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

Abstract

The invention discloses an organic compound, a preparation method thereof, a composition, a photoelectric device and a display device. The organic compound disclosed by the invention has good heat resistance and moisture resistance and is not easily influenced by temperature and humidity; the compound has good hole mobility and hole generation capacity, the hole generation capacity and the HOMO energy level of the compound can be regulated and controlled, and the compound can be applied as a hole injection material or a hole transport material.

Description

Technical Field

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

[0002] Hole injection materials refer to materials that can promote hole injection and enhance hole transport performance. Currently, the commonly used hole injection material is poly (3,4-ethylenedioxythiophene): polystyrene sulfonate (PEDOT:PSS), but PEDOT:PSS has high hygroscopicity due to its sulfonate structure, which is not conducive to its application in water and oxygen corrosion resistance.

[0003] Therefore, it is urgent to develop new hole injection materials and expand the types of hole injection materials to meet the needs of resistance to water and oxygen corrosion.

[0004] Application Contents

[0005] In view of this, the present application provides an organic compound and a preparation method, a composition, an optoelectronic device and a display device.

[0006] The embodiment of the present application is implemented as follows:

[0007] In a first aspect, the present invention provides an organic compound having a structure shown in formula (I):

[0008]

[0009] Among them, R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups;

[0010] Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures:

[0011]

[0012] Where X is CR 6R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S, m is 0 or 1;

[0013] R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 A combination of one or more of alkoxy;

[0014] R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms;

[0015] n1 and n2 are each independently selected from integers from 0 to 5;

[0016] n3 and n4 are each independently selected from integers of 0-4.

[0017] In a second aspect, the present invention also provides a method for preparing an organic compound, comprising the following steps:

[0018] Mixing compound m and an acidic solution to carry out a first reaction to obtain compound a;

[0019] The compound a is mixed with 2-aminobenzenethiol and subjected to a second reaction to obtain a compound b;

[0020] The compound b and the raw material c are mixed and subjected to a third reaction to obtain a compound d;

[0021] The compound d is reacted with a halogenating agent to generate a halogenated product, and the halogenated product is mixed with a raw material e to perform a fourth reaction to obtain an organic compound f;

[0022] Wherein, compound m, compound a, compound b, compound d, and organic compound f respectively have the following structural formulas:

[0023]

[0024] Among them, the raw material c includes the general formula R 1 The compound of Y, the general formula is R 2 Y, and a compound of the general formula R 3 A mixture of compounds of Y, wherein the raw material e includes a general formula of Ar1 B(OH) 2 Compounds with the general formula Ar 2 B(OH) 2 Compounds of the general formula Ar 3 B(OH) 2 A mixture of compounds of, Y, Y', Y" each appear independently selected from -Cl, -Br or -I;

[0025] R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups;

[0026] Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures:

[0027]

[0028] Where X is CR 6 R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S, m is 0 or 1;

[0029] R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 A combination of one or more of alkoxy;

[0030] R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms;

[0031] n1 and n2 are each independently selected from integers from 0 to 5;

[0032] n3 and n4 are each independently selected from integers of 0-4.

[0033] In a third aspect, the present application further proposes a composition comprising an organic compound and a solvent, wherein the organic compound comprises the organic compound described above, or comprises an organic compound prepared by the method for preparing the organic compound described above.

[0034] In a fourth aspect, an embodiment of the present application further provides a photoelectric device, comprising an anode, a hole functional layer and a cathode, wherein the material of the hole functional layer comprises the above-mentioned organic compound, or comprises an organic compound prepared by the above-mentioned preparation method of the organic compound, or is made of the above-mentioned composition.

[0035] In a fifth aspect, an embodiment of the present application further provides a display device, comprising the above-mentioned optoelectronic device.

[0036] The present application provides an organic compound, which has good heat resistance and moisture resistance and is not easily affected by temperature and humidity; the compound has good hole mobility and hole generation ability, and its hole generation ability and HOMO energy level are controllable, and can be used as a hole injection material or a hole transport material. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0038] Figure 1 It is a structural schematic diagram of an embodiment of a photoelectric device provided in the present application.

[0039] Figure numerals: 100 - optoelectronic device, 10 - anode, 20 - cathode, 30 - electronic functional layer, 40 - light-emitting layer, 50 - hole functional layer, 51 - hole injection layer, 52 - hole transport layer. DETAILED DESCRIPTION

[0040] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation methods 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 specified, the directional words such as "upper" and "lower" used are specifically the directions of the drawings in the accompanying drawings. In addition, in the description of the present application, the term "including" means "including but not limited to". 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 simplicity, and should not be understood as a hard limit on the scope of the present application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the range. For example, description of a range from 1 to 6 should be considered to have 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., as well as single numbers within the stated range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the stated range.

[0041] In this application, "and / or" describes the association relationship of associated objects, indicating that there may be three relationships. For example, A and / or B can represent: A exists alone, A and B exist at the same time, and B exists alone. A and B can be singular or plural.

[0042] In the present application, "at least one" means one or more, and "plurality" means two or more. "At least one", "at least one of the following" or similar expressions refer to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, c can be single or multiple, respectively.

[0043] In the present application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be interchanged.

[0044] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0045] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted and no additional definition is provided, "substituted" means that the hydrogen of the compound or group is replaced by the following substituents: a deuterium atom, a halogen, a hydroxyl group, a nitro group, a cyano group, an isocyano group, an amino group, an azido group, an amidino group, a hydrazine group, a hydrazone group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a silyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C30 aryl group, a C7-C30 aralkyl group, a C1-C30 alkoxy group, a C1-C20 heteroalkyl group, a C3-C20 heterocyclic group, a C3-C20 heteroaralkyl group, a C3-C30 cycloalkyl group, a C3-C15 cycloalkenyl group, a C6-C15 cycloalkynyl group, a C3-C30 heterocycloalkyl group, or a combination of one or more thereof.

[0046] In the present application, "ring atoms" means the number of atoms of the ring atoms constituting the ring itself in a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonding to form a ring, i.e., 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 is true for the "ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0047] In the present application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group with 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, and the aromatic group can be optionally further substituted. Preferably, substituted or unsubstituted aromatic groups with 6 to 30 ring atoms are substituted or unsubstituted, more preferably substituted or unsubstituted aromatic groups with 6 to 18 ring atoms, particularly preferably substituted or unsubstituted aromatic groups with 6 to 14 ring atoms, and the aromatic group can be optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthyl, fluorenyl, perylene, acenaphthene and derivatives thereof. It is understandable that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0048] In the present application, "heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, and the non-carbon atom can be an N atom, an O atom, an S atom, an Si atom, a P atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, Triazine, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0049] In the present application, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, such as "C 1-9 "Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, each occurrence of which can be independently C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9Alkyl. 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-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl decyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 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, and the like.

[0050] In this application, “-C n H 2n+1 "Unless otherwise specified or limited, it means a straight-chain alkyl group. For example, -C 4 H 9 It represents n-butyl.

[0051] In the present application, "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above is connected to another group via an oxygen atom. Phrases containing this term include, but are not limited to, methoxy (-O-CH 3 or -OMe), ethoxy (-O-CH 2 CH 3 or -OEt) and tert-butyloxy (-OC(CH 3 ) 3 or -OtBu).

[0052] In the present application, "alkylphenyl" is a phenyl group substituted with an alkyl group, and its structural formula may be "-phenyl-alkyl", and the alkyl group may refer to the description above. Suitable examples include, but are not limited to, tolyl, ethylphenyl, etc. 7 ~C 36 C in phenylalkyl 7 ~C36 is the number of carbon atoms in the entire group.

[0053] In the present application, "alkoxyphenyl" is a phenyl group substituted with an alkoxy group, and the alkoxy group can refer to the description above. Suitable examples include, but are not limited to: wait.

[0054] In the present application, "'*' connected to a single bond" indicates a connection site or a fusion site. When a connection site is not specified in a group, it indicates that an optional connection site in the group can be used as a connection site. For example, In the embodiment, any connectable sites on the two benzene rings and any connectable sites on M can be used as the connecting sites for connecting with the N atom in the main skeleton structure; it is understood that when M is used as the connectable site, M is N or SiR 10 In addition, it can also be when M is NR 9 , or SiR 10 R 11 When R 9 , R 10 or R 11 as a connection site.

[0055] In the present application, the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring. Medium R 4 It can be connected to any substitutable position in the benzene ring. Further, in the present application, when the same substituent appears multiple times, it can be independently selected from different groups; for example, the above general formula can contain n1 R 4 , then each R 4 Can be independently selected from different groups.

[0056] The terms "combination thereof", "any combination thereof", "any combination thereof" and the like used in this application include all suitable combinations of any two or more of the listed items.

[0057] The present application provides an organic compound having a structure shown in formula (I):

[0058]

[0059] Among them, R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36alkylphenyl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups;

[0060] Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures:

[0061]

[0062] Where X is CR 6 R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S, m is 0 or 1; R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 One or more combinations of alkoxy groups; R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms; n1 and n2 are each independently selected from integers of 0 to 5, for example, 0, 1, 2, 3, 4 or 5; n3 and n4 are each independently selected from integers of 0 to 4, for example, 0, 1, 2, 3 or 4.

[0063] The organic compound proposed in the embodiment of the present application contains a trimeric indenyl phenothiazine structural unit and has a unique aromatic heterocyclic unit for end group modification; the compound has a very rigid conjugated structure, has good heat resistance and moisture resistance, and is conducive to intramolecular charge transfer, so that the compound not only has good hole mobility and hole generation ability, but also its hole generation ability and HOMO energy level are controllable, can be used as a hole injection material or a hole transport material, and is not easily affected by temperature and humidity, and has good stability in a hot and humid environment.

[0064] In some embodiments, this organic compound can be used to prepare the hole functional layer 50 of the optoelectronic device 100. The compound is not easy to dissociate acid radicals in a liquid environment, and its acidity is weaker than that of PEDOT:PSS. When used to make the hole functional layer 50, it will not corrode the adjacent anode 10 or the light-emitting layer 40, thereby avoiding the risk of leakage current caused by film corrosion; the compound has good hole mobility and hole generation ability, and when used to make the hole functional layer 50, it can well enhance the hole injection ability, improve the carrier balance of the device, and enhance the photoelectric performance of the device; in addition, since the hydrophilicity of the compound is not as good as that of PEDOT:PSS, it can avoid absorbing external moisture and then affecting the light-emitting layer 40, resulting in quenching of the light-emitting layer 40 material, and since the compound has good heat resistance and moisture resistance, the device also has good stability in a hot and humid environment, which helps to extend the service life of the device.

[0065] In addition, the compound has good work function matching with the anode 10 material. When the compound is used as a hole injection material in the optoelectronic device 100, it helps to reduce the energy barrier between the anode 10 and the hole transport layer 52 / light-emitting layer 40, thereby promoting hole injection. In addition, by regulating the end group Ar in the organic compound 1 To Ar 3 The type can effectively regulate the hole generation ability and HOMO energy level of the organic compound, thereby improving the matching of the organic compound with the anode 10 material and better promoting hole injection.

[0066] End group (Ar 1 To Ar 3 ) can be connected to any connection site on the terminal benzene ring of the phenothiazine unit. In some embodiments, the organic compound has a structure shown in formula (II):

[0067]

[0068] In some embodiments, R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 One or more of the alkoxyaryl groups; it is understood that C7 ~C 36 In the alkylaryl group, the total number of carbon atoms in the alkyl and aryl groups is from 7 to 36; 7 ~C 36 In the alkoxyaryl group, the total number of carbon atoms of the alkoxy group and the aryl group is 7 to 36.

[0069] Furthermore, in some embodiments, R 1 , R 2 , R 3 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 Alkylphenyl, substituted or unsubstituted C 7 ~C 36 It is understood that phenyl is one of the aromatic groups, C 7 ~C 36 In alkylphenyl, the benzene ring itself has 6 carbon atoms, and the alkyl group is 1 to 30; similarly, C 7 ~C 36 In the alkoxyphenyl group, the benzene ring itself has 6 C atoms, and the number of carbon atoms in the alkoxy group is 1 to 30.

[0070] Furthermore, in some embodiments, R 1 , R 2 , R 3 Each independently selected from substituted or unsubstituted C 1 ~C 12 Alkyl, substituted or unsubstituted C 1 ~C 12 Alkoxy, substituted or unsubstituted C 7 ~C 18 Alkylphenyl, substituted or unsubstituted C 7 ~C 18 A combination of one or more groups in alkoxyphenyl; Further, in some embodiments, R 1 , R 2 , R 3 Each independently selected from C 1 ~C 12 Straight chain or branched alkyl, C 7 ~C 18 A type of alkoxyphenyl.

[0071] R 1 , R 2 , R 3can be selected from the same substituent or different substituents; in one embodiment, R 1 , R 2 , R 3 All are selected from the same substituent, which helps to reduce the difficulty of synthesizing organic compounds.

[0072] It is understood that in "substituted or unsubstituted", when substituted, the substituent may be any common substituent in the art, see the above term explanation for details. In some embodiments, the substituent is selected from a combination of one or more of hydrogen, deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, and cyano; further, the substituent is selected from hydrogen or deuterium.

[0073] In some embodiments, Ar 1 ,Ar 2 ,Ar 3 Each independently selected from one of the following structures:

[0074]

[0075] Further, in some embodiments, Ar 1 ,Ar 2 ,Ar 3 Each is independently selected from one of the following structural formulas (1-1) to (1-13), so that the organic compound has an energy level that is more compatible with the commonly used anode 10 material and has a better hole generation ability.

[0076]

[0077] In some embodiments, Ar 1 ,Ar 2 ,Ar 3 All are selected from the same substituent, which helps to reduce the difficulty of synthesizing organic compounds.

[0078] In one embodiment, n1 and n2 are each independently selected from integers of 0 to 1, for example, they can be selected from 0 or 1. For example, n1 is 0 and n2 is 1; or, n1 is 1 and n2 is 0; or, n1 is 0 and n2 is 0; or, n1 is 1 and n2 is 1. In one embodiment, n3 and n4 are each independently selected from integers of 0 to 1, for example, they can be selected from 0 or 1. For example, n3 is 0 and n4 is 1; or, n3 is 1 and n4 is 0; or, n3 is 0 and n4 is 0; or, n3 is 1 and n4 is 1.

[0079] In some embodiments, R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 10Alkyl, substituted or unsubstituted C 1 ~C 10 In some other embodiments, R 4 , R 5 Each independently selected from C 1 ~C 4 Alkyl, C 1 ~C 4 One of the alkoxy groups.

[0080] In some embodiments, R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 10 is a combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 10 ring atoms. 6 To R 11 Each independently selected from H, D, C 1 ~C 10 is a combination of one or more of an alkyl group and an aryl group having 6 to 10 ring atoms. 6 To R 11 Each independently selected from H, D, C 1 ~C 4 One of alkyl and phenyl.

[0081] In some specific embodiments, the organic compound includes one or more of the following structural formulas:

[0082]

[0083]

[0084]

[0085] The present application provides a method for preparing an organic compound, and the organic compound can be prepared through the following synthetic route.

[0086]

[0087] The preparation method comprises the following steps:

[0088] S10, mixing compound m and an acidic solution to perform a first reaction to obtain compound a;

[0089] S20, mixing the compound a with 2-aminobenzenethiol, and performing a second reaction to obtain a compound b;

[0090] S30, mixing the compound b and the raw material c, and performing a third reaction to obtain a compound d;

[0091] S40, after reacting the compound d with a halogenating agent to generate a halogenated product, the halogenated product is mixed with a raw material e to perform a fourth reaction to obtain an organic compound f;

[0092] Wherein, compound m, compound a, compound b, compound d, and organic compound f respectively have the structural formulas shown in the above synthesis routes.

[0093] Among them, the raw material c includes the general formula R 1 The compound of Y, the general formula is R 2 Y, and a compound of the general formula R 3 A mixture of compounds of Y, wherein the raw material e includes a general formula of Ar 1 B(OH) 2 Compounds with the general formula Ar 2 B(OH) 2 Compounds of the general formula Ar 3 B(OH) 2 A mixture of compounds of, Y, Y', Y" each appear independently selected from -Cl, -Br or -I;

[0094] R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups;

[0095] Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures:

[0096]

[0097] Where X is CR 6 R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S; m is 0 or 1; R 4 , R5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 A combination of one or more of alkoxy groups; R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group and a substituted or unsubstituted aryl group having 6 to 60 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.

[0098] In some embodiments, compound m is 5,6-dihalogen-1-indanone, such as 5,6-dichloro-1-indanone, CAS: 68755-31-7; or 5,6-dibromo-1-indanone, CAS: 1289167-38-9, etc. Specifically, taking 5,6-dibromo-1-indanone as an example, the synthetic route of compound a obtained by reacting compound m is as follows:

[0099]

[0100] In some embodiments, in step S10, the acidic solution includes a mixed solution of acetic acid and concentrated hydrochloric acid, and in the mixed solution, the volume ratio of the acetic acid to the concentrated hydrochloric acid is 1:(0.3-0.5). Wherein, the volume ratio of the acetic acid to the concentrated hydrochloric acid can be 1:0.3, 1:0.31, 1:0.33, 1:0.35, 1:0.38, 1:0.4, 1:0.43, 1:0.45, 1:0.47, 1:0.5 and values ​​between any two of the above values. The molar ratio of the compound m to the acetic acid is 1:(40-80); for example, it can be 1:40, 1:50, 1:60, 1:70, 1:80 and values ​​between any two of the above values. Referring to the above synthetic route, taking compound m as the starting material, a cyclization reaction is carried out in a mixed system of acetic acid and concentrated hydrochloric acid to generate a halogenated trimerized indene, i.e., compound a.

[0101] Specifically, the conditions of the first reaction can be: the reaction temperature of the first reaction is 80-130°C, for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C, 120°C, 130°C and values ​​between any two of the above values; the reaction time of the first reaction is 12-24h, for example, it can be 12h, 15h, 18h, 20h, 22h, 24h and values ​​between any two of the above values.

[0102] In some embodiments, step S20 can be specifically implemented according to the following steps: under the protection of inert gas, the compound a, 2-aminobenzenethiol and ferric citrate are mixed to carry out a second reaction to obtain compound b.

[0103] It can be understood that inert gas generally refers to protective gases such as nitrogen, helium, argon, etc., which can isolate or reduce water and oxygen in the reaction system.

[0104] Among them, the molar ratio of the compound a to 2-aminobenzenethiol is 1:(4-5), for example, it can be 1:4, 1:42, 1:45, 1:48, 1:5 and values ​​between any two of the above values; the molar ratio of the compound a to the ferric citrate is 1:(4-5), for example, it can be 1:4, 1:42, 1:45, 1:48, 1:5 and values ​​between any two of the above values.

[0105] In some embodiments, the reaction temperature of the second reaction is 80-110°C, for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C and values ​​between any two of the above values; the reaction time of the second reaction is 8-12h, for example, it can be 8h, 8.5h, 9h, 9.5h, 10h, 10.5h, 11h, 12h and values ​​between any two of the above values.

[0106] In step S30, the compound b and the raw material c may undergo a carbon-carbon coupling reaction under alkaline conditions to generate a compound d.

[0107] Among them, the alkaline condition can be achieved by adding strong alkaline substances such as sodium hydroxide and potassium hydroxide. The alkaline condition can specifically be that the pH of the entire solution system is greater than or equal to 9, for example, it can be pH9.0, pH9.3, pH9.5, pH9.8, pH10.0, pH10.5, pH11.0, etc.

[0108] Wherein, the molar ratio of the compound b to the raw material c is 1:(3-5); for example, it can be 1:3, 1:3.5, 1:4, 1:42, 1:45, 1:48, 1:5 and values ​​between any two of the above values.

[0109] In some embodiments, the reaction temperature of the third reaction is 80-110°C, for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C and values ​​between any two of the above values; the reaction time of the third reaction is 6-24h, for example, it can be 6h, 12h, 15h, 18h, 20h, 22h, 24h and values ​​between any two of the above values.

[0110] In step S40, the compound d is subjected to a halogenation reaction with a halogenating agent to generate a halogenated product f-1. The halogenating agent may be a halogenating agent RY commonly used in the art. In some specific embodiments, the halogenating agent may be N-bromosuccinimide (NBS, CAS: 128-08-5), liquid bromine, 1,3-dibromo-5,5-dimethylhydantoin (DBH), N-iodosuccinimide (NIS), and the like.

[0111] In some embodiments, the molar ratio of the compound d to the halogenating agent is 1:(3-6), for example, it can be 1:3, 1:3.5, 1:4, 1:42, 1:45, 1:48, 1:5, 1:55, 1:6, and values ​​between any two of the above values; the reaction temperature of the compound d and the halogenating agent is 40-60°C, for example, it can be 40°C, 45°C, 50°C, 55°C, 60°C, and values ​​between any two of the above values; the reaction time of the compound d and the halogenating agent is 6-12h, for example, it can be 6h, 6.5h, 7h, 7.5h, 8h, 8.5h, 9h, 9.5h, 10h, 10.5h, 11h, 12h, and values ​​between any two of the above values.

[0112] In step S40, the halogenated product f-1 undergoes a Suzuki coupling reaction with the raw material e under palladium catalyst conditions, thereby introducing Ar at the original halogen substitution position. 1 ,Ar 2 or Ar 3 , to obtain compound f.

[0113] Wherein, the molar ratio of the compound d to the raw material e is 1:(3-5); for example, it can be 1:3, 1:3.5, 1:4, 1:42, 1:45, 1:48, 1:5 and values ​​between any two of the above values.

[0114] In some embodiments, the reaction temperature of the fourth reaction is 80-110°C, for example, it can be 80°C, 85°C, 90°C, 95°C, 100°C, 105°C, 110°C and values ​​between any two of the above values; the reaction time of the fourth reaction is 12-24h, for example, it can be 12h, 15h, 18h, 20h, 22h, 24h and values ​​between any two of the above values.

[0115] In the above steps, the palladium catalyst used can be a palladium catalyst commonly used in the art, such as tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ), tetrakis(triphenylphosphine)palladium(pd(pph 3 ) 4) etc.; in some embodiments, the molar ratio of the halogenated product f-1 and the palladium catalyst is 1:(0.1-0.2); for example, it can be 1:0.1, 1:0.12, 1:0.15, 1:0.17, 1:0.18, 1:0.19, 1:0.2 and values ​​between any two of the above values.

[0116] It is understandable that the organic compound provided in the present application is not limited to being prepared by the preparation method of the organic compound provided in the present application.

[0117] Based on the above organic compound embodiment, the present application also proposes a composition, which includes the above organic compound and a solvent. The composition can be used as a hole functional layer 50 ink to prepare the hole functional layer 50 of the optoelectronic device 100.

[0118] In one embodiment, in the composition, the concentration of the organic compound is 5 to 30 mg / ml; for example, it can be 5 mg / ml, 10 mg / ml, 15 mg / ml, 20 mg / ml, 25 mg / ml, 30 mg / ml, and a value between any two of the above values.

[0119] In some embodiments, the solvent includes one or more of chlorobenzene, toluene, and xylene.

[0120] In some embodiments, the composition may contain one organic compound, or two or more organic compounds.

[0121] In some embodiments, in addition to the organic compound and the solvent, the composition may also include other conductive materials or semiconductor materials, such as other hole transport materials or hole injection materials, such as 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-methylphenyl)- phenylphenylamino)-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 compounds, 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'-di(naphthalene-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, PEDOT:PSS doped with s-MoO 3 One or more of derivatives of, 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.

[0122] The composition has good hole generation ability and hole mobility, and can effectively adjust its own HOMO energy level, and has good matching with the commonly used anode 10 material. It is used to prepare the hole functional layer 50 of the optoelectronic device 100, which helps to promote hole injection, improve carrier balance, and enhance the optoelectronic performance of the device; the acidity and hydrophilicity of the composition are both weak, and the prepared hole functional layer 50 will not corrode the adjacent anode 10 or the light-emitting layer 40, which can avoid the risk of leakage current caused by film corrosion, and will not absorb external moisture, which can avoid the device from absorbing moisture, thereby affecting the light-emitting layer 40 and causing quenching of the light-emitting layer 40 material; in addition, because the compound has good heat resistance and moisture resistance, the device also has good stability in a hot and humid environment, which helps to extend the service life of the device.

[0123] When the hole functional layer 50 is prepared by using the above composition, the solution method can be used for spin coating, scraping, printing or spraying on the substrate. After the film is formed, it is annealed at 100-160° C. for 10-60 minutes to obtain the hole functional layer 50.

[0124] 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. Figure 1 The photoelectric device 100 includes an anode 10, a hole functional layer 50 and a cathode 20. The material of the hole functional layer 50 includes the organic compound described above, or includes an organic compound prepared by the preparation method of the organic compound described above, or is made of the composition described above.

[0125] The hole functional layer 50 of the optoelectronic device 100 comprises an organic compound. Since the compound is weakly acidic, when used to make the hole functional layer 50, it will not corrode the adjacent anode 10 or the light-emitting layer 40, thereby avoiding the risk of leakage current caused by film corrosion. The compound has good hole mobility and hole generation ability. When used to make the hole functional layer 50, it can well enhance the hole injection ability, improve the carrier balance of the device, and enhance the photoelectric performance of the device. In addition, since the hydrophilicity of the compound is not as good as that of PEDOT:PSS, it can avoid absorbing external moisture and then affecting the light-emitting layer 40, resulting in quenching of the light-emitting layer 40 material. Moreover, since the compound has good heat resistance and moisture resistance, the device also has good stability in a hot and humid environment, which helps to extend the service life of the device.

[0126] In addition, the compound has good work function matching with the anode 10 material. When the compound is used as a hole injection material in the optoelectronic device 100, it helps to reduce the energy barrier between the anode 10 and the hole transport layer 52 / light-emitting layer 40, thereby promoting hole injection. In addition, by regulating the end group Ar in the organic compound1 To Ar 3 The type can effectively regulate the hole generation ability and HOMO energy level of the organic compound, thereby improving the matching of the organic compound with the anode 10 material and better promoting hole injection.

[0127] In some embodiments, the hole functional layer 50 includes one or two layers of a hole transport layer 52 and a hole injection layer 51. When the hole functional layer 50 includes the hole transport layer 52 and the hole injection layer 51, the hole injection layer 51 is located between the hole transport layer 52 and the anode 10. Further, the material of the hole injection layer 51 includes the above-mentioned organic compound, which has a better match with the anode 10 material and the commonly used hole transport material (such as TFB, PVK, etc.). When used as the hole injection layer 51, it is more conducive to promoting the injection of holes from the anode 10 into the light-emitting layer 40. It should be noted that when the material of the hole injection layer 51 includes the above-mentioned organic compound, the hole transport layer 52 can be made of hole transport materials commonly used in the art, for example, it can 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'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (NPB), spiro NPB or more thereof.

[0128] In some embodiments, the optoelectronic device 100 may further include a light-emitting layer 40 , which is disposed between the cathode 20 and the hole functional layer 50 .

[0129] In one embodiment, the material of the light-emitting layer 40 is selected from organic light-emitting materials or quantum dot light-emitting materials.

[0130] The organic light-emitting material can be selected from at least one of diaromatic anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, TBPe fluorescent materials emitting blue light, TTPA fluorescent materials emitting green light, TBRb fluorescent materials emitting orange light, and DBP fluorescent materials emitting red light.

[0131] The quantum dot luminescent material can be selected from at least one of a single structure quantum dot, a core-shell structure quantum dot and a perovskite semiconductor material. The single structure quantum dot is selected from at least one of a II-VI group compound, a IV-VI group compound, a III-V group compound and a I-III-VI group compound. The II-VI group compound is selected from CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdS At least one of dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, and the IV-VI group compound is selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, Sn At least one of PbTe, SnPbSSe, SnPbSeTe, and SnPbSTe, and the III-V compound is selected from 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 , at least one of GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb, the I-III-VI group compound is selected from at least one of CuInS, CuInSe and AgInS; the core of the quantum dots with core-shell structure is selected from any one of the above-mentioned single-structure quantum dots, and the shell material of the quantum dots with core-shell structure is selected from at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS and ZnS.

[0132] As an example, the core-shell structured quantum dots 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.

[0133] It should be noted that, for the material of the aforementioned single structure quantum dot, or the material of the core of the core-shell structure quantum dot, or the material of the shell of the core-shell structure quantum dot, the chemical formula provided only indicates the elemental composition, but does 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 indicated, it corresponds to Cd x Zn 1-x Se,0 <x<1。

[0134] The perovskite semiconductor material is selected from doped or undoped inorganic perovskite semiconductors, or organic-inorganic hybrid perovskite semiconductors; the inorganic perovskite semiconductor has a general structural formula of AMX 3 , 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+ At least one of, X is a halogen anion selected from Cl - Br - ,I - At least one of the following; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX 3 , wherein B is an organic amine cation selected from CH 3 (CH 2 ) n-2 NH 3 + or [NH 3 (CH 2 ) n NH 3 ]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+ At least one of, X is a halogen anion selected from Cl - Br - ,I - When n=2, the inorganic metal halide octahedral MX 6 4- The metal cation M is located at the center of the halogen octahedron, and the organic amine cation B fills the gap between the octahedrons to form an infinitely extended three-dimensional structure. When n>2, the inorganic metal halide octahedron MX connected in a top-sharing manner 6 4- It extends in two dimensions to form a layered structure, with an organic amine cation bilayer (protonated monoamine) or an organic amine cation monolayer (protonated diamine) inserted between the layers, and the organic layer and the inorganic layer overlap to form a stable two-dimensional layered structure.

[0135] In one embodiment, the quantum dot luminescent material includes one or more of red quantum dots, green quantum dots, and blue quantum dots.

[0136] In one embodiment, the optoelectronic device 100 further includes an electronic functional layer 30, and the electronic functional layer 30 is disposed between the cathode 20 and the light-emitting layer 40. The electronic functional layer 30 may include an electron injection layer and / or an electron transport layer. When the electronic functional layer 30 includes an electron injection layer and an electron transport layer, the electron injection layer is disposed close to the cathode 20 side, and the electron transport layer is disposed close to the light-emitting layer 40 side.

[0137] The electronic functional layer 30 can be prepared by using electronic functional materials known in the art for use in optoelectronic devices 100 and having electron transport properties or electron injection properties. Specifically, the electron transport layer material 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 ZnO, TiO 2 SnO 2 One or more of the following; the metal oxide in the doped metal oxide includes ZnO, TiO2 SnO 2 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 electron injection layer material includes at least one of cesium carbonate, cesium fluoride, cesium azide, and lithium fluoride. .

[0138] In one embodiment, the anode 10 and the cathode 20 are 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 fiber; the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, ITZO, ICO, AMO, SnO 2 、In 2 O 3 、Cd:ZnO、F:SnO 2 、In:SnO 2 、Ga:SnO 2 At least one of the following; the material of the composite electrode is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO 2 / Ag / TiO 2 、TiO 2 / Al / TiO 2 At least one of ZnS / Ag / ZnS and ZnS / Al / ZnS. Wherein, " / " represents a stacked structure, for example, the composite electrode AZO / Ag / AZO represents an electrode of a composite structure of three stacked layers consisting of an AZO layer, an Ag layer and an AZO layer.

[0139] It is understandable that, in addition to the above-mentioned functional layers, the optoelectronic device 100 may also be provided with some functional layers conventionally used in optoelectronic devices 100 that help improve 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.

[0140] It can be understood that the material and thickness of each layer of the optoelectronic device 100 can be set and adjusted accordingly according to the light emitting requirements of the optoelectronic device 100 .

[0141] In some embodiments, the optoelectronic device 100 further includes a substrate (not shown), which may also be referred to as a substrate, and the above-mentioned film layer structure is arranged on one side of the substrate. The substrate may be a rigid substrate or a flexible substrate. The rigid substrate may be a ceramic material or various glass materials, etc. The flexible substrate may be a substrate formed of materials such as polyimide film (PI) and its derivatives, polyethylene naphthalate (PEN), phosphoenolpyruvic acid (PEP) or diphenylene ether resin. In one embodiment, the material of the substrate includes a combination of one or more of glass, silicon wafer, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate, polyamide, and polyether sulfone.

[0142] It can be understood that the photoelectric device 100 can be an upright photoelectric device or an inverted photoelectric device. When the photoelectric device 100 is an upright photoelectric device, the substrate is combined with the side of the anode 10 away from the light-emitting layer 40. When the photoelectric device 100 is an inverted photoelectric device, the substrate is combined with the side of the cathode 20 away from the light-emitting layer 40.

[0143] It is understandable 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 50, the electronic functional layer 30 and other film layers, can be implemented by conventional techniques in the art, such as chemical methods or physical methods. Among them, the chemical method includes chemical vapor deposition, continuous ion layer adsorption and reaction method, anodization method, electrolytic deposition method, and coprecipitation method. The physical method includes physical plating method and solution method, wherein the physical plating method includes: thermal evaporation coating method, electron beam evaporation coating method, magnetron sputtering method, multi-arc ion plating method, physical vapor deposition method, atomic layer deposition method, pulsed laser deposition method, etc.; the solution method can be spin coating, printing method, inkjet printing method, blade coating method, printing method, dip pulling method, immersion method, spraying method, roll coating method, casting method, slit coating method and strip coating method, etc.

[0144] It is understandable that the optoelectronic device 100 may further include an encapsulation layer (not shown) to isolate water and oxygen (for example, to make the concentration of oxygen and water less than 0.1ppm) and improve the performance stability of the optoelectronic device 100. Specifically, the encapsulation material used to form the encapsulation layer may be selected from at least one of UV glue, metal film, and glass glue. In a specific embodiment, the encapsulation material may be acrylic resin or epoxy resin.

[0145] The present application also relates to a display device, which includes the optoelectronic device 100 provided in the present application. The display device can be any electronic product with a display function, including but not limited to smart phones, tablet computers, laptop computers, digital cameras, digital video cameras, smart wearable devices, smart weighing electronic scales, car displays, televisions or e-book readers, wherein the smart wearable device can be, for example, a smart bracelet, a smart watch, a virtual reality (VR) helmet, etc.

[0146] The present application is described in detail below by means of specific examples, which are only partial examples of the present application and are not intended to limit the present application. The raw materials used in the following examples are all commercially available products unless otherwise specified.

[0147] The structural formulas of compounds M1 to M10 mentioned in the following examples are as follows:

[0148]

[0149]

[0150]

[0151] Example 1: The synthetic route of the organic compound M1 of this example is as follows:

[0152]

[0153] Preparation of compound M1-2: Compound M1-1 (5,6-dibromo-1-indanone, 4 mmol, 1151 mg) (CAS: 1289167-38-9) was added to a 100 mL two-necked bottle, 20 ml of acetic acid and 10 ml of concentrated hydrochloric acid solution were added, and the mixture was heated to 110°C for 11 h. The reaction was stopped when the raw material was completely reacted by monitoring by thin layer chromatography (TLC). The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether: ethyl acetate (volume ratio of 10:1). Finally, compound M1-2 was obtained as a white solid product (1295 mg) with a yield of 40%.

[0154] Preparation of compound M1-3: Compound M1-2 (1 mmol, 809.6 mg) was added to a 100 mL two-necked bottle, 2-aminobenzenethiol (4 mmol, 500 mg) (CAS: 137-07-5), and ferric citrate (4 mmol, 980 mg) (CAS: 3522-50-7) were added, dissolved in 30 mL N, N-dimethylformamide, heated to 110 ° C, reacted for 10 h, and the reaction was stopped when the raw material was completely reacted by monitoring by thin layer chromatography (TLC). The reaction solution was distilled under reduced pressure to remove the solvent, and the crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether: ethyl acetate (volume ratio of 1:1), and finally 493 mg of compound M1-3 was obtained. Compound M1-3 was a white solid with a yield of 70%.

[0155] Preparation of compound M1-4: Compound M1-3 (2 mmol, 1410 mg) was added to a 100 mL two-necked flask, and 1-bromohexane (8 mmol, 1700 mg) (CAS: 111-25-1) and potassium hydroxide (8 mmol, 446 mg) were weighed and added. 40 ml of dimethyl sulfoxide was added, nitrogen was introduced and vacuumed for 15 minutes using a vacuum pump, stirred and heated to 85°C, and the reaction was continued for 24 hours. The reaction was stopped and cooled to room temperature, and the reaction solution was extracted. 200 ml of water and 1500 ml of dichloromethane were used for repeated extraction 3 to 4 times. The obtained organic extract was dried using anhydrous magnesium sulfate, and the filtrate was collected and mixed with 200 to 300 mesh silica gel for purification and separation using column chromatography. The eluent used petroleum ether, dichloromethane and ethyl acetate (volume ratio of 20:1:1). Finally, 1722 mg of compound M1-4 was obtained. Compound M1-3 was a white solid with a yield of 90%.

[0156] Preparation of compound M1: Compound M1-4 (1 mmol, 957 mg) was added to a 100 mL two-necked bottle and dissolved in 40 mL of chloroform. N-bromosuccinimide (NBS) (3 mmol, 534 mg) was dissolved in 10 mL of chloroform and gradually added dropwise to the solution. The mixture was stirred for 3 h in an ice bath. The reaction was stopped when the raw material was completely reacted by monitoring by thin layer chromatography (TLC). The reaction solution was distilled under reduced pressure to remove the solvent. The crude product was mixed with 200 to 300 mesh silica gel and separated by column chromatography. The mobile phase was petroleum ether: ethyl acetate (volume ratio of 20:1) to obtain an intermediate crude product. Then triphenylamine boric acid (4 mmol, 1156 mg) (CAS: 201802-67-7), Pd2(PP h3)4 (0.05mmol, 50mg) and sodium carbonate aqueous solution (5mmol, 480mg), then add redistilled toluene 40mL, ethanol 5ml, pass nitrogen, use vacuum pump to evacuate and replace with nitrogen for 15 minutes, cover the reaction bottle with tin foil to avoid light, stir and heat to 110℃ for 24h, stop the reaction, cool to room temperature, extract the reaction solution, use dichloromethane (1000mL) and water (250mL) to wash repeatedly 3 to 4 times, dry the organic phase with anhydrous magnesium sulfate, use column chromatography for crude separation, the developing solvent is petroleum ether: dichloromethane: acetone (volume ratio is 20:2:1), and 1180mg of the final product M1 is obtained. M1 is a white solid with a yield of 70%.

[0157] The NMR data are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.64-7.61(m,6H),7.60-7.59(m,3H),7.56-7.53(m,3H),7.34-7.33(m,3H),7.29-7.23(m,24H),7.19-7.18(m ,3H),7.16-7.11(m,15H),4.24(s,6H),3.91(t,J=6.3Hz,6H),1.71-1 .65(m,6H),1.43-1.37(m,6H),1.34-1.24(m,12H),0.91-0.88(m,9H).

[0158] Example 2: Preparation of organic compound M2:

[0159]

[0160] The synthesis of the organic compound M2 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by 1-bromooctane (CAS: 111-83-1), and triphenylamine boric acid in the preparation step of compound M1 is replaced by 9H-carbazole-9-phenylboronic acid (CAS: 419536-33-7). The reaction conditions and the amount of substances are not changed, and a white solid product M2 is finally obtained.

[0161] The NMR data of M2 are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.00-7.97(m,6H),7.71-7.67(m,6H),7.60-7.59(m,3 H),7.57-7.54(m,3H),7.53-7.50(m,6H),7.43-7.39(m,6H),7.36-7.34(m,3H),7.2 7-7.23(m,6H),7.20-7.16(m,9H),7.11-7.09(m,3H),4.24(s,6H),3.91(t,J=6.3Hz ,6H),1.71-1.65(m,6H),1.42-1.36(m,6H),1.33-1.25(m,24H),0.90-0.87(m,9H).

[0162] Example 3: Preparation of organic compound M3:

[0163]

[0164] The synthesis of the organic compound M3 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by p-hexyloxyiodobenzene (CAS: 85557-94-4), and triphenylamine boric acid in the preparation step of compound M1 is replaced by 9H-phenothiazine-9-phenylboric acid (CAS: 1246021-63-5). The reaction conditions and the amount of substances are not changed, and a white solid product M3 is finally obtained.

[0165] The NMR data of M3 are as follows: 1H NMR(500MHz,Chloroform-d)δ7.55-7.52(m,6H),7.48-7.44(m,6H),7.32-7.28(m,12H),7.27-7.22(m,12H),7.22-7.18(m,6H),7.08-7.03(m,15 H),6.87-6.84(m,6H),4.24(s,6H),4.01(t,J=6.0Hz,6H),1.79-1.73(m, 6H),1.45(dq,J=7.6,6.6Hz,6H),1.37-1.27(m,12H),0.93-0.89(m,9H).

[0166] Example 4: Preparation of organic compound M4:

[0167]

[0168] The synthesis of the organic compound M4 of this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by p-hexyloxyiodobenzene, and triphenylamine boric acid in the preparation step of compound M1 is replaced by 9-methyl-9H-carbazole-3-boric acid (CAS: 1039761-02-8). The reaction conditions and the amount of substances are not changed, and a white solid product M4 is finally obtained.

[0169] The NMR data of M4 are as follows: 1 H NMR(500MHz,Chloroform-d)δ8.17-8.14(m,3H),7.95(s,3H),7.61-7.58(m ,6H),7.48-7.35(m,15H),7.27-7.21(m,6H),7.19-7.15(m,3H),7.02-6.98( m,6H),6.87-6.83(m,6H),4.24(s,6H),4.01(t,J=6.0Hz,6H),3.63(s,9H),1 .79-1.73(m,6H),1.48-1.42(m,6H),1.36-1.27(m,12H),0.93-0.89(m,9H).

[0170] Example 5: Preparation of organic compound M5:

[0171]

[0172] The synthesis of the organic compound M5 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced with 4-bromobenzene (CAS: 30752-20-6), and triphenylamine boric acid in the preparation step of compound M1 is replaced with 9,9,10-trimethyl-9,10-dihydroacridine-2-boric acid (CAS: 1629720-84-8). The reaction conditions and the amount of substance are not changed, and a white solid product M5 is finally obtained.

[0173] The NMR data of M5 are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.61-7.60(m,3H),7.60-7.57(m,3H),7.55-7.52(m,3H),7.31-7.29( m,9H),7.27-7.26(m,3H),7.20-7.16(m,3H),7.15-7.11(m,3H),7.09-7.07(m,3H),7.06-7.03(m,3H ),7.02-6.99(m,6H),6.92-6.90(m,3H),6.86-6.83(m,6H),4.24(s,6H),4.02(t,J=6.1Hz,6H),3.58 (s,9H),1.79-1.74(m,6H),1.56(s,18H),1.49-1.43(m,6H),1.34-1.21(m,36H),0.90-0.87(m,9H).

[0174] Example 6: Preparation of organic compound M6:

[0175]

[0176] The synthesis of the organic compound M6 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by p-hexyloxyiodobenzene, and triphenylamine boric acid in the preparation step of compound M1 is replaced by 10-methyl-10H-phenothiazine-3-boric acid (CAS: 477930-12-4). The reaction conditions and the amount of substances are not changed, and a white solid product M6 is finally obtained.

[0177] The NMR data of M6 are as follows: 1H NMR(500MHz,Chloroform-d)δ7.61-7.60(m,3H),7.58-7.54(m,6H),7.35-7. 33(m,6H),7.27-7.21(m,9H),7.13-7.09(m,3H),7.08-7.04(m,6H),7.02-6.9 7(m,9H),6.86-6.83(m,6H),4.24(s,6H),4.01(t,J=6.0Hz,6H),3.57(s,9H), 1.79-1.74(m,6H),1.48-1.42(m,6H),1.36-1.28(m,12H),0.93-0.89(m,9H).

[0178] Example 7: Preparation of organic compound M7:

[0179]

[0180] The synthesis of the organic compound M7 of this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by p-hexyloxyiodobenzene, and triphenylamine boric acid in the preparation step of compound M1 is replaced by bis(4-methoxyphenyl)amine (CAS: 101-70-2). The reaction conditions and the amount of substances are not changed, and a white solid product M7 is finally obtained.

[0181] The NMR data of M7 are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.61-7.60(m,3H),7.27-7.26(m,3H),7.04-6.95(m,18H),6.93-6.90(m,6H),6.86-6.82(m,21H), 4.24(s,6H),4.01(t,J=6.0Hz,6H),3.78(s,18H),1.79-1.73(m,6H),1.48-1.42(m,6H),1.35-1.29(m,12H),0.93-0.89(m,9H).

[0182] Example 8: Preparation of organic compound M8:

[0183]

[0184] The synthesis of the organic compound M8 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by p-hexyloxyiodobenzene, and triphenylamine boric acid in the preparation step of compound M1 is replaced by 2-boronic acid phenoxazine (CAS: 2304440-01-3). The reaction conditions and the amount of substance are not changed, and a white solid product M8 is finally obtained.

[0185] The NMR data of M8 are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.61-7.60(m,3H),7.55-7.52(m,3H),7.43-7.40 (m,6H),7.31-7.29(m,3H),7.27-7.26(m,3H),7.23-7.21(m,3H),7.04-6.96(m ,18H),6.94-6.91(m,3H),6.86-6.83(m,6H),4.24(s,6H),4.01(t,J=6.0Hz,6H ),1.79-1.73(m,6H),1.48-1.42(m,6H),1.35-1.28(m,12H),0.92-0.88(m,9H).

[0186] Example 9: Preparation of organic compound M9:

[0187]

[0188] The synthesis of the organic compound M9 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced by 1-bromododecanyl (CAS: 143-15-7), and triphenylamine boric acid in the preparation step of compound M1 is replaced by 4-10H-phenoxazine-10-phenylboric acid (CAS: 1246021-62-4). The reaction conditions and the amount of substances are not changed, and a white solid product M9 is finally obtained.

[0189] The NMR data of M9 are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.55-7.53(m,6H),7.48-7.46(m,3H),7.45-7.43(m,3H),7.31-7.30(m,3H),7.27-7.23(m,9H),7.11-6.97(m ,21H),6.74-6.72(m,6H),4.24(s,6H),3.91(t,J=6.3Hz,6H),1.70-1 .65(m,6H),1.42-1.36(m,6H),1.32-1.23(m,48H),0.90-0.87(m,9H).

[0190] Example 10: Preparation of organic compound M10:

[0191]

[0192] The synthesis of the organic compound M10 in this example is similar to that of M1, except that in Example 1, 1-bromohexane in the preparation step of compound M1-4 is replaced with 1-bromododecanyl (CAS: 143-15-7), and triphenylamine boric acid in the preparation step of compound M1 is replaced with 4,4'-dimethoxy-4"-triphenylamine borate (CAS: 201802-29-1). The reaction conditions and the amount of substance are not changed, and a white solid product M10 is finally obtained.

[0193] The NMR data of M10 are as follows: 1 H NMR(500MHz,Chloroform-d)δ7.53-7.50(m,6H),7.47-7.43(m,6H),7.31-7.29(m,3H),7.27-7.22(m,9H),7.09-7.05(m,12H),7.00-6.99(m,3H),6. 86-6.83(m,12H),4.24(s,6H),3.91(t,J=6.3Hz,6H),3.78(s,18H),1.67( p,J=6.6Hz,6H),1.42-1.36(m,6H),1.32-1.23(m,48H),0.91-0.87(m,9H).

[0194] Comparative Example 1:

[0195] The comparative compound P1 is PEDOT:PSS.

[0196] Comparative Example 2:

[0197] The comparative compound P2 is the compound M1-4 prepared in Example 1.

[0198] Comparative Example 3:

[0199] The synthetic route of organic compound P3 is as follows:

[0200]

[0201] The synthesis of the organic compound P1 in this comparative example is similar to the synthesis method of compound M1 prepared from M1-4 in Example 1, except that M1-4 is replaced by P1-1 (CAS: 353752-14-4), triphenylamine boric acid is replaced by 10-methyl-10H-phenothiazine-3-boric acid (CAS: 477930-12-4), the reaction conditions and the amount of substances are not changed, and a white solid product P1 is finally obtained. NMR(500MHz,Chloroform-d)δ8.36-8.34(m,1H),7.96-.94(m,1H),7.88-7.85(m,1H),7.83-7.81(m,1H),7.74-7 .71(m,1H),7.69-7.66(m,1H),7.51-7.50(m,1H),7.48-7.44(m,1H),7.44-7.42(m,1H),7.38-7.21(m,9H),7.18- 7.14(m,1H),7.12-6.99(m,6H),6.91-6.87(m,1H),6.37-6.32(m,1H),6.29-6.24(m,1H),5.93-5.90(m,2H),4.3 3-4.29(m,2H),4.17-4.11(m,2H),4.08-4.04(m,3H),3.90-3.86(m,1H),3.60(s,3H),3.49(s,3H),2.97(s,3H)..

[0202] Device Example 1

[0203] The device embodiment provides a quantum dot light emitting diode and a method for preparing the same, which specifically includes the following steps.

[0204] Step 1: Place an ITO glass sheet in a glass dish filled with ethanol solution, and ultrasonicate with acetone, deionized water, and ethanol for 20 minutes respectively, and then blow dry with a nitrogen gun; then place the cleaned ITO glass sheet in oxygen plasma for further cleaning for 10 minutes; continue to use UV-ozone to treat the surface of the ITO substrate for 15 minutes;

[0205] Step 2: Disperse the compound M1 obtained in Example 1 in chlorobenzene to prepare a mixed solution with a compound concentration of 8 mg / ml, and spin-coat the cleaned ITO glass sheet with the mixed solution in air at a rotation speed of 5000 r / min for 30 seconds; after spin coating, place it in air for annealing at an annealing temperature of 150° C. for 30 minutes to obtain a hole injection layer with a thickness of 40 nm;

[0206] Step 3: Spin-coat TFB (8 mg / mL) on the hole injection layer at a rotation speed of 3000 r / min for 30 seconds; after spin coating, anneal in a glove box at a temperature of 120° C. for 10 minutes to obtain a hole transport layer;

[0207] Step 4: Spin-coat quantum dots QD (20 mg / mL) on the hole transport layer at a spin-coating speed of 2000 r / min for 30 seconds; then -2 MPa environment for 15 min to obtain a luminescent layer with a thickness of 30 nm;

[0208] Step 5: Spin-coat the luminescent layer with an ethanol solution of ZMO (30 mg / mL) at a speed of 3000 r / min for 30 seconds and then -2 MPa environment for 15 min to obtain a 10 nm electron transport layer;

[0209] Step 6: Through thermal evaporation, the vacuum degree is not higher than 3*10 -4 Pa, evaporate Ag at a rate of 1 angstrom / s for 200 seconds to form a top silver electrode with a thickness of 20 nm on the electron transport layer, and then perform epoxy resin encapsulation.

[0210] The device structure is: ITO / M1 (40nm) / TFB (8wt%) / QD (30nm) / ZMO (10nm) / Ag (20nm).

[0211] Device Examples 2-10

[0212] Device Example n is basically the same as Device Example 1, with the only difference being that in Device Example n: when preparing the electron transport layer in step 5, the organic compound M1 is replaced with the organic compound of Material Example n, n is an integer from 2 to 10, and the organic compound of Material Example n is M2 to M10.

[0213] Device Comparative Example 1

[0214] The device comparative example is basically the same as the device example 1, except that in step 2 of the device comparative example, the material of the hole injection layer is changed from the mixed solution containing compound M1 to PEDOT:PSS. Other parameters and steps remain unchanged.

[0215] Experimental example

[0216] (I) Hole mobility and material moisture resistance test

[0217] M1 to 10 and P1 to 3 were used as HTL materials, respectively, and the preparation process of each corresponding film layer in the above device embodiment 1 was referred to to construct a detection device with the following structure: ITO / organic compound / MoO 3 / Ag. Then the hole mobility and stability of the material were tested using a detection device. The results are shown in Table 1.

[0218] The hole mobility of the hole injection material is recorded by the space charge limited current (SCLC) method, which can be described by the Mott-Gurney equation: J = 9με 0 ε r V 2 / (8d 3 )

[0219] Where J is the current density, μ is the hole mobility, and ε 0 is the vacuum dielectric constant (8.85×10 -12 F / m), ε r is the dielectric constant of the material (usually approximately taken as 3 for organic semiconductors), V is the applied bias voltage and d is the film thickness.

[0220] Material moisture resistance test: In the above hole mobility test, the test object is placed in a closed environment with a humidity of 80% for 100 hours, and the hole mobility change after being placed in a high humidity environment is recorded, and the mobility decay rate is calculated. Mobility decay rate = mobility difference before and after placement / hole mobility before placement * 100%.

[0221] Table 1

[0222] <![CDATA[Hole mobility (10 -3 cm 2 V -1 s -1 )]]> Mobility decay rate (%) M1 4.55 8.1 M2 4.39 8.7 M3 4.84 7.6 M4 5.24 6.6 M5 4.54 6.1 M6 4.12 6.5 M7 4.35 7.9 M8 4.07 5.9 M9 4.19 6.4 M10 5.32 8.1 P1 2.54 25.4 P2 2.87 16.7 P3 2.41 17.1

[0223] It can be seen from Table 1 that:

[0224] The electron mobility of the organic compound provided in this application is 4.07×10 -3 cm 2 V -1 s -1 ~5.32×10 - 3 cm 2 V -1 s -1 The range is higher than that of PEDOT:PSS, which indicates that the organic compound proposed in this application has better hole mobility.

[0225] In addition, the mobility decay rate of the detection device corresponding to the organic compound of the present application after being placed in a closed environment with a humidity of 80% for 100 hours is much lower than that of PEDOT:PSS, indicating that the organic compound proposed in the present application has better moisture resistance.

[0226] (II) The photoelectric efficiency and working life test of the quantum dot light-emitting diodes of the device embodiment and the device comparison example are carried out, and the data are shown in Table 2. Specifically, the current efficiency C.Emax, the maximum brightness L max , measured lifespan T95, lifespan T95@1000nit, moisture resistance and heat resistance.

[0227] Among them, the maximum brightness L max The test method of current efficiency CE is as follows: using FPD optical property measurement equipment, controlling the efficiency test system built by QE PRO spectrometer, Keithley 2400, and Keithley 6485 through LabView, measuring parameters such as voltage, current, brightness, and luminous spectrum, and calculating the current efficiency CE;

[0228] The test method for the life span T95@1000nit is: the time required for the device to reduce its brightness to a certain proportion of the maximum brightness under constant current or voltage driving, and the time for the brightness to drop to 95% of the maximum brightness is defined as T95, and this life span is the measured life span. In order to shorten the test cycle, the device life span test is usually carried out at high brightness by accelerating device aging, and the life span at high brightness is obtained by fitting the extended exponential decay brightness decay fitting formula, for example: the life span at 1000nit is calculated as T95@1000nit. The specific calculation formula is as follows:

[0229]

[0230] Among them, T95 L For lifespan at low brightness, T95 H is the measured lifetime under high brightness, L H To accelerate the device to the highest brightness, L L is 1000nit, A is the acceleration factor, and this experiment measured the lifespan of several groups of green QLED devices at rated brightness and found that the A value was 1.7.

[0231] The method for heat resistance test is: testing the initial current efficiency CE of the device of the device embodiment and the device comparison example, and recording the initial data, placing it in a closed environment at a temperature of 80° C. for 100 hours, recording the CE value after being placed at high temperature, and calculating the CE decay rate a, which is characterized as heat resistance;

[0232] The method for moisture resistance testing is: testing the initial current efficiency CE of the device embodiment and the device comparison example, and recording the initial data, placing them in a closed environment with a humidity of 80% for 100 hours, recording the CE value after placement under high humidity, and calculating the CE decay rate b, which is characterized as moisture resistance.

[0233] Table 2

[0234]

[0235] It can be seen from Table 2 that:

[0236] Compared with the device comparison example, the device embodiments 1 to 10 all have higher maximum brightness L max , lifespan T95, lifespan T95@1000nit, current efficiency CE, and lower CE decay rate a and CE decay rate b, indicating that in the device, the balance between hole injection and electron injection is good, so that the device has higher photoelectric performance and lifespan; in addition, the organic compound of the present application has good tolerance to humid and hot environment and is not easily affected by temperature and humidity, so that the device has higher stability, which is specifically reflected in the lower CE decay rate a and CE decay rate b of the device embodiment.

[0237] The organic compounds and preparation methods, compositions, optoelectronic devices and display devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the methods and core ideas of the present application. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound, It is characterized in that Having the structure shown in formula (I): Among them, R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups; Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures: Where X is CR 6 R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S, m is 0 or 1; R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 a combination of one or more of alkoxy; R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers of 0-4.

2. The organic compound according to claim 1, It is characterized in that The organic compound has a structure shown in formula (II):

3. The organic compound according to claim 1 or 2, It is characterized in that Ar 1 ,Ar 2 ,Ar 3 Each independently selected from one of the following structures:

4. The organic compound according to claim 3, It is characterized in that Ar 1 ,Ar 2 ,Ar 3 Each independently selected from one of the following structural formulas (1-1) to (1-13):

5. The organic compound according to claim 3, It is characterized in that R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 10 Alkyl, substituted or unsubstituted C 1 ~C 10 One or more combinations of alkoxy; and / or, R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 10 A combination of one or more of an alkyl group and a substituted or unsubstituted aryl group having 6 to 10 ring atoms; 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.

6. The organic compound according to claim 1 or 2, It is characterized in that R 1 , R 2 , R 3 Each independently selected from substituted or unsubstituted C 1 ~C 12 Alkyl, substituted or unsubstituted C 1 ~C 12 Alkoxy, substituted or unsubstituted C 7 ~C 18 Alkylphenyl, substituted or unsubstituted C 7 ~C 18 One or more of alkoxyphenyl; and / or, The substituent is selected from one or more combinations of hydrogen, deuterium, amino, halogen, hydroxyl, carboxyl, nitro, sulfonic acid, mercapto, and cyano; and / or, Ar 1 ,Ar 2 ,Ar 3 the same; and / or, R 1 , R 2 , R 3 same.

7. The organic compound according to claim 1 or 2, It is characterized in that The organic compound includes one or more of the following structural formulas:

8. A method for preparing an organic compound, It is characterized in that The following steps are involved: Mixing compound m and an acidic solution to carry out a first reaction to obtain compound a; The compound a is mixed with 2-aminobenzenethiol and subjected to a second reaction to obtain a compound b; The compound b and the raw material c are mixed and subjected to a third reaction to obtain a compound d; The compound d is reacted with a halogenating agent to generate a halogenated product, and the halogenated product is mixed with a raw material e to perform a fourth reaction to obtain an organic compound f; Wherein, compound m, compound a, compound b, compound d, and organic compound f respectively have the following structural formulas: Among them, the raw material c includes the general formula R 1 The compound of Y, the general formula is R 2 Y, and a compound of the general formula R 3 A mixture of compounds of Y, wherein the raw material e includes a general formula of Ar 1 B(OH) 2 Compounds with the general formula Ar 2 B(OH) 2 Compounds of the general formula Ar 3 B(OH) 2 A mixture of compounds of, Y, Y 'each time appearing, each independently selected from -Cl, -Br or -I; R 1 , R 2 , R 3 Each independently selected from H, D, a halogen atom, a substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 7 ~C 36 alkylaryl, substituted or unsubstituted aryl having 6 to 30 ring atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms, substituted or unsubstituted C 7 ~C 36 one or more of alkoxyaryl groups; Ar 1 ,Ar 2 ,Ar 3 Each independently selected from the following structures: Where X is CR 6 R 7 , S, NR 8 or O; M is NR 9 、O、SiR 10 R 11 or S, m is 0 or 1; R 4 , R 5 Each independently selected from substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 1 ~C 30 A combination of one or more of alkoxy; R 6 To R 11 Each independently selected from H, D, substituted or unsubstituted C 1 ~C 30 A combination of one or more of an alkyl group, a substituted or unsubstituted aryl group having 6 to 60 ring atoms; n1 and n2 are each independently selected from integers from 0 to 5; n3 and n4 are each independently selected from integers of 0-4.

9. The preparation method according to claim 8, It is characterized in that The acidic solution comprises a mixed solution of acetic acid and concentrated hydrochloric acid, wherein the volume ratio of the acetic acid to the concentrated hydrochloric acid is 1:(0.3-0.5); and / or, The reaction temperature of the first reaction is 80-130° C.; and / or, The reaction time of the first reaction is 12 to 24 hours; and / or, The molar ratio of the compound a to 2-aminobenzenethiol is 1:(4-5); and / or, The reaction temperature of the second reaction is 80-110° C.; and / or, The reaction time of the second reaction is 8 to 12 hours; and / or, The molar ratio of the compound b to the raw material c is 1:(3-5); and / or, The reaction temperature of the third reaction is 80-110° C.; and / or, The reaction time of the third reaction is 6 to 24 hours; and / or, The halogenating agent includes one or more of N-bromosuccinimide, liquid bromine, 1,3-dibromo-5,5-dimethylhydantoin, and N-iodosuccinimide; and / or, The molar ratio of the compound d to the halogenating agent is 1:(3-6); and / or, The reaction temperature of the compound d and the halogenating agent is 40 to 60° C.; and / or, The reaction time of the compound d and the halogenating agent is 6 to 12 hours; and / or, The molar ratio of the compound d to the raw material e is 1:(3-5); and / or, The reaction temperature of the fourth reaction is 80-110° C.; and / or, The reaction time of the fourth reaction is 12 to 24 hours; and / or, The step of mixing the compound a with 2-aminobenzenethiol and performing a second reaction to obtain compound b comprises: under the protection of an inert gas, mixing the compound a, 2-aminobenzenethiol and ferric citrate, performing a second reaction to obtain compound b.

10. The preparation method according to claim 9, It is characterized in that The molar ratio of compound m to the acetic acid is 1:(40-80); and / or, The molar ratio of the compound a to the ferric citrate is 1:(4-5).

11. A composition, It is characterized in that The method comprises an organic compound and a solvent, wherein the organic compound comprises the organic compound according to any one of claims 1 to 7, or comprises the organic compound prepared by the preparation method according to any one of claims 8 to 10.

12. The composition according to claim 11, It is characterized in that In the composition, the concentration of the organic compound is 5 to 30 mg / ml; and / or, The solvent includes one or more of chlorobenzene, toluene and xylene; and / or, The composition also includes 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-methylphenylamino)-triphenylamine, poly(p-phenylenevinylene), poly[2 -methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene], poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene], 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compound, N,N,N',N'-tetraarylbenzidine, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine, spiro NPB, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO 3 One or more of derivatives of, 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.

13. A photoelectric device, It is characterized in that It comprises an anode, a hole functional layer and a cathode, wherein the material of the hole functional layer comprises the organic compound described in any one of claims 1 to 7, or comprises the organic compound prepared by the preparation method described in any one of claims 8 to 10, or is made of the composition described in claim 11 or 12.

14. The optoelectronic device according to claim 13, It is characterized in that The anode and the cathode are 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 fiber; the material of the doped or undoped metal oxide electrode is selected from ITO, FTO, ATO, AZO, GZO, IZO, MZO, ITZO, ICO, AMO, SnO 2 、In 2 O 3 、Cd:ZnO、Ga:SnO 2 At least one of the following; the material of the composite electrode is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO 2 / Ag / TiO 2 、TiO 2 / Al / TiO 2 , one of ZnS / Ag / ZnS and ZnS / Al / ZnS; and / or, The optoelectronic device comprises a light-emitting layer, which is arranged between the cathode and the hole functional layer, and the material of the light-emitting layer is selected from an organic light-emitting material or a quantum dot light-emitting material; the organic light-emitting material is selected from at least one of diaryl anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives or fluorene derivatives, TBPe fluorescent materials emitting blue light, TTPA fluorescent materials emitting green light, TBRb fluorescent materials emitting orange light and DBP fluorescent materials emitting red light; the quantum dot light-emitting material is selected from at least one of single-structure quantum dots, core-shell structure quantum dots and perovskite semiconductor materials, and the single-structure quantum dots are selected from II-VI compounds, IV-VI compounds, III-V compounds. The compound is selected from the group consisting 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, CdHgSe, Cd At least one of HgSTe, HgZnSeS, HgZnSeTe and HgZnSTe, the IV-VI group compound is 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 compound is selected from at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaN At least one of As, 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 Group I-III-VI compound is at least one of CuInS, CuInSe and AgInS;The core of the quantum dots of the core-shell structure is selected from any one of the above-mentioned single-structure quantum dots, and the shell material of the quantum dots of the 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 general structural formula of the inorganic perovskite semiconductor is AMX; 3 , 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+ At least one of, X is a halogen anion selected from Cl - Br - , I- at least one; the general structural formula of the organic-inorganic hybrid perovskite semiconductor is BMX 3 , wherein B is an organic amine cation selected from CH 3 (CH 2 ) n-2 NH 3 + or [NH 3 (CH 2 ) n NH 3 ] 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+ At least one of, X is a halogen anion selected from Cl - Br - ,I - At least one of .

15. A display device, It is characterized in that The optoelectronic device comprising claim 13 or 14.

Images