Composition, electronic device and display equipment

Abstract

The invention provides a composition, an electronic device and display equipment. The composition comprises a first hole transport material and an organic P-type semiconductor material, wherein the structure of the first hole transport material is shown as a formula (1), wherein * represents a chiral center; each monomer is an optical isomerization unit, and the optical isomerization unit forms a regular form in a molecular chain; ar appears each time and is independently selected from a hole transport group. The composition can improve the efficiency of an electronic device.

Description

Technical Field

[0001] The present invention relates to the field of functional devices, and in particular to a composition, an electronic device and a display device. Background Art

[0002] Electroluminescent devices such as organic light-emitting diodes (OLEDs), quantum dot light-emitting diodes (QLEDs), and perovskite light-emitting diodes (PeLEDs) have the characteristics of high contrast, low energy consumption, and bendability and curlability, and have received more and more attention in the fields of display and lighting.

[0003] Electroluminescent devices are usually "sandwich" structures, including an anode, a functional layer and a cathode arranged in sequence, and the functional layer includes a carrier transport layer and a light-emitting layer. In order to achieve better film-forming properties, traditional technologies generally use polymer hole transport materials to prepare carrier transport layers. However, compared with inorganic hole transport materials, traditional polymer hole transport materials have lower hole mobility, which leads to an imbalance in electron-hole transport in electroluminescent devices, shortening the working life of electroluminescent devices. Some technologies dope inorganic hole transport materials in polymer hole transport materials to form a composition, but the presence of inorganic hole transport materials is not conducive to film formation, resulting in an unstable film structure, which still shortens the working life of electroluminescent devices.

[0004] Therefore, the traditional technology still needs to be improved. Summary of the invention

[0005] Based on this, the present invention provides a composition, an electronic device and a display device.

[0006] The present invention is achieved through the following technical solutions.

[0007] In a first aspect of the present application, a composition is provided, the composition comprising a first hole transport material and an organic P-type semiconductor material, wherein the structure of the first hole transport material is as shown in formula (1):

[0008]

[0009] Wherein: * represents a chiral center; each monomer is an optically active isomer unit, and the optically active isomer unit forms a stereoregular form in the molecular chain;

[0010] Each occurrence of Ar is independently selected from the first hole transporting group.

[0011] The composition contains a first hole transport material with a specific structure, each monomer of which is equivalent to an optical isomer unit, and the stereo configuration of the optical isomer unit forms an isotactic or syndiotactic (collectively referred to as regular stereo) form in the polymer chain. The hole transport group Ar is located in the side chain of the polymer, and the isotactic structure of the main chain thereof limits the spatial orientation of the side chain aromatic group to a certain extent, thereby facilitating orderly arrangement, and at the same time can induce other organic P-type semiconductor materials to form a more orderly arrangement, forming a synergistic effect, further improving the hole mobility, and thus improving the efficiency of the organic electroluminescent device.

[0012] According to a second aspect of the present application, an electronic device is provided, comprising a first electrode, a carrier transport layer and a second electrode stacked in sequence, wherein the material of the carrier transport layer comprises a composition, wherein the composition comprises a first hole transport material and an organic P-type semiconductor material having different structures, and the structure of the first hole transport material is as shown in formula (1).

[0013] In the above-mentioned electronic device, the carrier transport layer includes a specific composition, which contains a first hole transport material with a specific structure, each monomer contained in the composition is equivalent to an optical isomer unit, and the stereo configuration of the optical isomer unit forms an isotactic or syndiotactic (collectively referred to as regular stereo) form in the polymer chain. The hole transport group Ar is located in the side chain of the polymer, and the above-mentioned isotactic structure of its main chain limits the spatial orientation of the side chain aromatic group to a certain extent, which is conducive to achieving an orderly arrangement, and at the same time can induce other organic P-type semiconductor materials to be arranged in a more orderly manner, and the synergistic effect further improves the hole mobility of the carrier transport layer, thereby improving the efficiency of the electronic device.

[0014] A third aspect of the present application further provides a display device, comprising the electronic device of the second aspect. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 A schematic diagram of the structure of an electronic device provided by an embodiment of the present invention;

[0016] Figure 2 A schematic diagram of the structure of an electronic device provided in another embodiment of the present invention.

[0017] Description of reference numerals:

[0018] 100, HOD device; 101, encapsulation layer; 102, first electrode; 103, electron blocking layer; 104, hole transport layer; 105, hole injection layer; 106, second electrode;

[0019] 200, electronic device; 201, first electrode; 202, hole injection layer; 203, hole transport layer; 204, light-emitting layer; 205, electron transport layer; 206, second electrode. DETAILED DESCRIPTION

[0020] For ease of understanding of the present invention, the present invention will be described more fully below with reference to relevant embodiments. Preferred embodiments of the present invention are provided in the embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0021] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used herein in the specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more related listed items.

[0022] In the present application, the term "unsubstituted or substituted" means that the group modified after the term may or may not contain a substituent. It should be understood that when the group contains a substituent, it means that at least one hydrogen atom in the group modified after the term is replaced by a substituent. For example, when A is a phenyl substituted with a methyl group, the total carbon number of A is 6, that is, A is a phenyl group formed after one hydrogen atom in the phenyl group with a carbon number of 6 is replaced by a methyl group.

[0023] In the present application, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of 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. 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 "number of 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.

[0024] Aromatic groups refer to hydrocarbon groups containing at least one aromatic ring. Heteroaromatic groups refer to aromatic hydrocarbon groups containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and is particularly preferably selected from Si, N, P, O and / or S. A condensed ring aromatic group refers to a ring of an aromatic group that can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., a condensed ring. A condensed heterocyclic aromatic group refers to a condensed ring aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, aromatic groups or heteroaromatic groups include not only systems of aromatic rings, but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are also considered to be aromatic groups or heterocyclic aromatic groups for the purposes of this invention. For the purposes of the present invention, fused aromatic or fused heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc. are also considered fused aromatic ring systems for the purposes of this invention.

[0025] In the present invention, "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. 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.

[0026] In the present application, "alkenyl" refers to a monovalent residue formed by the loss of a hydrogen atom from a hydrocarbon having at least one unsaturated site, i.e., a carbon-carbon sp2 double bond. Phrases containing this term, for example, "alkenyl having 2-10 carbon atoms" refer to straight-chain alkenyl having 2-10 carbon atoms and branched alkenyl having 3-10 carbon atoms. The number of carbon atoms of the alkenyl group is, for example, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Specific examples of alkenyl include, but are not limited to, vinyl (-CH=CH2) and allyl (-CH2CH=CH2).

[0027] In the present application, "stereoregular" includes isotactic (isotactic) and syndiotactic (syndiotactic). In isotactic, all optically active isomers have the same stereo configuration, while in syndiotactic polymers, two stereo configurations appear alternately, i.e., adjacent optically active isomers have opposite stereo configurations.

[0028] 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, for example R is connected to any substitutable position of the benzene ring.

[0029] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. Contains multiple R 14 When each R 14 can be independently selected from the same or different groups.

[0030] In the present invention, when it comes to a numerical interval (i.e., a numerical range), unless otherwise specified, the distribution of the optional numerical values ​​in the numerical interval is considered to be continuous, and includes the two numerical endpoints (i.e., the minimum value and the maximum value) of the numerical interval, and each numerical value between the two numerical endpoints. Unless otherwise specified, when the numerical interval only refers to the integers in the numerical interval, including the two endpoint integers of the numerical range, and each integer between the two endpoints, is equivalent to directly listing each integer. When multiple numerical ranges are provided to describe features or characteristics, these numerical ranges can be merged. In other words, unless otherwise specified, the numerical range disclosed herein should be understood to include any and all sub-ranges included therein. The "numerical value" in the numerical interval can be any quantitative value, such as a number, a percentage, a ratio, etc. "Numerical interval" allows broadly including numerical interval types such as percentage intervals, ratio intervals, and ratio intervals.

[0031] The temperature parameters in the present invention, if not specifically limited, are allowed to be either constant temperature treatment or to vary within a certain temperature range. It should be understood that the constant temperature treatment allows the temperature to fluctuate within the precision range controlled by the instrument. Fluctuations within the range of ±5°C, ±4°C, ±3°C, ±2°C, and ±1°C are allowed.

[0032] In the present invention, the term "room temperature" or "normal temperature" generally refers to 4°C to 35°C, such as 20°C ± 5°C or 10°C.

[0033] ~30℃, further refers to 20℃~30℃.

[0034] In one embodiment of the present application, a composition is provided, which comprises a first hole transport material and an organic P-type semiconductor material. The structure of the first hole transport material is shown in formula (1):

[0035]

[0036] Wherein: * represents chiral center; each monomer is an optical isomer unit, and the optical isomer unit forms a stereoregular form in the molecular chain;

[0037] Each occurrence of Ar is independently selected from the first hole transporting group.

[0038] x represents the degree of polymerization and is a positive integer. In a material represented by formula (1), Ar can appear repeatedly x times, and the group structure at each appearance can be the same or different.

[0039] In experimental research, it was found that the use of a specific benzene-containing stereoregular polymer mixed with other organic P-type semiconductor materials to prepare a hole transport layer can achieve an unexpected synergistic effect. Compared with the use of a benzene-containing stereoregular polymer or other organic P-type semiconductor materials alone, the mobility of the hole transport layer is further significantly improved when the two are mixed and compounded to prepare the hole transport layer. Thus, the composition of the present application is obtained.

[0040] The composition contains a first hole transport material with a specific structure, each monomer of which is equivalent to an optical isomer unit, and the stereo configuration of the optical isomer unit forms an isotactic or syndiotactic (collectively referred to as regular stereo) form in the polymer chain. The hole transport group Ar is located in the side chain of the polymer, and the isotactic structure of the main chain thereof limits the spatial orientation of the side chain aromatic group to a certain extent, thereby facilitating orderly arrangement, and at the same time can induce other organic P-type semiconductor materials to form a more orderly arrangement, forming a synergistic effect, further improving the hole mobility, and thus improving the efficiency of the organic electroluminescent device.

[0041] It can be understood that the above-mentioned hole transport groups can be various types of organic hole transport groups known in the art; the organic P-type semiconductor material is other types of organic P-type semiconductor materials known in the art, and in some embodiments, the structure of the organic P-type semiconductor material is different from the structure of the first hole transport material.

[0042] In some embodiments, x is an integer greater than 5.

[0043] In some of the embodiments, the mass ratio of the first hole transport material to the organic P-type semiconductor material is (1-7):(3-9).

[0044] In some of the embodiments, the mass ratio of the first hole transport material to the organic P-type semiconductor material is (2-6):(4-8).

[0045] The mass ratio of the first hole transport material and the organic P-type semiconductor material is further adjusted to enhance the synergistic effect between the first hole transport material and the organic P-type semiconductor material, thereby further enhancing the hole mobility of the composition.

[0046] In the above "(1-7):(3-9)", the values ​​include the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Specific examples include but are not limited to the point values ​​in the embodiments and: (1-7):3, (1-7):4, (1-7):5, (1-7):6, (1-7):7, (1-7):8, (1-7):9, (1-6):3, (1-76):4, (1-6):5, (1-6):6, (1-7):8 1-6):7, (1-6):8, (1-6):9, (1-5):3, (1-5):4, (1-5):5, (1-5):6, (1-5):7, (1-5):8, (1-5):9, (3-7):3, (3-7):4, (3-7):5, (3-7):6, (3-7):7, (3-7):8, (3-7):9, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8 or 9:1.

[0047] In one embodiment, based on the total mass of the first hole transport material and the organic P-type semiconductor material, the mass proportion of the first hole transport material is 10% to 70%.

[0048] In some of the embodiments, based on the total mass of the first hole transport material and the organic P-type semiconductor material, the mass proportion of the first hole transport material is 20% to 60%.

[0049] In the above “10% to 70%”, the values ​​include the minimum and maximum values ​​of the range, and every value between the minimum and maximum values. Specific examples include but are not limited to the point values ​​in the embodiments and: 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, or a range consisting of any two point values.

[0050] More specifically, the stereo configuration of the optically active isomer units forms isotactic or syndiotactic (collectively referred to as regular stereo) forms in the polymer chain. Among them, all optically active isomer units in isotactic polymers have the same stereo configuration, and its structure is shown in polymer A; in syndiotactic polymers, the two stereo configurations appear alternately, that is, adjacent optically active isomer units have opposite stereo configurations, and its structure is shown in polymer B (the wavy line indicates that the chemical bond is not fully presented).

[0051]

[0052] In some of the embodiments, at least a portion of the optically active units in the molecular chain of the first hole transport material form an isotactic form in the molecular chain.

[0053] It can be understood that the polymer represented by formula (1) is composed of a plurality of molecular chains. In other words, the first hole transport material includes a plurality of molecular chains having a structure as represented by formula (1). As long as some of them form an isotactic form, the synergistic effect of the first hole transport material and the organic P-type semiconductor material can be further improved, thereby improving the hole transport efficiency of the composition.

[0054] Furthermore, in the first hole transport material, the mass content of the optically active isomer units in the molecular chain forming an isotactic molecular chain can be 1% to 100%; can be 10% to 100%; further can be 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 99%.

[0055] In some embodiments, the organic P-type semiconductor material contains a second hole transport group, and at least a portion of the second hole transport group is of the same type as at least a portion of the first hole transport group.

[0056] The first hole transport material and the organic P-type semiconductor material are further regulated to contain at least part of the same type of hole transport groups, so as to further improve the hole mobility.

[0057] It should be noted that: "the second hole transport group is of the same type as the first hole transport group" means having the same hole transport unit, and does not require the structure to be exactly the same. For example, if the second hole transport group is a carbazole group, then the first hole transport group can be a carbazole group or a carbazole group derived from substitution with a substituent.

[0058] In some of the embodiments, based on the total mass of the first hole transport material, the mass proportion of the first hole transport material in which the type of the first hole transport group is the same as the type of the second hole transport group can be 1% to 100%; can be 10% to 100%; further can be 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 99%.

[0059] In some embodiments, the first hole transport group and the second hole transport group are independently selected from at least one of an unsubstituted or substituted aniline group and an unsubstituted or substituted carbazole group; the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a halogen group, a heteroaryl group having 5 to 30 ring atoms, and an aryl group having 6 to 30 ring atoms.

[0060] In some embodiments, at least part of the first hole transporting groups include at least one of unsubstituted or substituted aniline groups, and at least part of the second hole transporting groups include at least one of unsubstituted or substituted aniline groups.

[0061] In some embodiments, at least part of the first hole transporting groups includes at least one of unsubstituted or substituted carbazole groups, and at least part of the second hole transporting groups includes at least one of unsubstituted or substituted carbazole groups.

[0062] In some embodiments, the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a halogen group, a heteroaryl group having 5 to 15 ring atoms, and an aryl group having 6 to 15 ring atoms.

[0063] It can be understood that the above-mentioned “combination of multiple groups” refers to the combination of multiple groups connected by single bonds; further, the combination is connected by forming carbon-carbon single bonds.

[0064] In some embodiments, the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a halogen group, a heteroaryl group having 5 to 15 ring atoms, and an aryl group having 6 to 15 ring atoms.

[0065] In some embodiments, the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of chain alkyl groups with 1 to 10 carbon atoms, chain alkenyl groups with 2 to 10 carbon atoms, halogen groups, heteroaryl groups with 5 to 15 ring atoms, and aryl groups with 6 to 15 ring atoms.

[0066] In some embodiments, the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a halogen group, a heteroaryl group having 5 to 10 ring atoms, and an aryl group having 6 to 10 ring atoms.

[0067] In some embodiments, each occurrence of Ar is independently selected from any of the following groups:

[0068]

[0069] in:

[0070] X1 is selected from CR1; X2 is selected from CR2;

[0071] Each occurrence of R1 and R2 is independently selected from any one of H, D, hydroxyl, nitro, -N(R4)2, halogen, unsubstituted or substituted straight-chain alkyl having 1 to 20 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkyl having 3 to 30 C atoms, unsubstituted or substituted straight-chain alkenyl having 2 to 20 C atoms, unsubstituted or substituted branched alkenyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkenyl having 3 to 20 C atoms, hydroxyl, nitro, -N(R4)2, halogen, unsubstituted or substituted aromatic group having 6 to 60 ring atoms, and unsubstituted or substituted heteroaromatic group having 5 to 60 ring atoms.

[0072] Adjacent R1s may form a ring or not, and adjacent R2s may form a ring or not;

[0073] R3 and R4 are each independently selected from the group consisting of H, D, hydroxyl, nitro, amine, halogen, unsubstituted or substituted straight-chain alkyl having 1 to 20 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkyl having 3 to 30 C atoms, unsubstituted or substituted straight-chain alkenyl having 2 to 20 C atoms, unsubstituted or substituted branched alkenyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkenyl having 3 to 20 C atoms, hydroxyl, nitro, amine, halogen, unsubstituted or substituted aromatic having 6 to 60 ring atoms, and unsubstituted or substituted heteroaromatic having 5 to 60 ring atoms.

[0074] n is selected from any integer from 1 to 4, Indicates the connection site.

[0075] In some embodiments, the substituents of R1, R2, R3 and R4 are each independently selected from any one of a halogen group, a cyano group, a hydroxyl group, a nitro group, a carbonyl group, an alkenyl group having 2 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 ring atoms, a heteroaryl group having 5 to 30 ring atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0076] In some embodiments, the substituents of R1, R2, R3 and R4 are selected from any one of a halogen group, a cyano group, a hydroxyl group, a nitro group, a carbonyl group, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring atoms, a heteroaryl group having 5 to 30 ring atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0077] n is selected from any integer from 1 to 4, Indicates the connection site.

[0078] In some embodiments, each occurrence of Ar is independently selected from any of the following groups:

[0079]

[0080] In a specific example, each occurrence of R1 is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkenyl group having 1 to 20 C atoms.

[0081] In some embodiments, each occurrence of R1 is independently selected from: -H, -D, or a straight chain alkyl group having 1 to 10 C atoms or a straight chain alkenyl group having 1 to 10 C atoms.

[0082] In some embodiments, each occurrence of R3 is independently selected from: -H, -D, and a heteroaromatic group having 5 to 30 ring atoms.

[0083] In some embodiments, each occurrence of R4 is independently selected from any one of a cycloalkyl group having 3 to 20 C atoms, an aromatic group having 6 to 60 ring atoms, and a heteroaromatic group having 5 to 60 ring atoms.

[0084] In some embodiments, each occurrence of R4 is independently selected from any one of a cycloalkyl group having 3 to 10 C atoms, an aromatic group having 6 to 30 ring atoms, and a heteroaromatic group having 5 to 10 ring atoms.

[0085] In some embodiments, adjacent R1 do not form a ring, adjacent R2 do not form a ring, and each occurrence of R1, R2, and R3 is independently selected from H, D, or any one of the following groups:

[0086]

[0087] In some embodiments, adjacent R1 forms a ring and / or adjacent R2 forms a ring, and are independently selected from any one of the following groups:

[0088]

[0089] Where: · represents the fusion site.

[0090] In a specific example, each occurrence of Ar is independently selected from any of the following groups:

[0091]

[0092] In a specific example, each occurrence of Ar is independently selected from any of the following groups Ar1 to Ar8:

[0093]

[0094]

[0095] In some embodiments, each occurrence of Ar is independently selected from any one of Ar1, Ar3, Ar4 and Ar9.

[0096] The first hole transport material can be prepared by the following preparation method, comprising the following steps:

[0097] The first compound With the second compound Perform Suzuki reaction to prepare monomers

[0098] The monomers are polymerized to prepare the first hole transport material represented by the general formula (1).

[0099] The selection types of Ar are the same as above and will not be repeated here.

[0100] Among them, monomer It can also be purchased commercially.

[0101] In some of the embodiments, the catalyst used in the polymerization reaction is a metallocene catalyst.

[0102] In some of the embodiments, the metallocene catalyst comprises a main catalyst and a co-catalyst, the main catalyst comprises a Group IVB transition metal complex, and the main catalyst comprises at least one of an alkylaluminoxane and an organic boron compound.

[0103] In some of these embodiments, the alkylaluminoxane includes methylaluminoxane (MAO).

[0104] In some of these embodiments, the organic boron compound includes B(C6F5)3.

[0105] In some embodiments, the Group IVB transition metal element in the Group IVB transition metal element complex includes at least one of Ti (titanium), Zr (zirconium), and Hf (hafnium).

[0106] In a specific example, the metallocene catalyst is selected from at least one of a titanium complex, methylaluminoxane and trimethoxy(pentamethylcyclopentadienyl)titanium.

[0107] In some of the embodiments, the catalyst used to synthesize the isotactic polymer is a mixture of a titanium complex and methylaluminoxane.

[0108] In some of the embodiments, the catalyst used to synthesize the syndiotactic polymer is a mixture of trimethoxy(pentamethylcyclopentadienyl)titanium and methylaluminoxane.

[0109] In a more specific example, the route of the preparation method of the first hole transport material is as follows:

[0110]

[0111] Specifically, in the first step (Step 1) of the Suzuki reaction, the universal reaction conditions are: based on the molar amount of the first compound, 0.1 times the molar equivalent ratio of tetrakistriphenylphosphine palladium and 2 times the molar equivalent ratio of potassium carbonate are used as the catalysis, and the reaction is refluxed overnight in a mixture of toluene and water under a nitrogen environment. Furthermore, the volume ratio of toluene to water is 10:1.

[0112] Specifically, in the second step (Step 2) polymerization reaction, different metallocene catalysts are used in the polymerization reaction stage to obtain isotactic or syndiotactic polymers. Preferably, the catalyst used to synthesize isotactic polymers is a mixture of titanium complex M0 and methylaluminoxane MAO, and the catalyst used to synthesize syndiotactic polymers is a mixture of trimethoxy (pentamethylcyclopentadiene) titanium Cp * Ti (OMe) 3 and methylaluminoxane MAO. Wherein, the structural formulas of titanium complex M0 and Cp * Ti (OMe) 3 are as follows:

[0113]

[0114] In some of these embodiments, the composition consists of a first hole transport material and an organic P-type semiconductor material.

[0115] In at least some embodiments, the composition is composed of a first hole transport material and an organic P-type semiconductor material having different structures.

[0116] In some embodiments, the composition is a hole transport composition.

[0117] In some embodiments, x is an integer greater than 5.

[0118] In some embodiments, the number average molecular weight of the first hole transport material is 4 kDa to 50 kDa.

[0119] In some of the embodiments, the organic P-type semiconductor material includes at least one of an organic polymer P-type semiconductor material and a small molecule organic P-type semiconductor material.

[0120] In some of the embodiments, the organic P-type semiconductor material is an organic polymer P-type semiconductor material; further, the number average molecular weight of the organic polymer P-type semiconductor material is 5 kDa to 100 kDa.

[0121] The organic polymer P-type semiconductor material may be an organic polymer P-type semiconductor material known in the art that has a hole transport function and has a structure different from that shown in formula (1).

[0122] In some of the embodiments, the organic P-type semiconductor material includes an organic polymer P-type semiconductor material and a small molecule organic P-type semiconductor material; further, the mass ratio of the organic polymer P-type semiconductor material to the small molecule organic P-type semiconductor material is (1-9):(1-9).

[0123] In some of the embodiments, the mass ratio of the organic polymer P-type semiconductor material to the small molecule organic P-type semiconductor material is (1-9):(1-5).

[0124] In some of the embodiments, the mass ratio of the organic polymer P-type semiconductor material to the small molecule organic P-type semiconductor material is (1-5):(1-9).

[0125] The small molecule organic P-type semiconductor material can be a small molecule organic P-type semiconductor material with hole transport function known in the art, including but not limited to: at least one of 4,4',4"-tri(carbazole-9-yl)triphenylamine, 4,4'-di(9-carbazole)biphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, and N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine.

[0126] In some embodiments, the organic P-type semiconductor material is an organic polymer P-type semiconductor material.

[0127] In some of the embodiments, the organic P-type semiconductor material is selected from at least one of poly(9,9-dioctylfluorene-co-N-(4-butylphenyl)diphenylamine), polyvinylcarbazole, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), poly(9,9-dioctylfluorene-co-bis-N,N-phenyl-1,4-phenylenediamine), and poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid).

[0128] One embodiment of the present application also provides an electronic device, which includes a first electrode, a carrier transport layer, and a second electrode stacked in sequence, wherein the material of the carrier transport layer includes a composition, the composition includes a first hole transport material with different structures and an organic P-type semiconductor material, and the structure of the first hole transport material is shown in formula (1).

[0129]

[0130] Wherein: * represents a chiral center; each monomer is an optically active isomer unit, and the optically active isomer unit forms a stereoregular form in the molecular chain;

[0131] Each occurrence of Ar is independently selected from the first hole transporting group.

[0132] In the above-mentioned electronic device, the carrier transport layer includes a specific composition, which contains a first hole transport material with a specific structure, each monomer contained in the composition is equivalent to an optical isomer unit, and the stereo configuration of the optical isomer unit forms an isotactic or syndiotactic (collectively referred to as regular stereo) form in the polymer chain. The hole transport group Ar is located in the side chain of the polymer, and the above-mentioned isotactic structure of its main chain limits the spatial orientation of the side chain aromatic group to a certain extent, which is conducive to achieving an orderly arrangement, and at the same time can induce other organic P-type semiconductor materials to form a more ordered arrangement, synergistically, further improving the hole mobility of the carrier transport layer, thereby improving the efficiency of the electronic device.

[0133] In some of the embodiments, the mass ratio of the first hole transport material to the organic P-type semiconductor material is (1-7):(3-9).

[0134] The mass ratio of the first hole transport material and the organic P-type semiconductor material is further adjusted to enhance the synergistic effect between the first hole transport material and the organic P-type semiconductor material, thereby further enhancing the hole mobility of the composition.

[0135] In some of the embodiments, at least some of the optically active units in the molecular chain of the first hole transport material form an isotactic form in the molecular chain.

[0136] In some embodiments, the organic P-type semiconductor material contains a second hole transport group, and at least a portion of the second hole transport group is of the same type as at least a portion of the first hole transport group.

[0137] The first hole transport material and the organic P-type semiconductor material are further regulated to contain at least part of the same type of hole transport groups, so as to further improve the hole mobility.

[0138] The specific types of the first hole transport material and the organic P-type semiconductor material are the same as above and will not be described in detail here.

[0139] In some of the embodiments, the electronic device further includes a light-emitting layer, and the light-emitting layer is disposed between the carrier transport layer and the first electrode, or between the carrier transport layer and the second electrode.

[0140] In some embodiments, the carrier transport layer includes a hole transport layer, and the material of the hole transport layer includes the above composition.

[0141] In some embodiments, the carrier transport layer further includes a hole injection layer, and the hole injection layer is disposed between the hole transport layer and the second electrode.

[0142] In some embodiments, the material of the hole injection layer is selected from at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO3 derivatives, 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, polytriphenylamine, and tetracyanoquinodimethane; the material of the hole transport layer is selected from at least one of 4,4'-N,N'-dicarbazolyl-biphenyl, 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, 4,4',4'-tri(N-carbazolyl)-triphenylamine, 4,4',4'-tri(N-3-methylphenyl-N-phenylamino)triphenylamine, poly[(9,9'-dioctylfluorene-2,7-diyl)-co-(4,4'- (N-(4-sec-butylphenyl) diphenylamine))], poly(4-butylphenyl-diphenylamine), polyaniline, polypyrrole, poly(p-phenylene vinylene), poly(phenylene vinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] and poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylene vinylene], copper phthalocyanine, aromatic tertiary amines, polynuclear aromatic tertiary amines, 4,4'-bis(p-carbazolyl)-1,1'-biphenyl compounds, N,N,N',N'-tetraarylbenzidine, PEDOT: At least one of PSS and its derivatives, poly(N-vinylcarbazole) and its derivatives, polymethacrylate and its derivatives, poly(9,9-octylfluorene) and its derivatives, poly(spirofluorene) and its derivatives, N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine, spiro NPB, doped graphene, undoped graphene, C60, doped or undoped NiO, doped or undoped MoO3, doped or undoped WO3, doped or undoped V2O5, doped or undoped P-type gallium nitride, doped or undoped CrO3, and doped or undoped CuO.

[0143] In some embodiments, the carrier transport layer further includes an electron transport layer, and the electron transport layer and the hole transport layer are respectively disposed on both sides of the light-emitting layer.

[0144] In some embodiments, the carrier transport layer further includes an electron injection layer, and the electron injection layer is disposed between the electron transport layer and the first electrode.

[0145] In some embodiments, the material of the electron injection layer includes at least one of an alkali metal halide, an alkali metal organic complex or an organic phosphine compound, and the organic phosphine compound is selected from at least one of an organic phosphorus oxide, an organic thiophosphine compound or an organic selenium phosphine compound; the material of the electron transport layer is selected from at least one of a metal oxide, a doped metal oxide, a II-VI semiconductor material, a III-V semiconductor material and an I-III-VI semiconductor material, and the metal oxide is selected from at least one of ZnO, TiO2, and SnO2; the metal oxide in the doped metal oxide is selected from at least one of ZnO, TiO2, and SnO2, the doping element is selected from at least one of Al, Mg, Li, In, and Ga, the II-VI semiconductor material is selected from at least one of ZnS, ZnSe, and CdS; the III-V semiconductor material is selected from at least one of InP and GaP; the I-III-VI semiconductor material is selected from at least one of CuInS and CuGaS.

[0146] In some embodiments, the electronic device further includes an electron blocking layer, and the electron blocking layer is disposed between the carrier transport layer and the first electrode.

[0147] In some embodiments, the material of the light-emitting layer includes at least one of quantum dots or organic light-emitting materials.

[0148] In some embodiments, the quantum dots include at least one of single structure quantum dots and core-shell structure quantum dots.

[0149] In some of the embodiments, the material of the single-structure quantum dots is selected from at least one of II-VI compounds, IV-VI compounds, III-V compounds and I-III-VI compounds; the shell layer of the core-shell structure quantum dots is one or more layers.

[0150] In some embodiments, the II-VI Group compound is selected from at least one of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe.

[0151] In some embodiments, the IV-VI group compound includes at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe and SnPbSTe.

[0152] In some embodiments, the III-V compound includes at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb.

[0153] In some embodiments, the Group I-III-VI compound includes at least one of CuInS 2 , CuInSe 2 , and AgInS 2 .

[0154] In some of the embodiments, the core of the core-shell structured quantum dot includes any one of the single structure quantum dots.

[0155] In some of the embodiments, the shell material of the core-shell structured quantum dots includes at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS, ZnS and single structure quantum dots.

[0156] In some of the embodiments, the organic light-emitting material includes at least one of 4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridine-C2,N)iridium(III), 4,4',4"-tri(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridine-C2,N)iridium, diaromatic anthracene derivatives, distyrene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials and DBP fluorescent materials, polyacetylene and its derivatives, polyparaphenylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives.

[0157] Please refer to Figure 2In some specific examples, the electronic device 200 includes a first electrode 201, a hole injection layer 202, a hole transport layer 203, a light-emitting layer 204, an electron transport layer 205, and a second electrode 206 which are stacked in sequence.

[0158] In some embodiments, the first electrode and the second electrode are each independently selected from a metal electrode, a carbon silicon material electrode, an inorganic semiconductor particle electrode or a composite electrode, the material of the metal electrode is selected from at least one of Ag, Al, Mg, Au, Cu, Mo, Pt, Ca and Ba, the material of the carbon silicon material electrode is selected from at least one of silicon, graphite, carbon nanotubes, graphene and carbon fiber, the material of the inorganic semiconductor particle electrode is selected from at least one of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide and aluminum-doped magnesium oxide, and the composite electrode is selected from at least one of AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS or ZnS / Al / ZnS.

[0159] In one embodiment of the present application, a display device is also provided, comprising the above-mentioned electronic device.

[0160] The above-mentioned electronic device has high luminous efficiency, which is beneficial to improving the efficiency and life of the display device. The embodiments of the present invention will be described in detail below in conjunction with examples. It should be understood that these examples are only used to illustrate the present invention and are not used to limit the scope of this application. The experimental methods for which specific conditions are not specified in the following examples are preferably referred to the guidance given in the present invention, and can also be carried out according to the experimental manual or conventional conditions in the field, or according to the conditions recommended by the manufacturer, or with reference to experimental methods known in the art.

[0161] In the following specific embodiments, the measured parameters of raw material components may have slight deviations within the range of weighing accuracy unless otherwise specified. For temperature and time parameters, acceptable deviations caused by instrument test accuracy or operation accuracy are allowed.

[0162] Synthesis Example 1

[0163] (1) Monomer M1 was prepared by the following synthetic route:

[0164]

[0165] In a three-necked flask protected by argon, 2.18 g of compound S1 (CAS: 267221-88-5, 5 mmol) and 0.915 g of 4-bromostyrene (CAS: 2039-82-9, about 5 mmol) were dissolved in a mixture of 50 mL of toluene and 5 mL of water, 1.38 g of potassium carbonate (about 10 mmol) and 0.288 g of tetrakistriphenylphosphine palladium (about 0.25 mmol) were added thereto, and the reaction was refluxed overnight.

[0166] The reaction mixture was poured into a large amount of water, extracted three times with ether, and magnesium sulfate was added to the ether solution for drying. The desiccant was filtered off, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 1:1) as the elution solvent to obtain 1.30 g of monomer M1. The NMR test data are as follows:

[0167] 1 H NMR (400MHz, CDCl3, ppm): δ7.55(m,6H); 7.35(d 2H); 7.20(m,4H); 7.00(m,6H), 6.75(m,1H); 5.75(m,1H); 5.25(m,1H).

[0168] (2) Preparation of polymer P1, the preparation steps are as follows:

[0169]

[0170] Using double-row tube technology, 100 mg of methylaluminoxane (MAO) was added into a 100 mL reaction bottle under argon protection, and 15 mL of toluene and 1 g of monomer M1 (about 2.9 mmol) were added, and stirring was maintained at 20°C. Then, 2 mL of toluene solution (0.05 mmol) of titanium complex (M0) was injected into the reaction bottle to initiate the polymerization reaction, and ethanol was added after 10 minutes to terminate the reaction.

[0171] The mixture after the reaction was poured into an acidic ethanol solution for precipitation, and the precipitate was collected and washed with ethanol for multiple times, and finally vacuum dried to obtain an isotactic polymer P1.

[0172] Differential scanning calorimetry (DSC) testing of P1 revealed an endothermic peak near 180°C during the secondary heating process, but no obvious glass transition was observed, indicating that its isotactic polymer main chain prompted the polymer molecules to form crystals.

[0173] The elemental analysis results showed that C was 89.87, H was 6.12, and N was 4.00. The number average molecular weight of polymer P1 was 15 kDa as determined by gel chromatography.

[0174] Synthesis Example 2

[0175] The preparation steps of polymer P2 are as follows:

[0176]

[0177] Using double-row tube technology, 1 g of monomer M1 (about 2.9 mM) and 15 mL of toluene were added to a 100 mL reaction bottle under argon protection, and 100 mg of methylaluminoxane (MAO) was added under stirring. Then, 1 mL of Cp*Ti(OMe)3 toluene solution (0.01 mM) was injected into the reaction bottle to initiate the polymerization reaction. After stirring at 50°C for 3 h, ethanol was added to terminate the reaction.

[0178] The reaction mixture was poured into a large amount of acidic ethanol solution for precipitation, and the precipitate was collected and washed with ethanol for multiple times, and finally vacuum dried to obtain the syndiotactic polymer P2. P2 was tested by differential scanning calorimetry (DSC), and it was found that it had an endothermic peak near 200°C during the second heating process, but no obvious glass transition was observed, indicating that its syndiotactic polymer main chain caused the polymer molecules to form crystals.

[0179] The elemental analysis results showed that C was 89.85, H was 6.10, and N was 4.05. The number average molecular weight of polymer P2 was 18 kDa as determined by gel chromatography.

[0180] Synthesis Example 3

[0181] (1) Monomer M3 was prepared by the following synthetic route:

[0182]

[0183] 12.4g of reactant S2 (CAS: 14118-16-2, 30mmol) was dissolved in 200mL of carbon tetrachloride, and 1.69mL of liquid bromine (about 33mmol) was slowly added dropwise under continuous stirring at room temperature. After the addition was completed, the temperature was raised to 70°C for reaction for 4 hours. The solution after the reaction was washed with water three times and then dried by adding magnesium sulfate. The carbon tetrachloride solvent was recovered by distillation after filtering to remove the desiccant. Purification was performed by silica gel column chromatography with n-hexane / dichloromethane as the eluting solvent to obtain the intermediate product S3 (3.68g).

[0184] In a three-necked flask protected by argon, 2.46 g of the intermediate product S3 (5 mmol) was dissolved in 100 mL of dry THF, and the temperature was lowered to -78 °C. Under continuous stirring, 4.10 mL of n-butyl lithium in n-hexane (about 10.25 mmol of n-butyl lithium) was added dropwise, and the mixture was stirred at -78 °C for 1 hour. Subsequently, 2.25 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (about 2.05 g, 11 mmol) was quickly added to the reactant, and the temperature was kept at -78 °C for 1 hour and then warmed to room temperature overnight.

[0185] The reaction mixture was poured into a large amount of water, extracted three times with ether, and magnesium sulfate was added to the ether solution for drying. The desiccant was filtered off, the solvent was removed under reduced pressure, and the obtained solid was recrystallized in a methanol / acetone mixed solvent (volume ratio of 1:1) to obtain an intermediate product S4 (2.26 g).

[0186] In a three-necked flask protected by argon, 2.16g of intermediate product S4 (4mmol) and 0.73g of 4-bromostyrene (4mmol) were dissolved in a mixture of 50mL toluene and 5mL water, 1.10g of potassium carbonate (8mmol) and 0.23g of tetrakis triphenylphosphine palladium (0.2mmol) were added thereto, and the reaction was refluxed overnight. The mixture after the reaction was poured into a large amount of water, extracted three times with ether, and magnesium sulfate was added to the ether solution to dry. The solvent was evaporated under reduced pressure, and purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 1:1) as the eluting solvent to obtain 1.56g of monomer M3. The nuclear magnetic test data are as follows:

[0187] 1 H NMR (400MHz, CDCl3, ppm): δ7.55(m,6H); 7.35(d,2H); 7.20(m,6H); 7.10(m,4H),

[0188] 7.00(m,9H),6.70(m,1H); 5.72(m,1H); 5.20(m,1H).

[0189] (2) Preparation of polymer P3, the preparation steps are as follows:

[0190]

[0191] The preparation of polymer P3 refers to the preparation steps of polymer P1, except that monomer M1 is replaced with an equimolar amount of monomer M3 to prepare isotactic polymer P3. P3 was tested by differential scanning calorimetry (DSC), and it was found that it had an endothermic peak near 160°C during the second heating process, but no obvious glass transition was observed, indicating that its syndiotactic polymer main chain caused the polymer molecules to form crystals.

[0192] The elemental analysis results showed that C was 89.47, H was 5.76, and N was 4.77. The number average molecular weight of polymer P3 was 10 kDa as determined by gel chromatography.

[0193] Synthesis Example 4

[0194] (1) Monomer M4 was prepared by the following synthetic route:

[0195]

[0196] In a three-necked flask protected by argon, 1.85 g of compound S5 (CAS: 1547492-13-6, 5 mmol) and 0.915 g of 4-bromostyrene (about 5 mmol) were dissolved in a mixture of 50 mL of toluene and 5 mL of water, 1.38 g of potassium carbonate (about 10 mmol) and 0.288 g of tetrakistriphenylphosphine palladium (about 0.25 mmol) were added thereto, and the reaction was refluxed overnight.

[0197] The reaction mixture was poured into a large amount of water, extracted three times with ether, and magnesium sulfate was added to the ether solution to dry it. The solvent was evaporated under reduced pressure, and the product was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio of 1:1) as the elution solvent to obtain 1.24 g of monomer M4. The NMR data are as follows:

[0198] 1 H NMR (400MHz, CDCl3, ppm): δ 8.20 (m, 2H), 7.80 (m, 4H); 7.60 (m, 4H); 7.40 (m, 2H); 7.25 (m, 2H), 7.05 (m, 2H), 6.78 (m, 1H); 5.77 (m, 1H); 5.26 (m, 1H).

[0199] (2) Preparation of polymer P4, the preparation steps are as follows:

[0200]

[0201] The preparation of polymer P4 refers to the preparation steps of polymer P1, except that monomer M1 is replaced with an equimolar amount of monomer M4 to prepare isotactic polymer P4. Differential scanning calorimetry (DSC) test of P4 revealed that it had an endothermic peak near 220°C during the secondary heating process, but no obvious glass transition was observed, indicating that its syndiotactic polymer main chain caused the polymer molecules to form crystals.

[0202] The elemental analysis results showed that C was 90.41, H was 5.52, and N was 4.07. The number average molecular weight of polymer P4 was 12 kDa as determined by gel chromatography.

[0203] Example 5

[0204] (1) Preparation of the composition, the steps are as follows:

[0205] The polymer P1 prepared in the above Example 1 is used as the first hole transport material, and PVK (polyvinyl carbazole, number average molecular weight of 10 kDa) is mixed as the organic P-type semiconductor material to prepare a composition. In the composition, the mass proportion of the organic P-type semiconductor material is 90%, the mass proportion of the first hole transport material is 10%, and the mass ratio of the first hole transport material to the organic P-type semiconductor material is 1:9.

[0206] (2) The hole mobility of the composition is tested as follows:

[0207] 1. Preparation of HOD device (single hole device)

[0208] Please refer to Figure 1 , a HOD device 100, comprising:

[0209] 100, HOD device; 101, encapsulation layer; 102, first electrode; 103, electron blocking layer; 104, hole transport layer; 105, hole injection layer; 106, second electrode; its specific structure is: ITO (50nm) / PEDOT:PSS (50nm) / HTL (40nm) / MoO3 (10nm) / Al (100nm) / encapsulation layer (glass, 0.5mm, bonded to the substrate at the periphery of the pixel area with UV curing glue).

[0210] Among them, PEDOT:PSS is used as the hole injection layer (HIL) material, MoO3 is used as the electron blocking layer (EBL) material, and Al is used as the cathode. The structure of PEDOT:PSS is as follows:

[0211]

[0212] The hole transport layer is prepared using the composition obtained in step (1):

[0213] The above composition is dissolved in toluene, an organic solvent, and then coated on the hole injection layer by spin coating, and vacuum dried and heated for annealing to obtain a hole transport layer.

[0214] 2. Hole mobility test: Test the current density (J)-voltage (V) of the HOD device, draw a curve relationship diagram, fit the space charge limited current (SCLC) region in the relationship diagram, and then calculate the hole mobility according to the Child's law formula, which is the hole transfer rate of the composition:

[0215] J=(9 / 8)εr ε0μ e V 2 / d 3 , where J represents the current density in mAcm -2 ; ε r represents the relative dielectric constant, ε0 represents the vacuum dielectric constant; μ e Indicates hole mobility, unit: cm 2 V -1 s -1 ; V represents the driving voltage, unit: V; d represents the film thickness, unit: m. For specific test results, see Table 1.

[0216] Example 6

[0217] Example 6 is basically the same as Example 5, except that: the mass ratio of the components in the composition is changed while the total mass of the composition is kept the same as that of Example 5. In the composition, the mass ratio of the organic P-type semiconductor material is 70%, and the mass ratio of the first polyhole transport material is 30%, that is, the mass ratio of the first hole transport material to the organic P-type semiconductor material is 3:7.

[0218] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0219] Example 7

[0220] Example 7 is basically the same as Example 5, except that: on the basis of keeping the total mass of the composition the same as that of Example 5, the mass proportion of the components in the composition is changed. Among them, in the composition, the mass proportion of the organic P-type semiconductor material is 50%, and the mass proportion of the first polyhole transport material is 50%, that is, the mass ratio of the first hole transport material to the organic P-type semiconductor material is 5:5.

[0221] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0222] Example 8

[0223] Example 8 is basically the same as Example 5, except that: the mass ratio of the components in the composition is changed while the total mass of the composition is kept the same as that of Example 5. In the composition, the mass ratio of the organic P-type semiconductor material is 30%, and the mass ratio of the first polyhole transport material is 70%, that is, the mass ratio of the first hole transport material to the organic P-type semiconductor material is 7:3.

[0224] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0225] Example 9

[0226] Example 9 is substantially the same as Example 6, except that the types of components in the composition are changed while the total mass of the composition is kept the same as that of Example 6. In particular, the first polyhole transport material is replaced by polymer P2.

[0227] The other steps and process conditions are the same as those in Example 6, see Table 1 for details.

[0228] Example 10

[0229] Example 10 is substantially the same as Example 6, except that the types of components in the composition are changed while the total mass of the composition is kept the same as that of Example 6. In particular, the first polyhole transport material is replaced by polymer P3.

[0230] The other steps and process conditions are the same as those in Example 6, see Table 1 for details.

[0231] Embodiment 11

[0232] Example 11 is substantially the same as Example 6, except that the types of components in the composition are changed while the total mass of the composition is kept the same as that of Example 6. In particular, the first polyhole transport material is replaced by polymer P4.

[0233] The other steps and process conditions are the same as those in Example 6, see Table 1 for details.

[0234] Example 12

[0235] Example 12 is basically the same as Example 6, except that: on the basis of keeping the total mass of the composition the same as that of Example 6, the types of components in the composition are changed. In particular, the organic P-type semiconductor material is replaced with TFB (poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)], with a number average molecular weight of 10 kDa).

[0236] The other steps and process conditions are the same as those in Example 6, see Table 1 for details.

[0237] Embodiment 13

[0238] Example 13 is substantially the same as Example 6, except that the types of the components are changed while the total mass of the composition is kept the same as that of Example 6. In particular, the organic P-type semiconductor material is replaced with Poly-TPD (polytriphenylamine, with a number average molecular weight of 10 kDa).

[0239] The other steps and process conditions are the same as those in Example 6, see Table 1 for details.

[0240] Comparative Example 1

[0241] Comparative Example 1 is substantially the same as Example 5, except that: on the basis of maintaining the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the first hole transport material is replaced by PVK.

[0242] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0243] Comparative Example 2

[0244] Comparative Example 2 is substantially the same as Example 5, except that: on the basis of maintaining the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the first hole transport material is replaced by TFB.

[0245] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0246] Comparative Example 3

[0247] Comparative Example 3 is substantially the same as Example 5, except that: on the basis of maintaining the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the first hole transport material is replaced by Poly-TPD.

[0248] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0249] Comparative Example 4

[0250] Comparative Example 4 is substantially the same as Example 5, except that: on the basis of maintaining the total mass of the composition the same as that of Example 5, the component types of the composition are changed, and the organic P-type semiconductor material is replaced by the polymer P1.

[0251] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0252] Comparative Example 5

[0253] Comparative Example 5 is substantially the same as Example 5, except that: on the basis of maintaining the total mass of the composition the same as that of Example 5, the component types of the composition are changed, and the organic P-type semiconductor material is replaced by the polymer P2.

[0254] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0255] Comparative Example 6

[0256] Comparative Example 6 is substantially the same as Example 5, except that: while maintaining the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the organic P-type semiconductor material is replaced by polymer P3.

[0257] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0258] Comparative Example 7

[0259] Comparative Example 7 is substantially the same as Example 5, except that: while maintaining the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the organic P-type semiconductor material is replaced by polymer P4.

[0260] The other steps and process conditions are the same as those in Example 5, see Table 1 for details.

[0261] Comparative Example 8

[0262] Comparative Example 8 is substantially the same as Example 5, except that: on the basis of keeping the total mass of the composition the same as that of Example 5, the types of components of the composition are changed, and the polymer P1 is replaced by the polymer P5 of the same mass, wherein the preparation process of the polymer P5 is as follows:

[0263] Using double-row tube technology, 1 g of monomer M1 (about 2.9 mM) and 15 mL of toluene were added to a 100 mL reaction bottle under argon protection, and 25 mg of azobisisobutyronitrile (AIBN) polymerization initiator was added under stirring. After mixing evenly, the reactants were heated to 80°C for polymerization. After 8 hours of reaction, the reaction mixture was poured into a large amount of ethanol solution for precipitation, the precipitate was collected and washed with ethanol several times, and finally vacuum dried to obtain the atactic polymer P5.

[0264] Differential scanning calorimetry (DSC) testing of P5 revealed that it had a glass transition at around 100°C during the secondary heating process, but no endothermic peak was observed, indicating that its atactic polymer main chain caused the polymer molecules to be arranged in a disordered form.

[0265]

[0266] The elemental analysis results showed that C was 89.89, H was 6.08, and N was 4.03. The number average molecular weight of polymer P5 was 16 kDa as determined by gel chromatography.

[0267] The relevant parameters and test results of the compositions used in each embodiment and each comparative example are shown in Table 1, wherein in the composition, the mass proportion of the organic P-type semiconductor material is denoted as A%, the mass proportion of the first polyhole transport material is denoted as B%, and the mass ratio of the first hole transport material to the organic P-type semiconductor material is denoted as C.

[0268] Table 1

[0269]

[0270] Note: “ / ” represents the absence of the substance or parameter; “PVK” is polyvinylcarbazole, “TFB” is poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)], and “Poly-TPD” is polytriphenylamine.

[0271] As shown in Table 1, compared with a single first hole transport material or an organic P-type semiconductor material, the synergistic effect of the first hole transport material having a specific structure in the present application and other organic P-type semiconductor materials can further improve the hole mobility.

[0272] Any combination can be made. In order to make the description concise, not all possible combinations of the various technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0273] The above-described embodiments only express several implementation methods of the present invention, which is convenient for understanding the technical solution of the present invention in detail, but it cannot be understood as limiting the scope of protection of the invention patent. It should be pointed out that for ordinary technicians in this field, several modifications and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention. It should be understood that the technical solutions obtained by those skilled in the art through logical analysis, reasoning or limited experiments on the basis of the technical solution provided by the present invention are all within the protection scope of the claims attached to the present invention.

Claims

1. A composition, characterized in that The composition comprises a first hole transport material and an organic P-type semiconductor material, wherein the structure of the first hole transport material is as shown in formula (1): Wherein: * represents a chiral center; each monomer is an optically active isomer unit, and the optically active isomer unit forms a stereoregular form in the molecular chain; Each occurrence of Ar is independently selected from the first hole transporting group.

2. The composition according to claim 1, characterized in that The mass ratio of the first hole transport material to the organic P-type semiconductor material is (1-7):(3-9); and / or The composition consists of the first hole transport material and the organic P-type semiconductor material.

3. The composition according to claim 2, characterized in that The mass ratio of the first hole transport material to the organic P-type semiconductor material is (2-6):(4-8).

4. The composition according to claim 1, characterized in that The optically active units in at least part of the molecular chains of the first hole transport material form an isotactic form in the molecular chains.

5. The composition according to claim 1, characterized in that The organic P-type semiconductor material contains a second hole transport group, The first hole transport group and the second hole transport group are independently selected from at least one of an unsubstituted or substituted aniline group and an unsubstituted or substituted carbazole group; the substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a halogen group, a heteroaryl group having 5 to 30 ring atoms, and an aryl group having 6 to 30 ring atoms.

6. The composition according to claim 5, characterized in that The composition satisfies the following conditions (1) and / or (2): (1) at least part of the first hole transport group includes at least one of an unsubstituted or substituted aniline group, and at least part of the second hole transport group includes at least one of an unsubstituted or substituted aniline group; (2) At least part of the first hole transport group includes at least one of unsubstituted or substituted carbazole groups, and at least part of the second hole transport group includes at least one of unsubstituted or substituted carbazole groups.

7. The composition according to claim 5, characterized in that Each occurrence of Ar is independently selected from any of the following groups: Wherein: X1 is selected from CR1; X2 is selected from CR2; R1 and R2 are each independently selected from any one of H, D, hydroxyl, nitro, -N(R4)2, halogen, unsubstituted or substituted straight-chain alkyl having 1 to 20 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkyl having 3 to 30 C atoms, unsubstituted or substituted straight-chain alkenyl having 2 to 20 C atoms, unsubstituted or substituted branched alkenyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkenyl having 3 to 20 C atoms, unsubstituted or substituted aromatic having 6 to 60 ring atoms, and unsubstituted or substituted heteroaromatic having 5 to 60 ring atoms; Adjacent R1s may form a ring or not, and adjacent R2s may form a ring or not; R3 and R4 are each independently selected from the group consisting of H, D, hydroxyl, nitro, amino, halogen, unsubstituted or substituted straight-chain alkyl having 1 to 20 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkyl having 3 to 30 C atoms, unsubstituted or substituted straight-chain alkenyl having 2 to 20 C atoms, unsubstituted or substituted branched alkenyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkenyl having 3 to 20 C atoms, unsubstituted or substituted aromatic having 6 to 60 ring atoms, unsubstituted or substituted heteroaromatic having 5 to 60 ring atoms; n is selected from any integer from 1 to 4, represents the junction site; The substituents of R1, R2, R3 and R4 are independently selected from any one of a halogen group, a cyano group, a hydroxyl group, a nitro group, a carbonyl group, an alkenyl group having 2 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 ring atoms, a heteroaryl group having 5 to 30 ring atoms, and an alkoxy group having 1 to 10 carbon atoms; and / or At least part of the second hole transporting group is the same as at least part of the first hole transporting group.

8. The composition according to claim 7, characterized in that Ar satisfies at least one of the following conditions (1) to (2): (1) R1 and R2, at each occurrence, are independently selected from any one of H, D, -N(R4)2, unsubstituted or substituted straight-chain alkyl having 1 to 10 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 10 C atoms, unsubstituted or substituted cycloalkyl having 3 to 30 C atoms, unsubstituted or substituted aromatic group having 6 to 30 ring atoms, and unsubstituted or substituted heteroaromatic group having 5 to 30 ring atoms; (2) Each occurrence of R4 is independently selected from the group consisting of H, D, unsubstituted or substituted straight-chain alkyl having 1 to 20 C atoms, unsubstituted or substituted branched-chain alkyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkyl having 3 to 20 C atoms, unsubstituted or substituted straight-chain alkenyl having 2 to 20 C atoms, unsubstituted or substituted branched alkenyl having 3 to 20 C atoms, unsubstituted or substituted cycloalkenyl having 3 to 20 C atoms, unsubstituted or substituted aromatic groups having 6 to 60 ring atoms, and unsubstituted or substituted heteroaromatic groups having 5 to 60 ring atoms.

9. The composition according to claim 7, characterized in that Adjacent R1 do not form a ring, adjacent R2 do not form a ring, and each occurrence of R1 and R2 is independently selected from H, D or any one of the following groups: or Adjacent R1s form a ring and / or adjacent R2s form a ring, and are independently selected from any one of the following groups: Where: · represents the fusion site.

10. The composition according to claim 9, characterized in that Each occurrence of Ar is independently selected from any of the following groups:

11. The composition according to any one of claims 1 to 10, characterized in that The organic P-type semiconductor material includes at least one of an organic polymer P-type semiconductor material and a small molecule organic P-type semiconductor material; The organic polymer P-type semiconductor material is selected from at least one of poly(9,9-dioctylfluorene-co-N-(4-butylphenyl)diphenylamine), polyvinylcarbazole, poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine), poly(9,9-dioctylfluorene-co-bis-N,N-phenyl-1,4-phenylenediamine), and poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid); and / or The number average molecular weight of the organic polymer P-type semiconductor material is 4 kDa to 50 kDa; and / or The small molecule organic P-type semiconductor material is selected from at least one of 4,4',4"-tri(carbazole-9-yl)triphenylamine, 4,4'-di(9-carbazole)biphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine, and N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine; and / or x is an integer greater than 5.

12. An electronic device, characterized in that: The electronic device comprises a first electrode, a carrier transport layer and a second electrode stacked in sequence, the material of the carrier transport layer comprises a composition, the composition comprises a first hole transport material and an organic P-type semiconductor material, and the structure of the first hole transport material is shown in formula (1): Wherein: * represents a chiral center; each monomer is an optically active isomer unit, and the optically active isomer unit forms a stereoregular form in the molecular chain; Each occurrence of Ar is independently selected from the first hole transporting group.

13. The electronic device according to claim 12, characterized in that: The mass ratio of the first hole transport material to the organic P-type semiconductor material is (1-7):(3-9); and / or At least part of the optically active units in the molecular chain of the first hole transport material form an isotactic form in the molecular chain; and / or The organic P-type semiconductor material contains a second hole transport group, and at least part of the second hole transport group is of the same type as part of the first hole transport group.

14. The electronic device according to claim 13, characterized in that: The carrier transport layer satisfies the following conditions (1) or (2): (1) at least part of the first hole transport group includes at least one of an unsubstituted or substituted aniline group, and at least part of the second hole transport group includes at least one of an unsubstituted or substituted aniline group; (2) at least part of the first hole transport group includes at least one of an unsubstituted or substituted carbazole group, and at least part of the second hole transport group includes at least one of an unsubstituted or substituted carbazole group; The substituents of the aniline group and the carbazole group are independently selected from any one or more combinations of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, a halogen group, a heteroaryl group having 5 to 30 ring atoms, and an aryl group having 6 to 30 ring atoms; and / or At least part of the second hole transporting group is the same as at least part of the first hole transporting group.

15. The electronic device according to any one of claims 12 to 14, characterized in that: It also includes a light-emitting layer, which is arranged between the carrier transport layer and the first electrode, or between the carrier transport layer and the second electrode; the material of the light-emitting layer includes at least one of quantum dots or organic light-emitting materials, the quantum dots include at least one of single-structure quantum dots and core-shell structure quantum dots, and the shell layer of the core-shell structure quantum dots is one or more layers; the material of the single-structure quantum dots includes at least one of II-VI group compounds, IV-VI group compounds, III-V group compounds and I-III-VI group compounds; the II-VI group compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, Cd At least one of HgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and HgZnSTe; The IV-VI group compounds include at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, SnPbSSe, SnPbSeTe and SnPbSTe; the III-V group compounds include GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb , at least one of AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs and InAlPSb; the I-III-VI group compound includes at least one of CuInS2, CuInSe2 and AgInS2; The core of the core-shell structured quantum dot includes any one of the single structured quantum dots, and the shell material includes at least one of CdS, CdTe, CdSeTe, CdZnSe, CdZnS, CdSeS, ZnSe, ZnSeS, ZnS and the single structured quantum dots; The organic light-emitting material includes at least one of 4,4'-bis(N-carbazole)-1,1'-biphenyl:tris[2-(p-tolyl)pyridine-C2,N)iridium(III), 4,4',4"-tris(carbazole-9-yl)triphenylamine:tris[2-(p-tolyl)pyridine-C2,N)iridium, diaromatic anthracene derivatives, distilbene aromatic derivatives, pyrene derivatives, fluorene derivatives, TBPe fluorescent materials, TTPX fluorescent materials, TBRb fluorescent materials and DBP fluorescent materials, polyacetylene and its derivatives, polyparaphenylene and its derivatives, polythiophene and its derivatives, polyfluorene and its derivatives; and / or The first electrode and the second electrode are each independently selected from a metal electrode, a carbon silicon material electrode, an inorganic semiconductor particle electrode or a composite electrode. The material of the metal electrode is selected from at least one of Ag, Al, Mg, Au, Cu, Mo, Pt, Ca and Ba. The material of the carbon silicon material electrode is selected from at least one of silicon, graphite, carbon nanotubes, graphene and carbon fiber. The material of the inorganic semiconductor particle electrode is selected from at least one of indium-doped tin oxide, fluorine-doped tin oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, gallium-doped zinc oxide, indium-doped zinc oxide, magnesium-doped zinc oxide and aluminum-doped magnesium oxide. The composite electrode is selected from AZO / Ag / AZO, AZO / Al / AZO, ITO / Ag / ITO, ITO / Al / ITO, ZnO / Ag / ZnO, ZnO / Al / ZnO, TiO2 / Ag / TiO2, TiO2 / Al / TiO2, ZnS / Ag / ZnS or ZnS / Al / ZnS.

16. A display device, characterized in that: Comprising the electronic device according to any one of claims 12 to 15.

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