Organic material composition and use thereof

Abstract

The present application provides an organic material composition and its application, the organic material composition includes the fused heterocyclic compound containing quinoline structure and hole transport type compound, the fused heterocyclic compound containing quinoline structure has the structure as shown in formula (1), the hole transport type compound has the structure as shown in formula (2).The composition of the present application makes the organic electroluminescent device have lower driving voltage (3.85 V or less), higher current efficiency (25 Cd / A or more) and longer life (267 h or more).

Description

Technical Field

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

[0002] In display devices, electroluminescent devices (EL devices) are automatic light-emitting devices that offer advantages such as a wide viewing angle, a high contrast ratio, and a fast response time. The first organic EL device was developed by Eastman Kodak in 1987 using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Applied Physics, 51, 913, 1987].

[0003] The most important factor determining the luminescence efficiency of organic electroluminescent devices is the luminescent material. To date, fluorescent materials have been widely used as luminescent materials. However, given the electroluminescence mechanism, phosphorescent materials have been extensively studied because they theoretically enhance luminescence efficiency by four (4) times compared to fluorescent materials. Iridium (III) complexes are widely known as phosphorescent materials, and 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known host phosphorescent material.

[0004] Although these materials offer good luminescence characteristics, they have the following drawbacks: the power efficiency of organic electroluminescent devices is derived from [(π / voltage) × current efficiency], and power efficiency is inversely proportional to voltage. While organic electroluminescent devices containing phosphorescent host materials offer higher current efficiency (cd / A) than those containing fluorescent materials, significantly higher driving voltages are required. Therefore, there is no advantage in terms of power efficiency (lm / W). Furthermore, organic electroluminescent devices have a shorter lifespan, and improvements in luminescence efficiency are still needed. Therefore, the materials constituting the organic layers in the device, especially the host material constituting the luminescent material, should be appropriately selected to achieve the superior characteristics of organic EL devices. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide an organic material composition and its applications. The organic material composition of the present invention can provide an organic electroluminescent device with a long driving life.

[0006] To achieve this objective, the present invention adopts the following technical solution:

[0007] On one hand, the present invention provides an organic material composition comprising a fused heterocyclic compound containing a quinoxaline structure and a hole-transporting compound, wherein the fused heterocyclic compound containing the quinoxaline structure has a structure as shown in formula (1), and the hole-transporting compound has a structure as shown in formula (2):

[0008]

[0009] R 1 -R 6 Each 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 O or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted with -O- or -S- in a manner where O or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkynyl, etc. Substituted or unsubstituted C7-C30 aryl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-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, or substituted or unsubstituted C6-C30 aryloxy.

[0010] R 1 -R 6 Each exists independently or two adjacent rings are connected to form a ring A, wherein ring A is a substituted or unsubstituted benzene ring.

[0011] L is selected from the linking bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene.

[0012] Ar 1 Selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C60 aromatic amino, substituted or unsubstituted C5-C60 heteroaryl, and substituted or unsubstituted C5-C60 aryl heteroaryl.

[0013] n is an integer selected from 0 to 3 (for example, it can be 0, 1, 2 or 3).

[0014] m is selected from integers between 0 and 5 (for example, it can be 0, 1, 2, 3, 4, or 5).

[0015] n1 is an integer selected from 0 to 1.

[0016] m1 is selected from integers between 0 and 1;

[0017]

[0018] In equation (2), p is selected from integers from 0 to 4 (e.g., 0, 1, 2, 3, or 4).

[0019] q is an integer selected from 0 to 4 (e.g., 0, 1, 2, 3, or 4).

[0020] R 7 R 8 Each of the following is independently selected from substituted or unsubstituted C1-C30 alkyl groups, C1-C30 alkyl groups in which one or more methylene groups are substituted with -O- or -S- in a manner where O or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkenyl groups, C2-C30 alkenyl groups in which one or more methylene groups are substituted with -O- or -S- in a manner where O or S atoms are not adjacent, substituted or unsubstituted C2-C30 alkynyl groups, substituted or unsubstituted C7-C30 aryl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C3-C30 heterocycloalkyl groups, substituted or unsubstituted C3-C30 cycloalkenyl groups, substituted or unsubstituted C1-C30 alkoxy groups, or substituted or unsubstituted C6-C30 aryloxy groups.

[0021] R 7 R 8 Each exists independently, or two or four adjacent elements are linked by chemical bonds, or by phenylene groups, or by naphthyl groups to form a ring B;

[0022] L 2 L 3 Each is independently selected from the linking bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0023] Ar 4 -Ar 7 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups, where w1 is selected from integers between 0 and 1.

[0024] w2 is selected from integers between 0 and 1.

[0025] In the organic material composition of the present invention, by using fused heterocyclic compounds containing quinoxaline structures as electron transport materials and hole transport compounds as electron transport materials, the electron-hole binding rate is improved and the current efficiency is increased.

[0026] Preferably, ring B is a substituted or unsubstituted group of the following: benzene ring, naphthyl ring, benzothiophene ring, benzofuran ring, indole ring, indole ring, or seven-membered ring.

[0027] Preferably, in formula (2), L 2 L 3 Each is independently selected from the linking bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene;

[0028] Preferably, Ar 4 -Ar 7 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophenyl or dinaphthothiophenyl;

[0029] Preferably, w1 + w2 = 1;

[0030] Preferably, R 7 R 8 Each of the following groups, independently selected from deuterium, halogen, cyano, substituted or unsubstituted, is selected: methyl, ethyl, tert-butyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophene, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophene, dinaphthothiophene;

[0031] Preferably, in formula (2), when the group contains substituents, each substituent is independently selected from deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C6 alkyl, unsubstituted or R'-substituted C6-C12 aryl, unsubstituted or R'-substituted C2-C20 heteroaryl; R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl or halogen-substituted methyl.

[0032] Preferably, the compound with the structure shown in formula (2) comprises any one of the following compounds:

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040] Preferably, n1 + m1 = 1.

[0041] Preferably, -L-Ar 1 Selected from

[0042] Among them, Ar 2 Ar 3 Each is independently selected from substituted or unsubstituted C6-C60 aryl groups and substituted or unsubstituted C5-C60 heteroaryl groups.

[0043] Preferably, Ar 2 Ar 3 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, naphthyl-substituted carbazole, biphenyl-substituted carbazole, dibenzofuranyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, benzonaphthuryl, benzonaphthiophene, benzocarbazole, or dibenzocarbazole;

[0044] Preferably, -L-Ar 1 Selected from The dashed lines represent L and Ar. 3 They are linked together in rings by chemical bonds;

[0045] More preferably, -L-Ar 1 Selected from the following groups, whether substituted or unsubstituted:

[0046]

[0047] Preferably, -L-Ar 1 Selected from The dashed line represents Ar. 2 Ar 3 They are linked together to form rings through chemical bonds.

[0048] More preferably, -L-Ar 1 Selected from the following groups, whether substituted or unsubstituted

[0049]

[0050] Preferably, Ar 1 Selected from

[0051] Where X 1 Selected from N or CR X1 X 2Selected 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 ,

[0052] R X1 R X2 R X3 R X4 R X5 Each 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 C2-C30 heteroaryl, substituted or unsubstituted C3-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, or substituted or unsubstituted C6-C30 aryloxy.

[0053] R X1 R X2 R X3 R X4 R X5 Each exists independently, or two adjacent rings are connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring, pyridine ring, naphthyl ring, anthracene ring, phenanthrene ring, naphthooxazole ring, naphthothiazole ring, benzofuran ring, or benzothiophene ring.

[0054] Preferably, Ar 1 Selected from

[0055] Preferably, Ar 1 Selected from

[0056] Where X 1 X 2 X 5 Any two of them are selected from N.

[0057] Y 1 Selected from N, CR Y1 Y 2 Selected from N, CR Y2 Y 3 Selected from N, CR Y3 Y 4 Selected from N, CR Y4 ,

[0058] R Y1 R Y2 R Y3 R Y4 Each 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 C2-C30 heteroaryl, substituted or unsubstituted C3-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, or substituted or unsubstituted C6-C30 aryloxy.

[0059] R Y1 R Y2 R Y3 R Y4 Each exists independently, or two adjacent rings are connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring.

[0060] More preferably, X 2 X 5 Selected from N.

[0061] More preferably, X 1 X 5 Selected from N.

[0062] More preferably, Y 1 Selected from CR Y1 Y 2 Selected from CR Y2 Y 3 Selected from CR Y3 Y 4 Selected from CR Y4 ,

[0063] More preferably, R X1 R X2 R X3 R X4 R X5 R Y1 R Y2 R Y3 R Y4Each of the following groups, independently selected from hydrogen, substituted or unsubstituted, consists of: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoyl, phenyl-substituted carbazoyl, pyridyl-substituted carbazoyl, naphthyl-substituted carbazoyl, biphenyl-substituted carbazoyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, and spirodifluorenyl.

[0064] Preferably, each of the L molecules is independently selected from phenylene, biphenylene, and naphthylene.

[0065] Preferably, R 1 -R 6 Each is independently selected from hydrogen, deuterium, cyano, fluorine, methyl, ethyl, tert-butyl, deuterium-substituted methyl, fluorine-substituted methyl, phenyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiopheneyl, dimethylfluorenyl, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, naphthyl-substituted carbazole, and biphenyl-substituted carbazole.

[0066] Preferably, Ar1 is selected from phenyl, biphenyl, terphenyl, naphthyl, benzophenanthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiopheneyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, 2-phenylphenanthrene[3,4-d]oxazolyl, 2-phenylphenanthrene[3,4-d]thiazolyl;

[0067] In this invention, when the group contains substituents, each substituent is independently selected from deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C6 alkyl, unsubstituted or R'-substituted C6-C12 aryl, and unsubstituted or R'-substituted C2-C20 heteroaryl; R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl, and halogen-substituted methyl.

[0068] More preferably, the alkyl group of C1-C6 is selected from methyl, ethyl, and tert-butyl;

[0069] The aryl group of C6-C12 is selected from phenyl, biphenyl, and naphthyl;

[0070] The heteroaryl group of C3-C20 is selected from triazinyl, pyridyl, phenyl-substituted pyridyl, pyridyl-substituted phenyl, dibenzofuranyl, and dibenzothiopheneyl.

[0071] Preferably, the compound having the structure shown in formula (1) is any one of the following compounds:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] Where D represents deuterium.

[0091] Preferably, the thermal decomposition temperature difference of the organic material composition is not greater than 20°C, more preferably not greater than 10°C, and even more preferably not greater than 5°C.

[0092] As used in this invention, the term "halogen" may include fluorine, chlorine, bromine or iodine, preferably fluorine.

[0093] As used in this invention, the term "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.

[0094] As used herein, unless otherwise stated, the term "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic nonaromatic hydrocarbon having 3 to 30 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantane, etc.

[0095] In this invention, heteroaryl and hypoaryl groups include monocyclic, polycyclic, or fused-ring aryl groups, and the rings can be interrupted by short non-aromatic units, including but not limited to furanyl, phenylthio, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazolidyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzo[] Thiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxoxazolyl, isoindolyl, indolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, carbazoleyl, phenoxazinyl, phenthiazinyl, phenanthidyl, benzo-m-dioxacyclopentenyl, dihydroacridyl, and their derivatives, etc.

[0096] Preferably, the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl or spirodifluorenyl.

[0097] 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.

[0098] As used in this invention, the term "aryloxy group" 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.

[0099] 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.

[0100] As used in this invention, unless otherwise stated, a hydrogen atom includes protium, deuterium, and tritium.

[0101] 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 (Indicates density and location), and has the same meaning when the same description is used in the following text.

[0102] 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.

[0103] In this invention, the preparation route of the compound having the structure shown in formula (1) is as follows:

[0104]

[0105] Where OTf represents

[0106] In this invention, the preparation route of the compound having the structure shown in formula (2) is as follows:

[0107]

[0108] On the other hand, the present invention provides the application of the organic material composition described above in the preparation of optical devices.

[0109] 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.

[0110] 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 the organic material composition described above.

[0111] 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.

[0112] 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 as described above;

[0113] Preferably, the guest material includes a phosphorescent dopant, which includes a complex containing Ir or Pt.

[0114] Preferably, the material of the electron transport layer comprises at least one or a combination of at least two of the fused heterocyclic compounds with a quinoxaline structure as described above.

[0115] On the other hand, the present invention provides an organic electroluminescent device, which includes the organic electroluminescent device as described above.

[0116] Compared with the prior art, the present invention has the following beneficial effects:

[0117] The organic material composition of the present invention enables organic electroluminescent devices to have lower driving voltage (below 3.85V), higher current efficiency (above 25Cd / A) and longer lifespan (above 267h). Detailed Implementation

[0118] 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.

[0119] Synthesis Examples

[0120]

[0121] (1) Synthesis of 1-C: Take a 50 mL double-necked round-bottom flask and place a stir bar and a reflux tube on top. After drying, purge with nitrogen. Add compounds 1-A (1 mmol), 1-B (1 mmol), potassium carbonate (K2CO3, 1.5 mmol), ethanol (3 mL), water (3 mL), toluene (15 mL), and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.05 mmol), respectively. Heat to 60 °C and react for 12 hours. After the reaction is complete, cool to room temperature, add 20 mL of water to quench, and extract with dichloromethane (3 × 20 mL). Add magnesium sulfate to the obtained extract, dry, filter, and evaporate to dryness. Purify the crude product by column chromatography (ethyl acetate / n-hexane: 1 / 10 v / v) to obtain 1-C (0.17 g, yield 54%).

[0122] (2) Synthesis of 1-D: Take a 50 mL double-necked round-bottom flask, add a stir bar and a reflux tube, dry it and then purge it with nitrogen. Add 1-C (1 mmol), bis(pinacolyl)diboron (1.2 mmol), potassium acetate (2 mmol), and 1,4-dioxane (20 mL). Under nitrogen protection, add [1,1-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (0.05 mmol) and reflux for 12 hours. After the reaction is complete, the crude product is purified by column chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 1-D (0.27 g, yield 97%).

[0123] (3) Synthesis of 1-F: Same as the synthesis of 1-C, except that 1-D is used to replace 1-B and 1-E is used to replace 1-A, to obtain 1-F (0.24 g, yield 61%).

[0124] (4) Synthesis of 1-G: Take a 50 mL double-necked round-bottom flask, add a stir bar and a reflux tube, dry it and purge it with nitrogen. Add 1-F (1 mmol), dichlorobis(tricyclohexylphosphine)palladium (PdCl2(PCy3)2, 0.05 mmol), tervaponic acid (t-BuCO2H, 2 mmol), cesium carbonate (Cs2CO3, 2 mmol) and dimethylacetamide (20 mL). Stir at 120 °C for 10 hours. After the reaction is complete, cool to room temperature. The reaction system is concentrated and the crude product is purified by column chromatography (ethyl acetate / n-hexane: volume ratio 1 / 10) to obtain 1-G (0.17 g, yield 47%).

[0125] (5) Synthesis of 1-H: 1-G (1 mmol) and dichloromethane (20 mL) were added to a 50 mL three-necked flask. A dichloromethane solution of boron tribromide (2 mmol) was added dropwise at 0 °C. After the reaction was completed, the solvent was removed and the crude product was purified by column chromatography (ethyl acetate / n-hexane, 1 / 10) to give 1-H (0.29 g, yield 84%).

[0126] (6) Synthesis of 1-J: A 50 mL double-necked round-bottom flask was placed with a stir bar and a reflux tube attached. 1-H (1 mmol), dichloromethane (20 mL), and pyridine (6 mmol) were added. The reaction system was cooled to 0 °C, and Tf₂O (1.5 mmol) was added. The system was stirred at room temperature for 30 minutes, then cooled to 0 °C. 30 mL of dichloromethane and 40 mL of water were added. The organic phase was dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation. The crude product was separated by column chromatography (ethyl acetate / n-hexane, 1 / 10) to obtain 1-J (0.42 g, 88% yield).

[0127] (7) Synthesis of 1: Take a 50 mL double-necked round-bottom flask and place a stir bar and a reflux tube on top. After drying, purge with nitrogen. Add 1-J (1 mmol), 1-K (1 mmol), cesium carbonate (0.012 mol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.05 mmol) and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (xphos, 0.055 mmol), respectively. Then add toluene. Reflux the mixture for 24 hours. After the reaction, cool to room temperature. Filter the reaction system and concentrate. Purify the crude product by column chromatography (dichloromethane / n-hexane, 1 / 10 (volume ratio)) to obtain compound 1 (0.46 g, yield 70%).

[0128] Elemental analysis: C 48 H 31 Theoretical N3 values: C, 88.72; H, 4.81; N, 6.47; Measured values: C, 88.67; H, 4.83; N, 6.50; HRMS(ESI) m / z(M+): Theoretical value: 649.2518; Measured value: 649.2525.

[0129]

[0130] (1) Synthesis of 8-C: Same as the synthesis of 1-C, except that 1-B is replaced by 8-B, yielding 8-C (0.16 g, 51% yield). (2) Synthesis of 8-D: Same as the synthesis of 1-D, except that 1-C is replaced by 8-C, yielding 8-D (0.25 g, 90% yield).

[0131] (3) Synthesis of 8-F: Same as the synthesis of 1-C, except that 1-B is replaced by 8-D and 1-A is replaced by 8-E to obtain 8-F (0.21 g, yield 53%).

[0132] (4) Synthesis of 8-G: Same as the synthesis of 1-G, except that 8-F is used instead of 1-F to obtain 8-G (0.18 g, yield 50%).

[0133] (5) Synthesis of 8-H: Same as the synthesis of 1-H, except that 8-G is used instead of 1-G to obtain 8-H (0.31 g, yield 89%).

[0134] (6) Synthesis of 8-J: Same as the synthesis of 1-J, except that 8-H is used instead of 1-H to obtain 8-J (0.41 g, yield 86%).

[0135] (7) Synthesis of compound 8: Same as the synthesis of compound 1, except that 8-J is used to replace 1-J and 8-K is used to replace 1-K, to obtain compound 8 (0.53 g, yield 81%).

[0136] Elemental analysis: C 46 H25 Theoretical N3S values: C, 84.77; H, 3.87; N, 6.45; S, 4.92; Measured values: C, 84.76; H, 3.86; N, 6.47; S, 4.91; HRMS(ESI) m / z(M+): Theoretical value: 651.1769; Measured value: 651.1775.

[0137] The same preparation method as above was used, except that the raw materials listed in Table 1 were used to prepare the corresponding products. The elemental analysis and HRMS test results of the products are shown in Table 2.

[0138] Table 1

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] Table 2

[0145]

[0146]

[0147] Device Examples

[0148] An organic electroluminescent device is provided, having the following layer structure: substrate (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light emission layer (EML) / electron transport layer (ETL) / electron injection layer (EIL), and finally a cathode.

[0149] The specific materials used are shown in Table 2. The materials required to manufacture OLEDs are as follows.

[0150]

[0151]

[0152] The fabrication of the above-mentioned organic electroluminescent device includes the following steps:

[0153] (1) Substrate cleaning: The glass substrate coated with 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.

[0154] (2) Evaporation of organic light-emitting functional layer:

[0155] 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, HAT(CN)6 is vacuum-deposited on the above-mentioned anode layer as a hole injection layer, with a deposition thickness of 5 nm;

[0156] A hole transport layer is deposited on the hole injection layer, and the deposited film thickness is 80 nm.

[0157] 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.

[0158] An electron transport layer is vacuum-deposited on the light-emitting layer. The specific preparation method is as follows: Bphen and LiQ are vacuum-deposited by co-evaporation, and the total film thickness is 30 nm.

[0159] An electron injection layer is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0160] Al was deposited on the electron injection layer, with a total film thickness of 80 nm.

[0161] The parameters of each layer in the device, including its material and thickness, are shown in Table 3.

[0162] Table 3

[0163]

[0164]

[0165] Device performance testing:

[0166] 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;

[0167] Test conditions: Current density 20 mA / cm² 2 , room temperature.

[0168] Lifetime test: Record the time (in hours) when the device brightness drops to 98% of its original brightness.

[0169] The device performance test results are shown in Table 4:

[0170] Table 4

[0171]

[0172] As can be seen from Table 4, the composition of the present invention enables organic electroluminescent devices to have lower driving voltage (below 3.85V), higher current efficiency (above 25Cd / A) and longer lifetime (above 267h).

[0173] 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 a fused heterocyclic compound containing a quinoxaline structure and a hole-transporting compound, wherein the fused heterocyclic compound containing a quinoxaline structure has a structure as shown in formula (1), and the hole-transporting compound has a structure as shown in formula (2). Equation (1) R 1 -R 6 Each is independently selected from hydrogen; n is selected from integers from 0 to 3, m is selected from integers from 0 to 5, n1 is selected from integers from 0 to 1, and m1 is selected from integers from 0 to 1. L is selected as the linker key, n1 + m1 = 1, -L-Ar 1 Selected from , The dashed lines represent L and Ar. 3 Linked into rings by chemical bonds, or The dashed line represents Ar. 2 Ar 3 They are linked together in rings by chemical bonds; Ar 2 Ar 3 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, naphthyl-substituted carbazole, biphenyl-substituted carbazole, dibenzofuranyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, benzonaphthuryl, benzonaphthiophene, benzocarbazole, or dibenzocarbazole; or, L is selected from the linker key, n1 + m1 = 1, Ar 1 Selected from 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 , R X1 R X2 R X3 R X4 R X5 Each of the following groups, individually selected from hydrogen, substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, naphthyl-substituted carbazole, biphenyl-substituted carbazole, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl; or adjacent groups connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring, pyridine ring, naphthyl ring, anthracene ring, phenanthrene ring, naphthooxazole ring, naphthothiazole ring, benzofuran ring or benzothiophene ring; or, L is independently selected from the linking bond, phenylene, biphenylene, and naphthylene, n1+m1=1, Ar 1 Selected from phenyl, biphenyl, terphenyl, naphthyl, benzophenanthryl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiopheneyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl, 2-phenylphenanthrene[3,4-d]oxazolyl, 2-phenylphenanthrene[3,4-d]thiazolyl; When the group contains substituents, each substituent is independently selected from deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C6 alkyl, unsubstituted or R'-substituted C6-C12 aryl, and unsubstituted or R'-substituted C2-C20 heteroaryl; R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl, and halogen-substituted methyl; the C1-C6 alkyl is selected from methyl, ethyl, and tert-butyl; the C6-C12 aryl is selected from phenyl, biphenyl, and naphthyl; and the C3-C20 heteroaryl is selected from triazine, pyridyl, phenyl-substituted pyridyl, pyridyl-substituted phenyl, dibenzofuranyl, and dibenzothiopheneyl. Equation (2) In equation (2), p is selected from integers from 0 to 4. q is an integer selected from 0 to 4. R 7 R 8 Each of the following groups, independently selected from deuterium, halogen, cyano, substituted or unsubstituted: methyl, ethyl, tert-butyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophene, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, carbazole, phenyl-substituted carbazole, pyridyl-substituted carbazole, dibenzocarbazole, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophene, dinaphthothiophene; multiple R 7 Same or different, multiple R 8 Same or different; R 7 R 8 Each exists independently, or two to four adjacent members are linked by chemical bonds, or by phenylene, or by naphthylene to form ring B, wherein ring B is a substituted or unsubstituted group of the following: benzene ring, naphthyl ring, benzothiophene ring, benzofuran ring, indene ring, indole ring, or seven-membered ring; L 2 L 3 Each is independently selected from the linking bond, phenylene, biphenylene, or naphthylene; Ar 4 -Ar 7 Each of the following groups, whether substituted or unsubstituted, is independently selected: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, dibenzocarbazolyl, benzonaphthofuranyl, dinaphthofuranyl, benzonaphthothiophenyl or dinaphthothiophenyl; w1 is selected from integers between 0 and 1. w2 is selected from integers between 0 and 1; w1 + w2 = 1; In formula (2), when the group contains substituents, each substituent is independently selected from deuterium, halogen, cyano, unsubstituted or R'-substituted C1-C6 alkyl, unsubstituted or R'-substituted C6-C12 aryl, unsubstituted or R'-substituted C2-C20 heteroaryl; R' is selected from deuterium, halogen, cyano, deuterium-substituted methyl or halogen-substituted methyl.

2. The organic material composition according to claim 1, characterized in that, The compound with the structure shown in formula (2) includes any one of the following compounds: 。 3. The organic material composition according to claim 1, characterized in that, -L-Ar 1 Selected from the following groups, whether substituted or unsubstituted: 。 4. The organic material composition according to claim 1, characterized in that, -L-Ar 1 Selected from the following groups, whether substituted or unsubstituted: 。 5. The organic material composition according to claim 1, characterized in that, Ar 1 Selected from or .

6. The organic material composition according to claim 1, characterized in that, Ar 1 Selected from , Where X 1 X 2 X 5 Any two of them are selected from N. Y 1 Selected from N or CR Y1 Y 2 Selected from N or CR Y2 Y 3 Selected from N or CR Y3 Y 4 Selected from N or CR Y4 , R Y1 R Y2 R Y3 R Y4 Each of the following groups, independently selected from hydrogen, substituted or unsubstituted, consists of: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, dibenzofuranyl, dibenzothiophene, carbazoyl, phenyl-substituted carbazoyl, pyridyl-substituted carbazoyl, naphthyl-substituted carbazoyl, biphenyl-substituted carbazoyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirodifluorenyl; R Y1 R Y2 R Y3 R Y4 Each exists independently, or two adjacent rings are connected to form a ring, wherein the ring is a substituted or unsubstituted benzene ring.

7. The organic material composition according to claim 6, characterized in that, Y 1 Selected from CR Y1 Y 2 Selected from CR Y2 Y 3 Selected from CR Y3 Y 4 Selected from CR Y4 .

8. The organic material composition according to claim 1, characterized in that, The compound having the structure shown in formula (1) is any one of the following compounds: Where D represents deuterium.

9. The organic material composition according to claim 1, characterized in that, The thermal decomposition temperature difference of the organic material composition is no greater than 20°C.

10. The organic material composition according to claim 9, characterized in that, The thermal decomposition temperature difference of the organic material composition is no greater than 10°C.

11. The organic material composition according to claim 10, characterized in that, The thermal decomposition temperature difference of the organic material composition is no greater than 5°C.

12. The use of the organic material composition according to any one of claims 1-11 in the preparation of optical devices.

13. The application according to claim 12, characterized in that, 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.

14. 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 1-11.

15. The organic electroluminescent device according to claim 14, 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.

16. The organic electroluminescent device according to claim 15, 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 1-11.

17. The organic electroluminescent device according to claim 16, characterized in that, The guest material includes a phosphorescent dopant, which includes a complex containing Ir or Pt.

18. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes the organic electroluminescent device as described in any one of claims 1-11.

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