A compound containing a nitrogen-containing heteroarene structure and an organic electroluminescence device

Abstract

The application discloses a compound containing a nitrogen-containing heterobenzene structure and an organic electroluminescent device, and belongs to the technical field of semiconductor materials. The structure of the compound is shown in general formula (1-1). The compound containing the nitrogen-containing heterobenzene structure has good stability and electron resistance, and has good electron injection and electron transmission capacity. When the compound is used as an electron transmission layer material of an organic electroluminescent device, the driving voltage of the device is significantly reduced, and the service life of the device is significantly changed.

Description

Technical Field

[0001] This invention relates to the field of semiconductor materials technology, and in particular to a compound containing a nitrogen-containing heterobenzene structure and an organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) technology can be used to manufacture novel display products and lighting products, and is expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications. OLEDs have a sandwich-like structure, including electrode material layers and organic functional materials sandwiched between different electrode material layers. Various organic functional materials are stacked together according to their intended use to form the OLED. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is applied to the positive and negative charges in the organic functional material layers, the positive and negative charges recombine in the light-emitting layer, thus generating organic electroluminescence.

[0003] Currently, OLED display technology has been applied in smartphones, tablets, televisions, and other fields. However, compared with the requirements of actual product applications, the luminous efficiency and lifespan of organic electroluminescent devices still need further improvement. In order to continuously improve the performance of organic electroluminescent devices, it is necessary to continuously research and innovate organic optoelectronic functional materials to create higher-performance organic optoelectronic functional materials.

[0004] Organic optoelectronic functional materials used in organic electroluminescent devices can be broadly classified into two categories based on their applications: charge injection transport materials and luminescent materials. Further, charge injection transport materials can be categorized into electron injection transport materials, electron blocking materials, hole injection transport materials, and hole blocking materials. As charge transport materials, they require good carrier mobility and high glass transition temperature. In organic electroluminescent devices, electrons are injected from the cathode and then transported through the electron transport layer to the host material, where they recombine with holes to generate excitons. Therefore, improving the injection and transport capabilities of the electron transport layer helps reduce the device driving voltage while achieving high electron-hole recombination efficiency. Thus, the electron transport layer is crucial, requiring high electron injection and transport capabilities as well as high electron durability.

[0005] For device lifespan, the heat resistance and film stability of materials are also crucial. Materials with low heat resistance are prone to decomposition not only during material vapor deposition but also during device operation due to the heat generated, leading to material degradation. In cases of poor film phase stability, the material may also undergo rapid film crystallization, causing delamination of the organic film layer and resulting in device degradation. Therefore, materials with high heat resistance and good film stability are required.

[0006] With the increasing demand for improved performance in organic electroluminescent devices, the requirements for material properties are also rising. These materials need not only good stability but also high efficiency and lifespan at low driving voltages. However, current electron transport materials suffer from insufficient thermal stability and deficiencies in electron tolerance, leading to phase separation or decomposition during device operation and consequently, shorter device lifespans. Summary of the Invention

[0007] To address the aforementioned problems in the prior art, this invention provides a compound containing a nitrogen-containing phenylene structure and an organic electroluminescent device containing the same. The nitrogen-containing phenylene compound of this invention, as an electron transport material for organic electroluminescent devices, can effectively improve the lifespan and efficiency of organic electroluminescent devices.

[0008] This invention provides a technical solution: a compound containing a nitrogen-containing benzene structure, the structure of which is shown in general formula (1-1):

[0009]

[0010] General formula (1-1)

[0011] In general formula (1), X1 to X3 are independently represented as nitrogen atoms or CH, and at least one of them is represented as a nitrogen atom; X4 to X6 are independently represented as nitrogen atoms or CH, and at least one of them is represented as a nitrogen atom, and X1-X6 are not simultaneously represented as nitrogen atoms;

[0012] m and n are independently represented as the numbers 0, 1, 2, 3 or 4, and m + n ≥ 1;

[0013] R1 and R represent deuterium atoms or phenyl groups substituted or unsubstituted by Ra, and at least one of R1 and R is present and represented as a phenyl group substituted or unsubstituted by Ra;

[0014] L1 represents a deuterium-substituted or unsubstituted phenylene, a deuterium-substituted or unsubstituted naphthylene, or a deuterium-substituted or unsubstituted diphenylene.

[0015] Ar2, Ar3, and Ar4 are each independently represented as phenyl groups with or without Rb substitution, naphthyl groups with or without Rb substitution, diphenyl groups with or without Rb substitution, and triphenyl groups with or without Rb substitution.

[0016] Ar2, Ar3, and Ar4 may be the same or different;

[0017] Ra represents deuterium, cyano, phenyl, diphenyl, and triphenyl.

[0018] Rb represents deuterium, cyano, phenyl, diphenyl, and terphenyl.

[0019] Furthermore, the structure of the compound is shown in any one of general formulas (II-1) to (II-5):

[0020]

[0021] General Formula (II-1) General Formula (II-2) General Formula (II-3) General Formula (II-4) General Formula (II-5)

[0022] In general formulas (II-1) to (II-5), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3, and Ar4 are the same as those in general formula (1-1) above.

[0023] R1 and R represent phenyl groups that are substituted or unsubstituted by Ra;

[0024] Ra represents cyano, phenyl, diphenyl, or triphenyl.

[0025] Furthermore, the structure of the compound is any one of general formulas (Ⅲ-1) to (Ⅲ-12):

[0026] , , , ,

[0027] General Formula (Ⅲ-1) General Formula (Ⅲ-2) General Formula (Ⅲ-3) General Formula (Ⅲ-4)

[0028] , , , ,

[0029] General Formula (Ⅲ-5) General Formula (Ⅲ-6) General Formula (Ⅲ-7) General Formula (Ⅲ-8)

[0030] , , , ,

[0031] General Formula (Ⅲ-9) General Formula (Ⅲ-10) General Formula (Ⅲ-11) General Formula (Ⅲ-12)

[0032] In general formulas (Ⅲ-1) to (Ⅲ-12), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3 and Ar4 are the same as those in general formula (1-1) above.

[0033] Furthermore, the structure of the compound is shown in any one of general formulas (Ⅳ-1) to (Ⅳ-8):

[0034] , , , ,

[0035] General Formula (Ⅳ-1) General Formula (Ⅳ-2) General Formula (Ⅳ-3) General Formula (Ⅳ-4)

[0036] , , , ,

[0037] General Formula (Ⅳ-5) General Formula (Ⅳ-6) General Formula (Ⅳ-7) General Formula (Ⅳ-8)

[0038] In general formulas (Ⅳ-1) to (Ⅳ-8), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3 and Ar4 are the same as those in general formula (1-1) above.

[0039] Furthermore, the structure of the compound is shown in any one of general formulas (V-1) to (V-3):

[0040] , , ,

[0041] General formula (V-1) General formula (V-2) General formula (V-3)

[0042] In general formulas (V-1) to (V-3), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, Ar4, m, n, R1 and R are the same as those in general formula (1-1) above.

[0043] Furthermore, the structure of the compound is shown in any one of general formulas (VI-1) to (VI-3):

[0044] , , ,

[0045] General formula (VI-1) General formula (VI-2) General formula (VI-3)

[0046] In general formulas (VI-1) to (VI-3), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, Ar4, m, n, R1 and R are the same as those in general formula (1-1) above.

[0047] Furthermore, the structure of the compound is shown in any one of general formulas (VII-1) to (VII-11):

[0048]

[0049] General formula (Ⅶ-1) General formula (Ⅶ-2) General formula (Ⅶ-3) General formula (Ⅶ-4) General formula (Ⅶ-5)

[0050]

[0051] General formula (Ⅶ-6) General formula (Ⅶ-7) General formula (Ⅶ-8) General formula (Ⅶ-9) General formula (Ⅶ-10)

[0052]

[0053] General formula (Ⅶ-11)

[0054] In general formulas (VII-1) to (VII-11), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, and Ar4 are the same as those in general formula (1-1) above;

[0055] R1 and R represent phenyl groups that are substituted or unsubstituted by Ra;

[0056] Ra represents cyano, phenyl, diphenyl, or triphenyl.

[0057] Furthermore, among X1, X2, X3, X4, X5, and X6, only one is represented as CH, and the rest are represented as nitrogen atoms;

[0058] Preferably, X1, X2, and X3 are represented as nitrogen atoms, and only one of X4, X5, and X6 is represented as CH, while the rest are represented as nitrogen atoms;

[0059] X4, X5, and X6 are preferably represented as nitrogen atoms, and only one of X1, X2, and X3 is represented as CH, while the rest are represented as nitrogen atoms.

[0060] Furthermore, Ar2, Ar3, and Ar4 are each independently represented as any one of phenyl, naphthyl, diphenyl, terphenyl, deuterated phenyl, deuterated naphthyl, deuterated diphenyl, deuterated terphenyl, cyano-substituted phenyl, cyano-substituted diphenyl, cyano-substituted naphthyl, cyano-substituted terphenyl, and phenyl-substituted naphthyl.

[0061] R and R1 are each independently represented as any one of deuterium atom, phenyl, diphenyl, deuterated phenyl, or cyano-substituted phenyl.

[0062] At least one of R1 and R is represented as any one of phenyl, diphenyl, deuterated phenyl, or cyano-substituted phenyl.

[0063] At least one of R1 and R is represented as , Any one of them.

[0064] Furthermore, L1 represents the following groups, whether substituted or unsubstituted with a deuterium atom:

[0065] , , , , , , , , , , , , , , , , , , Any one of them.

[0066] Furthermore, the specific structure of the compound is any one of the following structures:

[0067] (1) (2) (3) (4)

[0068] (5) (6) (7) (8)

[0069] (9) (10) (11) (12)

[0070] (13) (14) (15) (16)

[0071] (17) (18) (19) (20)

[0072] (21) (22) (23) (24)

[0073] (25) (26) (27) (28)

[0074] (29) (30) (31) (32)

[0075] (33) (34) (35) (36)

[0076] (37) (38) (39) (40)

[0077] (41) (42) (43) (44)

[0078] (45) (46) (47) (48)

[0079] (49) (50) (51) (52)

[0080] (53) (54) (55) (56)

[0081] (57) (58) (59) (60)

[0082] (61) (62) (63) (64)

[0083] (65) (66) (67) (68)

[0084] (69) (70) (71) (72)

[0085] (73) (74) (75) (76)

[0086] (77) (78) (79) (80)

[0087] (81) (82) (83) (84)

[0088] (85) (86) (87) (88)

[0089] (89) (90) (91) (92)

[0090] (93) (94) (95) (96)

[0091] (97) (98) (99) (100)

[0092] (101) (102) (103) (104)

[0093] (105) (106) (107) (108)

[0094] (109) (110) (111) (112)

[0095] (113) (114) (115) (116)

[0096] (117) (118) (119) (120)

[0097] (121) (122) (123) (124)

[0098] (125) (126) (127) (128)

[0099] (129) (130) (131) (132)

[0100] (133) (134) (135) (136)

[0101] (137) (138) (139) (140)

[0102] (141) (142) (143) (144)

[0103] (145) (146) (147) (148)

[0104] (149) (150) (151) (152)

[0105] (153) (154) (155) (156)

[0106] (157) (158) (159) (160)

[0107] (161) (162) (163) (164)

[0108] (165) (166) (167) (168)

[0109] (169) (170) (171) (172)

[0110] (173) (174) (175) (176)

[0111] (177) (178) (179) (180)

[0112] (181) (182) (183) (184)

[0113] (185) (186) (187) (188)

[0114] (189) (190) (191) (192)

[0115] (193) (194) (195) (196)

[0116] (197) (198) (199) (200)

[0117] (201) (202) (203) (204)

[0118] (205) (206) (207) (208)

[0119] (209) (210) (211) (212)

[0120] (213) (214) (215) (216)

[0121] (217) (218) (219) (220)

[0122] (221) (222) (223) (224)

[0123] (225) (226) (227) (228)

[0124] (229) (230) (231) (232)

[0125] (233) (234) (235) (236)

[0126] (237) (238) (239) (240)

[0127] (241) (242) (243) (244)

[0128] (245) (246) (247) (248)

[0129] (249) (250) (251) (252)

[0130] (253) (254) (255) (256)

[0131] (257) (258) (259) (260)

[0132] (261) (262) (263) (264)

[0133] (265) (266) (267) (268)

[0134] (269) (270) (271) (272)

[0135] (273) (274) (275) (276)

[0136] (277) (278) (279) (280)

[0137] (281) (282) (283) (284)

[0138] (285) (286) (287) (288)

[0139] (289) (290) (291) (292)

[0140] (293) (294) (295) (296)

[0141] (297) (298) (299) (300)

[0142] (301) (302) (303) (304)

[0143] (305) (306) (307) (308)

[0144] (309) (310) (311) (312)

[0145] (313) (314) (315) (316)

[0146] (317) (318) (319) (320)

[0147] (321) (322) (323) (324)

[0148] (325) (326) (327) (328)

[0149] (329) (330) (331) (332)

[0150] (333) (334) (335) (336)

[0151] (337) (338) (339) (340)

[0152] (341) (342) (343) (344)

[0153] (345) (346) (347) (348)

[0154] (349) (350) (351) (352)

[0155] (353) (354) (355) (356)

[0156] (357) (358) (359) (360)

[0157] (361) (362) (363) (364)

[0158] (365) (366) (367) (368)

[0159] (369) (370) (371) (372)

[0160] (373) (374) (375) (376)

[0161] (377) (378) (379) (380)

[0162] (381) (382) (383) (384)

[0163] (385) (386) (387) (388)

[0164] (389) (390) (391) (392)

[0165] (393) (394) (395) (396)

[0166] (397) (398) (399) (400)

[0167] (401) (402) (403) (404)

[0168] (405) (406) (407) (408)

[0169] (409).

[0170] The present invention also provides an organic electroluminescent device comprising a substrate, a first electrode and a second electrode, wherein a multilayer organic thin film layer is provided between the first electrode and the second electrode, and the organic thin film layer contains a compound with a nitrogen-containing heterobenzene structure as described in the present invention;

[0171] Preferably, the organic thin film layer includes a hole transport region thin film layer, a light emission region thin film layer, and an electron transport region thin film layer, wherein the electron transport region thin film layer contains a compound with a nitrogen-containing heterobenzene structure as described in this invention.

[0172] Furthermore, the electron transport region thin film layer includes an electron transport layer containing a compound with the nitrogen-containing heterobenzene structure described in this invention.

[0173] Preferably, the hole transport region thin film layer comprises a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region thin film layer comprises a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the electron transport layer contains a compound with a nitrogen-containing heterobenzene structure as described in this invention.

[0174] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0175] The nitrogen-containing heterobenzene compounds described in this invention have excellent electron transport capabilities and electron mobility at high current densities, which are beneficial for improving device efficiency and device lifespan. Attached Figure Description

[0176] Figure 1 This is a schematic diagram of the structure of an OLED device using the materials listed in this invention.

[0177] In the figure, 1 is the transparent substrate layer; 2 is the anode layer; 3 is the hole injection layer; 4 is the hole transport layer; 5 is the electron blocking layer; 6 is the light-emitting layer; 7 is the hole blocking layer; 8 is the electron transport layer; 9 is the electron injection layer; 10 is the cathode layer; and 11 is the light extraction layer.

[0178] Figure 2 This is the NMR spectrum of compound 1 of the present invention. Detailed Implementation

[0179] The technical solution of the present invention will be described in detail below with reference to the implementation scheme.

[0180] In this invention, unless otherwise stated, HOMO refers to the highest occupied orbital of a molecule, and LUMO refers to the lowest empty orbital of a molecule. Furthermore, in this invention, HOMO and LUMO energy levels are represented by absolute values, and comparisons between energy levels are made by comparing their absolute values. Those skilled in the art know that the larger the absolute value of an energy level, the lower its energy.

[0181] In the accompanying drawings, the dimensions of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "above" another layer or substrate, the layer or element may be located directly above that other layer or substrate, or there may be intermediate layers. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or there may be one or more intermediate layers.

[0182] In this invention, the terms "upper" and "lower," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "lower" side of an electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "upper" side.

[0183] Organic electroluminescent devices

[0184] The organic electroluminescent device of the present invention can be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a multilayer organic electroluminescent device, and there is no specific limitation thereto.

[0185] The organic electroluminescent device of the present invention includes a substrate, a first electrode, a multilayer organic thin film layer, and a second electrode. The multilayer organic thin film layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer. Additionally, a capping layer may be disposed on the second electrode.

[0186] The organic electroluminescent device of the present invention may include the following layers and their positional relationships: it may include a substrate, a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a second electrode. If the above layers are present, the first electrode is on the substrate, the hole injection layer is on the first electrode, the hole transport layer is on the hole injection layer, the electron blocking layer is on the hole transport layer, the light-emitting layer is on the electron blocking layer, the hole blocking layer is on the light-emitting layer, the electron transport layer is on the hole blocking layer, the electron injection layer is on the electron transport layer, the second electrode is on the electron injection layer, and a capping layer is on the second electrode.

[0187] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; and flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred, and the thickness of the substrate is not particularly limited.

[0188] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode can be an anode or a cathode. In this invention, the first electrode serves as the anode, and the anode material is preferably a material with a high work function so that holes can be easily injected into the organic functional material layer. Non-limiting examples of anode materials include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The first electrode may have a single-layer structure or a multilayer structure comprising two or more layers. In addition, the thickness of the anode depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0189] The hole injection layer, hole transport layer, and electron blocking layer can be disposed between the first electrode and the light-emitting layer.

[0190] The hole injection layer may comprise a host material and a p-type doped material. The host material may be selected from conventional hole transport materials in the prior art, preferably the same organic material as the hole transport layer. The p-type doped material is selected from charge-conducting compounds disclosed in the prior art, and may be selected from compounds disclosed in the following patent documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2 045848A1, DE102007031220A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0191] For example, the compounds shown below:

[0192] P1, P2, P3.

[0193] According to the present invention, P1 is preferably used as the P-type doped material.

[0194] The thickness of the hole injection layer of the present invention can be 1-100 nm, preferably 2-50 nm and more preferably 5-20 nm.

[0195] The material of the hole transport layer is preferably a material with high hole mobility, which enables holes to be transferred from the anode or hole injection layer to the light-emitting layer.

[0196] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0197]

[0198] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-180 nm, and more preferably 20-150 nm.

[0199] The electron blocking layer requires that its triplet (T1) energy level be higher than that of the host material in the emissive layer, thus blocking energy loss from the emissive layer material. The HOMO energy level of the electron blocking layer material should be between that of the hole transport layer material and the host material of the emissive layer, facilitating hole injection from the positive electrode into the emissive layer. Simultaneously, the electron blocking layer material should possess high hole mobility to promote hole transport and reduce the power consumption of the device. The LUMO energy level of the electron blocking layer material should be higher than that of the host material of the emissive layer, serving as an electron blocker; that is, the electron blocking layer material should have a wide bandgap (Eg). Electron blocking layer materials meeting these conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc.

[0200] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0201]

[0202] According to the present invention, the thickness of the electron blocking layer may be 1-200 nm, preferably 5-150 nm, and more preferably 5-50 nm.

[0203] According to the present invention, the light-emitting layer is located between the electron blocking layer and the hole blocking layer. The material of the light-emitting layer is a material that emits visible light by respectively receiving holes from the hole transport region and electrons from the electron transport region, and combining the received holes and electrons. The light-emitting layer may include a host material and a dopant material. As the host material and guest material of the light-emitting layer of the organic electroluminescent device of the present invention, the host material may be one or a combination of two of anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthanone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives, or pyrimidine derivatives. The guest material may be a pyrene derivative, boron derivative, chrysodium derivative, spirofluorene derivative, iridium complex, or platinum complex.

[0204] The thickness of the light-emitting layer of the present invention can be 5-60 nm, preferably 10-50 nm, and more preferably 20-45 nm.

[0205] A hole-blocking layer can be disposed above the emissive layer. The triplet (T1) energy level of the hole-blocking layer material is higher than the T1 energy level of the main emissive layer material, thus preventing energy loss from the emissive layer material. The HOMO energy level of the material is lower than the HOMO energy level of the main emissive layer material, also serving to block holes. Simultaneously, the hole-blocking layer material is required to have high electron mobility to facilitate electron transport and reduce the power consumption of the device. Hole-blocking layer materials meeting these conditions can be triazine derivatives, azirene derivatives, etc. Triazine derivatives are preferred, but not limited to these.

[0206] As the hole-blocking layer of the organic electroluminescent device of the present invention, the hole-blocking layer materials for organic electroluminescent devices disclosed in the prior art can be used:

[0207]

[0208] The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm and more preferably 5-50 nm, but the thickness is not limited to this range.

[0209] An electron transport layer may be disposed above a hole blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. The electron transport layer comprises one or more compounds of the present invention containing a nitrogen-containing phenylene structure. Preferably, the electron transport layer consists of the compound of the present invention containing a nitrogen-containing phenylene structure and other electron transport layer materials. More preferably, the other electron transport layer materials are commonly used electron transport materials in the art. Most preferably, the electron transport layer consists of the compound of the present invention containing a nitrogen-containing phenylene structure and Liq, wherein the ratio of the compound of the present invention containing a nitrogen-containing phenylene structure to other electron transport layer materials is 1:9-9:1, preferably 2:8-8:2, more preferably 4:6-6:4, and most preferably 5:5.

[0210] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm.

[0211] According to the present invention, an electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material for the organic electroluminescent device of the present invention, the following electron injection layer materials for organic electroluminescent devices disclosed in the prior art can be used: LiF, Cs₂CO₃, CsF₂, Csq, NaF, MgF₂, CaF₂, Al₂O₃, and Yb.

[0212] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0213] According to the present invention, as previously described, the second electrode can be either a cathode or an anode. In this invention, the second electrode is used as the cathode. The material used to form the cathode can be a material with low work function, such as a metal, alloy, conductive compound, or a mixture thereof. Non-limiting examples of cathode materials may include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), as well as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode depends on the material used, typically 5-100 nm, preferably 7-50 nm, and more preferably 10-25 nm.

[0214] Optionally, to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer) may be added above the second electrode (i.e., the cathode) of the device. The following compounds disclosed in the art in the prior art can be used as CPL layer materials.

[0215]

[0216] The thickness of the CPL layer is typically 5-300 nm, preferably 20-100 nm, and more preferably 40-80 nm.

[0217] Organic electroluminescent devices may also include an encapsulation structure. The encapsulation structure may be a protective structure that prevents external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0218] Methods for fabricating organic electroluminescent devices

[0219] The present invention provides a method for fabricating the aforementioned organic electroluminescent device, comprising sequentially laminating a first electrode, a multilayer organic thin film layer, and a second electrode on a substrate. The multilayer organic thin film layer is formed by sequentially laminating a hole transport region, a light-emitting layer, and an electron transport region on the first electrode from bottom to top. The hole transport region is formed by sequentially laminating a hole injection layer, a hole transport layer, and an electron blocking layer on the first electrode from bottom to top, and the electron transport region is formed by sequentially laminating a hole blocking layer, an electron transport layer, and an electron injection layer on the light-emitting layer from bottom to top. Optionally, a CPL layer may also be laminated on the second electrode to improve the light extraction efficiency of the organic electroluminescent device.

[0220] Regarding lamination, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited to these. Among them, vacuum evaporation refers to heating the material and depositing it onto the substrate in a vacuum environment.

[0221] In this invention, vacuum evaporation is preferably used to form the various layers, wherein the vapor deposition process can be carried out at a temperature of about 100-500°C for about 10... -8 -10 -2 Vacuum deposition is performed at a vacuum level of approximately 0.01-50 Å / s. The vacuum level is preferably 10 Å. -6 -10 -2 Torr, more preferably 10 -5 -10 -3 Torr. The rate is about 0.05-20 Å / s, more preferably about 0.1-10 Å / s.

[0222] In addition, it should be noted that the materials used to form each layer described in this invention can be used as a single layer by forming a film on their own, or they can be used as a single layer by mixing with other materials to form a film. They can also be a stacked structure between layers that are formed on their own, a stacked structure between layers that are formed by mixing, or a stacked structure between layers that are formed on their own and layers that are formed by mixing.

[0223] Display device

[0224] The present invention also relates to a display device including the aforementioned organic electroluminescent devices, particularly a flat panel display device. In a preferred embodiment, the display device may include one or more of the aforementioned organic electroluminescent devices, and in the case of multiple devices, the devices are stacked laterally or vertically. The display device may also include at least one thin-film transistor. The thin-film transistor may include a gate electrode, a source electrode and a drain electrode, a gate insulating layer and an active layer, wherein one of the source electrode and the drain electrode may be electrically connected to a first electrode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, organic semiconductor or oxide semiconductor, but is not limited thereto.

[0225] Exemplary embodiments have been disclosed herein. While specific terminology has been used, it is intended and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, as will be apparent to those skilled in the art upon the filing of this application, features, characteristics, and / or elements described in connection with particular embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless specifically indicated otherwise. Accordingly, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention.

[0226] The following examples are intended to better explain the present invention, but the scope of the invention is not limited thereto.

[0227] Example

[0228] I. Compound Preparation Examples

[0229] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0230] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0231] Preparation of intermediates M and L:

[0232]

[0233]

[0234]

[0235] Preparation of intermediate M-1: In a round-bottom flask, raw material A-1 (1.84 g, 4 mmol), raw material B-1 (0.84 g, 4.4 mmol), KOAC (0.98 g, 10 mmol), and Pd(PPh3)4 (0.046 g, 0.04 mmol) were added sequentially. The mixture was then evacuated and purged with nitrogen, repeated three times. Finally, 80 mL of dried dioxane was added, and the mixture was heated under reflux for 20 h under nitrogen protection. TLC analysis of the reaction solution showed that raw material A-1 reacted completely. After the reaction was complete, the reaction system was cooled to room temperature. Then, 15 mL of ultrapure water was added, and the mixture was allowed to stand for separation. After separation, the organic phase was dried over anhydrous Na2SO4, filtered, and finally the organic solvent was removed using a rotary evaporator to obtain intermediate M-1.

[0236] Preparation of intermediate M-2: The preparation method is the same as that of intermediate M-1, except that raw material A-1 is replaced with raw material A-2 and raw material B-1 is replaced with raw material B-2.

[0237] Preparation of intermediate L-1: In a round-bottom flask, starting material C-1 (1.12 g, 4.4 mmol), intermediate M-2 (1.68 g, 4 mmol), palladium acetate (0.009 g, 0.04 mmol), DPEPos (0.043 g, 0.08 mmol), and anhydrous NaOAc (0.82 g, 10 mmol) were added sequentially. The mixture was evacuated and purged with nitrogen, repeated three times. Finally, tetrahydrofuran (60 mL) was added, and the mixture was heated under reflux for 18 h under nitrogen protection. TLC analysis of the reaction mixture showed that intermediate M-2 had reacted completely. The reaction system was cooled to room temperature. The solvent was removed by rotary evaporation to obtain intermediate L-1.

[0238] The synthesis of other intermediates M is similar to that of M-1, and the specific raw materials are shown in Table 1 below:

[0239] Table 1

[0240]

[0241]

[0242] Preparation of intermediate M-21:

[0243]

[0244] Preparation of intermediate M-21: Under argon atmosphere, starting materials A-7 (0.44 g, 1.92 mmol), B-7 (1.32 g, 3.83 mmol), Pd(PPh3)4 (0.022 g, 0.019 mmol), and K2CO3 (1.11 g, 8 mmol) were dissolved in dioxane / water (40 mL / 8 mL), and the mixture was heated to reflux and reacted overnight. After cooling to room temperature, the precipitate was filtered, washed with ethanol (20 mL × 3), and dried under vacuum to obtain intermediate M-21.

[0245]

[0246] The preparation method of intermediate M-23 is the same as that of intermediate M-21, except that raw material B-7 is replaced with raw material B-8.

[0247] The synthesis of other intermediates L is similar to that of L-1, and the specific raw materials are shown in Table 2 below:

[0248] Table 2

[0249]

[0250] Preparation of intermediate L-6:

[0251]

[0252] Preparation of intermediate L-6: In a three-necked flask under nitrogen protection, starting materials B-9 (0.89 g, 3 mmol) and C-1 (0.91 g, 3.6 mmol) were dissolved sequentially in 1,4-dioxane (30 mL). Potassium acetate (0.59 g, 6 mmol), tricyclohexylphosphine (0.13 g, 0.45 mmol), and tris(dibenzylacetone)palladium (0.14 g, 0.15 mmol) were added. The mixture was heated to 110 °C and stirred for 10 hours. After filtration, the filtrate was concentrated under reduced pressure and purified by column chromatography to obtain intermediate L-6.

[0253]

[0254] Preparation of intermediate L-7: The preparation method is the same as that of intermediate L-6, except that raw material B-9 is replaced with raw material B-10.

[0255]

[0256] Preparation of intermediate L-11: The preparation method is the same as that of intermediate L-6, except that the raw material B-9 is replaced with raw material intermediate M-21.

[0257]

[0258] Preparation of intermediate L-10: The preparation method is the same as that of intermediate L-6, except that raw material B-9 is replaced with raw material B-12.

[0259] Example 1: Synthesis of Compound 1

[0260]

[0261] Preparation of Compound 1: Under a nitrogen atmosphere, intermediates M-1 (1.78 g, 4 mmol), L-1 (2.25 g, 4.4 mmol), sodium tert-butoxide (0.58 g, 6 mmol), tetrahydrofuran (50 mL), and water (10 mL) were added sequentially to a round-bottom flask. Then, palladium acetate (0.025 g, 0.1 mmol) and xantphos (0.12 g, 0.2 mmol) were added. The mixture was heated under nitrogen protection and refluxed for 20 h. The reaction solution was collected, and the reaction of intermediate M-1 was monitored by TLC until complete. After the reaction was complete, the mixture was allowed to cool naturally to room temperature. The solvent was removed by rotary evaporation. The residue was dissolved in 30 mL of dichloromethane, and 10 mL of water was added. The mixture was poured into a separatory funnel, shaken, and allowed to stand for separation. The organic phase was dried over anhydrous MgSO4, filtered, and the filtrate was evaporated by rotary evaporation to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain Compound 1. Elemental analysis and structure (molecular formula C13) were performed. 56 H 36Elemental analysis results (N6): C, 84.79; H, 4.61; N, 10.63. LC-MS: Measured value: 793.41 ([M+H]). + ).

[0262] The following compounds were prepared using the same method as in Example 1, and the raw materials are shown in Table 3 below:

[0263] Table 3

[0264]

[0265]

[0266]

[0267] II. Device Fabrication Examples

[0268] The following describes in detail the application effects of the compounds synthesized according to the present invention as electron transport materials in devices through device Examples 1-21 and device Comparative Examples 1-12. Device Examples 1-21 and Comparative Examples 1-12 are manufactured using the same process, substrate and electrode materials, and the electrode film thickness is also kept consistent. The only difference is the electron transport layer material. The device layer structure is shown in Table 4, and the performance test results of each device are shown in Table 5.

[0269] The molecular structural formulas of the relevant materials are shown below:

[0270] HT-1 EB-1

[0271] HB-1

[0272] CP-1

[0273] ET-1 ET-2 ET-3

[0274] ET-4 ET-5 ET-6

[0275] ET-7 ET-8 ET-9

[0276] ET-10 ET-11 ET-12

[0277] The structures of the relevant compounds and comparative compounds ET-1 to ET-12 in the device fabrication examples are shown above.

[0278] Device Comparison Example 1

[0279] The specific preparation process is as follows:

[0280] like Figure 1 As shown, substrate 1 is transparent glass. Ag (100nm) is deposited as the anode layer 2. On the anode layer 2, HT-1 and P-1 with a thickness of 10nm are deposited using a vacuum evaporation apparatus as the hole injection layer 3, with a mass ratio of HT-1 to P-1 of 97:3. Next, HT-1 with a thickness of 130nm is deposited as the hole transport layer 4. Subsequently, EB-1 with a thickness of 5nm is deposited as the electron blocking layer 5. After the above electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using BH-1 as the host material and BD-1 as the dopant material, with a doping ratio of 3% by weight. The thickness of the light-emitting layer 6 is 20nm. After the above light-emitting layer 6, HB-1 is deposited with a thickness of 5nm as the hole blocking layer 7. On the above hole blocking layer 7, ET-1 and LiQ are deposited with a mass ratio of ET-1 to LiQ of 1:1. The vacuum evaporation film of this material has a thickness of 30nm, and this layer is the electron transport layer 8. On electron transport layer 8, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus; this layer serves as electron injection layer 9. On electron injection layer 9, a 16 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg to Ag mass ratio of 1:9; this layer serves as cathode layer 10. On cathode layer 10, a 65 nm thick CP-1 layer is vacuum-evaporated as CPL layer 11.

[0281] Device Examples 1-21 and Device Comparative Examples 2-12 were prepared in the same manner as Device Comparative Example 1, except that they used the electron transport layer materials listed in Table 4 below.

[0282] Table 4

[0283]

[0284]

[0285]

[0286]

[0287] III. Device Testing Examples

[0288] The devices fabricated in Part II were tested, including their drive voltage and LT95 lifetime. The voltage was measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.), with a current density of 10 mA / cm². 2 LT95 refers to the time it takes for the device's brightness to decay to 95% of its initial brightness, measured at a current density of 30 mA / cm². 2 The lifetime testing system is the EAS-62C OLED device lifetime tester from System Technology Inc., Japan. The high-temperature lifetime test temperature is 85℃. LT95 refers to the time it takes for the device's brightness to decay to 95% at a specific brightness level. The current density during the test is 20mA / cm². 2 ;

[0289] The test results are shown in Table 5 below.

[0290] Table 5

[0291]

[0292] As can be seen from the device test data results in Table 5 above, compared with the comparative devices that use ET-1 to ET-12 as electron transport layer materials, the devices prepared using the compound of the present invention as electron transport layer material in Device Examples 1-21 have significantly lower driving voltages and extended device lifespans, which are basically more than 1.29 times that of Device Examples 1-12.

[0293] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0294] For those skilled in the art, various modifications and improvements can be made without departing from the concept of the present invention, and these modifications and improvements are all within the scope of protection of the present invention. The scope of protection of the present invention is defined by the appended claims.

Claims

1. A compound containing a nitrogen-containing heterobenzene structure, characterized in that, The structure of the compound is shown in general formula (1-1): General formula (1-1) In general formula (1), X1 to X3 are independently represented as nitrogen atoms or CH, and at least one of them is represented as a nitrogen atom; X4 to X6 are independently represented as nitrogen atoms or CH, and at least one of them is represented as a nitrogen atom, and X1-X6 are not simultaneously represented as nitrogen atoms; m and n are independently represented as the numbers 0, 1, 2, 3 or 4, and m + n ≥ 1; R1 and R represent deuterium atoms or phenyl groups substituted or unsubstituted by Ra, and at least one of R1 and R is present and represented as a phenyl group substituted or unsubstituted by Ra; L1 represents a deuterium-substituted or unsubstituted phenylene, a deuterium-substituted or unsubstituted naphthylene, or a deuterium-substituted or unsubstituted diphenylene. Ar2, Ar3, and Ar4 are each independently represented as phenyl groups with or without Rb substitution, naphthyl groups with or without Rb substitution, diphenyl groups with or without Rb substitution, and triphenyl groups with or without Rb substitution. Ar2, Ar3, and Ar4 may be the same or different; Ra represents deuterium, cyano, phenyl, diphenyl, and triphenyl. Rb represents deuterium, cyano, phenyl, diphenyl, and terphenyl.

2. The compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (II-1) to (II-5): General Formula (II-1) General Formula (II-2) General Formula (II-3) General Formula (II-4) General Formula (II-5) In general formulas (II-1) to (II-5), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3, and Ar4 are the same as those defined in general formula (1-1) of claim 1; R1 and R represent phenyl groups that are substituted or unsubstituted by Ra; Ra represents cyano, phenyl, diphenyl, or triphenyl.

3. The compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is any one of general formulas (Ⅲ-1) to (Ⅲ-12): 、 、 、 、 General Formula (Ⅲ-1) General Formula (Ⅲ-2) General Formula (Ⅲ-3) General Formula (Ⅲ-4) 、 、 、 、 General Formula (Ⅲ-5) General Formula (Ⅲ-6) General Formula (Ⅲ-7) General Formula (Ⅲ-8) 、 、 、 、 General Formula (Ⅲ-9) General Formula (Ⅲ-10) General Formula (Ⅲ-11) General Formula (Ⅲ-12) In general formulas (Ⅲ-1) to (Ⅲ-12), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3 and Ar4 are the same as those defined in general formula (1-1) of claim 1.

4. A compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (Ⅳ-1) to (Ⅳ-8): 、 、 、 、 General Formula (Ⅳ-1) General Formula (Ⅳ-2) General Formula (Ⅳ-3) General Formula (Ⅳ-4) 、 、 、 、 General Formula (Ⅳ-5) General Formula (Ⅳ-6) General Formula (Ⅳ-7) General Formula (Ⅳ-8) In general formulas (Ⅳ-1) to (Ⅳ-8), the meanings of X1, X2, X3, X4, X5, X6, L1, Ar2, Ar3 and Ar4 are the same as those defined in general formula (1-1) of claim 1.

5. A compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (V-1) to (V-3): 、 、 、 General formula (V-1) General formula (V-2) General formula (V-3) In general formulas (V-1) to (V-3), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, Ar4, m, n, R1 and R are the same as those defined in general formula (1-1) of claim 1.

6. A compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (VI-1) to (VI-3): 、 、 、 General formula (VI-1) General formula (VI-2) General formula (VI-3) In general formulas (VI-1) to (VI-3), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, Ar4, m, n, R1 and R are the same as those defined in general formula (1-1) of claim 1.

7. A compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, The structure of the compound is shown in any one of general formulas (VII-1) to (VII-11): General formula (Ⅶ-1) General formula (Ⅶ-2) General formula (Ⅶ-3) General formula (Ⅶ-4) General formula (Ⅶ-5) General formula (Ⅶ-6) General formula (Ⅶ-7) General formula (Ⅶ-8) General formula (Ⅶ-9) General formula (Ⅶ-10) General formula (Ⅶ-11) In general formulas (VII-1) to (VII-11), the meanings of X1, X2, X3, X4, X5, X6, Ar2, Ar3, and Ar4 are the same as those defined in general formula (1-1) of claim 1; R1 and R represent phenyl groups that are substituted or unsubstituted by Ra; Ra represents cyano, phenyl, diphenyl, or triphenyl.

8. A compound containing a nitrogen-containing heterobenzene structure according to any one of claims 1-7, characterized in that, Of X1, X2, X3, X4, X5, and X6, only one is represented as CH, and the rest are represented as nitrogen atoms; Preferably, X1, X2, and X3 are represented as nitrogen atoms, and only one of X4, X5, and X6 is represented as CH, while the rest are represented as nitrogen atoms; X4, X5, and X6 are preferably represented as nitrogen atoms, and only one of X1, X2, and X3 is represented as CH, while the rest are represented as nitrogen atoms.

9. A compound containing a nitrogen-containing heterobenzene structure according to claim 1, characterized in that, Ar2, Ar3, and Ar4 are each independently represented as any one of phenyl, naphthyl, diphenyl, terphenyl, deuterated phenyl, deuterated naphthyl, deuterated diphenyl, deuterated terphenyl, cyano-substituted phenyl, cyano-substituted diphenyl, cyano-substituted naphthyl, cyano-substituted terphenyl, and phenyl-substituted naphthyl. R and R1 are each independently represented as any one of deuterium atom, phenyl, diphenyl, deuterated phenyl, or cyano-substituted phenyl.

10. The nitrogen-containing compound according to claim 1, characterized in that, The specific structure of the compound is any one of the following structures: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76) (77) (78) (79) (80) (81) (82) (83) (84) (85) (86) (87) (88) (89) (90) (91) (92) (93) (94) (95) (96) (97) (98) (99) (100) (101) (102) (103) (104) (105) (106) (107) (108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118) (119) (120) (121) (122) (123) (124) (125) (126) (127) (128) (129) (130) (131) (132) (133) (134) (135) (136) (137) (138) (139) (140) (141) (142) (143) (144) (145) (146) (147) (148) (149) (150) (151) (152) (153) (154) (155) (156) (157) (158) (159) (160) (161) (162) (163) (164) (165) (166) (167) (168) (169) (170) (171) (172) (173) (174) (175) (176) (177) (178) (179) (180) (181) (182) (183) (184) (185) (186) (187) (188) (189) (190) (191) (192) (193) (194) (195) (196) (197) (198) (199) (200) (201) (202) (203) (204) (205) (206) (207) (208) (209) (210) (211) (212) (213) (214) (215) (216) (217) (218) (219) (220) (221) (222) (223) (224) (225) (226) (227) (228) (229) (230) (231) (232) (233) (234) (235) (236) (237) (238) (239) (240) (241) (242) (243) (244) (245) (246) (247) (248) (249) (250) (251) (252) (253) (254) (255) (256) (257) (258) (259) (260) (261) (262) (263) (264) (265) (266) (267) (268) (269) (270) (271) (272) (273) (274) (275) (276) (277) (278) (279) (280) (281) (282) (283) (284) (285) (286) (287) (288) (289) (290) (291) (292) (293) (294) (295) (296) (297) (298) (299) (300) (301) (302) (303) (304) (305) (306) (307) (308) (309) (310) (311) (312) (313) (314) (315) (316) (317) (318) (319) (320) (321) (322) (323) (324) (325) (326) (327) (328) (329) (330) (331) (332) (333) (334) (335) (336) (337) (338) (339) (340) (341) (342) (343) (344) (345) (346) (347) (348) (349) (350) (351) (352) (353) (354) (355) (356) (357) (358) (359) (360) (361) (362) (363) (364) (365) (366) (367) (368) (369) (370) (371) (372) (373) (374) (375) (376) (377) (378) (379) (380) (381) (382) (383) (384) (385) (386) (387) (388) (389) (390) (391) (392) (393) (394) (395) (396) (397) (398) (399) (400) （401） (402) (403) (404) (405) (406) (407) (408) (409)。 11. An organic electroluminescent device, comprising a substrate, a first electrode, and a second electrode, wherein a multilayer organic thin film layer is disposed between the first electrode and the second electrode, characterized in that, The organic thin film layer contains a compound with a nitrogen-containing heterobenzene structure as described in any one of claims 1 to 10; Preferably, the organic thin film layer comprises a hole transport region thin film layer, a light emission region thin film layer, and an electron transport region thin film layer, wherein the electron transport region thin film layer contains a compound with a nitrogen-containing heterobenzene structure as described in any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, characterized in that, The electron transport region thin film layer includes an electron transport layer, and the electron transport layer contains a compound with a nitrogen-containing heterobenzene structure as described in any one of claims 1 to 10; Preferably, the hole transport region thin film layer comprises a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region thin film layer comprises a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the electron transport layer contains a compound with a nitrogen-containing phenylene structure as described in any one of claims 1 to 10.

Images