Organic compound and mixture, composition and organic electronic device comprising the same

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 an electron blocking material in an electron blocking 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] Organic optoelectronic materials are diverse in synthesis, relatively low in manufacturing cost, and have excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential due to their wide viewing angle, fast response time, low operating voltage, and thin panel thickness in the application of optoelectronic devices (such as flat panel displays and lighting).

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent devices that use organic electroluminescence usually have a structure with a positive electrode and a negative electrode and an organic functional layer between them. In order to improve the efficiency and life of organic electroluminescent devices, the organic functional layer usually has a multilayer structure, and each layer contains different organic substances. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic functional layer, and electrons are injected from the negative electrode into the organic functional layer. 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 device has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0004] In addition to the light-emitting layer, OLED devices also require organic functional layers involving hole transport, such as hole transport layers and electron blocking layers, in order to achieve balanced transmission of holes and electrons and recombination of holes and electrons in the light-emitting layer to improve the efficiency and life of the device. In order to obtain efficient organic electroluminescent devices, in addition to developing high-performance light-emitting layer materials, the development of corresponding electron blocking layer materials is also very important. In order to improve the efficiency and life of organic electroluminescent devices, especially the efficiency and life of red light OLED devices, new electron blocking layer materials are urgently needed to be developed. Summary of the invention

[0005] In view of this, the present application provides an organic compound as a new type of electron blocking material, which is used in organic electronic devices to improve the problems of low luminous efficiency and short life of organic electronic devices.

[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] R1 is selected from * indicates the attachment site;

[0011] Ar1 and Ar2 are independently 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] Y1 is selected from O, S or CR2R3;

[0013] R2 and R3 are independently selected from hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxy group having 2 to 20 C atoms. Oxycarbonyl, or aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, or olefin group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0014] Correspondingly, the present application also provides a mixture, including the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent guest material, a luminescent host material or an organic dye.

[0015] Correspondingly, the present application also provides a composition, comprising the above organic compound or the above mixture, and at least one organic solvent.

[0016] 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.

[0017] Compared with the prior art, the organic compound of the present application has the following beneficial effects:

[0018] The organic compound of the present application is Cyclohexylbenzene or cyclopentylbenzene is introduced into the cyclohexyl group and the cyclopentyl group is a non-conjugated group. It is a conjugated group, and the interaction between the non-conjugated group and the conjugated group is beneficial to improving the hole transport performance of the molecule. Therefore, the organic electronic device using the organic compound of the present application as the electron blocking layer material has a higher exciton utilization rate and device stability, and thus has a higher luminous efficiency and a longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] 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 paying any creative work.

[0020] Figure 1 is a schematic structural diagram of an organic electronic device provided in an embodiment of the present application;

[0021] Figure 2 is a mass spectrum of organic compound 13 of Example 13 of the present application;

[0022] Figure 3 It is the mass spectrum of the organic compound 22 of Example 22 of the present application. DETAILED DESCRIPTION

[0023] 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.

[0024] In the present application, the terms "and / or", "or / and", and "and / or" used have a selection range including any one of two or more related listed items, and also include any and all combinations of related listed items, wherein the any and all combinations include any combination of two related listed items, any more related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in the present application, the technical solution undoubtedly includes technical solutions connected by "logical and", and undoubtedly includes technical solutions connected by "logical or". For example, "A and / or B" includes three parallel solutions of A, B and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, the technical solution that is all connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, the combination of any two or any three of A, B, C, and D, and also includes the combination of four of A, B, C, and D (that is, the technical solution that is all connected by "logical AND").

[0025] In this application, composition and printing ink, or ink have the same meaning and can be interchanged.

[0026] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0027] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0028] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] 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.

[0030] 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, isocyano, nitro or halogen, alkyl containing 1-20 C 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, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understandable that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, cyano, isocyanate, isothiocyanate, hydroxyl, trifluoromethyl. In some embodiments, 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, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0031] 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.

[0032] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which 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 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 is optionally 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 understandable 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, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0033] In the present application, "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, 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.

[0034] In the present application, "alkyl" may refer to a linear, branched 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. 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.

[0035] 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.

[0036] In the present application, the silyl group may be represented by the chemical formula -Si(Y101)(Y102)(Y103), and Y101, Y102, and Y103 may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Examples of the silyl group include trialkylsilyl groups and triarylsilyl groups, and specific examples thereof include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, and the like, but examples are not limited thereto.

[0037] 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), -NH(alkyl), -N(cycloalkyl), -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.

[0038] 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 halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0039] 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).

[0040] In the present application, "*" connected to a single bond indicates a connection or 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 no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in adjacent positions in the group are fusion sites.

[0043] 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.

[0044] 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 R is connected to any substitutable position of the benzene ring.

[0045] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0046] In the present application, "two adjacent Rs form a ring with each other" means a ring system formed by two adjacent Rs connected to each other, and the ring system can be selected from an aliphatic hydrocarbon ring, an aliphatic heterocycle, an aromatic hydrocarbon ring or an aromatic heterocycle.

[0047] In the present application, the terms "combination thereof", "any combination thereof", "any combination thereof" and the like include all suitable combinations of any two or more items in the listed groups.

[0048] 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.

[0049] In this application, "optionally", "optional", and "optional" mean optional, that is, any one of the two parallel solutions 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.

[0050] 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.

[0051] The technical solution of this application is as follows:

[0052] An organic compound having a structure as shown in the general formula (1):

[0053]

[0054] in:

[0055] R1 is selected from * indicates the attachment site;

[0056] Ar1 and Ar2 are independently 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;

[0057] Y1 is selected from O, S or CR2R3;

[0058] R2 and R3 are independently selected from hydrogen, deuterium (D), or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or a 2 to 20 C atoms group. The invention also includes but is not limited to alkyl, alkyl, alkyl, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene, alkylene,

[0059] In some embodiments, the organic compound is selected from the structure shown in formula (2-1), (2-2) or (2-3):

[0060]

[0061] Further, in some embodiments, the organic compound is selected from the structure shown in formula (3-1), (3-2) or (3-3):

[0062]

[0063] In some embodiments, Y1 as mentioned above is selected from O or S.

[0064] In one embodiment, the organic compound is selected from the structure shown in formula (4):

[0065]

[0066] In some embodiments, Ar1 and Ar2 are 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.

[0067] In a specific embodiment, according to the organic compound of the present invention, Ar1 and Ar2 are each independently selected from any one of the structures shown in (B-1) to (B-6):

[0068]

[0069] in:

[0070] X1 is selected from N or CR4;

[0071] Y2 is selected from O, S, S=O, SO2, NR5, PR5, CR6R7 or SiR6R7;

[0072] R4, R5, R6, and R7 are each independently selected from the group consisting of hydrogen, deuterium, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched-chain alkyl group having 3 to 20 C atoms, or a branched-chain alkoxy group having 3 to 20 C atoms, or a branched-chain thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or a 2 to 2 0 C atoms, or aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, or olefin having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;

[0073] Ar3 is independently selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms.

[0074] In some embodiments, Ar3 is selected from

[0075] Further, in some embodiments, the formula (B-3) is selected from one of the following structures:

[0076]

[0077] In some embodiments, Ar1 and Ar2 are each independently selected from the following groups:

[0078]

[0079] Wherein: R4, R5, R6, and R7 have the same meanings as above.

[0080] In one embodiment, each occurrence of R4, R5, R6, and R7 is independently selected from hydrogen, deuterium, or a straight-chain alkyl group having 1 to 10 C atoms, or a branched-chain alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a combination of these groups.

[0081] In some embodiments, the group formed by Ar1, Ar2 and N in the organic compound Select one of the following structures:

[0082]

[0083]

[0084] The above H atoms may be further substituted.

[0085] 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:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] It can be understood that the H in the structural formula of the above organic compound can be further substituted.

[0092] In some embodiments, the organic compound of the present application can be used as an organic functional material in an organic functional layer of an organic electronic device, in particular, in an organic functional layer of an OLED device. The organic functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer (EBL), a hole blocking layer (HBL) and an emitting layer (EML).

[0093] In one embodiment, the organic compound according to the present application is used in an electron blocking layer. Furthermore, the organic compound according to the present application is used in an electron blocking layer of an organic electronic device.

[0094] The present application also relates to an electron blocking layer material, comprising the organic compound as described above.

[0095] The present application further relates to a mixture, comprising at least one organic compound as described above and at least another organic functional material. The another organic functional material may be selected from but not limited to at least one of 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, a luminescent host material (Host Emitter) and an organic dye. 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.

[0096] In one embodiment, the another organic functional material is selected from electron transport materials, and is mixed with the organic compound described in the present application as a co-host material and used in organic electronic devices.

[0097] 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.

[0098] 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.

[0099] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0106] 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.

[0107] 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.

[0108] In some embodiments, organic solvents suitable for the present application are solvents having a Hansen solubility parameter within the following ranges:

[0109] δd (dispersion force) is in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0110] δp (polar force) is in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0111] δh (hydrogen bonding force) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0112] 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.

[0113] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a film comprising the organic compound.

[0114] 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.

[0115] In the composition, the content of the organic compound or the mixture is 0.01-10wt%, preferably 0.1-8wt%, more preferably 0.2-5wt%, and most preferably 0.25-3wt%.

[0116] 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.

[0117] 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:

[0118] 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.

[0119] 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 is prepared from the above composition.

[0120] The organic functional layer may be, but is not limited to, a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron injection layer, an electron transport layer or a hole blocking layer. In at least one embodiment, the organic functional layer is an electron blocking layer.

[0121] 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), etc. Organic electroluminescent devices such as OLED, OLEEC, and organic light emitting field effect transistor are particularly preferred. OLED is further particularly preferred.

[0122] In some more preferred embodiments, the organic functional layer comprises at least a hole transport layer and an electron blocking layer, wherein the electron blocking layer comprises the organic compound as described above.

[0123] In at least one embodiment, the organic electronic device is a red light organic electronic device.

[0124] In one embodiment, the organic electronic device described in the present application comprises a cathode, an anode, a light-emitting layer between the cathode and the anode, and a hole transport region between the anode and the light-emitting layer. The hole transport region comprises a hole transport layer and an electron blocking layer, wherein the hole transport layer is located between the anode and the light-emitting layer, and the electron blocking layer is located between the hole transport layer and the light-emitting layer. The electron blocking layer comprises the organic compound or mixture as described above, or is prepared from the above composition.

[0125] 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 electron blocking layer contains at least one organic compound or mixture as described above, or the electron blocking layer is prepared from the composition as described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0126] 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).

[0127] 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 luminophore in the light-emitting layer or the n-type semiconductor material 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 of the device of the present application. Examples of cathode materials 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 cathode material 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] The light-emitting layer may emit red, green or blue light, and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoazole-based, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0132] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives or heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0133] When the light-emitting layer emits red light, the following can be used as a light-emitting dopant: a phosphorescent material, such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr) or platinum octaethylporphyrin (PtOEP); or a fluorescent material, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as face tris(2-phenylpyridine) iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, the following can be used as light-emitting dopants: phosphorescent materials, such as (4,6-F2ppy)2Irpic; or fluorescent materials, such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers or PPV-based polymers, but the light-emitting dopants are not limited thereto.

[0134] In one embodiment, the light-emitting layer material comprises a structure as shown in general formula (6):

[0135]

[0136] in:

[0137] q is selected from 1 or 2;

[0138] Ar7, when present, is independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0139] Ar8, when present, is 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;

[0140] R8 and R9, when they appear each time, are independently selected from: hydrogen, D, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0141] In one embodiment, each occurrence of Ar7 is independently selected from quinoline or isoquinoline and their derivatives.

[0142] In one embodiment, each occurrence of Ar8 is independently selected from phenyl and its derivatives.

[0143] In at least one embodiment, the general formula (6) is selected from any one of the structures shown in general formulas (7-1) to (7-3):

[0144]

[0145] in:

[0146] a is any integer selected from 0, 1, 2, 3, 4, 5, 6, b is any integer selected from 0, 1, 2, 3, 4;

[0147] R 10 , R 11 Each occurrence is independently selected from: D, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0148] In one embodiment, at least one R 10 or R 11 It is selected from a linear alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0149] In one embodiment, at least one R 11 is selected from a linear alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms. 10 It is selected from a linear alkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0150] The compounds described by the general formula (6) may be selected from but not limited to the following structures, which may be arbitrarily substituted:

[0151]

[0152]

[0153]

[0154] 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.

[0155] 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.

[0156] 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.

[0157] The light emitting wavelength of the organic electronic device is between 600 and 700 nm, preferably between 600 and 650 nm, and more preferably between 600 and 630 nm.

[0158] 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.

[0159] 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.

[0160] The present application also relates to an electronic device comprising the organic electronic device, which may be, but is not limited to, a display device, a lighting device, a light source, a sensor, and the like.

[0161] 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

[0163] Example 1

[0164] The synthetic route of organic compound 1 in this example is as follows:

[0165]

[0166] Synthesis of intermediate 1-2: Compound 1-1 (50 mmol), bipyralidin (50 mmol, CAS 73183-34-3), Pd(dppf)Cl2 (1,1'-bis(diphenylphosphino)ferrocenepalladium dichloride, 0.2 mmol) and potassium acetate (60 mmol) were added to 160 ml of 1,4-dioxane and stirred at 100 ° C for 5 h in a nitrogen environment. After cooling, the solvent was removed by rotary evaporation, the residue was dissolved in dichloromethane and the separated liquid was 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 75%.

[0167] Synthesis of intermediate 1-4: Add intermediate 1-2 (32 mmol), compound 1-3 (32 mmol), Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium, 0.2 mmol) and potassium carbonate (60 mmol) to 300 ml of 1,4-dioxane / water (volume ratio 9:1), and stir at 80 ° C for 6 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the liquid was extracted with dichloromethane and washed with water. The organic phase was collected, the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography to obtain intermediate 1-4 with a yield of 70%.

[0168] Synthesis of organic compound 1: Intermediate 1-4 (20 mmol), compound 1-5 (20 mmol), Pd(dba)2 (bis(dibenzylideneacetone)palladium, 0.1 mmol), tri-tert-butylphosphine (0.3 mmol) and sodium tert-butoxide (40 mmol) were added to 150 ml of toluene and stirred at 100°C for 8 h 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 crude product was purified by column chromatography and recrystallization to obtain organic compound 1 with a yield of 89% and MS (ASAP) = 645.

[0169] Example 2

[0170] The synthetic route of organic compound 2 in this example is as follows:

[0171]

[0172] The synthesis of organic compound 2 was carried out by referring to the synthesis of organic compound 1, except that compound 1-5 was replaced by compound 2-1. The yield was 86%, and MS (ASAP)=685.

[0173] Example 3

[0174] The synthetic route of organic compound 3 in this example is as follows:

[0175]

[0176] The synthesis of organic compound 3 was carried out by referring to the synthesis of organic compound 1, except that compound 1-5 was replaced by compound 3-1. The yield was 85%, and MS (ASAP)=685.

[0177] Example 4

[0178] The synthetic route of organic compound 4 in this example is as follows:

[0179]

[0180] The synthesis of intermediate 4-2 refers to the synthesis of intermediate 1-2, except that compound 1-1 is replaced by compound 4-1, and the yield is 85%.

[0181] The synthesis of intermediate 4-3 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 4-2, and the yield is 80%.

[0182] The synthesis of organic compound 4 was carried out by referring to the synthesis of organic compound 1, except that intermediate 1-4 was replaced by intermediate 4-3, and compound 1-5 was replaced by compound 4-4. The yield was 75%, and MS (ASAP)=725.

[0183] Example 5

[0184] The synthetic route of organic compound 5 in this example is as follows:

[0185]

[0186] The synthesis of intermediate 5-2 refers to the synthesis of 1-2, except that compound 1-1 is replaced by compound 5-1, and the yield is 80%.

[0187] The synthesis of intermediate 5-3 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 5-2, and the yield is 70%.

[0188] The synthesis of organic compound 5 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 5-3, and compound 1-5 is replaced by compound 5-4. The yield is 90%, MS (ASAP)=555.

[0189] Example 6

[0190] The synthetic route of organic compound 6 in this example is as follows:

[0191]

[0192] The synthesis of organic compound 6 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 5-3, and compound 1-5 is replaced by compound 2-1. The yield is 85%, MS (ASAP)=671.

[0193] Example 7

[0194] The synthetic route of organic compound 7 in this example is as follows:

[0195]

[0196] The synthesis of organic compound 7 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 5-3, and compound 1-5 is replaced by compound 7-1. The yield is 86%, MS (ASAP)=645.

[0197] Example 8

[0198] The synthetic route of organic compound 8 in this example is as follows:

[0199]

[0200] The synthesis of intermediate 8-2 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 5-2, and compound 1-3 is replaced by compound 8-1, and the yield is 70%.

[0201] The synthesis of organic compound 8 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 8-2, and compound 1-5 is replaced by compound 2-1. The yield is 90%, MS (ASAP)=687.

[0202] Example 9

[0203] The synthetic route of organic compound 9 in this example is as follows:

[0204]

[0205] The synthesis of intermediate 9-1 refers to the synthesis of intermediate 1-4, except that compound 1-3 is replaced by compound 8-1, and the yield is 72%.

[0206] The synthesis of organic compound 9 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 9-1, and compound 1-5 is replaced by compound 5-4. The yield is 91%, MS (ASAP)=585.

[0207] Example 10

[0208] The synthesis route of the organic compound 10 of this embodiment is as follows:

[0209]

[0210] Synthesis of intermediate 10-3: Compound 10-1 (30 mmol), compound 10-2 (30 mmol), Pd(dba)2 (0.2 mmol), tri-tert-butylphosphine (0.6 mmol) and sodium tert-butoxide (50 mmol) were added to 150 ml of toluene and stirred at 80°C for 5 h 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 crude product was purified by column chromatography to obtain intermediate 10-3 with a yield of 80%.

[0211] The synthesis of organic compound 10 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 9-1, and compound 1-5 is replaced by intermediate 10-3. The yield is 82%, MS (ASAP)=675.

[0212] Embodiment 11

[0213] The synthetic route of the organic compound 11 of this embodiment is as follows:

[0214]

[0215] The synthesis of intermediate 11-2 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 5-2, and compound 1-3 is replaced by compound 11-1, and the yield is 74%.

[0216] The synthesis of organic compound 11 was carried out by referring to the synthesis of organic compound 1, except that intermediate 1-4 was replaced by intermediate 11-2. The yield was 86%, and MS (ASAP)=631.

[0217] Example 12

[0218] The synthetic route of the organic compound 12 of this embodiment is as follows:

[0219]

[0220] The synthesis of organic compound 12 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 11-2, and compound 1-5 is replaced by compound 2-1. The yield is 85%, MS (ASAP)=671.

[0221] Embodiment 13

[0222] The synthetic route of the organic compound 13 of this example is as follows:

[0223]

[0224] The synthesis of intermediate 13-1 refers to the synthesis of intermediate 1-4, except that compound 1-3 is replaced by compound 11-1, and the yield is 71%.

[0225] The synthesis of organic compound 13 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 13-1, and compound 1-5 is replaced by compound 2-1. The yield is 86%, MS (ASAP)=685.

[0226] Embodiment 14

[0227] The synthetic route of the organic compound 14 of this embodiment is as follows:

[0228]

[0229] The synthesis of organic compound 14 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 13-1, and compound 1-5 is replaced by compound 3-1. The yield is 90%, MS (ASAP)=685.

[0230] Embodiment 15

[0231] The synthetic route of the organic compound 15 of this embodiment is as follows:

[0232]

[0233] The synthesis of intermediate 15-2 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 5-2, and compound 1-3 is replaced by compound 15-1, and the yield is 70%.

[0234] The synthesis of organic compound 15 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 15-2, and compound 1-5 is replaced by compound 3-1, MS (ASAP)=687.

[0235] Example 16

[0236] The synthetic route of organic compound 16 in this example is as follows:

[0237]

[0238] The synthesis of intermediate 16-1 refers to the synthesis of intermediate 1-4, except that compound 1-3 is replaced by compound 15-1, and the yield is 72%.

[0239] The synthesis of organic compound 16 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 16-1, and compound 1-5 is replaced by compound 5-4, MS (ASAP)=585.

[0240] Embodiment 17

[0241] The synthetic route of organic compound 17 in this example is as follows:

[0242]

[0243] The synthesis of intermediate 17-2 refers to the synthesis of intermediate 1-4, except that intermediate 1-2 is replaced by intermediate 5-2, and compound 1-3 is replaced by compound 17-1, and the yield is 74%.

[0244] The synthesis of organic compound 17 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 17-2, and compound 1-5 is replaced by compound 17-3. The yield is 90%, MS (ASAP)=687.

[0245] Embodiment 18

[0246] The synthetic route of organic compound 18 in this example is as follows:

[0247]

[0248] The synthesis of intermediate 18-2 refers to the synthesis of intermediate 1-4, except that compound 1-3 is replaced by compound 18-1, and the yield is 72%.

[0249] The synthesis of intermediate 18-5 refers to the synthesis of intermediate 10-3, except that compound 10-1 is replaced by compound 18-4, and compound 10-2 is replaced by compound 18-3, and the yield is 75%.

[0250] The synthesis of organic compound 18 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 18-2, and compound 1-5 is replaced by intermediate 18-5. The yield is 87%, MS (ASAP)=665.

[0251] Embodiment 19

[0252] The synthetic route of organic compound 19 in this example is as follows:

[0253]

[0254] The synthesis of intermediate 19-2 refers to the synthesis of intermediate 1-4, except that compound 1-3 is replaced by compound 19-1, and the yield is 70%.

[0255] The synthesis of organic compound 19 refers to the synthesis of organic compound 1, except that intermediate 1-4 is replaced by intermediate 19-2, and compound 1-5 is replaced by compound 5-4. The yield is 85%, MS (ASAP)=569.

[0256] Embodiment 20

[0257] The synthesis route of the organic compound 20 of this embodiment is as follows:

[0258]

[0259] The synthesis of intermediate 20-2 refers to the synthesis of intermediate 10-3, except that compound 10-1 is replaced by compound 20-1, and the yield is 70%.

[0260] The synthesis of organic compound 20 refers to the synthesis of organic compound 1, except that compound 1-5 is replaced by intermediate 20-2, and intermediate 1-4 is replaced by intermediate 13-1. The yield is 86%, MS (ASAP)=699.

[0261] Embodiment 21

[0262] The synthetic route of the organic compound 21 of this example is as follows:

[0263]

[0264] The synthesis of organic compound 21 was carried out by referring to the synthesis of organic compound 1, except that intermediate 1-4 was replaced by intermediate 18-2. The yield was 86%, and MS (ASAP)=671.

[0265] Embodiment 22

[0266] The synthetic route of the organic compound 22 of this embodiment is as follows:

[0267]

[0268] The synthesis of organic compound 22 was based on the synthesis of organic compound 1, except that intermediate 1-4 was replaced by intermediate 13-1. The yield was 85%, and MS (ASAP)=645.

[0269] Comparative Example

[0270] The chemical structural formula of the comparative compound 1 of this comparative example is as follows:

[0271]

[0272] Preparation of OLED devices

[0273] In the OLED device of this embodiment, ITO is used as the anode, HATCN is used as the hole injection layer material, HT1 is used as the hole transport material, the organic compound 1-22 of Embodiment 1-22 is used as the electron blocking layer material, RH1 is used as the main material of the light-emitting layer, RD2 or RD1 is used as the red light guest material of the light-emitting layer, ETM:Liq is used as the electron transport material, LiF is used as the electron injection material, and Al is used as the cathode, and the device structure is ITO / HATCN / HT1 / organic compound / RH1:RD2 or RH1:RD1 / ETM:Liq / LiF / Al.

[0274] 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.

[0275] The chemical structural formulas of HATCN, HT1, RH1, RD2, RD1, ETM and Liq are as follows:

[0276]

[0277]

[0278] The above materials HATCN, HT1, RH1, RD2, RD1, ETM, and Liq are all commercially available, or their synthesis methods are all prior art.

[0279] The preparation process of an OLED device using the above materials is described in detail below through specific examples.

[0280] Device Example 1

[0281] The method for preparing an OLED device in this embodiment comprises the following steps:

[0282] 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;

[0283] 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;

[0284] 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;

[0285] 4) forming an electron blocking layer: evaporating the organic compound 1 of Example 1 on the hole transport layer to a thickness of 20 nm;

[0286] 5) Forming a light-emitting layer: A light-emitting layer is formed on the electronic resistance layer, wherein RH1 is a main material of the light-emitting layer, RD2 is a guest material of the light-emitting layer, the mass ratio of RH1 to RD2 is 95:5, and the thickness is 40 nm.

[0287] 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;

[0288] 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;

[0289] 8) Forming a cathode layer: on the electron injection layer, vacuum evaporate cathode Al with a thickness of 150 nm;

[0290] 9) Packaging: The device was encapsulated with UV curable resin in a nitrogen glove box.

[0291] Device Example 2-22

[0292] It is basically the same as device embodiment 1, except that the electron blocking materials of device embodiments 2-22 are selected from organic compounds 2-22 of embodiments 2-22 respectively.

[0293] Device Example 23

[0294] It is basically the same as device embodiment 1, except that the guest material of the light-emitting layer of device embodiment 23 is RD1.

[0295] Device Example 24

[0296] It is basically the same as device embodiment 11, except that the guest material of the light-emitting layer of device embodiment 24 is RD1.

[0297] Device Example 25

[0298] It is basically the same as device embodiment 15, except that the guest material of the light-emitting layer of device embodiment 25 is RD1.

[0299] Device Comparison

[0300] It is basically the same as device embodiment 1, except that the electron blocking material of the device comparative example is comparative compound 1.

[0301] Performance testing and results

[0302] See also Figure 2-3 , mass spectrometry was performed on the organic compound 13 of Example 13 and the organic compound 22 of Example 22 to obtain mass spectra of the organic compound 13 and the organic compound 22.

[0303] The current-voltage (JV) characteristics of the OLED devices of device examples 1-25 and device comparison examples 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 lifespan LT95@1000nits refers to the time when the brightness of the device decreases from the initial brightness of 1000nits to 95% of the initial brightness under constant current. The external quantum efficiency and lifespan of the OLED devices of device embodiments 1-25 are relative values ​​relative to the OLED devices of the device comparison example. The test results are shown in Table 1 below.

[0304] Table 1:

[0305]

[0306]

[0307] From Table 1 we can see that:

[0308] Compared with the OLED devices of the device comparison examples, the OLED devices of device embodiments 1-25 of the present application have higher efficiency and longer life. It can be seen that the performance of the organic electronic device made based on the organic compound of the present application as the electron blocking layer material is significantly better than the organic electronic device made with the compound of the comparison example as the electron blocking layer material.

[0309] The electron blocking layer materials used in device examples 1 and 23 are both organic compound 1, and the guest materials of the light-emitting layer are RD2 and RD1, respectively. As a result, the external quantum efficiency and lifetime of device examples 1 and 23 do not change significantly. The electron blocking layer materials used in device examples 11 and 24 are both organic compound 11, and the guest materials of the light-emitting layer are RD2 and RD1, respectively. As a result, the external quantum efficiency and lifetime of device examples 11 and 24 do not change significantly. The electron blocking layer materials used in device examples 15 and 25 are both organic compound 15, and the guest materials of the light-emitting layer are RD2 and RD1, respectively. As a result, the external quantum efficiency and lifetime of device examples 15 and 25 do not change significantly. It can be seen that the organic compounds of the present application can be applied to a variety of different light-emitting materials as electron blocking layer materials.

[0310] The organic compound of the present application is Cyclohexylbenzene or cyclopentylbenzene is introduced into the cyclohexyl group and the cyclopentyl group is a non-conjugated group. It is a conjugated group, and the interaction between the non-conjugated group and the conjugated group is beneficial to improving the hole transport performance of the molecule. Therefore, the organic electronic device using the organic compound of the present application as the electron blocking layer material has a higher exciton utilization rate and device stability, and thus has a higher luminous efficiency and a longer life.

[0311] 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): in: R1 is selected from * indicates the attachment site; Ar1 and Ar2 are independently selected from any one of the following groups: or biphenyl; R4 is selected from hydrogen or tert-butyl; R6 and R7 are selected from methyl; Y1 is selected from O, S or CR2R3; R2 and R3 are independently selected from methyl.

2. The organic compound according to claim 1, characterized in that The organic compound is selected from the structure shown in formula (2-1), (2-2) or (2-3):

3. The organic compound according to claim 1, characterized in that The organic compound is selected from the structure shown in formula (3-1), (3-2) or (3-3):

4. The organic compound according to claim 1, characterized in that The organic compound is selected from the structure shown in formula (4):

5. The organic compound according to claim 1, 2, 3 or 4, characterized in that: The group formed by Ar1, Ar2 and N in the organic compound Select one of the following structures:

6. The organic compound according to claim 1, characterized in that The organic compound is selected from one of the following structures:

7. A mixture, characterized in that: The mixture comprises the organic compound described in any one of claims 1 to 6 and at least one organic functional material, wherein the organic functional material is a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent guest material, a luminescent host material or an organic dye.

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

9. An organic electronic device comprising at least one organic functional layer, characterized in that: The organic functional layer comprises the organic compound according to any one of claims 1 to 6, or the mixture according to claim 7, or the organic functional layer is prepared from the composition according to claim 8.

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