Organic compound, preparation method thereof, composition and photoelectric device

Abstract

The invention discloses an organic compound, a preparation method thereof, a composition and a photoelectric device. The organic compound disclosed by the invention has good heat resistance and moisture resistance and is not easily influenced by temperature and humidity; the compound has good hole mobility and hole generation capability, and can be used as a hole injection material or a hole transport material.

Description

Technical Field

[0001] This application relates to the field of organic materials, and particularly to an organic compound, a preparation method thereof, a composition, and an optoelectronic device. Background Art

[0002] Hole functional materials refer to materials with hole transport or hole injection properties. Currently, commonly used metal oxide-based electron transport materials usually have high electron mobility and require hole functional materials with good hole transport or injection characteristics to be matched.

[0003] Therefore, there is an urgent need to develop new hole functional materials and expand the types of hole functional materials. Summary of the Invention

[0004] In view of this, this application provides an organic compound, a preparation method thereof, a composition, and an optoelectronic device.

[0005] The embodiments of this application are implemented as follows:

[0006] In a first aspect, the embodiments of this application provide an organic compound having the structure shown in formula (I):

[0007]

[0008] Wherein, R1 and R2 are each independently selected from one or more of H, D, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted aryl having 6 to 40 ring atoms, and substituted or unsubstituted aryloxy having 6 to 40 ring atoms;

[0009] n1 and n2 are each independently selected from integers from 0 to 5;

[0010] Each occurrence of Ar1 and Ar2 is independently selected from H, D, or one of the following structures:

[0011]

[0012] Wherein, M is SiR7R8, NR9, O or S;

[0013] X is SiR 10 R 11 、CR 12 R 13 、S, O or NR 14 ;

[0014] R3, R4, R5, and R6 are each independently selected from substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C30 a combination of one or more of alkoxy groups;

[0015] R7 to R 14 each independently selected from a combination of one or more of H, D, substituted or unsubstituted C1-C 30 alkyl groups, and substituted or unsubstituted aryl groups having 6 to 60 ring atoms;

[0016] n3 and n4 are each independently selected from integers of 0 to 5;

[0017] n5 and n6 are each independently selected from integers of 0 to 4;

[0018] When substituted by substituents, each occurrence of the substituent is independently selected from a combination of one or more of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl groups, and aryl groups having 6 to 20 ring atoms.

[0019] In a second aspect, an embodiment of the present application further provides a method for preparing an organic compound, including the following steps:

[0020] Mix compound 1 and 2-aminobenzenethiol and carry out a first reaction to obtain compound 2;

[0021] Mix the compound 2 with compound a and carry out a second reaction to obtain compound 3;

[0022] Mix the compound 3 and halogenating agent b and carry out a third reaction to obtain compound 4;

[0023] Mix the compound 4 and compound c and carry out a fourth reaction to obtain organic compound M;

[0024] Wherein, compound 1, compound 2, compound 3, compound a, compound c, and organic compound M have the following structural formulas respectively:

[0025]

[0026] Wherein, R represents R1 or R2, Ar represents Ar1 or Ar2, and X1, X2, and X3 are each independently selected from halogen groups;

[0027] When the atom in Ar connected to Y is an N atom, Y is -H; when the atom in Ar connected to Y is a non-N atom, Y is -B(OH)2;

[0028] R1 and R2 are each independently selected from H, D, substituted or unsubstituted C1-C 30 alkyl groups, and substituted or unsubstituted C1-C 30One or more of alkoxy, substituted or unsubstituted aryl with 6 to 36 ring atoms, and substituted or unsubstituted aryloxy with 6 to 36 ring atoms;

[0029] n1 and n2 are each independently selected from integers of 0 to 5;

[0030] Each occurrence of Ar1 and Ar2 is independently selected from H, D, or one of the following structures:

[0031]

[0032] Wherein, M is SiR7R8, NR9, O or S;

[0033] X is SiR 10 R 11 , CR 12 R 13 , S, O or NR 14 ;

[0034] R3, R4, R5, R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C 30 alkyl, and substituted or unsubstituted C1-C 30 alkoxy;

[0035] R7 to R 14 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C 30 alkyl, and substituted or unsubstituted aryl with 6 to 60 ring atoms;

[0036] n3 and n4 are each independently selected from integers of 0 to 5;

[0037] n5 and n6 are each independently selected from integers of 0 to 4;

[0038] When substituted by substituents, each occurrence of the substituents is independently selected from one or more combinations of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl, and aryl with 6 to 20 ring atoms.

[0039] In a third aspect, the present application further provides a composition, comprising the organic compound described above, or comprising the organic compound prepared by the preparation method described above.

[0040] In a fourth aspect, an embodiment of the present application further provides an optoelectronic device, comprising an anode, a hole functional layer, and a cathode, wherein the material of the hole functional layer comprises the organic compound described above, or comprises the organic compound prepared by the preparation method described above, or the hole functional layer is made of the composition described above.

[0041] The present application provides an organic compound, which has good heat resistance and moisture resistance and is not easily affected by temperature and humidity; the compound has good hole mobility and hole generation ability and can be used as a hole injection material or a hole transport material. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the accompanying drawings required for the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings in the following description are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative efforts.

[0043] Figure 1 It is a schematic structural diagram of an embodiment of an optoelectronic device provided by the present application.

[0044] Reference numerals: optoelectronic device 100; anode 10; cathode 20; electron transport layer 30; light-emitting layer 40; hole injection layer 50; hole transport layer 60. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0045] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only some embodiments of the present application, rather than all embodiments. All other embodiments obtained by those skilled in the art based on the embodiments of the present application without creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific embodiments described herein are only for explaining and understanding the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the orientation terms such as "upper" and "lower" specifically refer to the drawing directions in the drawings. In addition, in the description of the present application, the term "including" means "including but not limited to". The various embodiments of the present application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and brevity, and should not be construed as a rigid limitation on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., 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 including any cited number (fraction or integer) within the indicated range.

[0046] In this application, "and / or" describes the association relationship of associated objects, indicating that there can be three relationships. For example, A and / or B can represent: A exists alone, A and B exist simultaneously, and B exists alone. Here, A and B can be singular or plural.

[0047] In this application, "at least one" means one or more, and "a plurality" means two or more. "At least one kind", "at least one of the following items (pieces)" or similar expressions refer to any combination of these items, including any combination of single item (piece) or plural items (pieces). For example, "at least one of a, b, or c", or "at least one of a, b, and c" can both represent: a, b, c, a - b (i.e., a and b), a - c, b - c, or a - b - c, where a, b, and c can be single or multiple respectively.

[0048] In this application, the aromatic group, aromatic, and aromatic ring system have the same meaning and can be interchanged.

[0049] In this application, the heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be interchanged.

[0050] In this application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted and no other definition is provided, "substituted" means that the hydrogen of the compound or group is replaced by a substituent.

[0051] In this application, "the number of ring atoms" represents the number of ring atoms that form the ring itself in a structural compound obtained by bonding atoms into a ring (for example, a monocyclic compound or a polycyclic compound), that is, the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same applies to the "number of ring atoms" described below without special instructions. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thiophenyl group is 5.

[0052] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, and the aryl group can optionally be further substituted. Preferably, it is a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthylenyl, acenaphthylenyl and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (for example, <10% non-H atoms, such as C, N or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0053] In the present application, "heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, a Si atom, a P atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms" refers to a heteroaryl group having 5 to 60 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, and the heteroaryl group is optionally further substituted; suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, peridinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and their derivatives.

[0054] In the present application, "alkyl" can represent a straight-chain, branched-chain and / or cyclic alkyl group. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. A phrase containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group, or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.

[0055] In this application, "-C n H 2n+1 ", without special indication or limitation, represents a straight-chain alkyl group. For example, -C4H9 represents n-butyl.

[0056] In this application, "alkoxy" refers to a group having the structure "-O-alkyl", that is, the alkyl group defined above is connected 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), tert-butoxy (-O-C(CH3)3 or -OtBu), n-hexyloxy (-O-C6H 13 ), n-decyloxy (-O-C 10 H 21 ), n-dodecyloxy (-O-C 12 H 25 ).

[0057] In the present application, "aryloxy" refers to a group with the structure "-O-aryl", that is, the aryl as defined above is connected to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: phenoxy, naphthyloxy, etc.

[0058] In the present application, "alkylphenyl" is a phenyl substituted by an alkyl group, and its structural formula can be "-phenyl-alkyl", and the alkyl group can refer to the description above. Suitable examples include, but are not limited to: tolyl, ethylphenyl, etc. Among them, C7~C 36 In C7~C of phenylalkyl 36 represents the number of carbon atoms in the whole group.

[0059] In the present application, "alkoxyphenyl" is a phenyl substituted by an alkoxy group, and the alkoxy group can refer to the description above. Suitable examples include, but are not limited to: etc.

[0060] In the present application, "*" connected to a single bond represents a connection site or a fusion site. When the connection site in the group is not specified, it means that any optional connection site in the group can be used as the connection site. For example, in, any optional connection site on the two benzene rings and the connection site on M can be used as the connection site for connecting to the N atom in the main skeleton structure; it can be understood that when M is used as the connection site, M is N or SiR7, in addition, it can also be when M is NR9, or SiR7R8, R7, R8 or R9 is used as the connection site.

[0061] In the present application, the single bond to which the substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any position of the ring. For example in, R4 can be connected to any substitutable site in this benzene ring. Further, in the present application, when the same substituent appears multiple times, it can be independently selected from different groups; for example, in the above general formula, it can contain n4 R4s, and each R4 can be independently selected from different groups.

[0062] In the present application, "its combination", "any combination thereof", "any combination mode thereof", etc. include all suitable combination modes of any two or any two or more items in the listed items.

[0063] In the present application, amino represents -NR 1 R 2 wherein, R 1 , R 2 each independently represents H or an alkyl group, that is, amino can refer to -NH2, or -NH(alkyl), or -N(alkyl)(alkyl).

[0064] In this application, "halogen group" represents -Cl, -Br, -F or -I; hydroxyl group represents -OH; carboxyl group represents -COOH; nitro group represents -NO2; sulfonic acid group represents -SO3H; mercapto group represents -SH; cyano group represents -C≡N.

[0065] This application provides an organic compound having the structure shown in formula (I-1) or (I-2):

[0066]

[0067] Wherein, R1 and R2 are each independently selected from H, D, substituted or unsubstituted C1-C 30 alkyl group, substituted or unsubstituted C1-C 30 alkoxy group, substituted or unsubstituted aryl group with 6 to 40 ring atoms, substituted or unsubstituted aryloxy group with 6 to 40 ring atoms; when substituted by a substituent, each occurrence of the substituent is independently selected from D, amino group, halogen, hydroxyl group, carboxyl group, nitro group, sulfonic acid group, mercapto group, cyano group, C1-C20 alkyl group, aryl group with 6 to 20 ring atoms, or a combination of one or more of them. In some embodiments, R1 and R2 can be the same or different.

[0068] Wherein, n1 and n2 are each independently selected from integers from 0 to 5, for example, can be selected from 0, 1, 2, 3, 4 or 5. In some embodiments, n1 and n2 can be the same or different. In some embodiments, n1 and n2 are each independently selected from 0 or 1.

[0069] Wherein, each occurrence is independently selected from H, D, or one of the following structures:

[0070]

[0071] Wherein, M is SiR7R8, NR9, O or S; X is SiR 10 R 11 、CR 12 R 13 、S, O or NR 14 ; R3, R4, R5, R6 are each independently selected from substituted or unsubstituted C1-C 30 alkyl group, substituted or unsubstituted C1-C 30 alkoxy group, or a combination of one or more of them; R7 to R 14 are each independently selected from H, D, substituted or unsubstituted C1-C 30 alkyl group, substituted or unsubstituted aryl group with 6 to 60 ring atoms, or a combination of one or more of them; n3, n4 are each independently selected from integers from 0 to 5; n5, n6 are each independently selected from integers from 0 to 4.

[0072] In some embodiments, when substituted by the substituents, each occurrence of the substituents is independently selected from one or more combinations of D, C1-C10 alkyl groups, and aryl groups having 6-10 ring atoms.

[0073] The organic compound proposed in the embodiments of the present application has fluorenone as the core and simultaneously has a phenothiazine structural unit fused with fluorenone. The organic compound has a large rigid structure and a conjugated structure, not only having good heat resistance and moisture resistance, making the properties of the compound not easily affected by temperature and humidity, but also being more conducive to intramolecular charge transfer, and having good hole mobility and hole generation ability, and can be used as a hole injection material or a hole transport material.

[0074] In addition, by finely tuning the compound structure, such as increasing or decreasing the number of fused phenothiazine structural units, changing the substituents R1 and / or R2 on the N atom, changing the type, number, and substitution sites of the end group substituents Ar1 / Ar2, etc., compounds with different hole mobilities and energy levels can be obtained, providing a more free and broad choice for the screening of the film layer materials of the optoelectronic device 100.

[0075] In some embodiments, such an organic compound can be used to prepare the hole functional layer of the optoelectronic device 100, such as the hole transport layer 60 or the hole injection layer 50. On the one hand, due to the high hole transport / injection performance of the compound, the hole injection ability can be well enhanced, the carrier balance of the device can be improved, which helps to enhance the optoelectronic performance and lifespan of the device. On the other hand, due to the high stability of the compound, the device can have good stability in a humid and hot environment, which helps to extend the service life of the device. In addition, the compound is not easily dissociated into acid radicals in a liquid environment and has relatively weak acidity. When used as a film layer material, it can avoid corroding adjacent film layers and causing leakage current.

[0076] In some embodiments, in the organic compound, two phenothiazine structural units are fused to the fluorenone unit, that is, the organic compound has the structure shown in the formula (I-2). The compound in this embodiment has a highly symmetric structure and a larger conjugated structure, further improving the heat resistance and hole mobility of the compound.

[0077] The organic compound has a relatively high hole mobility and can better match with common electron transport materials such as metal oxide nanoparticles; specifically, in some embodiments, the hole mobility of the organic compound is 3×10 - 3 cm 2 V -1 s -1 ~5×10 -3 cm 2 V -1 s-1 .

[0078] The terminal substituents Ar1 and Ar2 can be connected to any connection site on the benzene ring, and there can be 0, 1, 2, or more than two substituents on the benzene ring. In some embodiments, the organic compound has the structure shown in formula (II):

[0079]

[0080] Furthermore, in some embodiments, Ar1 and Ar2 are the same, and R1 and R2 are the same. The structure of the compound has better symmetry, which is not only easier to synthesize but also has higher heat resistance.

[0081] In order to better regulate the HOMO energy level and hole mobility of the compound, the terminal substituents Ar1 and Ar2 can be optimized. In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structures:

[0082]

[0083] Wherein, M is SiR7R8, NR9, O or S. X is SiR 10 R 11 , CR 12 R 13 , S, O or NR 14 .

[0084] Wherein, R3, R4, R5, and R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy. When substituted by a substituent, each occurrence of the substituent is independently selected from one or more combinations of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl, aryl with 6-20 ring atoms. In some embodiments, R3, R4, R5, and R6 are each independently selected from one or more combinations of C1-C 30 alkyl, C1-C 30 alkoxy. In other embodiments, R3, R4, R5, and R6 are each independently selected from one or more combinations of C1-C 10 alkyl, C1-C 10 alkoxy.

[0085] Wherein, R7 to R 14 are each independently selected from H, D, substituted or unsubstituted C1-C 30One or more combinations of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms. When substituted by a substituent, each occurrence of the substituent is independently selected from one or more combinations of D, amino, halogen, hydroxy, carboxy, nitro, sulfo, mercapto, cyano, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms. In some embodiments, they are independently selected from H, D, C1-C 30 One or more combinations of an alkyl group and an aryl group having 6 to 60 ring atoms; in other embodiments, R7 to R 14 Are independently selected from H, D, C1-C 10 One or more combinations of an alkyl group and an aryl group having 6 to 10 ring atoms; in still other embodiments, R7 to R 14 Are independently selected from H, D, C1-C 10 One of an alkyl group and a phenyl group.

[0086] Wherein, n3 and n4 are independently selected from integers from 0 to 5, for example, can be selected from 0, 1, 2, 3, 4 or 5; n3 and n4 can be the same or different. n5 and n6 are independently selected from integers from 0 to 4, for example, can be selected from 0, 1, 2, 3 or 4; n5 and n6 can be the same or different.

[0087] In some embodiments, each occurrence of Ar1 and Ar2 is independently selected from one of the following structures:

[0088]

[0089] Furthermore, in some embodiments, Ar1 and Ar2 are independently selected from one of the following structural formulas (1-1) to (1-13):

[0090]

[0091] To better adjust the solvent film-forming property of the organic compound, the substituents R1 and R2 on the N atom can be further optimized. In some embodiments, R1 and R2 are independently selected from H, D, a substituted or unsubstituted C1-C 12 Alkyl group, a substituted or unsubstituted C1-C 12 Alkoxy group, a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and a substituted or unsubstituted aryloxy group having 6 to 18 ring atoms. In other embodiments, R1 and R2 are independently selected from C1-C 12 Alkyl group, C1-C 12 Alkoxy group, and one or more of C7-C 18 Alkoxyphenyl groups.

[0092] It is understood that in some embodiments, when substituted by the substituents involved in the present application, each occurrence of the substituent is independently selected from one or more combinations of D, C1-C10 alkyl groups, and aryl groups having 6-10 ring atoms.

[0093] In some specific embodiments, the organic compound includes one or more of the following structural formulas:

[0094]

[0095]

[0096] The present application also provides a method for preparing an organic compound, and the organic compound can be prepared through the following synthetic route.

[0097]

[0098] The preparation method includes the following steps:

[0099] S10, Mix compound 1 and 2-aminobenzenethiol, and carry out a first reaction to obtain compound 2;

[0100] S20, Mix the compound 2 with compound a, and carry out a second reaction to obtain compound 3;

[0101] S30, Mix the compound 3 and halogenating agent b, and carry out a third reaction to obtain compound 4;

[0102] S40, Mix the compound 4 with compound c, and carry out a fourth reaction to obtain organic compound M;

[0103] Among them, compound 1, compound 2, compound 3, compound a, compound c, and organic compound M respectively have the structural formulas shown in the above synthetic route.

[0104] Among them, R represents R1 or R2, Ar represents Ar1 or Ar2. It is understood that in some embodiments, compound a includes compound a1 with the structural formula R1X1 and compound a2 with the structural formula R2X2. Mixing compound a1, compound a2, and compound 2 and carrying out the second reaction can obtain compound 3; similarly, compound c includes compound c1 with the structural formula Ar1Y and compound c2 with the structural formula Ar1Y. Mixing compound c1, compound c2, and compound 4 and carrying out the fourth reaction can obtain organic compound M. It is understood that when the atom connected to Y in Ar is an N atom, Y is -H, and when the atom connected to Y in Ar is a non-N atom, Y is -B(OH)2;

[0105] Among them, X1, X2, and X3 are each independently selected from halogen groups;

[0106] R1 and R2 are each independently selected from one or more of H, D, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted aryl having 6-36 ring atoms, and substituted or unsubstituted aryloxy having 6-36 ring atoms;

[0107] n1 and n2 are each independently selected from integers from 0 to 5;

[0108] Each occurrence of Ar1 and Ar2 is independently selected from H, D, or one of the following structures:

[0109]

[0110] wherein M is SiR7R8, NR9, O or S; X is SiR 10 R 11 、CR 12 R 13 、S, O or NR 14 ; R3, R4, R5, and R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy; R7 to R 14 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C 30 alkyl, and substituted or unsubstituted aryl having 6-60 ring atoms; n3 and n4 are each independently selected from integers from 0 to 5; n5 and n6 are each independently selected from integers from 0 to 4;

[0111] When substituted by a substituent, each occurrence of the substituent is independently selected from one or more combinations of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl, and aryl having 6-20 ring atoms.

[0112] In some embodiments, n1 and n2 are each independently selected from 0 or 1.

[0113] In some embodiments, both n1 and n2 are 1.

[0114] In some embodiments, the organic compound has the structure shown in formula (II):

[0115]

[0116] In some embodiments, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0117]

[0118] In some embodiments, Ar1 and Ar2 are the same.

[0119] In some embodiments, R1 and R2 are each independently selected from one or more of C1-C 12 alkyl, C1-C 12 alkoxy, C7-C 18 alkoxyphenyl. In some embodiments, R1 and R2 are the same.

[0120] In some embodiments, the first reaction is an elimination reaction. Step S10 specifically includes: adding compound 1, 2-aminobenzenethiol, and iron citrate to a first solvent to carry out the first reaction to obtain compound 2.

[0121] Wherein, the molar ratio of compound 1 to 2-aminobenzenethiol is 1:(4-5); for example, it can be 1:4, 1:4.1, 1:4.3, 1:4.5, 1:4.7, 1:4.9, 1:5, and values between any two of the above.

[0122] The molar ratio of compound 1 to iron citrate is 1:(4-5); for example, it can be 1:4, 1:4.1, 1:4.3, 1:4.5, 1:4.7, 1:4.9, 1:5, and values between any two of the above.

[0123] The reaction temperature of the first reaction is 80-110°C; for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, and values between any two of the above.

[0124] The reaction time of the first reaction is 8-12 h; for example, it can be 8 h, 8.5 h, 9 h, 9.5 h, 10 h, 10.5 h, 11 h, 12 h, and values between any two of the above.

[0125] The first solvent can be any organic solvent that can dissolve compound 1, 2-aminobenzenethiol, and iron citrate and provide a liquid reaction environment for the reaction. For example, the first solvent can include but is not limited to N,N-dimethylformamide.

[0126] In some embodiments, the second reaction is a carbon-carbon coupling reaction. Step S20 specifically includes: mixing compound 2, compound a, a base, and a second solvent to carry out the second reaction to obtain compound 3.

[0127] Among them, the molar ratio of the compound 2 to the compound a is 1:(3 - 5); for example, it can be 1:3, 1:3.2, 1:3.5, 1:3.8, 1:4, 1:4.1, 1:4.3, 1:4.5, 1:4.7, 1:4.9, 1:5, and values between any two of the above.

[0128] The reaction temperature of the second reaction is 80 - 110 °C; for example, it can be 80 °C, 85 °C, 90 °C, 95 °C, 100 °C, 105 °C, 110 °C, and values between any two of the above.

[0129] The reaction time of the second reaction is 6 - 24 h; for example, it can be 6 h, 6.5 h, 7 h, 7.5 h, 8 h, 8.5 h, 9 h, 9.5 h, 10 h, 10.5 h, 11 h, 12 h, 13 h, 14 h, 15 h, 16 h, 18 h, 20 h, 22 h, 24 h, and values between any two of the above.

[0130] The base can be an inorganic base commonly used in the art, for example, it can include but is not limited to sodium hydroxide, potassium hydroxide, etc.

[0131] The second solvent can be any organic solvent that can dissolve the compound 2, the compound a, and the base and provide a liquid reaction environment for the reaction. For example, the second solvent can include but is not limited to dimethyl sulfoxide.

[0132] In some embodiments, the step S20 can be carried out under the protection of an inert gas to isolate or reduce water and oxygen in the reaction system; it can be understood that the inert gas generally refers to protective gases such as nitrogen, helium, argon, etc.

[0133] In some embodiments, the third reaction is a halogenation reaction.

[0134] Among them, the halogenating agent b can be any common halogenating reagent in the art, such as brominating agent, chlorinating agent, iodinating agent, etc.; specifically, the halogenating agent includes but is not limited to any one of N - bromosuccinimide, liquid bromine, N - chlorosuccinimide.

[0135] In some embodiments, the molar ratio of the compound 3 to the halogenating agent b is 1:(3 - 6); for example, it can be 1:3, 1:3.2, 1:3.5, 1:3.8, 1:4, 1:4.1, 1:4.3, 1:4.5, 1:4.7, 1:4.9, 1:5, 1:5.2, 1:5.5, 1:5.8, 1:6, and values between any two of the above.

[0136] The reaction temperature of the third reaction is 40 - 60 °C; for example, it can be 40 °C, 45 °C, 50 °C, 55 °C, 60 °C, and values between any two of the above.

[0137] The reaction time of the third reaction is 6 to 12 h; for example, it can be 6 h, 6.5 h, 7 h, 7.5 h, 8 h, 8.5 h, 9 h, 9.5 h, 10 h, 10.5 h, 11 h, 12 h, and values between any two of the above values.

[0138] In some embodiments, the fourth reaction is a Suzuki coupling reaction. Step S40 may specifically include: mixing compound 4, compound c, and a palladium catalyst, and performing the fourth reaction to obtain organic compound M.

[0139] Wherein, the molar ratio of the compound 4 to the compound c is 1:(3 to 5); for example, it can be 1:3, 1:3.2, 1:3.5, 1:3.8, 1:4, 1:4.1, 1:4.3, 1:4.5, 1:4.7, 1:4.9, 1:5, and values between any two of the above values.

[0140] The reaction temperature of the fourth reaction is 80 to 110 °C; for example, it can be 80 °C, 85 °C, 90 °C, 95 °C, 100 °C, 105 °C, 110 °C, and values between any two of the above values.

[0141] The reaction time of the fourth reaction is 12 to 24 h; for example, it can be 8 h, 8.5 h, 9 h, 9.5 h, 10 h, 10.5 h, 11 h, 12 h, and values between any two of the above values.

[0142] The palladium catalyst can be a commonly used palladium catalyst in the art, such as tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), tetrakis(triphenylphosphine)palladium (pd(pph3)4), etc.

[0143] It can be understood that the organic compounds provided in this application are not limited to being prepared by the preparation methods of the organic compounds provided in this application.

[0144] Based on the above organic compound embodiments, this application also proposes a composition, which includes the above organic compound and a solvent. The composition can be used as a hole functional layer ink for preparing the hole functional layer of the optoelectronic device 100.

[0145] In one embodiment, in the composition, the concentration of the organic compound is 5 to 20 mg / ml; for example, it can be 5 mg / ml, 6 mg / ml, 7 mg / ml, 8 mg / ml, 9 mg / ml, 10 mg / ml, 12 mg / ml, 14 mg / ml, 15 mg / ml, 16 mg / ml, 18 mg / ml, 20 mg / ml, and values between any two of the above values.

[0146] In some embodiments, the solvent may include, but is not limited to, one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene.

[0147] In some embodiments, the composition may contain one of the above-mentioned organic compounds or two or more of the above-mentioned organic compounds.

[0148] In some embodiments, in the composition, in addition to the organic compound and the solvent, other conductive materials or semiconductor materials may also be included, such as other hole transport materials or hole injection materials, for example, 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro(spiro-TPD), N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), tris(3-methylphenylphenylamino)-triphenylamine (m-MTDATA), poly(p-phenylenevinylene) (PPV), poly[2-methoxy-5-(2-ethylhexoxy)-1,4-phenylenevinylene] (MEH-PPV), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MOMO-PPV), 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraaryldiphenylamine, poly(N-vinylcarbazole) (PVK) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, N,N'-bis(naphthalen-1-yl)-N,N'-diphenylbenzidine (NPB), spiro-NPB, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, derivatives of PEDOT:PSS doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide, etc.

[0149] The composition has good hole generation ability and hole mobility, has good compatibility with common electron transport materials, is used for preparing the hole functional layer of the optoelectronic device 100, helps to promote hole injection, improve carrier balance, and enhance the optoelectronic performance of the device.

[0150] When preparing the hole functional layer with the above composition, solution methods such as spin coating, blade coating, printing or spraying can be used on a substrate. After forming a film, annealing is carried out at 100 - 250 °C for 10 - 60 min to obtain the hole functional layer. Among them, the annealing temperature can be 100 °C, 120 °C, 130 °C, 150 °C, 170 °C, 180 °C, 200 °C, 220 °C, 230 °C, 250 °C and values between any two of the above.

[0151] Furthermore, the present application also proposes an optoelectronic device 100, which includes but is not limited to an organic light-emitting diode, a quantum dot light-emitting diode, and a photodetector. Please refer to Figure 1 , the optoelectronic device 100 includes an anode 10, a hole functional layer, and a cathode 20. The material of the hole functional layer includes the organic compound described above, or an organic compound prepared by the preparation method of the organic compound described above, or is made of the composition described above.

[0152] The hole functional layer of the optoelectronic device 100 contains an organic compound. On the one hand, since the compound has high hole transport / injection performance, it can well enhance the hole injection ability and improve the carrier balance of the device, which helps to enhance the optoelectronic performance and lifespan of the device. On the other hand, since the compound has high stability, the device can have good stability in a humid and hot environment, which helps to extend the service life of the device. In addition, the compound is not easily dissociated into acid radicals in a liquid environment and has relatively weak acidity. When used as a film layer material, it can avoid corroding adjacent film layers and causing leakage current.

[0153] In some embodiments, the hole functional layer includes one or both of a hole transport layer 60 and a hole injection layer 50. When the hole functional layer includes the hole transport layer 60 and the hole injection layer 50, the hole injection layer 50 is located between the hole transport layer 60 and the anode 10. In some embodiments, the material of the hole injection layer 50 includes the above-mentioned organic compound or is made of a composition. The hole transport layer 60 may be made of a material that also contains the above-mentioned organic compound, or may be made of a commonly used hole transport material in the art. For example, it may include, but is not limited to, 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro(spiro-TPD), N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine (DNTPD), tris(3-methylphenylphenylamino)-triphenylamine (m-MTDATA), poly(p-phenylene vinylene) (PPV), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] (MEH-PPV), poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene] (MOMO-PPV), 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, PEDOT:PSS and its derivatives, poly(N-vinylcarbazole) (PVK) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, N,N'-bis(naphthalen-1-yl)-N,N'-diphenylbenzidine (NPB), spiro NPB, or one or more of them.In some other embodiments, the material of the hole transport layer 60 includes the above-mentioned organic compound or is made of a composition. The hole injection layer 50 can adopt a material that also contains the above-mentioned organic compound, or can adopt a common hole injection material in the art. For example, it can include but is not limited to poly(ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS), 2,3,5,6-tetrafluoro-7,7’,8,8’-tetracyanoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPc), poly(9,9-dioctylfluorene-co-N-(4-butylphenyl)diphenylamine) (TFB), polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole, N,N,N’,N’-tetrakis(4-methoxyphenyl)-benzidine (TPD), 4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD), 4,4’,4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 4,4’,4”-tris(N-carbazolyl)-triphenylamine (TCTA), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), 4,4’,4”-tris(diphenylamino)triphenylamine (TDATA) doped with F4-TCNQ, p-doped phthalocyanine (for example, F4-TCNQ-doped zinc phthalocyanine (ZnPc)), F4-TCNQ-doped N,N’-diphenyl-N,N’-bis(1-naphthyl)-1,1’-biphenyl-4,4”-diamine (α-NPD), one or more of transition metal oxides, transition metal chalcogenides; wherein, the transition metal oxides include one or more of NiO, MoO2, WO3, CuO; the metal chalcogenides include one or more of MoS2, MoSe2, WS3, WSe3, CuS.

[0154] In some embodiments, the optoelectronic device 100 may further include a light-emitting layer 40, and the light-emitting layer 40 is disposed between the cathode 20 and the hole functional layer. In one embodiment, the material of the light-emitting layer 40 is selected from organic light-emitting materials or quantum dot light-emitting materials.

[0155] The organic light-emitting materials can be selected from at least one of diaryl anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, TBPe fluorescent material emitting blue light, TTPA fluorescent material emitting green light, TBRb fluorescent material emitting orange light, and DBP fluorescent material emitting red light.

[0156] The quantum dot light-emitting material can be selected from at least one of single-structure quantum dots, core-shell structure quantum dots, and perovskite semiconductor materials. The single-structure quantum dots are selected from at least one of II-VI group compounds, IV-VI group compounds, III-V group compounds, and I-III-VI group compounds. The II-VI group compounds are selected from at least one of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and HgZnSTe. The IV-VI group compounds are selected from at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe, and SnPbSTe. The III-V group compounds are selected from at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb. The I-III-VI group compounds are selected from at least one of CuInS, CuInSe, and AgInS. The core of the core-shell structure quantum dots is selected from any one of the above single-structure quantum dots, and the shell material of the core-shell structure quantum dots is selected from at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS, and ZnS.

[0157] As an example, the quantum dots of the core-shell structure may be selected from, but not limited to, at least one of CdZnSe / CdZnSe / ZnSe / CdZnS / ZnS, CdZnSe / CdZnSe / CdZnS / ZnS CdSe / CdSeS / CdS, InP / ZnSeS / ZnS, CdZnSe / ZnSe / ZnS, CdSeS / ZnSeS / ZnS, CdSe / ZnS, CdSe / ZnSe / ZnS, ZnSe / ZnS, ZnSeTe / ZnS, CdSe / CdZnSeS / ZnS, and InP / ZnSe / ZnS.

[0158] It should be noted that for the materials of the aforementioned single-structure quantum dots, or the core materials of the core-shell structure quantum dots, or the shell materials of the core-shell structure quantum dots, the chemical formulas provided only indicate the elemental composition and do not indicate the content of each element. For example, CdZnSe only indicates that it is composed of three elements, Cd, Zn, and Se. If the content of each element is to be expressed, it corresponds to Cd x Zn 1-x Se, where 0 < x < 1.

[0159] The perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the general structural formula of the inorganic perovskite semiconductor is AMX3, where A is a Cs + ion, M is a divalent metal cation selected from Pb 2+ 、Sn 2+ 、Cu 2+ 、Ni 2+ 、Cd 2+ 、Cr 2+ 、Mn 2+ 、Co 2+ 、Fe 2+ 、Ge 2+ 、Yb 2+ 、Eu 2+ and at least one of them, X is a halogen anion selected from Cl - 、Br - 、I - and at least one of them; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX3, where B is an organic amine cation selected from CH3(CH2) n-2 NH3 + or [NH3(CH2) n NH3] 2+ where n ≥ 2, M is a divalent metal cation selected from Pb 2+ 、Sn 2+ 、Cu 2+ 、Ni 2+ 、Cd2+ , Cr 2+ , Mn 2+ , Co 2+ , Fe 2+ , Ge 2+ , Yb 2+ , Eu 2+ at least one of, X is a halogen anion, selected from Cl - , Br - , I - at least one of. When n = 2, the inorganic metal halide octahedron MX6 4- is connected by sharing vertices. The metal cation M is located at the center of the halogen octahedron, and the organic amine cation B fills the voids between the octahedrons, forming an infinitely extended three-dimensional structure; when n > 2, the inorganic metal halide octahedrons MX6 4- extend in two-dimensional directions to form a layered structure. A bilayer of organic amine cations (protonated monoamine) or a monolayer of organic amine cations (protonated diamine) is inserted between the layers. The organic layer and the inorganic layer overlap with each other to form a stable two-dimensional layered structure.

[0160] In one embodiment, the quantum dot light-emitting material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0161] In one embodiment, the optoelectronic device 100 further includes an electronic functional layer disposed between the cathode 20 and the light-emitting layer 40. The electronic functional layer may include an electron injection layer and / or an electron transport layer 30. When the electronic functional layer includes two layers, namely an electron injection layer and an electron transport layer 30, the electron injection layer is disposed closer to the cathode 20, and the electron transport layer 30 is disposed closer to the light-emitting layer 40. The electronic functional layer may be prepared using known electronic functional materials in the art for the optoelectronic device 100 that have electron transport performance or electron injection performance. Specifically, the material of the electron transport layer 30 includes one or more of metal oxides, doped metal oxides, Group IIB-VIA materials, Group IIIB-VA materials, and Group IB-IIIB-VIA materials; the metal oxides include one or more of ZnO, TiO2, and SnO2; the metal oxides in the doped metal oxides include one or more of ZnO, TiO2, and SnO2, and the doping elements include one or more of Al, Mg, Li, In, and Ga; the Group IIB-VIA materials include one or more of ZnS, ZnSe, CdS, and CdSe; the Group IIIB-VA materials include one or more of InP and GaP; the Group IB-IIIB-VIA materials include one or more of CuInS and CuGaS; the material of the electron injection layer includes at least one of cesium carbonate, cesium fluoride, cesium azide, and lithium fluoride.

[0162] In one embodiment, the anode 10 and the cathode 20 are each independently selected from metal electrodes, carbon electrodes, doped or undoped metal oxide electrodes, and composite electrodes; wherein, the material of the metal electrode is selected from at least one of Al, Ag, Cu, Mo, Au, Ba, Ca, Ni, Ir, and Mg; the material of the carbon electrode is selected from at least one of graphite, carbon nanotubes, graphene, and carbon fibers; the material of the doped or undoped metal oxide electrode is selected from at least one of ITO, FTO, ATO, AZO, GZO, IZO, MZO, ITZO, ICO, AMO, SnO2, In2O3, Cd:ZnO, F:SnO2, In:SnO2, and Ga:SnO2; the material of the composite electrode is selected from at least one of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS, and ZnS / Al / ZnS. Herein, " / " represents a laminated structure. For example, the composite electrode AZO / Ag / AZO represents an electrode with a three-layer laminated composite structure composed of an AZO layer, an Ag layer, and an AZO layer.

[0163] It can be understood that in addition to the above-mentioned functional layers, the optoelectronic device 100 may further be provided with some functional layers that are commonly used in optoelectronic devices 100 and are helpful for improving the performance of the optoelectronic device 100, such as an electron blocking layer, an electron injection layer, a hole blocking layer, and / or an interface modification layer, etc.

[0164] It can be understood that the materials and thicknesses of the respective layers of the optoelectronic device 100 can be correspondingly set and adjusted according to the light emission requirements of the optoelectronic device 100.

[0165] In some embodiments, the optoelectronic device 100 further includes a substrate (not shown in the figure), and the substrate can also be referred to as a substrate, and the above-mentioned film layer structure is disposed on one side of the substrate. The substrate can be a rigid substrate or a flexible substrate. The rigid substrate can be a ceramic material or various glass materials, etc. The flexible substrate can be a substrate formed of materials such as polyimide film (PI) and its derivatives, polyethylene naphthalate (PEN), phosphoenolpyruvate (PEP), or polyphenylene ether resin. In one embodiment, the material of the substrate includes one or more combinations of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyethersulfone.

[0166] It can be understood that the optoelectronic device 100 can be a normal optoelectronic device 100 or an inverted optoelectronic device 100. When the optoelectronic device 100 is a normal optoelectronic device 100, the substrate is bonded to the side of the anode 10 away from the light emitting layer 40. When the optoelectronic device 100 is an inverted optoelectronic device 100, the substrate is bonded to the side of the cathode 20 away from the light emitting layer 40.

[0167] It can be understood that the preparation methods of the respective film layers in the optoelectronic device 100 provided in the present application, including the anode 10, the cathode 20, the light emitting layer 40, the hole functional layer, the electron functional layer, and other film layers, can be realized by conventional techniques in the art, such as chemical methods or physical methods. Among them, the chemical methods include chemical vapor deposition method, sequential ionic layer adsorption and reaction method, anodic oxidation method, electrolytic deposition method, and coprecipitation method. The physical methods include physical coating method and solution method. Among them, the physical coating method includes: thermal evaporation coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion coating method, physical vapor deposition method, atomic layer deposition method, pulsed laser deposition method, etc.; the solution method can be spin coating method, printing method, inkjet printing method, doctor blade coating method, printing method, dip coating method, immersion method, spraying method, roll coating method, casting method, slot die coating method, and bar coating method, etc.

[0168] It is understandable that the optoelectronic device 100 may further include a packaging layer (not shown in the figure) to isolate water and oxygen (for example, to make the concentrations of oxygen and water lower than 0.1 ppm), thereby improving the performance stability of the optoelectronic device 100. Specifically, the packaging material used to form the packaging layer may be selected from at least one of UV glue, metal thin film, and glass glue. In a specific embodiment, the packaging material may be acrylic resin or epoxy resin.

[0169] This application also relates to a display device, which includes the optoelectronic device 100 provided by this application. The display device may be any electronic product with a display function. The electronic products include but are not limited to smartphones, tablet computers, laptop computers, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, in-vehicle displays, televisions, or e-book readers. Among them, the smart wearable devices may be, for example, smart bracelets, smart watches, virtual reality (VR) helmets, etc.

[0170] The following will specifically illustrate this application through specific embodiments. The following embodiments are only partial embodiments of this application and do not limit this application. The raw materials used in the following embodiments are all commercially available products unless otherwise specified.

[0171] Example 1:

[0172] The structural formula of the organic compound M1 in this embodiment is as follows:

[0173]

[0174] The synthesis route of the organic compound M1 in this embodiment is as follows:

[0175]

[0176] Step 1: Add compound M1-1 (CAS: 858799-54-9) (1 mmol, 491.7 mg) to a 100 mL two-necked flask, add 2-aminobenzenethiol (CAS: 137-07-5) (4 mmol, 500 mg), add ferric citrate (4 mmol, 980 mg) (CAS: 3522-50-7), dissolve in 30 mL of N,N-dimethylformamide, heat to 110 °C, react for 12 h, stop the reaction when the raw materials are completely reacted monitored by thin-layer chromatography (TLC), distill the reaction solution under reduced pressure to remove the solvent, mix the crude product with silica gel of 200 to 300 mesh, perform column chromatography separation, and the mobile phase is petroleum ether:ethyl acetate (volume ratio 1:1). Finally, 346 mg of compound M1-2 is obtained. Compound M1-2 is a white solid with a yield of 82%.

[0177] Step 2: Add compound M1-2 (2 mmol, 844 mg) into a 100 mL two-necked flask, and weigh and add 1-bromohexane (8 mmol, 1700 mg) (CAS: 111-25-1), potassium hydroxide (8 mmol, 446 mg). Add 40 ml of dimethyl sulfoxide, introduce nitrogen and use a vacuum pump to evacuate for 15 min. Stir and heat to 85 °C, continue the reaction for 24 h, stop the reaction and cool to room temperature. Extract the reaction solution, and repeatedly extract with 200 ml of water and 1500 ml of dichloromethane for 3 to 4 times. The obtained organic extract is dried with anhydrous magnesium sulfate, and the filtrate is collected and mixed with silica gel of 200 to 300 meshes for purification by column chromatography. The eluent is petroleum ether, dichloromethane and ethyl acetate (volume ratio is 20:1:1). Finally, 1121 mg of compound M1-3 is obtained. Compound M1-3 is a white solid with a yield of 95%.

[0178] Step 3: Add compound M1-3 (1 mmol, 590 mg) into a 100 mL two-necked flask and dissolve it in 40 mL of chloroform. Dissolve N-bromosuccinimide (CAS: 128-08-5) (NBS) (3 mmol, 534 mg) in 10 mL of chloroform and gradually add it dropwise to the solution. Stir for 3 h in an ice bath. Stop the reaction when it is monitored by thin-layer chromatography (TLC) that the raw materials have completely reacted. Distill the reaction solution under reduced pressure to remove the solvent. The crude product is mixed with silica gel of 200 to 300 meshes for column chromatography separation. The mobile phase is petroleum ether:ethyl acetate (volume ratio is 20:1) to obtain the intermediate crude product M1-4. Then add diphenylamine (CAS: 122-39-4) (4 mmol, 676 mg), Pd2(PPh3)4 (0.05 mmol, 50 mg) and aqueous sodium carbonate solution (5 mmol, 480 mg). Then add 40 mL of redistilled toluene and 5 mL of ethanol, introduce nitrogen, use a vacuum pump to evacuate for nitrogen replacement for 15 min. Stir the reaction flask with tin foil to avoid light and heat to 110 °C for reaction for 24 h. Stop the reaction and cool to room temperature. Extract the reaction solution, and repeatedly wash with 1000 mL of dichloromethane and 250 mL of water for 3 to 4 times. The organic phase is dried with anhydrous magnesium sulfate, and the crude separation is carried out by column chromatography. The developing agent is petroleum ether:dichloromethane:acetone (volume ratio is 20:2:1) to obtain 677 mg of the final product M1. M1 is a white solid with a yield of 70%. The NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 7.78 (s, 2H), 7.64 (s, 2H), 7.26 - 7.22 (m, 8H), 7.10 - 7.02 (m, 14H), 6.99 - 6.95 (m, 4H), 4.15 (t, J = 6.4 Hz, 4H), 1.76 - 1.69 (m, 4H), 1.47 - 1.41 (m, 4H), 1.33 - 1.23 (m, 8H), 0.91 - 0.88 (m, 6H).

[0179] Example 2:

[0180] The structural formula of the organic compound M2 in this example is as follows:

[0181]

[0182] Preparation of the organic compound M2:

[0183]

[0184] The synthesis of the organic compound M2 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in Step 2 is replaced with 1-bromododecane (CAS: 143-15-7), and diphenylamine in Step 3 is replaced with triphenylamine boronic acid (CAS: 201802-67-7). The reaction conditions and the amount of substances remain unchanged, and finally a white solid product M2 is obtained. The NMR data is as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 7.77 - 7.74 (m, 4H), 7.69 (s, 2H), 7.61 (s, 2H), 7.47 - 7.46 (m, 2H), 7.44 - 7.41 (m, 2H), 7.28 - 7.22 (m, 10H), 7.15 - 7.10 (m, 12H), 7.06 - 7.01 (m, 4H), 3.89 (t, J = 6.4 Hz, 4H), 1.69 (p, J = 6.6 Hz, 4H), 1.44 - 1.38 (m, 4H), 1.33 - 1.22 (m, 32H), 0.90 - 0.87 (m, 6H).

[0185] Example 3

[0186] The structural formula of the organic compound M3 in this example is as follows:

[0187]

[0188] Preparation of the organic compound M3:

[0189]

[0190] The synthesis of organic compound M3 in this example is similar to that of M1. Only in Example 1, 1-bromohexane in step 2 is replaced with 1-bromooctane (CAS: 111-83-1), and diphenylamine in step 3 is replaced with bis(4-methoxyphenyl)aniline (CAS: 101-70-2). The reaction conditions and the amount of substances remain unchanged, and finally a white solid product M3 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ7.78(s,2H),7.64(s,2H),7.11-7.05(m,10H),6.98-6.93(m,4H),6.80-6.77(m,8H),4.15(t,J=6.4Hz,4H),3.78(s,12H),1.75-1.69(m,4H),1.46-1.40(m,4H),1.32-1.25(m,16H),0.90-0.87(m,6H).

[0191] Example 4

[0192] The structural formula of organic compound M4 in this example is as follows:

[0193]

[0194] Preparation of organic compound M4:

[0195]

[0196] The synthesis of organic compound M4 in this example is similar to that of M1. Only in Example 1, 1-bromohexane in step 2 is replaced with iodobenzene hexyl ether (CAS: 85557-94-4), and diphenylamine in step 3 is replaced with phenoxathiin-2-boronic acid (CAS: 2304440-01-3). The reaction conditions and the amount of substances remain unchanged, and finally a white solid product M4 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ7.72-7.68(m,6H),7.55-7.52(m,2H),7.49-7.48(m,2H),7.41-7.40(m,2H),7.20-7.12(m,8H),7.05-7.01(m,6H),6.99-6.96(m,2H),6.86-6.83(m,4H),4.00(t,J=6.1Hz,4H),1.79-1.73(m,4H),1.47-1.41(m,4H),1.35-1.28(m,8H),0.92-0.89(m,6H).

[0197] Example 5

[0198] The structural formula of the organic compound M5 in this embodiment is as follows:

[0199]

[0200] Preparation of the organic compound M5:

[0201]

[0202] The synthesis of the organic compound MM5 in this embodiment is similar to that of M1, except that in Example 1, 1-bromohexane in Step 2 is replaced with p-decyloxybromobenzene (CAS: 30752-20-6), and diphenylamine in Step 3 is replaced with 4-phenylboronic acid-10H phenoxazine (CAS: 1246021-62-4). The reaction conditions and the amount of substance remain unchanged, and finally a white solid product M5 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ7.57-7.51(m,8H),7.50-7.47(m,2H),7.30-7.23(m,8H),7.11-7.09(m,4H),7.07-7.03(m,8H),7.01-6.97(m,4H),6.87-6.84(m,4H),6.74-6.72(m,4H),4.01(t,J=6.1Hz,4H),1.79-1.73(m,4H),1.45-1.39(m,4H),1.29-1.22(m,24H),0.90-0.87(m,6H).

[0203] Example 6

[0204] The structural formula of the organic compound M6 in this embodiment is as follows:

[0205]

[0206] Preparation of the organic compound M6:

[0207]

[0208] The synthesis of the organic compound M6 in this embodiment is similar to that of M1, except that in Example 1, 1-bromohexane in Step 2 is replaced with p-dodecyloxyiodobenzene (CAS: 116223-59-7), and diphenylamine in Step 3 is replaced with 4-phenylboronic acid-9H carbazole (CAS: 419536-33-7). The reaction conditions and the amount of substance remain unchanged, and finally a white solid product M6 is obtained. The NMR data is as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.16 - 8.13 (m, 4H), 7.65 (s, 8H), 7.64 - 7.62 (m, 4H), 7.56 - 7.56 (m, 2H), 7.52 - 7.51 (m, 2H), 7.51 - 7.48 (m, 2H), 7.34 - 7.22 (m, 12H), 7.07 - 7.04 (m, 4H), 6.87 - 6.84 (m, 4H), 4.01 (t, J=6.1 Hz, 4H), 1.79 - 1.74 (m, 4H), 1.44 - 1.38 (m, 4H), 1.29 - 1.23 (m, 32H), 0.90 - 0.87 (m, 6H).

[0209] Example 7

[0210] The structural formula of the organic compound M7 in this example is as follows:

[0211]

[0212] Preparation of the organic compound M7:

[0213]

[0214] The synthesis of the organic compound M7 in this example is similar to that of M1, except that in step 3 of Example 1, diphenylamine is replaced with dimethoxytriphenylamine boronic acid (CAS: 201802 - 29 - 1), and the reaction conditions and amounts of substances remain unchanged. Finally, a white solid product M7 is obtained. The NMR data is as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.11 - 8.09 (m, 8H), 7.76 - 7.73 (m, 4H), 7.70 - 7.69 (m, 2H), 7.62 - 7.60 (m, 4H), 7.47 - 7.42 (m, 4H), 7.28 - 7.25 (m, 2H), 7.18 - 7.14 (m, 2H), 6.87 - 6.85 (m, 8H), 3.89 (t, J=6.4 Hz, 4H), 3.78 (s, 12H), 1.72 - 1.66 (m, 4H), 1.45 - 1.39 (m, 4H), 1.33 - 1.24 (m, 8H), 0.92 - 0.87 (m, 6H).

[0215] Example 8

[0216] The structural formula of the organic compound M8 in this example is as follows:

[0217]

[0218] Preparation of the organic compound M8:

[0219]

[0220] The synthesis of organic compound M8 in this example is similar to that of M1. Only in Example 1, diphenylamine in Step 3 is replaced by 4-(9,9-dimethyl-10(9H)-acridinyl)phenylboronic acid (CAS: 1246021-61-3). The reaction conditions and the amount of substances remain unchanged, and finally a white solid product M8 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.79-7.76(m,4H),7.69(s,2H),7.61(s,2H),7.44-7.41(m,2H),7.34-7.33(m,2H),7.25-7.19(m,12H),7.12-7.08(m,6H),7.02-7.00(m,4H),3.69(t,J=6.4Hz,4H),1.68-1.62(m,16H),1.42-1.36(m,4H),1.32-1.24(m,8H),0.91-0.88(m,6H).

[0221] Example 9

[0222] The structural formula of organic compound M9 in this example is as follows:

[0223]

[0224] Preparation of organic compound M9:

[0225]

[0226] The synthesis of organic compound M9 in this example is similar to that of M1. Only in Example 1, diphenylamine in Step 3 is replaced by 4-(10H-phenothiazin-10-yl)phenylboronic acid (CAS: 1246021-63-5). The reaction conditions and the amount of substances remain unchanged, and finally a white solid product M9 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.79-7.76(m,4H),7.69(s,2H),7.61(s,2H),7.53-7.49(m,4H),7.45-7.41(m,2H),7.35-7.33(m,2H),7.29-7.25(m,4H),7.22-7.16(m,8H),7.12-7.07(m,6H),3.71-3.68(m,4H),1.68-1.62(m,4H),1.42-1.36(m,4H),1.33-1.23(m,8H),0.92-0.88(m,6H).

[0227] Example 10

[0228] The organic compound M10 in this example is the organic compound M1-2 prepared in Example 1. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ9.36(s,2H),7.84(s,2H),7.76(s,2H),7.24-7.22(m,2H),7.18-7.15(m,2H),7.04-7.00(m,2H),6.96-6.92(m,2H).

[0229] Example 11

[0230] The organic compound M11 in this example is the organic compound M1-3 prepared in Example 1. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ7.78(s,2H),7.63(s,2H),7.24-7.16(m,4H),7.08-7.04(m,2H),7.02-6.97(m,2H),4.16-4.12(m,4H),1.75-1.68(m,4H),1.44-1.37(m,4H),1.35-1.24(m,4H),0.92-0.87(m,6H).

[0231] Comparative Example 1

[0232] Organic compound P1 (CAS: 113933-91-8)

[0233]

[0234] Comparative Example 2

[0235] Preparation of organic compound P2:

[0236]

[0237] The synthesis of the organic compound P2 in this example is similar to the steps of preparing M1 from M1-4 in Example 1, except that in step 3, M1-4 is replaced with P2-1 (CAS: 14348-75-5), and diphenylamine is replaced with 4-phenylboronic acid-9H-carbazole (CAS: 419536-33-7), and the remaining reaction conditions and amounts of substances remain unchanged. Finally, a white solid product P2 is obtained. The NMR data is as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.28 - 8.26 (m, 2H), 8.16 - 8.13 (m, 4H), 8.01 - 7.98 (m, 2H), 7.93 - 7.90 (m, 2H), 7.84 - 7.81 (m, 4H), 7.75 - 7.72 (m, 4H), 7.63 - 7.59 (m, 4H), 7.35 - 7.30 (m, 6H), 7.26 - 7.22 (m, 2H).

[0238] Comparative Example 3

[0239] Preparation of Organic Compound P3:

[0240]

[0241] The synthesis of the organic compound P2 in this example is similar to that of P2, except that diphenylamine is replaced with 4 - 10H - phenothiazine - 10 - phenylboronic acid (CAS: 1246021 - 63 - 5), and the remaining reaction conditions and amounts of substances remain unchanged. Finally, a white solid product P3 is obtained. The NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.28 - 8.25 (m, 2H), 8.02 - 7.99 (m, 2H), 7.94 - 7.90 (m, 2H), 7.70 - 7.67 (m, 4H), 7.50 - 7.46 (m, 4H), 7.46 - 7.42 (m, 4H), 7.24 - 7.17 (m, 8H), 7.08 - 7.03 (m, 4H).

[0242] Comparative Example 4

[0243] Preparation of Organic Compound P4:

[0244]

[0245] The synthetic route of the organic compound P4 is as shown above. Among them, the molar ratio of 2,7 - dibromofluorene - 9 - one (CAS: 113933 - 91 - 8) to trimethyl borate (CAS: 3349 - 42 - 6) is 1:2, and the reaction temperature is -80 °C; the molar ratio of P4 - 2 to 3,7 - dibromo - 10 - hexylphenothiazine (CAS: 312924 - 93 - 9) is 1:2. After mixing them, they are heated to reflux overnight to obtain P4 - 3; the molar ratio of P4 - 3 to diphenylamine is 1:2, and the reaction is carried out under nitrogen protection and in a light - protected environment, and the reaction temperature is 110 °C. The NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.09 - 8.06 (m, 2H), 7.88 - 7.82 (m, 4H), 7.51 - 7.48 (m, 2H), 7.47 - 7.45 (m, 2H), 7.35 - 7.32 (m, 2H), 7.28 - 7.22 (m, 10H), 7.15 - 7.05 (m, 16H), 4.13 (t, J = 6.4 Hz, 4H), 1.72 - 1.66 (m, 4H), 1.45 - 1.39 (m, 4H), 1.33 - 1.24 (m, 8H), 0.91 - 0.88 (m, 6H).

[0246] Device Example 1

[0247] This device example provides a quantum dot light-emitting diode and a preparation method thereof, which specifically include the following steps.

[0248] Step 1: Place the ITO glass sheet in a glass dish containing ethanol solution, ultrasonically clean it with acetone, deionized water, and ethanol for 20 minutes each in sequence, and then dry it with a nitrogen gun; then place the cleaned ITO glass sheet in an oxygen plasma for further cleaning for 10 minutes; continue to treat the surface of the ITO substrate with ultraviolet-ozone for 15 minutes;

[0249] Step 2: Disperse the organic compound M1 prepared in Example 1 in chlorobenzene to make a mixed solution with an M1 concentration of 8 mg / ml; spin-coat the mixed solution on the cleaned ITO glass sheet in air at a rotation speed of 3000 r / min for 30 s; after spin-coating, anneal it in a glove box at an annealing temperature of 80 - 120 °C for 5 - 20 minutes to obtain a hole transport layer with a thickness of 40 nm;

[0250] Step 3: Spin-coat a hexane solution of quantum dot QD (concentration: 20 mg / mL) on the hole transport layer at a spin-coating speed of 2000 r / min for 30 s; then let it stand for 15 minutes in an environment of 10 -2 MPa to obtain a light-emitting layer with a thickness of 30 nm;

[0251] Step 4: Disperse ZnMgO in ethanol to obtain a ZMO solution with a ZnMgO concentration of 30 mg / ml, spin-coat the ZMO solution on the light-emitting layer at a rotation speed of 3000 r / min for 30 s, and then let it stand for 15 minutes in an environment of 10 -2 MPa to obtain an electron transport layer with a thickness of 10 nm;

[0252] Step 5: By thermal evaporation, the vacuum degree is not higher than 3×10 -4Pa, evaporate Ag at a rate of 1 Å / s for 200 s to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and then perform epoxy resin encapsulation.

[0253] Its device structure is: ITO / M1(40nm) / QD(30nm) / ZMO(10nm) / Ag(20nm).

[0254] Device Example 2-11

[0255] Device Example n is basically the same as Device Example 1, except that in Device Example n: when preparing the hole transport layer in Step 2, the organic compound M1 is changed to the organic compound of Example n, where n is an integer from 2 to 11, and the organic compounds of Example n are M2 to M11.

[0256] Device Comparative Examples 1 to 4

[0257] Device Comparative Example m is basically the same as Device Example 1, except that in Device Comparative Example m: when preparing the hole transport layer in Step 2, the organic compound M1 is changed to the organic compound of Comparative Example m, where m is an integer from 1 to 4. Specifically, the organic compounds of the hole transport layer in Device Comparative Examples 1 to 4 are P1 to P4 in sequence.

[0258] Experimental Example

[0259] (I) Hole Mobility

[0260] Respectively use the organic compounds of Examples 1 to 11 and Comparative Examples 1 to 4 as hole transport materials, and refer to the preparation process of each corresponding film layer in Device Example 1 above to construct a detection device with the following structure: ITO / organic compound / MoO3 / Ag. Then use the detection device to detect the hole mobility of the materials, and the results are shown in Table 1.

[0261] The hole mobility of the hole transport material is recorded by the space charge limited current (SCLC) method, and this method can be described by the Mott-Gurney equation: J = 9με0ε r V 2 / (8d 3 )

[0262] where J is the current density, μ is the hole mobility, ε0 is the vacuum permittivity (8.85×10 -12 F / m), ε r is the dielectric constant of the material (for organic semiconductors, it is usually approximately taken as 3), V is the applied bias voltage, and d is the film thickness.

[0263] Table 1

[0264]

[0265]

[0266] As can be seen from the above table, the hole mobilities of the organic compounds proposed in this application are all in the range of 3×10 -3 ~5×10 - 3 cm 2 V -1 s -1 . They have relatively high hole mobilities and can be used as hole transport materials;

[0267] The hole mobility of M1 is significantly higher than that of P1 and P4, the hole mobility of M6 is significantly higher than that of P2, and the hole mobility of M9 is significantly higher than that of P3, indicating that the introduction of the phenothiazine structural unit in a fused manner helps to improve the hole mobility;

[0268] In addition, among the organic compounds M1 and M11, M1 has the best hole mobility, indicating that the introduction of the end group substituents of the heteroaromatic group helps to improve the hole mobility.

[0269] (2) Perform maximum brightness L max tests, lifetime T95 tests, lifetime T95@1000nit tests, current efficiency C.E tests, and stability tests on the quantum dot light-emitting diodes of device examples 1-11 and device comparative examples 1-4. The test results are shown in Table 1.

[0270] Among them, the test methods for the maximum brightness L max and the current efficiency C.E are as follows: Use the FushiDa FPD optical property measurement equipment, and measure parameters such as voltage, current, brightness, and emission spectrum through an efficiency test system built by controlling a QE PRO spectrometer, a Keithley 2400, and a Keithley 6485 with LabView, and calculate the current efficiency C.E through calculation;

[0271] The test method for the lifetime T95@1000nit is: The time required for the brightness of the device to decrease to a certain proportion of the highest brightness under constant current or voltage drive. The time when the brightness drops to 95% of the highest brightness is defined as T95, and this lifetime is the measured lifetime. To shorten the test cycle, the device lifetime test is usually carried out by accelerating the device aging at high brightness and fitting the lifetime at high brightness through an extended exponential decay brightness decay fitting formula, such as: The lifetime at 1000nit is denoted as T95@1000nit. The specific calculation formula is as follows:

[0272]

[0273] Among them, T95 LIt is the lifespan at low brightness, T95 H It is the measured lifespan at high brightness, L H It is when the device is accelerated to the maximum brightness, L L It is 1000 nit. A is the acceleration factor. In this experiment, the value of A is obtained as 1.7 by measuring the lifespans of several groups of QLED devices at the rated brightness

[0274] The method for the heat resistance test is as follows: Test the initial current efficiency C.E of the devices in the device examples and device comparative examples, record their initial data, then place them in a sealed environment at a temperature of 80 °C for 100 hours, record the C.E value after being placed at high temperature, and calculate the C.E decay rate a, which is characterized as the heat resistance

[0275] The method for the moisture resistance test is as follows: Test the initial current efficiency C.E of the devices in the device examples and device comparative examples, record their initial data, then place them in a sealed environment with a humidity of 80% for 100 hours, record the C.E value after being placed in high humidity, and calculate the C.E decay rate b, which is characterized as the moisture resistance

[0276] Table 2

[0277]

[0278]

[0279] It can be seen from Table 2 that

[0280] Compared with the device comparative examples, Device Examples 1 to 11 all have higher maximum brightness Lmax, lifespan T95, lifespan T95@1000 nit, current efficiency C.E, and lower C.E decay rate a and C.E decay rate b. This shows that in the device, the balance between hole injection and electron injection is better, thus enabling the device to have higher optoelectronic performance and lifespan; in addition, the organic compounds of the present application have good tolerance to the humid and hot environment and are not easily affected by temperature and humidity, thus enabling the device to have higher stability, specifically reflected in the lower C.E decay rate a and C.E decay rate b of the device examples

[0281] The above has introduced in detail the organic compounds, their preparation methods, compositions and optoelectronic devices provided by the embodiments of the present application. Specific examples are used in this article to elaborate on the principles and implementation manners of the present application. The descriptions of the above embodiments are only used to help understand the method and its core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, there will be changes in the specific implementation manners and application scopes. In summary, the content of this specification should not be construed as a limitation to the present application

Claims

1. An organic compound, characterized in that, Has the structure shown in formula (I): wherein, R1 and R2 are each independently selected from H, D, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted aryl having 6 to 40 ring atoms, substituted or unsubstituted aryloxy having 6 to 40 ring atoms, or one or more thereof; n1 and n2 are each independently selected from integers of 0 to 5; Each occurrence of Ar1 and Ar2 is independently selected from H, D, or one of the following structures: Wherein, M is SiR7R8, NR9, O or S; X is SiR 10 R 11 , CR 12 R 13 , S, O or NR 14 ; R3, R4, R5, and R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy; R7 to R 14 each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted aryl having 6 to 60 ring atoms; n3 and n4 are each independently selected from integers of 0 to 5; n5 and n6 are each independently selected from integers of 0 to 4; When substituted by substituents, each occurrence of the substituents is independently selected from one or more combinations of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl, aryl with 6-20 ring atoms.

2. The organic compound according to claim 1, characterized in that, R7 to R 14 each independently selected from one or more combinations of H, D, C1 to C 10 alkyl, and aryl having 6 to 10 ring atoms; and / or, R3, R4, R5, and R6 are each independently selected from one or more combinations of C1-C 10 alkyl, C1-C 10 alkoxy; and / or, n3 and n4 are each independently selected from 0 or 1; and / or, n5 and n6 are each independently selected from 0 or 1; and / or, Ar1 and Ar2 are each independently selected from one of the following structures:

3. The organic compound according to claim 2, characterized in that, Ar1 and Ar2 are each independently selected from one of the following structural formulas (1-1) to (1-13):

4. The organic compound according to claim 1, characterized in that, n1 and n2 are each independently selected from 0 or 1; and / or, R1 and R2 are each independently selected from H, D, substituted or unsubstituted C1-C 12 alkyl, substituted or unsubstituted C1-C 12 alkoxy, substituted or unsubstituted aryl having 6 to 18 ring atoms, substituted or unsubstituted aryloxy having 6 to 18 ring atoms, or one or more thereof; and / or, When substituted by substituents, each occurrence of the substituents is independently selected from one or more combinations of D, C1-C10 alkyl, aryl with 6-10 ring atoms.

5. The organic compound according to claim 4, characterized in that, R1 and R2 are each independently selected from one or more of C1-C 12 alkyl, C1-C 12 alkoxy, C7-C 18 alkoxyphenyl.

6. The organic compound according to claim 1, characterized in that, The organic compound includes one or more of the following structural formulas:

7. The organic compound according to claim 1, characterized in that, The hole mobility of the organic compound is 3×10 -3 ~5×10 -3 cm 2 V -1 s -1 。 8. A method for preparing an organic compound, characterized in that, Comprises the following steps: Mix compound 1 and 2-aminobenzenethiol, carry out the first reaction to obtain compound 2; Mix the compound 2 with compound a, carry out the second reaction to obtain compound 3; Mix the compound 3 and halogenating agent b, carry out the third reaction to obtain compound 4; Mix the compound 4 and compound c, carry out the fourth reaction to obtain organic compound M; Wherein, compound 1, compound 2, compound 3, compound a, compound c, and organic compound M have the following structural formulas respectively: Wherein, R represents R1 or R2, Ar represents Ar1 or Ar2, and X1, X2, X3 are each independently selected from halogen groups; When the atom in Ar connected to Y is an N atom, Y is -H, and when the atom in Ar connected to Y is a non-N atom, Y is -B(OH)2; R1 and R2 are each independently selected from H, D, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted aryl having 6 to 36 ring atoms, substituted or unsubstituted aryloxy having 6 to 36 ring atoms, or one or more thereof; n1 and n2 are each independently selected from integers of 0 to 5; Each occurrence of Ar1 and Ar2 is independently selected from H, D, or one of the following structures: Wherein, M is SiR7R8, NR9, O or S; X is SiR 10 R 11 、CR 12 R 13 、S, O or NR 14 ; R3, R4, R5, and R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C1-C 30 alkoxy; R7 to R 14 each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C 30 alkyl, and substituted or unsubstituted aryl having 6 to 60 ring atoms; n3 and n4 are each independently selected from integers of 0 to 5; n5 and n6 are each independently selected from integers of 0 to 4; When substituted by substituents, each occurrence of the substituents is independently selected from one or more combinations of D, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C20 alkyl, aryl with 6-20 ring atoms.

9. The preparation method according to claim 8, wherein, The molar ratio of the compound 1 to 2-aminobenzenethiol is 1:(4-5); and / or, The reaction temperature of the first reaction is 80-110°C; and / or, The reaction time of the first reaction is 8-12 h; and / or, The molar ratio of the compound 2 to the compound a is 1:(3-5); and / or, The reaction temperature of the second reaction is 80-110°C; and / or, The reaction time of the second reaction is 6 to 24 h; and / or, The halogenating agent b includes any one of N-bromosuccinimide, liquid bromine, and N-chlorosuccinimide; and / or, The molar ratio of the compound 3 to the halogenating agent b is 1:(3 to 6); and / or, The reaction temperature of the third reaction is 40 to 60 °C; and / or, The reaction time of the third reaction is 6 to 12 h; and / or, The molar ratio of the compound 4 to the compound c is 1:(3 to 5); and / or, The reaction temperature of the fourth reaction is 80 to 110 °C; and / or, The reaction time of the fourth reaction is 12 to 24 h.

10. A composition, wherein, It includes an organic compound and a solvent. The organic compound includes the organic compound described in any one of claims 1 to 7, or includes the organic compound prepared by the preparation method described in claim 8 or 9.

11. The composition according to claim 10, wherein, In the composition, the concentration of the organic compound is 5 to 20 mg / ml; and / or, The solvent includes one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene; and / or, The composition further includes one or more of 4,4'-N,N'-dicarbazolyl-biphenyl, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))], N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4''-diamine, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-spiro, N,N'-bis(4-(N,N'-diphenyl-amino)phenyl)-N,N'-diphenylbenzidine, tris(3-methylphenylphenylamino)-triphenylamine, poly(p-phenylene vinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene], 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbiphenylamine, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, N,N'-bis(naphthalen-1-yl)-N,N'-diphenylbenzidine, spiro-NPB, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, derivatives of PEDOT:PSS doped with s-MoO3, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane, copper phthalocyanine, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide, and copper oxide.

12. An optoelectronic device, wherein,It includes an anode, a hole functional layer, and a cathode. The material of the hole functional layer includes the organic compound described in any one of claims 1 to 7, or includes the organic compound prepared by the preparation method described in claim 8 or 9, or the hole functional layer is made of the composition described in claim 10 or 11.

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