Organic compounds and mixtures, compositions and organic electronic devices thereof

Abstract

This invention discloses an organic compound having the following structure: Furthermore, this invention also discloses a mixture, a composition, and an organic electronic device. Due to the presence of sp3 hybrid carbon in the organic compound of this invention, the influence between the two aromatic amine groups is small, resulting in a higher triplet energy level of the molecule. In addition, the two aromatic amine structures improve the carrier transport capability of this organic compound. Furthermore, as an electron blocking material, the organic compound can achieve carrier balance with the electron transport layer, effectively improving the luminous efficiency and lifetime of organic electroluminescent devices.

Description

Technical Field

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

[0002] Organic light-emitting diode (OLED) displays are a type of self-emissive display device. They generate excitons through the transfer and recombination of charge carriers between functional layers driven by an electric current, emitting light via highly quantum-efficient organic compounds or metal complexes. The structure of an OLED typically includes a positive electrode, a negative electrode, and an organic functional layer between them. To improve the efficiency and lifetime of OLEDs, the organic functional layer has a multi-layered structure, with each layer containing different organic materials. Specifically, it may include a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In such OLEDs, applying a voltage between the two electrodes injects holes into the organic functional layer from the positive electrode and electrons from the negative electrode. When the injected holes and electrons meet, they form excitons, which emit light when they transition back to the ground state. OLEDs possess characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0003] Currently, the luminous efficiency of organic light-emitting diodes (OLEDs) has been greatly improved, but their internal quantum efficiency is approaching the theoretical limit. The difference in mobility between holes and electrons prevents charge carriers from recombining completely uniformly within the emitting layer, thus reducing the device's luminous efficiency. Therefore, improving the material and device structures can reduce the difference in hole and electron mobility, preventing the shift of recombination regions and thereby improving the device's luminous efficiency and lifetime. Based on this, providing novel organic functional materials to enhance device performance is a pressing issue in this field. Summary of the Invention

[0004] In view of this, the present invention provides an organic compound, which aims to provide new organic functional materials to improve the performance of devices.

[0005] This invention is achieved through the following technical solution:

[0006] An organic compound having a structure as shown in general formula (1):

[0007]

[0008] in:

[0009] R1 is selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 10 to 20 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 10 to 20 cyclic atoms.

[0010] R2 is selected from hydrogen atom, deuterium atom, straight-chain alkyl group having 1 to 20 carbon atoms, straight-chain alkoxy group having 1 to 20 carbon atoms, straight-chain thioalkoxy group having 1 to 20 carbon atoms, branched alkyl or cyclic alkyl group having 3 to 20 carbon atoms, silyl group, substituted or unsubstituted amino group, -CF3, -Cl, -Br, -F, -CN, or substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms;

[0011] L1 to L4 are independently selected from aromatic groups with 6-20 single bonds, substituted or unsubstituted ring atoms, or heteroaromatic groups with 5-20 substituted or unsubstituted ring atoms.

[0012] Ar1 to Ar5 are independently selected from aromatic groups with 6-20 substituted or unsubstituted ring atoms, or heteroaromatic groups with 5-20 substituted or unsubstituted ring atoms.

[0013] Accordingly, the present invention also provides a mixture comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.

[0014] Accordingly, the present invention also provides a composition comprising the above-mentioned organic compound or mixture thereof, and at least one organic solvent.

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

[0016] Accordingly, the present invention also provides an organic electronic device comprising an anode, a cathode, a light-emitting layer located between the cathode and the anode, a hole transport layer located between the anode and the light-emitting layer, and an electron blocking layer located between the light-emitting layer and the hole transport layer; wherein the electron blocking layer comprises the above-mentioned organic compound, or a mixture thereof, or the electron blocking layer is prepared from the above-mentioned composition.

[0017] Compared with the prior art, the organic compounds of the present invention have the following beneficial effects:

[0018] The presence of sp3 hybrid carbon in the organic compound of this invention minimizes the influence between the two aromatic amine groups, resulting in a higher triplet energy level. Furthermore, the two aromatic amine structures enhance the carrier transport capability of this organic compound. Moreover, as an electron-blocking material, the organic compound achieves carrier balance with the electron transport layer, effectively improving the luminous efficiency and lifetime of organic electroluminescent devices. Attached Figure Description

[0019] To more clearly illustrate the technical solutions in the embodiments of the present invention, 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 the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0020] Figure 1 This is a schematic diagram of the OLED device shown in Embodiment 1 of the present invention;

[0021] In this design, 101 is the substrate, 102 is the anode, 103 is the hole injection layer, 104 is the hole transport layer, 105 is the electron blocking layer, 106 is the light-emitting layer, 107 is the electron transport layer, 108 is the electron injection layer, and 109 is the cathode.

[0022] Figure 2 This is the mass spectrum of compound R1 in Example 1 of the device of the present invention. Detailed Implementation

[0023] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. Furthermore, it should be understood that the specific embodiments described herein are only for illustration and explanation of the present invention and are not intended to limit the present invention.

[0024] In the description of this invention, the term "comprising" means "including but not limited to," and the term "a plurality of" means "two or more." Various embodiments of the invention may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the invention; therefore, it should be considered that the range description specifically discloses all possible subranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 specifically discloses subranges 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., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Furthermore, whenever a numerical range is referred to herein, it means including any referenced number (fraction or integer) within the range referred to.

[0025] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0026] The terms "and / or," "or / and," and "and / or" used in this invention encompass 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 using at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this invention, the technical solution undoubtedly includes solutions connected using "logical AND," and also undoubtedly includes solutions connected using "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").

[0027] In this invention, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0028] In this invention, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0029] In this invention, "heteroatoms" are non-carbon atoms, and can be N atoms, O atoms, S atoms, etc.

[0030] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0031] In this invention, 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.

[0032] In this invention, "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 not limited to: deuterium, 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", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, 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 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, 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.

[0033] In this invention, "ring atom number" refers to the number of ring atoms constituting the ring itself in a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound), i.e., the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atom. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0034] In this invention, "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. For polycyclic rings, at least one 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, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, with optional further substitution 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.

[0035] In this invention, "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, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0036] In this invention, "alkyl" can refer to a straight-chain, branched, and / or cyclic alkyl group. 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 ...

[0037] In this invention, 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.

[0038] In this invention, "amine group" refers to a derivative of an amine having the structural feature of formula -N(X)2, wherein each "X" is independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amine 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.

[0039] In this invention, 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.

[0040] In this invention, "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).

[0041] In this invention, "*" represents a linking site or a fusion site. When no linking site is specified in the group, any configurable site in the group is selected as the linking site. When no fusion site is specified in the group, any configurable site in the group is selected as the fusion site, preferably two or more adjacent sites in the group.

[0042] In this invention, 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.

[0043] In this invention, 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 can be attached to any substituted site on the benzene ring. For example... express Can be with The above can be selected at any replaceable position to form a loop.

[0044] In this invention, "adjacent groups" refers to two substituents that have no substituted sites between them.

[0045] The terms "combinations thereof", "arbitrary combinations thereof", and "arbitrary combinations thereof" used in this invention include all suitable combinations of any two or more of the listed items.

[0046] In this invention, terms such as "further," "even more," and "particularly" are used for descriptive purposes and to indicate differences in content, but should not be construed as limiting the scope of protection of this invention.

[0047] In this invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without." If multiple "options" appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "option" is independent.

[0048] In this invention, the technical features described in an open-ended manner include both closed-ended technical solutions composed of the listed features and open-ended technical solutions that include the listed features.

[0049] This invention provides an organic compound having the structure of general formula (1):

[0050]

[0051] in:

[0052] R1 is selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 10 to 20 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 10 to 20 cyclic atoms.

[0053] R2 is selected from hydrogen atom, deuterium atom, straight-chain alkyl group having 1 to 20 carbon atoms, straight-chain alkoxy group having 1 to 20 carbon atoms, straight-chain thioalkoxy group having 1 to 20 carbon atoms, branched alkyl or cyclic alkyl group having 3 to 20 carbon atoms, silyl group, substituted or unsubstituted amino group, -CF3, -Cl, -Br, -F, -CN, or substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms;

[0054] L1 to L4 are independently selected from aromatic groups with 6-20 single bonds, substituted or unsubstituted ring atoms, or heteroaromatic groups with 5-20 substituted or unsubstituted ring atoms.

[0055] Ar1 to Ar5 are independently selected from aromatic groups with 6-20 substituted or unsubstituted ring atoms, or heteroaromatic groups with 5-20 substituted or unsubstituted ring atoms.

[0056] In one embodiment, Ar5 is selected from aromatic groups with 6-10 substituted or unsubstituted ring atoms, or heteroaromatic groups with 5-10 substituted or unsubstituted ring atoms.

[0057] In one specific embodiment, Ar5 is selected from the following groups:

[0058]

[0059] in:

[0060] * indicates a connection point.

[0061] Each time X appears, it is independently selected from CR3 or N;

[0062] Each time R3 appears, it is independently selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 20 carbon atoms, a straight-chain alkoxy group having 1 to 20 carbon atoms, a straight-chain thioalkoxy group having 1 to 20 carbon atoms, a branched alkyl or cyclic alkyl group having 3 to 20 carbon atoms, a silyl group, a substituted or unsubstituted amino group, -CF3, -Cl, -Br, -F, -CN, 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, or a combination of these groups.

[0063] Furthermore, each time R3 appears, it is independently selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 10 carbon atoms, straight-chain alkoxy groups having 1 to 10 carbon atoms, straight-chain thioalkoxy groups having 1 to 10 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 10 carbon atoms, silyl groups, substituted or unsubstituted amino groups, -CF3, -Cl, -Br, -F, -CN, or substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 10 ring atoms, or combinations of these groups.

[0064] In one specific embodiment, each time R3 appears, it is independently selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 5 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 6 carbon atoms, phenyl, biphenyl, pyridyl, pyrimidinyl, triazine, naphthyl, quinolinyl, or isoquinolinyl, or combinations of these groups.

[0065] In one specific embodiment, R3 is independently selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 5 carbon atoms, branched alkyl groups or cyclic alkyl groups having 3 to 6 carbon atoms, phenyl, biphenyl or naphthyl.

[0066] In one embodiment, Ar5 is selected from phenyl, biphenyl, naphthyl, or phenyl substituted with an alkyl group having 1 to 4 carbon atoms, or biphenyl substituted with an alkyl group having 1 to 4 carbon atoms, or naphthyl substituted with an alkyl group having 1 to 4 carbon atoms.

[0067] In one embodiment, the organic compound is selected from the structure shown in formula (2-1) or (2-2):

[0068]

[0069] R3 has the same meaning as described above.

[0070] In one specific embodiment, the organic compound is selected from any of the structures shown in formulas (3-1) to (3-6):

[0071]

[0072] In one specific embodiment, R3 is selected from hydrogen or phenyl.

[0073] In one embodiment, R2 in the above-mentioned organic compound is selected from hydrogen atoms, deuterium atoms, or straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 10 carbon atoms, or silyl groups, -CF3, -Cl, -Br, -F, or substituted or unsubstituted aromatic groups having 6 to 10 ring atoms or aromatic heteroaromatic groups having 6 to 10 ring atoms, or combinations of these groups.

[0074] Furthermore, in one embodiment, R2 may be selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl substituted with an alkyl group having 1-10 carbon atoms, or biphenyl substituted with an alkyl group having 1-10 carbon atoms, or a combination of these groups.

[0075] In one specific embodiment, R2 is selected from hydrogen, methyl, phenyl, or a combination of these groups.

[0076] In the aforementioned organic compounds, R1 may further be selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 10 cyclic atoms, or substituted or unsubstituted heteroaromatic groups having 10 cyclic atoms.

[0077] In one embodiment, R1 is selected from methyl, ethyl, isopropyl, naphthyl, or naphthyl substituted with an alkyl group having 1-6 C atoms.

[0078] In one specific embodiment, R1 is selected from methyl, naphthyl, or naphthyl substituted with alkyl groups having 1-6 carbon atoms.

[0079] In the above-mentioned organic compounds, L1 to L4 can be independently selected from single bonds, substituted or unsubstituted aromatic groups with 6-13 ring atoms, or substituted or unsubstituted heteroaromatic groups with 6-13 ring atoms.

[0080] Furthermore, L1 to L4 are independently selected from single bonds or from the following groups:

[0081]

[0082] Where: * indicates a connection site.

[0083] In one specific embodiment, L1 to L4 are independently selected from single bonds or phenyl groups.

[0084] In the above-mentioned organic compounds, Ar1 to Ar4 can be independently selected from substituted or unsubstituted aromatic groups having 6-14 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5-14 ring atoms.

[0085] Furthermore, Ar1 to Ar4 can be selected from the following groups:

[0086]

[0087] in:

[0088] Each time Z appears, it is independently selected from CR4 or N;

[0089] Each time W appears, it is independently selected from O, S, CR5R6, and NR7.

[0090] Each time R4, R5, R6, and R7 appear, they are independently selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 20 carbon atoms, straight-chain alkoxy groups having 1 to 20 carbon atoms, straight-chain thioalkoxy groups having 1 to 20 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 20 carbon atoms, silyl groups, substituted or unsubstituted amino groups, -CF3, -Cl, -Br, -F, -CN, substituted or unsubstituted aromatic groups having 6 to 10 ring atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 10 ring atoms.

[0091] When Z is a connection site, Z is selected from CR4; when W is a connection site, W is selected from N.

[0092] Furthermore, Ar1 to Ar4 can be selected from the following groups:

[0093]

[0094] In a particular embodiment, each of the following groups, R4, R5, R6, and R7, is independently selected from hydrogen atoms, deuterium atoms, straight-chain alkyl groups having 1 to 10 carbon atoms, branched alkyl or cyclic alkyl groups having 3 to 10 carbon atoms, or phenyl, or biphenyl, or naphthyl, or pyridyl, or pyrimidinyl, or combinations of these groups.

[0095] Specifically, R4 is selected from hydrogen atom, deuterium atom, methyl, ethyl, tert-butyl, isopropyl, phenyl, or a combination of these groups.

[0096] Specifically, R5 and R6 are selected from methyl, phenyl, biphenyl, naphthyl, or combinations thereof.

[0097] Specifically, R7 is selected from methyl, phenyl, biphenyl, naphthyl, or a combination of these groups.

[0098] The organic compounds according to the present invention may be selected from, but are not limited to, the following structures, and the following structures may be arbitrarily substituted:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The presence of sp3 hybrid carbon in the organic compound of this invention minimizes the influence between the two aromatic amine groups, resulting in a higher triplet energy level. Furthermore, the two aromatic amine structures enhance the carrier transport capability of this organic compound. Moreover, as an electron-blocking material, the organic compound achieves carrier balance with the electron transport layer, effectively improving the luminous efficiency and lifetime of organic electroluminescent devices.

[0106] In one embodiment, the organic compound of the present invention can be used in an electron blocking layer. Furthermore, the organic compound of the present invention can be used in an electron blocking layer of an organic electronic device.

[0107] This invention relates to an electron blocking layer material comprising the organic compounds described above.

[0108] This invention relates to a mixture comprising at least one of the aforementioned organic compounds and at least one other organic functional material; said at least one other organic functional material may be selected from hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), luminescent guest material, luminescent host material, and organic dye. Various organic functional materials are described in detail, for example, in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0109] In one embodiment, the other organic functional material is selected from electron transport materials.

[0110] This invention also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent. The at least one organic solvent may be selected from aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, borate esters or phosphate esters. That is, the solvent contained in the composition of this invention may be any one of the above-mentioned organic solvents, or a mixture of two or more of them. In a preferred embodiment, the at least one organic solvent contained in the composition of this invention is selected from aromatic or heteroaromatic solvents.

[0111] Specifically, solvents based on aromatic or heteroaromatic compounds include, but are not limited to: p-diisopropylbenzene, pentaphenyl, 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- Isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanate, ethyl 2-furanate, etc.

[0112] Ester-based solvents include, but are not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc., are particularly preferred.

[0113] Solvents based on aromatic ketones include, but are not limited to: 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, or benzophenone and their derivatives; such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.

[0114] Solvents based on aromatic ethers include, but are not limited to: 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, ethyl-2-naphthyl ether, etc.

[0115] Solvents based on aliphatic ketones include, but are 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, tetraethylene glycol dimethyl ether, etc.

[0116] It is understood that the solvent may be used alone or as a mixture of two or more organic solvents.

[0117] In some embodiments, the compositions of the present invention comprise at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0118] Another organic solvent includes, but is not limited to, at least one of: 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, tetrahydronaphthalene, naphthane, and indene.

[0119] In some preferred embodiments, the organic solvent suitable for the present invention is a solvent with a Hansen solubility parameter within the following range:

[0120] 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;

[0121] 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;

[0122] 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.

[0123] In some embodiments, the organic solvent is selected in accordance with the composition of the invention, taking boiling point into consideration. In at least some embodiments, the organic solvent has a boiling point ≥150°C; preferably ≥180°C; more 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 printhead.

[0124] It is understood that the organic solvent can be evaporated from the composition system to form a thin film containing the organic compound of the present invention.

[0125] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.

[0126] In the composition, the content of the organic compound or mixture can be 0.01-10 wt%, preferably 0.1-5 wt%, more preferably 0.2-5 wt%, and even more preferably 0.25-3 wt%.

[0127] This invention 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 be, but is not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, gravure 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, nozzle printing, and inkjet printing are preferred.

[0128] The solution or suspension may further include additives for adjusting viscosity, film-forming properties, and improving adhesion. These additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives. Different printing or coating methods may have different requirements for coatings or printing inks; therefore, the concentration, viscosity, etc., of the solution or suspension can be adjusted accordingly to suit different printing or coating methods.

[0129] The present invention also provides the application of the organic compound, mixture, or composition as described above in organic electronic devices. The technical solution is as follows:

[0130] An organic electronic device comprising, or prepared from, the organic compound or mixture described above.

[0131] Furthermore, an organic electronic device includes a first electrode, a second electrode, and at least one organic functional layer located between the first and second electrodes. The at least one organic functional layer comprises an organic compound, mixture, or composition as described above. The first and second electrodes are a pair of electrodes; for example, if the first electrode is an anode, then the second electrode is a cathode, and vice versa.

[0132] The organic electronic devices can be, but are not limited to, organic light-emitting diodes (OLED devices), organic photovoltaic cells (OPV), organic light-emitting cells (OLEEC), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Preferably, the organic electronic devices are organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors.

[0133] The organic functional layer is selected from hole injection layer (HIL), hole transport layer (HTL), light emission layer (EML), electron blocking layer (EBL), electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0134] In some embodiments, one or more organic functional layers of the organic electronic device include at least an electron blocking layer. The electron blocking layer is made of an organic compound, mixture, or composition as described above. Further, the one or more organic functional layers may also include a light-emitting layer.

[0135] The present invention relates to an organic electronic device comprising: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, wherein the organic functional layer comprises at least an electron blocking layer, and the material of the electron blocking layer comprises the organic compound described above.

[0136] Furthermore, the organic functional layer also includes a light-emitting layer located between the electron blocking layer and the cathode. The material of the light-emitting layer can be a light-emitting layer material known in the art. The organic functional layer may also include a hole transport layer located between the anode and the electron blocking layer.

[0137] In one specific embodiment, the organic electronic device includes a cathode, an electron transport region, a light-emitting layer, a hole transport region, and an anode, which are sequentially stacked. The hole transport region includes an electron blocking layer and a hole transport layer, with the hole transport layer located between the anode and the light-emitting layer, and the electron blocking layer located between the hole transport layer and the light-emitting layer. The electron blocking layer is made of the organic compound, mixture, or composition described above.

[0138] In one embodiment, the material of the light-emitting layer comprises a structure as shown in general formula (4):

[0139]

[0140] in:

[0141] q is selected from 1 or 2;

[0142] Each time Ar6 appears, it is independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms;

[0143] Each time Ar7 appears, it is 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;

[0144] When R8 and R9 appear, they are each independently selected from H, D, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, or combinations of these groups.

[0145] In one embodiment, each occurrence of Ar6 is independently selected from quinoline or isoquinoline and their derivatives. Preferably, each occurrence of Ar6 is independently selected from quinoline or isoquinoline, or quinoline substituted with an alkyl group having 1-8 carbon atoms, or isoquinoline substituted with an alkyl group having 1-8 carbon atoms.

[0146] In one embodiment, Ar7 is selected independently from phenyl and its derivatives each time it appears. Preferably, Ar7 is selected independently from phenyl or phenyl substituted with an alkyl group having 1-8 carbon atoms each time it appears.

[0147] In one embodiment, each time R8 and R9 appear, they are independently selected from H, D, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, respectively.

[0148] Preferably, general formula (4) is selected from any structure of general formulas (5-1) to (5-3):

[0149]

[0150] in:

[0151] a is selected from any integer from 0 to 6, and b is selected from any integer from 0 to 4;

[0152] R 10 R 11 Each time it appears, it 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 6 to 60 cyclic atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 cyclic atoms, or a combination of these groups.

[0153] In one embodiment, at least one R 10 Or R 11 It is selected from straight-chain alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms.

[0154] In one embodiment, at least one R 10 Selected from straight-chain alkyl groups having 1 to 8 carbon atoms or branched or cyclic alkyl groups having 3 to 8 carbon atoms. Further, at least one R 11 It is selected from straight-chain alkyl groups having 1 to 8 carbon atoms or branched or cyclic alkyl groups having 3 to 8 carbon atoms.

[0155] Metal complexes as described in general formula (4) are selected from, but not limited to, the following structures, which can be arbitrarily replaced:

[0156]

[0157]

[0158] It is understood that, in addition to the electron blocking layer and hole transport layer mentioned above, organic functional layers can also include other functional layers to improve the performance of organic electronic devices, such as electron transport layers, electron injection layers, hole blocking layers, hole injection layers, hole blocking layers, and light extraction layers. Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0159] In some embodiments, the organic electronic device further includes a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. It is understood that when the substrate is transparent, the organic electronic device is a transparent light-emitting device. The substrate may also be rigid or flexible; for example, the substrate material may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is particularly desirable. In a preferred embodiment, the substrate is a flexible substrate. The flexible substrate material may be a polymer film or plastic. The glass transition temperature (Tg) of the flexible substrate is above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. As an example, the flexible substrate material may be polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0160] The anode material can be any anode material known in the art for use in organic electronic devices, such as conductive metals, conductive metal oxides, or conductive polymers. In some embodiments, the absolute value of the difference between the work function of the anode material and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as a hole injection layer, hole transport layer, or electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. As an example, the anode material can be selected from, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, and aluminum-doped zinc oxide (AZO). 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 devices according to the present invention.

[0161] The cathode material can be any cathode material known in the art for use in organic electronic devices, such as a conductive metal or conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the cathode material and the LUMO level or conduction band level of the luminescent material or the n-type semiconductor material serving as an electron injection layer, electron transport layer, or hole blocking layer 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. In principle, all materials that can be used as cathodes for OLEDs can be used as cathode materials for the devices of the present invention. As an example, the cathode material can be selected from, but is not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0162] The material of the hole transport layer can be any material known in the art for hole transport layers, for example, selected from, but not limited to, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spiro-omeTXD, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TXPC), N,N′-bis(1-naphthyl)-N,N′-diphenyl-1,1′-diphenyl-4 At least one of the following: 4′-diamine (NPB), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), polytriphenylamine (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTX).

[0163] The material of the electron transport layer can be any material known in the art for use in electron transport layers, for example, it can be selected from, but is not limited to, at least one of ET and Liq, PBD (2-(4-biphenyl)-5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Alq3) and graphene.

[0164] The chemical structural formulas of ET and Liq are as follows:

[0165]

[0166] The material of the hole injection layer can be any material known in the art for hole injection layers, for example, it can be selected from, but not limited to, at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HXT-CN), F4TCNQ, F6TCNNQ, and NDP-9.

[0167] In at least one preferred embodiment, the organic electronic device is an OLED device. More preferably, the organic electronic device is a solution-type OLED.

[0168] This invention also relates to electronic devices incorporating the aforementioned organic electronic devices. This invention relates to the application of electroluminescent devices in various electronic devices. These electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0169] The present invention will be specifically described below through specific embodiments. These embodiments are only some embodiments of the present invention and are not intended to limit the present invention.

[0170] Example 1

[0171] The synthetic route of compound R1 in this embodiment is as follows:

[0172]

[0173] Compound Z1 (7.72 g, 20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 12.5 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of p-chloroacetophenone (20 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, deionized water was added, and the mixture was extracted with ethyl acetate. The organic phase was concentrated and separated by silica gel column chromatography to give a total of 5.42 g of compound Z2, with a yield of 61%.

[0174] Compound Z2 (4.44 g, 10 mmol) and diphenylamine (3.72 g, 22 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (2.3 g, 24 mmol) and tris(dibenzylacetone)palladium (0.46 g, 0.5 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.5 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 4.46 g of compound R1, yield 67%; MS: 667 [M]. + See the mass spectrum of compound R1. Figure 2 .

[0175] Example 2

[0176] The synthetic route of compound R14 in this embodiment is as follows:

[0177]

[0178] Compounds Z2 (4.44 g, 10 mmol) and Z3 (2.85 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 4.61 g of compound Z4, with a yield of 71%.

[0179] Compound Z4 (3.25 g, 5 mmol) and diphenylamine (0.85 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and tris(2,2-benzylacetone) dipalladium (0.14 g, 0.15 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.15 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 3.21 g of compound R14, yield 82%; MS: 782 [M]. + ].

[0180] Example 3

[0181] The synthetic route of compound R18 in this embodiment is as follows:

[0182]

[0183] Compound Z2 (4.44 g, 10 mmol) and diphenylamine (1.69 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 4 g of product Z5, with a yield of 75%.

[0184] Compounds Z5 (3.2 g, 6 mmol) and Z6 (1.65 g, 6 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.69 g, 7.2 mmol) and tris(dibenzylacetone)palladium (0.16 g, 0.18 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.18 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 3.24 g of product R18 (70% yield). MS: 772 [M] + ].

[0185] Example 4

[0186] The synthetic route of compound R25 in this embodiment is as follows:

[0187]

[0188] Compound Z7 (13.08 g, 30 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 18.7 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of p-chloroacetophenone (30 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, deionized water was added, and the solution was extracted with ethyl acetate. After concentration, the solution was separated by silica gel column chromatography to give 8.6 g of compound Z8, in 58% yield.

[0189] Compounds Z8 (7.41 g, 15 mmol) and Z9 (3.67 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and tris(dibenzylacetone)dipalladium (0.41 g, 0.45 mmol) were added, and the mixture was purged with nitrogen three times. Then, tri-tert-butylphosphine (0.45 mmol) was added, and the mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 6.82 g of compound Z10, with a yield of 69%.

[0190] Compound Z10 (6.59 g, 10 mmol) and diphenylamine (1.69 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone) dipalladium (0.27 g, 0.3 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.3 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 6.1 g of compound R25, yield 77%; MS: 792 [M]. + ].

[0191] Example 5

[0192] The synthetic route of compound R83 in this embodiment is as follows:

[0193]

[0194] Z1 (3.86 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of o-bromoacetophenone (10 mmol L) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. Then, the temperature was raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography to give 3.03 g of compound Z11, with a yield of 62%.

[0195] Compounds Z11 (2.44 g, 5 mmol) and Z12 (2.63 g, 11 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.25 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.11 g of compound R83, yield 55%; MS: 766 [M]. + ].

[0196] Example 6

[0197] The synthetic route of compound R120 in this embodiment is as follows:

[0198]

[0199] Compound Z1 (3.86 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of Z13 (10 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to obtain 2.61 g of compound Z14, with a yield of 52%.

[0200] Compounds Z14 (2.51 g, 5 mmol) and Z12 (1.1 g, 11 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.25 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 3.35 g of compound R120, yield 86%; MS: 780 [M]. + ].

[0201] Example 7

[0202] The synthesis route of R150 in this embodiment is as follows:

[0203]

[0204] Compound Z15 (4.24 g, 20 mmol) and diphenylamine (3.55 g, 21 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (2.3 g, 24 mmol) and tris(dibenzylacetone)dipalladium (0.55 g, 0.6 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.6 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 4.45 g of product Z16, with a yield of 74%.

[0205] Compound Z1 (5.4 g, 14 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 8.7 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of compound Z16 (14 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to obtain 4.38 g of compound Z17, with a yield of 53%.

[0206] Compounds Z17 (2.96 g, 5 mmol) and Z9 (1.22 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and tris(dibenzylacetone)palladium (0.14 g, 0.15 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.15 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.72 g of compound R150, yield 72%. MS: 756 [M] + ].

[0207] Example 8

[0208] The synthetic route of compound R168 in this embodiment is as follows:

[0209]

[0210] Compound Z18 (4.36 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of compound Z16 (10 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to obtain 3.97 g of compound Z19, with a yield of 62%.

[0211] Compounds Z19 (3.2 g, 5 mmol) and Z9 (1.22 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and tris(dibenzylacetone)palladium (0.14 g, 0.15 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.15 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The extract was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.82 g of compound R168 (70% yield). MS: 806 [M] + ].

[0212] Example 9

[0213] The synthetic route for compound R170 in this embodiment is as follows:

[0214]

[0215] Compound Z1 (3.86 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of Z20 (10 mmol / L) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography to remove the solvent, yielding 3.78 g of compound Z21, in 63% yield.

[0216] Compound Z21 (3 g, 5 mmol) and diphenylamine (1.86 g, 11 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol) were added, and the mixture was purged with nitrogen three times. Then, tri-tert-butylphosphine (0.25 mmol) was added, and the mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.57 g of compound R170, yield 66%; MS: 778 [M]. + ].

[0217] Example 10

[0218] The synthetic route of compound R199 in this embodiment is as follows:

[0219]

[0220] Compound Z22 (6.96 g, 30 mmol), phenylboronic acid (3.66 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was then heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The solution was then separated by silica gel column chromatography with stirring to give 4.97 g of compound Z23, with a yield of 72%.

[0221] Compound Z1 (7.72 g, 20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 12.5 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of compound Z23 (20 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography to give 6.54 g of compound Z24, in 58% yield.

[0222] Compound Z24 (5.64 g, 10 mmol) and diphenylamine (3.72 g, 22 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (2.3 g, 24 mmol) and tris(dibenzylacetone)palladium (0.46 g, 0.5 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.5 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 4.38 g of compound R199, yield 59%; MS: 742 [M]. + ].

[0223] Example 11

[0224] The synthetic route of compound R203 in this embodiment is as follows:

[0225]

[0226] Compound Z25 (4.62 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of p-bromoacetophenone (10 mmol / L) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give 2.93 g of compound Z26, with a yield of 52%.

[0227] Compound Z26 (2.82 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.25 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and separated by silica gel column chromatography to give 2.86 g of compound R203, yield 77%; MS: 742 [M]. + ].

[0228] Example 12

[0229] The synthetic route of compound R212 in this embodiment is as follows:

[0230]

[0231] Compound Z27 (4.96 g, 20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 12.5 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of Z28 (20 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction continued for another 8 hours. The solvent was removed under reduced pressure, and 10% hydrochloric acid was added. After another 2 hours, deionized water was added, and the mixture was extracted with ethyl acetate. The organic phase was concentrated and separated by silica gel column chromatography to give 3.5 g of compound Z29, in 54% yield.

[0232] Compound Z1 (3.86 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of compound Z29 (10 mmol / L) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give 3.68 g of compound Z30, in 60% yield.

[0233] Compound Z30 (3.07 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol) were added. After purging with nitrogen three times, tri-tert-butylphosphine (0.25 mmol) was added. The mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After cooling, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and purified by silica gel column chromatography to give 2.81 g of compound R212, yield 71%; MS: 792 [M]. + ].

[0234] Example 13

[0235] The synthetic route of compound R217 in this embodiment is as follows:

[0236]

[0237] Compound Z31 (4.08 g, 20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 12.5 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of Z28 (20 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction continued for another 8 hours. The solvent was removed under reduced pressure, 10% hydrochloric acid was added, and the reaction was continued for another 2 hours. Deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give 3.3 g of compound Z32, with a yield of 59%.

[0238] Compound Z1 (3.86 g, 10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 6.3 mL) was slowly added. After about 0.5 hours, a tetrahydrofuran solution of compound Z32 (10 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. The temperature was then raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added, followed by reflux for about 2 hours. The mixture was cooled to room temperature, and deionized water was added, followed by extraction with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography to remove the solvent, yielding 3.59 g of compound Z33, in 63% yield.

[0239] Compound Z33 (2.85 g, 5 mmol) and diphenylamine (2.03 g, 12 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and tris(dibenzylacetone) dipalladium (0.23 g, 0.25 mmol) were added, and the mixture was purged with nitrogen three times. Then, tri-tert-butylphosphine (0.25 mmol) was added, and the mixture was gradually heated to 80 °C and stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The organic phase was concentrated under reduced pressure and separated by silica gel column chromatography to give 2.61 g of compound R217, yield 66%; MS: 792 [M]. + ].

[0240] Fabrication and characterization of OLED devices:

[0241] The fabrication process of the OLED device comprising the above-described compound is described in detail below through specific embodiments. The structure of the OLED device is: anode substrate / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode. A schematic diagram of the OLED device is shown below. Figure 1 As shown, 101 is the substrate, 102 is the anode, 103 is the hole injection layer, 104 is the hole transport layer, 105 is the electron blocking layer, 106 is the light-emitting layer, 107 is the electron transport layer, 108 is the electron injection layer, and 109 is the cathode.

[0242] The fabrication steps of OLED-1 are as follows:

[0243] a. Clean the ITO (indium tin oxide) conductive glass with various solvents (such as one or more of deionized water, acetone or isopropanol) for 15 minutes, and then treat it in a plasma cleaner for 5 minutes to improve the electrode power function.

[0244] b. A 5nm thick HATCN layer was deposited as a hole injection layer using vacuum evaporation, with the deposition rate being...

[0245] c. Hole transport material HT is deposited as a hole transport layer by vacuum evaporation, with a thickness of 90nm.

[0246] d. Electron blocking layer material R1 is deposited on the hole transport layer by vacuum evaporation to form an electron blocking layer with a thickness of 20 nm.

[0247] e. A light-emitting layer with a thickness of 40 nm is deposited on the electron blocking layer. In the light-emitting layer material, RH is used as the host material for light emission, and RD is used as the guest material for light emission, with a mass ratio of RD to RH of 2:98.

[0248] f. On top of the light-emitting layer, a mixed electron transport material of ET and LiQ is deposited by vacuum evaporation, with a weight ratio of 5:5, to form an electron transport layer with a thickness of 30nm.

[0249] g. On top of the electron transport layer, electron injection material LiQ is vacuum evaporated to form an electron injection layer with a thickness of 2nm.

[0250] h. On top of the electron injection layer, metal Al is vacuum-deposited to form a cathode with a thickness of 80 nm.

[0251] i. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0252] The fabrication schemes of the devices OLED-2 to OLED-13 in the embodiments and the comparative examples OLED-Ref-1 to OLED-Ref-3 are the same as those of OLED-1, except that the electron blocking layer material R1 in OLED-1 of the embodiments is replaced with the compound corresponding to the electron blocking layer material in Table 1.

[0253] The following are some of the compound structures that may be involved in the OLED fabrication process:

[0254]

[0255] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and the LT95 lifetime and luminous efficiency were recorded. The results are shown in Table 1 below. LT95 lifetime refers to the time to 10 mA / cm² under constant current. 2 The LT95 lifetime and luminous efficiency are calculated relative to OLED-Ref-1 (corresponding to C1 electron blocking layer material), i.e., the lifetime and luminous efficiency of OLED-Ref-1 are 1.

[0256] Table 1:

[0257] Device Examples Electron blocking layer material Luminous efficiency (relative value) LT95 lifespan (relative value) OLED-1 R1 1.25 1.24 OLED-2 R14 1.23 1.22 OLED-3 R18 1.22 1.25 OLED-4 R25 1.18 1.20 OLED-5 R83 1.16 1.20 OLED-6 R120 1.20 1.23 OLED-7 R150 1.27 1.30 OLED-8 R168 1.24 1.28 OLED-9 R170 1.19 1.16 OLED-10 R199 1.21 1.25 OLED-11 R203 1.23 1.27 OLED-12 R212 1.20 1.23 OLED-13 R217 1.22 1.26 OLED-Ref-1 C1 1.0 1 OLED-Ref-2 C2 0.94 0.98 OLED-Ref-3 C3 0.97 1.02

[0258] As shown in Table 1, compared to the OLED-Ref-1 to OLED-Ref-3 OLED devices prepared using compounds C1, C2, and C3 as electron blocking layer materials in Comparative Examples 1-3, the OLED-1 to OLED-13 OLED devices prepared using the organic compounds of the present invention as electron blocking layer materials exhibit better luminous efficiency and longer luminous lifetime. This means that the organic compounds of the present invention, as electron blocking materials, can effectively improve the luminous efficiency and lifetime of organic electroluminescent devices. In the present invention, due to the presence of sp3 hybrid carbon, the influence between the two aromatic amine groups is small, and the triplet energy level of the molecule is relatively high. Furthermore, the two aromatic amine structures improve the carrier transport capability of the molecule, achieving a balance between it and the electron transport layer, thus improving the luminous efficiency of the device. In the comparative examples, compounds C1 and C2 did not have aromatic substituents attached to the fluorene, resulting in a shallower HOMO of the molecules. Compound C3 did not have aromatic amines attached to the fluorene, failing to fully utilize its carrier transport capabilities, thus affecting the luminous efficiency of the device.

[0259] The organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of the present invention have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of the present invention. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of the present invention. 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 the present invention. Therefore, the content of this specification should not be construed as a limitation of the present invention.

Claims

1. An organic compound characterized in that, The organic compound is selected from a structure represented by any one of formulae (2-1) or (2-2): wherein: R1is selected from a methyl group or a naphthyl group; R2is selected from a hydrogen atom, a methyl group or a phenyl group; R3is independently selected at each occurrence from a hydrogen atom or a phenyl group; L1to L4are selected from a single bond; Ar1and Ar2are independently selected from the following groups: Ar3and Ar4are independently selected from the following groups: R4is selected from a hydrogen atom or a phenyl group; R5, R6are selected from a methyl group; * indicates the site of attachment.

2. The organic compound according to claim 1, wherein The organic compound is selected from a structure represented by any one of formulae (3-1) to (3-6):

3. The organic compound according to claim 1, wherein The organic compound is selected from a structure represented by any one of formulae R1to R217:

4. A mixture characterized in that, The mixture comprises the organic compound according to any one of claims 1 to 3 and at least one organic functional material selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitting guest material, an emitting host material or an organic dye.

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

6. An organic electronic device comprising at least one functional layer, characterized in that The functional layer comprises the organic compound according to any one of claims 1 to 3 or the mixture according to claim 4 or is produced from the composition according to claim 5.

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