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 ultraviolet absorption performance, can absorb ultraviolet rays and avoid ultraviolet light damage, and has relatively good light stability; in addition, the compound also has good hole mobility and hole generation capability, and can be applied 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 performance or hole injection performance, including but not limited to poly(N-vinylcarbazole) (PVK), 4,4'-N,N'-dicarbazolyl-biphenyl (CBP), etc. However, with the increasingly in-depth research and development of hole functional materials, the existing material types are gradually difficult to meet the requirements of more and more application scenarios. Therefore, it is urgent to develop new hole functional materials to expand the types of hole functional materials. Summary of the Invention

[0003] In view of this, this application provides an organic compound, a preparation method thereof, a composition, and an optoelectronic device.

[0004] The embodiments of this application are implemented as follows:

[0005] In a first aspect, the embodiments of this application provide an organic compound having a structure shown in formula (I-1) or (I-2):

[0006]

[0007] Wherein, Ar1, Ar2, and Ar3 are each independently selected from H, D, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, and one of the following structures:

[0008]

[0009] Wherein, M is SiR5R6, NR7, O, or S;

[0010] X is SiR8R9, CR 10 R 11 , S, O, or NR 12 ;

[0011] R1, R2, R3, and R4 are each independently selected from one or a combination of more of a substituted or unsubstituted C1-C30 alkyl group and a substituted or unsubstituted C1-C30 alkoxy group;

[0012] R5 to R 12 are each independently selected from one or a combination of more of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group with 6-20 ring atoms;

[0013] n1 and n2 are each independently selected from integers from 0 to 5;

[0014] n3 and n4 are each independently selected from integers from 0 to 4;

[0015] When substituted by substituents, 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, C1-C20 alkoxy, and aryl with 6-20 ring atoms.

[0016] In a second aspect, an embodiment of the present application further provides a method for preparing an organic compound, including the following steps:

[0017] Using compound a as a raw material, performing a ring-closing reaction to obtain compound b;

[0018] Mixing the compound b with compound c and performing a nitrogen-nitrogen coupling reaction to obtain an organic compound M;

[0019] Among them, the organic compound includes a compound having the structure shown in formula (I-1) and / or (I-2), and compound a, compound b, and compound c have the following structural formulas respectively:

[0020]

[0021] Among them, Ar represents Ar1, Ar2 or Ar3;

[0022] 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 a halogen group;

[0023] Ar1, Ar2, and Ar3 are each independently selected from H, D, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and one of the following structures:

[0024]

[0025] Among them, M is SiR5R6, NR7, O or S; X is SiR8R9, CR 10 R 11 , S, O or NR 12 ; R1, R2, R3, and R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl and substituted or unsubstituted C1-C30 alkoxy; R5 to R 12 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted aryl with 6-20 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers from 0 to 4;

[0026] When substituted by substituents, 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, C1-C20 alkoxy, and aryl having 6-20 ring atoms.

[0027] In a third aspect, the present application further provides a composition, including the organic compound described above, or including the organic compound prepared by the preparation method described above.

[0028] In a fourth aspect, an embodiment of the present application further provides an optoelectronic device, including an anode, a hole functional layer, and a cathode. The material of the hole functional layer includes the organic compound described above, or includes the organic compound prepared by the preparation method described above. Alternatively, the hole functional layer is made of the composition described above.

[0029] The present application provides an organic compound, which has ultraviolet absorption performance, can absorb ultraviolet light, avoid ultraviolet light damage, and has better light stability. In addition, the compound also has good hole mobility and hole generation ability, and can be used as a hole injection material or a hole transport material. Description of the Drawings

[0030] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for the description of the embodiments will be briefly introduced below. Obviously, the drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0031] Figure 1 It is a schematic structural diagram of an embodiment of an optoelectronic device provided by the present application.

[0032] 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 Embodiments

[0033] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain 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" are specifically 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 described range description has specifically disclosed all possible sub-ranges and single values within that 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 that 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.

[0034] In the present application, "and / or" describes the association relationship of associated objects and indicates that three relationships may exist. For example, A and / or B may indicate: A exists alone, A and B exist simultaneously, or B exists alone. Wherein A and B may be singular or plural.

[0035] In the present application, "at least one" means one or more, and "a plurality" means two or more. "At least one kind", "at least one item (piece) below" 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 item (piece) among a, b, or c", or, "at least one item (piece) among a, b, and c" can both represent: a, b, c, a - b (that is, a and b), a - c, b - c, or a - b - c, where a, b, and c can be single or plural respectively.

[0036] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. 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 one or more combinations of the following substituents: deuterium (D), amino group, halogen, hydroxyl group, carboxyl group, nitro group, sulfonic acid group, mercapto group, cyano group, C1-C20 alkyl group, C1-C20 alkoxy group, aryl group having 6-20 ring atoms.

[0037] In the present application, "number of ring atoms" means the number of ring atoms constituting the ring itself in a structural compound obtained by bonding atoms in 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 thienyl group is 5.

[0038] In the present application, "aryl group or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which may be a monocyclic aryl group, a fused-ring aryl group, or a polycyclic aryl group. For a polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 60 ring atoms" refers to an aryl group containing 6 to 60 ring atoms, and the aryl group may 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 group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, perylenyl group, tetracenyl group, fluorenyl group, dinaphthylphenyl group, acenaphthylenyl group and its derivatives. It can be understood that multiple aryl groups may 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.

[0039] In the present application, the "heteroaryl or heteroaromatic group" means that 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, the "substituted or unsubstituted heteroaryl having 5 to 60 ring atoms" means a heteroaryl having 5 to 60 ring atoms, preferably a substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 5 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl having 5 to 14 ring atoms, and the heteroaryl 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 derivatives thereof.

[0040] In the present application, the "alkyl" can represent a straight-chain, branched-chain and / or cyclic alkyl. The number of carbon atoms of the alkyl can be 1 to 30, 1 to 20, 1 to 10 or 1 to 6. A phrase containing this term, for example, "C" 1-9"Alkyl" means 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, etc.

[0041] 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.

[0042] In this application, "alkoxy" means a group with 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 ).

[0043] In the present application, "aryloxy" refers to a group having 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.

[0044] In the present application, "*" connected to a single bond represents a connection site or a fusion site. When the connection site in a 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 SiR5, in addition, it can also be when M is NR7, or SiR5R6, R5, R6 or R7 is used as the connection site.

[0045] In the present application, the single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example in, R1 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, if it contains n1 R1s, each R1 can be independently selected from different groups.

[0046] 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.

[0047] 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).

[0048] In the present application, "halogen group" or "halogen" represents -Cl, -Br, -F or -I; hydroxyl represents -OH; carboxyl represents -COOH; nitro represents -NO2; sulfonic acid group represents -SO3H; mercapto represents -SH; cyano represents *-C≡N.

[0049] The present application provides an organic compound having the structure shown in formula (I-1) or (I-2):

[0050]

[0051] wherein, Ar1, Ar2, and Ar3 are each independently selected from H, D, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, and one of the following structures:

[0052]

[0053] Among them, M is SiR5R6, NR7, O or S; X is SiR8R9, CR 10 R 11 , S, O or NR 12 ; R1, R2, R3, and R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl groups and substituted or unsubstituted C1-C30 alkoxy groups; R5 to R 12 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl groups, and substituted or unsubstituted aryl groups having 6 to 20 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers from 0 to 4.

[0054] In some embodiments, when substituted by the substituent, each occurrence of the substituent is independently selected from one or more combinations of D, C1-C10 alkyl groups, and aryl groups having 6 to 10 ring atoms.

[0055] The organic compound proposed in the embodiments of the present application has dibenzothiophene as the core and also has a benzotriazole structural unit. The organic compound has a relatively large rigid structure and conjugated structure. It not only has ultraviolet absorption performance and can absorb ultraviolet light, making the properties of the compound not easily affected by ultraviolet light and having better light stability, but also is more conducive to intramolecular charge transfer and thus has good hole mobility and hole generation ability, and can be used as a hole injection material or a hole transport material.

[0056] In addition, by finely tuning the compound structure and changing the types of end group substituents Ar1 / Ar2, 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.

[0057] 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 better ultraviolet absorption performance and light stability of the compound, it can absorb the ultraviolet light generated during the device preparation process, reduce the damage of ultraviolet light to the material, and improve the light stability of the device.

[0058] In some embodiments, in the organic compound, there are two benzotriazole structural units, that is, the organic compound has the structure shown in the formula (I-2). The compound of this embodiment has a highly symmetric structure and a larger conjugated structure, further improving the stability and hole mobility of the compound.

[0059] In some embodiments, the two connecting sites a1 and b1 on the triazole can serve as the fusion sites, and the corresponding connecting sites on the benzene ring, such as any two adjacent sites among c1, d1, e1, and f1, can serve as the fusion sites. a1, b1 are fused with the fusion sites on the benzene ring to form a fused structure; in other embodiments, the two connecting sites a2 and b2 on the triazole can serve as the fusion sites, and the corresponding connecting sites on the benzene ring, such as any two adjacent sites among c2, d2, e2, and f2, can serve as the fusion sites. a2, b2 are fused with the fusion sites on the benzene ring to form a fused structure.

[0060]

[0061] In some embodiments, a1, b1, d1, and e1 serve as the fusion sites, and a2, b2, d2, and e2 serve as the fusion sites. Correspondingly, the organic compound has the structure shown in the formula (II):

[0062]

[0063] In some embodiments, the hole mobility of the organic compound is 3×10 -5 ~8×10 -5 cm 2 V -1 s -1 .

[0064] In the formula (I-1) or the formula (II), Ar1 and Ar2 may be the same or different. In some embodiments, Ar1 and Ar2 are the same, and the compound structure has better symmetry, which is not only easier to synthesize but also has higher stability.

[0065] In order to better regulate the HOMO energy level and hole mobility of the compound, the end group substituents Ar1, Ar2, and Ar3 can be optimized. In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from one of the following structures:

[0066]

[0067] Among them, M is SiR5R6, NR7, O or S.

[0068] Among them, X is SiR8R9, CR 10 R 11, S, O or NR 12 .

[0069] Wherein, R1, R2, R3, and R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl groups and substituted or unsubstituted C1-C30 alkoxy groups. 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 group, cyano group, C1-C20 alkyl groups, C1-C20 alkoxy groups, and aryl groups having 6 to 20 ring atoms. In some embodiments, R3, R4, R5, and R6 are each independently selected from one or more combinations of C1-C10 alkyl groups and C1-C10 alkoxy groups.

[0070] Wherein, R5 to R 12 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl groups, and substituted or unsubstituted aryl groups having 6 to 20 ring atoms. 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 group, cyano group, C1-C20 alkyl groups, C1-C20 alkoxy groups, and aryl groups having 6 to 20 ring atoms. In some embodiments, R5 to R 12 are each independently selected from one or more combinations of H, D, C1-C10 alkyl groups, and aryl groups having 6 to 10 ring atoms; in other embodiments, R5 to R 12 are each independently selected from one of H, D, C1-C10 alkyl groups, and phenyl.

[0071] 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; n1 and n2 can be the same or different.

[0072] Wherein, n3 and n4 are each independently selected from integers from 0 to 4, for example, can be selected from 0, 1, 2, 3, or 4; n3 and n4 can be the same or different.

[0073] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from one of the following structures:

[0074]

[0075] Furthermore, in some embodiments, Ar1, Ar2, and Ar3 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0076]

[0077] In some specific embodiments, the organic compound includes one or more of the following structural formulas:

[0078]

[0079] This application also provides a method for preparing an organic compound, and the organic compound can be prepared through the following synthetic route.

[0080]

[0081] The preparation method includes the following steps:

[0082] S10, using compound a as a raw material, performing a ring-closing reaction to obtain compound b;

[0083] S20, mixing the compound b with compound c, and performing a nitrogen-nitrogen coupling reaction to obtain the organic compound M;

[0084] Among them, compound a, compound b, compound c, and the organic compound M respectively have the structural formulas shown in the above synthetic route.

[0085] Among them, in the structure of compound a, the two amino groups on each benzene ring are respectively connected to two adjacent connection sites on the benzene ring. For example, its structure can be one of the following structures:

[0086]

[0087] Among them, Ar represents Ar1, Ar2 or Ar3. It can be understood that in some embodiments, compound c includes compound c1 with the structural formula Ar1Y and compound c2 with the structural formula Ar2Y. Mixing compound c1, compound c2 and compound b and performing a nitrogen-nitrogen coupling reaction can obtain the organic compound I-1. In other embodiments, compound c includes compound c3 with the structural formula Ar3Y, and correspondingly, the organic compound I-2 can be prepared. It can be 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 a halogen group.

[0088] Ar1, Ar2, Ar3 are each independently selected from H, D, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl and one of the following structures:

[0089]

[0090] Among them, M is SiR5R6, NR7, O or S; X is SiR8R9, CR 10 R 11 、S、O or NR 12; R1, R2, R3, and R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl groups and substituted or unsubstituted C1-C30 alkoxy groups; R5 to R 12 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl groups, and substituted or unsubstituted aryl groups having 6 to 20 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers from 0 to 4.

[0091] In some embodiments, the organic compound has the structure shown in formula (II). Correspondingly, the corresponding raw material can be 2,3,7,8-aminodibenzothiophene, CAS: 866363-49-7.

[0092]

[0093] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from one of the following structural formulas (1-1) to (1-13):

[0094]

[0095] In some embodiments, Ar1 and Ar2 are the same.

[0096] In some embodiments, step S10 specifically includes: mixing compound a, sodium nitrite, acid, and water, and performing a ring-closure reaction to obtain compound b.

[0097] Among them, the acid can be acetic acid.

[0098] Among them, the molar ratio of compound a to sodium nitrite is 1:(5-20); for example, it can be 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, and values between any two of the above.

[0099] The reaction temperature of the ring-closure reaction is 20-30°C; for example, it can be 20°C, 21°C, 22°C, 23°C, 24°C, 25°C, 26°C, 27°C, 28°C, 29°C, 30°C, and values between any two of the above.

[0100] The reaction time of the ring-closure reaction is 10-60 min; for example, it can be 10 min, 20 min, 30 min, 40 min, 50 min, 60 min, and values between any two of the above.

[0101] Among them, the molar ratio of the compound b 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.

[0102] The reaction temperature of the nitrogen-nitrogen coupling 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.

[0103] The reaction time of the nitrogen-nitrogen coupling reaction is 6 to 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.

[0104] 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, and argon.

[0105] It can be understood that the organic compounds provided in this application are not limited to being prepared by the preparation method of the organic compounds provided in this application.

[0106] 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.

[0107] 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.

[0108] In some embodiments, the solvent can include but is not limited to one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene.

[0109] In some embodiments, the composition can contain one of the above organic compounds, or can contain two or more of the above organic compounds.

[0110] 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-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, 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, or one or more of them.

[0111] The composition has good hole generation ability and hole mobility, and can be used to prepare the hole functional layer of the optoelectronic device 100; and the composition has good light stability, and when preparing the hole functional layer, the film layer can be prevented from being damaged by ultraviolet light.

[0112] When preparing the hole functional layer using the above composition, solution methods such as spin coating, blade coating, printing, or spraying can be employed on a substrate. After forming a film, annealing is carried out at 100 - 130 °C for 5 - 30 min to obtain the hole functional layer. Among them, the annealing temperature can be 100 °C, 105 °C, 110 °C, 115 °C, 120 °C, 125 °C, 130 °C, and values between any two of the above-mentioned values.

[0113] Furthermore, the present application also proposes an optoelectronic device 100, which includes but is not limited to an organic light-emitting diode (OLED), a quantum dot light-emitting diode (QLED). 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 from the composition described above.

[0114] The hole functional layer of the optoelectronic device 100 contains an organic compound. On the one hand, due to the excellent hole transport / injection performance of the compound, the device can have better optoelectronic performance and lifespan. On the other hand, due to the ultraviolet absorption performance of the compound, it can absorb ultraviolet light, avoid ultraviolet light damage, and has better light stability. It can absorb the ultraviolet light generated during the device preparation process. Thus, during device preparation, the damage to the materials caused by the ultraviolet light involved in the device preparation process is reduced, and the light stability of the device is improved.

[0115] 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):polystyrenesulfonate (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’-di(1-naphthyl)-1,1’-biphenyl-4,4”-diamine (α-NPD), one or more of transition metal oxides and 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.

[0116] 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.

[0117] The organic light-emitting materials can be selected from at least one of diaryl anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, the TBPe fluorescent material that emits blue light, the TTPA fluorescent material that emits green light, the TBRb fluorescent material that emits orange light, and the DBP fluorescent material that emits red light.

[0118] 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.

[0119] 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.

[0120] 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 represented, it corresponds to Cd x Zn 1-x Se, where 0 < x < 1.

[0121] 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 at least one of 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 X is a halogen anion selected from at least one of Cl - 、Br - 、I - ; 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, and 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- connected by sharing vertices extend in the two-dimensional direction 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, and the organic layer and the inorganic layer overlap with each other to form a stable two-dimensional layered structure.

[0122] In one embodiment, the quantum dot light-emitting material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0123] 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 from 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, IIB-VIA group materials, IIIB-VA group materials, and IB-IIIB-VIA group 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 IIB-VIA group materials include one or more of ZnS, ZnSe, CdS, and CdSe; the IIIB-VA group materials include one or more of InP and GaP; the IB-IIIB-VIA group 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.

[0124] 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, 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.

[0125] 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.

[0126] 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-emitting requirements of the optoelectronic device 100.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] It can be understood 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.

[0131] This application also relates to a display device, and the display device includes the optoelectronic device 100 provided in this application. The display device may be any electronic product with a display function, and 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.

[0132] The following specifically describes 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.

[0133] Example 1:

[0134] The structural formula of the organic compound M1 in this embodiment is as follows:

[0135]

[0136] The synthesis route of the organic compound M1 in this embodiment is as follows:

[0137]

[0138] Step 1: Add compound M1-1 (1 mmol, CAS: 866363-49-7) to a 100 mL two-necked flask, add sodium nitrite (10 mmol, CAS: 137-07-5), add 20 mL of acetic acid, dissolve it in 10 mL of water, stir at room temperature for 30 min, stop the reaction when it is monitored that the raw materials have completely reacted, distill the reaction solution under reduced pressure to remove the solvent, mix the crude product with silica gel of 200 to 300 mesh, and perform column chromatography separation. The mobile phase is petroleum ether: ethyl acetate (volume ratio is 1:1). Finally, 207 mg of product M1-2 is obtained. The compound M1-2 is a white solid, and the yield is 79%. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ8.93-8.89(m,4H).

[0139] Step 2: Add compound M1-2 (1 mmol) into a 100 mL two-necked flask, dissolve it in 40 mL of toluene, then add diphenylamine (3 mmol, CAS: 122-39-4), CuCl (0.5 mmol), pass in nitrogen, use a vacuum pump to evacuate and replace with nitrogen for 15 minutes. Wrap the reaction flask with tin foil, stir it in the dark and heat it to 110 °C for reaction for 24 h. Stop the reaction and cool it to room temperature. Extract the reaction solution, and use dichloromethane (1000 mL) and water (250 mL) to wash it repeatedly for 3 to 4 times. Dry the organic phase with anhydrous magnesium sulfate, and perform rough separation by column chromatography. The eluent is petroleum ether:dichloromethane:ethyl acetate (volume ratio is 20:1:1) to obtain 467 mg of the final product M1. M1 is a white solid, and the yield is 70%. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ8.64(s,2H),8.42(s,2H),7.29-7.25(m,8H),7.15-7.12(m,8H),7.06-7.02(m,4H).

[0140] Example 2:

[0141] The structural formula of the organic compound M2 in this example is as follows:

[0142]

[0143] Preparation of the organic compound M2:

[0144]

[0145] The synthesis of the organic compound M2 in this example is similar to that of M1, except that in Step 2 of Example 1, diphenylamine is replaced with 4-bromotriphenylamine (CAS: 36809-26-4), and the reaction conditions and the amount of substances remain unchanged. Finally, a white solid product M2 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ8.72(s,2H),8.48(s,2H),7.77-7.73(m,4H),7.27-7.21(m,8H),7.19-7.15(m,4H),7.11-7.07(m,8H),7.06-7.00(m,4H).

[0146] Example 3

[0147] The structural formula of the organic compound M3 in this example is as follows:

[0148]

[0149] Preparation of the organic compound M3:

[0150]

[0151] The synthesis of organic compound M3 in this example is similar to that of M1. Only in Example 1, diphenylamine in step 2 is replaced with 4,4'-dimethoxydiphenylamine (CAS: 101-70-2). The reaction conditions and amounts of substances remain unchanged, and finally a white solid product M3 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.64(s,2H),8.40(s,2H),7.16-7.11(m,8H),6.87-6.79(m,8H),3.79(s,12H).

[0152] Example 4

[0153] The structural formula of organic compound M4 in this example is as follows:

[0154]

[0155] Preparation of organic compound M4:

[0156]

[0157] The synthesis of organic compound M4 in this example is similar to that of M1. Only in Example 1, diphenylamine in step 2 is replaced with 2-bromophenoxazine (CAS: 10230-35-0). The reaction conditions and amounts of substances remain unchanged, and finally a white solid product M4 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.74(s,2H),8.50(s,2H),7.83-7.80(m,2H),7.73-7.69(m,2H),7.31-7.28(m,2H),7.11-7.06(m,4H),7.06-6.98(m,4H).

[0158] Example 5

[0159] The structural formula of organic compound M5 in this example is as follows:

[0160]

[0161] Preparation of organic compound M5:

[0162]

[0163] The synthesis of organic compound M5 in this example is similar to that of M1, except that in Example 1, diphenylamine in Step 2 is replaced with 10-(4-bromophenyl)-10H-phenoxazine (CAS: 71041-21-9). The reaction conditions and the amounts of substances remain unchanged, and finally a white solid product M5 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.73(s,2H),8.50(s,2H),7.86-7.82(m,4H),7.42-7.38(m,4H),7.21-7.17(m,4H),7.04-6.97(m,8H),6.93(m,4H).

[0164] Example 6

[0165] The structural formula of organic compound M6 in this example is as follows:

[0166]

[0167] Preparation of organic compound M6:

[0168]

[0169] The synthesis of organic compound M6 in this example is similar to that of M1, except that in Example 1, diphenylamine in Step 2 is replaced with 9-(4-bromophenyl)-9H-carbazole (CAS: 57102-42-8). The reaction conditions and the amounts of substances remain unchanged, and finally a white solid product M6 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.73(s,2H),8.49(s,2H),8.16-8.12(m,4H),7.93-7.84(m,8H),7.62-7.57(m,4H),7.35-7.30(m,6H),7.26-7.21(m,2H).

[0170] Example 7

[0171] The structural formula of organic compound M7 in this example is as follows:

[0172]

[0173] Preparation of organic compound M7:

[0174]

[0175] The synthesis of organic compound M7 in this example is similar to that of M1, except that in Step 2 of Example 1, diphenylamine is replaced with N-(4-bromophenyl)-4-methoxy-N-(4-methylphenyl)aniline (CAS: 194416-45-0). The reaction conditions and the amounts of substances remain unchanged, and finally a white solid product M7 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.72(s,2H),8.48(s,2H),7.75-7.70(m,4H),7.17-7.14(m,4H),7.12-7.10(m,8H),6.84-6.81(m,8H),3.78(s,12H).

[0176] Example 8

[0177] The structural formula of organic compound M8 in this example is as follows:

[0178]

[0179] Preparation of organic compound M8:

[0180]

[0181] The synthesis of organic compound M8 in this example is similar to that of M1, except that in Step 2 of Example 1, diphenylamine is replaced with 10-(4-bromophenyl)-9,10-dihydro-9,9-dimethylacridine (CAS: 1342892-15-2). The reaction conditions and the amounts 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)δ8.73(s,2H),8.49(s,2H),7.81-7.78(m,4H),7.33-7.30(m,4H),7.24-7.20(m,4H),7.17-7.13(m,4H),7.04-7.00(m,8H),1.59(s,12H).

[0182] Example 9

[0183] The structural formula of organic compound M9 in this example is as follows:

[0184]

[0185] Preparation of organic compound M9:

[0186]

[0187] The synthesis of organic compound M9 in this example is similar to that of M1. Only in Example 1, diphenylamine in Step 2 is replaced with 10-(4-bromophenyl)-10H-phenothiazine (CAS: 63524-03-8). The reaction conditions and the amount of substances do not change, and finally a white solid product M9 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ8.73(s,2H),8.50(s,2H),7.86-7.82(m,4H),7.46-7.42(m,4H),7.41-7.38(m,4H),7.25-7.22(m,4H),7.21-7.17(m,4H),7.07-7.03(m,4H).

[0188] Example 10

[0189] The structural formula of organic compound M10 in this example is as follows:

[0190]

[0191] Preparation of organic compound M10:

[0192]

[0193] The synthesis of organic compound M10 in this example is similar to that of M1-2. Only in Example 1, M1-1 in Step 1 is replaced with M10-1 (CAS: 106020-19-3). The reaction conditions do not change, and the amount of the remaining reaction substances is halved accordingly. Finally, a white solid product M10 is obtained. The NMR data is as follows: 1 H NMR(500MHz,Chloroform-d)δ8.63(s,1H),8.41-8.38(m,1H),8.09(s,1H),7.94-7.88(m,1H),7.55-7.49(m,1H),7.31-7.24(m,1H).

[0194] Example 11

[0195] Organic compound M11 in this example is the organic compound M1-2 prepared in Example 1.

[0196] Comparative Example 1

[0197] Organic compound P1

[0198]

[0199] The synthesis of organic compound P1 in this example is similar to that of M1, except that M1-2 is replaced with P1-1 (CAS: 83834-10-0) in step 2, and the remaining reaction conditions and amounts of substances remain unchanged, and finally a white solid product P1 is obtained. 1 H NMR(500MHz,Chloroform-d)δ7.95(d,J=8.4Hz,2H),7.68(d,J=2.2Hz,2H),7.28-7.23(m,8H),7.19-7.16(m,2H),7.11-7.07(m,8H),7.06-7.01(m,4H).

[0200] Comparative Example 2

[0201] Preparation of organic compound P2:

[0202]

[0203] The synthesis of organic compound P2 in this example is similar to that of P1, except that diphenylamine is replaced with 4-phenylboronic acid-9H-carbazole (CAS: 419536-33-7), and the remaining reaction conditions and amounts of substances remain unchanged, and finally a white solid product P2 is obtained. The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.41-8.38(m,2H),8.26-8.23(m,2H),8.16-8.12(m,4H),7.99-7.96(m,2H),7.76-7.73(m,4H),7.63-7.59(m,4H),7.43-7.40(m,4H),7.35-7.30(m,6H),7.26-7.21(m,2H).

[0204] Comparative Example 3

[0205] Preparation of organic compound P3:

[0206]

[0207] The synthesis of organic compound P3 in this comparative example is similar to that of P1, 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, and finally a white solid product P3 is obtained. The NMR data are as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.37 - 8.35 (m, 2H), 8.24 - 8.21 (m, 2H), 7.99 - 7.96 (m, 2H), 7.69 - 7.66 (m, 4H), 7.48 - 7.42 (m, 8H), 7.25 - 7.17 (m, 8H), 7.07 - 7.02 (m, 4H).

[0208] Comparative Example 4

[0209] Preparation of Organic Compound P4:

[0210]

[0211] The synthetic route of organic compound P4 is as follows:

[0212] Add compound P4-1 (1 mmol, CAS: 248954-03-2) into a 100 mL two-necked flask, add 4,7-dibromo-2-methylbenzotriazole (3 mmol, CAS: 300684-26-8), add tetrakis(triphenylphosphine)palladium(0) (0.1 mmol), dissolve in 30 mL of toluene, add 2 mL of ethanol, stir at 110 °C for 6 h. Stop the reaction when it is monitored 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 - 300 mesh, and column chromatography separation is carried out. The mobile phase is petroleum ether:ethyl acetate (volume ratio 1:1). Finally, 427 mg of compound P4-2 is obtained as a white solid, and the yield is 71%.

[0213] Add compound P4-2 (1 mmol) into a 100 mL two-necked flask, dissolve in 40 mL of toluene, then add 4-borotriphenylamine (3 mmol, CAS: 201802-67-7), add tetrakis(triphenylphosphine)palladium(0) (0.1 mmol), dissolve in 30 mL of toluene, add 2 mL of ethanol, stir at 110 °C for 6 h. Stop the reaction when it is monitored 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 - 300 mesh, and column chromatography separation is carried out. The mobile phase is petroleum ether:ethyl acetate (volume ratio 1:1). 656 mg of the final product P4 is obtained. P4 is a white solid, and the yield is 70%. The NMR data is as follows: 11H NMR (500 MHz, Chloroform-d) δ 8.58 - 8.56 (m, 2H), 8.23 - 8.19 (m, 2H), 8.05 - 8.02 (m, 2H), 7.96 - 7.88 (m, 4H), 7.67 - 7.63 (m, 4H), 7.32 - 7.28 (m, 4H), 7.27 - 7.22 (m, 8H), 7.11 - 7.08 (m, 8H), 7.06 - 7.01 (m, 4H), 4.57 (s, 3H).

[0214] Comparative Example 5

[0215] Preparation of Organic Compound P5:

[0216]

[0217] The synthesis of organic compound P5 in this example is similar to that of M2, except that sodium nitrite and acetic acid in step 1 are replaced with iron(III) oxide and fluoboric acid, and the remaining reaction conditions and amounts of substances remain unchanged. Finally, a white solid product P5 is obtained. The NMR data are as follows: 1 1H NMR (500 MHz, Chloroform-d) δ 8.96 - 8.95 (m, 2H), 8.82 - 8.80 (m, 2H), 8.40 - 8.38 (m, 2H), 7.78 - 7.74 (m, 4H), 7.27 - 7.22 (m, 8H), 7.20 - 7.17 (m, 4H), 7.11 - 7.07 (m, 8H), 7.05 - 7.01 (m, 4H).

[0218] Device Example 1

[0219] This device example provides a quantum dot light-emitting diode and its preparation method, which specifically includes the following steps.

[0220] 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 min each in turn, and then dry it with a nitrogen gun; then place the cleaned ITO glass sheet in oxygen plasma for further cleaning for 10 min; continue to treat the surface of the ITO substrate with ultraviolet-ozone for 15 min; spin-coat PEDOT:PSS on the cleaned ITO glass sheet in air at a rotation speed of 5000 r / min; after spin-coating, place it in air for annealing at an annealing temperature of 150 °C for 30 min to obtain a hole injection layer with a thickness of 40 nm;

[0221] 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 hole injection layer at a speed of 3000 r / min; after spin-coating, anneal in a glove box at an annealing temperature of 120 °C for 10 min to obtain a hole transport layer with a thickness of 20 nm;

[0222] Step 3: Spin-coat a hexane solution of quantum dots QD (concentration of 20 mg / mL) on the hole transport layer at a spin-coating speed of 2000 r / min; then let it stand for 15 min under an environment of 10 -2 MPa to obtain a light-emitting layer with a thickness of 30 nm;

[0223] 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 speed of 3000 r / min, and then let it stand for 15 min under an environment of 10 -2 MPa to obtain a 50-nm electron transport layer;

[0224] Step 5: Through thermal evaporation, with a vacuum degree not higher than 3×10 -4 Pa, evaporate Ag at a speed of 1 Å / s to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and perform epoxy resin encapsulation.

[0225] Its device structure is: ITO / PEDOT:PSS(40 nm) / M1(20 nm) / QD(30 nm) / ZMO(50 nm) / Ag(20 nm).

[0226] Device Example 2 - 11

[0227] Device Example n is basically the same as Device Example 1, the difference is only 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 compound of Example n is M2 to M11.

[0228] Device Comparative Examples 1 to 5

[0229] Device Comparative Example m is basically the same as Device Example 1, the difference is only 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 5. Specifically, the organic compounds in the hole transport layers of Device Comparative Examples 1 to 5 are P1 to P5 in sequence.

[0230] Experimental Example

[0231] (I) Hole Mobility

[0232] The organic compounds of Examples 1 to 11 and Comparative Examples 1 to 5 were used as hole transport materials respectively. Referring to the preparation processes of the corresponding film layers in Device Example 1 above, a detection device with the following structure was constructed: ITO / organic compound / MoO3 / Ag. Then, the hole mobility of the materials was detected using the detection device, and the results are shown in Table 1.

[0233] The hole mobility of the hole transport material was recorded by the space charge limited current (SCLC) method, which can be described by the Mott - Gurney equation: J = 9με0ε r V 2 / (8d 3 )

[0234] 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 permittivity 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.

[0235] Table 1

[0236] <![CDATA[Hole mobility (10 -5 cm 2 V -1 s -1 )]]> M1 6.36 M2 6.4 M3 6.48 M4 7.41 M5 7.17 M6 6.84 M7 6.26 M8 6.74 M9 6.96 M10 5.05 M11 5.36 P1 4.31 P2 4.07 P3 4.4 P4 3.58 P5 3.1

[0237] 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 -5 ~8×10 - 5 cm 2 V -1 s -1 and can be used as hole transport materials;

[0238] The hole mobility of M1 is significantly higher than that of P1, the hole mobility of M6 is significantly higher than that of P2, the hole mobility of M9 is significantly higher than that of P3, and the hole mobility of M2 is significantly higher than that of P4 and P5. Obviously, the organic compounds proposed in this application have higher hole transport performance.

[0239] (2) Perform maximum brightness L max testing, lifetime T95 testing, lifetime T95@1000nit testing, current efficiency C.E testing, and stability testing on the quantum dot light - emitting diodes of Device Examples 1 - 11 and Device Comparative Examples 1 - 5. The test results are shown in Table 1.

[0240] Among them, the maximum brightness L maxThe test method for voltage and current efficiency C.E is as follows: Using a Fosida FPD optical property measurement device, an efficiency test system is built by controlling a QE PRO spectrometer, Keithley 2400, and Keithley 6485 through LabView to measure parameters such as voltage, current, brightness, and emission spectrum, and the current efficiency C.E is obtained through calculation.

[0241] The test method for lifespan T95@1000nit is as follows: When the device is driven under a constant current or voltage, the time required for the brightness to decrease to a certain proportion of the maximum brightness is measured. The time when the brightness drops to 95% of the maximum brightness is defined as T95, and this lifespan is the measured lifespan. To shorten the test cycle, the device lifespan test is usually carried out by accelerating the device aging at high brightness, and the lifespan at high brightness is obtained by fitting with an extended exponential decay brightness decay fitting formula. For example, the lifespan at 1000nit is denoted as T95@1000nit. The specific calculation formula is as follows:

[0242]

[0243] where T95 L is the lifespan at low brightness, T95 H is the measured lifespan at high brightness, L H is the device accelerated to the maximum brightness, L L is 1000nit, A is the acceleration factor, and 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.

[0244] The method for stability test is as follows: After testing the initial current efficiency C.E of the device examples and device comparative examples of the device and recording their initial data, the device is placed in a sealed environment under a standard ultraviolet light source (350nm) and irradiated with a power of 100mW / cm 2 for 6h, and the current efficiency C.E after UV irradiation is recorded, and the decay rate is calculated to characterize the photo stability.

[0245] Table 2

[0246]

[0247]

[0248] As can be seen from Table 2,

[0249] Compared with the device comparative examples, Device Examples 1 to 11 all have relatively high maximum brightness Lmax, lifetime T95, lifetime T95@1000nit, current efficiency C.E, and relatively low C.E decay rate, indicating that in the device, the balance between hole injection and electron injection is relatively good, thus enabling the device to have relatively high optoelectronic performance and lifetime; in addition, the organic compounds of the present application have relatively good tolerance to ultraviolet light and are not easily damaged by ultraviolet light, thus enabling the device to have relatively high light stability, which is specifically reflected in the relatively low C.E decay rate of the device examples.

[0250] 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 herein to elaborate on the principles and implementation manners of the present application. The description of the above embodiments is 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-1) or (I-2): Wherein, Ar1, Ar2, and Ar3 are each independently selected from H, D, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and one of the following structures: Wherein, M is SiR5R6, NR7, O, or S; X is SiR8R9, CR 10 R 11 , S, O or NR 12 ; R1, R2, R3, and R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl and substituted or unsubstituted C1-C30 alkoxy; R5 to R 12 each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted aryl having 6 to 20 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers from 0 to 4; 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, C1-C20 alkoxy, and aryl with 6 to 20 ring atoms.

2. The organic compound according to claim 1, characterized in that, R5 to R 12 each independently selected from one or more combinations of H, D, C1-C10 alkyl, and aryl having 6-10 ring atoms; and / or, R1, R2, R3, and R4 are each independently selected from one or more combinations of C1-C10 alkyl and C1-C10 alkoxy; and / or, n1 and n2 are each independently selected from 0 or 1; and / or, n3 and n4 are each independently selected from 0 or 1; and / or, Ar1, Ar2, and Ar3 are each independently selected from one of the following structures:

3. The organic compound according to claim 2, characterized in that, Ar1, Ar2, and Ar3 are each independently selected from one of the following structural formulas (1-1) to (1-13):

4. The organic compound according to any one of claims 1 to 3, characterized in that, The organic compound has the structure shown in formula (II):

5. The organic compound according to claim 1, wherein The organic compound includes One or more of the following structural formulas:

6. The organic compound according to claim 1, characterized in that, The hole mobility of the organic compound is 3×10 -5 ~8×10 -5 cm 2 V -1 s -1 。 7. A method for preparing an organic compound, characterized in that, Including the following steps: Using compound a as a raw material, carrying out a ring-closing reaction to obtain compound b; Mixing the compound b with compound c and carrying out an azo coupling reaction to obtain an organic compound M; Wherein, the organic compound includes a compound having the structure shown in formula (I-1) and / or (I-2), and compound a, compound b, and compound c have the following structural formulas respectively: Wherein, Ar represents Ar1, Ar2, or Ar3; 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 a halogen group; Ar1, Ar2, and Ar3 are each independently selected from H, D, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, and one of the following structures: wherein, M is SiR5R6, NR7, O or S; X is SiR8R9, CR 10 R 11 , S, O or NR 12 ; R1, R2, R3, R4 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkoxy groups; R5 to R 12 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted aryl groups having 6 to 20 ring atoms; n1 and n2 are each independently selected from integers of 0 to 5; n3 and n4 are each independently selected from integers of 0 to 4; 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, C1-C20 alkoxy, and aryl with 6 to 20 ring atoms.

8. The preparation method according to claim 7, wherein, The step of using compound a as a raw material and carrying out a ring-closing reaction to obtain compound b includes: mixing compound a, sodium nitrite, acid, and water, and carrying out a ring-closing reaction to obtain compound b; Wherein, the molar ratio of the compound a to the sodium nitrite is 1:(5-20); and / or, The temperature of the ring-closing reaction is 20-30°C; and / or, The time of the ring-closing reaction is 10-60 min.

9. The preparation method according to claim 7, characterized in that, The molar ratio of the compound b to the compound c is 1:(3 to 5); and / or, The temperature of the azo coupling reaction is 80 to 110 °C; and / or, The time of the azo coupling reaction is 6 to 24 h.

10. A composition, characterized in that, It includes an organic compound and a solvent, where the organic compound includes the organic compound according to any one of claims 1 to 6, or includes the organic compound prepared by the preparation method according to any one of claims 7 to 9.

11. The composition according to claim 10, characterized in that, 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-ethylhexoxy)-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, characterized in that, It includes an anode, a hole functional layer, and a cathode, where the material of the hole functional layer includes the organic compound according to any one of claims 1 to 6, or includes the organic compound prepared by the preparation method according to any one of claims 7 to 9, or the hole functional layer is made of the composition according to claim 10 or 11.

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