Organic compounds and their applications, organic electroluminescent devices and electronic devices

Abstract

This application relates to the field of organic materials, providing an organic compound, its applications, and organic electroluminescent devices and electronic devices. The organic compound has a structure as shown in Formula I, and when applied as an organic light-emitting material to the light-emitting layer of an organic electroluminescent device, it can improve the device's performance.

Description

Technical Field

[0001] This application relates to the field of organic materials, and in particular to an organic compound and its applications, as well as organic electroluminescent devices and electronic devices. Background Technology

[0002] With the development of emerging technologies, display technology plays an increasingly important role in daily production and life, and its application fields are becoming increasingly wide. Therefore, it is extremely necessary to develop new display technologies to meet the needs of different fields. Organic light-emitting diodes (also known as organic light-emitting devices, OLED devices), as a new generation of display technology, have many advantages over traditional liquid crystal displays, such as being lightweight, energy-saving, and flexible, and have therefore received widespread attention from industry, academia, and research institutions.

[0003] The light-emitting layer of organic light-emitting diodes (OLEDs) is formed using various organic light-emitting materials. Based on different light-emitting mechanisms, these organic light-emitting materials are classified into traditional fluorescent materials, heavy metal complex phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. Among them, traditional fluorescent materials have a very low theoretical exciton utilization rate (maximum only 25%), while heavy metal organic complex phosphorescent materials can achieve a theoretical exciton utilization rate of 100%, but are expensive. TADF materials, due to their relatively low singlet-triplet splitting energy, can utilize triplet excitons through reverse intersystem crossing during radiative transitions, theoretically also achieving a 100% exciton utilization rate. This is comparable to the light-emitting performance of heavy metal-containing phosphorescent materials, and compared to phosphorescent materials, TADF materials are simpler to synthesize and have lower production costs. However, currently, as novel organic light-emitting materials, the performance of organic OLED devices prepared using TADF materials is difficult to guarantee in terms of efficiency, stability, and lifetime, which limits the large-scale commercial production and application of this type of OLED device. Summary of the Invention

[0004] Therefore, the purpose of this application is to provide an organic compound, its application, and an organic electroluminescent device and electronic device. The organic compound can be used as a thermally activated delayed phosphor material in organic electroluminescent devices to improve device efficiency and lifespan.

[0005] In a first aspect, this application provides an organic compound having a structure as shown in Formula 1:

[0006]

[0007] Among them, X1 and X2 may be the same or different, and each is independently C(H) or N;

[0008] R 1 and R 2They may be the same or different, and each independently is H, halogen, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, or aralkyl with 7-18 carbon atoms;

[0009] L1 and L2 may be the same or different, and each is independently: a single bond, or a substituted or unsubstituted aryl group with 6-30 carbon atoms;

[0010] Ar1 and Ar2 may be the same or different, and each independently consists of: a substituted or unsubstituted aryl group with 6-50 carbon atoms, a substituted or unsubstituted heteroaryl group with 12-50 carbon atoms, or a substituted or unsubstituted diarylamino group with 12-50 carbon atoms.

[0011] In L1, L2, Ar1, and Ar2, the substituents are the same or different, and each is independently D, halogen, cyano, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, heteroaryl with 5-18 carbon atoms, alkoxy with 1-10 carbon atoms, or aralkyl with 7-18 carbon atoms; optionally, in at least one of Ar1 and Ar2, any two adjacent substituents form a ring.

[0012] Secondly, this application provides a thermally activated delayed fluorescent material, comprising the aforementioned organic compound.

[0013] Thirdly, this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other; and an organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer contains the organic compound described in the first aspect of this application.

[0014] Fourthly, this application provides an electronic device including the organic electroluminescent device described in the third aspect of this application.

[0015] The organic compound provided in this application is a thermally activated delayed fluorescence material with a dicarbonylphenanthrene group as the core structure and two acceptor groups attached. Due to the superior electron-withdrawing ability and the twisted spatial configuration within the molecule, the dicarbonylphenanthrene group, together with the attached acceptor groups, results in a lower singlet-triplet splitting energy in the compound. This is beneficial for increasing the triplet exciton anti-gap transition rate, thereby improving the external quantum efficiency of the light-emitting device and resulting in a lower start-up voltage. Furthermore, the dicarbonylphenanthrene compound itself possesses a relatively stable molecular structure and thermal stability, which can improve the lifespan of the light-emitting device.

[0016] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0017] Figure 1This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0018] Explanation of reference numerals in the attached figures

[0019] 100: Organic electroluminescent device; 1: Anode; 2: Hole injection layer; 3: Hole transport layer

[0020] 4: Organic light-emitting layer; 5: Electron transport layer; 6: Electron injection layer; 7: Cathode Detailed Implementation

[0021] To facilitate understanding of this application, a more complete description will be provided below with reference to the accompanying drawings. Preferred embodiments of this application are shown in the drawings. However, this application can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of this application.

[0022] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0023] A first aspect of this application provides an organic compound having a structure as shown in Formula I:

[0024]

[0025] Among them, X1 and X2 may be the same or different, and each is independently C(H) or N;

[0026] R 1 and R 2 They may be the same or different, and each independently is H, halogen, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, or aralkyl with 7-18 carbon atoms;

[0027] L1 and L2 may be the same or different, and each is independently: a single bond, or a substituted or unsubstituted aryl group with 6-30 carbon atoms;

[0028] Ar1 and Ar2 may be the same or different, and each independently consists of: a substituted or unsubstituted aryl group with 6-50 carbon atoms, a substituted or unsubstituted heteroaryl group with 12-50 carbon atoms, or a substituted or unsubstituted diarylamino group with 12-50 carbon atoms.

[0029] In L1, L2, Ar1, and Ar2, the substituents are the same or different, and each is independently D, halogen, cyano, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, heteroaryl with 5-18 carbon atoms, alkoxy with 1-10 carbon atoms, or aralkyl with 7-18 carbon atoms; optionally, in at least one of Ar1 and Ar2, any two adjacent substituents form a ring.

[0030] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents. For example, "substituted or unsubstituted phenyl" refers to a phenyl with substituents or an unsubstituted phenyl. The number of substituents can be one or more, and the types of substituents can be deuterium (D), halogen, cyano, alkyl, aryl, heteroaryl, alkoxy, aralkyl, etc. When the number of substituents is greater than one, any two substituents may be the same or different. It should be understood that when the functional group has substituents, the number of carbon atoms refers to the total number of carbon atoms of the functional group and its substituents. For example, in Formula I, when Ar1 is a methyl-substituted carbazolyl group, the total number of carbon atoms in Ar1 is 13, and Ar1 is a methyl-substituted carbazolyl group with 13 carbon atoms.

[0031] In this application, the term "optionally" means that the events or circumstances described below may or may not occur. For example, "optionally, in at least one of Ar1 and Ar2, any two adjacent substituents form a ring" includes both the scenario where the two substituents are connected to form a ring and the scenario where the two substituents exist alone and do not form a ring.

[0032] In this application, "two adjacent substituents" can include either two substituents attached to the same atom in a functional group, or one substituent attached to each of two adjacent atoms in a functional group. When two substituents are attached to the same atom, the two substituents and the atom they are attached to can form a spirocyclic ring; when two adjacent atoms are attached to substituents respectively, the two substituents and the functional group they are attached to can form a fused ring. When Ar1 and Ar2 are substituted dibenzo-6-membered rings, and the dibenzo-6-membered ring is... When Y is O, S, or N(Ph)), the ring formed by two adjacent substituents attached to the C atom of the six-membered ring containing Y can be any of the following structures:

[0033] Here, "*" indicates the site of insemination with a C atom. For example, in Ar1, when... In this context, Y is S, and the ring formed by the C atom on the six-membered ring containing Y and the two substituents attached to it is... At that time, Ar1 was When Ar1 and Ar2 are substituted groups At that time, the ring formed by two adjacent substituents attached to the C atom of the six-membered ring containing the N atom can be... Here, "*" indicates a helical bonding site with a C atom. For example, in Ar2, when... The ring formed by the two substituents on the C atom of the six-membered ring is At that time, Ar2 was

[0034] In this application, aryl refers to an aromatic hydrocarbon group derived from an aromatic ring compound by losing one hydrogen atom. Aryl can be a monocyclic aryl (such as phenyl), a fused-ring aryl (such as naphthyl), two or more monocyclic aryl groups (such as biphenyl) conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. Specific examples of aryl include, but are not limited to, phenyl, naphthyl, anthracene, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Benzyl, fluorene, etc.

[0035] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0036] In this application, a heteroaryl group refers to a group formed by replacing at least one carbon atom with a heteroatom on the basis of an aryl group. The heteroatom can be at least one of B, O, N, P, Si, Se, and S. The number of heteroatoms in a heteroaryl group can be 1, 2, 3, 4, 5, or more. A heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl. Specific examples of heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, thiophenothiophene, benzofuranyl, phenanthrololinyl, isoxazolyl, thiazolyl, phenothiazinyl, phenothiazinyl, dibenzo-p-dioxinyl, quinazolinone, benzothiazolyl, benzotriazolyl, thianthyl, phenothiazinyl, phenothiazinyl, etc.

[0037] In this application, the alkyl group can be an alkyl group having 1-10 carbon atoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH(CH3)CH2CH3), 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3), and 1-pentyl. (n-pentyl, -CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-CH(CH2CH3)2), 2-methyl-2-butyl (-C(CH3)2CH2CH3), 3-methyl-2-butyl (-CH(CH3)CH(CH3)2), 3-methyl-1-butyl (-CH2CH2CH(CH3)2), 2-methyl-1-butyl ( -CH2CH(CH3)CH2CH3), 1-hexyl(-CH2CH2CH2CH2CH2CH3), 2-hexyl(-CH(CH3)CH2CH2CH2CH3), 3-hexyl(-CH(CH2CH3)(CH2CH2CH3)), 2-methyl-2-pentyl(-C(CH3)2CH2CH2CH3), 3-methyl-2-pentyl(-CH(CH3)CH(CH3)CH2CH3), 4-methyl-2-pentyl(-CH(CH3)CH2CH(CH3)2), 3-methyl-3-pentyl(-C(CH3)(CH2CH3)2), 2-methyl-3-pentyl(-CH(CH2CH3)CH(CH3)2), 2,3-dimethyl-2-butyl(-C(CH3)2CH(CH3)2), 3,3-dimethyl-2-butyl(-CH(CH3)C(CH3)3 and octyl.

[0038] In this application, "alkoxy group" refers to the structure -OR c The group, namely the alkyl group as defined above. c It is attached to an adjacent group via an oxygen atom. Phrases containing this term, such as "alkoxy group with 1-10 carbon atoms," refer to alkyl moieties containing 1-10 carbon atoms. Examples of alkoxy groups include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0039] In this application, halogens include chlorine, fluorine, bromine, and iodine.

[0040] In this application, the number of carbon atoms in the aryl group used as a substituent can be 6-18, for example 6, 10, 12, 13, 14, or 18. Examples of aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, fluorenyl, and phenanthrene.

[0041] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 5-18, for example 5, 6, 10, 12, 13, 14, or 18. Examples of heteroaryl groups used as substituents include, but are not limited to, pyridyl, quinolinyl, and carbazole.

[0042] In this application, The term "linking bond" refers to a non-positioned linking bond that extends from the ring system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the molecule. For example, as shown in formula Q, the naphthyl group represented by formula Q is connected to other positions in the molecule via two non-positional linkers that traverse different benzene rings, representing any possible connection configuration shown in formulas Q-1 to Q-6:

[0043]

[0044] For another example, as shown in formula Z, the naphthyl group represented by formula Z is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This can represent any of the connection methods shown in formulas Z-1 and Z-2.

[0045]

[0046] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula E, the substituent R in formula E is connected to the naphthalene ring by a non-orienting linking bond, which means that it includes any of the possible connection methods shown in formulas E-1 to E-14:

[0047]

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40.

[0049] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40.

[0050] In this application, the diarylamino group can be represented as -N(Ar) a Ar b Ar a and Ar b Whether they are the same or different, they can each be an aryl group with 6-25 carbon atoms.

[0051] In some implementations, X1 and X2 in Formula I are both C(H).

[0052] In other embodiments, X1 and X2 in Formula I are both N.

[0053] In some implementations, R 1 and R 2 They may be the same or different, and each independently is H, F, an alkyl group with 1-4 carbon atoms, an aryl group with 6-12 carbon atoms, or an aralkyl group with 7-12 carbon atoms.

[0054] In some implementations, R 1 and R 2 They may be the same or different, and each independently is H, F, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0055] In some embodiments, L1 and L2 may be the same or different, and each is independently: a single bond, or a substituted or unsubstituted aryl group having 6-18 carbon atoms; in L1 and L2, the substituent is independently D, F, cyano, alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, or aryl having 6-10 carbon atoms.

[0056] In some embodiments, L1 and L2 may be the same or different, and each independently is: a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene.

[0057] In some embodiments, in L1 and L2, the substituents are independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, or phenyl.

[0058] In some embodiments, L1 and L2 may be the same or different, and each is independently a single bond or any of the following groups:

[0059]

[0060] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently a group W that is substituted or unsubstituted by one or more substituents V, wherein group W is any one of the following groups:

[0061]

[0062] Z is a single bond, O, S, N(R), C(R1R2) or Si(R3R4), R, R1, R2, R3 and R4 are the same or different, and each is independently H, an alkyl group with 1-5 carbon atoms or an aryl group with 6-12 carbon atoms;

[0063] Z1, Z2, Z3, Z4, Z5, Z6, Z7 and Z8 are the same or different, and each is independently C(H) or N;

[0064] Y1 and Y2 may be the same or different, and each is independently O, S, C (R5R6) or Si (R7R8). R5, R6, R7 and R8 may be the same or different, and each is independently H, an alkyl group with 1-5 carbon atoms or an aryl group with 6-12 carbon atoms.

[0065] Each substituent V is independently D, F, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenyl, naphthyl, or phenylalkyl.

[0066] In some embodiments, the structure of the organic compound is shown as any one of Formulas I-1 to I-4:

[0067]

[0068] In Equations I-1 and I-2, n1 represents the number of substituents V, and each n1 is independently 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0069] In equations I-3 and I-4, n2 represents the number of substituents V, and each n2 is independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0070] The definition of substituent V is as shown above.

[0071] In some implementations, both L1 and L2 are single bonds.

[0072] In other embodiments, the structure of the organic compound is shown in Formula I-5 or Formula I-6:

[0073]

[0074] Among them, Ar a and Ar bThe same or different, and each independently, are: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthraquinyl, substituted or substituted phenanthryl, or substituted or unsubstituted fluorenyl;

[0075] Ar a and Ar b In this context, the substituents are independently D, F, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, phenyl, or naphthyl.

[0076] In some implementations, L1 and L2 are the same, both being single bonds or phenylene oxides.

[0077] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from any of the following groups:

[0078]

[0079] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from any of the following groups:

[0080]

[0081] In some embodiments, the organic compound is selected from any one of the following compounds:

[0082]

[0083]

[0084]

[0085] In some implementations, in formula I, and Similarly, in this embodiment, the organic compound can be prepared by a method including the following steps:

[0086]

[0087] a: Under inert gas protection, the raw material Sub I and 1,3-bis(4-bromophenyl)propane-2-propanone undergo a Diels-Alder reaction in the presence of an organic base to prepare intermediate IM X-1.

[0088] b: In an oxygen-containing atmosphere, intermediate IM X-1 is oxidized with diphenyl ether solvent to prepare intermediate IM X-2;

[0089] c: Under inert gas protection, intermediate IM X-2 and raw material Sub II undergo a coupling reaction in the presence of an organometallic catalyst to obtain the organic compound shown in Formula I.

[0090] In step a, optionally, the molar ratio of raw material Sub I to 1,3-bis(4-bromophenyl)propane-2-propanone is 1:(2-4); for example, 1:2, 1:2.5, 1:3 or 1:4.

[0091] Optionally, the organic base is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0092] Further optionally, the molar ratio of raw material Sub I to DBU is 1:(8-10); for example, 1:8, 1:9 or 1:10.

[0093] Optionally, the reaction conditions for the Diels-Alder reaction include: a reaction temperature of 75-85°C and a reaction time of 2-6 hours.

[0094] Optionally, the Diels-Alder reaction is carried out in the presence of an organic solvent. The organic solvent may include ethanol.

[0095] In step b, optionally, the reaction conditions for the oxidation reaction include: a reaction temperature of 140-170℃ and a reaction time of 12-24h.

[0096] In step c, the raw material Sub II is

[0097] Optionally, the organometallic catalyst is tris(dibenzylacetone)palladium (Pd2(dba)3) or tetra(triphenylphosphine)palladium (Pd(PPh3)4).

[0098] Optionally, the coupling reaction is carried out in the presence of substance A, which is sodium tert-butoxide (t-BuONa) and tert-butylphosphine (P(t-Bu)3), or potassium phosphate (K3PO4).

[0099] In one embodiment, the molar ratio of tris(dibenzylacetone)palladium, sodium tert-butoxide and tert-butylphosphine is 1:(90-110):(90-110).

[0100] In one embodiment, the molar ratio of tetra(triphenylphosphine)palladium to potassium phosphate is 1:(80-100).

[0101] In step c, optionally, the molar ratio of the intermediate IM X-2 to the raw material Sub II is 1:(2-4); for example, 1:2, 1:2.5, 1:3 or 1:4.

[0102] In step c, optionally, the molar ratio of the intermediate IM X-2 to the organometallic catalyst is : (0.01-0.05).

[0103] Optionally, the conditions for the coupling reaction include: a reaction temperature of 85-110℃ and a reaction time of 18-28h.

[0104] In steps a and c, the inert gas is, for example, nitrogen.

[0105] In step b, the oxygen-containing atmosphere is, for example, air.

[0106] This application does not particularly limit the synthetic methods of the provided organic compounds. Those skilled in the art can determine suitable synthetic methods based on the structure of the organic compounds, combined with the preparation methods described above and the synthetic examples below. The synthetic examples section below also exemplarily provides methods for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all the organic compounds provided in this application based on these exemplary preparation methods, and the provided preparation methods should not be construed as limiting this application.

[0107] A second aspect of this application provides a thermally activated delayed fluorescence material, wherein the thermally activated delayed fluorescence material comprises the organic compound of this application. The organic compound of this application belongs to the category of thermally activated delayed fluorescence materials and is particularly suitable for use in fabricating the organic light-emitting layer of organic electroluminescent devices. The organic light-emitting material containing the organic compound can be applied by inkjet printing, spin coating, or vacuum evaporation to form the organic light-emitting layer of an OLED device.

[0108] A third aspect of this application provides an organic electroluminescent device, comprising: an anode and a cathode disposed opposite to each other; and an organic light-emitting layer disposed between the anode and the cathode, wherein the functional layer includes the organic light-emitting layer, and the organic light-emitting layer contains the organic compound described in this application.

[0109] In some embodiments, the organic light-emitting layer comprises a host material and a guest material, wherein the guest material includes the organic compounds described in this application.

[0110] In some embodiments, the mass ratio of the host material to the guest material in the organic light-emitting layer is (70-90):(30-10).

[0111] In this application, the host material can be a metal chelating compound, a bis(styrene) derivative, an aromatic amine derivative, or a biphenyl derivative substituted with a carbazole, and this application does not impose any special limitations on this. In some embodiments, the host material is at least one of CBP (CAS No.: 58328-31-7), TATC (CAS No.: 139092-78-7), TPD (CAS No.: 65181-78-4), and mCP (CAS No.: 550378-78-4).

[0112] This application does not particularly limit the material of the anode, and it can be any anode material capable of transporting holes. Anode materials include, for example, one or a combination of metals, metal oxides, and conductive polymers. In some embodiments, the anode material is selected from at least one of indium tin oxide (ITO), indium zinc oxide (IZO), and indium gallium zinc oxide (IGZO).

[0113] This application does not specifically limit the material of the cathode; it can be any cathode material capable of transporting electrons. The cathode material may include metals, such as one or more of magnesium (Mg), calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum (Al), silver (Ag), tin, and lead, or an alloy of at least two of these. In some embodiments, the cathode material is selected from at least one of Al, Ag, Mg, and Mg-Ag alloys.

[0114] In some embodiments, the organic electroluminescent device further includes a hole functional layer disposed between the anode and the organic light-emitting layer, and an electron functional layer disposed between the cathode and the organic light-emitting layer. The hole functional layer includes a hole injection layer and / or a hole transport layer. The electron functional layer includes an electron injection layer and / or an electron transport layer.

[0115] In one implementation, such as Figure 1 As shown, the organic electroluminescent device 100 includes an anode 1, a hole injection layer 2, an organic light-emitting layer 4, an electron transport layer 5, and a cathode 7, which are stacked sequentially.

[0116] In this application, the material of the hole injection layer 2 can be a benzidine derivative, a starburst-shaped aryl amine compound, a phthalocyanine derivative, or a conductive polymer, etc., and this application does not impose any special restrictions on it. For example, the material of the hole injection layer 2 is PEDOT:PPS.

[0117] Optionally, a hole transport layer 3 is further provided between the hole injection layer 2 and the organic light-emitting layer 4. The hole transport material of the hole transport layer 3 can be selected from various electron-rich organic materials that are conducive to hole transport, such as aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the hole transport material include, but are not limited to, TCP or NPB.

[0118] In this application, the material of the electron transport layer 5 may typically include metal complexes and / or nitrogen-containing heterocyclic derivatives, specific examples including but not limited to TPBi, BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc.

[0119] Optionally, an electron injection layer 6 is further provided between the electron transport layer 5 and the cathode 7 to enhance the ability of the cathode 7 to inject electrons into the electron transport layer 5. The material of the electron injection layer may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the material of the electron injection layer 6 is LiQ or CsF.

[0120] A fourth aspect of this application provides an electronic device including the aforementioned organic electroluminescent device.

[0121] In this application, the electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices. Specific examples include, but are not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, and optical modules.

[0122] The present application will be described below with specific synthesis examples and embodiments.

[0123] I. Synthesis of intermediates

[0124] 1. Synthesis of intermediate IM X-1

[0125] 1) Taking IM 1-1 as an example, the synthesis of each IM X-1 is explained.

[0126]

[0127] Add Sub 1 (840 mg, 4 mmol), bis(4-bromophenyl) ketone (3.4 g, 10 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 36 mmol, 5.5 mL) to a 100 mL two-necked flask, along with 50 mL of ethanol. Purge with nitrogen and evacuate under vacuum for 10 minutes. Stir and heat to 75 °C, continuing the reaction for 3 hours. Stop the reaction when the starting material has completely reacted, cool to room temperature, and pour the reaction solution into a 150 mL ground glass flask for vacuum distillation to remove the solvent. The crude product is mixed with 200-300 mesh silica gel and separated by column chromatography (mobile phase: petroleum ether: ethyl acetate, volume ratio 10:1) to obtain intermediate IM 1-1 (1.7 g, yield 80%) as a black solid product with a melting point of 145.2–146.2 °C. 1H NMR (500MHz, CDCl3) δ8.10-8.09 (m, 2H), 7.78-7.75 (m, 6H), 7.66-7.57 (m, 8H).

[0128] 2) Synthesize each of the IM X-1 listed in Table 1 according to the method of IM 1-1, except that raw material Sub 1 is replaced with raw material 1.

[0129] Table 1

[0130]

[0131] 2. Synthesis of intermediate IM X-2.

[0132] 1) Taking IM 1-2 as an example, the synthesis of each IM X-2 is explained.

[0133]

[0134] Add 1.59 g (3 mmol) of IM 1-1 to a 250 mL single-necked flask, followed by 150 mL of diphenyl ether. Purge with nitrogen and evacuate under vacuum for 30 minutes. Stir and heat to 150 °C under reflux for 24 h. Stop the reaction and remove the diphenyl ether by vacuum distillation. Separate the crude product by column chromatography (using petroleum ether:dichloromethane, volume ratio 2:1) to obtain an intermediate IM 1-2 (1.14 g, yield 70%) as a yellowish-brown solid with a melting point of 206.5–207.2 °C. 1 H NMR (400MHz, CDCl3) δ8.81 (d, J=8Hz, 2H), 7.77-7.72 (m, 4H), 7.66 (d, J=8Hz, 2H), 7.54-7.50 (m, 4H), 7.37-7.33 (m, 4H).

[0135] 2) Synthesize each of the IM X-2 listed in Table 2 according to the method of IM 1-2, except that raw material 2 is used instead of IM 1-1.

[0136] Table 2

[0137]

[0138] II. Synthesis of Compounds

[0139] Synthesis Example 1: Synthesis of Compound M1

[0140]

[0141] Add IM 1-2 (544 mg, 1 mmol), 9H-carbazole (501 mg, 3 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), sodium tert-butoxide (480 mg, 5 mmol), and tert-butylphosphine (450 mg, 5 mmol) to a 100 mL two-necked flask. Then add 40 mL of redistilled toluene, purge with nitrogen, and evacuate the flask for 15 minutes. Protect the reaction flask from light by stirring with aluminum foil and heat to 110 °C for 24 h. Stop the reaction and cool to room temperature. Extract the reaction solution and wash three times with dichloromethane (1000 mL) and water (250 mL). Dry the organic phase with anhydrous magnesium sulfate and collect the filtrate. Perform crude separation of the filtrate by column chromatography (petroleum ether:dichloromethane:acetone, volume ratio 20:2:1) to obtain a white solid, namely compound M1 (573 mg, yield 80%). Compound M1 has a melting point of 250.1–252.3 °C and a mass spectrometry m / z of 717.25 [M+H]. + NMR data: 1 H NMR (400MHz, CDC13) δ8.81 (d, J=8Hz, 2H), 8.13-8.12 (m, 4H), 7.77-7.72 (m, 4H), 7.66 (d, J=8Hz, 2H ), 7.61-7.58(m, 4H), 7.54-7.50(m, 4H), 7.37-7.33(m, 4H), 7.30-7.26(m, 4H), 7.25-7.22(m, 4H).

[0142] Synthesis Example 2: Synthesis of Compound M2

[0143]

[0144] Add IM 1-2 (544 mg, 1 mmol), 9,9-dimethyl-9,10-dihydroacrylidine (627 mg, 3 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), sodium tert-butoxide (480 mg, 5 mmol), and tert-butylphosphine (450 mg, 5 mmol) to a 100 mL two-necked flask. Then add 40 mL of redistilled toluene, purge with nitrogen, and evacuate the flask for 15 minutes using a vacuum pump. Protect the reaction flask from light by stirring while covering it with aluminum foil. The reaction mixture was heated to 110℃ for 24 hours, then stopped and cooled to room temperature. The reaction solution was extracted, and the mixture was washed three times repeatedly with dichloromethane (1000 mL) and water (250 mL). The organic phase was dried with anhydrous magnesium sulfate, and the filtrate was collected. The filtrate was crudely separated by column chromatography (developing solvent: petroleum ether:dichloromethane:acetone, volume ratio 25:2:1) to obtain a white solid, namely compound M2 (681 mg, yield 85%). The melting point of compound M2 is 235.1–236.3℃, and the mass spectrometry m / z = 801.34 [M+H]. + .

[0145] Synthesis Example 3: Synthesis of Compound M3

[0146]

[0147] Add IM 1-2 (544 mg, 1 mmol), 10H-phenothiazine (597 mg, 3 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), sodium tert-butoxide (480 mg, 5 mmol), and tert-butylphosphine (450 mg, 5 mmol) to a 100 mL two-necked flask. Then add 40 mL of redistilled toluene, purge with nitrogen, and evacuate the flask using a vacuum pump for 15 minutes. Cover the reaction flask with aluminum foil to protect it from light, stir, and heat to 110 °C for 24 h. Stop the reaction and cool to room temperature. The reaction solution was extracted at a low temperature and washed four times with dichloromethane (1000 mL) and water (250 mL). The organic phase was dried with anhydrous magnesium sulfate, and the filtrate was collected. The filtrate was crudely separated by column chromatography (petroleum ether:dichloromethane:acetone (volume ratio 25:2:1)) to give a white solid, compound M3 (620 mg, yield 79%). The melting point of compound M3 is 255.1–256.3 °C, and the mass spectrometry m / z = 781.19 [M+H]. + NMR data: 1H NMR (400MHz, CDCl3) δ8.81 (d, J=8Hz, 2H), 7.77-7.72 (m, 4H), 7.66 (d, J=8Hz, 2H), 7.54-7.50 (m, 4H), 7.46 (dd, J= 7.8, 1.6Hz, 4H), 7.42 (td, J=7.7, 1.5Hz, 4H), 7.37-7.33 (m, 4H), 7.20 (dd, J=7.8, 1.4Hz, 4H), 7.12-7.04 (m, 4H).

[0148] Synthesis Example 4: Synthesis of Compound M4

[0149]

[0150] Add IM to a 100mL two-necked flask 1-2 (544 mg, 1 mmol), 3,6-di-tert-butyl-9H-carbazole (837 mg, 3 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), sodium tert-butoxide (480 mg, 5 mmol), and tert-butylphosphine (450 mg, 5 mmol) were added, followed by 40 mL of redistilled toluene. Nitrogen gas was introduced, and the mixture was evacuated for 15 minutes using a vacuum pump. The reaction flask was protected from light by stirring with aluminum foil and heated to 110 °C for 24 h. The reaction was then stopped and cooled to room temperature. The reaction solution was extracted and washed three times with dichloromethane (1000 mL) and water (250 mL). The organic phase was dried with anhydrous magnesium sulfate, and the filtrate was collected. The filtrate was crudely separated by column chromatography (developing solvent: petroleum ether: dichloromethane: acetone, volume ratio 25:2:1) to obtain a white solid, namely compound M4 (828 mg, yield 88%). Compound M4 has a melting point of 222.1–224.3 °C and a mass spectrometry m / z of 941.50 [M+H]. + .

[0151] Synthesis example 5-15

[0152] The compounds listed in Table 3 were synthesized using the same method as compound M4, except that starting material 3 was used instead of IM 1-2, and starting material 4 was used instead of 3,6-di-tert-butyl-9H-carbazole. The synthesized compounds, their yields, and mass spectrometry results are shown in Table 3.

[0153] Table 3

[0154]

[0155]

[0156] NMR data for some compounds are shown in Table 4.

[0157] Table 4

[0158]

[0159]

[0160] Example 1

[0161] Fabrication of organic electroluminescent devices

[0162] The coated glass with indium tin oxide (ITO) coating (thickness 45 nm, sheet resistance 10 Ωm-) 2 The ITO glass substrate (15mm × 15mm) underwent pretreatment: it was sequentially cleaned with acetone, isopropanol, semiconductor cleaning solution, and deionized water, with each cleaning step involving ultrasonication for 10 minutes to remove stains and dust from the surface. It was then dried in an electrically heated drying oven. The dried glass substrate was subsequently treated with O2 plasma for 20 minutes. The pretreated ITO glass substrate was used as the anode of the device.

[0163] In a vacuum glove box, PEDOT:PPS spin-coating solution (anisole solution with a concentration of 10 mg / mL) was spin-coated onto a pretreated ITO glass substrate and annealed at 150°C for 10 minutes to form a hole injection layer with a thickness of 40 nm.

[0164] Then, it was quickly transferred to another vacuum glove box, and TCB dissolved in xylene was spin-coated onto the hole injection layer at a rate of 2500 r / min. Then, it was annealed at 230°C for 30 min to form a hole transport layer with a thickness of 50 nm. After that, organic light-emitting material dissolved in chlorobenzene (composed of CBP and compound M1 in a mass ratio of 80:20, with an organic light-emitting material concentration of 20 mg / mL) was spin-coated onto the hole transport layer and annealed at 150°C for 10 min to form an organic light-emitting layer with a thickness of 40 nm.

[0165] The glass plate on which the organic light-emitting layer is formed is transferred into a vacuum evaporation chamber (vacuum degree 5×10). -5 Pa), to perform vacuum evaporation, specifically...

[0166] First, TPBi is vacuum-deposited onto the organic light-emitting layer to form an electron transport layer with a thickness of 30nm;

[0167] CsF is then vacuum-deposited onto the electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0168] Next, Al was vacuum-deposited onto the electron injection layer to form a cathode with a thickness of 150 nm.

[0169] Finally, the organic electroluminescent device was fabricated by UV curing and encapsulation followed by heating and baking for 20 minutes.

[0170] Example 2-15

[0171] Organic electroluminescent devices were prepared according to the method of Example 1, except that, when forming the organic light-emitting layer, compounds M2 to M15 (see the “Guest Material for Light-Emitting Layer” column in Table 5) were used instead of compound M1.

[0172] Comparative Example 1

[0173] Organic electroluminescent devices were prepared according to the method of Example 1, except that compound M1 was replaced with thermally delayed fluorescent material PIAnCz when forming the organic light-emitting layer.

[0174] Comparative Example 2

[0175] Organic electroluminescent devices were prepared according to the method of Example 1, except that compound M1 was replaced with compound A when forming the organic light-emitting layer.

[0176] The structures of some of the compounds used in the above embodiments and comparative examples are shown below:

[0177]

[0178] The performance of the organic electroluminescent devices prepared in the above examples and comparative examples was analyzed. At 60 mA / cm², the results showed... 2 The IVL performance of the device was tested at a current density of 1000 Cd / m. 2 The T95 lifetime of the device was tested under the specified brightness conditions, and the results are shown in Table 5.

[0179] Table 5

[0180]

[0181] As shown in Table 5, the organic light-emitting layers of OLED devices prepared in Examples 1-15 using the organic compounds of this application have better electroluminescence efficiency than the devices prepared in Comparative Examples 1-2, which can effectively improve the photoelectric performance and lifespan of OLED devices, and have a lower start-up voltage.

[0182] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0183] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the protection scope of this application. Therefore, the protection scope of this patent application should be determined by the appended claims.

Claims

1. An organic compound, characterized in that, The organic compound has a structure as shown in Formula I: Formula I Among them, X1 and X2 may be the same or different, and each is independently C(H) or N; R 1 and R 2 They may be the same or different, and each is independently H or an alkyl group having 1-10 carbon atoms; Both L1 and L2 are single bonds; Ar1 and Ar2 may be the same or different, and each is independently a group W that is substituted or unsubstituted by one or more substituents V, wherein group W is any one of the following groups: ； Z is a single bond, O, S, N(R) or C(R1R2); R, R1 and R2 may be the same or different, and each is independently H, an alkyl group with 1 to 5 carbon atoms, or an aryl group with 6 to 12 carbon atoms; Z1, Z2, Z3, Z4, Z5, Z6, Z7 and Z8 are all C(H); Y1 and Y2 may be the same or different, and each can be O or S independently; Each substituent V is independently D, methyl, ethyl, n-propyl, isopropyl, or tert-butyl; Alternatively, the structure of the organic compound is shown in Formula I-5 or Formula I-6: ； Ar a and Ar b The same or different, and each independently being: substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl, wherein the substituent is independently D, cyano, methyl, methoxy or phenyl.

2. The organic compound according to claim 1, characterized in that, R 1 and R 2 Each can be independently H, methyl, ethyl, n-propyl, isopropyl, or tert-butyl.

3. The organic compound according to claim 1, characterized in that, The structure of the organic compound is shown in any one of Formula I-1 to I-4: ； In Equations I-1 and I-2, n1 represents the number of substituents V, and each n1 is independently 0, 1, 2, 3, 4, 5, 6, 7 or 8; In Equations I-3 and I-4, n2 represents the number of substituents V, and each n2 is independently 0, 1, 2, 3, 4, 5, 6 or 7.

4. The organic compound according to claim 1, characterized in that, In the structure shown in Formula I, Ar1 and Ar2 are each independently selected from any one of the following groups: ； In the structure shown in Equation I-5 or Equation I-6, Each is independently selected from any one of the following groups: 。 5. The organic compound according to claim 1, characterized in that, In the structure shown in Formula I, Ar1 and Ar2 are each independently selected from any one of the following groups: ； In the structure shown in Equation I-5 or Equation I-6, Each is independently selected from any one of the following groups: 。 6. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds: 。 7. A thermally activated delayed fluorescent material, characterized in that, Includes the organic compounds described in any one of claims 1-6.

8. An organic electroluminescent device, characterized in that, include: Anode and cathode arranged opposite each other; as well as An organic light-emitting layer disposed between the anode and the cathode, wherein the organic light-emitting layer comprises an organic compound as described in any one of claims 1-6.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic light-emitting layer comprises a host material and a guest material, wherein the guest material includes the organic compound; The host material includes at least one of CBP, TATC, TPD and mCP.

10. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 8 or 9.

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