Organic compound containing benzophenanthrene and application of organic compound in organic photoelectric device

Abstract

The invention relates to a benzophenanthrene-containing organic compound and application thereof in an organic photoelectric device, the benzophenanthrene-containing organic compound has a structure as shown in a general formula (I), the benzophenanthrene-containing organic compound can be used as an organic photoelectric material, and by introducing a rigid benzophenanthrene structural unit into a BN compound, the organic photoelectric device can be used for preparing the organic photoelectric device. A stable organic light-emitting material can be obtained, and a material solution of an organic photoelectric device is provided. # imgabs0 #

Description

An organic compound containing triphenylene and its application in organic photoelectric devices Technical Field

[0001] The present invention relates to the technical field of organic electronic materials and devices, and in particular to an organic compound containing triphenylene, a polymer, a mixture, and a composition thereof, and applications thereof in organic photoelectric devices, in particular in organic electroluminescent devices. Background Art

[0002] Organic semiconductor materials have great potential in applications in optoelectronic devices such as flat panel displays and lighting due to their diversity in synthesis, relatively low manufacturing costs, and excellent optical and electrical properties.

[0003] To date, luminescent material systems based on BN fused rings with multiple resonance fluorescence have been developed. In blue-light emitting layer materials, triphenylene groups have excellent stability and are widely used as luminescent host materials. Compared with BN fused ring-based multiple resonance luminescent guest materials, the addition of triphenylene groups further narrows the emission spectrum and improves thermal stability. Therefore, the development of more BN-based multiple resonance luminescent materials containing triphenylene groups is of great significance for OLED light-emitting devices.

[0004] For multiple resonance narrow spectrum light emitting devices, the performance of the guest material determines the efficiency and life of the light emitting device. The currently commonly used BN guest material is a multiple resonance BN organic compound, but due to the particularity of its structure, the material thermal stability problem is still large and other shortcomings, and the photoelectric stability of this type of material is limited, resulting in a low device life. In order to further improve the stability of the guest material, the prior art realizes the multiple resonance effect of the molecule by introducing a boron aza-condensed ring unit, forming a better rigid structure, obtaining better material thermal stability, and realizing a narrow emission spectrum. The present invention finds that by introducing a triphenylene group into a BN condensed ring structure, the stability of the material can be further improved without reducing the multiple resonance effect of the material. This type of triphenylene boron aza-condensed organic compound can be applied to fluorescent guest materials, providing a basic structural unit with better performance for the development of multiple resonance fluorescent luminescent materials.

[0005] Therefore, existing technologies, especially material solutions, still need to be improved and developed.

[0006] Summary of the Invention

[0007] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide an organic compound containing triphenylene, a polymer, a mixture, a composition containing the same, and their application in organic optoelectronic devices, aiming to solve the problem of insufficient performance of existing blue light materials.

[0008] The technical solution of the present invention is as follows: an organic compound containing triphenylene has a structure as shown in the general formula (I):

[0009] Wherein: A, B, C, D are the same or different from each other and are independently selected from substituted or unsubstituted C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C 10 -C 60 The present invention relates to a fused ring structural unit, and at least one of A, B, and C is triphenylene. X and Y are independently selected from N or B, and X and Y are different. Ar is selected from formula (a) or formula (b), and the dotted line represents the bonding position, and when Ar is formula (a), L1 and L2 are independently selected from none or a single bond, and when Ar is formula (b), L1 and L2 are both single bonds. Z1, Z2, Z3, Z4, Z5, and Z6 are independently selected from CR1, NR1, N, O, S, S=O, S(=O)2, or C=O, so that chemical formula (a) becomes a five-membered heteroaromatic ring and chemical formula (b) becomes a six-membered aromatic ring or heteroaromatic ring, wherein any two adjacent substituents in Z1-Z6 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring bonded to the group.

[0010] R1, at each occurrence, may be identical or different and is selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 aryloxy group having 4 to 20 C atoms carbonyl, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, 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 an arylamine or heteroarylamine group having 5 to 40 ring atoms, or a combination of these groups.

[0011] The triphenylene-containing organic compound according to the general formula (I) may be further substituted with any substituent R; the substituent R may be the same or different at each occurrence and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, 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 an arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination of these groups.

[0012] The present invention also relates to a polymer comprising at least one repeating unit, wherein the repeating unit comprises a structure corresponding to the above-mentioned triphenylene-containing organic compound.

[0013] The present invention further relates to a mixture comprising an organic compound containing triphenylene as described above, and at least one organic functional material, wherein the organic functional material can be selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminophores or host materials.

[0014] The present invention also relates to a composition comprising the above-mentioned triphenylene-containing organic compound, polymer or mixture, and at least one organic solvent.

[0015] The present invention further relates to an organic optoelectronic device comprising at least one triphenylene-containing organic compound or polymer or mixture as described above.

[0016] The present invention further relates to a color conversion layer comprising a luminophore, wherein the luminophore is a chiral molecule and is selected from the chiral triphenylene-containing organic compound described above.

[0017] Beneficial Effects: By introducing triphenylene structural units into BN compounds, the triphenylene organic compound of the present invention can produce a stable organic light-emitting material. Light-emitting devices prepared with the triphenylene organic compound exhibit high efficiency and longevity. The triphenylene organic compound of the present invention can be used as a functional material in OLED devices. By combining it with other suitable functional materials, the luminous efficiency and lifespan of the OLED device can be improved, thereby providing a material solution for high-efficiency and long-life light-emitting devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1: Absorption and emission spectra of 0.5 mol / L toluene solution of compound 1. DETAILED DESCRIPTION

[0019] The present invention provides an organic compound containing triphenylene and its use in an organic optoelectronic device. To clarify the objectives, technical solutions, and effects of the present invention, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are intended only to illustrate the present invention and are not intended to limit the present invention.

[0020] In the present invention, "substituted" means that a hydrogen atom of a compound is replaced by a substituent.

[0021] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0022] An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. The heteroatom is preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S. A fused ring aromatic group refers to an aromatic group having two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., a fused ring. A fused heterocyclic aromatic group refers to a fused heterocyclic aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, aromatic or heteroaromatic groups include not only aromatic ring systems, but also non-aromatic ring systems. Thus, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, and carbene are also considered aromatic or heterocyclic aromatic groups for the purposes of this invention. For the purposes of this invention, fused aromatic or fused heteroaromatic ring systems include not only systems containing aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, and diaryl ethers are also considered fused aromatic ring systems for the purposes of this invention.

[0023] In the embodiments of the present invention, the energy level structure of the organic material, the singlet energy level S1, the triplet energy level T1, the HOMO, and the LUMO play a key role. The determination of these energy levels is described below.

[0024] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0025] The singlet energy level S1 of an organic material can be determined by luminescence spectroscopy, and the triplet energy level T1 can be measured by low-temperature time-resolved luminescence spectroscopy. S1 and T1 can also be obtained by quantum simulation calculations (e.g., by time-dependent DFT), such as using the commercial software Gaussian 09W (Gaussian Inc.). Specific simulation methods can be found in WO2011141110 or described below in the Examples. ΔE ST Defined as (S1-T1).

[0026] It should be noted that the absolute values ​​of HOMO, LUMO, S1, and T1 depend on the measurement or calculation method used. Even for the same method, different evaluation methods, such as the onset and peak points on a CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement and evaluation methods. In the description of the embodiments of the present invention, the values ​​of HOMO, LUMO, S1, and T1 are based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0027] In the present invention, (HOMO-1) is defined as the second-highest occupied molecular orbital energy level, (HOMO-2) is the third-highest occupied molecular orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied molecular orbital energy level, (LUMO+2) is the third-lowest occupied molecular orbital energy level, and so on.

[0028] The present invention relates to an organic compound containing triphenylene, which has a structure as shown in the general formula (I):

[0029] Wherein: A, B, C, D are the same or different from each other and are independently selected from substituted or unsubstituted C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C 10 -C 60The present invention relates to a fused ring structural unit, wherein at least one of A, B, and C is triphenylene. X and Y are independently selected from N or B, and X and Y are not simultaneously N or B; Ar is selected from formula (a) or formula (b), and the dotted line indicates the bonding position. When Ar is formula (a), L1 and L2 are independently selected from none or a single bond, and when Ar is formula (b), L1 and L2 are both single bonds. Z1, Z2, Z3, Z4, Z5, and Z6 are independently selected from CR1, NR1, N, O, S, S=O, S(=O)2, or C=O, so that chemical formula (a) becomes a five-membered heteroaromatic ring and chemical formula (b) becomes a six-membered aromatic ring or heteroaromatic ring, wherein any two adjacent substituents in Z1-Z6 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring bonded to the group.

[0030] R1, at each occurrence, may be identical or different and is selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 aryloxy group having 4 to 20 C atoms carbonyl, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, I, 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 an arylamine or heteroarylamine group having 5 to 40 ring atoms, or a combination of these groups.

[0031] The triphenylene-containing organic compound according to the general formula (I) may be further substituted with any substituent R; the substituent R may be the same or different at each occurrence and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, 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 an arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination of these groups.

[0032] In some preferred embodiments, A, B, C, and D are the same or different and are independently selected from substituted or unsubstituted C6-C 50 Aromatic ring, C5-C 50 Heteroaromatic ring or C 10 -C 50 In some preferred embodiments, A, B, C, and D are the same or different and are independently selected from substituted or unsubstituted C6-C 40 Aromatic ring, C5-C 40 Heteroaromatic ring or C 10 -C 40 In some more preferred embodiments, A, B, C, and D are the same or different and are independently selected from substituted or unsubstituted C6-C 30 Aromatic ring, C5-C 30 Heteroaromatic ring or C 10 -C 30 In some preferred embodiments, A, B, C, and D are the same or different and are independently selected from substituted or unsubstituted C6-C 20 Aromatic ring, C5-C 20 Heteroaromatic ring or C 10 -C 20 A fused ring structural unit, and at least one of A, B, and C is triphenylene.

[0033] In certain preferred embodiments, A, B, and C are independently selected from benzene or triphenylene, and at least one of A, B, and C is triphenylene. In certain preferred embodiments, A, B, and C are independently selected from benzene or triphenylene, and at least two of A, B, and C are triphenylene. In certain preferred embodiments, A, B, and C are all triphenylene.

[0034] In certain preferred embodiments, D is a group with a large steric hindrance structure, wherein a "large steric hindrance group" refers to a group that can significantly improve molecular planarity. By introducing a large steric hindrance group, the planarity of the overall molecular structure can be greatly improved, thereby improving packing. "Planarity" refers to the difference between a molecule and an ideal plane. The degree of overall molecular planarity can be measured by theoretically calculating the "Molecular Planarity Parameter" value. A smaller MPP value indicates a more planar molecule, and an MPP value of 0 represents an ideal plane.

[0035] In certain embodiments, the triphenylene-containing organic compound is selected from the structure shown in one of the general formulas (I-1) to (I-14):

[0036] Wherein, L1-L2, Z1-Z6, A, B, C, D, X and Y are defined as above.

[0037] In certain preferred embodiments, when only one of A, B, and C is triphenylene, the triphenylene-containing organic compound is not a structure represented by the following general formula:

[0038] Wherein, L1-L2, Z1-Z6, B, C, D, X and Y are defined as above.

[0039] In certain preferred embodiments, when only two of A, B, and C are triphenylene, the triphenylene-containing organic compound is not of the structure shown in the following general formula:

[0040] Wherein, L1-L2, Z1-Z6, C, D, X and Y are defined as above.

[0041] In some embodiments, the triphenylene-containing organic compound is selected from the structures shown in Formula (Ia-1) to Formula (Ia-13) and Formula (Ib-1) to Formula (Ib-37):

[0042] Wherein, the definitions of X and Y are the same as above.

[0043] In some preferred embodiments, the triphenylene-containing organic compound is selected from the structures shown in formula (IIa-1) to formula (IIa-7) and formula (IIb-1) to formula (IIb-31):

[0044] Wherein, X, Y, and R are as defined above, and n is selected from 0, 1, 2, 3, and 4.

[0045] In certain embodiments, A, B, C, and D, at each occurrence, are independently selected from the following groups:

[0046] Where: w appears each time and is independently selected from CR 1 R 2 NR 1 、O、S、SiR 1 R 2 PR 1 、P(=O)R 1 , S=O, S(=O)2 or C=O; v each occurrence is independently selected from CR 3 or N; R 1 -R 3Each occurrence is independently selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1-20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl group having 3-20 C atoms, or a keto group having 1-20 C atoms, or an alkoxycarbonyl group having 2-20 C atoms, or an aryloxycarbonyl group having 7-20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic group or heteroaromatic group having 5-60 ring atoms, or an aryloxy or heteroaryloxy group having 5-60 ring atoms, or a combination of these groups.

[0047] In some preferred embodiments, the aromatic group or heteroaromatic group is selected from the following groups:

[0048] Wherein, the definitions of w and v are the same as above.

[0049] More preferably, the aromatic group or heteroaromatic group is selected from:

[0050] Wherein, the definitions of w and v are the same as above.

[0051] Furthermore, the aromatic group is selected from the group consisting of benzene, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; the heteroaromatic group is selected from the group consisting of benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0052] In some preferred embodiments, A, B, C, and D, at each occurrence, are independently selected from the following groups:

[0053] Among them: The H atoms on the ring can be further substituted.

[0054] In certain preferred embodiments, the above-mentioned triphenylene-containing organic compound, wherein A, B, C, and D, when each occurs, may be further selected from the following structural units or their combinations:

[0055] Where n1 is 1 or 2 or 3 or 4.

[0056] In certain embodiments, each occurrence of the substituent R is independently selected from the following groups:

[0057] Wherein, the definitions of w and v are the same as above.

[0058] In some preferred embodiments, the organic compound containing phenylene is selected from the structures shown in general formula (IIc-1) to general formula (IIc-31), and its planar configuration is distorted by introducing a large steric group (Z ring). By adjusting the different substituents contained in the large steric group, the π-π mutual attraction caused by the introduction of the benzene ring is weakened, and the intermolecular force is further weakened, thereby reducing the adverse effect of the concentration quenching effect on the efficiency. At the same time, the introduction of a large steric group can reduce stacking, which is beneficial to maintaining the stability of the PL spectrum.

[0059] Wherein: X, Y, R, and n are as defined above.

[0060] In certain preferred embodiments, D is selected from C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C 10 -C 60 fused ring structural unit.

[0061] In certain preferred embodiments, the substituent Z is selected from bulky steric groups represented by formula (IIIa) or formula (IIIb):

[0062] Wherein: P is substituted at the adjacent position relative to Q, and P and Q are independently selected from substituted or unsubstituted C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C8-C 60 Each time V0 appears, it is independently selected from CR 4 or N; R 4 The definition of is the same as that of R1 above, and * represents the connection site (the site where the connecting body and D are fused).

[0063] In some preferred embodiments, at least one V0 in the general formula (IIIb) is N; in some more preferred embodiments, at least two V0 in the general formula (IIIb) are N; in some more preferred embodiments, all three V0 in the general formula (IIIb) are N.

[0064] In some embodiments, P and Q are independently selected from the following structures:

[0065] Wherein: the definitions of w and v are the same as above.

[0066] In certain preferred embodiments, the substituent Z is selected from the following bulky steric groups:

[0067] Wherein: w and v are defined as above. P, as a substituent, can replace any H on the ring. At the same time, when there is any substitution of P in the above-mentioned groups with large steric structure, at least one v on the corresponding ring is selected from CR 3 , and R 3 Selected from H.

[0068] Specific: Structural formula For example, some of its combinations are as follows:

[0069] Wherein: * represents the connection site, and the definitions of w and v are the same as above.

[0070] In certain preferred embodiments, R is selected from benzene or naphthalene.

[0071] In certain preferred embodiments, R is selected from heteroaromatic groups.

[0072] In some preferred embodiments, the organic compound containing triphenylene is at least partially deuterated, preferably 10% or more of the H is deuterated, more preferably 20% or more of the H is deuterated, very preferably 30% or more of the H is deuterated, and most preferably 40% or more of the H is deuterated.

[0073] In a preferred embodiment, the triphenylene-containing organic compound is a chiral molecule, and its preferred spin mode is a P-type chiral molecule; in other embodiments, the triphenylene-containing organic compound is an M-type chiral molecule.

[0074] The general method for separating chiral molecules is to dissolve the chiral compound in an organic solvent and separate and purify the P- and M-type chiral compounds by chiral separation column chromatography.

[0075] Preferably, the chiral triphenylene-containing organic compound is selected from one of the aforementioned general formulas (I-4) to (I-7) and (I-11) to (I-14).

[0076] More preferably, the above-mentioned chiral triphenylene-containing organic compound is selected from one of the aforementioned general formulas (Ia-6), (Ia-7), (Ib-6), (Ib-7), (Ib-13), (Ib-14), (Ib-15), (Ib-17), (Ib-23)-(Ib-31).

[0077] The specific structures of the organic compounds containing triphenylene according to the present invention are listed below, but are not limited thereto, wherein the bonds indicated in bold are chiral molecules:

[0078] The organic compound containing triphenylene according to the present invention can be used as a functional material in optical devices, such as color converters, or electronic devices, especially electroluminescent devices. The electroluminescent device can be selected from OLED, OLEEC, and organic light-emitting field-effect transistors; OLED devices are particularly preferred. Organic functional materials can be divided into 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, host materials (Host) and organic dyes. In some preferred embodiments, the organic compound containing triphenylene according to the present invention can be used as a host material, an electron transport material or a hole transport material.

[0079] In some preferred embodiments, the light emission wavelength of the electroluminescent device is 300 nm-1500 nm, preferably 400 nm-1000 nm, and more preferably 400 nm-800 nm.

[0080] In certain embodiments, the triphenylene-containing organic compound according to the present invention has a luminescent function, and the luminescent wavelength is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm. The luminescence referred to here refers to photoluminescence or electroluminescence.

[0081] In some preferred embodiments, the triphenylene-containing organic compound according to the present invention can be used as a fluorescent guest material.

[0082] The fluorescent guest material must have an appropriate singlet energy level, i.e., S1. In certain embodiments, the triphenylene-containing organic compound according to the present invention has S1 ≥ 2.3 eV, preferably ≥ 2.4 eV, more preferably ≥ 2.5 eV, and most preferably ≥ 2.6 eV.

[0083] As a fluorescent guest material, it must have a high photoluminescence quantum efficiency, i.e., PLQY. In certain embodiments, the triphenylene-containing organic compound according to the present invention has a PLQY of ≥40%, preferably ≥50%, more preferably ≥60%, and most preferably ≥70%.

[0084] The PLQY of a compound is generally positively correlated with its resonance factor f1 (calculated as follows). In a preferred embodiment, the f1 of the triphenylene-containing organic compound is ≥0.3, preferably ≥0.4, more preferably ≥0.5, and most preferably ≥0.6.

[0085] In a preferred embodiment, the organic compound containing triphenylene is a green light emitting material; in other embodiments, the organic compound containing triphenylene is an orange or red light emitting material.

[0086] In other preferred embodiments, the full width at half maximum (FWHM) of the luminescence spectrum of the triphenylene-containing organic compound is ≤40 nm, preferably ≤35 nm, and most preferably ≤35 nm.

[0087] In certain preferred embodiments, the triphenylene-containing organic compound according to the present invention is a thermally excited delayed fluorescent material (TADF material). Generally, the triphenylene-containing organic compound according to the present invention has a ΔE ST ≤0.3eV, preferably ≤0.25eV, more preferably ≤0.2eV, most preferably ≤0.15eV.

[0088] As an organic functional material, it is desirable to have good thermal stability. Generally, the triphenylene-containing organic compound according to the present invention has a glass transition temperature (Tg) of ≥ 100°C, preferably Tg ≥ 140°C, and more preferably Tg ≥ 180°C.

[0089] In certain preferred embodiments, the triphenylene-containing organic compound according to the present invention has (HOMO-(HOMO-1)) ≥ 0.2 eV, preferably ≥ 0.3 eV, more preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0090] In other preferred embodiments, the triphenylene-containing organic compound according to the present invention has ((LUMO+1)-LUMO) ≥ 0.15 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.30 eV, and most preferably ≥ 0.35 eV.

[0091] The present invention also relates to a polymer comprising at least one repeating unit, wherein the repeating unit comprises a structure corresponding to the above-mentioned triphenylene-containing organic compound.

[0092] In certain embodiments, the polymer is a non-conjugated polymer, wherein the structure shown in formula (I) is on the side chain. In another preferred embodiment, the polymer is a conjugated polymer.

[0093] In a preferred embodiment, the synthesis method of the polymer is selected from SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, HARTWIG-BUCHWALD- and ULLMAN.

[0094] In a preferred embodiment, the polymer according to the present invention has a glass transition temperature (Tg) ≥ 100°C, preferably ≥ 120°C, more preferably ≥ 140°C, even more preferably ≥ 160°C, and most preferably ≥ 180°C.

[0095] In a preferred embodiment, the molecular weight distribution (PDI) of the polymer according to the present invention is preferably in the range of 1 to 5, more preferably 1 to 4, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1 to 1.5.

[0096] In a preferred embodiment, the weight average molecular weight (Mw) of the polymer according to the present invention is preferably in the range of 10,000 to 1,000,000, more preferably 50,000 to 500,000, more preferably 100,000 to 400,000, even more preferably 150,000 to 300,000, and most preferably 200,000 to 250,000.

[0097] In certain preferred embodiments, the polymer according to the present invention has (HOMO-(HOMO-1)) ≥ 0.2 eV, preferably ≥ 0.3 eV, more preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0098] The present invention also relates to a mixture comprising an organic compound or polymer containing triphenylene as described above, and at least one organic functional material. The organic functional material is 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, a luminophore or a host material. The luminophore is selected from a singlet luminophore (fluorescent luminophore), a triplet luminophore (phosphorescent luminophore) and an organic thermally excited delayed fluorescence material (TADF material). For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0099] In certain embodiments, the mixture comprises at least one triphenylene-containing organic compound according to the present invention and a fluorescent host. The triphenylene-containing organic compound according to the present invention can be used as the fluorescent guest material in an amount of ≤10 wt %, preferably ≤9 wt %, more preferably ≤8 wt %, particularly preferably ≤7 wt %, and most preferably ≤5 wt %.

[0100] In other preferred embodiments, the mixture comprises at least one triphenylene-containing organic compound according to the present invention, a blue-light emitting material, and a fluorescent host material. The triphenylene-containing organic compound according to the present invention and the blue-light emitting material form a fluorescent co-guest material, with a weight ratio of 2:8 to 8:2, preferably 3:7 to 7:3, and most preferably 4:6 to 6:4. In a preferred embodiment, the emission spectrum of the blue-light emitting material and the absorption spectrum of the triphenylene-containing organic compound according to the present invention at least partially overlap, thereby enabling efficient energy transfer from the blue-light emitting material to the triphenylene-containing organic compound according to the present invention.

[0101] A detailed description of the host material, fluorescent light-emitting material, TADF material and other organic functional materials can be found in WO2018095395. The entire contents of this patent document are hereby incorporated herein by reference.

[0102] One object of the present invention is to provide a material solution for vapor deposition type OLEDs.

[0103] In certain embodiments, the triphenylene-containing organic compound according to the present invention has a molecular weight of ≤1100 g / mol, preferably ≤1000 g / mol, very preferably ≤950 g / mol, more preferably ≤900 g / mol, and most preferably ≤800 g / mol.

[0104] Another object of the present invention is to provide a material solution for printed OLEDs.

[0105] In certain embodiments, the triphenylene-containing organic compound according to the present invention has a molecular weight of ≥700 g / mol, preferably ≥900 g / mol, more preferably ≥1000 g / mol, and most preferably ≥1100 g / mol.

[0106] In other embodiments, the solubility of the triphenylene-containing organic compound according to the present invention in toluene at 25° C. is ≥10 mg / mL, preferably ≥15 mg / mL, and most preferably ≥20 mg / mL.

[0107] The present invention further relates to a composition or ink comprising a triphenylene-containing organic compound or polymer or mixture as described above, and at least one organic solvent.

[0108] When used in printing processes, ink viscosity and surface tension are important parameters. The appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method.

[0109] In a preferred embodiment, the surface tension of the ink according to the present invention at operating temperature or at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0110] In another preferred embodiment, the viscosity of the ink according to the present invention at operating temperature or 25° C. is in the range of about 1 cps to 100 cps; more preferably, in the range of 1 cps to 50 cps; more preferably, in the range of 1.5 cps to 20 cps; and most preferably, in the range of 4.0 cps to 20 cps. Such a formulated composition will facilitate inkjet printing.

[0111] Viscosity can be adjusted by various methods, such as by selecting the appropriate solvent and adjusting the concentration of the functional material in the ink. The ink containing the metal organic complex or polymer according to the present invention facilitates adjustment of the printing ink within an appropriate range according to the printing method used. Generally, the weight ratio of the functional material contained in the composition of the present invention is in the range of 0.3% to 30% by weight, preferably in the range of 0.5% to 20% by weight, more preferably in the range of 0.5% to 15% by weight, even more preferably in the range of 0.5% to 10% by weight, and most preferably in the range of 1% to 5% by weight.

[0112] In some embodiments, according to the ink of the present invention, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents, in particular aliphatic chain / ring substituted aromatic solvents, or aromatic ketone solvents or aromatic ether solvents.

[0113] Examples of organic solvents suitable for the present invention include, but are not limited to: aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dimethylbenzene, Hexylbenzene, dibutylbenzene, p-diisopropylbenzene, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzoic acid benzyl esters, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.; ketone-based solvents: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, isophorone, 2,6,8-trimethyl-4- Nonanone, fenchone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-amyl ketone; aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylhexane, 1,2,4-trimethoxybenzene, 4- (1-Propylene)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether; ester solvents: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0114] Further, according to the ink of the present invention, the at least one organic solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0115] In some other embodiments, the printing ink further comprises another organic solvent. Examples of the other organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0116] In a preferred embodiment, the composition according to the present invention is a solution.

[0117] In another preferred embodiment, the composition according to the present invention is a suspension.

[0118] The composition in the embodiment of the present invention may include 0.01wt% to 20wt% of the organic compound containing triphenylene according to the present invention or a mixture thereof, preferably 0.1wt% to 15wt%, more preferably 0.2wt% to 10wt%, and most preferably 0.25wt% to 5wt% of the organic compound containing triphenylene or a mixture thereof.

[0119] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of an organic optoelectronic device, and is particularly preferably prepared by printing or coating.

[0120] Suitable printing or coating techniques include, but are not limited to, inkjet printing, nozzle printing, gravure printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush coating or pad printing, slot die coating, and the like. Inkjet printing, nozzle printing, and gravure printing are preferred. The solution or suspension may further include one or more components, such as a surfactant, lubricant, wetting agent, dispersant, hydrophobic agent, adhesive, etc., to adjust viscosity, film-forming properties, and improve adhesion. For detailed information on printing techniques and their requirements for the relevant solutions, such as solvents, concentrations, and viscosities, please refer to "Handbook of Print Media: Technologies and Production Methods," edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0121] Based on the above-mentioned triphenylene-containing organic compound, the present invention further provides an application of the above-mentioned triphenylene-containing organic compound or polymer, that is, applying the triphenylene-containing organic compound or polymer to an organic optoelectronic device. The organic optoelectronic device can be selected from, but not limited to, color converters, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPEDs). Organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors (OLEDs), are particularly preferred. In an embodiment of the present invention, the triphenylene-containing organic compound is preferably used in the light-emitting layer of an electroluminescent device.

[0122] The present invention further relates to an organic optoelectronic device comprising at least one triphenylene-containing organic compound, polymer, or mixture as described above. Generally, such an organic optoelectronic device comprises at least one cathode, an anode, and a functional layer disposed between the cathode and the anode, wherein the functional layer comprises at least one triphenylene-containing organic compound or polymer as described above. The organic optoelectronic device may be selected from, but is not limited to, color converters, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes (OPDs). Organic electroluminescent devices, such as OLEDs, OLEECs, and OLEDs, are particularly preferred.

[0123] In some particularly preferred embodiments, the organic optoelectronic device comprises a light-emitting layer, which comprises an organic compound or polymer or mixture containing triphenylene, or comprises an organic compound containing triphenylene and a phosphorescent light-emitting body, or comprises an organic compound containing triphenylene and a host material, or comprises an organic compound containing triphenylene, a phosphorescent light-emitting body and a host material.

[0124] The organic photoelectric device described above, especially the OLED, includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0125] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic with a glass transition temperature (Tg) of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene (2,6-naphthalene) (PEN).

[0126] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most 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 and can be readily selected for use by one of ordinary skill in the art. 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, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0127] The cathode can comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In a preferred embodiment, the absolute difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes in OLEDs are possible cathode materials for the devices of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, 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, electron beam (e-beam), and the like.

[0128] OLEDs may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Suitable materials for these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated by reference.

[0129] In a preferred embodiment, in the organic optoelectronic device according to the present invention, the light-emitting layer thereof is prepared by the composition according to the present invention.

[0130] The organic optoelectronic device according to the present invention, especially the OLED, has a light emission wavelength between 300 nm and 1500 nm, preferably between 350 nm and 1200 nm, and more preferably between 400 nm and 800 nm.

[0131] For the purposes of the present invention, color converter, color conversion layer, and CCL have the same meaning.

[0132] The present invention further relates to a color conversion layer comprising a light emitter, wherein the light emitter is a chiral molecule.

[0133] In some embodiments, the luminescent body comprises the chiral triphenylene-containing organic compound or polymer.

[0134] In a preferred embodiment, the color conversion layer comprises a host material and a triphenylene-containing organic compound or polymer according to the present invention as a guest material, as described in the prior application WO2022213993A1, the entire contents of which are hereby incorporated by reference.

[0135] In a preferred embodiment, in the color conversion layer, the chiral light-emitting body is selected from the above-mentioned chiral triphenylene-containing organic compounds.

[0136] Preferably, in the color conversion layer, the chiral triphenylene-containing organic compound is selected from one of the aforementioned general formulas (I-4) to (I-7) and (I-11) to (I-14).

[0137] More preferably, in the color conversion layer, the chiral organic compound containing benzophenone is selected from one of the aforementioned general formulas (Ia-6), (Ia-7), (Ib-6), (Ib-7), (Ib-13), (Ib-14), (Ib-15), (Ib-17), (Ib-23)-(Ib-31).

[0138] The present invention also relates to applications of the organic optoelectronic device according to the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0139] The present invention also relates to electronic devices comprising the organic optoelectronic device according to the present invention, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0140] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0141] Specific embodiments

[0142] 1. Synthesis of compounds

[0143] Example 1

[0144] The synthetic route of compound 1 is as follows:

[0145] The specific synthesis steps are as follows:

[0146] Synthesis of Compound 1-1: Under argon atmosphere, 3,6-di-tert-butylcarbazole (5.58 g, 20.0 mmol), cesium carbonate (9.77 g, 30.0 mmol), 1-bromo-2,6-difluorobenzene (5.64 g, 30.0 mmol), and 60 mL of ultra-dry DMF were added to a 250 mL single-necked flask and stirred at 150°C for 22 h. The reaction system was cooled to room temperature and poured into water. The crude product obtained by filtration was purified by column chromatography (eluent: PE) and recrystallized from dichloromethane and methanol to obtain 5.03 g of a white solid (Compound 1-1) with a yield of 56%. 1 HNMR (400MHz, CDCl3, 297K, ppm) δ8.16 (d, J = 2.0Hz, 2H), 7.50-7.43 (m, 3H), 7.34-7.26 (m, 2H), 7.00 (dd, J = 8.8Hz, 2.4Hz, 2H), 1.48 (s, 18H). 13 C NMR (101MHz, CDCl3, 297K, ppm) δ143.25,139.50,139.30,129.22,129.13,126.42,123.83,123.51,116.52,116.24,111.60,109.62,34.90,32.17. 19 F NMR(376MHz,CDCl3,297K,ppm)δ-102.47.HRMS(MALDI)m / z:Calcd.for C 26 H 27 BrFN:451.1311;Found:451.1305[M] + .

[0147] Synthesis of Compound 1-2: Under argon atmosphere, compound 1-1 (321 mg, 0.710 mmol), 7H-diphenanthrocarbazole (500 mg, 1.07 mmol), cesium carbonate (1.16 g, 3.56 mmol), and 12 mL of ultra-dry DMF were added to a 50 mL Schlenk flask and stirred at 155°C for 16 h. After the reaction system was cooled to room temperature, the mixture was extracted three times with dichloromethane. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The crude product obtained by filtration was purified by column chromatography (eluent: PE / CH2Cl2 = 10:1) and recrystallized from dichloromethane and methanol to obtain 338 mg of a light yellow solid (Compound 1-2) in a 53% yield. 1 HNMR (400MHz, CD2Cl2, 297K, ppm) δ8.91-8.81(m,2H),8.80-8.70(m,4H),8.48(t,J=8.0Hz,2H), 8.23-8.18(m,2H),8.08-7.84(m,6H),7.78-7.67(m,5H),7.65-7.53(m,3H),7.31-7.20(m,3H),6.42-6.34(m,2H).1.47(s,18H). 13 C NMR (101MHz, CDCl3, 297K, ppm) δ143.46,143.44,141.24,140.87,140.21,139.34,139.27,138.86,132.02,131.64,13 0.84,130.64,129.78,129.55,129.52,128.73,128.68,128.44,128.16,127.86,127.28,127.25,127.11,127.09,126. 58,126.18,126.14,124.98,124.89,124.67,124.03,124.02,123.76,123.69,123.68,123.61,123.42,123.38,121.96 ,121.87,118.98,118.79,116.72,116.67,110.38,110.26,109.64,109.56,34.97,32.20.HRMS(MALDI)m / z:Calcd.for C 62 H 47 BrN2:898.2923; Found:898.2936[M] + .

[0148] Synthesis of Compound 1: Under argon, compound 1-2 (300 mg, 0.334 mmol) and 4 mL of o-dichlorobenzene were added to a 50 mL Shrek tube. n-Butyl lithium (0.668 mmol, 1.6 M in hexane) was added at 0°C and stirred for 2 h. Boron tribromide (10.8 mmol, 1.0 M in heptane) was then added dropwise at 0°C. The mixture was then stirred at room temperature for 16 h. After removing the low-boiling solvent under reduced pressure, N,N-diisopropylethylamine (0.1 mL) was added dropwise at 0°C and stirred at 180°C for 12 h. The mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the product was purified by column chromatography (eluent: PE / CH2Cl2 = 5:1). The product was recrystallized from dichloromethane and methanol to afford 50 mg of an orange solid (Compound 1) in an 18% yield. 1 HNMR (400MHz, CD2Cl2, 297K, ppm) δ10.03(s,1H),9.03(d,J=1.6Hz,1H),8.84(d,J=8Hz,1H ),8.61-8.53(m,2H),8.48-8.44(m,1H),8.42(d,J=1.6Hz,1H),8.37-8.31(m,4H),8.20(d, J=2.4Hz,1H),8.10(d,J=8.8Hz,1H),7.98(t,J=7.6Hz,2H),7.77-7.72(m,2H),7.68-7.63( m,1H),7.61-7.50(m,5H),7.19-7.12(m,2H),6.26-6.20(m,2H),1.69(s,9H),1.55(s,9H). 13C NMR (101MHz, CD2Cl2, 297K, ppm) δ145.88,145.16,144.09,143.65,142.59,141.90,140.21,138.70,133.33,131.41,130.70,1 30.57,130.52,130.04,129.94,129.84,129.36,129.33,129.27,128.17,127.96,127.86,127.77,127.60,127.56,127.46,126 .84,125.91,125.75,125.16,125.11,124.96,124.34,124.08,124.03,123.78,123.50,123.25,122.43,122.36,122.27,121. 74,121.55,121.25,118.94,117.85,114.74,114.16,109.64,109.57,35.65,35.24,32.51,32.16.HRMS(MALDI)m / z:Calcd.for C 62 H 45 BN2:828.3676; Found:828.3675[M] + .

[0149] Example 2

[0150] The synthetic route of compound 2 is as follows:

[0151] The specific synthesis steps are as follows:

[0152] Synthesis of compound 2-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 2-2 was formed under the action of a base with a yield of 30% and MS (ASAP) = 787.76.

[0153] Synthesis of Compound 2: The synthesis process is similar to that of Compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product Compound 2 is formed with a yield of 15% and MS (ASAP) = 716.65.

[0154] Example 3

[0155] The synthetic route of compound 3 is as follows:

[0156] Synthesis of compound 3-1: The synthesis steps were similar to those of compound 1-1. The intermediate compound 3-1 was formed under the action of a base with a yield of 54% and MS (ASAP) = 490.38.

[0157] Synthesis of compound 3-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 3-2 was formed under the action of a base with a yield of 50% and MS (ASAP) = 937.94.

[0158] Synthesis of compound 3: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 3 is formed with a yield of 21% and MS (ASAP) = 866.83.

[0159] Example 4

[0160] The synthetic route of compound 4 is as follows:

[0161] Synthesis of compound 4-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 4-2 was formed under the action of a base with a yield of 28% and MS (ASAP) = 1088.12.

[0162] Synthesis of compound 4: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 4 is formed with a yield of 12% and MS (ASAP) = 1003.99.

[0163] Example 5

[0164] The synthetic route of compound 5 is as follows:

[0165] Synthesis of compound 5-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 5-2 was formed under the action of a base with a yield of 58% and MS (ASAP) = 749.80.

[0166] Synthesis of Compound 5: The synthesis process was similar to that of Compound 1. Under the action of n-butyl lithium, Li salt was formed, and then under the action of BBr 3 , the final product Compound 5 was formed with a yield of 25% and MS (ASAP) = 678.69.

[0167] Example 6

[0168] The synthetic route of compound 6 is as follows:

[0169] Synthesis of compound 6-1: The synthesis steps were similar to those of compound 1-1. The intermediate compound 6-1 was formed under the action of a base with a yield of 50% and MS (ASAP) = 380.22.

[0170] Synthesis of compound 6-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 6-2 was formed under the action of a base with a yield of 44% and MS (ASAP) = 827.78.

[0171] Synthesis of compound 6: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 6 is formed with a yield of 10% and MS (ASAP) = 756.67.

[0172] Example 7

[0173] The synthetic route of compound 7 is as follows:

[0174] Synthesis of compound 7-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 7-2 was formed under the action of a base with a yield of 48% and MS (ASAP) = 667.56.

[0175] Synthesis of compound 7: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 7 is formed with a yield of 16% and MS (ASAP) = 596.45.

[0176] Example 8

[0177] The synthetic route of compound 8 is as follows:

[0178] Synthesis of compound 8-1: The synthesis steps were similar to those of compound 1-1. The intermediate compound 8-1 was formed under the action of a base with a yield of 45% and MS (ASAP) = 546.46.

[0179] Synthesis of compound 8-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 8-2 was formed under the action of a base with a yield of 47% and MS (ASAP) = 849.86.

[0180] Synthesis of Compound 8: The synthesis process was similar to that of Compound 1. Under the action of n-butyllithium, Li salt was formed, and then under the action of BBr3, the final product, Compound 8, was formed with a yield of 14% and MS (ASAP) = 778.75.

[0181] Example 9

[0182] The synthetic route of compound 9 is as follows:

[0183] Synthesis of compound 9-2: The classical Hartwig reaction was used to synthesize the compound. The difference in the reactivity of halogen atoms was utilized to preferentially react with iodine to form a CN bond. Under the catalysis of Pd, the reaction yield was 50%, and its MS (ASAP) = 855.10.

[0184] Synthesis of compound 9: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 9 is formed with a yield of 45% and MS (ASAP) = 713.45.

[0185] Example 10

[0186] The synthetic route of compound 10 is as follows:

[0187] Synthesis of compound 10-1: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 70%, MS (ASAP) = 364.24.

[0188] Synthesis of compound 10-2: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 80%, MS (ASAP) = 735.48.

[0189] Synthesis of compound 10: The synthesis process is similar to that of compound 9. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 10 is formed with a yield of 48% and MS (ASAP) = 593.26.

[0190] Example 11

[0191] The synthetic route of compound 11 is as follows:

[0192] Synthesis of compound 11-1: The synthesis steps were similar to those of compound 1-1. The intermediate compound 11-1 was formed under the action of a base with a yield of 64% and MS (ASAP) = 330.16.

[0193] Synthesis of compound 11-2: The synthesis steps were similar to those of compound 1-2. The intermediate compound 11-2 was formed under the action of a base with a yield of 62% and MS (ASAP) = 627.54.

[0194] Synthesis of compound 11: The synthesis process is similar to that of compound 1. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 11 is formed with a yield of 18% and MS (ASAP) = 556.43.

[0195] Example 12

[0196] The synthetic route of compound 12 is as follows:

[0197] Synthesis of compound 12-1: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 66%, MS (ASAP) = 330.24.

[0198] Synthesis of compound 12-2: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 68% and MS (ASAP) = 711.52.

[0199] Synthesis of compound 12: The synthesis process is similar to that of compound 9. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 12 is formed with a yield of 25% and MS (ASAP) = 569.30.

[0200] Example 13

[0201] The synthetic route of compound 13 is as follows:

[0202] The specific synthesis steps are as follows:

[0203] Synthesis of Compound 13b: Under argon, 7H-diphenanthrocarbazole (5 g, 10.7 mmol), cesium carbonate (20 g, 300.0 mmol), Compound 13a, and 300 mL of ultra-dry DMF were added to a 5000 mL single-necked flask and stirred at 150°C for 22 h. The reaction system was cooled to room temperature and poured into water. The crude product was filtered and purified by column chromatography (eluent: PE). The product was recrystallized from dichloromethane and methanol to afford 4.03 g of a white solid (Compound 13b) in a 42% yield.

[0204] Synthesis of Compound 13c: Under argon, compound 13b (3 g, 2.4 mmol), carbazole (1 g, 2.14 mmol), cesium carbonate (1.16 g, 3.56 mmol), and 12 mL of ultra-dry DMF were added to a 50 mL Schlenk flask and stirred at 155°C for 16 h. After the reaction system was cooled to room temperature, the mixture was extracted three times with dichloromethane. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The crude product obtained by filtration was purified by column chromatography (eluent: PE / CH2Cl2 = 10:1) and recrystallized from dichloromethane and methanol to give 2.1 g of a light yellow solid (Compound 13c) in a 53% yield.

[0205] Synthesis of Compound 13: Under argon, compound 13c (300 mg, 0.114 mmol) and 4 mL of o-dichlorobenzene were added to a 50 mL Shrek tube. n-Butyl lithium (0.3 mmol, 1.6 M in hexane) was added at 0°C and stirred for 2 h. Boron tribromide (5.4 mmol, 1.0 M in heptane) was then added dropwise at 0°C. The mixture was then stirred at room temperature for 16 h. After removing the low-boiling solvent under reduced pressure, N,N-diisopropylethylamine (0.1 mL) was added dropwise at 0°C and stirred at 180°C for 12 h. The mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the product was purified by column chromatography (eluent: PE / CH2Cl2 = 5:1). The product was recrystallized from dichloromethane and methanol to afford 50.12 mg of an orange solid (Compound 13) in a 10% yield.

[0206] Example 14

[0207] The synthetic route of compound 14 is as follows:

[0208] The specific synthesis steps are as follows:

[0209] Synthesis of Compound 14b: Under argon, 7H-diphenanthrocarbazole (5 g, 10.7 mmol), cesium carbonate (20 g, 300.0 mmol), Compound 14a, and 300 mL of ultra-dry DMF were added to a 5000 mL single-necked flask and stirred at 150°C for 22 h. The reaction system was cooled to room temperature and poured into water. The crude product was filtered and purified by column chromatography (eluent: PE). Recrystallization from dichloromethane and methanol afforded 4.12 g of a white solid (Compound 14b) in a 43% yield.

[0210] Synthesis of Compound 14c: Under argon, compound 14b (3 g, 2.7 mmol), carbazole (1.5 g, 3.21 mmol), cesium carbonate (1.16 g, 3.56 mmol), and 12 mL of ultra-dry DMF were added to a 50 mL Schlenk flask and stirred at 155°C for 16 h. After the reaction system was cooled to room temperature, the mixture was extracted three times with dichloromethane. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The crude product obtained by filtration was purified by column chromatography (eluent: PE / CH2Cl2 = 10:1) and recrystallized from dichloromethane and methanol to give 2.18 mg of a light yellow solid (Compound 14c) in a 53% yield.

[0211] Synthesis of Compound 14: Under argon, compound 14c (300 mg, 0.114 mmol) and 4 mL of o-dichlorobenzene were added to a 50 mL Shrek tube. n-Butyl lithium (0.3 mmol, 1.6 M in hexane) was added at 0°C and stirred for 2 h. Boron tribromide (5.4 mmol, 1.0 M in heptane) was then added dropwise at 0°C. The mixture was then stirred at room temperature for 16 h. After removing the low-boiling solvent under reduced pressure, N,N-diisopropylethylamine (0.1 mL) was added dropwise at 0°C and stirred at 180°C for 12 h. The mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the product was purified by column chromatography (eluent: PE / CH2Cl2 = 5:1). The product was recrystallized from dichloromethane and methanol to afford 50.23 mg of an orange solid (Compound 14) in an 11% yield.

[0212] Example 15

[0213] The synthetic route of compound 15 is as follows:

[0214] Synthesis of compound 15b: The synthesis steps were similar to those of compound 14c. An intermediate compound was formed under the action of a base with a yield of 51% and MS (ASAP) = 1183.

[0215] Synthesis of compound 15: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 15 is formed with a yield of 12% and MS (ASAP) = 1157.

[0216] Example 16

[0217] The synthetic route of compound 16 is as follows:

[0218] Synthesis of compound 16a: The synthesis steps were similar to those of compound 14c. An intermediate compound was formed under the action of a base with a yield of 51% and MS (ASAP) = 1147.

[0219] Synthesis of compound 16: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 16 is formed with a yield of 12% and MS (ASAP) = 1121.

[0220] Example 17

[0221] The synthetic route of compound 17 is as follows:

[0222] Synthesis of compound 17a: The synthesis steps were similar to those of compound 14c. An intermediate compound was formed under the action of a base with a yield of 51% and MS (ASAP) = 1382.

[0223] Synthesis of compound 17: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 17 is formed with a yield of 11% and MS (ASAP) = 1357.

[0224] Example 18

[0225] The synthetic route of compound 18 is as follows:

[0226] Synthesis of compound 18b: The synthesis steps were similar to those of compound 14b. An intermediate compound was formed under the action of a base with a yield of 50% and MS (ASAP) = 903.46.

[0227] Synthesis of compound 18c: The synthesis steps were similar to those of compound 14c. An intermediate compound was formed under the action of a base with a yield of 51% and MS (ASAP) = 1050.

[0228] Synthesis of compound 18: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 18 is formed with a yield of 10% and MS (ASAP) = 1024.

[0229] Example 19

[0230] The synthetic route of compound 19 is as follows:

[0231] Synthesis of compound 19a: The synthesis steps were similar to those of compound 14c. An intermediate compound was formed under the action of a base with a yield of 52% and MS (ASAP) = 1159.

[0232] Synthesis of compound 19: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 19 is formed with a yield of 12% and MS (ASAP) = 1133.

[0233] Example 20

[0234] The synthetic route of compound 20 is as follows:

[0235] Synthesis of compound 20b: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 66%, a yield of 51%, and MS (ASAP) = 1161.

[0236] Synthesis of compound 20: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 20 is formed with a yield of 11% and MS (ASAP) = 1135.

[0237] Example 21

[0238] The synthetic route of compound 21 is as follows:

[0239] Synthesis of compound 21b: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 67% and a yield of 51%, MS (ASAP) = 1162.

[0240] Synthesis of compound 21: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 21 is formed with a yield of 11% and MS (ASAP) = 1136.

[0241] Synthesis of compound 22b: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 78% and a yield of 51%, MS (ASAP) = 1218.

[0242] Synthesis of compound 22: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 22 is formed with a yield of 10% and MS (ASAP) = 1191.

[0243] Example 23

[0244] The synthetic route of compound 23 is as follows:

[0245] Synthesis of compound 23b: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 67% and a yield of 51%, MS (ASAP) = 1174.

[0246] Synthesis of compound 23: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 23 is formed with a yield of 10% and MS (ASAP) = 1148.

[0247] Example 24

[0248] The synthetic route of compound 24 is as follows:

[0249] Synthesis of compound 24b: The synthesis steps were similar to those of compound 9-2, using the classic Hartwig reaction, with a yield of 67% and a yield of 51%, MS (ASAP) = 1264.

[0250] Synthesis of compound 24: The synthesis process is similar to that of compound 14. Under the action of n-butyl lithium, Li salt is formed, and then under the action of BBr3, the final product compound 24 is formed with a yield of 12% and MS (ASAP) = 1237.

[0251] 2. Energy structure of compounds

[0252] The energy levels of organic compound materials can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian09W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. The molecular geometry is first optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is then calculated using TD-DFT (time-dependent density functional theory) using the "TD-SCF / DFT / Default Spin / B3PW91" basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, with S1, T1, and the resonance factor f(S1) used directly.

[0253] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0254] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0255] The HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1:

[0256] Table 1

[0257] The "planarity" of organic molecules can be measured by theoretically calculating the "Molecular Planarity Parameter" value to measure the overall planarity of the molecule. Table 2 calculates the MPP values ​​of some molecules. It can be seen that the introduction of different large steric groups can significantly improve the planarity of the molecule, thereby improving the stacking effect of the molecule in the device and improving the efficiency and spectral stability of the molecule in the device.

[0258] Table 2

[0259] 3. Preparation and performance of OLED devices

[0260] Preparation of OLED devices:

[0261] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Use various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) to clean, and then perform ultraviolet ozone treatment.

[0262] b. Evaporation: Move the ITO substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6 At 100 mbar, a resistive heating evaporation source was used to form a 30nm thick HI layer. HT-1 was then heated on the HI layer to form a 50nm thick HT-2 layer. Compound 1 was then evaporated on the HT-1 layer to form a 10nm thick HT-2 layer. Two evaporation sources were then used to vaporize the materials at different rates, with the weight ratio of BH:BD:GD packaged at 94:3:3, forming a 50nm light-emitting layer. The first electron transport layer (ET) was then evaporated, and then ET and LiQ were placed in different evaporation units and co-deposited at a ratio of 50 wt% to form the second electron transport layer. Subsequently, 1nm of LiQ was deposited as the electron injection layer, and finally a 100nm thick Al cathode was deposited on the electron injection layer.

[0263] c. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0264] The device structure is HI(10) / HT-1(50) / HT-2(10) / BH:BD:GD=94:3:3(50) / first ET transport layer (5) / second ET transport layer ET:LiQ=50:50(25) / LiQ(1) / Al(100).

[0265] The device performance of the above embodiment and comparative example was tested, as shown in Table 3. The driving voltage and current efficiency were measured at 10 mA / cm 2 The device life of T95 is tested at a constant current density of 20mA / cm 2The time it takes for the brightness to decay to 95%. The current efficiency and T95 are both based on the comparative example.

[0266] Table 3

[0267] Compared to Comparative Example 1, the device in Example 1 has a narrower FWMH and significantly improved current efficiency and lifetime. This is due to the presence of the triphenylene group and the BN fused ring resonance system, which better balances the electron and hole transport properties of the material, improving the device's luminous efficiency and enhancing the material's stability.

[0268] 4. Preparation and performance of color converter

[0269] The absorption and emission spectra of a 0.5 mol / L toluene solution of compound 1 are shown in FIG1 .

[0270] The preparation of the color converter is based on WO2022213993A1. The guest used is compound 1, and the structure of the host is as follows. Its synthesis is described in WO2022213993A1:

[0271] 100 mg of polymethyl methacrylate (PMMA), 50 mg of the color conversion material host (H1), and 5 mg of compound 1 (the green color conversion material guest) were weighed and dissolved in 1 mL of n-butyl acetate to obtain a clear solution, i.e., a printing ink. Using a KW-4a spin coater, the solution was spin-coated onto a quartz glass surface to form a uniform film, resulting in an organic functional material thin film, i.e., a color conversion film. The resulting color conversion film, with a thickness of approximately 3 μm, achieved an optical density of ≥3.

[0272] The above green color conversion film can be placed on a blue self-luminous device, which emits blue light with a luminescence peak at 460nm; the blue light passes through the green color converter and emits green light with a luminescence peak between 523-525nm, and the FWMH is 28nm.

[0273] 5. Color converter with chirality

[0274] Separation of chiral molecules: Compound 1 is dissolved in an organic solvent, and the chiral compounds of P and M configurations are separated and purified by chiral separation column chromatography to obtain a chiral molecular compound of P configuration (1-P).

[0275] The chiral color converter containing the chiral molecular compound (1-P) was prepared by the same method as in Example 4. Its chiral asymmetry factor g was measured to be 5.2×10 -4 , where g=(I left -I right ) / (Ileft +I right ), I right , I left is the intensity of right-handed and left-handed light.

[0276] It should be understood that the application of the present invention is not limited to the above examples. For those skilled in the art, improvements or changes can be made based on the above description. All these improvements and changes should fall within the scope of protection of the claims attached to the present invention.

Claims

1. An organic compound containing triphenylene, having a structure as shown in general formula (I): in: A, B, C, and D are the same or different from each other and are independently selected from substituted or unsubstituted C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C 10 -C 60 A fused ring structural unit, and at least one of A, B, and C is triphenylene; X and Y are independently selected from N or B, and X and Y are different; Ar is selected from formula (a) or formula (b), the dotted line indicates the bonding position, and when Ar is formula (a), L1 and L2 are independently selected from none or a single bond, and when Ar is formula (b), L1 and L2 are both single bonds; Z1, Z2, Z3, Z4, Z5, and Z6 are independently selected from CR1, NR1, N, O, S, S=O, S(=O)2, or C=O, such that chemical formula (a) becomes a five-membered heteroaromatic ring and chemical formula (b) becomes a six-membered aromatic ring or heteroaromatic ring, wherein any two adjacent substituents in Z1-Z6 can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which they are bonded; R1, at each occurrence, may be identical or different and is selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 aryloxy group having 4 to 20 C atoms a carbonyl group, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, 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 an arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination of these groups; The triphenylene-containing organic compound according to the general formula (I) may be further substituted with any substituent R; the substituent R may be the same or different at each occurrence and is selected from a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, 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 or an aryloxycarbonyl group having 4 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a CF3 group, a Cl group, a Br group, a F group, an I group, 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 an arylamino or heteroarylamino group having 5 to 40 ring atoms, or a combination of these groups.

2. The triphenylene-containing organic compound according to claim 1, selected from the structures represented by any one of the general formulas (I-1) to (I-14): in, The definitions of L1-L2, Z1-Z6, A, B, C, D, X and Y are the same as those in claim 1.

3. The triphenylene-containing organic compound according to claim 1 or 2, wherein A, B, C, and D are independently selected from the following groups: in: w, at each occurrence, is independently selected from CR 1 R 2 NR 1 、O、S、SiR 1 R 2 PR 1 、P(=O)R 1 , S=O, S(=O)2 or C=O; v is independently selected from CR at each occurrence 3 or N; R 1 -R 3 At each occurrence, each is independently selected from H, D, or a linear alkyl, haloalkyl, alkoxy, thioalkoxy group having 1-20 C atoms, or a branched or cyclic alkyl, haloalkyl, alkoxy, thioalkoxy, silyl group having 3-20 C atoms, or a keto group having 1-20 C atoms, or an alkoxycarbonyl group having 2-20 C atoms, or an aryloxycarbonyl group having 7-20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic group or heteroaromatic group having 5-60 ring atoms, or an aryloxy or heteroaryloxy group having 5-60 ring atoms, or a combination of these groups.

4. The triphenylene-containing organic compound according to any one of claims 1 to 3, wherein D is selected from C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C8-C 60 The fused ring structural unit is selected from the bulky steric groups represented by the following general formula (IIIa) or (IIIb): Wherein: P and Q are independently selected from substituted or unsubstituted C6-C 60 Aromatic ring, C5-C 60 Heteroaromatic ring or C 10 -C 60 Each time V0 appears, it is independently selected from CR 4 or N; R 4 The definition is the same as R1 in claim 1, and * represents a connection site.

5. A polymer comprising at least one repeating unit, wherein the repeating unit comprises a structure corresponding to the triphenylene-containing organic compound according to any one of claims 1 to 4.

6. A mixture comprising an organic compound containing triphenylene as described in any one of claims 1 to 4, and at least one organic functional material, wherein the organic functional material is 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, a luminophore or a host material.

7. A composition comprising a triphenylene-containing organic compound according to any one of claims 1 to 4, or the polymer according to claim 5, or the mixture according to claim 6, and at least one organic solvent.

8. An organic optoelectronic device comprising at least one triphenylene-containing organic compound according to any one of claims 1 to 4, or the polymer according to claim 5, or the mixture according to claim 6.

9. The organic optoelectronic device according to claim 8, characterized in that: The organic optoelectronic device is selected from color converters, organic light emitting diodes, organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors or organic plasmon emission diodes.

10. The organic optoelectronic device according to claim 8, characterized in that The organic photoelectric device comprises a light-emitting layer, wherein the light-emitting layer comprises an organic compound containing triphenylene according to any one of claims 1 to 4, or a polymer according to claim 5, or a mixture according to claim 6.

11. A color conversion layer comprising a luminescent body, characterized in that: The luminophore is a chiral molecule.

12. The color conversion layer according to claim 11, characterized in that The luminophore is selected from the chiral triphenylene-containing organic compound according to any one of claims 1 to 4.

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