Organic materials, organic electroluminescent devices and electronic devices

Abstract

This application relates to an organic material, an organic electroluminescent device, and an electronic device. The organic material of this application has a structure as shown in Formula 1. Applying this organic compound to an organic electroluminescent device can significantly improve the device's performance.

Description

Technical Field

[0001] This application relates to the field of organic materials technology, and in particular to an organic material, an organic electroluminescent device, and an electronic device. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Organic light-emitting diodes (OLEDs) typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light. According to the statistical theorem of electron spin, singlet and triplet excitons are generated in a ratio of 1:3. The limit of the internal quantum efficiency of fluorescent organic light-emitting diodes utilizing singlet excitons is 25%. On the other hand, it is known that phosphorescent organic light-emitting devices that utilize the emission of triplet excitons can achieve an internal quantum efficiency of up to 100% when intersystem crossing is efficiently performed from singlet excitons.

[0003] Nevertheless, many problems still exist in the field of organic electroluminescent materials, particularly phosphorescent materials. For example, they suffer from short lifespan and low efficiency. Therefore, it is necessary to develop new materials to improve the performance of electronic components.

[0004] The information disclosed in the background section is only for enhancing the understanding of the background of this application, and therefore may include information that does not constitute prior art known to those skilled in the art. Summary of the Invention

[0005] To address the aforementioned problems, this application aims to provide an organic material and an organic electroluminescent device and electronic device comprising the organic material. The organic material can improve the performance of the organic electroluminescent device and electronic device, for example, by reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0006] According to a first aspect of this application, an organic material is provided having a structure as shown in Formula 1:

[0007]

[0008] Wherein, L is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

[0009] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms;

[0010] L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 30 carbon atoms.

[0011] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 30 carbon atoms respectively;

[0012] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms;

[0013] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0014] According to a second aspect of this application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned organic material.

[0015] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0016] The core structure of the organic material in this application is benzo[c]phenanthrene bonded to a triarylamine at a specific site. This bonding mechanism allows the compound to maintain a high triplet energy level while possessing high carrier transport capability, energy transfer capability to guest materials, and stability in the excited state of the structure itself. When this type of material is used as the host material of the emitting layer in a red organic electroluminescent device, it can significantly improve the device performance. Attached Figure Description

[0017] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0018] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0019] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0020] Figure Labels

[0021] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0022] 320, Hole transport layer; 321, First hole transport layer; 322, Second hole transport layer; 330, Organic light-emitting layer.

[0023] 340, Electron transport layer; 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0024] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic material and an organic electroluminescent device and electronic device containing the organic material. The organic material can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0025] According to a first aspect of this application, an organic material is provided having a structure as shown in Formula 1:

[0026]

[0027] Wherein, L is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

[0028] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms;

[0029] L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 30 carbon atoms.

[0030] Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 30 carbon atoms respectively;

[0031] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, and cycloalkyl groups with 3 to 10 carbon atoms;

[0032] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0033] In this application, the terms "optionally" or "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. As another example, "optionally, in Ar1 and Ar2, any two adjacent substituents form a ring" means that any two adjacent substituents in Ar1 and Ar2 can connect with each other to form a ring, or any two adjacent substituents in Ar1 and Ar2 can exist independently. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0034] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0035] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, cyano, halogen group, alkyl, haloalkyl, deuteralkyl, trialkylsilyl, aryl, deuterated aryl, heteroaryl, cycloalkyl, etc. The number of substituents can be one or more.

[0036] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0037] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0038] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups 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. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0039] In this application, terphenyl includes

[0040] In this application, the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0041] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25, or 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0042] In this application, the fluorene group can be replaced by one or more substituents, wherein any two adjacent substituents can combine with each other to form a substituted or unsubstituted spirocyclic structure. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0043] In this application, aryl groups used as substituents for L, L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, etc.

[0044] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenothiazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0045] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 12 to 20, while in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 1 to 18.

[0046] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0047] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0048] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0049] In this application, specific examples of arylphosphoxy groups include, but are not limited to, diphenylphosphoxy groups.

[0050] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0051] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0052] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0053]

[0054] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0055]

[0056] In some embodiments of this application, L is selected from single-bonded substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0057] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0058] Further optionally, L is selected from phenylene, naphthylene, or biphenylene.

[0059] In other embodiments of this application, L is selected from the group consisting of:

[0060]

[0061] Specifically, L is selected from the group consisting of the following groups:

[0062]

[0063] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0064] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0065] In other embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0066] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0067] Further optionally, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted phenylene oxides.

[0068] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0069]

[0070] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.

[0071] Optionally, L1 and L2 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0072]

[0073] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0074] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, and aryl groups having 6 to 12 carbon atoms;

[0075] Optionally, in Ar1 and Ar2, any two adjacent substituents form a saturated or unsaturated ring with 3 to 15 carbon atoms.

[0076] Optionally, any two adjacent substituents in Ar1 and Ar2 can form cyclohexane. cyclopentane Benzene ring, naphthalene ring or fluorene ring

[0077] In other embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0078] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0079] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted groups W; wherein, the unsubstituted group W is selected from the group consisting of:

[0080]

[0081] The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl, and when the number of substituents on group W is greater than 1, the substituents may be the same or different.

[0082] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0083]

[0084] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0085]

[0086]

[0087] Further optionally, when at least one of Ar1 and Ar2 is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzothiophene, the molecular spatial configuration of the compound of this application is more stereochemical, thereby increasing the T1 level, effectively blocking the diffusion of excitons, and increasing the overall molecular rigidity and thermal stability. When used as the organic light-emitting layer of an organic electroluminescent device, it significantly improves the lifespan of the device.

[0088] In some embodiments of this application, and Each is independently selected from the group consisting of the following groups:

[0089]

[0090]

[0091] In some embodiments of this application, Selected from the group consisting of the following groups:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] In some embodiments of this application, the organic material is selected from the group consisting of the following compounds:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] According to a second aspect of this application, this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.

[0110] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light-emitting layer 340, an electron transport layer 350, and a cathode 200, which are stacked sequentially.

[0111] Optionally, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, indium tin oxide (ITO) is included as the transparent electrode for the anode.

[0112] Optionally, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can refer to existing technologies for selection, and this application does not impose any special limitations in this regard. In some embodiments of this application, the first hole transport layer 320 is HT-17, and the second hole transport layer 330 is HT-19.

[0113]

[0114]

[0115] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;

[0116]

[0117] In some embodiments of this application, the hole injection layer 310 is composed of HI-01.

[0118] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or it may include a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0119] The main material of the organic light-emitting layer 340 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. This application does not impose any special restrictions on this.

[0120] In one embodiment of this application, the organic light-emitting layer 340 comprises the organic material of this application.

[0121] Optionally, the organic material of this application is used as the host material (hole-type host material) of the organic light-emitting layer 340.

[0122] In some embodiments of this application, the electronic host material of the organic light-emitting layer 340 is...

[0123] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also referred to as a dopant or dopant. Specific examples of red phosphorescent dopants used in red organic electroluminescent devices include, but are not limited to, […].

[0124]

[0125] In a more specific embodiment, the host material of the organic light-emitting layer 340 is RH-01 of this application, and the guest material is RD-01.

[0126] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can be selected from, but are not limited to, ET-01, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0127]

[0128]

[0129] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-01 and LiQ.

[0130] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0131] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0132] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0133] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0134] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0135] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0136] This application does not specifically limit the synthesis method of the provided organic materials. Those skilled in the art can determine a suitable synthesis method based on the organic materials and the preparation methods provided in the preparation examples section of this application. Those skilled in the art can obtain all the organic materials provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic materials will not be detailed here, and should not be construed as limitations on this application.

[0137] Preparation of compounds

[0138] Synthesis of intermediate m1:

[0139]

[0140] Sub 1 (20.0 g; 65.1 mmol), 4-chlorophenylboronic acid (10.7 g; 68.4 mmol), tetratetraphenylphosphine palladium (1.5 g; 1.3 mmol), potassium carbonate (18.0 g; 130.2 mmol), tetrabutylammonium bromide (4.2 g; 13.0 mmol), toluene (160 mL), ethanol (40 mL), and deionized water (40 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 75 °C–80 °C and stirred for 18 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate m1 (17.1 g; yield 78%).

[0141] Following the synthetic method of intermediate m1, the intermediate compounds shown in Table 1 below are used, except that reactant A is used instead of 4-chlorophenylboronic acid:

[0142] Table 1

[0143]

[0144] Synthesis of compound A3:

[0145]

[0146] Intermediate M1 (10.0 g; 29.5 mmol), N-phenyl-4-benzidine (7.2 g; 29.5 mmol), tris(dibenzylacetone)dipalladium (0.3 g; 0.3 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (0.2 g; 0.6 mmol), sodium tert-butoxide (4.3 g; 44.3 mmol), and toluene (100 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 105 °C–110 °C with stirring and reacted for 12 hours. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the eluent, and then purified by recrystallization using a dichloromethane / n-heptane mixed solvent to give a white solid compound A2 (10.6 g; yield 66%).

[0147] Following the synthetic method for compound A2, synthesize the compounds listed in Table 2 below, except that reactant C from Table 2 is used instead of the one listed in Table 2.

[0148] Intermediate m1, reactant B replaces N-phenyl-4-benzidine:

[0149] Table 2

[0150]

[0151]

[0152]

[0153]

[0154] Mass spectrometry data for some compounds are shown in Table 3 below:

[0155] Table 3

[0156] compound <![CDATA[Mass spectrometry data (M+H) + > compound <![CDATA[Mass spectrometry data (M+H) + > A2 <![CDATA[m / z=548.2(M+H) + ]]> B10 <![CDATA[m / z=598.3(M+H) + ]]> A11 <![CDATA[m / z=578.2(M+H) + ]]> B25 <![CDATA[m / z=674.3(M+H) + ]]> A19 <![CDATA[m / z=637.3(M+H) + ]]> B39 <![CDATA[m / z=664.3(M+H) + ]]> A35 <![CDATA[m / z=572.2(M+H) + ]]> B45 <![CDATA[m / z=714.3(M+H) + ]]> A50 <![CDATA[m / z=598.3(M+H) + ]]> C1 <![CDATA[m / z=472.2(M+H) + ]]> A71 <![CDATA[m / z=664.3(M+H) + ]]> C6 <![CDATA[m / z=562.2(M+H) + ]]> A75 <![CDATA[m / z=698.3(M+H) + ]]> C12 <![CDATA[m / z=710.3(M+H) + ]]> A84 <![CDATA[m / z=674.3(M+H) + ]]> C21 <![CDATA[m / z=638.2(M+H) + ]]> A89 <![CDATA[m / z=638.2(M+H) + ]]> D13 <![CDATA[m / z=628.2(M+H) + ]]> A109 <![CDATA[m / z=714.3(M+H) + ]]> D24 <![CDATA[m / z=762.3(M+H) + ]]> A119 <![CDATA[m / z=740.3(M+H) + ]]> D37 <![CDATA[m / z=664.3(M+H) + <!-- 33 -->]]> B8 <![CDATA[m / z=572.2(M+H) + ]]> A126 <![CDATA[m / z=710.3(M+H) + ]]> A125 <![CDATA[m / z=567.2(M+H) + ]]> B55 <![CDATA[m / z=714.4(M+H) + ]]> B54 <![CDATA[m / z=713.3(M+H) + ]]> C31 <![CDATA[m / z=704.1(M+H) + ]]>

[0157] NMR data for some compounds are shown in Table 4 below:

[0158] Table 4

[0159]

[0160] Fabrication of organic electroluminescent devices

[0161] Example 1: Fabrication of a red organic electroluminescent device

[0162] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO / Ag / ITO substrate is cleaned with organic solvents to remove impurities and oil stains.

[0163] HI-01 was vacuum-deposited onto the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and then HT-17 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. The first hole transport layer.

[0164] Compound HT-19 was vacuum-deposited onto the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0165] Next, on the second hole transport layer, RH-01:compound Al:RD-01 were co-deposited at a deposition rate of 48%:48%:4% to form a layer with a thickness of [missing information]. Organic light-emitting layer (EML).

[0166] On the organic light-emitting layer, compounds ET-01 and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition. A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0167] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0168] Examples 2-28

[0169] Organic electroluminescent devices were prepared using the same method as in Example 1, except that the compounds listed in Table 5 below (collectively referred to as "Compound X") were used instead of Compound A2 in Example 1 when fabricating the light-emitting layer.

[0170] Comparative Examples 1-3

[0171] Except that, when fabricating the light-emitting layer, compounds I, II, and III were used instead of compound A2 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0172] The main compound structures used in the preparation of each example and comparative example are as follows:

[0173]

[0174]

[0175] The performance of the red organic electroluminescent devices prepared in Examples 1-28 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 5.

[0176] Table 5

[0177]

[0178]

[0179] According to the data in Table 5, compared with Comparative Examples 1 to 4, using the organic material of this application as the host material (hole-type host material) of the red organic light-emitting layer in Device Examples 1 to 28 improved the current efficiency by at least 10.6% and the lifetime by at least 17.3%.

[0180] Compared with Comparative Examples 1 and 2, the organic material of this application has an improved current efficiency of at least 10.6% and a lifetime T95(h) of at least 17.3%. The reason for this may be that the 2-position of benzo[c]phenanthrene used in the organic material of this application is used as the linking site with the triarylamine, which improves the conjugation properties by reducing the degree of molecular twisting, resulting in a device with a lower driving voltage and improved luminous efficiency.

[0181] Compared with Comparative Example 3, the organic material of this application has an improved current efficiency of at least 38% and a T95 lifetime of at least 25.8%. The reason for this may be that the organic material of this application is formed by the combination of benzo[c]phenanthrene with arylene and triarylamine at specific sites. This connection mode gives the material a higher triplet energy level, thereby effectively improving the energy transfer characteristics to the guest and giving the device a higher luminous efficiency.

[0182] The organic material of this application is formed by the combination of benzo[c]phenanthrene and triarylamine at specific sites via arylene groups. The compound molecule maintains a high triplet energy level while possessing high carrier transport capability, energy transfer capability to guest materials, and stability in the excited state of the structure itself. When this type of material is used as the host material of the emitting layer in a red organic electroluminescent device, the device can have a lower operating voltage, higher luminous efficiency, and longer lifetime. In particular, when benzo[c]phenanthrene is linked to a triarylamine group via a phenylene group, and the triarylamine contains at least one dibenzo five-membered ring aromatic group (such as dibenzofuranyl, dibenzothiophenyl, carbazoleyl, or fluoreneyl), the device performance is even better.

[0183] It should be understood that this application is not limited to the precise structure described above and shown in the accompanying drawings, and various modifications and changes can be made without departing from its scope. The scope of this application is limited only by the appended claims.

Claims

1. An organic material, characterized in that, This organic material has the structure shown in Formula 1: Wherein, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; The substituents in L, L1, and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. Furthermore, the organic material is not one of the following compounds:

2. The organic material according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted groups W; wherein, the unsubstituted group W is selected from the group consisting of the following groups: The substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl, and when the number of substituents on group W is greater than 1, the substituents may be the same or different.

3. The organic material according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are independently selected from the group consisting of the following groups:

4. The organic material according to claim 1, characterized in that, Each is independently selected from the group consisting of the following groups:

5. The organic material according to claim 1, characterized in that, Selected from the group consisting of the following groups:

6. The organic material according to claim 1, characterized in that, The organic material is selected from the group consisting of the following compounds:

7. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises the organic material as described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The functional layer includes an organic light-emitting layer.

9. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device is a red organic electroluminescent device.

10. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 7 to 9.

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