Organic material composition and use thereof

Abstract

The present application provides an organic material composition and its application, the organic material composition makes the device have lower driving voltage, higher current efficiency and higher life by coordination between the contained compounds when being an organic functional layer material.

Description

Technical Field

[0001] This invention belongs to the field of electroluminescent materials technology, and relates to an organic material composition and its application. Background Technology

[0002] An electroluminescent device (EL device) is a self-emissive display device that offers advantages such as a wider viewing angle, a higher contrast ratio, and a faster response time.

[0003] The most important factor determining the luminescence efficiency of organic EL devices is the luminescent material, which must have the following characteristics: high quantum efficiency, high mobility of electrons and holes, and uniformity and stability of the formed luminescent material layer.

[0004] Recently, the urgent task is to develop organic EL devices with high efficiency and long lifespan. Specifically, considering the EL characteristics required for medium and large OLED panels, there is an urgent need to develop highly superior luminescent materials that outperform conventional materials. To this end, the host material is required to have high glass transition temperature and pyrolysis temperature to achieve thermal stability, high electrochemical stability to achieve long lifespan, easy formability of amorphous thin films, good adhesion to adjacent layers, and no migration between layers.

[0005] Luminescent materials can be used as a combination of host and dopant to improve color purity, luminous efficiency, and stability. Typically, high-performance EL devices have a luminescent layer structure formed by incorporating dopant into the host. When using such a dopant / host material system as the luminescent material, the host material significantly affects the efficiency and lifetime of the EL device; therefore, further development of host materials is crucial in this field. Summary of the Invention

[0006] In view of the shortcomings of the prior art, the purpose of this invention is to provide an organic material composition and its application.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] On one hand, the present invention provides an organic material composition comprising at least one compound with the structure shown in formula (1) and at least one compound with the structure shown in formula (2).

[0009]

[0010] Wherein, R is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0011] R1 Selected from -L 1 Ar 1 R 2 Selected from -L 2 Ar 2 R 3 Selected from -L 3 Ar 3 R 4 Selected from -L 4 Ar 4 ,

[0012] L 1 -L 4 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene.

[0013] Ar 1 -Ar 4 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0014]

[0015] Ar W1 Ar W2 Ar W3 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups.

[0016] L W1 L W2 L W3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 aryl group, or substituted or unsubstituted C3-C30 heteroaryl group.

[0017] In this invention, by combining at least one compound with the structure shown in formula (1) and at least one compound with the structure shown in formula (2), the energy level is matched with the adjacent layer, and the triplet energy level is higher, which is beneficial for the carriers to combine in the light-emitting layer and improve the luminescence efficiency.

[0018] Preferably, in formula 1,

[0019] Ar 1 -Ar 4 At least one of them is selected from the group shown in formula (a):

[0020] X 1 Selected from N or CR X1 X 2 Selected from N or CR X2 X3 Selected from N or CR X3 X 4 Selected from N or CR X4 X 5 Selected from N or CR X5 ,

[0021] R X1 -R X5 Each is independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, R X1 -R X5 Each exists independently, or two adjacent elements are connected to form a ring, wherein the ring is a benzene ring;

[0022] Preferably, X 1 Selected from N, X 2 Selected from N, X 3 Selected from CR X3 X 4 Selected from CR X4 X 5 Selected from CR X5 ;

[0023] Preferably, X 1 Selected from N, X 3 Selected from N, X 2 Selected from CR X2 X 4 Selected from CR X4 X 5 Selected from CR X5 ;

[0024] Preferably, X 1 Selected from N, X 2 Selected from N, X 3 Selected from N, X 4 Selected from CR X4 X 5 Selected from CR X5 ;

[0025] Preferably, formula a is selected from... R X5 As with the above limitations, they will not be repeated here;

[0026] Preferably, formula a is selected from... R X2 Similar to the limitations mentioned above, they will not be repeated here.

[0027] Preferably, the R X1 -R X5Each of the following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, consists of: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, cyclopyridyl, dibenzofuranyl, dibenzothiophene, carbazoyl, carbazoyl-substituted phenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazoyl, benzonaphthofuranyl, and benzonaphthothiophene.

[0028] Preferably, the R 1 R 2 R 3 R 4 At least one of them is selected from hydrogen;

[0029] Preferably, the R 1 R 2 R 3 R 4 At least two of them are selected from hydrogen;

[0030] Preferably, the R 1 R 2 R 3 R 4 The three items are selected from hydrogen;

[0031] Preferably, the R 2 Selected from L 2 Ar 2 R 1 R 3 R 4 All are selected from hydrogen;

[0032] Preferably, the R 3 Selected from L 3 Ar 3 R 1 R 2 R 4 All are selected from hydrogen;

[0033] Preferably, R is selected from substituted or unsubstituted groups such as phenyl and biphenyl.

[0034] Preferably, L 1 -L 4 Each is independently selected from the linking bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene.

[0035] Preferably, the compound with the structure shown in formula (1) is selected from the compounds described below.

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] Where D represents deuterium.

[0047] Preferably, Ar in formula (2) W1 Ar W2 Ar W3 Each group is independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracene, phenanthrene, triphenylene, pyridyl, or the group shown in formula (b-1):

[0048] W is selected from O, S, and CR. W1 R W2 NL W R W3 ,

[0049] Ar W1 Ar W2 Ar W3 When any one, two, or three of the factors are selected from equation (b-1), R in equation (b-1) 10 -R 17 R W1 R W2 R W3 Either one is chemically bonded to L W1 L W2 L W3 connect,

[0050] Multiple formulas (b-1) may have the same or different groups.

[0051] R 10 -R 17 R W1 R W2 R W3Each of the following is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, C1-C30 alkyl in which one or more methylene groups are substituted with -O- or -S- in a manner where the O or S atom is not adjacent, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy.

[0052] R 10 -R 17 Each exists independently or two adjacent rings are connected to form a ring A, wherein ring A is a substituted or unsubstituted C6-C30 aromatic ring.

[0053] L W Selected from the linking bond, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C3-C30 heteroaryl group.

[0054] Preferably, in formula (b-1), ring A is a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring;

[0055] Preferably, formula (b-1) is selected from the structure shown in any of the following:

[0056] Preferably, R 10 -R 17 Each is independently selected from hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthraquinone, phenanthrene, benzo[phenanthrene], pyridyl, dibenzofuranyl, dibenzothiophene, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, benzonaphthofuranyl, benzonaphthothiophene;

[0057] R W1 -R W2 Each is independently selected from hydrogen, deuterium, methyl, ethyl, phenyl, or R W1 -R W2 The spiro rings are formed by chemical bonds and are fluorene rings.

[0058] Preferably, R W3Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridylylene, dibenzofuranyl, dibenzothiophene, benzonaphthiophene, dinaphthiophene, dibenzofuranyl, dibenzothiophene, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dimethylfluorenyl-substituted phenyl;

[0059] Preferably,

[0060] L W Each is independently selected from the linking bond, phenylene, biphenylene, and naphthylene;

[0061] Preferably, formula (b-1) is selected from substituted or unsubstituted groups of the following:

[0062]

[0063] This indicates the location where the functional group is attached.

[0064] In this invention, preferably, each of the substituents is independently selected from deuterium, halogen, cyano, nitro, unsubstituted or R'-substituted C1-C4 straight-chain or branched alkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and C6-C20 aromatic amino; R' is selected from deuterium, halogen, cyano, or nitro.

[0065] Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, or spirodifluorenyl;

[0066] Preferably, the heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, naphthyl-substituted carbazole, biphenyl-substituted carbazole, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthiofuranyl, benzonaphthiophenyl, benzocarbazole, or dibenzocarbazole;

[0067] Preferably, the alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, or adamantyl.

[0068] Preferably, the compound with the structure shown in formula (2) is selected from the following compounds:

[0069]

[0070]

[0071]

[0072] Preferably, the weight ratio of the compound with the structure shown in formula (1) to the compound with the structure shown in formula (2) in the organic material composition is 1:9-9:1, for example 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2 or 9:1, etc., preferably 2:8-8:2, more preferably 3:7-7:3, and even more preferably 4:6-6:4.

[0073] As used in this invention, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent element and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent element. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, an electron blocking material, a light-emitting auxiliary material, a light-emitting layer material (comprising a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0074] As used in this invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0075] As used in this invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0076] As used in this invention, the term "C3-C30 cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon derived from a main chain of 1 to 30 carbon atoms, including cyclopropyl, cyclobutyl, adamantyl, etc.

[0077] In this invention, aryl and arylene groups include monocyclic, polycyclic, or fused-ring aryl groups, and the rings may be interrupted by short non-aromatic units, and may contain spiro structures, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, spirodifluorenyl, etc.

[0078] In this invention, heteroaryl and hypoaryl groups include monocyclic, polycyclic, or fused-ring heteroaryl groups, and the rings can be interrupted by short non-aromatic units. The heteroatoms include nitrogen, oxygen, and sulfur. Including but not limited to furanyl, phenylthio, pyrroloyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, benzothiazolyl, benziisothiazolyl, benziisooxazolyl, benzooxazolyl, isoindolyl, indolyl, inzolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridinyl, and their derivatives.

[0079] Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl or spirodifluorenyl.

[0080] Preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, triazinyl, pyridyl, pyrimidinyl, imidazoleyl, oxazolyl, thiazolyl, benzimidazoleyl, benzoxazolyl, benzothiazolyl, naphthimazoleyl, naphthiazolyl, naphthiazolyl, phenanthimazoleyl, phenanthiazolyl, phenanthiazolyl, quinoxalinyl, quinazolinyl, indole-carbazoleyl Azolyl, indolofluorenyl, benzothiophene-pyrazinyl, benzothiophene-pyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, indolopyrazinyl, indolopyrimidinyl, indenepyrazinyl, indenepyrimidinyl, spiro(fluorene-9,1'-indene)pyrazinyl, spiro(fluorene-9,1'-indene)pyrimidinyl, benzofuranocarbazoyl or benzothiophene-carbazoyl.

[0081] As used in this invention, the term "C6-C30 aryloxy" refers to a monovalent substituent represented by RO-, where R represents an aryl group having 6 to 30 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, etc.

[0082] As used in this invention, the term "C1-C30 alkoxy" refers to a monovalent substituent represented by R'O-, wherein R' represents an alkyl group having 1 to 30 carbon atoms.

[0083] As used in this invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. This position is not limited to a specific position, as long as the hydrogen at that position can be replaced by a substituent. When two or more substituents are present, the two or more substituents can be the same or different.

[0084] As used in this invention, unless otherwise stated, a hydrogen atom includes protium, deuterium, and tritium.

[0085] In this invention, "two adjacent groups linked together to form a ring" means that two substituents located in adjacent positions within the same ring or adjacent rings can be linked together to form a ring through chemical bonds. This invention does not limit the specific method of ring formation (examples include single-bond linkage, linkage through a benzene ring, linkage through a naphthalene ring, etc.). Thick and through Thick and through Thick and through Thick and through Thick and; of which (Indicating density and location), as used in the following text when the same description is used, it has the same meaning.

[0086] In this invention, the definition of a group specifies a range of carbon atoms, and the number of carbon atoms is any integer within the defined range, such as C6-C60 aryl. The number of carbon atoms representing an aryl group can be any integer within the range of 6-60, such as 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55 or 60, etc.

[0087] In this invention, the organic compounds substituted at each position are prepared via the following synthetic route:

[0088]

[0089] R 5” For chlorine, R 5’ for X is a halogen, preferably chlorine or bromine;

[0090]

[0091] R 6” For chlorine, R 6’ for X is a halogen, preferably chlorine or bromine;

[0092]

[0093] R 7” For chlorine, R 7’ for X is a halogen, preferably chlorine or bromine;

[0094]

[0095] R 8” For chlorine, R 8’ for X is a halogen, preferably chlorine or bromine.

[0096] The synthesis method of formula (2) mainly adopts the Buchwald-Hartwig synthesis method.

[0097] On the other hand, the present invention provides an organic electroluminescent material comprising the organic material composition described above.

[0098] On the other hand, the present invention provides the application of the organic material composition or organic electroluminescent material as described above in the preparation of optical devices;

[0099] Preferably, the optical device includes any one of organic electroluminescent devices, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic integrated circuits, organic solar cells, organic field quenching devices, luminescent electrochemical cells, organic laser diodes, or organic photoreceptors.

[0100] On the other hand, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising an organic material composition or an organic electroluminescent material as described above.

[0101] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, which are stacked sequentially from the anode side to the cathode side.

[0102] Preferably, the material of the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic material composition or an organic electroluminescent material as described above.

[0103] Preferably, the guest material includes a phosphorescent dopant, which includes a transition metal complex.

[0104] On the other hand, the present invention provides an organic electroluminescent device, which includes the organic electroluminescent device as described above.

[0105] Compared with the prior art, the present invention has the following beneficial effects:

[0106] The organic material composition of the present invention, through the combination of at least one compound with the structure shown in formula (1) and at least one compound with the structure shown in formula (2), significantly improves the luminous efficiency of organic light-emitting elements. Attached Figure Description

[0107] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device provided in an application example of the present invention, wherein 1 is the anode, 2 is the hole injection layer, 3 is the hole transport layer, 4 is the light-emitting layer, 5 is the electron transport layer, 6 is the electron injection layer, and 7 is the cathode. Detailed Implementation

[0108] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0109] Preparation Examples

[0110]

[0111] Synthesis of 1B: 1A (10 mmol), nitrobenzene (10 mmol), potassium hydroxide (22 mmol), and cuprous thiocyanate (1 mmol), along with anhydrous tetrahydrofuran (10 mL), were added to a 25 mL three-necked flask. The mixture was purged with nitrogen three times and heated to 90°C under nitrogen protection. After 48 hours, the reaction was complete, quenched with water, and the system was extracted with ethyl acetate. The organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate:n-hexane (v / v 1:50)) to give 1B (1.34 g, 49% yield).

[0112] Synthesis of 1B': 2-Bromo-4-chlorobenzaldehyde (10 mmol), pinacol diborate (12 mmol), potassium acetate (100 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.2 mmol), and 1,-dioxane (25 mL) were added to a 50 mL three-necked flask. The mixture was purged with nitrogen and heated to 100 °C under nitrogen protection. After the reaction was complete, the mixture was quenched with water and extracted with dichloromethane. The crude product was separated by column chromatography (dichloromethane:n-hexane (v / v 1:50)) to give 1B' (1.7 g, 64% yield).

[0113] Synthesis of 1C: 1B (10 mmol), 1B' (10 mmol), sodium bicarbonate (20 mmol), tetraphenylphosphine palladium (0.2 mmol), tetrahydrofuran (20 mL), and water (10 mL) were added to a 50 mL three-necked flask. The mixture was purged with nitrogen and heated to 60 °C overnight under nitrogen protection. After the reaction was complete, the mixture was quenched with water, extracted with dichloromethane, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate:n-hexane (v / v 1:50)) to give 1C (3.06 g, 92% yield).

[0114] Synthesis of 1D: In a 50 mL three-necked flask, 1C (10 mmol), (methoxymethyl)triphenylphosphine chloride (20 mmol), and tetrahydrofuran (10 mL) were added. The temperature was lowered to 0 °C. Potassium tert-butoxide (2 mmol) was dissolved in 5 mL of tetrahydrofuran, and the mixture was purged with nitrogen. Under nitrogen protection, the potassium tert-butoxide solution was added dropwise at 0 °C. After the addition was complete, the mixture was stirred for half an hour. After the reaction was completed, the mixture was quenched with water, extracted with dichloromethane, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate:n-hexane (v / v 1:50)) to give 1D (1.8 g, 50% yield).

[0115] Synthesis of 1E: 1E (1 mmol) and hexafluoroisopropanol (5 mL) were added to a 25 mL three-necked flask, the temperature was lowered to 0 °C, nitrogen was used for purging, and trifluoromethanesulfonic acid (1 mL) was added dropwise under nitrogen protection. The reaction was stirred for another half hour. The crude product was separated by column chromatography (ethyl acetate: n-hexane (v / v 1:50)) to give 1E (0.24 g, yield 73%).

[0116] Synthesis of 1F: In a 50 mL three-necked round-bottom flask, 1E (10 mmol), pinacol diborate (12 mmol), sodium acetate (20 mmol), tris(dibenzylacetone)dipalladium (0.5 mmol), and 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl (1.5 mmol) were added, followed by 1,4-dioxane (20 mL). The mixture was purged with nitrogen three times. Under nitrogen protection, the reaction was heated to 100 °C. After the reaction was complete, the mixture was quenched with water, extracted with dichloromethane, and the organic solvent was removed by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate:n-hexane (v / v 1:50)) to give 1F (3.24 g, 77% yield).

[0117] Synthesis of Compound 1: A 100 mL three-necked round-bottom flask was placed with a stir bar and a reflux tube attached. After drying, nitrogen gas was introduced. 1F (10 mmol), 1G (10 mmol, CAS 1689576-03-1), sodium bicarbonate (23 mmol), tetrakis(triphenylphosphine)palladium (0.5 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine-palladium (0.5 mmol), toluene (25 mL), ethanol (7 mL), and water (7 mL) were added, followed by nitrogen purging three times. Under nitrogen protection, the mixture was heated to 80 °C and reacted for 8 hours. After the reaction, the mixture was extracted with ethyl acetate. The extract was then dried with magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography (ethyl acetate:n-hexane (v / v 1:10)) to give Compound 1 (4.13 g, 69% yield). Elemental analysis: C 41 H 26Theoretical N6 values: C, 81.71; H, 4.35; N, 13.94; Measured values: C, 81.78; H, 4.33; N, 13.89; HRMS(ESI) m / z[M+H]+: Theoretical value: 602.22; Measured value: 603.40.

[0118]

[0119] Synthesis of 1B”: Same as the synthesis of 1B', except that 2-bromo-5-chlorobenzaldehyde is used instead of 2-bromo-4-chlorobenzaldehyde to obtain 1B” (1.60 g, yield 60%).

[0120] Synthesis of 10C: Same as the synthesis of 1C, except that 5-chloro-2-aldehyde-phenylboronic acid pinacol ester was replaced with 4-chloro-2-aldehyde-phenylboronic acid pinacol ester, yielding 10C (2.13 g, yield 64%).

[0121] Synthesis of 10D: Same as the synthesis of 1D, except that 10C is used instead of 1C to obtain 10D (3.21 g, yield 89%).

[0122] Synthesis of 10E: Same as the synthesis of 1E, except that 1D is replaced with 10D to obtain 10E (0.16 g, yield 48%).

[0123] Synthesis of 10F: Same as the synthesis of 1F, except that 1E is replaced with 10E to obtain 10F (4.00 g, 95% yield).

[0124] Synthesis of compound 10: Same as the synthesis of compound 1, except that 10F is used instead of 1F and 10G is used instead of 1G, to obtain compound 10 (4.70 g, yield 78%).

[0125] Elemental analysis: C 41 H 26 Theoretical N6 values: C, 81.71; H, 4.35; N, 13.94; Measured values: C, 81.73; H, 4.37; N, 13.90; HRMS(ESI) m / z(M+): Theoretical value: 602.22; Measured value: 603.29.

[0126] Using raw materials 1 and 2 as shown in Table 1, the corresponding products were prepared according to the method described above, as shown in Table 1. The structural characterization data of the products are shown in Table 1.

[0127] Table 1

[0128]

[0129]

[0130] Table 2

[0131]

[0132]

[0133]

[0134] Synthesis of H1: H1-A (1 mmol), H1-B (1 mmol), Pd2(dba)3 (0.05 mmol), 50% tri-tert-butylphosphine solution (0.1 mmol), NaOtBu (2.2 mmol), and toluene (10 mL) were added to a 25 mL three-necked flask and stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic solvent was removed by vacuum distillation. The crude product was purified by chromatography (ethyl acetate:n-hexane (v / v 1:10)) to give compound H1 (0.28 g, yield 48%).

[0135] Elemental analysis: C 48 H 31 NO2 theoretical values: C, 88.18; H, 4.78; N, 2.14; measured values: C, 88.24; H, 4.76; N, 2.13; HRMS(ESI) m / z[M+H]+: theoretical value: 653.24; measured value: 654.30.

[0136] Compounds H2-H6 were synthesized using the same synthetic method as H1. The raw materials used and the products obtained are shown in Table 3, and the structural characterization of the products is shown in Table 4.

[0137] Table 3

[0138]

[0139]

[0140] Table 4

[0141]

[0142] Application examples

[0143] An organic electroluminescent device is provided, the structure of which is as follows: Figure 1 As shown, it has the following layer structure: substrate (indium tin oxide (ITO, as anode 1) coated glass substrate) / hole injection layer (HIL) 2 / hole transport layer (HTL) 3 / light emission layer (EML) 4 / electron transport layer (ETL) 5 / electron injection layer (EIL) 6, and finally cathode 7.

[0144] The materials required to manufacture OLEDs are as follows:

[0145]

[0146] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0147] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent are: ethylene glycol solvent ≤10wt%, triethanolamine ≤1wt%), rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio 1:1), baked in a clean environment until all moisture is removed, and then cleaned with ultraviolet light and ozone.

[0148] (2) Evaporation of organic light-emitting functional layer:

[0149] The glass substrate with the anode layer was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -6 Up to 2×10 -4 Pa, a mixture of HAT(CN)6 and HT is vacuum-deposited on the above-mentioned anodic layer film, wherein the mass ratio of NDP-9 to HT is 3:97, as a hole injection layer, and the deposition thickness is 10 nm.

[0150] A hole transport layer is deposited on the hole injection layer, and the deposited film thickness is 80 nm.

[0151] A light-emitting layer is deposited on the hole transport layer. The specific preparation method is as follows: the light-emitting host material and the guest material are vacuum-deposited by co-evaporation, and the total film thickness is 30nm.

[0152] An electron transport layer is deposited on the electron buffer layer. The specific preparation method is as follows: BPhen and LiQ are vacuum-deposited by co-evaporation, and the total film thickness is 30nm.

[0153] An electron injection layer is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0154] Al was deposited on the electron injection layer, with a total film thickness of 80 nm.

[0155] The parameters of each layer in the device, including its material and thickness, are shown in Table 5.

[0156] Table 5

[0157]

[0158]

[0159]

[0160] Device performance testing:

[0161] Instruments: The current, voltage, brightness, emission spectrum and other characteristics of the device were tested simultaneously using a PR 650 spectral scanning luminance meter and a Keithley K 2400 digital source meter system;

[0162] Photoelectric property test conditions: current density 10 mA / cm² 2 .

[0163] Lifetime test: Current density 20mA / cm 2 The recording time (in hours) is recorded when the device brightness drops to 98% of its original brightness.

[0164] The device performance test results are shown in Table 6:

[0165] Table 6

[0166] Device Implementation Example Number Drive voltage (V) Current efficiency (Cd / A) Lifespan (h) 1 3.85 23 165 2 3.86 21 160 3 3.97 21 168 4 4.02 18 155 5 4.07 19 150 6 3.97 19 158 7 4.04 20 150 8 4.01 18 145 9 3.89 19 150 10 3.87 24 185 11 3.95 19 150 12 4.35 12 34 13 4.12 17 95 14 4.27 15 85

[0167] As can be seen from Table 6, the organic material composition of the present invention can significantly improve current efficiency. When the organic material composition is used as an organic functional layer material, it enables the device to have a lower driving voltage (below 4.07V), higher current efficiency (above 18Cd / A), and higher lifetime (above 145h).

[0168] The applicant declares that the organic material composition and its application of the present invention are illustrated through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic material composition, characterized in that, The organic material composition comprises at least one compound with the structure shown in formula (1) and at least one compound with the structure shown in formula (2). Equation (1) Wherein, R is selected from the following groups, whether substituted or unsubstituted: phenyl, biphenyl; R 1 Selected from -L 1 Ar 1 R 2 Selected from -L 2 Ar 2 R 3 Selected from -L 3 Ar 3 R 4 Selected from -L 4 Ar 4 The R 1 R 2 R 3 R 4 The three items are selected from hydrogen; L 1 -L 4 Each is independently selected from the linking bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Ar 1 -Ar 4 One of them is selected from the group shown in formula (a): Equation (a), X 1 Selected from N or CR X1 X 2 Selected from N or CR X2 X 3 Selected from N or CR X3 X 4 Selected from N or CR X4 X 5 Selected from N or CR X5 , The R X1 -R X5 Each of the following groups, independently selected from hydrogen, deuterium, substituted or unsubstituted, consists of: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridylylene, dibenzofuranyl, dibenzothiophene, carbazoyl, carbazoyl-substituted phenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl-substituted phenyl, benzocarbazoyl, benzonaphthuryl, and benzonaphthiophene. Equation (2) Ar W1 Ar W2 Ar W3 Each group is independently selected from phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracene, phenanthrene, triphenylene, pyridyl, or the group shown in formula (b-1): Equation (b-1), W is selected from O, S, and CR. W1 R W2 NL W R W3 , Ar W1 Ar W2 Ar W3 When any one, two, or three of the factors are selected from equation (b-1), R in equation (b-1) 10 -R 17 R W1 R W2 R W3 Either one is chemically bonded to L W1 L W2 L W3 Connected, multiple formulas (b-1) may have the same or different groups; R 10 -R 17 Each is independently selected from hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthraquinone, phenanthrene, benzo[a]phenanthrene, pyridyl, dibenzofuranyl, dibenzothiophene, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, benzonaphthofuranyl, benzonaphthothiophene; R 10 -R 17 Each exists independently or two adjacent rings are connected to form a ring A, wherein ring A is a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; R W1 -R W2 Each is independently selected from hydrogen, deuterium, methyl, ethyl, phenyl, or R W1 -R W2 The spiro rings are formed by chemical bonds and are fluorene rings. R W3 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridylylene, dibenzofuranyl, dibenzothiophene, benzonaphthiophene, dinaphthiophene, dibenzofuranyl, dibenzothiophene, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, benzodimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, dimethylfluorenyl-substituted phenyl; L W Each is independently selected from the linking bond, phenylene, biphenylene, and naphthylene; L W1 L W2 L W3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene; In formulas (1) and (2), each of the substituents is independently selected from deuterium, halogen, cyano, nitro, unsubstituted or R'-substituted C1-C4 straight-chain or branched alkyl, unsubstituted or R'-substituted C6-C20 aryl, unsubstituted or R'-substituted C3-C20 heteroaryl, and C6-C20 arylamino; R' is selected from deuterium, halogen, cyano, or nitro. The aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, benzo[a]phenanthryl, naphthyl-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, or spirodifluorenyl; The heteroaryl group is selected from pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, phenyl-substituted carbazoyl, pyridyl-substituted carbazoyl, naphthyl-substituted carbazoyl, biphenyl-substituted carbazoyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, benzonaphthuryl, benzonaphthiophenyl, benzocarbazoyl or dibenzocarbazoyl; The alkyl group is selected from methyl, ethyl, propyl, tert-butyl, cyclohexyl, or adamantyl.

2. The organic material composition according to claim 1, characterized in that, X 1 Selected from N, X 2 Selected from N, X 3 Selected from CR X3 X 4 Selected from CR X4 X 5 Selected from CR X5 .

3. The organic material composition according to claim 1, characterized in that, X 1 Selected from N, X 3 Selected from N, X 2 Selected from CR X2 X 4 Selected from CR X4 X 5 Selected from CR X5 .

4. The organic material composition according to claim 1, characterized in that, X 1 Selected from N, X 2 Selected from N, X 3 Selected from N, X 4 Selected from CR X4 X 5 Selected from CR X5 .

5. The organic material composition according to claim 1, characterized in that, The formula a is selected from 。 6. The organic material composition according to claim 1, characterized in that, The formula a is selected from 。 7. The organic material composition according to claim 1, characterized in that, The R 2 Selected from L 2 Ar 2 R 1 R 3 R 4 All are selected from hydrogen.

8. The organic material composition according to claim 1, characterized in that, The R 3 Selected from L 3 Ar 3 R 1 R 2 R 4 All are selected from hydrogen.

9. The organic material composition according to claim 1, characterized in that, The compounds with the structure shown in formula (1) are selected from the compounds described below. Where D represents deuterium.

10. The organic material composition according to claim 1, characterized in that, Equation (b-1) is selected from any of the following structures: b-11 b-12 b-13 b-14 b-15 b-16.

11. The organic material composition according to claim 1, characterized in that, Formula (b-1) is selected from the following groups, whether substituted or unsubstituted: ； " "" represents the location where the functional group is attached.

12. The organic material composition according to claim 1, characterized in that, The compounds with the structure shown in formula (2) are selected from the following compounds: 。 13. The organic material composition according to claim 1, characterized in that, The weight ratio of the compound with the structure shown in formula (1) to the compound with the structure shown in formula (2) in the organic material composition is 1:9-9:

1.

14. The organic material composition according to claim 13, characterized in that, The weight ratio of the compound with the structure shown in formula (1) to the compound with the structure shown in formula (2) in the organic material composition is 2:8-8:

2.

15. The organic material composition according to claim 14, characterized in that, The weight ratio of the compound with the structure shown in formula (1) to the compound with the structure shown in formula (2) in the organic material composition is 3:7-7:

3.

16. The organic material composition according to claim 15, characterized in that, The weight ratio of the compound with the structure shown in formula (1) to the compound with the structure shown in formula (2) in the organic material composition is 4:6-6:

4.

17. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises the organic material composition as described in any one of claims 1-16.

18. The use of the organic material composition according to any one of claims 1-16 or the organic electroluminescent material according to claim 17 in the fabrication of optical devices.

19. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode and a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising an organic material composition as described in any one of claims 1-16 or an organic electroluminescent material as described in claim 17.

20. The organic electroluminescent device according to claim 19, characterized in that, The organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, which are stacked sequentially from the anode side to the cathode side.

21. The organic electroluminescent device according to claim 20, characterized in that, The material of the light-emitting layer comprises a host material and a guest material, wherein the host material comprises an organic material composition as described in any one of claims 1-16 or an organic electroluminescent material as described in claim 17.

22. The organic electroluminescent device according to claim 21, characterized in that, The guest material includes a phosphorescent dopant, which includes a transition metal complex.

23. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes the organic electroluminescent device as described in any one of claims 19-22.

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