Organic electroluminescent device

Abstract

The organic EL device includes an anode, a light-emitting layer, an anode-side hole transport layer between the anode and the light-emitting layer, the anode-side hole transport layer including an anode-side hole transport material and doped with an electron accepting material, an intermediate hole transport layer between the anode-side hole transport layer and the light-emitting layer, the intermediate hole transport layer including an intermediate hole transport material, and a light-emitting layer-side hole transport layer between the intermediate hole transport layer and the light-emitting layer, the light-emitting layer-side hole transport layer being adjacent to the light-emitting layer, wherein the light-emitting layer-side hole transport layer includes a light-emitting layer-side hole transport material represented by the following formula 1: [Formula 1]

Description

[0001] This application is a divisional application of an invention patent application with an application date of December 2, 2015, application number 201510870448.3, and invention name “Organic electroluminescent device”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] Japanese Patent Application No. 2014-244485 and Japanese Patent Application No. 2014-244490, both filed on Dec. 2, 2014 with the Japan Intellectual Property Office and both entitled “ORGANIC ELECTROLUMINESCENT DEVICE,” are hereby incorporated by reference in their entirety. Technical Field

[0004] Embodiments relate to organic electroluminescent devices. Background Art

[0005] Recently, the development of organic electroluminescent (EL) displays is actively being advanced. At the same time, the development of organic EL devices, which are self-luminous type light-emitting devices used in organic EL displays, is also actively being advanced.

[0006] The organic EL device may have, for example, a stacked structure of an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode in this order.

[0007] In such an organic EL device, holes and electrons injected from the anode and the cathode may be recombined in the light-emitting layer to generate excitons, and light emission may be achieved through the generated excitons transitioning to the ground state. Summary of the invention

[0008] Embodiments relate to organic electroluminescent devices.

[0009] An embodiment may be implemented by providing an organic EL device including an anode, a light-emitting layer, an anode-side hole transport layer between the anode and the light-emitting layer, the anode-side hole transport layer including an anode-side hole transport material and doped with an electron accepting material, an intermediate hole transport layer between the anode-side hole transport layer and the light-emitting layer, the intermediate hole transport layer including an intermediate hole transport material, and a light-emitting layer-side hole transport layer between the intermediate hole transport layer and the light-emitting layer, the light-emitting layer-side hole transport layer being adjacent to the light-emitting layer, wherein the light-emitting layer-side hole transport layer includes a light-emitting layer-side hole transport material represented by the following Formula 1:

[0010] [Formula 1]

[0011]

[0012] Wherein, in Formula 1, Ar 1 and Ar 2are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, R 1 To R 3 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms, R 1 To R 3 wherein two or more adjacent groups are separated or combined to form a ring, m is an integer from 0 to 4, p and q are each independently an integer from 0 to 5, L 1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and the carbon atoms a and b are separated or bonded via a direct bond.

[0013] The intermediate hole transport material may include a compound represented by the following Formula 2:

[0014] [Formula 2]

[0015]

[0016] Among them, in formula 2, Ar 1 To Ar 3 Ar may be each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms. 4 L may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

[0017] The anode-side hole transport material may include a compound represented by Formula 2 below.

[0018] The electron accepting material may have a lowest unoccupied molecular orbital (LUMO) level of about -9.0 eV to about -4.0 eV.

[0019] An anode-side hole transport layer may be adjacent to the anode.

[0020] The light emitting layer may include a compound represented by the following Formula 3:

[0021] [Formula 3]

[0022]

[0023] Wherein, in Formula 3, each Ar 1 The radicals may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and n may be an integer from 1 to 10.

[0024] An embodiment may be implemented by providing an organic EL device including an anode, a light-emitting layer, an anode-side hole transport layer between the anode and the light-emitting layer, the anode-side hole transport layer mainly including an electron accepting material, an intermediate hole transport layer between the anode-side hole transport layer and the light-emitting layer, the intermediate hole transport layer including an intermediate hole transport material, and a light-emitting layer-side hole transport layer between the intermediate hole transport layer and the light-emitting layer, the light-emitting layer-side hole transport layer being adjacent to the light-emitting layer, wherein the light-emitting layer-side hole transport layer includes a light-emitting layer-side hole transport material represented by the following Formula 1:

[0025] [Formula 1]

[0026]

[0027] Wherein, in Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, R 1 To R 3 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms, R 1 To R 3 wherein two or more adjacent groups are separated or combined to form a ring, m is an integer from 0 to 4, p and q are each independently an integer from 0 to 5, L 1is a direct bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and the carbon atoms a and b are separated or bonded via a direct bond.

[0028] The intermediate hole transport material may include a compound represented by the following Formula 2:

[0029] [Formula 2]

[0030]

[0031] Among them, in formula 2, Ar 1 To Ar 3 Ar may be each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms. 4 L may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

[0032] The electron accepting material may have a lowest unoccupied molecular orbital (LUMO) level of about -9.0 eV to about -4.0 eV.

[0033] An anode-side hole transport layer may be adjacent to the anode.

[0034] The light emitting layer may include a compound represented by the following Formula 3:

[0035] [Formula 3]

[0036]

[0037] Wherein, in Formula 3, each Ar 1The radicals may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and n may be an integer from 1 to 10. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Features will become apparent to those skilled in the art by describing exemplary embodiments in detail with reference to the accompanying drawings, in which:

[0039] Figure 1 Illustrations of organic EL devices according to embodiments are illustrated. DETAILED DESCRIPTION

[0040] Example embodiments will now be described in more detail below with reference to the accompanying drawings; however, they may be implemented in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

[0041] In the accompanying drawings, the dimensions of layers and regions may be exaggerated for clarity. It should also be understood that when a layer or element is referred to as being "on" another layer or element, it can be directly on the other layer or element, or there may be intervening elements. In addition, it should also be understood that when an element is referred to as being "between" two elements, it can be the only element between the two elements, or there may be one or more intervening elements. The same reference numerals refer to the same elements throughout.

[0042] <1-1. Configuration of organic EL device>

[0043] (1-1-1. Overall configuration)

[0044] First, based on Figure 1 , the overall configuration of the organic EL device 100 according to the embodiment will be described.

[0045] like Figure 1As shown, the organic EL device 100 according to the embodiment may include, for example, a substrate 110, a first electrode 120 on the substrate 110, a hole transport layer 130 on the first electrode 120, a light emitting layer 140 on the hole transport layer 130, an electron transport layer 150 on the light emitting layer 140, an electron injection layer 160 on the electron transport layer 150, and a second electrode 170 on the electron injection layer 160. In implementation, the hole transport layer 130 may be formed to have a multilayer structure consisting of a plurality of layers 131, 133, and 135.

[0046] (1-1-2. Configuration of substrate)

[0047] The substrate 110 may be a substrate suitably used for an organic EL device, for example, the substrate 110 may be a glass substrate, a semiconductor substrate, or a transparent plastic substrate.

[0048] (1-1-3. Configuration of First Electrode)

[0049] The first electrode 120 may be, for example, an anode, and may be formed on the substrate 110 by evaporation, sputtering, or the like. For example, the first electrode 120 may be formed as a transmissive electrode using a metal, an alloy, a conductive compound, or the like having a high work function. The first electrode 120 may be formed using, for example, indium tin oxide (In2O3) having good transparency and conductivity. 2 O 3 -SnO 2 :ITO), indium zinc oxide (In 2 O 3 -ZnO:IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO), etc. In implementation, the first electrode 120 may be formed as a reflective electrode formed by stacking magnesium (Mg), aluminum (Al), etc.

[0050] (1-1-4. Configuration of hole transport layer)

[0051] The hole transport layer 130 may include a hole transport material and may have a hole transport function. The hole transport layer 130 may be formed, for example, on the first electrode 120 to a layer thickness of about 10 nm to about 150 nm (eg, a total layer thickness of a multilayer structure).

[0052] The hole transport layer 130 of the organic EL device 100 according to the embodiment may be formed as a multilayer by stacking an anode-side hole transport layer 131 , an intermediate hole transport layer 133 , and a light-emitting layer-side hole transport layer 135 one by one (from the first electrode 120 ).

[0053] (1-1-4-1. Configuration of hole transport layer on the anode side)

[0054] The anode-side hole transport layer 131 may be a layer including an anode-side hole transport material and may be doped with an electron accepting material. For example, the anode-side hole transport layer 131 may be formed on the first electrode 120 (eg, directly formed thereon).

[0055] The anode-side hole transport layer 131 may be doped with an electron accepting material, and hole injection properties from the first electrode 120 may be improved. In implementation, the anode-side hole transport layer 131 may be provided near the first electrode 120, for example, may be provided adjacent to (eg, directly adjacent to or in direct contact with) the first electrode 120.

[0056] The anode-side hole transport material included in the anode-side hole transport layer 131 may include a suitable hole transport material. Examples of the anode-side hole transport material included in the anode-side hole transport layer 131 may include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), and the like.

[0057] The electron accepting material included in the anode-side hole transport layer 131 may include a suitable electron accepting material. In implementations, the electron accepting material included in the anode-side hole transport layer 131 may have a LUMO level of about -9.0 eV to about -4.0 eV, for example, about -6.0 eV to about -4.0 eV.

[0058] Examples of electron accepting materials having a LUMO level of about -9.0 eV to about -4.0 eV may include

[0059] One of the compounds represented by formulae 4-1 to 4-14.

[0060]

[0061] In the above formulae 4-1 to 4-14, each R may independently be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heteroaryl group having 5 to 50 ring carbon atoms.

[0062] Each Ar may independently be or include, for example, a substituted aromatic group having an electron withdrawing group or an unsubstituted aromatic group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaromatic group having 5 to 50 ring carbon atoms, each Y may independently be, for example, a methylene group (-CH=) or a nitrogen atom (-N=), each Z may independently be, for example, a pseudohalogen atom or a sulfur (S) atom, n may be an integer of 10 or less, and each X may independently be a substituent represented by one of the following X1 to X7.

[0063]

[0064] In the above formulae X1 to X7, each Ra may independently be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.

[0065] Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R, Ar and Ra may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-, 2-biphenyl-, 3-biphenyl-, 4-biphenyl-, 4-ter ... 4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, fluoranthenyl, fluorenyl and the like.

[0066] Examples of the substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms represented by R, Ar and Ra may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-benzofuranyl, -isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-isoquinolyl, 2-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, -quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4- Acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8 ...8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl yl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furoxyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, etc.

[0067] Examples of the substituted or unsubstituted fluoroalkyl group having 1 to 50 carbon atoms represented by R and Ra may include perfluoroalkyl groups such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl and heptadecafluorooctyl, monofluoromethyl, difluoromethyl, trifluoroethyl, tetrafluoropropyl, octafluoropentyl and the like.

[0068] Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by R and Ra may include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, , 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-di Iodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-tert-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diamino-tert-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyano isopropyl, 2,3-dicyano-tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like.

[0069] The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms represented by R and Ra may be a group represented by —OY. Examples of Y may include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl , 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-tert-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diamino-tert-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-Cyanoethyl, 2-Cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, and the like.

[0070] Examples of the halogen atom represented by R and Ra may include fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the like.

[0071] In implementations, the electron accepting material may include one of the following compounds 4-15 and 4-16. For example, the LUMO level of compound 4-15 may be about -4.40 eV, and the LUMO level of compound 4-16 may be about -5.20 eV.

[0072]

[0073] In implementation, the doping amount of the electron accepting material may be a suitable amount that can be doped into the anode-side hole transport layer 131. For example, the doping amount of the electron accepting material may be about 0.1 wt% to about 50 wt% based on the total amount or total weight of the anode-side hole transport material included in the anode-side hole transport layer 131. In implementation, the doping amount may be about 0.5 wt% to about 5 wt%.

[0074] (1-1-4-2. Configuration of Intermediate Hole Transport Layer)

[0075] The intermediate hole transport layer 133 may include an intermediate hole transport material. The intermediate hole transport layer 133 may be formed, for example, on the anode-side hole transport layer 131 .

[0076] The intermediate hole transport material included in the intermediate hole transport layer 133 may include a suitable hole transport material. For example, the intermediate hole transport material may include the hole transport material described above as the anode-side hole transport material.

[0077] In implementations, the intermediate hole transport material may include a compound represented by Formula 2 below.

[0078] [Formula 2]

[0079]

[0080] In the above formula 2, Ar 1 To Ar 3 Ar may each independently be or include, for example, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms. 4 It may be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. 1 It may be or may include, for example, a direct bond (single bond), a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

[0081] Ar 1 To Ar 3 Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzothiazolyl, quinoxalinyl, benzoxazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, etc. In implementation, Ar 1 To Ar 3 The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, the dibenzofuranyl group, and the like may be included.

[0082] Ar 4Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, methyl, ethyl, propyl, isopropyl, n-butyl, and the like. In implementations, Ar 4 The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, the dibenzofuranyl group, the methyl group, the ethyl group, and the like may be included.

[0083] L 1 Examples of (except for direct linkages) may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenylene, fluorenylene, indenylene, pyrenylene, acenaphtheneylene, fluoranthenylene, triphenylene, pyridylene, furanylene, pyranylene, thienylene, quinolylene, isoquinolylene, benzofuranylene, benzothienylene, indolylene, carbazolylene, benzoxazolylene, benzothiazolylene, quinoxalinyl, benzimidazolylene, pyrazolylene, dibenzofuranylene, dibenzothienylene, and the like. In implementations, L 1 The direct bond, the phenylene group, the biphenylene group, the terphenylene group, the fluorenylene group, the carbazolylene group, or the dibenzofuranylene group may be included.

[0084] Examples of the compound represented by Formula 2 may include one of the following Compounds 2-1 to 2-16.

[0085]

[0086] The intermediate hole transport layer 133 may include the compound represented by Formula 2 above as an intermediate hole transport material and may contribute to improving the hole transport property of the hole transport layer 130. Therefore, the light emission efficiency of the organic EL device 100 may be improved.

[0087] In implementation, the compound represented by Formula 2 may be included in the anode-side hole transport layer 131 as an anode-side hole transport material. In the case where the anode-side hole transport layer 131 includes the compound represented by Formula 2 as an anode-side hole transport material, the hole transport property of the hole transport layer 130 is improved, and the light emission efficiency of the organic EL device 100 may be improved.

[0088] In practice, in the case where the ratio of the carbazole derivative, such as the compound represented by Formula 2, included in the hole transport layer 130 is high, the light emission lifetime of the organic EL device 100 may be improved.

[0089] The anode-side hole transport layer 131 may further include other hole transport materials in addition to the compound represented by Formula 2 as the anode-side hole transport material.

[0090] (1-1-4-3. Configuration of hole transport layer on the light-emitting layer side)

[0091] The light emitting layer-side hole transport layer 135 may include a compound represented by the following Formula 1. The light emitting layer-side hole transport layer 135 may be formed, for example, on the intermediate hole transport layer 133 , adjacent to (eg, directly adjacent to or directly in contact with) the light emitting layer 140 .

[0092] [Formula 1]

[0093]

[0094] In formula 1, Ar 1 and Ar 2 Each independently may be or include, for example, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.

[0095] R 1 To R 3 Each independently may be or include, for example, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms. 1 To R 3 Two or more adjacent groups in the may be separated from each other or may be combined to form a ring.

[0096] Furthermore, m may be an integer from 0 to 4, and p and q may each independently be an integer from 0 to 5. 1 It may be or may include, for example, a direct bond (e.g., a single bond), a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms. Carbon atoms a and b may be separated from each other or may be bonded or combined via a direct bond.

[0097] Ar 1 and Ar 2 Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, etc. In implementation, Ar 1 and Ar 2The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, and the dibenzofuranyl group may be included.

[0098] R 1 To R 3 Examples of may include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, tert-butyl, cyclobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, nonyl, decyl, etc., except Ar 1 and Ar 2 specific instance of .

[0099] Ar 1 and Ar 2 and R 1 To R 3 The substituents of may include alkyl, alkoxy, aryl and heteroaryl. Examples of the alkyl, aryl and heteroaryl may be the same as described above. Examples of alkoxy may include alkoxy substituted by alkyl.

[0100] L 1 Examples (except for direct linkage / single bond) may include divalent substituents or 1 and Ar 2 Describes the form of the group in question. For example, L 1 The phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorenyl, fluorene diyl, indandiyl, pyrene diyl, acenaphthene diyl, fluoranthene diyl, triphenylene diyl, pyridine diyl, pyran diyl, quinoline diyl, isoquinoline diyl, benzofuran diyl, benzothiophene diyl, indole diyl, carbazole diyl, benzooxazole diyl, benzothiazole diyl, quinoxaline diyl, benzimidazole diyl and dibenzofuran diyl may be included. In implementation, the phenylene, terphenylene, fluorene diyl, carbazole diyl and dibenzofuran diyl may be used.

[0101] In implementations, the compound represented by Formula 1 may include one of the following Compounds 1 to 12.

[0102]

[0103]

[0104] The light-emitting layer-side hole transport layer 135 may include a compound represented by Formula 1 above as a light-emitting layer-side hole transport material, and the electrons from the light-emitting layer 140 that are not consumed may passivate the hole transport layer 130. In implementation, the light-emitting layer-side hole transport layer 135 may include a compound represented by Formula 1 above, and may reduce and / or prevent the energy of an excited state generated in the light-emitting layer 140 from diffusing into the hole transport layer 130. Therefore, according to this configuration, the light-emitting layer-side hole transport layer 135 may contribute to improving the current durability of the hole transport layer 130.

[0105] The light-emitting layer-side hole transport layer 135 may be formed close to the light-emitting layer 140. For example, the light-emitting layer-side hole transport layer 135 may be formed adjacent to (eg, directly adjacent to or directly in contact with) the light-emitting layer 140, thereby helping to effectively prevent electrons or energy from diffusing from the light-emitting layer 140.

[0106] The light-emitting layer-side hole transport layer 135 may include the compound represented by Formula 1 above, the charge balance of the entire organic EL device 100 may be controlled, and the electron accepting material doped into the anode-side hole transport layer 131 may be inhibited from diffusing to the light-emitting layer 140. Therefore, the light-emitting layer-side hole transport layer 135 may contribute to improving the overall charge transport properties of the hole transport layer 130.

[0107] In implementation, the light emitting layer side hole transport layer 135 may include the compound represented by Formula 1 above, and the charge transport property and current durability of the hole transport layer 130 may be improved. Therefore, the light emission efficiency and light emission lifetime of the organic EL device 100 may be improved.

[0108] As described above, the hole transport layer 130 including the anode side hole transport layer 131, the intermediate hole transport layer 133 and the light emitting layer side hole transport layer 135 can help improve the current durability and hole transport properties of the organic EL device 100. Therefore, the organic EL device 100 according to the embodiment can have improved luminous efficiency and luminous lifetime.

[0109] (1-1-5. Configuration of Light Emitting Layer)

[0110] The light emitting layer 140 may include a host material, a dopant material as a light emitting material, etc., and emit light via fluorescence or phosphorescence. The light emitting layer 140 may be formed on the hole transport layer 130 to a layer thickness ranging from about 10 nm to about 60 nm, for example.

[0111] The host material and the dopant material included in the light emitting layer 140 may include suitable host materials and dopant materials. For example, the light emitting layer 140 may include fluoranthene derivatives, pyrene (and its derivatives), arylacetylene derivatives, fluorene derivatives, perylene (and its derivatives), chrysene derivatives, styryl derivatives, etc. as host materials or dopant materials. More specifically, the light emitting layer 140 may include tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazole)-2,2'-dimethyl-biphenyl (dmCBP), bis(2,2-diphenylvinyl)-1,1 '-Biphenyl (DPVBi), 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)phenyl]stilbene (DPAVB), N-(4-(E)-2-(6-((E)-4-(diphenylamino)phenyl)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), 1,1-bipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc. are used as host materials or dopant materials.

[0112] In implementations, the light emitting layer 140 may include a compound represented by Formula 3 below.

[0113] [Formula 3]

[0114]

[0115] In the above formula 3, each Ar 1 The radical may independently be or include, for example, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group, and n may be an integer from 1 to 10.

[0116] In implementations, the compound represented by Formula 3 may include one of the following compounds 3-1 to 3-12.

[0117]

[0118] In the case where the light emitting layer 140 includes the compound represented by Formula 3, the anode-side hole transport layer 131 can contribute to significantly improve the hole injection property from the first electrode 120. Therefore, the light emitting layer 140 can contribute to further improving the light emission efficiency and light emission life of the organic EL device 100 by including the compound represented by Formula 3.

[0119] The light emitting layer 140 may include the compound represented by Formula 3 as a host material or as a dopant material.

[0120] The light emitting layer 140 may be formed as a layer that emits light of a specific color, for example, a red light emitting layer, a green light emitting layer, or a blue light emitting layer.

[0121] When the light emitting layer 140 is a blue light emitting layer, a suitable blue dopant may be used. For example, perylene and its derivatives, iridium (Ir) complexes such as bis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium (III) (FIrpic) may be used as blue dopants.

[0122] In the case where the light-emitting layer 140 is a red light-emitting layer, a suitable red dopant may be used. For example, rubrene and its derivatives, 4-dicyanomethylene-2-(p-dimethylaminophenylvinyl)-6-methyl-4H-pyran (DCM) and its derivatives, iridium complexes such as bis(1-phenylisoquinoline)(acetylacetonate)iridium(III) (Ir(piq) 2 Osmium (acac), osmium (Os) complex, platinum complex, etc. can be used as a red dopant.

[0123] When the light-emitting layer 140 is a green light-emitting layer, a suitable green dopant may be used. For example, coumarin and its derivatives, iridium complexes such as tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 )wait.

[0124] (1-1-6. Configuration of electron transport layer)

[0125] The electron transport layer 150 is a layer including an electron transport material and having an electron transport function. The electron transport layer 150 may be formed, for example, on the light emitting layer 140 to a layer thickness ranging from about 15 nm to about 50 nm. The electron transport material included in the electron transport layer 150 may include a suitable electron transport material. Examples of the electron transport material may include quinoline derivatives such as tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,2,4-triazole derivatives (TAZ), bis(2-methyl-8-hydroxyquinolinato)-(p-phenylphenolato)-aluminum (BAlq), bis(10-hydroxybenzoquinolinato)beryllium (BeBq2), Li complexes such as 8-hydroxyquinolinato lithium (LiQ), nitrogen-containing aromatic rings, etc. Examples of nitrogen-containing aromatic rings may include pyridine ring-containing materials such as 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, triazine ring-containing materials such as 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, imidazole derivative-containing materials such as 2-(4-(N-phenylbenzimidazol-1-ylphenyl)-9,10-dinaphthylanthracene), etc.

[0126] (1-1-7. Configuration of electron injection layer)

[0127] The electron injection layer 160 is a layer having a function of promoting the injection of electrons from the second electrode 170. The electron injection layer 160 may be formed, for example, on the electron transport layer 150 to a layer thickness in the range of about 0.3 nm to about 9 nm. The electron injection layer 160 may be formed using a suitable material (which may be used as a material for forming the electron injection layer 160). Examples of materials for forming the electron injection layer 160 may include lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide (Li 2 O), barium oxide (BaO), 8-hydroxyquinoline lithium (LiQ), etc.

[0128] (1-1-8. Configuration of Second Electrode)

[0129] The second electrode 170 may be, for example, a cathode, and may be formed on the electron injection layer 160 using an evaporation method or a sputtering method. For example, the second electrode 170 may be formed as a reflective electrode using a metal, an alloy, a conductive compound, etc. having a low work function. The second electrode 170 may be formed using, for example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag). The second electrode 170 may be formed as a thin film of a material having a thickness of about 20 nm or less, and may be formed as a transmissive electrode using ITO, IZO, etc.

[0130] (1-1-9. Improved Example of Organic EL Device)

[0131] Figure 1 The structure of the organic EL device 100 shown is for illustration only. In the organic EL device 100 according to the embodiment, some layers may be formed as a multilayer, or another layer may be additionally formed. In the organic EL device 100 according to the embodiment, at least one of the electron transport layer 150 and the electron injection layer 160 may not be provided.

[0132] In implementation, in the organic EL device 100 according to the embodiment, a hole injection layer may be provided between the first electrode 120 and the hole transport layer 130 .

[0133] The hole injection layer is a layer having a function of promoting the injection of holes from the first electrode 120. The hole injection layer can be formed, for example, on the first electrode 120 to a layer thickness in the range of about 10 nm to about 150 nm. The hole injection layer can be formed using a suitable material (the suitable material is a material for forming the hole injection layer). Examples of materials for forming the hole injection layer may include triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), phthalocyanine compounds such as copper phthalocyanine, 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N' -diphenylbenzidine (NPB), 4,4',4"-tri{N,N-diphenylamino}triphenylamine (TDATA), 4,4',4"-tri(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), or polyaniline / poly(4-styrenesulfonate (PANI / PSS), etc.

[0134] (1-1-10. Method for manufacturing organic EL device)

[0135] Each layer of the organic EL device 100 according to the embodiment as described above may be formed by selecting an appropriate layer forming method such as vacuum evaporation, sputtering, and various coating methods according to the material used.

[0136] For example, metal layers such as the first electrode 120, the second electrode 170, and the electron injection layer 160 may be formed using evaporation methods including electron beam evaporation, hot wire evaporation, and vacuum evaporation, sputtering, and plating methods such as electroplating and electroless plating.

[0137] The organic layers such as the hole transport layer 130 , the light emitting layer 140 , and the electron transport layer 150 may be formed using a physical vapor deposition (PVD) method such as a vacuum deposition method, a printing method such as a screen printing method and an inkjet printing method, a laser transfer method, or a coating method such as a spin coating method.

[0138] Hereinabove, the embodiment of the organic EL device 100 according to the embodiment has been explained in detail.

[0139] [Example]

[0140] The following examples and comparative examples are provided to emphasize the features of one or more embodiments, but it should be understood that the examples and comparative examples should not be interpreted as limiting the scope of the embodiments, and the comparative examples should not be interpreted as being outside the scope of the embodiments. In addition, it should be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0141] <1-2. Example>

[0142] Hereinafter, an organic EL device according to an exemplary embodiment will be explained with particular reference to Examples and Comparative Examples.

[0143] (1-2-1. Synthesis of Compounds)

[0144] (Synthesis Example 1: Synthesis of Compound 1)

[0145] Compound 1 was synthesized according to the following reaction scheme.

[0146]

[0147] (Synthesis of Compound A)

[0148] Under an argon atmosphere, 53.8 g of N-[1,1'-biphenyl]-4-yl-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine and 6.46 g of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium·CH 2 Cl 2 (Pd(dppf)Cl 2 ·CH 2 Cl 2 ), 33.3 g of potassium acetate (KOAc) and 33.0 g of bis(pinacolato)diboron were added to a 2 L flask, followed by degassing under vacuum and stirring in 750 mL of dioxane solvent at about 100° C. for about 12 hours. Then, the solvent was distilled off, and CH 2 Cl 2The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) to produce 56.8 g (yield 98%) of compound A as a white solid (FAB-MS: C 36 H 34 BNO 2 , measured value 523).

[0149] (Synthesis of Compound 1)

[0150] Under an argon atmosphere, 1.66 g of compound A, 1.52 g of compound B, 0.11 g of tetrakis(triphenylphosphine)palladium(0)(Pd(PPh 3 ) 4 ) and 1.1g of sodium carbonate were added to a 200mL three-necked flask, followed by heating and stirring at about 80°C in a mixed solvent of 40mL toluene, 19mL EtOH and 9.0L water for about 2 hours. After air cooling, water was added to the reactants, the organic phase was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of toluene and hexane) and recrystallized using a mixed solvent of toluene and EtOH to produce 1.96g (yield 84%) of compound 1 as a white solid. The molecular weight of compound 1 measured by FAB-MS was 713. By 1 H NMR (300 MHz, CDCl 3 ) measured the chemical shift values ​​(δ) of compound 1 to be 7.82-7.76 (m, 2H), 7.62-7.56 (m, 6H), 7.53-7.49 (m, 5H), 7.47 (d, 2H, J=6.0 Hz), 7.45-7.39 (m, 4H), 7.37-7.29 (m, 3H), 7.27-7.18 (m, 17H). Thus, the synthesis of compound 1 was confirmed.

[0151] (Synthesis Example 2: Synthesis of Compound 5)

[0152] Compound 5 was synthesized according to the following reaction scheme.

[0153]

[0154] (Synthesis of Compound C)

[0155] Under an argon atmosphere, 2.32 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 4.00 g of 2-bromo-9,9-diphenylfluorene, 1.04 g of Pd(PPh 3 ) 4, 2.79 g of potassium carbonate were added to a 500 mL three-necked flask, followed by heating and stirring at about 90° C. in a mixed solvent of 200 mL of toluene, 32 mL of water and 12 mL of ethanol for about 14 hours. After air cooling, water was added, the organic layer was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and recrystallized using a mixed solvent of ethyl acetate and hexane to produce 2.18 g (yield 53%) of compound C as a white solid (FAB-MS: C 31 H 23 N, measured value 409).

[0156] (Synthesis of Compound 5)

[0157] Under an argon atmosphere, 2.11 g of compound C, 3.15 g of bromodibenzofuran, and 0.384 g of tris(dibenzylideneacetone)dipalladium·CHCl were added. 3 ((Pd 2 (dba) 3 ·CHCl 3 and 2.06 g t-BuONa were added to a 200 mL three-necked flask, and 65 mL dehydrated toluene and 0.56 mL 2M (t-Bu) 3 P / dehydrated toluene, then heated and refluxed for about 7 hours. After air cooling, water was added, the organic phase was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and recrystallized using a mixed solvent of dichloromethane and ethanol to produce 3.30 g (yield 62%) of compound 5 as a white solid. Compound 5 (C 55 H 35 NO 2 ) has a molecular weight of 741. 1 H NMR (300 MHz, CDCl 3 The chemical shift values ​​(δ) of compound 5 measured by HPLC were 7.87 (dd, 2H), 7.81 (d, 2H), 7.80 (dd, 2H), 7.54-7.46 (4H), and 7.46-7.13 (25H). The synthesis of compound 5 was thus confirmed.

[0158] (1-2-2. Production of an organic EL device including an anode-side hole transport material and an anode-side hole transport layer doped with an electron accepting material)

[0159] The organic EL device according to the embodiment is manufactured by the following manufacturing method.

[0160] First, on the ITO-glass substrate that had been patterned and washed in advance, UV-ozone (O 3). The layer thickness of the ITO layer (first electrode) on the glass substrate was about 150 nm. After the ozone treatment, the surface-treated substrate was inserted into a glass bell-jar type evaporator for forming an organic layer and heated for about 10 -4 to about 10 -5 The anode side hole transport layer, the intermediate hole transport layer, the light emitting layer side hole transport layer, the light emitting layer and the electron transport layer were evaporated one by one at a vacuum degree of 1.5 Pa. The layer thickness of each of the anode side hole transport layer, the intermediate hole transport layer and the light emitting layer side hole transport layer was about 10 nm. The layer thickness of the light emitting layer was about 25 nm, and the layer thickness of the electron transport layer was about 25 nm. Then, the substrate was moved into a glass bell jar type evaporator for forming a metal layer, and the substrate was evaporated with about 10 -4 to about 10 -5 The electron injection layer and the second electrode were evaporated at a vacuum degree of 100 Pa. The layer thickness of the electron injection layer was about 1 nm and the layer thickness of the second electrode was about 100 nm.

[0161] Here, the anode side hole transport layer, the intermediate hole transport layer and the light emitting layer side hole transport layer correspond to a hole transport layer having a stacked structure. The anode side hole transport layer, the intermediate hole transport layer and the light emitting layer side hole transport layer were manufactured in Examples and Comparative Examples using the materials shown in Table 1 below.

[0162] In Table 1, for example, the expression "Compound 2-3, 4-15" means that Compound 2-3 as an anode-side hole transport material is doped with Compound 4-15 as an electron accepting material. The doping amount of the electron accepting material is about 3 wt % based on the amount of the anode-side hole transport material.

[0163] In Table 1, Compounds 6-1, 6-2 and 6-3 refer to the following hole transport materials.

[0164]

[0165] 9,10-di(2-naphthyl)anthracene (AND, compound 3-2) was used as the host material of the light-emitting layer, and 2,5,8,11-tetra-tert-butylperylene (TBP) was used as the dopant material. 3 wt% of the dopant material was added based on the amount of the host material. In addition, Alq3 was used to form an electron transport layer, LiF was used to form an electron injection layer, and aluminum (Al) was used to form a second electrode.

[0166] (1-2-3. Evaluation results)

[0167] Then, the driving voltage, luminous efficiency and half-life (luminous lifetime) of the organic EL device thus manufactured were evaluated. The evaluation results are shown in the following Table 2. 2The current density of each embodiment and comparative example was measured to obtain the driving voltage and luminous efficiency. The luminance was increased from about 1,000 cd / m 2 The half-life is obtained by the time period from the initial brightness to half.

[0168] The measurements were performed in a dark room using a 2400 series source meter from Keithley Instruments, a Color Photometer CS-200 (KONICA MINOLTA HOLDINGS CO., LTD., at a measurement angle of 1°), and a PC program LabVIEW 8.2 (National Instruments, Inc., Japan).

[0169] [Table 1]

[0170] Anode side hole transport layer Intermediate hole transport layer Hole transport layer on the light-emitting layer side Example 1-1 Compounds 2-3, 4-15 Compound 2-3 Compound 1 Example 1-2 Compounds 2-3, 4-15 Compound 2-3 Compound 5 Examples 1-3 Compound 6-2, 4-15 Compound 2-3 Compound 1 Examples 1-4 Compounds 2-3, 4-15 Compound 6-3 Compound 1 Comparative Example 1-1 Compounds 2-3, 4-15 Compound 1 Compound 2-3 Comparative Example 1-2 Compound 2-3 Compound 2-3 Compound 1 Comparative Examples 1-3 Compounds 2-3, 4-15 Compound 2-3 Compound 6-1

[0171] [Table 2]

[0172] Voltage (V) Luminous efficiency (cd / A) Luminescence lifetime (h) Example 1-1 6.1 7.7 3,800 Example 1-2 6.4 7.6 3,700 Examples 1-3 6.3 7.6 3,100 Examples 1-4 6.3 7.7 2,900 Comparative Example 1-1 6.3 7.3 2,000 Comparative Example 1-2 7.4 6.9 2,100 Comparative Examples 1-3 6.4 7.3 2,300

[0173] Referring to Tables 1 and 2, it can be seen that the luminous efficiency of Examples 1-1 to 1-4 is improved and the half-life is increased when compared with those of Comparative Examples 1-1 to 1-3. It can be seen that the luminous efficiency and luminous life of the organic EL device are improved by arranging the anode-side hole transport layer, the intermediate hole transport layer, and the light-emitting layer-side hole transport layer between the first electrode and the light-emitting layer.

[0174] For example, when comparing Example 1-1 with Comparative Example 1-2, it can be seen that the properties of Example 1-1 are better. In Comparative Example 1-2, the electron accepting material (e.g., compound 4-15) is not doped in the anode side hole transport layer. Therefore, it is desirable for the electron accepting material to be doped in the anode side hole transport layer.

[0175] Comparing Example 1-1 with Comparative Example 1-1, the properties of Example 1-1 are better. In Comparative Example 1-1, the compounds included in the intermediate hole transport layer and the light-emitting layer side hole transport layer are opposite to those in Example 1-1. Therefore, it is desirable that the light-emitting layer side hole transport layer (including the compound represented by Formula 1) is adjacent to the light-emitting layer. In addition, by replacing the compounds included in the intermediate hole transport layer and the light-emitting layer side hole transport layer, significant property differences can be obtained.

[0176] Comparing Examples 1-1 to 1-3 with Comparative Example 1-3, the properties of Examples 1-1 to 1-3 are better. In Comparative Example 1-3, the light-emitting layer-side hole transport material included in the light-emitting layer-side hole transport layer is Compound 6-1 instead of the compound represented by Formula 1. Therefore, it is desirable that the light-emitting layer-side hole transport layer includes the compound represented by Formula 1.

[0177] Comparing Examples 1-1 and 1-2 with Example 1-3, the properties of Examples 1-1 and 1-2 are better. In Example 1-3, the anode-side hole transport material included in the anode-side hole transport layer is a hole transport material that does not include a carbazole group, that is, Compound 6-2, instead of the compound represented by Formula 2. Therefore, in practice, it is desirable that the anode-side hole transport material included in the anode-side hole transport layer is a compound represented by Formula 2.

[0178] Comparing Examples 1-1 and 1-2 with Example 1-4, the properties of Examples 1-1 and 1-2 are better. In Example 1-4, the intermediate hole transport material included in the intermediate hole transport layer is a hole transport material that does not include a carbazole group, that is, Compound 6-3, instead of the compound represented by Formula 2. Therefore, in practice, it is desirable that the intermediate hole transport material included in the intermediate hole transport layer is a compound represented by Formula 2.

[0179] As described above, an anode-side hole transport layer doped with an electron accepting material, an intermediate hole transport layer, and a light-emitting layer-side hole transport layer including a compound represented by Formula 1 are stacked between the first electrode (anode) and the light-emitting layer, and the luminescence efficiency and luminescence life of the organic EL device are improved.

[0180] It is considered that by arranging a hole transport layer on the light-emitting layer side including a compound represented by Formula 1, the hole transport layer can be passivated by electrons not consumed in the light-emitting layer, the excited state energy generated from the light-emitting layer can be prevented from diffusing to the hole transport layer, and the charge balance of the entire device can be controlled. It is considered that by arranging a hole transport layer on the light-emitting layer side including a compound represented by Formula 1, the hole transport layer on the light-emitting layer side can help suppress the electron accepting material included in the anode side hole transport layer provided adjacent to the first electrode (anode) from diffusing to the light-emitting layer.

[0181] <2-1. Configuration of an organic EL device including an anode-side hole transport layer (mainly including an electron accepting material)>

[0182] In the following, reference will be made to Figure 1 An organic EL device including an anode-side hole transport layer mainly including an electron accepting material is explained.

[0183] The organic EL device including the anode-side hole transport layer may include the electron accepting material included in the above-mentioned anode-side hole transport material and may have the same general configuration as the organic EL device described above (for example, including the anode-side hole transport layer doped with the electron accepting material), for example, the same substrate configuration, the same first electrode configuration, the same light-emitting layer configuration, the same electron transport layer configuration, the same electron injection layer configuration, the same second electrode configuration and the same method for manufacturing the organic EL device, and may have a different hole transport layer configuration. Therefore, in particular, the configuration of the hole transport layer will be explained below.

[0184] (2-1-1. Configuration of hole transport layer)

[0185] The hole transport layer 130 may include a hole transport material and may have a hole transport function. The hole transport layer 130 may be formed, for example, on the first electrode 120 to a layer thickness (total layer thickness of the stack structure) ranging from about 10 nm to about 150 nm.

[0186] The hole transport layer 130 of the organic EL device 100 according to the embodiment may be formed as a multilayer by stacking an anode-side hole transport layer 131, an intermediate hole transport material layer 133, and a light-emitting layer-side hole transport layer 135 one by one from the first electrode 120. In addition, the ratio of the thickness of the layers is not specifically limited.

[0187] (2-1-1-1. Configuration of hole transport layer on the anode side)

[0188] The anode-side hole transport layer 131 may include an anode-side hole transport material and may be a layer doped with an electron accepting material. For example, the anode-side hole transport layer 131 may be formed on the first electrode 120 .

[0189] The anode-side hole transport layer 131 may be formed by doping an electron accepting material and may help improve hole injection properties from the first electrode 120. Therefore, the anode-side hole transport layer 131 may be provided near the first electrode 120. For example, the anode-side hole transport layer 131 may be provided adjacent to (e.g., directly adjacent to or in direct contact with) the first electrode 120.

[0190] The anode-side hole transport material included in the anode-side hole transport layer 131 may include a suitable hole transport material. Examples of the anode-side hole transport material included in the anode-side hole transport layer 131 may include 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), and the like.

[0191] The electron accepting material included in the anode-side hole transport layer 131 may include a suitable electron accepting material. In implementation, the electron accepting material included in the anode-side hole transport layer 131 may have a LUMO level in the range of about -9.0 eV to about -4.0 eV, for example, about -6.0 eV to about -4.0 eV.

[0192] Examples of the electron accepting material having a LUMO level in the range of about -9.0 eV to about -4.0 eV may include a compound represented by one of the following Formulae 4-1 to 4-14.

[0193]

[0194] In the above formulae 4-1 to 4-14, each R may independently be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heteroaryl group having 5 to 50 ring carbon atoms.

[0195] Each Ar may independently be or include, for example, an aryl group having 6 to 50 ring carbon atoms substituted by an electron withdrawing group or an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, each Y may be, for example, a methylene group (-CH=) or a nitrogen atom (-N=), each Z may be, for example, a pseudohalogen atom or a sulfur (S) atom, n is an integer of 10 or less, and each X may be, for example, a substituent represented by one of the following formulae X1 to X7.

[0196]

[0197] In X1 to X7, each Ra can be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a fluoroalkyl group having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.

[0198] Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R, Ar and Ra may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-, 2-biphenyl-, 3-biphenyl-, 4-biphenyl-, 4-ter ... 4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, fluoranthenyl, fluorenyl and the like.

[0199] Examples of the substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms represented by R, Ar and Ra may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-benzofuranyl, -isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-isoquinolyl, 2-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, -quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4- Acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl, 1,8-phenanthroline 1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl, 2,8 ...8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl yl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furoxyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, etc.

[0200] Examples of the substituted or unsubstituted fluoroalkyl group having 1 to 50 carbon atoms represented by R and Ra may include perfluoroalkyl groups such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl and heptadecafluorooctyl, monofluoromethyl, difluoromethyl, trifluoroethyl, tetrafluoropropyl, octafluoropentyl and the like.

[0201] Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by R and Ra may include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, , 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-di Iodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-tert-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diamino-tert-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyano isopropyl, 2,3-dicyano-tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like.

[0202] The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms represented by R and Ra may be a group represented by —OY. Examples of Y may include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-tert-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-tert-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-tert-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl, 2-iodoethyl , 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-tert-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl, 2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl, 2,3-diamino-tert-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl, 2-Cyanoethyl, 2-Cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-tert-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-tert-butyl, 1,2,3-trinitropropyl, and the like.

[0203] Examples of the halogen atom represented by R and Ra may include fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the like.

[0204] In implementations, the electron accepting material may include one of the following compounds 4-15 and 4-16. For example, the LUMO level of compound 4-15 may be about -4.40 eV, and the LUMO level of compound 4-16 may be about -5.20 eV.

[0205]

[0206] The doping amount of the electron accepting material may be a suitable amount that can be doped into the anode side hole transport layer 131. For example, based on the total amount of the anode side hole transport material included in the anode side hole transport layer 131, the doping amount of the electron accepting material may be about 0.1 wt % to about 50 wt %, for example, about 0.5 wt % to about 5 wt %.

[0207] (2-1-1-2. Configuration of Intermediate Hole Transport Layer)

[0208] The intermediate hole transport layer 133 may include an intermediate hole transport material. The intermediate hole transport layer 133 may be formed, for example, on the anode-side hole transport layer 131 .

[0209] The intermediate hole transport material included in the intermediate hole transport layer 133 may include a suitable hole transport material. In implementation, the intermediate hole transport material may include the hole transport material mentioned above with respect to the anode-side hole transport material.

[0210] In implementations, the hole transport material may include a compound represented by Formula 2 below.

[0211] [Formula 2]

[0212]

[0213] In the above formula 2, Ar 1 To Ar 3 Ar may each independently be or include, for example, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms. 4 It may be or include, for example, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. 1 It may be a direct bond (eg, a single bond), a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms.

[0214] Ar 1 To Ar 3 Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, etc. In implementation, Ar 1 To Ar 3 The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, the dibenzofuranyl group, and the like may be included.

[0215] Ar 4Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, methyl, ethyl, propyl, isopropyl, n-butyl, and the like. In implementations, Ar 4 The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, the dibenzofuranyl group, the methyl group, the ethyl group, and the like may be included.

[0216] L 1 Examples of (except for direct linkages / single bonds) may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenylene, fluorenylene, indenylene, pyrenylene, acenaphtheneylene, fluoranthenylene, triphenylene, pyridylene, furanylene, pyranylene, thienylene, quinolylene, isoquinolylene, benzofuranylene, benzothienylene, indolylene, carbazolylene, benzoxazolylene, benzothiazolylene, quinoxalinyl, benzimidazolylene, pyrazolylene, dibenzofuranylene, dibenzothienylene, etc. In implementations, L 1 A direct bond, the phenylene group, the biphenylene group, the terphenylene group, the fluorenylene group, the carbazolylene group, or the dibenzofuranylene group may be included.

[0217] In implementations, the compound represented by Formula 2 may include one of the following compounds 2-1 to 2-16.

[0218]

[0219] The intermediate hole transport layer 133 may include the compound represented by Formula 2 above as an intermediate hole transport material and may contribute to improving the hole transport property of the hole transport layer 130. Therefore, the light emission efficiency of the organic EL device 100 may be improved.

[0220] The compound represented by Formula 2 may be included in the anode-side hole transport layer 131 as an anode-side hole transport material. In the case where the anode-side hole transport layer 131 includes the compound represented by Formula 2 as an anode-side hole transport material, the hole transport property of the hole transport layer 130 may be improved. Therefore, the luminous efficiency of the organic EL device 100 may be improved.

[0221] In practice, in the case where the ratio of the carbazole derivative, such as the compound represented by Formula 2, included in the hole transport layer 130 is high, the light emission lifetime of the organic EL device 100 may be improved.

[0222] The anode-side hole transport layer 131 may further include other hole transport materials in addition to the compound represented by Formula 2 as the anode-side hole transport material.

[0223] (2-1-1-3. Configuration of hole transport layer on the light-emitting layer side)

[0224] The light emitting layer-side hole transport layer 135 may include a compound represented by the following Formula 1. The light emitting layer-side hole transport layer 135 may be formed, for example, on the intermediate hole transport layer 133 , adjacent to (eg, directly adjacent to or directly in contact with) the light emitting layer 140 .

[0225] [Formula 1]

[0226]

[0227] In formula 1, Ar 1 and Ar 2 Each independently may be or include, for example, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.

[0228] R 1 To R 3 Each independently may be or include, for example, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms. 1 To R 3 Two or more adjacent groups in may be separated, or may be combined to form a ring.

[0229] In an implementation, m may be an integer from 0 to 4 and p and q may each independently be an integer from 0 to 5. 1 It may be, for example, a direct bond (e.g., a single bond), a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms. In implementation, carbon atoms a and b may be separated from each other or may be bonded via a direct bond.

[0230] Ar 1 and Ar 2 Examples of Ar may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, acenaphthenyl, fluoranthenyl, triphenylenyl, pyridyl, furanyl, pyranyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, etc. In implementation, Ar 1 and Ar 2The phenyl group, the biphenyl group, the terphenyl group, the fluorenyl group, the carbazolyl group, and the dibenzofuranyl group may be included.

[0231] R 1 To R 3 Examples may include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, tert-butyl, cyclobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, nonyl, decyl and the like, in addition to the specific examples of Ar1 and Ar2.

[0232] Ar 1 and Ar 2 and R 1 To R 3 The substituents of may include alkyl, alkoxy, aryl and heteroaryl. Examples of the alkyl, aryl and heteroaryl may be the same as described above. An example of the alkoxy may be an alkoxy substituted by an alkyl.

[0233] L 1 Examples (other than direct linkage / single bond) may include Ar 1 and Ar 2 For example, in addition to the directly linked L 1 Examples of may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorenylene, fluorene diyl, indan diyl, pyrene diyl, acenaphthene diyl, fluoranthene diyl, triphenylene diyl, pyridine diyl, pyran diyl, quinoline diyl, isoquinoline diyl, benzofuran diyl, benzothiophene diyl, indole diyl, carbazole diyl, benzoxazole diyl, benzothiazole diyl, quinoxaline diyl, benzimidazole diyl, dibenzofuran diyl. In implementation, the phenylene, terphenylene, fluorene diyl, carbazole diyl and dibenzofuran diyl may be used.

[0234] In implementations, the compound represented by Formula 1 may include one of the following Compounds 1 to 12.

[0235]

[0236]

[0237] The light-emitting layer-side hole transport layer 135 may include the compound represented by the above formula 1 as the light-emitting layer-side hole transport material and may passivate the hole transport layer 130 from the electrons not consumed in the light-emitting layer 140. In addition, the light-emitting layer-side hole transport layer 135 may include the compound represented by the above formula 1 and may reduce and / or prevent the energy of the excited state generated in the light-emitting layer 140 from diffusing into the hole transport layer 130. Therefore, according to this configuration, the light-emitting layer-side hole transport layer 135 may contribute to improving the current durability of the hole transport layer 130.

[0238] The light-emitting layer-side hole transport layer 135 may be formed close to the light-emitting layer 140. For example, the light-emitting layer-side hole transport layer 135 may be formed adjacent to (eg, directly adjacent to or directly in contact with) the light-emitting layer 140, thereby helping to effectively prevent electrons or energy from diffusing from the light-emitting layer 140.

[0239] The light-emitting layer-side hole transport layer 135 may include the compound represented by Formula 1 above, the charge balance of the entire organic EL device 100 may be controlled, and the electron accepting material doped into the anode-side hole transport layer 131 may be inhibited from diffusing to the light-emitting layer 140. Therefore, the light-emitting layer-side hole transport layer 135 may contribute to improving the overall charge transport properties of the hole transport layer 130.

[0240] The light emitting layer-side hole transport layer 135 may include the compound represented by Formula 1 above, and the charge transport property and current durability of the hole transport layer 130 may be improved. Therefore, the light emission efficiency and light emission lifetime of the organic EL device 100 may be improved.

[0241] As described above, the hole transport layer 130 including the anode-side hole transport layer 131, the intermediate hole transport layer 133, and the light-emitting layer-side hole transport layer 135 can help improve the current durability and hole transport properties of the organic EL device 100. Therefore, the organic EL device 100 according to the embodiment can have improved luminous efficiency and luminous lifetime.

[0242] <2-2. Example>

[0243] Hereinafter, an organic EL device according to an exemplary embodiment will be explained with particular reference to Examples and Comparative Examples. The following embodiments are for illustration only, and the organic EL device according to the exemplary embodiment is not limited thereto.

[0244] (2-2-1. Synthesis of Compounds)

[0245] (Synthesis Example 1: Synthesis of Compound 1)

[0246] Compound 1 was synthesized according to the following reaction scheme.

[0247]

[0248] (Synthesis of Compound A)

[0249] Under an argon atmosphere, 53.8 g of N-[1,1'-biphenyl]-4-yl-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine and 6.46 g of [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium·CH 2 Cl 2 (Pd(dppf)Cl2 ·CH 2 Cl 2 ), 33.3 g of potassium acetate (KOAc) and 33.0 g of bis(pinacolato)diboron were added to a 2 L flask, followed by degassing under vacuum and stirring in 750 mL of dioxane solvent at about 100° C. for about 12 hours. Afterwards, the solvent was distilled off and CH 2 Cl 2 The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) to produce 56.8 g (yield 98%) of compound A as a white solid (FAB-MS: C 36 H 34 BNO 2 , measured value 523).

[0250] (Synthesis of Compound 1)

[0251] Under an argon atmosphere, 1.66 g of compound A, 1.52 g of compound B, 0.11 g of tetrakis(triphenylphosphine)palladium(0)(Pd(PPh 3 ) 4 ) and 1.1g of sodium carbonate were added to a 200mL three-necked flask, followed by heating and stirring at about 80°C in a mixed solvent of 19mL EtOH and 9.0L water for about 2 hours. After air cooling, water was added, the organic layer was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of toluene and hexane) and recrystallized using a mixed solvent of toluene and EtOH to produce 1.96g (yield 84%) of compound 1 as a white solid. Compound 1 (C 55 H 39 N) has a molecular weight of 713. 1 H NMR (300 MHz, CDCl 3 ) measured the chemical shift values ​​(δ) of compound 1 to be 7.82-7.76 (m, 2H), 7.62-7.56 (m, 6H), 7.53-7.49 (m, 5H), 7.47 (d, 2H, J=6.0 Hz), 7.45-7.39 (m, 4H), 7.37-7.29 (m, 3H), 7.27-7.18 (m, 17H). Thus, the synthesis of compound 1 was confirmed.

[0252] (Synthesis Example 2: Synthesis of Compound 5)

[0253] Compound 5 was synthesized according to the following reaction scheme.

[0254]

[0255] (Synthesis of Compound C)

[0256] Under an argon atmosphere, 2.32 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 4.00 g of 2-bromo-9,9-diphenylfluorene, 1.04 g of Pd(PPh 3 ) 4 and 2.79 g of potassium carbonate were added to a 500 mL three-necked flask, followed by heating and stirring at about 90° C. in a mixed solvent of 200 mL of toluene, 32 mL of water and 12 mL of ethanol for about 14 hours. After air cooling, water was added, the organic layer was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and recrystallized using a mixed solvent of ethyl acetate and hexane to produce 2.18 g (yield 53%) of compound C as a white solid. (FAB-MS: C 31 H 23 N, measured value, 409)

[0257] (Synthesis of Compound 5)

[0258] Under an argon atmosphere, 2.11 g of compound C, 3.15 g of 3-bromodibenzofuran, and 0.384 g of tris(dibenzylideneacetone)dipalladium·CHCl were added. 3 (Pd 2 (dba) 3 ·CHCl 3 ), 2.06 g t-BuONa was added to a 200 mL three-necked flask, to which 65 mL dehydrated toluene and 0.56 mL 2M (t-Bu) were added. 3 P / dehydrated toluene, then heated, refluxed and stirred for about 7 hours. After air cooling, water was added, the organic layer was separated, and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and recrystallized using a mixed solvent of dichloromethane and ethanol to produce 3.30 g (yield 62%) of compound 5 as a white solid. Compound 5 (C 55 H 35 NO 2 ) has a molecular weight of 741. 1 H NMR (300 MHz, CDCl 3 The chemical shift values ​​(δ) of compound 5 measured by HPLC were 7.87 (dd, 2H), 7.81 (d, 2H), 7.80 (dd, 2H), 7.54-7.46 (4H), and 7.46-7.13 (25H). The synthesis of compound 5 was thus confirmed.

[0259] (2-2-2. Production of an organic EL device including an anode-side hole transport material (mainly including an electron accepting material))

[0260] The organic EL device according to the embodiment is manufactured by the following manufacturing method.

[0261] First, on the ITO-glass substrate that had been patterned and washed in advance, UV-ozone (O 3 ). The layer thickness of the ITO layer (first electrode) on the glass substrate was about 150 nm. After the ozone treatment, the surface-treated substrate was inserted into a glass bell-jar type evaporator for forming an organic layer and heated for about 10 -4 to about 10 -5 The anode side hole transport layer, the intermediate hole transport layer, the light emitting layer side hole transport layer, the light emitting layer and the electron transport layer were evaporated one by one at a vacuum degree of 1.5 Pa. The layer thickness of each of the anode side hole transport layer, the intermediate hole transport layer and the light emitting layer side hole transport layer was about 10 nm. The layer thickness of the light emitting layer was about 25 nm, and the layer thickness of the electron transport layer was about 25 nm. Then, the substrate was moved into a glass bell jar type evaporator for forming a metal layer, and the substrate was evaporated with about 10 -4 to about 10 -5 The electron injection layer and the second electrode were evaporated at a vacuum degree of 100 Pa. The layer thickness of the electron injection layer was about 1 nm and the layer thickness of the second electrode was about 100 nm.

[0262] The anode-side hole transport layer, the intermediate hole transport layer and the light-emitting layer-side hole transport layer correspond to hole transport layers having a stacked structure. The anode-side hole transport layer, the intermediate hole transport layer and the light-emitting layer-side hole transport layer were manufactured in Examples and Comparative Examples using the materials shown in Table 3 below.

[0263] In Table 3, for example, the expression "Compound 2-3, 4-15" means that Compound 2-3 as an anode-side hole transport material is doped with Compound 4-15 as an electron accepting material. The doping amount of the electron accepting material is about 3 wt % based on the amount of the anode-side hole transport material.

[0264] In Table 3, Compounds 6-1, 6-2 and 6-3 refer to the following hole transport materials.

[0265]

[0266] 9,10-di(2-naphthyl)anthracene (ADN, compound 3-2) was used as the host material of the light-emitting layer, and 2,5,8,11-tetra-tert-butylperylene (TBP) was used as the dopant material. 3 wt% of the dopant material was added based on the amount of the host material. In addition, Alq3 was used to form an electron transport layer, LiF was used to form an electron injection layer, and aluminum (Al) was used to form a second electrode.

[0267] (2-2-3. Evaluation results)

[0268] Then, the driving voltage, luminous efficiency and half-life (luminous lifetime) of the organic EL device thus manufactured were evaluated. The evaluation results are shown together in the following Table 4. 2 The current density of each embodiment and comparative example was measured to obtain the driving voltage and luminous efficiency. The luminance was increased from about 1,000 cd / m 2 The luminescence lifetime is obtained by the time period from the initial brightness to half.

[0269] The measurements were performed in a dark room using a 2400 series source meter from Keithley Instruments, a Color Photometer CS-200 (KONICA MINOLTA HOLDINGS CO., LTD., at a measurement angle of 1°), and a PC program LabVIEW 8.2 (National Instruments, Inc., Japan).

[0270] [Table 3]

[0271] Anode side hole transport layer Intermediate hole transport layer Hole transport layer on the light-emitting layer side Example 2-1 Compounds 2-3, 4-15 Compound 2-3 Compound 1 Example 2-2 Compounds 2-3, 4-15 Compound 2-3 Compound 5 Example 2-3 Compound 6-2, 4-15 Compound 2-3 Compound 1 Embodiment 2-4 Compounds 2-3, 4-15 Compound 6-3 Compound 1 Comparative Example 2-1 Compounds 2-3, 4-15 Compound 1 Compound 2-3 Comparative Example 2-2 Compound 2-3 Compound 2-3 Compound 1 Comparative Examples 2-3 Compounds 2-3, 4-15 Compound 2-3 Compound 6-1

[0272] [Table 4]

[0273] Voltage (V) Luminous efficiency (cd / A) Luminescence lifetime (h) Example 2-1 6.1 7.7 3,800 Example 2-2 6.4 7.6 3,700 Example 2-3 6.3 7.6 3,100 Embodiment 2-4 6.3 7.7 2,900 Comparative Example 2-1 6.3 7.3 2,000 Comparative Example 2-2 7.4 6.9 2,100 Comparative Examples 2-3 6.4 7.3 2,300

[0274] Referring to the results of Tables 3 and 4, the luminous efficiency of Examples 2-1 to 2-4 is improved and the half-life is increased relative to Comparative Examples 2-1 to 2-3. It can be seen that the luminous efficiency and luminous life of the organic EL device are improved by providing the anode-side hole transport layer, the intermediate hole transport layer and the light-emitting layer-side hole transport layer between the first electrode and the light-emitting layer.

[0275] For example, when comparing Example 2-1 with Comparative Example 2-2, it can be seen that the properties of Example 2-1 are better. In Comparative Example 2-2, the electron accepting material (e.g., compound 4-15) is not doped in the anode side hole transport layer. Therefore, it is desirable for the electron accepting material to be doped in the anode side hole transport layer.

[0276] Comparing Example 2-1 with Comparative Example 2-1, the properties of Example 2-1 are better. In Comparative Example 2-1, the compounds included in the intermediate hole transport layer and the light-emitting layer side hole transport layer are opposite to those in Example 2-1. Therefore, it is desirable that the light-emitting layer side hole transport layer including the compound represented by Formula 1 is adjacent to the light-emitting layer. In addition, by changing the compounds included in the intermediate hole transport layer and the light-emitting layer side hole transport layer, significantly improved properties can be obtained.

[0277] Comparing Examples 2-1 to 2-3 with Comparative Example 2-3, the properties of Examples 2-1 to 2-3 are better. In Comparative Example 2-3, the light-emitting layer-side hole transport material included in the light-emitting layer-side hole transport layer is compound 6-1 instead of the compound represented by Formula 1. Therefore, it is desirable that the light-emitting layer-side hole transport layer includes the compound represented by Formula 1.

[0278] Comparing Examples 2-1 and 2-2 with Example 2-3, the properties of Examples 2-1 and 2-2 are better. In Example 2-3, the anode-side hole transport material included in the anode-side hole transport layer is compound 6-2 instead of the compound represented by Formula 2. Therefore, in practice, it is desirable that the anode-side hole transport material included in the anode-side hole transport layer is a compound represented by Formula 2.

[0279] Comparing Examples 2-1 and 2-2 with Example 2-4, the properties of Examples 2-1 and 2-2 are better. In Example 2-4, the intermediate hole transport material included in the intermediate hole transport layer is a hole transport material that does not include a carbazole group, that is, Compound 6-3, instead of the compound represented by Formula 2. Therefore, in practice, it is desirable that the intermediate hole transport material included in the intermediate hole transport layer is a compound represented by Formula 2.

[0280] As explained above, when an anode-side hole transport layer doped with an electron-accepting material, an intermediate hole transport layer, and a light-emitting layer-side hole transport layer including a compound represented by Formula 1 are stacked between the first electrode (anode) and the light-emitting layer, the luminescence efficiency and luminescence life of the organic EL device are improved.

[0281] It is considered that by arranging a hole transport layer on the light-emitting layer side including a compound represented by Formula 1, the hole transport layer can be passivated by electrons not consumed in the light-emitting layer, the excited state energy generated from the light-emitting layer can be prevented from diffusing to the hole transport layer, and the charge balance of the entire device can be controlled. It is considered that by arranging a hole transport layer on the light-emitting layer side including a compound represented by Formula 1, the hole transport layer on the light-emitting layer side can help suppress the electron accepting material included in the anode side hole transport layer provided adjacent to the first electrode (anode) from diffusing to the light-emitting layer.

[0282] As described above, the anode-side hole transport layer, the intermediate hole transport layer, and the light-emitting layer-side hole transport layer may be provided between the anode and the light-emitting layer, and the light emission efficiency and light emission lifetime of the organic EL device are increased.

[0283] By summarizing and reviewing, a hole transport material or a hole transport layer may be included in an organic EL device. For example, a hole transport material may include a carbazole group and may be used in a hole transport layer. In addition, an electron accepting material may be added to the hole transport layer, and the hole transport layer may be formed by a stacked structure using a plurality of layers.

[0284] Embodiments may provide a device having satisfactory values ​​for luminous efficiency and luminous lifetime of an organic EL device.

[0285] Embodiments may provide an organic EL device having improved luminous efficiency and luminous lifetime.

[0286] Example embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted in a generic and descriptive sense only and not for limiting purposes. In some cases, it will be apparent to one of ordinary skill in the art from the filing of this application that the features, characteristics, and / or elements described with respect to a particular embodiment may be used alone or in combination with the features, characteristics, and / or elements described with respect to other embodiments, unless otherwise expressly indicated. Therefore, it will be understood by those skilled in the art that various changes in form and details may be made without departing from the spirit and scope described in the following claims.

Claims

1. An organic electroluminescent device, comprising: anode; Luminescent layer; an anode-side hole transport layer, the anode-side hole transport layer being between the anode and the light-emitting layer, the anode-side hole transport layer comprising a hole transport material and being doped with an electron accepting material; A light-emitting layer side hole transport layer, the light-emitting layer side hole transport layer is between the anode and the light-emitting layer, and the light-emitting layer side hole transport layer includes a light-emitting layer side hole transport material represented by the following formula 1; as well as An intermediate hole transport layer, the intermediate hole transport layer is between the anode-side hole transport layer and the light-emitting layer-side hole transport layer, the intermediate hole transport layer comprising an intermediate hole transport material represented by the following formula 2: [Formula 1] Among them, in formula 1, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, R1 to R3 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring carbon atoms, or two or more adjacent groups among R1 to R3 are separated or combined to form a ring, m is an integer from 0 to 4, p and q are each independently an integer from 0 to 5, L1 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and Carbon atoms a and b are separated or joined via a direct bond, [Formula 2] Among them, in formula 2, Ar1 to Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, or Ar1 and Ar2 are combined to form a ring, Ar4 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 15 ring carbon atoms. 2 . The organic electroluminescent device according to claim 1 , wherein the light-emitting layer-side hole transport layer is adjacent to the light-emitting layer.

3. The organic electroluminescent device according to claim 1, wherein the anode-side hole transport layer is between the anode and the intermediate hole transport layer, and The hole transport material includes an anode-side hole transport material represented by Formula 2. The organic electroluminescent device as claimed in claim 3 , wherein the anode-side hole transport layer is adjacent to the anode.

5. The organic electroluminescent device according to claim 1, wherein the light-emitting layer comprises a compound represented by the following formula 3: [Formula 3] in, In formula 3, each Ar1 is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and n is an integer of 1 to 10. The organic electroluminescent device as claimed in claim 1 , wherein L1 is a substituted or unsubstituted phenylene group.

7. The organic electroluminescent device according to claim 1, wherein the hole transport layer on the light-emitting layer side comprises one of the following compounds 1 to 12:

8. The organic electroluminescent device according to claim 1, wherein the intermediate hole transport material comprises one of the following compounds 2-1 to 2-16:

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