Arylamine compound, organic electroluminescent element and electronic device

Abstract

The purpose of the present invention is to provide: an organic compound represented by general formula (A), which is a material for an organic electroluminescent (EL) element having high efficiency and high durability, has excellent hole injection / transport performance, has electron blocking ability, and has high stability in a thin film state; and an organic EL element having high efficiency and high durability by using the compound. In general formula (A), A and B represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aryl group; each of L1 to L4 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group, a substituted or unsubstituted divalent aromatic heterocyclic group, or a substituted or unsubstituted divalent condensed polycyclic aryl group; r is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aryl group, which are the same or different. The arylamine compound provided by the invention has excellent heat resistance and also has good hole transport capability. An organic EL element using the compound in a hole transport layer, an electron blocking layer, a light emitting layer, and a hole injection layer of the organic EL element exhibits good element performance.

Description

Technical field

[0001] The present invention relates to a compound and a component suitable for an organic electroluminescent component (hereinafter referred to as an organic EL component) used as a self-luminous component for various display devices, and more particularly to an aromatic amine compound and an organic EL component using the same. [Prior Art]

[0002] Organic EL components are self-luminous components that are brighter and have excellent visibility than liquid crystal components. Therefore, they can display clearly and have been actively studied.

[0003] In 1987, CW Tang and others at Eastman Kodak developed a multilayer structure device that divided the roles among the materials, thus making organic EL devices using organic materials a reality. They stacked a phosphor that can transport electrons and an organic substance that can transport holes, and injected charges from both sides into the phosphor layer to cause it to emit light, thus achieving 1000 cd / m at a voltage of less than 10V. 2 The above high brightness (for example, refer to Patent Documents 1 and 2).

[0004] To date, many improvements have been made to the practical application of organic EL components, and the various functions of the layered structure have been further refined, thereby achieving high efficiency and durability by having an electroluminescent component in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode are arranged in sequence on a substrate (for example, refer to non-patent document 1).

[0005] In order to further improve luminous efficiency, efforts are being made to utilize triplet excitons, and research is underway into the use of phosphorescent compounds (e.g., see Non-Patent Document 2). Furthermore, a device utilizing luminescence via thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. of Kyushu University achieved an external quantum efficiency of 5.3% using a device using a thermally activated delayed fluorescence material (e.g., see Non-Patent Document 3).

[0006] The light-emitting layer can also be produced by doping a charge-transporting compound, generally referred to as a host material, with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. As described in the aforementioned non-patent literature, the choice of organic material in an organic EL device significantly influences various characteristics of the device, including efficiency and durability (see, for example, non-patent literatures 1-3).

[0007] In organic EL devices, charges injected from the two electrodes recombine in the light-emitting layer to produce light. However, it is crucial to efficiently transfer both holes and electrons to the light-emitting layer, thus requiring a device with excellent carrier balance. Therefore, by using materials that enhance hole injection, supplying holes injected from the anode to the light-emitting layer, and enhance electron-blocking properties, blocking electrons injected from the cathode, the probability of hole and electron recombination within the light-emitting layer can be increased. This, in turn, results in high luminous efficiency by confining excitons generated within the light-emitting layer. To this end, hole transport materials play a crucial role, requiring a material with high hole injectability, high hole mobility, high electron-blocking properties, and, consequently, high durability against electrons.

[0008] Furthermore, the material's heat resistance and amorphous properties are crucial for device lifespan. Materials with low heat resistance undergo thermal decomposition at relatively low temperatures due to the heat generated during device operation, leading to material degradation. Materials with low amorphous properties also experience thin film crystallization over a relatively short period of time, causing device degradation. Therefore, materials used are required to possess both high heat resistance and good amorphous properties.

[0009] Hole-transport materials used in organic EL devices to date include N,N'-diphenyl-N,N'-di(α-naphthyl)benzidine (NPD) and various aromatic amine derivatives (see, for example, Patent Documents 1 and 2). However, while NPD exhibits excellent hole-transporting properties, its glass transition point (Tg), an indicator of heat resistance, is as low as 96°C. Crystallization at high temperatures degrades device performance (see, for example, Non-Patent Document 4).

[0010] In addition, among the aromatic amine derivatives described in the above patent documents, there is a compound having a hole mobility of 10 -3 cm 2 Although there are reports of compounds with excellent mobility of 100 nm / Vs or higher (e.g., see Patent Documents 1 and 2), their electron-blocking properties are insufficient, causing some electrons to escape from the light-emitting layer, thus preventing the expectation of improved luminous efficiency. To further achieve higher efficiency, there is a demand for materials with even higher electron-blocking properties, more stable thin films, and higher heat resistance. Furthermore, although there are reports of aromatic amine derivatives with high durability (e.g., see Patent Document 3), their use as charge transport materials in electrophotographic photoreceptors is unheard of. Their use in organic EL devices has not been documented.

[0011] In order to solve the above-mentioned problems, a substituted carbazole structure or aromatic amine compound has been proposed as a compound having improved properties such as heat resistance and hole injection properties (for example, see Patent Documents 4 and 5). These compounds are used in components with hole injection layers or hole transport layers. Although the component life and luminous efficiency have been improved, they are still insufficient, and further efforts are required to achieve lower driving voltage or higher luminous efficiency and longer component life.

[0012]

Previous Technical Literature

[0013] [Patent Literature]

[0014] U.S. Patent No. 5,792,557

[0015] U.S. Patent No. 5,639,914

[0016] U.S. Patent No. 7,759,030

[0017] Japanese Patent Laid-Open No. 2009-076817

[0018] Japanese Patent No. 6674892

[0019] European Patent Specification No. 2684932

[0020] Korean Patent No. 10-2452568

[0021] Korean Patent No. 10-2242490

[0022]

Non-patent literature

[0023] Proceedings of the 9th Workshop of the Society of Applied Physics, pp. 55-61 (2001)

[0024] Proceedings of the 9th Workshop of the Society of Applied Physics, pp. 23-31 (2001)

[0025] Appl.Phys.Let.,98,083302(2011)

[0026] Organic EL Symposium Third Regular Meeting Draft Proceedings, pp. 13-14 (2006) [Summary of the invention] [Problems to be solved by the invention]

[0027] The object of the present invention is to provide a material for an organic EL component having the following properties as a material for a high-efficiency and high-durability organic EL component: (1) excellent hole injection and transport performance, (2) electron blocking ability, (3) high stability in a thin film state, and (4) excellent durability.

[0028] Furthermore, by using the material of the present invention, an organic EL device is provided that has (1) high luminous efficiency and power efficiency, (2) low luminous starting voltage and practical driving voltage, and (3) long life.

Technical means to solve the problem

[0029] To achieve the above objectives, the inventors focused on the excellent hole injection and transport capabilities, thin film stability, and durability of aromatic amine compounds. They sought to optimize the substitution position and substituents of the carbazole group, significantly improving the material's properties. Furthermore, the luminous efficiency and power efficiency of organic EL devices were improved, thereby suppressing the emission onset voltage and practical driving voltage, thereby achieving a longer lifespan than previously possible. This led to the completion of the present invention.

[0030] Specifically, the present invention provides the following aromatic amine compounds, and organic EL devices and electronic apparatuses using the same.

[0031] (1) An aromatic amine compound represented by the following general formula (A):

[0032]

[0033] In the above general formula (A), A and B represent:

[0034] a substituted or unsubstituted aromatic hydrocarbon group,

[0035] a substituted or unsubstituted aromatic heterocyclic group, or

[0036] a substituted or unsubstituted condensed polycyclic aromatic group;

[0037] L1 to L4 indicate:

[0038] single bond,

[0039] a substituted or unsubstituted divalent aromatic hydrocarbon group,

[0040] a substituted or unsubstituted divalent aromatic heterocyclic group, or

[0041] a substituted or unsubstituted divalent condensed polycyclic aromatic group;

[0042] R are the same or different

[0043] Hydrogen atoms, deuterium atoms,

[0044] a substituted or unsubstituted aromatic hydrocarbon group,

[0045] a substituted or unsubstituted aromatic heterocyclic group, or

[0046] a substituted or unsubstituted condensed polycyclic aromatic group;

[0047] However, at least one of R is a substituted aromatic hydrocarbon group.

[0048] (2) The aromatic amine compound according to (1) above,

[0049] Wherein at least one of the R in the general formula (A) is a deuterated phenyl group.

[0050] (3) The aromatic amine compound according to (1) or (2) above, which is represented by the following general formula (B), (C), (D) or (E):

[0051]

[0052]

[0053]

[0054]

[0055] A, B, R and L1 to L4 in the above general formula (B), (C), (D) or (E) have the same meanings as in the above general formula (A).

[0056] (4) The aromatic amine compound according to (3) above, wherein in the general formula (B), (C), (D) or (E),

[0057] R is a hydrogen atom or a deuterium atom.

[0058] (5) The aromatic amine compound according to (4) above, wherein in the general formula (B), (C), (D) or (E),

[0059] L1 to L4 are:

[0060] single bond,

[0061] Substituted or unsubstituted phenylene,

[0062] Substituted or unsubstituted naphthylene, or

[0063] Substituted or unsubstituted biphenylene.

[0064] (6) The aromatic amine compound according to (5) above, wherein in the general formula (B), (C), (D) or (E),

[0065] L4 is:

[0066] Substituted or unsubstituted 1,2-phenylene,

[0067] Substituted or unsubstituted 1,3-phenylene,

[0068] Substituted or unsubstituted 1,4-phenylene,

[0069] Substituted or unsubstituted 1,2-naphthylene,

[0070] Substituted or unsubstituted 1,3-naphthylene, or

[0071] Substituted or unsubstituted 1,4-naphthylene.

[0072] (7) The aromatic amine compound according to (6) above, wherein in the general formula (B), (C), (D) or (E),

[0073] L4 is:

[0074] Unsubstituted 1,2-phenylene,

[0075] Unsubstituted 1,3-phenylene,

[0076] Unsubstituted 1,4-phenylene,

[0077] Unsubstituted 1,2-naphthylene,

[0078] Unsubstituted 1,3-naphthylene, or

[0079] Substituted or unsubstituted 1,4-naphthylene.

[0080] (8) An organic EL device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the aromatic amine compound described in (1) or (2) above.

[0081] (9) The organic EL device according to (8) above, wherein the organic layer is a hole transport layer.

[0082] (10) The organic EL device according to (8) above, wherein the organic layer is an electron blocking layer.

[0083] (11) The organic EL device according to (8) above, wherein the organic layer is a hole injection layer.

[0084] (12) The organic EL device according to (8) above, wherein the organic layer is a light-emitting layer.

[0085] (13) An electronic device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the aromatic amine compound described in (1) or (2) above.

[0086] As represented by A, B or R in the general formula (A)

[0087] "substituted or unsubstituted aromatic hydrocarbon group",

[0088] "substituted or unsubstituted aromatic heterocyclic group", or

[0089] "Substituted or unsubstituted condensed polycyclic aromatic group"

[0090] "aromatic hydrocarbon group",

[0091] "aromatic heterocyclic group", or

[0092] "Condensed polycyclic aromatic groups",

[0093] Specific examples include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, pyrenyl, peryl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyridyl, pyrimidinyl, triazinyl, furyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, fluorenyl, spirobifluorenyl, azafluorenyl, diazafluorenyl, azaspirobifluorenyl, diazaspirobifluorenyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, and carbolinyl. In addition, the group may be selected from aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 2 to 20 carbon atoms.

[0094] In the general formula (A)

[0095] A, B or R

[0096] "Substituted aromatic hydrocarbon groups",

[0097] "substituted aromatic heterocyclic group", or

[0098] In the "substituted condensed polycyclic aromatic group",

[0099] As a "substituent",

[0100] Specific examples include deuterium, cyano, and nitro groups; halogen atoms such as fluorine, chlorine, bromine, and iodine atoms; silyl groups such as trimethylsilyl and triphenylsilyl groups; linear or branched alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, and propyl groups; linear or branched alkoxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, and propoxy groups; alkenyl groups such as vinyl and allyl groups; aryloxy groups such as phenoxy and tolyloxy groups; aralkyloxy groups such as benzyloxy and phenethoxy groups; phenyl, biphenyl, and terphenyl groups. , naphthyl, anthracenyl, phenanthrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, peryl, fluoranthenyl, benzo[9,10]phenanthrenyl, and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbolinyl, and other aromatic heterocyclic groups. These substituents may also be substituted with the substituents exemplified above. In addition, these substituents, the benzene ring substituted by the substituents, or multiple substituents on the same benzene ring may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

[0101] In the general formula (A), L1 to L4 represent

[0102] "a divalent radical of a substituted or unsubstituted aromatic hydrocarbon",

[0103] "a substituted or unsubstituted divalent aromatic heterocyclic group", or

[0104] In the "substituted or unsubstituted condensed polycyclic aromatic divalent group",

[0105] "Divalent radical of aromatic hydrocarbon",

[0106] "a divalent aromatic heterocyclic group", or

[0107] "Condensed polycyclic aromatic divalent radical"

[0108] "Aromatic hydrocarbon", "aromatic heterocycle", or "condensed polycyclic aromatic" can be exemplified by

[0109] The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" represented by A, B or R in the general formula (A) is the same as those exemplified above, except that one hydrogen atom is removed from the exemplified group to form a divalent group.

[0110] In the “divalent aromatic hydrocarbon group having a substituent”, “divalent aromatic heterocyclic group having a substituent”, or “divalent condensed polycyclic aromatic group having a substituent” represented by L1 to L4 in the general formula (A), the “substituent” may be, for example, the same as the “substituent” exemplified in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group”, or “substituted condensed polycyclic aromatic group” represented by A, B or R in the general formula (A), and the exemplified embodiment modes are also the same.

[0111] In the general formula (A), L4 is preferably unsubstituted 1,2-phenylene, unsubstituted 1,3-phenylene or unsubstituted 1,4-phenylene, more preferably unsubstituted 1,2-phenylene or unsubstituted 1,3-phenylene, particularly preferably unsubstituted 1,2-phenylene.

[0112] In the general formula (A), one or both of A and B are preferably substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted phenanthryl, more preferably substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, and particularly preferably substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0113] The aromatic amine compound represented by the general formula (A) suitable for use in the organic EL device of the present invention is preferably used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light-emitting layer of the organic EL device, and more preferably used as a constituent material of the hole transport layer or electron blocking layer.

[0114] Furthermore, the aromatic amine compound represented by the general formula (A) of the present invention is preferably used as a constituent material of the organic layer in an electronic device comprising a pair of electrodes and at least one organic layer interposed therebetween. Effects of the invention

[0115] Compared with conventional hole transport materials, the aromatic amine compound represented by the general formula (A) of the present invention has the following properties: (1) excellent hole injection characteristics, (2) large hole mobility, (3) excellent electron blocking ability, (4) high electron tolerance, (5) stable thin film state, and (6) excellent heat resistance. By using the aromatic amine compound represented by the general formula (A) of the present invention in an organic EL device, the following properties can be obtained: (1) high luminous efficiency, (2) low luminescence starting voltage, (3) low practical driving voltage, and (4) long life.

[0116] The aromatic amine compound represented by general formula (A) of the present invention exhibits excellent hole injection and transport properties, thin film stability, and durability. Thus, using this compound as a hole injection material and / or hole transport material, an organic EL device having a hole injection layer and / or hole transport layer can improve the efficiency of hole transport to the light-emitting layer, thereby increasing luminous efficiency. Furthermore, by reducing the driving voltage, the durability of the device can be improved, resulting in high efficiency, low driving voltage, and long life.

[0117] The aromatic amine compound represented by general formula (A) of the present invention exhibits excellent electron-blocking properties, high electron tolerance, and stable thin-film properties, effectively trapping excitons generated within the light-emitting layer. Consequently, organic EL devices fabricated with this compound as an electron-blocking material in an electron-blocking layer can enhance the recombination rate of holes and electrons, suppress thermal deactivation, and thus achieve high luminous efficiency, lower driving voltage, and improved current tolerance, thereby increasing maximum luminous brightness.

[0118] The aromatic amine compound represented by general formula (A) of the present invention exhibits excellent hole-transporting properties and a wide band gap. Consequently, organic EL devices using this compound as a primary material in a light-emitting layer can achieve reduced driving voltage and improved luminous efficiency by forming a light-emitting layer that supports a fluorescent, phosphorescent, or delayed fluorescent emitter, commonly known as a "dopant."

[0119] Therefore, the aromatic amine compound represented by the general formula (A) of the present invention can be effectively used as a constituent material of the hole injection layer, hole transport layer, electron blocking layer or light-emitting layer of an organic EL component, and can improve the luminous efficiency, driving voltage, and durability of conventional organic EL components.

[0120] Furthermore, the aromatic amine compound represented by the general formula (A) of the present invention can be used not only in organic EL devices but also in the field of electronic devices such as electrophotographic photoreceptors, image sensors, photoelectric conversion devices, and solar cells.

Brief description of the attached figure

[0121] Figure 1 This is a structural diagram of compounds (1) to (15) among the aromatic amine compounds represented by general formula (A).

[0122] Figure 2 This is a structural diagram of compounds (16) to (27) among the aromatic amine compounds represented by general formula (A).

[0123] Figure 3 This is a structural diagram of compounds (28) to (39) among the aromatic amine compounds represented by general formula (A).

[0124] Figure 4This is a structural diagram of compounds (40) to (51) among the aromatic amine compounds represented by general formula (A).

[0125] Figure 5 This is a structural diagram of compounds (52) to (63) among the aromatic amine compounds represented by general formula (A).

[0126] Figure 6 This is a structural diagram of compounds (64) to (78) among the aromatic amine compounds represented by general formula (A).

[0127] Figure 7 This is a structural diagram of compounds (79) to (90) among the aromatic amine compounds represented by general formula (A).

[0128] Figure 8 This is a structural diagram of compounds (91) to (105) among the aromatic amine compounds represented by general formula (A).

[0129] Figure 9 This is a structural diagram of compounds (106) to (118) among the aromatic amine compounds represented by general formula (A).

[0130] Figure 10 This is a structural diagram of compounds (119) to (130) among the aromatic amine compounds represented by general formula (A).

[0131] Figure 11 This is a structural diagram of compounds (131) to (142) among the aromatic amine compounds represented by general formula (A).

[0132] Figure 12 This is a structural diagram of compounds (143) to (157) among the aromatic amine compounds represented by general formula (A).

[0133] Figure 13 This is a structural diagram of compounds (158) to (169) among the aromatic amine compounds represented by general formula (A).

[0134] Figure 14 It is a structural diagram of the organic EL modules of Examples 9 to 14 and Comparative Examples 1 and 2. [Implementation Method]

[0135] The aromatic amine compounds represented by the general formula (A) of the present invention are novel compounds and can be synthesized according to known methods.

[0136] Among the aromatic amine compounds represented by the general formula (A) above that are suitable for use in the organic EL device of the present invention, specific examples of preferred compounds are shown below. Figures 1 to 13 , but are not limited to these compounds.

[0137] The purification of the aromatic amine compound represented by the general formula (A) of the present invention can be carried out by the following well-known methods: purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization and crystallization using a solvent, and sublimation purification, and finally purification by sublimation purification. The identification of the compound is carried out by NMR analysis. As physical property values, the melting point, glass transition point (Tg) and work function can be listed. The melting point is an indicator of vapor deposition properties, the glass transition point (Tg) is an indicator of the stability of the thin film state, and the work function is an indicator of hole injection properties, hole transport properties, or electron blocking properties.

[0138] Furthermore, the compounds used in the organic EL device of the present invention are purified by, for example, column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization and crystallization using a solvent, and finally purified by sublimation purification.

[0139] The melting point and the glass transition point (Tg) can be measured using a powder, for example, with a high-sensitivity differential scanning calorimeter (DSC3100SA manufactured by Bruker AXS).

[0140] The work function can be determined, for example, by forming a 100 nm thin film on an ITO (Indium Tin Oxides) substrate and using an ionization potential measuring apparatus (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).

[0141] The structure of the organic EL component of the present invention includes: an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially included on a substrate; an electron blocking layer is provided between the hole transport layer and the light-emitting layer; and a hole blocking layer is provided between the light-emitting layer and the electron transport layer. In these multilayer structures, one organic layer can serve as multiple layers. For example, one organic layer can be configured as follows: it can serve as both a hole injection layer and a hole transport layer; or it can serve as both an electron injection layer and an electron transport layer. In addition, it can be configured as a stack of two or more organic layers having the same function, or it can be configured as follows: two hole transport layers are stacked; two light-emitting layers are stacked; and two electron transport layers are stacked.

[0142] As the anode of the organic EL device of the present invention, an electrode material having a large work function such as ITO or gold is used.

[0143] The hole injection layer material of the organic EL device of the present invention preferably uses an aromatic amine compound having only one triphenylamine structure in the molecule, such as the aromatic amine compound represented by general formula (A) of the present invention. Other materials that can be used include porphyrin compounds such as copper phthalocyanine; starburst triphenylamine derivatives; aromatic amine compounds having two or more triphenylamine structures or carbazole structures in the molecule, each linked by a single bond or a divalent group containing no heteroatoms; acceptor heterocyclic compounds such as hexacyanoazatriphenylene; and coating-type polymer materials. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet methods.

[0144] The hole injection layer and hole transport layer materials of the organic EL device of the present invention preferably use an aromatic amine compound having only one triphenylamine structure in the molecule, such as the aromatic amine compound represented by the general formula (A) of the present invention. In addition, benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)-benzidine (TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (NPD), and N,N,N',N'-tetraphenylbenzidine; 1,1-bis[(di-4-toluidino)phenyl]cyclohexane (TAPC); and aromatic amine compounds having two or more triphenylamine structures or carbazole structures in the molecule, each linked by a single bond or a divalent group containing no heteroatoms. These materials can be formed into a film alone, or a mixture of multiple types can be formed into a film, each used as a single layer. Alternatively, a structure may be formed by stacking layers of these materials individually, layers formed by mixing them, or layers formed by mixing multiple layers of these materials individually. Furthermore, coating-type polymer materials such as poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(styrenesulfonate) (PSS) can be used as materials for the hole injection / transport layer. These materials can be formed into thin films using known methods such as vapor deposition, spin coating, and inkjet.

[0145] In addition, the hole injection layer or hole transport layer can be made of materials commonly used in these layers that have been further doped with P such as tribromophenylamine hexachloroantimony or a radialene derivative (see, for example, Patent Document 6). Alternatively, a polymer compound having a structure of a benzidine derivative such as TPD in part of its structure can be used.

[0146] The electron blocking layer material of the organic EL device of the present invention preferably uses an aromatic amine compound represented by the general formula (A) of the present invention. In addition, carbazole derivatives such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), and 2,2-bis(4-carbazol-9-yl)phenyl)adamantane (Ad-Cz) can also be used; and compounds having a triphenylsilyl group and a triarylamine, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, can also be used. Compounds with electron blocking effects such as compounds with structures. These materials can also serve as materials for the hole transport layer. These materials can be formed into films alone or as a mixture of multiple materials, and can be used as a single layer. In addition, it can also be a laminated structure of layers formed by forming these materials alone, a laminated structure of layers formed by mixing these materials together; or a laminated structure of layers formed by forming these materials alone and layers formed by mixing multiple materials. These materials can be formed into thin films by well-known methods such as vapor deposition, spin coating, and inkjet.

[0147] As the light-emitting layer material of the organic EL device of the present invention, the aromatic amine compound represented by the general formula (A) of the present invention is preferably used. In addition, metal complexes of quinolinol derivatives, such as tris(8-quinolinol)aluminum (Alq3), various metal complexes, anthracene derivatives, bis(styrylbenzene) derivatives, pyrene derivatives, oxazole derivatives, and poly(p-phenylene vinylene) derivatives may also be used. Furthermore, the light-emitting layer may be composed of a host material and a dopant material. As the host material, the aromatic amine compound represented by the general formula (A) of the present invention or an anthracene derivative is preferably used. In addition to the above materials, heterocyclic compounds having an indole ring as a condensed ring structure, heterocyclic compounds having a carbazole ring as a condensed ring structure, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, and polydialkylfluorene derivatives may also be used. Furthermore, heterocyclic compounds having S, B, N, etc. as ring constituent elements are preferably used as dopant materials. In addition, for example, quinacridone, coumarin, rubrene, perylene and their derivatives, benzopyran derivatives, rhodamine derivatives and aminostyryl derivatives can also be used. These materials can be formed into films alone or as a mixture of multiple materials, and can be used as a single layer. In addition, a laminated structure of layers formed by forming these materials alone, a laminated structure of layers formed by forming a mixture, or a laminated structure of layers formed by forming these materials alone and layers formed by forming a mixture of multiple materials can be used. These materials can be formed into thin films by known methods such as vapor deposition, spin coating and inkjet methods.

[0148] In addition, phosphorescent light-emitting bodies can also be used as light-emitting materials. As phosphorescent light-emitting bodies, phosphorescent light-emitting bodies of metal complexes such as iridium or platinum can be used. For example, green phosphorescent light-emitting bodies such as Ir(ppy)3, blue phosphorescent light-emitting bodies such as FIrpic and FIr6, and red phosphorescent light-emitting bodies such as Btp2Ir(acac) can be listed. As the main material at this time, the main material for hole injection and transport properties can include carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP, and the aromatic amine compounds of the present invention can be listed. The main material for electron transport properties can include para-bis(triphenylsilyl)benzene (UGH2) or 2,2',2"-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI). By using this material, high-performance organic EL components can be produced.

[0149] When the host material is doped with a phosphorescent light-emitting material, in order to avoid concentration quenching, it is preferably doped in a range of 1 to 30 weight percent relative to the entire light-emitting layer by co-evaporation.

[0150] In addition, as light-emitting materials, PIC-TRZ (2-biphenyl-4,6-bis(12-phenylindole[2,3-a]carbazol-11-yl)-1,3,5-triazine, 2-biphenyl-4,6-bis(12-phenylindole[2,3-a]carbazol-11-yl)-1,3,5-triazine), CC2TA (2,4-bis{3-(9H-carbazol-9-yl)-9H-carbazol-9-yl}-6-phenyl-1,3,5-triazine) Materials that emit delayed fluorescence include CDCB (Carbazolyl Dicyanobenzene) derivatives such as 2,4-bis{3-(9H-carbazol-9-yl)-9H-carbazol-9-yl}-6-phenyl-1,3,5-triazine), PXZ-TRZ (benzoxazine-2,4,6-triphenyl-1,3,5-triazine), and 4CzIPN (2,4,5,6-Tetrakis(9-carbazol)-4,6-dicyanobenzene, 2,4,5,6-tetrakis(9-carbazolyl)isophthalonitrile) (for example, see Non-Patent Document 3). These materials can be formed into thin films by known methods such as vapor deposition, spin coating, and inkjet methods.

[0151] As the material of the hole blocking layer of the organic EL component of the present invention, metal complexes of quinolinol derivatives such as Vasocuproine (BCP), bis (2-methyl-8-quinolinol) -4- (phenylphenol) aluminum (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives and triazine derivatives can be used. Compounds with hole blocking effects can also be used as materials for the electron transport layer. These materials can be formed into films alone or mixed into multiple films, and can be used as single layers respectively. In addition, it is also possible to set the layers obtained by forming these materials into films alone, the layers obtained by mixing the layers into films, or the layers obtained by forming these materials into films alone and the layers obtained by mixing multiple films. These materials can be formed into thin films by well-known methods such as evaporation, spin coating and inkjet.

[0152] The electron transport layer material of the organic EL component of the present invention preferably uses, for example: benzimidazole derivatives, anthracene derivatives, pyrimidine derivatives, triazine derivatives. In addition, metal complexes of quinolinephenol derivatives such as Alq3 and BAlq can also be used; as well as various metal complexes, triazole derivatives, oxadiazole derivatives, pyridine derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, and silanol derivatives. These materials can be formed into a film alone or mixed into a film, and can be used as a single layer. In addition, it is also possible to set it as a laminated structure of layers obtained by forming these materials into films alone, a laminated structure of layers formed into films mixed together, or a laminated structure of layers obtained by forming these materials into films alone and layers formed into films mixed together. These materials can be formed into thin films by well-known methods such as evaporation, spin coating, and inkjet.

[0153] Materials for the electron injection layer of the organic EL device of the present invention include alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinolate, metal oxides such as aluminum oxide, and metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs). The electron injection layer can be omitted by selecting an optimal electron transport layer and cathode.

[0154] Furthermore, for the electron injection layer and the electron transport layer, metal N such as cesium may be doped into conventional materials of these layers.

[0155] As the cathode of the organic EL device of the present invention, metals with relatively low work functions such as aluminum and alloys with even lower work functions such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-magnesium alloys can be used as electrode materials. [Example]

[0156] Hereinafter, the embodiments of the present invention will be described in more detail in Examples. However, the present invention is not limited to the following Examples unless the gist of the invention is exceeded.

[0157] [Example 1]

[0158] Synthesis of N-(4-naphthyl-2-yl-phenyl)-N-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}-aniline (Compound 3)

[0159] To a nitrogen-substituted reaction vessel, 7.7 g of 9-(2-bromophenyl)-2-(phenyl-d5)-9H-carbazole, 9.0 g of N-(4-naphth-2-yl-phenyl)-N-{4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-aniline, 0.4 g of tetrakis(triphenylphosphine)palladium(0), and 5.0 g of potassium carbonate were added. The mixture was refluxed and stirred overnight in a toluene / ethanol / water mixture. After confirming the completion of the reaction, methanol was added to the system to precipitate a solid, which was then filtered to obtain a crude product. The crude product was purified by recrystallization using acetone to obtain 3.8 g (yield: 30.3%) of white powder of N-(4-naphthyl-2-yl-phenyl)-N-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}-aniline (compound: 3).

[0160]

[0161] The structure of the obtained white powder was identified using NMR.

[0162] use 1 H-NMR (CDCl3) detected the following 31 hydrogen signals:

[0163] δ(ppm)=8.09(2H), 7.89(2H), 7.86(1H), 7.84(1H), 7.74(2H), 7.68-7.52(4H), 7.47(3H), 7.40(2H) ), 7.33(1H), 7.26(1H), 7.19(1H), 7.17(1H), 7.10(2H), 6.92(1H), 6.86(2H), 6.81(3H), 6.72(2H).

[0164] [Example 2]

[0165] Synthesis of N,N-bis[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 24)

[0166] To a nitrogen-substituted reaction vessel, 8.0 g of N-[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine, 3.6 g of 4-bromo-[1,1'-biphenyl], 0.3 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, and 2.7 g of sodium tert-butoxide were added. The mixture was stirred under reflux overnight in xylene. After confirming the completion of the reaction, methanol was added to the system to precipitate a solid, which was filtered to obtain a crude product. The crude product was purified by crystallization using a tetrahydrofuran / acetone mixed solvent to obtain 5.6 g (yield: 55.2%) of white powder of N,N-bis[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (compound: 24).

[0167]

[0168] The structure of the obtained white powder was identified using NMR.

[0169] use 1 H-NMR (CDCl3) detected the following 33 hydrogen signals:

[0170] δ(ppm)=8.10(2H), 7.75(1H), 7.65-7.55(4H), 7.50(5H), 7.41(4H), 7.38-7.27(7H), 7.19(2H), 6.88(2H), 6.82(4H), 6.75(2H).

[0171] [Example 3]

[0172] Synthesis of N-[1,1'-biphenyl-4-yl]-N-(4-naphth-1-yl-phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 25)

[0173] To a nitrogen-substituted reaction vessel, 8.0 g of N-[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine, 4.4 g of 1-(4-bromophenyl)naphthalene, 0.3 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, and 2.7 g of sodium tert-butoxide were added. The mixture was stirred under reflux overnight in xylene. After confirming the completion of the reaction, methanol was added to the system to precipitate a solid, which was filtered to obtain a crude product. The crude product was purified by crystallization using a tetrahydrofuran / ethyl acetate mixed solvent to obtain 3.0 g (yield: 27.7%) of white powder of N-[1,1'-biphenyl-4-yl]-N-(4-naphth-1-yl-phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (compound: 25).

[0174]

[0175] The structure of the obtained white powder was identified using NMR.

[0176] use 1 H-NMR (CDCl3) detected the following 35 hydrogen signals:

[0177] δ(ppm)=8.11(1H), 8.09(1H), 7.95(1H), 7.90(1H), 7.83(1H), 7.77(1H), 7. 67-7.54(3H), 7.54-7.26(14H), 7.23(2H), 7.20(2H), 6.89(6H), 6.81(2H).

[0178] [Example 4]

[0179] Synthesis of N-[1,1'-biphenyl-4-yl]-N-(4-naphth-2-yl-phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 26)

[0180] To a nitrogen-substituted reaction vessel, 8.0 g of N-[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine, 4.4 g of 2-(4-bromophenyl)naphthalene, 0.3 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, and 2.7 g of sodium tert-butoxide were added. The mixture was stirred under reflux overnight in xylene. After confirming the completion of the reaction, methanol was added to the system to precipitate a solid, which was filtered to obtain a crude product. The crude product was purified by crystallization using a tetrahydrofuran / ethyl acetate mixed solvent to obtain 6.8 g (yield: 62.7%) of white powder of N-[1,1'-biphenyl-4-yl]-N-(4-naphth-2-yl-phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (compound: 26).

[0181]

[0182] The structure of the obtained white powder was identified using NMR.

[0183] use 1 H-NMR (CDCl3) detected the following 35 hydrogen signals:

[0184] δ(ppm)=8.11(2H), 7.93(1H), 7.88(2H), 7.85(1H), 7.77(1H), 7.68-7.55(4 H), 7.50(4H), 7.47-7.26(10H), 7.21(1H), 7.19(1H), 6.87(6H), 6.77(2H).

[0185] [Example 5]

[0186] Synthesis of N-phenyl-N-(4-(8-phenyl-2-naphthyl)phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 162)

[0187] To a nitrogen-substituted reaction vessel, 12.0 g of N-[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine, 8.5 g of 7-(4-chlorophenyl)-1-phenylnaphthalene, 0.5 g of tris(dibenzylideneacetone)palladium(0), 0.2 g of tri-tert-butylphosphine, and 4.7 g of sodium tert-butoxide were added. The mixture was stirred under reflux overnight in xylene. After confirming the completion of the reaction, methanol was added to the system to precipitate a solid, which was filtered to obtain a crude product. The crude product was purified by crystallization using a toluene / ethyl acetate mixed solvent to obtain 6.2 g (yield: 33.0%) of white powder of N-phenyl-N-(4-(8-phenyl-2-naphthyl)phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 162).

[0188]

[0189] The structure of the obtained white powder was identified using NMR.

[0190] use 1 H-NMR (DMSO-d6) detected the following 35 hydrogen signals:

[0191] δ(ppm)=8.18(2H), 8.08(1H), 7.98(1H), 7.92(1H), 7.83-7.67(5H), 7.64-7.50(7H), 7.47(1H) ), 7.38(1H), 7.32-7.24(3H), 7.15(3H), 7.09(1H), 6.96(1H), 6.86(2H), 6.69(2H), 6.58(4H).

[0192] [Example 6]

[0193] Synthesis of N-[1,1'-biphenyl-4-yl]-N-(4-(7-phenyl-1-naphthyl)phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (Compound 163)

[0194] To a nitrogen-substituted reaction vessel were added: 9.5 g of N-[1,1'-biphenyl-4-yl]-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine, 5.5 g of 1-(4-chlorophenyl)-7-phenylnaphthalene, 0.3 g of tris(dibenzylideneacetone)palladium(0), 0.1 g of tri-tert-butylphosphine, and 3.2 g of sodium tert-butoxide, and the mixture was refluxed and stirred in a xylene solvent overnight. After confirming completion of the reaction, the reaction mixture was isolated by column chromatography (support: silica gel, eluent: dichloromethane / n-heptane) and purified by crystallization using a tetrahydrofuran / methanol mixed solvent to obtain 12.0 g (yield: 84.8%) of white powder of N-[1,1'-biphenyl-4-yl]-N-(4-(7-phenyl-1-naphthyl)phenyl)-{2'-(2-phenyl-d5-9H-carbazol-9-yl)-[1,1'-biphenyl-4-yl]}amine (compound: 163).

[0195]

[0196] The structure of the obtained white powder was identified using NMR.

[0197] use 1 H-NMR (DMSO-d6) detected the following 39 hydrogen signals:

[0198] δ(ppm)=8.22-8.18(2H), 8.10(1H), 8.06(1H), 7.97(1H), 7.88-7.82(2H), 7.75-7.69(3H), 7.64(2H), 7 .60-7.53(4H), 7.47-7.37(9H), 7.32-7.26(4H), 7.17(1H), 7.12(1H), 6.91(2H), 6.79(4H), 6.72(2H).

[0199] [Example 7]

[0200] The DSC was measured by a high-sensitivity differential scanning calorimeter (made by Bruker AXS). 31 00SA), the melting point and glass transition point of the aromatic amine compound represented by general formula (A) were measured. The measurement results are summarized in Table 1.

[0201]

Table 1

[0202] The aromatic amine compound represented by the general formula (A) has a glass transition point of 100° C. or higher, indicating that the thin film state is stable.

[0203] [Example 8]

[0204] Using the aromatic amine compound represented by general formula (A), a 100 nm thick vapor-deposited film was formed on an ITO substrate, and the work function was measured using an ionization potential analyzer (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.). The measurement results are summarized in Table 2.

[0205]

Table 2

[0206] It can be seen that compared with the work function of 5.4 eV of common hole transport materials such as NPD and TPD, the aromatic amine compound represented by general formula (A) exhibits a better band gap, and is found to have better hole transport ability and excellent electron blocking ability.

[0207] [Example 9]

[0208] The organic EL components are prepared as follows: Figure 14 As shown, after a reflective ITO electrode serving as a transparent anode 2 is pre-formed on a glass substrate 1, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a covering layer 10 are sequentially vapor-deposited thereon.

[0209] Specifically, a 50nm-thick ITO film, a 100nm-thick silver alloy reflective film, and a 5nm-thick ITO film were sequentially formed on a glass substrate 1 as a transparent anode 2. The substrate was then ultrasonically cleaned in isopropyl alcohol for 20 minutes and dried on a hot plate heated to 250°C for 10 minutes. After a 2-minute UV ozone treatment, the ITO-coated glass substrate was placed in a vacuum deposition machine and the pressure was reduced to below 0.001 Pa.

[0210] Subsequently, an electron acceptor of the following structural formula and a compound (HTM-1) of the following structural formula were binary deposited at a deposition rate ratio of acceptor (Acceptor)-1:compound (HTM (Hole Transport Material)-1) = 3:97, thereby forming a hole injection layer 3 with a film thickness of 10 nm to cover the transparent anode 2.

[0211] On the hole injection layer 3 , a compound (HTM-1) of the following structural formula was formed as the hole transport layer 4 to a film thickness of 140 nm.

[0212] On the hole transport layer 4 , the compound (2) of Example 1 was formed as the electron blocking layer 5 to a film thickness of 5 nm.

[0213] The compound of the following structural formula (EMD-1) and the compound of the following structural formula (EMH-1) were binary evaporated at an evaporation rate ratio of EMD (N,N-bis(5-ethyl-2-hydroxybenzyl)methylamine, N,N-bis(5-ethyl-2-hydroxybenzyl)methylamine)-1:EMH (5-Ethyl-5-methylhydantoin, 5-ethyl-5-methylhydantoin)-1 = 5:95, thereby forming a light-emitting layer 6 on the electron blocking layer 5 in a film thickness of 20 nm.

[0214] The compound of the following structural formula (ETM-1) and the compound of the following structural formula (ETM-2) are binary evaporated at an evaporation rate ratio of ETM (Electron Transport Material)-1:ETM-2=50:50, thereby forming an electron transport layer 7 on the light-emitting layer 6 in a manner that has a film thickness of 30 nm.

[0215] On the electron transport layer 7 , lithium fluoride was formed as the electron injection layer 8 to a film thickness of 1 nm.

[0216] On the electron injection layer 8 , a magnesium-silver alloy was formed as a cathode 9 to a film thickness of 12 nm.

[0217] Finally, a compound of the following structural formula (CPL (Caprolactam, caprolactam)-1) was formed as the cover layer 10 to a film thickness of 60 nm.

[0218] The characteristics of the fabricated organic EL device were measured at room temperature in the atmosphere.

[0219] Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL devices.

[0220]

[0221]

[0222] [Examples 10-14]

[0223] An organic EL device was produced under the same conditions, except that in Example 9, the compound (3) of Example 1 was replaced with the compounds obtained in Examples 2 to 6 as the material for the electron blocking layer 5. The characteristics of the produced organic EL device were measured in the atmosphere at room temperature. The results of the measurement of the luminescence characteristics of the produced organic EL device when a DC voltage was applied are summarized in Table 3.

[0224] [Comparative Example 1]

[0225] For comparison, in Example 9, an organic EL device was produced under the same conditions, except that the compound (HTM-2) having the following structural formula (see, for example, Patent Document 7) was used instead of the compound (3) in Example 1 as the material for the electron blocking layer 5. The characteristics of the produced organic EL device were measured in the atmosphere at room temperature. The results of the measurement of the luminescence characteristics of the produced organic EL device when a DC voltage was applied are summarized in Table 3.

[0226]

[0227] [Comparative Example 2]

[0228] For comparison, in Example 9, an organic EL device was produced under the same conditions, except that the compound (HTM-3) of the following structural formula (see, for example, Patent Document 8) was used instead of the compound (3) of Example 1 as the material for the electron blocking layer 5. The characteristics of the produced organic EL device were measured in the atmosphere at room temperature. The results of the measurement of the luminescence characteristics of the produced organic EL device when a DC voltage was applied are summarized in Table 3.

[0229]

[0230] The organic EL devices prepared in Examples 9 to 14 and Comparative Examples 1 to 2 were used to measure the device life. The results are summarized in Table 3. The device life is calculated by setting the luminance at the start of luminescence (initial luminance) to 1000 cd / m 2 When static current driving is applied, the luminous brightness is measured to decay to 950cd / m 2 (This corresponds to the time from 95% to 95% attenuation when the initial brightness is 100%).

[0231]

Table 3

[0232] As shown in Table 3, the flow current density is 10 mA / cm 2 The luminous efficiency at current was higher, reaching 8.61 to 9.52 cd / A for the organic EL devices of Comparative Examples 1 and 2, compared to 8.24 to 8.26 cd / A. Furthermore, the power efficiency was also higher, reaching 8.02 to 8.66 lm / W for the organic EL devices of Comparative Examples 1 and 2, compared to 7.19 to 7.28 lm / W for the organic EL devices of Comparative Examples 1 and 2. Furthermore, the device lifespan (95% decay) was extended to 425 to 488 hours for the organic EL devices of Examples 9 to 14, compared to 349 to 364 hours for the organic EL devices of Comparative Examples 1 and 2.

[0233] The above results indicate that the organic EL device of the present invention can achieve higher luminous efficiency and longer life than conventional organic EL devices because it uses an aromatic amine compound with high hole mobility and excellent electron blocking ability.

[0234]

Explanation of symbols

[0235] 1: Glass substrate

[0236] 2: Transparent anode

[0237] 3: Hole injection layer

[0238] 4: Hole transport layer

[0239] 5: Electron blocking layer

[0240] 6: Luminous layer

[0241] 7: Electron transport layer

[0242] 8: Electron injection layer

[0243] 9: cathode

[0244] 10: Covering layer Industrial Applicability

[0245] The organic EL device using the aromatic amine compound having a specific structure of the present invention can enhance luminous efficiency and improve durability of the organic EL device, and thus can be developed for applications such as home telephone products and lighting.

Claims

1. An aromatic amine compound represented by the following general formula (A): In formula (A), A and B represent: a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; L1 to L4 indicate: single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group, a substituted or unsubstituted divalent aromatic heterocyclic group, or a substituted or unsubstituted divalent condensed polycyclic aromatic group; R is the same or different hydrogen atom, deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; However, at least one of R is a substituted aromatic substituent. 2 . The aromatic amine compound according to claim 1 , wherein at least one of R in the general formula (A) is a deuterated phenyl group.

3. The aromatic amine compound according to claim 2, which is represented by the following general formula (B), (C), (D) or (E): A, B, R and L1 to L4 in formula (B), (C), (D) or (E) have the same meanings as in the above general formula (A). 4 . The aromatic amine compound according to claim 3 , wherein in the general formula (B), (C), (D) or (E), R is a hydrogen atom or a deuterium atom.

5. The aromatic amine compound according to claim 4, wherein in the general formula (B), (C), (D) or (E), L1 to L4 are: single bond, Substituted or unsubstituted phenylene, Substituted or unsubstituted naphthylene, or Substituted or unsubstituted biphenylene.

6. The aromatic amine compound according to claim 5, wherein in the general formula (B), (C), (D) or (E), L4 is: Substituted or unsubstituted 1,2-phenylene, Substituted or unsubstituted 1,3-phenylene, Substituted or unsubstituted 1,4-phenylene, Substituted or unsubstituted 1,2-naphthylene, Substituted or unsubstituted 1,3-naphthylene, or Substituted or unsubstituted 1,4-naphthylene.

7. The aromatic amine compound according to claim 6, wherein in the general formula (B), (C), (D) or (E), L4 is: Unsubstituted 1,2-phenylene, Unsubstituted 1,3-phenylene, Unsubstituted 1,4-phenylene, Unsubstituted 1,2-naphthylene, Unsubstituted 1,3-naphthylene, or Substituted or unsubstituted 1,4-naphthylene.

8. An organic electroluminescent (EL) component comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer comprises the aromatic amine compound according to claim 1 or 2. 9 . The organic EL device according to claim 8 , wherein the organic layer is a hole transport layer. 10 . The organic EL device according to claim 8 , wherein the organic layer is an electron blocking layer.

11. The organic EL device according to claim 8, wherein the organic layer is a hole injection layer.

12. The organic EL device according to claim 8, wherein the organic layer is a light-emitting layer. 13 . An electronic device comprising a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer comprises the aromatic amine compound according to claim 1 or 2 .

Images