Mixture, composition, organic compound constituting same, and use thereof in organic electronic device

Abstract

Disclosed in the present invention is a mixture, comprising at least one first compound H1 represented by formula (I) or formula (III), and at least one second compound H2 represented by formula (II). The mixture according to the present invention, as a phosphorescent light-emitting host material, can properly balance hole and electron transport and prevent exciton diffusion, thereby improving the efficiency of a blue phosphorescent device and prolonging the device life. The present invention further relates to a composition and an organic electronic device, particularly an organic electroluminescent device. The present invention further relates to an organic compound, comprising an aza or non-aza oxygen-containing fused ring and 3,9'-bicarbazole, wherein the oxygen-containing fused ring and the 3,9'-bicarbazole portions are linked via a single bond or a bridging group. Due to the relatively high stability and appropriate energy level characteristics, the organic compound can be used as a non-luminescent material of a blue phosphorescent OLED to improve device performance.

Description

A mixture, a composition comprising the same, an organic compound constituting the same, and use thereof in an organic electronic device TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electronic materials and devices, and in particular to a mixture, a composition comprising the same, use thereof in an organic electronic device, and an organic compound constituting the same. BACKGROUND

[0002] Organic semiconductor materials have the characteristics of rich structural diversity, relatively low manufacturing cost, and superior optoelectronic performance, and have great potential in the application of optoelectronic devices such as organic light-emitting diodes (OLEDs) in flat panel displays and lighting.

[0003] In order to improve the light-emitting performance of organic light-emitting diodes and promote the large-scale industrialization process of organic light-emitting diodes, various types of organic optoelectronic performance material systems have been widely developed. However, the performance of OLEDs, especially the lifetime, still needs to be further improved; high-efficiency stable organic optoelectronic performance materials and their combinations are urgently needed to be developed. Among them, the development of excellent blue light materials has long been recognized as a great challenge. In particular, blue phosphor OLEDs, which can achieve nearly 100% internal quantum efficiency (significantly higher than the theoretical limit of blue fluorescent systems), are widely considered as the next generation of high-performance blue OLED technology solutions that are expected to replace fluorescent material systems in recent years and have attracted widespread attention.

[0004] The existing blue phosphor organic electroluminescent element light-emitting layer adopts a host-guest doping structure, and one of the more effective host materials is based on 3,9'-biscarbazole derivatives, as described in patents WO2009086028 and WO2012048266. On the other hand, there is a tendency to design a mixed host with bipolar transmission as a double host material to benefit the balance of charge transport. Blue phosphor OLEDs using multiple host materials are disclosed in documents Nat. Photonics 16, 212-218 (2022) and patent US20220251121, in which the P-type host material contains a compound with a 3,9'-biscarbazole structure, but the performance and lifetime of the obtained device still need to be continuously improved.

[0005] In addition, an effective blocking layer is usually needed to be introduced in the blue phosphorescent OLED scheme to ensure the reliable performance of the device; the blocking layer material on the hole transport side is usually selected from the same type of compound as the P-type host to achieve effective hole transport and exciton blocking; this layer structure has a significant impact on the efficiency and lifetime of the blue phosphorescent OLED device. However, the compounds in the existing disclosed schemes still have deficiencies in energy level and stability, etc., resulting in the corresponding devices still having the problem that the driving power consumption, luminous efficiency and lifetime are difficult to achieve a good balance, which is difficult to meet the requirements of industrial applications.

[0006] In order to meet the requirements of practical application, it is necessary to develop new host material combinations and corresponding new P-type compounds. SUMMARY

[0007] Based on this, in view of the deficiencies of the prior art described above, the purpose of the present application is to provide a mixture, an organic compound, a composition comprising the same and an organic electronic device. It aims to solve the problem of low luminous efficiency and device lifetime of the existing organic electronic device.

[0008] The technical scheme of the present application is as follows:

[0009] A mixture, comprising a first compound H1, and a second compound H2, wherein the first compound H1 has a structure as shown in general formula (I) or general formula (III):

[0010] Wherein:

[0011] X1 is selected from O, S or Se;

[0012] Y1-Y4 are selected from N or CR 16 ;

[0013] Ar is selected from a substituted or unsubstituted aromatic group having 6-30 ring atoms or a heteroaromatic group having 2-30 ring atoms;

[0014] R1-R 16independently from each other selected from H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group with 3 to 20 C atoms, or a keto group with 1 to 20 C atoms, or an alkoxycarbonyl group with 2 to 20 C atoms, or an aryloxycarbonyl group with 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group with 5 to 40 ring atoms, or a combination of these groups; one or more H in the various groups mentioned above can be further replaced by D;

[0015] L1is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group with 6 to 30 ring atoms;

[0016] A1is selected from a substituted or unsubstituted heteroaromatic group with 8 to 40 ring atoms, or a heteroaryloxy group with 8 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a mono- or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bound, and A1contains at least one O, S or Se hetero ring atom; at least one of the hetero ring atoms in X1and A1is selected from O; when both are selected from O, the ring atoms of A1do not contain N; when one of them is O and the other is selected from S, Se, then at least one of the ring atoms of A1and Y1-Y4is selected from N;

[0017] the second compound H2has the structure according to general formula (II):

[0018] wherein:

[0019] Z1-Z3are selected from N or CR 17 , and at least one of them is selected from N;

[0020] L2-L4are defined as L1above;

[0021] Ar1-Ar3are independently from each other selected from one of the groups according to general formula (II-1) to (II-7):

[0022] wherein:

[0023] " " indicates the position of the bond;

[0024] W1-W2are selected from O, S or Se;

[0025] m1 is an integer from 0 to 3, m2 is an integer from 0 to 4, and m3 is an integer from 0 to 5;

[0026] R 1 -R 17 R1is as defined above.

[0027] The present application also provides a composition comprising a mixture as described above and at least one organic solvent.

[0028] The present application also provides an organic electronic device comprising at least one mixture as described above.

[0029] The present application further provides an organic compound having a structure as shown in general formula (I-A) or (I-B) or (III-A) or (III-B):

[0030] wherein:

[0031] X1, X2, X3are independently selected from O, S or Se, and at least one of X1, X2in general formula (I-A) or (III-A) is O, and at least one of X1, X3in general formula (I-B) or general formula (III-B) is O;

[0032] Y1-Y8are selected from N or CR 16 ;

[0033] when X1, X2, X3are all O, Y1-Y8are all selected from CR 16 ; when X1and X2are different from O, or X1and X3are different from O, at least one of Y2, Y3, Y6and Y7is selected from N;

[0034] L1is selected from a single bond, or a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 30 ring atoms;

[0035] Ar is selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group having 2 to 30 ring atoms;

[0036] R is a substituent independently selected from D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above-mentioned groups can be further replaced by D;

[0037] R1-R 16 are each independently selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above-mentioned groups can be further replaced by D.

[0038] Beneficial effects: The mixture according to the present application comprises a first compound H1 and a second compound H2 capable of forming a complexed excited state, and the first compound H1 and the second compound H2 can effectively form an exciplex, thereby enabling efficient formation of triplet excitons in an electroluminescent device and enabling the device to have a relatively ideal electron-hole balance. The mixture according to the present application can be used as an electrophosphorescent co-host material, and by cooperating with a suitable guest material, the luminous efficiency and the lifetime of an organic electroluminescent device can be improved, thereby providing a material solution for a high-efficiency and long-lifetime light-emitting device.

[0039] The organic compound according to the present application has a high triplet excited state energy level and a strong hole transport ability, and can be used as a barrier layer material for preparing an organic electronic device, in particular a blue organic electroluminescent element, in which the excitation state-polaron quenching phenomenon is inhibited by effectively limiting the exciton distribution in the light-emitting layer, thereby obtaining a high efficiency and a long device lifetime. DETAILED DESCRIPTION

[0040] For the purposes of this disclosure, reference will be made to the accompanying drawings which form a part of the specification. The drawings are for illustrative purposes and are not intended to limit the application as encompassed by the claims. Embodiments of the application will be disclosed with additional specificity and detail through use of the accompanying drawings in which:

[0041] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used in the description of the application herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety.

[0042] In the description of embodiments of the present application, the numerical range represented by "~" means a range including the numerical values written before and after "~" as lower limit values and upper limit values.

[0043] In the description of embodiments of the present application, a substituent group can be further substituted by a substituent group, and "substituted group a" can mean that group a is substituted by a substituent group, which can be substituted by at least one further substituent group or unsubstituted.

[0044] In the present application, the term "and / or" describes the association relationship of the associated objects, which means that there can be three kinds of relationships, for example, A and / or B can mean that A exists alone, A and B exist together, and B exists alone. Wherein A and B can be singular or plural. The character " / " generally represents that the associated objects before and after it are in an "or" relationship.

[0045] In the present application, "at least one" means one or more, and "multiple" means two or more. "At least one of the following" or the like means any combination of these items, including any combination of single item or multiple items. For example, "at least one of a, b, or c", or "at least one of a, b, and c", can mean a, b, c, a-b (i.e. a and b), a-c, b-c, or a-b-c, wherein a, b, and c can be single or multiple.

[0046] It should be understood that the size of the sequence number of each process described above in various embodiments of the present application does not mean the order of execution, and part or all of the steps can be executed in parallel or in sequence. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present application.

[0047] The terminology used in the description of the application herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used in the description of the application and the appended claims, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0048] The term "OLED" is the abbreviation of "Organic Light Emitting Diode", which means organic electroluminescent diode, also known as organic electroluminescent display, organic light-emitting semiconductor (Organic Electroluminescence Display, OLED). OLED is a current type of organic light-emitting device, which is a phenomenon of light emission by injection and recombination of carriers. The light emission intensity is proportional to the injected current. Under the action of electric field, the holes generated by the anode and the electrons generated by the cathode will move and inject into the hole transport layer and the electron transport layer, respectively, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, thereby exciting light-emitting molecules to finally produce visible light.

[0049] The term "TADF" is the abbreviation of "Thermally Activated Delayed Fluorescence", which means thermally activated delayed fluorescence. When the energy of the triplet excited state is close to that of the singlet excited state, the triplet excited state can be transferred to the singlet excited state through thermally activated reverse intersystem crossing. Traditional luminescence is fluorescence and phosphorescence, which are singlet and triplet excitons, respectively, in the form of radiative luminescence back to the ground state. Moreover, the energy level difference between the lower singlet and the lower triplet is generally large, so that the exciton cannot return to the singlet state after reaching the triplet state through intersystem crossing ISC process.

[0050] In the present application, the host material, matrix material, Host material and Matrix material have the same meaning and can be interchanged.

[0051] In the present application, the P-type host, hole-type host, hole transport type host, hole-type compound have the same meaning and can be interchanged; the N-type host, electron-type host, electron transport type host, electron-type compound have the same meaning and can be interchanged.

[0052] In the present application, the metal organic complex, metal organic complex, organic metal complex have the same meaning and can be interchanged.

[0053] In the present application, the energy level structure of the organic material, the singlet energy level E S1 , the triplet energy level E T1 , HOMO, LUMO plays a key role. The following describes the confirmation of these energy levels.

[0054] HOMO and LUMO energy levels can be measured by photoelectric effect, for example XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereinafter CV). Recently, quantum chemical methods, for example density functional theory (hereinafter DFT), have also become a valid method to calculate the molecular orbital energy levels.

[0055] Singlet energy level E S1 Triplet energy level E T1 Singlet energy level E S1 Triplet energy level E T1 Also by quantum simulation calculation, for example by Time-dependent DFT, for example by the commercial software Gaussian 09W (Gaussian Inc.), see WO2011141110 for the specific simulation method. ΔE ST defined as (E S1 -E T1 ).

[0056] It should be noted that the absolute values of HOMO, LUMO, E S1 , E T1 depend on the used measurement or calculation method, and even for the same method, different evaluation methods, for example the starting point and the peak point on the CV curve can give different HOMO / LUMO values. Therefore, a reasonable and meaningful comparison should be made with the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the values of HOMO, LUMO, E S1 , E T1 are based on the simulation of Time-dependent DFT, but the application of other measurement or calculation methods is not affected.

[0057] In the present application, (HOMO-1) is defined as the second highest occupied orbital energy level, (HOMO-2) is the third highest occupied orbital energy level, and so on. (LUMO+1) is defined as the second lowest unoccupied orbital energy level, (LUMO+2) is the third lowest unoccupied orbital energy level, and so on.

[0058] In the present application, ΔHOMO is defined as the energy value of HOMO-(HOMO-1), and ΔLUMO is defined as the energy value of (LUMO+1)-(LUMO).

[0059] The present application provides a mixture comprising a first compound H1, and a second compound H2, wherein the first compound H1 has a structure as shown in general formula (I) or general formula (III):

[0060] wherein: X1is selected from O, S or Se; Y1-Y4are selected from N or CR 16 ; Ar is selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group having 2 to 30 ring atoms;

[0061] R1-R 16 are each independently selected from H, D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in the various groups mentioned above can also be further replaced by D;

[0062] L1is selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group;

[0063] A1is selected from a substituted or unsubstituted heteroaromatic group having 8 to 40 ring atoms, or a heteroaryloxy group having 8 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded, and A1contains at least one O, S or Se hetero ring atom; the hetero ring atoms in X1and A1are at least one selected from O; when both are selected from O, the ring atoms of A1do not contain N; when one of them is O and the other is selected from S, Se, then at least one of the ring atoms of A1and Y1-Y4is selected from N;

[0064] the second compound H2has a structure as shown in general formula (II):

[0065] wherein:

[0066] Z1-Z3are selected from N or CR 17 , and wherein at least one is selected from N; L2-L4are defined as above for L1; Ar1-Ar3are each independently selected from one of the groups shown in general formula (II-1) to general formula (II-7):

[0067] wherein: "*" indicates the position of the bond; W1-W2 is selected from O, S or Se; m1 is an integer from 0 to 3, m2 is an integer from 0 to 4, and m3 is an integer from 0 to 5; R 1 -R 17 R1is as defined above.

[0068] In a preferred embodiment, the mixture, the first compound H1 and / or the second compound H2 is partially deuterated, preferably 10% and more of the H are replaced by deuterium, more preferably 20% and more of the H are replaced by deuterium, very preferably 30% and more of the H are replaced by deuterium, most preferably 40% and more of the H are replaced by deuterium.

[0069] In another preferred embodiment, the mixture, the first compound H1 is partially deuterated, preferably 10% and more of the H are replaced by deuterium, more preferably 20% and more of the H are replaced by deuterium, very preferably 30% and more of the H are replaced by deuterium, most preferably 40% and more of the H are replaced by deuterium.

[0070] In a preferred embodiment, the mixture according to the present application is used in an evaporation type OLED device. For this purpose, the first compound H1 and / or the second compound H2 according to the present application has a molecular weight of < 1000 g / mol, preferably < 900 g / mol, more preferably < 850 g / mol, even more preferably < 800 g / mol, most preferably < 700 g / mol.

[0071] In certain preferred embodiments, the mixture according to the present application, wherein at least one of the first compound H1 and the second compound H2 has a ΔLUMO > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0072] In certain preferred embodiments, the mixture according to the present application, wherein at least one of the first compound H1 and the second compound H2 has a ΔHOMO > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0073] In a preferred embodiment, the mixture according to the present application, wherein the first compound H1 has a ΔHOMO > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0074] In a preferred embodiment, the mixture according to the present application, wherein ΔLUMO of the second compound H2 is > 0.2 eV, preferably > 0.25 eV, more preferably > 0.3 eV, even more preferably > 0.35 eV, very preferably > 0.4 eV, most preferably > 0.45 eV.

[0075] In a preferred embodiment, the mixture according to the present application, wherein the first compound H1 and the second compound H2 have a type II semiconductor heterojunction, and the first compound H1 comprises a structure according to formula (I) or formula (III), and min[LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1)] < min[E T1 (H1), E T1 (H2)] + 0.1 eV, wherein LUMO(H1), HOMO(H1) and E T1 (H1) are the lowest unoccupied molecular orbital, the highest occupied molecular orbital and the triplet energy level of the first compound H1, respectively, LUMO(H2), HOMO(H2) and E T1 (H2) are the lowest unoccupied molecular orbital, the highest occupied molecular orbital and the triplet energy level of the second compound H2, respectively. Ex = min[LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1)] is defined as follows, preferably Ex < min[E T1 (H1), E T1 (H2)]; more preferably Ex < min[E T1 (H1), E T1 (H2)] - 0.1 eV; most preferably Ex < min[E T1 (H1), E T1 (H2)] - 0.2 eV.

[0076] In a preferred embodiment, the mixture according to the present application, wherein the molar ratio of the first compound H1 and the second compound H2 is from 1 :9 to 9:1, preferably from 2:8 to 8:2, more preferably from 3:7 to 7:3, even more preferably from 4:6 to 6:4.

[0077] In a preferred embodiment, the mixture according to the present application, wherein the difference between the molecular weight of the first compound H1 and the second compound H2 is not more than 100 Dalton, preferably not more than 80 Dalton, more preferably not more than 70 Dalton, even more preferably not more than 60 Dalton, very preferably not more than 40 Dalton, most preferably not more than 30 Dalton.

[0078] In another preferred embodiment, the mixture, wherein the difference in sublimation temperature of the first compound H1 and the second compound H2 is not more than 50 K, more preferably the difference in sublimation temperature is not more than 30 K, even more preferably the difference in sublimation temperature is not more than 20 K, most preferably the difference in sublimation temperature is not more than 10 K.

[0079] In a preferred embodiment, at least one of the first compound H1 and the second compound H2 in the mixture according to the present application has a glass transition temperature (Tg) > 100 °C; in a more preferred embodiment, at least one has a Tg > 120 °C; in an even more preferred embodiment, at least one has a Tg > 140 °C; in a further even more preferred embodiment, at least one has a Tg > 160 °C; in a most preferred embodiment, at least one has a Tg > 180 °C.

[0080] The term "small molecule" as defined herein refers to a molecule which is not a polymer, oligomer, dendrimer, or blend. In particular, small molecules do not have repeating structures. Small molecules have a molecular weight < 3000 g / mol, more preferably < 2000 g / mol, most preferably < 1500 g / mol.

[0081] In certain preferred embodiments of the first compound H1 in the mixture described above, X1 is selected from O or S, most preferably O; Y1-Y4 are selected from N or CH or CD. In certain preferred embodiments, Y1-Y4 are selected from N or CH or CD, wherein the number of selections from N is < 2, and no adjacent positions are selected from N.

[0082] In certain preferred embodiments, R1-R 16 are each independently selected from H, D, or a linear alkyl, alkoxy, or thioalkoxy group having 1 to 15 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 15 C atoms, or a keto group having 1 to 15 C atoms, or an alkoxycarbonyl group having 2 to 15 C atoms, or an aryloxycarbonyl group having 7 to 15 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups; one or more H in each of the aforementioned groups can be further replaced by D.

[0083] In other preferred embodiments, R1-R 16independently from each other selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 10 C atoms, or a keto group having 1 to 10 C atoms, or an alkoxycarbonyl group having 2 to 10 C atoms, or an aryloxycarbonyl group having 7 to 10 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 20 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups; one or more H in each of the above mentioned groups can be further replaced by D.

[0084] In certain more preferred embodiments, R1-R 16 independently from each other selected from H or D, or a substituted or unsubstituted benzene ring, carbazole, dibenzofuran, dibenzothiophene and combinations thereof.

[0085] In certain preferred embodiments, R1-R 16 one or more of the groups R1-R 16 one or more of the groups R1-R

[0086] In certain preferred embodiments, L1is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 20 ring atoms. In other preferred embodiments, L1is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 15 ring atoms. In certain more preferred embodiments, L1is selected from a single bond, or a substituted or unsubstituted benzene ring, carbazole, dibenzofuran, dibenzothiophene and combinations thereof.

[0087] In certain preferred embodiments, A1is selected from a substituted or unsubstituted heteroaromatic group having 8 to 30 ring atoms, and A1contains at least one O, S or Se hetero ring atom. In certain more preferred embodiments, A1is selected from a substituted or unsubstituted heteroaromatic group having 8 to 20 ring atoms, and A1contains at least one O, S hetero ring atom.

[0088] In certain preferred embodiments, at least one of the hetero ring atoms in X1and A1is selected from O, preferably both are selected from O; when one of the hetero ring atoms in X1or A1is selected from S, Se, then at least one of the ring atoms of A1and Y1-Y4is selected from N.

[0089] In certain more preferred embodiments, at least one of the hetero ring atoms in X1and A1is selected from O, preferably both are selected from O; when one of the hetero ring atoms in X1or A1is selected from S, then at least one of the ring atoms of A1and Y1-Y4is selected from N.

[0090] Aromatic or heteroaromatic ring systems as used herein refer to hydrocarbon radicals comprising at least one aromatic ring, including monocyclic radicals and polycyclic ring systems. Heteroaromatic ring systems as used herein refer to hydrocarbon radicals comprising at least one heteroaromatic ring (containing heteroatoms), including monocyclic radicals and polycyclic ring systems. These polycyclic rings can have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e. fused rings. Of these polycyclic rings, at least one is aromatic or heteroaromatic. For the purposes of the present invention, aromatic or heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also, wherein the plurality of aromatic or heteroaromatic groups can be interrupted by short non-aromatic units (<10% non-H atoms, preferably <5% non-H atoms, such as C, N or O atoms). Thus, for example, systems such as 9,9'-spirobifluorene, 9,9-dialkylfluorene, triarylamine, diaryl ether, etc. are also considered aromatic ring systems for the purposes of the present invention.

[0091] Specific examples of aromatic groups are benzene, naphthalene, anthracene, phenanthrene, rylenes, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, spirofluorene and derivatives thereof.

[0092] Specific examples of heteroaromatic groups are furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, perylene, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone and derivatives thereof. In some preferred embodiments, A1as described above can comprise one or a combination of the following structural groups:

[0093] wherein,

[0094] A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 each independently represent CR 18 or N;

[0095] W 1 , W 2are independently selected from C(R 19 R 20 ), Si(R 19 R 20 ), NR 18 , C(=0), S or O;

[0096] R 18 , R 19 , R 20 at each occurrence, are the same or different selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bound.

[0097] In a more preferred embodiment, A1comprises one of the following structural groups, wherein the H on the ring can be arbitrarily substituted:

[0098] In some more preferred embodiments, the first compound H1in the mixture has a structure according to Formula (I-1) to Formula (I-8):

[0099] X1, X2, X3are at each occurrence selected from O, S or Se, and at least one of X1and X2is selected from O, or at least one of X1and X3is selected from O; Y1-Y8are at each occurrence selected from N or CR 16 ; n1is selected from an integer from 0 to 2; n2is selected from an integer from 0 to 1; and:

[0100] For Formula (I-1) to Formula (I-8), when X1, X2, X3are all O, Y1-Y8are all selected from CR 16 ;

[0101] For Formula (I-1), when X1and X2are both different from O, at least one of Y3, Y6and Y7is selected from N;

[0102] For general formula (I-2), when X1and X2are different and are O, at least one of Y2, Y3, Y6and Y7is selected from N;

[0103] For general formula (I-3), when X1and X2are different and are O, at least one of Y2, Y3, Y6and Y7is selected from N;

[0104] R is a substituent independently selected from D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above-mentioned groups can be further replaced by D.

[0105] In some preferred embodiments, X1and X2are selected from O, or X1and X3are selected from O, and: Y1-Y8are all selected from CR 16 .

[0106] In some preferred embodiments, X1and X2are selected from O, or X1and X3are selected from O, and: Y1-Y8are all selected from CR 16 .

[0107] In some preferred embodiments, L1-L4are selected from a single bond or the following groups or combinations thereof:

[0108] wherein: Y 1 -Y 14 is independently selected at each occurrence from CR 18 or N; X is independently selected from NR 19 , O, S or Se; R 18 -R 19each occurrence is independently selected from H, D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group having 3 to 20 C atoms, or a branched or cyclic alkoxy group having 3 to 20 C atoms, or a branched or cyclic thioalkoxy group having 3 to 20 C atoms, or a branched or cyclic silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, or a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0109] In some more preferred embodiments, L1-L4 are selected from the following groups or combinations thereof:

[0110] wherein: "*" indicates the position of the bond, and the above groups are unsubstituted, or at least one H is replaced by R 17 as defined above for R1; in some embodiments, the H atoms on the ring can be further substituted. 17

[0111] The following illustrate specific examples of the first compound H1, but are not limited thereto, which can be further arbitrarily substituted:

[0112] In some preferred embodiments, the second compound H2 has a singlet energy level and a triplet energy level difference ΔE ST ≤ 0.50 eV, preferably ≤ 0.40 eV, more preferably ≤ 0.30 eV, and most preferably ≤ 0.20 eV.

[0113] In some preferred embodiments, the second compound H2 has a triplet energy level E T1 ≥ 2.70 eV, preferably ≥ 2.80 eV, more preferably ≥ 2.85 eV, and most preferably ≥ 2.90 eV.

[0114] ​In some preferred embodiments, the second compound H2 according to general formula (II) is selected, wherein Z1-Z3 are each selected from N.

[0115] In some preferred embodiments, Ar1-Ar3 are each independently selected from a group according to general formula (II-1) or general formula (II-3) or general formula (II-5) or general formula (II-6).

[0116] In a preferred embodiment, at least one of Ar1-Ar3 is selected from general formula (II-3).

[0117] In another preferred embodiment, at least one of Ar1-Ar3 is selected from general formula (II-5).

[0118] In a preferred embodiment, at least one of Ar1-Ar3 is selected from general formula (II-6).

[0119] The following examples illustrate specific examples of the second compound H2, but are not limited thereto, which can be further arbitrarily substituted:

[0120] wherein H can be partially or completely substituted by D.

[0121] The mixture according to the present application can be used as functional material in electronic devices. Functional materials can be classified as hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), emitter, host material. In a preferred embodiment, the mixture according to the present application can be used as host material. In a more preferred embodiment, the mixture according to the present application can be used as phosphorescent host material. As phosphorescent host material, appropriate energy levels are required, i.e. Exor E T1 .

[0122] In some preferred embodiments, the mixture according to the present application, wherein the first compound H1 and the second compound H2 have a type II semiconductor heterojunction, and Ex≥ 2.30 eV, preferably ≥ 2.40 eV, more preferably ≥ 2.50 eV, most preferably ≥ 2.60 eV.

[0123] In other embodiments, Ex≥ 2.65 eV, preferably ≥ 2.70 eV, more preferably ≥ 2.75 eV, most preferably ≥ 2.80 eV.

[0124] In a preferred embodiment, the mixture further comprises at least one further organic functional material selected from hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emitters (including fluorescent, phosphorescent and TADF materials), host materials or organic dyes. Various organic functional materials are described in detail, for example, in WO 2010135519 A1, US 20090134784 A1 and WO 2011110277 A1, the entire contents of which are hereby incorporated by reference.

[0125] In a preferred embodiment, the further organic functional material is selected from triplet emitters (phosphorescent emitters). Here the mixture according to the application (first compound H1 + second compound H2) can be used as a mixed host, wherein the weight percentage of the triplet emitter is < 20 wt%, preferably < 15 wt%, more preferably < 10 wt%, more preferably < 8 wt%.

[0126] In certain embodiments, the further organic functional material comprises a TADF material.

[0127] In certain embodiments, the further organic functional material comprises a singlet emitter.

[0128] Singlet emitters, triplet emitters and TADF materials are described in more detail below (but not limited thereto).

[0129] 1. Singlet Emitters

[0130] Singlet emitters often have a long conjugated pi-electron system. To date, there are many examples, such as the styryl amines and derivatives thereof disclosed in JP 2913116 B and WO 2001021729 A1, the indenofluorenes and derivatives thereof disclosed in WO 2008 / 006449 and WO 2007 / 140847 and the triarylamine derivatives of pyrene disclosed in US 7233019, KR 2006-0006760.

[0131] In some preferred embodiments, the singlet emitter can be selected from the group consisting of monostyryl amines, distyryl amines, tristyryl amines, tetrastyryl amines, styryl phosphines, styryl ethers and aryl amines.

[0132] A monostyrylamine is a compound comprising one unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tristyrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styryl group is a distyryl group, which can be further substituted. Corresponding phosphines and ethers are defined analogously to amines. An arylamine or aromatic amine is a compound comprising three directly linked unsubstituted or substituted aromatic or heterocyclic ring systems with at least one nitrogen. Preferably at least one of these aromatic or heterocyclic ring systems is a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples are anthracene amines, anthracene diamines, pyrene amines, pyrene diamines, chrysene amines and chrysene diamines. An anthracene amine is a compound in which one arylamine group is directly linked to an anthracene, preferably at the 9-position. An anthracene diamine is a compound in which two arylamine groups are directly linked to an anthracene, preferably at the 9,10-positions. Pyrene amines, pyrene diamines, chrysene amines and chrysene diamines are defined analogously, wherein the arylamine groups are preferably linked to the pyrene at the 1 or 1,6 positions.

[0133] Examples of singlet emitters based on vinylamines and arylamines, which are also preferred examples, can be found in the following patent documents: WO 2006 / 000388, WO 2006 / 058737, WO 2006 / 000389, WO 2007 / 065549, WO 2007 / 115610, US 7250532 B2, DE 102005058557 Al, CN 1583691 A, JP 08053397 A, US 6251531 Bl, US 2006 / 210830 A, EP 1957606 Al and US 2008 / 0113101 Al, the entire contents of which are hereby incorporated by reference.

[0134] Examples of singlet emitters based on distyrylbenzenes and derivatives thereof are US 5121029.

[0135] Further preferred singlet emitters can be selected from indenofluorene- amines and indenofluorene-diamines as disclosed in WO 2006 / 122630, benzindenofluorene- amines and benzindenofluorene-diamines as disclosed in WO 2008 / 006449, dibenzindenofluorene- amines and dibenzindenofluorene-diamines as disclosed in WO 2007 / 140847.

[0136] Further preferred singlet emitters can be selected from fused ring systems based on fluorene, as disclosed in US2015333277A1, US2016099411A1, US2016204355A1.

[0137] More preferred singlet emitters can be selected from derivatives of pyrene, such as the structures disclosed in US2013175509A1; triarylamine derivatives of pyrene containing dibenzofuran units, as disclosed in CN102232068B; other triarylamine derivatives of pyrene with specific structures, as disclosed in CN105085334A, CN105037173A. Other materials that can be used as singlet emitters are polycyclic aromatic hydrocarbon compounds, in particular derivatives of anthracene such as 9,10-bis(2-naphthyl)anthracene, naphthalene, tetracene, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, benzo fused rings such as (4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl), indenopyrene, decacyclene, hexa pentalene, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylenevinylene (such as US5121029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4(dicyanomethylene)-6-(4-p-dimethylaminostyryl-2-methyl)-4H-pyran (DCM), thiopyran, bis(azinyl)imine boron compounds (US2007 / 0092753A1), bis(azinyl)methylene compounds, carbostyryl compounds, oxazinone, benzoxazole, benzothiazole, benzimidazole and pyrrolopyrrolidinone, indolocarbazole ring derivatives (WO2019111971A1, WO2020250961A1, US2020212315A1). Some materials of singlet emitters can be found in the following patent documents: US20070252517A1, US4769292, US6020078. The entire contents of the above listed patent documents are hereby incorporated by reference.

[0138] Some examples of suitable singlet emitters are listed below:

[0139] 2. Triplet Emitter

[0140] A triplet emitter is also called a phosphorescent emitter. In a preferred embodiment, the triplet emitter is a metal complex of the general formula M(L)n3, wherein M is a metal atom, L, which can be the same or different at each occurrence, is an organic ligand which is bonded or coordinated to the metal atom M via one or more sites, and n3 is an integer greater than 1, preferably selected from 1, 2, 3, 4, 5 or 6. Optionally, the metal complex is bonded to a polymer via one or more sites, preferably via the organic ligand.

[0141] In a preferred embodiment, the metal atom M is selected from a transition metal or a lanthanide or an actinide, preferably from Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, and particularly preferably from Os, Ir, Ru, Rh, Re, Pd, Au or Pt.

[0142] Preferably, the triplet emitter comprises a chelating ligand, i.e. a ligand which is coordinated to the metal via at least two binding sites, and particularly preferably the triplet emitter comprises two or three identical or different bidentate or polydentate ligands. Chelating ligands are advantageous for improving the stability of the metal complex.

[0143] Examples of organic ligands can be selected from phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2-(2-thienyl)pyridine derivatives, 2-(1-naphthyl)pyridine derivatives or 2-phenylquinoline derivatives. All these organic ligands can be substituted, e.g. by fluorine or trifluoromethyl groups. The auxiliary ligand can preferably be selected from acetonitrile or picolinic acid.

[0144] In a preferred embodiment, the metal complex which can be used as triplet emitter has the following form:

[0145] wherein M1 is a metal selected from a transition metal or a lanthanide or an actinide, and particularly preferably from Ir, Pt or Au.

[0146] Ar 1 which can be the same or different at each occurrence, is a cyclic group which comprises at least one donor atom, i.e. an atom having a lone pair of electrons, such as nitrogen or phosphorus, via which the cyclic group is coordinated to the metal; Ar 2 which can be the same or different at each occurrence, is a cyclic group which comprises at least one C atom, via which the cyclic group is coordinated to the metal; Ar 1 and Ar 2which can each carry one or more substituent groups, which can also be linked together by substituent groups; L' can be the same or different at each occurrence and is a bidentate ancillary ligand, preferably a monanionic bidentate ancillary ligand; q1 can be 0, 1, 2 or 3, preferably 2 or 3; q2 can be 0, 1, 2 or 3, preferably 1 or 0.

[0147] Examples of some triplet emitters and their applications can be found in the following patent documents and literature: WO200070655, WO200141512, WO200202714, WO200215645, EP1191613, EP1191612, EP1191614, WO2005033244, WO2005019373, US2005 / 0258742, WO2009146770, WO2010015307, WO2010031485, WO2010054731, WO2010054728, WO2010086089, WO2010099852, WO2010102709, US20070087219A1, US20090061681A1, US20010053462A1, Baldo, Thompson et al. Nature 403, (2000), 750-753, Adachi et al. Appl. Phys. Lett. 78 (2001), 1622-1624, J. Kido et al. Appl. Phys. Lett. 65 (1994), 2124, Kido et al. Chem. Lett. 657, 1990, US2007 / 0252517A1, Johnson et al., JACS 105, 1983, 1795, Wrighton, JACS 96, 1974, 998, Ma et al., Synth. Metals 94, 1998, 245, US6824895, US7029766, US6835469, US6830828, WO2007095118A1, US2012004407A1, WO2012007088A1, WO2012007087A1, WO2012007086A1, US2008027220A1, WO2011157339A1, CN102282150A, WO2009118087A1, WO2013107487A1, WO2013094620A1, WO2013174471A1, WO2014031977A1, WO2014112450A1, WO2014007565A1, WO2014038456A1, WO2014024131A1, WO2014008982A1, WO2014023377A1, US20230329086A1, US20230270000A1, US20230269998A1, US20230065887A1, US2023167145A1.The contents of the above-listed patent documents and literature are hereby incorporated by reference in their entirety.

[0148] Some examples of suitable triplet emitters are listed below:

[0149] 3. Thermally Activated Delayed Fluorescence Materials (TADF Materials)

[0150] Conventional organic fluorescent materials can only utilize 25% singlet excitons generated by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). Although phosphorescent materials can effectively utilize singlet excitons and triplet excitons generated by electrical excitation to emit light due to the strong spin-orbital coupling of heavy atom centers, which enhances intersystem crossing, the internal quantum efficiency of the device can reach 100%. However, the high cost, poor material stability, and severe efficiency roll-off of phosphorescent materials limit their application in OLEDs. Thermally activated delayed fluorescence materials are the third generation of organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. Such materials generally have a small singlet-triplet energy level difference (ΔE ST ), and triplet excitons can be converted into singlet excitons through reverse intersystem crossing to emit light. This can make full use of singlet excitons and triplet excitons generated under electrical excitation. The internal quantum efficiency of the device can reach 100%. At the same time, the material structure is controllable, the properties are stable, the price is cheap, and no noble metal is needed, so it has a broad application prospect in the field of OLEDs.

[0151] TADF materials need to have a small singlet-triplet energy level difference, preferably ΔE ST <0.3 eV, secondly ΔE ST <0.25 eV, better ΔE ST <0.20 eV, and best ΔE ST <0.1 eV. In some preferred embodiments, TADF materials have a relatively small ΔE STIn another preferred embodiment, the TADF material has a good fluorescence quantum efficiency. Some TADF emitting materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et. al. Adv. Mater., 21, 2009, 4802, Adachi, et. al. Appl. Phys. Lett., 98, 2011, 083302, Adachi, et. al. Appl. Phys. Lett., 101, 2012, 093306, Adachi, et. al. Chem. Commun., 48, 2012, 11392, Adachi, et. al. Nature Photonics, 6, 2012, 253, Adachi, et. al. Nature, 492, 2012, 234, Adachi, et. al. J. Am. Chem. Soc, 134, 2012, 14706, Adachi, et. al. Angew. Chem. Int. Ed, 51, 2012, 11311, Adachi, et. al. Chem. Commun., 48, 2012, 9580, Adachi, et. al. Chem. Commun., 49, 2013, 10385, Adachi, et. al. Adv. Mater., 25, 2013, 3319, Adachi, et. al. Adv. Mater., 25, 2013, 3707, Adachi, et. al. Chem. Mater., 25, 2013, 3038, Adachi, et. al. Chem. Mater., 25, 2013, 3766, Adachi, et. al. J. Mater. Chem. C., 1, 2013, 4599, Adachi, et. al. J. Phys. Chem. A., 117, 2013, 5607.

[0152] More preferred TADF emitters can be selected from boron-nitrogen compounds such as those disclosed in WO2015102118A1, WO2020251049A1, US2020395553A1, US20230240142A1, US20230255100A1, US20230279027A1; the entire contents of the above-listed patent or article documents are hereby incorporated by reference.

[0153] Some examples of suitable TADF emitters are listed below:

[0154] The above-occurring publications of organic functional materials are incorporated herein by reference for disclosure purposes.

[0155] Based on the above mixture, the present application further provides the use of a mixture as described above, i.e. the use of the mixture for an organic electronic device, which can be selected from, but is not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting electric cell (OLEEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spintronics device, a photodiode, an organic sensor or an organic plasmon emitting diode (Organic Plasmon Emitting Diode), and is particularly preferred for an organic electroluminescent device, such as an OLED, an OLEEC, an organic light emitting field effect transistor. Preferably, the mixture is used in the light emitting layer of an electroluminescent device.

[0156] In some preferred embodiments, the mixture according to the present application is used in a vacuum deposited OLED device. For this purpose, the mixture according to the present application, wherein the first compound H1 and / or the second compound H2 has a molecular weight of < 1000 g / mol, preferably < 900 g / mol, very preferably < 850 g / mol, more preferably < 800 g / mol, most preferably < 700 g / mol.

[0157] It is a further object of the present application to provide a material solution for printed OLEDs.

[0158] For this purpose, the mixture according to the present application, wherein the first compound H1 and / or the second compound H2 has a molecular weight of > 700 g / mol, preferably > 800 g / mol, very preferably > 900 g / mol, more preferably > 1000 g / mol, most preferably > 1100 g / mol.

[0159] In some preferred embodiments, the mixture according to the present application has a solubility of the first compound H1 and / or the second compound H2 in toluene of > 10 mg / mL, preferably > 15 mg / mL, most preferably > 20 mg / mL at 25 °C.

[0160] It is a further object of the present application to provide an organic compound having a structure according to general formula (I-A) or (I-B) or (III-A) or (III-B):

[0161] wherein: X1, X2, X3are independently selected from O, S or Se, and at least one of X1, X2in general formula (I-A) or (III-A) is O, and at least one of X1, X3in general formula (I-B) or general formula (III-B) is O; Y1-Y8are selected from N or CR 16 ; n is selected from an integer from 0 to 2; when X1, X2, X3are all O, Y1-Y8are all selected from CR 16 ; when X1and X2are different from O, or X1and X3are different from O, at least one of Y2, Y3, Y6and Y7is selected from N;

[0162] L1is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms;

[0163] Ar is selected from a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms, or a heteroaromatic group having 2 to 30 ring atoms;

[0164] R is a substituent independently selected from D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above-mentioned groups can be further replaced by D;

[0165] R1-R 16 are each independently selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above-mentioned groups can be further replaced by D.

[0166] The organic compound according to the present application fulfills the structure of general formula (I-A) or (I-B) or (III-A) or (III-B) as described above and at the same time contains a 3,9'-bicarbazole and an oxygen-containing fused ring. Without being bound to a particular theory, it is believed that due to the two moieties in the organic compound being connected by a single bond or a conjugated bridging group, a greater delocalization of the charge over the organic compound is achieved, thereby improving the stability of the organic compound.

[0167] In certain preferred embodiments, the organic compound has a structure according to any one of general formula (I-1) to general formula (I-8):

[0168] X1, X2, X3are independently selected from O, S or Se at each occurrence, and at least one of X1and X2is selected from O, or at least one of X1and X3is selected from O; Y1-Y8are selected from N or CR 16 ; n1is selected from an integer from 0 to 2; n2is selected from an integer from 0 to 1;

[0169] and: for general formula (I-1) to general formula (I-8), when X1, X2, X3are all O, Y1-Y8are all selected from CR 16 ;

[0170] for general formula (I-1), when X1and X2are different from O, at least one of Y3, Y6and Y7is selected from N;

[0171] for general formula (I-2), when X1and X2are different from O, at least one of Y2, Y3, Y6and Y7is selected from N;

[0172] for general formula (I-3), when X1and X2are different from O, at least one of Y2, Y3, Y6and Y7is selected from N.

[0173] R is a substituent independently selected from D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in the various groups mentioned above can further be replaced by D.

[0174] The following illustrates some specific examples of the organic compounds, but is not limited thereto:

[0175] Meanwhile, the organic compound as described in the present application has a higher E T1 and adjustable LUMO, which is helpful to achieve higher performance of blue phosphorescent devices in applications. The following are the calculation results of the energy levels of some molecular structure fragments (calculated by TD-DFT method based on B3PW91 functional and 6-31G(d) basis set):

[0176] Table 1

[0177] From the comparison of structure fragment 1 and comparative structures 1-4, structure fragment 6 and comparative structures 7-10, it can be seen that the triplet energy level of the oxygen-containing hetero-element fused ring is related to the atomic number of the contained oxygen hetero atom: when the contained oxygen hetero atom is all O, the above structure fragments have the highest triplet energy level (E T1 ≥ 3.00 eV); as the atomic number of the contained oxygen hetero atom increases, the triplet energy level gradually decreases; when at least one of the contained oxygen hetero atom is O, the above structure fragments have a relatively high triplet energy level (E T1 ≥ 2.90 eV).

[0178] From the comparison of structure fragments 2-5 and comparative structures 3-6, structure fragments 7-8 and comparative structures 9-14, it can be seen that the triplet energy level of the fused ring is also related to whether there is N hetero on the fused ring and the position of the N hetero; at the same time, the position of the N hetero also affects the LUMO energy level of the above structure fragments. From the above comparison, it can be seen that the oxygen-containing hetero-element fused ring structure fragment defined according to the present application has a relatively high triplet energy level and a relatively shallow LUMO compared to other structure similar fragments, which is helpful to form an excimer in the light-emitting layer and inhibit the diffusion of excitons to the hole transport layer.

[0179] Due to such structural characteristics, the hole-type compound (first compound H1) represented by general formula (I) or general formula (III) can effectively regulate the distribution of excitons in an organic electronic device in applications. Therefore, the organic electronic device, especially the electroluminescent device using the fused ring compound (first compound H1) represented by general formula (I) or general formula (III) can have the characteristics of high efficiency and long service life.

[0180] In some preferred embodiments, the organic compound according to the present application is deuterated at least at one H, preferably at 10% and more of the H, more preferably at 20% and more of the H, very preferably at 30% and more of the H, most preferably at 40% and more of the H.

[0181] In some preferred embodiments, the mixture and / or the organic compound according to the present application is used in an OLED device of the evaporation type. For this purpose, the organic compound according to the present application has a molecular weight of < 1000 g / mol, preferably < 900 g / mol, very preferably < 850 g / mol, more preferably < 800 g / mol, most preferably < 700 g / mol.

[0182] In some preferred embodiments, the organic compound according to the present application has a ΔHOMO of > 0.2 eV, preferably of > 0.25 eV, more preferably of > 0.3 eV, even more preferably of > 0.35 eV, very preferably of > 0.4 eV, most preferably of > 0.45 eV.

[0183] In some preferred embodiments, the organic compound according to the present application has an E T1 > 2.80 eV, preferably of > 2.90 eV, more preferably of > 2.95 eV, very preferably of > 3.00 eV.

[0184] The present application further relates to a composition or ink comprising at least one mixture or organic compound according to the present application and at least one organic solvent.

[0185] In some embodiments, the composition according to the present application, wherein the mixture or organic compound is used as a host material.

[0186] In some preferred embodiments, the composition according to the present application comprises at least one mixture or organic compound according to the present application and at least one triplet emitter.

[0187] In some preferred embodiments, the composition according to the present application comprises at least one mixture or organic compound according to the present application and at least one thermally activated delayed fluorescence emitter.

[0188] In some preferred embodiments, the composition according to the present application comprises at least one mixture or organic compound according to the present application, at least one triplet emitter and at least one thermally activated delayed fluorescence emitter.

[0189] In some preferred embodiments, the composition according to the present application is a solution.

[0190] In some preferred embodiments, the composition according to the present application is a suspension.

[0191] The composition according to the present application can comprise from 0.01 wt% to 20 wt% of the mixture or organic compound, preferably from 0.1 wt% to 15 wt%, more preferably from 0.2 wt% to 10 wt%, and most preferably from 0.25 wt% to 5 wt% of the mixture or organic compound.

[0192] In some preferred embodiments, the composition according to the present application comprises an organic solvent selected from the group consisting of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or inorganic ester compound such as borate or phosphate ester, or a mixture of two or more solvents.

[0193] In some other preferred embodiments, the composition according to the present application comprises at least 50 wt% of aromatic or heteroaromatic solvent; preferably at least 80 wt% of aromatic or heteroaromatic solvent; and most preferably at least 90 wt% of aromatic or heteroaromatic solvent.

[0194] Examples of aromatic or heteroaromatic solvents according to the present application include, but are not limited to, 1-tetralone, 3-phenoxytoluene, acetophenone, 1-methoxynaphthalene, p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, diamylbenzene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, diphenyl ether, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, 2-phenoxytoluene, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, and the like.

[0195] In some other embodiments, suitable and preferred solvents are aliphatic, alicyclic or aromatic hydrocarbons, amines, mercaptans, amides, nitriles, esters, ethers, polyethers, alcohols, diols or polyols.

[0196] In some other embodiments, alcohols represent a suitable class of solvents. Preferred alcohols include alkylcyclohexanols, particularly methylated aliphatic alcohols, naphthols, and the like.

[0197] The solvent can be a cycloalkane, such as decalin.

[0198] The solvent can be used alone or as a mixture of two or more organic solvents.

[0199] In certain embodiments, the composition according to the present application, comprising a mixture or organic compound as described above, and at least one organic solvent, can further comprise another organic solvent. Examples of another organic solvent include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, dimethylsulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0200] In some preferred embodiments, solvents particularly suitable for the present application are solvents having Hansen Solubility Parameters in the following ranges:

[0201] δ d (Dispersion) in the range of 17.0 MPa 1 / 2 ~ 23.2 MPa 1 / 2 , especially in the range of 18.5 MPa 1 / 2 ~ 21.0 MPa 1 / 2 .

[0202] δ p (Polar) in the range of 0.2 MPa 1 / 2 ~ 12.5 MPa 1 / 2 , especially in the range of 2.0 MPa 1 / 2 ~ 6.0 MPa 1 / 2 .

[0203] δ h (Hydrogen Bonding) in the range of 0.9 MPa 1 / 2 ~ 14.2 MPa 1 / 2 , especially in the range of 2.0 MPa 1 / 2 ~ 6.0 MPa 1 / 2 .

[0204] The organic solvent in the composition according to the present application is selected with consideration of its boiling point parameter. In the present application, the boiling point of the organic solvent is > 150°C; preferably > 180°C; more preferably > 200°C; even more preferably > 250°C; most preferably > 275°C or > 300°C. A boiling point in these ranges is beneficial to prevent clogging of the nozzles of the inkjet printing head. The organic solvent can evaporate from the solvent system to form a thin film comprising the functional material.

[0205] In some preferred embodiments, a composition according to the present application:

[0206] 1) a viscosity of the ink at 25°C in the range of 1 cps to 100 cps, and / or;

[0207] 2) a surface tension of the ink at 25°C in the range of 19 dyne / cm to 50 dyne / cm.

[0208] The organic solvent in the composition according to the present application is selected taking into account the surface tension parameter of the ink. The suitable ink surface tension parameter is suitable for the specific substrate and the specific printing method. For example, for inkjet printing, in some preferred embodiments, the surface tension of the organic solvent at 25°C is in the range of about 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0209] In some preferred embodiments, the ink according to the present application has a surface tension at 25°C in the range of about 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0210] The organic solvent in the composition according to the present application is selected taking into account the viscosity parameter of the ink. The viscosity can be adjusted by different methods, such as by selection of the suitable organic solvent and the concentration of the functional material in the ink. In some preferred embodiments, the viscosity of the organic solvent is less than 100 cps; more preferably less than 50 cps; most preferably in the range of 1.5 cps to 20 cps. The viscosity herein refers to the viscosity at the ambient temperature during printing, which is generally in the range of 15°C to 30°C, preferably in the range of 18°C to 28°C, more preferably in the range of 20°C to 25°C, most preferably in the range of 23°C to 25°C. The composition thus formulated is particularly suitable for inkjet printing.

[0211] In some preferred embodiments, the composition according to the present application has a viscosity at 25°C in the range of about 1 cps to 100 cps; more preferably in the range of 1 cps to 50 cps; most preferably in the range of 1.5 cps to 20 cps.

[0212] The ink obtained from the organic solvent satisfying the above-mentioned boiling point and surface tension parameters and viscosity parameter is capable of forming a functional material thin film having uniform thickness and compositional properties.

[0213] It is a further object of the present application to provide the use of the mixture and / or the organic compound as described above in an organic electronic device.

[0214] The organic electronic device can be selected from the group consisting of an organic light emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light emitting cell (OLEC), an organic field effect transistor (OFET), an organic light emitting field effect transistor, an organic laser, an organic spintronics device, an organic sensor or an Organic Plasmon Emitting Diode.

[0215] The present application further relates to an organic electronic device comprising at least one of the mixtures and / or organic compounds according to the present application or at least one functional layer which is prepared using the composition according to the present application. Typically, such an organic electronic device comprises at least one cathode, one anode and at least one functional layer between the cathode and the anode, wherein the functional layer comprises at least one of the organic compounds as described above and has a thickness in the range of 5 nm to 1000 nm.

[0216] In some more preferred embodiments, the organic electronic device as described above is an electroluminescent device, in particular an OLED, comprising a substrate, an anode on the substrate, a cathode on the top layer and at least one light emitting layer between the anode and the cathode.

[0217] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light emitting device. See, for example, Bulovic et al. Nature 1996, 380, p29, and Gu et al. Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface. Substrates without surface defects are particularly desirable. In some preferred embodiments, the substrate is flexible and can be selected from a polymeric film or plastic having a glass transition temperature (Tg) of 150°C or more, preferably more than 200°C, more preferably more than 250°C, and most preferably more than 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene naphthalate (PEN).

[0218] The anode can comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or the light emitting layer. In some embodiments, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light emitter in the light emitting layer or a p-type semiconductor material as a HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. Examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known to those of ordinary skill in the art and can be readily selected for use. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate devices according to the present application.

[0219] The cathode can comprise a conductive metal or metal oxide. The cathode can readily inject electrons into an EIL or ETL or directly into the light emitting layer. In some embodiments, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light emitter in the light emitting layer or an n-type semiconductor material as an electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. In principle, all materials that can be used as a cathode for an OLED can be used as a cathode material for a device according to the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0220] The OLED can also contain other functional layers, such as a hole injection layer (HIL) or a hole transport layer (HTL) between the anode and the light emitting layer, an electron blocking layer (EBL), an electron injection layer (EIL) or an electron transport layer (ETL) between the light emitting layer and the cathode, a hole blocking layer (HBL). Suitable materials for use in these functional layers are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

[0221] In some preferred embodiments, the organic electronic device according to the present application, wherein the light-emitting layer is prepared by vacuum evaporation, the evaporation source comprising a mixture according to the present application.

[0222] In some preferred embodiments, the organic electronic device according to the present application, wherein the light-emitting layer is prepared by vacuum evaporation, the evaporation source comprising a mixture according to the present application.

[0223] The organic electronic device according to the present application has a peak of the emission wavelength between 300 nm and 700 nm, preferably between 350 nm and 600 nm, more preferably between 400 nm and 500 nm, and most preferably between 450 nm and 470 nm.

[0224] The present application also relates to the use of the organic electronic device according to the present application in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0225] The present application also relates to electronic devices comprising the organic electronic device according to the present application, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0226] Examples

[0227] The present application will be described in connection with preferred embodiments, however, it will be understood that the application is not limited to the described embodiments, but can be practiced with modification and alteration within the spirit and scope of the present inventive concept. The description of the embodiments is intended to be illustrative, and not to limit the scope of the application, as defined by the appended claims.

[0228] 1. Synthesis of compounds

[0229] Synthesis of intermediate 1-1 : In a dry round bottom flask, 1-1a (synthesis method refer to the literature J. Am. Chem. Soc. 138, 14582-14585 (2016)) (32.41 g, 180.04 mmol) and 1-1b (48.98 g, 283.08 mmol) were added and stirred in 2 L of dichloromethane until completely dissolved. To the above solution, trifluoroacetic anhydride (55.50 g, 264.21 mmol) was added and stirred at 25 °C for 2 h. After the reaction was completed, saturated aqueous sodium bicarbonate solution was added to the reaction solution, and extracted with ethyl acetate several times. The organic phase was combined and washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The crude product was concentrated and further purified by column chromatography (n-hexane / ethyl acetate) and dried to obtain an oily liquid 36.15 g, yield 60%. MS (ASAP) = 334.1.

[0230] Synthesis of intermediate 1-2: Intermediate 1-1 (33.40 g, 100.00 mmol) was dissolved in 300 mL of dichloromethane under ice bath condition, and 1 equivalent of m-chloroperoxybenzoic acid (17.95 g, 104.00 mmol) was added to the above solution. After natural warming to room temperature, the reaction was continued, and the progress of the reaction was monitored by thin layer chromatography (TLC). After the reaction was completed, saturated aqueous sodium bicarbonate solution was added to the reaction solution, and it was extracted with ethyl acetate several times. The organic phase was combined and washed with saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The crude product was concentrated, and then purified by column chromatography (n-hexane / ethyl acetate) and dried to obtain the product 18.02 g, with a yield of 63%. MS (ASAP) = 285.2.

[0231] Synthesis of intermediate 2-1: A dry three-necked flask was charged with 2-1a (synthesis method refer to patent CN110903294A) (10.52 g, 31.35 mmol), bis(pinacolato)diboron (12.21 g, 48.06 mmol), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (1.33 g, 1.80 mmol), Xphos (1.72 g, 3.60 mmol), and potassium acetate (6.82 g, 69.56 mmol), and 250 mL of 1,4-dioxane was added. After vacuum-nitrogen circulation was repeated three times, the reaction was stirred at 100°C overnight. After the reaction was completed, the reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane, washed with water, and then combined. The organic phase was purified by column chromatography (petroleum ether) and dried to obtain intermediate 2-1, 5.78 g, with a yield of 48%. MS (ASAP) = 384.3.

[0232] Synthesis of intermediate 2-2: A dry three-necked flask was charged with 2-2a (24.87 g, 74.89 mmol), 2-2b (31.70 g, 112.48 mmol), potassium carbonate (15.50 g, 112.17 mmol), copper (0.95 g, 14.92 mmol), cuprous iodide (2.85 g, 14.97 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (2.76 g, 14.98 mmol), and 150 mL of N,N-dimethylacrylamide was added to dissolve. After vacuum-nitrogen circulation was repeated three times, the reaction was stirred at 110°C for 18 hours, and then the reaction solution was cooled. The reaction solution was added to saturated ammonium chloride solution, and white solid was precipitated during stirring. The solid was filtered, and the obtained crude product was further purified by ethanol slurry. The product intermediate 2-2 was obtained by filtration and drying, about 18.56 g, with a yield of 51%. MS (ASAP) = 486.5.

[0233] Synthesis of Intermediate 3-1 : In a dry reaction flask, add 3-1a (4.76 g, 24.17 mmol), dissolve in 15 mL THF under magnetic stirring, and cool to -15 °C; after temperature stabilization, add 20.5 mL of isopropylmagnesium chloride-lithium chloride THF solution (1.3 M) dropwise, and continue stirring for 24 h. Subsequently, add a saturated THF solution containing 3.63 g of zinc chloride to it, and restore the reaction system to room temperature (25 °C); after temperature stabilization, continue stirring for 30 min to obtain solution A. Take another dry reaction flask, add 3-1b (5.87 g, 22.24 mmol), bis(dibenzylideneacetone)palladium (0.33 g, 0.58 mmol), tris(2-furyl)phosphine (0.27 g, 1.15 mmol), and 30 mL THF, and dissolve thoroughly to obtain solution B. Warm solution B to 50 °C, and add solution A dropwise to it over 2 h; after the addition is complete, continue to react for 1 h. After the reaction is complete, dilute the reaction solution with 400 mL of ethyl ether slowly, wash with 150 mL of saturated brine solution (repeat 3 times), and finally combine the organic phases, dry over anhydrous magnesium sulfate, filter, concentrate, and purify by silica gel column chromatography (n-hexane / ethyl acetate) to obtain 6.91 g of intermediate 3-1 in total, with a yield of 81%. MS (ASAP) = 353.1.

[0234] Synthesis of Intermediate 3-2: In a dry reaction flask, add intermediate 3-1 (6.50 g, 18.42 mmol), dissolve in 20 mL THF under magnetic stirring, and cool to 0 °C; after temperature stabilization, add 17.67 mL of 2,2,6,6-tetramethylpiperidinylmagnesium chloride-lithium chloride complex THF solution (1.15 M, 20.32 mmol) dropwise, and continue stirring for 2 h. Subsequently, add 22 mL of a dichloromethane solution containing 3.96 g of bis(thiocarbonyldimethylamine) disulfide (16.47 mmol) to it, and restore the reaction system to room temperature (25 °C) naturally; then add 30 mL of saturated aqueous ammonium chloride solution to quench the reaction, and extract the product with dichloromethane (100 mL each time, 3 times of extraction), dry the combined organic phases over anhydrous magnesium sulfate, concentrate, and purify by silica gel column chromatography (n-hexane / ethyl acetate) to obtain 7.56 g of intermediate 3-2 in total, with a yield of 87%. MS (ASAP) = 471.8.

[0235] Synthesis of Intermediate 3-3: In a dry reaction flask, Intermediate 3-2 (7.14 g, 15.13 mmol) was dissolved in 150 mL of THF under magnetic stirring and cooled to -20 °C. After the temperature was stabilized, n-butyllithium solution in n-pentane (9.84 mL, 1.6 M, 15.74 mmol) was added dropwise. After 1 h of reaction, a total of 1 mL of methanol was added to terminate the reaction. The reaction solution was concentrated, and Intermediate 3-3 was obtained by silica gel column chromatography (n-hexane / ethyl acetate) with a yield of 4.12 g, 86%. MS (ASAP) = 303.1.

[0236] Synthesis of Intermediate 4-1 (Pentacyclic DBF 4-Br): In a dry three-necked flask, 4-1a (synthesis method refer to patent CN110903294A) (10.05 g, 29.80 mmol), bis(pinacolato)diboron (1158 g, 45.59 mmol), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (1.44 g, 1.97 mmol), Xphos (2.13 g, 4.47 mmol), and potassium acetate (6.87 g, 70.03 mmol) were added, 300 mL of 1,4-dioxane was added, vacuumed and filled with nitrogen for three times, and the reaction was stirred at reflux overnight after being warmed to reflux. After the reaction was completed, the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporation, and then dissolved in dichloromethane, washed with water, combined the organic phase, and purified by column chromatography (petroleum ether) to obtain Intermediate 4-1 with a yield of 7.67 g, 67%. MS (ASAP) = 384.2.

[0237] Synthesis of Intermediate 1-3: In a dry three-necked flask, Intermediate 1-2 (11.51 g, 40.10 mmol), bis(pinacolato)diboron (14.05 g, 55.34 mmol), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (1.61 g, 2.21 mmol), Xphos (2.29 g, 4.81 mmol), and potassium acetate (8.66 g, 88.22 mmol) were added, 300 mL of 1,4-dioxane was added, vacuumed and filled with nitrogen for three times, and the reaction was stirred at 90 °C for 24 h. After the reaction was completed, the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporation, and then dissolved in dichloromethane, washed with water, combined the organic phase, and purified by column chromatography (petroleum ether) to obtain Intermediate 1-3 with a yield of 7.52 g, 56%. MS (ASAP) = 334.1.

[0238] The synthesis of Intermediate 5-1 to Intermediate 7-1 was similar to the synthesis method of Intermediate 3-1, except that some raw materials were replaced. The reactants and products of each step are shown in Table 2 below:

[0239] Synthesis of Intermediates 5-1 to 7-1 in Table 2

[0240] The synthesis of Intermediates 5-2 to 7-2 was similar to that of Intermediate 3-2, except for the replacement of some starting materials. The reactants and products of each step are shown in Table 3 below:

[0241] Synthesis of Intermediates 5-2 to 7-2 in Table 3

[0242] The synthesis of Intermediates 5-3 to 7-3 was similar to that of Intermediate 3-3, except for the replacement of some starting materials. The reactants and products of each step are shown in Table 4 below:

[0243] Synthesis of Intermediates 5-3 to 7-3 in Table 4

[0244] The synthesis of Intermediates 5-4 to 7-4 was similar to that of Intermediate 1-2, except for the replacement of some starting materials. The reactants, products and yields are shown in Table 5 below:

[0245] Synthesis of Intermediates 5-4 to 7-4 in Table 5

[0246] Synthesis of Compound 1: In a dry reaction flask, 2-2a (4.98 g, 15 mmol), Intermediate 1-2 (4.57 g, 16 mmol), potassium carbonate (2.96 g, 21.4 mmol), copper powder (0.10 g, 1.6 mmol), cuprous iodide (0.29 g, 1.5 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (524 mg, 2.85 mmol) were placed, then N,N-dimethylacrylamide 100 mL was added, vacuumed and nitrogen was circulated for three times, stirred at 180 °C for 14 hours, cooled to room temperature, the reaction solution was slowly dropped into 300 mL of water, white solid was precipitated in stirring, filtered, the filter cake was dissolved with toluene and passed through a short silica gel column, the mother liquor was concentrated and purified by column chromatography (dichloromethane / n-hexane) to obtain Compound 1 about 4.68 g, yield 58%. MS (ASAP) = 538.3.

[0247] Synthesis of compound 2: In a dry three necked flask was placed intermediate 2-1 (5.07 g, 13.21 mmol), intermediate 2-2 (5.35 g, 11.01 mmol), tetrakis(triphenylphosphine)palladium (0.38 g, 0.33 mmol), Xphos (0.32 g, 0.66 mmol), potassium carbonate (2.3 g, 17.05 mmol), added 50 mL DMF, vacuum-nitrogen cycle three times, stirred at 130 °C for 12 h, cooled, removed solvent by rotary evaporation to get crude product. The crude product was purified by column chromatography (petroleum ether / dichloromethane) to get compound 2 about 2.98 g, yield 41%. MS (ASAP) = 664.2.

[0248] Synthesis of compound 3:

[0249] In a dry reaction flask was placed intermediate 3-3 (3.86 g, 12.71 mmol), 2-2a (4.02 g, 12.10 mmol), tris(dibenzylideneacetone)dipalladium (0.66 g, 0.73 mmol), XPhos (1.21 g, 2.54 mmol), sodium tert-butoxide (2.36 g, 24.56 mmol), then added xylene 250 mL, vacuum-nitrogen cycle three times, refluxed overnight, cooled to room temperature, washed with water three times, concentrated by rotary evaporation, purified by column chromatography (dichloromethane / n-hexane) to get compound 3 about 3.09 g, yield 46%. MS (ASAP) = 555.2.

[0250] Synthesis of compound 4: In a dry three necked flask was placed intermediate 4-1 (4.59 g, 11.94 mmol), intermediate 2-2 (4.85 g, 9.95 mmol), tetrakis(triphenylphosphine)palladium (0.35 g, 0.30 mmol), Xphos (0.24 g, 0.50 mmol), potassium carbonate (1.62 g, 11.74 mmol), added 50 mL DMF, vacuum-nitrogen cycle three times, stirred at 140 °C for 12 h, cooled, removed solvent by rotary evaporation to get crude product. The crude product was purified by column chromatography (petroleum ether / dichloromethane), further purified by slurry in dichloromethane and ethyl acetate to get compound 4 about 3.51 g, yield 53%. MS (ASAP) = 664.22.

[0251] Synthesis of compound 5: In a dry three-necked flask, intermediate 1-3 (5.38 g, 16.10 mmol), intermediate 2-2 (6.84 g, 14.01 mmol), tris(dibenzylideneacetone)dipalladium (0.97 g, 0.84 mmol), Xphos (0.53 g, 1.12 mmol), potassium carbonate (2.28 g, 16.52 mmol) were added and dissolved in 50 mL DMF, vacuumed and filled with nitrogen for three times, stirred at 120 °C for 24 h, then cooled down, the solvent was removed by rotary evaporation to get the crude product. The crude product was purified by column chromatography (petroleum ether / dichloromethane), further purified by slurry with dichloromethane and ethyl acetate to get compound 5 about 3.10 g, yield 36%. MS (ASAP) = 613.22.

[0252] Synthesis of compound 6: In a dry reaction flask, 6-1a (synthesis method refer to patent CN110903294A) (8.08 g, 23.98 mmol), 2-2a (7.45 g, 22.41 mmol), tris(dibenzylideneacetone)dipalladium (1.03 g, 1.12 mmol), XPhos (2.03 g, 4.26 mmol), sodium tert-butoxide (4.24 g, 44.15 mmol) were added, then added xylene 400 mL, vacuumed and filled with nitrogen for three times, refluxed overnight, cooled to room temperature, the reaction liquid was washed with water three times, the organic phase was concentrated by rotary evaporation, then purified by column chromatography (dichloromethane / n-hexane), dried and further purified by sublimation to get compound 6 about 3.13 g, yield 25%. MS (ASAP) = 587.9.

[0253] Synthesis of compound 7: In a dry reaction flask, 7-2a (7.29 g, 21.63 mmol), 2-2a (6.98 g, 21.00 mmol), tris(dibenzylideneacetone)dipalladium (0.87 g, 0.95 mmol), XPhos (2.10 g, 4.41 mmol), sodium tert-butoxide (4.10 g, 42.63 mmol) were added, then added xylene 400 mL, vacuumed and filled with nitrogen for three times, refluxed overnight, cooled to room temperature, the reaction liquid was washed with water three times, the organic phase was concentrated by rotary evaporation, then purified by column chromatography (dichloromethane / n-hexane), dried and further purified by sublimation to get compound 7 about 6.34 g, yield 54%. MS (ASAP) = 587.8.

[0254] The synthesis of compounds 8-10 is similar to the synthesis method of compound 1, the difference is only the replacement of part of the raw materials, the reactants and products of each step are shown in Table 6 below:

[0255] Table 6 Synthesis of compounds 8-10

[0256] The synthesis of compound 11-13 is similar to that of compound 5, except for the replacement of some raw materials. The reactants and products of each step are shown in Table 7 below:

[0257] Table 7 Synthesis of compound 11-13

[0258] 2. Energy structure of organic compound

[0259] The energy structure of the organic molecule is calculated by TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formula, and S1 and T1 are used directly.

[0260] HOMO (eV) = ((HOMO(G) x 27.212) - 0.9899) / 1.1206

[0261] LUMO (eV) = ((LUMO(G) x 27.212) - 2.0041) / 1.385

[0262] Where (HOMO(G) and (LUMO(G) are the results of direct calculation by TD-DFT.

[0263] The results are shown in Table 8:

[0264] Table 8

[0265] 3. Device preparation and characterization

[0266] Among them, compound HI and LiQ are purchased from Jilin Aolide Optoelectronic Material Co., Ltd., and the rest of the materials are compounds disclosed in the prior art, the synthesis of which is referred to the literature of the prior art.

[0267] The preparation process of the above OLED device is described in detail by specific examples. The blue phosphor device structure is HI (10 nm) / HT (60 nm) / barrier layer 1 (15 nm) / (host 1 + host 2): guest = 92:8 (35 nm) / barrier layer 2 (5 nm) / ET: LiQ = 50:50 (30 nm) / LiQ (2 nm) / Al (100 nm).

[0268] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrate: cleaned with various solvents (e.g. one or more of chloroform, acetone or isopropanol) followed by UV ozone treatment.

[0269] b. Evaporation: the ITO substrate was moved into a vacuum vapor deposition apparatus, and a 10 nm thick layer of HI was formed using a resistive heating evaporation source under high vacuum (1 x 10 -6 -6 bar), followed by evaporation of a HT compound to form a 60 nm thick hole transport layer HT, followed by formation of a 15 nm thick barrier layer 1 on the HT layer. Subsequently, using multiple evaporation sources, the materials were vaporized at different rates such that the weight ratio of (H1+H2):BD was 92:8, to form a 35 nm thick light emitting layer. This was followed by evaporation of a barrier layer 2 (5 nm), after which the ET and LiQ were placed in different evaporation units and co-deposited at a 50 weight % ratio each to form a 30 nm thick electron transport layer, followed by deposition of 2 nm of LiQ as an electron injection layer, and finally an Al cathode with a thickness of 100 nm was deposited on the electron injection layer.

[0270] c. Encapsulation: the device was encapsulated with UV hardening resin in a nitrogen glove box.

[0271] The device performance of the above examples and comparative examples was tested, and the results are shown in Table 9; wherein B.I. (Blue Index) @ 1000 nits is defined as the ratio of current efficiency (cd / A) to CIE-y at 1000 nits brightness; and device lifetime T95@1000 nits is defined as the time for the brightness to decay to 95% of the initial value under constant current conditions when the initial brightness of the device is 1000 nits (the results of the examples and other comparative examples in the table are all relative values based on the values of Comparative Example 1).

[0272] Table 9

[0273] As can be seen from the device data results in Table 9, the device examples 1-23 using the mixture according to the application as the host have improved overall performance in terms of blue light efficiency (B.I.) and lifetime compared to the comparative examples using a single host, or using prior art comparative compounds or mixtures; and the device examples 4 and 6 using the organic compound according to the application as the barrier layer have further improved lifetime performance compared to the device examples 2 and 5 which have the same structure but use comparative compounds as the barrier layer 1.

[0274] The blue phosphorescent sensitized OLED device structure is HI (30 nm) / HT (60 nm) / Barrier 1 (15 nm) / Host 1:Host 2:Sensitizer:Guest = 54:39.5:6:0.5 (35 nm) / Barrier 2 (5 nm) / ET:LiQ = 50:50 (30 nm) / LiQ (2 nm) / Al (100 nm).

[0275] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrate: cleaned with various solvents (e.g. one or several of chloroform, acetone or isopropanol) followed by UV ozone treatment.

[0276] b. Evaporation: The ITO substrate is moved into a vacuum vapor deposition apparatus, and a 30 nm thick layer of HI is formed using a resistive heating evaporation source under high vacuum (1 x 10 -6 -6 millibar). The HT compound is then evaporated to form a 60 nm thick hole transport layer HT on the HI layer, followed by a 15 nm thick barrier layer 1. Subsequently, using multiple evaporation sources, the materials are vaporized at different rates such that the weight ratio of Host 1:Host 2:Sensitizer:Guest is 54:39.5:6:0.5, to form a 35 nm thick emissive layer. A barrier layer 2 (HB, 5 nm) is then evaporated, followed by co-deposition of ET and LiQ at a 50 weight percent ratio each, to form a 30 nm thick electron transport layer, followed by deposition of a 2 nm thick LiQ as an electron injection layer, and finally a 100 nm thick Al cathode is deposited on the electron injection layer.

[0277] c. Encapsulation: The device is encapsulated with UV-cured resin in a nitrogen glovebox.

[0278] The device performance of the above examples and comparative examples is tested, as shown in Table 10; wherein the blue light efficiency (B.I.) and T95 lifetime are taken at the initial luminance of 1000 nits; (the results of the examples and other comparative examples in the table are uniformly compared with the values of comparative example 1 as the benchmark).

[0279] Table 10

[0280] As can be seen from the device data results of Table 10, the comprehensive performance of blue light efficiency (B.I.) and lifetime of device example 1-device example 3 is improved compared to comparative example 1.

[0281] The technical features of the above-described examples can be combined in any manner. In order to make the description concise, not all possible combinations of the technical features in the above-described examples are described, however, as long as the combinations of the technical features do not contradict each other, they should be considered within the scope of the present disclosure.

[0282] The above embodiments only express several implementation manners of the present application, and the description is relatively specific and detailed, but should not be understood as a limitation on the patent scope of the present application. It should be noted that, for ordinary skilled persons in the art, several modifications and improvements can be made without departing from the concept of the present application, and these all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application should be subject to the appended claims.

Claims

1. A mixture comprising a first compound H1, and a second compound H2, wherein the first compound H1 has a structure as shown in general formula (I) or general formula (III): ###0001### ###0002### H1 H2 wherein X1is selected from O, S or Se; Y1-Y4are selected from N or CR 16 ; Ar is selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group having 2 to 30 ring atoms; R1-R 16 each independently selected from H, D, or a linear alkyl, alkoxy, or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above groups can be further replaced by D; L1is selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group; A1is selected from a substituted or unsubstituted heteroaromatic group having 8 to 40 ring atoms, or a heteroaryloxy group having 8 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bound, and A1contains at least one O, S or Se hetero ring atom; at least one of the hetero ring atoms in X1and A1is O; when both are O, the ring atoms of A1do not contain N; when one of them is O and the other is selected from S, Se, then at least one of the ring atoms of A1and Y1-Y4is N; The second compound H2 has a structure as shown in general formula (II): wherein Z1-Z3are selected from N or CR 17 and wherein at least one is selected from N; L2-L4are defined as L1above; Ar1-Ar3are each independently selected from one of the groups depicted in general formula (II-1) to general formula (II-7): wherein "*" indicates the position of the bond; W1-W2are selected from O, S or Se; m1is an integer from 0 to 3, m2is an integer from 0 to 4, and m3is an integer from 0 to 5; R 1 -R 17 R1is as defined above.

2. The mixture of claim 1, wherein, The first compound H1 and the second compound H2 have a semiconductor heterojunction structure of Type II, and the first compound H1 comprises a structure represented by General Formula (I) or General Formula (III), and min [LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1)] ≤ min [E T1 (H1), E T1 (H2)] + 0.1 eV, where LUMO(H1), HOMO(H1), and E T1 (H1) are the lowest unoccupied orbital, the highest occupied orbital, and the triplet energy level of the first compound H1, respectively, and LUMO(H2), HOMO(H2), and E T1 (H2) are the lowest unoccupied orbital, the highest occupied orbital, and the triplet energy level of the second compound H2, respectively.

3. The mixture according to claim 1 or 2, characterized in that, The first compound H1 has a structure as shown in general formula (I-1) - general formula (I-8): X1, X2, X3are independently selected from O, S or Se at each occurrence, and at least one of X1and X2is O, or at least one of X1and X3is O; Y1-Y8are, at each occurrence, selected from N or CR 16 ; n1is an integer from 0 to 2; n2is an integer from 0 to 1; and For general formula (I-1) to general formula (I-8), when X1, X2, X3 are all O, Y1-Y8 are all selected from CR 16 ; for formula (I-1), when X1and X2are different from O, at least one of Y3, Y6and Y7is N; for formula (I-2), when X1and X2are different from O, at least one of Y2, Y3, Y6and Y7is N; for formula (I-3), when X1and X2are different from O, at least one of Y2, Y3, Y6and Y7is N; R is a substituent independently selected from D, or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, cross-linkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in the various groups mentioned above can further be replaced by D.

4. The mixture according to any one of claims 1 to 3, wherein L1 is selected from the group consisting of a single bond or the following bridging groups and combinations thereof: * indicates the position of the bond; the above groups are unsubstituted or at least one H is replaced by R 17 substituted; R 17 R1as defined in claim 1.

5. The mixture according to any one of claims 1 to 4, characterized in that, The mixture further comprises at least one organic functional material, which can be selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitter or host material.

6. A composition comprising a mixture according to any one of claims 1 to 5 and at least one organic solvent.

7. An organic electronic device, characterized in that The organic electronic device comprises at least one mixture according to any of claims 1 to 5.

8. Organic electronic device according to claim 7, characterized in that The organic electronic device is selected from the group consisting of an organic light emitting diode, an organic photovoltaic cell, an organic photoelectric cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronics device, a photodiode, an organic sensor or an organic plasmon emitting diode.

9. Organic electronic device according to claim 8, characterized in that The organic electronic device comprises: a first electrode; a second electrode; and a first organic layer between the first electrode and the second electrode, which first organic layer is an emitting layer and comprises at least one mixture according to any of claims 1 to 5.

10. An organic compound having a structure according to Formula (I-A) or (I-B) or (III-A) or (III-B): ###00009### ###00010### ###00011### ###00012### (I-A) (I-B) (III-A) (III-B) wherein: X1, X2, X3are independently selected from O, S or Se, and at least one of X1, X2in general formula (I-A) or (III-A) or at least one of X1, X3in general formula (I-B) or general formula (III-B) is O; Y1-Y8are selected from N or CR 16 ; n is selected from an integer from 0 to 2; when X1, X2, X3 are all O, Y1-Y8 are all selected from CR 16 ; when X1 and X2 are different from O, or X1 and X3 are different from O, at least one of Y2, Y3, Y6 and Y7 is selected from N; L1is selected from a single bond, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 30 ring atoms; Ar is selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a heteroaromatic group having 2 to 30 ring atoms; R is a substituent independently selected from D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above mentioned groups can be further replaced by D; The organic electronic device is selected from the group consisting of an organic light emitting diode, an organic photovoltaic cell, an organic photoelectric cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronics device, a photodiode, an organic sensor or an organic plasmon emitting diode. R1-R 16 each independently selected from H, D, or a linear alkyl, alkoxy, or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano, carbamoyl, halogenformyl, formyl, isocyano, isocyanate, isothiocyanate, hydroxyl, nitro, CF3, CI, Br, F, crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups; one or more H in each of the above groups can be further replaced by D.

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