replaced by M6, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,5-triazine to obtain compound 21. 1 H NMR (500MHz, Chloroform) δ9.25 (d, J = 5.5 Hz, 2H), 8.36 (s, 4H), 8.18 (m, 2H), 7.69 (s, 2H), 7.50 (s, 6H), 7.33 (s, 2H), 7.10-6.95 (m, 5H).

[0444] Synthesis of intermediate M9: The synthesis of intermediate M9 was similar to that of intermediate M8, except that 7-bromo-9H-indolo[1,2-b]pyrazol-9-one was replaced by 3-bromo-9H-cyclopenta[1,2-c:4,3-c']bipyridin-9-one, and 2-([1,1'-diphenyl]-4-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was replaced by 2,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-ddioxaborolan-2-yl)-1,3,5-triazine. 1 H NMR (500MHz, Chloroform) δ9.17(s,1H),9.08(s,1H),9.06(s,1H),8.74(s,1H),8.36(s,4H),7.77(s,1H),7.50(s,6H).

[0445] Synthesis of compound 22: The synthesis of compound 22 was similar to that of compound 11, except that intermediate M8 was replaced by M9. 1 H NMR(500MHz,Chloroform)δ8.95(s,1H),8.71(s,1H),8.63(s,1H),8.53(s,1H) ,8.36(s,4H),7.56(s,1H),7.48(m,8H),7.40(s,2H),7.15(s,4H),1.69(s,6H).

[0446] Synthesis of Intermediate M10: M4 (3.0 g, 7.2 mmol), bis(pinacolato)diboron (2.13 g, 8.40 mmol), Pd(dppf)Cl2 (256 mg, 0.35 mmol), potassium acetate (2.06 g, 21.1 mmol), and 1,4-dioxane (35 mL) were added to a 125 mL round-bottom flask. Under argon, the mixture was heated to 100°C and refluxed for 12 h. After the reaction, the mixture was cooled to room temperature and the 1,4-dioxane was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (petroleum ether:DCM = 20:1) to obtain a light yellow powder (2.48 g, 5.4 mmol). Yield: 75%. 1 H NMR(500MHz,Chloroform)δ8.95(s,1H),8.95(s,1H),8.63(s,1H),8.63(s,1H),8.52(s,1H),8.52 (s,1H),7.63(s,1H),7.63(s,1H),7.56(s,1H),7.31(s,2H),7.18(d,J=15.0Hz,4H),7.00(s,2H), 1.14 (s, 12H). Synthesis of Compound 23: Intermediate M10 (2.48 g, 5.4 mmol) was added to a 200 mL pressure bottle with 2-bromobenzo[d]oxazole (1.18 g, 6 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), potassium carbonate (2.76 g, 20 mmol), and THF / H2O (60 mL / 12 mL). The mixture was heated to 100°C under argon and reacted under pressure for 12 h. After the reaction, the mixture was cooled to room temperature, resulting in the precipitation of a large amount of solid. The reaction mixture was filtered, and the filtered solid was washed with ethanol (100 mL) and dried to obtain a yellow powder (1.95 g, 4.32 mmol). Yield: 80%. 1H NMR(500MHz,Chloroform)δ8.95(s,1H),8.71(s,1H),8.63(s,1H),8.53(s,1H),7.74 (s,2H),7.56(s,1H),7.38(s,2H),7.31(s,2H),7.18(d,J=15.0Hz,4H),7.00(s,2H).

[0447] Synthesis of compound 24: The synthesis of compound 24 is similar to that of compound 1, except that M1 is replaced by M7, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline is replaced by 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole to obtain compound 24. 1 H NMR(500MHz,Chloroform)δ9.17(s,2H),8.47(s,2H),8.33(s,2H),8.15(s,2H) ,7.98(s,2H),7.72(m,6H),7.38(s,4H),7.31(s,2H),7.18(m,4H),7.00(s,2H).

[0448] Synthesis of intermediate M11: The synthesis of intermediate M11 was similar to that of intermediate M10, except that intermediate M4 was replaced by M6. 1 H NMR (500 MHz, Chloroform) δ9.24 (s, 1H), 8.89 (s, 1H), 8.20 (s, 1H), 7.69 (s, 2H), 7.42 (s, 1H), 7.33 (s, 2H), 7.12-6.95 (m, 5H), 1.14 (s, 12H). Synthesis of compound 25: The synthesis of compound 25 was the same as that of compound 23, except that intermediate M10 was replaced by M11. 1 H NMR (500MHz, Chloroform) δ9.24 (s, 1H), 9.11 (s, 1H), 8.18 (d, J = 20.0Hz, 2H), 7.71 (m, 4H), 7.36 (m, 4H), 7.11-6.92 (m, 5H).

[0449] 2. Physical and chemical properties of the compound:

[0450] 1. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of the compounds of the present disclosure were simulated using quantum chemistry simulation software at the B3LYP / 6-31G* level. HOMO and LUMO energy levels and reorganization energies (ROEs) were simulated using DFT methods and the B3LYP functional. Some exemplary results are shown in Tables 1-1 and 1-2 below.

[0451] Table 1-1

[0452] Table 1-2

[0453] 2. The glass transition temperature (Tg) determines the thermal stability of the electron transport material during evaporation. The higher the Tg, the better the thermal stability of the electron transport material. The measuring instrument is a DSC differential scanning calorimeter, the test atmosphere is nitrogen, the heating rate is 10°C / min, and the temperature range is 50-300°C. The T1 energy level is calculated using the TDDFT method and B3LYP functional. Some exemplary results of the compounds disclosed herein are shown in Tables 2-1 to 2-2 below.

[0454] Table 2-1

[0455] Table 2-2

[0456] Experimental Example 1

[0457] The functional layer materials of the light-emitting device in this experimental example are: HAT-CN as the hole injection layer, NPB as the hole transport layer, TCTA as the electron blocking layer, DPEPO as the hole blocking layer, ADN as the blue light host, DPAVBi as the blue light dopant (these materials are commercially available), and the electron transport layer material adopts the compound provided by the present disclosure; the specific chemical structure is shown below:

[0458] The preparation process of the light emitting device in this experimental example is as follows:

[0459] The base substrate (glass plate) provided with the first electrode 1 (ITO) was ultrasonically treated in a cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone-ethanol mixed solvent, and baked in a clean environment until the moisture was completely removed.

[0460] The glass plate with ITO is placed in a vacuum chamber, and the vacuum is evacuated to 1×10-5 to 1×10-6. A hole injection material is vacuum-deposited on the side of the ITO away from the glass plate to form a hole injection layer.

[0461] A hole transport material is evaporated on the side of the hole injection layer away from the ITO to form a hole transport layer.

[0462] An electron blocking material is vacuum evaporated on a side of the hole transport layer away from the hole injection layer to form an electron blocking layer.

[0463] A light-emitting material is vacuum evaporated on the side of the electron blocking layer away from the hole transport layer to form a light-emitting layer. The light-emitting material includes a host material and a guest material. The weight ratio of the host material to the guest material is 95:5 using a multi-source co-evaporation method.

[0464] A hole blocking material is vacuum evaporated on a side of the light emitting layer away from the electron blocking layer to form a hole blocking layer.

[0465] An electron transport material is vacuum evaporated on the side of the hole blocking layer away from the light-emitting layer to form an electron transport layer.

[0466] An inorganic substance (LiF) as an electron injection material was vacuum-deposited to a thickness of 1 nm on the side of the electron transport layer away from the hole blocking layer to form an electron injection layer.

[0467] An Al layer is plated on the electron injection layer away from the evaporated electron transport layer as a cathode.

[0468] The device structure of this experimental example is:

[0469] Substrate / ITO / HAT-CN(20nm) / NPB(50nm) / TCTA(6nm) / ADN+5%DPAVBi(20nm) /

[0470] DPEPO (10 nm) / Compound 1 (40 nm) / LiF (1 nm) / Al (100 nm); Compound 1 serves as the electron transport layer.

[0471] Experimental Examples 2 to 25

[0472] The difference from Experimental Example 1 is that the electron transport layer uses the above compounds 2 to 25 respectively instead of the compound 1 in Experimental Example 1. The other steps are the same as those in Experimental Example 1.

[0473] Comparative Example

[0474] The difference from Experimental Example 1 is that the electron transport layer uses compound Ref.1 instead of compound 1 in Experimental Example 1, and the other steps are the same as Experimental Example 1.

[0475] The performance of the electroluminescent devices prepared in the above experimental examples 1 to 25 and the comparative example was tested. The test method was as follows: the prepared devices were tested at a current density of 15 mA / cm 2 The luminescence performance test (turn-on voltage, brightness, external quantum efficiency, and lifespan) was conducted under the following conditions. The results are shown in Tables 3-1 and 3-2.

[0476] Table 3-1

[0477] Table 3-2

[0478] From the exemplary results in Tables 3-1 to 3-2 above, it can be seen that the compound disclosed herein is an electron transport material with good device performance. OLED devices using it as an electron transport layer all show high efficiency, low driving voltage, and long life electroluminescent performance.

Claims

1. A compound represented by formula O, or a stereoisomer or tautomer of said compound, in: X 1 , X 2 , X 3 , X 4 are each independently selected from CH, N, and X 1 , X 2 , X 3 , X 4 At least one of them is N, X 3 , X 4 Not all are N; X 5 , X 6 , X 7 are each independently selected from CH, N, and X 6 , X 7 Not all are N; A1 ring and A2 ring are each independently selected from C6-C12 aromatic rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b are each independently selected from hydrogen, methyl; Preferably, Y is selected from -O-, -S-, -CH2-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; L 1 , L 2 are each independently selected from a direct bond, a C6-C18 arylene group, and the C6-C18 arylene group is optionally substituted by 1 R L replaced by; R L Selected from benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl; R 1 , R 2 Each is independently selected from phenanthroline, 6-membered nitrogen-containing heteroaryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, and the phenanthroline, 6-membered nitrogen-containing heteroaryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl are each independently optionally substituted by 1-2 R R replaced by; R R Selected from C6-C18 aryl and fluorenyl, wherein the C6-C18 aryl and fluorenyl are each independently optionally substituted by 1-3 (preferably 1-2, more preferably 2) C1-C6 alkyl groups; R 3 , R 4 Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R 3 , R 4 For hydrogen.

2. The compound according to claim 1, or a stereoisomer or tautomer of the compound, wherein: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A1 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A2 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring.

3. A compound according to any one of claims 1 to 2, or a stereoisomer or tautomer of said compound, wherein: Selected from: Among them, carbon atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the right. even; Preferably, Selected from: Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the aromatic ring carbon atom on the right.

4. The compound according to any one of claims 1 to 3, or a stereoisomer or tautomer of the compound, wherein: Selected from: Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; Preferably, Selected from: Among them, C atom No. 1 is connected to the central spiro carbon atom, and carbon atom No. 2 is connected to the carbon atom of the aromatic ring on the left.

5. The compound according to any one of claims 1 to 4, or a stereoisomer or tautomer of the compound, wherein: L 1 , L 2 Each is independently selected from a direct bond, a phenyl subunit, a naphthalene subunit, and a biphenyl subunit, and the phenyl subunit, the naphthalene subunit, and the biphenyl subunit are each independently optionally substituted by one R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L Selected from Most preferably, L 1 , L 2 Each independently selected from: Direct key, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected.

6. The compound according to any one of claims 1 to 5, or a stereoisomer or tautomer of the compound, wherein: R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazine, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazine, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, wherein the phenyl, biphenyl, naphthyl, fluorenyl is independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from:

7. The compound according to any one of claims 1 to 6, or a stereoisomer or tautomer of the compound, wherein: R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

8. The compound according to claim 1, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in Formula I, in: X 1 , X 2 , X 3 , X 4 are each independently selected from CH, N, and X 1 , X 2 , X 3 , X 4 At least one of them is N, X 3 , X 4 Not all are N; Preferably, X 1 , X 2 , X 3 , X 4 are each independently selected from CH, N, and X 1 , X 2 , X 3 , X 4 There are two N, X 3 , X 4 Not all are N; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; More preferably, Selected from: Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; A1 ring is selected from benzene ring and naphthalene ring; Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A1 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; A2 ring is selected from benzene ring and naphthalene ring; Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A2 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b are each independently selected from hydrogen, methyl; Preferably, Y is selected from -O-, -S-, -CH2-, More preferably, Y is selected from -O-, -S-; L 1 , L 2 Each is independently selected from a direct bond, a phenyl subunit, a naphthalene subunit, and a biphenyl subunit, and the phenyl subunit, the naphthalene subunit, and the biphenyl subunit are each independently optionally substituted by one R L replaced by; Preferably, L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the The phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L for Most preferably, L 1 , L 2 Each independently selected from a direct bond, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the pyridyl, pyrimidinyl, triazine are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazinyl, and each is independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 (preferably 2) R R replaced by; R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, wherein the phenyl, biphenyl, naphthyl, fluorenyl is independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from: R 3 , R 4 Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R 3 , R 4 For hydrogen.

9. The compound according to claim 8, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in Formula I-1, in: A1 ring is selected from benzene ring and naphthalene ring; Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A1 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; A2 ring is selected from benzene ring and naphthalene ring; Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A2 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b are each independently selected from hydrogen, methyl; Preferably, Y is selected from -O-, -S-, -CH2-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 Each is independently selected from a direct bond, a phenyl subunit, a naphthalene subunit, and a biphenyl subunit, and the phenyl subunit, the naphthalene subunit, and the biphenyl subunit are each independently optionally substituted by one R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L for Most preferably, L 1 , L 2 Each independently selected from a direct bond, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the pyridyl, pyrimidinyl, triazine are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazinyl, and each is independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 (preferably 2) R R replaced by; R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, wherein the phenyl, biphenyl, naphthyl, fluorenyl is independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

10. The compound according to claim 8, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula I-2, in: A1 ring is selected from benzene ring and naphthalene ring; Preferably, the A1 ring is selected from Among them, C atom No. 1 and The carbon atom close to Y on the middle six-membered ring is fused, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A1 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; A2 ring is selected from benzene ring and naphthalene ring; Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A2 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b are each independently selected from hydrogen, methyl; Preferably, Y is selected from -O-, -S-, -CH2-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, n1 is 0 and n2 is 1; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from in, C atom 1 is connected to the central spiro carbon atom, and C atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group; Preferably, L 1 , L 2 is a direct key; R 1 , R 2 Each is independently selected from phenanthroline, and the phenanthroline is optionally substituted by 1-2 (preferably 2) R R Replaced by R R is phenyl; Preferably, R 1 , R 2 are each independently selected from diazaphenanthroline; More preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

11. The compound according to claim 8, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in Formula I-3, in: A1 ring is selected from benzene ring and naphthalene ring; Preferably, the A1 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A1 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; A2 ring is selected from benzene ring and naphthalene ring; Preferably, the A2 ring is selected from Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; More preferably, the A2 ring is Among them, the No. 1 C atom is fused with the carbon atom close to Y on the middle six-membered ring, and the No. 2 C atom is fused with the carbon atom far from Y on the middle six-membered ring; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b are each independently selected from hydrogen, methyl; Preferably, Y is selected from -O-, -S-, -CH2-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, n1 is 0 and n2 is 1; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group; Preferably, L 1 , L 2 is a direct key; R 1 , R 2 Each is independently selected from phenanthroline, and the phenanthroline is optionally substituted by 1-2 (preferably 2) R R Replaced by R R is phenyl; Preferably, R 1 , R 2 are each independently selected from diazaphenanthroline; More preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

12. The compound according to claim 1, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in Formula II, X 2 , X 3 are each independently selected from CH, N, and X 2 , X 3 At least one of them is N; X 5 , X 6 are each independently selected from CH, N, and X 5 , X 6 At least one of them is N; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; More preferably, Selected from: Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; More preferably, Selected from: Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, and a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by 1 R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L replaced by; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L Selected from Most preferably, L 1 , L 2 Each independently selected from: Direct key, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each independently selected from diazophanol, pyridinyl, pyrimidinyl, triazine, benzoxazole The phenanthroline, pyridyl, pyrimidinyl, triazine, benzoxazolyl and benzothiazolyl groups are each independently optionally substituted by 1 to 2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 (preferably 2) R R replaced by; R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, wherein the phenyl, biphenyl, naphthyl, fluorenyl is independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from: R 3 , R 4 Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R 3 , R 4 For hydrogen.

13. The compound according to claim 12, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula II-1, in: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Place Replacement, R L is benzoxazolyl; Preferably, L 1 , L 2 Each independently selected from a direct bond, R 1 , R 2 Each is independently selected from phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, triazine, benzoxazolyl, and the pyridinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, s-triazine, benzoxazolyl, and the pyridyl, s-triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 (preferably 2) R R replaced by; R R is selected from phenyl, biphenyl and fluorenyl, wherein the phenyl, biphenyl and fluorenyl are each independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl and fluorenyl, wherein the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

14. The compound according to claim 12, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula II-2, in: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Replaced by R L is benzoxazolyl; Preferably, L 1 , L 2 Each independently selected from a direct bond, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl, and the pyridinyl, pyrimidinyl, triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl, biphenyl and fluorenyl, wherein the phenyl, biphenyl and fluorenyl are each independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl and fluorenyl, wherein the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

15. The compound according to claim 12, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula II-3, in: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L Replaced by R L is benzoxazolyl; Preferably, L 1 , L 2 Each independently selected from a direct bond, R 1 , R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazine, benzoxazolyl, and the pyrimidinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl and fluorenyl, wherein the phenyl and fluorenyl are each independently optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl and fluorenyl, wherein the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl and fluorenyl, wherein the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

16. The compound according to claim 12, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula II-4, in: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, and a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by 1 R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Optionally 1 R L replaced by; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L for Most preferably, L 1 , L 2 Each independently selected from a direct bond, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each is independently selected from phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyridyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, triazine, benzoxazolyl, and the pyridinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, s-triazine, benzoxazolyl, and the pyridyl, s-triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl and biphenyl, wherein the phenyl and biphenyl are each independently optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R Selected from phenyl and biphenyl; More preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

17. The compound according to claim 12, or a stereoisomer or tautomer of the compound, wherein: The compound has a structure shown in formula II-5, in: A1 ring and A2 ring are each independently selected from a benzene ring and a naphthalene ring; Preferably, the A1 ring and the A2 ring are benzene rings; Y is selected from -O-, -S-, -CR a R b -; R a , R b Each is independently selected from hydrogen, C1-C6 alkyl; Preferably, R a , R b Each independently selected from C1-C6 alkyl; More preferably, R a , R b is methyl; Preferably, Y is selected from -O-, -S-, More preferably, Y is selected from -O-, -S-; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the right; Preferably, Selected from Among them, C atom 1 is connected to the central spiro carbon atom, and carbon atom 2 is connected to the aromatic ring carbon atom on the left; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, and a naphthalene group, and the phenylene group and the naphthalene group are each independently optionally substituted by 1 R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L replaced by; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L Selected from Most preferably, L 1 , L 2 Each independently selected from: Direct key, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 (preferably 2) R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyrimidinyl, triazine, benzoxazolyl, and the pyrimidinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyrimidinyl, s-triazinyl, benzoxazolyl, and the pyrimidinyl, s-triazinyl, benzoxazolyl are each independently optionally substituted by 1-2 (preferably 2) R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl, biphenyl and naphthyl, wherein the phenyl, biphenyl and naphthyl are each independently optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl and naphthyl; More preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

18. The compound according to claim 1, or a stereoisomer or tautomer of the compound, wherein: The compound has the structure shown in formula Oc-1, formula Oc-2, and formula Oc-3, in: Y is selected from O, S; n1 and n2 are each independently selected from 0 and 1, and n1 and n2 are not 0 at the same time; L 1 , L 2 Each is independently selected from a direct bond, a phenylene group, a naphthalene group, and a biphenylene group, and the phenylene group, the naphthalene group, and the biphenylene group are each independently optionally substituted by one R L replaced by; Preferably, L 1 , L 2 are each independently selected from a direct bond, a phenylene group, a naphthalene group, a biphenylene group, and the phenylene group is optionally substituted by 1 R L replaced by; More preferably, L 1 , L 2 Each independently selected from a direct bond, and Each independently optionally replaced by 1 R L The bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R L Selected from benzoxazolyl and benzothiazolyl; Preferably, R L is benzoxazolyl; More preferably, R L Selected from Most preferably, L 1 , L 2 Each independently selected from: Direct key, Among them, the bonds marked with * are connected to the parent ring, and the bonds without * are connected to R 1 or R 2 connected; R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and each of the phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl is independently optionally substituted by 1-2 R R replaced by; Preferably, R 1 , R 2 Each is independently selected from phenanthroline, pyridinyl, pyrimidinyl, triazine, benzoxazolyl, benzothiazolyl, and the pyridinyl, pyrimidinyl, triazine, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by; More preferably, R 1 , R 2 Each is independently selected from o-phenanthroline, pyridyl, pyrimidinyl, s-triazine, benzoxazolyl, and the pyridyl, pyrimidinyl, s-triazine, benzoxazolyl are each independently optionally substituted by 1-2 R R replaced by; More preferably, R 1 , R 2 Each independently selected from and Each independently optionally 1-2 R R replaced by; R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, wherein the phenyl, biphenyl, naphthyl, fluorenyl is independently and optionally substituted by 2 C1-C6 alkyl groups; Preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 C1-C6 alkyl groups; More preferably, R R is selected from phenyl, biphenyl, naphthyl, fluorenyl, and the fluorenyl is optionally substituted by 2 methyl groups; Most preferably, R R Selected from Most preferably, R 1 , R 2 Each independently selected from: Most preferably, R 1 -L 1 -、R 2 -L 2 - Each independently selected from:

19. A compound according to any one of claims 1 to 18, or a stereoisomer or tautomer of said compound, wherein: The compound is selected from:

20. An electron transport material comprising the compound according to any one of claims 1 to 19, or a stereoisomer or tautomer of the compound.

21. An organic electroluminescent device comprising an electron transport layer, wherein the material of the electron transport layer comprises the compound according to any one of claims 1 to 19, or a stereoisomer or tautomer of the compound; Preferably, the organic electroluminescent device comprises a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a second electrode which are stacked in sequence, and the material of the electron transport layer comprises the compound according to any one of claims 1 to 19, or a stereoisomer or tautomer of the compound.

22. An electronic device comprising the organic electroluminescent device according to claim 21.

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