Organic optoelectronic diode and display device

Abstract

The present invention relates to an organic optoelectronic diode and a display device, the organic optoelectronic diode comprising: an anode and a cathode that face each other; a light-emitting layer disposed between the anode and the cathode; a hole transport layer disposed between the anode and light-emitting layer; and an auxiliary hole transport layer disposed between the hole transport layer and the light-emitting layer, wherein the auxiliary hole transport layer includes: a first auxiliary hole transport layer adjacent to the hole transport layer; and a second auxiliary hole transport layer adjacent to the light-emitting layer, the first auxiliary hole transport layer includes a first compound represented by chemical formula 1, and the second auxiliary hole transport layer includes a second compound represented by a combination of chemical formula 2 and chemical formula 3. The details of chemical formula 1 to chemical formula 3 are the same as those defined in the specification.

Description

Organic optoelectronic devices and displays

[0001] It relates to organic optoelectronic devices and display devices.

[0002] Organic optoelectronic diodes are devices that can convert electrical energy and light energy to each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One type is a photoelectric device, in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device, in which light energy is generated from electrical energy by supplying voltage or current to an electrode.

[0004] Examples of organic optoelectronic devices include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photoconductor drums.

[0005] Among these, organic light-emitting diodes (OLEDs) have recently attracted significant attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is significantly influenced by the organic materials located between the electrodes.

[0006] One embodiment provides an organic optoelectronic device capable of implementing long-life characteristics.

[0007] Another embodiment provides a display device including the organic optoelectronic device.

[0008] According to one embodiment, an organic optoelectronic device is provided, comprising: an anode and a cathode facing each other; a light-emitting layer positioned between the anode and the cathode; a hole transport layer positioned between the anode and the light-emitting layer; and a hole transport auxiliary layer positioned between the hole transport layer and the light-emitting layer, wherein the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, wherein the first hole transport auxiliary layer includes a first compound represented by the following chemical formula 1, and the second hole transport auxiliary layer includes a second compound represented by a combination of the following chemical formulas 2 and 3.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X 1 is O or S,

[0013] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0014] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0015] R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0016] m1 is one of the integers 1 to 4,

[0017] m2 is an integer between 1 and 3,

[0018] If m1 is 2 or more, each R 1 are identical or different from each other,

[0019] If m2 is 2 or more, each R 2 are identical or different from each other;

[0020] [Chemical Formula 2] [Chemical Formula 3]

[0021]

[0022] In the above chemical formulas 2 and 3,

[0023] X 2 and X 3 are each independently O, S or CR a R b And,

[0024] X 2 and X 3 At least one of them is O or S,

[0025] R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0026] In chemical formula 2, a1* to a4* are each independently a connecting carbon (C) or CR c And,

[0027] * in chemical formula 3 is a connecting carbon (C),

[0028] Among a1* to a4* of chemical formula 2, two adjacent ones are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to chemical formula 3 are each independently CR c And,

[0029] R c and R 3 Inland R 7are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0030] L 4 Inland L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0031] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0032] m3 is one of the integers 1 to 3,

[0033] If m3 is 2 or more, each R 7 are identical or different from each other.

[0034] According to another embodiment, a display device including the above-described organic optoelectronic device is provided.

[0035] It is possible to realize organic optoelectronic devices with long-life characteristics.

[0036] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0037] <Explanation of symbols>

[0038] 10: Anode 20: Cathode

[0039] 30: Organic layer 31: Emissive layer

[0040] 32: Hole transport layer 33: Hole transport auxiliary layer

[0041] 33a: First hole transport auxiliary layer 33b: Second hole transport auxiliary layer

[0042] 34: Hole injection layer 35: Electron transport layer

[0043]

[0044] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0045] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof, unless otherwise defined.

[0046] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is replaced with a deuterium group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0047] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.

[0048] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0049] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0050] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0051] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0052] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0053] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0054] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0055] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthfuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0056] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

[0057] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0058] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0059] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described as an example, but the present invention is not limited thereto and can be equally applied to other organic optoelectronic devices.

[0060] To clearly illustrate various layers and regions in the drawings, the thicknesses are enlarged. Similar parts are designated by the same drawing reference numerals throughout the specification. When an element, such as a layer, film, region, or plate, is said to be "on" another element, this includes not only the case where it is "directly on" the other element, but also the case where there are other elements in between. Conversely, when an element is said to be "directly on" another element, it means that there are no other elements in between.

[0061] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0062] An organic light-emitting device according to an embodiment will be described with reference to FIG. 1 below.

[0063] Referring to FIG. 1, an organic light-emitting device according to one embodiment includes an anode (10) and a cathode (20) facing each other, and an organic layer (30) positioned between the anode (10) and the cathode (20).

[0064] The anode (10) can be made of a conductor with a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (10) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0065] The cathode (20) can be made of a conductor with a low work function to facilitate electron injection, for example, and can be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (20) can be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0066] The organic layer (30) includes a light-emitting layer (31), a hole transport layer (32), and a hole transport auxiliary layer (33) located between the hole transport layer (32) and the light-emitting layer (31).

[0067] The light-emitting layer (31) includes a host and a dopant, and the host may be, for example, a phosphorescent host.

[0068] A phosphorescent host must facilitate the injection and transport of holes and electrons within the emitting layer, ultimately allowing holes and electrons to meet to form excitons, and must be able to transfer the energy of the formed excitons to the dopant. Examples of phosphorescent hosts include organic compounds containing carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0069] The above phosphorescent host can be used without limitation as long as it is a known material, and may be, for example, a single host or a mixed host.

[0070] The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0071] A dopant is a substance that causes light emission when mixed in a small amount with a host. Typically, a metal complex that emits light by multiple excitation that excites beyond the triplet state can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may contain one or more types.

[0072] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0073] [Chemical formula Z]

[0074] L 7 MX 4

[0075] In the above chemical formula Z, M is a metal, and L7 and X 4 are ligands that are the same or different and form complexes with M.

[0076] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the above L 7 and X 4 may be, for example, a bidentate ligand.

[0077] L 7 and X 4 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0078] [Group A]

[0079]

[0080] In the above group A,

[0081] R 300 Inland R 302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0082] R 303 Inland R 324are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group,

[0083] n1 is one of the integers from 1 to 5,

[0084] n2 is one of the integers from 1 to 4,

[0085] n3 is one of the integers 1 to 3,

[0086] n4 is an integer of 1 or 2,

[0087] n5 is one of the integers 1 to 6.

[0088] When n1 is 2 or more, each substituent may be the same or different.

[0089] When n2 is 2 or more, each substituent may be the same or different.

[0090] When n3 is 2 or more, each substituent may be the same or different.

[0091] When n4 is 2 or more, each substituent may be the same or different.

[0092] When n5 is 2 or more, each substituent may be the same or different.

[0093] The dopant according to one embodiment may be an iridium complex, for example, represented by the following chemical formula 6-1 or chemical formula 6-2.

[0094] [Chemical Formula 6-1]

[0095]

[0096] In the above chemical formula 6-1,

[0097] R 101 Inland R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0098] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0099] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,

[0100] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0101] m19 and m20 are independently any integer from 0 to 3, and m19 + m20 is any integer from 1 to 3,

[0102] [Chemical Formula V-1]

[0103]

[0104] In the above chemical formula V-1,

[0105] R 135 Inland R 139are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0106] * indicates a part connected to a carbon atom.

[0107] [Chemical Formula 6-2]

[0108]

[0109] In the above chemical formula 6-2,

[0110] R 101 Inland R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0111] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0112] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0113] n1 and n2 are independently any integer from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0114] For example, it may include a dopant represented by the following chemical formula Z-1.

[0115] [Chemical Formula Z-1]

[0116]

[0117] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0118] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0119] L B , L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0120] If nA is 1, L E is selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist;

[0121] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are randomly connected to form a ring; X B , X C , XD , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0122] The platinum complex may be represented, for example, by the following chemical formula 7-1 or chemical formula 7-2.

[0123] [Chemical Formula 7-1]

[0124]

[0125] [Chemical Formula 7-2]

[0126]

[0127] In the above chemical formulas 7-1 and 7-2,

[0128] X 100 Silver O, S and NR 132 Selected from among,

[0129] R 118 Inland R 132 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - Si R 133 R 134 R 135 And,

[0130] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0131] R 118 Inland R 132 At least one of them is -SiR 132 R 133 R 134 or tert-butyl group,

[0132] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.

[0133] The composition further comprising a dopant may be, for example, a green luminescent composition.

[0134] The above organic light-emitting device may further include a hole injection layer (34) in addition to the light-emitting layer.

[0135] The hole injection layer (34) is a layer for facilitating hole injection from the anode (10) to the hole transport layer (32), and may include a material having a HOMO energy level between the work function of the conductor forming the anode (10) and the HOMO energy level of the material forming the hole transport layer (32).

[0136] For example, at least one of the hole transport layer (32) and the hole injection layer (34) may include at least one of the compounds listed in Group B below, and is different from the materials of the first hole transport auxiliary layer and the second hole transport auxiliary layer described below.

[0137] [Group B]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0172] In addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure thereto may also be used in the hole transport layer (32) and hole injection layer (34).

[0173] The above hole transport auxiliary layer (33) includes a first hole transport auxiliary layer (33a) adjacent to the hole transport layer and a second hole transport auxiliary layer (33b) adjacent to the light-emitting layer.

[0174] The first hole transport auxiliary layer includes a first compound represented by the following chemical formula 1, and the second hole transport auxiliary layer includes a second compound represented by a combination of the following chemical formulas 2 and 3.

[0175] [Chemical Formula 1]

[0176]

[0177] In the above chemical formula 1,

[0178] X 1 is O or S,

[0179] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0180] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0181] R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0182] m1 is one of the integers 1 to 4,

[0183] m2 is an integer between 1 and 3;

[0184] [Chemical Formula 2] [Chemical Formula 3]

[0185]

[0186] In the above chemical formulas 2 and 3,

[0187] X 2 and X 3 are each independently O, S or CR a R b And,

[0188] X 2 and X 3 At least one of them is O or S,

[0189] R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0190] In chemical formula 2, a1* to a4* are each independently a connecting carbon (C) or CR c And,

[0191] * in chemical formula 3 is a connecting carbon (C),

[0192] Among a1* to a4* of chemical formula 2, two adjacent ones are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to chemical formula 3 are each independently CR c And,

[0193] R c and R 3 Inland R 7 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0194] L 4 Inland L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0195] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0196] m3 is an integer between 1 and 3.

[0197] An organic light-emitting device according to one embodiment can have improved lifespan characteristics by applying a combination of two hole transport auxiliary layers at the interface between a hole transport layer and a light-emitting layer, thereby adjusting the hole injection ability in the first hole transport auxiliary layer to balance the charge in the light-emitting layer, and blocking electrons in the second hole transport auxiliary layer to achieve a balance of hole and electron densities.

[0198] If the above m1 is 2 or more, each R 1 may be identical or different.

[0199] If the above m2 is 2 or more, each R 2 may be identical or different.

[0200] For example, the above chemical formula 1 can be expressed by any one of the following chemical formulas 1-1 to 1-4.

[0201] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0202]

[0203] [Chemical Formula 1-3] [Chemical Formula 1-4]

[0204]

[0205] In the above chemical formulas 1-1 to 1-4,

[0206] L 1 Inland L3 , R 1 Inland R 4 , Ar 1 , Ar 2 , m1 and m2 are defined as in Chemical Formula 1.

[0207] For example, the first compound can be represented by the chemical formula 1-1 or chemical formula 1-3.

[0208] As a specific example, Ar of the above chemical formula 1 1 and Ar 2 may each independently be 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0209] For example, Ar of the above chemical formula 1 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0210] For example, the above R 1 and R 2 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0211] As a specific example, the above R 1 and R 2 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0212] For example, the above R3 and R 4 Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0213] As a specific example, the above R 3 and R 4 Each may independently be a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0214] For example, the above L 1 Inland L 3 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0215] In one embodiment, the L 2 -Ar 1 and L 3 -Ar 2 Each of the substituents may be independently selected from the substituents listed in Group I below.

[0216] [Group Ⅰ]

[0217]

[0218] In the above group Ⅰ,

[0219] R 10 Inland R 13 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0220] R 14 and R 15 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

[0221] m4 is an integer between 1 and 5,

[0222] m5 is one of the integers 1 to 4,

[0223] m6 is one of the integers 1 to 3,

[0224] m7 is an integer of 1 or 2,

[0225] * is a connection point.

[0226] If the above m4 is 2 or more, each R 10 may be identical or different.

[0227] If the above m5 is 2 or more, each R 11 may be identical or different.

[0228] If the above m6 is 2 or more, each R 12 may be identical or different.

[0229] If the above m7 is 2 or more, each R 13 may be identical or different.

[0230] For example, the first compound may be, but is not limited to, one selected from the compounds listed in Group 1 below.

[0231] [Group 1]

[0232]

[0233] [1-1] [1-2] [1-3] [1-4] [1-5]

[0234]

[0235] [1-6] [1-7] [1-8] [1-9] [1-10]

[0236]

[0237] [1-11] [1-12] [1-13] [1-14] [1-15]

[0238]

[0239] [1-16] [1-17] [1-18] [1-19] [1-20]

[0240]

[0241] [1-21] [1-22] [1-23] [1-24] [1-25]

[0242]

[0243] [1-26] [1-27] [1-28] [1-29] [1-30]

[0244]

[0245] [1-31] [1-32] [1-33] [1-34] [1-35]

[0246]

[0247] [1-36] [1-37] [1-38] [1-39] [1-40]

[0248]

[0249] [1-41] [1-42] [1-43] [1-44] [1-45]

[0250]

[0251] [1-46] [1-47] [1-48] [1-49] [1-50]

[0252]

[0253] [1-51] [1-52] [1-53] [1-54] [1-55]

[0254]

[0255] [1-56] [1-57] [1-58] [1-59] [1-60]

[0256]

[0257] [1-61] [1-62] [1-63] [1-64] [1-65]

[0258]

[0259] [1-66] [1-67] [1-68] [1-69] [1-70]

[0260]

[0261] [1-71] [1-72] [1-73] [1-74] [1-75]

[0262]

[0263] [1-76] [1-77] [1-78] [1-79] [1-80]

[0264]

[0265] [1-81] [1-82] [1-83] [1-84] [1-85]

[0266]

[0267] [1-86] [1-87] [1-88] [1-89] [1-90]

[0268]

[0269] [1-91] [1-92] [1-93] [1-94] [1-95]

[0270]

[0271] [1-96] [1-97] [1-98] [1-99] [1-100]

[0272]

[0273] [1-101] [1-102][1-103][1-104][1-105]

[0274]

[0275] [1-106] [1-107][1-108][1-109][1-110]

[0276]

[0277] [1-111] [1-112][1-113][1-114][1-115]

[0278]

[0279] [1-116] [1-117][1-118][1-119][1-120]

[0280]

[0281] [1-121] [1-122][1-123][1-124][1-125]

[0282]

[0283] [1-126] [1-127][1-128][1-129][1-130]

[0284]

[0285] [1-131] [1-132][1-133][1-134][1-135]

[0286]

[0287] [1-136] [1-137][1-138][1-139][1-140]

[0288]

[0289] [1-141] [1-142][1-143][1-144][1-145]

[0290]

[0291] [1-146] [1-147][1-148][1-149][1-150]

[0292]

[0293] [1-151] [1-152][1-153][1-154][1-155]

[0294]

[0295] [1-156] [1-157][1-158][1-159][1-160]

[0296]

[0297] [1-161] [1-162][1-163][1-164][1-165]

[0298]

[0299] [1-166] [1-167][1-168][1-169][1-170]

[0300]

[0301] [1-171] [1-172][1-173][1-174][1-175]

[0302]

[0303] [1-176] [1-177][1-178][1-179][1-180]

[0304]

[0305] [1-181] [1-182][1-183][1-184][1-185]

[0306]

[0307] [1-186] [1-187][1-188][1-189][1-190]

[0308]

[0309] [1-191] [1-192][1-193][1-194][1-195]

[0310]

[0311] [1-196] [1-197][1-198][1-199][1-200]

[0312]

[0313] [1-201] [1-202][1-203][1-204][1-205]

[0314]

[0315] [1-206] [1-207][1-208][1-209][1-210]

[0316]

[0317] [1-211] [1-212][1-213][1-214][1-215]

[0318]

[0319] [1-216] [1-217][1-218][1-219][1-220]

[0320]

[0321] [1-221] [1-222][1-223][1-224][1-225]

[0322]

[0323] [1-226] [1-227][1-228][1-229][1-230]

[0324]

[0325] [1-231] [1-232][1-233][1-234][1-235]

[0326]

[0327] [1-236] [1-237][1-238][1-239][1-240]

[0328]

[0329] [1-241] [1-242][1-243][1-244][1-245]

[0330]

[0331] [1-246] [1-247][1-248][1-249][1-250]

[0332]

[0333] [1-251] [1-252][1-253][1-254][1-255]

[0334]

[0335] [1-256] [1-257][1-258][1-259][1-260]

[0336]

[0337] [1-261] [1-262][1-263][1-264][1-265]

[0338]

[0339] [1-266] [1-267][1-268][1-269][1-270]

[0340]

[0341] [1-271] [1-272][1-273][1-274][1-275]

[0342]

[0343] [1-276] [1-277][1-278][1-279][1-280]

[0344]

[0345] [1-281] [1-282][1-283][1-284][1-285]

[0346]

[0347] [1-286] [1-287][1-288][1-289][1-290]

[0348]

[0349] [1-291] [1-292][1-293][1-294][1-295]

[0350]

[0351] [1-296] [1-297][1-298][1-299][1-300]

[0352]

[0353] [1-301] [1-302][1-303][1-304][1-305]

[0354]

[0355] [1-306] [1-307][1-308][1-309][1-310]

[0356]

[0357] [1-311] [1-312][1-313][1-314][1-315]

[0358]

[0359] [1-316] [1-317][1-318][1-319][1-320]

[0360]

[0361] [1-321] [1-322][1-323][1-324][1-325]

[0362]

[0363] [1-326] [1-327] [1-328] [1-329] [1-330]

[0364]

[0365] [1-331] [1-332] [1-333] [1-334] [1-335]

[0366]

[0367] [1-336] [1-337] [1-338] [1-339] [1-340]

[0368]

[0369] [1-341] [1-342] [1-343] [1-344] [1-345]

[0370]

[0371] [1-346] [1-347] [1-348] [1-349][1-350]

[0372] The above second compound includes a structure in which an amine is substituted on a 6-5-6-5-6 fused ring.

[0373] The inclusion of a fusion ring can further improve the lifetime characteristics by increasing the stability against excitons and minimizing thermal decomposition.

[0374] For example, the second compound may be represented by any one of the following chemical formulas 2A, 2B, 2C, 2D, 2E, and 2F.

[0375] [Chemical Formula 2A] [Chemical Formula 2B]

[0376]

[0377] [Chemical Formula 2C] [Chemical Formula 2D]

[0378]

[0379] [Chemical Formula 2E] [Chemical Formula 2F]

[0380]

[0381] In the above chemical formulas 2A, 2B, 2C, 2D, 2E and 2F,

[0382] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 and Ar 4 and m3 are as defined in Chemical Formula 2 and Chemical Formula 3,

[0383] R c1 Inland R c4 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0384] The above chemical formula 2A can be represented by any one of the following chemical formulas 2A-1 to 2A-4, depending on the substitution point of the amine group.

[0385] [Chemical Formula 2A-1] [Chemical Formula 2A-2]

[0386]

[0387] [Chemical Formula 2A-3] [Chemical Formula 2A-4]

[0388]

[0389] In the above chemical formulas 2A-1 to 2A-4,

[0390] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c1 and R c4 is as described above.

[0391] The above chemical formula 2B can be represented by, for example, any one of the following chemical formulas 2B-1 to 2B-4, depending on the substitution point of the amine group.

[0392] [Chemical Formula 2B-1] [Chemical Formula 2B-2]

[0393]

[0394] [Chemical Formula 2B-3] [Chemical Formula 2B-4]

[0395]

[0396] In the above chemical formulas 2B-1 to 2B-4,

[0397] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c1 and R c2 is as described above.

[0398] The above chemical formula 2C can be represented by any one of the following chemical formulas 2C-1 to 2C-4, depending on the substitution point of the amine group.

[0399] [Chemical Formula 2C-1] [Chemical Formula 2C-2]

[0400]

[0401] [Chemical Formula 2C-3] [Chemical Formula 2C-4]

[0402]

[0403] In the above chemical formulas 2C-1 to 2C-4,

[0404] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c3 and R c4 is as described above.

[0405] The above chemical formula 2D can be represented by, for example, any one of the following chemical formulas 2D-1 to 2D-4, depending on the substitution point of the amine group.

[0406] [Chemical Formula 2D-1] [Chemical Formula 2D-2]

[0407]

[0408] [Chemical Formula 2D-3][Chemical Formula 2D-4]

[0409]

[0410] In the above chemical formulas 2D-1 to 2D-4,

[0411] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c1 and R c4 is as described above.

[0412] The above chemical formula 2E can be represented by any one of the following chemical formulas 2E-1 to 2E-4, depending on the substitution point of the amine group.

[0413] [Chemical Formula 2E-1][Chemical Formula 2E-2]

[0414]

[0415] [Chemical Formula 2E-3][Chemical Formula 2E-4]

[0416]

[0417] In the above chemical formulas 2E-1 to 2E-4,

[0418] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c3 and R c4 is as described above.

[0419] The above chemical formula 2F can be represented by any one of the following chemical formulas 2F-1 to 2F-4, depending on the substitution point of the amine group.

[0420] [Chemical Formula 2F-1] [Chemical Formula 2F-2]

[0421]

[0422] [Chemical Formula 2F-3] [Chemical Formula 2F-4]

[0423]

[0424] In the above chemical formulas 2F-1 to 2F-4,

[0425] X 2 , X 3 , R 3 Inland R 7 , L 4 Inland L 6 , Ar 3 , Ar 4 , m3, R c1 and R c2 is as described above.

[0426] For example, Ar of the above chemical formula 3 3 and Ar 4may each independently be 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0427] As a specific example, Ar of the above chemical formula 3 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0428] For example, L of the above chemical formula 3 4 Inland L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0429] For example, L of the above chemical formula 3 5 -Ar 3 and L 6 -Ar 4 Each of the substituents may be independently selected from the substituents listed in Group II below.

[0430] [Group II]

[0431]

[0432] In the above group II,

[0433] R 16 Inland R 20 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0434] R 21 and R22 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

[0435] m8 is an integer between 1 and 5,

[0436] m9 is one of the integers 1 to 4,

[0437] m10 is one of the integers 1 to 3,

[0438] m11 is an integer of 1 or 2,

[0439] m12 is 1,

[0440] * is a connection point.

[0441] If m8 is 2 or more, each R 16 may be identical or different.

[0442] If m9 is 2 or more, each R 17 may be identical or different.

[0443] If m10 is 2 or more, each R 18 may be identical or different.

[0444] If m11 is 2, each R 19 may be identical or different.

[0445] For example, the above R 3 Inland R 7 and R c1 Inland R c4 Each of may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0446] As a specific example, the above R 3 Inland R 7 and R c1 Inland R c4may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0447] For example, the second compound may be, but is not limited to, one selected from the compounds listed in Group 2 below.

[0448] [Group 2]

[0449]

[0450] [A-1] [A-2] [A-3] [A-4] [A-5]

[0451]

[0452] [A-6] [A-7] [A-8] [A-9] [A-10]

[0453]

[0454] [A-11] [A-12] [A-13] [A-14] [A-15]

[0455]

[0456] [A-16] [A-17] [A-18] [A-19] [A-20]

[0457]

[0458] [A-21] [A-22] [A-23] [A-24] [A-25]

[0459]

[0460] [A-26] [A-27] [A-28] [A-29] [A-30]

[0461]

[0462] [A-31] [A-32] [A-33] [A-34] [A-35]

[0463]

[0464] [A-36] [A-37] [A-38] [A-39] [A-40]

[0465]

[0466] [A-41] [A-42] [A-43] [A-44] [A-45]

[0467]

[0468] [A-46] [A-47] [A-48] [A-49] [A-50]

[0469]

[0470] [A-51] [A-52] [A-53] [A-54] [A-55]

[0471]

[0472] [A-56] [A-57] [A-58] [A-59] [A-60]

[0473]

[0474] [A-61] [A-62] [A-63] [A-64] [A-65]

[0475]

[0476] [A-66] [A-67] [A-68] [A-69] [A-70]

[0477]

[0478] [A-71] [A-72] [A-73] [A-74] [A-75]

[0479]

[0480] [A-76] [A-77] [A-78] [A-79] [A-80]

[0481]

[0482] [A-81] [A-82] [A-83] [A-84] [A-85]

[0483]

[0484] [A-86] [A-87] [A-88] [A-89] [A-90]

[0485]

[0486] [A-91] [A-92] [A-93] [A-94] [A-95]

[0487]

[0488] [A-96] [A-97] [A-98] [A-99] [A-100]

[0489]

[0490] [A-101] [A-102][A-103][A-104][A-105]

[0491]

[0492] [A-106] [A-107][A-108][A-109][A-110]

[0493]

[0494] [A-111] [A-112][A-113][A-114][A-115]

[0495]

[0496] [A-116] [A-117][A-118][A-119][A-120]

[0497]

[0498] [A-121] [A-122][A-123][A-124][A-125]

[0499]

[0500] [A-126] [A-127][A-128][A-129][A-130]

[0501]

[0502] [A-131] [A-132][A-133][A-134][A-135]

[0503]

[0504] [A-136] [A-137][A-138][A-139][A-140]

[0505]

[0506] [A-141] [A-142][A-143][A-144][A-145]

[0507]

[0508] [A-146] [A-147][A-148][A-149][A-150]

[0509]

[0510] [A-151] [A-152][A-153][A-154][A-155]

[0511]

[0512] [A-156] [A-157][A-158][A-159][A-160]

[0513]

[0514] [A-161] [A-162][A-163][A-164][A-165]

[0515]

[0516] [A-166] [A-167][A-168][A-169][A-170]

[0517]

[0518] [A-171] [A-172][A-173][A-174][A-175]

[0519]

[0520] [A-176] [A-177][A-178][A-179][A-180]

[0521]

[0522] [A-181] [A-182][A-183][A-184][A-185]

[0523]

[0524] [A-186] [A-187][A-188][A-189][A-190]

[0525]

[0526] [A-191] [A-192][A-193][A-194][A-195]

[0527]

[0528] [A-196] [A-197][A-198][A-199][A-200]

[0529]

[0530] [B-1] [B-2] [B-3] [B-4] [B-5]

[0531]

[0532] [B-6] [B-7] [B-8] [B-9] [B-10]

[0533]

[0534] [B-11] [B-12] [B-13] [B-14] [B-15]

[0535]

[0536] [B-16] [B-17] [B-18] [B-19] [B-20]

[0537]

[0538] [B-21] [B-22] [B-23] [B-24] [B-25]

[0539]

[0540] [B-26] [B-27] [B-28] [B-29] [B-30]

[0541]

[0542] [B-31] [B-32] [B-33] [B-34] [B-35]

[0543]

[0544] [B-36] [B-37] [B-38] [B-39] [B-40]

[0545]

[0546] [B-41] [B-42] [B-43] [B-44] [B-45]

[0547]

[0548] [B-46] [B-47] [B-48] [B-49] [B-50]

[0549]

[0550] [B-51] [B-52] [B-53] [B-54] [B-55]

[0551]

[0552] [B-56] [B-57] [B-58] [B-59] [B-60]

[0553]

[0554] [B-61] [B-62] [B-63] [B-64] [B-65]

[0555]

[0556] [B-66] [B-67] [B-68] [B-69] [B-70]

[0557]

[0558] [B-71] [B-72] [B-73] [B-74] [B-75]

[0559]

[0560] [B-76] [B-77] [B-78] [B-79] [B-80]

[0561]

[0562] [B-81] [B-82] [B-83] [B-84] [B-85]

[0563]

[0564] [B-86] [B-87] [B-88] [B-89] [B-90]

[0565]

[0566] [B-91] [B-92] [B-93] [B-94] [B-95]

[0567]

[0568] [B-96] [B-97] [B-98] [B-99] [B-100]

[0569]

[0570] [B-101] [B-102][B-103][B-104][B-105]

[0571]

[0572] [B-106] [B-107][B-108][B-109][B-110]

[0573]

[0574] [B-111] [B-112][B-113][B-114][B-115]

[0575]

[0576] [B-116] [B-117][B-118][B-119][B-120]

[0577]

[0578] [B-121] [B-122][B-123][B-124][B-125]

[0579]

[0580] [B-126] [B-127][B-128][B-129][B-130]

[0581]

[0582] [B-131] [B-132][B-133][B-134][B-135]

[0583]

[0584] [B-136] [B-137][B-138][B-139][B-140]

[0585]

[0586] [B-141] [B-142][B-143][B-144][B-145]

[0587]

[0588] [B-146] [B-147][B-148][B-149][B-150]

[0589]

[0590] [B-151] [B-152][B-153][B-154][B-155]

[0591]

[0592] [B-156] [B-157][B-158][B-159][B-160]

[0593]

[0594] [B-161] [B-162][B-163][B-164][B-165]

[0595]

[0596] [B-166] [B-167][B-168][B-169][B-170]

[0597]

[0598] [B-171] [B-172][B-173][B-174][B-175]

[0599]

[0600] [B-176] [B-177][B-178][B-179][B-180]

[0601]

[0602] [B-181] [B-182][B-183][B-184][B-185]

[0603]

[0604] [B-186] [B-187][B-188][B-189][B-190]

[0605]

[0606] [B-191] [B-192][B-193][B-194][B-195]

[0607]

[0608] [B-196] [B-197][B-198][B-199][B-200]

[0609]

[0610] [C-1] [C-2] [C-3] [C-4] [C-5]

[0611]

[0612] [C-6] [C-7] [C-8] [C-9] [C-10]

[0613]

[0614] [C-11] [C-12] [C-13] [C-14] [C-15]

[0615]

[0616] [C-16] [C-17] [C-18] [C-19] [C-20]

[0617]

[0618] [C-21] [C-22] [C-23] [C-24] [C-25]

[0619]

[0620] [C-26] [C-27] [C-28] [C-29] [C-30]

[0621]

[0622] [C-31] [C-32] [C-33] [C-34] [C-35]

[0623]

[0624] [C-36] [C-37] [C-38] [C-39] [C-40]

[0625]

[0626] [C-41] [C-42] [C-43] [C-44] [C-45]

[0627]

[0628] [C-46] [C-47] [C-48] [C-49] [C-50]

[0629]

[0630] [C-51] [C-52] [C-53] [C-54] [C-55]

[0631]

[0632] [C-56] [C-57] [C-58] [C-59] [C-60]

[0633]

[0634] [C-61] [C-62] [C-63] [C-64] [C-65]

[0635]

[0636] [C-66] [C-67] [C-68] [C-69] [C-70]

[0637]

[0638] [C-71] [C-72] [C-73] [C-74] [C-75]

[0639]

[0640] [C-76] [C-77] [C-78] [C-79] [C-80]

[0641]

[0642] [C-81] [C-82] [C-83] [C-84] [C-85]

[0643]

[0644] [C-86] [C-87] [C-88] [C-89] [C-90]

[0645]

[0646] [C-91] [C-92] [C-93] [C-94] [C-95]

[0647]

[0648] [C-96] [C-97] [C-98] [C-99] [C-100]

[0649]

[0650] [C-101] [C-102][C-103][C-104][C-105]

[0651]

[0652] [C-106] [C-107][C-108][C-109][C-110]

[0653]

[0654] [C-111] [C-112][C-113][C-114][C-115]

[0655]

[0656] [C-116] [C-117][C-118][C-119][C-120]

[0657]

[0658] [C-121] [C-122][C-123][C-124][C-125]

[0659]

[0660] [C-126] [C-127][C-128][C-129][C-130]

[0661]

[0662] [C-131] [C-132][C-133][C-134][C-135]

[0663]

[0664] [C-136] [C-137][C-138][C-139][C-140]

[0665]

[0666] [C-141] [C-142][C-143][C-144][C-145]

[0667]

[0668] [C-146] [C-147][C-148][C-149][C-150]

[0669]

[0670] [C-151] [C-152][C-153][C-154][C-155]

[0671]

[0672] [C-156] [C-157][C-158][C-159][C-160]

[0673]

[0674] [C-161] [C-162][C-163][C-164][C-165]

[0675]

[0676] [C-166] [C-167][C-168][C-169][C-170]

[0677]

[0678] [C-171] [C-172][C-173][C-174][C-175]

[0679]

[0680] [C-176] [C-177][C-178][C-179][C-180]

[0681]

[0682] [C-181] [C-182][C-183][C-184][C-185]

[0683]

[0684] [C-186] [C-187][C-188][C-189][C-190]

[0685]

[0686] [C-191] [C-192][C-193][C-194][C-195]

[0687]

[0688] [C-196] [C-197][C-198][C-199][C-200]

[0689]

[0690] [D-1] [D-2] [D-3] [D-4] [D-5]

[0691]

[0692] [D-6] [D-7] [D-8] [D-9] [D-10]

[0693]

[0694] [D-11] [D-12] [D-13] [D-14] [D-15]

[0695]

[0696] [D-16] [D-17] [D-18] [D-19] [D-20]

[0697]

[0698] [D-21] [D-22] [D-23] [D-24] [D-25]

[0699]

[0700] [D-26] [D-27] [D-28] [D-29] [D-30]

[0701]

[0702] [D-31] [D-32] [D-33] [D-34] [D-35]

[0703]

[0704] [D-36] [D-37] [D-38] [D-39] [D-40]

[0705]

[0706] [D-41] [D-42] [D-43] [D-44] [D-45]

[0707]

[0708] [D-46] [D-47] [D-48] [D-49] [D-50]

[0709]

[0710] [D-51] [D-52] [D-53] [D-54] [D-55]

[0711]

[0712] [D-56] [D-57] [D-58] [D-59] [D-60]

[0713]

[0714] [D-61] [D-62] [D-63] [D-64] [D-65]

[0715]

[0716] [D-66] [D-67] [D-68] [D-69] [D-70]

[0717]

[0718] [D-71] [D-72] [D-73] [D-74] [D-75]

[0719]

[0720] [D-76] [D-77] [D-78] [D-79] [D-80]

[0721]

[0722] [D-81] [D-82] [D-83] [D-84] [D-85]

[0723]

[0724] [D-86] [D-87] [D-88] [D-89] [D-90]

[0725]

[0726] [D-91] [D-92] [D-93] [D-94] [D-95]

[0727]

[0728] [D-96] [D-97] [D-98] [D-99] [D-100]

[0729]

[0730] [D-101] [D-102][D-103][D-104][D-105]

[0731]

[0732] [D-106] [D-107][D-108][D-109][D-110]

[0733]

[0734] [D-111] [D-112][D-113][D-114][D-115]

[0735]

[0736] [D-116] [D-117][D-118][D-119][D-120]

[0737]

[0738] [D-121] [D-122][D-123][D-124][D-125]

[0739]

[0740] [D-126] [D-127][D-128][D-129][D-130]

[0741]

[0742] [D-131] [D-132][D-133][D-134][D-135]

[0743]

[0744] [D-136] [D-137][D-138][D-139][D-140]

[0745]

[0746] [D-141] [D-142][D-143][D-144][D-145]

[0747]

[0748] [D-146] [D-147][D-148][D-149][D-150]

[0749]

[0750] [D-151] [D-152][D-153][D-154][D-155]

[0751]

[0752] [D-156] [D-157][D-158][D-159][D-160]

[0753]

[0754] [D-161] [D-162][D-163][D-164][D-165]

[0755]

[0756] [D-166] [D-167][D-168][D-169][D-170]

[0757]

[0758] [D-171] [D-172][D-173][D-174][D-175]

[0759]

[0760] [D-176] [D-177][D-178][D-179][D-180]

[0761]

[0762] [D-181] [D-182][D-183][D-184][D-185]

[0763]

[0764] [D-186] [D-187][D-188][D-189][D-190]

[0765]

[0766] [D-191] [D-192][D-193][D-194][D-195]

[0767]

[0768] [D-196] [D-197][D-198][D-199][D-200]

[0769]

[0770] [E-1] [E-2] [E-3] [E-4] [E-5]

[0771]

[0772] [E-6] [E-7] [E-8] [E-9] [E-10]

[0773]

[0774] [E-11] [E-12] [E-13] [E-14] [E-15]

[0775]

[0776] [E-16] [E-17] [E-18] [E-19] [E-20]

[0777]

[0778] [E-21] [E-22] [E-23] [E-24] [E-25]

[0779]

[0780] [E-26] [E-27] [E-28] [E-29] [E-30]

[0781]

[0782] [E-31] [E-32] [E-33] [E-34] [E-35]

[0783]

[0784] [E-36] [E-37] [E-38] [E-39] [E-40]

[0785]

[0786] [E-41] [E-42] [E-43] [E-44] [E-45]

[0787]

[0788] [E-46] [E-47] [E-48] [E-49] [E-50]

[0789]

[0790] [E-51] [E-52] [E-53] [E-54] [E-55]

[0791]

[0792] [E-56] [E-57] [E-58] [E-59] [E-60]

[0793]

[0794] [E-61] [E-62] [E-63] [E-64] [E-65]

[0795]

[0796] [E-66] [E-67] [E-68] [E-69] [E-70]

[0797]

[0798] [E-71] [E-72] [E-73] [E-74] [E-75]

[0799]

[0800] [E-76] [E-77] [E-78] [E-79] [E-80]

[0801]

[0802] [E-81] [E-82] [E-83] [E-84] [E-85]

[0803]

[0804] [E-86] [E-87] [E-88] [E-89] [E-90]

[0805]

[0806] [E-91] [E-92] [E-93] [E-94] [E-95]

[0807]

[0808] [E-96] [E-97] [E-98] [E-99] [E-100]

[0809]

[0810] [E-101] [E-102][E-103][E-104][E-105]

[0811]

[0812] [E-106] [E-107][E-108][E-109][E-110]

[0813]

[0814] [E-111] [E-112][E-113][E-114][E-115]

[0815]

[0816] [E-116] [E-117][E-118][E-119][E-120]

[0817]

[0818] [E-121] [E-122][E-123][E-124][E-125]

[0819]

[0820] [E-126] [E-127][E-128][E-129][E-130]

[0821]

[0822] [E-131] [E-132][E-133][E-134][E-135]

[0823]

[0824] [E-136] [E-137][E-138][E-139][E-140]

[0825]

[0826] [E-141] [E-142][E-143][E-144][E-145]

[0827]

[0828] [E-146] [E-147][E-148][E-149][E-150]

[0829]

[0830] [E-151] [E-152][E-153][E-154][E-155]

[0831]

[0832] [E-156] [E-157][E-158][E-159][E-160]

[0833]

[0834] [E-161] [E-162][E-163][E-164][E-165]

[0835]

[0836] [E-166] [E-167][E-168][E-169][E-170]

[0837]

[0838] [E-171] [E-172][E-173][E-174][E-175]

[0839]

[0840] [E-176] [E-177][E-178][E-179][E-180]

[0841]

[0842] [E-181] [E-182][E-183][E-184][E-185]

[0843]

[0844] [E-186] [E-187][E-188][E-189][E-190]

[0845]

[0846] [E-191] [E-192][E-193][E-194][E-195]

[0847]

[0848] [E-196] [E-197][E-198][E-199][E-200]

[0849]

[0850] [F-1] [F-2] [F-3] [F-4] [F-5]

[0851]

[0852] [F-6] [F-7] [F-8] [F-9] [F-10]

[0853]

[0854] [F-11] [F-12] [F-13] [F-14] [F-15]

[0855]

[0856] [F-16] [F-17] [F-18] [F-19] [F-20]

[0857]

[0858] [F-21] [F-22] [F-23] [F-24] [F-25]

[0859]

[0860] [F-26] [F-27] [F-28] [F-29] [F-30]

[0861]

[0862] [F-31] [F-32] [F-33] [F-34] [F-35]

[0863]

[0864] [F-36] [F-37] [F-38] [F-39] [F-40]

[0865]

[0866] [F-41] [F-42] [F-43] [F-44] [F-45]

[0867]

[0868] [F-46] [F-47] [F-48] [F-49] [F-50]

[0869]

[0870] [F-51] [F-52] [F-53] [F-54] [F-55]

[0871]

[0872] [F-56] [F-57] [F-58] [F-59] [F-60]

[0873]

[0874] [F-61] [F-62] [F-63] [F-64] [F-65]

[0875]

[0876] [F-66] [F-67] [F-68] [F-69] [F-70]

[0877]

[0878] [F-71] [F-72] [F-73] [F-74] [F-75]

[0879]

[0880] [F-76] [F-77] [F-78] [F-79] [F-80]

[0881]

[0882] [F-81][F-82] [F-83] [F-84] [F-85]

[0883]

[0884] [F-86] [F-87] [F-88] [F-89] [F-90]

[0885]

[0886] [F-91] [F-92] [F-93] [F-94] [F-95]

[0887]

[0888] [F-96] [F-97] [F-98] [F-99] [F-100]

[0889]

[0890] [F-101] [F-102][F-103][F-104][F-105]

[0891]

[0892] [F-106] [F-107][F-108][F-109][F-110]

[0893]

[0894] [F-111] [F-112][F-113][F-114][F-115]

[0895]

[0896] [F-116] [F-117][F-118][F-119][F-120]

[0897]

[0898] [F-121] [F-122][F-123][F-124][F-125]

[0899]

[0900] [F-126] [F-127][F-128][F-129][F-130]

[0901]

[0902] [F-131] [F-132][F-133][F-134][F-135]

[0903]

[0904] [F-136] [F-137][F-138][F-139][F-140]

[0905]

[0906] [F-141] [F-142][F-143][F-144][F-145]

[0907]

[0908] [F-146] [F-147][F-148][F-149][F-150]

[0909]

[0910] [F-151] [F-152][F-153][F-154][F-155]

[0911]

[0912] [F-156] [F-157][F-158][F-159][F-160]

[0913]

[0914] [F-161] [F-162][F-163][F-164][F-165]

[0915]

[0916] [F-166] [F-167][F-168][F-169][F-170]

[0917]

[0918] [F-171] [F-172][F-173][F-174][F-175]

[0919]

[0920] [F-176] [F-177][F-178][F-179][F-180]

[0921]

[0922] [F-181] [F-182][F-183][F-184][F-185]

[0923]

[0924] [F-186] [F-187][F-188][F-189][F-190]

[0925]

[0926] [F-191] [F-192][F-193][F-194][F-195]

[0927]

[0928] [F-196] [F-197][F-198][F-199][F-200]

[0929]

[0930] [F-201] [F-202][F-203][F-204][F-205]

[0931]

[0932] [F-206] [F-207][F-208][F-209][F-210]

[0933]

[0934] [F-211] [F-212][F-213][F-214][F-215]

[0935]

[0936] [F-216] [F-217][F-218][F-219][F-220]

[0937]

[0938] [F-221] [F-222][F-223][F-224][F-225]

[0939]

[0940] [F-226] [F-227][F-228][F-229][F-230]

[0941]

[0942] [F-231] [F-232][F-233][F-234][F-235]

[0943]

[0944] [F-236] [F-237][F-238][F-239][F-240]

[0945]

[0946] [F-241] [F-242][F-243][F-244][F-245]

[0947]

[0948] [F-246] [F-247][F-248][F-249][F-250]

[0949]

[0950] [F-251] [F-252][F-253][F-254][F-255]

[0951]

[0952] [F-256] [F-257][F-258][F-259][F-260]

[0953]

[0954] [F-261] [F-262][F-263][F-264][F-265]

[0955]

[0956] [F-266] [F-267][F-268][F-269][F-270]

[0957]

[0958] [F-271] [F-272][F-273][F-274][F-275]

[0959]

[0960] [F-276] [F-277][F-278][F-279][F-280]

[0961]

[0962] [F-281] [F-282][F-283][F-284][F-285]

[0963]

[0964] [F-286] [F-287][F-288][F-289][F-290]

[0965]

[0966] [F-291] [F-292][F-293][F-294][F-295]

[0967]

[0968] [F-296] [F-297][F-298][F-299][F-300]

[0969]

[0970] [F-301] [F-302][F-303][F-304][F-305]

[0971]

[0972] [F-306] [F-307][F-308][F-309][F-310]

[0973]

[0974] [F-311] [F-312][F-313][F-314][F-315]

[0975]

[0976] [F-316] [F-317][F-318][F-319][F-320]

[0977]

[0978] [F-321] [F-322][F-323][F-324][F-325]

[0979]

[0980] [F-326] [F-327][F-328][F-329][F-330]

[0981]

[0982] [F-331] [F-332][F-333][F-334][F-335]

[0983]

[0984] [F-336] [F-337][F-338][F-339][F-340]

[0985]

[0986] [F-341] [F-342][F-343][F-344][F-345]

[0987]

[0988] [F-346] [F-347][F-348][F-349][F-350]

[0989]

[0990] [F-351] [F-352][F-353][F-354][F-355]

[0991]

[0992] [F-356] [F-357][F-358][F-359][F-360]

[0993]

[0994] [F-361] [F-362][F-363][F-364][F-365]

[0995]

[0996] [F-366] [F-367][F-368][F-369][F-370]

[0997]

[0998] [F-371] [F-372][F-373][F-374][F-375]

[0999]

[1000] [F-376] [F-377][F-378][F-379][F-380]

[1001]

[1002] [F-381] [F-382][F-383][F-384][F-385]

[1003]

[1004] [F-386] [F-387][F-388][F-389][F-390]

[1005]

[1006] [F-391] [F-392][F-393][F-394][F-395]

[1007]

[1008] [F-396] [F-397][F-398][F-399][F-400]

[1009]

[1010] [F-401] [F-402][F-403][F-404][F-405]

[1011]

[1012] [F-406] [F-407][F-408][F-409][F-410]

[1013]

[1014] [F-411] [F-412][F-413][F-414][F-415]

[1015]

[1016] [F-416] [F-417][F-418][F-419][F-420]

[1017]

[1018] [F-421] [F-422][F-423][F-424][F-425]

[1019]

[1020] [F-426] [F-427][F-428][F-429][F-430]

[1021]

[1022] [F-431] [F-432][F-433][F-434][F-435]

[1023]

[1024] [F-436] [F-437][F-438][F-439][F-440]

[1025] In a most specific embodiment of the present invention, the first compound may be represented by the chemical formula 1-3, and the second compound may be represented by 2F.

[1026] In a more specific embodiment, the first compound may be represented by the chemical formula 1-3, and the second compound may be represented by 2F-4.

[1027] The above organic layer (30) may include an electron transport region.

[1028] The above electron transport region can further increase electron injection and / or electron mobility between the cathode (20) and the light-emitting layer (31) and block holes.

[1029] Specifically, the electron transport region may include an electron transport layer (35) between the cathode (20) and the light-emitting layer (31), and an electron transport auxiliary layer (not shown) between the light-emitting layer (31) and the electron transport layer (35), and at least one of the compounds listed in Group C below may be included in at least one layer of the electron transport layer (35) and the electron transport auxiliary layer.

[1030] [Group C]

[1031]

[1032]

[1033]

[1034]

[1035]

[1036]

[1037]

[1038]

[1039]

[1040]

[1041]

[1042]

[1043]

[1044]

[1045]

[1046]

[1047]

[1048] An example of an embodiment may be an organic light-emitting device including an organic layer as a light-emitting layer (31), a hole transport layer (32), a first hole transport layer (33a), and a second hole transport layer (33b).

[1049] Another embodiment may be an organic light-emitting device that additionally includes a hole injection layer as an organic layer.

[1050] Another embodiment may be an organic light-emitting device that additionally includes an electron transport region as an organic layer.

[1051] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown) in addition to the light-emitting layer as the aforementioned organic layer.

[1052] An organic light-emitting device can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film deposition method such as evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or anode thereon.

[1053] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[1054] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[1055] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[1056]

[1057] (Preparation of the first compound)

[1058] Synthesis Example 1: Synthesis of Compound 1-139

[1059] [Reaction Formula 1]

[1060]

[1061] Int-1 (CAS No. 2379717-75-4) (5 g, 15.7 mmol) was dissolved in toluene (80 mL), and Int-2 (CAS No. 897671-69-1) (5.29 g, 16.5 mmol), NaOtBu (2.26 g, 23.5 mmol), Pd2(dba)3 (0.72 g, 0.8 mmol), and P(tBu)3 (1.13 mL, 2.4 mmol) were added and refluxed for 3 hours. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting compound was separated through a silica gel column and recrystallized to obtain 6.95 g (yield 73%) of compound 1-139.

[1062]

[1063] Synthesis Example 2: Synthesis of Compound 1-233

[1064]

[1065] Compound 1-233 was synthesized using the same method as Synthesis Example 1, except that 10 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine and 10.91 g of 1-chloro-9-phenyldibenzo[b,d]furan were used in an equivalent ratio of 1:1.1 (4.86 g, yield 51%).

[1066]

[1067] (Preparation of the second compound)

[1068] Synthesis Example 3: Synthesis of Compound F-56

[1069]

[1070] Compound F-56 was synthesized (13.52 g, yield 72%) in the same manner as in Synthesis Example 1, except that 10 g of di([1,1'-biphenyl]-4-yl)amine and 10.91 g of 11-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran were used in an equivalent ratio of 1:1.1.

[1071]

[1072] Synthesis Example 4: Synthesis of Compound F-83

[1073]

[1074] Compound F-83 was synthesized (13.48 g, yield 75%) in the same manner as in Synthesis Example 1, except that 10 g of di([1,1'-biphenyl]-4-yl)amine and 10.02 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[1075]

[1076] Synthesis Example 5: Synthesis of Compound F-110

[1077]

[1078] Compound F-110 was synthesized using the same method as Synthesis Example 1, except that 10 g of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine and 6.12 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1 (12.20 g, yield 82%).

[1079]

[1080] Synthesis Example 6: Synthesis of Compound F-137

[1081]

[1082] Compound F-137 was synthesized using the same method as Synthesis Example 1, except that 10 g of 9,9-dimethyl-N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine and 6.95 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1 (12.11 g, yield 78%).

[1083]

[1084] (Preparation of comparative compounds)

[1085] Comparative Example 1: Synthesis of Compound R-1

[1086]

[1087] Compound R-1 was synthesized in the same manner as in Synthetic Example 1, except that 15 g of the intermediate 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine and 6.93 g of the intermediate 3-chlorodibenzo[b,d]furan were used in an equivalent ratio of 1:1.2 (15 g, yield 76%).

[1088]

[1089] Example 1

[1090] A glass substrate coated with a thin film of ITO / Ag / ITO was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as acetone or isopropyl alcohol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO / Ag / ITO (reflective electrode) prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO / Ag / ITO substrate to form a hole injection layer with a thickness of 100 Å, and Compound A was deposited on the hole injection layer with a thickness of 1350 Å to form a hole transport layer. Compound 1-139 obtained in Synthesis Example 1 was deposited on the hole transport layer to a thickness of 285 Å to form a first hole transport auxiliary layer, and compound F-56 obtained in Synthesis Example 3 was deposited on the first hole transport auxiliary layer to a thickness of 50 Å to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, a light-emitting layer having a thickness of 380 Å was formed by vacuum deposition using 85 wt% of host H1 (40%) and host H2 (60%) as a host and doping with 15 wt% of PtGD as a dopant. Subsequently, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum-deposited at a 1:1 ratio to form an electron transport layer having a thickness of 310 Å. An organic light-emitting device was manufactured by sequentially vacuum-depositing Yb and AgMg on top of the electron transport layer to form a cathode.

[1091] It was fabricated with the structure of ITO / Ag / ITO / hole injection layer (compound A doped with 3% NDP-9, 100Å) / hole transport layer (compound A, 1350Å) / first hole transport auxiliary layer (285Å) / second hole transport auxiliary layer (50Å) / emission layer [Host (host H1: host H2 = 40 wt%: 60 wt%): PtGD = 85 wt%: 15 wt%] (380Å) / electron transport auxiliary layer (compound C, 50Å) / electron transport layer (compound D: Liq, 310Å) / Yb / AgMg.

[1092] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[1093] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[1094] Compound D: 2-(4-{2-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-1-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[1095] Host H1: Host H2: PtGD:

[1096]

[1097]

[1098] Examples 2 to 11 and Comparative Examples 1 to 3

[1099] An organic light-emitting device was manufactured in the same manner as Example 1, except that the composition was changed to that described in Table 1 below.

[1100]

[1101] evaluation

[1102] The luminous efficiency and lifespan characteristics of the organic light-emitting devices according to Examples 1 to 11 and Comparative Examples 1 to 3 were evaluated.

[1103] The specific measurement method is as follows, and the results are as shown in Tables 1 and 2.

[1104] (1) Measurement of changes in current density according to voltage changes

[1105] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[1106] (2) Measurement of luminance change according to voltage change

[1107] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[1108] (3) Life span measurement

[1109] Luminance (cd / m 2 ) to 24000cd / m 2 The results were obtained by maintaining the current at 97% and measuring the time until the current efficiency (cd / A) decreased to 97%.

[1110] The life measurement values ​​of Examples 1 to 11 and Comparative Examples 2 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[1111] No. 1st hole transport auxiliary layer 2nd hole transport auxiliary layer Lifespan (%) Example 11-139F56 100 Example 21-139F83 109 Example 31-139F110 110 Example 41-139F137 113 Example 51-233F56 109 Example 61-233F83 118 Example 71-233F110 119 Example 81-233F137 125 Comparative Example 11-139R-181 Comparative Example 21-233R-187 Comparative Example 3-R-179 Comparative Example 41-139-85

[1112] Referring to Table 1, it can be confirmed that the lifespan characteristics of the organic light-emitting devices according to Examples 1 to 11 are significantly improved compared to the organic light-emitting devices according to Comparative Examples 1 to 3.

Claims

1. Positive and negative poles facing each other, A light-emitting layer positioned between the anode and the cathode, A hole transport layer positioned between the anode and the light-emitting layer, A hole transport auxiliary layer located between the above hole transport layer and the above light emitting layer Including, The above hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, The first positive hole transport auxiliary layer comprises a first compound represented by the following chemical formula 1, The second hole transport auxiliary layer is an organic optoelectronic device including a second compound represented by a combination of the following chemical formulas 2 and 3: [Chemical Formula 1] In the above chemical formula 1, X 1 is O or S, L 1 Inside L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is one of the integers 1 to 4, m2 is one of the integers 1 to 3, If m1 is 2 or more, each R 1 are identical or different from each other, If m2 is 2 or more, each R 2 are identical or different from each other; [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, X 2 and X 3 are each independently O, S or CR a R b And, X 2 and X 3 At least one of them is O or S, R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, In chemical formula 2, a1* to a4* are each independently a connecting carbon (C) or CR. c And, In chemical formula 3, * is a connecting carbon (C), Among a1* to a4* of chemical formula 2, two adjacent ones are connected to * of chemical formula 3, and among a1* to a4* of chemical formula 2, the remaining two that are not connected to chemical formula 3 are each independently CR. c And, R c and R 3 Inland R 7 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 Inside L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m3 is one of the integers 1 to 3, If m3 is 2 or more, each R 7 are identical or different from each other.

2. In paragraph 1, The above chemical formula 1 is an organic optoelectronic device represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, L 1 Inside L 3 , X 1 , R 1 , R 2 , Ar 1 , Ar 2 , m1 and m2 are defined as in Chemical Formula 1.

3. In paragraph 1, Above Ar 1 and Ar 2 An organic optoelectronic device, wherein each independently represents 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

4. In paragraph 1, Above L 2 -Ar 1 and L 3 -Ar 2 An organic optoelectronic device, wherein each of the substituents is independently selected from the substituents listed in Group I below: [Group I] In the above group I, R 10 Inland R 13 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, R 14 and R 15 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, m4 is one of the integers 1 to 5, m5 is one of the integers 1 to 4, m6 is one of the integers 1 to 3, m7 is an integer of 1 or 2, * is a connection point.

5. In paragraph 1, The first compound is an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1] [1-1] [1-2] [1-3] [1-4] [1-5] [1-6] [1-7] [1-8] [1-9] [1-10] [1-11] [1-12] [1-13] [1-14] [1-15] [1-16] [1-17] [1-18] [1-19] [1-20] [1-21] [1-22] [1-23] [1-24] [1-25] [1-26] [1-27] [1-28] [1-29] [1-30] [1-31] [1-32] [1-33] [1-34] [1-35] [1-36] [1-37] [1-38] [1-39] [1-40] [1-41] [1-42] [1-43] [1-44] [1-45] [1-46] [1-47] [1-48] [1-49] [1-50] [1-51] [1-52] [1-53] [1-54] [1-55] [1-56] [1-57] [1-58] [1-59] [1-60] [1-61] [1-62] [1-63] [1-64] [1-65] [1-66] [1-67] [1-68] [1-69] [1-70] [1-71] [1-72] [1-73] [1-74] [1-75] [1-76] [1-77] [1-78] [1-79] [1-80] [1-81] [1-82] [1-83] [1-84] [1-85] [1-86] [1-87] [1-88] [1-89] [1-90] [1-91] [1-92] [1-93] [1-94] [1-95] [1-96] [1-97] [1-98] [1-99] [1-100] [1-101] [1-102][1-103][1-104][1-105] [1-106] [1-107][1-108][1-109][1-110] [1-111] [1-112][1-113][1-114][1-115] [1-116] [1-117][1-118][1-119][1-120] [1-121] [1-122][1-123][1-124][1-125] [1-126] [1-127][1-128][1-129][1-130] [1-131] [1-132][1-133][1-134][1-135] [1-136] [1-137][1-138][1-139][1-140] [1-141] [1-142][1-143][1-144][1-145] [1-146] [1-147][1-148][1-149][1-150] [1-151] [1-152][1-153][1-154][1-155] [1-156] [1-157][1-158][1-159][1-160] [1-161] [1-162][1-163][1-164][1-165] [1-166] [1-167][1-168][1-169][1-170] [1-171] [1-172][1-173][1-174][1-175] [1-176] [1-177][1-178][1-179][1-180] [1-181] [1-182][1-183][1-184][1-185] [1-186] [1-187][1-188][1-189][1-190] [1-191] [1-192][1-193][1-194][1-195] [1-196] [1-197][1-198][1-199][1-200] [1-201] [1-202][1-203][1-204][1-205] [1-206] [1-207][1-208][1-209][1-210] [1-211] [1-212][1-213][1-214][1-215] [1-216] [1-217][1-218][1-219][1-220] [1-221] [1-222][1-223][1-224][1-225] [1-226] [1-227][1-228][1-229][1-230] [1-231] [1-232][1-233][1-234][1-235] [1-236] [1-237][1-238][1-239][1-240] [1-241] [1-242][1-243][1-244][1-245] [1-246] [1-247][1-248][1-249][1-250] [1-251] [1-252][1-253][1-254][1-255] [1-256] [1-257][1-258][1-259][1-260] [1-261] [1-262][1-263][1-264][1-265] [1-266] [1-267][1-268][1-269][1-270] [1-271] [1-272][1-273][1-274][1-275] [1-276] [1-277][1-278][1-279][1-280] [1-281] [1-282][1-283][1-284][1-285] [1-286] [1-287][1-288][1-289][1-290] [1-291] [1-292][1-293][1-294][1-295] [1-296] [1-297][1-298][1-299][1-300] [1-301] [1-302][1-303][1-304][1-305] [1-306] [1-307][1-308][1-309][1-310] [1-311] [1-312][1-313][1-314][1-315] [1-316] [1-317][1-318][1-319][1-320] [1-321] [1-322][1-323][1-324][1-325] [1-326] [1-327] [1-328] [1-329] [1-330] [1-331] [1-332] [1-333] [1-334] [1-335] [1-336] [1-337] [1-338] [1-339] [1-340] [1-341] [1-342] [1-343] [1-344] [1-345] [1-346] [1-347] [1-348] [1-349][1-350].

6. In paragraph 1, The second compound is an organic optoelectronic device represented by any one of the following chemical formulas 2A, 2B, 2C, 2D, 2E and 2F: [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] [Chemical Formula 2D] [Chemical Formula 2E] [Chemical Formula 2F] In the above chemical formulas 2A, 2B, 2C, 2D, 2E and 2F, X 2 , X 3 , R 3 Inland R 7 , L 4 Inside L 6 , Ar 3 and Ar 4 and m3 are as defined in chemical formula 2 and chemical formula 3, R c1 Inland R c4 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

7. In paragraph 1, Ar of the above chemical formula 3 3 and Ar 4 An organic optoelectronic device, wherein each independently represents 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

8. In paragraph 1, L of the above chemical formula 3 5 -Ar 3 and L 6 -Ar 4 Organic optoelectronic devices, each independently selected from the substituents listed in Group II below: [Group II] In the above group II, R 16 Inland R 20 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, R 21 and R 22 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, m8 is an integer between 1 and 5, m9 is one of the integers 1 to 4, m10 is one of the integers 1 to 3, m11 is an integer of 1 or 2, m12 is 1, * is a connection point.

9. In paragraph 1, The second compound is an organic optoelectronic device selected from the compounds listed in Group 2 below: [Group 2] [A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-13] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] [A-41] [A-42] [A-43] [A-44] [A-45] [A-46] [A-47] [A-48] [A-49] [A-50] [A-51] [A-52] [A-53] [A-54] [A-55] [A-56] [A-57] [A-58] [A-59] [A-60] [A-61] [A-62] [A-63] [A-64] [A-65] [A-66] [A-67] [A-68] [A-69] [A-70] [A-71] [A-72] [A-73] [A-74] [A-75] [A-76] [A-77] [A-78] [A-79] [A-80] [A-81] [A-82] [A-83] [A-84] [A-85] [A-86] [A-87] [A-88] [A-89] [A-90] [A-91] [A-92] [A-93] [A-94] [A-95] [A-96] [A-97] [A-98] [A-99] [A-100] [A-101] [A-102][A-103][A-104][A-105] [A-106] [A-107][A-108][A-109][A-110] [A-111] [A-112][A-113][A-114][A-115] [A-116] [A-117][A-118][A-119][A-120] [A-121] [A-122][A-123][A-124][A-125] [A-126] [A-127][A-128][A-129][A-130] [A-131] [A-132][A-133][A-134][A-135] [A-136] [A-137][A-138][A-139][A-140] [A-141] [A-142][A-143][A-144][A-145] [A-146] [A-147][A-148][A-149][A-150] [A-151] [A-152][A-153][A-154][A-155] [A-156] [A-157][A-158][A-159][A-160] [A-161] [A-162][A-163][A-164][A-165] [A-166] [A-167][A-168][A-169][A-170] [A-171] [A-172][A-173][A-174][A-175] [A-176] [A-177][A-178][A-179][A-180] [A-181] [A-182][A-183][A-184][A-185] [A-186] [A-187][A-188][A-189][A-190] [A-191] [A-192][A-193][A-194][A-195] [A-196] [A-197][A-198][A-199][A-200] [B-1] [B-2] [B-3] [B-4] [B-5] [B-6] [B-7] [B-8] [B-9] [B-10] [B-11] [B-12] [B-13] [B-14] [B-15] [B-16] [B-17] [B-18] [B-19] [B-20] [B-21] [B-22] [B-23] [B-24] [B-25] [B-26] [B-27] [B-28] [B-29] [B-30] [B-31] [B-32] [B-33] [B-34] [B-35] [B-36] [B-37] [B-38] [B-39] [B-40] [B-41] [B-42] [B-43] [B-44] [B-45] [B-46] [B-47] [B-48] [B-49] [B-50] [B-51] [B-52] [B-53] [B-54] [B-55] [B-56] [B-57] [B-58] [B-59] [B-60] [B-61] [B-62] [B-63] [B-64] [B-65] [B-66] [B-67] [B-68] [B-69] [B-70] [B-71] [B-72] [B-73] [B-74] [B-75] [B-76] [B-77] [B-78] [B-79] [B-80] [B-81] [B-82] [B-83] [B-84] [B-85] [B-86] [B-87] [B-88] [B-89] [B-90] [B-91] [B-92] [B-93] [B-94] [B-95] [B-96] [B-97] [B-98] [B-99] [B-100] [B-101] [B-102][B-103][B-104][B-105] [B-106] [B-107][B-108][B-109][B-110] [B-111] [B-112][B-113][B-114][B-115] [B-116] [B-117][B-118][B-119][B-120] [B-121] [B-122][B-123][B-124][B-125] [B-126] [B-127][B-128][B-129][B-130] [B-131] [B-132][B-133][B-134][B-135] [B-136] [B-137][B-138][B-139][B-140] [B-141] [B-142][B-143][B-144][B-145] [B-146] [B-147][B-148][B-149][B-150] [B-151] [B-152][B-153][B-154][B-155] [B-156] [B-157][B-158][B-159][B-160] [B-161] [B-162][B-163][B-164][B-165] [B-166] [B-167][B-168][B-169][B-170] [B-171] [B-172][B-173][B-174][B-175] [B-176] [B-177][B-178][B-179][B-180] [B-181] [B-182][B-183][B-184][B-185] [B-186] [B-187][B-188][B-189][B-190] [B-191] [B-192][B-193][B-194][B-195] [B-196] [B-197][B-198][B-199][B-200] [C-1] [C-2] [C-3] [C-4] [C-5] [C-6] [C-7] [C-8] [C-9] [C-10] [C-11] [C-12] [C-13] [C-14] [C-15] [C-16] [C-17] [C-18] [C-19] [C-20] [C-21] [C-22] [C-23] [C-24] [C-25] [C-26] [C-27] [C-28] [C-29] [C-30] [C-31] [C-32] [C-33] [C-34] [C-35] [C-36] [C-37] [C-38] [C-39] [C-40] [C-41] [C-42] [C-43] [C-44] [C-45] [C-46] [C-47] [C-48] [C-49] [C-50] [C-51] [C-52] [C-53] [C-54] [C-55] [C-56] [C-57] [C-58] [C-59] [C-60] [C-61] [C-62] [C-63] [C-64] [C-65] [C-66] [C-67] [C-68] [C-69] [C-70] [C-71] [C-72] [C-73] [C-74] [C-75] [C-76] [C-77] [C-78] [C-79] [C-80] [C-81] [C-82] [C-83] [C-84] [C-85] [C-86] [C-87] [C-88] [C-89] [C-90] [C-91] [C-92] [C-93] [C-94] [C-95] [C-96] [C-97] [C-98] [C-99] [C-100] [C-101] [C-102][C-103][C-104][C-105] [C-106] [C-107][C-108][C-109][C-110] [C-111] [C-112][C-113][C-114][C-115] [C-116] [C-117][C-118][C-119][C-120] [C-121] [C-122][C-123][C-124][C-125] [C-126] [C-127][C-128][C-129][C-130] [C-131] [C-132][C-133][C-134][C-135] [C-136] [C-137][C-138][C-139][C-140] [C-141] [C-142][C-143][C-144][C-145] [C-146] [C-147][C-148][C-149][C-150] [C-151] [C-152][C-153][C-154][C-155] [C-156] [C-157][C-158][C-159][C-160] [C-161] [C-162][C-163][C-164][C-165] [C-166] [C-167][C-168][C-169][C-170] [C-171] [C-172][C-173][C-174][C-175] [C-176] [C-177][C-178][C-179][C-180] [C-181] [C-182][C-183][C-184][C-185] [C-186] [C-187][C-188][C-189][C-190] [C-191] [C-192][C-193][C-194][C-195] [C-196] [C-197][C-198][C-199][C-200] [D-1] [D-2] [D-3] [D-4] [D-5] [D-6] [D-7] [D-8] [D-9] [D-10] [D-11] [D-12] [D-13] [D-14] [D-15] [D-16] [D-17] [D-18] [D-19] [D-20] [D-21] [D-22] [D-23] [D-24] [D-25] [D-26] [D-27] [D-28] [D-29] [D-30] [D-31] [D-32] [D-33] [D-34] [D-35] [D-36] [D-37] [D-38] [D-39] [D-40] [D-41] [D-42] [D-43] [D-44] [D-45] [D-46] [D-47] [D-48] [D-49] [D-50] [D-51] [D-52] [D-53] [D-54] [D-55] [D-56] [D-57] [D-58] [D-59] [D-60] [D-61] [D-62] [D-63] [D-64] [D-65] [D-66] [D-67] [D-68] [D-69] [D-70] [D-71] [D-72] [D-73] [D-74] [D-75] [D-76] [D-77] [D-78] [D-79] [D-80] [D-81] [D-82] [D-83] [D-84] [D-85] [D-86] [D-87] [D-88] [D-89] [D-90] [D-91] [D-92] [D-93] [D-94] [D-95] [D-96] [D-97] [D-98] [D-99] [D-100] [D-101] [D-102][D-103][D-104][D-105] [D-106] [D-107][D-108][D-109][D-110] [D-111] [D-112][D-113][D-114][D-115] [D-116] [D-117][D-118][D-119][D-120] [D-121] [D-122][D-123][D-124][D-125] [D-126] [D-127][D-128][D-129][D-130] [D-131] [D-132][D-133][D-134][D-135] [D-136] [D-137][D-138][D-139][D-140] [D-141] [D-142][D-143][D-144][D-145] [D-146] [D-147][D-148][D-149][D-150] [D-151] [D-152][D-153][D-154][D-155] [D-156] [D-157][D-158][D-159][D-160] [D-161] [D-162][D-163][D-164][D-165] [D-166] [D-167][D-168][D-169][D-170] [D-171] [D-172][D-173][D-174][D-175] [D-176] [D-177][D-178][D-179][D-180] [D-181] [D-182][D-183][D-184][D-185] [D-186] [D-187][D-188][D-189][D-190] [D-191] [D-192][D-193][D-194][D-195] [D-196] [D-197][D-198][D-199][D-200] [E-1] [E-2] [E-3] [E-4] [E-5] [E-6] [E-7] [E-8] [E-9] [E-10] [E-11] [E-12] [E-13] [E-14] [E-15] [E-16] [E-17] [E-18] [E-19] [E-20] [E-21] [E-22] [E-23] [E-24] [E-25] [E-26] [E-27] [E-28] [E-29] [E-30] [E-31] [E-32] [E-33] [E-34] [E-35] [E-36] [E-37] [E-38] [E-39] [E-40] [E-41] [E-42] [E-43] [E-44] [E-45] [E-46] [E-47] [E-48] [E-49] [E-50] [E-51] [E-52] [E-53] [E-54] [E-55] [E-56] [E-57] [E-58] [E-59] [E-60] [E-61] [E-62] [E-63] [E-64] [E-65] [E-66] [E-67] [E-68] [E-69] [E-70] [E-71] [E-72] [E-73] [E-74] [E-75] [E-76] [E-77] [E-78] [E-79] [E-80] [E-81] [E-82] [E-83] [E-84] [E-85] [E-86] [E-87] [E-88] [E-89] [E-90] [E-91] [E-92] [E-93] [E-94] [E-95] [E-96] [E-97] [E-98] [E-99] [E-100] [E-101] [E-102][E-103][E-104][E-105] [E-106] [E-107][E-108][E-109][E-110] [E-111] [E-112][E-113][E-114][E-115] [E-116] [E-117][E-118][E-119][E-120] [E-121] [E-122][E-123][E-124][E-125] [E-126] [E-127][E-128][E-129][E-130] [E-131] [E-132][E-133][E-134][E-135] [E-136] [E-137][E-138][E-139][E-140] [E-141] [E-142][E-143][E-144][E-145] [E-146] [E-147][E-148][E-149][E-150] [E-151] [E-152][E-153][E-154][E-155] [E-156] [E-157][E-158][E-159][E-160] [E-161] [E-162][E-163][E-164][E-165] [E-166] [E-167][E-168][E-169][E-170] [E-171] [E-172][E-173][E-174][E-175] [E-176] [E-177][E-178][E-179][E-180] [E-181] [E-182][E-183][E-184][E-185] [E-186] [E-187][E-188][E-189][E-190] [E-191] [E-192][E-193][E-194][E-195] [E-196] [E-197][E-198][E-199][E-200] [F-1] [F-2] [F-3] [F-4] [F-5] [F-6] [F-7] [F-8] [F-9] [F-10] [F-11] [F-12] [F-13] [F-14] [F-15] [F-16] [F-17] [F-18] [F-19] [F-20] [F-21] [F-22] [F-23] [F-24] [F-25] [F-26] [F-27] [F-28] [F-29] [F-30] [F-31] [F-32] [F-33] [F-34] [F-35] [F-36] [F-37] [F-38] [F-39] [F-40] [F-41] [F-42] [F-43] [F-44] [F-45] [F-46] [F-47] [F-48] [F-49] [F-50] [F-51] [F-52] [F-53] [F-54] [F-55] [F-56] [F-57] [F-58] [F-59] [F-60] [F-61] [F-62] [F-63] [F-64] [F-65] [F-66] [F-67] [F-68] [F-69] [F-70] [F-71] [F-72] [F-73] [F-74] [F-75] [F-76] [F-77] [F-78] [F-79] [F-80] [F-81][F-82] [F-83] [F-84] [F-85] [F-86] [F-87] [F-88] [F-89] [F-90] [F-91] [F-92] [F-93] [F-94] [F-95] [F-96] [F-97] [F-98] [F-99] [F-100] [F-101] [F-102][F-103][F-104][F-105] [F-106] [F-107][F-108][F-109][F-110] [F-111] [F-112][F-113][F-114][F-115] [F-116] [F-117][F-118][F-119][F-120] [F-121] [F-122][F-123][F-124][F-125] [F-126] [F-127][F-128][F-129][F-130] [F-131] [F-132][F-133][F-134][F-135] [F-136] [F-137][F-138][F-139][F-140] [F-141] [F-142][F-143][F-144][F-145] [F-146] [F-147][F-148][F-149][F-150] [F-151] [F-152][F-153][F-154][F-155] [F-156] [F-157][F-158][F-159][F-160] [F-161] [F-162][F-163][F-164][F-165] [F-166] [F-167][F-168][F-169][F-170] [F-171] [F-172][F-173][F-174][F-175] [F-176] [F-177][F-178][F-179][F-180] [F-181] [F-182][F-183][F-184][F-185] [F-186] [F-187][F-188][F-189][F-190] [F-191] [F-192][F-193][F-194][F-195] [F-196] [F-197][F-198][F-199][F-200] [F-201] [F-202][F-203][F-204][F-205] [F-206] [F-207][F-208][F-209][F-210] [F-211] [F-212][F-213][F-214][F-215] [F-216] [F-217][F-218][F-219][F-220] [F-221] [F-222][F-223][F-224][F-225] [F-226] [F-227][F-228][F-229][F-230] [F-231] [F-232][F-233][F-234][F-235] [F-236] [F-237][F-238][F-239][F-240] [F-241] [F-242][F-243][F-244][F-245] [F-246] [F-247][F-248][F-249][F-250] [F-251] [F-252][F-253][F-254][F-255] [F-256] [F-257][F-258][F-259][F-260] [F-261] [F-262][F-263][F-264][F-265] [F-266] [F-267][F-268][F-269][F-270] [F-271] [F-272][F-273][F-274][F-275] [F-276] [F-277][F-278][F-279][F-280] [F-281] [F-282][F-283][F-284][F-285] [F-286] [F-287][F-288][F-289][F-290] [F-291] [F-292][F-293][F-294][F-295] [F-296] [F-297][F-298][F-299][F-300] [F-301] [F-302][F-303][F-304][F-305] [F-306] [F-307][F-308][F-309][F-310] [F-311] [F-312][F-313][F-314][F-315] [F-316] [F-317][F-318][F-319][F-320] [F-321] [F-322][F-323][F-324][F-325] [F-326] [F-327][F-328][F-329][F-330] [F-331] [F-332][F-333][F-334][F-335] [F-336] [F-337][F-338][F-339][F-340] [F-341] [F-342][F-343][F-344][F-345] [F-346] [F-347][F-348][F-349][F-350] [F-351] [F-352][F-353][F-354][F-355] [F-356] [F-357][F-358][F-359][F-360] [F-361] [F-362][F-363][F-364][F-365] [F-366] [F-367][F-368][F-369][F-370] [F-371] [F-372][F-373][F-374][F-375] [F-376] [F-377][F-378][F-379][F-380] [F-381] [F-382][F-383][F-384][F-385] [F-386] [F-387][F-388][F-389][F-390] [F-391] [F-392][F-393][F-394][F-395] [F-396] [F-397][F-398][F-399][F-400] [F-401] [F-402][F-403][F-404][F-405] [F-406] [F-407][F-408][F-409][F-410] [F-411] [F-412][F-413][F-414][F-415] [F-416] [F-417][F-418][F-419][F-420] [F-421] [F-422][F-423][F-424][F-425] [F-426] [F-427][F-428][F-429][F-430] [F-431] [F-432][F-433][F-434][F-435] [F-436] [F-437][F-438][F-439][F-440].

10. A display device comprising an organic optoelectronic device according to any one of claims 1 to 9.

Images