Composition, light-emitting material, light-emitting ink, and photoelectric device

Abstract

The invention discloses a composition, a luminescent material, luminescent ink and a photoelectric device, the composition comprises a first phosphorescent material and a second phosphorescent material, the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01 eV, and the absolute value of the difference between the LUMO energy level of the first phosphorescent material and the LUMO energy level of the second phosphorescent material is not greater than 0.3 eV. The composition can be used as a light-emitting guest material of a photoelectric device, and is beneficial to adjusting the electric balance in the photoelectric device, so that the position of a carrier recombination region is improved, and the performance of the photoelectric device is effectively improved.

Description

Technical Field

[0001] The present application relates to the technical field of optoelectronic materials, and in particular to a composition, a luminescent material, a luminescent ink and an optoelectronic device. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the characteristics of self-luminescence, high brightness, wide viewing angle, high contrast, flexibility, low energy consumption, fast response speed, etc., and is widely used in display devices, lighting and other technical fields. In order to improve the device efficiency and device life of OLED, OLED generally has a multilayer structure. For example, OLED includes an anode, a hole functional layer, a light-emitting layer, an electronic functional layer and a cathode stacked in sequence. The light-emitting principle of OLED is: when a voltage is applied between the anode and the cathode, electrons are injected from the cathode to the light-emitting layer via the electronic functional layer, and holes are injected from the anode to the light-emitting layer via the hole functional layer. Electrons and holes recombine in the light-emitting area to form excitons, and the recombined excitons release photons in the form of radiation transition, thereby emitting light. After years of development, OLED has made great progress in performance indicators and has shown great potential for application development, but the performance of OLED needs to be further improved. Summary of the invention

[0003] In view of the deficiencies in the prior art, the present application provides a composition, a luminescent material, a luminescent ink and a photoelectric device.

[0004] In a first aspect, the present application provides a composition comprising a first phosphorescent material and a second phosphorescent material, wherein the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01 eV, and the absolute value of the difference between the LUMO energy level of the first phosphorescent material and the LUMO energy level of the second phosphorescent material is not greater than 0.3 eV.

[0005] In a second aspect, the present application provides a light-emitting material, which includes a host material and a guest material, and the guest material includes the composition described in the first aspect.

[0006] In a third aspect, the present application provides a luminescent ink, wherein the luminescent ink comprises the composition as described in the first aspect, or the luminescent material as described in the second aspect;

[0007] The luminescent ink also includes at least one first organic solvent; optionally, the first organic solvent is selected from one or more of aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0008] In a fourth aspect, the present application provides an optoelectronic device, comprising:

[0009] an anode and a cathode disposed opposite to each other; and

[0010] A plurality of functional layers are disposed between the anode and the cathode;

[0011] Among them, the material of at least one of the multiple functional layers includes the composition described in the first aspect, or the luminescent material described in the second aspect, or at least one of the multiple functional layers is prepared using the luminescent ink described in the third aspect.

[0012] The composition of the embodiment of the present application can be used as a luminescent guest material of an optoelectronic device, which is beneficial for adjusting the electrical balance inside the optoelectronic device, thereby improving the position of the carrier recombination zone and effectively improving the performance of the optoelectronic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] The technical solution and other beneficial effects of the present application will be made apparent by describing in detail the specific implementation methods of the present application in conjunction with the accompanying drawings.

[0014] Figure 1 A schematic diagram of the structure of a photoelectric device provided in an embodiment of the present application.

[0015] The reference numerals are as follows:

[0016] 10: optoelectronic device, 101: anode, 102: cathode, 103: functional layer, 104: light extraction layer, 1031: light emitting layer, 1032: hole functional layer, 1033: electron functional layer, 10321: hole injection layer, 10322: hole transport layer, 10331: electron transport layer, 10332: electron injection layer. DETAILED DESCRIPTION

[0017] The technical solutions in the embodiments of the present application will be described clearly and completely below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application.

[0018] Unless otherwise defined, all professional and scientific terms used herein have the same meanings as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to those described herein may be applied to the present invention. The preferred implementation methods and materials described herein are for demonstration purposes only and are not intended to limit the content of this application.

[0019] It should be noted that the description order of the following embodiments is not intended to limit the preferred order of the embodiments. The various embodiments of the present application may be presented 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 rigid limitation on the scope of the present invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single values ​​within the range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which apply regardless of the range. In addition, whenever a numerical range is indicated in this article, it is meant to include any cited numbers (fractions or integers) within the indicated range.

[0020] In this application, unless otherwise stated, directional words such as "upper" and "lower" generally refer to the upper and lower parts of the optoelectronic device in actual use or working state, specifically the drawing direction in the attached drawings; while "inner" and "outer" refer to the outline of the optoelectronic device. The terms first, second, third, etc. are used only as labels and do not impose numerical requirements or establish a sequence.

[0021] In the present application, “layer A is formed on one side of layer B”, “layer A is formed on the side of layer B away from layer C” or similar descriptions can be expressed as layer A is directly formed on one side of layer B or on the side of layer B away from layer C, that is, layer A is in direct contact with layer B, or as layer A is indirectly formed on one side of layer B or on the side of layer B away from layer C, that is, other spacing structure layers can be formed between layer A and layer B. Similarly, “layer A is arranged on one side of layer B”, “layer A is arranged on the side of layer B away from layer C” can be expressed as layer A is in direct contact with layer B, or as other spacing structure layers are arranged between layer A and layer B; “layer A is arranged between layer B and layer C” can be expressed as layer A is in direct contact with layer B and layer A is in direct contact with layer C, or layer A is in direct contact with layer B and one or more spacing structure layers are arranged between layer A and layer C, or one or more spacing structure layers are arranged between layer A and layer B and one or more spacing structure layers are arranged between layer A and layer C, or one or more spacing structure layers are arranged between layer A and layer B and layer A is in direct contact with layer C.

[0022] The term "including" means "including but not limited to".

[0023] The term "and / or" is used to describe the association relationship of associated objects, indicating that there may be three relationships. For example, A and / or B can mean: A exists alone, A and B exist at the same time, and B exists alone. A and B can be singular or plural.

[0024] The term "at least one" refers to one or more, and "more than one" refers to two or more. The term "at least one", "the following at least one" or similar expressions refer to any combination of these items, including any combination of a single or multiple. For example, "at least one of a, b or c" or "at least one of a, b and c" can be expressed as: a, b, c, ab (i.e. a and b), ac, bc or abc, where a, b and c can be single or multiple, respectively.

[0025] In the present application, "amino" refers to a group of the general formula -NR'R", wherein R' and R" are independently selected from but not limited to a hydrogen atom, a deuterium atom, a cyano group, an isocyano group, a nitro group, a halogen atom, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched alkyl group or a cycloalkyl group having 3 to 10 carbon atoms, an aliphatic cycloalkyl group having 3 to 10 ring atoms, an alicyclic group having 3 to 10 ring atoms, an aromatic group having 6 to 14 ring atoms, a heteroaryl group having 5 to 14 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0026] The term "chain hydrocarbon group" refers to an aliphatic straight chain hydrocarbon group or an aliphatic branched chain hydrocarbon group, and the "aliphatic chain hydrocarbon group of C1 to C30" may be, for example, a straight chain alkyl group having 1 to 30 carbon atoms, a straight chain alkenyl group having 2 to 30 carbon atoms, a straight chain alkynyl group having 2 to 30 carbon atoms, a branched chain alkyl group having 3 to 30 carbon atoms, a branched chain alkenyl group having 4 to 30 carbon atoms, or a branched chain alkynyl group having 4 to 30 carbon atoms. The number of carbon atoms in the chain hydrocarbon group may be, for example, 1 to 5, 5 to 8, 5 to 10, 5 to 15, 5 to 20, or 10 to 20, exemplified by 1, 3, 5, 8, 10, 15, 20, 25, 30, or a value between any two of the foregoing values. For example, it may be a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group, a C8 alkyl group, a C9 alkyl group or a C10 alkyl group.

[0027] The term "alkoxy" refers to a group of the general formula *-O-alkoxy, where * represents the attachment site and O represents an oxygen atom.

[0028] The term "aliphatic cycloalkyl" refers to an aliphatic cyclic hydrocarbon group. The number of ring atoms in the "aliphatic cycloalkyl group having 3 to 30 ring atoms" can be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, or 5 to 10, exemplified by 3, 5, 6, 8, 10, 14, 20, 24, 28, 30, or a value between any two of the foregoing values. Suitable examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or adamantyl.

[0029] The term "aliphatic heterocyclic hydrocarbon group" means that at least one carbon atom in the aliphatic cyclic hydrocarbon group is replaced by a non-carbon atom, and the non-carbon atom may be one or more of an N atom, an O atom, an S atom, an Si atom and a P atom, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group is independently 1 to 20. The number of ring atoms in the "aliphatic heterocyclic hydrocarbon group having 3 to 30 ring atoms" may be, for example, 3 to 5, 3 to 8, 3 to 10, 3 to 14, 3 to 20, or 5 to 10, exemplified by 3, 5, 6, 8, 10, 14, 20, 24, 28, 30, or a value between any two of the foregoing values.

[0030] The term "aryl" 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 a polycyclic ring, at least one is an aromatic ring system. "Aryl having 6 to 40 ring atoms" can be an aromatic group having 6 to 30 ring atoms, an aromatic group having 6 to 18 ring atoms, an aromatic group having 6 to 16 ring atoms, an aromatic group having 6 to 14 ring atoms, or an aromatic group having 6 to 10 ring atoms, and the number of ring atoms can be, for example, 6, 10, 12, 14, 16, 18, 20, 24, 26, 28, 30 or a value between any two of the aforementioned values. Suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylene, naphthylene, 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.

[0031] The term "heteroaryl" means that at least one carbon atom on the basis of an aryl group is replaced by a non-carbon atom, and the non-carbon atom may be one or more of an N atom, an O atom, an S atom, an Si atom and a P atom, and the number of heteroatoms is, for example, 1 to 20. "Heteroaryl having 5 to 30 ring atoms" may be a heteroaryl having 5 to 20 ring atoms, a heteroaryl having 5 to 18 ring atoms, a heteroaryl having 5 to 16 ring atoms, a heteroaryl having 5 to 14 ring atoms, a heteroaryl having 5 to 12 ring atoms, or a heteroaryl having 5 to 10 ring atoms, and the number of ring atoms may be, for example, 5, 10, 12, 14, 18, 20, 24, 26, 28, 30 or a value between any two of the foregoing values. Suitable examples include, but are not limited to, thienyl, furanyl, pyrrolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primidyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.

[0032] In the present application, "halogen group" or "halogen" represents -Cl, -Br, -F or -I; hydroxyl represents -OH; carboxyl represents -COOH; nitro represents -NO2; sulfonic acid represents -SO3H; mercapto represents -SH; cyano represents *-C≡N.

[0033] 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.

[0034] In the present application, a single bond to which a substituent is attached runs through the corresponding ring, indicating that the substituent can be attached to any position of the ring.

[0035] In the present application, the HOMO energy level and LUMO energy level of the material are both based on the vacuum energy level of 0 as a reference value.

[0036] It should be noted that the method for determining the HOMO energy level and the LUMO energy level in the present application is: using TD-DFT (time-dependent density functional theory) through Gaussian 09W (Gaussian Inc.), first using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet) to optimize the molecular geometry, and then the energy structure of the organic molecule is calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / DefaultSpin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet).

[0037] The HOMO and LUMO energy levels are calculated according to the following calibration formula:

[0038] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206;

[0039] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385.

[0040] An embodiment of the present application provides a composition, which includes a first phosphorescent material and a second phosphorescent material, wherein the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01 eV, so that the second phosphorescent material has the effect of a hole trap; and the absolute value of the difference between the LUMO energy level of the first phosphorescent material and the LUMO energy level of the second phosphorescent material is not greater than 0.3 eV, so that the second phosphorescent material does not have the effect of an electron trap or the electron trap effect of the second phosphorescent material is weakened.

[0041] The composition of the embodiment of the present application can be used as a light-emitting guest material of an optoelectronic device (such as an OLED), which is beneficial for adjusting the electrical balance inside the optoelectronic device, thereby improving the position of the carrier recombination zone and effectively improving the performance of the optoelectronic device.

[0042] In order to control the depth of the hole trap and thus further improve the carrier transport performance, in some embodiments of the present application, the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01eV and less than 0.5eV, and the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is, for example, 0.01eV, 0.05eV, 0.08eV, 0.1eV, 0.2eV, 0.3eV, 0.4eV, 0.5eV or a value between any two of the foregoing values.

[0043] In order to enhance the hole trapping effect of the second phosphorescent material, in some embodiments of the present application, the absolute value of the LUMO energy level of the second phosphorescent material is not greater than the absolute value of the LUMO energy level of the first phosphorescent material.

[0044] In order to further improve the luminescent performance of the composition, in some embodiments of the present application, the mass ratio of the second phosphorescent material to the first phosphorescent material is 1:(1-150), for example, it can be 1:1, 1:2.5, 1:10, 1:30, 1:50, 1:80, 1:100, 1:120, 1:150 or a value between any two of the foregoing ratios.

[0045] In order to further improve the color purity of the luminescence, in some embodiments of the present application, the absolute value of the difference between the photoluminescence peak of the first phosphorescent material and the photoluminescence peak of the second phosphorescent material is not greater than 15nm, for example, not greater than 13nm, not greater than 10nm, not greater than 8nm, not greater than 5nm, not greater than 3nm or not greater than 1nm.

[0046] In some embodiments of the present application, the photoluminescence peak of the first phosphorescent material is 500nm-650nm, and / or the photoluminescence peak of the second phosphorescent material is 500nm-650nm. For example, the first phosphorescent material and the second phosphorescent material are both green phosphorescent materials, the photoluminescence peak of the first phosphorescent material is 525nm-540nm, and / or the photoluminescence peak of the second phosphorescent material is 525nm-540nm; for another example, the first phosphorescent material and the second phosphorescent material are both red phosphorescent materials, the photoluminescence peak of the first phosphorescent material is 580nm-650nm, and / or the photoluminescence peak of the second phosphorescent material is 580nm-650nm.

[0047] In some embodiments of the present application, the first phosphorescent material and the second phosphorescent material are independently selected from iridium complexes represented by the general formula Ir-(L1)(L2)(L3), wherein L1, L2 and L3 are independently selected from any one of the following structural formulas:

[0048]

[0049] Among them, Ar1 to Ar3 are independently selected from an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 6-10, 6-12, 6-14, 6-16, 6-18, 6-20, 6-24, or 6-30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 5-10, 5-12, 5-14, 5-16, 5-18, 5-20, 5-24, or 5-30), an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted by at least one R, or a combination of these groups.

[0050] R1 to R3 are independently selected from -H, -D, a C1-C30 aliphatic chain hydrocarbon group, a C1-C30 aliphatic chain hydrocarbon oxy group, an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 6-10, 6-12, 6-14, 6-16, 6-18, 6-20, 6-24, or 6-30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 5-10, 5-12, 5-14, 5-16, 5-18, 5-20, 5-24, or 5-30), an An aliphatic cycloalkyl group having 3 to 40 ring atoms (the number of ring atoms may be, for example, 3 to 10, 3 to 12, 3 to 14, 3 to 16, 3 to 18, 3 to 20, 3 to 24, or 3 to 30) which is substituted or substituted by at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms (the number of ring atoms may be, for example, 3 to 10, 3 to 12, 3 to 14, 3 to 16, 3 to 18, 3 to 20, 3 to 24, or 3 to 30) which is substituted or substituted by at least one R, an amino group, a halogen group, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, an aldehyde group, a carbonyl group, a thiol group, a cyano group, or a combination of these groups.

[0051] Each time R appears, it is independently selected from -H, -D, a C1-C10 aliphatic chain hydrocarbon group, a C1-C10 aliphatic chain hydrocarbon oxy group, an aryl group having 6 to 20 ring atoms (the number of ring atoms can be, for example, 6 to 10, 6 to 12, 6 to 14, 6 to 16, or 6 to 18), a heteroaryl group having 5 to 20 ring atoms (the number of ring atoms can be, for example, 5 to 10, 5 to 12, 5 to 14, 5 to 16, or 5 to 18), an aliphatic cycloalkyl group having 3 to 30 ring atoms, an aliphatic heterocycloalkyl group having 3 to 30 ring atoms, an amino group, a halogen group, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, an aldehyde group, a carbonyl group, a thiol group, a cyano group, or a combination of these groups.

[0052] * indicates the connection site between L1, L2 or L3 and Ir.

[0053] In some embodiments of the present application, the first phosphorescent material and the second phosphorescent material are both selected from iridium complexes, for example, the first phosphorescent material and the second phosphorescent material are both selected from green light iridium complexes or red light iridium complexes.

[0054] In some embodiments of the present application, the first phosphorescent material and the second phosphorescent material are independently selected from green phosphorescent materials, the first phosphorescent material is selected from one or more of Ir(mppy)3 (CAS No. 149005-33-4), Ir(ppy)3 (CAS No. 94928-86-6) and Ir(ppy)2(acac) (CAS No. 337526-85-9), and the second phosphorescent material is selected from one or more of Ir(Dppy)3, Ir(Buppy)3, (pbi)2Ir(acac), (cbi)2Ir(acac), (tbi)2Ir(acac), Ir(fbi)2(acac), Ir(dmppy-pro)2tmd, fac-Ir(ppy)3, (3-PEC)2Ir(acac), Ir(mchpy)3 and Ir(BPPya)3.

[0055] In some other embodiments of the present application, the first phosphorescent material and the second phosphorescent material are independently selected from red phosphorescent materials, the first phosphorescent material is selected from one or more of Ir(piq)2acac, Ir(pcpiq)2acac, Ir(hpiq)3 and Ir(piq)3, and the second phosphorescent material is selected from (pq)2Ir(acac), (bpiq)2Ir(acac), (ppz)2Ir(piq), Ir(btp)2(acac), Ir(2 -phq)2(acac), Ir(bt)2(acac), acetylacetonate di(4-phenyl-thiophene[3,2-c]pyridine-C2,N)iridium(III) (abbreviated as PO-01, CAS No. 1258323-36-2) and acetylacetonate di(4-(4-tert-butyl-phenyl)-thiophene[3,2-c]pyridine-C2,N)iridium(III) (abbreviated as PO-01-TB, CAS No. 1267497-10-8).

[0056] The embodiment of the present application further provides a luminescent material, which includes a host material and a guest material, and the guest material includes any one of the compositions described above.

[0057] In some embodiments of the present application, the host material is a green phosphorescent host material, and the first phosphorescent material and the second phosphorescent material are independently selected from green light iridium complexes.

[0058] In some other embodiments of the present application, the host material is a red phosphorescent host material, and the first phosphorescent material and the second phosphorescent material are independently selected from red iridium complexes.

[0059] In order to further enhance the luminescent effect of the luminescent material, in some embodiments of the present application, calculated by mass percentage, the luminescent material includes 81% to 95.9% of the host material and 4.1% to 19% of the guest material; and / or the mass of the first phosphorescent material accounts for 4% to 15% of the total mass of the luminescent material; and / or the mass of the second phosphorescent material accounts for 0.1% to 4% of the total mass of the luminescent material.

[0060] In some embodiments of the present application, the main material includes a first compound and / or a second compound. The main material is composed of, for example, a first compound and a second compound, wherein the first compound has a structure shown in the following general formula (I):

[0061]

[0062] In the general formula (I), Ar4 is selected from an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 6-10, 6-12, 6-14, 6-16, 6-18, 6-20, 6-24, or 6-30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 5-10, 5-12, 5-14, 5-16, 5-18, 5-20, 5-24, or 5-30), or a combination of these groups; A is an electron-rich group; n1 is selected from any integer from 1 to 6; when n1 is greater than 1, the multiple electron-rich groups are the same or different.

[0063] In some embodiments of the present application, A has one or more of the following structures:

[0064]

[0065] wherein Ar6 is selected from an aryl group having 6 to 40 ring atoms (for example, the number of ring atoms may be 6 to 10, 6 to 12, 6 to 14, 6 to 16, 6 to 18, 6 to 20, 6 to 24, or 6 to 30) which is unsubstituted or substituted with at least one R, a heteroaryl group having 5 to 40 ring atoms (for example, the number of ring atoms may be 5 to 10, 5 to 12, 5 to 14, 5 to 16, 5 to 18, 5 to 20, 5 to 24, or 5 to 30) which is unsubstituted or substituted with at least one R, or a combination of these groups;

[0066] Y1 and Y2 are independently selected from a single bond, N(R 12 )、C(R 13 R 14)、Si(R 15 R 16 )、O、S、C=N(R 17 )、C=C(R 18 R 19 ) or P(R 20 ); R4 to R 20 are independently selected from -H, -D, a C1-C30 aliphatic chain hydrocarbon group, a C1-C30 aliphatic chain hydrocarbon oxy group, an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 6 to 10, 6 to 12, 6 to 14, 6 to 16, 6 to 18, 6 to 20, 6 to 24, or 6 to 30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 5 to 10, 5 to 12, 5 to 14, 5 to 16, 5 to 18, 5 to 20 , 5-24, or 5-30), an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms can be, for example, 3-10, 3-12, 3-14, 3-16, 3-18, 3-20, 3-24, or 3-30), an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted with at least one R (the number of ring atoms can be, for example, 3-10, 3-12, 3-14, 3-16, 3-18, 3-20, 3-24, or 3-30), or a combination of these groups.

[0067] The second compound has the structure shown in the following general formula (II):

[0068]

[0069] In the general formula (II), Ar5 is selected from an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 6-10, 6-12, 6-14, 6-16, 6-18, 6-20, 6-24, or 6-30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 5-10, 5-12, 5-14, 5-16, 5-18, 5-20, 5-24, or 5-30), or a combination of these groups; E is an electron-deficient group; n2 is selected from any integer from 1 to 6; when n1 is greater than 1, the multiple electron-deficient groups are the same or different.

[0070] In some embodiments of the present application, E is selected from F, cyano or one or more of the following structures:

[0071]

[0072] Wherein, a is 1, 2 or 3;

[0073] Each time X appears, it is independently selected from C, CR 27 or N, and at least one of them is N;

[0074] M 1 、M 2 and M 3 are independently selected from N(R 28 )、C(R 29 R 30 )、Si(R 31 R 32 )、O、C=N(R 33 )、C=C(R 34 R 35 )、P(R 36 )、P(=O)R 37 , S, S=O, SO2 or none;

[0075] R 21 To R 37 Each of the following is independently selected from -H, -D, a C1-C30 aliphatic chain hydrocarbon group, a C1-C30 aliphatic chain hydrocarbonoxy group, an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 6-10, 6-12, 6-14, 6-16, 6-18, 6-20, 6-24, or 6-30), a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms may be, for example, 5-10, 5-12, 5-14, 5-16, 5-18, 5-20, 5-24, or 5-30), an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted with at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted with at least one R, or a combination of these groups.

[0076] In some embodiments of the present application, the first compound has a structure shown in the following formula (1-1):

[0077]

[0078] And / or, the second compound has a structure represented by the following general formula (2-1):

[0079]

[0080] Among them, Ar7 to Ar 11 are selected from an aryl group having 6 to 30 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 30 ring atoms which is unsubstituted or substituted by at least one R, or a combination of the foregoing groups;

[0081] In the general formula (I), Z, when present, is independently selected from C or CR 39 , R 39 Each occurrence is independently selected from -H, -D, C1-C30 aliphatic chain hydrocarbon group, C1-C30 aliphatic chain hydrocarbon oxy group, unsubstituted or substituted with at least one R aryl group with 6 to 30 ring atoms, unsubstituted or substituted with at least one R heteroaryl group with 5 to 30 ring atoms, or a combination of the foregoing groups, and two adjacent R 39 They may or may not form a loop with each other;

[0082] R 38 is a single bond, or R 38 The invention is selected from a C1-C30 aliphatic chain alkylene group, a C1-C30 aliphatic chain alkylene oxy group, an unsubstituted or at least one R substituted arylene group having 6 to 30 ring atoms, an unsubstituted or at least one R substituted heteroarylene group having 5 to 30 ring atoms, or a combination of the foregoing groups.

[0083] In some embodiments of the present application, Ar7 is selected from an aryl group having 6 to 14 ring atoms, which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 14 ring atoms, which is unsubstituted or substituted by at least one R, or a combination of the foregoing groups, for example, selected from phenyl, phenyl substituted by at least one C1 to C30 aliphatic chain hydrocarbon group, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, 9,9-dimethylfluorenyl, or dibenzofuranyl.

[0084] In some embodiments of the present application, Ar8 has a structure shown in the following formula (1-a):

[0085]

[0086] Among them, Ar 12 It is selected from an aryl group having 6 to 20 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 6 to 10, 6 to 12, 6 to 14, 6 to 16, or 6 to 18), a heteroaryl group having 5 to 20 ring atoms which is unsubstituted or substituted by at least one R (the number of ring atoms can be, for example, 5 to 10, 5 to 12, 5 to 14, 5 to 16, or 5 to 18), or a combination of the foregoing groups, and * represents a connection site. Ar 12 For example, it is selected from phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, terphenyl or triphenylene.

[0087] In some embodiments of the present application, the first compound is selected from one or more of the following compounds:

[0088]

[0089]

[0090] In some embodiments of the present application, Ar9 to Ar 11 Each independently represents a group represented by any of the following structural formulas:

[0091]

[0092] Wherein, each occurrence of X1, X2 or X3 is independently selected from C or CR 40 , R 40 Each occurrence is independently selected from -H, -D, an aryl group having 6 to 20 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms can be, for example, 6 to 10, 6 to 12, 6 to 14, 6 to 16, or 6 to 18), a heteroaryl group having 5 to 20 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms can be, for example, 5 to 10, 5 to 12, 5 to 14, 5 to 16, or 5 to 18), or a combination of the foregoing groups.

[0093] In the general formula (2-a), Ar 13 Does not exist, or Ar 12 An arylene group having 6 to 20 ring atoms (for example, the number of ring atoms may be 6 to 10, 6 to 12, 6 to 14, 6 to 16, or 6 to 18) which is unsubstituted or substituted with at least one R, a heteroarylene group having 5 to 20 ring atoms (for example, the number of ring atoms may be 5 to 10, 5 to 12, 5 to 14, 5 to 16, or 5 to 18) which is unsubstituted or substituted with at least one R, or a combination of the foregoing groups;

[0094] In the general formula (2-b), Ar 14 The group is selected from an aryl group having 6 to 20 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms can be, for example, 6 to 10, 6 to 12, 6 to 14, 6 to 16, or 6 to 18), a heteroaryl group having 5 to 20 ring atoms which is unsubstituted or substituted with at least one R (the number of ring atoms can be, for example, 5 to 10, 5 to 12, 5 to 14, 5 to 16, or 5 to 18), or a combination of the foregoing groups.

[0095] In some embodiments of the present application, the second compound is selected from one or more of the following compounds:

[0096]

[0097] In order to further enhance the luminescent effect of the luminescent material, in some embodiments of the present application, the main material is composed of a first compound and a second compound, and the mass ratio of the first compound to the second compound is 1:(0.1-9), for example, it can be 1:0.1, 1:0.5, 1:1, 1:3, 1:5, 1:9 or a value between any two of the aforementioned ratios.

[0098] The embodiment of the present application further provides a luminescent ink, which includes a composition as described in any one of the foregoing texts, or a luminescent material as described in any one of the foregoing texts.

[0099] In some embodiments of the present application, the luminescent ink further comprises at least one first organic solvent. The composition may be a solution or a suspension. Further, the luminescent ink may be ink, and the first organic solvent may be a solvent having a Hansen solubility parameter within the following range:

[0100] δd (dispersion force) is in the range of 17.0 to 23.2 MPa1 / 2, especially in the range of 18.5 to 21.0 MPa1 / 2;

[0101] δp (polar force) is in the range of 0.2 to 12.5 MPa1 / 2, especially in the range of 2.0 to 6.0 MPa1 / 2;

[0102] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa1 / 2, and particularly in the range of 2.0 to 6.0 MPa1 / 2.

[0103] According to the luminescent ink of the present application, the first organic solvent needs to consider its boiling point parameter when selecting. In some embodiments of the present application, the boiling point of the first organic solvent is not less than 150°C, for example, not less than 180°C, not less than 200°C, not less than 250°C, not less than 275°C or not less than 300°C, which is beneficial to prevent the "nozzle clogging" problem of the inkjet print head and improve the film quality.

[0104] When the luminescent ink is used in the printing process, the viscosity and surface tension of the luminescent ink are important parameters. The surface tension parameters of suitable luminescent inks are suitable for specific substrates and specific printing methods. In some embodiments, the surface tension of the luminescent ink according to the embodiment of the present application at working temperature or at 25°C ranges from 19dyne / cm to 60dyne / cm, for example, 22dyne / cm to 55dyne / cm, for example, 25dyne / cm to 40dyne / cm, and for example, 30dyne / cm to 40dyne / cm. In some embodiments, the viscosity of the luminescent ink according to the embodiment of the present application at working temperature or 25°C ranges from 1cps to 100cps, for example, 1cps to 10cps, 1cps to 50cps, for example, 1.5cps to 20cps, and for example, 2.0cps to 15cps. The luminescent ink prepared in this way will be beneficial to inkjet printing.

[0105] In some embodiments of the present application, the weight ratio of the luminescent material in the luminescent ink is 0.3wt% to 30wt%, for example, 0.5wt% to 20wt%, 0.5wt% to 15wt%, 0.5wt% to 10wt% or 1wt% to 5wt%.

[0106] In some embodiments of the present application, the first organic solvent is selected from at least one of aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

[0107] The aromatic or heteroaromatic solvent may be selected from, but not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, di ... At least one of propylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate and ethyl 2-furoate.

[0108] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Preferably, the ester-based solvent may be selected from one or more of ethyl p-methylbenzoate, ethyl benzoate, octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0109] The aromatic ketone-based solvent may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives of the above solvents. As an example, the derivative may be selected from, but not limited to, one or more of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0110] The aromatic ether-based solvent may be selected from, but is not limited to, one or more of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethyl acetate, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, tetralin, decalin, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0111] The aliphatic ketone-based solvent can be selected from, but is not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, one or more of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.

[0112] In some embodiments of the present application, the composition may further include a second organic solvent, which may be selected from but not limited to methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin and one or more of indene.

[0113] It is understandable that when the luminescent ink is a solution or a suspension, the luminescent ink may further include one or more additives, including but not limited to one or more of surfactants, lubricants, wetting agents, dispersants, hydrophobic agents and adhesives.

[0114] An embodiment of the present application also provides an optoelectronic device, which includes but is not limited to an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor or an organic plasmon emission diode.

[0115] Continue reading Figure 1The optoelectronic device 10 includes an anode 101, multiple functional layers and a cathode 102 which are stacked in sequence, wherein the anode 101 and the cathode 102 are arranged opposite to each other, the multiple functional layers are arranged between the anode 101 and the cathode 102, and the material of at least one of the multiple functional layers is as follows: The embodiment of the present application also provides an optoelectronic device, and the optoelectronic device includes but is not limited to an organic light emitting diode, an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor or an organic plasmon emission diode.

[0116] Continue reading Figure 1 The photoelectric device 10 includes an anode 101, a plurality of functional layers and a cathode 102 which are stacked in sequence, wherein the anode 101 and the cathode 102 are arranged opposite to each other, and the plurality of functional layers are arranged between the anode 101 and the cathode 102. The material of at least one of the plurality of functional layers includes the composition described in any one of the foregoing texts, or the luminescent material described in any one of the foregoing texts, or at least one of the plurality of functional layers is prepared using the luminescent ink described in any one of the foregoing texts, so as to improve the device efficiency and performance stability of the photoelectric device 10.

[0117] In some embodiments of the present application, multiple functional layers include a light-emitting layer 1031, and the material of the light-emitting layer 1031 includes a composition as described in any one of the foregoing texts, or a light-emitting material as described in any one of the foregoing texts, or the light-emitting layer 1031 is prepared using a light-emitting ink as described in any one of the foregoing texts, which can adjust the electrical balance of the optoelectronic device, effectively improve the position of the carrier recombination zone, promote the electron-hole transfer balance, improve the device efficiency and performance stability of the optoelectronic device 10, and ensure that the optoelectronic device 10 has good luminescence purity.

[0118] It should be noted that for organic light-emitting diodes, top-emitting organic light-emitting diodes are more sensitive to the position of the exciton recombination zone. If the recombination zone deviates too much, for example, it is too close to the cathode or anode, it is not conducive to optical light emission, and the device efficiency cannot be significantly improved. The position of the exciton recombination zone is affected by the electron-hole balance. In theory, it is believed that the recombination zone will be dispersed in the entire light-emitting layer. If the recombination zone is too close to the anode or cathode, quenching will occur at the interface, resulting in reduced device performance of the organic light-emitting diode. Therefore, it is necessary to adjust the position of the recombination zone by adjusting the electrical balance to improve the performance of the organic light-emitting diode. Some organic light-emitting diodes are based on phosphorescence, such as green organic light-emitting diodes, and there is a phenomenon that the recombination zone is too close to the cathode side. Based on this, the guest material in the light-emitting layer is optimized to be a mixture composed of a first phosphorescent material and a second phosphorescent material, the second phosphorescent material has a hole trap function, and the second phosphorescent material does not have an electron trap function or the electron trap function is very weak, so as to promote the internal electrical balance of the optoelectronic device, thereby improving the efficiency of the optoelectronic device.

[0119] In some embodiments of the present application, the plurality of functional layers include a hole functional layer 1032, see Figure 1 The hole function layer 1032 is disposed between the anode 101 and the light emitting layer 1031. The hole function layer 1032 may be a single layer structure or a multi-layer structure, and the thickness of the hole function layer 1032 is, for example, 10 nm to 100 nm.

[0120] When the hole functional layer 1032 is a multi-layer structure, the hole functional layer 1032, for example, includes one or more of a hole injection layer, a hole transport layer and an electron blocking layer. For the hole functional layer 1032 including the hole injection layer, the hole transport layer and the electron blocking layer, the hole transport layer is located between the hole injection layer and the electron blocking layer, and the hole injection layer is closer to the anode 101 than the electron blocking layer; for the hole functional layer 1032 including the hole transport layer and the electron blocking layer, the hole transport layer is closer to the anode 101 than the electron blocking layer; for the hole functional layer 1032 including the hole injection layer and the hole transport layer, the hole injection layer is closer to the anode 101 than the hole transport layer.

[0121] The hole injection layer is a layer used to promote the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can skillfully receive holes injected from the positive electrode at a low voltage. The highest occupied molecular orbital (HOMO) of the hole injection material is, for example, between the work function of the anode material and the HOMO of the surrounding organic material layer. In principle, all materials that can be used as hole injection layers of organic light-emitting diodes may be used as hole injection materials for optoelectronic devices in this application. Non-limiting examples of hole injection materials are one or more of NDP-2 (manufactured by Novaled), NDP-9 (manufactured by Novaled), F4-TCNQ, and F6-TCNNQ as p-type doping materials; tetrafluorotetracyanoquinodimethane, 7,7,8,8-tetracyanoquinodimethane, 4,4',4"-tri(2-naphthylphenylamino)triphenylamine (m-MTDATA), perylenetetracarboxylic acid dianhydride, pentacene, 2,3,6,7,10,11-hexacyano- One or more of 1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), PEDOT, PEDOT:PSS, PEDOT:PSS doped with s-MoO3 derivatives (PEDOT:PSS:s-MoO3), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine, tetracyanoquinodimethane (F4-TCQN), copper phthalocyanine, hexafluorophthalocyanine copper, nickel oxide, molybdenum oxide, tungsten oxide, vanadium oxide, molybdenum sulfide, tungsten sulfide and copper oxide.

[0122] The hole transport layer can be used to smoothly transport holes. The hole transport material known in the art for the hole transport layer is suitably a material with a high hole mobility, which can receive holes transmitted from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Non-limiting examples of hole transport materials are organic materials based on arylamines, organic materials based on carbazoles, conductive polymers, or block copolymers having both conjugated and non-conjugated parts. In principle, all materials that can be used as hole transport layers of organic light-emitting diodes may be used as hole transport materials for optoelectronic devices in this application. Non-limiting examples of hole transport materials include HTM014 (manufactured by Merck), HTM081 (manufactured by Merck), HTM163 (manufactured by Merck), HTM222 (manufactured by Merck), NHT-5 (manufactured by Novaled), NHT-18 (manufactured by Novaled), NHT-49 (manufactured by Novaled), NHT-51 (manufactured by Novaled), EL-301 (manufactured by Hodogaya), EL-22T (manufactured by Hodogaya Company), polyaniline (CAS No. 25233-30-1), polypyrrole (CAS No. 30604-81-0), 3-hexyl substituted polythiophene (CAS No. 104934-50-1), poly (9-vinyl carbazole) (abbreviated as PVK, CAS No. 25067-59-8), 4,4'-bis (9-carbazole) biphenyl (abbreviated as CBP, CAS No. 58328-31-7), poly [bis (4-phenyl) (4-butylphenyl) amine], 4,4'-cyclohexyl bis [N, N-bis (4-methylphenyl) aniline] (abbreviated as TAP C, CAS No. 58473-78-2), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine)] (abbreviated as TFB, CAS No. 220797-16-0), poly[(N,N'-(4-n-butylphenyl)-N,N'-diphenyl-1,4-phenylenediamine)-ALT-(9,9-di-n-octylfluorenyl-2,7-diyl)] (CAS No. 223569-31-1), 4,4',4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (C AS number is 124729-98-2), 4,4',4"-tri(carbazol-9-yl)triphenylamine (abbreviated as TCTA, CAS number is 139092-78-7), 4,4',4'-tri(2-naphthylphenylamino)triphenylamine (CAS number is 185690-41-9), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as NPB, CAS number is 123847-85-8), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (abbreviated as TPD, CAS No. 65181-78-4), N,N'-bis[4-(diphenylamino)phenyl]-N,N'-diphenylbenzidine (CAS No. 209980-53-0), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirobifluorene-2,7-diamine (abbreviated as Spiro-TPD, CAS No. 1033035-83-4), N2,N7-di-1-naphthyl-N2,N7-diphenyl -9,9'-spirobi[9H-fluorene]-2,7-diamine (CAS No. 932739-76-9), poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTTA, CAS No. 1333317-99-9) and 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (Spiro-omeTAD, CAS No. 207739-72-8) or one or more thereof.

[0123] In some embodiments of the present application, the plurality of functional layers include an electronic functional layer 1033, as described below. Figure 1 , the electronic functional layer 1033 is arranged between the light-emitting layer 1031 and the cathode 102. The electronic functional layer 1033 can be a single-layer structure or a multi-layer structure, and the thickness of the electronic functional layer 1033 is, for example, 10nm to 100nm. When the electronic functional layer 1033 is a multi-layer structure, the electronic functional layer 1033, for example, includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. For the electronic functional layer 1033 including the electron injection layer, the electron transport layer, and the hole blocking layer, the electron transport layer is located between the electron injection layer and the hole blocking layer, and the electron injection layer is closer to the cathode 102 than the hole blocking layer; for the electronic functional layer 1033 including the electron transport layer and the hole blocking layer, the electron transport layer is closer to the cathode 102 than the hole blocking layer; for the electronic functional layer 1033 including the electron injection layer and the electron transport layer, the electron injection layer is closer to the cathode 102 than the electron transport layer. It should be noted that when the electronic functional layer 1033 includes multiple materials and has a multi-layer structure, the multiple materials may all be in the same layer, or respectively in different layers, or partially in the same layer.

[0124] The electron transport layer can be used to smoothly transport electrons. The electron transport material can be a material with high electron mobility, which can skillfully receive electrons injected from the cathode 102 and transfer the electrons to the light-emitting layer 1031. Non-limiting examples of electron transport materials are one or more of an Al complex of 8-hydroxyquinoline, a complex comprising Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), or a benzimidazole-based compound. In principle, all materials that can be used as an electron transport layer of an organic light-emitting diode may be used as an electron transport material for an optoelectronic device in the present application. The electron transport material is selected from one or more of an inorganic electron transport material and an organic electron transport material.

[0125] Among them, the inorganic electron transport material includes but is not limited to one or more of doped metal oxide particles, non-doped metal oxide particles, ceramic semiconductor materials, IIB-VIA semiconductor materials, IIIA-VA semiconductor materials and IB-IIIA-VIA semiconductor materials. The metal oxide in the non-doped metal oxide particles includes but is not limited to one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5. The metal oxide in the doped metal oxide includes but is not limited to one or more of ZnO, TiO2, SnO2, ZrO2, Ta2O5, Al2O3, and the doping elements in the doped metal oxide include but are not limited to one or more of Al, Mg, Li, Mn, Y, La, Cu, Ni, Zr, Ce, In, Ga, Sn. As an example, the doped metal oxide can be aluminum zinc oxide (AZO), lithium-doped zinc oxide (LZO), magnesium-doped zinc oxide (MZO), tin-doped zinc oxide (Sn-ZnO), etc. The ceramic semiconductor material includes but is not limited to barium titanate. The IIB-VIA semiconductor materials include but are not limited to one or more of ZnS, ZnSe, and CdS. The IIIA-VA semiconductor materials include but are not limited to one or more of InP and GaP. The IB-IIIA-VIA semiconductor materials include but are not limited to one or more of CuInS and CuGaS.

[0126] Non-limiting examples of organic electron transport materials are NET-164 (manufactured by Novaled), NDN-87 (manufactured by Novaled), NDN-45 (manufactured by Novaled), NDN-18 (manufactured by Novaled), NDN-218 (manufactured by Novaled), ET093 (manufactured by Idemitsu Kosan), ETM020 (manufactured by Merck), ETM033 (manufactured by Merck), ETM034 (manufactured by Merck), ETM036 (manufactured by Merck), 4,6-bis(3,5-di(pyridin-3-yl)phenyl)-2-methylpyrimidine, 2,9-dimethyl-4,7-biphenyl-1,10-o-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tri(1-phenyl-1H-benzimidazol-2-yl)benzene, 8-hydroxyquinoline aluminum, 8-hydroxyquinoline lithium, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum or more.

[0127] The electron injection layer can be used to smoothly inject electrons. The electron injection material is preferably: having the ability to transmit electrons, having the effect of injecting electrons from the negative electrode, and having an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, preventing the excitons generated by the light-emitting layer from moving to the hole injection layer, and also having an excellent ability to form a thin film. Non-limiting examples of electron injection materials are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc. and one or more of their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives. In principle, all materials that can be used as electron injection layers of organic light-emitting diodes may be used as electron injection materials for optoelectronic devices in this application. Non-limiting examples of electron injection materials are one or more of Yb (ytterbium), yttrium fluoride, Li, LiF, NaF, CsCO3, Cs and KBH4.

[0128] The hole blocking layer is a layer that blocks holes from reaching the cathode, and non-limiting examples of the hole blocking material are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, or aluminum complexes.

[0129] It should be noted that the materials of the hole injection layer, the hole transport layer, the electron transport layer, the electron injection layer, the electron blocking layer and the hole blocking layer are not limited to the materials listed above, and can be selected from conventional materials in the art. Various organic functional materials are described in detail in patent documents WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0130] In the optoelectronic device 10 of the embodiment of the present application, the anode 101 is an electrode for injecting holes, and the anode 101 can easily inject holes into the hole injection layer, or the hole transport layer, or the light-emitting layer. The anode 101 may include one or more of a conductive metal, a conductive metal oxide, or a conductive polymer. In at least one embodiment of the present application, the absolute value of the difference between the work function of the anode 101 and the HOMO energy level or valence band energy level of the luminophore in the light-emitting layer 1031 is less than 0.5 eV, or the absolute value of the difference between the work function of the anode 101 and the HOMO energy level or valence band energy level of the P-type semiconductor material in the hole functional layer (one or more of the hole injection layer, the hole transport layer, or the electron blocking layer) is less than 0.5 eV. Non-limiting examples of the material of the anode 101 are Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, or aluminum-doped zinc oxide (AZO).

[0131] The cathode 102 is an electrode for injecting electrons, and the cathode 102 can easily inject electrons into the electron injection layer, or the electron transport layer, or the light-emitting layer 1031. The cathode 102 may include one or more of a conductive metal, a conductive metal oxide, or a conductive polymer. In at least one embodiment of the present application, the absolute value of the difference between the work function of the cathode 102 and the LUMO energy level or the conduction band energy level of the luminophore in the light-emitting layer 1031 is less than 0.5 eV, or the absolute value of the difference between the work function of the cathode 102 and the LUMO energy level or the conduction band energy level of the N-type semiconductor material in the electron functional layer (one or more of the electron injection layer, the electron transport layer, or the hole blocking layer) is less than 0.5 eV. Non-limiting examples of cathode 102 materials are Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, or ITO.

[0132] It can be understood that the optoelectronic device 10 may also include a substrate, which is arranged on the side of the anode 101 away from the multiple functional layers or the side of the cathode 102 away from the multiple functional layers. The substrate can be a rigid substrate or a flexible substrate. The material of the rigid substrate includes but is not limited to one or more of glass, ceramic and silicon wafer, and the material of the flexible substrate includes but is not limited to one or more of polyimide, polycarbonate, polymethyl methacrylate, polyethylene terephthalate, polyethylene naphthalate and polyether sulfone.

[0133] It should be noted that the preparation methods of each functional layer in the optoelectronic device 10 include but are not limited to chemical methods and / or physical methods. Among them, the chemical method includes but is not limited to one or more of chemical vapor deposition, continuous ion layer adsorption and reaction, anodization, electrolytic deposition and coprecipitation. The physical method includes but is not limited to physical plating and solution method. The physical plating method includes but is not limited to one or more of thermal evaporation coating, electron beam evaporation coating, magnetron sputtering, multi-arc ion plating, physical vapor deposition, atomic layer deposition and pulsed laser deposition. The solution method includes but is not limited to spin coating, printing, inkjet printing, scraping, printing, dip pulling, immersion, spraying, rolling, casting, slit coating and strip coating. After the preparation of each functional layer of the optoelectronic device, a packaging process is required. The packaging process can be carried out by commonly used machine packaging or manual packaging. In the packaging process environment, the oxygen content and water content are both lower than 0.1ppm to ensure the stability of the optoelectronic device. Specifically, the packaging material used to form the packaging layer is selected from one or more of ultraviolet glue, metal film and glass glue. As an example, the packaging material is acrylic resin or epoxy resin.

[0134] Taking the preparation of the light-emitting layer by the solution method as an example, the preparation method of the light-emitting layer includes the steps of: depositing any one of the light-emitting inks described above, and then drying to solidify into a film to obtain the light-emitting layer. The deposition method includes but is not limited to one or more of spin coating, printing, inkjet printing, blade coating, printing, dip-coating, immersion, spraying, roll coating, casting, slit coating and strip coating, and the drying treatment includes but is not limited to one or more of heating and vacuum drying.

[0135] The present application also provides an electronic device, which includes any of the optoelectronic devices described above. The electronic device can be, for example, any electronic product with a display function, including but not limited to a smartphone, a tablet personal computer, a mobile phone, a video phone, an e-book reader, a laptop PC, a netbook computer, a workstation, a server, a personal digital assistant, a portable multimedia player, an MP3 player, a mobile medical machine, a camera, a game console, a digital camera, a car navigation system, an electronic billboard, an ATM, a smart bracelet, a smart watch, a virtual reality (VR) device or a wearable device.

[0136] The technical scheme and technical effects of the present application are described in detail below through specific embodiments, comparative examples and experimental examples. The following embodiments are only some embodiments of the present application and do not specifically limit the present application.

[0137] Material Example 1

[0138] This embodiment provides a luminescent ink. Calculated by mass percentage, the luminescent ink consists of 4% of luminescent material and 96% of organic solvent, wherein the organic solvent is p-methylanisole.

[0139] Calculated by mass percentage, the luminescent material consists of 10% of a first phosphorescent material, 0.1% of a second phosphorescent material and 89.9% of a host material, wherein the first phosphorescent material is Ir(mppy)3 (CAS No. 149005-33-4), and the second phosphorescent material is bis(1,2-diphenyl 1-1H-benzimidazole)iridium(acetylacetonate)[(pbi)2Ir(acac)].

[0140] Calculated by mass percentage, the main material consists of 50% of the first compound and 50% of the second compound, wherein the first compound is the EDM1 compound (CAS number is 1643479-47-3), and the second compound is the EAM1 compound (for details of the synthesis method, see WO2023128513A1).

[0141] Material Example 2

[0142] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in this embodiment is that, calculated by mass percentage, the luminescent material is composed of 10% of a first phosphorescent material, 0.5% of a second phosphorescent material, and 89.5% of a host material. The specific types of the first phosphorescent material, the second phosphorescent material, and the host material are consistent with those in material embodiment 1.

[0143] Material Example 3

[0144] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Example 1, the difference of the luminescent ink in this embodiment is that, calculated by mass percentage, the luminescent material is composed of 10% of a first phosphorescent material, 2% of a second phosphorescent material, and 88% of a host material. The specific types of the first phosphorescent material, the second phosphorescent material, and the host material are consistent with those in Material Example 1.

[0145] Material Example 4

[0146] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Example 1, the difference of the luminescent ink in this embodiment is that, calculated by mass percentage, the luminescent material is composed of 10% of a first phosphorescent material, 4% of a second phosphorescent material, and 86% of a host material. The specific types of the first phosphorescent material, the second phosphorescent material, and the host material are consistent with those in Material Example 1.

[0147] Material Example 5

[0148] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in this embodiment is that the second phosphorescent material is replaced by "Ir(fbi)2(acac) (CAS No. 725251-25-2)".

[0149] Material Example 6

[0150] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Embodiment 1, the difference of the luminescent ink in this embodiment is that the second phosphorescent material is replaced with "Ir(fbi)2(acac) (CAS No. 725251-25-2)", and the luminescent material is composed of 10% of the first phosphorescent material, 0.5% of the second phosphorescent material and 89.5% of the host material in terms of mass percentage. The specific types of the first phosphorescent material and the host material are consistent with those in Material Embodiment 1.

[0151] Material Example 7

[0152] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in this embodiment is that the second phosphorescent material is replaced by "Ir(dmppy-pro)2tmd (CAS No. 2050041-60-4)".

[0153] Material Example 8

[0154] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Embodiment 1, the difference of the luminescent ink in this embodiment is that the second phosphorescent material is replaced with "Ir(dmppy-pro)2tmd (CAS No. 2050041-60-4)", and the luminescent material is composed of 10% of the first phosphorescent material, 0.5% of the second phosphorescent material and 89.5% of the host material according to the mass percentage. The specific types of the first phosphorescent material and the host material are consistent with those in Material Embodiment 1.

[0155] Material Example 9

[0156] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in this embodiment is that the first compound is replaced by EDM3 compound (CAS number is 1548581-42-5), and the second compound is replaced by EAM9 (CAS number is 3025723-32-1).

[0157] Material Example 10

[0158] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in this embodiment is that the first compound is replaced by the EDM2 compound (CAS number is 57102-51-9), and the second compound is replaced by the EAM5 compound (CAS number is 2950259-57-9).

[0159] Material Example 11

[0160] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Embodiment 1, the luminescent ink in this embodiment is different in that the first phosphorescent material is replaced by Ir(ppy)3.

[0161] Material Example 12

[0162] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the first phosphorescent material is replaced by Ir(ppy)2(acac).

[0163] Material Example 13

[0164] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by Ir(Dppy)3.

[0165] Material Example 14

[0166] This embodiment provides a luminescent ink. Compared with the luminescent ink in Material Embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by Ir(Buppy)3.

[0167] Material Example 15

[0168] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by (cbi)2Ir(acac).

[0169] Material Example 16

[0170] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by (tbi)2Ir(acac).

[0171] Material Example 17

[0172] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by fac-Ir(ppy)3.

[0173] Material Example 18

[0174] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by (3-PEC)2Ir(acac).

[0175] Material Example 19

[0176] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the second phosphorescent material is replaced by Ir(mchpy)3.

[0177] Material Example 20

[0178] This embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the luminescent ink in this embodiment is different in that the first compound is replaced by the EDM4 compound (CAS number is 1392844-41-5).

[0179] Material Example 21

[0180] The present embodiment provides a luminescent ink. Compared with the luminescent ink in material embodiment 1, the difference of the luminescent ink in the present embodiment is that the first phosphorescent material is replaced by Ir(hpiq)3 (CAS number is 1240249-29-9), and the second phosphorescent material is replaced by PO-01 (CAS number is 1258323-36-2).

[0181] Material Comparative Example 1

[0182] This comparative example provides a luminescent ink. Compared with the luminescent ink in Material Example 1, the luminescent ink in this comparative example is different in that, calculated by mass percentage, the luminescent material is composed of 10% of a first phosphorescent material and 90% of a host material. The specific types of the first phosphorescent material and the host material are consistent with those in Material Example 1.

[0183] Material Comparative Example 2

[0184] This comparative example provides a luminescent ink. Compared with the luminescent ink in material example 1, the difference of the luminescent ink in this comparative example is that the first compound is replaced by the EDM3 compound (CAS number is 1548581-42-5), and the second compound is replaced by EAM9 (CAS number is 3025723-32-1), and the luminescent material is composed of 10% of the first phosphorescent material (the same as that in material example 1) and 90% of the main material, calculated by mass percentage.

[0185] Material Comparative Example 3

[0186] This comparative example provides a luminescent ink. Compared with the luminescent ink in material example 1, the difference of the luminescent ink in this comparative example is that the first compound is replaced by the EDM2 compound (CAS number is 57102-51-9), and the second compound is replaced by the EAM5 compound (CAS number is 2950259-57-9), and the luminescent material is composed of 10% of the first phosphorescent material (the same as in material example 1) and 90% of the main material, calculated by mass percentage.

[0187] Material Comparative Example 4

[0188] This comparative example provides a luminescent ink. Compared with the luminescent ink in material example 21, the luminescent ink in this comparative example is different in that, calculated by mass percentage, the luminescent material is composed of 10% of a first phosphorescent material and 90% of a host material. The specific types of the first phosphorescent material and the host material are consistent with those in material example 21.

[0189] Device Example 1

[0190] This embodiment provides a photoelectric device and a method for preparing the same. The photoelectric device is an organic light emitting diode having a positive structure, such as Figure 1 As shown, from bottom to top, the optoelectronic device 10 includes an anode 101, a plurality of functional layers 103, a cathode 102, and a light extraction layer 104 stacked in sequence, wherein the plurality of functional layers include a hole functional layer 1032, a light emitting layer 1031, and an electron functional layer 1033 stacked in sequence, wherein the electron functional layer 1033 is closer to the cathode 102 than the hole functional layer 1032. The hole functional layer 1032 is composed of a hole injection layer 10321 and a hole transport layer 10322 stacked in sequence, wherein the hole transport layer 10322 is closer to the light emitting layer 1031 than the hole injection layer 10321; the electron functional layer 1033 is composed of an electron transport layer 10331 and an electron injection layer 10332 stacked in sequence, wherein the electron injection layer 10332 is closer to the cathode 102 than the electron transport layer 10331. The light emitting area of ​​the optoelectronic device 10 is 0.0314 cm 2 .

[0191] The materials and thicknesses of the various layers in the optoelectronic device 10 are as follows:

[0192] The material of the anode 101 is ITO (average thickness of 7 nm) / Ag (average thickness of 110 nm) / ITO (average thickness of 10 nm);

[0193] The material of cathode 102 is Ag, and the average thickness of cathode 102 is 18 nm;

[0194] The hole injection layer 10321 is made of HTM163 material (manufactured by Merck) and NDP-9 material (manufactured by Novaled), the mass ratio of HTM163 material to NDP-9 material is 1:0.08, and the average thickness of the hole injection layer 10321 is 60 nm;

[0195] The material of the hole transport layer 10322 is HTM163 material, and the average thickness of the HTM163 material is 100 nm;

[0196] The light-emitting layer 1031 is made of the light-emitting ink in Material Example 1, and the average thickness of the light-emitting layer 1031 is 55 nm;

[0197] The materials of the electron transport layer 10331 are NET164 material (manufactured by Novaled) and Liq (CAS No. 25387-93-3), the mass ratio of NET164 material: Liq is 2:8, and the average thickness of the electron transport layer 10331 is 24 nm;

[0198] The material of the electron injection layer 10332 is Yb, and the average thickness of the electron injection layer 10332 is 1 nm;

[0199] The material of the light extraction layer 104 is CPL008 material (manufactured by Huarui Optoelectronics), and the average thickness of the light extraction layer 104 is 80 nm.

[0200] The method for preparing the optoelectronic device in this embodiment comprises the following steps:

[0201] S1.1. In a nitrogen glove box, provide a substrate including an anode, deposit a solution including an HTM163 material and an NDP-9 material on one side of the anode, and then place the substrate under a nitrogen atmosphere at 230° C. for 30 min to obtain a hole injection layer;

[0202] S1.2, in a nitrogen glove box, deposit a solution containing HTM163 material on the side of the hole injection layer away from the anode, and then place it in a nitrogen atmosphere at 230° C. for 30 min to obtain a hole transport layer;

[0203] S1.3, in a nitrogen glove box, depositing the luminescent ink in Material Example 1 on the side of the hole transport layer away from the hole injection layer, and then heat treating at a constant temperature of 230° C. in a nitrogen atmosphere to obtain a luminescent layer;

[0204] S1.4, transfer the prefabricated device completed in step S1.3 to a vacuum chamber with a degree of vacuum of 9×10 -7 In a vacuum chamber of 100 torr, a mixed material consisting of NET164 and Liq is deposited on the side of the light-emitting layer away from the hole transport layer to obtain an electron transport layer;

[0205] S1.5, evaporating Yb on the side of the electron transport layer away from the light-emitting layer to obtain an electron injection layer;

[0206] S1.6, evaporating Ag on the side of the electron injection layer away from the electron transport layer to obtain a cathode;

[0207] S1.7. Evaporate CPL008 material on the side of the cathode away from the electron injection layer to form a light extraction layer to obtain a photoelectric device.

[0208] Device Example 2

[0209] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 2.

[0210] Device Example 3

[0211] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 3.

[0212] Device Example 4

[0213] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the photoelectric device in this embodiment is different in that: the light-emitting layer is prepared by using the light-emitting ink in material embodiment 4.

[0214] Device Example 5

[0215] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the photoelectric device in this embodiment is different in that: the light-emitting layer is prepared by using the light-emitting ink in material embodiment 5.

[0216] Device Example 6

[0217] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 6.

[0218] Device Example 7

[0219] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 7.

[0220] Device Example 8

[0221] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 8.

[0222] Device Example 9

[0223] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the photoelectric device in this embodiment is different in that: the light-emitting layer is prepared by using the light-emitting ink in material embodiment 9.

[0224] Device Example 10

[0225] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 10.

[0226] Device Example 11

[0227] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 11.

[0228] Device Example 12

[0229] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 12.

[0230] Device Example 13

[0231] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 13.

[0232] Device Example 14

[0233] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 14.

[0234] Device Example 15

[0235] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 15.

[0236] Device Example 16

[0237] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 16.

[0238] Device Example 17

[0239] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 17.

[0240] Device Example 18

[0241] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 18.

[0242] Device Example 19

[0243] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 19.

[0244] Device Example 20

[0245] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 20.

[0246] Device Example 21

[0247] This embodiment provides a photoelectric device. Compared with the photoelectric device in device embodiment 1, the difference of the photoelectric device in this embodiment is that the light-emitting layer is prepared by using the light-emitting ink in material embodiment 21, and the average thickness of the hole injection layer is replaced by "120nm".

[0248] Device Comparison Example 1

[0249] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the difference of the photoelectric device in this comparative example is that the light-emitting layer is prepared by using the light-emitting ink in material comparative example 1.

[0250] Device Comparison Example 2

[0251] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the difference of the photoelectric device in this comparative example is that the light-emitting layer is prepared by using the light-emitting ink in material comparative example 2.

[0252] Device Comparison Example 3

[0253] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the photoelectric device in this comparative example is different in that the light-emitting layer is prepared by using the light-emitting ink in material comparative example 3.

[0254] Device Comparison Example 4

[0255] This comparative example provides a photoelectric device. Compared with the photoelectric device in device example 1, the photoelectric device in this comparative example is different in that the light-emitting layer is prepared by using the light-emitting ink in material comparative example 4.

[0256] It should be noted that the LUMO energy levels and HOMO energy levels of the first phosphorescent material and the second phosphorescent material in Material Example 1, Material Example 5, Material Example 7, Material Example 11 to Material Example 19 and Material Example 21 are shown in Table 1 below:

[0257] Table 1

[0258]

[0259] Experimental example

[0260] The performance of the optoelectronic devices in device examples 1 to device examples 21, device comparative examples 1 and device comparative examples 4 was tested. The current-voltage (JV) characteristics of each optoelectronic device were tested using IVL optical property measurement equipment, and important parameters were recorded: CIE color coordinates (x, y), current efficiency at a brightness of 1000 nit (CE@1000nit, cd / A), current density of 10 mA / cm 2 Device voltage (U@10mA / cm 2 ,V) and device life (T95,h). The performance test was carried out in an environment with a temperature of 25℃ and a humidity of 40%. The performance test results are shown in Table 2 below:

[0261] Table 2

[0262]

[0263] It can be seen from Table 2 that compared with the comprehensive performance of the optoelectronic devices in device comparison examples 1 to 4, the comprehensive performance of the optoelectronic devices in device examples 1 to 21 has significant advantages, specifically: the color purity and device efficiency of the optoelectronic devices in device examples 1 to 21 are better, and they have good device life and lower operating voltage. The reason is that: the second phosphorescent material is introduced into the light-emitting layer as a dopant, which has a carrier trap effect, can promote carrier transport balance, and improve the position of the carrier recombination zone through electrical balance, which is beneficial to improving the device efficiency of the optoelectronic device; in addition, since the second phosphorescent material has a high degree of overlap with the first phosphorescent material, it will not have a negative impact on the device efficiency and color purity of the optoelectronic device.

[0264] The above is a detailed introduction to a composition, luminescent material, luminescent ink and optoelectronic device provided in the embodiments of the present application. 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 technical solution and its core idea of ​​the present application; ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or replace some of the technical features therein with equivalents; and these modifications or replacements do not make the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A composition, characterized in that The composition includes a first phosphorescent material and a second phosphorescent material, the absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01eV, and the absolute value of the difference between the LUMO energy level of the first phosphorescent material and the LUMO energy level of the second phosphorescent material is not greater than 0.3eV.

2. The composition according to claim 1, characterized in that The absolute value of the difference between the HOMO energy level of the first phosphorescent material and the HOMO energy level of the second phosphorescent material is greater than or equal to 0.01 eV and less than or equal to 0.5 eV; and / or The absolute value of the LUMO energy level of the second phosphorescent material is not greater than the absolute value of the LUMO energy level of the first phosphorescent material; and / or The mass ratio of the second phosphorescent material to the first phosphorescent material is 1:(1-150); and / or The photoluminescence peak of the first phosphorescent material is 500nm to 650nm; and / or The photoluminescence peak of the second phosphorescent material is 500nm to 650nm; and / or The absolute value of the difference between the photoluminescence peak position of the first phosphorescent material and the photoluminescence peak position of the second phosphorescent material is no greater than 40 nm; and / or The first phosphorescent material and the second phosphorescent material are independently selected from iridium complexes represented by the general formula Ir-(L1)(L2)(L3), wherein L1, L2 and L3 are independently selected from any one of the following structural formulas: wherein Ar1 to Ar3 are independently selected from an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted by at least one R, or a combination of these groups; R1 to R3 are independently selected from -H, -D, C1-C30 aliphatic chain hydrocarbon group, C1-C30 aliphatic chain hydrocarbon oxy group, unsubstituted or substituted by at least one R aryl group with 6 to 40 ring atoms, unsubstituted or substituted by at least one R heteroaryl group with 5 to 40 ring atoms, unsubstituted or substituted by at least one R aliphatic cycloalkyl group with 5 to 40 ring atoms, substituted or substituted by at least one R aliphatic heterocycloalkyl group with 5 to 40 ring atoms, amino, halogen group, hydroxyl, carboxyl, nitro, sulfonic acid group, aldehyde group, carbonyl, thiol, cyano group, or a combination of these groups; Each occurrence of R is independently selected from -H, -D, a C1-C10 aliphatic chain hydrocarbon group, a C1-C10 aliphatic chain hydrocarbon oxy group, an aryl group having 6 to 20 ring atoms, a heteroaryl group having 5 to 20 ring atoms, an aliphatic cycloalkyl group having 3 to 30 ring atoms, an aliphatic heterocycloalkyl group having 3 to 30 ring atoms, an amino group, a halogen group, a hydroxyl group, a carboxyl group, a nitro group, a sulfonic acid group, an aldehyde group, a carbonyl group, a mercapto group, a cyano group, or a combination of these groups; The heteroatoms in the aliphatic heterocyclic hydrocarbon group are independently selected from one or more of N, S, O, P and Si, and the number of heteroatoms in the aliphatic heterocyclic hydrocarbon group is independently 1 to 20; * indicates the connection site between L1, L2 or L3 and Ir.

3. The composition according to claim 1 or 2, characterized in that The first phosphorescent material and the second phosphorescent material are independently selected from green phosphorescent materials, the first phosphorescent material is selected from one or more of Ir(mppy)3, Ir(ppy)3 and Ir(ppy)2(acac), and the second phosphorescent material is selected from one or more of Ir(Dppy)3, Ir(Buppy)3, (pbi)2Ir(acac), (cbi)2Ir(acac), (tbi)2Ir(acac), Ir(fbi)2(acac), Ir(dmppy-pro)2tmd, fac-Ir(ppy)3, (3-PEC)2Ir(acac), Ir(mchpy)3, Ir(pbi)2(acac) and Ir(BPPya)3; Alternatively, the first phosphorescent material and the second phosphorescent material are independently selected from red phosphorescent materials, the first phosphorescent material is selected from one or more of Ir(piq)2acac, Ir(pcpiq)2acac, Ir(hpiq)3 and Ir(piq)3, and the second phosphorescent material is selected from one or more of (pq)2Ir(acac), (bpiq)2Ir(acac), (ppz)2Ir(piq), Ir(btp)2(acac), Ir(2-phq)2(acac), Ir(bt)2(acac), acetylacetonate di(4-phenyl-thiophene[3,2-c]pyridine-C2,N)iridium(III) and acetylacetonate di(4-(4-tert-butyl-phenyl)-thiophene[3,2-c]pyridine-C2,N)iridium(III).

4. A luminescent material, characterized in that: The light-emitting material comprises a host material and a guest material, and the guest material comprises the composition as claimed in any one of claims 1 to 3.

5. The luminescent material according to claim 4, characterized in that The host material is a green phosphorescent host material, and the first phosphorescent material and the second phosphorescent material are independently selected from green iridium complexes; or, the host material is a red phosphorescent host material, and the first phosphorescent material and the second phosphorescent material are independently selected from red iridium complexes; and / or Calculated by mass percentage, the luminescent material includes 81% to 95.9% of the host material and 4.1% to 19% of the guest material; and / or The mass of the first phosphorescent material accounts for 4% to 15% of the total mass of the luminescent material; and / or The mass of the second phosphorescent material accounts for 0.1% to 4% of the total mass of the luminescent material; and / or The host material includes a first compound having a structure shown in the following general formula (I): In the general formula (I), Ar4 is selected from an aryl group having 6 to 60 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 3 to 60 ring atoms which is unsubstituted or substituted by at least one R, or a combination of these groups; A is an electron-rich group; n1 is selected from any integer of 1 to 6; when n1 is greater than 1, the multiple electron-rich groups are the same or different; and / or The host material includes a second compound, and the second compound has a structure shown in the following general formula (II): In the general formula (II), Ar5 is selected from an unsubstituted or at least R substituted aryl group having 6 to 60 ring atoms, an unsubstituted or at least R substituted heteroaryl group having 3 to 60 ring atoms, or a combination of these groups; E is an electron-deficient group; n2 is selected from any integer from 1 to 6; when n1 is greater than 1, the multiple electron-deficient groups are the same or different.

6. The luminescent material according to claim 5, characterized in that A has one or more of the following structures: wherein Ar6 is selected from an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 3 to 40 ring atoms which is unsubstituted or substituted by at least one R, or a combination of these groups; Y1 and Y2 are independently selected from a single bond, N(R 12 )、C(R 13 R 14 )、Si(R 15 R 16 )、O、S、C=N(R 17 )、C=C(R 18 R 19 ) or P(R 20 ); R4 to R 20 Each of the following groups is independently selected from -H, -D, a C1-C30 aliphatic chain hydrocarbon group, a C1-C30 aliphatic chain hydrocarbonoxy group, an aryl group having 6 to 60 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 60 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted by at least one R, or a combination of these groups; and / or E is selected from F, cyano or one or more of the following structures: Wherein, a is 1, 2 or 3; Each time X appears, it is independently selected from C, CR 27 or N, and at least one of them is N; M 1 、M 2 and M 3 are independently selected from N(R 28 )、C(R 29 R 30 )、Si(R 31 R 32 )、O、C=N(R 33 )、C=C(R 34 R 35 ), P(R 36 )、P(=O)R 37 , S, S=O, SO2 or none; R 21 To R 37 Each of the following groups is independently selected from -H, -D, a C1-C30 aliphatic chain hydrocarbon group, a C1-C30 aliphatic chain hydrocarbon oxy group, an aryl group having 6 to 40 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic cycloalkyl group having 3 to 40 ring atoms which is unsubstituted or substituted by at least one R, an aliphatic heterocycloalkyl group having 3 to 40 ring atoms which is substituted or substituted by at least one R, or a combination of these groups.

7. The luminescent material according to claim 5 or 6, characterized in that: The first compound has a structure shown in the following formula (1-1): And / or, the second compound has a structure shown by the following general formula (2-2): Among them, Ar7 to Ar 11 are selected from an aryl group having 6 to 60 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 60 ring atoms which is unsubstituted or substituted by at least one R, or a combination of the foregoing groups; In the general formula (I), Z, when present, is independently selected from C or CR 39 , R 39 Each occurrence is independently selected from -H, -D, C1-C30 aliphatic chain hydrocarbon group, C1-C30 aliphatic chain hydrocarbon oxy group, unsubstituted or substituted with at least one R aryl group with 6 to 30 ring atoms, unsubstituted or substituted with at least one R heteroaryl group with 5 to 30 ring atoms, or a combination of the foregoing groups, and two adjacent R 39 They may or may not form a ring with each other; R 38 is a single bond, or R 38 The invention is selected from a C1-C30 aliphatic chain alkylene group, a C1-C30 aliphatic chain alkylene oxy group, an unsubstituted or at least one R substituted arylene group having 6 to 30 ring atoms, an unsubstituted or at least one R substituted heteroarylene group having 5 to 30 ring atoms, or a combination of the foregoing groups.

8. The luminescent material according to claim 7, characterized in that Ar7 is selected from an aryl group having 6 to 14 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 14 ring atoms which is unsubstituted or substituted by at least one R, or a combination of the foregoing groups; and / or The Ar8 has a structure shown in the following formula (1-a): Among them, Ar 12 The group selected from an alkyl group having 1 to 30 ring atoms which is unsubstituted or substituted by at least one R, an alkoxy group having 1 to 30 ring atoms which is unsubstituted or substituted by at least one R, a cycloalkyl group having 3 to 30 ring atoms which is unsubstituted or substituted by at least one R, an aryl group having 6 to 60 ring atoms which is unsubstituted or substituted by at least one R, a heteroaryl group having 5 to 60 ring atoms which is unsubstituted or substituted by at least one R, or a combination of the foregoing groups, and * represents a connection site.

9. The luminescent material according to claim 8, characterized in that Ar7 is selected from phenyl, phenyl substituted by at least one C1-C30 aliphatic chain hydrocarbon group, naphthyl, biphenyl, terphenyl, anthracenyl, phenanthrenyl, 9,9-dimethylfluorenyl, or dibenzofuranyl; and / or The Ar 12 is selected from phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, terphenyl or triphenylene; and / or The first compound is selected from one or more of the following compounds:

10. The luminescent material according to claim 7, characterized in that Ar9 to Ar 11 Each independently represents a group represented by any of the following structural formulas: Wherein, each occurrence of X1, X2 or X3 is independently selected from C or CR 40 , R 40 Each occurrence is independently selected from -H, -D, aryl having 6 to 20 ring atoms which is unsubstituted or substituted by at least one R, heteroaryl having 5 to 20 ring atoms which is unsubstituted or substituted by at least one R, or a combination of the foregoing; In the general formula (2-a), Ar 13 Does not exist, or Ar 12 is selected from an unsubstituted or substituted arylene group having 6 to 20 ring atoms, an unsubstituted or substituted heteroarylene group having 5 to 20 ring atoms, or a combination of the foregoing groups; In the general formula (2-b), Ar 14 The group is selected from an unsubstituted or substituted aryl group having 6 to 20 ring atoms, an unsubstituted or substituted heteroaryl group having 5 to 20 ring atoms, or a combination of the foregoing groups.

11. The luminescent material according to claim 10, characterized in that The second compound is selected from one or more of the following compounds:

12. The luminescent material according to claim 5, characterized in that The main material consists of the first compound and the second compound, and the mass ratio of the first compound to the second compound is 1:(0.1-9).

13. A luminous ink, characterized in that: The luminescent ink comprises the composition as claimed in any one of claims 1 to 3, or the luminescent material as claimed in any one of claims 4 to 12; The luminescent ink also includes at least one first organic solvent; optionally, the first organic solvent is selected from one or more of aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate ester compounds and phosphate ester compounds.

14. A photoelectric device, characterized in that: include: An anode and a cathode arranged opposite to each other; as well as A plurality of functional layers are disposed between the anode and the cathode; Among them, the material of at least one of the multiple functional layers includes the composition described in any one of claims 1 to 3, or the luminescent material described in any one of claims 4 to 12, or at least one of the multiple functional layers is prepared using the luminescent ink described in claim 13.

15. The optoelectronic device according to claim 14, characterized in that: The multiple functional layers include a light-emitting layer, the material of the light-emitting layer includes the composition described in any one of claims 1 to 3, or the light-emitting material described in any one of claims 4 to 12, or the light-emitting layer is prepared using the light-emitting ink described in claim 13; and / or the optoelectronic device is an organic light-emitting diode; optionally, the optoelectronic device is a green organic light-emitting diode or a red organic light-emitting diode.

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