Organic compounds, compositions and organic electronic devices

Abstract

The application relates to the technical field of light-emitting materials, in particular to an organic compound, a composition and an organic electronic device. The organic compound has a structure as shown in any one of general formula (I) to (III). The organic compound is a novel light-emitting material, and when the organic compound is used in an organic electronic device, the problems of low light-emitting efficiency and short service life of the organic electronic device can be solved.

Description

Technical Field

[0001] This invention relates to the field of luminescent materials technology, and particularly to organic compounds, compositions and organic electronic devices. Background Technology

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

[0003] To improve the luminous efficiency of organic light-emitting diodes (OLEDs), various luminescent material systems based on fluorescence and phosphorescence have been developed. Among these, OLEDs using fluorescent materials exhibit high reliability, but their internal electroluminescence quantum efficiency under electrical excitation is limited to 25% due to the 1:3 branching ratio of singlet to triplet excited states of the exciton. OLEDs using phosphorescent materials have achieved nearly 100% internal electroluminescence quantum efficiency; however, phosphorescent OLEDs also suffer from the roll-off effect, where luminous efficiency decreases rapidly with increasing current or brightness, which is particularly detrimental to high-brightness applications.

[0004] To date, conventional phosphorescent materials with practical application value are iridium- and platinum-containing metal complexes. However, these raw materials are rare and expensive, and the synthesis of metal complexes is complex, resulting in high costs. To overcome these problems, Adachi proposed the concept of reverse internal conversion, which utilizes organic compounds instead of metal complexes as luminescent materials, achieving high efficiency comparable to phosphorescent OLEDs. This concept has been realized through various material combinations, such as composite excited-state materials and thermally excited delayed fluorescence (TADF) materials.

[0005] However, traditional blue TADF materials still lag behind phosphorescent materials in terms of both efficiency and lifespan. Summary of the Invention

[0006] Based on this, the purpose of the present invention is to provide an organic compound that can solve the problems of low efficiency and lifespan of traditional blue light TADF materials.

[0007] The technical solution of the present invention is as follows:

[0008] An organic compound having a structure as shown in any of the general formulas (I) to (III):

[0009]

[0010]

[0011] in:

[0012] Y1 and Y2 are independently selected from B or do not exist, and Y1 and Y2 do not exist at the same time;

[0013] X1, X2, X3, and X4 are each independently selected from NR 01 CR 01 R 02 SiR 01 R 02 , O, S, S(=O)2, S(=O) or do not exist, and X1, X2, X3, X4 do not exist simultaneously;

[0014] R 01 R 02 Each occurrence is independently selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano groups, and so on. Carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups; or R 01 It does not exist;

[0015] M1, M2, M3, and M4 are each independently selected from substituted or unsubstituted aromatic groups having 10 to 40 C atoms, or substituted or unsubstituted heteroaromatic groups having 9 to 40 cyclic atoms.

[0016] A1, A2, A3, A4, A5, A6, N1, N2, N3, and N4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 30 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 cyclic atoms.

[0017] R1, R2, R3, R4, R5, R6, R7, and R8, each appearing independently, are selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, and groups having 7 to 20 carbon atoms. The group may contain aryloxycarbonyl, cyano, carbamoyl, halocarbamoyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups.

[0018] The present invention further relates to 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, light emitters, host materials and organic dyes.

[0019] The present invention further relates to a composition comprising the above-described organic compound or mixture thereof, and at least one organic solvent.

[0020] The present invention further relates to an organic electronic device comprising at least one organic functional layer, wherein the organic functional layer comprises the above-mentioned organic compound, or a mixture thereof, or the organic functional layer is prepared from the above-mentioned composition.

[0021] Beneficial effects:

[0022] The organic compound of this application is linked to at least one boron heteroatom compound and spirocyclopentane, resulting in better conjugation and planarity of the overall molecular structure, thereby improving the rigidity and stability of the organic compound molecule. Furthermore, the introduction of spirocyclopentane can further improve the solubility of the organic compound molecule, making it easier to purify and thus increasing its purity. Increased purity means fewer impurities, preventing the recombination of holes and electrons or the quenching of excitons formed after recombination due to impurities, thereby extending the luminous efficiency and lifespan of the device. In addition, the boron- and heteroatom-containing organic compound described in this application can serve as a blue light guest material, effectively improving the luminous efficiency and lifespan of electroluminescent devices when combined with the host material. Attached Figure Description

[0023] Figure 1 This is a schematic diagram of the structure of an organic electronic device. Detailed Implementation

[0024] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only for illustration and explanation of this application and are not intended to limit this application. In this application, unless otherwise stated, directional terms such as "upper" and "lower" generally refer to the upper and lower positions of the device in actual use or operation, specifically the drawing directions in the accompanying drawings. Furthermore, in the description of this application, the term "comprising" means "including but not limited to," and the term "a plurality of" means "two or more." The term "and / or" includes any and all combinations of one or more of the associated listed items. Various embodiments of this application 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 hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible subranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has 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., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it means to include any referenced number (fraction or integer) within the indicated range.

[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 specification of this application is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0026] In this application, composition and printing ink, or ink, have the same meaning and are interchangeable.

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

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

[0029] In this invention, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0030] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, the general formula contains multiple R... 03 Then R 03 It can be independently selected from different substituents.

[0031] 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.

[0032] In this invention, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0033] "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" means an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N, or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0034] "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, imidazole, triazolyl, imidazole, diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridine, pyridazinyl, pyridinyl, etc. Azinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, pyrazinylpyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzothiopheneyl, benzofuranyl, indolyl, carbazoleyl, pyrroloimidazolyl, pyrrolopyrrololyl, thienopyrrololyl, thienopyrrololyl, furanolol, furanol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, o-diazonaphthyl, quinoxalinyl, phenanthridine, primidyl, quinazolinyl, quinazolinone, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0035] 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 C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-butyl... 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 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-heptadecyl, n-octadecyl, n-heptadecyl, n-heptadecyl, n-heptadecyl, n-heptadecyl, 2-ethylhexane, n-butylhexane, 2-hexylhexane, 2-octylhexane, n-monodecyl, n-hepta ...

[0036] 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.

[0037] In this invention, the silane group can be represented by the chemical formula -Si(Y101)(Y102)(Y103), and Y101, Y102, and Y103 can each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Examples of silane groups include trialkylsilane and triarylsilane, and specific examples include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but the examples are not limited thereto.

[0038] In this invention, "amino group" refers to an amine derivative having the structural feature of formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

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

[0041] In this invention, the "*" connected to the single bond, Indicates a connection or fusion site.

[0042] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0043] In this invention, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0044] 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.

[0045] In this invention, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be connected to any position on the ring, for example... R is attached to any substituted site on the benzene ring, such as... express Can be with The above can be selected at any replaceable position to form a loop.

[0046] In this invention, "adjacent groups" refers to two substituents that have no substituted sites between them.

[0047] In this invention, "two adjacent Rs forming a ring" means a ring system formed by connecting two adjacent Rs. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form an aromatic group or heteroaromatic group with 5-10 substituted or unsubstituted ring atoms; more preferably, it can form an aromatic group or heteroaromatic group with 6 substituted or unsubstituted ring atoms. Preferably, it can form...

[0048] The terms “combinations thereof,” “any combination thereof,” “any combination thereof,” and “combination” used in this invention include all suitable combinations of any two or more items among the listed groups.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] An organic compound having a structure as shown in any of the general formulas (I) to (III):

[0053]

[0054]

[0055] in:

[0056] Y1 and Y2 are independently selected from B or do not exist, and Y1 and Y2 do not exist at the same time;

[0057] X1, X2, X3, and X4 are each independently selected from NR 01 CR 01 R 02 SiR 01 R 02 , O, S, S(=O)2, S(=O) or do not exist, and X1, X2, X3, X4 do not exist simultaneously;

[0058] R 01 R 02 Each occurrence is independently selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, cyano groups, and so on. Carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups; or R 01 It does not exist;

[0059] M1, M2, M3, and M4 are each independently selected from substituted or unsubstituted aromatic groups having 10 to 40 C atoms, or substituted or unsubstituted heteroaromatic groups having 9 to 40 cyclic atoms.

[0060] A1, A2, A3, A4, A5, A6, N1, N2, N3, and N4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 30 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 30 cyclic atoms.

[0061] R1, R2, R3, R4, R5, R6, R7, and R8, each appearing independently, are selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, and groups having 7 to 20 carbon atoms. The group may contain aryloxycarbonyl, cyano, carbamoyl, halocarbamoyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups.

[0062] In some embodiments, the structure of formula (I) selected from any one of formulas (I-1) to (I-2) is as follows:

[0063]

[0064] In some embodiments, A1, A2, A5, and A6 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms. Further, A1, A2, A5, and A6 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms.

[0065] Optionally, A1, A2, A5, and A6 are each independently selected from one or more combinations of the structures shown in formulas (B-1) to (B-6):

[0066]

[0067] in:

[0068] Each time X appears, it is independently selected from N or CR. 03 ;

[0069] Each time Y appears, it is independently selected from CR. 04 R 05 SiR 04 R 05 NR 06 PR 06C = O, S or O;

[0070] R 03 R 04 R 05 R 06 Each occurrence is independently selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, and cyano groups. Carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups.

[0071] Optionally, A1, A2, A5, and A6 are each independently selected from one of the following groups:

[0072]

[0073] In some embodiments, in formula (I-1), A1 and A2 are each independently selected from one of the following groups:

[0074]

[0075] A5 and A6 are each independently selected from one of the following groups:

[0076]

[0077] In some embodiments, in formula (I-2), A1, A2, A5, and A6 are each independently selected from one of the following groups:

[0078]

[0079] Further, optionally, the R 03 Selected from -H, -D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched or cyclic alkyl groups having 3 to 6 carbon atoms, aryl groups having 6 to 10 ring atoms, or one of the following substituents:

[0080]

[0081] In some embodiments, A1, A2, A5, and A6 are selected from the same group.

[0082] Preferably, X1, X2, X3, and X4 are each independently selected from NR. 01 、O、or S.

[0083] Optionally, the R 01 R 02 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, an aromatic group having 6 to 10 ring atoms, or an unsubstituted aromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0084] Further, optionally, the R 01 R 02 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or one of the following substituents:

[0085]

[0086] In some embodiments, X1, X2, X3, and X4 are selected from the same group.

[0087] Preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms. More preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 5 carbon atoms. Even more preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 3 carbon atoms.

[0088] In some embodiments, formula (II) is selected from any one of the structures in formulas (II-1) to (II-2):

[0089]

[0090] in:

[0091] M11, M12, M21, M22, M31, M32, M41, and M42 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 13 C atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 13 cyclic atoms.

[0092] Z is selected from CR 01 R 02 SiR 01 R 02 O, S, S(=O)2 or S(=O).

[0093] Furthermore, formula (II) is selected from any one of the structures in formulas (II-a) to (II-d):

[0094]

[0095] Optionally, M11, M12, M21, M22, M31, M32, M41, and M42 are each independently selected from one or more combinations of the structures shown in formulas (B-1) to (B-6):

[0096]

[0097] in:

[0098] Each time X appears, it is independently selected from N or CR. 03 ;

[0099] Each time Y appears, it is independently selected from CR. 04 R 05 SiR 04 R 05 NR 06 PR 06 C = O, S or O;

[0100] R 03 R 04 R 05 R 06Each occurrence is independently selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, and cyano groups. Carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups.

[0101] Optionally, M11, M12, M21, M22, M31, M32, M41, and M42 are each independently selected from...

[0102] In some embodiments, in formula (II-a), M11, M21, M31, and M41 are each independently selected from... M12, M22, M32, and M42 are each independently selected from

[0103] In some embodiments, in formula (II-b), M11, M21, M31, M32, M41, and M42 are each independently selected from... M12 and M22 are selected independently from

[0104] In some embodiments, in formula (II-c), M11, M21, M31, and M41 are each independently selected from... M12, M22, M32, and M42 are each independently selected from

[0105] In some embodiments, in formula (II-d), M11, M21, M31, M32, M41, and M42 are each independently selected from... M12 and M22 are selected independently from

[0106] Preferably, formula (II) is selected from any of the following structures:

[0107]

[0108] Further, optionally, the R 03 Selected from -H, -D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched or cyclic alkyl groups having 3 to 6 carbon atoms, aryl groups having 6 to 10 ring atoms, or one of the following substituents:

[0109]

[0110] In some embodiments, M11, M12, M21, M22, M31, M32, M41, and M42 are selected from the same group.

[0111] Preferably, X1, X2, X3, and X4 are each independently selected from NR. 01 .

[0112] Optionally, the R 01 R 02 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, an aromatic group having 6 to 10 ring atoms, or an unsubstituted aromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0113] Further, optionally, the R 01 R 02 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or one of the following substituents:

[0114]

[0115] In some embodiments, X1, X2, X3, and X4 are selected from the same group.

[0116] Preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms. More preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 5 carbon atoms. Even more preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 3 carbon atoms.

[0117] In some embodiments, formula (III) is selected from any one of formulas (III-1) to (III-2):

[0118]

[0119] In some embodiments, N1, N2, N3, and N4 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 20 ring atoms. Further, A1, A2, A5, and A6 are each independently selected from substituted or unsubstituted aromatic groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms.

[0120] Optionally, N1, N2, N3, and N4 are each independently selected from one or more combinations of the structures shown in formulas (B-1) to (B-6):

[0121]

[0122] in:

[0123] Each time X appears, it is independently selected from N or CR. 03 ;

[0124] Each time Y appears, it is independently selected from CR. 04 R 05 SiR 04 R 05 NR 06 PR 06 C = O, S or O;

[0125] R 03 R 04 R 05 R 06 Each occurrence is independently selected from -H, -D, 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 or cyclic alkyl groups having 3 to 20 carbon atoms, branched or cyclic alkoxy groups having 3 to 20 carbon atoms, branched or cyclic thioalkoxy groups having 3 to 20 carbon atoms, silyl groups, ketone groups having 1 to 20 carbon atoms, alkoxycarbonyl groups having 2 to 20 carbon atoms, aryloxycarbonyl groups having 7 to 20 carbon atoms, and cyano groups. Carbamoyl, halocarbamoyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amino, -CF3, -Cl, -Br, -F, -I, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring atoms, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring atoms, or combinations of these groups.

[0126] Optionally, N1, N2, N3, and N4 are each independently selected from one of the following groups:

[0127]

[0128] In some embodiments, in formulas (III-1), (III-2), and (III-3), N1 and N3 are each independently selected from one of the following groups:

[0129] N2 and N4 are each independently selected from one of the following groups:

[0130]

[0131] In some embodiments, N1, N2, N3, and N4 are selected from the same group.

[0132] In some embodiments, N1, N2, N3, and N4 are selected from different functional groups.

[0133] Preferably, formula (III) is selected from any of the following structures:

[0134]

[0135] R 03 Each occurrence is independently selected from -H, straight-chain alkyl groups having 1 to 6 carbon atoms, or branched alkyl groups having 3 to 6 carbon atoms.

[0136] Further optional, R 03 Each occurrence is independently selected from -H or tBu.

[0137] Preferably, X1, X2, X3, and X4 are each independently selected from NR. 01 .

[0138] Optionally, the R 01 R 02 Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, an aromatic group having 6 to 10 ring atoms, or an unsubstituted aromatic group having 6 to 10 ring atoms, or a combination of these groups.

[0139] Further, optionally, the R 01 R 02Each occurrence is independently selected from -H, -D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched or cyclic alkyl group having 3 to 6 carbon atoms, or one of the following substituents:

[0140]

[0141]

[0142] In some embodiments, X1, X2, X3, and X4 are selected from the same group.

[0143] Preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 10 carbon atoms. More preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 5 carbon atoms. Even more preferably, each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 3 carbon atoms.

[0144] As an example, in some embodiments, the organic compounds described in this invention may be selected from, but are not limited to, any of the following structures:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] It is understandable that the H in the structural formula of the above organic compounds can be further substituted.

[0155] In some embodiments, the organic compounds of this application can be used as organic functional materials in the functional layers of organic electronic devices, particularly in the functional layers of OLED devices. The organic functional materials can be, but are not limited to, hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent guest materials, luminescent host materials, and organic dyes.

[0156] In some embodiments, the organic compound of this application is used in the light-emitting layer. In at least one embodiment, the organic compound of this application is used as a guest material in the light-emitting layer.

[0157] In some embodiments, the organic compound described in this application is used as a blue light-emitting material in the light-emitting layer.

[0158] This application further relates to a composition comprising at least one organic compound as described above and at least another organic functional material. The other organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes. The luminescent material is selected from singlet luminescent materials (fluorescent materials), triplet luminescent materials (phosphorescent materials), and organic thermally excited delayed fluorescence materials (TADF materials). Detailed descriptions of various organic functional materials can be found in WO2010135519A1, US20090134784A1, and WO 2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0159] In one embodiment, the other organic functional material is selected from the host material; further, the other organic functional material is selected from the blue light host material.

[0160] Furthermore, the composition also includes at least one organic solvent.

[0161] It is understood that the composition may also be referred to as ink.

[0162] When used in printing processes, the viscosity and surface tension of ink are important parameters. Suitable surface tension parameters are appropriate for specific substrates and printing methods. In some embodiments, the surface tension of the ink according to this application ranges from 19 dyne / cm to 50 dyne / cm at operating temperature or 25°C; more preferably from 22 dyne / cm to 35 dyne / cm; and most preferably from 25 dyne / cm to 33 dyne / cm. In some embodiments, the viscosity of the ink according to this application ranges from 1 cps to 100 cps at operating temperature or 25°C; more 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. Inks formulated in this way are advantageous for inkjet printing.

[0163] The organic solvent is selected from at least one of aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate esters, and phosphate esters.

[0164] In at least one embodiment, the organic solvent in the composition is selected from aromatic or heteroaromatic solvents.

[0165] The aromatic or heteroaromatic solvents may be selected from, but are not limited to, p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene. At least one of the following: biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanoate, and ethyl 2-furanoate.

[0166] The ester-based solvent may be selected from, but is not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. At least one of octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0167] The aromatic ketone-based solvent may be selected from, but is not limited to, 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and derivatives thereof. As an example, the derivative may be selected from, but is not limited to, at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, and 2-methylphenylacetone.

[0168] The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0169] The aliphatic ketone-based solvent may be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0170] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0171] In some embodiments, the composition of this application includes at least one organic compound or mixture as described above, and at least one organic solvent, and may further include another organic solvent.

[0172] The other organic solvent may be selected from, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetrahydronaphthalene, naphthane, and indene.

[0173] In some embodiments, suitable organic solvents for this application are solvents with Hansen solubility parameters within the following ranges:

[0174] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0175] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0176] δh (hydrogen bond strength) is in the range of 0.9 to 14.2 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2.

[0177] In some embodiments, the boiling point of the organic solvent is taken into consideration when selecting the composition according to this application. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.

[0178] It is understood that the organic solvent can evaporate from the solvent system to form a thin film comprising the organic compound.

[0179] In some embodiments, the composition is a solution. In still other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, modifying film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0180] In the composition, the content of the organic compound or mixture is 0.01-10 wt%, preferably 0.1-5 wt%, more preferably 0.2-5 wt%, and most preferably 0.25-3 wt%.

[0181] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating method. The printing or coating method may include, but is not limited to, inkjet printing, gravure printing, inkjet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot extrusion coating, etc. Gravure printing, inkjet printing, and inkjet printing are preferred.

[0182] This application also relates to the application of the organic compound or composition described above in organic electronic devices. The specific implementation is as follows:

[0183] An organic electronic device includes at least one organic functional layer. The organic functional layer comprises at least one organic compound or mixture as described above, or the organic functional layer is prepared from the above-described composition.

[0184] Furthermore, the organic electronic device includes a cathode, an anode, and at least one organic functional layer. The organic functional layer comprises at least one organic compound as described above, or the organic functional layer is prepared from the above-described composition.

[0185] The organic functional layer may be, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron blocking layer, an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer (HBL). In at least one embodiment, the organic functional layer is an emissive layer.

[0186] The organic electronic devices mentioned can be, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Organic electroluminescent devices such as OLEDs and organic light-emitting field-effect transistors are particularly preferred. OLEDs are even more particularly preferred.

[0187] In one embodiment, the organic electronic device includes a substrate and an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode sequentially stacked on the substrate. The light-emitting layer contains at least one organic compound or mixture as described above, or the light-emitting layer is prepared from a composition as described above. It is understood that the structure of the organic electronic device is not limited thereto.

[0188] The substrate may be transparent or opaque. The substrate may be rigid or flexible. The substrate may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface; a substrate without surface defects is particularly desirable. In one embodiment, the substrate is flexible, and its material may be selected from, but is not limited to, polymer films or plastics, with a glass transition temperature (Tg) of 150°C or higher, preferably 200°C or higher, more preferably 250°C or higher, and most preferably 300°C or higher. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0189] The anode is the electrode for injecting holes, and the anode can readily inject holes into the hole injection layer, hole transport layer, or light-emitting layer. The anode may comprise a conductive metal, a conductive metal oxide, or a conductive polymer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter or p-type semiconductor material serving as a HIL, HTL, or electron blocking layer (EBL) in the light-emitting layer is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be readily selected by those skilled in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention. The cathode is an electron-injecting electrode, and electrons can be readily injected into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may contain a conductive metal or a conductive metal oxide. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light-emitting material in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials suitable for use as cathodes in organic electronic devices may be used as cathode materials for the devices of the present invention. 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 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.

[0190] The hole injection layer is used to facilitate the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material capable of receiving holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0191] The hole transport layer can be used to transport holes. The hole transport material known in the art for use in the hole transport layer appropriately has a hole mobility > 10. -4 cm 2 ·v -1 ·s -1 Materials that can receive holes transported from the anode or hole injection layer and transfer the holes to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

[0192] The electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. As the electron blocking layer, compounds based on spiroindolazidine or materials known in the art can be used.

[0193] The electron transport layer can be used to transport electrons. Suitable electron transport materials have an electron mobility > 10. -5 cm 2 ·v -1 ·s -1 Materials that can receive electrons injected from the negative electrode and transfer them to the light-emitting layer. Specific examples may include, but are not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.

[0194] The electron injection layer can be used to inject electrons. The preferred electron injection material is one that possesses the ability to transport electrons, has the effect of injecting electrons from the negative electrode, and has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation capabilities. Specific examples include fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but is not limited to these.

[0195] It is understood that the organic electronic device may also include a hole-blocking layer located between the light-emitting layer and the electron transport layer. This hole-blocking layer is a layer that prevents holes from reaching the negative electrode and can typically be formed under the same conditions as the hole injection layer. Specific examples include, but are not limited to, diazole or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0196] The light emission wavelength of the organic electronic device is between 300 and 1000 nm, preferably between 350 and 900 nm, and even more preferably between 400 and 800 nm.

[0197] In one embodiment, the organic electronic device described in this application is a solution-type organic electronic device, wherein one or more functional layers are fabricated by printing; further, the solution-type organic electronic device is a solution-type OLED.

[0198] The present invention also relates to the application of the organic electronic device according to the invention in various electronic devices, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, etc.

[0199] This application also relates to electronic devices that include the aforementioned organic electronic devices. The electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0200] The present application will be specifically described below through specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application. Specific Implementation

[0202] 1. Synthesis of compounds

[0203] Example 1

[0204] The synthetic route of organic compound 1 in this embodiment is as follows:

[0205]

[0206] Synthesis of intermediates 1-2:

[0207] Add 20 mmol of intermediate 1-1 dropwise to a mixture of 10 mmol potassium hydroxide, 10 mL acetone, 50 mL water, and 50 mL ethanol, and stir overnight at room temperature. Filter the precipitate to obtain a solid. Then, add 1 g of Pd / C (5%) to a solution of 100 mL glacial acetic acid / ethyl acetate (1:4), and stir the mixture in a 200 mL autoclave at 4 bar H2 pressure. When hydrogen absorption is complete (approximately 30 minutes), stir the mixture under hydrogen pressure for another 2 hours. Filter the catalyst, and wash the filtrate with 200 mL saturated NaHCO3 solution and 200 mL water. Remove the solvent and dry the residue. Dissolve the residue in 400 mL diethyl ether, 2 g sodium dichromate dihydrate, and concentrated sulfuric acid aqueous solution (3 mL / 20 mL). Stir the mixture overnight at room temperature. The phases were separated, with the aqueous phase washed with 100 mL of diethyl ether each time, and the combined organic phase washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of water each time, and dried with sodium sulfate. The solvent was then removed under reduced pressure and the product was dried under vacuum to give intermediate 1-2 in 83.1% yield, MS (ASAP) = 549.3.

[0208] Synthesis of intermediates 1-3:

[0209] In a flask, add 10 mmol of intermediate 1-2, 1.5 g (0.5 mmol) of molybdic acid, and 60 mL of benzene. Attach a water separator, reflux condenser, and heat to reflux for dehydration. After the reaction is complete, filter to remove insoluble solids, wash with chloroform, combine with the organic phase, evaporate to remove solvent, and purify by rapid column chromatography to give intermediate 1-3 in 45.7% yield, MS (ASAP) = 531.4.

[0210] Synthesis of intermediates 1-5:

[0211] Under a nitrogen atmosphere, 10 mmol of intermediates 1-3 and 40 mmol of intermediates 1-4, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 1-5 in 86.3% yield. MS (ASAP) = 888.1.

[0212] Synthesis of Organic Compound 1:

[0213] Prepare a dry 100mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 1-5 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 120°C; slowly add 20mmol of boron triiodide to the reaction flask, tighten the cap, react for 12h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 1, with a yield of 57.1% and MS (ASAP) = 896.7.

[0214] Example 2

[0215] The synthetic route of organic compound 2 in this embodiment is as follows:

[0216]

[0217] Synthesis of intermediate 2-2:

[0218] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 2-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 2-2 in 80.8% yield. MS (ASAP) = 1288.7.

[0219] Synthesis of organic compound 2:

[0220] Prepare a dry 100mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 2-2 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 120°C; slowly add 20mmol of boron triiodide to the reaction flask, tighten the cap, react for 12 hours, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 2, with a yield of 68.4% and MS (ASAP) = 1296.8.

[0221] Example 3

[0222] The synthetic route of organic compound 3 in this embodiment is as follows:

[0223]

[0224] Synthesis of intermediate 3-2:

[0225] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 3-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 3-2 in 78.9% yield. MS (ASAP) = 1320.4.

[0226] Synthesis of organic compound 3:

[0227] Prepare a dry 100 mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10 mmol of intermediate 3-2 and 20 mL of toluene, evacuate and purge with nitrogen three times, and heat to 120 degrees; slowly add 20 mmol of boron triiodide to the reaction flask, tighten the cap, react for 12 h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 3, with a yield of 63.7% and MS (ASAP) = 1328.5.

[0228] Example 4

[0229] The synthetic route for organic compound 4 in this embodiment is as follows:

[0230]

[0231] Synthesis of intermediate 4-2:

[0232] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 4-1, 0.2 mmol of Pd-132, 0.2 mmol of SPhos, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was extinguished by water extraction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. The crude intermediate 4-2 was purified by rapid column chromatography in 74.9% yield. MS (ASAP) = 892.7.

[0233] Synthesis of intermediate 4-4:

[0234] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 4-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 4-4 in 55.7% yield. MS (ASAP) = 948.6.

[0235] Synthesis of organic compound 4:

[0236] Prepare a dry 100 mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10 mmol of intermediate 4-4 and 20 mL of toluene, evacuate and purge with nitrogen three times, and heat to 120 degrees Celsius; slowly add 20 mmol of boron triiodide to the reaction flask, tighten the cap, react for 12 h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 4, with a yield of 45.8% and MS (ASAP) = 956.7.

[0237] Example 5

[0238] The synthetic route of organic compound 5 in this embodiment is as follows:

[0239]

[0240] Synthesis of intermediate 5-2:

[0241] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 5-1, 0.2 mmol of Pd-132, 0.2 mmol of SPhos, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. The crude intermediate 5-2 was purified by rapid column chromatography in 71.8% yield. MS (ASAP) = 892.9.

[0242] Synthesis of intermediate 5-3:

[0243] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 5-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 5-3 in 49.7% yield. MS (ASAP) = 948.7.

[0244] Synthesis of organic compound 5:

[0245] Prepare a dry 100mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 5-3 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 120°C; slowly add 20mmol of boron triiodide to the reaction flask, tighten the cap, react for 12 hours, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 5, with a yield of 50.7% and MS (ASAP) = 956.1.

[0246] Example 6

[0247] The synthetic route for organic compound 6 in this embodiment is as follows:

[0248]

[0249] Synthesis of intermediate 6-2:

[0250] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 6-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 6-2 in 83.7% yield. MS (ASAP) = 840.6.

[0251] Synthesis of intermediate 6-3:

[0252] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 6-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 6-3 in 60.7% yield. MS (ASAP) = 896.7.

[0253] Synthesis of organic compound 6:

[0254] Prepare a dry 500mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 6-3 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 150°C; slowly add 40mmol of boron triiodide to the reaction flask, tighten the cap, react for 48h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 6, with a yield of 57.8% and MS (ASAP) = 912.7.

[0255] Example 7

[0256] The synthetic route for organic compound 7 in this embodiment is as follows:

[0257]

[0258] Synthesis of intermediate 7-2:

[0259] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 7-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 7-2 in 82.9% yield. MS (ASAP) = 840.8.

[0260] Synthesis of intermediate 7-3:

[0261] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 7-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 7-3 in 63.8% yield. MS (ASAP) = 896.9.

[0262] Synthesis of Organic Compound 7:

[0263] Prepare a dry 500mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 7-3 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 150°C; slowly add 40mmol of boron triiodide to the reaction flask, tighten the cap, react for 48h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 7, with a yield of 50.2% and MS (ASAP) = 912.8.

[0264] Example 8

[0265] The synthetic route for organic compound 8 in this embodiment is as follows:

[0266]

[0267] Synthesis of intermediate 8-2:

[0268] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 8-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. Water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 8-2 in 84.6% yield. MS (ASAP) = 880.6.

[0269] Synthesis of intermediate 8-3:

[0270] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 8-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 8-3 in 74.8% yield. MS (ASAP) = 936.7.

[0271] Synthesis of organic compound 8:

[0272] Prepare a dry 500mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 8-3 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 150°C; slowly add 40mmol of boron triiodide to the reaction flask, tighten the cap, react for 48h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 8, with a yield of 48.4% and MS (ASAP) = 952.8.

[0273] Example 9

[0274] The synthetic route for organic compound 9 in this embodiment is as follows:

[0275]

[0276] Synthesis of intermediate 9-2:

[0277] Under a nitrogen atmosphere, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 9-1, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 9-2 in 87.5% yield. MS (ASAP) = 992.7.

[0278] Synthesis of intermediate 9-3:

[0279] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 9-2 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. After removing the solvent, silica gel was added, and column chromatography was performed using petroleum ether as the eluent to obtain intermediate 9-3 in 80.6% yield. MS (ASAP) = 1048.8.

[0280] Synthesis of Organic Compound 9:

[0281] Prepare a dry 500mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 9-3 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 150°C; slowly add 40mmol of boron triiodide to the reaction flask, tighten the cap, react for 48h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 9, with a yield of 43.4% and MS (ASAP) = 1064.6.

[0282] Example 10

[0283] The synthetic route of organic compound 10 in this embodiment is as follows:

[0284]

[0285] Synthesis of intermediate 10-2:

[0286] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 1-3 and 40 mmol of intermediate 10-1, 0.2 mmol of Pd-132, 0.2 mmol of SPhos, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was extinguished by water extraction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 10-2 in 70.4% yield. MS (ASAP) = 956.4.

[0287] Synthesis of intermediate 10-3:

[0288] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 10⁻² were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4⁻³ was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. The solvent was removed, and the mixture was stirred into silica gel and eluented with petroleum ether for column chromatography separation, yielding intermediate 10⁻³ in 51.3% yield. MS (ASAP) = 10¹².5.

[0289] Synthesis of organic compound 10:

[0290] Prepare a dry 500mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 10⁻³ and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 150°C; slowly add 40mmol of boron triiodide to the reaction flask, tighten the cap, react for 48h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 10, with a yield of 47.8% and MS (ASAP) = 1028.6.

[0291] Example 11

[0292] The synthetic route of organic compound 11 in this embodiment is as follows:

[0293]

[0294] Synthesis of intermediate 11-3:

[0295] 10 mmol of intermediate 11-1 and 10 mmol of intermediate 11-2 were added dropwise to a mixture of 10 mmol of potassium hydroxide, 10 mL of acetone, 50 mL of water, and 50 mL of ethanol, and stirred overnight at room temperature. The precipitate was filtered to obtain a solid, which was then added to a solution of 100 mL of glacial acetic acid / ethyl acetate (1:4), along with 1 g of Pd / C (5%). The mixture was stirred in a 200 mL autoclave at 4 bar H2 pressure. When hydrogen absorption was complete (approximately 30 minutes), the mixture was stirred for another 2 hours under hydrogen pressure. The catalyst was filtered, and the filtrate was washed with 200 mL of saturated NaHCO3 solution and 200 mL of water. The solvent was removed, and the residue was dried. The residue was dissolved in 400 mL of diethyl ether, 2 g of sodium dichromate dihydrate, and concentrated sulfuric acid aqueous solution (3 mL / 20 mL). The mixture was stirred overnight at room temperature. The phases were separated, with the aqueous phase washed with 100 mL of diethyl ether each time, and the combined organic phase washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of water each time, and dried with sodium sulfate. The solvent was then removed under reduced pressure and the product was dried under vacuum to give intermediate 11-3 in 64.1% yield, MS (ASAP) = 393.6.

[0296] Synthesis of intermediate 11-4:

[0297] In a flask, 10 mmol of intermediate 11-3, 1.5 g (0.5 mmol) of molybdic acid, and 60 mL of benzene were added. A water separator was fitted, a reflux condenser was used, and the mixture was heated to reflux for dehydration. After the reaction was complete, the insoluble solids were removed by filtration and washed with chloroform. The organic phase was combined, the solvent was removed by evaporation, and the mixture was purified by rapid column chromatography to give intermediate 11-4 in 35.6% yield, MS (ASAP) = 375.3.

[0298] Synthesis of intermediate 11-6:

[0299] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 11-4 and 20 mmol of intermediate 11-5, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 11-6 in 74.1% yield. MS (ASAP) = 402.7.

[0300] Synthesis of intermediate 11-8:

[0301] Under a nitrogen atmosphere, 10 mmol of intermediate 11-6 and 20 mmol of intermediate 11-7, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 60 °C and reacted for 12 hours. After the reaction was complete, water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 11-8 in 60.8% yield. MS (ASAP) = 710.5.

[0302] Synthesis of intermediate 11-9:

[0303] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 11-8 and 20 mmol of intermediate 1-4, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, along with 150 mL of toluene to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 11-9 in 73.3% yield. MS (ASAP) = 888.6.

[0304] Synthesis of organic compound 11:

[0305] Prepare a dry 100mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10mmol of intermediate 11-9 and 20mL of toluene, evacuate and purge with nitrogen three times, and heat to 120°C; slowly add 20mmol of boron triiodide to the reaction flask, tighten the cap, react for 12h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 11, with a yield of 29.4% and MS (ASAP) = 904.6.

[0306] Example 12

[0307] The synthetic route of organic compound 12 in this embodiment is as follows:

[0308]

[0309] Synthesis of intermediate 12-1:

[0310] 20 mmol of intermediate 11-2 was added dropwise to a mixture of 10 mmol potassium hydroxide, 10 mL acetone, 50 mL water, and 50 mL ethanol, and stirred overnight at room temperature. The precipitate was filtered to obtain a solid, which was then added to a solution of 100 mL glacial acetic acid / ethyl acetate (1:4), along with 1 g of Pd / C (5%). The mixture was stirred in a 200 mL autoclave at 4 bar H2 pressure. When hydrogen absorption was complete (approximately 30 minutes), the mixture was stirred for another 2 hours under hydrogen pressure. The catalyst was filtered, and the filtrate was washed with 200 mL saturated NaHCO3 solution and 200 mL water. The solvent was removed, and the residue was dried. The residue was dissolved in 400 mL diethyl ether, 2 g sodium dichromate dihydrate, and concentrated sulfuric acid aqueous solution (3 mL / 20 mL). The mixture was stirred overnight at room temperature. The phases were separated, with the aqueous phase washed with 100 mL of diethyl ether each time, and the combined organic phase washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of water each time, and dried with sodium sulfate. The solvent was then removed under reduced pressure and the product was dried under vacuum to give intermediate 12-1 in 59.5% yield, MS (ASAP) = 393.2.

[0311] Synthesis of intermediate 12-2:

[0312] In a flask, 10 mmol of intermediate 12-1, 1.5 g (0.5 mmol) of molybdic acid, and 60 mL of benzene were added. A water separator was fitted, a reflux condenser was used, and the mixture was heated to reflux for dehydration. After the reaction was complete, the insoluble solids were removed by filtration and washed with chloroform. The organic phase was combined, the solvent was removed by evaporation, and the mixture was purified by rapid column chromatography to give intermediate 12-2 in 44.2% yield (MS (ASAP) = 375.4).

[0313] Synthesis of intermediate 12-4:

[0314] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 12-2 and 20 mmol of intermediate 12-3, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 12-4 in 81.5% yield. MS (ASAP) = 430.7.

[0315] Synthesis of intermediate 12-5:

[0316] Under a nitrogen atmosphere, 10 mmol of intermediate 12-4 and 20 mmol of intermediate 11-7, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve them. The mixture was heated to 60 °C and reacted for 12 hours. After the reaction was complete, water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 12-5 in 67.9% yield. MS (ASAP) = 738.6.

[0317] Synthesis of intermediate 12-7:

[0318] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 12-5 and 20 mmol of intermediate 12-6, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was then extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude intermediate. This crude intermediate was purified by rapid column chromatography to obtain intermediate 12-7 in 75.7% yield. MS (ASAP) = 944.6.

[0319] Synthesis of organic compound 12:

[0320] Prepare a dry 100 mL Schlenk flask, set up the reaction apparatus, evacuate and purge with nitrogen; keep nitrogen flowing in the reaction flask, add 10 mmol of intermediate 12-7 and 20 mL of toluene, evacuate and purge with nitrogen three times, and heat to 120 degrees; slowly add 20 mmol of boron triiodide to the reaction flask, tighten the cap, react for 12 h, extract with DCM, evaporate the solvent, and then use column chromatography (eluent: PE) to obtain a yellow-green solid, namely organic compound 12, with a yield of 33.8% and MS (ASAP) = 960.7.

[0321] Example 13

[0322] The synthetic route of organic compound 13 in this embodiment is as follows:

[0323]

[0324] Synthesis of intermediate 13-2:

[0325] 10 mmol of intermediate 11-2 and 10 mmol of intermediate 13-1 were added dropwise to a mixture of 10 mmol of potassium hydroxide, 10 mL of acetone, 50 mL of water, and 50 mL of ethanol, and stirred overnight at room temperature. The precipitate was filtered to obtain a solid. This solid was then added to a solution of 100 mL of glacial acetic acid / ethyl acetate (1:4), along with 1 g of Pd / C (5%). The mixture was stirred in a 200 mL autoclave at 4 bar H2 pressure. When hydrogen absorption was complete (approximately 30 minutes), the mixture was stirred for another 2 hours under hydrogen pressure. The catalyst was filtered, and the filtrate was washed with 200 mL of saturated NaHCO3 solution and 200 mL of water. The solvent was removed, and the residue was dried. The residue was dissolved in 400 mL of diethyl ether, 2 g of sodium dichromate dihydrate, and concentrated sulfuric acid aqueous solution (3 mL / 20 mL). The mixture was stirred overnight at room temperature. The phases were separated, with the aqueous phase washed with 100 mL of diethyl ether each time, and the combined organic phase washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of water each time, and dried with sodium sulfate. The solvent was then removed under reduced pressure and the product was dried under vacuum to give intermediate 13-2 in 57.3% yield, MS (ASAP) = 316.3.

[0326] Synthesis of intermediate 13-3:

[0327] In a flask, 10 mmol of intermediate 13-2, 1.5 g (0.5 mmol) of molybdic acid, and 60 mL of benzene were added. A water separator was fitted, a reflux condenser was used, and the mixture was heated to reflux for dehydration. After the reaction was complete, the insoluble solids were removed by filtration and washed with chloroform. The organic phase was combined, the solvent was removed by evaporation, and the mixture was purified by rapid column chromatography to give intermediate 13-3 in 41.5% yield (MS (ASAP) = 298.4).

[0328] Synthesis of intermediate 13-5:

[0329] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 13-3 and 10 mmol of intermediate 13-4, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, and 150 mL of toluene was added to dissolve them. The mixture was heated to 110 °C and refluxed for 12 hours until the reaction was complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 13-5 in 82.6% yield. MS (ASAP) = 367.5.

[0330] Synthesis of intermediate 13-7:

[0331] Under a nitrogen atmosphere, 10 mmol of intermediate 13-5 and 10 mmol of intermediate 13-6, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added to a dry three-necked flask. 150 mL of toluene was added to dissolve the substances. The mixture was heated to 60 °C and reacted for 12 hours. After the reaction was complete, water was added to extinguish the reaction, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. The crude solution was purified by rapid column chromatography to obtain intermediate 13-7 in 61.3% yield. MS (ASAP) = 511.0.

[0332] Synthesis of intermediate 13-9:

[0333] Under a nitrogen atmosphere, in a dry three-necked flask, 10 mmol of intermediate 13-7 and 10 mmol of intermediate 13-8, 0.2 mmol of palladium acetate, 0.2 mmol of tri-tert-butylphosphine, and 1.38 g of potassium carbonate were added, dissolved in 150 mL of toluene. The mixture was heated to 110 °C and refluxed for 12 hours until complete. The reaction was extinguished by extraction with water, and the organic phase was extracted with dichloromethane. The organic phases were combined and washed several times, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated by rotary evaporation to obtain a crude solution. This crude solution was purified by rapid column chromatography to obtain intermediate 13-9 in 66.4% yield. MS (ASAP) = 756.7.

[0334] Synthesis of intermediate 13-10:

[0335] Under anhydrous and oxygen-free conditions, 100 mL of freshly treated THF and 10 mmol of intermediate 13-9 were added to a 250 mL three-necked flask. After stirring to form a suspension, 15.0 mL (42 mmol) of a 2.8 M n-BuLi hexane solution was slowly added under ice bath conditions. The reaction was maintained at this temperature for 30 min, followed by another 30 min at room temperature. The mixture was then cooled using an ice-salt bath, and 40 mmol of intermediate 4-3 was slowly added using a syringe. After stirring at room temperature for 4 hours, the reaction mixture was poured into water, extracted with dichloromethane, and dried over anhydrous sodium sulfate. The solvent was removed, and the mixture was stirred into silica gel and eluented with petroleum ether for column chromatography separation, yielding intermediate 13-10 in 41.7% yield. MS (ASAP) = 812.1.

[0336] Synthesis of organic compound 13:

[0337] In a 250 mL three-necked flask, 10 mmol of intermediate 13-10 and 100 mL of dry tert-butylbenzene were added. Under a nitrogen atmosphere, the mixture was cooled to -30 °C, and (21 mmol) of t-BuLi (tert-butyllithium) hexane solution was added dropwise. The temperature was raised to 60 °C and the reaction was carried out for 2 hours. The hexane solvent was then removed by vacuum distillation. The reaction mixture was cooled again to -30 °C, and 21 mmol of boron tribromide solution was added. The mixture was heated to room temperature and stirred for 0.5 hours. Then, the reaction mixture was cooled to 0 °C, and 42 mmol of N,N-diisopropylethylamine was added. After the addition was complete, the temperature was raised to room temperature and stirred, then further raised to 120 °C and stirred for 3 hours. The reaction mixture was then cooled to room temperature. The reaction was quenched with an aqueous sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The solvent was removed by rotary evaporation to obtain the crude product, which was then purified by rapid silica gel column chromatography to obtain the pure product. Recrystallization from toluene and ethyl acetate yielded a pale yellow solid powder, namely organic compound 13, with a yield of 33.8% and MS (ASAP) = 786.7.

[0338] Comparative Example

[0339] The organic compound in this comparative example is BD-Ref1, and its chemical structural formula is as follows:

[0340]

[0341] 2. Organic Light Emitting Diode Components and Their Fabrication

[0342] In the OLED device of this embodiment, ITO is used as the anode, and PEDOT (polyethylene dioxythiophene, Clevios) is used as the cathode. TM Al4083 was used as the hole injection layer material, PVK (Sigma Aldrich, average Mn 25,000-50,000) was used as the hole transport material, BH was used as the host material of the luminescent material, BD-Ref1 in Examples 1-17 and the comparative examples was used as the guest material of the luminescent material, ET and Liq (8-hydroxyquinoline lithium) were used as electron transport materials, and Al was used as the cathode. The device structure was ITO / PEDOT / PVK / BH:organic compound / ET:Liq / Al.

[0343] A schematic diagram of an OLED device is shown below. Figure 1 As shown in the figure. In this figure, 10 is the substrate, 20 is the anode, 30 is the hole injection layer, 40 is the hole transport layer, 50 is the light-emitting layer, 60 is the electron transport layer, and 70 is the cathode.

[0344] The chemical structural formulas of BH, ET, and Liq are as follows:

[0345]

[0346] The aforementioned BH, ET, Liq, and BD-Ref1 are all commercially available, or their synthesis methods are existing technologies.

[0347] The following specific examples illustrate the fabrication process of OLED devices using the above-mentioned materials.

[0348] Device Example 1

[0349] The method for fabricating an OLED device in this embodiment includes the following steps:

[0350] a. Cleaning of the ITO (Indium Tin Oxide) anode layer: Clean the ITO conductive glass with chloroform, acetone and / or isopropanol, and then perform ultraviolet ozone treatment;

[0351] b. Formation of the hole injection layer: Spin-coating the hole injection layer material PEDOT (polyethylene dioxythiophene, Clevios) onto the ITO anode layer. TM AI4083), and was treated on a hot plate at 180°C for 10 minutes, with a hole injection layer thickness of 40nm;

[0352] c. Formation of hole transport layer: A toluene solution of PVK (Sigma Aldrich, average Mn 25,000-50,000) with a concentration of 5 mg / ml was spin-coated onto the hole injection layer, and then treated on a hot plate at 180°C for 60 minutes. The thickness of the hole transport layer was 20 nm.

[0353] d. Forming the luminescent layer: In a nitrogen glove box, spin-coat the luminescent layer material onto the hole transport layer, and then treat it on a hot plate at 140°C for 10 minutes. The host material of the luminescent layer material is BH, the guest material is organic compound 1 of Example 1 of this application, the solvent is methyl benzoate solution, the mass ratio of the host material to the guest material is 95:5, the concentration of the luminescent layer material is 15 mg / ml, and the thickness of the luminescent layer is 40 nm.

[0354] e. Formation of electron transport layer: In the vacuum chamber, above the light-emitting layer, ET and Liq are placed in different evaporation units and co-deposited in a high vacuum (1×10-6 mbar) at a weight ratio of 50:50 to form an electron transport layer with a thickness of 20 nm.

[0355] f. Formation of cathode layer: Al is deposited on top of the electron transport layer to obtain an Al cathode with a thickness of 100 nm;

[0356] g. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0357] Device Examples 2-13

[0358] The devices are basically the same as in Example 1, except that the guest materials of the light-emitting layers in Examples 2-13 are selected from the organic compounds of Examples 2-13.

[0359] Device Comparison

[0360] It is basically the same as the device in Example 1, except that the guest material of the light-emitting layer in the comparative example of the device is the organic compound BD-Ref1.

[0361] Performance testing and results

[0362] The current-voltage (JV) characteristics of the OLED devices in Examples 1-13 and the comparative examples were tested using characterization equipment. Important parameters such as CIE color coordinates (x, y), voltage @ 1 knits [V], luminous efficacy, and lifetime LT95 @ 1000 nits were recorded. Luminous efficacy is a relative value obtained at a current density of 10 mA / cm². Lifetime LT95 @ 1000 nits refers to the time it takes for the device's brightness to decrease from an initial brightness of 1000 nits to 95% of its initial brightness under constant current. The test results are shown in Table 1.

[0363] Table 1

[0364]

[0365]

[0366] As shown in Table 1:

[0367] The blue OLED devices of Examples 1-13 of this invention exhibit superior luminous efficiency and lifetime compared to OLED-Ref1. Specifically, compared to the blue light devices prepared using the organic compound BD-Ref1 as the guest material in the emitting layer in the comparative example, the blue light devices prepared using organic compounds 1-13 of Examples 1-13 as the guest material in the emitting layer generally show an efficiency improvement of 5-32%.

[0368] The organic compounds of the present invention, by introducing spirocyclopentane, can improve the solubility of organic compound molecules. Compared with the organic compound BD-Ref1 in the comparative example, the solubility of the organic compounds used in Examples 1-13 is generally increased by 6-55%. On the one hand, this makes the organic compounds of the present application easier to purify, thereby improving the purity of the organic compounds and thus achieving the purpose of improving the luminous efficiency of the device and extending its service life; on the other hand, it makes it easier to prepare solution-processed devices and improve the film uniformity.

[0369] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0370] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

1. An organic compound, characterized in that, It has a structure as shown in any of the general formulas (I-1) to (I-2): （I-1）； （I-2）； in: X1, X2, X3, and X4 are each independently selected from NR 01 , O or S; A1, A2, A5, and A6 are each independently selected from one of the following groups: ； R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from -H, -D, or straight-chain alkyl groups having 1 to 10 C atoms. R 01 Selected from -H, -D, straight-chain alkyl groups having 1 to 6 carbon atoms, or one of the following substituents: ； R 03 Selected from -H, -D, or aromatic groups having 6 to 10 ring atoms.

2. The organic compound according to claim 1, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 5 C atoms.

3. The organic compound according to claim 2, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 3 C atoms.

4. The organic compound according to claim 1, characterized in that, The R 03 Selected from phenyl.

5. The organic compound according to claim 1, characterized in that, It has one of the following structures: 。 6. An organic compound, characterized in that, It has a structure as shown in general formula (II-a): (II-a): in: X1, X2, X3, and X4 are each independently selected from N; M11, M12, M21, M22, M31, M32, M41, and M42 are each independently selected from... ; R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from -H, -D, or straight-chain alkyl groups having 1 to 10 C atoms. R 03 Selected from -H, -D, or straight-chain alkyl groups having 1 to 6 carbon atoms.

7. The organic compound according to claim 6, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 5 C atoms.

8. The organic compound according to claim 7, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 3 C atoms.

9. The organic compound according to claim 6, characterized in that, It has one of the following structures: 。 10. An organic compound, characterized in that, It has a structure as shown in any of the general formulas (III-1) to (III-2): (III-1); (III-2); in: X1, X2, X3, and X4 are each independently selected from NR 01 ; N1, N2, N3, and N4 are each independently selected from... ; R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from -H, -D, or straight-chain alkyl groups having 1 to 10 C atoms. R 01 Selected from -H, -D, or one of the following substituents: ； R 03 Each occurrence is independently selected from -H, straight-chain alkyl groups having 1 to 6 carbon atoms, or branched alkyl groups having 3 to 6 carbon atoms.

11. The organic compound according to claim 10, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 5 C atoms.

12. The organic compound according to claim 11, characterized in that, Each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from -H, -D, or straight-chain alkyl groups having 1 to 3 C atoms.

13. The organic compound according to claim 10, characterized in that, It has one of the following structures: 。 14. An organic compound, characterized in that, It has the following structure: 。 15. A composition, characterized in that, It includes the organic compound as described in any one of claims 1-14, 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, and light emitters.

16. The composition according to claim 15, characterized in that, It also contains at least one organic solvent.

17. An organic electronic device, characterized in that, It comprises at least one organic functional layer, wherein the organic functional layer includes the organic compound of any one of claims 1-14, or the organic functional layer is prepared from the composition of claim 15 or 16.

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