Organic compound, mixture, composition and organic electronic device

Abstract

The present application discloses an organic compound and a mixture, a composition and an organic electronic device comprising the organic compound. The organic compound has a structure as shown in the general formula (1): The organic compound is used in an organic electronic device, in particular, as a main material in a light-emitting layer of an organic electronic device to improve the efficiency and life of the organic electronic device.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to an organic compound, and a mixture, a composition and an organic electronic device comprising the organic compound. Background Art

[0002] In order to improve the luminous efficiency of organic light-emitting diodes, various luminescent material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes using fluorescent materials have the characteristics of high reliability. However, the electroluminescent quantum efficiency inside organic light-emitting diodes using fluorescent materials under electrical excitation is limited to 25%, mainly because the ratio of the singlet excited state and triplet excited state of the excitons generated by the current is 1:3. Organic light-emitting diodes using phosphorescent materials have achieved almost 100% internal electroluminescent quantum efficiency, so the development of phosphorescent luminescent materials has been widely studied.

[0003] The light-emitting layer materials of existing organic electronic devices generally include matrix materials (host materials) and light-emitting materials (guest materials). Organic electronic devices with excellent color purity, luminous efficiency and stability are obtained by matching the host materials with the guest materials. Since the host material has a great influence on the efficiency and characteristics of the electroluminescent device when the host-guest system is used as the light-emitting layer material of the light-emitting device, the selection of the host material is very important. At present, the host materials used in organic electronic devices mainly include 4,4'-dicarbazole-biphenyl (CBP), BAlq (bis(2-methyl)-8-hydroxyquinoline-4-phenylphenol aluminum (III)), phenanthroline (BCP), or matrix materials with bipolar transport hosts containing electron transport groups and hole transport groups as disclosed in patents US2016329506, US20170170409, and CN104541576A. Although this type of organic electronic device can obtain good device performance, the luminous efficiency and life of the device still need to be improved.

[0004] Therefore, the existing main material solutions for the light-emitting layer materials need to be further improved and developed. Summary of the invention

[0005] In view of this, the present application provides an organic compound as a new type of host material, which is used in the light-emitting layer of an organic electronic device to improve the problems of low light-emitting efficiency and short life of the organic electronic device.

[0006] The technical solution of this application is as follows:

[0007] An organic compound having a structure as shown in the general formula (1):

[0008]

[0009] in:

[0010] Y 1 Selected from O or S;

[0011] Ar 1 is selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0012] M is selected from any one of the structures represented by formula (A-1) to (A-4):

[0013]

[0014] Y 2 Selected from O or S;

[0015] Ar 2 ,Ar 3 ,Ar 4 are independently selected from: a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0016] Z 1 Each occurrence is independently selected from CR 1 or N, and at least one Z 1 Selected from N;

[0017] R 1 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, -CN, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 6 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0018] * indicates the attachment site.

[0019] Correspondingly, the present application also provides a mixture, comprising the above-mentioned organic compound 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 guest materials, luminescent host materials or organic dyes.

[0020] Correspondingly, the present application also provides a composition, comprising the above organic compound or the above mixture, and at least one organic solvent.

[0021] Correspondingly, the present application also provides an organic electronic device, comprising at least one organic functional layer, wherein the organic functional layer comprises the above-mentioned organic compound or the above-mentioned mixture, or the organic functional layer is prepared from the above-mentioned composition.

[0022] Compared with the prior art, the organic compound of the present application has the following beneficial effects:

[0023] The organic compound of the present application is prepared by using The structure is bridged with the nitrogen-containing electron-withdrawing group M through the benzene ring, and the benzene ring is introduced Group, The group has a non-completely conjugated five-membered ring structure. Through the interaction between the conjugated group and the non-conjugated group, the charge transfer ability of the organic compound molecule can be effectively improved; the nitrogen-containing electron-withdrawing group has electron transfer ability, The combination of the two groups has hole transport capability, and helps to achieve balanced carrier transport in the light-emitting layer. In this way, the exciton utilization rate and device stability of the organic electronic device using the organic compound as the main material can be effectively improved, thereby improving the luminous efficiency and life of the organic electronic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0025] Figure 1 It is a schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0026] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise specified, the directional words such as "upper" and "lower" used generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to", the term "multiple" means "two or more", and the term "and / or" includes any and all combinations of one or more related listed items. Various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and simplicity, and should not be understood as a hard limit to the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the range. For example, description of a range from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the stated range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the stated range.

[0027] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art to which this application belongs. The terms used herein in the specification of this application are only for the purpose of describing specific embodiments and are not intended to limit this application. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0028] In the present application, composition, printing ink and ink have the same meaning and can be interchangeable.

[0029] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0030] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0031] In the present application, "D" represents a deuterium atom; and "H" represents a hydrogen atom.

[0032] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0033] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0034] 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 atoms, cyano groups, isocyano groups, nitro groups, halogen groups, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups, 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 atoms ... Preferably, R is selected from but not limited to deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group and trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0035] In the present application, the "number of 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) formed 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 "number of 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.

[0036] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which may 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 aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group may be further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthyl, fluorenyl, dinaphthylenyl, acenaphthene and derivatives thereof. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aromatic groups.

[0037] "Heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom may be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted, and suitable examples include but are not limited to thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, 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, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0038] In the present application, "alkyl" may mean a straight chain, branched chain and / or cyclic alkyl 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. A phrase containing this term, for example, "alkyl containing 1-10 C atoms" means an alkyl containing 1 to 10 carbon atoms, which may be a straight chain alkyl containing C1-10 carbon atoms, or a branched chain alkyl containing 3-10 carbon atoms or a cyclic alkyl group. When "alkyl containing 1-10 C atoms" appears each time, it may be C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 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, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, adamantane, and the like.

[0039] In the present application, the substituent abbreviations 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.

[0040] In the present application, "*" connected to a single bond indicates a linking site or a fusion site.

[0041] 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.

[0042] 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.

[0043] 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 above optional substitutable positions form a ring.

[0044] In the present application, "cyclic alkyl group" and "cycloalkyl group" have the same meaning.

[0045] In the present application, the terms "combination thereof", "any combination thereof", "any combination thereof", "group combination" and the like include all suitable combinations of any two or more groups in the listed items.

[0046] In the present application, “further”, “furthermore”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0047] In this application, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel schemes of "yes" or "no". If there are multiple "options" in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction, each "option" is independent.

[0048] In the present application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0049] The technical solution of this application is as follows:

[0050] An organic compound having a structure as shown in the general formula (1):

[0051]

[0052] in:

[0053] Y 1 Selected from O or S;

[0054] Ar 1 is selected from substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0055] M is selected from any one of the structures represented by formula (A-1) to (A-4):

[0056]

[0057] Y 2 Selected from O or S;

[0058] Ar 2 ,Ar 3 ,Ar 4 are independently selected from: a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0059] Z 1 Each occurrence is independently selected from CR 1 or N, and at least one Z 1 Selected from N;

[0060] R 1 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, -CN, -CF 3 , -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, an aryloxy group having 6 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0061] * indicates the attachment site.

[0062] In some embodiments, the organic compound is selected from the structure shown in formula (2-1) or (2-2):

[0063]

[0064] In some embodiments, Ar 1 It is selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms.

[0065] In some embodiments, Ar 1 Selected from one of the following groups:

[0066]

[0067] in:

[0068] X 1 Each occurrence, independently selected from N or CR 2 ;

[0069] Y 3 Each occurrence is independently selected from O, S, S=O, SO 2 NR 3 , PR 3 , CR 4 R 5 or SiR 4 R 5 ;

[0070] R 2 , R 3 , R 4 , R 5 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF 3 , -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 20 ring atoms, a heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups.

[0071] When X 1 When X is the attachment site, 1 Selected from C atoms.

[0072] In a specific embodiment, Ar 1 Selected from one of the following groups:

[0073]

[0074]

[0075] Wherein: * indicates the connection site.

[0076] In a specific embodiment, R 2 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0077] Further, R 2 Each occurrence is independently selected from -H, -D, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, pyridyl, pyrimidinyl, naphthyl, or a combination of these groups.

[0078] In a specific embodiment, Ar 1 Selected from phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethyl-fluorenyl; these groups are unsubstituted or further substituted by alkyl groups having 1 to 10 C atoms.

[0079] In one embodiment, M is selected from one of the structures shown in formula (B-1)-(B-6):

[0080]

[0081] In one embodiment, Ar 2 ,Ar 3 ,Ar 4 The group is independently selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0082] In some embodiments, the Ar 2 ,Ar 3 ,Ar 4 Each is independently selected from any one of the structures represented by formula (C-1) to (C-6):

[0083]

[0084] in:

[0085] X 3 Each occurrence, independently selected from N or CR 6 ;

[0086] Y 4 Each occurrence is independently selected from O, S, S=O, SO 2 NR 7 , PR 7 , CR 8 R 9or SiR 8 R 9 ;

[0087] R 6 , R 7 , R 8 , R 9 Each occurrence is independently selected from: -H, -D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF 3 , -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 20 ring atoms, a heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups;

[0088] Ar 5 Independently selected from substituted or unsubstituted aromatic or heteroaromatic groups having 6 to 20 ring atoms.

[0089] In some embodiments, Ar 5 Selected from one of the following groups:

[0090]

[0091] It should be noted that when X 3 When X is the attachment site, 3 is selected from C atoms; when Y 4 When Y is the linking site, 4 Selected from N atoms.

[0092] In one embodiment, R 6 , R 7 , R 8 , R 9 Each occurrence is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0093] In one embodiment, Ar2 ,Ar 3 ,Ar 4 Each is independently selected from the following groups:

[0094]

[0095] Specifically, R 6 Each occurrence is independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidyl, triazine, naphthyl, biphenyl, or a combination of these groups.

[0096] In some embodiments, the Ar 2 ,Ar 3 ,Ar 4 Selected from the following groups:

[0097]

[0098] Wherein: the above groups may be further substituted.

[0099] As an example, in some embodiments, the organic compound of the present application can be selected from but not limited to any one of the following structures:

[0100]

[0101]

[0102]

[0103] It can be understood that the H in the structural formula of the above organic compound can be further substituted.

[0104] In some embodiments, the organic compound of the present application can be used as an organic functional material in a functional layer of an organic electronic device, in particular, in a functional layer of an OLED device. The organic functional material can be, but is not limited to, a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a luminescent guest material (Emitter), a luminescent host material (Host Emitter) and an organic dye.

[0105] In some embodiments, the organic compounds described herein are used in a light-emitting layer. In at least some embodiments, the organic compounds described herein are used as a host material in a light-emitting layer. In at least one embodiment, the organic compounds described herein are used as a phosphorescent host material in a light-emitting layer.

[0106] In some embodiments, the organic compound described in the present application has a light-emitting function, and the light-emitting wavelength ranges from 300 to 1000 nm. It should be noted that the light-emitting here refers to photoluminescence or electroluminescence.

[0107] One purpose of the present application is to provide a material solution for vapor deposition type OLED.

[0108] In some embodiments, the molecular weight of the organic compound according to the present application is ≤1200 g / mol, preferably ≤1100 g / mol, more preferably ≤1000 g / mol, more preferably ≤950 g / mol, and most preferably ≤900 g / mol. At this time, the organic compound can be formed into a film by evaporation.

[0109] In some embodiments, the molecular weight of the organic compound according to the present application is ≥800 g / mol, preferably ≥900 g / mol, more preferably ≥1000 g / mol, more preferably ≥1100 g / mol, and most preferably ≥1200 g / mol. At this time, the organic compound can be formed into a film by printing.

[0110] The present application further relates to a mixture, comprising a first organic functional material and a second organic functional material. The first organic functional material includes at least one organic compound described in the present application, and the second organic functional material can be selected from but not limited to at least one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials and organic dyes. Wherein, the luminescent guest material is selected from singlet luminophores (fluorescent luminophores), triplet luminophores (phosphorescent luminophores) and organic thermally excited delayed fluorescence materials (TADF materials). Detailed descriptions of various organic functional materials are detailed in WO2010135519A1, US20090134784A1 and WO 2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0111] It can be understood that the second organic functional material can be a small molecule organic material or a polymer material.

[0112] In some embodiments, in the mixture, the mass ratio of the first organic functional material to the second organic functional material ranges from (2:8) to (8:2), preferably from (3:7) to (7:3), more preferably from (4:6) to (6:4), and most preferably 5:5.

[0113] In some embodiments, in the mixture, the absolute value of the difference in molecular weight between the first organic functional material and the second organic functional material does not exceed 100 Dalton, preferably does not exceed 80 Dalton, better does not exceed 70 Dalton, even better does not exceed 60 Dalton, very preferably does not exceed 40 Dalton, and most preferably does not exceed 30 Dalton.

[0114] In some embodiments, in the mixture, the absolute value of the difference in sublimation temperature between the first organic functional material and the second organic functional material does not exceed 50K (Kelvin); more preferably, it does not exceed 30K; more preferably, it does not exceed 20K; and most preferably, it does not exceed 10K.

[0115] In some embodiments, according to the mixture described in the present application, at least one of the first organic functional material and the second organic functional material has a glass transition temperature Tg ≥ 1100°C; preferably, at least one of the organic functional materials has a Tg ≥ 120°C; more preferably, at least one of the organic functional materials has a Tg ≥ 140°C; more preferably, at least one of the organic functional materials has a Tg ≥ 160°C; most preferably, at least one of the organic functional materials has a Tg ≥ 180°C.

[0116] In some embodiments, the second organic functional material in the mixture is selected from a luminescent guest material, and the luminescent guest material is selected from a singlet luminophore, a triplet luminophore or a TADF luminophore. For a detailed description of the singlet luminophore, triplet luminophore, TADF material and host material in this application, please refer to patent WO2018095390A1.

[0117] In some embodiments, the second organic functional material in the mixture is selected from a singlet luminophore, wherein the weight percentage of the singlet luminophore in the mixture is greater than 0 and less than or equal to 10 wt %, preferably greater than 0 and less than or equal to 9 wt %, more preferably greater than 0 and less than or equal to 8 wt %, particularly preferably greater than 0 and less than or equal to 7 wt %, and most preferably greater than 0 and less than or equal to 5 wt %.

[0118] In other embodiments, the second organic functional material in the mixture is selected from a triplet light emitter, wherein the weight percentage of the triplet light emitter in the mixture is greater than 0 and less than or equal to 25wt%, preferably greater than 0 and less than or equal to 20wt%, and more preferably greater than 0 and less than or equal to 15wt%.

[0119] In some other embodiments, the second organic functional material in the mixture is selected from a TADF material, wherein the weight percentage of the TADF main material in the mixture is greater than 0 and less than or equal to 15wt%, preferably greater than 0 and less than or equal to 10wt%, and more preferably greater than 0 and less than or equal to 5wt%.

[0120] In at least one embodiment, the second organic functional material in the mixture is selected from the main material. In the mixture, the weight percentage of the first organic functional material in the mixture ranges from 30 to 70%. Preferably, the weight ratio of the first organic functional material to the second organic functional material is 1:1.

[0121] In some embodiments, the second organic functional material has a structure as shown in formula (4):

[0122]

[0123] Among them, R 11 Each occurrence is independently selected from the structure represented by formula (4-1), -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a branched or cyclic alkoxy group having 3 to 20 C atoms, a branched or cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, -CF 3 , -Cl, -Br, -F, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring atoms, a heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups, at least one R 11 Selected from (4-1);

[0124] Adjacent R 11 Can be connected to form a ring.

[0125] The structure of formula (4-1) is:

[0126]

[0127] in:

[0128] Ar 6 ,Ar 7 independently selected from substituted or unsubstituted aromatic or heteroaromatic groups having 6 to 30 ring atoms, or substituted or unsubstituted non-aromatic ring groups having 5 to 30 ring atoms;

[0129] L 2is selected from a single bond, a substituted or unsubstituted aryl or heteroaryl group having 6 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring group having 5 to 30 ring atoms;

[0130] Ar 6 ,Ar 7 , L 2 Any two of them can be connected to form a ring.

[0131] In some embodiments, the second organic functional material is selected from one of the structures shown in the following general formula:

[0132]

[0133] In one embodiment, the second organic functional material is selected from the following general formula:

[0134]

[0135] As an example, the second organic functional material may be selected from but not limited to any one of the following structures:

[0136]

[0137]

[0138] It can be understood that the H in the structural formula of the second organic functional material can be further substituted.

[0139] The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0140] The organic solvent is selected from at least one of aromatic or heteroaromatic based solvents, ester based solvents, aromatic ketone based solvents, aromatic ether based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0141] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0142] The aromatic or heteroaromatic based solvent may be selected from, but not limited to, 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-isopropyl At least one of biphenyl, 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,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0143] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0144] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0145] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 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, and ethyl-2-naphthyl ether.

[0146] The aliphatic ketone-based solvent can be selected from, but not limited to, 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 an aliphatic ether, for example, at least one of 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 and tetraethylene glycol dimethyl ether.

[0147] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0148] In some embodiments, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0149] The other organic solvent can be selected from but not limited to 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 (DMSO), tetralin, decalin and indene.

[0150] In some embodiments, organic solvents suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0151] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0152] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0153] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0154] In some embodiments, according to the composition of the present application, the boiling point of the organic solvent should be considered when selecting. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; preferably ≥200°C; more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head.

[0155] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a film comprising the organic compound.

[0156] In some embodiments, the composition is a solution. In some other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from but not limited to at least one of a surfactant compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0157] In the composition, the content of the organic compound or the mixture in the composition is 0.01 to 10 wt %, preferably 0.1 to 8 wt %, more preferably 0.2 to 5 wt %, and most preferably 0.25 to 3 wt %.

[0158] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used to prepare an organic electronic device by a printing or coating preparation method. The printing or coating preparation method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roller printing, lithography, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, etc. Preferred are gravure printing, spray printing and inkjet printing.

[0159] The present application also relates to an application of the organic compound, mixture or composition as described above in an organic electronic device. The specific scheme is as follows:

[0160] An organic electronic device comprises at least one organic functional layer, wherein the organic functional layer comprises at least one organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0161] Furthermore, the organic electronic device comprises a cathode, an anode and at least one organic functional layer. The organic functional layer comprises at least one organic compound or mixture as described above, or the organic functional layer is prepared from the above composition.

[0162] The organic functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL) or a hole blocking layer (HBL). In at least one embodiment, the organic functional layer is an emitting layer.

[0163] In some embodiments, the organic electronic device is an electroluminescent device, whose light-emitting layer comprises an organic compound as described above, or comprises an organic compound as described above and a phosphorescent material, or comprises an organic compound as described above and a host material, or comprises an organic compound as described above and a TADF material.

[0164] In one embodiment, the organic electronic device comprises an anode, a cathode, and a light-emitting layer located between the anode and the cathode, wherein the light-emitting layer comprises an organic compound as shown in formula (1), an organic compound as shown in formula (4), and a phosphorescent light-emitting body.

[0165] The organic electronic device may be, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor, and an organic plasmon emitting diode (Organic Plasmon Emitting Diode). Particularly preferred are organic electroluminescent devices such as OLED and organic light emitting field effect transistor. Further particularly preferred are OLEDs.

[0166] In one embodiment, the organic electronic device includes a substrate and an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode sequentially stacked on the substrate. The light-emitting layer contains at least one organic compound or mixture as described above, or the light-emitting layer is prepared from the composition as described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0167] The substrate may be transparent or opaque. The substrate may be rigid or elastic. The substrate may be plastic, metal, semiconductor wafer or glass. The substrate preferably has a smooth surface, and substrates without surface defects are particularly ideal. In one embodiment, the substrate is flexible, and its material may be selected from but not limited to polymer films or plastics, and its glass transition temperature Tg is above 150°C, preferably above 200°C, more preferably above 250°C, and preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0168] The anode is an electrode for injecting holes, and the anode can easily inject holes into the hole injection layer, or the hole transport layer, or the light-emitting layer. The anode may include a conductive metal, a conductive metal oxide, or a conductive polymer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials 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 anode materials are known and can be easily selected for use by ordinary technicians in this field. The anode material can be deposited using any suitable technology, 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 anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application. The cathode is an electrode that injects electrons, and the cathode can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer. The cathode may comprise a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or the electron transport layer (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 organic electronic devices may be used as cathode materials for the devices of the present application. Examples of cathode materials include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode 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.

[0169] The hole injection layer 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 skillfully 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.

[0170] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamines, organic materials based on carbazoles, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0171] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a spiroindoloacridine-based compound or a material known in the art may be used.

[0172] The electron transport layer can be used to smoothly transport electrons. The electron transport material is suitably a material with high electron mobility, which can skillfully 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.

[0173] The electron injection layer 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 fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.

[0174] It is understood that the organic electronic device may further include a hole blocking layer between the light-emitting layer and the electron transport layer, the hole blocking layer being a layer that blocks holes from reaching the negative electrode, and may 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.

[0175] In one embodiment, the organic electronic device described in the present application is a solution-type organic electronic device, and one or more functional layers thereof are prepared by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0176] The present application also relates to applications of the organic electronic device according to the present application in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0177] The present application also relates to an electronic device comprising the organic electronic device. The electronic device may be, but is not limited to, a display device, a lighting device, a light source, a sensor, and the like.

[0178] The present application is described in detail below through specific embodiments. The following embodiments are only partial embodiments of the present application and are not limitations of the present application. Specific embodiments

[0180] Example 1

[0181] The synthetic route of organic compound 1 in this example is as follows:

[0182]

[0183]

[0184] Synthesis of intermediate 1-2: Compound 1-1 (60 mmol), bipyralidone (60 mmol, CAS No.: 73183-34-3), Pd(dppf)Cl 2 (1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride, 0.2mmol) and potassium acetate (70mmol) were added to 180ml 1,4-dioxane and stirred at 100℃ for 8h in a nitrogen environment. After cooling, the solvent was removed by rotary evaporation, the residue was dissolved in dichloromethane and washed with water, and the organic phase was collected. After the organic phase was rotary evaporated to remove the solvent, the obtained crude product was recrystallized to obtain intermediate 1-2 with a yield of 76%.

[0185] The synthesis of intermediate 1-4 refers to the synthesis of intermediate 1-2, except that compound 1-1 is replaced by compound 1-3, with a yield of 75%.

[0186] Synthesis of intermediate 1-6: Compound 1-5 (40 mmol) and intermediate 1-4 (40 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (150 / 15 ml), and Pd(PPh 3 ) 4 (tetrakis(triphenylphosphine)palladium, 0.3mmol) and potassium carbonate (60mmol). Stir at 80°C for 5h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the product was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediate 1-6 with a yield of 75%.

[0187] Synthesis of intermediate 1-7: Intermediate 1-6 (30 mmol) and intermediate 1-2 (30 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (150 / 15 ml), and Pd(PPh3 ) 4 (0.3mmol) and potassium carbonate (60mmol). Stir at 100°C for 5h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the product was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediate 1-7 with a yield of 75%.

[0188] Synthesis of intermediate 1-9: Intermediate 1-7 (20 mmol), compound 1-8 (20 mmol), Pd(dba) 2 (Bisdibenzylideneacetone palladium, CAS No. 32005-36-0, 0.1mmol), tri-tert-butylphosphine (0.3mmol) and sodium tert-butoxide (40mmol) were added to 150ml toluene and stirred at 80°C for 5h in a nitrogen environment. After cooling, water was added to wash the reaction solution, and the organic phase was separated and collected. After the organic phase was evaporated to remove the solvent, the obtained crude product was sequentially subjected to column chromatography to obtain intermediate 1-9 with a yield of 82%.

[0189] Synthesis of intermediate 1-10: Intermediate 1-9 (15 mmol) was dissolved in 1,4-dioxane (150 ml), and diboric acid pinacol ester (15 mmol), Pd(dba) 2 (0.2mmol), tricyclohexylphosphine (0.6mmol) and potassium acetate (30mmol), heated to 80℃ in a nitrogen environment for 20h. After cooling, most of the solvent was removed by rotary evaporation, and then the product was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediate 1-10 with a yield of 65%.

[0190] Synthesis of organic compound 1: Intermediate 1-10 (9 mmol), compound 1-11 (9 mmol), Pd(PPh 3 ) 4 (0.03mmol) and potassium carbonate (20mmol). Stir at 80°C for 5h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and then the product was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain organic compound 1 with a yield of 85% and MS (ASAP) = 722.

[0191] Example 2

[0192] The synthetic route of organic compound 2 in this example is as follows:

[0193]

[0194] The synthesis of organic compound 2 was carried out by referring to the synthesis of organic compound 1, except that compound 1-11 was replaced by compound 2-1. The yield was 90%, and MS (ASAP)=695.

[0195] Example 3

[0196] The synthetic route of organic compound 3 in this example is as follows:

[0197]

[0198] The synthesis of organic compound 3 was carried out by referring to the synthesis of organic compound 1, except that compound 1-11 was replaced by compound 3-1. The yield was 87%, and MS (ASAP)=751.

[0199] Example 4

[0200] The synthetic route of organic compound 4 in this example is as follows:

[0201]

[0202] The synthesis of intermediate 4-2 refers to the synthesis of intermediate 1-9, except that compound 1-8 is replaced by compound 4-1, and the yield is 82%.

[0203] The synthesis of intermediate 4-3 refers to the synthesis of intermediate 1-10, except that intermediate 1-9 is replaced by intermediate 4-2, and the yield is 64%.

[0204] The synthesis of organic compound 4 refers to the synthesis of organic compound 1, except that compound 1-11 is replaced by compound 2-1, and intermediate 1-10 is replaced by intermediate 4-3. The yield is 90%, and MS (ASAP)=785.

[0205] Example 5

[0206] The synthetic route of organic compound 5 in this example is as follows:

[0207]

[0208] The synthesis of intermediate 5-2 refers to the synthesis of intermediate 1-2, except that compound 1-1 is replaced by compound 5-1, and the yield is 82%.

[0209] The synthesis of intermediate 5-3 refers to the synthesis of intermediate 1-6, except that intermediate 1-4 is replaced by intermediate 5-2, and the yield is 80%.

[0210] The synthesis of intermediate 5-4 refers to the synthesis of intermediate 1-7, except that intermediate 1-6 is replaced by intermediate 5-3, and the yield is 75%.

[0211] The synthesis of intermediate 5-5 refers to the synthesis of intermediate 1-9, except that intermediate 1-7 is replaced by intermediate 5-4, with a yield of 85%.

[0212] The synthesis of intermediate 5-6 refers to the synthesis of intermediate 1-10, except that intermediate 1-9 is replaced by intermediate 5-5, and the yield is 65%.

[0213] The synthesis of organic compound 5 was carried out by referring to the synthesis of organic compound 1, except that intermediate 1-10 was replaced by intermediate 5-6, with a yield of 89% and MS (ASAP)=706.

[0214] Example 6

[0215] The synthetic route of organic compound 6 in this example is as follows:

[0216]

[0217] The synthesis of organic compound 6 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 5-6, and compound 1-11 is replaced by compound 6-1, with a yield of 84%, MS (ASAP)=769.

[0218] Example 7

[0219] The synthetic route of organic compound 7 in this example is as follows:

[0220]

[0221] The synthesis of organic compound 7 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 5-6, and compound 1-11 is replaced by compound 7-1, with a yield of 86%, MS (ASAP)=729.

[0222] Example 8

[0223] The synthetic route of organic compound 8 in this example is as follows:

[0224]

[0225] The synthesis of intermediate 8-2 refers to the synthesis of intermediate 1-9, except that intermediate 1-7 is replaced by intermediate 5-4, and compound 1-8 is replaced by compound 8-1, with a yield of 82%.

[0226] The synthesis of intermediate 8-3 refers to the synthesis of intermediate 1-10, except that intermediate 1-9 is replaced by intermediate 8-2, and the yield is 64%.

[0227] The synthesis of organic compound 8 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by 8-3, and compound 1-11 is replaced by compound 2-1, with a yield of 87%, and MS (ASAP)=755.

[0228] Example 9

[0229] The synthetic route of organic compound 9 in this example is as follows:

[0230]

[0231] The synthesis of organic compound 9 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 5-6, and compound 1-11 is replaced by compound 9-1, with a yield of 86%, MS (ASAP)=705.

[0232] Example 10

[0233] The synthesis route of the organic compound 10 of this embodiment is as follows:

[0234]

[0235] The synthesis of organic compound 10 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 5-6, and compound 1-11 is replaced by compound 10-1, with a yield of 85%, and MS (ASAP)=719.

[0236] Embodiment 11

[0237] The synthetic route of the organic compound 11 of this embodiment is as follows:

[0238]

[0239] The synthesis of intermediate 11-2 refers to the synthesis of intermediate 1-9, except that compound 1-8 is replaced by compound 11-1, and the yield is 83%.

[0240] The synthesis of intermediate 11-3 refers to the synthesis of intermediate 1-10, except that intermediate 1-9 is replaced by intermediate 11-2, and the yield is 65%.

[0241] The synthesis of organic compound 11 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 11-3, and compound 1-11 is replaced by compound 2-1, with a yield of 86%, MS (ASAP)=745.

[0242] Example 12

[0243] The synthetic route of the organic compound 12 of this embodiment is as follows:

[0244]

[0245] The synthesis of organic compound 12 refers to the synthesis of organic compound 1, except that intermediate 1-10 is replaced by intermediate 5-6, and compound 1-11 is replaced by compound 12-1, with a yield of 80%, MS (ASAP)=679.

[0246] Comparative Example 1

[0247] The organic compound in this comparative example is comparative compound 1, and its chemical structure is as follows:

[0248]

[0249] Comparative Example 2

[0250] The organic compound in this comparative example is H2-1, and its chemical structure is as follows:

[0251]

[0252] Preparation of OLED devices

[0253] In the OLED device of this embodiment, ITO is used as the anode, HATCN is used as the hole injection layer material, HTM is used as the hole transport material, EBM is used as the electron blocking layer material, the organic compound 1 of Example 1 is used as the main material of the light-emitting layer, RD is used as the guest material of the light-emitting layer, ETM:Liq is used as the electron transport material, Liq is used as the electron injection material, and Al is used as the cathode, and the device structure is ITO / HATCN / HTM / EBM / main material (organic compound 1): RD / ETM:Liq / Liq / Al.

[0254] The schematic diagram of OLED device is shown in Figure 1 As shown, 10 is a substrate, 20 is an anode, 30 is a hole injection layer, 40 is a hole transport layer, 50 is an electron blocking layer, 60 is a light-emitting layer, 70 is an electron transport layer, 80 is an electron injection layer, and 90 is a cathode.

[0255] The chemical structural formulas of HATCN, HTM, EBM, RD, ETM and Liq are as follows:

[0256]

[0257] The above-mentioned HATCN, HTM, EBM, RD, ETM and Liq are all commercially available, or their synthesis methods are all prior art.

[0258] The preparation process of an OLED device using the above materials is described in detail below through specific examples.

[0259] Device Example 1

[0260] The method for preparing an OLED device in this embodiment comprises the following steps:

[0261] 1) Cleaning of ITO (Indium Tin Oxide) anode layer: Clean the ITO conductive glass anode layer, then use chloroform, ketone, isopropanol ultrasonic cleaning, and then perform UV ozone plasma treatment;

[0262] 2) Formation of hole injection layer: On the ITO anode layer, high vacuum (1×10 -6 mbar) evaporate the hole injection material HATCN with a thickness of 5 nm;

[0263] 3) Forming a hole transport layer: On the hole injection layer, a hole transport material HT1 is deposited by vacuum evaporation to a thickness of 90 nm;

[0264] 4) Forming an electron blocking layer: on the hole transport layer, an electron blocking layer material EBM is deposited by vacuum evaporation with a thickness of 20 nm;

[0265] 5) Formation of light-emitting layer: In high vacuum (1×10 -6 mbar), evaporating a light-emitting layer material on the electron blocking layer, wherein the light-emitting layer material comprises a main material organic compound 1 and a guest material RD, wherein the mass ratio of the main material organic compound 1 to the guest material RD is 95:5, and obtaining a light-emitting layer with a thickness of 40 nm;

[0266] 6) Forming an electron transport layer: on the light-emitting layer, vacuum evaporation is used to deposit electron transport materials ETM and Liq in a mass ratio of 1:1 and a thickness of 25 nm;

[0267] 7) Forming an electron injection layer: On the electron transport layer, vacuum evaporate the electron injection material LiF to a thickness of 0.5 nm;

[0268] 8) Forming the cathode layer: On the electron injection layer, vacuum evaporate the cathode Al layer with a thickness of 150nm

[0269] 9) Packaging: The device was encapsulated with UV curable resin in a nitrogen glove box.

[0270] Device Examples 2-12

[0271] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device embodiments 2-12 is selected from the organic compounds of embodiments 2-12 respectively.

[0272] Device Example 13

[0273] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device embodiment 13 includes organic compound 1 and organic compound H2-1, which are blended in a mass ratio of 1:1.

[0274] Device Example 14

[0275] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device embodiment 13 includes organic compound 2 and organic compound H2-1, which are blended in a mass ratio of 1:1.

[0276] Device Example 15

[0277] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device embodiment 13 includes organic compound 4 and organic compound H2-1, which are blended in a mass ratio of 1:1.

[0278] Device Example 16

[0279] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device embodiment 13 includes organic compound 8 and organic compound H2-1, which are blended in a mass ratio of 1:1.

[0280] Device Comparative Example 1

[0281] It is basically the same as device embodiment 1, except that the main material of the light-emitting layer of device comparative example 1 is comparative compound 1.

[0282] Device Comparison Example 2

[0283] It is basically the same as the device embodiment 1, except that the main material of the light-emitting layer of the device comparative example 1 is the organic compound H2-1.

[0284] Performance testing and results

[0285] The current-voltage (JV) characteristics of the OLED devices of device examples 1-16 and device comparison examples 1-2 were tested using a characterization device, and important parameters such as external quantum efficiency and lifetime LT95@1000nits were recorded. The external quantum efficiency is the current density of 10mA / cm 2 The relative value obtained when the device is in a constant current state; the lifespan LT95@1000nits refers to the time it takes for the device's brightness to drop from an initial brightness of 1000nits to 95% of the initial brightness. Among them, the lifespan LT95 and the external quantum efficiency are calculated relative to the device comparative example 1, that is, the lifespan of the device comparative example 1 is 1 and the external quantum efficiency is 100%. The test results are shown in Table 1 below.

[0286] Table 1:

[0287]

[0288]

[0289] From Table 1 we can see that:

[0290] The external quantum efficiency and lifetime of the OLED devices of device examples 1-12 are significantly higher than those of the OLED devices of device comparison examples 1-2. It can be seen that the OLED devices prepared using the organic material of the present application have higher luminous efficiency and lifetime.

[0291] The lifespan of the OLED devices of device embodiments 13-16 is significantly longer than that of the OLED devices of device embodiments 1-12. It can be seen that the use of the organic compound described in the present application as a co-host material can further improve the lifespan of the OLED device.

[0292] The organic compound of the present application is prepared by using The structure is bridged with the nitrogen-containing electron-withdrawing group M through the benzene ring, and the benzene ring is introduced Group, The group has a non-completely conjugated five-membered ring structure. Through the interaction between the conjugated group and the non-conjugated group, the charge transfer ability of the organic compound molecule can be effectively improved; the nitrogen-containing electron-withdrawing group has electron transfer ability, The combination of the two groups has hole transport capability, and helps to achieve balanced carrier transport in the light-emitting layer. In this way, the exciton utilization rate and device stability of the organic electronic device using the organic compound of the present application as the main material can be effectively improved, thereby improving the luminous efficiency and life of the organic electronic device.

[0293] The organic compounds, mixtures, compositions and organic electronic devices provided in the embodiments of the present application are introduced in detail above. 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 method of the present application and its core idea. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as limiting the present application.

Claims

1. An organic compound, characterized in that It has a structure as shown in the general formula (1): （1） in: Y1 is selected from O or S; Ar1 is selected from one of the following groups: ； R2, when present, is independently selected from -H, phenyl; Y3 is selected from O; M is selected from any one of the structures represented by formula (A-1) to (A-4): ， Y2 is selected from O or S; Ar2, Ar3, Ar4 are independently selected from the following groups: ； R6 is selected from -H; Y4 is selected from O; Each occurrence of Z1 is independently selected from CR1 or N, and at least one Z1 is selected from N; R1 is selected from -H; * indicates the attachment site.

2. The organic compound according to claim 1, characterized in that M is selected from one of the structures represented by formula (B-1) to (B-6): 。 3. The organic compound according to claim 1, characterized in that The organic compound is selected from the following structures: 。 4. A mixture, characterized in that: The mixture comprises the organic compound described in any one of claims 1 to 3 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 guest materials, luminescent host materials or organic dyes.

5. A composition, characterized in that: The composition comprises the organic compound according to any one of claims 1 to 3 or the mixture according to claim 4, and at least one organic solvent.

6. An organic electronic device comprising at least one organic functional layer, characterized in that: The organic functional layer is a light-emitting layer, and the light-emitting layer includes the organic compound described in any one of claims 1 to 3, or the mixture described in claim 4, or the light-emitting layer is prepared from the composition described in claim 5.

Images