Organic electronic element having improved lateral resistance change rate and electronic device thereof

Abstract

The present invention provides an organic electronic element comprising: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode; wherein the organic material layer comprises a hole transport layer, a light-emitting layer and an electron transport layer, and a light-emitting auxiliary layer is formed between the hole transport layer and the light-emitting layer; and the driving voltage of the organic electronic element can be reduced and the luminous efficiency and the service life can be improved by controlling the lateral resistance change rate according to the hole transport layer and the light-emitting auxiliary layer.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0164627 filed in the Korean Patent Office on November 23, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to an organic electronic element having an improved lateral resistance change rate and an electronic device thereof. Background Art

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic electronic element using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer disposed therebetween. Here, the organic material layer generally consists of a multilayer structure composed of different materials to increase the efficiency and stability of the organic electronic element, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.

[0005] Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons through recombination.

[0006] However, the material used for the hole transport layer has a low HOMO value and therefore generally has a low T1 value, so the excitons generated in the light-emitting layer are transferred to the hole transport layer, resulting in charge imbalance in the light-emitting layer and light emission at the interface of the hole transport layer. In order to solve the light emission problem in these hole transport layers, organic electronic elements are being proposed that form a plurality of hole transport layers or form a light-emitting auxiliary layer between the hole transport layer and the light-emitting layer.

[0007] By using a light-emitting auxiliary layer, problems such as light emission in the hole transport layer and charge imbalance in the light-emitting layer can be solved. However, in order to achieve the goal of high brightness, hole injection and transport between the hole transport layer and the light-emitting auxiliary layer or between the light-emitting auxiliary layer and the light-emitting layer must be controlled, and in particular, the interaction between the hole transport layer and the light-emitting auxiliary layer plays an important role.

[0008] [Prior art literature]

[0009] [Patent Document]

[0010] (Patent Document 1) Korean Patent Document 10-1647160 Summary of the invention

[0011] An object of the present invention is to provide an organic electronic element and an electronic device thereof comprising a compound capable of reducing the driving voltage of the element and improving the luminous efficiency, color purity, stability and service life of the element.

[0012] [Technical solution]

[0013] In one aspect, an organic electronic element according to the present invention provides an organic electronic element, comprising: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a hole transport layer, a light-emitting layer and an electron transport layer, and a light-emitting auxiliary layer is formed between the hole transport layer and the light-emitting layer, wherein the hole transport layer and the light-emitting auxiliary layer satisfy the following formula 1.

[0014] [Formula 1]

[0015]

[0016] In another aspect, the present invention provides an electronic device including the organic electronic element.

[0017] [Effects of the invention]

[0018] The present invention can limit the parasitic current by controlling the lateral resistance change rate, thereby achieving high luminous efficiency, low driving voltage and high thermal resistance of the element, and can significantly improve the color purity and service life of the element. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 Examples of the organic electronic element according to the present invention are illustrated.

[0020] Figure 2 is a schematic diagram of an experimental setup as a device for measuring lateral resistance.

[0021] Figure 3 is a graph showing efficiency and lateral resistance change rate according to one embodiment of the present invention. DETAILED DESCRIPTION

[0022] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

[0023] In addition, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to limit the substance, order or sequence of the corresponding component, but is only used to distinguish the corresponding component from other components. It should be noted that if a component is described as being "connected", "coupled" or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected", "coupled" or "connected" between the components.

[0024] As used in the specification and appended claims, unless otherwise specified, the following terms have the following meanings.

[0025] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

[0026] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms and means a saturated aliphatic functional group, including a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted by an alkyl group, or an alkyl group substituted by a cycloalkyl group.

[0027] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond of 2 to 60 carbon atoms, but is not limited thereto, and includes a straight chain or branched chain group.

[0028] Unless otherwise specified, the term "cycloalkyl group" as used herein means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0029] Unless otherwise specified, the term "alkoxy group," "alkoxy group," or "alkyloxy group" as used herein means an oxy group attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

[0030] Unless otherwise specified, the term "aryloxy group" or "aryloxy group" as used herein means an oxy group attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0031] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic group, and includes an aromatic ring formed by bonding or reaction of adjacent substituents. For example, an "aryl group" may include a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0032] The prefix "aryl" or "ar" means a group substituted by an aryl group. For example, arylalkyl can be an alkyl substituted by an aryl group, and arylalkenyl can be an alkenyl substituted by an aryl group, and the group substituted by an aryl group has the number of carbon atoms as defined herein.

[0033] In addition, when the prefixes are named sequentially, this means listing the substituents in the order first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted with an aryl group.

[0034] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of a monocyclic ring and a polycyclic ring, and may include a heteroaliphatic ring and / or a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0035] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0036] In addition, the term "heterocyclic group" may include SO 2 A ring replacing a carbon constituting the ring. For example, the "heterocyclic group" includes the following compounds.

[0037]

[0038] Unless otherwise specified, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which R, R' and R" in the following structure are all hydrogen, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0039]

[0040] The term "spiro compound" as used herein has "spiro connection", and spiro connection means a connection in which two rings share only one atom. The atom shared between the two rings is called a "spiro atom", and these compounds are respectively called "monospiro-", "dispiro-" and "trispiro-" according to the number of atoms contained in the compound.

[0041] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0042] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0043] Other hetero compounds or hetero groups other than the above-mentioned hetero compounds contain one or more hetero atoms, but are not limited thereto.

[0044] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substitution is substituted by at least one substituent selected from deuterium, halogen, amino group, nitrile group, nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, C 1 -C 20 Alkylamine group, C 1 -C 20 Alkylthiophene group, C 6 -C 20 Arylthiophene group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 3 -C 20 Cycloalkyl groups, C 6 -C 20 Aryl groups, deuterated C 6 -C 20 Aryl group, C 8 -C 20 Arylene groups, silane groups, boron groups, germanium groups and C 2 -C 20 Heterocyclic groups, but not limited thereto.

[0045] Unless otherwise expressly specified, the formulae used in the present invention as used herein apply in the same manner as the definitions of substituents according to the definitions of the indices of the following formulae.

[0046]

[0047] When a is an integer of 0, the substituent R 1 does not exist. When a is an integer equal to 1, the only substituent R 1 When a is an integer of 2 or 3, each substituent R 1may be the same or different, and when a is an integer from 4 to 6, is connected to the carbon of the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0048]

[0049] The term "composition" as used herein is intended to be broadly interpreted to include not only compounds, but also solutions, dispersions, liquid and solid mixtures (mixtures, admixtures).

[0050] The composition of the present invention may contain the compound of the present invention alone, or may contain a combination of 2 or more different compounds, or may contain a combination of a compound and 2 or more other compounds. In other words, the composition may contain a compound corresponding to Formula 1 alone, may contain a mixture of 2 or more compounds of Formula 1, or may contain a mixture of a compound of Formula 1 and a compound not corresponding to the present invention. Among them, the compound not corresponding to the present invention may be a single compound, or may be 2 or more compounds. At this time, when the compound is contained in a combination of 2 or more other compounds, the other compounds may be known compounds of each organic material layer, or compounds to be developed in the future. At this time, the compound contained in the organic material layer may be composed only of homogeneous compounds, but may also be a mixture of 2 or more heterogeneous compounds represented by Formula 1.

[0051] Hereinafter, an organic electronic element according to an aspect of the present invention will be described.

[0052] refer to Figure 1 , an organic electronic element according to one aspect of the present invention includes a first electrode formed on a substrate (not shown), a second electrode, and an organic material layer formed between the first electrode and the second electrode.

[0053] Among them, the first electrode may be an anode (positive electrode) and the second electrode may be a cathode (negative electrode), and in the case of an inverted organic electronic element, the first electrode may be a cathode and the second electrode may be an anode.

[0054] The organic material layer may include a hole transport layer, a light emitting layer, and an electron transport layer, and a light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer.

[0055] The interaction between the hole transport layer and the light-emitting auxiliary layer can be determined by the lateral resistance change rate. When the lateral resistance change rate is large, the hole injection between the hole transport layer and the light-emitting auxiliary layer is smooth, so the amount of holes in the light-emitting layer increases, resulting in an imbalance between holes and electrons in the light-emitting layer. This leads to the generation of non-luminescent annihilation holes, reducing the luminous efficiency of the element. Therefore, when the energy levels or inherent properties (mobility, interface properties, etc.) of the materials between the hole transport layer and the light-emitting auxiliary layer are optimally combined, the performance of the organic electronic element can be improved.

[0056] At this time, the hole transport layer and the light-emitting auxiliary layer satisfy the following Formula 1.

[0057] [Formula 1]

[0058]

[0059] In formula 1,

[0060] 1) ΔRs p It is the difference in lateral resistance according to the thickness of the light-emitting auxiliary layer.

[0061] 2)Δd p is the difference in thickness of the light-emitting auxiliary layer.

[0062] More specifically, by changing the light-emitting auxiliary layer in an element having a hole transport layer made of the same compound, the lateral resistance change rate, ΔRs, is controlled. p It means the difference of lateral resistance value measured by changing the thickness of the light-emitting auxiliary layer, Δd p Indicates the difference in thickness of the light-emitting auxiliary layer.

[0063] For example, when the thickness of the light-emitting auxiliary layer is 56 nm and 20 nm, the difference in lateral resistance is ΔRs. p , and Δd p It is 36nm, which is the difference in thickness of the light-emitting auxiliary layer.

[0064] In Formula 1, the lateral resistance change rate according to the thickness of the light-emitting auxiliary layer is expressed as ΔRs p / Δd p The absolute value of the ratio.

[0065] The lateral resistance change rate of the light emitting auxiliary layer may have an absolute value of 1.1 or less. It is preferred that the absolute value has a value less than or equal to 1.0, and more preferably, the absolute value has a value less than or equal to 0.9.

[0066] The lateral resistance change rate is determined by the degree of hole injection and hole migration between the hole transport layer and the light-emitting auxiliary layer, and the closer the value is to 0, the fewer holes are injected from the hole transport layer to the light-emitting auxiliary layer.

[0067] Figure 3 is a graph showing efficiency and lateral resistance change rate. Figure 3 , it can be seen that the closer the lateral resistance change rate is to 1.1, the more the efficiency decreases, and when the lateral resistance change rate has a value of 1.1 to 1.4, the efficiency decreases rapidly. This can also be confirmed in Table 6.

[0068] The organic material layer may further include a hole injection layer between the first electrode and the hole transport layer, and an electron injection layer between the second electrode and the electron transport layer.

[0069] In addition, a buffer layer may be further formed between the hole transport layer and the light emitting auxiliary layer.

[0070] although Figure 1 Although not shown, an electron transport auxiliary layer may be further formed between the light emitting layer and the electron transport layer.

[0071] In addition, the organic electronic element according to one embodiment of the present invention may further include a protective layer or a light efficiency enhancement layer. The light efficiency enhancement layer may be formed on the surfaces of both sides of the first electrode (the surfaces not in contact with the organic material layer), or on the surfaces of both sides of the second electrode (the surfaces not in contact with the organic material layer).

[0072] According to one embodiment of the present specification, the hole transport layer or the light-emitting auxiliary layer may be represented by Formula 1 or Formula 2.

[0073]

[0074] in:

[0075] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 Each is selected from: a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; and C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring fused ring group,

[0076] L 8 Selected from: single bond; C 6 -C 60Arylene group; Fluorenylene group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; and C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring fused groups;

[0077] When L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 is an arylene group, preferably C 6 -C 30 Arylene group, more preferably C 6 -C 25 In the case of an arylene group, for example, it may be phenylene, biphenylene, naphthylene, terphenylene, anthrylene, phenanthrylene, or the like.

[0078] When L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 is a heterocyclic group, preferably C 2 -C 30 Heterocyclic group, more preferably C 2 -C 24 When the heterocyclic group is used, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0079] When L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 When it is a fused ring group, preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring condensed ring group, more preferably C 3 -C24 Aliphatic ring and C 6 -C 24 Aromatic ring fused group.

[0080] Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 Each selected from: C 6 -C 60 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 60 Heterocyclic group; and C 3 -C 60 Aliphatic ring and C 6 -C 60 Aromatic ring condensed ring group; C 3 -C 60 Aliphatic ring; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; C 6 -C 30 Aryloxy group; and -L'-N(R')(R"); or Ar 4 and Ar 5 , or Ar 6 and Ar 7 may be bonded to each other to form a ring.

[0081] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 is an aryl group, preferably C 6 -C 30 Aryl group, more preferably C 6 -C 25 When it is an aryl group, for example, it may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, and the like.

[0082] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar5 ,Ar 6 and Ar 7 is a heterocyclic group, preferably C 2 -C 30 Heterocyclic group, more preferably C 2 -C 24 When the heterocyclic group is used, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0083] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 When it is a fused ring group, preferably C 3 -C 30 Aliphatic ring and C 6 -C 30 Aromatic ring condensed ring group, more preferably C 3 -C 24 Aliphatic ring and C 6 -C 24 Aromatic ring fused group.

[0084] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 When it is an aliphatic ring group, preferably C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0085] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 When it is an alkyl group, preferably C 1 -C 30 Alkyl group, more preferably C 1 -C 24 Alkyl group.

[0086] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 When it is an alkoxy group, preferably C 1 -C 24 Alkoxy groups.

[0087] When Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 When it is an aryloxy group, preferably C 6 -C 24 Aryloxy group.

[0088] Wherein L' is selected from: a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 an aliphatic ring; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group.

[0089] When L' is an arylene group, it is preferably C 6 -C 30 Arylene group, more preferably C 6 -C 25 Arylene groups, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracene, phenanthrene and the like.

[0090] When L' is an aliphatic ring group, preferably C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0091] When L' is a heterocyclic group, preferably C 2 -C 30 Heterocyclic group, more preferably C 2 -C 24 When the heterocyclic group is used, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0092] R' and R" are each independently selected from: 6 -C 60 Aryl group; Fluorenyl group; C 3 -C 60 an aliphatic cyclic group; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group.

[0093] When R' and R" are aryl groups, preferably C 6 -C 30 Aryl group, more preferably C 6 -C 25 When it is an aryl group, for example, it may be phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, and the like.

[0094] When R' and R" are aliphatic cyclic groups, preferably C 3 -C 30 Aliphatic cyclic group, more preferably C 3 -C 24 Aliphatic cyclic group.

[0095] When R' and R" are heterocyclic groups, preferably C 2 -C 30 Heterocyclic group, more preferably C 2 -C 24 When the heterocyclic group is used, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0096] n is an integer from 1 to 3,

[0097] wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, condensed ring group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from: deuterium; halogen; C 1 -C 20 Alkyl group; or 6 -C 20 Aryl group substituted or unsubstituted silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 1 -C20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 Aryl group; C substituted by deuterium 6 -C 20 Aryl group; Fluorenyl group; C 2 -C 20 Heterocyclic group; C 3 -C 20 Cycloalkyl group; C 7 -C 20 Arylalkyl group; C 8 -C 20 arylalkenyl group; and -L'-N(R')(R"); in addition, the hydrogen of these substituents may be further replaced by one or more deuterium, and the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means C 3 -C 60 Aliphatic ring or C 6 -C 60 Aromatic ring or C 2 -C 60 A heterocyclic group or a condensed ring formed by a combination thereof.

[0098] Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 At least one of the following formulas Ar-a to Ar-d is represented by any one of:

[0099]

[0100] in:

[0101] Y A , Y B and Y C Each independently is O, S, NR 1A 、Si(R 1B )(R 1C ) or C(R 1B )(R 1C ),

[0102] R A , R B , R C , R D , R E , RF , R 1A , R 1B and R 1C are each independently the same or different and are each independently selected from: hydrogen; deuterium; halogen; cyano group; C 6 -C 20 Aryl group; C substituted by deuterium 6 -C 20 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 20 Heterocyclic group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; and -L'-N(R')(R"); or adjacent multiple R A or multiple R B or multiple R C or multiple R D or multiple R E or multiple R F may be bonded to each other to form a ring, or R 1B and R 1C may be bonded to each other to form a spiro ring,

[0103] ta and tc are each independently an integer from 0 to 3, tb and td are each independently an integer from 0 to 4, te is an integer from 0 to 5, tf is an integer from 0 to 7,

[0104] L', R' and R" are as defined above,

[0105] Indicates the location to be bonded.

[0106] Formula Ar-a can be represented by any one of the following formulas Ar-a-1 to Ar-a-4.

[0107]

[0108] Among them, R A , R B , Y A ,ta,tb and The same as defined in formula Ar-a.

[0109] Formula Ar-b can be represented by the following formula Ar-b-1 or formula Ar-b-2.

[0110]

[0111] Among them, R C , R D , Y B , Y C , tc, td, and The same as defined in formula Ar-b.

[0112] The formula Ar-d can be represented by the following formula Ar-d-1 or formula Ar-d-2.

[0113]

[0114] Among them, R F , tf and The same as defined in formula Ar-d.

[0115] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 may be represented by a single bond or any one of Formula b-1 to Formula b-13, and L 8 It can be represented by any one of Formula b-1 to Formula b-13.

[0116]

[0117] in,

[0118] Z 10 O, S, NR 1D or C(R 1E )(R 1F ),

[0119] a", c", d", e" and i" are independently integers from 0 to 4, b" is an integer from 0 to 6, f" and g" are independently integers from 0 to 3, h" is an integer from 0 to 2, j" is an integer from 0 or 1,

[0120] R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R 1D , R 1E and R 1F are independently the same or different and are independently selected from: hydrogen; deuterium; C substituted or unsubstituted by deuterium 6 -C20 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 20 Heterocyclic group; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; and C 6 -C 30 aryloxy group; alternatively, adjacent groups may be bonded to each other to form a ring,

[0121] Z 49 , Z 50 and Z 51 Each is independently CR 1G or N,

[0122] The condition is Z 49 , Z 50 and Z 51 At least one of them is N,

[0123] R 1G Each independently selected from: hydrogen; deuterium; C 6 -C 20 An aryl group; a fluorenyl group; a C containing at least one heteroatom selected from O, N, S, Si or P; 2 -C 20 Heterocyclic group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; and C 6 -C 30 Aryloxy groups;

[0124] Indicates the location of the bond.

[0125] Specifically, the compound represented by Formula 1 may be any one of the following Compound P1-1 to Compound P1-97, but is not limited thereto.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] Specifically, the compound represented by Formula 2 may be any one of the following Compound P2-1 to Compound P2-79, but is not limited thereto.

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] The luminescent auxiliary layer plays the role of transferring holes from the hole transport layer to the luminescent layer, injecting holes from the luminescent auxiliary layer to the luminescent layer, and blocking electrons from the luminescent auxiliary layer to the luminescent layer. At this time, by controlling the hole injection between the hole transport layer and the luminescent auxiliary layer, the amount of holes and electrons in the luminescent layer can be controlled to reach a balance. Among them, the balance between the amount of holes and the amount of electrons means that the holes and electrons injected into the luminescent layer recombine in the luminescent layer to effectively form excitons for luminescence. For example, when the amount of holes in the luminescent layer is greater than the amount of electrons, in addition to the holes participating in the recombination, non-luminescent annihilation holes will also be generated, resulting in a loss in the quantum efficiency of the component. Therefore, by achieving a quantitative balance of injected holes and electrons, the amount of holes and electrons that are annihilated and not involved in luminescence can be reduced, thereby affecting the component characteristics.

[0141] For example, it is important to control the lateral resistance of the organic layer including the hole transport layer and the light-emitting auxiliary layer as a means to ensure the quantitative balance of holes and electrons in the light-emitting layer. When there are too many holes in the light-emitting layer, the amount of holes injected between the hole transport layer and the light-emitting auxiliary layer can be reduced to achieve a balance between holes and electrons in the light-emitting layer. Generally, the hole mobility of the material that is disposed between the anode side end of the light-emitting unit adjacent to the cathode and the light-emitting layer and transports holes exhibits a faster characteristic than the electron mobility of the material that is disposed between the cathode and the light-emitting layer and transports electrons.

[0142] Therefore, in order to increase the luminous efficiency of the element, it is important to reduce the amount of holes injected into the light-emitting layer, and limiting the injection of holes between the hole transport layer and the light-emitting auxiliary layer is more effective than limiting the injection of holes from the light-emitting auxiliary layer to the light-emitting layer.

[0143] The lateral resistance change rate can be controlled according to the hole transport layer and the light-emitting auxiliary layer. When the hole transport layer contacts the light-emitting auxiliary layer and the lateral resistance change rate of the light-emitting auxiliary layer gradually decreases, this means that the hole injection between the hole transport layer and the light-emitting auxiliary layer has a greater effect than the hole mobility of the light-emitting auxiliary layer, because the lateral resistance changes less with the thickness change. Therefore, when the lateral resistance change rate of the light-emitting auxiliary layer is close to 0, the hole injection between the hole transport layer and the light-emitting auxiliary layer is limited, and the amount of holes injected into the light-emitting layer is reduced, so that the amount of holes and the amount of electrons in the light-emitting layer can be balanced. Therefore, a quantitative balance of injected holes and electrons can be achieved, which can increase the efficiency of the element.

[0144] In an OLED display, each pixel is composed of sub-pixels of different colors to emit the desired color. The sub-pixels are manufactured by depositing a white-light OLED stack covering the entire surface of the matrix and placing an RGB (red, green, and blue) or RGBW (red, green, blue, and white) color filter on top of the OLED stack. Alternatively, different primary color OLED layers are configured in the sub-pixels. In this case, it is necessary to construct only the light-emitting layer after depositing the common layer (layer before the light-emitting layer, hole injection layer, hole transport layer, light-emitting auxiliary layer, etc.). However, it is observed that in the above two cases, they can interact through parasitic currents passing through the common layer of the OLED stack. Undesirable interactions between adjacent pixels or sub-pixels are called "crosstalk". Crosstalk causes undesirable color shifts, especially in the case of color screens. (See Korean Patent No. 10-1647160)

[0145] In such Figure 1 In the case of OLED devices, parasitic currents are observed in adjacent pixels or sub-pixels not only in common layers but also in layers formed by overlapping layers of each color that are not deposited completely separately during processing.

[0146] In this case, it is believed that limiting the parasitic current by controlling the lateral resistance change rate will improve the stability of the OLED device.

[0147] Preferably, the light-emitting layer according to the present invention is a red-emitting layer or a green-emitting layer and preferably comprises a phosphorescent emitter.

[0148] According to another embodiment of the present invention, the organic material layer may be formed in a form in which a plurality of stacked bodies including a hole transport layer, a light emitting auxiliary layer, a light emitting layer, and an electron transport layer are formed.

[0149] Generally, organic light-emitting devices can be divided into single light-emitting structural elements (SingleOLED) and multi-layer light-emitting structural elements (tandem OLED) according to the number of light-emitting components. Tandem OLED is an OLED element composed of 2 or more light-emitting components (stack), and can easily improve efficiency and service life compared with existing single OLED.

[0150] Specifically, an organic electronic element according to an embodiment of the present invention may include a first electrode, a first stack formed on the first electrode, a second stack formed on the first stack, and a second electrode, wherein the stack may correspond to an organic material layer, and a light efficiency enhancement layer may be further formed on a surface of the first electrode and / or the second electrode that is not in contact with the organic material layer.

[0151] The first stacked body and the second stacked body are respectively organic material layers including a hole transport layer, a light emitting layer, and an electron transport layer, and the first stacked body and the second stacked body may be formed with the same or different stacked structures.

[0152] At least one of the first stack and the second stack includes a light-emitting auxiliary layer mixed with a third compound according to the present invention, adjacent to the light-emitting layer. That is, a plurality of light-emitting auxiliary layers according to the present invention are included between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer may be included in the first stack and / or the second stack.

[0153] In addition, a charge generation layer (CGL) may be formed between the first stack and the second stack. The charge generation layer (CGL) may include a first charge generation layer and a second charge generation layer. The charge generation layer (CGL) is formed between the light emitting layer of the first stack and the light emitting layer of the second stack to increase the current efficiency generated in each light emitting layer and to smoothly distribute the charges.

[0154] These organic layer stacks may be formed in 2 or more layers. For example, when 3 stacks are formed, a charge generation layer (CL) and a third stack may be additionally stacked on the second stack.

[0155] In this way, when a plurality of light-emitting layers are formed by a multi-layer stack structure, an organic light-emitting device that emits white light by a mixing effect of light emitted by each light-emitting layer can be manufactured, and an organic light-emitting device that emits light of various colors can also be manufactured.

[0156] The present invention may further include a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

[0157] In addition, the organic material layer may include 2 or more stacks, wherein the stack includes a hole transport layer, a light-emitting layer and an electron transport layer sequentially formed on the anode, wherein the organic material layer may also include a charge generation layer formed between the 2 or more stacks.

[0158] The organic material layer according to the present invention can be manufactured with a small number of layers by using various polymer materials and not by a deposition method, but by a solution process or a solvent process, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a doctor blade process, a screen printing process or a thermal transfer method, etc. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0159] The organic electronic element according to one embodiment of the present invention may be a front emission type, a rear emission type, or a double-side emission type according to the material used.

[0160] Furthermore, the organic electronic element according to an embodiment of the present invention may be selected from an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.

[0161] Another embodiment of the present invention may include an electronic device, the electronic device including a display device and a control unit for driving the display device, the display device including the organic electronic element of the present invention. At this time, the electronic device can be a current or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, PMPs, remote controllers, navigation units, game consoles, various kinds of TVs, and various kinds of computers.

[0162] Hereinafter, synthesis examples of the compounds represented by Formula 1 and Formula 2 and examples of manufacturing an organic electronic element according to the present invention will be described in detail through examples, but the present invention is not limited to the following examples.

[0163] [Synthesis Example 1] Synthesis Example of Formula 1

[0164] The compound represented by Formula 1 according to the present invention (final product 1) may be synthesized according to the reaction path of the following Reaction Scheme 1, but is not limited thereto.

[0165] <Reaction Scheme 1> (Hal 1 is I, Br or Cl. )

[0166]

[0167] The compounds belonging to Sub 1 of Reaction Scheme 1 may be, but are not limited to, the following compounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of these compounds.

[0168]

[0169]

[0170]

[0171]

[0172] [Table 1]

[0173]

[0174]

[0175] The compounds belonging to Sub 2 of Reaction Scheme 1 may be, but are not limited to, the following compounds, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of these compounds.

[0176]

[0177]

[0178]

[0179]

[0180] [Table 2]

[0181]

[0182]

[0183]

[0184] Synthesis example of final compound

[0185] 1. Synthesis Example of P1-21

[0186]

[0187] (1) Synthesis of Sub 2-28

[0188] Sub 2-104 (23.7 g, 113.3 mmol), toluene (340 mL), Sub 1-55 (25 g, 103.0 mmol), Pd 2(dba) 3 (2.83 g, 3.09 mmol), P(t-Bu) 3 (1.25 g, 6.18 mmol), NaOt-Bu (19.8 g, 206.0 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain the product (26.1 g, 61%).

[0189] (2) Synthesis of P1-21

[0190] Sub 2-28 (26.1 g, 62.8 mmol), toluene (210 mL), Sub 1-47 (25.0 g, 62.8 mmol), Pd 2 (dba) 3 (1.73 g, 1.88 mmol), P(t-Bu) 3 (0.76 g, 3.77 mmol), NaOt-Bu (12.1 g, 125.6 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (31.3 g, 68%).

[0191] 2. Synthesis Example of P1-48

[0192]

[0193] Sub 1-32 (16 g, 42.6 mmol), toluene (140 mL), Sub 2-50 (17.5 g, 42.6 mmol), Pd 2 (dba) 3 (1.17 g, 1.28 mmol), P(t-Bu) 3 (0.52 g, 2.56 mmol), NaOt-Bu (8.20 g, 85.2 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (23.5 g, 78%).

[0194] 3. Synthesis Example of P1-49

[0195]

[0196] Sub 2-50 (25 g, 66.6 mmol), toluene (220 mL), Sub 1-51 (26.4 g, 66.6 mmol), Pd 2 (dba) 3 (1.83 g, 2.00 mmol), P(t-Bu) 3 (0.81 g, 3.99 mmol), NaOt-Bu (12.8 g, 133.2 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (33.2 g, 72%).

[0197] 4. Synthesis Example of P1-50

[0198]

[0199] Sub 2-79 (20 g, 40.0 mmol), toluene (130 mL), Sub 1-8 (11.8 g, 40.0 mmol), Pd 2 (dba) 3 (1.10 g, 1.20 mmol), P(t-Bu) 3 (0.49 g, 2.40 mmol), NaOt-Bu (7.69 g, 80.1 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (24.6 g, 81%).

[0200] 5. Synthesis Example of P1-54

[0201]

[0202] Sub 2-78 (25.0 g, 47.6 mmol), toluene (160 mL), Sub 1-37 (14.4 g, 47.6 mmol), Pd 2 (dba) 3 (1.3 g, 1.43 mmol), P(t-Bu) 3 (0.58 g, 2.85 mmol), NaOt-Bu (9.14 g, 95.1 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain the product (29.2 g, 82%).

[0203] 6. Synthesis Example of P1-66

[0204]

[0205] (1) Synthesis of Sub 2-91

[0206] Sub 1-8 (20 g, 67.8 mmol), toluene (230 mL), Sub 1-31 (19.3 g, 74.6 mmol), Pd 2 (dba) 3 (1.86 g, 2.04 mmol), P(t-Bu) 3 (0.82 g, 4.07 mmol), NaOt-Bu (13.0 g, 135.7 mmol) and stirred at 70°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Dry, concentrate, and the resulting compound was recrystallized using a silica gel column to obtain the product (26.7 g, 76%).

[0207] (2) Synthesis of P1-66

[0208] Sub 2-91 (26.7 g, 51.6 mmol), toluene (170 mL), Sub 1-88 (12.7 g, 51.6 mmol), Pd 2 (dba) 3 (1.4 g, 1.55 mmol), P(t-Bu) 3 (0.63 g, 3.09 mmol), NaOt-Bu (9.91 g, 103.2 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (26.5 g, 75%).

[0209] 7. Synthesis Example of P1-76

[0210]

[0211] Sub 2-91 (25 g, 48.3 mmol), toluene (160 mL), Sub 1-33 (13.5 g, 48.3 mmol), Pd 2 (dba) 3 (1.33 g, 1.45 mmol), P(t-Bu) 3(0.59 g, 2.90 mmol), NaOt-Bu (9.28 g, 96.6 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (23.9 g, 65%).

[0212] 8. Synthesis Example of P1-77

[0213]

[0214] Sub 2-91 (25 g, 48.3 mmol), toluene (160 mL), Sub 1-34 (13.5 g, 48.3 mmol), Pd 2 (dba) 3 (1.33 g, 1.45 mmol), P(t-Bu) 3 (0.59 g, 2.90 mmol), NaOt-Bu (9.28 g, 96.6 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (25.3 g, 69%).

[0215] 9. Synthesis Example of P1-78

[0216]

[0217] Sub 2-91 (25 g, 48.3 mmol), toluene (160 mL), Sub 1-75 (13.5 g, 48.3 mmol), Pd 2 (dba) 3 (1.33 g, 1.45 mmol), P(t-Bu) 3 (0.59 g, 2.90 mmol), NaOt-Bu (9.28 g, 96.6 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (26.8 g, 73%).

[0218] 10. Synthesis Example of P1-96

[0219]

[0220] Sub 1-76 (10 g, 47.8 mmol), toluene (160 mL), Sub 2-104 (27.1 g, 100.3 mmol), Pd 2 (dba) 3 (2.19 g, 2.39 mmol), P(t-Bu) 3 (0.97 g, 4.78 mmol), NaOt-Bu (13.8 g, 143.3 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Dry, concentrate, and the resulting compound was recrystallized using a silica gel column to obtain the product (25.2 g, 75%).

[0221] Table 3 shows the FD-MS values ​​of Compound P1-1 to Compound P1-97 of the present invention prepared according to the above Synthesis Examples.

[0222] [Table 3]

[0223]

[0224]

[0225] [Synthesis Example 2] Synthesis Example of Formula 2

[0226] The compound represented by Formula 2 according to the present invention (final product 2) may be synthesized according to the reaction path of the following Reaction Scheme 2, but is not limited thereto.

[0227] <Reaction Scheme 2> (Hal 2 and Hal 3 are I, Br or Cl. )

[0228]

[0229] The compounds belonging to Sub 3 of Reaction Scheme 2 may be, but are not limited to, the following compounds, and Table 4 shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of these compounds.

[0230]

[0231]

[0232] [Table 4]

[0233]

[0234]

[0235] Synthesis example of final compound

[0236] 1. Synthesis Example of P2-31

[0237]

[0238] Sub 2-27 (25.7 g, 64.1 mmol), toluene (105 mL), Sub 3-3 (10 g, 32.1 mmol), Pd 2 (dba) 3 (1.47 g, 1.60 mmol), P(t-Bu) 3 (0.65 g, 3.21 mmol), NaOt-Bu (9.24 g, 96.2 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain the product (25.7 g, 84%).

[0239] 2. Synthesis Example of P2-37

[0240]

[0241] Sub 2-12 (16 g, 94.5 mmol), toluene (160 mL), Sub 3-9 (15 g, 47.2 mmol), Pd 2 (dba) 3 (2.16 g, 2.36 mmol), P(t-Bu) 3 (0.96 g, 4.72 mmol), NaOt-Bu (13.6 g, 141.7 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (18.1 g, 71%).

[0242] 3. Synthesis Example of P2-52

[0243]

[0244] (1) Synthesis of Inter 2-52

[0245] Sub 2-12 (15 g, 88.6 mmol), toluene (300 mL), Sub 3-14 (26.4 g, 88.6 mmol), Pd 2 (dba) 3 (2.44 g, 2.66 mmol), P(t-Bu) 3(1.08 g, 5.32 mmol), NaOt-Bu (17.0 g, 177.3 mmol) and stirred at 70°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (23.6 g, 69%).

[0246] (2) Synthesis of P2-52

[0247] Sub 2-85 (18 g, 55.3 mmol), toluene (180 mL), Inter 2-52 (21.4 g, 55.3 mmol), Pd 2 (dba) 3 (1.52 g, 1.66 mmol), P(t-Bu) 3 (0.67 g, 3.32 mmol), NaOt-Bu (10.6 g, 110.6 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound were recrystallized using a silica gel column to obtain the product (27.6 g, 74%).

[0248] 4. Synthesis of P2-68

[0249]

[0250] (1) Synthesis of Inter 2-68

[0251] Sub 2-12 (10 g, 59.1 mmol), toluene (200 mL), Sub 3-33 (25.5 g, 59.1 mmol), Pd 2 (dba) 3 (1.62 g, 1.77 mmol), P(t-Bu) 3 (0.72 g, 3.55 mmol), NaOt-Bu (11.4 g, 118.2 mmol) and stirred at 70°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound was recrystallized using a silica gel column to obtain the product (20.0 g, 65%).

[0252] (2) Synthesis of P2-68

[0253] Sub 2-105 (15 g, 36.5 mmol), toluene (120 mL), Inter 2-68 (19.0 g, 36.5 mmol), Pd 2 (dba)3 (1.0 g, 1.09 mmol), P(t-Bu) 3 (0.44 g, 2.19 mmol), NaOt-Bu (7.01 g, 72.9 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Dry, concentrate, and the resulting compound was recrystallized using a silica gel column to obtain the product (25.1 g, 77%).

[0254] 5. Synthesis of P2-77

[0255]

[0256] (1) Synthesis of Sub 2-95

[0257] Sub 2-94 (30 g, 81.1 mmol), THF (270 mL), Sub 1-91 (12.7 g, 81.1 mmol), Pd(PPh 3 ) 4 (2.81 g, 2.43 mmol), 2M K 2 CO 3 (81 mL, 162.2 mmol) and stirred at 70° C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 Drying, concentration, and the resulting compound was recrystallized using a silica gel column to obtain the product (23.5 g, 65%).

[0258] (2) Synthesis of P2-77

[0259] Sub 2-95 (23.5 g, 52.7 mmol), toluene (175 mL), Sub 2-56 (13.7 g, 52.7 mmol), Pd 2 (dba) 3 (1.45 g, 1.58 mmol), P(t-Bu) 3 (0.64 g, 3.16 mmol), NaOt-Bu (10.1 g, 105.4 mmol) and stirred at 100°C. After the reaction was completed, the organic layer was extracted with toluene and water, and the mixture was purified by MgSO 4 It was dried, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain the product (27.1 g, 77%).

[0260] Table 5 shows the FD-MS values ​​of Compound P2-1 to Compound P2-81 of the present invention prepared according to Synthesis Examples.

[0261] [Table 5]

[0262]

[0263]

[0264] Meanwhile, exemplary synthesis examples of the present invention represented by Formula 1 or Formula 2 have been described above, but these are all based on Buchwald-Hartwig cross-coupling reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd (II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh 3 The present invention relates to a reductive cyclization reaction mediated by hydroxybenzoic acid (J. Org. Chem. 2005, 70, 5014.), and it will be easily understood by those skilled in the art that the above reaction proceeds even if substituents other than those specified in the specific synthesis examples are combined.

[0265] Experimental example of measuring the rate of change of lateral resistance

[0266] 1. Measurement of lateral resistance

[0267] The term "lateral resistance" used in this specification is a numerical value indicating the resistance to leakage current in the organic layer, and the higher the lateral resistance value, the lower the lateral leakage current. The lateral resistance can be obtained by measuring the value using a MaxScience M 6100 source meter.

[0268]

[0269] (R: resistance, I: current, V: voltage)

[0270] Figure 2 is a schematic diagram of the experimental setup for measuring lateral resistance using the MaxScience M6100 source meter.

[0271] exist Figure 2 In , a is an insulator, b1 is a cathode, b2 is an anode, d is a distance between b1 and b2, and L represents the length of the electrode through which current can flow between b1 and b2 (hereinafter, active electrode length). Figure 2 Only electrode b1 and electrode b2 are disclosed, but these electrodes can be composed of an even number of electrodes from 2 to 20. The hole injection layer, the hole transport layer and the light-emitting auxiliary layer are sequentially stacked between the anode and the cathode. Among them, the hole injection layer can be composed of 10nm, the hole transport layer can be composed of 110nm, and the light-emitting auxiliary layer can be composed of 10nm to 75nm.

[0272] In such Figure 2In the configured element, d was set to 40 μm, a voltage of 100 V was applied, the current was measured, and the resistance value was calculated using the resistance-current equation.

[0273] The resistance value obtained by calculation is multiplied by the number of electrodes in the element. In the experiment, the number of electrodes was set to 20, so the value (A) was obtained by multiplying by 20 (20 pairs, 1 pair of anode and cathode) and then multiplying by the length of the active electrode (L).

[0274] Then, the experiment was conducted in the same manner as above, except that the d value was adjusted to 80 μm, 160 μm, and 320 μm, to obtain the value (A).

[0275] By adjusting the d value in this manner, the value (A) obtained is used to calculate the resistance value ohm / sq. using the LINEST formula in Excel, and the unit of the resistance value is expressed as Gohm (GΩ) for convenience.

[0276] 2. Calculation of lateral resistance change rate

[0277] In such Figure 2 In the element shown in, as shown in Formula 1, the lateral resistance change rate is calculated by calculating the ratio of the difference in lateral resistance measured according to the thickness of the light-emitting auxiliary layer on the hole transport layer to the difference in the thickness of the light-emitting auxiliary layer. The lateral resistance change rate is calculated using the formula shown in Formula 1 of this specification.

[0278] The transverse resistance change rate measured according to the above transverse resistance change rate measurement method is shown in Table 6.

[0279] [Table 6]

[0280]

[0281]

[0282] Hereinafter, the production and evaluation of an organic electronic device using the compound of the present invention will be described with examples, but the present invention is not limited to the following examples.

[0283] Organic Electronics Component Manufacturing Evaluation

[0284] [Example 1] Green organic light-emitting device

[0285] A hole injection layer having a thickness of 60 nm was formed by vacuum depositing 4,4'4" (hereinafter abbreviated as 2-TNATA) on the ITO layer (anode) formed on the glass substrate, and then a hole transport layer was formed by vacuum depositing Compound C-1 to a thickness of 80 nm on the hole injection layer.

[0286] After forming a light-emitting auxiliary layer by vacuum-depositing the compound P1-78 of the present invention on the hole transport layer to a thickness of 45 nm, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) was used as a host material, and tris(2-phenylpyridine)iridium(III) (hereinafter abbreviated as Ir(ppy)) was used. 3 ) as a dopant material, and the dopant was doped at a weight ratio of 93:7 to form a light emitting layer having a thickness of 35 nm.

[0287] Subsequently, (1,1'-biphenyl-4-yl)bis(2-methyl-8-hydroxyquinoline)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited on the light-emitting layer to a thickness of 5 nm to form a hole blocking layer. An electron transport layer was formed by vacuum depositing 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (hereinafter abbreviated as BCP) to a thickness of 30 nm on the hole blocking layer.

[0288] Hereinafter, LiF was deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited with a thickness of 150 nm on the electron injection layer to form a cathode.

[0289] [Comparative Example 1] to [Comparative Example 2], [Example 2] to [Example 18]

[0290] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 7 were used.

[0291] By applying a forward bias DC voltage to the organic electroluminescent devices manufactured according to Examples 1 to 18 of the present invention and Comparative Examples 1 and 2, electroluminescent (EL) characteristics were measured using PR-650 of Photoresearch, and a lifetime measurement device manufactured by Maxscience was used at 5000 cd / m 2 The T95 service life was measured at a standard brightness of . The measurement results are shown in Table 7.

[0292]

[0293] This measurement setup allows the performance of new materials to be evaluated compared to comparative compounds under identical conditions, without being influenced by possible daily variations in deposition rate, vacuum quality or other parameters.

[0294] Since during the evaluation one batch contained 4 identically prepared OLEDs comprising the comparative compound and the performance of a total of 12 OLEDs was evaluated in 3 batches, the values ​​of the experimental results obtained in this way show statistical significance.

[0295] [Table 7]

[0296]

[0297]

[0298] It can be seen from the results in Table 7 that when a green organic light-emitting device is manufactured using a material having an improved lateral resistance change rate as a light-emitting auxiliary layer, efficiency and lifetime can be improved compared to the comparative example.

[0299] In Comparative Examples 1 and 2, a light-emitting auxiliary layer having a lateral resistance change rate of 1.1 or more was formed. In this case, due to excessive hole injection between the hole injection layer and the light-emitting auxiliary layer, the charge imbalance of holes in the light-emitting layer was increased, and thus the device characteristics seemed to be degraded.

[0300] Compared with Comparative Examples 1 and 2, Examples 1 to 18 form a light-emitting auxiliary layer, but the lateral resistance change rate is small and is 1.1 or less than 1.1, so it can be confirmed that the efficiency and service life of the element are significantly improved.

[0301] This appears to be because the amount of holes injected into the light-emitting layer is reduced by limiting hole injection between the hole transport layer and the light-emitting auxiliary layer, thereby increasing the charge balance between holes and electrons in the light-emitting layer.

[0302] Although the exemplary embodiments of the present invention are described for the purpose of illustration, it will be appreciated by those skilled in the art that various modifications, additions and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments.

[0303] The scope of the present invention should be interpreted based on the appended claims, and should be interpreted that all technical concepts included in the scope equivalent to the claims belong to the present invention.

[0304] [Description of Reference Signs]

[0305] a: insulator b1: cathode

[0306] b2: anode d: distance between b1 and b2

[0307] L: The length of the electrode through which current can flow between b1 and b2.

Claims

1. Organic electronic components, including: a first electrode; a second electrode; and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a hole transport layer, a light emitting layer and an electron transport layer, and a light emitting auxiliary layer is formed between the hole transport layer and the light emitting layer, wherein the hole transport layer and the light emitting auxiliary layer satisfy the following formula 1: [Formula 1] in: 1) ΔRs p is the difference in lateral resistance according to the thickness of the light-emitting auxiliary layer, 2)Δd p is the difference in thickness of the light-emitting auxiliary layer. 2 . The organic electronic element according to claim 1 , wherein the lateral resistance change rate has a value smaller than 1.

0. The organic electronic element according to claim 1 , wherein the lateral resistance variation ratio has a value smaller than 0.

9.

4. The organic electronic element according to claim 1, wherein the hole transport layer or the light-emitting auxiliary layer is represented by Formula 1 or Formula 2: in: L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 Each is selected from: a single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group, L 8 Selected from: single bond; C6-C 60 Arylene group; Fluorenylene group; C2-C ... 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused groups; Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 6 and Ar 7 Each selected from: C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; and C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring condensed group; C3-C 60 Aliphatic cyclic group; C1-C 50 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; and -L'-N(R')(R"); or Ar 4 and Ar 5 , or Ar 6 and Ar 7 can be bonded to each other to form a ring, Wherein L' is selected from: single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 an aliphatic ring; and a C2-C 60 Heterocyclic groups; R' and R" are each independently selected from: C6-C 60 Aryl group; Fluorenyl group; C3-C 60 an aliphatic cyclic group; and a C2-C 60 Heterocyclic groups; n is an integer from 1 to 3, wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the condensed ring group, the aliphatic ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group and the aryloxy group may be substituted by one or more substituents selected from the group consisting of: deuterium; halogen; C1-C 20 Alkyl group; or C6-C 20 Aryl group substituted or unsubstituted silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1-C 20 Alkylthio group; C1-C 20 Alkoxy group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C6-C 20 Aryl group; C6-C substituted by deuterium 20 Aryl group; Fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl group; C7-C 20 Arylalkyl group; C8-C 20 arylalkenyl group; and -L'-N(R')(R"); in addition, the hydrogen of these substituents may be further replaced by one or more deuterium, and the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 Aliphatic ring or C6-C 60 Aromatic ring or C2-C 60 A heterocyclic group or a condensed ring formed by a combination thereof. 5 . The organic electronic element according to claim 1 , further comprising a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer. 6 . The organic electronic element according to claim 1 , wherein the organic material layer comprises 2 or more stacked bodies, and the stacked body comprises a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 7 . The organic electronic element according to claim 6 , wherein the organic material layer further comprises a charge generation layer formed between the two or more stacked bodies. 8 . The organic electronic element according to claim 1 , further comprising a buffer layer between the light-emitting auxiliary layer and the hole transport layer. 9 . An electronic device comprising a display device and a control unit for driving the display device, the display device comprising the organic electronic element according to claim 1 . 10 . The electronic device according to claim 9 , wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochrome or white lighting.

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