Compound for organic electronic element, organic electronic element using the compound, and electronic device thereof

Abstract

The present invention provides an organic electronic element and an electronic device thereof. The mixture of the compounds of the present invention is used as a phosphorescent host material, thereby achieving high luminous efficiency and low driving voltage of the organic electronic element and greatly improving the life of the device.

Description

Technical Field

[0001] The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device thereof. Background Art

[0002] Generally speaking, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electronic components that use organic light emitting phenomenon usually have a structure including an anode, a cathode, and an organic layer between the two. The organic layer here is composed of a multilayer structure composed of various substances for the purpose of improving the efficiency and stability of organic electronic components, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] According to different functions, the materials used as organic layers in organic electronic components can be divided into: light-emitting materials, charge transport materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] Polycyclic compounds containing heteroatoms have been used in various layers as materials for organic electronic devices due to the huge differences in properties caused by the material structure. In particular, they have different characteristics such as band gap (HOMO, LUMO), electrical properties, chemical properties, and physical properties depending on the number of rings, fused positions, and the type and arrangement of heteroatoms, so they are being developed for various layers of organic electronic devices.

[0005] As a typical example, Patent Documents 1 to 4 disclose that pentacyclic compounds among polycyclic compounds have different properties depending on the type and arrangement of heteroatoms, the type of substituents, the condensation position, and the like.

[0006] Patent Document 1: U.S. registered patent 5843607

[0007] Patent Document 2: Japanese Patent Publication No. 1999-162650

[0008] Patent Document 3: Korean Publication Patent 2008-0085000

[0009] Patent Document 4: U.S. Patent Publication 2010-0187977

[0010] Patent Document 5: Korean Publication Patent 2011-0018340

[0011] Patent Document 6: Korean Publication Patent 2009-0057711

[0012] Patent Documents 1 and 2 use an indolecarbazole core in which the heteroatom in the pentacyclic compound is composed only of nitrogen (N), and disclose examples of using an aryl group substituted or not substituted by the N of the indolecarbazole. However, in Patent Document 1, only pure aryl groups substituted or not substituted by substituents such as alkyl, amino, and alkoxy groups are present, which is insufficient to prove the substituent effect of the polycyclic compound, and only the use of hole transport materials is described, but not the use as a phosphorescent host material.

[0013] Although Patent Documents 3 and 4 describe compounds in which the indolecarbazole 4-core in which the heteroatom is N is substituted with pyridine, pyrimidine, triazine, etc. containing aromatic groups and N, respectively, in the same pentacyclic compounds as Patent Documents 1 and 2, they only describe examples of the use of phosphorescent green host materials, and do not describe the performance of other heterocyclic compounds substituted with the indolecarbazole core.

[0014] Although Patent Document 5 describes the heteroatoms in the pentacyclic compound as nitrogen (N), oxygen (O), sulfur (S), carbon, etc., the performance test data only describes embodiments that all use the same isomeric heteroatoms, and it is impossible to confirm the performance characteristics of the pentacyclic compound containing isomeric heteroatoms.

[0015] Therefore, the patent document does not describe a solution to the low charge mobility and low oxidation stability of the pentacyclic compound containing isostructural heteroatoms.

[0016] Pentacyclic compound molecules generally obtain strong electrical interactions as the number of adjacent π-electrodes increases when stacked, which is closely related to charge mobility. In particular, the molecular arrangement order of isomeric pentacyclic compounds in the NN form becomes an edge-to-face morphology when the molecules are stacked; while isomeric pentacyclic compounds with different heteroatoms are the opposite, the molecular stacking structure becomes an antiparallel cofacial π-stacking structure, so the molecular arrangement order becomes a face-to-face morphology. The reason for this stacking structure is that the asymmetrically distributed heteroatom N and the steric effect of the substituents replaced by the heteroatom N bring about relatively high mobility and a high level of oxidative stability. (Org.Lett.2008,10,1199)

[0017] Patent Document 6 describes cases where various polycyclic compounds having 7 or more rings are used as fluorescent host materials.

[0018] As mentioned above, the changes in properties caused by the fused position, number of rings, arrangement and type of heteroatoms of polycyclic compounds have not been fully developed.

[0019] The reason is that, especially for phosphorescent organic electronic components using phosphorescent dopant materials, the LUMO and HOMO energy levels of the main material are the main factors that seriously affect the efficiency and life of the organic electronic components. It can prevent the problems of low efficiency and shortened life caused by adjusting the charge balance in the light-emitting layer, dopant quenching and luminescence on the surface of the hole transport layer, depending on whether the electron and hole injection in the light-emitting layer can be efficiently adjusted.

[0020] Regarding host materials for fluorescent and phosphorescent luminescence, recent research is underway to improve the efficiency and life of organic electronic components using TADF (Thermal activated delayed fluorescent) and exciplex (laser complex). In particular, a lot of research is being conducted on methods to clearly determine how energy is transferred from the host material to the dopant material.

[0021] There are various clear methods for transferring energy within the light-emitting layer of TADF (Thermal activated delayed fluorescent) and exciplex (laser complex), which can be easily confirmed through the PL lifetime (TRTP) measurement method.

[0022] TRTP (Time resolved transient PL) testing is a method of observing the decay time over time after irradiating a thin film with a pulsed light source. The energy transfer mode can be determined by observing the energy transfer and the luminescence delay time. The TRTP test is a testing method that can distinguish between fluorescence and phosphorescence, as well as the energy transfer mode in mixed host materials, exciplex energy transfer mode, TADF energy transfer mode, etc.

[0023] As such, there are many factors that affect efficiency and lifespan depending on the way energy is transferred from the host material to the dopant material. Different substances also have different ways of transferring energy, and host materials for stable and efficient electronic devices have not yet been fully developed. Therefore, there is a growing demand for the development of new materials, especially the host material for the light-emitting layer. Summary of the invention

[0024] (Problem to be solved)

[0025] The present invention is developed to solve the problem of the above-mentioned phosphorescent host material, and its purpose is to improve the following compounds for organic electronic components, organic electronic components using the compounds and electronic devices thereof: by adjusting the HOMO energy level of the host material of the phosphorescent organic electronic component including the phosphorescent dopant, the charge balance is adjusted accordingly, and the efficiency and life are improved.

[0026] (Methods of solving the problem)

[0027] In order to effectively regulate the hole injection in the light-emitting layer of a phosphorescent organic electronic element, the present invention combines a specific first host material with a specific second host material as a main component and includes the main component, thereby reducing the energy barrier and maximizing the charge balance in the light-emitting layer, thereby improving the efficiency and life of the organic electronic element.

[0028] The present invention provides an organic electronic component, characterized in that, in the organic electronic component comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a first host compound represented by the following chemical formula 1 and a second host compound represented by the following chemical formula 2:

[0029]

[0030] In addition, the present invention provides an organic electronic element and an electronic device using the compound represented by the chemical formula.

[0031] (Effects of the Invention)

[0032] The mixture of the present invention is used as a phosphorescent host material to achieve high luminous efficiency and low driving voltage of organic electronic components, and also can significantly increase the life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 This is an exemplary diagram of an organic electronic light-emitting element of the present invention.

[0034] (Explanation of Reference Numerals)

[0035] 100: Organic electronic component 110: Substrate

[0036] 120: first electrode (anode) 130: hole injection layer

[0037] 140: hole transport layer 141: buffer layer

[0038] 150: light-emitting layer 151: light-emitting auxiliary layer

[0039] 160: electron transport layer 170: electron injection layer

[0040] 180: second electrode (cathode) DETAILED DESCRIPTION

[0041] The present invention is described in detail below in conjunction with the embodiments of the present invention. When describing the present invention, if it is considered that the detailed description of the related known structures and functions may confuse the main points of the present invention, the detailed description will be omitted.

[0042] In addition, the terms first, second, A, B, (a), (b), etc. may be used when introducing the components of the present invention. Such terms are only used to distinguish the component from other components, and such terms are not limited to the nature or order, sequence, etc. of the corresponding components. When a component is "connected", "combined" or "contacted" with other components, it should be understood that the component is directly connected to the other components, or although it can be connected, each component may also be "connected", "combined" or "contacted" with other components.

[0043] As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings:

[0044] Unless otherwise specified, the term "halo" or "halogen" as used herein refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0045] Unless otherwise specified, the term "alkyl" used in the present invention has a single bond with a carbon number of 1 to 60 and means a free radical of a saturated aliphatic functional group such as a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl group (alicyclic group), an alkyl-substituted cycloalkyl group, a cycloalkyl-substituted alkyl group, etc.

[0046] As used herein, unless otherwise stated, the term "haloalkyl" or "haloalkyl" means an alkyl group substituted with a halogen.

[0047] The term "heteroalkyl" used in the present invention refers to a product in which more than one carbon atom constituting an alkyl group is substituted by a heteroatom.

[0048] Unless otherwise specified, the term "alkenyl", "alkenyl" or "alkynyl" used in the present invention respectively has a double bond or a triple bond with a carbon number between 2 and 60, and contains a straight chain or a side chain, but is not limited thereto.

[0049] Unless otherwise specified, the term "cycloalkyl group" used in the present invention means an alkyl group having 3 to 60 carbon atoms forming a ring, but is not limited thereto.

[0050] The term "alkoxy" used in the present invention means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, the carbon number of the alkoxy group is between 1 and 60, but is not limited thereto.

[0051] The term "alkenyloxy" used in the present invention means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, the carbon number of the alkenyl group is between 2 and 60, but is not limited thereto.

[0052] The term "aryloxy" used in the present invention means an aryl group to which an oxygen radical is attached, and unless otherwise specified, the carbon number of the aryl group is between 6 and 60, but is not limited thereto.

[0053] Unless otherwise specified, the carbon numbers of the terms "aryl" and "arylene" used in the present invention are between 6 and 60, but are not limited thereto. The aryl or arylene in the present invention means a single ring or side chain aromatic group, and contains an aromatic ring formed after the adjacent substituents are combined or reacted. For example, the aryl group can be phenyl, non-phenyl, fluorenyl, spirobifluorenyl.

[0054] The prefix "ar" refers to a radical substituted with an aryl group. For example, aralkyl is an alkyl substituted with an aryl group, and aralkenyl is an alkenyl substituted with an aryl group. The radical substituted with an aryl group has the carbon number described in this specification.

[0055] In addition, the case of naming with consecutive prefixes means listing the substituents in the order in which they are written. For example, aralkyloxy means alkoxy substituted with aryl, alkoxycarbonyl means carbonyl substituted with alkoxy, arcarbonylalkenyl means alkenyl substituted with arylcarbonyl, and arylcarbonyl here means carbonyl substituted with aryl.

[0056] Unless otherwise specified, the term "heteroalkyl" used in this specification means an alkyl group containing at least one heteroatom. Unless otherwise specified, the term "heteroaryl" or "heteroarylene" used in the present invention means an aryl or arylene group containing at least one heteroatom and having a carbon number between 2 and 60, but is not limited thereto, and contains at least one of a monocyclic ring and a polycyclic ring, which can also be formed by combining adjacent functional groups.

[0057] Unless otherwise specified, the term "heterocyclic group" used in the present invention contains at least one heteroatom, has a carbon number between 2 and 60, and contains at least one of a monocyclic ring and a polycyclic ring, and also contains heteroaliphatic rings and heteroaromatic rings. Adjacent functional groups can also be combined to form a heterocyclic group.

[0058] Unless otherwise specified, the term "heteroatom" used in the present specification means N, O, S, P or Si.

[0059] In addition, "heterocyclic groups" may also contain SO2 in the ring instead of the carbon forming the ring. For example, "heterocyclic groups" include the following compounds.

[0060]

[0061] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "alicyclic" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0062] Unless otherwise specified, the term "ring" used in the present invention refers to an alicyclic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring composed of these rings, including saturated or unsaturated rings.

[0063] Other hetero compounds or hetero radicals other than the above hetero compounds contain at least one hetero atom, but are not limited thereto.

[0064] Unless otherwise specified, the term "carbonyl" as used in the present invention refers to the substance represented by -COR', where R' refers to hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and combinations thereof.

[0065] Unless otherwise specified, the term "ether" used in the present invention refers to a substance represented by -RO-R', where R or R' independently refers to hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and combinations thereof.

[0066] In addition, unless otherwise specified, the term "substituted or unsubstituted" as used in the present invention means a substituted or unsubstituted substituted group selected from deuterium, halogen, amino, cyano, nitro, (C1-C 20 )alkyl, (C1-C 20 ) alkoxy, (C1-C 20 ) alkylamino, (C1-C 20 ) alkylthiophene, (C 6- C 20 ) arylthiophene, (C 2- C 20 )alkenyl, (C2-C 20) Alkynyl, (C3-C 20 )cycloalkyl, (C 6- C 20 ) aryl, deuterated (C6-C 20 ) aryl, (C8-C 20 ) aryl, silane, boron, germanium and (C2-C 20 ) is substituted by one or more substituents in the group consisting of heterocyclic groups, but is not limited to the substituents mentioned above.

[0067] Furthermore, unless otherwise specified, the chemical formulae used in the present invention also apply definitions of substituents based on the indices defined in the following chemical formulae.

[0068]

[0069] When a is an integer of 0, the substituent R 1 does not exist; when a is an integer of 1, a substituent R 1 It combines with any carbon in the benzene ring; when a is an integer of 2 or 3, it combines according to the following diagram. 1 When a is an integer from 4 to 6, the carbon atoms on the benzene ring are bonded in a similar manner, while the hydrogen atoms bonded to the carbon atoms forming the benzene ring are omitted.

[0070]

[0071] In addition, unless otherwise specified, the terms "ortho", "meta" and "para" used in the present invention refer to the substitution positions of all substituents. The ortho position refers to the compound where the position of the substituent is adjacent to each other, and in the case of benzene, it refers to the 1 and 2 positions; the meta position refers to the next substitution position adjacent to the substitution position, and in the case of benzene, it refers to the 1 and 3 positions; the para position is the next substitution position after the meta position, and in the case of benzene, it refers to the 1 and 4 positions. The substitution positions are explained in more detail as follows: It can be confirmed that the ortho position and the meta position are non-linear types; the para position is linear type.

[0072] (Example of ortho)

[0073]

[0074] (Example of meta)

[0075]

[0076] (Example of para)

[0077]

[0078] Next, a compound according to one aspect of the present invention and an organic electronic device including the compound are described.

[0079] The present invention provides an organic electronic component, comprising a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, characterized in that the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a first host compound represented by the following chemical formula 1 and a second host compound represented by the following chemical formula 2:

[0080]

[0081] {In the chemical formulas 1 and 2,

[0082] 1) Ar 1 ,Ar 2 ,Ar 3 and Ar 4 Independently from C6-C 60 aryl, fluorenyl, C2-C 60 Heterocyclic group, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 30 Alkoxy, C6-C 30 The aryloxy group and -L'-N(R a )(R b ) (herein, L' is selected from a group consisting of a single bond, C6-C 60 Arylene, fluorenyl, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group and C2-C 60 The R a and R b Independently from C6-C 60 Aryl, fluorenyl, C3-C 60 Alicyclic and C6-C 60 A mixed ring group of an aromatic ring and a C2-C 60 ) and Ar 2 and Ar 3 Combine to form a ring;

[0083] 2) a is an integer from 0 to 4; b is an integer from 0 to 3; c and e are integers from 0 to 10; d is an integer from 0 to 2;

[0084] 3) R 1 , R2 , R 3 , R 4 and R 5 The same or different, each independently selected from deuterium, halogen, C6-C 60 aryl, fluorenyl, C2-C 60 Heterocyclic group, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 30 Alkoxy, C6-C 30 The aryloxy group and -L'-N(R a )(R b ) are selected from a group consisting of; in the case where a, b, c and e are 2 or more and d is 2, they are respectively the same or different as a plurality of numbers, multiple R 1 , R 2 , R 3 , R 4 or R 5 They are combined with each other to form a ring;

[0085] 4) L 1 , L 2 are independently derived from single bonds, C6-C 60 Arylene, fluorenyl, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group and C2-C 60 is selected from the group consisting of heterocyclic groups;

[0086] 5) A and B are independent of each other C6-C 20 Aryl or C2-C 20 Heterocyclic group;

[0087] However, when both A and B are substituted or unsubstituted C6 aryl (phenyl), d is 2, and R4 is bonded to form a ring, thereby forming an aromatic or heterocyclic ring;

[0088] 6) i and j are 0 or 1 and are independent of each other;

[0089] However, i+j is greater than 1, and here if i or j is 0, it means direct binding;

[0090] 7)X 1 and X 2 NR', O, S or CR'R" and are independent of each other;

[0091] R' and R" are hydrogen, C6-C 60 Aryl, fluorenyl, C3-C 60 Heterocyclic or C1-C 50 alkyl, and are independent of each other; R' and R" are combined with each other to form a spiral ring;

[0092] 8) n is an integer of 1 or 2; when n is 2, 2 Ar 2 The same or different, 2 Ar 3 respectively the same or different;

[0093] (Herein, the aryl, fluorenyl, arylene, heterocyclic, mixed cyclic, alkyl, alkenyl, alkoxy and aryloxy groups are also respectively derived from deuterium, halogen, C1-C 20 Alkyl or C6-C 20 substituted or unsubstituted silyl; siloxane, boron, germanium, cyano, nitro; -L'-N(R a )(R b )、C1-C 20 Alkylthio; C1-C 20 Alkoxy; C1-C 20 Alkyl; C2-C 20 Alkenyl; C2-C 20 Alkynyl; C6-C 20 Aryl; C6-C substituted by deuterium 20 Aryl; fluorenyl, C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl; C7-C 20 Aralkyl; and C8-C 20 The substituents are also combined with each other to form a ring, where "ring" refers to an alicyclic ring with 3 to 60 carbon atoms, an aromatic ring with 6 to 60 carbon atoms, a heterocyclic ring with 2 to 60 carbon atoms, or a condensed ring formed by a combination of these rings, including saturated or unsaturated rings).

[0094] In addition, the present invention provides a compound represented by the chemical formula 2.

[0095] In another specific aspect of the present invention, the first host compound represented by the chemical formula 1 comprises a compound represented by the following chemical formula 3 or chemical formula 4:

[0096]

[0097] {In the chemical formulae 3 and 4, R 1 , R 2 , L1 ,Ar 1 ,Ar 2 ,Ar 3 , a and b are the same as defined in claim 2 above}.

[0098] In addition, the following organic electronic element is provided: In the chemical formula 1, the L 1 , L 2 is selected from the group consisting of the following chemical formulas (A-1) to (A-12):

[0099]

[0100]

[0101] {In the chemical formulas (A-1) to (A-12),

[0102] 1) a', c', d' and e' are integers from 0 to 4; b' is an integer from 0 to 5; f' and g' are integers from 0 to 3; h' is an integer from 0 to 1;

[0103] 2) R 6 , R 7 and R 8 are identical or different, are independent of each other and are derived from deuterium, halogen, C6-C 60 aryl, fluorenyl, C2-C 60 Heterocyclic group, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 30 Alkoxy, C6-C 30 The aryloxy group and -L'-N(R a )(R b )

[0104] Alternatively, if f' and g' are 2 or more, they are identical or different as plural numbers, and the plurality of R 6 Or multiple R 7 , multiple R 8 The same type of groups can combine with each other to form aromatic or heteroaromatic rings;

[0105] Adjacent R 6 , R 7 Or the adjacent R 7 , R 8 Combined with each other, they can form aromatic or heteroaromatic rings;

[0106] 3) Y is NR', O, S or CR'R";

[0107] 4) R' and R" are the same as those defined in claim 2;

[0108] 5) Z 1 , Z 2 and Z 3 are CR' or N and are independent of each other, and at least one of them is N}.

[0109] In addition, the present invention is characterized in that the first host compound represented by the chemical formula 1 is represented by one of the following chemical formulas 5 to 8:

[0110]

[0111] {In the chemical formulae 5 to 8,

[0112] 1) R 1 , R 2 ,Ar 1 ,Ar 2 ,Ar 3 , a, b, R' and R" are the same as those defined in claim 2;

[0113] 2) R 6 and R 7 identical or different from each other, independent of each other and consisting of deuterium, halogen, C6-C 60 aryl, fluorenyl, C2-C 60 Heterocyclic group, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 30 Alkoxy, C6-C 30 The aryloxy group and -L'-N(R a )(R b ) or, if f' and g' are greater than 2, they are respectively the same or different as plural numbers, and multiple R 6 Or multiple R 7 , multiple R 8 R of the same type combined with each other or adjacent 6 With R 7 Or the adjacent R 7 With R 8 Combined with each other to form aromatic or heteroaromatic rings;

[0114] 3) a', c' and d' are integers from 0 to 4, and f' and g' are integers from 0 to 3;

[0115] 4) Y is NR', O, S or CR'R"}.

[0116] In addition, the present invention provides the following organic electronic device: the first host compound represented by the chemical formula 1 is a compound represented by one of the following chemical formulas 9 to 20:

[0117]

[0118] {In the chemical formulas 9 to 20,

[0119] R 1 , R 2 , L 1 ,Ar 1 ,Ar 2 ,Ar 3 , a and b are the same as defined in claim 2}.

[0120] In addition, the first host compound represented by Chemical Formula 1 of the present invention includes compounds represented by the following Chemical Formulas 21 to 22:

[0121]

[0122] {In the chemical formulas 21 and 22, R 1 , R 2 , L 1 ,Ar 1 ,Ar 2 ,Ar 3 , a and b are the same as defined in claim 2}.

[0123] In addition, the present invention provides an organic electronic device characterized by: a compound in which n is 1 in the chemical formula 1; and a compound in which n is 2 in the chemical formula 2.

[0124] The present invention provides the following organic electronic device: the first host compound represented by the chemical formula 1 comprises a compound represented by the following chemical formula 23

[0125]

[0126] {In the chemical formula 23,

[0127] 1) R 1 , R 2 , L 1 ,Ar 1 ,Ar 2, a, b and n are the same as those defined in claim 2;

[0128] 2) f is an integer from 0 to 3, and g is an integer from 0 to 4;

[0129] 3) R 9 and R 10 are identical or different and are independently derived from deuterium, halogen, C6-C 60 aryl, fluorenyl, C2-C 60 Heterocyclic group, C3-C 60 Alicyclic and C6-C 60 Aromatic ring mixed ring group, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 Alkynyl, C1-C 30 Alkoxy, C6-C 30 The aryloxy group and -L'-N(R a )(R b ) is selected from a group consisting of; if the f and g are greater than 2, they are respectively identical or different as plural numbers, and multiple R 9 Or multiple R 10 R of the same type combined with each other or adjacent 9 With R 10 They can combine with each other to form aromatic or heteroaromatic rings;

[0130] 4) Y is NR', O, S or CR'R";

[0131] 5) R' and R" are the same as defined in claim 2}.

[0132] The present invention provides the following organic electronic device: the second host compound represented by the chemical formula 2 comprises a compound represented by the following chemical formula 24 or chemical formula 25

[0133]

[0134] {In the chemical formulas 24 and 25, R 3 , R 4 , R 5 ,Ar 4 , L 2 ,c,d,e,A,B,X 1 and X 2 Same as defined in claim 2}.

[0135] In addition, the present invention provides the following organic electronic device: A and B in the chemical formula 2 include a compound selected from the group consisting of chemical formulas (B-1) to (B-7):

[0136]

[0137] {In the chemical formulas (B-1) to (B-7),

[0138] 1) Z 4 To Z 50 CR' or N;

[0139] 2) R' is the same as defined in claim 2;

[0140] 3)* indicates the position of condensation}.

[0141] As a specific example of the present invention, the following organic electronic component is provided: comprising R of the chemical formula 2 4 Compounds that must form aromatic or heteroaromatic rings.

[0142] As another example, the present invention provides the following organic electronic device: comprising a compound represented by the second host compound represented by the chemical formula 2 and represented by one of the following chemical formulas 26 to 45:

[0143]

[0144]

[0145]

[0146] {In the chemical formulas 26 to 45,

[0147] Ar 4 , X 1 , X 2 , R 3 , R 4 , R 5 , c, d and e are the same as defined in claim 2}.

[0148] The present invention provides the following organic electronic device: the second host compound represented by the chemical formula 2 comprises one of the compounds represented by the following chemical formulas 46 to 52:

[0149]

[0150]

[0151] {In the chemical formulas 46 to 52,

[0152] R3 , R 4 , R 5 ,Ar 4 , L 2 , c, d, e, A, B, R' and R" are the same as defined in claim 2}.

[0153] Taking a specific example of the present invention, the first host compound represented by the chemical formula 1 is one of the following compounds 1-1 to 1-68 and compounds 2-1 to 2-68:

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] In addition, the present invention provides the following organic electronic device, wherein the second host compound represented by the chemical formula 2 comprises one of the following compounds 3-1 to 3-86:

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] Please refer to the attached Figure 1 For illustration, the organic electronic element 100 of the present invention comprises: a first electrode 120 and a second electrode 180 formed on a substrate 110, and an organic layer disposed between the first electrode 120 and the second electrode 180, wherein the organic layer comprises a compound represented by Chemical Formula 1. In this case, the first electrode 120 may be an anode, and the second electrode 180 may be a cathode. In the case of a converter type, the first electrode is a cathode, and the second electrode is an anode.

[0168] The organic layer may include, on the first electrode 120, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 in sequence. In this case, no other layers may be formed except the light emitting layer 150. It may also include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc. The electron transport layer 160, etc. may also play the role of a hole blocking layer.

[0169] Although not shown in the drawings, the organic electronic element of the present invention may further include the organic layer on at least one side of the first electrode and the second electrode and a protective layer formed on the opposite side.

[0170] On the other hand, even with the same core, different band gaps, electronic properties, surface properties, etc. will be exhibited depending on which substituent is combined at which position. Therefore, the choice of the core and the combination of sub-substituents combined with it are also very important. In particular, when the energy levels and T1 values ​​between the organic layers, the inherent properties of the material (mobility, surface properties, etc.), etc. reach the optimal combination, the goals of long life and high efficiency can be achieved at the same time.

[0171] The organic light-emitting element according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, after a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, an organic layer including a hole injection layer 130, a hole transport layer 140, a light-emitting layer 150, an electron transport layer 160 and an electron injection layer 170 is formed, and then a material that can be used as a cathode is deposited.

[0172] In addition, a light-emitting auxiliary layer 151 may be formed between the hole transport layer 140 and the light-emitting layer 150 , and an electron transport auxiliary layer may be formed between the light-emitting layer 150 and the electron transport layer 160 .

[0173] Thus, the present invention provides an organic electronic element further comprising a light efficiency improvement layer formed on at least one of the first electrode side opposite to the organic layer or the second electrode side opposite to the organic layer.

[0174] In addition, the organic layer of the present invention can be formed by any method of spin coating, nozzle coating, inkjet coating, slit coating, dip coating or double roll coating. The organic layer of the present invention can be formed by various methods, but the formation method does not limit the scope of the claims of the present invention.

[0175] As another specific example, the compound of the present invention is included in the light-emitting layer in the organic layer. In addition, the present invention provides an organic electronic device that can be used as a phosphorescent host material for the light-emitting layer.

[0176] In addition, the present invention provides an organic electronic device in which the light-emitting layer of the organic layer contains the compounds represented by Chemical Formula 1 and Chemical Formula 2 mixed in a ratio of 1:9 to 9:1.

[0177] In addition, the present invention provides an organic electronic device as follows: in the light-emitting layer of the organic layer, the compounds represented by the chemical formula 1 and the chemical formula 2 are mixed in any one ratio of 1:9 to 5:5 and contained in the light-emitting layer. More preferably, the compounds represented by the chemical formula 1 and the chemical formula 2 are contained in the light-emitting layer in a mixing ratio of 2:8 or 3:7.

[0178] The organic electronic device according to an embodiment of the present invention can be a front-side light-emitting type, a rear-side light-emitting type, or a dual-side light-emitting type according to the materials used.

[0179] White organic light emitting diodes (WOLED) can easily achieve high definition and have excellent processability. At the same time, they can be manufactured using the existing LCD color filter technology. Existing patents mainly disclose white organic light emitting devices for backlight devices. Representatively, the R (Red), G (Green), and B (Blue) light emitting parts are arranged in parallel (side-by-side) on the same plane, and the R, G, and B light emitting layers are stacked up and down. There is also a color conversion material (color conversion material, CCM) method that utilizes the electroluminescence of the blue (B) organic light emitting layer and the photoluminescence (photo-luminescence) of the inorganic phosphor. The present invention can also be applied to such WOLEDs.

[0180] Meanwhile, the present invention provides an electronic device, comprising: a display device including the organic electronic element; and a control unit for driving the display device.

[0181] On the other hand, the present invention also provides an electronic device, characterized in that the organic electronic element is at least any one of an organic electronic light-emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and a monochrome or white lighting device. In this case, the electronic device can be a current or future communication terminal, including mobile terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controllers, navigation, game consoles, various televisions, various computers, and all other electronic devices.

[0182] Hereinafter, examples are given to specifically illustrate the synthesis of the compound represented by Chemical Formula 1 in the present invention and the manufacturing of the organic electronic device of the present invention, but the present invention is not limited to the following examples.

[0183] (Synthesis example 1)

[0184] The compound represented by the chemical formula 1 of the present invention (final products 1) is prepared by reacting Sub1 and Sub2 in the following reaction formula 1.

[0185] <Reaction formula 1>

[0186]

[0187] Sub1 synthesis example

[0188] In Sub1 of reaction equation 1, if L 1 If it is not a single bond, it can be synthesized through the reaction pathway of the following reaction formula 2, but is not limited thereto.

[0189] <Reaction 2>

[0190]

[0191] Sub1-3(1) synthesis example

[0192]

[0193] 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) was dissolved in 980 mL of DMF, and then pinacol diborate was added.

[0194] (Bispinacolborate) (39.1 g, 154 mmol), palladium chloride (PdCl2) (dppf) catalyst (3.43 g, 4.2 mmol), potassium acetate (KOAc) (41.3 g, 420 mmol) were added and stirred for 24 hours to synthesize a boronic acid compound. The obtained compound was then separated by silica gel column chromatography and recrystallization to obtain 35.2 g of boronic acid compound (reaction yield: 68%).

[0195] Sub1-3(2) synthesis example

[0196]

[0197] 2-Bromo-9-phenyl-9H-carbazole (76.78 g, 238.3 mmol), Bis(pinacolato)diboron (66.57 g, 262.1 mmol), palladium chloride (dppf) (5.84 g, 7.1 mmol), and potassium acetate (70.16 g, 714.9 mmol) were tested by the same test method as Sub1-3(1) to obtain 73.92 g of the product Sub1-3(2) (reaction yield: 84%).

[0198] Sub1(10) synthesis example

[0199]

[0200] 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

[0201] (9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole) (29.5 g, 80 mmol) was dissolved in 360 mL of THF, and then 3-bromo-3'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), tetrakis(triphenylphosphine)palladium (2.8 g, 2.4 mmol), sodium hydroxide (9.6 g, 240 mmol), and 180 mL of water were added and stirred and refluxed. After the reaction was completed, it was extracted with ether and water, and then the organic layer was dried and concentrated with magnesium sulfate. Then, the generated organic matter was subjected to silica gel column chromatography and recrystallization to obtain 26.56 g of the product (reaction yield: 70%).

[0202] Sub1(3) synthesis example

[0203]

[0204] 9-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), tetrakis(triphenylphosphine)palladium (2.8 g, 2.4 mmol), sodium hydroxide (9.6 g, 240 mmol), and water 180 mL were tested by the same test method as Sub1(10) to obtain 22.9 g of product Sub1(3) (reaction yield: 72%).

[0205] Sub1(5) synthesis example

[0206]

[0207] 9-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (73.92 g, 200.2 mmol) was placed in a round-bottom flask and dissolved with 880 mL of THF. Then, 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), tetrakis(triphenylphosphine)palladium (11.6 g, 10 mmol), potassium carbonate (83 g, 600.6 mmol) and 440 mL of water were added and tested by the same test method as Sub1(10) to obtain 55.8 g of the product Sub1(5) (reaction yield: 70%).

[0208] Sub1(15) synthesis example

[0209]

[0210] 9-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (73.92 g, 200.2 mmol) was placed in a round-bottom flask and dissolved with 880 mL of THF. Then, 2-bromo-7-iododibenzo[b,d]furan (112.0 g, 300.3 mmol), tetrakis(triphenylphosphine)palladium (11.6 g, 10 mmol), potassium carbonate (83 g, 600.6 mmol) and 440 mL of water were added and tested by the same test method as Sub1 (10) to obtain 72.4 g of the product Sub1 (15) (reaction yield: 74%).

[0211] Sub1(22) synthesis example

[0212]

[0213] 9-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole) was placed in a round-bottom flask and dissolved with 880 mL of THF. Then, 1,3-dibromo-5-iodobenzene (108.65 g, 300.3 mmol), tetrakis(triphenylphosphine)palladium (11.6 g, 10 mmol), potassium carbonate (83 g, 600.6 mmol) and 440 mL of water were added and tested by the same test method as Sub1(10) to obtain 69.7 g of the product Sub1(22) (reaction yield: 73%).

[0214] An example of Sub1 is as follows, but is not limited to this:

[0215]

[0216]

[0217]

[0218] (Table 1)

[0219] Compound FD-MS Compound FD-MS Sub 1(1) m / z=321.02(C18H12BrN=322.21) Sub 1(2) m / z=321.02(C18H12BrN=322.21) Sub 1(3) m / z=397.05(C24H16BrN=398.30) Sub 1(4) m / z=563.12(C37H26BrN=564.53) Sub 1(5) m / z=397.05(C24H16BrN=398.30) Sub 1(6) m / z=397.05(C24H16BrN=398.30) Sub 1(7) m / z=473.08(C30H20BrN=474.40) Sub 1(8) m / z=473.08(C30H20BrN=474.40) Sub 1(9) m / z=473.08(C30H20BrN=474.40) Sub 1(10) m / z=473.08(C30H20BrN=474.40) Sub 1(11) m / z=473.08(C30H20BrN=474.40) Sub 1(12) m / z=473.08(C30H20BrN=474.40) Sub 1(13) m / z=497.08(C32H20BrN=498.42) Sub 1(14) m / z=503.03(C30H18BrNS=504.45) Sub 1(15) m / z=487.06(C30H18BrNO=488.38) Sub 1(16) m / z=513.11(C33H24BrN=514.47) Sub 1(17) m / z=473.08(C30H20BrN=474.40) Sub 1(18) m / z=628.13(C39H25BrN4=629.56) Sub 1(19) m / z=589.14(C39H28BrN=590.56) Sub 1(20) m / z=627.13(C40H26BrN3=628.57) Sub 1(21) m / z=473.08(C30H20BrN=474.40) Sub 1(22) m / z=474.96(C24H15Br2N=477.20) Sub 1(23) m / z=550.99(C30H19Br2N=553.30) Sub 1(24) m / z=580.94(C30H17Br2N=580.34) Sub 1(25) m / z=477.94(C21H12Br2N4=480.16) Sub 1(26) m / z=630.01(C33H20Br2N4=632.36) Sub 1(27) m / z=574.99(C32H19Br2N=577.32) Sub 1(28) m / z=550.99(C30H19Br2N=553.30) Sub 1(29) m / z=524.97(C28H17Br2N=527.26) Sub 1(30) m / z=524.97(C28H17Br2N=527.26) Sub 1(31) m / z=574.99(C32H19Br2N=577.32) Sub 1(32) m / z=513.11(C33H24BrN=514.47)

[0220] Sub2 synthesis example

[0221] Sub2 of Reaction Formula 1 can be synthesized through the reaction pathway of the following Reaction Formula 3, but is not limited thereto.

[0222] (Reaction 3)

[0223]

[0224] Bromobenzene (37.1 g, 236.2 mmol) was placed in a round-bottom flask and dissolved in toluene (2200 mL), and then aniline (20 g, 214.8 mmol), tris(dibenzylideneacetone)dipalladium (9.83 g, 10.7 mmol), tri-tert-butylphosphine (4.34 g, 21.5 mmol), sodium tert-butoxide (62 g, 644.3 mmol) were added in sequence and stirred at 100° C. After the reaction was completed, the mixture was extracted with ether and water, and then the organic layer was dried and concentrated with magnesium sulfate. The generated compound was subjected to silica gel column chromatography and recrystallization to obtain 28 g of the product (reaction yield: 77%).

[0225] Sub2-13 synthesis example

[0226]

[0227] The Sub2-1 synthesis method was used to obtain 37.9 g of the product (reaction yield: 73%) using 3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1550 mL), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), tri(dibenzylideneacetone)dipalladium (6.76 g, 7.4 mmol), tri-tert-butylphosphine (3 g, 14.8 mmol), and sodium tert-butoxide (42.6 g, 443.2 mmol).

[0228] Examples of Sub2 are as follows, but are not limited to these:

[0229]

[0230]

[0231]

[0232] (Table 2)

[0233]

[0234]

[0235] Synthesis example of final product 1

[0236] 1-37 Synthesis example

[0237]

[0238] Sub2-1 (8.0 g, 47.3 mmol) was placed in a round-bottom flask and dissolved in toluene (500 mL), and then Sub1 (6) (20.7 g, 52.0 mmol), tris(dibenzylideneacetone)dipalladium (2.4 g, 2.6 mmol), tri-tert-butylphosphine (1.05 g, 5.2 mmol), sodium tert-butoxide (13.6 g, 141.8 mmol) were added and stirred at 100° C. After the reaction was completed, it was extracted with dichloromethane and water, and then dried with magnesium sulfate and the organic layer was concentrated. Then, the generated compound was subjected to silica gel column chromatography and recrystallization to obtain 16.1 g of the product (reaction yield: 70%).

[0239] 1-10 synthesis example

[0240]

[0241] Sub2-35 (19.4 g, 47.3 mmol), toluene (500 mL), Sub1 (5) (20.7 g, 52.0 mmol), tris(dibenzylideneacetone)dipalladium (2.4 g, 2.6 mmol), tri-tert-butylphosphine (1.05 g, 5.2 mmol), sodium tert-butoxide (13.6 g, 141.8 mmol) were tested by the same test method as 1-37 to obtain product 1-10 24.1 g (reaction yield: 70%).

[0242] 1-54 synthesis example

[0243]

[0244] Inter_A-1 Synthesis

[0245] Sub2-2 (11.6 g, 47.3 mmol), toluene (500 mL), Sub1 (22) (24.8 g, 52.0 mmol), tris(dibenzylideneacetone)dipalladium (2.4 g, 2.6 mmol), tri-tert-butylphosphine (1.05 g, 5.2 mmol), sodium tert-butoxide (13.6 g, 141.8 mmol) were tested by the same test method as 1-37 to obtain 22.8 g of the product Inter_A-1 (reaction yield: 75%).

[0246] 1-54 Synthesis

[0247] Sub2-13 (8 g, 29.05 mmol), the Inter_A-1 (20.5 g, 32 mmol), toluene (305 mL), tris(dibenzylideneacetone)dipalladium (1.5 g, 1.6 mmol), tri-tert-butylphosphine (0.65 g, 3.2 mmol), and sodium tert-butoxide (8.4 g, 87.2 mmol) were tested by the same test method as 1-37 to obtain product 1-54 18 g (reaction yield: 74%).

[0248] 2-5 Synthesis Example

[0249]

[0250] Sub2-46 (7.2 g, 20 mmol), Sub1 (33) (8.73 g, 22 mmol), tris(dibenzylideneacetone)dipalladium (1 g, 1.1 mmol), tri-tert-butylphosphine (0.4 g, 2.2 mmol), sodium tert-butoxide (5.74 g, 60 mmol), and toluene (210 mL) were tested in the same manner as described for 1-37 to obtain 11.5 g of product 2-5 (reaction yield: 85%).

[0251] 2-18 Synthesis example

[0252]

[0253] Sub2-12 (9.7 g, 20 mmol), Sub1 (34) (12.2 g, 22 mmol), tris(dibenzylideneacetone)dipalladium (1.0 g, 1.1 mmol), tri-tert-butylphosphine (0.4 g, 2.2 mmol), sodium tert-butoxide (5.8 g, 60 mmol), and toluene (210 mL) were tested by the same test method as that of 1-37 to obtain 15.5 g of product 2-18 (reaction yield: 81%).

[0254] 2-60 synthesis example

[0255]

[0256] Sub1 (35) (13.9 g, 24.1 mmol), Sub2-16 (6.3 g, 28.9 mmol), tris(dibenzylideneacetone)dipalladium (2.2 g, 2.4 mmol), tri-tert-butylphosphine (1 g, 4.8 mmol), sodium tert-butoxide (8.3 g, 86.7 mmol), and toluene (260 mL) were tested in the same manner as described for 1-37 to obtain 16.5 g of product 2-60 (reaction yield: 80%).

[0257] (Table 3)

[0258]

[0259]

[0260]

[0261] (Synthesis example 2)

[0262] As shown in the following reaction formula 4, the compound represented by the chemical formula 2 of the present invention (final product 2) is produced by reacting with Sub3 and Sub4.

[0263] (Reaction 4)

[0264]

[0265] Sub3 synthesis example

[0266] Sub3 of Reaction Formula 4 can be synthesized through the reaction pathway of the following Reaction Formula 5, but is not limited thereto.

[0267] (Reaction 5)

[0268]

[0269] Sub3(1) synthesis example

[0270]

[0271] Sub3-2-1 Synthesis

[0272] Sub3-1-1 (48.5 g, 155 mmol), biboronic acid pinacol ester (43.4 g, 171 mmol), potassium acetate (46 g, 466 mmol), palladium chloride (dppf) (3.8 g, 4.7 mmol) were dissolved in DMF (980 mL) and circulated at 120°C for 12 hours. After the reaction was completed, the reactant was cooled to room temperature, extracted with dichloromethane, and then washed with water. The organic layer was dried and concentrated with magnesium sulfate, and then the generated organic matter was recrystallized with dichloromethane and methanol solvents to obtain the desired Sub3-2-1 (41.9 g, 75%).

[0273] Sub3-4-1 Synthesis

[0274] Sub3-2-1 (40 g, 111 mmol), bromo-2-nitrobenzene (26.91 g, 133 mmol), potassium carbonate (46.03 g, 333 mmol), and tetrakis(triphenylphosphine)palladium (7.7 g, 6.66 mmol) obtained by the above process were placed in a round-bottom flask, and then THF (490 mL) and water (245 mL) were added to dissolve, and then circulated at 80°C for 12 hours. After the reaction was completed, the reactant was cooled to room temperature, extracted with dichloromethane, and then washed with water. The organic layer was dried with magnesium sulfate and concentrated, and then separated by silica gel column chromatography to obtain the desired Sub3-4-1 (30.8 g, 78%).

[0275] Sub3(1) Synthesis

[0276] Sub3-4-1 (20 g, 56.3 mmol) and triphenylphosphine (37 g, 141 mmol) obtained in the above process were dissolved in o-dichlorobenzene (235 mL) and circulated for 24 hours. After the reaction was completed, the solvent was removed by vacuum distillation, and the product was concentrated by silica gel column chromatography and recrystallization to obtain the desired Sub3 (1) (14.4 g, 79%).

[0277] Sub3(2) synthesis example

[0278]

[0279] Sub3-2-2 Synthesis

[0280] Sub3-1-2 (48.5 g, 155 mmol) was subjected to the synthesis method of Sub3-2-1 to obtain the desired Sub3-2-2 (44.7 g, 80%).

[0281] Sub3-4-2 Synthesis

[0282] Sub3-2-2 (40.0 g, 111 mmol) was subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-2 (31.2 g, 79%).

[0283] Sub3(2) Synthesis

[0284] Sub3-4-2 (20 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub3(2) (14.9 g, 82%).

[0285] Sub3(7) synthesis example

[0286]

[0287] Sub3-2-3 Synthesis

[0288] Sub3-1-3 (57.7 g, 155 mmol) was subjected to the synthesis method of Sub3-2-1 to obtain the desired Sub3-2-3 (49.9 g, 76%).

[0289] Sub3-4-3 Synthesis

[0290] Sub3-2-3 (46.5 g, 111 mmol) was subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-3 (35.9 g, 79%).

[0291] Sub3(7) synthesis method

[0292] Sub3-4-3 (23.3 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub3(7) (17.2 g, 82%).

[0293] Sub3(13) synthesis example

[0294]

[0295]

[0296] Sub3-2-4 Synthesis

[0297] Sub3-1-4 (53.8 g, 155 mmol) was subjected to the synthetic method of Sub3-2-1 to obtain the desired Sub3-2-4 (45.2 g, 74%).

[0298] Sub3-4-4 Synthesis

[0299] Sub3-2-4 (43.8 g, 111 mmol) was subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-4 (33.7 g, 78%).

[0300] Sub3(13) Synthesis

[0301] Sub3-4-4 (21.9 g, 56.3 mmol) was subjected to the synthetic method of Sub (1) to obtain the desired Sub3(13) (16.1 g, 80%).

[0302] Sub3(26) synthesis example

[0303]

[0304] Sub3-2-5 Synthesis

[0305] Sub3-1-5 (50.1 g, 155 mmol) was subjected to the synthesis method of Sub3-2-1 to obtain the desired Sub3-2-5 (43.6 g, 76%).

[0306] Sub3-4-5 Synthesis

[0307] Sub3-2-5 (41.1 g, 111 mmol) and Sub3-3-1 (33.5 g, 133 mmol) were subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-5 (36.9 g, 80%).

[0308] Sub3(26) synthesis method

[0309] Sub3-4-5 (23.4 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub3(26) (17.5 g, 80%).

[0310] Sub3(39) synthesis example

[0311]

[0312] Sub3-2-6 Synthesis

[0313] Sub3-1-6 (57.7 g, 155 mmol) was subjected to the synthesis method of Sub3-2-1 to obtain the desired Sub3-2-6 (50.7 g, 78%).

[0314] Sub3-4-6 Synthesis

[0315] Sub3-2-6 (46.5 g, 111 mmol) and Sub3-3-2 (33.5 g, 133 mmol) were subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-6 (47.8 g, 81%).

[0316] Sub3(39) Synthesis

[0317] Sub3-4-6 (26.2 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub3(39) (19.2 g, 79%).

[0318] Sub3(45) synthesis example

[0319]

[0320] Sub3-2-7 Synthesis

[0321] Sub3-1-7 (46.1 g, 155 mmol) was subjected to the synthetic method of Sub3-2-1 to obtain the desired Sub3-2-7 (43.8 g, 82%).

[0322] Sub3-4-7 Synthesis

[0323] Sub3-2-7 (38.2 g, 111 mmol) and Sub3-3-1 (33.5 g, 133 mmol) were subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-7 (35.9 g, 83%).

[0324] Sub3(45) synthesis method

[0325] Sub3-4-7 (21.9 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub(45) (16.1 g, 80%).

[0326] Sub3(66) synthesis example

[0327]

[0328] Sub3-2-8 Synthesis

[0329] Sub3-1-8 (42.3 g, 155 mmol) was subjected to the synthesis method of Sub3-2-1 to obtain the desired Sub3-2-8 (40.2 g, 81%).

[0330] Sub3-4-8 Synthesis

[0331] Sub3-2-8 (35.5 g, 112 mmol) and Sub3-3-3 (40.2 g, 133 mmol) were subjected to the synthetic method of Sub3-4-1 to obtain the desired Sub3-4-8 (37.8 g, 82%).

[0332] Sub3(66) synthesis method

[0333] Sub3-4-8 (23.4 g, 56.3 mmol) was subjected to the synthetic method of Sub3(1) to obtain the desired Sub3(66) (17.5 g, 80%).

[0334] Examples of Sub3 are as follows, but are not limited to these:

[0335]

[0336]

[0337]

[0338] (Table 4)

[0339]

[0340]

[0341] Sub4 Example

[0342] Examples of Sub4 are as follows, but are not limited to these:

[0343]

[0344]

[0345]

[0346] (Table 5)

[0347]

[0348]

[0349] Synthesis example of final product 2

[0350] 3-6 Synthesis Example

[0351]

[0352] Sub3(1) (15.3 g, 47.3 mmol) was placed in a round-bottom flask and dissolved in toluene (500 mL), and then Sub4-15 (14.8 g, 52.0 mmol), tris(dibenzylideneacetone)dipalladium (2.4 g, 2.6 mmol), tri-tert-butylphosphine (1.1 g, 5.2 mmol), sodium tert-butoxide (15 g, 156.1 mmol) were added and stirred at 100°C. After the reaction was completed, extraction was performed with dichloromethane and water, and then the organic layer was dried and concentrated with magnesium sulfate. Then, the generated compound was subjected to silica gel column chromatography and recrystallization to obtain 18.5 g of the product (reaction yield: 74%).

[0353] 3-1 Synthesis example

[0354]

[0355] Sub3(7) (18.1 g, 47.3 mmol), toluene (500 mL), Sub4-1 (8.2 g, 52.0 mmol), tris(dibenzylideneacetone)dipalladium (2.0 g, 2.2 mmol), tri-tert-butylphosphine (0.9 g, 4.4 mmol), and sodium tert-butoxide (12.7 g, 132 mmol) were synthesized using the 3-6 synthesis method to obtain 16.9 g of the final product (reaction yield: 78%).

[0356] 3-7 Synthesis Example

[0357]

[0358] Sub3(1) (15.3 g, 47.3 mmol) and Sub4-25 (15.4 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 20.4 g of the final product (reaction yield: 74%).

[0359] 3-8 Synthesis Example

[0360]

[0361] Sub3(1) (15.3 g, 47.3 mmol) and Sub4-53 (15.1 g, 52 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 19.7 g of the final product (reaction yield: 72%).

[0362] 3-11 Synthesis example

[0363]

[0364] Sub3(13) (16.9 g, 47.3 mmol) and Sub4-55 (16.1 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 19.7 g of the final product (reaction yield: 71%).

[0365] 3-16 Synthesis example

[0366]

[0367] Sub3(17) (18.1 g, 47.2 mmol) and Sub4-56 (16.7 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 19.5 g of the final product (reaction yield: 66%).

[0368] 3-17 Synthesis example

[0369]

[0370] Sub3(59) (20.5 g, 47.4 mmol) and Sub4-57 (13.7 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 20.4 g of the final product (reaction yield: 70%).

[0371] 3-47 Synthesis example

[0372]

[0373] Sub3(45) (16.9 g, 47.3 mmol) and Sub4-58 (14.6 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 19.6 g of the final product (reaction yield: 69%).

[0374] 3-52 Synthesis example

[0375]

[0376] Sub3(50) (15.8 g, 47.4 mmol) and Sub4-12 (20.2 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 21.2 g of the final product (reaction yield: 70%).

[0377] 3-70 synthesis example

[0378]

[0379] Sub3(60) (17.7 g, 47.4 mmol) and Sub4-59 (17.8 g, 52.0 mmol) were subjected to the above-mentioned 3-6 synthesis method to obtain 23.4 g of the final product (reaction yield: 73%).

[0380] (Table 6)

[0381]

[0382]

[0383]

[0384] On the other hand, exemplary synthesis examples of the present invention represented by the chemical formulas 1 and 2 are described, but these are based on Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction,

[0385] Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Grignard reaction, cyclic dehydration reaction and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), in addition to the substituents explicitly stated in the specific synthesis examples, other substituents (R) defined by chemical formulas 1 and 2 are combined. 1 To R 5 ,Ar 1 To Ar 4 , L 1 To L 2 , X 1 To X 2 ) can also react, and can be easily understood by those skilled in the art.

[0386] For example, the reaction of Sub1+Sub2->Final Products1 in reaction formula 1, the reaction of synthesizing Sub2 in reaction formula 3, and the reaction of Sub3+Sub4->Final Products2 in reaction formula 4 are all based on Buchwald-Hartwig cross coupling reaction, the reaction of Sub1-3+Sub1-4->Sub1 in reaction formula 2 and the reaction of Sub3-2+Sub3-3->Sub3-4 in reaction formula 5 are all based on Suzuki cross-coupling reaction, and the reaction of Sub3-4->Sub3 in reaction formula 5 is based on PPh3-mediated reductive cyclization reaction (J.Org.Chem.2005,70,5014.). Specifically, the above reaction can be carried out even if unspecified substituents are combined.

[0387] Fabrication and evaluation of organic electrochemical devices

[0388] Example 1) Fabrication and testing of red organic light-emitting devices

[0389] First, a film of N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter referred to as "2-TNATA") was vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate. Then, a hole transport layer was formed by vacuum-depositing N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter referred to as "NPB") to a thickness of 60 nm. A mixture of the inventive compounds represented by Chemical Formula 1 and Chemical Formula 2 in a ratio of 50:50 is used as the main body on the upper part of the hole transport layer, and (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] is added in a weight ratio of 95:5, thereby vapor-depositing a 30nm thick light-emitting layer on the hole transport layer. (1,1'-biphenyl)-4-oleate)bis(2-methyl-8-hydroxyquinoline)aluminum (hereinafter referred to as "BAlq") is vacuum-deposited with a thickness of 10nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter referred to as "Alq3") is vacuum-deposited with a thickness of 40nm to form an electron transport layer. Then, LiF as an alkali metal halide is vapor-deposited with a thickness of 0.2nm on the electron injection layer, and then Al is vapor-deposited with a thickness of 150nm to form a cathode, thereby manufacturing an organic electronic light-emitting element.

[0390] A forward bias DC voltage was applied to the organic light-emitting devices in the embodiments and comparative examples manufactured as described above, and the electronic light-emitting (EL) characteristics were measured using a PR-650 produced by Photoresearch. 2 The life of T95 was measured using a life measurement device manufactured by mcscience at a standard brightness of . The following table shows the device manufacturing and evaluation results.

[0391] (Comparative Examples 1 to 3)

[0392] An organic light emitting device was manufactured by the same method as in Example 1 except that the compound represented by Chemical Formula 2 was used alone as a host.

[0393] (Comparative Example 4)

[0394] An organic electroluminescent element was manufactured by the same method as in Example 1 except that Comparative Compound 1 was used alone as a host.

[0395] (Comparative Example 5)

[0396] An organic electroluminescent element was manufactured by the same method as in Example 1 except that Comparative Compound 2 was used alone as a host.

[0397] (Comparative Example 6)

[0398] An organic electroluminescent element was manufactured by the same method as in Example 1 except that Comparative Compound 3 was used alone as a host.

[0399] (Comparative Example 7)

[0400] An organic electroluminescent element was manufactured by the same method as in Example 1 except that Comparative Compound 4 was used alone as a host.

[0401] (Comparative Example 8)

[0402] An organic light emitting device was manufactured by the same method as in Example 1 except that the comparative compound 1 and the comparative compound 2 were mixed and used as the host.

[0403] (Comparative Example 9)

[0404] An organic light emitting device was manufactured by the same method as in Example 1 except that the comparative compound 3 and the comparative compound 4 were mixed and used as the host.

[0405] (Comparative Example 10)

[0406] An organic electroluminescent element was manufactured by the same method as in Example 1 except that the compound represented by Chemical Formula 1 and Comparative Compound 4 were mixed and used as a host.

[0407]

[0408] (Table 7)

[0409]

[0410]

[0411]

[0412]

[0413]

[0414] As shown in the results of Table 7, when the materials for organic electronic light-emitting elements of the present invention represented by Chemical Formula 1 and Chemical Formula 2 are mixed and used as the phosphorescent host (Examples 1 to 100), the driving voltage, efficiency and life are significantly improved compared to devices using a single substance (Comparative Examples 1 to 7).

[0415] In more detail, Comparative Examples 1 to 7 use the compounds of the present invention represented by Chemical Formula 2 and Comparative Compounds 1 to 4 as phosphorescent hosts alone, wherein Comparative Examples 1 to 3 using the comparative compounds of the present invention (3-6, 3-61, 3-74) exhibit higher efficiency and longer life than Comparative Examples 4 to 7 using the comparative compounds.

[0416] Furthermore, it was confirmed that Comparative Examples 8 and 9 in which Comparative Compound 1 and Comparative Compound 2 or Comparative Compound 3 and Comparative Compound 4 were mixed and used as phosphorescent hosts exhibited higher efficiency than Comparative Examples 1 to 7 in which the single substances were used.

[0417] By comparing Comparative Example 8 with Comparative Example 9, it can be confirmed that Comparative Example 9 using a mixture of isomeric polycyclic compounds having mutually different heteroatoms (N, S) in the 5-ring heterocyclic compounds exhibits higher efficiency than Comparative Example 8 in which a 5-ring heterocyclic compound having isomeric nitrogen atoms is mixed.

[0418] By comparing Comparative Example 10 with Comparative Example 9, it can be confirmed that when Comparative Compound 3 is used together and the dicarbazole material (Comparative Example 9) and the compound 2-5 equivalent to the chemical formula 1 of the present invention are used as the main materials respectively, Comparative Example 10 using the compound 2-5 of the present invention shows higher efficiency and relatively long life, wherein Comparative Example 10 uses a mixture of the compound 2-5 equivalent to the chemical formula 1 in the compound of the present invention and the comparative compound 3, and Comparative Example 9 includes the use of a mixture of the comparative compound 3 and the comparative compound 4.

[0419] In addition, it can be confirmed that compared with the cases of Comparative Examples 1 to 10, Examples 1 to 100 using the mixture of Chemical Formula 1 and Chemical Formula 2 (the compound of the present invention) as the main material significantly exhibit high efficiency, long life and low driving voltage.

[0420] Based on the above experimental results, the inventors believe that when the substance of Chemical Formula 1 and the substance of Chemical Formula 2 are mixed, in addition to the characteristics of each substance, other new characteristics are also obtained. Therefore, the photoluminescence lifetime (PL lifetime) is tested using the substance of Chemical Formula 1, the substance of Chemical Formula 2, and the mixture of the present invention respectively.

[0421] As a result, it can be confirmed that in the case of mixing chemical formula 1 and chemical formula 2, unlike the single compound, a new PL wavelength can be confirmed to be formed, and it can be confirmed that the newly formed PL wavelength attenuation and decay time are about 60 times to 360 times greater than the attenuation and decay time of each of the chemical formula 1 and chemical formula 2 substances. Accordingly, in the case of mixing the compounds of the present invention, not only are electrons and holes moved through the energy levels possessed by each substance, but also the new region (exciplex) of the new energy level formed by mixing is used to improve the efficiency and life of electron and hole movement or energy transfer. As a result, the use of the mixture of the present invention is an important example of the laser composite energy transfer and light emission process embodied in the mixed film.

[0422] In addition, compared to Comparative Examples 8 to 10 using a phosphorescent host of a mixed comparative compound, the reason why the combination of the present invention is better is as follows: in the case of a compound represented by Chemical Formula 1 having a strong hole property, the polycyclic compound represented by Chemical Formula 2, which is not only an electron but also has characteristics such as stability to holes and high T1, is mixed with the compound represented by Chemical Formula 1 having a strong hole property, because the high T1 and high LUMO energy value improve the electron blocking ability, and more holes move quickly and easily to the light-emitting layer. Accordingly, the charge balance in the light-emitting layer of holes and electrons is increased, thereby achieving good light emission inside the light-emitting layer instead of the hole transport layer, and thus also reducing degradation at the HTL interface, thereby maximizing the optimization of the driving voltage, efficiency and life of the device as a whole. That is, the combination of Chemical Formula 1 and Chemical Formula 2 plays a synergistic role in electrochemical properties, thereby improving the overall performance of the device.

[0423] Example 2) Preparation and testing of red organic electronic components according to the mixing ratio

[0424] (Table 8)

[0425]

[0426] As shown in Table 8, for the compounds of the present invention, devices were manufactured and tested according to the ratios (2:8, 3:7, 4:6, 5:5).

[0427] As shown in the above results, in the structure of the mixture of compound 1-54 and compound 3-6, in the case of 2:8 and 3:7, the results of driving voltage, efficiency and life are excellent, and the results of the two are similar, while in the case of 4:6 and 5:5, it is confirmed that the driving voltage, efficiency and life results gradually decrease while the proportion of the first host increases. Based on this, the same phenomenon is also reflected in the results of the mixture of compound 2-5 and compound 3-61. This is because, as in the case of 2:8 and 3:7, if the compound represented by chemical formula 1 with excellent hole properties is mixed in an appropriate amount, the charge balance in the light-emitting layer can be maximized.

[0428] The above description is only an example of the present invention, and any person with ordinary knowledge in the technical field to which the present invention belongs can make various modifications within the scope that does not exceed the essential characteristics of the present invention. Therefore, the embodiments listed in this specification are only used to illustrate the present invention, and do not limit the idea and scope of the present invention. The scope of protection of the present invention should be in accordance with the scope of the above claims, and all technologies within the equivalent scope should be interpreted as included in the scope of the present invention.

Claims

1. An organic electronic component, characterized in that: include: A first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode; wherein the organic layer includes a phosphorescent light-emitting layer, and the light-emitting layer includes a first host compound represented by the following chemical formula 1 and a second host compound represented by the following chemical formula 2: In the chemical formulas 1 and 2, 1) Ar 1 It is C6-C 60 Aryl; 2 ,Ar 3 and Ar 4 Independently from C6-C 60 and C2-C 60 is selected from the group consisting of heterocyclic groups; 2) a is 0; b is 0; c and e are integers from 0 to 10; d is an integer from 0 to 2; 3) R 3 , R 4 and R 5 Does not exist, or there are multiple R 3 , R 4 or R 5 They combine like species to form benzene rings; 4) L 1 From the single bond and C6-C 60 is selected from the group consisting of arylene groups; L 2 From a single bond, C6-C 60 Arylene and C2-C 60 is selected from the group consisting of heterocyclic groups; 5) A and B are selected from the group consisting of chemical formulas (B-1) to (B-7): In the chemical formulas (B-1) to (B-7), Z 4 To Z 50 is CR' or N, R' is hydrogen, C6-C 60 Aryl or C1-C 50 The alkyl group of ; * indicates the position of condensation; However, when both A and B are phenyl, d is 2, and R 4 Like species combine to form a ring, thus forming a benzene ring; 6) i and j are 0 or 1 and are independent of each other; However, i+j is greater than 1, and here if i or j is 0, it means direct binding; 7)X 1 and X 2 NR', O, S or CR'R" and are independent of each other; R' and R" are hydrogen, C6-C 60 Aryl or C1-C 50 alkyl, and are independent of each other; R' and R" are combined with each other to form a spiral ring; 8) n is an integer of 1 or 2; when n is 2, 2 Ar 2 The same or different, 2 Ar 3 are the same or different; wherein the aryl, fluorenyl, arylene, heterocyclic, alkyl, and alkenyl are each replaced by deuterium, halogen, cyano, and nitro; C1-C 20 Alkyl; C2-C 20 Alkenyl; C2-C 20 Alkynyl; C6-C 20 Aryl; and C6-C 20 substituted with one or more substituents selected from the group consisting of aryl groups; The compounds represented by the chemical formula 1 and the chemical formula 2 are mixed in any weight ratio of 2:8 to 5:5 for use in the light emitting layer.

2. The organic electronic device according to claim 1, characterized in that The first host compound represented by the Chemical Formula 1 is represented by the following Chemical Formula 3 or the following Chemical Formula 4: In the chemical formulae 3 and 4, R 1 , R 2 , L 1 ,Ar 1 ,Ar 2 ,Ar 3 , a and b are the same as defined in claim 1 above.

3. The organic electronic device according to claim 1, characterized in that: The L 1 Selected from the group consisting of the following chemical formulae (A-1) to (A-9) and (A-11), wherein L 2 Selected from the group consisting of the following chemical formulas (A-1) to (A-12): In the chemical formulas (A-1) to (A-12), 1) a', c', d' and e' are integers from 0 to 4; b' is an integer from 0 to 5; f' and g' are integers from 0 to 3; h' is an integer from 0 to 1; 2) R 6 , R 7 and R 8 are identical or different, are independent of each other and are derived from deuterium, halogen, C6-C 60 Aryl, C1-C 50 Alkyl, C2-C 20 Alkenyl, C2-C 20 is selected from the group consisting of alkynyl groups; 3) Y is NR', O, S or CR'R"; 4) R' and R" are the same as those defined in claim 1; 5) Z 1 , Z 2 and Z 3 are CR' or N and are independent of each other, and at least one of them is N.

4. The organic electronic device according to claim 1, characterized in that The first host compound represented by the chemical formula 1 is represented by one of the following chemical formulas 5 to 7: (Chemical formula 7) In the chemical formulae 5 to 7, 1) R 1 , R 2 ,Ar 1 ,Ar 2 ,Ar 3 , a, b, R' and R" are the same as those defined in claim 1; 2) R 6 and R 7 identical or different from each other, independent of each other and consisting of deuterium, halogen, C6-C 20 Aryl, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 is selected from the group consisting of alkynyl groups; 3) a', c' and d' are integers from 0 to 4.

5. The organic electronic device according to claim 1, characterized in that: The first host compound represented by the chemical formula 1 is represented by one of the following chemical formulas 21 to 22: In the chemical formulas 21 and 22, R 1 , R 2 , L 1 ,Ar 1 ,Ar 2 ,Ar 3 , a and b are the same as those defined in claim 1.

6. The organic electronic device according to claim 1, characterized in that: The compound in the case where n is 1 in the chemical formula 1.

7. The organic electronic device according to claim 1, characterized in that: The compound in the case where n is 2 in the chemical formula 1.

8. The organic electronic device according to claim 1, characterized in that: The first host compound shown in the chemical formula 1 is represented by the following chemical formula 23: (Chemical formula 23) In the chemical formula 23, 1) R 1 , R 2 , L 1 ,Ar 1 ,Ar 2 , a, b and n are the same as those defined in claim 1; 2) f is an integer from 0 to 3, and g is an integer from 0 to 4; 3) R 9 and R 10 are identical or different and are independently derived from deuterium, halogen, C6-C 20 Aryl, C1-C 20 Alkyl, C2-C 20 Alkenyl, C2-C 20 is selected from the group consisting of alkynyl groups; 4) Y is NR', O, S or CR'R"; 5) R' and R" are the same as defined in claim 1.

9. The organic electronic device according to claim 1, characterized in that: The second host compound shown in the chemical formula 2 is represented by the following chemical formula 24 or chemical formula 25: In the chemical formulas 24 and 25, R 3 , R 4 , R 5 ,Ar 4 , L 2 ,c,d,e,A,B,X 1 and X 2 Same as defined in claim 1.

10. The organic electronic device according to claim 1, characterized in that: R of the chemical formula 2 4 A benzene ring must be formed.

11. The organic electronic device according to claim 1, characterized in that: The second host compound represented by the chemical formula 2 is represented by one of the following chemical formulas 26 to 45: In the chemical formulae 26 to 45, Ar 4 , X 1 , X 2 , R 3 , R 4 , R 5 , c, d and e are the same as those defined in claim 1.

12. The organic electronic device according to claim 1, characterized in that: The second host compound represented by the chemical formula 2 is represented by one of the following chemical formulas 46 to 53: In the chemical formulas 46 to 52, R 3 , R 4 , R 5 ,Ar 4 , L 2 , c, d, e, A, B, R' and R" are the same as defined in claim 1.

13. The organic electronic device according to claim 1, characterized in that: The compounds represented by the chemical formula 1 and the chemical formula 2 are used in the light emitting layer at a weight mixing ratio of 3:

7.

14. An electronic device, characterized in that: include: A display device comprising the organic electronic element according to any one of claims 1 to 13; and a control unit for driving the display device.

15. The electronic device according to claim 14, characterized in that: The organic electronic element is at least any one of an organic electronic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting device.

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