Organic compound, preparation method thereof, composition, photoelectric device and display device

Abstract

The invention discloses an organic compound and a preparation method thereof, a composition, a photoelectric device and a display device.The organic compound provided by the technical scheme of the invention is an organic free radical compound, organic free radicals exist in the molecular structure of the organic free radical compound, the organic compound has high conductivity, and the spin multiplicity of the organic free radicals is always 2, 2 '-biphenyl. The possibility of fluorescence quenching caused by intersystem energy transfer is eliminated; the organic compound has good hole mobility and low ionization potential, and can be used as a hole injection material or a hole transport material.

Description

Technical Field

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

[0002] A hole functional material refers to a material having hole transport performance or hole injection performance. Currently, commonly used metal oxide-based electron transport materials usually have a relatively high electron mobility, and hole functional materials with good hole transport or injection characteristics are required to be matched.

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

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

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

[0006] In a first aspect, an embodiment of the present application provides an organic compound having the structure shown in formula (I):

[0007] (I):

[0008] Wherein, L is selected from any one of the following structures:

[0009]

[0010] Wherein, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocycle having 5 to 40 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 40 ring atoms;

[0011] W is selected from NR3 or CR4R5;

[0012] n1 is selected from 0 or 1, and n2 is selected from 0 or 1;

[0013] R1, R2, R3, R4, R5 are each independently selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 40 ring atoms, and R4 and R5 are bonded to form a ring or not form a ring;

[0014] When being substituted, the substituents each independently selected from one or more combinations of D, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms each time they appear.

[0015] Second aspect, the present application also provides a method for preparing an organic compound, comprising the following steps:

[0016] Mix compound a and compound b and conduct a first reaction to obtain intermediate A;

[0017] Mix the intermediate A and compound c and conduct a second reaction to obtain intermediate B;

[0018] Mix the intermediate B and a radical catalyst and conduct a third reaction to obtain organic compound M;

[0019] Wherein, the structural formulas of the compound a, compound b, compound c, intermediate A, intermediate B and organic compound M are as follows:

[0020]

[0021] Wherein, R represents R1 or R2, Ar represents Ar1 or Ar2, n represents n1 or n2, and Z represents H or Si(CH3)3;

[0022] X and Y are each independently selected from halogen groups;

[0023] L is selected from any one of the following structures:

[0024]

[0025] Wherein, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocycle having 5 to 40 ring atoms and a substituted or unsubstituted arene having 6 to 40 ring atoms;

[0026] W is selected from NR3 or CR4R5;

[0027] n1 is selected from 0 or 1, and n2 is selected from 0 or 1;

[0028] R1, R2, R3, R4, R5 are each independently selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 40 ring atoms, and a ring is formed or not formed between R4 and R5;

[0029] When being substituted, the substituents are each independently selected from one or more combinations of D, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms each time they appear.

[0030] Third aspect, the present application also provides a composition, comprising an organic compound and a solvent, wherein the organic compound comprises the organic compound described above, or comprises the organic compound prepared by the preparation method described above.

[0031] Fourth aspect, the present application also 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, or is made of the composition described above.

[0032] Fifth aspect, the present application also provides a display device, including the optoelectronic device described above.

[0033] The organic compound provided by the technical solution of the present application is an organic radical compound, and there is an organic radical in its molecular structure. The organic compound has a relatively high conductivity, and the spin multiplicity of the organic radical is always 2, which excludes the possibility of fluorescence quenching caused by intersystem energy transfer; the organic compound has good hole mobility and a low ionization potential, and can be used as a hole injection material or a hole transport material. Description of the Drawings

[0034] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings 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.

[0035] Figure 1 It is a schematic structural diagram of an embodiment of an optoelectronic device provided by the present application;

[0036] 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

[0037] The following will clearly and completely describe the technical solutions in the embodiments of the present application with reference to 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 of 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" specifically refer to the drawing directions in the accompanying 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 description of the range has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that the description of the range 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 individual 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.

[0038] In the present application, "and / or" describes the association relationship of associated objects, indicating that three relationships may exist. For example, A and / or B may represent: A exists alone, A and B exist simultaneously, or B exists alone. Wherein A and B may be singular or plural.

[0039] 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 of the following items (pieces)" or similar expressions refer to any combination of these items, including any combination of single items (pieces) 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 plural respectively.

[0040] Term Explanation

[0041] 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, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to: hydroxyl, amino, halogen, carboxyl, nitro, sulfonic acid group, mercapto, cyano, C1-C5 alkoxy, C1-C5 alkylcarbonyl, heteroaryl having 5-20 ring atoms, aryl having 6-20 ring atoms, heteroaryloxy having 5-20 ring atoms, aryloxy having 6-20 ring atoms, or a combination of one or more of them. In the present application, "combination of multiple" means the case where at least one hydrogen in a group is substituted by other groups (it may be substituted by one other group or by multiple other groups). For example, the combination of hydroxyl, halogen and amino may mean that at least two hydrogens in the amino group are respectively substituted by hydroxyl and halogen. The combination of aryl and alkyl may be a substituent formed by substituting one or more hydrogens in the aryl substituent by alkyl, or a substituent formed by substituting one or more hydrogens in the alkyl substituent by aryl.

[0042] In the present application, when the same substituent appears multiple times, it may be independently selected from different groups. For example, if the general formula contains multiple R1s, then R1s may be independently selected from different groups. Six Rs on the benzene ring 1 may be the same as or different from each other.

[0043] In the present application, "alkyl" may represent a straight-chain alkyl, a branched-chain alkyl and / or a cyclic alkyl. The number of carbon atoms of the alkyl may be 1-50, 1-30, 1-20, 1-10 or 1-6. Phrases 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-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc. Thioalkyl refers to a group in which at least one hydrogen in the alkyl group is replaced by a sulfur atom.

[0044] In this application, "-C n H 2n+1 ", without special annotation or limitation, represents a straight-chain alkyl group. For example, -C6H 13 represents n-hexyl, and -C 12 H 25 represents n-dodecyl.

[0045] In this application, "the number of ring atoms" represents the number of atoms in the ring itself of a structural compound formed by bonding atoms in a ring (e.g., a monocyclic compound or a polycyclic compound). It can be understood that the ring atoms are not limited to carbon atoms. When a heterocycle is contained in a cyclic compound, the heteroatoms are also atoms constituting the heterocycle and belong to the ring atoms. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to "the number of ring atoms" described below without special explanation. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophenyl group is 5.

[0046] In the present application, "aryl, aryl group or aromatic group" refers to a hydrocarbon group containing at least one aromatic ring, such as a monocyclic compound, a fused-ring compound or a polycyclic non-fused compound, etc. "Heterocycle" includes two categories: aliphatic heterocycle and aromatic heterocycle. Among them, "aliphatic heterocycle" is a heterocycle in which the heterocycle in the molecular skeleton does not exhibit aromaticity, and it can be a ring formed by replacing at least one ring carbon atom in an alicyclic compound with a heteroatom; "aromatic heterocycle, heteroaryl group or heteroaromatic group" refers to an aromatic hydrocarbon group containing at least one heteroatom, such as a monocyclic compound containing at least one heteroatom, a fused-ring compound containing at least one heteroatom or a polycyclic non-fused compound containing at least one heteroatom, etc. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S. Among them, the fused-ring compound or the fused compound has the same meaning and can be interchanged. Specifically, it means that the compound can have two or more rings, and two ring atoms are shared by two adjacent rings, that is, a fused ring. For the purposes of the present application, the aromatic group or heteroaromatic group includes not only the system of aromatic rings, but also a non-aromatic ring system. Therefore, for example, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered aromatic groups or heteroaromatic groups for the purposes of this invention. For the purposes of the present application, the fused-ring aromatic or fused heteroaromatic ring system includes not only the system of aromatic groups or heteroaromatic groups, but also, in which, multiple aromatic groups or heteroaromatic groups can also be interrupted by short non-aromatic units (<10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Therefore, for example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered fused-ring aromatic ring systems for the purposes of this invention.

[0047] In a certain preferred embodiment, the aromatic group is selected from: benzene, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives; the heteroaromatic group is selected from triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzoisoxazole, benzoisothiazole, benzimidazole, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthridine, perimidine, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and their derivatives.

[0048] In the present application, amino represents -NR 1 R 2 wherein, R 1 R 2Each independently represents H or an alkyl group, that is, the amino group can refer to -NH2, -NH(alkyl), or -N(alkyl)(alkyl).

[0049] In this application, the "halogen group" represents -Cl, -Br, -F, or -I.

[0050] An embodiment of this application provides an organic compound having the structure shown in formula (I):

[0051] (I):

[0052] Among them, L is selected from one of the following structures:

[0053]

[0054] Among them, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocyclic ring having 5 to 40 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 40 ring atoms;

[0055] W is selected from NR3 or CR4R5;

[0056] n1 is selected from 0 or 1, and n2 is selected from 0 or 1;

[0057] R1, R2, R3, R4, and R5 are each independently selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 40 ring atoms, and a ring is formed or not formed between R4 and R5;

[0058] When being substituted, the substituents each independently selected from one or more combinations of D, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms each time they appear.

[0059] The organic compound provided by the technical solution of this application is an organic radical compound having a ·B2-L-B1· molecular structure. In the molecular structure, -B1· (that is ) and -B2· (that is ) is an organic free radical. In terms of electricity, the existence of the organic free radical makes the molecule have a relatively high conductivity. The spin multiplicity of the organic free radical is always 2, which excludes the possibility of fluorescence quenching caused by intersystem energy transfer; L is a conjugated unit with electron-donating properties, which not only has good hole mobility and a low ionization potential, but also can improve the stability of the organic free radical and achieve greater electron delocalization, thereby further enhancing the hole mobility of the material. The organic compound can be used as a hole injection material or a hole transport material, and is used to form the hole transport layer 60 or the hole injection layer 50 of the optoelectronic device 100. Moreover, due to its high hole migration performance, it has better compatibility with electron transport materials with high electron mobility such as metal oxide nanoparticles, which helps to improve the balance of hole injection and electron injection in the device, and further improves the optoelectronic performance and service life of the device.

[0060] Ar1 and Ar2 are each independently selected from one or more of a substituted or unsubstituted heterocyclic ring having 5 to 40 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 40 ring atoms. Among them, the heterocyclic ring can be a heterocyclic ring having 5 to 30 ring atoms, or a heterocyclic ring having 5 to 20 ring atoms, or a heterocyclic ring having 5 to 10 ring atoms. For example, it can be a pyridine ring, a nitrogen-containing five-membered aliphatic ring, a nitrogen-containing six-membered aliphatic ring, a diazole, a triazole, etc.; the aromatic ring can be an aromatic ring having 6 to 30 ring atoms, or an aromatic ring having 6 to 20 ring atoms, or an aromatic ring having 6 to 10 ring atoms. For example, it can be benzene, naphthalene, anthracene, phenanthrene, biphenyl, etc. When Ar1 and Ar2 are each independently selected from a substituted heterocyclic ring or aromatic ring by a substituent, the substituent can each independently be selected from one or more combinations of D, a C1-C20 alkyl group, and an aromatic group having 6 to 20 ring atoms each time it appears. For example, methyl, ethyl, propyl, butyl, adamantyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, alkylphenyl, phenylalkyl, etc. Ar1 and Ar2 can be the same or different.

[0061] In some embodiments, n1 can be 0 or 1; n2 can be 0 or 1; n1 and n2 can be the same or different. Correspondingly, the organic compound can have one of the following structures:

[0062]

[0063] Among them, R1 and R2 can each independently be selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aromatic group having 6 to 40 ring atoms each time they appear. In some embodiments, R1 and R2 can each independently be selected from any one of H, D, and a C1-C30 alkyl group each time they appear; in other embodiments, R1 and R2 can each independently be selected from H or a C1-C10 alkyl group each time they appear.

[0064] In some specific embodiments, -B1· (i.e., ), -B2· (i.e., ) are each independently selected from the following structures:

[0065]

[0066] In some embodiments, W is selected from NR3 or CR4R5; R3, R4, and R5 are each independently selected from one or more combinations of H, D, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted aryl having 6-40 ring atoms, and when W is selected from CR4R5, R4 and R5 can be bonded to form a ring or not. When R4 and R5 are bonded to form a ring, -W- can be Correspondingly, L can be Or, For example, -W- can be

[0067] Wherein, when R3, R4, and R5 are each independently selected from alkyl or aromatic rings substituted by substituents, the substituents can each independently be selected from one or more combinations of D, C1-C20 alkyl, and aryl having 6-20 ring atoms each time they appear. For example, methyl, ethyl, propyl, butyl, adamantyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, phenyl substituted by C1-C20 alkyl, C1-C20 alkyl substituted by phenyl, etc.

[0068] Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of substituted or unsubstituted heterocycles having 5 to 40 ring atoms and substituted or unsubstituted aromatic rings having 6 to 40 ring atoms. Among them, the heterocycle can be a heterocycle having 5 to 30 ring atoms, or a heterocycle having 5 to 20 ring atoms, or a heterocycle having 5 to 10 ring atoms. For example, it can be a thiophene ring, a furan ring, a pyrazole ring, a pyridine ring, a diazole, a triazole, etc.; the aromatic ring can be an aromatic ring having 6 to 30 ring atoms, or an aromatic ring having 6 to 20 ring atoms, or an aromatic ring having 6 to 10 ring atoms. For example, it can be benzene, naphthalene, anthracene, phenanthrene, biphenyl, etc. When Ar3, Ar4, Ar5, and Ar6 are each independently selected from heterocycles or aromatic rings substituted by substituents, the substituents can each independently be selected from one or more combinations of D, C1-C20 alkyl, and aryl having 6-20 ring atoms each time they appear. For example, methyl, ethyl, propyl, butyl, adamantyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, phenyl substituted by C1-C20 alkyl, C1-C20 alkyl substituted by phenyl, etc. Ar3 and Ar4 can be the same or different. Ar5 and Ar6 can be the same or different.

[0069] In some embodiments, L is selected from any one of the following structures:

[0070]

[0071] When L is selected from the above structures, L has a conjugated unit and has an electron-donating property. Taking the triphenylamine structural unit as an example of L, this structure is centered on a nitrogen atom. The large steric hindrance and hyperconjugation effect promote the nitrogen atom to have high stability and strong modifiability, making the organic compound have a high hole mobility and a low ionization potential; at the same time, when this L structure is connected to a radical group, a larger electron delocalization can be achieved, thereby improving the stability of the organic radical and further enhancing the hole mobility of the material.

[0072] In some specific embodiments, the organic compound includes one or more of the following structural formulas:

[0073]

[0074] The embodiment of the present application also provides a preparation method of an organic compound. The synthesis route of the preparation method is as follows:

[0075]

[0076] Specifically, the preparation method includes the following steps:

[0077] S10. Mix compound a and compound b and carry out a first reaction to obtain intermediate A;

[0078] S20. Mix the intermediate A and compound c and carry out a second reaction to obtain intermediate B;

[0079] S30. Mix the intermediate B and a radical catalyst and carry out a third reaction to obtain an organic compound M.

[0080] The structural formulas of the compound a, compound b, compound c, intermediate A, intermediate B, and organic compound M are as shown above, where R represents R1 or R2, Ar represents Ar1 or Ar2, and n represents n1 or n2. It can be understood that in some embodiments, the structural formula of the compound a is as shown in a1, and correspondingly, the obtained intermediate A has the structure shown in A1; in other embodiments, the structural formula of the compound a is as shown in a2, and correspondingly, the obtained intermediate A has the structure shown in A2. Among them, both A1 and A2 are named intermediate A; mix A1, A2, and compound c and carry out a second reaction to obtain intermediate B.

[0081]

[0082] In some embodiments, Z represents H or Si(CH3)3; during actual preparation, the appropriate starting material compound a can be selected according to the structure of the organic compound M to be prepared. Specifically, according to the ease of obtaining compound a, compound a with Z being H or compound a with Z being Si(CH3)3 can be selected.

[0083] Returning to the above synthetic route, X and Y are each independently selected from halogen groups; for example, they can be -F, -Cl, -Br, or -I. In some embodiments, X and Y are each independently selected from -Br or -I.

[0084] Among them, L is selected from any one of the following structures:

[0085]

[0086] Among them, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of substituted or unsubstituted heterocycles with 5 to 40 ring atoms and substituted or unsubstituted aromatic rings with 6 to 40 ring atoms;

[0087] W is selected from NR3 or CR4R5;

[0088] n1 is selected from 0 or 1, and n2 is selected from 0 or 1;

[0089] R1, R2, R3, R4, and R5 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 with 6 to 40 ring atoms, and R4 and R5 form a ring or do not form a ring when bonded;

[0090] When substituted, the substituents each independently selected from one or more combinations of D, C1-C20 alkyl groups, and aryl groups with 6 to 20 ring atoms each time they appear.

[0091] In step S10:

[0092] The temperature of the first reaction is -80°C to -70°C; for example, it can be -80°C, -79°C, -78°C, -76°C, -75°C, -74°C, -73°C, -72°C, -70°C, and values between any two of the above.

[0093] The time of the first reaction is 1 to 5 h; for example, it can be 1 h, 1.5 h, 2 h, 2.5 h, 3 h, 3.5 h, 4 h, 4.5 h, 5 h, and values between any two of the above.

[0094] The molar ratio of the said compound a to the said compound b is 1:(1 - 1.5); for example, it can be 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5 and the values between any two of the above.

[0095] In step S20:

[0096] The molar ratio of the said intermediate A to the said compound c is 1:(0.3 - 0.5); for example, it can be 1:0.3, 1:0.4, 1:0.5 and the values between any two of the above.

[0097] The second reaction is a reflux reaction. During actual synthesis, heat the mixture of intermediate A and compound c to the reflux state and keep it for 20h - 30h to obtain product intermediate B. During actual synthesis, a palladium catalyst can also be added to the mixture of intermediate A and compound c to promote the reaction. 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.

[0098] In step S30:

[0099] The temperature of the said third reaction is 15°C - 40°C; for example, it can be 15°C, 20°C, 25°C, 30°C, 35°C, 40°C and the values between any two of the above.

[0100] The time of the said third reaction is 0.5 - 2h; for example, it can be 0.5h, 1h, 1.5h, 2h and the values between any two of the above.

[0101] The said radical catalyst includes one or more of lead dioxide and lead tetraacetate.

[0102] It can be understood that the organic compounds provided by this application are not limited to being prepared by the preparation method of the organic compounds provided by this application.

[0103] Based on the above organic compound examples, this application also proposes a composition. The said composition includes a first compound and a solvent. The first compound includes the organic compounds provided by the foregoing examples. The said composition can be used as hole functional layer ink for preparing the hole functional layer of optoelectronic device 100.

[0104] 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.

[0105] In some embodiments, the solvent may include, but is not limited to, one or more of toluene, chlorobenzene, chloroform, tetralin, and chloronaphthalene.

[0106] In some embodiments, the composition may contain one of the above organic compounds, or may contain two or more of the above organic compounds.

[0107] In some embodiments, in the composition, in addition to including the organic compound and the solvent, a second compound may also be included. The second compound may be other conductive materials or semiconductor materials, 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.

[0108] The composition has good hole generation ability and hole mobility, and has good compatibility with common electron transport materials. It is used to prepare the hole functional layer of the optoelectronic device 100, which helps to promote hole injection, improve carrier balance, and enhance the optoelectronic performance of the device.

[0109] 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 the 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.

[0110] 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 from the composition described above.

[0111] The hole functional layer of the optoelectronic device 100 contains an organic compound. Since the compound has good hole mobility and hole generation ability, when used to make the hole functional layer, it can well enhance the hole injection ability, improve the carrier balance of the device, enhance the optoelectronic performance of the device, and extend the service life of the device.

[0112] 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'-tetraarylbiphenylamine, 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), one or more of spiro NPB.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, 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] As an example, the quantum dots of the core-shell structure can 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.

[0117] 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 represents being 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.

[0118] 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 two-dimensional directions to form a layered structure, and 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.

[0119] In one embodiment, the quantum dot light-emitting material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0120] 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 electronic functional materials known in the art for the optoelectronic device 100 and having 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.

[0121] 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.

[0122] 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.

[0123] It can be understood that the materials and thicknesses of the various layers of the optoelectronic device 100 can be correspondingly set and adjusted according to the light-emitting requirements of the optoelectronic device 100.

[0124] 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 a combination of more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyethersulfone.

[0125] 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.

[0126] It can be understood that the preparation methods of the various 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, blade coating method, printing method, dip coating method, immersion method, spraying method, roller coating method, casting method, slot die coating method, and bar coating method, etc.

[0127] 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, glass glue, etc. In a specific embodiment, the packaging material may be acrylic resin or epoxy resin.

[0128] 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.

[0129] 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.

[0130] Material Example 1

[0131] The structural formula of the organic compound M1 in this embodiment is as follows:

[0132]

[0133] The synthesis route of the organic compound in this embodiment is as follows:

[0134]

[0135] The specific preparation method is as follows:

[0136] Synthesis of compound a1-3: Compound a1-2 (13.4 g, 37.6 mmol, CAS: 27329-74-4) was dissolved in tetrahydrofuran (200 mL). After dropping hexane solvent and 2.5 M n-butyllithium (18 mL, 41.3 mmol) at -78 °C, it was stirred for 1 h. Then, trimethyl borate (9.5 mL, 41.3 mmol, CAS: 3349-42-6) was slowly dropped, and after stirring for 2 h. Then, 2 mol / L hydrochloric acid was dropped for neutralization, and the product was extracted with ethyl acetate and water. Recrystallization with dichloromethane and hexane gave compound a1-3 (8.8 g, 73%).

[0137] Synthesis of Compound a1-4: Dissolve Compound a1-1 (120 mg, 0.3 mmol, CAS: 81090-53-1), Compound a1-3 (386 mg, 0.6 mmol) and palladium tetrakis(triphenylphosphine) (6.9 mg, 0.006 mmol) in 20 mL of dioxane, and add 3 mL of 1 mol / L aqueous sodium carbonate solution. Heat the mixture to reflux overnight,

[0138] Then, cool the reaction mixture to room temperature, quench it with 2 mol / L HCl(aq.), extract with dichloromethane, and wash with water. The obtained organic phase after washing is dried over anhydrous sodium sulfate, and the solvent is removed under reduced pressure. The residue is purified by silica gel column chromatography to obtain a red solid a1-4 with a yield of 46% (90 mg).

[0139] Synthesis of Compound M1: Dissolve Compound a1-4 (0.001 mmol, 0.4 mg) in 50 ml of toluene, add PbO2 (0.78 mmol) to obtain a suspension; stir the suspension at room temperature for 40 min, and then filter to remove the excess PbO2 to obtain the radical product M1 with a yield of 95% (0.38 mg). 1 1H NMR (CDCl3): 7.56 (s, 4H), 7.55 (d, 4H), 7.37 (d, 4H), 7.0 - 7.24 (m, 5H), 1.40 (s, 36H).

[0140] Material Example 2

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

[0142]

[0143] The synthetic route of the organic compound in this example is as follows:

[0144]

[0145] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1-1 is changed to a2-1 (CAS: 136630-39-2). The NMR data of the obtained product M2 are as follows: 1 1H NMR (CDCl3): 11.66 (s, 1H), 8.31 (d, 2H), 7.91 (d, 2H), 7.74 (s, 2H), 7.56 (s, 4H), 1.40 (s, 36H).

[0146] Material Example 3

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

[0148]

[0149] The synthetic route of the organic compound in this example is as follows:

[0150]

[0151] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1-2 is changed to a3-2 (CAS: 40686-35-9). The NMR data of the obtained product M3 are as follows: 1 H NMR(CDCl3): 7.55(d,4H),7.49(d,4H),7.37(d,4H),7.0 - 7.24(m,5H),6.86(d.4H),1.40(s,18H).

[0152] Material Example 4

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

[0154]

[0155] The synthetic route of the organic compound in this example is as follows:

[0156]

[0157] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1-1 is changed to a4-1 (CAS: 16433-88-8). The NMR data of the obtained product M4 are as follows: 1 H NMR(CDCl3): 8.09(d,2H), 7.89(d,2H),7.78(d,2H),7.56(s,4H),4.12(s,2H),1.40(s,36H).

[0158] Material Example 5

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

[0160]

[0161] The synthetic route of the organic compound in this example is as follows:

[0162]

[0163] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1-1 is changed to a5-1 (CAS: 171408-84-7). The NMR data of the obtained product M2 are as follows:1 1H NMR (CDCl3): δ 8.08 (d, 2H), 7.90 (d, 2H), 7.79 (d, 2H), 7.68 (d, 2H), 7.56 (s, 4H), 7.55 (s, 2H), 7.25 - 7.35 (m, 4H), 1.40 (s, 36H).

[0164] Material Example 6

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

[0166]

[0167] The synthetic route of the organic compound in this example is as follows:

[0168]

[0169] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M4, except that a1 - 2 is changed to a3 - 2 (CAS: 40686 - 35 - 9). The NMR data of the obtained product M6 are as follows: 1 1H NMR (CDCl3): δ 8.08 (d, 2H), 7.90 (d, 2H), 7.79 (d, 2H), 7.68 (d, 2H), 7.55 (s, 2H), 7.49 (d, 4H), 7.25 - 7.35 (m, 4H), 6.86 (d, 4H), 1.40 (s, 18H).

[0170] Material Example 7

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

[0172]

[0173] The synthetic route of the organic compound in this example is as follows:

[0174]

[0175] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1 - 1 is changed to a7 - 1 (CAS: 663943 - 27 - 9). The NMR data of the obtained product M7 are as follows: 1 1H NMR (CDCl3): δ 7.56 (s, 4H), 7.55 (d, 4H), 7.37 (d, 4H), 6.77 (s, 2H), 2.12 (s, 9H), 1.40 (s, 36H).

[0176] Material Example 8

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

[0178]

[0179] The synthesis route of the organic compound in this example is as follows:

[0180]

[0181] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M1, except that a1-1 is changed to a8-1 (CAS: 884530-69-2). The NMR data of the obtained product M8 are as follows: 1 H NMR(CDCl3): 7.56(s,4H),7.55(d,8H),7.49(d,2H),7.41,(d,2H),7.37(d,6H),1.40(s,36H).

[0182] Material Example 9

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

[0184]

[0185] The synthesis route of the organic compound in this example is as follows:

[0186]

[0187] The specific preparation method is as follows: The preparation steps of the compound in this example are basically the same as those of M3, except that a1-1 is changed to a9-1 (CAS: 198964-46-4). The NMR data of the obtained product M7 are as follows: 1 H NMR(CDCl3): 8.09(d,2H),7.89(s,2H),7.78(d,2H),7.49(d,4H),6.86(d,4H),1.83(d,4H),1.35(s,18H),1.26-1.30(m,16H),0.88(m,6H),

[0188] Material Example 10

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

[0190]

[0191] The synthesis route of the organic compound in this example is as follows:

[0192]

[0193] The preparation method is specifically as follows: The preparation steps of the compound in this example are basically the same as those of W3, except that a1-1 is changed to a4-1 (CAS: 16433-88-8). The NMR data of the obtained product W7 are as follows: 1 1H NMR(CDCl3): 7.05(s, 2H), 6.93(d, 4H), 6.86(d, 4H), 3.91(s, 2H), 1.35(s, 18H).

[0194] Material Comparative Example 1

[0195] The material of this comparative example is TFB, also known as poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine)], CAS: 220797-16-0.

[0196] Material Comparative Example 2

[0197] The material of this comparative example is PVK, also known as poly(N-vinylcarbazole), CAS: 25067-59-8.

[0198] Device Example 1

[0199] This device example provides a quantum dot light-emitting diode and its preparation method, which specifically includes the following steps.

[0200] Step 1: After cleaning and drying the ITO substrate (with a thickness of 100 nm), it is treated in an ultraviolet ozone cleaning instrument for 15 min. Then, a PEDOT:PSS solution is spin-coated on the ITO substrate at a rotation speed of 5000 rpm, and then heated at 230 °C for 15 min to obtain a hole injection layer with a thickness of 45 nm.

[0201] Step 2: The organic compound M1 of Material Example 1 is dispersed in a chlorobenzene solvent to form a mixed solution with a concentration of 10 mg / ml. The mixed solution is spin-coated on the hole injection layer at a rotation speed of 2500 rpm, and then heated at 200 °C for 30 min to obtain a hole transport layer with a thickness of 40 nm.

[0202] Step 3: A hexane solution (with a concentration of 40 mg / ml) of blue ZnCdSeS / ZnS quantum dots is spin-coated on the hole transport layer at a rotation speed of 1500 rpm, and then heated at 100 °C for 5 min to obtain a light-emitting layer with a thickness of 40 nm.

[0203] Step 4: An ethanol solution (40 mg / ml) of ZnO is spin-coated on the light-emitting layer at a rotation speed of 3000 rpm, and then heated at 100 °C for 15 min to obtain an electron transport layer with a thickness of 25 nm;

[0204] Step 5: Vacuum deposit an Ag cathode with a thickness of 100 nm on the electron transport layer; then perform encapsulation to obtain the QLED device.

[0205] Device Examples 2 to 10

[0206] Device Example n is basically the same as Device Example 1, except that in Device Example n: in Step 2, the organic compound prepared by Material Example n is used to prepare the hole transport layer on the hole injection layer, where n is any integer from 2 to 10. Other parameters and steps remain unchanged.

[0207] Device Comparative Example 1

[0208] This device comparative example is basically the same as Device Example 1, except that in Step 2 of this device comparative example, TFB is used to prepare the hole transport layer on the hole injection layer, and other parameters and steps remain unchanged.

[0209] Device Comparative Example 2

[0210] This device comparative example is basically the same as Device Example 1, except that in Step 2 of this device comparative example, PVK is used to prepare the hole transport layer on the hole injection layer, and other parameters and steps remain unchanged.

[0211] Experimental Example

[0212] (1) Using M1 to 5, TFB, and PVK 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 is constructed: ITO / PEDDOT:PSS / organic compound / QD / MoO x / Ag. Then use the detection device to detect the hole mobility of the materials, and the results are shown in Table 1.

[0213] 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 )

[0214] 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.

[0215] Table 1

[0216] <![CDATA[Hole mobility (cm 2 V -1 s -1 ) <!-- 23 -->]]> M1 <![CDATA[7.8ⅹ10 -3 > M2 <![CDATA[5.8ⅹ10 -3 > M3 <![CDATA[6.3ⅹ10 -3 > M4 <![CDATA[4.7ⅹ10 -3 > M5 <![CDATA[1.1ⅹ10 -2 > M6 <![CDATA[9.2ⅹ10 -3 > M7 <![CDATA[8.8ⅹ10 -3 > M8 <![CDATA[1.2ⅹ10 -2 > M9 <![CDATA[5.6ⅹ10 -3 > M10 <![CDATA[5.3ⅹ10 -3 > TFB <![CDATA[3.6ⅹ10 -3 > PVK <![CDATA[2.5ⅹ10 -6 >

[0217] As can be seen from the above table, the organic compounds proposed in this application all have a high hole mobility and can be used as hole transport materials.

[0218] (2) Performance tests were carried out on the quantum dot light-emitting diodes of the device examples and device comparative examples, and the test results are shown in Table 2.

[0219] (1) The test method for the external quantum efficiency EQE is as follows:

[0220] The ratio of the number of electron-hole pairs injected into the quantum dots converted into the number of emitted photons, with the unit of %, is an important parameter to measure the quality of electroluminescent devices and can be obtained by measuring with an EQE optical test instrument. The specific calculation formula is as follows:

[0221]

[0222] Among them, ηe is the optical output coupling efficiency, ηr is the ratio of the number of recombined carriers to the number of injected carriers, χ is the ratio of the number of excitons generating photons to the total number of excitons, K R is the radiation process rate, and K NR is the non-radiation process rate.

[0223] Test conditions: Conducted at room temperature, with an air humidity of 30 - 60%.

[0224] (2) The test method for the lifetime T95@1000nit is as follows:

[0225] The time required for the device to reduce the brightness to a certain proportion of the maximum brightness under constant current or voltage drive. The time when the brightness drops to 95% of the maximum 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 obtaining the lifetime at high brightness through fitting with an extended exponential decay brightness decay fitting formula. For example, the lifetime at 1000nit is denoted as T95@1000nit. The specific calculation formula is as follows:

[0226]

[0227] Among them, T95 L is the lifetime at low brightness, T95 H is the measured lifetime at high brightness, L H is the device accelerated to the maximum brightness, L L is 1000nit, and A is the acceleration factor. In this experiment, the A value was obtained as 1.7 by measuring the lifetimes of several groups of red QLED devices at the rated brightness.

[0228] Table 2

[0229] T95@1000nit(h) EQE(%) Device Example 1 118 16.7 Device Example 2 104 14.9 Device Example 3 115 17.0 Device Example 4 98 14.8 Device Example 5 135 18.3 Device Example 6 126 17.6 Device Example 7 120 17.1 Device Example 8 141 18.9 Device Example 9 99 14.5 Device Example 10 90 14.3 Device Comparative Example 1 71 13.6 Device Comparative Example 2 31 9.98

[0230] As can be seen from the above table, each device embodiment has a high EQE and T95@1000nit, and is superior to Device Comparative Examples 1 and 2, indicating that the organic compound proposed in this application has a high hole mobility. When used as a hole transport layer material, it helps to improve the carrier balance in the device, improve the light-emitting efficiency of the device, and extend the service life of the device.

[0231] The technical solutions provided in the embodiments of this application have been introduced in detail above. Specific examples are used in this article to elaborate on the principles and implementation manners of this application. The descriptions of the above embodiments are only used to help understand the method and its core idea of this application; at the same time, for those skilled in the art, based on the idea of this 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 this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (I): (I)： Wherein, L is selected from any one of the following structures: Wherein, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocycle having 5 to 40 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 40 ring atoms; W is selected from NR3 or CR4R5; n1 is selected from 0 or 1, and n2 is selected from 0 or 1; R1, R2, R3, R4, and R5 are each independently selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 40 ring atoms, and a ring is formed or not formed between R4 and R5; When being substituted, the substituents are each independently selected from one or more combinations of D, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms each time they appear.

2. The organic compound according to claim 1, characterized in that, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocycle having 5 to 10 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 10 ring atoms.

3. The organic compound according to claim 1, characterized in that, R1, R2, R3, R4, and R5 are each independently selected from one or more combinations of H, a C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 10 ring atoms.

4. The organic compound according to any one of claims 1 to 3, characterized in that, L is selected from any one of the following structures: Wherein, R6 and R7 are each independently selected from one of H, D, and a substituted or unsubstituted C1-C30 alkyl group.

5. The organic compound according to claim 2 or 3, characterized in that, Each independently selected from any one of the following structures:

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

7. A method for preparing an organic compound, characterized in that, Comprising the following steps: Mix compound a and compound b, carry out a first reaction to obtain intermediate A; Mix the intermediate A and compound c, carry out a second reaction to obtain intermediate B; Mix the intermediate B and a radical catalyst, carry out a third reaction to obtain organic compound M; Wherein, the structural formulas of the compound a, compound b, compound c, intermediate A, intermediate B, and organic compound M are as follows: Wherein, R represents R1 or R2, Ar represents Ar1 or Ar2, n represents n1 or n2, and Z represents H or Si(CH3)3; X and Y are each independently selected from halogen groups; L is selected from any one of the following structures: Wherein, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are each independently selected from one or more of a substituted or unsubstituted heterocycle having 5 to 40 ring atoms and a substituted or unsubstituted aromatic ring having 6 to 40 ring atoms; W is selected from NR3 or CR4R5; n1 is selected from 0 or 1, and n2 is selected from 0 or 1; R1, R2, R3, R4, and R5 are each independently selected from one or more combinations of H, D, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted aryl group having 6 to 40 ring atoms, and a ring is formed or not formed between R4 and R5; When being substituted, the substituents are each independently selected from one or more combinations of D, a C1-C20 alkyl group, and an aryl group having 6 to 20 ring atoms each time they appear.

8. The preparation method according to claim 7, characterized in that, The temperature of the first reaction is -80°C to -70°C; and / or, The time of the first reaction is 1 to 5 h; and / or, The molar ratio of the compound a to the compound b is 1:(1 to 1.5); and / or, The molar ratio of the intermediate A to the compound c is 1:(0.3 to 0.5); and / or, The temperature of the third reaction is 15°C to 40°C; and / or, The time of the third reaction is 0.5 to 2 h; and / or, The radical catalyst includes one or more of lead dioxide and lead tetraacetate.

9. A composition, characterized in that, It includes a first compound and a solvent, and the first compound includes the organic compound described in any one of claims 1 to 6, or includes the organic compound prepared by the preparation method described in claim 7 or 8.

10. The composition according to claim 9, 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 a second compound, and the second compound 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'-tetraarylbenzidine, 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.

11. An optoelectronic device, characterized in that, It includes an anode, a hole functional layer, and a cathode, and the material of the hole functional layer includes the organic compound described in any one of claims 1 to 6, or includes the organic compound prepared by the preparation method described in claim 7 or 8, or is made of the composition described in claim 9 or 10.

12. The optoelectronic device according to claim 11, characterized in that, The anode and the cathode are each independently selected from a metal electrode, a carbon electrode, a doped or undoped metal oxide electrode, and a composite electrode; 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, Ga:SnO2; the material of the composite electrode is selected from 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; and / or, The optoelectronic device includes a light-emitting layer disposed between the cathode and the hole functional layer, and the material of the light-emitting layer is selected from organic light-emitting materials or quantum dot light-emitting materials; the organic light-emitting materials are selected from at least one of diaryl anthracene derivatives, stilbene aromatic derivatives, pyrene derivatives, 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; the quantum dot light-emitting materials are 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, and the I-III-VI group compounds are selected from at least one of CuInS, CuInSe, and AgInS;The core of the quantum dots with a core-shell structure is selected from any one of the above single-structure quantum dots, and the shell material of the quantum dots with a core-shell structure is selected from at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS, and ZnS; the perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the structural general formula of the inorganic perovskite semiconductor is AMX3, where A is 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 structural general 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+ 、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.

13. A display device, characterized in that, comprising the optoelectronic device according to claim 11 or 12.

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