Organic light-emitting device
By using fluorene compounds as electron transport materials in OLEDs, the problem of imbalance between hole and electron transport was solved, improving luminous efficiency and extending lifespan.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-12-11
- Publication Date
- 2026-03-31
AI Technical Summary
The imbalance between hole and electron transport in existing OLEDs leads to low luminous efficiency and short lifespan. The hole blocking layer material also has insufficient electron transport performance and thermal stability.
Using fluorene compounds represented by formula I as electron transport region materials improves electron transport capability, blocks holes, balances charge transport, and extends device lifetime.
This achieves an effective balance between holes and electrons, improving the luminous efficiency and stability of OLEDs and extending their lifespan.
Smart Images

Figure BDA0005736189860000011 
Figure BDA0005736189860000021 
Figure BDA0005736189860000031
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescence technology, and more specifically to an organic electroluminescent device. Background Technology
[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, offer advantages over traditional liquid crystal displays (LCDs). OLEDs are self-emissive, have high luminous efficiency, low power consumption, are lightweight, thin, and have wide viewing angles, making them the future trend of flat panel displays and possessing broad market prospects.
[0003] The light-emitting principle of OLEDs is that, under the influence of an applied electric field, holes injected from the anode and electrons injected from the cathode migrate and recombine in the organic layer, transferring energy to the light-emitting material and exciting it to form excitons. When the excitons return from the excited state to the ground state, they emit radiation attenuation, and the attenuated energy is emitted in the form of light, thus achieving the purpose of light emission. OLEDs consist of an anode, a cathode, and an intermediate organic layer. The organic layer of an OLED can contain hole transport regions, light-emitting regions, electron transport regions, etc. The injection and transport layers in the hole / electron transport regions improve the transport of charge to the emission layer, while the blocking layer prevents charge loss in the opposite direction and confines the excitons. This multi-layered structure lowers the injection barrier for holes and electrons, improving the stability, luminous efficiency, and lifespan of OLEDs.
[0004] Currently, the hole mobility of hole transport materials used in OLEDs is generally much higher than that of electron transport materials. This leads to an inability to achieve an effective balance between hole and electron transport, causing some holes to easily pass through the emissive layer and recombine with electrons at the interface between the emissive and electron transport layers or within the electron transport layer itself. Furthermore, existing hole-blocking layer materials suffer from poor film stability and heat resistance due to their low electron transport performance and glass transition temperature, failing to adequately improve the characteristics of OLED devices. Therefore, to effectively improve the luminous efficiency and extend the lifespan of OLEDs, it is necessary to seek electron transport or hole-blocking materials with high electron injection performance, high electron mobility, high hole blocking ability, high hole durability, and high glass transition temperature. Summary of the Invention
[0005] To address the aforementioned problems, the present invention aims to provide an organic electroluminescent device that can improve the luminous efficiency of the organic electroluminescent device and extend its service life.
[0006] This invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a hole transport region, an electron transport region, and a light-emitting layer. The hole transport region is located between the light-emitting layer and the anode, and the electron transport region is located between the light-emitting layer and the cathode. The electron transport region comprises a fluorene compound represented by Formula I.
[0007]
[0008] Wherein, X is independently selected from either C(R0) or N;
[0009] The z is independently selected from either CH or N;
[0010] Z1 and Z2 are independently selected from any one of O, S, and N (R6);
[0011] R0, R1, R2, R3, R4, and R5 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R4 and R5 are connected to form a substituted or unsubstituted ring;
[0012] The R6 is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl;
[0013] The n1 is selected from 0, 1, 2, 3 or 4; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;
[0014] The n2 is selected from 0, 1, 2, 3 or 4; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;
[0015] The a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3s, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;
[0016] The L1 and L2 are independently selected from single bonds or any one of the following groups, or from two or more of the following groups:
[0017]
[0018] X1 is selected from O, S, N(R) t Any one of the following;
[0019] X2 is selected from O, S, C(R) p R q ), N(R t Any one of the following;
[0020] The u is independently selected from either CH or N;
[0021] The u' is independently selected from either CH or N, and at least two of u' are selected from N;
[0022] The ring A is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0023] The R b R b '、R p R q Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R p R q The links between them form substituted or unsubstituted rings;
[0024] The R tIt is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0025] The q is selected from 1, 2, 3, or 4;
[0026] b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;
[0027] The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They may be the same as or different from each other;
[0028] The L3 and L5 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;
[0029] The L4 is selected from any one of the following groups or from a combination of two or more of the following groups;
[0030]
[0031] X5 is selected from O, S, N(R) v Any one of the following;
[0032] X6 is selected from either O or S;
[0033] The i is independently selected from either CH or N;
[0034] The i' is independently selected from either CH or N, and at most two of the i' are selected from N;
[0035] The ring C is selected from substituted or unsubstituted C3 to C10 alicyclic rings;
[0036] The R c R c Independently selected from Group 1, hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, and R c At least one of the following is selected from Group 1: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic groups, and fused cycloalkanes of C6-C30 aromatic groups;
[0037] The R v It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0038] The value of r is selected from 1, 2, 3, or 4;
[0039] c1 is selected from 1, 2, 3, or 4; c2 is selected from 1, 2, 3, 4, 5, or 6; c3 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 1 or 2; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;
[0040] The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c'They may be the same as or different from each other;
[0041] Group 1:
[0042]
[0043] Y1, Y2, and Y3 are independently selected from O, S, and N(R). r Any one of the following;
[0044] The v is independently selected from either CH or N, and at least one of v is selected from N;
[0045] The R f R f 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0046] The R r It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0047] The s is selected from 1, 2, 3 or 4;
[0048] f1 is selected from 0, 1, 2, 3, or 4; f2 is selected from 0, 1, 2, 3, 4, 5, or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; f4 is selected from 0, 1, 2, or 3; when there are two or more R... f At that time, two or more R f The same or different between each other, or two adjacent R f They connect with each other to form substituted or unsubstituted rings;
[0049] The f'1 is selected from 0, 1, or 2; when there are two or more R... f At that time, two or more R f 'They are the same as or different from each other.'
[0050] Beneficial effects
[0051] The organic electroluminescent device provided by this invention includes a compound of formula I in its electron transport region. This compound exhibits good thermal stability, electron transport capability, and hole blocking capability. When used in the electron transport layer of the device, it can effectively balance the transport of holes and electrons, improving the luminous efficiency of the device. When used in the hole blocking layer, it can block holes that penetrate the light-emitting layer, preventing hole leakage into the electron transport layer and thus avoiding device aging, improving device stability, and extending the device's lifespan. The compound provided by this invention has a simple preparation method, readily available raw materials, and can meet industrialization needs, showing good prospects for industrialization. Detailed Implementation
[0052] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.
[0053] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.
[0054] In this instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the attached group / fragment.
[0055] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.
[0056] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.
[0057] For example, Can represent Can represent Can represent And so on.
[0058] The aryl group described in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule; examples include phenyl, etc., but are not limited thereto. The polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule; examples include biphenyl, terphenyl, tetraphenyl, etc., but are not limited thereto. The fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms; examples include naphthyl, anthracene, phenanthryl, pyrene, perylene, etc. It includes, but is not limited to, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzo[a]fluorenyl, 9,9'-spirodifluorenyl, etc.
[0059] The heteroaryl group referred to in this invention refers to the general term for the group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group with heteroatoms. It can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, and phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples of monocyclic heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto. Examples of polycyclic heteroaryl groups may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto. Examples of fused-ring heteroaryl groups may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinoxalinyl, benzo[a]quinoxalinyl The following are examples of compounds, but not limited to: phenanthroline, naphthidyl, indolyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazole, benzocarbazole, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc.
[0060] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples of the fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentane, and naphthocyclohexyl.
[0061] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the general term for the monovalent group obtained after removing one hydrogen atom from the fused heterocyclic alkanes and aromatic rings. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples of the fused cyclic group of heterocyclic alkanes and aromatic rings may include benzo[a]tetrahydropyrrole, naph[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naph[a]piperidinyl, phenanthrene[a]piperidinyl, etc., but are not limited thereto.
[0062] The fused cyclic groups of alicyclic and heteroaromatic rings described in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom after alicyclic and heteroaromatic rings are fused together. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 12, and more preferably 3 to 8. The aromatic ring has 2 to 30 carbon atoms, preferably 2 to 18, and more preferably 2 to 15. Examples of fused cyclic groups of C3-C12 alicyclic and C2-C30 heteroaromatic rings may include pyridocyclopropane, pyridocyclobutane, pyridocyclopentane, pyridocyclohexane, pyridocycloheptane, pyridocyclobutenyl, pyridocyclopentenyl, pyridocyclohexenyl, pyrimidinylcyclopropyl, pyrimidinylcyclobutane, pyrimidinylcyclopentane, pyrimidinylcyclohexane, pyrimidinylbenzocycloheptane, benzofuranocyclopentane, and benzothiophene. Cyclopentyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazoleocyclopropyl, carbazoleocyclobutyl, carbazoleocyclopentyl, carbazoleocyclohexyl, carbazoleocycloheptyl, etc., but not limited to these.
[0063] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of monocyclic arylene groups may include phenylene, but are not limited thereto; examples of polycyclic arylene groups may include biphenylene, terphenylene, etc., but are not limited thereto; examples of fused-ring arylene groups may include naphthylene, anthraceneene, phenanthrene, pyreneene, trimethyleneene, fluoranthracene, etc., but are not limited thereto.
[0064] The heteroarylene group described in this invention refers to the general term for the group obtained by replacing one or more aromatic carbon atoms in the arylene group with heteroatoms. The heteroatoms include, but are not limited to, O, S, N, Si, or P atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. Examples of monocyclic and fused-ring heteroarylene groups may include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, and dibenzocarbazolyl. Examples of polycyclic heteroarylene groups may include, but are not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl.
[0065] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for the divalent groups obtained after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples of fused alicyclic and heteroaromatic ring groups may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium-benzocycloheptyl, pyrimidinium-cyclopropyl, pyrimidinium-cyclobutyl, pyrimidinium-cyclopentyl, pyrimidinium-benzocycloheptyl, and dibenzofuran-cyclopropyl. Propyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc., but not limited to these.
[0066] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for the divalent groups obtained after removing two hydrogen atoms from the fused alicyclic and heteroaromatic rings. Preferably, they have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples of the fused alicyclic and heteroaromatic ring groups may include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, and dibenzofuranocyclopropyl. Examples of compounds include, but are not limited to, thiophenecyclohexyl, dibenzothiophenecycloheptyl, benzoxazolylcyclopropyl, benzoxazolylcyclobutyl, benzoxazolylcyclopentyl, benzoxazolylcyclohexyl, pyridinylcyclopropyl, pyridinylcyclobutyl, pyridinylcyclopentyl, pyridinylcyclohexyl, pyridinylbenzocycloheptyl, pyrimidinylcyclopropyl, pyrimidinylcyclobutyl, pyrimidinylcyclopentyl, pyrimidinylbenzocyclohexyl, etc.
[0067] The alkyl group referred to in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, isomers of n-hexyl, isomers of n-heptyl, isomers of n-octyl, isomers of n-nonyl, isomers of n-decyl, etc., but is not limited thereto.
[0068] The cycloalkyl group described in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc., but are not limited thereto.
[0069] The heterocyclic alkyl group described in this invention refers to a group formed by removing a hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, O, S, N, Si, or P atoms, preferably having 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Examples may include piperidinyl, piperazineyl, tetrahydropyrrolyl, ethylene oxide, cyclothioethanedialkyl, morpholinyl, thiomorpholinyl, ethylene oxide, cyclothioethanedialkyl, propylenediyl, etc., but are not limited thereto.
[0070] The “substituted or unsubstituted silyl group” as described in this invention refers to the -Si(R)3 group, wherein each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenyl, phenyl, biphenyl, naphthyl. Examples may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.
[0071] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, 9,9-dimethylfluorenyl, 9 9-Diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indoleyl, pyrrololyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, benzocyclobutane, benzocyclobutene, benzocyclopentane, benzocyclopentene, benzocyclohexane, benzocyclohexene, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.
[0072] In this invention, "at least one" includes one, two, three, or more. "Two or more" may include two, three, four, or more, where permissible.
[0073] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:
[0074]
[0075] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.
[0076] This invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a hole transport region, an electron transport region, and a light-emitting layer. The hole transport region is located between the light-emitting layer and the anode, and the electron transport region is located between the light-emitting layer and the cathode. The electron transport region comprises a fluorene compound represented by Formula I.
[0077]
[0078] Wherein, X is independently selected from either C(R0) or N;
[0079] The z is independently selected from either CH or N;
[0080] Z1 and Z2 are independently selected from any one of O, S, and N (R6);
[0081] R0, R1, R2, R3, R4, and R5 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, or R4 and R5 are connected to form a substituted or unsubstituted ring;
[0082] The R6 is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl;
[0083] The n1 is selected from 0, 1, 2, 3 or 4; when there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;
[0084] The n2 is selected from 0, 1, 2, 3 or 4; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;
[0085] The a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when there are two or more R3s, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;
[0086] The L1 and L2 are independently selected from single bonds or any one of the following groups, or from two or more of the following groups:
[0087]
[0088] X1 is selected from O, S, N(R) t Any one of the following;
[0089] X2 is selected from O, S, C(R) p R q ), N(R t Any one of the following;
[0090] The u is independently selected from either CH or N;
[0091] The u' is independently selected from either CH or N, and at least two of u' are selected from N;
[0092] The ring A is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0093] The R b R b '、Rp R q Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R p R q The links between them form substituted or unsubstituted rings;
[0094] The R t It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0095] The q is selected from 1, 2, 3, or 4;
[0096] b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;
[0097] The b'1 is selected from 0, 1, or 2; when there are two or more R... b At that time, two or more R b 'They may be the same as or different from each other;
[0098] The L3 and L5 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;
[0099] The L4 is selected from any one of the following groups or from a combination of two or more of the following groups;
[0100]
[0101] X5 is selected from O, S, N(R) v Any one of the following;
[0102] X6 is selected from either O or S;
[0103] The i is independently selected from either CH or N;
[0104] The i' is independently selected from either CH or N, and at most two of the i' are selected from N;
[0105] The ring C is selected from substituted or unsubstituted C3 to C10 alicyclic rings;
[0106] The R c R c Independently selected from Group 1, hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group, and R c At least one of the following is selected from Group 1: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic groups, and fused cycloalkanes of C6-C30 aromatic groups;
[0107] The R vIt is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0108] The value of r is selected from 1, 2, 3, or 4;
[0109] c1 is selected from 1, 2, 3, or 4; c2 is selected from 1, 2, 3, 4, 5, or 6; c3 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 1 or 2; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings;
[0110] The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They may be the same as or different from each other;
[0111] Group 1:
[0112]
[0113] Y1, Y2, and Y3 are independently selected from O, S, and N(R). r Any one of the following;
[0114] The v is independently selected from either CH or N, and at least one of v is selected from N;
[0115] The R f R f'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0116] The R r It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0117] The s is selected from 1, 2, 3 or 4;
[0118] f1 is selected from 0, 1, 2, 3, or 4; f2 is selected from 0, 1, 2, 3, 4, 5, or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; f4 is selected from 0, 1, 2, or 3; when there are two or more R... f At that time, two or more R f The same or different between each other, or two adjacent R f They connect with each other to form substituted or unsubstituted rings;
[0119] The f'1 is selected from 0, 1, or 2; when there are two or more R... f At that time, two or more R f 'They are the same as or different from each other.'
[0120] Preferably, formula I is selected from any of the following structures:
[0121]
[0122]
[0123]
[0124] The R0 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclobutenyl, benzocyclohexyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclohex ... Cyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoleyl, benzene Any one of the following: carbazolyl, pyrrololyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl;
[0125] f1 is selected from 0, 1, 2 or 3; f2 is selected from 0, 1 or 2; f3 is selected from 0 or 1; when there are two or more R0s, the two or more R0s are the same as or different from each other;
[0126] The definitions of R1, R2, R3, R4, R5, L1, L2, L3, L4, L5, Z1, Z2, n1, n2, a, and z are the same as those in claim 1.
[0127] Preferably, the Choose any one of the following structures:
[0128]
[0129] The R d R d'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclocyclohexane, benzocyclo ...hexane, benzocyclohexane, benzocyclohexane Pentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoleyl, benzene Any one of the following: carbazolyl, pyrrololyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl;
[0130] The R4, R5, R i R j The group is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, peryl, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;
[0131] The R k Selected from hydrogen, deuterium, tritium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0132] The L' is selected from the following groups, which are single-bonded, substituted, or unsubstituted: phenylene, biphenylene, terphenylene, naphthylene, anthraceneylene, phenanthrene, phenylenetriphenylene, pyreneylene, perylene, fluoranthylene, pyridylene, pyrimidinylene, triazineylene, furanylene, thiopheneylene, carbazolylene, benzofuranylene, benzothiopheneylene, benzocarbazolylene, dibenzofuranylene, dibenzothiopheneylene, dibenzofuranylene, dibenzothiopheneylene, dibenzofuranylene Any one of carbazolyl, benzo[a]dibenzofuranyl, benzo[a]dibenzothiophenel, oxazolyl, thiazolyl, imidazolyl, benzo[a]oxazolyl, benzo[a]thiazolyl, benzo[a]imidazolyl, dibenzo[a]oxazolyl, dibenzo[a]thiazolyl, dibenzo[a]imidazolyl, quinolinyl, isoquinolinyl, quinolinyl, quinoxolinyl, bipyridyl, bipyrimidinyl, phenylpyridyl, and phenylpyrimidinyl.
[0133] The d1 is selected from 0, 1, 2, 3 or 4; when there are two or more R d At that time, two or more R d The same or different between each other, or two adjacent R d They connect with each other to form substituted or unsubstituted rings;
[0134] The d'1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d'2 is selected from 0, 1, 2, 3, 4, 5, or 6; the d'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R... d At that time, two or more R d'They are the same as or different from each other.'
[0135] More preferably, the Choose any one of the following structures:
[0136]
[0137]
[0138] d1 is selected from 0, 1, 2, 3, or 4; d2 is selected from 0, 1, 2, or 3; d3 is selected from 0, 1, or 2; when there are two or more R... d At that time, two or more R d The same or different between each other, or two adjacent R d They connect with each other to form substituted or unsubstituted rings;
[0139] The R d R d '、R4、R5、R i R j R k The definitions of L', d'1, d'2, d'3, and d'4 are the same as those in claim 3.
[0140] More preferably, the Choose any one of the following structures:
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148] Preferably, the Independently selected from any of the following structures:
[0149]
[0150] The R eThe group independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentane Alkenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoleyl, benzo[] Any one of the following: carbazolyl, pyrrololyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalolinyl, benzoquinoxalolinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl;
[0151] The R u Selected from hydrogen, deuterium, tritium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0152] The value of e1 is selected from 0, 1, 2, 3, or 4; when there are two or more R...e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings.
[0153] More preferably, the Independently selected from any of the following structures:
[0154]
[0155] Preferably, L1 and L2 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:
[0156]
[0157]
[0158] The R b R b '、R p R q The group independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane. The following are all of the following: benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridinyl, indolyl, acridineyl, phenoxazinyl, phenthiazinyl;
[0159] The R tThe following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;
[0160] b1 is selected from 0, 1, 2, 3, or 4; b2 is selected from 0, 1, 2, 3, 4, 5, or 6; b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b4 is selected from 0, 1, or 2; b5 is selected from 0, 1, 2, or 3; b6 is selected from 0 or 1; when there are two or more R... b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings;
[0161] The b'1 is selected from 0, 1, or 2; the b'2 is selected from 0, 1, 2, 3, or 4; the b'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R b At that time, two or more R b 'They are the same as or different from each other.'
[0162] More preferably, L1 and L2 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:
[0163]
[0164]
[0165] Preferably, L3 and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:
[0166]
[0167] X3 is selected from O, S, N(R) s Any one of the following;
[0168] X4 is selected from O, S, C(R) x R y ), N(R s Any one of the following;
[0169] The term 'e' is independently selected from either CH or N;
[0170] The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0171] The R a R a '、R x R y Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings;
[0172] The R s It is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;
[0173] p is selected from 1, 2, 3, or 4;
[0174] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a4 is selected from 0, 1, or 2; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings;
[0175] The a'1 is selected from 0, 1, or 2; when there are two or more R a At that time, two or more R a 'They are the same as or different from each other.'
[0176] More preferably, L3 and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:
[0177]
[0178] The R a R a '、R x R y The group independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane. The following are all of the following: benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, oxazolyl, benzooxazolyl, dibenzooxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, quinoxolinyl, benzoquinoxolinyl, phenantholinyl, naphridinyl, indolyl, acridineyl, phenoxazinyl, phenthiazinyl;
[0179] The R sThe following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;
[0180] a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, 3, 4, 5, or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a4 is selected from 0, 1, or 2; a5 is selected from 0, 1, 2, or 3; a6 is selected from 0 or 1; when there are two or more R... a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings;
[0181] a'1 is selected from 0, 1, or 2; a'2 is selected from 0, 1, 2, 3, or 4; a'3 is selected from 0, 1, 2, 3, 4, 5, or 6; a'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; a'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R... a At that time, two or more R a 'They are the same as or different from each other.'
[0182] More preferably, L3 and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:
[0183]
[0184] Preferably, L4 is selected from any one of the following groups or from a combination of two or more of the following groups:
[0185]
[0186]
[0187] The R c R c 'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or any of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, group 1, any one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cyclic groups, and R c At least one of the following is selected from Group 1: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic groups, and fused cycloalkanes of C6-C30 aromatic groups;
[0188] The R v The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl;
[0189] c1 is selected from 1, 2, 3, or 4; c2 is selected from 1, 2, 3, 4, 5, or 6; c3 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 1 or 2; c5 is selected from 1, 2, or 3; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent Rc They connect with each other to form substituted or unsubstituted rings;
[0190] The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'
[0191] Preferred, "R" c At least one of them includes R c One, two, or more.
[0192] Preferred, "R" c The other groups besides "at least one" are selected from hydrogen, deuterium, and tritium.
[0193] More preferably, the L4 is selected from any one of the following groups or from a combination of two or more of the following groups:
[0194]
[0195] Preferably, the R c The phrase "Group 1, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic groups and C6-C30 aromatic fused cyclic groups" is selected from any one of the following groups or from a combination of two or more of the following groups:
[0196]
[0197] The R g R g '、R h R h'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclo...' Butyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, carbazolyl, pyrroleyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxolinyl, benzoquinoxolinyl, phenanthrolyl, naphridyl, indolyl, acridineyl, phenazinyl, phenoxazinyl, phenothiazinyl;
[0198] The R r The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilane. The following are all of the following: alkyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, pyridinyl;
[0199] g1 is selected from 0, 1, 2, 3, 4, or 5; g2 is selected from 0, 1, 2, 3, or 4; g3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; g5 is selected from 0, 1, or 2; g6 is selected from 0, 1, 2, or 3; g7 is selected from 0, 1, 2, 3, 4, 5, or 6; g8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... g At that time, two or more R g The same or different between each other, or two adjacent R g They connect with each other to form substituted or unsubstituted rings;
[0200] The g'1 is selected from 0, 1, or 2; the g'2 is selected from 0, 1, 2, 3, or 4; the g'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the g'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the g'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the g'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R... g At that time, two or more R g 'They are the same as or different from each other.'
[0201] More preferably, the R c Selected from any one of the following groups or from two or more of the following groups:
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210] Most preferably, formula I is selected from any of the following structures:
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232]
[0233]
[0234]
[0235]
[0236]
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253] The above lists some specific structural forms of aromatic amine compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.
[0254] Preferably, the electron transport region comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the compounds of Formula I described in this invention.
[0255] Preferably, the electron transport region comprises an electron transport layer and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises at least one of the compounds of Formula I described in this invention.
[0256] Preferably, the electron transport region includes an electron transport layer, which includes at least one of the compounds of Formula I described in this invention.
[0257] Preferably, the electron transport region includes a hole blocking layer, which includes at least one of the compounds of Formula I described in this invention.
[0258] Preferably, the thickness of the electron transport layer is
[0259] More preferably, the thickness of the electron transport layer is
[0260] More preferably, the thickness of the electron transport layer is
[0261] Preferably, the thickness of the hole-blocking layer is
[0262] More preferably, the thickness of the hole-blocking layer is
[0263] More preferably, the thickness of the hole-blocking layer is
[0264] Preferably, the electron transport layer and the hole blocking layer satisfy the following:
[0265] LUMO(G) - LUMO(K) < 0.5 eV;
[0266] Wherein, LUMO(G) is the lowest unoccupied molecular orbital energy level of the hole blocking layer;
[0267] LUMO(K) is the lowest unoccupied molecular orbital energy level of the electron transport layer.
[0268] More preferably, the electron transport layer and the hole blocking layer satisfy the following:
[0269] LUMO(G) - LUMO(K) < 0.3 eV;
[0270] Wherein, LUMO(G) is the lowest unoccupied molecular orbital energy level of the hole blocking layer;
[0271] LUMO(K) is the lowest unoccupied molecular orbital energy level of the electron transport layer.
[0272] The anode of this invention is preferably made of a material with a high work function, including metals, alloys, conductive compounds, and mixtures thereof. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode can be selected from metals, such as gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or alloys thereof; metal oxides, such as zinc oxide (ZnO), indium oxide (InO), tin oxide (SnO2), zinc oxide (ZnO), indium tin oxide (ITO), or indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited thereto.
[0273] The hole injection layer described in this invention is preferably made of a material with high hole injectability. It may include metalloporphyrins, oligothiophenes, anthraquinone compounds, aromatic amine derivatives, polycyano-conjugated organic compounds, quinacridone compounds, polymers, etc. Examples include, but are not limited to, 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene (HAT-CN), copper phthalocyanine (CuPC), 4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 7,7,8,8-tetracyano-p-benzoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-p-benzoquinone dimethyl ether (F4-TCNQ), and 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB).
[0274] The hole transport layer described in this invention is preferably made of a material with high hole transport properties. It may include benzidine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc. Examples include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA).
[0275] The electron blocking layer described in this invention is preferably made of a material with good hole transport capability and electron blocking capability. It may include aromatic amine derivatives, carbazole derivatives, etc. Examples include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), but it is not limited thereto.
[0276] The luminescent layer of this invention can use red, green, or blue luminescent materials, and typically contains a guest (doped) material and a host material. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer not only needs to possess bipolar charge transport properties, but also needs appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material can be selected from materials such as stilbene aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives. Specific examples include 4,4'-bis(9-carbazole)biphenyl (CBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9, Examples of such products include, but are not limited to, 9'-(2,6-pyridinidyldi-3,1-phenylene)bis-9H-carbazole (26DCZPPY), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazole)benzene (MCP), 9,10-bis(2-naphthyl)anthracene (ADN), and 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN). The guest material can be a metal complex (e.g., iridium complex, platinum complex, osmium complex, rhodium complex, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc. Specific examples include bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium acetylacetone (Ir(ppy)2(acac)), and tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir... (3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetone)iridium (Ir(bzq)2(acac)), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), etc., but not limited to these.
[0277] The hole blocking layer described in this invention, in addition to the compound of formula I provided in this invention, preferably has good electron transport performance and can block or restrict hole transport. It can usually be formed under the same conditions as the hole injection layer. This may include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers, such as bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terbiphenyl]-3,3”-diyl]dipyridine (TmPyPB), tris(8-hydroxyquinoline)aluminum(III) (Alq3), etc., but is not limited thereto. Compounds of Formula I of the present invention are preferred.
[0278] The electron transport layer described in this invention, in addition to the compound of formula I provided by this invention, preferably comprises materials with high electron transport properties. These may include metal complexes, pyridine derivatives, imidazole derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, etc., such as tris(8-hydroxyquinoline)aluminum(III) (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but are not limited thereto. The compound of formula I of this invention is preferred.
[0279] The electron injection layer described in this invention is preferably made of a material with high electron injection capability. It may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron injection capability. Examples include lithium (Li), lithium fluoride (LiF), cesium fluoride (CsF), cesium carbonate (Cs₂CO₃), aluminum oxide (Al₂O₃), lithium 8-hydroxyquinoline (Liq), etc., but are not limited thereto.
[0280] The cathode described in this invention is preferably made of a low work function material. It can be a transmission electrode, a semi-reflective electrode, or a reflection electrode. When the cathode is a transmission electrode, the cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflection electrode, the cathode material can be selected from aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg:Al), lithium-aluminum alloy (Li:Al), calcium / silver (Ca / Ag), but is not limited to these.
[0281] The capping material described in this invention is preferably a material with a high refractive index. It may include imidazole derivatives, oxazole derivatives, thiazole derivatives, aromatic amine derivatives, etc. Specific examples of the capping material include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), N4,N4,N4',N4'-tetra(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), lithium fluoride (LiF), magnesium fluoride (MgF2), etc., but are not limited thereto.
[0282] The organic layer of the aforementioned organic electroluminescent device can be deposited by vacuum deposition, spin coating, casting, Langmuir-Brønder (LB) method, etc. When using vacuum deposition, the vacuum deposition conditions vary depending on the compound.
[0283] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.
[0284] The fabrication of the above-described organic electroluminescent device is specifically described in the following embodiments. However, the following embodiments are merely illustrative of this specification, and the scope of this specification is not limited to these embodiments.
[0285] In addition, this invention also provides a method for preparing the compound of formula I, the specific synthetic route of which is shown below, but is not limited thereto:
[0286] [Synthesis Route]
[0287] Preparation of compound I:
[0288]
[0289] Xa, Xb, and Xc are each independently selected from any one of Cl, Br, and I; the limitations of Z1, Z2, L1, L2, L3, L4, L5, X, R1, R2, R3, R4, R5, n1, n2, a, and z are the same as those described above.
[0290] Description of raw materials, reagents, and characterization equipment:
[0291] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared by methods known to those skilled in the art.
[0292] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.
[0293] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.
[0294] [Synthetic Example 1] Synthesis of Compound 56
[0295]
[0296] Synthetic intermediate A-56
[0297] Under nitrogen protection, a-56 (34.91 g, 110.00 mmol), b-56 (64.95 g, 110.00 mmol), and K₂CO₃ (30.41 g, 220.00 mmol) were dissolved in 660 mL toluene, 330 mL ethanol, and 330 mL distilled water. Pd(PPh₃)₄ (1.27 g, 1.10 mmol) was added with stirring, and the mixture was heated to reflux for 3.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate A-56 (53.95 g, 75% yield); HPLC purity ≥ 99.75%. Mass spectrometry m / z: 652.0567 (theoretical value: 652.0553).
[0298] Synthetic intermediate B-56
[0299] Under nitrogen protection, A-56 (52.32 g, 80.00 mmol), c-56 (16.33 g, 80.00 mmol), and K₂CO₃ (18.38 g, 133.00 mmol) were dissolved in 450 mL toluene, 230 mL ethanol, and 230 mL distilled water. Pd(PPh₃)₄ (0.92 g, 0.80 mmol) was added with stirring, and the mixture was heated under reflux for 4.0 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate B-56 (37.51 g, 72% yield); HPLC purity ≥ 99.81%. Mass spectrometry m / z: 650.1748 (theoretical value: 650.1761).
[0300] Synthetic compound 56
[0301] Under nitrogen protection, B-56 (19.53 g, 30.00 mmol), d-56 (11.89 g, 30.00 mmol), and K₂CO₃ (6.22 g, 45.00 mmol) were dissolved in 240 mL toluene, 120 mL ethanol, and 120 mL distilled water. Pd(dppf)Cl₂ (0.22 g, 0.30 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 56 (18.06 g, 68%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 884.3421 (theoretical value: 884.3403). Theoretical elemental content (%) C 65 H 44 N2O2: C, 88.21; H, 5.01; N, 3.17. Measured elemental content (%): C, 88.23; H, 5.05; N, 3.14.
[0302] [Synthetic Example 2] Synthesis of Compound 71
[0303]
[0304] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-71, and d-56 with an equimolar amount of d-71, yielding compound 71 (17.30 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 800.2664 (theoretical value: 800.2651). Theoretical elemental content (%) C 54 H 35 F3N2O2: C, 80.99; H, 4.41; N, 3.50. Measured elemental content (%): C, 80.96; H, 4.45; N, 3.52.
[0305] [Synthetic Example 3] Synthesis of Compound 97
[0306]
[0307] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-97, and d-56 was replaced with an equimolar amount of d-97 to obtain compound 97 (17.24 g). HPLC analysis showed that the solid purity was ≥99.94%. Mass spectrometry m / z: 844.3077 (theoretical value: 844.3090). Theoretical elemental content (%) C 62 H 40N2O2: C, 88.13; H, 4.77; N, 3.32. Measured elemental content (%): C, 88.16; H, 4.79; N, 3.34.
[0308] [Synthetic Example 4] Synthesis of Compound 133
[0309]
[0310] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-133, b-56 with an equimolar amount of b-133, and d-56 with an equimolar amount of d-133, yielding compound 133 (17.70 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 830.2924 (theoretical value: 830.2933). Theoretical elemental content (%) C 61 H 38 N2O2: C, 88.17; H, 4.61; N, 3.37. Measured elemental content (%): C, 88.13; H, 4.57; N, 3.34.
[0311] [Synthetic Example 5] Synthesis of Compound 138
[0312]
[0313] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, c-56 with an equimolar amount of c-138, and d-56 with an equimolar amount of d-138, yielding compound 138 (17.45 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 830.2942 (theoretical value: 830.2933). Theoretical elemental content (%): C 61 H 38 N2O2: C, 88.17; H, 4.61; N, 3.37. Measured elemental content (%): C, 88.14; H, 4.63; N, 3.35.
[0314] [Synthetic Example 6] Synthesis of Compound 170
[0315]
[0316] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-133, c-56 with an equimolar amount of c-170, and d-56 with an equimolar amount of d-138, yielding compound 170 (19.36 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 962.2953 (theoretical value: 962.2967). Theoretical elemental content (%) C 69 H 42N2O2S: C, 86.05; H, 4.40; N, 2.91. Measured elemental content (%): C, 86.08; H, 4.46; N, 2.87.
[0317] [Synthetic Example 7] Synthesis of Compound 206
[0318]
[0319] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, and d-56 was replaced with an equimolar amount of d-206 to obtain compound 206 (18.25 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 856.3099 (theoretical value: 856.3090). Theoretical elemental content (%) C 63 H 40 N2O2: C, 88.29; H, 4.70; N, 3.27. Measured elemental content (%): C, 88.27; H, 4.72; N, 3.24.
[0320] [Synthetic Example 8] Synthesis of Compound 214
[0321]
[0322] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, and d-56 was replaced with an equimolar amount of d-214 to obtain compound 214 (18.51 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 856.3101 (theoretical value: 856.3090). Theoretical elemental content (%) C 63 H 40 N2O2: C, 88.29; H, 4.70; N, 3.27. Measured elemental content (%): C, 88.30; H, 4.68; N, 3.25.
[0323] [Synthetic Example 9] Synthesis of Compound 245
[0324]
[0325] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, c-56 with an equimolar amount of c-245, and d-56 with an equimolar amount of d-245, yielding compound 245 (18.57 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 896.3023 (theoretical value: 896.3039). Theoretical elemental content (%) C 65 H 40N2O3: C, 87.03; H, 4.49; N, 3.12. Measured elemental content (%): C, 87.01; H, 4.52; N, 3.17.
[0326] [Synthetic Example 10] Synthesis of Compound 309
[0327]
[0328] According to the preparation method in Example 1, d-56 was replaced with an equimolar amount of d-138 to obtain compound 309 (19.60 g, 70%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 932.3387 (theoretical value: 932.3403). Theoretical elemental content (%) C 69 H 44 N2O2: C, 88.82; H, 4.75; N, 3.00. Measured elemental content (%): C, 88.85; H, 4.77; N, 3.04.
[0329] [Synthetic Example 11] Synthesis of Compound 372
[0330]
[0331] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-372, b-56 was replaced with an equimolar amount of b-372, and d-56 was replaced with an equimolar amount of d-138, yielding compound 372 (22.01 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1032.3730 (theoretical value: 1032.3716). Theoretical elemental content (%) C 77 H 48 N2O2: C, 89.51; H, 4.68; N, 2.71. Measured elemental content (%): C, 89.53; H, 4.67; N, 2.68.
[0332] [Synthetic Example 12] Synthesis of Compound 403
[0333]
[0334] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-71, and d-56 was replaced with an equimolar amount of d-403 to obtain compound 403 (17.77 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 870.3237 (theoretical value: 870.3246). Theoretical elemental content (%) C 64 H 42N2O2: C, 88.25; H, 4.86; N, 3.22. Measured elemental content (%): C, 88.31; H, 4.82; N, 3.26.
[0335] [Synthetic Example 13] Synthesis of Compound 448
[0336]
[0337] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-133, c-56 with an equimolar amount of c-448, and d-56 with an equimolar amount of d-138, yielding compound 448 (20.59 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 914.3892 (theoretical value: 914.3872). Theoretical elemental content (%) C 67 H 50 N2O2: C, 87.94; H, 5.51; N, 3.06. Measured elemental content (%): C, 87.98; H, 5.49; N, 3.11.
[0338] [Synthetic Example 14] Synthesis of Compound 453
[0339]
[0340] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-453, c-56 with an equimolar amount of c-453, and d-56 with an equimolar amount of d-138, yielding compound 453 (18.90 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 874.2979 (theoretical value: 874.2996). Theoretical elemental content (%) C 63 H 39 FN2O2: C, 86.48; H, 4.49; N, 3.20. Measured elemental content (%): C, 86.41; H, 4.54; N, 3.24.
[0341] [Synthetic Example 15] Synthesis of Compound 485
[0342]
[0343] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-372, b-56 with an equimolar amount of b-133, c-56 with an equimolar amount of c-485, and d-56 with an equimolar amount of d-138, yielding compound 485 (16.27 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 785.3077 (theoretical value: 785.3091). Theoretical elemental content (%) C 57 H 31 D5N2O2: C, 87.11; H, 5.26; N, 3.56. Measured elemental content (%): C, 87.15; H, 5.28; N, 3.50.
[0344] [Synthetic Example 16] Synthesis of Compound 490
[0345]
[0346] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, and d-56 was replaced with an equimolar amount of d-490, yielding compound 490 (18.08 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 860.3359 (theoretical value: 860.3341). Theoretical elemental content (%) C 63 H 36 D4N2O2: C, 87.88; H, 5.15; N, 3.25. Measured elemental content (%): C, 87.95; H, 5.20; N, 3.23.
[0347] [Synthetic Example 17] Synthesis of Compound 499
[0348]
[0349] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-133, c-56 with an equimolar amount of c-499, and d-56 with an equimolar amount of d-138, yielding compound 499 (19.19 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 852.3187 (theoretical value: 852.3172). Theoretical elemental content (%) C 60 H 44 N2O2Si: C, 84.47; H, 5.20; N, 3.28. Measured elemental content (%): C, 84.53; H, 5.18; N, 3.32.
[0350] [Synthetic Example 18] Synthesis of Compound 550
[0351]
[0352] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-71, c-56 with an equimolar amount of c-550, and d-56 with an equimolar amount of d-550, yielding compound 550 (20.10 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 970.3546 (theoretical value: 970.3559). Theoretical elemental content (%) C 72 H 46 N2O2: C, 89.05; H, 4.77; N, 2.88. Measured elemental content (%): C, 89.07; H, 4.74; N, 2.85.
[0353] [Synthetic Example 19] Synthesis of Compound 597
[0354]
[0355] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-597, and d-56 with an equimolar amount of d-597, yielding compound 597 (17.23 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 786.3138 (theoretical value: 786.3122). Theoretical elemental content (%) C 57 H 26 D8N2O2: C, 87.00; H, 5.38; N, 3.56. Measured elemental content (%): C, 86.94; H, 5.43; N, 3.58.
[0356] [Synthetic Example 20] Synthesis of Compound 615
[0357]
[0358] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-615, and d-56 was replaced with an equimolar amount of d-615 to obtain compound 615 (17.24 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 797.3135 (theoretical value: 797.3122). Theoretical elemental content (%) C 58 H 35 D3N2O2: C, 87.30; H, 5.18; N, 3.51. Measured elemental content (%): C, 87.32; H, 5.17; N, 3.53.
[0359] [Synthetic Example 21] Synthesis of Compound 640
[0360]
[0361] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-133, c-56 with an equimolar amount of c-640, and d-56 with an equimolar amount of d-640, yielding compound 640 (19.27 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 930.3257 (theoretical value: 930.3246). Theoretical elemental content (%) C 69 H 42 N2O2: C, 89.01; H, 4.55; N, 3.01. Measured elemental content (%): C, 89.03; H, 4.56; N, 2.98.
[0362] [Synthetic Example 22] Synthesis of Compound 691
[0363]
[0364] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-372, b-56 with an equimolar amount of b-133, and d-56 with an equimolar amount of d-691, yielding compound 691 (15.73 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 748.3083 (theoretical value: 748.3090). Theoretical elemental content (%) C 54 H 40 N2O2: C, 86.60; H, 5.38; N, 3.74. Measured elemental content (%): C, 86.62; H, 5.37; N, 3.72.
[0365] [Synthetic Example 23] Synthesis of Compound 708
[0366]
[0367] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-133, and d-56 was replaced with an equimolar amount of d-708, yielding compound 708 (17.17 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 794.2578 (theoretical value: 794.2569). Theoretical elemental content (%) C 57 H 34 N2O3: C, 86.13; H, 4.31; N, 3.52. Measured elemental content (%): C, 86.11; H, 4.30; N, 3.54.
[0368] [Synthetic Example 24] Synthesis of Compound 785
[0369]
[0370] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-785, and d-56 with an equimolar amount of d-785, yielding compound 785 (16.63 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 780.2787 (theoretical value: 780.2777). Theoretical elemental content (%) C 57 H 36 N2O2: C, 87.67; H, 4.65; N, 3.59. Measured elemental content (%): C, 87.68; H, 4.66; N, 3.58.
[0371] [Synthetic Example 25] Synthesis of Compound 865
[0372]
[0373] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-865, b-56 with an equimolar amount of b-865, and d-56 with an equimolar amount of c-550, yielding compound 865 (17.28 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 788.2332 (theoretical value: 788.2320). Theoretical elemental content (%) C 55 H 36 N2S2: C, 83.72; H, 4.60; N, 3.55. Measured elemental content (%): C, 83.75; H, 4.56; N, 3.57.
[0374] [Synthetic Example 26] Synthesis of Compound 930
[0375]
[0376] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-930, c-56 with an equimolar amount of c-930, and d-56 with an equimolar amount of d-138, yielding compound 930 (17.61 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 862.2463 (theoretical value: 862.2476). Theoretical elemental content (%) C 61 H 38 N2S2: C, 84.89; H, 4.44; N, 3.25. Measured elemental content (%): C, 84.85; H, 4.49; N, 3.27.
[0377] [Synthetic Example 27] Synthesis of Compound 978
[0378]
[0379] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-372, b-56 with an equimolar amount of b-930, and d-56 with an equimolar amount of d-978, yielding compound 978 (19.49 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 889.2598 (theoretical value: 889.2585). Theoretical elemental content (%) C 62 H 39 N3S2: C, 83.66; H, 4.42; N, 4.72. Measured elemental content (%): C, 83.69; H, 4.37; N, 4.74.
[0380] [Synthetic Example 28] Synthesis of Compound 1038
[0381]
[0382] According to the preparation method in Synthesis Example 1, a-56 was replaced with an equimolar amount of a-71, b-56 with an equimolar amount of b-930, and d-56 with an equimolar amount of d-1038, yielding compound 1038 (16.69 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 817.2642 (theoretical value: 817.2634). Theoretical elemental content (%) C 57 H 31 D5N2S2: C, 83.69; H, 5.05; N, 3.42. Measured elemental content (%): C, 83.67; H, 5.09; N, 3.41.
[0383] [Synthetic Example 29] Synthesis of Compound 1105
[0384]
[0385] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-930, and d-56 was replaced with an equimolar amount of d-1105, yielding compound 1105 (19.67 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 922.3429 (theoretical value: 922.3415). Theoretical elemental content (%) C 65 H 50 N2S2: C, 84.56; H, 5.46; N, 3.03. Measured elemental content (%): C, 84.57; H, 5.42; N, 3.05.
[0386] [Synthetic Example 30] Synthesis of Compound 1161
[0387]
[0388] According to the preparation method in Example 1, b-56 was replaced with an equimolar amount of b-930, and d-56 was replaced with an equimolar amount of d-1161 to obtain compound 1161 (20.13 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 918.2181 (theoretical value: 918.2197). Theoretical elemental content (%) C 63 H 38 N2S3: C, 82.32; H, 4.17; N, 3.05. Measured elemental content (%): C, 82.29; H, 4.18; N, 3.04.
[0389] [Synthetic Example 31] Synthesis of Compound 1223
[0390]
[0391] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-133, b-56 with an equimolar amount of b-1223, and d-56 with an equimolar amount of d-1223, yielding compound 1223 (17.71 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 880.2959 (theoretical value: 880.2946). Theoretical elemental content (%) C 62 H 44 N2S2: C, 84.51; H, 5.03; N, 3.18. Measured elemental content (%): C, 84.55; H, 5.01; N, 3.19.
[0392] [Synthetic Example 32] Synthesis of Compound 1237
[0393]
[0394] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-1237, c-56 was replaced with an equimolar amount of c-1237, and d-56 was replaced with an equimolar amount of d-1237, yielding compound 1237 (18.57 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 883.3691 (theoretical value: 883.3675). Theoretical elemental content (%) C 64 H 45 N5: C, 86.95; H, 5.13; N, 7.92. Measured element content (%): C, 86.91; H, 5.11; N, 7.95.
[0395] [Synthetic Example 33] Synthesis of Compound 1327
[0396]
[0397] According to the preparation method in Example 1, a-56 was replaced with an equimolar amount of a-372, b-56 with an equimolar amount of b-1327, and d-56 with an equimolar amount of d-138, yielding compound 1327 (16.87 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 780.2763 (theoretical value: 780.2777). Theoretical elemental content (%) C 57 H 36 N2O2: C, 87.67; H, 4.65; N, 3.59. Measured elemental content (%): C, 87.64; H, 4.61; N, 3.63.
[0398] [Synthetic Example 34] Synthesis of Compound 1355
[0399]
[0400] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-1355, and d-56 was replaced with an equimolar amount of d-1355, yielding compound 1355 (19.00 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 855.2898 (theoretical value: 855.2886). Theoretical elemental content (%) C 62 H 37 N3O2: C, 87.00; H, 4.36; N, 4.91. Measured elemental content (%): C, 87.04; H, 4.31; N, 4.92.
[0401] [Synthetic Example 35] Synthesis of Compound 1418
[0402]
[0403] According to the preparation method in Synthesis Example 1, b-56 was replaced with an equimolar amount of b-1418, and d-56 was replaced with an equimolar amount of d-138, yielding compound 1418 (20.04 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 967.2811 (theoretical value: 967.2803). Theoretical elemental content (%) C 66 H 41 N5S2: C, 81.88; H, 4.27; N, 7.23. Measured elemental content (%): C, 81.87; H, 4.24; N, 7.25.
[0404] [Device Examples]
[0405] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.
[0406] [Example 1]
[0407] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, it was transferred to a plasma cleaner, and then transferred to a vapor deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was vapor deposited onto the anode to form a thickness of [missing information]. A hole injection layer. HT-2 is deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using BH-1 as the host material and 4wt% BD-1 doped with it, forming a layer with a thickness of [missing information]. The light-emitting layer. Compound 56 of the present invention is deposited on the light-emitting layer to form a thickness of... A hole-blocking layer is formed. ET-1:LiQ (mass ratio 1:1) is deposited on the hole-blocking layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.
[0408]
[0409] [Examples 2-35]
[0410] Compounds 71, 97, 133, 138, 170, 206, 214, 245, 309, 372, 403, 448, 453, 485, 490, 499, 550, 597, 615, 640, 691, 708, 785, 865, 930, 978, 1038, 1105, 1161, 1223, 1237, 1327, 1355, and 1418 of this invention were used to replace compound 56 in Example 1 as hole blocking layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.
[0411] [Comparative Examples 1-3]
[0412] Compounds P-1, P-2, and P-3 were used to replace compound 56 in Example 1 as hole blocking layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.
[0413] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-35 and comparative examples 1-3 in the embodiments of the present invention are shown in Table 1 below.
[0414] Table 1:
[0415]
[0416]
[0417] As shown in Table 1, when the compound described in this invention is applied to the hole blocking layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and a longer lifespan.
[0418] [Example 36]
[0419] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-2 was then deposited onto the anode to form a layer with a thickness of [missing information]. A hole injection layer was formed. HT-3 was deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer is formed. A light-emitting layer is deposited on the hole transport layer, using GH-2 as the host material and doped with 5wt% GD-2, forming a layer with a thickness of [missing information]. The light-emitting layer. HB-2 is deposited on the light-emitting layer to form a thickness of [missing information]. A hole-blocking layer. Compound 56 of the present invention is deposited on the hole-blocking layer to form a thickness of [missing information]. An electron transport layer is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer is formed. Al is deposited on the electron-injected layer to form a layer with a thickness of [missing information]. The cathode is used to form an organic light-emitting device.
[0420]
[0421] [Examples 37-70]
[0422] Compounds 71, 97, 133, 138, 170, 206, 214, 245, 309, 372, 403, 448, 453, 485, 490, 499, 550, 597, 615, 640, 691, 708, 785, 865, 930, 978, 1038, 1105, 1161, 1223, 1237, 1327, 1355, and 1418 of the present invention were used to replace compound 56 in Example 36 as the electron transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 36.
[0423] [Comparative Examples 4-6]
[0424] Organic electroluminescent devices were prepared by replacing compound 56 in Example 36 with compounds P-4, P-5, and P-6 as electron transport layer materials, except that the preparation method was the same as that in Example 36.
[0425] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 36-70 and comparative examples 4-6 in the embodiments of the present invention are shown in Table 2 below.
[0426] Table 2:
[0427]
[0428]
[0429] As shown in Table 2, when the compound described in this invention is applied to the electron transport layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and a longer lifespan.
[0430] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.
Claims
1. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a hole-transporting region, an electron-transporting region, and a light-emitting layer, the hole-transporting region being between the light-emitting layer and the anode, the electron-transporting region being between the light-emitting layer and the cathode, characterized in that, The electron transport region comprises a fluorene compound represented by Formula I, wherein the X is independently selected from any one of C(R0), N; the z is independently selected from any one of CH, N; the Z1, Z2 is independently selected from any one of O, S, N(R6); the R0, R1, R2, R3, R4, R5 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C30 arycycle, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 arycycle, substituted or unsubstituted fused ring group of C3-C25 alicycle and C2-C30 heteroarycyclyl, or R4 and R5 are connected to form a substituted or unsubstituted ring; the R6 is independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C30 arycycle, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 arycycle, substituted or unsubstituted fused ring group of C3-C25 alicycle and C2-C30 heteroarycyclyl; the n1 is selected from 0, 1, 2, 3 or 4; when two or more R1 are present, the two or more R1 are the same as or different from each other, or adjacent two R1 are connected to each other to form a substituted or unsubstituted ring; the n2 is selected from 0, 1, 2, 3 or 4; when two or more R2 are present, the two or more R2 are the same as or different from each other, or adjacent two R2 are connected to each other to form a substituted or unsubstituted ring; the a is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when two or more R3 are present, the two or more R3 are the same as or different from each other, or adjacent two R3 are connected to each other to form a substituted or unsubstituted ring; L1, L2are independently selected from a single bond or any one of the following groups or from a combination of two or more of the following groups: said X1is selected from any one of O, S, N(R t ) ; said X2is selected from O, S, C(R p R q ), N(R t ) in any combination; the u is independently selected from any one of CH, N; the u' is independently selected from any one of CH, N, and at least two of u' are selected from N; the ring A is selected from substituted or unsubstituted C3-C10 alicycle; said R b , R b , R p , R q are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C30 aryl ring, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 aryl ring, substituted or unsubstituted fused ring group of C3-C25 alicycle and C2-C30 heteroaromatic ring, or R p , R q are linked to form a substituted or unsubstituted ring; said R t is independently selected from any of hydrogen, deuterium, tritium, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroarycyclo fused ring group; the q is selected from 1, 2, 3 or 4; said b1 is selected from 0, 1, 2, 3, or 4; said b2 is selected from 0, 1, 2, 3, 4, 5, or 6; said b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said b4 is selected from 0, 1, or 2; when there are two or more R b groups, two or more R b groups are the same or different from each other, or two adjacent R b groups are connected to each other to form a substituted or unsubstituted ring; said b'1 is selected from 0, 1 or 2; when two or more R b ' are present, two or more R b ' are identical or different from each other; L3, L5are independently selected from any one of a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroarycyclo fused ring group; L4is selected from any one of the following groups or a combination of two or more of the following groups; said X5is selected from any one of O, S, N(R v ) ; X6is selected from any one of O, S; i is independently selected from any one of CH, N; i' is independently selected from any one of CH, N, and at most two of i' are selected from N; ring C is selected from substituted or unsubstituted C3-C10 alicyclo; The R c , R c ' is independently selected from any of Group 1, hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C25 alicyclic and C2-C30 heteroaromatic ring, and R c at least one is selected from any of Group 1, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic and C6-C30 aromatic ring; said R v is independently selected from any of hydrogen, deuterium, tritium, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroarycyclo fused ring group; r is selected from 1, 2, 3, or 4; said c1 is selected from 1, 2, 3 or 4; said c2 is selected from 1, 2, 3, 4, 5 or 6; said c3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 1 or 2; when there are two or more R c groups, two or more R c groups are the same or different from each other, or two adjacent R c groups are connected to each other to form a substituted or unsubstituted ring; said c'1 is selected from 0, 1 or 2; when two or more R c ' are present, two or more R c ' are identical or different from each other; Group 1: Y1, Y2, Y3are independently selected from O, S, N(R r ) any one of; v is independently selected from any one of CH, N, and at least one of v is selected from N; R f , R f ' is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C25 alicyclic and C2-C30 heteroaromatic ring. said R r is independently selected from any of hydrogen, deuterium, tritium, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroarycyclo fused ring group; s is selected from 1, 2, 3, or 4; said f1 is selected from 0, 1, 2, 3, or 4; said f2 is selected from 0, 1, 2, 3, 4, 5, or 6; said f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said f4 is selected from 0, 1, 2, or 3; when there are two or more R f groups, two or more R f groups are the same or different from each other, or two adjacent R f groups are connected to each other to form a substituted or unsubstituted ring; said f'1 is selected from 0, 1 or 2; when two or more R f ' are present, two or more R f ' are the same or different from each other.
2. The organic electroluminescent device according to claim 1, wherein Formula I is selected from any one of the following structures: R0is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzcyclopropanyl, naphthocyclopropanyl, benzcyclobutanyl, naphthocyclobutanyl, benzcyclopentanyl, naphthocyclopentanyl, benzcyclohexanyl, naphthocyclohexanyl, benzcycloheptanyl, benzo-cyclobutenyl, benzo-cyclopentenyl, benzo-cyclohexenyl, benzo-cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzdibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzdibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthidinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; f1is selected from 0, 1, 2, or 3; f2is selected from 0, 1, or 2; f3is selected from 0 or 1; when two or more R0are present, two or more R0are the same as or different from each other; The definitions of R1, R2, R3, R4, R5, L1, L2, L3, L4, L5, Z1, Z2, n1, n2, a, and z are the same as those in claim 1.
3. The organic electroluminescent device according to claim 1, wherein The is selected from any one of the following structures: R d , R d ' are independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzcyclopropanyl, naphthocyclopropanyl, benzcyclobutanyl, naphthocyclobutanyl, benzcyclopentanyl, naphthocyclopentanyl, benzcyclohexanyl, naphthocyclohexanyl, benzcycloheptanyl, benzcyclobutenyl, benzcyclopentenyl, benzcyclohexenyl, benzcycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzdibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzdibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthrydinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl, any of which is substituted or unsubstituted; R4, R5, R i , R j are independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted any one of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzcyclopropanyl, naphthocyclopropanyl, benzcyclobutanyl, naphthocyclobutanyl, benzcyclopentanyl, naphthocyclopentanyl, benzcyclohexanyl, naphthocyclohexanyl, benzcycloheptanyl, benzcyclobutenyl, benzcyclopentenyl, benzcyclohexenyl, benzcycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R k Selected from hydrogen, deuterium, tritium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The L' is selected from a single bond, or any one of the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, triphenylylene, pyrenylene, pyrylenylene, fluoranthenylene, pyridylene, pyrimidylene, triazylene, furanylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, dibenzocarbazolylene, benzodibenzofuranylene, benzodibenzothienylene, oxazolylene, thiazolylene, imidazolylene, benzoxazolylene, benzothiazolylene, benzimidazolylene, dibenzoxazolylene, dibenzothiazolylene, dibenzimidazolylene, quinolylene, isoquinolylene, quinazolylene, quinoxalylene, bipyridylene, bipyrimidylene, phenylpyridylene, phenylpyrimidylene, or a combination of two or more thereof; said d1 is selected from 0, 1, 2, 3 or 4; when two or more R d are present, two or more R d are the same or different from each other, or two adjacent R d are connected to each other to form a substituted or unsubstituted ring; d'1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; d'2 is selected from 0, 1, 2, 3, 4, 5, or 6; d'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; d'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when two or more R d ' are present, two or more R d ' are the same or different from each other.
4. The organic electroluminescent device according to claim 1, wherein The is selected from any one of the following structures: said d1 is selected from 0, 1, 2, 3 or 4; said d2 is selected from 0, 1, 2 or 3; said d3 is selected from 0, 1 or 2; when there are two or more R d groups, two or more R d groups are the same or different from each other, or two adjacent R d groups are connected to each other to form a substituted or unsubstituted ring; R d , R d , R i , R j , R k , L', d'1, d'2, d'3, d'4 are defined as in claim 3.
5. The organic electroluminescent device according to claim 1, wherein the is independently selected from any one of the following structures: R e is independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, and any one of the following groups which is substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzcyclopropanyl, naphthocyclopropanyl, benzcyclobutanyl, naphthocyclobutanyl, benzcyclopentanyl, naphthocyclopentanyl, benzcyclohexanyl, naphthocyclohexanyl, benzcycloheptanyl, benzcyclobutenyl, benzcyclopentenyl, benzcyclohexenyl, benzcycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzdibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzdibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthidinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl, The R u Selected from hydrogen, deuterium, tritium, and the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethyl The following are all of the following: silyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluorenyl, spirofluorenyl, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; said e1 is selected from 0, 1, 2, 3, or 4; when there are two or more R e , each of which is the same or different from each other, or adjacent two R e are connected to each other to form a substituted or unsubstituted ring. e 6. The organic electroluminescent device according to claim 1, wherein The L1and L2are independently selected from a single bond, or any one of the following groups: said R b , R b , R p , R q are independently selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropanyl, naphthocyclopropanyl, benzocyclobutanyl, naphthocyclobutanyl, benzocyclopentanyl, naphthocyclopentanyl, benzocyclohexanyl, naphthocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolinyl, benzquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthrydinyl, indolyl, acridinyl, phenoxazinyl, phenothiazinyl, and any combination thereof; The R t The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; said b1 is selected from 0, 1, 2, 3, or 4; said b2 is selected from 0, 1, 2, 3, 4, 5, or 6; said b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said b4 is selected from 0, 1, or 2; said b5 is selected from 0, 1, 2, or 3; said b6 is selected from 0 or 1; when there are two or more R b groups, two or more R b groups are the same or different from each other, or two adjacent R b groups are connected to each other to form a substituted or unsubstituted ring; said b'1 is selected from 0, 1 or 2; said b'2 is selected from 0, 1, 2, 3 or 4; said b'3 is selected from 0, 1, 2, 3, 4, 5 or 6; said b'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said b'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said b'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when two or more R b ' are present, two or more R b ' are the same or different from each other.
7. The organic electroluminescent device according to claim 1, wherein The L3and L5are independently selected from a single bond, or any one of the following groups, or a combination of two or more thereof: said X3is selected from any one of O, S, N(R s ) ; said X4is selected from the group consisting of O, S, C(R x R y ), N(R s ) in any order; The e is independently selected from any one of CH and N; The ring B is selected from a substituted or unsubstituted C3-C10 alicycle; said R a , R a , R x , R y are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C30 aryl ring, substituted or unsubstituted fused ring group of C1-C25 heterocycloalkane and C6-C30 aryl ring, substituted or unsubstituted fused ring group of C3-C25 alicycle and C2-C30 heteroaromatic ring, or R x , R y are linked to form a substituted or unsubstituted ring; said R s is independently selected from any of hydrogen, deuterium, tritium, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C30 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C25 alicyclo and C2-C30 heteroarycyclo fused ring group; The p is selected from 1, 2, 3, or 4; said a1 is selected from 0, 1, 2, 3, or 4; said a2 is selected from 0, 1, 2, 3, 4, 5, or 6; said a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said a4 is selected from 0, 1, or 2; when there are two or more R a groups, two or more R a groups are the same or different from each other, or two adjacent R a groups are connected to each other to form a substituted or unsubstituted ring; said a'1 is selected from 0, 1 or 2; when two or more R a ' are present, two or more R a ' are identical or different from each other.
8. The organic electroluminescent device according to claim 1, wherein The L4is selected from any one of the following groups, or a combination of two or more thereof: The R c R c 'Independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, or any of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, group 1, any one of the following: substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cyclic groups, and R c At least one of the following is selected from Group 1: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic groups, and fused cycloalkanes of C6-C30 aromatic groups; The R v The following groups are independently selected from hydrogen, deuterium, tritium, and substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl The following are all of the following: vinyl dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; said c1 is selected from 1, 2, 3 or 4; said c2 is selected from 1, 2, 3, 4, 5 or 6; said c3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; said c4 is selected from 1 or 2; said c5 is selected from 1, 2 or 3; when there are two or more R c groups, two or more R c groups are the same or different from each other, or two adjacent R c groups are connected to each other to form a substituted or unsubstituted ring; said c'1 is selected from 0, 1 or 2; when two or more R c ' are present, two or more R c ' are identical or different from each other.
9. The organic electroluminescent device according to claim 1, wherein The formula I is selected from any one of the following structures:
10. The organic electroluminescent device according to claim 1, wherein The electron transport layer satisfies: LUMO(G)-LUMO(K) < 0.5 eV; LUMO(G) is the lowest unoccupied molecular orbital energy level of the hole blocking layer; LUMO(K) is the lowest unoccupied molecular orbital energy level of the electron transport layer.