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

Abstract

The present application discloses an organic compound and a mixture, composition, and organic electronic device comprising the organic compound. The organic compound has a structure as shown in the general formula (1): the organic compound of the present application includes at least 3 nitrogen atoms and 2 boron atoms in the same rigid plane, and includes a non-aromatic cyclic group on the side, which well combines the high fluorescence quantum efficiency of the rigid plane and the advantages of flexible editing to reduce π-π stacking. The organic compound is used in organic electronic devices, especially as a luminescent material in the light-emitting layer of an organic electronic device, and can better improve the luminous efficiency and stability of this type of compound.

Description

Technical Field

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

[0002] Organic semiconductor materials offer diverse synthesis, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad potential for development in optoelectronic devices (such as flat-panel displays and lighting) due to their advantages, including wide viewing angles, fast response times, low operating voltages, and thin panels.

[0003] The principle of organic light-emitting diodes (OLEDs) is organic electroluminescence, which refers to the phenomenon of converting electrical energy into light energy using organic substances. OLEDs that utilize organic electroluminescence typically have a positive electrode and a negative electrode, with a functional layer containing organic matter between them. To improve the efficiency and lifespan of OLEDs, the functional layers have a multilayer structure, with each layer containing different organic substances. Specifically, these layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, or an electron injection layer. In an OLED, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, which then emit light when they transition back to the ground state. This type of organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the luminous efficiency of organic light-emitting diodes (OLEDs), various fluorescent and phosphorescent luminescent material systems have been developed. Organic light-emitting diodes (OLEDs) using fluorescent materials are known for their high reliability. However, the development of blue fluorescent materials with excellent optical and electrical properties faces a significant challenge. Most traditional blue fluorescent materials have low luminous efficiency and poor color purity, making them unsuitable for high-end displays. OLED devices made with these blue fluorescent materials also suffer from poor luminous efficiency and stability, requiring further improvement.

[0005] Therefore, it is of great significance to develop blue fluorescent materials with high efficiency and good stability. Summary of the Invention

[0006] In view of this, the present application provides an organic compound as a new type of fluorescent luminescent material, which is used in organic electronic devices to improve the problems of low luminous efficiency and short life of organic electronic devices.

[0007] The technical solution of this application is as follows:

[0008] An organic compound having a structure as shown in general formula (1):

[0009]

[0010] in:

[0011] Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 40 ring atoms;

[0012] Ar6 is selected from a substituted or unsubstituted non-aromatic cyclic group having 5 to 30 ring atoms, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0013] Ar7 is selected from substituted or unsubstituted non-aromatic cyclic groups having 5 to 30 ring atoms.

[0014] Correspondingly, the present application also provides a mixture comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminophores or organic dyes.

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

[0016] Correspondingly, the present application also provides an organic electronic device, comprising at least one functional layer, wherein the functional layer comprises the above-mentioned organic compound or the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

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

[0018] The organic compound represented by the general formula (1) of the present application includes at least three nitrogen atoms and two boron atoms in the same rigid plane, and includes non-aromatic cyclic groups on the side, which well combines the high fluorescence quantum efficiency of the rigid plane and the advantages of the flexible side group that can reduce π-π stacking. The organic compound is used in organic electronic devices, especially as a luminescent material in the light-emitting layer of an organic electronic device, and can effectively improve the luminescence efficiency and stability of this type of compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0020] Figure 1 Schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application, wherein: 10 is a substrate; 20 is an anode; 30 is a hole injection layer; 40 is a hole transport layer; 50 is a light-emitting layer; 60 is an electron transport layer; and 70 is a cathode. DETAILED DESCRIPTION

[0021] The following, in conjunction with the accompanying drawings, provides a clear and complete description of the technical solutions in the embodiments of this application. It should be understood that the described embodiments are only some of the embodiments of this application, and not all of them. Based on the embodiments of this application, all other embodiments derived by those skilled in the art without inventive effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are intended only to illustrate and explain this application and are not intended to limit this application. In this application, unless otherwise indicated, directional terms such as "upper" and "lower" generally refer to the upper and lower parts of a device in actual use or operation, specifically the directions of the drawings in the accompanying drawings. Furthermore, in the description of this application, the term "including" means "including but not limited to," the term "plurality" means "two or more," and the term "and / or" includes any and all combinations of one or more of the associated listed items. The various embodiments of this application may be presented in the form of a range. It should be understood that describing in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of this application. Therefore, the range description should be considered to have specifically disclosed all possible subranges and individual numerical values ​​within the range. For example, description of a range from 1 to 6 should be considered to have specifically disclosed 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., as well as individual numbers within that range, such as 1, 2, 3, 4, 5, and 6. Furthermore, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.

[0022] In this application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0023] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0024] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0025] 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.

[0026] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group 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", silanyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium atom, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may be further substituted by substituents acceptable in the art.

[0027] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0028] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For 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 group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0029] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of aryl is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, triazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyridinyl, oxazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzothiophenyl, benzofuranyl, indolyl, carbazolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, o-naphthyl, quinoxalinyl, phenanthridinyl, primary pyridyl, quinazolinyl, quinazolinonyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0030] In this application, a "non-aromatic cyclic group" refers to a cyclic group other than an aromatic group or a heteroaromatic group. Non-aromatic cyclic groups include non-aromatic carbocycles or non-aromatic heterocycles. Non-aromatic heterocycles refer to non-aromatic cyclic groups that include at least one non-carbon atom, which may be an N atom, an O atom, an S atom, etc. For example, a "substituted or unsubstituted non-aromatic cyclic group having 5 to 30 ring atoms" refers to a non-aromatic carbocycle or non-aromatic heterocycle having 5 to 30 ring atoms, preferably a substituted or unsubstituted non-aromatic carbocycle or non-aromatic heterocycle having 6-14 ring atoms. In some embodiments, the non-aromatic cyclic group may be a saturated carbocycle or an unsaturated carbocycle, such as a substituted or unsubstituted cycloalkyl, cycloalkenyl, or bridged ring group. Suitable examples include, but are not limited to, cyclopentanyl, cyclohexanyl, cyclopentenyl, cyclohexenyl, bicyclo[2,2.1]heptanyl, and their derivatives.

[0031] In this application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9 The term "alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl at each occurrence. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, tert-butyl, 2-ethylbutyl, 2-pentyl ... Pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, adamantane, and the like.

[0032] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0033] As used herein, "amino" refers to an amine derivative having the structural characteristics of the formula -N(X)2, wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, etc. Non-limiting types of amino groups include -NH2, -N(alkyl), -NH(alkyl), -N(cycloalkyl), -NH(cycloalkyl), -N(heterocyclyl), -NH(heterocyclyl), -N(aryl), -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclyl), -N(cycloalkyl)(heterocyclyl), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0034] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0035] In the present application, when a linking site is not specified in a group, it means that an optional linking site in the group can be used as the linking site.

[0036] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in adjacent positions in the group are fusion sites.

[0037] In this application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0038] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring, such as express Can be used with The above optional substitutable positions form a ring.

[0039] In the present application, "adjacent groups" means that there is no substitutable site between two substituents.

[0040] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0041] The technical solution of this application is as follows:

[0042] An organic compound, characterized in that it has a structure as shown in general formula (1):

[0043]

[0044] in:

[0045] Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 40 ring atoms;

[0046] Ar6 is selected from a substituted or unsubstituted non-aromatic cyclic group having 5 to 30 ring atoms, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0047] Ar7 is selected from substituted or unsubstituted non-aromatic cyclic groups having 5 to 30 ring atoms.

[0048] In one embodiment, Ar7 is selected from a substituted or unsubstituted non-aromatic cyclic group having 5 to 6 ring atoms.

[0049] Furthermore, Ar7 is selected from any one of the structures shown in formula (A-1) to (A-5):

[0050]

[0051] in:

[0052] Each occurrence of V is independently selected from CR2R3;

[0053] R1, R2, and R3, when each occurs, are independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a cycloalkyl group having 3 to 10 C atoms, or a combination of these groups;

[0054] * indicates the fusion site.

[0055] In one embodiment, each occurrence of R1, R2, and R3 is independently selected from: -H, -D, methyl, or a combination thereof.

[0056] In one embodiment, Ar7 is selected from any one of the structures shown in formula (B-1) to (B-7):

[0057]

[0058] In one embodiment, Ar6 is selected from a substituted or unsubstituted non-aromatic cyclic group having 5 to 6 ring atoms; further, Ar6 is selected from any one of the structures shown in formulas (A-1) to (A-5); further, Ar6 is selected from any one of the structures shown in formulas (B-1) to (B-7).

[0059] In one embodiment, Ar6 and Ar7 are selected from the same group.

[0060] In another embodiment, Ar6 is selected from a substituted or unsubstituted aromatic group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 25 ring atoms. Further, Ar6 is selected from a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 13 ring atoms.

[0061] Further, Ar6 is selected from any one of the structures shown in formula (C-1) to (C-9):

[0062]

[0063] in:

[0064] Each occurrence of X is independently selected from CR4 or N;

[0065] Each occurrence of Y is independently selected from NR5, PR5, CR6R7, SiR6R7, O, S, S(=O)2 or S(=O);

[0066] R4, R5, R6, and R7 are each independently selected from the group consisting of: -H, -D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a substituted or unsubstituted silyl group, a 1 to 20 C atom , keto, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, -CF3, -OCF3, -Cl, -Br, -F, substituted or unsubstituted aromatic groups having 6 to 40 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 40 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 40 ring atoms, or substituted or unsubstituted heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these groups.

[0067] Furthermore, Ar6 is selected from any one of the structures shown in formula (D-1) to (D-13):

[0068]

[0069] Where: * indicates the fusion site.

[0070] In one embodiment, Ar1 to Ar5 are independently selected from 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;

[0071] In one embodiment, Ar1 to Ar5 are independently selected from a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms.

[0072] In one embodiment, Ar1 to Ar5 are independently selected from any one of formula (E-1) to (E-4):

[0073]

[0074] Wherein: X, Y have the same meanings as above.

[0075] In one embodiment, Ar2 and Ar3 are selected from (E-1) or (E-2). In one embodiment, the organic compound is represented by formula (2-1) or (2-2):

[0076]

[0077] In one embodiment, Ar1, Ar4 and Ar5 are selected from (E-1) or (E-2) or (E-3) or (E-4).

[0078] Furthermore, the above organic compound has a structure as shown in any one of formulas (3-1) to (3-11):

[0079]

[0080] Wherein: Ar6 and Ar7 have the same meanings as above.

[0081] In one embodiment, in the above organic compound, each occurrence of X is selected from CR4; further, each occurrence of R4 is independently selected from: -H, -D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination thereof.

[0082] Further, each occurrence of R4 is independently selected from: -H, -D, a straight-chain alkyl group having 1 to 8 carbon atoms, a branched-chain alkyl group having 3 to 8 carbon atoms; further, at least one R4 is selected from a straight-chain alkyl group having 1 to 8 carbon atoms or a branched-chain alkyl group having 3 to 8 carbon atoms; further, at least one R4 is selected from a methyl group, an isopropyl group, or a group as shown below:

[0083] Wherein n1 is selected from any integer from 0 to 4.

[0084] In some embodiments, each occurrence of Y is independently selected from NR5, CR6R7, O or S; further, each occurrence of R5, R6, and R7 is independently selected from -H, -D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cycloalkyl group having 3 to 10 C atoms, an unsubstituted aromatic group having 6 to 20 ring atoms, an unsubstituted heteroaromatic group having 5 to 20 ring atoms, or an aromatic group having 6 to 20 ring atoms substituted by a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a cycloalkyl group having 3 to 10 C atoms, or a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms, or a combination of these groups.

[0085] In one embodiment, when Ar1, Ar2, Ar3, Ar4, and Ar5 are independently selected from formula (E-1), formula (E-1) is selected from the following structures:

[0086]

[0087] Wherein: R4 has the same meaning as above.

[0088] Furthermore, (E-1) is selected from the following structures:

[0089]

[0090] In one embodiment, the organic compound represented by formula (1) is a symmetrical structure compound.

[0091] In one embodiment, the organic compound represented by formula (1) is an asymmetric structure compound.

[0092] Further, examples of the organic compounds of the present invention include but are not limited to the following structures:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] It is understood that the H in the structural formula of the above organic compound can be further substituted. In some embodiments, the organic compound of the present application can be partially deuterated, for example, 10% of the H is deuterated, preferably 20% of the H is deuterated, more preferably 30% of the H is deuterated, and most preferably 40% of the H is deuterated.

[0100] In one embodiment, the organic compound of the present application can be used as an organic functional material in a functional layer of an organic electronic device, particularly in a functional layer of an OLED device. The organic functional material can be, but is not limited to, a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a guest emitter, a host emitter, and an organic dye.

[0101] In one embodiment, the organic compound of the present application is used in a light-emitting layer. Preferably, the organic compound of the present application is used in the light-emitting layer as a guest material of the light-emitting layer.

[0102] In a specific embodiment, the organic compound according to the present application is used as a blue light emitting guest material in the light emitting layer.

[0103] The present application further provides a mixture comprising at least one organic compound as described above and at least another organic functional material. The another 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 and organic dyes. Wherein, the luminophore is selected from singlet luminophores (fluorescent luminophores) or triplet luminophores (phosphorescent luminophores) grade organic thermally excited delayed fluorescence materials (TADF materials). Detailed descriptions of various organic functional materials are detailed in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these 3 patent documents are hereby incorporated herein by reference. It is understood that the another organic functional material can be a small molecule organic material and a polymer material.

[0104] In one embodiment, the other organic functional material is selected from a host material; further, the other organic functional material is selected from a blue light host material. The weight percentage of the organic compound of the present invention in the mixture is greater than 0 and less than 25 wt %, preferably greater than 0 and less than 15 wt %, and more preferably greater than 0 and less than 5 wt %.

[0105] The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.

[0106] 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 ester compounds and phosphate ester compounds.

[0107] In at least one embodiment, in the composition, the organic solvent is selected from aromatic or heteroaromatic solvents.

[0108] The aromatic or heteroaromatic based solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropyl At least one of biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0109] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Particularly preferred is at least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0110] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. For example, the derivative may be selected from, but not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0111] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0112] The aliphatic ketone-based solvent can be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or an aliphatic ether, for example, at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0113] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0114] In one embodiment, the composition of the present application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0115] The other organic solvent can be selected from, but not limited to, at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetralin, decalin and indene.

[0116] In one embodiment, the organic solvent suitable for the present application is a solvent having a Hansen solubility parameter within the following range:

[0117] δd (dispersion force) at 17.0 MPa 1 / 2 -23.2MPa 1 / 2 range, especially at 18.5MPa 1 / 2 -21.0MPa 1 / 2 within the scope;

[0118] δp (polar force) at 0.2MPa 1 / 2 -12.5MPa 1 / 2 range, especially at 2.0MPa 1 / 2 -6.0MPa 1 / 2 within the scope;

[0119] δh (hydrogen bond strength) at 0.9 MPa 1 / 2 -14.2MPa 1 / 2 range, especially at 2.0MPa 1 / 2 -6.0MPa 1 / 2 within the range.

[0120] In one embodiment, the boiling point of the organic solvent used in the composition of the present application should be considered when selecting the solvent. In at least some embodiments, the boiling point of the organic solvent is ≥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 in inkjet printheads.

[0121] It will be appreciated that the organic solvent may be evaporated from the solvent system to form a thin film comprising the organic compound.

[0122] In one embodiment, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of a surfactant, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0123] The composition may also be referred to as ink.

[0124] When used in printing processes, the viscosity and surface tension of ink are important parameters. The appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method.

[0125] In one embodiment, the surface tension of the ink according to the present application at operating temperature or 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably 22 dyne / cm to 35 dyne / cm; and most preferably 25 dyne / cm to 33 dyne / cm.

[0126] In one embodiment, the viscosity of the ink according to the present application at working temperature or 25° C. ranges from 1 cps to 100 cps; preferably from 1 cps to 50 cps; more preferably from 1.5 cps to 20 cps; and most preferably from 4.0 cps to 20 cps.

[0127] It will be appreciated that inks having the above surface tension and viscosity will facilitate inkjet printing.

[0128] It will be appreciated that the viscosity of the ink can be adjusted by various methods, such as by selecting an appropriate solvent and adjusting the concentration of the functional material in the ink. The ink comprising the organic compound described herein facilitates adjusting the viscosity of the printing ink within an appropriate range depending on the printing method used. The composition of the present invention comprises the organic compound or mixture in an amount of 0.01 wt% to 10 wt%, preferably 0.1 wt% to 15 wt%, more preferably 0.2 wt% to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0129] The present application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In one embodiment, the composition is used to prepare an organic electronic device by a printing or coating method. The printing or coating method can be, but is not limited to, inkjet printing, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slot extrusion coating, etc. Gravure printing, spray printing, and inkjet printing are preferred.

[0130] The present application also relates to the use of the organic compound, mixture, or composition described above in an organic electronic device. In one embodiment, the present application provides an organic electronic device comprising at least one functional layer. The functional layer comprises at least one organic compound or mixture described above, or the functional layer is prepared from the composition described above.

[0131] Furthermore, the organic electronic device comprises a cathode, an anode and at least one functional layer, wherein the functional layer comprises at least one organic compound or mixture as described above, or is prepared from the above composition.

[0132] The functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer. Preferably, the functional layer is a light-emitting layer. The light-emitting layer comprises at least one organic compound or mixture as described above, or the light-emitting layer is prepared from the composition as described above.

[0133] In one embodiment, the light-emitting layer includes a light-emitting host material and a light-emitting guest material, wherein the light-emitting guest material is the aforementioned organic compound or mixture. Furthermore, the mass ratio of the light-emitting guest material to the host material is greater than or equal to 25%; further, the mass ratio of the light-emitting guest material to the host material is greater than or equal to 15%; further, the mass ratio of the light-emitting guest material to the host material is greater than or equal to 5%.

[0134] The organic electronic device may be, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLED), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPD). Particularly preferred are organic electroluminescent devices such as OLEDs, OLEECs, and organic light-emitting field-effect transistors. OLEDs are even more particularly preferred.

[0135] In one embodiment, if Figure 1 As shown, the organic electronic device includes a substrate and an anode 10, a hole injection layer 20, a hole transport layer 30, an electron blocking layer 40, a light-emitting layer 50, an electron transport layer 60, and a cathode 70 sequentially stacked on the substrate. In one embodiment, an electron injection layer may be further provided between the electron transport layer 60 and the cathode 70.

[0136] It can be understood that the structure of the organic electronic device is not limited thereto.

[0137] The substrate can be transparent or opaque. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can also be rigid or elastic. In one embodiment, the substrate is plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface, and substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics with a glass transition temperature Tg of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0138] The anode is a hole-injecting electrode, and the anode can easily inject holes into the hole injection layer, the hole transport layer, or the 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 energy level or valence band energy level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected and used by one of ordinary skill 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), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.

[0139] The cathode is an electrode that injects electrons, and the cathode can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer. The cathode may comprise a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of organic electronic devices may be used as cathode materials of the organic electronic device of the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

[0140] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a 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 by reference.

[0141] The hole injection layer is a layer for promoting the injection of holes from the anode into the light-emitting layer, and the hole injection material is a material that can skillfully receive holes injected from the positive electrode at a low voltage, and preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, etc., but are not limited thereto.

[0142] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.

[0143] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a spiroindoloacridine-based compound or a material known in the art may be used.

[0144] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives or heterocyclic compounds. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples thereof are not limited thereto.

[0145] The electron transport layer can be used to smoothly transport electrons. The electron transport material is suitably a material with high electron mobility, which can skillfully receive electrons injected from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof may include, but are not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), ET1, and a benzimidazole-based compound.

[0146] The electron injection layer can be used to smoothly inject electrons. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability. Specific examples include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0147] The hole blocking layer is a layer that blocks holes from reaching the negative electrode and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

[0148] The light emitting wavelength of the organic electronic device is between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0149] In one embodiment, the organic electronic device described in the present application is a solution-type organic electronic device, and one or more functional layers thereof are prepared by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0150] The present application also relates to applications of the organic electronic device according to the present application in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0151] The present application also relates to electronic devices comprising the organic electronic device, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and other electronic devices.

[0152] The present application is described in detail below through specific examples. The following examples are only some examples of the present application and are not intended to limit the present application. The present application is not limited to the following examples. Specific embodiments

[0154] Example 1

[0155] This example involves the synthesis of organic compound M1

[0156] The synthetic route is as follows:

[0157]

[0158] (1) Synthesis of intermediate M1-3: Under nitrogen environment, compound M1-1 (8.6 g, 50 mmol), compound M1-2 (10.5 g, 50 mmol), cesium carbonate (32.6 g, 100 mmol) and 150 mL of N,N-dimethylformamide were added to a 300 mL three-necked flask, heated to 150 ° C and reacted for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and most of the solvent was removed by rotary evaporation. The reaction solution was poured into 400 mL of pure water, the precipitated solid was filtered, and the filter residue was collected for recrystallization and purification, with a yield of 82%.

[0159] (2) Synthesis of intermediate M1-5: Referring to the synthesis method of compound M1-3, compound M1-4 was used instead of compound M1-1 to prepare intermediate M1-5 with a yield of 85%.

[0160] (3) Synthesis of intermediate M1-7: Under nitrogen environment, intermediate M1-5 (10.7 g, 30 mmol), compound M1-6 (2.8 g, 30 mmol), compound Pd2(dba)3 (0.92 g, 1 mmol), compound tri-tert-butylphosphine (0.4 g, 2 mmol), compound sodium tert-butoxide (5.48 g, 60 mmol) and 150 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask, heated to 80 ° C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent. The reaction solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-7. The eluent was petroleum ether: dichloromethane = 3:1 (volume ratio), with a yield of 75%.

[0161] (4) Synthesis of intermediate M1-8: Referring to the synthesis method of intermediate M1-7, compounds M1-5 and M1-6 were replaced by compounds M1-3 and M1-7, respectively, to synthesize intermediate M1-8 with a yield of 72%.

[0162] (5) Synthesis of Compound M1: Under nitrogen, compound M1-8 (13.0 g, 20 mmol) and 100 mL of anhydrous toluene were added to a 300 mL three-necked flask, stirred and dissolved, and the mixture was cooled to -78°C. 45 mmol of tert-butyl lithium was slowly added dropwise and allowed to react for 2 hours. 50 mmol of boron tribromide was added all at once, and the reaction solution was allowed to slowly warm to room temperature. The reaction was stirred and continued for 3 hours. 80 mmol of diisopropylethylamine was added all at once, and the mixture was heated to 100°C and allowed to react for 4 hours. After the reaction was complete, the reaction solution was rotary evaporated to remove most of the solvent, and the mixture was washed three times with dichloromethane. The organic solution was collected, mixed with silica gel, and purified by column chromatography to obtain compound M1. The eluent was a petroleum ether:dichloromethane volume ratio of 4:1. The yield was 35%. MS (ASAP): 595.

[0163] Example 2

[0164] This example involves the synthesis of organic compound M2

[0165] The synthetic route is as follows:

[0166]

[0167] (1) Synthesis of intermediate M2-3: Referring to the synthesis method of compound M1-3, compounds M2-1 and M2-2 were used to replace compounds M1-1 and M1-2, respectively, to synthesize compound M2-3 with a yield of 76%.

[0168] (2) Synthesis of intermediate M2-5: Referring to the synthesis method of compound M1-3, compounds M2-4 and M2-2 were used to replace compounds M1-1 and M1-2, respectively, to synthesize compound M2-5 with a yield of 80%.

[0169] (3) Synthesis of intermediate M2-6: Referring to the synthesis method of compound M1-7, compound M2-5 was used instead of compound M1-5 to synthesize compound M2-6 with a yield of 74%.

[0170] (4) Synthesis of intermediate M2-7: Referring to the synthesis method of compound M1-7, compounds M2-3 and 2-6 were used to replace compounds M1-5 and M1-6, respectively, to synthesize compound M2-7 with a yield of 71%.

[0171] (5) Synthesis of Compound M2: Referring to the synthesis method of Compound M1, Compound M2-7 was used instead of Compound M1-8 to synthesize Compound M2 with a yield of 33%. MS (ASAP): 654.

[0172] Example 3

[0173] This example involves the synthesis of organic compound M3

[0174] The synthetic route is as follows:

[0175]

[0176] (1) Synthesis of intermediate M3-3: Referring to the synthesis method of compound M1-3, compounds M3-1 and M3-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 75%.

[0177] (2) Synthesis of intermediate M3-5: Referring to the synthesis method of compound M1-3, compounds M3-4 and M3-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 78%.

[0178] (3) Synthesis of intermediate M3-6: Referring to the synthesis method of compound M1-7, compound M3-5 was used instead of compound M1-5, with a yield of 72%.

[0179] (4) Synthesis of intermediate M3-7: Referring to the synthesis method of compound M1-7, compounds M3-3 and M3-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0180] (5) Synthesis of Compound M3: Referring to the synthesis method of Compound M1, Compound M3-7 was used instead of Compound M1-8, with a yield of 34%. MS (ASAP): 750.

[0181] Example 4

[0182] This example involves the synthesis of organic compound M4

[0183] The synthetic route is as follows:

[0184]

[0185] (1) Synthesis of intermediate M4-3: Referring to the synthesis method of compound M1-3, compounds M4-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0186] (2) Synthesis of intermediate M4-5: Referring to the synthesis method of compound M1-3, compounds M4-4 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 74%.

[0187] (3) Synthesis of intermediate M4-7: Referring to the synthesis method of compound M1-7, compounds M4-5 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 73%.

[0188] (4) Synthesis of intermediate M4-8: Referring to the synthesis method of compound M1-7, compounds M4-3 and M4-7 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0189] (5) Synthesis of Compound M4: Referring to the synthesis method of Compound M1, Compound M4-8 was used instead of Compound M1-8, with a yield of 32%. MS (ASAP): 864.

[0190] Example 5

[0191] This example involves the synthesis of organic compound M5

[0192] The synthetic route is as follows:

[0193]

[0194] (1) Synthesis of intermediate M5-2: Referring to the synthesis method of compound M1-3, compounds M5-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 70%.

[0195] (2) Synthesis of intermediate M5-3: Referring to the synthesis method of compound M1-7, compounds M5-2 and M4-7 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 72%.

[0196] (3) Synthesis of Compound M5: Referring to the synthesis method of Compound M1, Compound M5-3 was used instead of Compound M1-8, with a yield of 32%. MS (ASAP): 792.

[0197] Example 6

[0198] This example involves the synthesis of organic compound M6

[0199] The synthetic route is as follows:

[0200]

[0201] (1) Synthesis of intermediate M6-2: Referring to the synthesis method of compound M1-3, compounds M6-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0202] (2) Synthesis of intermediate M6-4: Referring to the synthesis method of compound M1-3, compounds M6-3 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 73%.

[0203] (3) Synthesis of intermediate M6-5: Referring to the synthesis method of compound M1-7, compound M6-4 was used instead of compound M1-5, with a yield of 74%.

[0204] (4) Synthesis of intermediate M6-6: Referring to the synthesis method of compound M1-7, compounds M6-2 and M6-5 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0205] (5) Synthesis of Compound M6: Referring to the synthesis method of Compound M1, Compound M6-6 was used instead of Compound M1-8, with a yield of 31%. MS (ASAP): 788.

[0206] Example 7

[0207] This example involves the synthesis of organic compound M7

[0208] The synthetic route is as follows:

[0209]

[0210] (1) Synthesis of intermediate M7-2: Referring to the synthesis method of compound M1-3, compounds M7-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0211] (2) Synthesis of intermediate M7-3: Referring to the synthesis method of compound M1-3, compounds M1-1 and M1-2 were replaced by compounds M1-4 and M4-2, respectively, with a yield of 76%.

[0212] (3) Synthesis of intermediate M7-5: Referring to the synthesis method of compound M1-7, compounds M7-3 and M7-4 were used instead of compounds M1-5 and M1-6, with a yield of 75%.

[0213] (4) Synthesis of intermediate M7-6: Referring to the synthesis method of compound M1-7, compounds M7-2 and M7-5 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 72%.

[0214] (5) Synthesis of Compound M7: Referring to the synthesis method of Compound M1, Compound M7-6 was used instead of Compound M1-8, with a yield of 23%. MS (ASAP): 772.

[0215] Example 8

[0216] This example involves the synthesis of organic compound M8

[0217] The synthetic route is as follows:

[0218]

[0219] (1) Synthesis of intermediate M8-1: Referring to the synthesis method of compound M1-3, compounds M3-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 76%.

[0220] (2) Synthesis of intermediate M8-3: Referring to the synthesis method of compound M1-3, compounds M8-2 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 77%.

[0221] (3) Synthesis of intermediate M8-4: Referring to the synthesis method of compound M1-7, compounds M8-3 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 74%.

[0222] (4) Synthesis of intermediate M8-5: Referring to the synthesis method of compound M1-7, compounds M8-1 and M8-4 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 72%.

[0223] (5) Synthesis of Compound M8: Referring to the synthesis method of Compound M1, Compound M8-5 was used instead of Compound M1-8, with a yield of 31%. MS (ASAP): 866.

[0224] Example 9

[0225] This example involves the synthesis of organic compound M9

[0226] The synthetic route is as follows:

[0227]

[0228] (1) Synthesis of intermediate M9-2: Referring to the synthesis method of compound M1-3, compounds M9-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 76%.

[0229] (2) Synthesis of intermediate M9-3: Referring to the synthesis method of compound M1-7, compounds M9-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 73%.

[0230] (3) Synthesis of intermediate M9-4: Referring to the synthesis method of compound M1-7, compounds M4-3 and M9-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 74%.

[0231] (4) Synthesis of Compound M9: Referring to the synthesis method of Compound M1, Compound M9-4 was used instead of Compound M1-8, with a yield of 28%. MS (ASAP): 869.

[0232] Example 10

[0233] This example involves the synthesis of organic compound M10

[0234] The synthetic route is as follows:

[0235]

[0236] The specific synthesis steps are as follows:

[0237] (1) Synthesis of intermediate M10-1: Referring to the synthesis method of compound M1-3, compound M4-2 was used instead of compound M1-2, with a yield of 78%.

[0238] (2) Synthesis of intermediate M10-3: Referring to the synthesis method of compound M1-3, compounds M10-2 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 75%.

[0239] (3) Synthesis of intermediate M10-4: Referring to the synthesis method of compound M1-7, compounds M10-3 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 74%.

[0240] (4) Synthesis of intermediate M10-5: Referring to the synthesis method of compound M1-7, compounds M10-1 and M10-4 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 72%.

[0241] (5) Synthesis of Compound M10: Referring to the synthesis method of Compound M1, Compound M10-5 was used instead of Compound M1-8, with a yield of 30%. MS (ASAP): 854.

[0242] Example 11

[0243] This example involves the synthesis of organic compound M11

[0244] The synthetic route is as follows:

[0245]

[0246] (1) Synthesis of intermediate M11-1: Referring to the synthesis method of compound M1-3, compounds M2-1 and M4-2 were used instead of compounds M1-1 and M1-2, with a yield of 75%.

[0247] (2) Synthesis of intermediate M11-3: Referring to the synthesis method of compound M1-3, compounds M11-2 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0248] (3) Synthesis of intermediate M11-4: Referring to the synthesis method of compound M1-7, compounds M11-3 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0249] (4) Synthesis of intermediate M11-5: Referring to the synthesis method of compound M1-7, compounds M11-1 and M11-4 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 68%.

[0250] (5) Synthesis of Compound M11: Referring to the synthesis method of Compound M1, Compound M11-5 was used instead of Compound M1-8, with a yield of 33%. MS (ASAP): 872.

[0251] Example 12

[0252] This example involves the synthesis of organic compound M12

[0253] The synthetic route is as follows:

[0254]

[0255] (1) Synthesis of intermediate M12-2: Referring to the synthesis method of compound M1-3, compounds M12-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 73%.

[0256] (2) Synthesis of intermediate M12-3: Referring to the synthesis method of compound M1-7, compounds M12-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 71%.

[0257] (3) Synthesis of intermediate M12-4: Referring to the synthesis method of compound M1-7, compounds M8-1 and M12-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 67%.

[0258] (4) Synthesis of Compound M12: Referring to the synthesis method of Compound M1, Compound M12-4 was used instead of Compound M1-8, with a yield of 32%. MS (ASAP): 850.

[0259] Example 13

[0260] This example involves the synthesis of organic compound M13

[0261] The synthetic route is as follows:

[0262]

[0263] (1) Synthesis of intermediate M13-2: Referring to the synthesis method of compound M1-3, compounds M13-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 76%.

[0264] (2) Synthesis of intermediate M13-3: Referring to the synthesis method of compound M1-7, compounds M13-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 73%.

[0265] (3) Synthesis of intermediate M13-4: Referring to the synthesis method of compound M1-7, compounds M4-3 and M13-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0266] (4) Synthesis of Compound M13: Referring to the synthesis method of Compound M1, Compound M13-4 was used instead of Compound M1-8, with a yield of 31%. MS (ASAP): 902.

[0267] Example 14

[0268] This example involves the synthesis of organic compound M14

[0269] The synthetic route is as follows:

[0270]

[0271] (1) Synthesis of intermediate M14-2: Referring to the synthesis method of compound M1-3, compounds M14-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 71%.

[0272] (2) Synthesis of intermediate M14-3: Referring to the synthesis method of compound M1-7, compounds M14-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0273] (3) Synthesis of intermediate M14-4: Referring to the synthesis method of compound M1-7, compounds M10-1 and M14-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 67%.

[0274] (4) Synthesis of Compound M14: Referring to the synthesis method of Compound M1, Compound M14-4 was used instead of Compound M1-8, with a yield of 33%. MS (ASAP): 1002.

[0275] Example 15

[0276] This example involves the synthesis of organic compound M15

[0277] The synthetic route is as follows:

[0278]

[0279] (1) Synthesis of intermediate M15-2: Referring to the synthesis method of compound M1-3, compounds M15-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 76%.

[0280] (2) Synthesis of intermediate M15-3: Referring to the synthesis method of compound M1-7, compounds M15-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 72%.

[0281] (3) Synthesis of intermediate M15-4: Referring to the synthesis method of compound M1-7, compounds M8-1 and M15-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0282] (4) Synthesis of Compound M15: Referring to the synthesis method of Compound M1, Compound M15-4 was used instead of Compound M1-8, with a yield of 34%. MS (ASAP): 806.

[0283] Example 16

[0284] This example involves the synthesis of organic compound M8

[0285] The synthetic route is as follows:

[0286]

[0287] (1) Synthesis of intermediate M16-1: Referring to the synthesis method of compound M1-7, 2-fold molar amount of compound M1-3 and 1-fold molar amount of compound M1-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 63%.

[0288] (2) Synthesis of Compound M16: Referring to the synthesis method of Compound M1, Compound M16-1 was used instead of Compound M1-8, with a yield of 32%. MS (ASAP): 600.

[0289] Example 17

[0290] This example involves the synthesis of organic compound M17

[0291] The synthetic route is as follows:

[0292]

[0293] (1) Synthesis of intermediate M17-2: Referring to the synthesis method of compound M16-1, compounds M2-3 and M17-1 were used to replace compounds M1-3 and M1-6, respectively, with a yield of 65%.

[0294] (2) Synthesis of Compound M17: Referring to the synthesis method of Compound M1, Compound M17-2 was substituted for Compound M1-8, with a yield of 34%. MS (ASAP): 646.

[0295] Example 18

[0296] This example involves the synthesis of organic compound M18

[0297] The synthetic route is as follows:

[0298]

[0299] (1) Synthesis of intermediate M18-2: Referring to the synthesis method of compound M16-1, compounds M3-3 and M18-1 were used to replace compounds M1-3 and M1-6, respectively, with a yield of 66%.

[0300] (2) Synthesis of Compound M17: Referring to the synthesis method of Compound M1, Compound M18-2 was used instead of Compound M1-8, with a yield of 35%. MS (ASAP): 698.

[0301] Example 19

[0302] This example involves the synthesis of organic compound M19

[0303] The synthetic route is as follows:

[0304]

[0305] (1) Synthesis of intermediate M19-1: Referring to the synthesis method of compound M16-1, compounds M5-2 and M4-6 were used to replace compounds M1-3 and M1-6, respectively, with a yield of 62%.

[0306] (2) Synthesis of Compound M19: Referring to the synthesis method of Compound M1, Compound M19-1 was used instead of Compound M1-8, with a yield of 28%. MS (ASAP): 800.

[0307] Example 20

[0308] This example involves the synthesis of organic compound M20

[0309] The synthetic route is as follows:

[0310]

[0311] (1) Synthesis of intermediate M20-1: Referring to the synthesis method of compound M1-3, compound M4-1 was used instead of compound M1-1, with a yield of 75%.

[0312] (2) Synthesis of intermediate M20-3: Referring to the synthesis method of compound M16-1, compounds M20-1 and M20-2 were used to replace compounds M1-3 and M1-6, respectively, with a yield of 64%.

[0313] (3) Synthesis of Compound M20: Referring to the synthesis method of Compound M1, Compound M20-3 was used instead of Compound M1-8, with a yield of 30%. MS (ASAP): 646.

[0314] Example 21

[0315] This example involves the synthesis of organic compound M21

[0316] The synthetic route is as follows:

[0317]

[0318] (1) Synthesis of intermediate M21-1: Referring to the synthesis method of compound M1-3, compounds M2-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0319] (2) Synthesis of intermediate M21-2: Referring to the synthesis method of compound M1-3, M4-2 was used instead of compound M1-2, with a yield of 73%.

[0320] (3) Synthesis of intermediate M21-3: Referring to the synthesis method of compound M1-7, compounds M21-2 and M7-4 were used instead of compounds M1-5 and M1-6, with a yield of 71%.

[0321] (4) Synthesis of intermediate M21-4: Referring to the synthesis method of compound M1-7, compounds M21-1 and M21-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 68%.

[0322] (5) Synthesis of Compound M21: Referring to the synthesis method of Compound M1, Compound M21-4 was used instead of Compound M1-8, with a yield of 22%. MS (ASAP): 764.

[0323] Example 22

[0324] This example involves the synthesis of organic compound M22

[0325] The synthetic route is as follows:

[0326]

[0327] (1) Synthesis of intermediate M22-2: Referring to the synthesis method of compound M1-3, compound M22-1 was used instead of compound M1-1, with a yield of 72%.

[0328] (2) Synthesis of intermediate M22-4: Referring to the synthesis method of compound M1-3, compound M22-3 was used instead of compound M1-1, with a yield of 71%.

[0329] (3) Synthesis of intermediate M22-5: Referring to the synthesis method of compound M1-7, compounds M22-4 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 68%.

[0330] (4) Synthesis of intermediate M22-6: Referring to the synthesis method of compound M1-7, compounds M22-2 and M22-5 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0331] (5) Synthesis of Compound M22: Referring to the synthesis method of Compound M1, Compound M22-6 was used instead of Compound M1-8, with a yield of 31%. MS (ASAP): 742.

[0332] Example 23

[0333] This example involves the synthesis of organic compound M23

[0334] The synthetic route is as follows:

[0335]

[0336] (1) Synthesis of intermediate M23-2: Referring to the synthesis method of compound M1-3, compounds M4-1 and M23-1 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 68%.

[0337] (2) Synthesis of intermediate M23-3: Referring to the synthesis method of compound M1-3, compounds M2-1 and M23-1 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 66%.

[0338] (3) Synthesis of intermediate M23-4: Referring to the synthesis method of compound M1-7, compounds M23-3 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 65%.

[0339] (4) Synthesis of intermediate M23-5: Referring to the synthesis method of compound M1-7, compounds M23-2 and M23-4 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 63%.

[0340] (5) Synthesis of Compound M23: Referring to the synthesis method of Compound M1, Compound M23-5 was used instead of Compound M1-8, with a yield of 30%. MS (ASAP): 746.

[0341] Example 24

[0342] This example involves the synthesis of organic compound M24

[0343] The synthetic route is as follows:

[0344]

[0345] (1) Synthesis of intermediate M24-2: Referring to the synthesis method of compound M1-3, compounds M24-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 71%.

[0346] (2) Synthesis of intermediate M24-3: Referring to the synthesis method of compound M1-7, compounds M24-2 and M4-7 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 70%.

[0347] (3) Synthesis of Compound M24: Referring to the synthesis method of Compound M1, Compound M24-3 was used instead of Compound M1-8, with a yield of 26%. MS (ASAP): 992.

[0348] Example 25

[0349] This example involves the synthesis of organic compound M25

[0350] The synthetic route is as follows:

[0351]

[0352] (1) Synthesis of intermediate M25-2: Referring to the synthesis method of compound M1-3, compounds M25-1 and M4-2 were used to replace compounds M1-1 and M1-2, respectively, with a yield of 72%.

[0353] (2) Synthesis of intermediate M25-3: Referring to the synthesis method of compound M1-7, compounds M25-2 and M4-6 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 74%.

[0354] (3) Synthesis of intermediate M25-4: Referring to the synthesis method of compound M1-7, compounds M24-2 and M25-3 were used to replace compounds M1-5 and M1-6, respectively, with a yield of 71%.

[0355] (4) Synthesis of Compound M25: Referring to the synthesis method of Compound M1, Compound M25-4 was used instead of Compound M1-8, with a yield of 24%. MS (ASAP): 874.

[0356] Example 26

[0357] This example provides the preparation and characterization of OLED devices

[0358] The structure of the OLED device is: ITO / HIL (40nm) / HTL (100nm) / light-emitting layer (50nm) / ETL (25nm) / LiQ (1nm) / Al (150nm).

[0359] The steps for preparing OLED are as follows:

[0360] a. Cleaning of the conductive glass substrate: When using it for the first time, it can be cleaned with a variety of solvents, such as chloroform, ketone, and isopropyl alcohol, and then treated with ultraviolet ozone plasma;

[0361] b. Prepare a hole injection layer (HIM) with a thickness of 40 nm on the ITO anode layer by solution processing;

[0362] c. Prepare a hole transport layer (HTM) with a thickness of 100 nm on the hole injection layer by solution processing;

[0363] d. Preparing a light-emitting layer on the hole transport layer by solution processing (the weight ratio of the guest material is 5% of the host material, the guest material is selected from organic compounds M1-M25 and Ref-1; the host material is selected from Host);

[0364] e. Vacuum evaporation method (1×10 -6 mbar) evaporated electron transport layer (material ET1) with a thickness of 25 nm;

[0365] f. Cathode: LiQ / Al (1nm / 150nm) in high vacuum (1×10 -6 mbar) by thermal evaporation, with a thickness of 150nm;

[0366] g. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0367] The compound structures required for OLED preparation are as follows:

[0368]

[0369] The current-voltage (JV) characteristics of the organic light-emitting diodes of Examples M1 to M25 and Comparative Example 1 were measured using characterization equipment. The external quantum dot efficiency and lifetime were also recorded (see Table 1). In Table 1, all external quantum efficiencies and lifetimes are relative to the organic light-emitting diode of Comparative Example 1.

[0370] Among them, LT90 life refers to the current density of 10mA / cm under constant current. 2 , the time it takes for the device's brightness to drop from the initial brightness to 90% of the initial brightness.

[0371] Table 1

[0372]

[0373]

[0374] Compared to OLED devices prepared using the organic compounds of the comparative example, the OLED devices prepared using the organic compounds of Examples 1-25 as guest materials for the light-emitting layer exhibit significantly higher external quantum dot efficiency and T90@1000 nits lifetime than the comparative example. The organic compounds of Examples 1-25 of the present application, which include three nitrogen atoms and two boron atoms in the same rigid plane, exhibit superior fluorescence quantum efficiency.

[0375] Furthermore, the external quantum dot efficiencies and T90@1000 nits of Examples 16-23 exhibit superior luminous efficiency and lifetime compared to the other examples. This may be due to the non-aromatic groups on both sides of the organic compounds in Examples 16-23 acting as flexible side groups, further reducing the π-π stacking effect in the molecular structure and improving the efficiency and stability of the organic compounds in OLED devices.

[0376] The organic compounds, mixtures, compositions and organic electronic devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method and core ideas of the present application. At the same time, for those skilled in the art, according to the ideas of the present application, there may be changes in the specific implementation methods and application scopes. In summary, the contents of this specification should not be understood as limiting the present application.

Claims

1. An organic compound, characterized in that It has the structure shown in the general formula (1): （1） in: Ar7 is selected from any one of the structures shown in formula (B-1) to (B-7): ； Ar6 is selected from any one of the structures represented by formulas (A-1) to (A-5) and (D-1) to (D-13): ， in: Each occurrence of V is independently selected from CR2R3, R2 and R3 are independently selected from: -H or -D; R1, at each occurrence, is independently selected from: -H, -D, or a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, or a cycloalkyl group having 3 to 10 C atoms; Each occurrence of X is independently selected from CR4, and R4 is selected from: -H, -D, a straight chain alkyl group having 1 to 8 C atoms, or a branched chain alkyl group having 3 to 8 C atoms; Y, at each occurrence, is independently selected from NR5, CR6R7, O or S, R5, R6, R7 are independently selected from: -H, -D, straight-chain alkyl having 1 to 10 C atoms or branched-chain alkyl having 3 to 10 C atoms; Ar1 to Ar5 are independently selected from any one of formulas (E-1) to (E-4): in: Each occurrence of X is independently selected from CR4, and R4 is selected from: -H, -D, a straight chain alkyl group having 1 to 8 C atoms, or a branched chain alkyl group having 3 to 8 C atoms; Each occurrence of Y is independently selected from CR6R7 or NR5, and R5, R6, and R7 are independently selected from: -H, -D, or a straight-chain alkyl group having 1 to 10 C atoms or a branched-chain alkyl group having 3 to 10 C atoms; * indicates the fusion site.

2. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the structures shown in formulas (3-1) to (3-11): 。 3. The organic compound according to claim 1, wherein The organic compound is selected from any one of the following compounds: 。 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, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.

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

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

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