Organic compound, mixture, composition, organic light-emitting device and display panel

Abstract

The invention discloses an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. The organic compound has a structure as shown in a general formula (1): # imgabs0 #, wherein L1 is selected from substituted or unsubstituted aryl with the carbon atom number of 6 to 20 and substituted or unsubstituted heteroaryl with the carbon atom number of 5 to 20; l2 is selected from aryl which has 6 to 20 carbon atoms and is substituted to be unsubstituted; x1 is selected from C or CR1, and when X1 is selected from C, X1 is a connection site; x2 is selected from CR2, and X3 is selected from CR3; r1, R2 and R3 are selected from H, D and substituted or unsubstituted aryl with 6 to 20 carbon atoms; the organic compound provided by the invention can enhance the ability of a light-emitting layer to form an exciplex, thereby improving the efficiency and service life of the organic light-emitting device.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. Background Art

[0002] Organic optoelectronic materials are diverse in synthesis, relatively low in manufacturing cost, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) are used in the preparation of optoelectronic devices, such as flat panel displays and lighting, and have advantages such as wide viewing angle, fast response time, low operating voltage, and thin panel thickness, so they have broad development potential.

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent elements that use organic electroluminescence usually have an anode, a cathode, and an organic functional layer located between the anode and the cathode. In order to improve the efficiency and life of the organic electroluminescent element, the organic functional layer has a multilayer structure, and each layer contains different organic substances. Specifically, the organic functional layer may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected into the organic functional layer from the anode, and electrons are injected into the organic functional layer from the cathode. When the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to the ground state. This organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0004] At present, the light-emitting layer materials of organic electroluminescent devices mainly adopt the host-guest doping form, and the transmission of holes and electrons is carried out by matching the host material and the guest material, so as to improve the life and efficiency of the device. Therefore, the host material plays an important role in organic electroluminescent devices. At present, although a large number of host materials have been developed, the corresponding devices still have problems such as unbalanced carrier transmission and insufficient device life. How to design new host materials with better performance to improve the efficiency and life of the device has always been a problem to be solved by those skilled in the art. Summary of the invention

[0005] The embodiments of the present application provide an organic compound, a mixture, a composition, an organic light-emitting device and a display panel, which can be used to improve the efficiency and life of the organic light-emitting device.

[0006] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0007]

[0008] Wherein, L1 is selected from a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms;

[0009] L2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms;

[0010] X1 is selected from C or CR1. When X1 is selected from C, X1 is a linking site;

[0011] X2 is selected from CR2, X3 is selected from CR3;

[0012] R1, R2 and R3 are selected from H, D, and a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms.

[0013] In one embodiment of the present application, L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl.

[0014] In one embodiment of the present application, L2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl.

[0015] In one embodiment of the present application, the organic compound has a structure as shown in general formula (1-a):

[0016]

[0017] Wherein, R4 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms.

[0018] In one embodiment of the present application, the organic compound is selected from any one of the following compounds 1 to 106:

[0019]

[0020]

[0021]

[0022]

[0023] According to the above-mentioned purpose of the present application, an embodiment of the present application also provides a mixture, which includes the organic compound and at least one organic functional material, and the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

[0024] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a composition, which includes the organic compound and at least one organic solvent, or the composition includes the mixture and at least one organic solvent.

[0025] According to the above-mentioned purpose of the present application, the embodiment of the present application further provides an organic light-emitting device, which includes:

[0026] a first electrode;

[0027] a second electrode, disposed opposite to the first electrode; and

[0028] an organic functional layer, located between the first electrode and the second electrode;

[0029] The material of the organic functional layer includes one or more of the organic compounds, or the material of the organic functional layer includes the mixture, or the material of the organic functional layer includes the combination.

[0030] In one embodiment of the present application, the organic functional layer includes at least a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material, the host material includes one or more of the organic compounds, or the host material includes the mixture, or the host material includes the composition.

[0031] According to the above-mentioned purpose of the present application, an embodiment of the present application further provides a display panel, which includes the organic light-emitting device.

[0032] The present application provides an organic compound, a mixture, a composition, an organic light-emitting device and a display panel. By connecting a biphenyl group and an aromatic group (or a heteroaromatic group) to a nitrogen heterocyclic ring, the electron transport ability of the organic compound can be enhanced, and the molecular weight of the organic compound can be effectively increased, and the glass transition temperature Tg and the thermal decomposition temperature Td of the organic compound can be increased; and it is more conducive to matching with a P-type material to achieve co-evaporation; therefore, the organic compound provided in the present application can enhance the ability of the light-emitting layer to form an excimer complex, thereby improving the efficiency and life of the organic light-emitting device.

[0033] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application, and those skilled in the art can obtain other drawings based on these drawings without creative work.

[0035] In order to more completely understand the present application and its beneficial effects, the following description will be given in conjunction with the accompanying drawings, wherein the same figure numbers represent the same parts in the following description.

[0036] Figure 1 A schematic diagram of the structure of an organic light-emitting device provided in an embodiment of the present application.

[0037] 100. Organic light-emitting device; 110. Substrate; 101. First electrode; 102. Second electrode; 103. Organic functional layer; 104. Hole injection layer; 105. Hole transport layer; 106. Electron blocking layer; 107. Light-emitting layer; 108. Electron transport layer; 109. Electron injection layer. DETAILED DESCRIPTION

[0038] The present application will be further described in detail below in conjunction with the accompanying drawings provided by the embodiments of the present application. It should be understood that the specific embodiments described herein are only used to explain the present application and are not used to limit the present application. The description order of the following embodiments is not used as a limitation on the preferred order of the embodiments.

[0039] Unless otherwise defined, all terms (including technical and scientific terms) used in this document have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0040] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0041] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0042] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0043] In the present application, when the same substituent appears multiple times, it can be independently selected from the same or different groups. If the general formula contains multiple R, then R can be independently selected from different or the same groups.

[0044] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen (e.g., F, Cl, Br or I), alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, cyano group, isocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group. Cyano, nitro or halogen (such as F, Cl, Br or I), alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro or halogen (such as F, Cl, Br or I), alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups can also be further substituted by substituents acceptable in the art.

[0045] In the present application, "ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by atoms bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0046] In the present application, "aryl" or "aromatic group" refers to an aromatic hydrocarbon group whose ring atoms derived from an aromatic ring compound by removing a hydrogen atom are all carbon atoms. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For a polycyclic ring, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthyl, fluorenyl, acenaphthene and derivatives thereof. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (for example, based on the total number of atoms in the system, the non-aromatic units preferably contain <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0047] In the present application, "heteroaryl" or "heteroaromatic group" means that at least one carbon atom on the ring skeleton is replaced by a non-carbon atom on the basis of the aryl, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. That is, the ring atoms of the heteroaryl include one or more non-carbon atoms selected from N atoms, O atoms, and S atoms. For example, "substituted or unsubstituted heteroaryl with 5 to 40 ring atoms" refers to a heteroaryl with 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl with 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl with 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl with 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, and suitable examples include but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, furidinyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0048] In this application, "alkyl" may refer to a fully saturated straight chain, branched chain and / or cyclic aliphatic hydrocarbon group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 2-Hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, 2-undecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-octadecyl, 2-octadecyl, 2-nonadecyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, 2-heneicosyl, 2-heneicosyl, 2-heconicosyl, 2-docosyl, 2-tricosyl, 2-tetracosyl, 2-pentacosyl, 2-hexacosyl, 2-heptacosyl, 2-octacosyl, 2-nonacosyl, 2-triacontyl, etc.

[0049] In the present application, the abbreviations of substituents correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-n-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0050] In the present application, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amines include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0051] Herein, the term "cycloalkyl" or "cyclic alkyl" refers to a monovalent group having one or more saturated rings in which all ring members are carbon, wherein the term "alkyl" has the same meaning as described above.

[0052] In the present application, the term "heterocyclyl", "heterocyclic" or "heterocycle" refers to a fully saturated or partially unsaturated, but non-aromatic cyclic group having one or more oxygen, sulfur, silicon or nitrogen heteroatoms in the ring, the nitrogen and sulfur heteroatoms may be optionally oxidized and the nitrogen heteroatom may be optionally quaternized. The heterocyclic group may be attached at any atom or carbon atom of the ring or ring system and may be unsubstituted or substituted with one or more moieties as described above for the aryl group.

[0053] In the present application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (wherein Z represents a halogen (e.g., F, Cl, Br or I)), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0054] In the present application, the term "alkoxy" refers to a group having a structure of "-O-alkyl", i.e., an alkyl group as defined above is connected to other groups via an oxygen atom. Phrases containing the term, suitable examples include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0055] In the present application, "*" connected to a single bond indicates a connection or fusion site.

[0056] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as a linking site.

[0057] In the present application, when the fusion site is not specified in the group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the ortho position in the group are fusion sites.

[0058] In the present application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0059] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0060] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0061] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0062] In the present application, "two adjacent R1 or two adjacent R3 or two adjacent R5 form a ring with each other" means a ring system formed by two adjacent R1 or two adjacent R3 or two adjacent R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0063] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0064]

[0065] Wherein, L1 is selected from a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms;

[0066] L2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms;

[0067] X1 is selected from C or CR1. When X1 is selected from C, X1 is a linking site;

[0068] X2 is selected from CR2, X3 is selected from CR3;

[0069] R1, R2 and R3 are selected from H, D, and a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms.

[0070] In the implementation and application process, the embodiments of the present application can enhance the electron transport ability of the organic compound by connecting a biphenyl group and an aromatic group (or a heteroaromatic group) to the nitrogen heterocycle, and can effectively increase the molecular weight of the organic compound, thereby increasing the glass transition temperature Tg and the thermal decomposition temperature Td of the organic compound; and, the organic compound can be better matched with a P-type material with a relatively large molecular weight to achieve co-evaporation, for example, with a P-type material with a molecular weight range of 630-670; therefore, the organic compound provided in the present application can enhance the ability of the light-emitting layer to form an excited radical complex, thereby improving the efficiency and life of the organic light-emitting device.

[0071] Specifically, in some embodiments, L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl. It should be noted that in L1, any H on the phenyl group may be replaced by D, and any H on the dibenzofuranyl group may be replaced by D.

[0072] In some embodiments, L2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl. It should be noted that in L2, any H on the phenyl group may be replaced by D, and any H on the biphenyl group may be replaced by D.

[0073] In some embodiments, R1, R2 and R3 are selected from H, D, substituted or unsubstituted phenyl. It should be noted that in R1, R2 and R3, any H on the phenyl group may be substituted by D.

[0074] Further, in some embodiments, the organic compound has a structure as shown in the general formula (1-a):

[0075]

[0076] Wherein, R4 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms.

[0077] It should be pointed out that the embodiments of the present application can effectively reduce the glass transition temperature Tg and thermal decomposition temperature Td of the organic compound by performing meta-substitution on the same benzene ring of carbazole, that is, forming an aromatic group at the meta-position of the same benzene ring of carbazole; it can be better matched with a P-type material with a relatively small molecular weight to achieve co-evaporation, for example, with a P-type material with a molecular weight range of 560-590; therefore, the organic compound provided in the present application can enhance the ability of the light-emitting layer to form an excimer complex, thereby improving the efficiency and life of the organic light-emitting device.

[0078] In some embodiments, R4 can be selected from substituted or unsubstituted phenyl groups; it should be noted that, in R4, any H on the phenyl group can be replaced by D.

[0079] In some embodiments, the organic compound is selected from any one of the following compounds 1 to 106:

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] In some embodiments, organic compounds can be used as functional materials in the functional layers of electronic devices. The organic functional layers include hole injection layer (HIL), hole transport layer (HTL), electron transport layer (ETL), electron injection layer (EIL), electron blocking layer (EBL), hole blocking layer (HBL), and emission material layer (EML).

[0086] In some embodiments, organic compounds are used in the light-emitting layer.

[0087] The embodiments of the present application can enhance the electron transport ability of the organic compound by connecting a biphenyl group and an aromatic group (or a heteroaromatic group) to the nitrogen heterocycle, and can effectively increase the molecular weight of the organic compound, and increase the glass transition temperature Tg and the thermal decomposition temperature Td of the organic compound; it can be better matched with a P-type material with a relatively large molecular weight to achieve co-evaporation, for example, with a P-type material with a molecular weight range of 630-670; therefore, the organic compound provided in the present application can enhance the ability of the light-emitting layer to form an excimer complex, thereby improving the efficiency and life of the organic light-emitting device.

[0088] In addition, an embodiment of the present application further provides a mixture, which includes the organic compound described in the above embodiment and at least one organic functional material.

[0089] In some embodiments, when the mixture provided in the embodiments of the present application is used in an organic light-emitting device, the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0090] In some embodiments, the organic functional material is selected from hole transport materials and used as a co-host in an organic light-emitting device, that is, the organic functional material is selected from materials with good hole transport properties and is used together with the organic compounds described in the above embodiments to prepare the light-emitting layer in the organic light-emitting device.

[0091] It should be noted that the above-mentioned organic functional material is a P-type material, which is combined with an organic compound to achieve co-evaporation, thereby enhancing the ability of the light-emitting layer in the organic light-emitting device to form an excited complex, thereby improving the efficiency and life of the organic light-emitting device.

[0092] In some embodiments, the molar ratio of the organic compound to the organic functional material is 4:6 to 6:4.

[0093] In some embodiments, the molar ratio of the organic compound to the organic functional material is 5:5.

[0094] In some embodiments, the organic light-emitting material has a structure shown in formula (2-a) or formula (2-b):

[0095]

[0096] Wherein, Ar1, Ar2, Ar3 and Ar4 are selected from substituted or unsubstituted aromatic groups having 6-30 ring atoms and substituted or unsubstituted heteroaromatic groups having 5-30 ring atoms; the H atom in formula (2-a) and formula (2-b) can be substituted by D.

[0097] In some embodiments, the organic functional material is preferably selected from at least one of the following compounds 1-1 to 1-73:

[0098]

[0099]

[0100]

[0101] In addition, an embodiment of the present application further provides a composition, which includes the organic compound described in the above embodiment and at least one organic solvent, or the composition includes the mixture described in the above embodiment and at least one organic solvent.

[0102] In some embodiments, the organic solvent is selected from at least one of aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, boric acid esters or phosphate esters.

[0103] In some embodiments, the organic solvent is selected from aromatic or heteroaromatic based solvents.

[0104] In some embodiments, the aromatic or heteroaromatic organic solvents include p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, -Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α, αα dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0105] In some embodiments, the aromatic ketone-based organic solvents include: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0106] In some embodiments, the aromatic ether-based organic solvent includes: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0107] In some embodiments, the organic solvent based on aliphatic ketone includes: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0108] In some embodiments, ester-based organic solvents include alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0109] In some embodiments, the composition further comprises a second organic solvent, and the second organic solvent is selected from at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0110] In some embodiments, organic solvents particularly suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0111] δd (dispersion force) at 17.0MPa 1 / 2 ~23.2MPa 1 / 2 range, especially in the range of 18.5~21.0MPa 1 / 2 range.

[0112] δp (polar force) at 0.2MPa 1 / 2 ~12.5MPa 1 / 2 range, especially at 2.0MPa 1 / 2 ~6.0MPa 1 / 2 range.

[0113] δh (hydrogen bond force) at 0.9MPa 1 / 2 ~14.2MPa 1 / 2 range, especially at 2.0MPa 1 / 2 ~6.0MPa 1 / 2 range.

[0114] In some embodiments, the boiling point of the dispersant is greater than or equal to 150°C; preferably greater than or equal to 180°C; more preferably greater than or equal to 200°C; more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C and most preferably greater than or equal to 300°C. The boiling point of the dispersant is at least greater than or equal to 150°C, which is beneficial to preventing the nozzle of the inkjet print head from clogging during inkjet printing, and the higher the boiling point, the more beneficial it is to prevent clogging. The organic solvent can evaporate from the solvent system to form a film containing a functional material.

[0115] In some embodiments, the composition is a solution.

[0116] In some embodiments, the composition is a suspension.

[0117] In some embodiments, based on the total mass of the composition, the organic compound may be 0.01 wt% to 15 wt%, 0.1 wt% to 10 wt%, 0.2 wt% to 5 wt%, or 0.25 wt% to 3 wt%.

[0118] The present application also provides an embodiment of the use of the above-mentioned composition as a coating or printing ink in the preparation of an organic light-emitting device, and a printing or coating method is particularly preferred.

[0119] Among them, suitable printing or coating techniques include (but are not limited to) inkjet printing, nozzle printing, gravure printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. The most preferred ones are gravure printing, nozzle printing and inkjet printing.

[0120] In some embodiments, the solution or suspension may further include one or more components such as surfactant compounds, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.

[0121] The embodiments of the present application also provide a use of the above-mentioned organic compound containing a heterocyclic group, the above-mentioned mixture or the above-mentioned composition in an organic light-emitting device.

[0122] For further information, please refer to Figure 1 The embodiment of the present application further provides an organic light-emitting device 100 , which includes a first electrode 101 , a second electrode 102 and an organic functional layer 103 .

[0123] The first electrode 101 and the second electrode 102 are arranged opposite to each other, and the organic functional layer 103 is arranged between the first electrode 101 and the second electrode 102. The material of the organic functional layer 103 includes at least one of the organic compounds described in the above embodiments, or the material of the organic functional layer 103 includes the mixture described in the above embodiments, or the material of the organic functional layer 103 includes the combination described in the above embodiments.

[0124] In some embodiments, the organic functional layer 103 includes a light-emitting layer 107 , and the light-emitting layer 107 includes at least one organic compound described in the above embodiments, or a mixture described in the above embodiments, or a combination described in the above embodiments.

[0125] In some embodiments, the material of the light-emitting layer 107 includes a host material and a guest material, and the host material includes at least one of the organic compounds described in the above embodiments, or the mixture described in the above embodiments, or the combination described in the above embodiments.

[0126] In some embodiments, the organic light-emitting device comprises a light-emitting layer 107, wherein the main material of the light-emitting layer 107 comprises at least one organic compound described in the above embodiments, or a mixture described in the above embodiments, or a combination described in the above embodiments.

[0127] In some embodiments, the organic light-emitting device may include an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic luminescent electrochemical cell (OLEEC), an organic field effect tube (OFET), an organic light-emitting field effect tube, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode), etc. Particularly preferred are organic electroluminescent devices such as OLED, OLEEC, and organic light-emitting field effect tubes.

[0128] In some embodiments, when the organic light-emitting device is an organic light-emitting diode device, the organic functional layer 103 includes a first common layer, a light-emitting layer 107 and a second common layer, and the material of the first common layer includes at least one of organic compounds, or the material of the first common layer includes a mixture, or the material of the first common layer includes a composition; wherein the first common layer includes a hole transport layer 105 and / or an electron blocking layer 106.

[0129] In some embodiments, the first electrode 101 may be an anode, and the second electrode 102 may be a cathode; and the first electrode 101 is placed on the substrate 110, and the organic functional layer 103 also includes a hole injection layer 104 arranged on the first electrode 101, a hole transport layer 105 arranged on the hole injection layer 104, an electron blocking layer 106 arranged on the hole transport layer 105, a light-emitting layer 107 arranged on the electron blocking layer 106, an electron transport layer 108 arranged on the light-emitting layer 107, and an electron injection layer 109 arranged on the electron transport layer 108, and the second electrode 102 is arranged on the electron injection layer 109; in other embodiments of the present application, the organic functional layer 103 may also include a hole blocking layer arranged between the light-emitting layer 107 and the electron transport layer 108, which is not shown in the figure.

[0130] In some embodiments, the organic light-emitting device may include a substrate 110, a first electrode 101 disposed on the substrate 110, an electron blocking layer 106 disposed on the first electrode 101, a light-emitting layer 107 disposed on the electron blocking layer 106, and a second electrode 102 disposed on the light-emitting layer 107.

[0131] In some embodiments, substrate 110 may be opaque or transparent. A transparent substrate may be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. Substrate 110 may be rigid or elastic. Substrate 110 may be plastic, metal, semiconductor wafer or glass. Substrate 110 has a smooth surface. Substrates 110 without surface defects are particularly ideal. In a preferred embodiment, substrate 110 is flexible and may be selected from polymer films or plastics having a glass transition temperature Tg of 150°C or more, preferably more than 200°C, more preferably more than 250°C, and most preferably more than 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0132] In some embodiments, the first electrode 101 may include a conductive metal or metal oxide, or a conductive polymer. The first electrode 101 can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the first electrode 101 and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer 107 or the p-type semiconductor material as the HIL or HTL or the electron blocking layer 106 (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of materials for the first electrode 101 include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable materials for the first electrode 101 are known and can be easily selected and used by those of ordinary skill in the art. The first electrode 101 material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the first electrode 101 is patterned, such as patterned ITO.

[0133] In some embodiments, the second electrode 102 may include a conductive metal or metal oxide. The second electrode 102 can easily inject electrons into the EIL or ETL or directly into the light-emitting layer 107. In some embodiments, the absolute value of the difference between the work function of the second electrode 102 and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer 107 or the n-type semiconductor material as the electron injection layer 109 (EIL) or the electron transport layer 108 (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as materials for the second electrode 102 of the organic light-emitting device in the embodiments of the present application. Examples of materials for the second electrode 102 include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the second electrode 102 may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0134] In some embodiments, the hole injection layer 104 is a layer for promoting the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0135] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material, which receives holes transmitted from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and the hole transport material may include but is not limited to at least one of an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, and the like.

[0136] In some embodiments, the electron transport layer 108 can be used to smoothly transport electrons. The electron transport material is suitably a material with high electron mobility, which can receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof may include, but are not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (Liq), and a benzimidazole-based compound.

[0137] In some embodiments, the electron injection layer 109 can be used to smoothly inject electrons. The electron injection material is preferably: having the ability to transport electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Specific examples thereof include 8-hydroxyquinoline lithium (Liq), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0138] In some embodiments, the hole blocking layer is a layer that blocks holes from reaching the negative electrode, and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

[0139] In some embodiments, the organic light-emitting device provided in the embodiments of the present application can also be used in the preparation of various electronic devices, such as display devices, lighting devices, light sources, sensors, and the like.

[0140] Furthermore, the embodiments of the present application also provide the preparation process of the organic compounds and organic functional materials described in the above embodiments, and provide Examples 1 to 14 to detail the preparation process of the organic compounds and organic functional materials provided in the embodiments of the present application.

[0141] Example 1

[0142] Organic compound 1 synthesis route:

[0143]

[0144] Synthesis of intermediate 1-3:

[0145] Intermediate 1-1 (10 mmol) and intermediate 1-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 1-3 with a molar weight of 8.33 mmol and a yield of 83.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 1-3 was: MS (ASAP) = 508.

[0146] Synthesis of organic compound 1:

[0147] Intermediate 1-3 (10 mmol) and intermediate 1-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain organic compound 1 with a yield of 87.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 1 was: MS (ASAP) = 640.

[0148] Example 2

[0149] Synthesis route of organic compound 2:

[0150]

[0151] Synthesis of intermediate 2-2:

[0152] Intermediate 2-1 (10 mmol) and intermediate 1-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-2 with a molar weight of 8.57 mmol and a yield of 85.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 2-2 was: MS (ASAP) = 508.

[0153] Synthesis of organic compound 2:

[0154] Intermediate 2-2 (10 mmol) and intermediate 1-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain organic compound 2 with a yield of 89.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 2 was: MS (ASAP) = 640.

[0155] Example 3

[0156] Synthesis route of organic compound 7:

[0157]

[0158] Synthesis of intermediate 3-2:

[0159] Intermediate 3-1 (10 mmol) and intermediate 1-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 3-2 with a molar weight of 8.39 mmol and a yield of 83.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 3-2 was: MS (ASAP) = 508.

[0160] Synthesis of organic compound 7:

[0161] Intermediate 3-2 (10 mmol) and intermediate 3-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 7 with a yield of 84.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 7 was: MS (ASAP) = 640.

[0162] Example 4

[0163] Synthesis route of organic compound 8:

[0164]

[0165] Synthesis of organic compound 8:

[0166] Intermediate 1-3 (10 mmol) and intermediate 4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 8 with a yield of 86.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 8 was: MS (ASAP) = 640.

[0167] Example 5

[0168] Synthesis route of organic compound 13:

[0169]

[0170] Synthesis of intermediate 5-3:

[0171] Intermediate 5-1 (10 mmol) and intermediate 5-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 5-3 with a molar weight of 8.61 mmol and a yield of 86.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 5-3 was: MS (ASAP) = 495.

[0172] Synthesis of organic compound 13:

[0173] Intermediate 5-3 (10 mmol) and intermediate 5-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd-132 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100° C. and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain organic compound 13 with a yield of 81.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 13 was: MS (ASAP) = 778.

[0174] Example 6

[0175] Synthesis route of organic compound 14:

[0176]

[0177] Synthesis of intermediate 6-2:

[0178] Intermediate 4-1 (10 mmol) and intermediate 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2 with a molar weight of 8.19 mmol and a yield of 81.9%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 6-2 was: MS (ASAP) = 495.

[0179] Synthesis of organic compound 14:

[0180] Intermediate 6-2 (10 mmol) and intermediate 4-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd-132 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100° C. and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 14 with a yield of 81.6%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 14 was: MS (ASAP) = 778.

[0181] Example 7

[0182] Synthesis route of organic compound 19:

[0183]

[0184] Synthesis of intermediate 7-2:

[0185] Intermediate 7-1 (10 mmol) and intermediate 5-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 7-2 with a molar weight of 8.92 mmol and a yield of 89.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 7-2 was: MS (ASAP) = 495.

[0186] Synthesis of organic compound 19:

[0187] Intermediate 7-2 (10 mmol) and intermediate 5-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd-132 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100° C. and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain organic compound 19 with a yield of 88.4%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 19 was: MS (ASAP) = 778.

[0188] Example 8

[0189] Synthesis route of organic compound 20:

[0190]

[0191] Synthesis of intermediate 8-1:

[0192] Intermediate 7-1 (10 mmol) and intermediate 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 8-1 with a molar weight of 9.12 mmol and a yield of 91.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 8-1 was: MS (ASAP) = 495.

[0193] Synthesis of organic compound 20:

[0194] Intermediate 8-1 (10 mmol) and intermediate 4-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd-132 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100° C. and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 20 with a yield of 83.7%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 20 was: MS (ASAP) = 778.

[0195] Example 9

[0196] Synthesis route of organic compound 29:

[0197]

[0198] Synthesis of intermediate 9-3:

[0199] Intermediate 9-1 (10 mmol) and intermediate 9-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 9-3 with a molar weight of 8.62 mmol and a yield of 86.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of intermediate 9-3 was: MS (ASAP) = 521.

[0200] Synthesis of organic compound 29:

[0201] Intermediate 9-3 (10 mmol) and intermediate 9-4 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100°C and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 29 with a yield of 88.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 29 was: MS (ASAP) = 660.

[0202] Example 10

[0203] Synthesis route of organic compound 82:

[0204]

[0205] Synthesis of organic compound 82:

[0206] Intermediate 5-3 (10 mmol) and intermediate 10-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd-132 (0.1 mmol) and potassium carbonate (30 mmol) were added. The temperature was raised to 100° C. and stirred for 6 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain organic compound 13 with a yield of 89.1%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 82 was: MS (ASAP) = 794.

[0207] Embodiment 11

[0208] Organic compound 66 synthesis route:

[0209]

[0210] Synthesis of organic compound 66:

[0211] The organic compound 1 (10 mmol) was dissolved in a mixed solvent of deuterated benzene and deuterated water (1:1100 ml), and sodium hydroxide (30 mmol) was added. The temperature was raised to 80°C and stirred for 2 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain organic compound 66 with a yield of 57.3%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of organic compound 66 was: MS (ASAP) = 668.

[0212] Example 12

[0213] Synthesis route of organic compound 106:

[0214]

[0215] Synthesis of organic compound 106:

[0216] The organic compound 13 (10 mmol) was dissolved in a mixed solvent of deuterated benzene and deuterated water (1:1100 ml), and sodium hydroxide (30 mmol) was added. The temperature was raised to 80°C and stirred for 2 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water. The organic phase was subjected to column chromatography and recrystallization to obtain the organic compound 106 with a yield of 53.2%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic compound 106 was: MS (ASAP) = 816.

[0217] Example 13

[0218] Synthesis route of organic functional material 1-1:

[0219]

[0220] Synthesis of organic functional material 1-1: Under nitrogen environment, N-biphenylcarbazole-4-pinacol boron ester (10mmol), N-biphenylcarbazole-4-bromide (10mmol), Pd2(dba)3 (0.1mmol), tri-tert-butylphosphine (0.3mmol), sodium tert-butoxide (30mmol) and 100mL of anhydrous toluene solvent were added to a 300mL two-necked bottle, heated to 60°C, stirred for reaction for 6 hours, cooled to room temperature, quenched with water, and the reaction liquid was rotary evaporated to remove most of the solvent, dissolved with dichloromethane, washed with water 3 times, and the organic liquid was collected and mixed with silica gel column for purification to obtain organic functional material 1-1 with a yield of 75%. MS (ASAP): 636.

[0221] Embodiment 14

[0222] Synthesis route of organic functional material 1-64:

[0223]

[0224] The organic functional material 1-1 (10 mmol) was dissolved in a mixed solvent of deuterated benzene and deuterated water (1:1100 ml), and sodium hydroxide (30 mmol) was added. The temperature was raised to 80°C and stirred for 2 h under a nitrogen atmosphere. After the reaction solution was cooled, most of the solvent was removed by rotary evaporation, and then the reaction solution was extracted and washed with water, and the organic phase was subjected to column chromatography and recrystallization to obtain the organic functional material 1-64 with a yield of 75.8%. The atmospheric pressure solid phase analysis probe mass spectrometry (ASAP-MS) result of the organic functional material 1-64 was: MS (ASAP) = 668.

[0225] It should be noted that the synthesis methods of the above-mentioned organic functional materials 1-2 to 1-73 refer to organic functional material 1-1, wherein the deuterated compounds in organic functional materials 1-2 to 1-73 refer to Example 14.

[0226] Furthermore, the embodiments of the present application provide device embodiments 1 to 12 and device comparative examples 1 and 2 to verify the performance of the organic light-emitting device provided by the embodiments of the present application.

[0227] Please refer to Figure 1 The structure of the organic light-emitting device includes a substrate 110, and a first electrode 101, a hole injection layer 104, a hole transport layer 105, an electron blocking layer 106, a light-emitting layer 107, an electron transport layer 108, an electron injection layer 109 and a second electrode 102 which are sequentially arranged on the substrate 110.

[0228] Specifically, the preparation process of the organic light-emitting device in device embodiment 1 includes:

[0229] First, the ITO conductive glass is cleaned, then ultrasonically cleaned with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode work function; wherein the glass is the substrate 110, and the ITO conductive layer located on the glass is the first electrode 101.

[0230] Then, the hole injection layer 104 material HATCN is deposited on the first electrode 101 by vacuum evaporation with a thickness of 30 nm and a deposition rate of

[0231] Next, a hole transport material HT is deposited on the hole injection layer 104 by vacuum evaporation to form a hole transport layer 105 with a thickness of 60 nm.

[0232] Furthermore, material GP is evaporated on the hole transport layer 104 to form an electron blocking layer 106 with a thickness of 10 nm.

[0233] Then, the light emitting layer 107 is evaporated on the electron blocking layer 106, with the organic compound 1 as the main material GH, GD as the doping material, the mass ratio of GD to GH is 8:100, and the thickness is 40 nm.

[0234] Next, electron transport materials ET and Liq are deposited on the light emitting layer 107 by vacuum evaporation to form an electron transport layer 108 with a mass ratio of 5:5 and a thickness of 30 nm.

[0235] Furthermore, Liq is vacuum-evaporated on the electron transport layer 108 to form an electron injection layer 109 with a thickness of 1 nm.

[0236] On the electron injection layer 109 , an Al layer was vacuum-deposited to form the second electrode 102 with a thickness of 100 nm.

[0237] It should be noted that in device embodiments 2 to 12, the main material of the light-emitting layer 107 in the organic light-emitting device is replaced by organic compounds 2 to 106 from organic compound 1, and other conditions remain unchanged. The main material of the light-emitting layer 107 in device comparative examples 1 and 2 is replaced by comparative compounds 1 and 2, respectively, instead of organic compound 1 in device embodiment 1, and other conditions remain unchanged.

[0238] In the embodiment of the present application, in the green light device, the main material is selected from the organic compound or mixture provided in the embodiment of the present application, HATCN is used as the hole injection layer material, HT is used as the hole transport material, GP is used as the electron blocking layer material, GD is used as the doping material of the light-emitting material, ET is used as the electron transport material, and Liq (8-hydroxyquinoline lithium) is used as the electron injection material, and the device structure is ITO / HATCN / HT / GP / main material: GD (8% wt) / ET: Liq / Liq / Al. The structures of the compounds involved in the above device comparative examples 1 and 2 and device embodiments 1 to 12 are as follows:

[0239]

[0240] The structures of the comparative compounds Ref-1 and Ref-2 are shown below:

[0241]

[0242] The current-voltage (JV) characteristics of the organic light-emitting diodes of green light device embodiments 1 to 12 and device comparison examples 1 to 2 were tested using a characterization device, and important parameters such as efficiency and lifetime, and external quantum efficiency were recorded. The results are shown in Table 1.

[0243] Table 1

[0244]

[0245]

[0246] Among them, the luminous efficiency is the current density of 10mA / cm 2 As can be seen from Table 1, all luminous efficiencies and lifetimes are relative values ​​relative to the organic light emitting diode of device comparative example 2. It can be seen that the efficiency and lifetime of the organic light emitting device prepared based on the organic compound provided in the embodiment of the present application are significantly improved compared with the device comparative example. The embodiment of the present application uses an organic compound as the main material of the light-emitting layer 107, while the device comparison example uses other organic compounds as the main material of the light-emitting layer 107. Compared with the comparative compound Ref-1 and the comparative compound Ref-2, the organic compound provided in the embodiment of the present application has an aromatic group added between the nitrogen heterocycle and the carbazole, and the phenyl group connected to the nitrogen heterocycle is also replaced by a biphenyl group, which can enhance the electron transmission ability, increase the molecular weight of the organic compound, and increase the Tg temperature and Td temperature; or the embodiment of the present application performs meta-position substitution on the same benzene ring of carbazole, that is, forms an aromatic group at the meta-position of the same benzene ring of carbazole, which can effectively reduce the glass transition temperature Tg and the thermal decomposition temperature Td of the organic compound, thereby facilitating the combination with different types of P-type materials and making it easier to co-evaporate, thereby enhancing the ability of the light-emitting layer 107 to form an excimer complex; and thus the OLED device prepared by the organic compound provided in the embodiment of the present application has been greatly improved in terms of efficiency and life.

[0247] Furthermore, the embodiments of the present application verify the performance of an organic light-emitting device formed by combining an organic compound with an organic functional material to form a host material.

[0248] Among them, device embodiments 13 to 24 use organic compounds 1 to 106 in combination with organic functional material 1-1; device embodiment 25 and device embodiment 26 use organic compound 66 and organic compound 106 in combination with organic functional material 1-64 respectively; device comparison example 3 and device comparison example 4 use comparative compound Ref-1 and comparative compound Ref-2 in combination with organic functional material 1-1 respectively; and the conditions except the main material in device embodiments 13 to 26, device comparison example 3 and device comparison example 4 remain unchanged.

[0249] The current-voltage (JV) characteristics of the organic light-emitting diodes of green light device embodiments 13 to 26 and device comparison examples 3 and 4 were tested using characterization equipment, and important parameters such as efficiency, lifetime and external quantum efficiency were recorded. The results are shown in Table 2.

[0250] Table 2

[0251] serial number Main material Molar Ratio Luminous efficiency life Device Example 13 1：1-1 3:7 1.72 1.54 Device Example 14 2：1-1 3:7 1.71 1.61 Device Example 15 7：1-1 3:7 1.65 1.31 Device Example 16 8：1-1 3:7 1.63 1.45 Device Example 17 13：1-1 3:7 1.54 1.42 Device Example 18 14：1-1 3:7 1.61 1.57 Device Example 19 19：1-1 3:7 1.53 1.59 Device Example 20 20：1-1 3:7 1.68 1.62 Device Example 21 29：1-1 3:7 1.78 1.81 Device Example 22 82：1-1 3:7 1.85 2.01 Device Example 23 66：1-1 3:7 1.88 1.98 Device Example 24 106：1-1 3:7 1.91 2.03 Device Example 25 66：1-64 3:7 1.94 2.27 Device Example 26 106：1-64 3:7 1.96 2.29 Device Comparison Example 3 Ref-1:1-1 3:7 1.06 1.10 Device Comparison Example 4 Ref-2:1-1 3:7 1 1

[0252] Among them, the luminous efficiency is the current density of 10mA / cm 2 As can be seen from Table 2, all luminous efficiencies and lifespans are relative values ​​relative to the organic light emitting diode of device comparison example 4. It can be seen that the efficiency and lifespan of the organic light emitting device prepared by combining the organic compound and the organic functional material provided in the embodiment of the present application are significantly improved compared to the device comparison example. The OLED device prepared by using the organic compound and the organic functional material as the co-host material of the light emitting layer 107 in the embodiment of the present application has been greatly improved in terms of efficiency and lifespan.

[0253] In addition, an embodiment of the present application further provides a display panel, which includes the organic light-emitting device described in the above embodiment.

[0254] It is understandable that, since the display panel includes the organic light-emitting device described in the above embodiment, the display panel has the same beneficial effects as the organic light-emitting device, which will not be described in detail here. In the above embodiment, the description of each embodiment has its own emphasis, and for the part not described in detail in one embodiment, please refer to the relevant description of other embodiments.

[0255] The above is a detailed introduction to an organic compound, a mixture, a composition, an organic light-emitting device and a display panel provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the technical solution and its core idea of ​​the present application. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein; and these modifications or replacements do not make the essence of the corresponding technical solution deviate from the scope of the technical solution of the embodiments of the present application.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in general formula (1): Wherein, L1 is selected from a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 20 carbon atoms; L2 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms; X1 is selected from C or CR1. When X1 is selected from C, X1 is a linking site; X2 is selected from CR2, X3 is selected from CR3; R1, R2 and R3 are selected from H, D, and a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that L1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl.

3. The organic compound according to claim 1, characterized in that L2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl.

4. The organic compound according to any one of claims 1 to 3, characterized in that The organic compound has a structure as shown in the general formula (1-a): Wherein, R4 is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms.

5. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following compounds 1 to 106:

6. A mixture, characterized in that The mixture comprises the organic compound according to any one of claims 1 to 5 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials or organic dyes.

7. A composition, characterized in that The composition comprises the organic compound according to any one of claims 1 to 5 and at least one organic solvent, or the composition comprises the mixture according to claim 6 and at least one organic solvent.

8. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as an organic functional layer, located between the first electrode and the second electrode; The material of the organic functional layer includes one or more of the organic compounds described in any one of claims 1 to 5, or the material of the organic functional layer includes the mixture described in claim 6, or the material of the organic functional layer includes the composition described in claim 7.

9. The organic light emitting device according to claim 8, characterized in that: The organic functional layer at least includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material. The host material includes one or more of the organic compounds, or the host material includes the mixture, or the host material includes the combination.

10. A display panel, characterized in that: The display panel comprises the organic light emitting device according to claim 8 or 9.

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