Organic compounds and mixtures, compositions and organic electronic devices comprising the same

Abstract

Disclosed herein is an organic compound having a structure as shown in general formula (1): and mixtures, compositions and organic electronic devices comprising the organic compound, which is used in organic electronic devices, in particular as electron blocking layer material in the electron blocking layer of organic electronic devices, to improve the efficiency and lifetime of organic electronic devices.

Description

Technical Field

[0001] This application relates to the field of luminescent materials technology, and more particularly to an organic compound, and mixtures, compositions and organic electronic devices comprising said organic compound. Background Technology

[0002] Organic optoelectronic materials offer diverse synthesis options, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs), used in the fabrication of optoelectronic devices such as flat panel displays and lighting devices, offer advantages such as wide viewing angles, fast response times, low operating voltages, and thin panel thicknesses, thus possessing broad development potential.

[0003] Organic electroluminescence (OEC) refers to the phenomenon of converting electrical energy into light energy using organic materials. OEC devices typically have a structure with a positive electrode, a negative electrode, and an organic functional layer between them. To improve the efficiency and lifespan of OEC devices, the organic functional layer generally has a multi-layered structure, with each layer containing different organic materials to form organic functional layers with different functions. Specifically, the organic functional layer may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such OEC devices, when a voltage is applied between the two electrodes, holes are injected into the organic functional layer from the positive electrode, and electrons are injected into the organic functional layer from the negative electrode. When the injected holes and electrons meet, excitons are formed, and when these excitons transition back to the ground state, they emit light. Such OEC devices possess characteristics such as self-illumination, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0004] To improve the performance of organic electroluminescent devices, in addition to developing high-performance luminescent materials, the development of luminescent auxiliary materials is also crucial. Currently, although a large number of luminescent auxiliary materials have been developed, the corresponding devices still suffer from many problems, such as carrier transport imbalance and insufficient device lifetime. How to design new, higher-performance materials to regulate transport balance and improve device efficiency and lifetime remains a pressing issue for those skilled in the art. Summary of the Invention

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

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

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

[0008]

[0009] in,

[0010] Ar1, Ar2, and Ar3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms.

[0011] R1 is selected from substituted or unsubstituted alkyl groups having 1 to 20 C atoms, or substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, or combinations of these groups.

[0012] R2 is selected from substituted or unsubstituted alkyl groups having 1 to 20 C atoms, or silyl groups, cyano groups, isocyano groups, hydroxyl groups, nitro groups, -CF3 groups, -Cl groups, -Br groups, -F groups, -I groups, or substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, or combinations of these groups.

[0013] This 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 materials, host materials or organic dyes.

[0014] This application also provides a composition comprising the above-described organic compound or mixture thereof, and at least one organic solvent.

[0015] This application also provides an organic electronic device comprising at least one functional layer, wherein the functional layer contains the above-described organic compound or mixture thereof, or the functional layer is prepared from the above-described composition.

[0016] Compared with the prior art, the organic compounds of this application have the following beneficial effects:

[0017] The organic compounds in this application have the combined effect of steric hindrance groups and fused-ring fluorene groups, which can effectively regulate the hole transport performance of the organic compounds. Therefore, when the organic compounds in this application are used as electron blocking layer materials in organic electronic devices, the luminous efficiency and lifetime of organic electronic devices can be improved more effectively. Attached Figure Description

[0018] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0019] Figure 1 This is a schematic diagram of the structure of an organic electronic device provided in an embodiment of this application. Detailed Implementation

[0020] This application provides an organic compound, mixture, composition, and its application in organic electronic devices. To make the objectives, technical solutions, and effects of this application clearer and more explicit, the following provides a more detailed description. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the scope of this application.

[0021] The terms "and / or," "or / and," and "and / or" as used herein include any one of two or more of the related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of 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 this application, the technical solution undoubtedly includes technical solutions connected by "logical AND," and also undoubtedly includes technical solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: 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, a technical solution that is connected by "logical OR"), as well as any and all combinations of A, B, C, and D, that is, combinations of any two or three of A, B, C, and D, and also combinations of all four of A, B, C, and D (that is, a technical solution that is connected by "logical AND").

[0022] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0023] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0024] In this application, "heteroatom" refers to a non-carbon atom, which can be an N atom, an O atom, an S atom, etc.

[0025] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0026] In this 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.

[0027] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to: H, deuterium atom The group R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but is not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0028] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic 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-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0029] In this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and for polycyclic rings, at least one of them is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives. Understandably, multiple aryl groups can 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, and diaryl ether systems should also be included in the definition of aryl.

[0030] In this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, diazolyl, triazolyl, imidazole, pyridyl, bipyridyl, pyrimidinyl, etc. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolololyl, furanolofuranyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0031] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The number of carbon atoms in an alkyl group can 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 time it appears, it can independently be a 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, etc. tert-amyl, 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 The compounds include 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0032] In this application, the abbreviations for substituents are: n-n-, sec-sec-, i-iso-, t-tert-, o-ortho-, m-me-, p-para-, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0033] In this application, silane 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, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Examples of silane include trialkylsilane and triarylsilane, and specific examples include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these examples.

[0034] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0035] In this 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 (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0036] In this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0037] In this application, the "*" connected to a single bond indicates a connection or fusion site;

[0038] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site;

[0039] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites;

[0040] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring can be the same or different from each other.

[0041] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring, such as... express Can be with The above can be selected at any replaceable position to form a loop.

[0042] The technical solution of this application is as follows:

[0043] An organic compound having a structure as shown in general formula (1):

[0044]

[0045] in,

[0046] Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms.

[0047] R1 is selected from substituted or unsubstituted alkyl groups having 1 to 20 C atoms, or substituted or unsubstituted aromatic groups having 6 to 60 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 60 cyclic atoms, or combinations of these groups.

[0048] R2 is selected from substituted or unsubstituted alkyl groups having 1 to 20 C atoms, or silyl groups, cyano groups, isocyano groups, hydroxyl groups, nitro groups, -CF3 groups, -Cl groups, -Br groups, -F groups, -I groups, or substituted or unsubstituted aromatic groups having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms, or combinations of these groups.

[0049] In one embodiment, Ar1, Ar2, and Ar3 each independently represent a substituted or unsubstituted aromatic group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 25 ring atoms.

[0050] Furthermore, Ar1, Ar2, and Ar3 are each independently selected from the following groups:

[0051]

[0052] in,

[0053] Each time X appears, it is independently selected from CR3 or N;

[0054] Each time Y appears, it is independently selected from NR4, PR4, CR5R6, SiR5R6, O, S, S(=O)2 or S(=O);

[0055] R3, R4, R5, and R6 are each independently selected from: -H, -D (deuterium), straight-chain alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, thioalkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, alkoxy groups having 3 to 20 carbon atoms, thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, and aryloxycarbonyl groups having 7 to 20 carbon atoms. The group may contain: alkyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 50 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 50 ring atoms, aryloxy groups having 6 to 50 ring atoms, heteroaryloxy groups having 5 to 50 ring atoms, or combinations of these groups.

[0056] In this application, when X is a connection site, X is C; when Y is a connection site, Y is N.

[0057] In one embodiment, Ar1 is selected from the following groups:

[0058]

[0059] Where * represents a fusion site.

[0060] In some of these embodiments, Ar1 is selected from the following groups:

[0061]

[0062] Wherein: the above groups are either unsubstituted or substituted by substituents; the meaning of the substituents is the same as described above.

[0063] In one embodiment, the organic compound is selected from any structure of formula (2-1)-(2-6):

[0064]

[0065] Where: m is selected from 0, 1, 2, 3, 4, 5 or 6; n is selected from 0, 1, 2, 3 or 4.

[0066] In one embodiment, R1 is selected from substituted or unsubstituted alkyl groups having 1 to 10 C atoms, or substituted or unsubstituted aromatic groups having 6 to 30 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 cyclic atoms, or combinations of these groups.

[0067] Furthermore, R1 is selected from substituted or unsubstituted alkyl groups having 1 to 6 C atoms, or substituted or unsubstituted aromatic groups having 6 to 18 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 18 cyclic atoms, or combinations of these groups.

[0068] In a specific embodiment, R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, or the following groups:

[0069]

[0070] in:

[0071] Each time X1 appears, it is independently selected from CR7 or N;

[0072] Y1 is selected from NR8 and CR9R. 10 SiR9R 10 , O, S, S=O or SO2;

[0073] R7, R8, R9, R 10 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a silyl group, cyano, isocyano, hydroxyl, nitro, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0074] In this application, when X1 is a connection site, X1 is C; when Y1 is a connection site, Y1 is N.

[0075] In a specific embodiment, R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, pyridyl, pyrimidinyl, triazine, naphthyl, phenanthrene, triphenylene, or the following groups:

[0076] Or a combination of these groups.

[0077] Furthermore, in one embodiment, R1 is selected from methyl.

[0078] In one embodiment, R2 is selected from alkyl groups having 1 to 6 carbon atoms, or silyl groups, cyano groups, isocyano groups, hydroxyl groups, nitro groups, -CF3 groups, -Cl groups, -Br groups, -F groups, -I groups, or substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 13 ring atoms, or combinations of these groups.

[0079] In one specific embodiment, R2 is selected from 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, cyano, isocyano, hydroxyl, nitro, -CF3, -Cl, -Br, -F, -I, or the following groups:

[0080]

[0081] in:

[0082] Each time X2 appears, it is independently selected from CR. 11 Or N;

[0083] Y2 is selected from NR 12 CR 13 R 14 SiR 13 R 14 , O, S, S=O or SO2;

[0084] R 11 R 12 R 13 R 14 Each occurrence is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a silyl group, cyano, isocyano, hydroxyl, nitro, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0085] In this application, when X2 is a connection site, X2 is C; when Y2 is a connection site, Y2 is N.

[0086] In a specific embodiment, R2 is selected from methyl, ethyl, n-propyl, n-butyl, sec-butyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, cyano, -F, -CF3, -CN, phenyl, biphenyl, pyridyl, pyrimidinyl, triazine, naphthyl, phenanthrene, or the following groups:

[0087] Or a combination of these groups.

[0088] In one embodiment, R1 is selected from an alkyl group having 1 to 10 carbon atoms, and R2 is selected from an alkyl group having 1 to 10 carbon atoms. Further, R1 is selected from methyl, and R2 is selected from methyl, ethyl, n-propyl, n-butyl, sec-butyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, or adamantyl.

[0089] In one embodiment, Ar2 and Ar3 are selected from the following groups:

[0090]

[0091] Wherein: R3 is selected from -H, -D, alkyl groups having 1 to 6 C atoms, or silyl, cyano, isocyano, hydroxy, nitro, -CF3, -Cl, -Br, -F, -I, or substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, or substituted or unsubstituted heteroaromatic groups having 6 to 13 ring atoms, or combinations of these groups.

[0092] In one embodiment, R3 is selected from -H, -D, methyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, cyano, -F, phenyl, biphenyl, pyridyl, pyrimidinyl, naphthyl, phenanthrene, or the following groups:

[0093] Or a combination of these groups.

[0094] In some embodiments, Ar2, Ar3, and N connected to both Ar2 and Ar3 form... The structure is as follows:

[0095]

[0096]

[0097] In some embodiments, Ar2, Ar3, and N connected to both Ar2 and Ar3 form... The structure is as follows:

[0098]

[0099]

[0100] In this context, * indicates a connection site.

[0101] As an example, in some embodiments, the organic compounds of this application may be selected from, but are not limited to, any of the following structures:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] It is understandable that the H in the structural formula of the above organic compounds can be further substituted.

[0109] The organic compounds according to this application can be used as functional materials in the organic functional layers of organic electronic devices. The organic functional layers can be, but are not limited to, hole injection layer (HIL), hole transport layer (HTL), electron transport layer (ETL), electron injection layer (EIL), electron blocking layer (EBL), hole blocking layer (HBL), and light-emitting layer (EML).

[0110] In one embodiment, the organic compound according to the invention is used in an electron blocking layer; further, the organic compound according to the invention is used in an electron blocking layer of an organic electronic device.

[0111] This application also relates to an electron blocking layer material comprising the organic compound described above.

[0112] This application further relates to a mixture comprising at least one organic compound as described above and at least another organic functional material. The other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, and organic dyes. Detailed descriptions of the other organic functional material are available in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0113] In one embodiment, the other organic functional material is selected from electron transport materials and is blended with the organic compound described in this application as a co-host material for use in organic electronic devices.

[0114] This application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0115] The organic solvent is selected from at least one of aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate esters, and phosphate esters.

[0116] In at least one embodiment, the organic solvent in the composition is selected from aromatic or heteroaromatic solvents.

[0117] The aromatic or heteroaromatic solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, 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-isopropylbenzene. At least one of the following: 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-furanoate, and ethyl 2-furanoate.

[0118] The ester-based solvent may be selected from, but is 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 octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0119] The aromatic ketone-based solvent may be selected from, but is not limited to, 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but is not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, and 2-methylphenylacetone.

[0120] 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-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl 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.

[0121] The aliphatic ketone-based solvent may be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentyl 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.

[0122] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0123] In some embodiments, the composition of this 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.

[0124] The other organic solvent may be selected from, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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), tetrahydronaphthalene, naphthane, and indene.

[0125] In some embodiments, suitable organic solvents for this application are solvents with Hansen solubility parameters within the following ranges:

[0126] 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;

[0127] 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;

[0128] δh (hydrogen bond strength) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0129] In some embodiments, the boiling point of the organic solvent is taken into consideration when selecting the composition according to this application. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.

[0130] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the organic compound.

[0131] In some embodiments, the composition is a solution. In still other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, modifying film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0132] In the composition, the content of the organic compound or mixture is 0.01-10 wt%, preferably 0.1-8 wt%, more preferably 0.2-5 wt%, and most preferably 0.25-3 wt%.

[0133] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method may include, but is not limited to, inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and inkjet printing are preferred.

[0134] This application also relates to the use of the organic compound, mixture, or composition as described above in organic electronic devices. Specific details are as follows:

[0135] An organic electronic device includes at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or is prepared from the above-described composition.

[0136] Furthermore, the organic electronic device includes a cathode, an anode, and at least one functional layer. The functional layer comprises at least one organic compound or mixture as described above, or the functional layer is prepared from the above-described composition.

[0137] The functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer. Preferably, the functional layer is an electron blocking layer.

[0138] In one embodiment, the organic functional layer includes at least an electron blocking layer, which comprises an organic compound or mixture as described above. The specific organic compound is defined as stated above.

[0139] The organic electronic devices mentioned can be, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Organic electroluminescent devices such as OLEDs, OLEECs, and organic light-emitting field-effect transistors are particularly preferred. OLEDs are even more particularly preferred.

[0140] 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 light-emitting layer is prepared from a composition as described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0141] The substrate can be transparent or opaque; a transparent substrate can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface; a substrate without surface defects is particularly desirable. In one embodiment, the substrate is flexible, and its material can be selected from, but is not limited to, polymer films or plastics, with a glass transition temperature (Tg) of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Suitable examples of flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0142] The anode is the electrode for injecting holes, and the anode can readily inject holes into the hole injection layer, hole transport layer, or light-emitting layer. The anode may comprise 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 level or valence band level of the light emitter or p-type semiconductor material serving as a HIL, HTL, or electron blocking layer (EBL) in the light-emitting layer 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 readily selected by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to this application. The cathode is an electron-injecting electrode, and electrons can be readily injected into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may contain 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 level or conduction band level of the light-emitting material in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or 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 suitable for use as cathodes in organic electronic devices can be used as cathode materials for the devices of this 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. Cathode materials 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.

[0143] The hole injection layer is used to facilitate the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can readily receive holes injected from the positive electrode at low voltage. 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, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0144] The hole transport layer can be used to efficiently transport holes. Hole transport materials known in the art for use in the hole transport layer are suitably materials with high hole mobility, capable of receiving holes transported from the anode or hole injection layer and transferring the holes to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions.

[0145] The electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. The compound described in this application or other materials known in the art can be used as the electron blocking layer.

[0146] The light-emitting layer can emit red, green, or blue light and can be composed of phosphorescent or fluorescent materials. The light-emitting material is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining 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 include: 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds based on benzoazole, benzothiazole, and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; fluorene, etc., but are not limited thereto.

[0147] Examples of host materials used for the luminescent layer include fused aromatic ring derivatives or heterocyclic compounds. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds, while examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these examples.

[0148] When the emissive layer emits red light, the following can be used as luminescent dopants: phosphorescent materials, such as bis(1-phenylisoquinoline)acetylacetone iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetone iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr), or octaethylporphyrin platinum (PtOEP); or fluorescent materials, such as tris(8-hydroxyquinoline)aluminum (Alq3), but the luminescent dopants are not limited to these. When the emissive layer emits green light, phosphorescent materials such as planar tris(2-phenylpyridine)iridium (Ir(ppy)3) or fluorescent materials such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used as luminescent dopants, but the luminescent dopants are not limited to these. When the luminescent layer emits blue light, the following can be used as luminescent dopants: phosphorescent materials, such as (4,6-F2ppy)2Irpic; or fluorescent materials, such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylaryl (DSA), PFO-based polymers, or PPV-based polymers, but the luminescent dopants are not limited to these.

[0149] The electron transport layer can be used to efficiently transport electrons. The electron transport material is suitable as a material with high electron mobility, capable of efficiently receiving electrons injected from the negative electrode and transferring them to the light-emitting layer. Specific examples may include, but are not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.

[0150] The electron injection layer can be used to smoothly inject electrons. The preferred electron injection material has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation capabilities. Specific examples include fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but are not limited to these.

[0151] The hole-blocking layer is a layer that prevents holes from reaching the negative electrode, and it can typically be formed under the same conditions as the hole injection layer. Specific examples include, but are not limited to, diazole or triazole derivatives, phenanthrene-rholine derivatives, BCP, aluminum complexes, etc.

[0152] The light emission wavelength of the organic electronic device is between 300 and 1000 nm, preferably between 350 and 900 nm, and even more preferably between 400 and 800 nm.

[0153] In one embodiment, the organic electronic device described in this application is a solution-type organic electronic device, wherein one or more functional layers are fabricated by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0154] This application also relates to the application of the organic electronic device according to this application in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0155] This application also relates to electronic devices that include the aforementioned organic electronic devices. The electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0156] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application. Specific Implementation

[0158] Example 1

[0159] The synthetic route of organic compound M1 in this embodiment is as follows:

[0160]

[0161] 1) Synthesis of intermediate M1-3:

[0162] Under nitrogen atmosphere, (28.3 g, 100 mmol) of compound M1-1 and 200 mL of anhydrous tetrahydrofuran solvent were added to a 500 mL two-necked flask, stirred to dissolve, cooled to -78 °C, and 100 mmol of n-butyllithium was slowly added dropwise. The temperature was maintained, and the reaction was stirred for 2 hours. The reaction solution was slowly transferred to 100 mL of anhydrous tetrahydrofuran solution containing (21.3 g, 100 mmol) of compound M1-2. The reaction was stirred at room temperature for 6 hours, quenched with water, and most of the solvent was evaporated by rotary evaporation. The solution was washed three times with water dissolved in dichloromethane, and the organic phase was collected and evaporated to dryness to obtain intermediate M1-3.

[0163] 2) Synthesis of intermediate M1-4:

[0164] The intermediate M1-3 obtained in the previous step, 150 mL of acetic acid, and 30 mL of hydrobromic acid were added to a 500 mL two-necked flask. The mixture was heated to 100 °C and stirred for 12 hours. After the reaction was completed, the reaction solution was added to 500 mL of water, filtered, and the residue was recrystallized from an ethyl acetate / ethanol mixture to obtain intermediate M1-4. The combined yield of steps 1) and 2) was 70%.

[0165] 3) Synthesis of organic compound M1:

[0166] Under nitrogen atmosphere, (11.9 g, 30 mmol) of intermediate M1-4, (10.9 g, 30 mmol) of compound M1-5, (0.55 g, 0.6 mmol) of compound Pd2(dba)3, (0.24 g, 1.2 mmol) of compound tri-tert-butylphosphine, (4.1 g, 45 mmol) of compound sodium tert-butoxide, and 100 mL of anhydrous toluene solvent were added to a 300 mL two-necked flask. The mixture was heated to 60 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was washed three times with water after being dissolved in dichloromethane. The organic liquid was collected and purified by silica gel column chromatography to obtain organic compound M1 in 72% yield. MS (ASAP) = 680.

[0167] Example 2

[0168] The synthetic route of organic compound M2 in this embodiment is as follows:

[0169]

[0170] Synthesis of organic compound M2: Following the synthesis method of organic compound M1, compound M2-1 was substituted for compound M1-5, with a yield of 74%. MS (ASAP) = 622.

[0171] Example 3

[0172] The synthetic route of organic compound M3 in this embodiment is as follows:

[0173]

[0174] 1) Synthesis of intermediate M3-3:

[0175] Under nitrogen atmosphere, 50 mL of aqueous solution of compound M3-1 (31.7 g, 100 mmol), compound M3-2 (19.6 g, 100 mmol), tetrakis(triphenylphosphine)palladium (3.31 g, 3 mmol), potassium carbonate (27.6 g, 200 mmol), and 200 mL of toluene were added to a 500 mL three-necked flask. The mixture was heated and stirred at 110 °C for 12 hours. After the reaction was stopped, the mixture was cooled to room temperature, and the filtrate was filtered. Most of the solvent was evaporated by rotary evaporation. The filtrate was dissolved in dichloromethane and washed three times with water. The organic liquid was collected, mixed with silica gel, and purified by column chromatography to obtain intermediate M3-3 in 65% yield.

[0176] 2) Synthesis of intermediate M3-5:

[0177] Under nitrogen atmosphere, (15.6 g, 60 mmol) intermediate M3-3, (0.2 g, 3 mmol) zinc powder, (0.68 g, 3 mmol) zinc bromide, (0.65 g, 3 mmol) cobalt bromide, and 200 mL of acetonitrile were added to a 500 mL three-necked flask and stirred to dissolve. 10 mL of trifluoroacetic acid was added, and the mixture was stirred for 1 hour. Then, (4.7 g, 60 mmol) compound M3-4 was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was neutralized with sodium bicarbonate aqueous solution. The filtrate was filtered, and most of the solvent was evaporated by rotary evaporation. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected, mixed with silica gel, and purified by column chromatography to obtain intermediate M3-5 with a yield of 53%.

[0178] 3) Synthesis of intermediate M3-6: Following the synthesis method of intermediate M1-3, intermediate M3-5 was used to replace compound M1-2.

[0179] 4) Synthesis of intermediate M3-7: Following the synthesis method of intermediate M1-4, intermediate M3-6 replaces intermediate M1-3. The combined yield of steps 3) and 4) is 68%.

[0180] 5) Synthesis of organic compound M3: Following the synthesis method of organic compound M1, intermediate M3-7 and compound M3-8 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 70%. MS (ASAP) = 632.

[0181] Example 4

[0182] The synthetic route of organic compound M4 in this embodiment is as follows:

[0183]

[0184] 1) Synthesis of intermediate M4-2: Following the synthesis method of intermediate M1-3, replace compound M1-2 with compound M4-1.

[0185] 2) Synthesis of intermediate M4-3: Following the synthesis method of intermediate M1-4, intermediate M4-2 replaces intermediate M1-3. The combined yield of steps 1) and 2) is 69%.

[0186] 3) Synthesis of organic compound M4: Following the synthesis method of organic compound M1, intermediate M4-3 and compound M4-4 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 72%. MS (ASAP) = 630.

[0187] Example 5

[0188] The synthetic route of organic compound M5 in this embodiment is as follows:

[0189]

[0190] 1) Synthesis of intermediate M5-2: Following the synthesis method of intermediate M3-5, compound M5-1 was used to replace intermediate M3-3, with a yield of 51%.

[0191] 2) Synthesis of intermediate M5-3: Following the synthesis method of intermediate M1-3, intermediate M5-2 was used to replace compound M1-2.

[0192] 3) Synthesis of intermediate M5-4: Following the synthesis method of intermediate M1-4, intermediate M5-3 is used to replace intermediate M1-3. The combined yield of steps 2) and 3) is 66%.

[0193] 4) Synthesis of organic compound M5: Following the synthesis method of organic compound M1, intermediate M5-4 and compound M1-5 were substituted for intermediate M1-4 and compound M1-5, respectively, with a yield of 70%. MS(ASAP) = 656.

[0194] Example 6

[0195] The synthetic route of organic compound M6 in this embodiment is as follows:

[0196]

[0197] 1) Synthesis of intermediate M6-2: Following the synthesis method of intermediate M3-3, compound M6-1 was substituted for compound M3-2, with a yield of 62%.

[0198] 2) Synthesis of intermediate M6-3: Following the synthesis method of intermediate M3-5, intermediate M6-2 was used to replace intermediate M3-3, with a yield of 52%.

[0199] 3) Synthesis of intermediate M6-4: Following the synthesis method of intermediate M1-3, intermediate M6-3 was used to replace compound M1-2.

[0200] 4) Synthesis of intermediate M6-5: Following the synthesis method of intermediate M1-4, intermediate M6-4 replaces intermediate M1-3, wherein the combined yield of steps 3) and 4) is 65%.

[0201] 5) Synthesis of organic compound M6: Following the synthesis method of organic compound M1, intermediate M1-4 and compound M1-5 were replaced by intermediate M6-5 and compound M6-6, respectively, with a yield of 72%. MS(ASAP) = 666.

[0202] Example 7

[0203] The synthetic route of organic compound M7 in this embodiment is as follows:

[0204]

[0205] 1) Synthesis of intermediate M7-2: Following the synthesis method of intermediate M1-3, replace compound M1-2 with compound M7-1.

[0206] 2) Synthesis of intermediate M7-3: Following the synthesis method of intermediate M1-4, intermediate M7-2 was used to replace intermediate M1-3. The combined yield of steps 1) and 2) was 67%.

[0207] 3) Synthesis of organic compound M7: Following the synthesis method of organic compound M1, intermediate M1-4 and compound M1-5 were replaced by intermediate M7-3 and compound M7-4, respectively, with a yield of 74%. MS(ASAP) = 707.

[0208] Example 8

[0209] The synthetic route of organic compound M8 in this embodiment is as follows:

[0210]

[0211] 1) Synthesis of intermediate M8-2: Following the synthesis method of intermediate M1-3, replace compound M1-2 with compound M8-1.

[0212] 2) Synthesis of intermediate M8-3: Following the synthesis method of intermediate M1-4, intermediate M8-2 was used to replace intermediate M1-3. The combined yield of steps 1) and 2) was 68%.

[0213] 3) Synthesis of organic compound M8: Following the synthesis method of organic compound M1, intermediate M1-4 and compound M1-5 were replaced by intermediate M8-3 and compound M8-4, respectively, with a yield of 72%. MS(ASAP) = 716.

[0214] Example 9

[0215] The synthetic route of organic compound M9 in this embodiment is as follows:

[0216]

[0217] 1) Synthesis of intermediate M9-2: Following the synthesis method of intermediate M3-3, compound M9-1 was substituted for compound M3-2, with a yield of 60%.

[0218] 2) Synthesis of intermediate M9-4: Following the synthesis method of intermediate M3-5, intermediate M9-2 and compound M9-3 were used to replace intermediate M3-3 and compound M3-4, respectively, with a yield of 54%.

[0219] 3) Synthesis of intermediate M9-5: Following the synthesis method of intermediate M1-3, intermediate M9-4 was used to replace compound M1-2.

[0220] 4) Synthesis of intermediate M9-6: Following the synthesis method of intermediate M1-4, intermediate M9-5 replaces intermediate M1-3, wherein the combined yield of steps 3) and 4) is 63%.

[0221] 5) Synthesis of organic compound M9: Following the synthesis method of organic compound M1, intermediate M9-6 and compound M9-7 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 70%. MS (ASAP) = 698.

[0222] Example 10

[0223] The synthetic route of organic compound M10 in this embodiment is as follows:

[0224]

[0225] 1) Synthesis of intermediate M10-3: Following the synthesis method of intermediate M3-5, compounds M10-1 and M10-2 were used to replace intermediates M3-3 and M3-4, respectively, with a yield of 45%.

[0226] 2) Synthesis of intermediate M10-4: Following the synthesis method of intermediate M1-3, intermediate M10-3 was used to replace compound M1-2.

[0227] 3) Synthesis of intermediate M10-5: Following the synthesis method of intermediate M1-4, intermediate M10-4 is used to replace intermediate M1-3. The combined yield of steps 2) and 3) is 64%.

[0228] 4) Synthesis of organic compound M10: Following the synthesis method of organic compound M1, intermediate M10-5 and compound M10-6 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 65%. MS (ASAP) = 701.

[0229] Example 11

[0230] The synthetic route of organic compound M11 in this embodiment is as follows:

[0231]

[0232] 1) Synthesis of intermediate M11-2: Following the synthesis method of intermediate M1-3, replace compound M1-2 with compound M11-1.

[0233] 2) Synthesis of intermediate M11-3: Following the synthesis method of intermediate M1-4, intermediate M11-2 was used to replace intermediate M1-3. The combined yield of steps 1) and 2) was 63%.

[0234] 3) Synthesis of organic compound M11: Following the synthesis method of organic compound M1, intermediate M11-3 and compound M11-4 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 71%. MS(ASAP) = 676.

[0235] Example 12

[0236] The synthetic route of organic compound M12 in this embodiment is as follows:

[0237]

[0238] 1) Synthesis of intermediate M12-2: Following the synthesis method of intermediate M3-5, compounds M5-1 and M12-1 were used to replace intermediates M3-3 and M3-4, respectively, with a yield of 43%.

[0239] 2) Synthesis of intermediate M12-3: Following the synthesis method of intermediate M1-3, intermediate M12-2 was used to replace compound M1-2.

[0240] 3) Synthesis of intermediate M12-4: Following the synthesis method of intermediate M1-4, intermediate M12-3 is used to replace intermediate M1-3. The combined yield of steps 2) and 3) is 63%.

[0241] 4) Synthesis of organic compound M12: Following the synthesis method of organic compound M1, intermediate M12-4 and compound M12-5 were substituted for intermediate M1-4 and compound M1-5, respectively, with a yield of 72%. MS(ASAP) = 778.

[0242] Example 13

[0243] The synthetic route of organic compound M13 in this embodiment is as follows:

[0244]

[0245] 1) Synthesis of intermediate M13-3: Following the synthesis method of intermediate M3-5, compounds M13-1 and M13-4 were substituted for intermediate M3-3 and compound M3-4, respectively, with a yield of 45%.

[0246] 2) Synthesis of intermediate M13-4: Following the synthesis method of intermediate M1-3, intermediate M13-3 was used to replace compound M1-2.

[0247] 3) Synthesis of intermediate M13-5: Following the synthesis method of intermediate M1-4, intermediate M13-4 is used to replace intermediate M1-3. The combined yield of steps 2) and 3) is 64%.

[0248] 4) Synthesis of organic compound M13: Following the synthesis method of organic compound M1, intermediate M13-5 and compound M13-6 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 75%. MS (ASAP) = 700.

[0249] Example 14

[0250] The synthetic route of organic compound M14 in this embodiment is as follows:

[0251]

[0252] 1) Synthesis of intermediate M14-2: Following the synthesis method of intermediate M3-5, compounds M5-1 and M14-1 were used to replace intermediates M3-3 and M3-4, respectively, with a yield of 46%.

[0253] 2) Synthesis of intermediate M14-3: Following the synthesis method of intermediate M1-3, intermediate M14-3 was used to replace compound M1-2.

[0254] 3) Synthesis of intermediate M14-4: Following the synthesis method of intermediate M1-4, intermediate M1-3 is replaced by intermediate M14-3, wherein the combined yield of steps 2) and 3) is 65%.

[0255] 4) Synthesis of organic compound M14: Following the synthesis method of organic compound M1, intermediate M14-4 and compound M14-5 were substituted for intermediate M1-4 and compound M1-5, respectively, with a yield of 74%. MS(ASAP) = 728.

[0256] Example 15

[0257] The synthetic route of organic compound M15 in this embodiment is as follows:

[0258]

[0259] 1) Synthesis of intermediate M15-2: Following the synthesis method of intermediate M1-3, replace compound M1-1 with compound M15-1.

[0260] 2) Synthesis of intermediate M15-3: Following the synthesis method of intermediate M1-4, intermediate M15-2 was used to replace intermediate M1-3. The combined yield of steps 1) and 2) was 65%.

[0261] 3) Synthesis of organic compound M15: Following the synthesis method of organic compound M1, intermediate M15-3 and compound M12-5 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 73%. MS(ASAP) = 654.

[0262] Example 16

[0263] The synthetic route of organic compound M16 in this embodiment is as follows:

[0264]

[0265] 1) Synthesis of intermediate M16-3: Following the synthesis method of intermediate M3-3, compounds M16-2 and M16-1 were substituted for compounds M3-1 and M3-2, respectively, with a yield of 65%.

[0266] 2) Synthesis of intermediate M16-4: Following the synthesis method of intermediate M1-3, intermediate M16-3 was used to replace compound M1-1.

[0267] 3) Synthesis of intermediate M16-5: Following the synthesis method of intermediate M1-4, intermediate M16-4 was used to replace intermediate M1-3. The combined yield of steps 2) and 3) was 62%.

[0268] 4) Synthesis of organic compound M16: Following the synthesis method of organic compound M1, intermediate M16-5 and compound M16-6 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 72%. MS(ASAP) = 684.

[0269] Example 17

[0270] The synthetic route of organic compound M17 in this embodiment is as follows:

[0271]

[0272] 1) Synthesis of intermediate M17-2: Following the synthesis method of intermediate M1-3, compounds M17-1 and M4-1 were used to replace compounds M1-1 and M1-2, respectively.

[0273] 2) Synthesis of intermediate M17-3: Following the synthesis method of intermediate M1-4, intermediate M17-2 was used to replace intermediate M1-3. The combined yield of steps 1) and 2) was 63%.

[0274] 3) Synthesis of organic compound M17: Following the synthesis method of organic compound M1, intermediates M17-3 and M17-4 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 75%. MS (ASAP) = 618.

[0275] Example 18

[0276] The synthetic route of organic compound M18 in this embodiment is as follows:

[0277]

[0278] Synthesis of organic compound M18: Following the synthetic method of organic compound M1, compound M8-4 was substituted for compound M1-5, yield 76%. MS (ASAP) = 654.

[0279] Example 19

[0280] The synthetic route of organic compound M19 in this embodiment is as follows:

[0281]

[0282] Synthesis of organic compound M19: Following the synthetic method of organic compound M1, compounds M8-3 and M4-4 were used to replace intermediates M1-4 and M1-5, respectively, with a yield of 74%. MS (ASAP) = 702.

[0283] Example 20

[0284] The synthetic route of organic compound M20 in this embodiment is as follows:

[0285]

[0286] 1) Synthesis of intermediate M20-2: Following the synthesis method of intermediate M3-3, compounds M16-2 and M20-1 were used to replace compounds M3-1 and M3-2, respectively, with a yield of 67%.

[0287] 2) Synthesis of intermediate M20-3: Following the synthesis method of intermediate M1-3, intermediate M20-2 was used to replace compound M1-1.

[0288] 3) Synthesis of intermediate M20-4: Following the synthesis method of intermediate M1-4, intermediate M20-3 was used to replace intermediate M1-3. The combined yield of steps 2) and 3) was 64%.

[0289] 4) Synthesis of organic compound M20: Following the synthesis method of organic compound M1, intermediate M20-4 and compound M17-4 were used to replace intermediate M1-4 and compound M1-5, respectively, with a yield of 73%. MS (ASAP) = 680.

[0290] Example 21

[0291] The synthetic route of organic compound M21 in this embodiment is as follows:

[0292]

[0293] 1) Synthesis of intermediate M21-2: Following the synthesis method of intermediate M3-3, compounds M16-2 and M21-1 were used to replace compounds M3-1 and M3-2, respectively, with a yield of 65%.

[0294] 2) Synthesis of intermediate M21-3: Following the synthesis method of intermediate M1-3, intermediate M21-2 was used to replace compound M1-1.

[0295] 3) Synthesis of intermediate M21-4: Following the synthesis method of intermediate M1-4, intermediate M21-3 was used to replace intermediate M1-3. The combined yield of steps 2) and 3) was 62%.

[0296] 4) Synthesis of organic compound M21: Following the synthesis method of organic compound M1, intermediate M21-4 and compound M1-5 were substituted for intermediate M1-4 and compound M1-5, respectively, with a yield of 71%. MS (ASAP) = 840.

[0297] Comparative Example 1

[0298] The organic compound in this comparative example is Ref.-1, and its chemical structural formula is as follows:

[0299]

[0300] Comparative Example 2

[0301] The organic compound in this comparative example is Ref.-2, and its chemical structural formula is as follows:

[0302]

[0303] Fabrication of OLED devices

[0304] In the OLED device of this embodiment, HATCN is used as the hole injection layer material, HT is used as the hole transport material, the organic compound in Examples 1-20 and Comparative Examples 1-2 is used as the electron blocking layer material, RH is used as the main material of the light-emitting material, RD is used as the red light-emitting material, ET and Liq are used as the electron transport materials, and Liq is used as the electron injection material. The device structure is ITO / HATCN / HT / organic compound / RH:GD / ET:Liq / Liq / Al.

[0305] A schematic diagram of an OLED device is shown below. Figure 1 As shown in the figure. In this figure, 10 is the substrate, 20 is the anode, 30 is the hole injection layer (HIL), 40 is the hole transport layer (HTL), 50 is the electron blocking layer, 60 is the light-emitting layer, 70 is the electron transport layer (ETL), 80 is the electron injection layer (EIL), and 90 is the cathode.

[0306] The chemical structural formulas of HATCN, HT, RD, RH, ET, and Liq are as follows:

[0307]

[0308] The above-mentioned materials HATCN, HT, RD, RH, ET, and Liq are all commercially available, or their synthesis methods are existing technologies.

[0309] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0310] Device Example 1

[0311] The method for fabricating an OLED device in this embodiment includes the following steps:

[0312] 1) Cleaning of ITO (Indium Tin Oxide) Anode Layer: Clean the ITO conductive glass anode layer, then ultrasonically clean it with deionized water, acetone, and isopropanol for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode power function.

[0313] 2) Formation of the hole injection layer: On the ITO anode layer, the hole injection layer material HATCN is deposited by vacuum evaporation, with a thickness of 30 nm, and the evaporation rate is...

[0314] 3) Formation of hole transport layer: Hole transport material HT is deposited on the hole injection layer by vacuum evaporation, with a thickness of 60nm.

[0315] 4) Forming an electron blocking layer: An electron blocking material is deposited on the hole transport layer to form an electron blocking layer, wherein the electron blocking material is the organic compound M1 obtained in Example 1, and the thickness is 10 nm.

[0316] 5) Forming the light-emitting layer: The light-emitting layer is deposited on the electron blocking layer, with RH as the host material and RD as the dopant material. The mass ratio of RD to RH is 3:100, and the thickness is 40nm.

[0317] 6) Forming an electron transport layer: Electron transport materials ET and Liq are deposited on the light-emitting layer by vacuum evaporation in a mass ratio of 5:5 and a thickness of 30nm.

[0318] 7) Formation of electron injection layer: An electron injection layer Liq with a thickness of 1 nm is vacuum-deposited on top of the electron transport layer.

[0319] 8) Forming a cathode layer: A cathode Al layer with a thickness of 100 nm is vacuum-deposited on top of the electron injection layer.

[0320] Device Examples 2-21: These are basically the same as Device Example 1, except that the electron blocking layer materials of Device Examples 2-21 are selected from organic compounds M2 to M21 of Examples 2-21, as shown in Table 1.

[0321] Comparative Examples 1-2: These are basically the same as those in Example 1, except that the electron blocking layer materials in Comparative Examples 1-2 are Ref.-1 and Ref.-2, respectively.

[0322] Performance testing and results

[0323] The current-voltage (JV) characteristics of the OLED devices in Examples 1-21 and Comparative Examples 1-2 were tested using characterization equipment, and important parameters such as luminous efficiency and lifetime were recorded. Luminous efficiency was defined as a current density of 10 mA / cm². 2 The device lifetime, LT90@1000nit, is the time it takes for the brightness to drop to 90% of the initial brightness@10000nit under constant current. The luminous efficiency and lifetime of the OLED devices in Device Examples 1-21 are relative values ​​to the OLED device in Device Comparative Example 1. The test results are shown in Table 1 below.

[0324] Table 1:

[0325]

[0326]

[0327] As shown in Table 1, compared with the OLED devices made using the organic compounds of Comparative Examples 1-2, the OLED devices made using the organic compounds of Examples 1-21 of this application as electron transport layer materials have higher efficiency and longer lifespan.

[0328] The organic compounds in this application have the combined effect of steric hindrance groups and fused-ring fluorene groups, which can effectively regulate the hole transport performance of the organic compounds. Therefore, when the organic compounds in this application are used as electron blocking layer materials in organic electronic devices, the luminous efficiency and lifetime of organic electronic devices can be improved more effectively.

[0329] The organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound, characterized in that, It has a structure as shown in general formula (1): （1） in, Ar1 is selected from the following groups: ； R5 and R6 are selected from methyl groups; Ar2 and Ar3 are selected from the following groups: ； R3 is selected from -H, methyl, adamantyl, phenyl, or phenanthrene; R1 is selected from methyl, cyclopentyl, phenyl, naphthyl, triphenylene, or... ; R2 is selected from methyl, cyclopentyl, adamantyl, -F, -CN, phenyl, or... ; In this context, * indicates a fusion site or a connection site.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from any structure of formula (2-1)-(2-6): ； Where m is selected from 0, 1, 2, 3, 4, 5 or 6; n is selected from 0, 1, 2, 3 or 4; Y is selected from CR5R6 or O.

3. The organic compound according to claim 1, characterized in that, Ar2, Ar3, and N connected to both Ar2 and Ar3 form The structure is as follows: ； In this context, * indicates a connection site.

4. The organic compound according to claim 1, characterized in that, The organic compound is selected from the following structures: 。 5. A mixture, characterized in that: The mixture comprises the organic compound as described in any one of claims 1-4 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, or organic dyes.

6. A composition, characterized in that: The composition comprises an organic compound as described in any one of claims 1-4 or a mixture as described in claim 5, and at least one organic solvent.

7. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer is an electron blocking layer, and the functional layer includes the organic compound according to any one of claims 1-4, or the mixture according to claim 5, or the functional layer is prepared from the composition according to claim 6.

Images