A nitrogen-containing fused heterocyclic compound and its application

Abstract

The present invention provides a nitrogen-containing fused heterocyclic compound and an application thereof. When the nitrogen-containing fused heterocyclic compound of the present invention is used as a main material of a light-emitting layer, an organic light-emitting device can have a lower driving voltage (3.8-4.1V), a higher current efficiency (above 15-23Cd / A) and a longer life (above 273h).

Description

Technical Field

[0001] The invention belongs to the field of organic electroluminescent materials and relates to a nitrogen-containing condensed heterocyclic compound and application thereof. Background Art

[0002] Recently, the development of organic electroluminescent displays as image display devices is actively being carried out. Unlike liquid crystal display devices, etc., organic electroluminescent displays are self-luminous display devices in which holes and electrons injected from the first electrode and the second electrode are recombined in the emission layer, and thus the light-emitting material including organic compounds in the emission layer emits light to realize the display of images.

[0003] So far, luminescent material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantum efficiency under electrical excitation is limited to 25%, because the branching ratio of the singlet excited state and triplet excited state of the exciton is 1:3. In contrast, organic light-emitting diodes using phosphorescent materials have achieved an internal electroluminescence quantum efficiency of almost 100%. However, the stability of phosphorescent OLEDs needs to be improved. In addition to the luminescent body itself, the main material is the key to the stability of OLEDs.

[0004] For red and green phosphorescent devices, the performance of the main material determines the efficiency and life of the red and green phosphorescent devices. The currently commonly used main material is a class of organic compounds containing carbazole groups, but this type of material has disadvantages such as unbalanced charge transfer. At the same time, the stability of this type of material is limited, resulting in a short device life.

[0005] Therefore, in this field, it is crucial to develop new high-performance host materials. Summary of the invention

[0006] In view of the deficiencies in the prior art, the present invention aims to provide a nitrogen-containing fused heterocyclic compound and its application.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In one aspect, the present invention provides a nitrogen-containing fused heterocyclic compound having a structure shown in formula (1):

[0009]

[0010] Among them, Ar, Ar 2 are each independently selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,

[0011] L, L 2are each independently selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,

[0012] R 1 -R 4 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaralkyl, 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, R 1 -R 4 They exist independently or are adjacent to each other to form ring A, and the ring A is a C6-C30 aromatic ring.

[0013] Preferably, the ring A is a benzene ring.

[0014] Preferably, Ar is selected from

[0015] or a substituted or unsubstituted C6-C60 aryl group,

[0016] Y is selected from O or S,

[0017] R Y is selected from substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C3-C30 heteroarylene groups,

[0018] R 5 -R 12 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 by -O- or -S- in a non-adjacent O atom or S atom, substituted or unsubstituted C2-C30 alkenyl, C2-C30 alkenyl in which one or more methylene groups are substituted by -O- or -S- in a non-adjacent O atom or S atom, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C4-C30 heteroaralkyl, 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,

[0019] R 5 -R12 Each exists independently or two to four of them are connected to form ring B, and the ring B is a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C5-C30 heteroaromatic ring;

[0020] Preferably, the ring B is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzoindole ring or a substituted or unsubstituted naphthoindole ring.

[0021] Preferably, Ar is selected from the following substituted or unsubstituted groups:

[0022]

[0023]

[0024]

[0025] Preferably, Ar 2 is selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenyl substituted naphthyl, naphthyl substituted phenyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl substituted carbazolyl, pyridyl substituted carbazolyl, naphthyl substituted carbazolyl, biphenyl substituted carbazolyl, dibenzofuran substituted phenyl, dibenzothiophene substituted phenyl, dimethylfluorenyl, diphenyl substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl or dibenzocarbazolyl,

[0026] Preferably, L2 is selected from the following groups: connecting bonds, substituted or unsubstituted: phenylene, biphenylene, naphthylene,

[0027] Preferably, L is selected from the following substituted or unsubstituted groups: phenylene, biphenylene, naphthylene.

[0028] Preferably, the nitrogen-containing fused heterocyclic compound is any one of the following compounds:

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043] The alkyl group of the present invention may be any one of a straight chain and a branched chain. Optionally, the alkyl group includes but is not limited to a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group or a tert-butyl group.

[0044] The cycloalkyl group described in the present invention includes but is not limited to cyclopropane, cyclobutane and cyclohexane.

[0045] The alkenyl group of the present invention refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having one or more carbon-carbon double bonds and 2 to 40 carbon atoms, and examples thereof include but are not limited to vinyl, allyl, isopropenyl, 2-butenyl, and the like.

[0046] The aryl group of the present invention includes monocyclic, polycyclic and condensed ring aryl groups, and the rings may be interrupted by short non-aromatic units (e.g., methylene groups). The aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthacene, peryl, chrysene, condensed tetraphenyl, fluoranthenyl or spirobifluorenyl.

[0047] The heteroaryl group of the present invention includes monocyclic, polycyclic and condensed rings, and the rings may be interrupted by short non-aromatic units (such as methylene, O, S, N). The heteroaryl group is selected from furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl or dihydroacridinyl.

[0048] In the present invention, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, C6-C60 aromatic group, the number of carbon atoms representing the aromatic group can be any integer within the range of 6-60, for example 6, 8, 10, 15, 20, 30, 35, 40, 45, 50, 55 or 60, etc.

[0049] In the present invention, the preparation route of the nitrogen-containing fused heterocyclic compound of the structure represented by formula (1) is as follows:

[0050]

[0051]

[0052] In another aspect, the present invention provides use of the nitrogen-containing fused heterocyclic compound described above in preparing an optical device.

[0053] Preferably, the optical device comprises any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.

[0054] On the other hand, the present invention provides an organic electroluminescent device, comprising an anode and a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises any one or a combination of at least two of the nitrogen-containing fused heterocyclic compounds described above.

[0055] 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 stacked in sequence from the anode side to the cathode side;

[0056] Preferably, the material of the light-emitting layer includes a host material and a guest material, and the host material comprises any one or a combination of at least two of the nitrogen-containing fused heterocyclic compounds described above;

[0057] Preferably, the guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a complex containing Ir, Os or Pt.

[0058] In another aspect, the present invention provides an organic electroluminescent device, comprising the organic electroluminescent device as described above.

[0059] Compared with the prior art, the present invention has the following beneficial effects:

[0060] When the nitrogen-containing fused heterocyclic compound of the present invention is used as a main material of the light-emitting layer, the organic light-emitting device can have a lower driving voltage (3.8-4.1V), a higher current efficiency (above 15-23Cd / A) and a longer life (above 273h). DETAILED DESCRIPTION

[0061] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0062] Synthesis Example

[0063]

[0064] (1) Synthesis of 1-B: In a 50 ml three-necked flask, add 1-A (1 mmol) and hydrazine hydrate (20 ml), and stir at 60 °C for 2 hours. After the reaction is completed, add water to quench, extract with dichloromethane, and remove the solvent by rotary evaporation to obtain 1-B.

[0065] (2) Synthesis of 1-C: In a 50 ml three-necked flask, the product of step (1), 2-bromobenzaldehyde (1 mmol), and ethanol (20 ml) were added, and the mixture was stirred at 90°C for 5 hours. After the reaction was completed, water was added to quench the mixture, and the mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The organic phase was filtered to remove the solvent by rotary evaporation. The crude product was separated by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)) to obtain 1-C (0.27 g, yield 67%).

[0066] (3) Synthesis of 1-D: In a 50 ml three-necked flask, 1-C (1 mmol), iodophenyldiacetic acid (2 mmol), and dichloromethane (20 ml) were added and stirred at room temperature for 6 hours. After the reaction, the solvent was removed and separated by column chromatography (ethyl acetate: n-hexane = 1:10 (volume ratio)) to obtain 1-D (0.25 g, yield 62%).

[0067] (4) Synthesis of 1-F: In a 50 ml three-necked flask, 1-D (1 mmol), potassium carbonate (2 mmol), and 1,2-dichlorobenzene (20 ml) were added and stirred at 190 °C for 3 hours. After the reaction, the solvent was removed and the crude product was separated by column chromatography (ethyl acetate: n-hexane = 1:10 (volume ratio)) to obtain 1-F (0.28 g, yield 70%).

[0068] (5) Synthesis of compound 1: In a 50 ml double-necked round-bottom flask, after drying and filling with nitrogen, 1-F (1 mmol), 1-G (1 mmol), cesium carbonate (0.012 mol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.05 mmol) and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (xphos, 0.055 mmol) were added respectively, and then toluene was added. The mixture was refluxed for 24 hours and cooled to room temperature after the reaction. The reaction system was filtered and concentrated, and the crude product was purified by chromatography (dichloromethane / n-hexane = 1:10 (volume ratio)) to obtain compound 1 (0.49 g, yield 80%).

[0069] HRMS-ESI m / z[M+H]+:612.17.

[0070] Elemental analysis: C 43 H 25 N5 theoretical value: C, 84.43; H, 4.12; N, 11.45; found value: C, 84.50; H, 4.10; N, 11.40.

[0071]

[0072] (1) Synthesis of 2-B: The same as the synthesis of 1-B, except that 2-A is used instead of 1-A to obtain 2-B.

[0073] (2) Synthesis of 2-C: The synthesis was the same as that of 1-C, except that 2-B was used instead of 1-B, and m-bromobenzaldehyde was used instead of 2-bromobenzaldehyde to obtain 2-C (0.32 g, yield 65%).

[0074] (3) Synthesis of 2-D: The synthesis was the same as that of 1-D, except that 2-C was used instead of 1-C to obtain 2-D (0.49 g, yield 62%).

[0075] (4) Synthesis of 2-F: The synthesis was the same as that of 1-F, except that 2-D was used instead of 1-D to obtain 2-F (0.38 g, yield 78%).

[0076] (5) Synthesis of Compound 2: The synthesis was the same as that of Compound 1, except that 2-F was used instead of 1-F to obtain Compound 2 (0.59 g, yield 84%).

[0077] HRMS-ESI m / z[M+H]+:702.14.

[0078] Elemental analysis: C 49 H 27 Theoretical value of N5O: C, 83.86; H, 3.88; N, 9.98; Found value: C, 83.82; H, 3.89; N, 10.01.

[0079]

[0080] (1) Synthesis of 3-B: The synthesis is the same as that of 1-B, except that 3-A is used instead of 1-A to obtain 3-B.

[0081] (2) Synthesis of 3-C: The synthesis was the same as that of 1-C, except that 3-B was used instead of 1-B to obtain 3-C (0.30 g, yield 67%).

[0082] (3) Synthesis of 3-D: The synthesis was the same as that of 1-D, except that 3-C was used instead of 1-C to obtain 3-D (0.29 g, yield 64%).

[0083] (4) Synthesis of 3-F: The synthesis was the same as that of 1-F, except that 3-D was used instead of 1-D to obtain 3-F (0.37 g, yield 82%).

[0084] (5) Synthesis of compound 3: The synthesis was the same as that of compound 1, except that 3-F was used instead of 1-F to obtain compound 3 (0.51 g, yield 77%).

[0085] HRMS-ESI m / z[M+H]+:662.17.

[0086] Elemental analysis: C 47 H 27 N5 theoretical value: C, 85.30; H, 4.11; N, 10.58; found value: C, 85.31; H, 4.09; N, 10.60.

[0087]

[0088] (1) Synthesis of 4-C: The synthesis was the same as that of 1-C, except that 1-bromo-4-naphthaldehyde was used instead of 2-bromobenzaldehyde to obtain 4-C (0.3 g, yield 67%).

[0089] (2) Synthesis of 4-D: The synthesis was the same as that of 1-D, except that 4-C was used instead of 1-C to obtain 4-D (0.45 g, yield 62%).

[0090] (3) Synthesis of 4-F: The synthesis was the same as that of 1-F, except that 4-D was used instead of 1-D to obtain 4-F (0.36 g, yield 80%).

[0091] (4) Synthesis of compound 4: The synthesis was the same as that of compound 1, except that 4-F was used instead of 1-F to obtain compound 4 (0.56 g, yield 85%).

[0092] HRMS-ESI m / z[M+H]+:662.25.

[0093] Elemental analysis: C 47 H 27 N5 theoretical value: C, 85.30; H, 4.11; N, 10.58; found value: C, 85.30; H, 4.09; N, 10.61.

[0094]

[0095] (1) Synthesis of 5-C: The synthesis was the same as that of 1-C, except that 4-bromobenzaldehyde was used instead of 2-bromobenzaldehyde to obtain 5-C (0.28 g, yield 70%).

[0096] (2) Synthesis of 5-D: The synthesis was the same as that of 1-D, except that 5-C was used instead of 1-C to obtain 5-D (0.26 g, yield 65%).

[0097] (3) Synthesis of 5-F: The synthesis was the same as that of 1-F, except that 5-D was used instead of 1-D to obtain 5-F (0.32 g, yield 80%).

[0098] (4) Synthesis of compound 5: The synthesis was the same as compound 1, except that 5-F was used instead of 1-F, and 5-G was used instead of 1-G, to obtain compound 5 (0.58 g, yield 83%).

[0099] HRMS-ESI m / z[M+H]+:703.18.

[0100] Elemental analysis: C 49 H 30 Theoretical value of N6: C, 83.74; H, 4.30; N, 11.96; Found value: C, 83.69; H, 4.31; N, 12.00.

[0101]

[0102] (1) Synthesis of 6-C: The synthesis was the same as that of 1-C, except that 3-bromobenzaldehyde was used instead of 2-bromobenzaldehyde to obtain 6-C (0.26 g, yield 65%).

[0103] (2) Synthesis of 6-D: The synthesis was the same as that of 1-D, except that 6-C was used instead of 1-C to obtain 6-D (0.24 g, yield 60%).

[0104] (3) Synthesis of 6-F: The synthesis was the same as that of 1-F, except that 6-D was used instead of 1-D to obtain 6-F (0.31 g, yield 77%).

[0105] (4) Synthesis of compound 6: The synthesis was the same as compound 1, except that 6-F was used instead of 1-F, and 6-G was used instead of 1-G, to obtain compound 6 (0.54 g, yield 83%).

[0106] HRMS-ESI m / z[M+H]+:654.22.

[0107] Elemental analysis: C 44 H 27 N7 theoretical value: C, 80.84; H, 4.16; N, 15.00; found value: C, 80.78; H, 4.17; N, 15.05.

[0108]

[0109] Synthesis of compound 7: In a 50 ml three-necked flask, 6-F (1 mmol), raw material 7-G (1 mmol), potassium carbonate (1.2 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), toluene (10 ml), water (3 ml) were added, and the reaction was carried out at 60°C for 10 hours. After the reaction was completed, it was cooled to room temperature, quenched by adding 3 ml of ice water, and extracted with dichloromethane (10×3 ml). The obtained extract was dried by adding magnesium sulfate, filtered and spin-dried, and the crude product was purified by chromatography (ethyl acetate / n-hexane, 1 / 10 (volume ratio)) to obtain compound 7 (0.44 g, yield 71%).

[0110] HRMS-ESI m / z[M+H]+:625.19.

[0111] Elemental analysis: C 45 H 28 Theoretical value of N4: C, 86.51; H, 4.52; N, 8.97; Found value: C, 86.50; H, 4.50; N, 9.00.

[0112]

[0113] (1) Synthesis of 8-B: The same as the synthesis of 1-B, except that 8-A is used instead of 1-A to obtain 8-B.

[0114] (2) Synthesis of 8-C: The synthesis was the same as that of 1-C, except that 8-B was used instead of 1-B, and m-bromobenzaldehyde was used instead of 2-bromobenzaldehyde to obtain 8-C (0.32 g, yield 65%).

[0115] (3) Synthesis of 8-D: The synthesis was the same as that of 1-D, except that 8-C was used instead of 1-C to obtain 8-D (0.3 g, yield 61%).

[0116] (4) Synthesis of 8-F: The synthesis was the same as that of 1-F, except that 8-D was used instead of 1-D to obtain 8-F (0.38 g, yield 77%).

[0117] (5) Synthesis of compound 8: The synthesis was the same as that of compound 1, except that 8-F was used instead of 1-F, and 8-G was used instead of 1-G, to obtain compound 8 (0.58 g, yield 80%).

[0118] HRMS-ESI m / z[M+H]+:727.27.

[0119] Elemental analysis: C 52 H 30 Theoretical value of N4O: C, 85.93; H, 4.16; N, 7.71; Found value: C, 85.97; H, 4.14; N, 7.69.

[0120]

[0121] Synthesis of compound 9: The synthesis of compound 7 was the same as that of compound 7, except that 9-G was used instead of 7-G to obtain compound 9 (0.49 g, yield 78%)

[0122] HRMS-ESI m / z[M+H]+:632.18.

[0123] Elemental analysis: C 45 H 25 N5S theoretical value: C, 79.85; H, 3.99; N, 11.09; S, 5.07; found value: C, 79.89; H, 4.00; N, 11.06; S, 5.05.

[0124]

[0125] Synthesis of compound 10: The same as the synthesis of compound 1, except that 6-F was used instead of 1-F, and 10-G was used instead of 1-G, to obtain compound 10 (0.64 g, yield 88%)

[0126] HRMS-ESI m / z[M+H]+:729.28.

[0127] Elemental analysis: C 51 H 32Theoretical value of N6: C, 84.04; H, 4.43; N, 11.53; Found value: C, 84.00; H, 4.44; N, 11.56.

[0128]

[0129] (1) Synthesis of 11-B: The same as the synthesis of 1-B, except that 11-A is used to replace 1-A to obtain 11-B.

[0130] (2) Synthesis of 11-C: The synthesis was the same as that of 1-C, except that 11-B was used instead of 1-B, and m-bromobenzaldehyde was used instead of 2-bromobenzaldehyde, to obtain 11-C (0.36 g, yield 69%).

[0131] (3) Synthesis of 11-D: The synthesis was the same as that of 1-D, except that 1-C was replaced by 11-C to obtain 11-D (0.33 g, yield 64%).

[0132] (4) Synthesis of 11-F: The synthesis was the same as that of 1-F, except that 11-D was used instead of 1-D to obtain 11-F (0.41 g, yield 79%).

[0133] (5) Synthesis of compound 11: The synthesis was the same as compound 1, except that 11-F was used instead of 1-F, and 11-G was used instead of 1-G, to obtain compound 11 (0.64 g, yield 84%).

[0134] HRMS-ESI m / z[M+H]+:760.28.

[0135] Elemental analysis: C 52 H 33 N5S theoretical value: C, 82.19; H, 4.38; N, 9.22; S, 4.22; found value: C, 82.16; H, 4.39; N, 9.25; S, 4.20.

[0136] Device Example 1

[0137] An organic electroluminescent device comprises an anode (ITO), a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode stacked on a substrate; the preparation method is as follows:

[0138] (1) Substrate cleaning: The ITO-coated glass substrate was ultrasonically treated in an aqueous detergent, rinsed in deionized water, ultrasonically degreased in an acetone / ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water was completely removed, and then cleaned with ultraviolet light and ozone;

[0139] (2) Evaporation of hole injection layer: Place the glass substrate with the anode layer in a vacuum chamber and evacuate the vacuum to 1×10-6 ~2×10 -4 Pa, vacuum evaporating NDP-9 on the above anode layer as a hole injection layer, with an evaporation thickness of 5 nm;

[0140] H was evaporated on the hole injection layer as a second hole injection layer with a thickness of 10 nm;

[0141] (3) Evaporation of hole transport layer: HT was evaporated on the hole injection layer as a hole transport layer with a film thickness of 80 nm;

[0142] (4) Evaporation of the light-emitting layer: vacuum evaporation of the compound 1 (host material) provided by the present invention and the guest material (piq)2Ir(acac) on the hole transport layer in a co-evaporation manner, the mass ratio of the host material to the guest material is 95:5, and the total film thickness of the evaporation is 30 nm;

[0143] (5) Evaporation of electron transport layer: ET1 and LiQ (mass ratio of 1:1) were vacuum evaporated on the light-emitting layer by co-evaporation, and the total film thickness was 30 nm;

[0144] (6) Evaporation of electron injection layer: Vacuum evaporation of LiQ on the electron transport layer as an electron injection layer, with a total evaporation film thickness of 1 nm;

[0145] (7) Cathode: Mg:Ag (mass ratio is 9:1) is evaporated on the electron injection layer as a cathode, and the evaporated film thickness is 20 nm; and the organic electroluminescent device is obtained.

[0146] Device Examples 2-11, Comparative Example 1

[0147] An organic electroluminescent device, which differs from Example 1 only in that the main material of the light-emitting layer is replaced by the compounds corresponding to the device Examples 2-11 and Comparative Example 1 in Table 2, respectively.

[0148] The material structures involved in the above embodiments and comparative examples are as follows:

[0149]

[0150] Performance Test:

[0151] The current, voltage, brightness and other characteristics of the organic electroluminescent devices provided in the above embodiments and comparative examples were tested synchronously using a PR650 spectrum scanning brightness meter and a Keithley K 2400 digital source meter system;

[0152] Test conditions: current density is 10mA / cm 2 , room temperature;

[0153] Life test: The time (in hours) when the device brightness drops to 95% of the original brightness is recorded. The test results are shown in Table 2.

[0154] Table 2

[0155]

[0156] It can be seen from Table 2 that the compounds of the present invention enable the organic electroluminescent device to have a lower driving voltage (3.8-4.1 V), a higher current efficiency (above 15-23 Cd / A) and a longer life (above 273 h).

[0157] The applicant declares that the present invention illustrates the nitrogen-containing fused heterocyclic compound and its application through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various 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. A nitrogen-containing fused heterocyclic compound, characterized in that: The nitrogen-containing fused heterocyclic compound has a structure shown in formula (1): in, Ar 2 is selected from the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenyl-substituted carbazolyl, pyridyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, dimethylfluorenyl, diphenyl-substituted fluorenyl, spirobifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl or dibenzocarbazolyl, L is selected from the following groups: phenylene, biphenylene, naphthylene, L 2 Select from the connection key, R 1 -R 4 are each independently selected from hydrogen, deuterium; or R 1 -R 4 Two adjacent rings are connected to form a ring A, wherein the ring A is a benzene ring. Ar is selected from the following groups:

2. A nitrogen-containing fused heterocyclic compound, characterized in that: The nitrogen-containing fused heterocyclic compound is any one of the following compounds:

3. Use of the nitrogen-containing fused heterocyclic compound according to claim 1 or 2 in the preparation of optical devices.

4. The use according to claim 3, characterized in that: The optical device includes any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.

5. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode and a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises any one or a combination of at least two of the nitrogen-containing fused heterocyclic compounds as claimed in claim 1 or 2.

6. The organic electroluminescent device according to claim 5, characterized in that: The organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer which are sequentially stacked from the anode side to the cathode side.

7. The organic electroluminescent device according to claim 6, characterized in that: The material of the light-emitting layer comprises a host material and a guest material, and the host material comprises any one or a combination of at least two of the nitrogen-containing fused heterocyclic compounds as claimed in claim 1 or 2.

8. The organic electroluminescent device according to claim 7, characterized in that: The guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a complex containing Ir, Os or Pt.

9. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the organic electroluminescent device according to any one of claims 5 to 8.

Images