Compound for organic electric element, organic electric element using same, and electronic device therefor

Abstract

The present invention provides a novel compound capable of improving luminous efficiency, stability, and lifespan of a device, an organic electrical element using the same, and an electronic device thereof.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application is a divisional application of Chinese Patent Application No. 201980008721.8, and claims priority and benefits of Korean Patent Application No. KR1020180013219, all of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to a compound for an organic electric element, an organic electric element using the compound, 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 electrical element using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer inserted therebetween. Here, in order to improve the efficiency and stability of the organic electronic element, the organic material layer is generally composed of a multilayer structure composed of different materials and may include, for example, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and the like.

[0005] Materials used as an organic material layer in an organic electrical element can be divided into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like.

[0006] Moreover, the luminescent material can be divided into a polymer type and a low molecular type according to the molecular weight, and can be divided into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the luminescent mechanism. In addition, the luminescent material can be divided into a blue luminescent material, a green luminescent material, and a red luminescent material according to the luminescent color, as well as a yellow luminescent material and an orange luminescent material necessary to achieve a better natural color.

[0007] At the same time, when only one material is used as a light-emitting material, there will be problems such as the maximum light-emitting wavelength shifting to a long wavelength due to intermolecular interactions, the color purity decreasing, or the efficiency of the device decreasing due to the light-emitting attenuation effect. Therefore, a host / dopant system can be used as a light-emitting material to improve the light-emitting efficiency by improving the color purity and energy transfer. When a small amount of a dopant having a smaller energy band gap than the host forming the emission layer is mixed on the emission layer, the excitons generated in the emission layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light of the desired wavelength can be obtained according to the type of dopant used.

[0008] Currently, the size of large-screen displays in the portable display market continues to increase, which requires more power than what is required by existing portable displays. Therefore, for portable displays with limited power sources such as batteries, power consumption is a very important factor, and efficiency and life issues must be addressed.

[0009] Efficiency, life, driving voltage, etc. are interrelated. As efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials caused by Joule heating generated during driving decreases, and therefore the life tends to increase. However, simply improving the organic material layer cannot maximize efficiency. This is because only when the optimal combination of energy levels and T1 values ​​between each organic material layer and the inherent properties of the material (mobility, interface characteristics, etc.) is achieved, can long life and high efficiency be achieved at the same time. Therefore, it is necessary to develop a luminescent material with high thermal stability and effectively achieve charge balance in the emission layer.

[0010] That is, in order to fully demonstrate the excellent characteristics of organic electrical elements, the materials used to form the organic material layer in the element (such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, emission auxiliary layer materials, etc.) should be stable and effective materials. However, such stable and effective organic material layer materials for organic electrical elements have not been fully developed. Therefore, there is a continuous need to develop new materials, and it is particularly urgent to develop host materials for the emission layer.

[0011] In addition, in the case of a polycyclic compound containing heteroatoms, the properties generated according to the material structure vary greatly, so that it is applied to various layers as an OLED material. Specifically, depending on the number of rings, the condensation position, and the type and arrangement of heteroatoms, the polycyclic compound containing heteroatoms has characteristics of different band gaps (HOMO, LUMO), electrical properties, chemical properties, and physical properties, and thus application development of various OLED layers using the compound has been developed. Recently, the development of OLED materials for the type, number, and position of heteroatoms of pentacyclic compounds has been actively carried out.

[0012] As a prior reference, reference is made to US Pat. No. 8,334,058 B2. Summary of the invention

[0013] Utilizing the characteristics of a polycyclic compound, the present invention provides a compound capable of maximizing the effects of improving luminous efficiency and long life while maintaining or slightly reducing the driving voltage of a device, and an organic electric element and an electronic device thereof using the compound.

[0014] [Technical solution]

[0015] The present invention provides compounds represented by formula (1) and formula (18), organic electric elements comprising the compounds, and electronic devices thereof.

[0016]

[0017] [Effects of the invention]

[0018] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the element can be achieved, and the color purity and life of the element can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

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

[0020] 100: Organic electrical components, 110: Substrate

[0021] 120: first electrode (anode), 130: hole injection layer

[0022] 140: hole transport layer, 141: buffer layer

[0023] 150: emission layer, 151: emission auxiliary layer

[0024] 160: electron transport layer, 170: electron injection layer

[0025] 180: Second electrode (cathode) DETAILED DESCRIPTION

[0026] Hereinafter, some embodiments of the present invention will be described in detail.In addition, in the following description of the present invention, when incorporating known functions and configurations herein may make the subject matter of the present invention rather unclear, the detailed description thereof will be omitted.

[0027] 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 coupled to the other component, but other components may be "connected", "coupled" or "connected" between the components.

[0028] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0029] Unless otherwise stated, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine or iodine.

[0030] 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.

[0031] Unless otherwise stated, the term "haloalkyl" or "haloalkyl" as used herein includes alkyl groups substituted with halogen.

[0032] Unless otherwise specified, the term "heteroalkyl group" as used herein means an alkyl group in which one or more carbon atoms constituting the alkyl group are substituted with a heteroatom.

[0033] 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.

[0034] 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.

[0035] Unless otherwise specified, the term “alkoxy,” “alkoxy group,” or “alkyloxy” as used herein means an oxy group attached to an alkyl group, and has 1 to 60 carbon atoms, but is not limited thereto.

[0036] Unless otherwise specified, the term “alkenoxy”, “alkenoxy group” or “alkenyloxy” as used herein means an oxy group is attached to an alkenyl group, and has 2 to 60 carbon atoms, but is not limited thereto.

[0037] Unless otherwise specified, the term “aryloxy” or “aryloxy group” as used herein means an oxy group is attached to an aryl group, and has 6 to 60 carbon atoms, but is not limited thereto.

[0038] Unless otherwise specified, the term "aryl group" or "arylene group" as used herein has 6 to 60 carbon atoms, but is not limited thereto. Herein, aryl groups or arylene groups mean monocyclic and polycyclic aromatic groups, and may also be formed by combining with adjacent groups. Examples of "aryl groups" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0039] 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.

[0040] In addition, when the prefixes are named sequentially, this means that the substituents are listed in the order in which they are first described. For example, arylalkoxy means an alkoxy group substituted by an aryl group, alkoxycarbonyl means a carbonyl group substituted by an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted by an arylcarbonyl group, wherein the arylcarbonyl group may be a carbonyl group substituted by an aryl group.

[0041] Unless otherwise specified, the term "heteroalkyl" as used herein means an alkyl group containing one or more heteroatoms. Unless otherwise specified, the term "heteroaryl group" or "heteroarylene group" as used herein means a C 2 To C 60 The aryl group or arylene group is not limited thereto and includes at least one of a monocyclic ring and a polycyclic ring, and may also be formed by combining with an adjacent group.

[0042] Unless otherwise specified, the term "heterocyclic group" as used herein contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any one of a monocyclic and a polycyclic ring, and may include a heteroalicyclic ring and / or a heteroaromatic ring. In addition, it may also be combined with adjacent groups to form a heterocyclic group.

[0043] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0044] 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.

[0045]

[0046] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "alicyclic" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0047] Unless otherwise specified, the term "ring" as used herein means an alicyclic 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.

[0048] In addition to the above mentioned hetero compounds, other hetero compounds or hetero groups contain but are not limited to one or more hetero atoms.

[0049] Unless otherwise indicated, the term "carbonyl" as used herein is represented by -COR', wherein R' can be 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, or a combination of these.

[0050] Unless otherwise indicated, the term "ether" as used herein is represented by -RO-R', wherein R or R' can independently be 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, or a combination of these.

[0051] Unless otherwise specified, the term "substituted or unsubstituted" as used herein means that the substituent is substituted by at least one substituent, and the at least one substituent includes but is not limited to deuterium, hydrogen, 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 group.

[0052] Unless expressly stated otherwise, the formulae for 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.

[0053]

[0054] When a is an integer of 0, it means that the substituent R 1is not present. That is, when a is 0, this means that all carbons forming the benzene ring are bonded to hydrogen. In this case, the symbol of the hydrogen bonded to the carbon can be omitted, and the formula or compound can be described. When a is an integer of 1, the only substituent R 1 When a is an integer of 2 or 3, they are respectively bonded as follows, wherein R 1 may be the same as or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner but the sign of hydrogen bonded to the carbon forming the benzene ring is omitted.

[0055]

[0056] Hereinafter, a compound according to aspects of the present invention and an organic electric element including the compound will be described.

[0057] According to a specific example of the present invention, a compound represented by formula (1) is provided.

[0058] Formula (1)

[0059]

[0060] {In formula (1),

[0061] 1) Ar 1 ,Ar 2 and Ar 3 Each independently is C 6 -C 60 Aryl groups;

[0062] 2) l and e are integers from 0 to 4, d and m are integers from 0 to 4, a and b are integers from 0 to 3, n is an integer from 1 to 3, and c is an integer from 0 to 4,

[0063] 3) R 1 , R 2 , R 3 , R 4 and R 5 Each is independently selected from hydrogen; deuterium; halogen; C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Alicyclic and C 6 -C 60 Aromatic ring fused group; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C2 -C 20 Alkynyl group; C 1 -C 30 Alkoxy group; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b );

[0064] Wherein, L' can be selected from a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused aromatic ring group; and C 2 -C 60 Heterocyclic groups;

[0065] And R a and R b Each independently selected from C 6 -C 60 Aryl group; Fluorenyl group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused ring group of an aromatic ring; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; or multiple R 1 , multiple R 2 , multiple R 3 , multiple R 4 and multiple R 5 may combine with each other to form an aromatic ring and / or a heteroaromatic ring,

[0066] Among them, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenyl group, condensed ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group can be substituted by one or more substituents selected from deuterium; halogen; 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 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20Aryl 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 groups and C 8 -C 20 The arylalkenyl group, wherein the substituents may be combined with each other to form a ring, wherein the term "ring" means C 3 -C 60 Alicyclic or C 6 -C 60 Aromatic ring or C 2 -C 60 A heterocyclic group or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

[0067] In a specific aspect of the present invention, the compound represented by formula (1) includes a compound represented by any one of the following formulas (2) to (7).

[0068]

[0069]

[0070] {In equations (2) to (7),

[0071] Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined above.}

[0072] Preferably, Ar in formula (1) 1 ,Ar 2 and Ar 3 At least one of the 6 -C 24 Aryl group, more preferably, Ar in formula (1) 1 or Ar 3 Including C 6 -C 24 Aryl group.

[0073] In addition, R in formula (1) 3 C 6 -C 24 Aryl group.

[0074] In addition, Formula (1) includes compounds represented by any one of the following Formulas (8) to (10):

[0075] {In equations (8) to (10),

[0076] Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined above.}

[0077] Furthermore, the compound represented by formula (1) includes a compound represented by formula (11)

[0078] <Formula (11)>

[0079]

[0080] {In formula (11),

[0081] Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined above.}

[0082] Specifically, in the present invention, the compound represented by formula (1) includes the following Compound P-1 to Compound P-160.

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In another aspect, the present invention provides an organic electric element including: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and including the compound included in formula (1).

[0089] The organic material layer includes at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer, an emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one of the hole injection layer, the hole transport layer, the emission auxiliary layer, the emission layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer contains one or two or more than two compounds of formula (1). Preferably, the emission layer contains the compound.

[0090] More specifically, the present invention provides an organic electronic element further comprising a compound represented by formula (12) in an emission layer.

[0091] <Formula (12)>

[0092]

[0093] {In formula (12),

[0094] 1) Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 and Z 16 are each independently CR or N,

[0095] Where R is hydrogen; C 6 -C 60 Aryl group; C containing at least one heteroatom of O, N, S, Si or P 3 -C 60 Heterocyclic group; C 1 -C 50 Alkyl group; C 6 -C 60 an arylamine group; a fluorene group; and can form a ring by combining with an adjacent group,

[0096] 2) L 2 Selected from single bonds; C 6 -C 60 Arylene group; C 3 -C 60 a heteroarylene group; and a divalent aliphatic hydrocarbon group;

[0097] 3)W is NAr 5, O, S or CR'R";

[0098] R' and R" are each independently selected from C 1 -C 50 Alkyl group; C 6 -C 60 Aryl group; C containing at least one heteroatom of O, N, S, Si or P 3 -C 60 heterocyclic group; and R' and R" may be combined with each other to form a spiro ring,

[0099] 4) Ar 4 and Ar 5 Each independently selected from C 6 -C 60 Aryl group; C containing at least one heteroatom of O, N, S, Si or P 3 -C 60 Heterocyclic group; C 1 -C 50 Alkyl group; C 6 -C 60 Arylamine group; Fluorene group.}

[0100] The compound represented by formula (12) includes a compound represented by any one of the following formula (13) to formula (16).

[0101]

[0102] {In equations (13) to (16),

[0103] Ar 4 ,Ar 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , L 2 , R', R" are the same as defined above.}

[0104] Preferably, Ar of formula (12) 4 and Ar 5 Including C 6 -C 30Compounds represented by aryl groups.

[0105] In addition, the compound represented by formula (12) includes a compound represented by formula (17)

[0106] Formula (17)

[0107]

[0108] {In formula (17),

[0109] Ar 4 ,Ar 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 and L 2 Same as defined above.

[0110] 1) L 1 Selected from single bonds; C 6 -C 60 Arylene group; C 3 -C 60 a heteroarylene group; and a divalent aliphatic hydrocarbon group;

[0111] 2) Y is O, S or NAr 5 ,

[0112] 3) R a and R b Each is independently selected from hydrogen; deuterium; halogen; C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Alicyclic and C 6 -C 60 Aromatic ring fused group; C 1 -C 50 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20Alkynyl group; C 1 -C 30 Alkoxy group; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b ); or multiple R a and multiple R b may be combined with each other to form an aromatic ring and / or a heteroaromatic ring,

[0113] 4) y is an integer from 0 to 3, and z is an integer from 0 to 4.}

[0114] Specifically, the compounds represented by formula (12) include the following Compound 4-1 to Compound 4-52.

[0115]

[0116]

[0117]

[0118]

[0119] As another example, the present invention provides an organic electronic element, comprising: an anode; a cathode; an organic material layer formed between the anode and the cathode, wherein the organic material layer includes an emission layer; a hole transport layer formed between the anode and the emission layer; an emission auxiliary layer formed between the emission layer and the hole transport layer; wherein the hole transport layer or the emission auxiliary layer contains a compound represented by formula (18), and the emission layer contains a compound represented by formula (1).

[0120]

[0121] {In formula (1) and formula (18),

[0122] 1) Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined above.

[0123] 2) Ar 4 and Ar 5 Each independently selected from C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2-C 60 Heterocyclic group; C 3 -C 60 Alicyclic and C 6 -C 60 Aromatic ring fused 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; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b );

[0124] Wherein, L' can be selected from a single bond; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused aromatic ring group; and C 2 -C 60 Heterocyclic groups;

[0125] And R a and R b Each independently selected from C 6 -C 60 Aryl group; Fluorenyl group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused ring group of an aromatic ring; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups;

[0126] or Ar 4 and Ar 5 can be combined with each other to form a ring.

[0127] 3) Ar 6 Selected from C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; or at least one of the following formula (1-a), formula (1-b), formula (1-c)

[0128]

[0129] 4) Ar 9 ,Ar 10 and Ar 11 Each independently selected from C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Alicyclic and C 6 -C 60 Aromatic ring fused 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; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b );

[0130] 5) h, i and g are integers from 0 to 4; j is an integer from 0 to 3; R 6 , R 7 , R 8 and R 9 are the same as or different from each other and are each independently selected from hydrogen; deuterium; halogen; C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group; C 3 -C 60 Alicyclic and C 6 -C 60 Aromatic ring fused 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; C 6 -C 30 Aryloxy group; and -L'-N(R a )(R b );

[0131] When g, h, i, and j are 2 or greater than 2, multiple R6 , R 7 , R 8 and R 9 are identical to or different from each other and can combine with each other to form a ring,

[0132] 6) L 6 Selected from single bonds; C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused ring group of an aromatic ring; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups;

[0133] 7) L 5 Selected from C 6 -C 60 Arylene group; Fluorenylene group; C 3 -C 60 Alicyclic and C 6 -C 60 A fused ring group of an aromatic ring; and a C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic group.

[0134] The present invention also provides an organic electronic element comprising at least one compound represented by formula (12) in an emission layer.

[0135] Furthermore, the hole transport layer contains the compound represented by Formula (19) or Formula (20), and the emission assisting layer contains the compound represented by Formula (21) or Formula (22).

[0136]

[0137] {In equations (19) to (22),

[0138] 1) Ar 6 Selected from C 6 -C 60 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 60 Heterocyclic groups;

[0139] 2) Ar 4 ,Ar 5 ,Ar 9 ,Ar 10 ,Ar 11 ,h,i,g,L 5 , L6 , R 6 , R 7 , R 8 and R 9 Same as defined above.}

[0140] Specifically, the compounds represented by formula (18) include the following Compound 13-1 to Compound 13-79 and Compound 2-1 to Compound 2-76.

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] As another example, the present invention provides an organic electronic element, comprising: an anode; a cathode; an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises an emission layer, a hole transport layer formed between the anode and the emission layer, and an emission auxiliary layer or an electron blocking layer (EBL) formed between the emission layer and the hole transport layer; wherein the emission auxiliary layer or the electron blocking layer contains a compound represented by formula (30).

[0153] Formula (30)

[0154]

[0155] {In formula (30),

[0156] R 20 , R 21 , R 22 , R 23 , R 24 and R 25 Each is independently selected from hydrogen; deuterium; halogen; C 6-C 30 Aryl group; fluorenyl group; C containing at least one heteroatom of O, N, S, Si or P 2 -C 30 Heterocyclic group; C 3 -C 30 Alicyclic and C 6 -C 30 Aromatic ring fused group; C 1 -C 30 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; or multiple R 20 , multiple R 22 , multiple R 23 , multiple R 24 and multiple R 25 may be combined with each other to form an aromatic ring and / or a heteroaromatic ring,

[0157] v is an integer from 0 to 3,

[0158] u, w, x and y are each independently an integer from 0 to 4,

[0159] Z is an integer from 0 to 5,

[0160] L 20 and L 21 Each is independently a single bond; C 6 -C 30 Arylene group; C 3 -C 30 heteroarylene groups;

[0161] Ar 20 It is C 6 -C 30 Aryl group; or C 3 -C 30 heteroarylene groups;

[0162] X 20 is O, S, NR' or CR'R";

[0163] R' and R" are each independently selected from C 1 -C 30 Alkyl group; C 6 -C 30 Aryl group; C containing at least one heteroatom of O, N, S, Si or P 3 -C30 heterocyclic group; and R' and R" may be combined with each other to form a spiro ring.}

[0164] In the present invention, the compound represented by formula (30) is represented by any one of formula (31) to formula (38).

[0165]

[0166]

[0167] {In equations (31) to (40),

[0168] R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , L 20 , L 21 ,Ar 20 and X 20 , u, v, w, x, y, and z are the same as defined above.}

[0169] In the present invention, the compound represented by formula (30) includes the following compounds.

[0170]

[0171]

[0172]

[0173]

[0174] refer to Figure 1 The organic electrical element (100) according to the present invention includes a first electrode (120) formed on a substrate (110), a second electrode (180), and an organic material layer containing a compound represented by formula (1) between the first electrode (120) and the second electrode (180). Here, the first electrode (120) may be an anode (positive electrode), and the second electrode (180) may be a cathode (negative electrode). In the case of an inverted organic electrical element, the first electrode may be a cathode, and the second electrode may be an anode.

[0175] The organic material layer may include a hole injection layer (130), a hole transport layer (140), an emission layer (150), an emission auxiliary layer (151), an electron transport layer (160) and an electron injection layer (170) sequentially formed on the first electrode (120). Here, the remaining layers except the emission layer (150) may not be formed. The organic material layer may also include a hole blocking layer, an electron blocking layer, an emission auxiliary layer (151), an electron transport auxiliary layer, a buffer layer (141), etc., and the electron transport layer (160) etc. may play the role of a hole blocking layer.

[0176] Although not shown, the organic electric element according to the present invention may further include a protective layer formed on at least one side of the first electrode and the second electrode, the side being a side opposite to the organic material layer.

[0177] Otherwise, even if the same core is used, the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is bound at which position. Therefore, the selection of the core and its associated sub-substituent combination is also very important. In particular, when the optimal combination of the energy levels and T1 values ​​of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) is achieved, long life and high efficiency can be achieved at the same time.

[0178] The organic electroluminescent device according to the embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or an alloy thereof is deposited on a substrate to form a cathode, and an organic material layer including a hole injection layer (130), a hole transport layer (140), an emission layer (150), an electron transport layer (160) and an electron injection layer (170) is formed thereon, and then a material that can be used as a cathode is deposited thereon, thereby manufacturing an organic electroluminescent device according to the embodiment of the present invention. In addition, an emission auxiliary layer (151) can also be formed between the hole transport layer (140) and the emission layer (150), and an electron transport auxiliary layer can also be formed between the emission layer (150) and the electron transport layer (160).

[0179] As another specific example, the present invention provides an organic electrical element, wherein the emission layer in the organic material layer is a phosphorescent light-emitting layer.

[0180] The compounds represented by formula (1) and formula (18) are mixed at any one ratio of 1:9 to 9:1 to be contained in the emission layer of the organic material layer, wherein the compound represented by formula (12) is also mixed to be contained in the emission layer.

[0181] The present invention may further include a light efficiency enhancement layer formed on at least one of a side of the first electrode opposite to the organic material layer or a side of the second electrode opposite to the organic material layer.

[0182] As another example, the present invention provides an organic electronic device, wherein the compound represented by formula (30) is used in an emission auxiliary layer or an electron blocking layer, and is preferably contained in a green emission auxiliary layer. More specifically, the compound represented by formula (39) or formula (40) is contained in a green emission auxiliary layer.

[0183] In addition, the present invention provides an organic electrical element, in which an organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a narrow coating process, a dip coating process or a roll-to-roll process, and 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 method of forming the organic material layer.

[0184] The organic electric element according to the 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.

[0185] WOLED (white organic light emitting device) has the advantages of achieving high resolution and excellent processability, and can be manufactured using conventional LCD color filter technology. Various structures of white organic light emitting devices, which are mainly used as backlight devices, have been proposed and patented. Representatively, radiation components of R (red), G (green) and B (blue) are arranged side by side, a lamination method in which an R emission layer, a G emission layer and a B emission layer are laminated on the top and bottom, electroluminescence through a blue (B) organic emission layer, and by using light from this method, a color conversion material (CCM) method using photoluminescence of an inorganic phosphor, etc. and the present invention can be applied to such WOLED.

[0186] The present invention also provides an electronic device, which includes a display device having the organic electric element; and a control unit for driving the display device.

[0187] According to another aspect, the present invention provides a display device, wherein the organic electrical element is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor (organic TFT), and an element for monochrome or white lighting. Here, the electronic device may be a wired / wireless communication terminal currently used or to be used in the future, and covers all kinds of electronic devices, including mobile communication terminals such as portable phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various televisions, and various computers.

[0188] Hereinafter, synthesis examples of the compounds represented by formula (1) and formula (2) of the present invention and preparation examples of the organic electric element of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0189] [Synthesis example 1]

[0190] The final product 1 represented by formula (1) according to the present invention is prepared by reacting Core and Sub as shown in the following Reaction Scheme 1, but is not limited thereto.

[0191] <Reaction Scheme 1>

[0192]

[0193] Nuclear synthesis example

[0194] The core of Reaction Scheme 1 can be synthesized via the reaction pathway of Reaction Scheme 2 below, but is not limited thereto.

[0195] <Reaction Scheme 2>

[0196]

[0197] Synthesis of Intermediate-1

[0198] In a round-bottom flask, 2,4,6-trichloro-1,3,5-triazine (50 g, 410.1 mmol), phenylboronic acid (83.2 g, 451.1 mmol), Pd(PPh 3 ) 4 (14.2 g, 12.3 mmol), K 2 CO 3 (170 g, 1.2 mol), THF (1.3 L) and water (700 ml), and stirred at 90 °C. When the reaction was complete, 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 55 g (yield: 60%) of Intermediate 1.

[0199] Nuclear synthesis

[0200] In a round-bottom flask, intermediate-1 (10 g, 47 mmol), dibenzo[b,d]furan-3-ylboronic acid (12 g, 51.9 mmol), Pd(PPh 3 ) 4 (1.6 g, 1.4 mmol), K 2 CO 3 (20 g, 141 mmol), THF (160 ml) and water (80 ml), and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 5.7 g (yield: 53%) of Core 1.

[0201] Examples of the core are as follows, but are not limited thereto. In addition, [Table 1] shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of some compounds belonging to the core.

[0202]

[0203]

[0204] [Table 1]

[0205]

[0206] Sub Example

[0207] Examples of Sub are as follows, but are not limited thereto. In addition, [Table 2] shows FD-MS (Field Desorption-Mass Spectrometry) values ​​of some compounds belonging to Sub.

[0208]

[0209]

[0210] [Table 2]

[0211] Compound FD-MS Compound FD-MS Sub 1 <![CDATA[m / z=304.07(C 18 H 13 B.O. 2 S=304.17)]]> Sub 2 <![CDATA[m / z=304.07(C 18 H 13 B.O. 2 S=304.17)]]> Sub 3 <![CDATA[m / z=354.09(C 22 H 15 B.O. 2 S=354.23)]]> Sub 4 <![CDATA[m / z=354.09(C 22 H 15 B.O. 2 S=354.23)]]> Sub 5 <![CDATA[m / z=354.09(C 22 H 15 B.O. 2 S=354.23)]]> Sub 6 <![CDATA[m / z=380.10(C 24 H 17 B.O. 2 S=380.27)]]> Sub 7 <![CDATA[m / z=404.10(C 26 H 17 B.O. 2 S=404.29)]]> Sub 8 <![CDATA[m / z=380.10(C 24 H 17 B.O. 2 S=380.27)]]> Sub9 <![CDATA[m / z=385.14(C 24 H 12 D 5 BO 2 S=385.30)]]> Sub 10 <![CDATA[m / z=430.12(C 28 H 19 B.O. 2 S=430.33)]]> Sub 11 <![CDATA[m / z=430.12(C 28 H 19 B.O. 2 S=430.33)]]> Sub 12 <![CDATA[m / z=480.14(C 32 H 21 B.O. 2 S=480.39)]]> Sub 13 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]> Sub 14 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]> Sub 15 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]> Sub 16 <![CDATA[m / z=380.10(C 24 H 17 B.O. 2 S=380.27)]]> Sub 17 <![CDATA[m / z=385.14(C 24 H 12 D 5 BO 2 S=385.30)]]> Sub 18 <![CDATA[m / z=430.12(C 28 H 19 B.O. 2 S=430.33)]]> Sub 19 <![CDATA[m / z=430.12(C 28 H 19 B.O. 2 S=430.33)]]> Sub 20 <![CDATA[m / z=480.14(C 32 H 21 B.O. 2 S=480.39)]]> Sub 21 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]> Sub 22 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]> Sub 23 <![CDATA[m / z=456.14(C 30 H 21 B.O. 2 S=456.37)]]>

[0212] Synthesis example of product

[0213] Synthesis Example of P-41

[0214]

[0215] In a round-bottom flask, core 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (5.7 g, 41.3 mmol), THF and water, and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.6 g (yield: 57%) of P-41.

[0216] Synthesis Example of P-91

[0217]

[0218] In a round-bottom flask, core 1 (5 g, 14 mmol), Sub 9 (5.8 g, 15.4 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (5.8 g, 41.9 mmol), THF and water, and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.7 g (yield: 51%) of P-91.

[0219] Synthesis Example of P-106

[0220]

[0221] In a round-bottom flask, core 1 (5 g, 14 mmol), Sub 16 (5.8 g, 15.4 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (5.8 g, 41.9 mmol), THF and water, and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 5.8 g (yield: 63%) of P-106.

[0222] Synthesis Example of P-146

[0223]

[0224] In a round-bottom flask, core 11 (5 g, 14 mmol), Sub 2 (5.8 g, 15.4 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (5.8 g, 41.9 mmol), THF and water, and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.7 g (yield: 51%) of P-146.

[0225] Synthesis Example of P-4

[0226]

[0227] In a round-bottom flask, core 1 (5 g, 14 mmol), Sub 6 (5.9 g, 15.4 mmol), Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (5.8 g, 41.9 mmol), THF and water, and stirred at 90°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 6.1 g (yield: 66%) of P-4.

[0228] [Table 3] shows FD-MS (field desorption-mass spectrometry) values ​​of some compounds belonging to the products.

[0229] [Table 3]

[0230]

[0231]

[0232]

[0233]

[0234] [Synthesis example 2]

[0235] The compound represented by formula (12) according to the present invention (final product 2) can be prepared by reacting Sub 3-1 and Sub 3-2 as shown in the following Reaction Scheme 4, but is not limited thereto.

[0236] <Reaction Scheme 4>

[0237]

[0238] Synthesis Example 4-1

[0239]

[0240] 3-Bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF, and (9-(4,6-diphenyl-1,3,5-triazine-2-yl)-9H-carbazole-3-yl)boronic acid (8.8 g, 20 mmol), Pd(PPh 3 ) 4 (0.03 equivalent), K 2 CO 3 (3 equivalents) and water, and stirred at reflux. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was washed with MgSO 4 Dried and concentrated. The resulting organic matter was separated by silica gel column chromatography and recrystallized to obtain 9.2 g (yield: 72%) of a product.

[0241] Synthesis Example of 4-21

[0242]

[0243] 10-Bromo-7-(pyridin-2-yl)-7H-benzo[c]carbazole (7.5 g, 2 mmol) and dibenzo[b,d]furan-2-ylboronic acid (4.2 g, 20 mmol) were reacted in the same manner as 4-1 to obtain 6.5 g (yield: 71%) of the product.

[0244] Synthesis Example 4-25

[0245]

[0246] 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol) and (9-(naphthalene-2-yl)-9H-carbazole-3-yl)boronic acid (6.7 g, 20 mmol) were reacted in the same manner as 4-1 to obtain 9.2 g (yield: 75%) of the product.

[0247] Synthesis Example of 4-31

[0248]

[0249] 3'-Bromo-9-phenyl-9H-2,9'-bicarbazole (9.7 g, 20 mmol) and (9-phenyl-9H-carbazole-3-yl)boronic acid (5.7 g, 20 mmol) were reacted in the same manner as 4-1 to obtain 9.5 g (yield: 73%) of the product.

[0250] Synthesis Example of 4-32

[0251]

[0252] 3-Bromo-9-(dibenzo[b,d]furan-2-yl)-9H-carbazole (8.2 g, 20 mmol) and (12-([1,1':4',1"-triphenyl]-4-yl)-12H-benzo[4,5]thienyl[2,3-a]carbazole-3-yl)boronic acid (10.9 g, 20 mmol) were reacted in the same manner as 4-1 to obtain 11.5 g (yield: 69%) of the product.

[0253] Synthesis Example of 4-34

[0254]

[0255] 4-Bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) and (4-(dibenzo[b,d]thiophen-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) were reacted in the same manner as 4-1 to obtain 6.7 g (yield: 67%) of the product.

[0256] Synthesis Example of 4-35

[0257]

[0258] 3-Bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) and 9(9,9-dimethyl-9H-fluoren-3-yl)boronic acid (4.8 g, 20 mmol) were reacted in the same manner as in 4-1 to obtain 6.1 g (yield: 70%) of the product.

[0259] [Table 4]

[0260]

[0261]

[0262] [Synthesis example 3]

[0263] The final product represented by formula (18) according to the present invention may be prepared by the following reaction, but is not limited thereto.

[0264] Synthesis Example of 13-17

[0265]

[0266] 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, and di([1,1'-biphenyl]-4-yl)amine (6.4 g, 20 mmol), Pd 2 (dba) 3 (0.05 equivalent), PPh 3(0.1 eq.), NaOt-Bu (3 eq.), and stirred at 100°C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting organic matter was separated by silica gel column chromatography and recrystallized to obtain 12.9 g (yield: 84%) of a product.

[0267] Synthesis Example of 13-32

[0268]

[0269] 3-(4-bromophenyl)-9-phenyl-9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene, and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), Pd 2 (dba) 3 (0.05 equivalent), PPh 3 (0.1 eq.), NaOt-Bu (3 eq.), and stirred at 100°C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was washed with MgSO 4 Dried and concentrated. The resulting organic matter was separated by silica gel column chromatography and recrystallized to obtain 13.8 g (yield: 85%) of a product.

[0270] Synthesis Example of 2-34

[0271]

[0272] In a round bottom flask, Sub 4 (19) (9.5 g, 20 mmol), Sub 5 (4) (4.7 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL), and reacted at 100°C. When the reaction was complete, CH 2 Cl 2 The reaction mixture was extracted with water. The organic layer was purified by MgSO 4 Dried and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 9.8 g (yield: 78%) of 2-34.

[0273] Synthesis Example of 2-58

[0274]

[0275] In a round-bottom flask, Sub 4 (35) (8.4 g, 20 mmol), Sub 5 (7) (5.7 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-58 (10.4 g, 83%).

[0276] Synthesis Example of 2-59

[0277]

[0278] In a round bottom flask, Sub 4 (32) (12.9 g, 20 mmol), Sub 5 (11) (7.9 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-59 (5.2 g, 79%).

[0279] Synthesis Example of 2-69

[0280]

[0281] In a round-bottom flask, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), 4-(2-bromophenyl)-9,9-diphenyl-9H-fluorene (9.5 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-69 (12.2 g, 81%).

[0282] Synthesis Example of 2-71

[0283]

[0284] In a round-bottom flask, N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (7.5 g, 20 mmol), N-(3-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (10.6 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-71 (12.9 g, 78%).

[0285] [Synthesis Example 4]

[0286] The final product represented by Formula (30) according to the present invention is prepared by reacting Sub 30 and Sub 31 as shown in the following Reaction Scheme 5, but is not limited thereto.

[0287] <Reaction Scheme 5>

[0288]

[0289] Synthesis example of Sub 30

[0290] <Reaction Scheme 6>

[0291]

[0292] Synthesis Example of Sub30(81)

[0293]

[0294] In a round-bottom flask, 3-(9-phenyl-9H-fluoren-9-yl)aniline (6.7 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give Sub 30 (81) (8.83 g, 84%).

[0295] Example of Sub 31

[0296] Examples of Sub 31 are as follows, but are not limited thereto.

[0297]

[0298]

[0299] [Table 5]

[0300]

[0301] Synthesis Example of 2-72

[0302]

[0303] In a round-bottom flask, N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)dibenzo[b,d]furan-1-amine (10.0 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-72 (12.2 g, 81%).

[0304] Synthesis Example of 2-81

[0305]

[0306] In a round bottom flask, Sub 30 (81) (10.3 g, 20 mmol), Sub 31-4 (4.66 g, 20 mmol), Pd 2 (dba) 3 (0.5 g, 0.6 mmol), P(t-Bu) 3 (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were reacted to give 2-81 (10.3 g, 76%).

[0307] [Table 6]

[0308]

[0309]

[0310] Fabrication and evaluation of organic electronic components

[0311] Example 1) Fabrication and evaluation of green organic light emitting diodes

[0312] (main body)

[0313] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60 nm, and on this layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound was vacuum deposited to form a hole transport layer having a thickness of 60 nm. Then, the compound of the present invention represented by formula (1) as a host and Ir(ppy) as a dopant doped at a weight ratio of 95:5 were added. 3 [Tris(2-phenylpyridine)-iridium] is deposited on the hole transport layer to form an emission layer with a thickness of 30nm. (1,1'-biphenyl)-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited to a thickness of 40nm as an electron transport layer. Afterwards, alkali metal halide (LiF) is vacuum deposited to a thickness of 0.2nm as an electron injection layer, and Al is deposited to a thickness of 150nm to form a cathode, thereby manufacturing an OLED.

[0314] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m 2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0315] [Comparative Examples 1 to 4]

[0316] An OLED was prepared in the same manner as in Example 1, except that Comparative Compound A, Comparative Compound B, Comparative Compound C, and Comparative Compound D were used as hosts.

[0317]

[0318] [Table 7]

[0319]

[0320] Example 2) Fabrication and evaluation of green organic light emitting diodes

[0321] (Mixed Subject)

[0322] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60 nm, and on this layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound was vacuum deposited to form a hole transport layer having a thickness of 60 nm. Then, a mixture of the compound of the present invention represented by formula (1) and the compound represented by formula (12) at a ratio of 6:4 as a host and Ir(ppy) as a dopant doped at a weight ratio of 95:5 was added. 3 [Tris(2-phenylpyridine)-iridium] is deposited on the hole transport layer to form an emission layer with a thickness of 30nm. (1,1'-biphenyl)-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited to a thickness of 40nm as an electron transport layer. Afterwards, alkali metal halide (LiF) is vacuum deposited to a thickness of 0.2nm as an electron injection layer, and Al is deposited to a thickness of 150nm to form a cathode, thereby manufacturing an OLED.

[0323] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m 2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0324] [Comparative Examples 5 to 8, Comparative Examples 10 to 13]

[0325] An OLED was prepared in the same manner as in Example 2 except that Comparative Compound A, Comparative Compound B, Comparative Compound C and Comparative Compound D were used as a host instead of the compound of the present invention represented by formula (1).

[0326] [Comparative Example 9 and Comparative Example 14]

[0327] An OLED was prepared in the same manner as in Example 2 except that Comparative Compound E was used as a host instead of the compound of the present invention represented by Formula (12).

[0328] Comparative Compound E

[0329]

[0330] [Table 8]

[0331]

[0332]

[0333] Example 3) Fabrication and evaluation of green organic light emitting diodes

[0334] (Emission auxiliary layer + main body of the blend)

[0335] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) is vacuum deposited to form a hole injection layer with a thickness of 60nm. Then, on this layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound is vacuum deposited to a thickness of 60nm to form a hole transport layer. Then, the compound of the present invention represented by formula (18) as an emission auxiliary layer material is vacuum deposited to a thickness of 20nm to form an emission auxiliary layer. After the emission auxiliary layer is formed, a mixture of the compound of the present invention represented by formula (1) and the compound represented by formula (12) at a ratio of 6:4 and Ir(ppy) as a dopant doped with a weight ratio of 95:5 is added. 3 [Tris(2-phenylpyridine)-iridium] is deposited on the emission auxiliary layer to form an emission layer with a thickness of 30nm. (1,1'-biphenyl)-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited to a thickness of 40nm as an electron transport layer. Afterwards, alkali metal halide (LiF) is vacuum deposited to a thickness of 0.2nm as an electron injection layer, and Al is deposited to a thickness of 150nm to form a cathode, thereby manufacturing an OLED.

[0336] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0337] [Comparative Examples 15 to 29]

[0338] OLEDs were prepared in the same manner as in Example 3 except that Comparative Compounds A to E were each used as a host instead of the compound of the present invention represented by Formula (1).

[0339] [Table 9]

[0340]

[0341]

[0342] Example 4) Fabrication and evaluation of green organic light emitting diodes

[0343] (hole transport layer + emission auxiliary layer + mixed host)

[0344] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer having a thickness of 60nm. Then, the compound represented by formula (18) was vacuum deposited to a thickness of 60nm to form a hole transport layer. Then, the compound represented by formula (18) as an emission auxiliary layer material was vacuum deposited to a thickness of 20nm to form an emission auxiliary layer. After the emission auxiliary layer is formed, a mixture of a compound represented by formula (1) of the present invention and a compound represented by formula (12) at a ratio of 6:4 as a host and Ir(ppy) doped as a dopant at a weight ratio of 95:5 was added. 3 [Tris(2-phenylpyridine)-iridium] was deposited to form an emission layer having a thickness of 30 nm. (1,1'-biphenyl)-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. Afterwards, alkali metal halide (LiF) was vacuum deposited to a thickness of 0.2 nm as an electron injection layer, and Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an OLED.

[0345] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m 2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0346] [Table 10]

[0347]

[0348]

[0349] It can be seen from the results of Tables 7 to 10 that the organic electronic element using the organic electronic device material of the present invention as a phosphorescent host can significantly improve high luminous efficiency, low driving voltage and lifespan.

[0350] Table 7 shows that when the compounds of the present invention represented by formula (1) is used as a single subject, the superiority of the compounds of the present invention compared with the comparative compound. In the result of comparative compound A and comparative compound C, when 3-dibenzofurans are substituted, compared with 4-dibenzofurans, the performance of all aspects of driving voltage, efficiency and life span is improved. In the result of comparative compound A and comparative compound B or comparative compound C and comparative compound D, it can be confirmed that, compared with the triazine substituted with a dibenzothiophene or dibenzofuran moiety, the performance of the triazine substituted with two dibenzothiophenes or dibenzofuran moieties is improved. Therefore, it can be confirmed at last that the compounds of the present invention wherein triazine is substituted by 3-dibenzofurans and connected to the other side by the linker with 4-dibenzothiophenes show the result of improvement significantly different from comparative compound A to comparative compound D. It is suggested that the energy levels (HOMO, LUMO, T1, etc.) of a compound can vary significantly depending on the type or substitution position of the substituents, and the difference in the physical properties of the compounds can serve as a key factor in improving device performance (e.g., energy balance) during device deposition, leading to different device results.

[0351] Table 8 shows that when the compound represented by formula (12) and the compound represented by formula (1) are mixed, they are significantly better than other comparative combinations. This result also supports the explanation of the case of a single host, and when combined with the compound of formula (12), the driving voltage and efficiency can be improved by about 24% and the life can be improved by about 63% compared with the single host. When the two hosts are pre-mixed, the aging rate is very important for deposition at a certain rate, and the aging rate of the compounds of the present invention is better than other materials, and in particular, Ar 1 ,Ar 3 and R3 At least one of them is C 6 -C 24 Compounds with aryl groups gave the best results in the aging tests.

[0352] Table 9 is an example of using a mixed compound of the compound of formula (1) and the compound of formula (12) as the emission layer host and using the compound represented by formula (18) in the emission auxiliary layer, and shows that the efficiency is improved by about 60% and the life is improved by about 20% compared with Table 8. Here, compared with the results in Table 7, the use of the compound represented by formula (18) as the hole transport compound also produces slightly improved results in terms of driving voltage, efficiency and life.

[0353] That is, the compounds of the present invention show improved results compared to known compounds even when used as a single host, but significant results are obtained when used in combination with the compound represented by formula (12), or when the compound represented by formula (18) is used in an emission auxiliary layer or a hole transport layer.

[0354] Example 5) Fabrication and evaluation of blue organic light emitting diodes

[0355] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1 -phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) is vacuum deposited to form a hole injection layer with a thickness of 60nm. Then, on this layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) is vacuum deposited to a thickness of 60nm to form a hole transport layer. Then, the compound of the present invention as an emission auxiliary layer material is vacuum deposited to a thickness of 20nm to form an emission auxiliary layer. After the emission auxiliary layer is formed, on the emission auxiliary layer, 9,10-di(naphthalene-2-yl)anthracene as the main body and BD-052X (Idemitsu kosan) as a dopant are used at a ratio of 96:4, thereby depositing an emission layer with a thickness of 30nm on the emission auxiliary layer. (1,1'-biphenyl)-4-aluminum (2-methyl-8-quinolinolato) (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. Thereafter, alkali metal halide (LiF) was vacuum deposited to a thickness of 0.2 nm as an electron injection layer, and Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an OLED.

[0356] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m 2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0357] [Comparative Example 35 to Comparative Example 37]

[0358] An OLED was prepared in the same manner as in Comparative Example 5, except that the emission auxiliary layer was not used and Comparative Compound F, Comparative Compound G, and Inventive Compound 2-81 were used as hole transport layer materials.

[0359] [Comparative Example 38]

[0360] An OLED was prepared in the same manner as in Comparative Example 5, except that the emission auxiliary layer was not used.

[0361] [Comparative Examples 39 to 40]

[0362] An OLED was prepared in the same manner as in Comparative Example 5, except that Comparative Compound F or Comparative Compound G was used as the emission auxiliary layer material.

[0363]

[0364] [Table 11]

[0365]

[0366] Example 6) Fabrication and evaluation of green organic light emitting diodes

[0367] First, N 1 -(Naphthalen-2-yl)-N 4 ,N 4 -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1-phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) is vacuum deposited to form a hole injection layer with a thickness of 60nm. Then, on this layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound is vacuum deposited to a thickness of 60nm to form a hole transport layer. Then, the compound of the present invention represented by formula (30) as an emission auxiliary layer material is vacuum deposited to a thickness of 20nm to form an emission auxiliary layer. After the emission auxiliary layer is formed, on the emission auxiliary layer, 4,4-bis(9H-carbazole-9-yl)-1,1'-biphenyl as a host and Ir(ppy) as a dopant are used at a ratio of 95:5. 3 [Tris(2-phenylpyridine)-iridium], thereby depositing an emission layer with a thickness of 30nm. (1,1'-biphenyl)-4-radical)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10nm as a hole blocking layer, and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) is deposited to a thickness of 40nm as an electron transport layer. Afterwards, alkali metal halide (LiF) is vacuum deposited to a thickness of 0.2nm as an electron injection layer, and Al is deposited to a thickness of 150nm to form a cathode, thereby manufacturing an OLED.

[0368] A forward bias DC voltage was applied to the OLEDs manufactured in the examples and comparative examples, and electroluminescence (EL) was measured using PR-650 manufactured by Photoresearch Co., and a lifetime measurement device manufactured by McScience Inc. was used at 5000 cd / m 2 The T95 lifetime was measured at a reference brightness of . In the following table, the fabrication and evaluation results of the devices are shown.

[0369] [Comparative Example 41 to Comparative Example 42]

[0370] An OLED was prepared in the same manner as in Comparative Example 5, except that Comparative Compound F or Comparative Compound G was used as the emission auxiliary layer material.

[0371] [Table 12]

[0372]

[0373]

[0374] It can be seen from the results of Tables 11 to 12 that when an OLED is manufactured by using the material for an organic electroluminescent device of the present invention as an emission auxiliary layer material, the driving voltage of the organic electroluminescent device can be reduced and the luminous efficiency and lifespan can be significantly improved compared with the comparative examples that do not use the material for the emission auxiliary layer or use comparison compound F or comparison compound G.

[0375] Table 11 shows the production results of blue organic light-emitting devices. It can be confirmed that when the compounds of the present invention are used as emission auxiliary layers, excellent results are obtained. The results of Comparative Example 39 or Comparative Example 40 and Examples 57 to 70 show that the compounds of the present invention substituted with specific substituents such as DBT, DBF, Cz and fluorene are significantly better than the comparative compounds substituted with general aryl groups, even if the parent compounds are similar. That is, when specific substituents such as DBT, DBF, Cz and fluorene are introduced, the refractive index, Tg and energy levels (HOMO, LUMO, T1, etc.) of the compounds become significantly different, and the difference in such physical properties is the main factor in improving device performance (e.g., such as energy balance) during device deposition, so that different device results can be obtained.

[0376] Table 12 shows the production results of green organic light-emitting devices. When the compounds of the present invention are used in the emission auxiliary layer, the results are significantly better than the comparative compounds. This is also the influence of specific substituents such as DBT, DBF, Cz and fluorene, and the specific feature is that the advantage of the green auxiliary layer is significantly higher than that of the blue auxiliary layer. In addition, in the case of the blue auxiliary layer, the compounds substituted by DBT and DBF show the most excellent properties, but the results of the green auxiliary layer show that the compounds substituted by fluorene have the best results. This shows that even if the emission auxiliary layer compound is the same, the properties required according to the color of the emission layer are different, so that results that cannot be inferred by those skilled in the art can be obtained.

[0377] Although the exemplary embodiments of the present invention have been described for illustrative purposes, it will be understood by those skilled in the art that various modifications, additions and substitutions are feasible 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. The scope of the present invention should be interpreted based on the appended claims, and should be interpreted as all technical concepts included in the scope equivalent to the claims belong to the present invention.

Claims

1. Compound represented by formula (1) Formula (1) in, In formula (1), 1) Ar 1 ,Ar 2 and Ar 3 Each independently is C6-C 60 Aryl groups, 2) l and e are integers from 0 to 4, d and m are integers from 0 to 4, a and b are integers from 0 to 3, n is an integer from 1 to 3, and c is an integer from 0 to 4, 3) R 1 , R 2 , R 3 , R 4 and R 5 Each independently selected from hydrogen; deuterium; halogen; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Aromatic fused ring 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 a )(R b ); wherein L' can be selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Alicyclic and C6-C 60 Aromatic ring fused group; and C2-C 60 a heterocyclic group; and R a and R b Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Alicyclic and C6-C 60 A fused ring group of an aromatic ring; and a C2-C 60 Heterocyclic group; or multiple R 1 , multiple R 2 , multiple R 3 , multiple R 4 and multiple R 5 may combine with each other to form an aromatic ring or a heteroaromatic ring, The aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenyl group, condensed ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted by one or more substituents selected from deuterium; halogen; 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 groups and C8-C 20 Arylalkenyl group, wherein the substituents may be combined with each other to form a ring, wherein the term "ring" means a C3-C 60 Alicyclic or C6-C 60 Aromatic ring or C2-C 60 The heterocyclic group or a condensed ring formed by a combination thereof, and includes a saturated ring or an unsaturated ring.

2. The compound according to claim 1, wherein the compound represented by formula (1) is any one of the following formulas (2) to (7) In equations (2) to (7), Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined in claim 1.

3. The compound according to claim 1, wherein Ar in formula (1) 1 ,Ar 2 and R 3 At least one of them is C6-C 24 Aryl group.

4. The compound according to claim 1, wherein Ar in formula (1) 1 or Ar 3 It is C6-C 24 Aryl group.

5. The compound according to claim 1, wherein R in formula (1) 3 It is C6-C 24 Aryl group.

6. The compound according to claim 1, wherein the formula (1) is any one of the following formulas (8) to (10): In equations (8) to (10), Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined in claim 1.

7. The compound according to claim 1, wherein the compound represented by formula (1) is formula (11): In formula (11), Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined in claim 1.

8. The compound according to claim 1, wherein the compound represented by formula (1) is any one of the following compounds 9. Organic electronic components, including: a first electrode; a second electrode; and an organic material layer provided between the first electrode and the second electrode and including the compound according to any one of claims 1 to 4.

10. An organic electronic element according to claim 9, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer, an emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and at least one of the hole injection layer, the hole transport layer, the emission auxiliary layer, the emission layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer contains one or two or more than two compounds according to claim 1. The organic electronic element according to claim 10 , wherein the compound is contained in the emission layer.

12. The organic electronic element according to claim 11, wherein the emission layer further comprises a compound represented by formula (12): <Formula (12)> In formula (12), 1) Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 and Z 16 are each independently CR or N, Where R is hydrogen; C6-C 60 Aryl group; C3-C4-C6 ... 60 Heterocyclic group; C1-C 50 Alkyl group; C6-C 60 an arylamine group; a fluorene group; and can form a ring by combining with an adjacent group, 2) L 2 Selected from single bonds; C6-C 60 Arylene group; C3-C 60 a heteroarylene group; and a divalent aliphatic hydrocarbon group; 3)W is NAr 5 , O, S or CR'R"; R' and R" are each independently selected from C1-C 50 Alkyl group; C6-C 60 Aryl group; C3-C4-C6 ... 60 a heterocyclic group; and R' and R" may be combined with each other to form a spiro ring; 4) Ar 4 and Ar 5 Each independently selected from C6-C 60 Aryl group; C3-C4-C6 ... 60 Heterocyclic group; C1-C 50 Alkyl group; C6-C 60 Arylamine group; fluorene group.

13. The organic electronic device according to claim 12, wherein the formula (12) is any one of the following formulas (13) to (16): In equations (13) to (16), Ar 4 ,Ar 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , L 2 , R', and R" are the same as defined in claim 12.

14. The organic electronic device according to claim 12, wherein Ar in formula (12) 4 and Ar 5 All are C6-C 30 Aryl group.

15. The organic electronic element according to claim 12, wherein the compound represented by formula (12) is a compound represented by formula (17) <Formula (17)> In formula (17), Ar 4 ,Ar 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 and L 2 As defined in claim 12, 1) L 1 Selected from single bonds; C6-C 60 Arylene group; C3-C 60 a heteroarylene group; and a divalent aliphatic hydrocarbon group, 2) Y is O, S or NAr 5 , 3) R a and R b Each independently selected from hydrogen; deuterium; halogen; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Aromatic fused ring 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 a )(R b ); or multiple R a , multiple R b may combine with each other to form an aromatic ring and / or a heteroaromatic ring, in, L' can be selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Alicyclic and C6-C 60 Aromatic ring fused group; and C2-C 60 a heterocyclic group; and R a and R b Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Alicyclic and C6-C 60 A fused ring group of an aromatic ring; and a C2-C 60 Heterocyclic group; or multiple R 1 , multiple R 2 , multiple R 3 , multiple R 4 and multiple R 5 may combine with each other to form an aromatic ring and / or a heteroaromatic ring, 4) y is an integer from 0 to 3, and z is an integer from 0 to 4.

16. The organic electronic element according to claim 12, wherein the compound represented by formula (12) is any one of the following compounds 17. Organic electronic components, including: anode; cathode; forming an organic material layer between the anode and the cathode; wherein the organic material layer comprises an emission layer, a hole transport layer formed between the anode and the emission layer, and an emission auxiliary layer formed between the emission layer and the hole transport layer; wherein the hole transport layer or the emission auxiliary layer comprises a compound represented by formula (18), and the emission layer comprises a compound represented by formula (1) In formula (1) and formula (18), 1) Ar 1 ,Ar 2 ,Ar 3 ,l,m,n,a,b,c,d,e,R 1 , R 2 , R 3 , R 4 and R 5 Same as defined in claim 1, 2) Ar 4 and Ar 5 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Aromatic fused ring 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 a )(R b ); Wherein, L' can be selected from a single bond; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Alicyclic and C6-C 60 Aromatic ring fused group; and C2-C 60 a heterocyclic group; and R a and R b Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C3-C 60 Alicyclic and C6-C 60 A fused ring group of an aromatic ring; and a C2-C 60 Heterocyclic group; or Ar 4 and Ar 5 can combine with each other to form a ring, 3) Ar 6 Selected from C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; or at least one of the following formula (1-a), formula (1-b), formula (1-c) 4) Ar 9 ,Ar 10 and Ar 11 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Aromatic fused ring 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 a )(R b ), 5) h, i and g are integers from 0 to 4; j is an integer from 0 to 3; and R 6 , R 7 , R 8 and R 9 are the same as or different from each other and are each independently selected from hydrogen; deuterium; halogen; C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Aromatic fused ring 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 a )(R b ), When g, h, i, j are 2 or greater than 2, R 6 , R 7 , R 8 and R 9 Each is the same as or different from each other, and can be combined with each other to form a ring, 6) L 6 Selected from single bonds; C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Alicyclic and C6-C 60 A fused ring group of an aromatic ring; and a C2-C 60 Heterocyclic groups, 7) L 5 Selected from C6-C 60 Arylene group; Fluorenylene group; C3-C 60 Alicyclic and C6-C 60 A fused ring group of an aromatic ring; and a C2-C 60 Heterocyclic group.

18. The organic electronic device according to claim 17, wherein the emission layer further comprises at least one compound represented by formula (12): <Formula (12)> In formula (12), 1) Z 1 and Z 2 and Z 3 and Z 4 and Z 5 and Z 6 and Z 7 and Z 8 and Z 9 and Z 10 and Z 11 and Z 12 and Z 13 and Z 14 and Z 15 and Z 16 each independently is CR or N Where R is hydrogen; C6-C 60 Aryl group; C3-C4-C6 ... 60 Heterocyclic group; C1-C 50 Alkyl group; C6-C 60 an arylamine group; a fluorene group; and can form a ring by combining with an adjacent group, 2) L 2 Selected from single bonds; C6-C 60 Arylene group; C3-C 60 a heteroarylene group; and a divalent aliphatic hydrocarbon group, 3)W is NAr 5 , O, S or CR'R"; R' and R" are each independently C1-C 50 Alkyl group; C6-C 60 Aryl group; C3-C4-C6 ... 60 heterocyclic group; and R' and R" may be combined with each other to form a spiro ring, 4) Ar 4 and Ar 5 Each independently selected from C6-C 60 Aryl group; C3-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; C1-C 50 Alkyl group; C6-C 60 Arylamine group; fluorene group.

19. The organic electronic element according to claim 17, wherein the hole transport layer comprises a compound represented by formula (19) or formula (20), and the emission assisting layer comprises a compound represented by formula (21) or formula (22) In equations (19) to (22), 1) Ar 6 Selected from C6-C 60 Aryl group; Fluorenyl group; C2-C 60 Heterocyclic groups, 2) Ar 4 ,Ar 5 ,Ar 9 ,Ar 10 ,Ar 11 ,h,i,g,L 5 , L 6 , R 6 , R 7 , R 8 and R 9 Same as defined in claim 17.

20. The organic electronic element according to claim 17, wherein the compound represented by formula (18) is one of the following compounds: 21 . The organic electronic element according to claim 17 , wherein the compound represented by formula (1) and the compound represented by formula (18) are mixed at a ratio of any one of 1:9 to 9:1 for use in the emission layer.

22. The organic electronic element according to claim 17, wherein the compound represented by formula (1) is used as a phosphorescent host material of the emission layer. 23 . The organic electronic element according to claim 17 , further comprising a light efficiency enhancement layer formed on at least one of sides of the first electrode and the second electrode opposite to the organic material layer. 24 . The organic electronic element according to claim 17 , wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a narrow coating process, a dip coating process, or a roll-to-roll process.

25. Organic electronic components, including: anode; cathode; An organic material layer is formed between the anode and the cathode, wherein the organic material layer includes an emission layer, a hole transport layer formed between the anode and the emission layer, and an emission auxiliary layer or an electron blocking layer (EBL) formed between the emission layer and the hole transport layer; wherein the emission auxiliary layer or the electron blocking layer comprises a compound represented by formula (30), wherein formula (30) In formula (30), R 20 , R 21 , R 22 , R 23 , R 24 and R 25 Each independently selected from hydrogen; deuterium; halogen; C6-C 30 Aryl group; Fluorenyl group; C2-C 30 Heterocyclic group; C3-C 30 Alicyclic and C6-C 30 Aromatic fused ring group; C1-C 30 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 Aryloxy group; or multiple R 20 , multiple R 22 , multiple R 23 , multiple R 24 and multiple R 25 may combine with each other to form an aromatic ring and / or a heteroaromatic ring, v is an integer from 0 to 3, u, w, x and y are each independently an integer from 0 to 4, Z is an integer from 0 to 5, L 20 and L 21 Each is independently a single bond; C6-C 30 Arylene group; C3-C 30 heteroarylene groups; Ar 20 It is C6-C 30 Aryl group; or C3-C 30 Heteroarylene groups, X 20 is O, S, NR' or CR'R", R' and R" are each independently selected from C1-C 30 Alkyl group; C6-C 30 Aryl group; C3-C4-C6 ... 30 a heterocyclic group; and R' and R" may be combined with each other to form a spiro ring.

26. The organic electronic element according to claim 25, wherein the compound represented by formula (30) is any one of formula (31) to formula (33) In equations (31) to (33), R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , L 20 , L 21 ,Ar 20 and X 20 , u, v, w, x, y and z are the same as defined in claim 25.

27. The organic electronic element according to claim 25, wherein the compound represented by formula (30) is any one of formula (34) to formula (37) In equations (34) to (37), R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , L 20 , L 21 ,Ar 20 and X 20 , u, v, w, x, y and z are the same as defined in claim 25.

28. The organic electronic element according to claim 25, wherein the compound represented by formula (30) is a compound represented by formula (38) Formula (38) In formula (38), R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , L 20 , L 21 ,Ar 20 and X 20 , u, v, w, x, y and z are the same as defined in claim 25.

29. The organic electronic element according to claim 25, wherein the compound represented by formula (30) is formula (39) or formula (40) In formula (39) and formula (40), R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , L 20 , L 21 ,Ar 20 and X 20 , u, v, w, x, y and z are the same as defined in claim 25.

30. The organic electronic element according to claim 25, wherein the compound represented by formula (30) comprises the following compound 31. The organic electronic element according to claim 25, wherein the compound represented by formula (30) is used as a green emission auxiliary layer material.

32. The organic electronic element according to claim 29, wherein the compound represented by Formula (39) or Formula (40) is used as the green emission auxiliary layer material.

33. A display device comprising the organic electronic element according to claim 9, 17 or 25; and a control component for driving the display device.

34. The display device according to claim 33, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and an element for monochrome or white lighting.

Images