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

Abstract

Provided are a novel compound capable of improving luminous efficiency, stability, and lifespan of a device, an organic electric element using the compound, and an electronic device thereof.

Description

background [Technical Field]

[0002] This invention relates to compounds for use in organic electrical components, organic electrical components using said compounds, and electronic devices thereof. [Background Technology]

[0004] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical components utilizing organic light emission generally have a structure comprising an anode, a cathode, and layers of organic material inserted therebetween. To improve the efficiency and stability of organic electronic components, the organic material layers are typically composed of a multilayer structure made of different materials, and may include, for example, hole injection layers, hole transport layers, emission layers, electron transport layers, and electron injection layers.

[0005] Materials used as organic material layers in organic electrical components can be classified into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

[0006] Furthermore, luminescent materials can be classified into polymeric and low-molecular-weight types based on molecular weight, and into fluorescent materials derived from singlet excited states and phosphorescent materials derived from triplet excited states based on their luminescence mechanism. Additionally, luminescent materials can be classified into blue, green, and red luminescent materials based on their emission color, as well as yellow and orange luminescent materials necessary for achieving better natural colors.

[0007] Meanwhile, when only one material is used as the luminescent material, problems arise such as the maximum emission wavelength shifting to longer wavelengths due to intermolecular interactions, resulting in decreased color purity, or the device efficiency decreasing due to luminescence attenuation effects. Therefore, a host / dopant system can be used as the luminescent material to improve luminescence efficiency by enhancing color purity and energy transfer. When a small amount of dopant with a smaller band gap than the host forming the emission layer is mixed onto the emission layer, excitons generated in the emission layer are transported to the dopant for efficient luminescence. At this time, because the wavelength of the host shifts to the wavelength band of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

[0008] Currently, the portable display market is seeing a continuous increase in the size of large-screen displays, requiring significantly more power than existing portable displays. Therefore, power consumption is a critical factor for portable displays with limited power sources such as batteries, and efficiency and lifespan must be addressed.

[0009] Efficiency, lifetime, and driving voltage are interconnected. As efficiency increases, the driving voltage relatively decreases. Conversely, as the driving voltage decreases, the crystallization of organic materials due to Joule heating during driving decreases, thus increasing lifetime. However, simply improving the organic material layers does not maximize efficiency. This is because long lifetime and high efficiency can only be achieved simultaneously when the optimal combination of energy levels and T1 values ​​between the organic material layers, as well as the inherent properties of the materials (mobility, interfacial characteristics, etc.), is realized. Therefore, it is necessary to develop luminescent materials with high thermal stability and the ability to effectively achieve charge balance in the emitting layer.

[0010] In other words, to fully demonstrate the superior properties of organic electrical components, the materials used to form the organic material layer in the component (such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, emission auxiliary layer materials, etc.) should be stable and effective. However, such stable and effective organic material layer materials for organic electrical components have not yet been fully developed. Therefore, there is a continuous need to develop new materials, and there is an urgent need to develop host materials for emission layers.

[0011] Furthermore, polycyclic compounds containing heteroatoms exhibit significant differences in properties depending on their material structure, making them suitable for use as OLED materials in various layers. Specifically, depending on the number of rings, fusion positions, and the type and arrangement of heteroatoms, polycyclic compounds containing heteroatoms possess different band gaps (HOMO, LUMO), electrical properties, chemical properties, and physical properties, thus leading to the development of various OLED layer applications using these compounds. Recently, OLED materials using pentacyclic compounds with varying heteroatom types, numbers, and positions have been actively developed.

[0012] As a prior art reference, see U.S. Patent No. 8,334,058B2.

[0013] Detailed description of the invention Summary of the Invention

[0014] Utilizing the properties of polycyclic compounds, the present invention provides compounds that can maximize the effects of improved luminous efficiency and long lifespan while maintaining or slightly reducing the driving voltage of the device, as well as organic electrical components and electronic devices using said compounds.

[0015] [Technical Solution]

[0016] The present invention provides compounds represented by formulas (1) and (18), organic electrical components and electronic devices thereof containing said compounds.

[0017]

[0018]

[0019] [Invention Effects]

[0020] By using the compounds according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved. Brief description of the attached diagram

[0021] Figure 1 Examples of organic electrical components according to the present invention are illustrated.

[0022] 100: Organic electrical components; 110: Substrate

[0023] 120: First electrode (anode), 130: Hole injection layer

[0024] 140: Hole transport layer, 141: Buffer layer

[0025] 150: Launch layer, 151: Launch auxiliary layer

[0026] 160: Electron transport layer, 170: Electron injection layer

[0027] 180: Second electrode (cathode) Detailed Implementation

[0028] Some embodiments of the invention will be described in detail below. Furthermore, in the following description of the invention, detailed descriptions of known functions and configurations incorporated herein will be omitted where such inclusion might make the subject matter of the invention quite unclear.

[0029] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b) may be used herein. Each of these terms is not intended to define the substance, order, or sequence of the respective component, but only to distinguish the respective component from other components. It should be noted that if a component is described as “connected,” “linked,” or “attached” to another component, then the component may be directly connected or linked to another component, but may be “connected,” “linked,” or “attached” to other components between components.

[0030] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0031] Unless otherwise stated, the term "halogenated" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0032] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein means having a single bond of 1 to 60 carbon atoms and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), alkyl-substituted cycloalkyl groups, or cycloalkyl-substituted alkyl groups.

[0033] Unless otherwise stated, the term “halogenated alkyl” or “halogenated alkyl” as used herein includes alkyl groups that have been substituted with halogens.

[0034] Unless otherwise stated, the term “heteroalkyl” as used herein means an alkyl group in which one or more carbon atoms constituting the alkyl group are replaced by heteroatoms.

[0035] Unless otherwise stated, the terms “alkenyl” or “alkynyl” as used herein have, but are not limited to, two to 60 carbon atoms in double or triple bonds, and include straight or branched groups.

[0036] Unless otherwise stated, the term "cycloalkyl" as used herein means, but is not limited to, an alkyl group that forms a ring having 3 to 60 carbon atoms.

[0037] Unless otherwise stated, the terms “alkoxy,” “alkoxy group,” or “alkyloxy” as used herein mean an oxygen group attached to an alkyl group and having, but not limited to, 1 to 60 carbon atoms.

[0038] Unless otherwise stated, the terms “olefinic group”, “olefinic group” or “olefinic group” as used herein mean an olefinic group attached to an olefinic group and having 2 to 60 carbon atoms, but not limited thereto.

[0039] Unless otherwise stated, the term “aryloxy group” or “aryloxy group” as used herein means an oxygen group attached to an aryl group and having 6 to 60 carbon atoms, but not limited thereto.

[0040] Unless otherwise stated, the terms "aryl group" or "arylene group" as used herein refer to, but are not limited to, a group having 6 to 60 carbon atoms. In this document, aryl group or arylene group means monocyclic and polycyclic aromatic groups, and can also be formed by combining with adjacent groups. Examples of "aryl group" may include phenyl groups, biphenyl groups, fluorene groups, or spirofluorene groups.

[0041] The prefix “aryl” or “aromatic” indicates a group that is substituted by an aryl group. For example, an arylalkyl group can be an aryl-substituted alkyl group, and an arylalin group can be an aryl-substituted alkenyl group, and the aryl-substituted group has the number of carbon atoms as defined herein.

[0042] Furthermore, when prefixes are named sequentially, this means that substituents are listed in the order they are 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 means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0043] Unless otherwise stated, the term "heteroalkyl" as used herein means an alkyl group containing one or more heteroatoms. Unless otherwise stated, the terms "heteroaryl group" or "heteroaryl derivative group" as used herein mean a C2 to C3 group containing one or more heteroatoms. 60 Aryl or arylene groups, but not limited thereto, and including at least one of monocyclic and polycyclic groups, and may also be formed by combination with adjacent groups.

[0044] Unless otherwise stated, the term "heterocyclic group" as used herein contains one or more heteroatoms and has, but is not limited to, 2 to 60 carbon atoms, including any of monocyclic and polycyclic rings, and may include heteroaliphatic and / or heteroaromatic rings. Furthermore, it may combine with adjacent groups to form heterocyclic groups.

[0045] Unless otherwise stated, the term "heteroatom" as used herein means at least one of N, O, S, P, or Si.

[0046] Furthermore, the term "heterocyclic group" can include rings in which SO2 replaces the carbon atoms that make up the ring. For example, "heterocyclic group" includes the following compounds.

[0047]

[0048] Unless otherwise stated, as used herein, the term "aliphatic" 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.

[0049] Unless otherwise stated, as used herein, the term "ring" means an alicyclic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by combination thereof, and includes saturated or unsaturated rings.

[0050] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain, but are not limited to, one or more heteroatoms.

[0051] Unless otherwise stated, the term "carbonyl" as used herein is represented by -COR', where 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 thereof.

[0052] Unless otherwise stated, the term "ether" as used herein is indicated by -RO-R', wherein R or R' may 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 thereof.

[0053] Unless otherwise stated, the term "substituted or unsubstituted" as used herein means that a substituent is substituted by at least one substituent, including but not limited to deuterium, hydrogen, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl groups, C1-C 20 alkoxy groups, C1-C 20 Alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C3-C 20 Cycloalkyl groups, C6-C 20 aryl group, deuterated C6-C 20 aryl group, C8-C 20 Aryl alkenyl groups, silyl groups, boron groups, germanium groups and C2-C 20 Heterocyclic groups.

[0054] Unless otherwise explicitly stated, the formulas used herein for the purposes of this invention are applied in the same manner as the definitions of substituents according to the definition of the exponents in the following formulas.

[0055]

[0056] Where a is an integer of 0, it refers to the substituent R. 1 This does not exist. That is, when a is 0, it means that all the carbons forming the benzene ring are bonded to hydrogen. In this case, the symbol for 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, the carbons attached to any one of the carbons forming the benzene ring bond as follows, where R 1They can be the same or different from each other, and when a is an integer from 4 to 6, it binds to the carbon of the benzene ring in a similar way, but omits the symbol for the hydrogen that binds to the carbon that forms the benzene ring.

[0057]

[0058] The compounds according to aspects of the present invention and organic electrical components comprising said compounds will be described below.

[0059] According to a specific example of the invention, a compound represented by formula (1) is provided.

[0060]

[0061] In equation (1),

[0062] 1)Ar 1 Ar 2 and Ar 3 Each is independently C6-C 60 aryl group;

[0063] 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.

[0064] 3)R 1 R 2 R 3 R 4 and R 5 Each is independently selected from hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups; and -L'-N(R) a (R) b );

[0065] L' can be selected from a single bond; C6-C 60 arylene group; fluorene group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; and C2-C 60 Heterocyclic groups;

[0066] And R a and R b Each is independently selected from C6-C 60 Aryl group; fluorenyl group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups; or multiple R groups 1 Multiple R 2 Multiple R 3 Multiple R 4 and multiple R 5 They can combine with each other to form aromatic rings and / or heteroaromatic rings.

[0067] The aryl group, fluorene group, arylene group, heterocyclic group, fluorene group, fused ring group, alkyl group, alkenyl group, alkoxy group, and aryloxy group may be substituted by one or more substituents, wherein the substituents are selected from deuterium; halogens; silyl groups; siloxane groups; boron groups; germanium groups; cyano groups; nitro groups; C1-C 20 Alkyl thio 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 with deuterium 20 Aryl group; fluorenyl group; C2-C 20 Heterocyclic group; C3-C 20 Cycloalkyl groups; C7-C 20 arylalkyl groups and C8-C 20 aryl alkenyl groups, wherein the substituents can combine with each other to form a ring, wherein the term "ring" means C3-C. 60 Alicyclic or C6-C 60 Aromatic rings or C2-C 60 Heterocyclic groups or fused rings formed by combinations thereof, including saturated or unsaturated rings.

[0068] In a specific aspect of the invention, the compound represented by formula (1) includes compounds represented by any one of the following formulas (2) to (7).

[0069]

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

[0071] Ar 1 Ar 2 Ar3 ,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 them includes C6-C 24 Aryl groups, more preferably, Ar in formula (1) 1 Or Ar 3 Including C6-C 24 Aryl group.

[0073] Furthermore, R in equation (1) 3 For C6-C 24 Aryl group.

[0074] Furthermore, formula (1) includes compounds represented by any one of 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, compounds represented by formula (1) include compounds represented by formula (11).

[0078]

[0079] In equation (11),

[0080] 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.

[0081] Specifically, in this invention, the compounds represented by formula (1) include compounds P-1 to P-160.

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In another aspect, the present invention provides an organic electrical element comprising: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode and comprising a 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, hole transport layer, emission auxiliary layer, emission layer, electron transport auxiliary layer, electron transport layer, and electron injection layer contains one or more compounds of formula (1). Preferably, the emission layer contains the compound.

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

[0091]

[0092] In equation (12),

[0093] 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 Each can be CR or N independently.

[0094] Where R is hydrogen; C6-C60 aryl group; C3-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C6-C 60 Arylamine group; fluorene group; and can combine with adjacent groups to form rings.

[0095] 2)L 2 Selected from single bonds; C6-C 60 arylene group; C3-C 60 Heteroaryl groups; and divalent aliphatic hydrocarbon groups;

[0096] 3) W is NAr 5 、O、S or CR'R”;

[0097] R' and R” are each independently selected from C1-C 50 Alkyl group; C6-C 60 aryl group; C3-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; and R' and R” can combine with each other to form spirocyclic rings.

[0098] 4)Ar 4 and Ar 5 Each is independently selected from C6-C 60 aryl group; C3-C containing at least one heteroatom of O, N, S, Si or P. 60 Heterocyclic groups; C1-C 50 Alkyl group; C6-C 60 Arylamine group; fluorene group.

[0099] The compounds represented by formula (12) include those represented by any one of the following formulas (13) to (16).

[0100]

[0101] {In equations (13) to (16),

[0102] 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 Z13 Z 14 Z 15 Z 16 L 2 The definitions of 、R'、R” are the same as those above.

[0103] Preferably, Ar of formula (12) 4 and Ar 5 Including C6-C 30 Compounds represented by aryl groups.

[0104] Furthermore, the compounds represented by formula (12) include those represented by formula (17).

[0105]

[0106] In equation (17),

[0107] 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.

[0108] 1)L 1 Selected from single bonds; C6-C 60 arylene group; C3-C 60 Heteroaryl groups; and divalent aliphatic hydrocarbon groups;

[0109] 2) Y is O, S, or NAr 5 ,

[0110] 3)R a and R b Each is independently selected from hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; C1-C 50Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups; and -L'-N(R) a (R) b ); or multiple R a and multiple R b They can combine with each other to form aromatic rings and / or heteroaromatic rings.

[0111] 4) y is an integer from 0 to 3, and z is an integer from 0 to 4.

[0112] Specifically, the compounds represented by formula (12) include compounds 4-1 to 4-52.

[0113]

[0114]

[0115]

[0116]

[0117] 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; 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).

[0118]

[0119]

[0120] {In equations (1) and (18),

[0121] 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.

[0122] 2)Ar 4 and Ar 5 Each is independently selected from C6-C60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups; and -L'-N(R) a (R) b );

[0123] L' can be selected from a single bond; C6-C 60 arylene group; fluorene group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; and C2-C 60 Heterocyclic groups;

[0124] And R a and R b Each is independently selected from C6-C 60 Aryl group; fluorenyl group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups;

[0125] Or Ar 4 and Ar 5 They can combine to form a ring.

[0126] 3)Ar 6 Selected from C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; or at least one of the following formulas (1-a), (1-b), and (1-c).

[0127]

[0128] 4)Ar 9 Ar 10 and Ar 11 Each is independently selected from C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60Alicyclic and C6-C 60 Fused ring groups of aromatic rings; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups; and -L'-N(R) a (R) b );

[0129] 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 They may be the same as or different from each other, and each is independently selected from hydrogen; deuterium; halogen; C6-C. 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; C1-C 50 Alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups; and -L'-N(R) a (R) b );

[0130] Where g, h, i, j are 2 or greater than 2, multiple R 6 R 7 R 8 and R 9 They may be the same or different from each other, and they can combine to form a ring.

[0131] 6)L 6 Selected from single bonds; C6-C 60 arylene group; fluorene group; C3-C 60 Alicyclic and C6-C 60 Fused ring groups of aromatic rings; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups;

[0132] 7)L 5 Selected from C6-C 60 arylene group; fluorene group; C3-C 60 Alicyclic and C6-C 60Fused ring groups of aromatic rings; and C2-C groups containing at least one heteroatom of O, N, S, Si, or P. 60 Heterocyclic groups.

[0133] The present invention also provides an organic electronic element comprising at least one compound represented by formula (12) in the emitter layer.

[0134] Furthermore, the hole transport layer contains a compound represented by formula (19) or formula (20), and the emission auxiliary layer contains a compound represented by formula (21) or formula (22).

[0135]

[0136] {In equations (19) to (22),

[0137] 1)Ar 6 Selected from C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic groups;

[0138] 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 above.

[0139] Specifically, the compounds represented by formula (18) include compounds 13-1 to 13-79 and compounds 2-1 to 2-76.

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] As another example, the present invention provides an organic electronic element comprising: an anode; a cathode; and 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 electron blocking layer (EBL) formed between the emission layer and the hole transport layer; wherein the emission auxiliary layer or electron blocking layer comprises a compound represented by formula (30).

[0152]

[0153] In equation (30),

[0154] R 20 R 21 R 22 R 23 R 24 and R 25 Each is independently selected from hydrogen; deuterium; halogen; C6-C 30 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 30 Heterocyclic group; C3-C 30 Alicyclic and C6-C 30 Fused ring groups of aromatic rings; 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 They can combine with each other to form aromatic rings and / or heteroaromatic rings.

[0155] v is an integer between 0 and 3.

[0156] u, w, x, and y are each an independent integer from 0 to 4.

[0157] Z is an integer from 0 to 5.

[0158] L 20 and L 21Each is a single bond independently; C6-C 30 arylene group; C3-C 30 heteroaryl groups;

[0159] Ar 20 It is C6-C 30 Aryl group; or C3-C 30 heteroaryl groups;

[0160] X 20 It is O, S, NR' or CR'R";

[0161] R' and R” are each independently selected from C1-C 30 Alkyl group; C6-C 30 aryl group; C3-C containing at least one heteroatom of O, N, S, Si or P. 30 Heterocyclic groups; and R' and R” can combine with each other to form spirocyclic rings.

[0162] In this invention, the compound represented by formula (30) is represented by any one of formulas (31) to (38).

[0163]

[0164]

[0165] {In equations (31) to (40),

[0166] R 20 R 21 R 22 R 23 R 24 R 25 L 20 L 21 Ar 20 and X 20 The values ​​of u, v, w, x, y, and z are the same as those defined above.

[0167] In this invention, the compounds represented by formula (30) include the following compounds.

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] refer to Figure 1 The organic electrical component (100) according to the present invention includes a first electrode (120), a second electrode (180) formed on a substrate (110), and an organic material layer comprising 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 component, the first electrode may be a cathode, and the second electrode may be an anode.

[0174] 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 layers other than 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 function as a hole blocking layer.

[0175] Although not shown, the organic electrical component according to the invention may further include a protective layer formed on at least one side of the first electrode and the second electrode, the side being the side opposite to the organic material layer.

[0176] Otherwise, even if the same core is used, the band gap, electrical properties, interface properties, etc. can vary depending on which substituent is bonded to which position. Therefore, the choice of the combination of the core and its associated sub-substitutes 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 lifetime and high efficiency can be achieved at the same time.

[0177] The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a conductive metal or metal oxide or alloy thereof is deposited on a substrate to form a cathode, and an organic material layer comprising 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 the organic electroluminescent device according to an embodiment of the present invention. Furthermore, an emission auxiliary layer (151) can 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).

[0178] As another specific example, the present invention provides an organic electrical component in which the emitting layer in the organic material layer is a phosphorescent emitting layer.

[0179] The compounds represented by formulas (1) and (18) are mixed in a ratio of 1:9 to 9:1 to be included in the emission layer of the organic material layer, wherein the compound represented by formula (12) is also mixed to be included in the emission layer.

[0180] The present invention may further include a light efficiency enhancement layer formed on at least one side of the first electrode on the side opposite to the organic material layer or on the side of the second electrode on the side opposite to the organic material layer.

[0181] As another example, the present invention provides an organic electronic device in which a compound represented by formula (30) is used in an emission assist layer or an electron blocking layer, and preferably is contained in a green emission assist layer. More specifically, a compound represented by formula (39) or formula (40) is contained in a green emission assist layer.

[0182] Furthermore, the present invention provides organic electrical components in which an organic material layer is formed by one of spin coating, nozzle printing, inkjet printing, narrow coating, dip coating, or roll-to-roll processes. 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.

[0183] The organic electrical components according to embodiments of the present invention can be front-emitting, rear-emitting, or dual-sided emitting types, depending on the materials used.

[0184] WOLED (White Organic Light Emitting Diode) offers advantages in achieving high resolution and excellent processability, and can be manufactured using conventional LCD color filter technology. Various structures of WOLEDs, primarily used as backlight devices, have been proposed and patented. Representatively, this includes a lamination method where R (red), G (green), and B (blue) radiating elements are arranged side-by-side, with the R, G, and B emitting layers laminated on top and bottom; electroluminescence via a blue (B) organic emitting layer; and a photoluminescent color conversion material (CCM) method using an inorganic phosphor, employing light from this method. The present invention can be applied to such WOLEDs.

[0185] The present invention also provides an electronic device comprising a display device having the organic electrical components, and a control unit for driving the display device.

[0186] According to another aspect, the present invention provides a display device in which 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 illumination. Here, the electronic device can be a wired / wireless communication terminal currently in use or to be used in the future, and encompasses all kinds of electronic devices, including mobile communication terminals such as portable telephones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP) devices, remote controllers, navigation units, game consoles, various televisions, and various computers.

[0187] In the following, examples of the synthesis of compounds represented by formulas (1) and (2) of the present invention and examples of the preparation of organic electrical components of the present invention will be described in detail by way of examples, but are not limited to the following examples.

[0188] [Synthesis example 1]

[0189] The final product 1 according to the invention, represented by formula (1), is prepared by reacting the nucleus and the sub as shown in reaction scheme 1 below, but is not limited thereto.

[0190] <Reaction Scheme 1>

[0191]

[0192] Example of nuclear synthesis

[0193] The nucleus of reaction scheme 1 can be synthesized through the reaction pathway of reaction scheme 2, but is not limited to this.

[0194] <Reaction Scheme 2>

[0195]

[0196] Synthesis of Intermediate-1

[0197] 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(PPh3)4 (14.2 g, 12.3 mmol), K2CO3 (170 g, 1.2 mol), THF (1.3 L), and water (700 mL) were added and stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The obtained compound was separated by silica gel column chromatography and recrystallized to obtain 55 g (yield: 60%) of intermediate 1.

[0198] Nucleosynthesis

[0199] In a round-bottom flask, intermediate-1 (10 g, 47 mmol), dibenzo[b,d]furan-3-ylboronic acid (12 g, 51.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), K2CO3 (20 g, 141 mmol), THF (160 mL), and water (80 mL) were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 5.7 g (yield: 53%) of core 1.

[0200] Examples of nuclei are shown below, but are not limited to. Furthermore, [Table 1] shows the FD-MS (field desorption-mass spectrometry) values ​​of some compounds belonging to the nucleus.

[0201]

[0202] [Table 1]

[0203]

[0204] Instances of Sub

[0205] Examples of Subs are shown below, but not limited to. Furthermore, [Table 2] shows the FD-MS (field desorption-mass spectrometry) values ​​of some compounds belonging to the Subs.

[0206]

[0207] [Table 2]

[0208] compound FD-MS compound FD-MS Sub 1 m / z = 304.07 (C 18 H 13 BO2S = 304.17)]]> Sub 2 m / z = 304.07 (C 18 H 13 BO2S = 304.17)]]> Sub 3 m / z = 354.09 (C 22 H 15 BO2S = 354.23)]]> Sub 4 m / z = 354.09 (C 22 H 15 BO2S = 354.23)]]> Sub 5 m / z = 354.09 (C 22 H 15 BO2S = 354.23)]]> Sub 6 m / z = 380.10 (C 24 H 17 BO2S = 380.27)]]> Sub 7 m / z = 404.10 (C 26 H 17 BO2S = 404.29)]]> Sub 8 m / z = 380.10 (C 24 H 17 BO2S = 380.27)]]> Sub9 m / z = 385.14 (C 24 H 12 D5BO2S = 385.30)]]> Sub 10 m / z = 430.12 (C 28 H 19 BO2S = 430.33) <!-- 37 -->]]> Sub 11 m / z = 430.12 (C 28 H 19 BO2S = 430.33)]]> Sub 12 <![CDATA[m / z=480.14(C 32 H 21 BO2S=480.39)]]> Sub 13 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]> Sub 14 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]> Sub 15 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]> Sub 16 <![CDATA[m / z=380.10(C 24 H 17 BO2S=380.27)]]> Sub 17 <![CDATA[m / z=385.14(C 24 H 12 D5BO2S=385.30)]]> Sub 18 <![CDATA[m / z=430.12(C 28 H 19 BO2S=430.33)]]> Sub 19 <![CDATA[m / z=430.12(C 28 H 19 BO2S=430.33)]]> Sub 20 <![CDATA[m / z=480.14(C 32 H 21 BO2S=480.39)]]> Sub 21 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]> Sub 22 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]> Sub 23 <![CDATA[m / z=456.14(C 30 H 21 BO2S=456.37)]]>

[0209] Synthesis example of the product

[0210] Synthesis example of P-41

[0211]

[0212] In a round-bottom flask, nucleus 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (5.7 g, 41.3 mmol), THF, and water were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.6 g (yield: 57%) of P-41.

[0213] Synthesis example of P-91

[0214]

[0215]

[0216] In a round-bottom flask, nucleus 1 (5 g, 14 mmol), Sub 9 (5.8 g, 15.4 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (5.8 g, 41.9 mmol), THF, and water were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.7 g (yield: 51%) of P-91.

[0217] Synthesis example of P-106

[0218] In a round-bottom flask, nucleus 1 (5 g, 14 mmol), Sub 16 (5.8 g, 15.4 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (5.8 g, 41.9 mmol), THF, and water were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 5.8 g (yield: 63%) of P-106.

[0219] Synthesis example of P-146

[0220]

[0221] In a round-bottom flask, nucleus 11 (5 g, 14 mmol), Sub 2 (5.8 g, 15.4 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (5.8 g, 41.9 mmol), THF, and water were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 4.7 g (yield: 51%) of P-146.

[0222] Synthesis example of P-4

[0223]

[0224] In a round-bottom flask, nucleus 1 (5 g, 14 mmol), Sub 6 (5.9 g, 15.4 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (5.8 g, 41.9 mmol), THF, and water were added, and the mixture was stirred at 90 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silica gel column chromatography and recrystallized to obtain 6.1 g (yield: 66%) of P-4.

[0225] [Table 3] shows the FD-MS (field desorption-mass spectrometry) values ​​of some compounds that belong to the products.

[0226] [Table 3]

[0227]

[0228]

[0229]

[0230]

[0231] [Synthesis example 2]

[0232] The compound represented by formula (12) according to the invention (final product 2) can be prepared by reacting Sub 3-1 and Sub 3-2 as shown in reaction scheme 4 below, but is not limited thereto.

[0233] <Reaction Scheme 4>

[0234]

[0235] Synthesis example 4-1

[0236]

[0237] 3-Bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) was dissolved in THF, and (9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole-3-yl)boric acid (8.8 g, 20 mmol), Pd(PPh3)4 (0.03 equivalents), K2CO3 (3 equivalents), and water were added and stirred under reflux. After the reaction was complete, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO4 and concentrated. The obtained organic matter was separated by silica gel column chromatography and recrystallized to obtain 9.2 g (yield: 72%) of product.

[0238] Synthesis example 4-21

[0239]

[0240] The reaction of 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) was carried out in the same manner as in 4-1 to give 6.5 g (yield: 71%) of the product.

[0241] Synthesis example 4-25

[0242]

[0243] The reaction of 9-([1,1'-biphenyl]-4-yl)-3-bromo-9H-carbazole (8.0 g, 20 mmol) and (9-(naphthyl-2-yl)-9H-carbazole-3-yl)boronic acid (6.7 g, 20 mmol) was carried out in the same manner as in 4-1 to give 9.2 g (yield: 75%) of the product.

[0244] Synthesis example 4-31

[0245]

[0246] The reaction of 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) was carried out in the same manner as in 4-1 to give 9.5 g (yield: 73%) of the product.

[0247] Synthesis example 4-32

[0248]

[0249] The reaction of 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]thieno[2,3-a]carbazole-3-yl)boronic acid (10.9 g, 20 mmol) was carried out in the same manner as in 4-1 to give 11.5 g (yield: 69%) of the product.

[0250] Synthesis example 4-34

[0251]

[0252] The reaction of 4-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) and (4-(dibenzo[b,d]thiophene-3-yl)phenyl)boronic acid (6.1 g, 20 mmol) was carried out in the same manner as in 4-1 to give 6.7 g (yield: 67%) of the product.

[0253] Synthesis example 4-35

[0254]

[0255] The reaction of 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) was carried out in the same manner as in 4-1 to give 6.1 g (yield: 70%) of the product.

[0256] [Table 4]

[0257]

[0258]

[0259] [Synthesis example 3]

[0260] The final product according to the invention, represented by formula (18), can be prepared by the following reaction, but is not limited thereto.

[0261] Synthesis examples 13-17

[0262]

[0263] 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), Pd2(dba)3 (0.05 equivalents), PPh3 (0.1 equivalents), and NaOt-Bu (3 equivalents) were added. The mixture was stirred and refluxed at 100 °C for 24 hours. After the reaction was complete, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO4 and concentrated. The obtained organic matter was separated by silica gel column chromatography and recrystallized to obtain 12.9 g (yield: 84%) of product.

[0264] Synthetic examples 13-32

[0265]

[0266] 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-fluorene-2-amine (7.2 g, 20 mmol), Pd2(dba)3 (0.05 equivalents), PPh3 (0.1 equivalents), and NaOt-Bu (3 equivalents) were added, and the mixture was stirred and refluxed at 100 °C for 24 hours. After the reaction was complete, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO4 and concentrated. The obtained organic matter was separated by silica gel column chromatography and recrystallized to obtain 13.8 g (yield: 85%) of product.

[0267] Synthesis examples 2-34

[0268]

[0269]

[0270] In a round-bottom flask, Sub 4(19) (9.5 g, 20 mmol), Sub 5(4) (4.7 g, 20 mmol), Pd2(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 added, and the reaction was carried out at 100 °C. When the reaction was complete, the reaction mixture was extracted with CH2Cl2 and water. The organic layer was dried over MgSO4 and concentrated. The obtained compound was separated by silica gel column chromatography and recrystallized to obtain 9.8 g (yield: 78%) of 2-34.

[0271] Synthesis example 2-58

[0272] In a round-bottom flask, Sub 4(35) (8.4 g, 20 mmol), Sub 5(7) (5.7 g, 20 mmol), Pd2(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 in the same manner as in 2-34 to give 2-58 (10.4 g, 83%).

[0273] Synthesis examples 2-59

[0274]

[0275] In a round-bottom flask, Sub 4(32) (12.9 g, 20 mmol), Sub 5(11) (7.9 g, 20 mmol), Pd2(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 in the same manner as in 2-34 to give 2-59 (5.2 g, 79%).

[0276] Synthesis examples 2-69

[0277]

[0278] In a round-bottom flask, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (7.2 g, 20 mmol), 4-(2-bromophenyl)-9,9-diphenyl-9H-fluorene (9.5 g, 20 mmol), Pd2(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 in the same manner as in 2-34 to give 2-69 (12.2 g, 81%).

[0279] Synthesis example 2-71

[0280]

[0281] 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), Pd2(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 in the same manner as in 2-34 to give 2-71 (12.9 g, 78%).

[0282] [Synthesis Example 4]

[0283] The final product represented by formula (30) according to the invention is prepared by reacting Sub 30 and Sub 31 as shown in reaction scheme 5 below, but is not limited thereto.

[0284] <Reaction Scheme 5>

[0285]

[0286] Sub Synthesis example of 30

[0287] <Reaction Scheme 6>

[0288]

[0289] Synthesis example of Sub 30(81)

[0290]

[0291] In a round-bottom flask, 3-(9-phenyl-9H-fluorene-9-yl)aniline (6.7 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd2(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 in the same manner as in 2-34 to give Sub 30(81) (8.83 g, 84%).

[0292] Instance of Sub 31

[0293] Examples of Sub 31 are as follows, but not limited to these.

[0294]

[0295] [Table 5]

[0296]

[0297] Synthesis example 2-72

[0298]

[0299] In a round-bottom flask, N-(3-(9-phenyl-9H-fluorene-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), Pd2(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 in the same manner as in 2-34 to give 2-72 (12.2 g, 81%).

[0300] Synthesis example 2-81

[0301]

[0302] In a round-bottom flask, Sub 30(81) (10.3 g, 20 mmol), Sub 31-4 (4.66 g, 20 mmol), Pd2(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 in the same manner as in 2-34 to give 2-81 (10.3 g, 76%).

[0303] [Table 6]

[0304]

[0305]

[0306] Manufacturing and evaluation of organic electronic components

[0307] Example 1) Fabrication and Evaluation of Green Organic Light Emitting Diodes

[0308] (main body)

[0309] First, on the ITO layer (anode) formed on the glass substrate, N... 1 -(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1 1,4-Phenylenol-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with 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 with a thickness of 60 nm. Then, the compound of the present invention represented by formula (1) as the main component and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant with a weight ratio of 95:5 were deposited on the hole transport layer to form an emitter layer with a thickness of 30 nm. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0310] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2 The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0311] [Comparative Examples 1 to 4]

[0312] OLEDs were prepared in the same manner as in Example 1, but comparative compounds A, B, C and D were used as the main components.

[0313]

[0314] [Table 7]

[0315]

[0316] Example 2) Fabrication and Evaluation of Green Organic Light Emitting Diodes

[0317] (The mixed main body)

[0318] First, on the ITO layer (anode) formed on the glass substrate, N... 1 -(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1 1,4-Phenylenol-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with 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 with 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) in a 6:4 ratio as the main body and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant in a 95:5 weight ratio was deposited on the hole transport layer to form an emitter layer with a thickness of 30 nm. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0319] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2 The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0320] [Comparative Examples 5 to 8, Comparative Examples 10 to 13]

[0321] OLEDs were prepared in the same manner as in Example 2, but comparative compounds A, B, C and D were used instead of the compounds of the present invention represented by formula (1) as the main body.

[0322] [Compare Example 9 and Compare Example 14]

[0323] OLEDs were prepared in the same manner as in Example 2, but comparative compound E was used instead of the compound of the present invention represented by formula (12) as the main body.

[0324]

[0325] [Table 8]

[0326]

[0327]

[0328] Example 3) Fabrication and Evaluation of Green Organic Light Emitting Diodes

[0329] (Launching auxiliary layer + hybrid main body)

[0330] First, on the ITO layer (anode) formed on the glass substrate, N... 1 -(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1-Phenylen-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with a thickness of 60 nm. Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Then, the compound of the present invention represented by formula (18) as an emission assist layer material was vacuum deposited to a thickness of 20 nm to form an emission assist layer. After the emission assist layer was formed, a mixture of the compound of the present invention represented by formula (1) and the compound represented by formula (12) in a 6:4 ratio and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant was deposited on the emission assist layer at a weight ratio of 95:5 to form an emission layer with a thickness of 30 nm. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0331] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2 The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0332] [Comparative Examples 15 to 29]

[0333] OLEDs were prepared in the same manner as in Example 3, but each was prepared using comparative compounds A to E instead of the compounds of the present invention represented by formula (1) as the main body.

[0334] [Table 9]

[0335]

[0336]

[0337] Example 4) Fabrication and Evaluation of Green Organic Light Emitting Diodes (Hole transport layer + emission auxiliary layer + hybrid main body)

[0338] First, on the ITO layer (anode) formed on the glass substrate, N... 1-(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1 -Phenylen-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with a thickness of 60 nm. Then, the compound represented by formula (18) was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Then, the compound represented by formula (18) as the emission assist layer material was vacuum deposited to a thickness of 20 nm to form an emission assist layer. After the emission assist layer was formed, a mixture of the compound of the present invention represented by formula (1) and the compound represented by formula (12) in a 6:4 ratio as the main body and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as a dopant in a 95:5 weight ratio was deposited to form an emission layer with a thickness of 30 nm. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0339] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2 The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0340] [Table 10]

[0341]

[0342]

[0343] As can be seen from the results in Tables 7 to 10, organic electronic components using the organic electronic device material of the present invention as the phosphorescent host can significantly improve high luminous efficiency, low driving voltage, and lifetime.

[0344] Table 7 shows the superiority of the compounds of the present invention compared to the comparative compounds when the compounds of the present invention represented by formula (1) are used as a single host. In the results for comparative compounds A and C, when 3-dibenzofuran is substituted, performance in all aspects of driving voltage, efficiency, and lifetime is improved compared to 4-dibenzofuran. In the results for comparative compounds A and B, or comparative compounds C and D, it can be confirmed that the performance of triazine partially substituted with two dibenzothiophenes or dibenzofurans is improved compared to triazine partially substituted with one dibenzothiophene or dibenzofuran. Therefore, it can finally be confirmed that the compounds of the present invention wherein the triazine is substituted with 3-dibenzofuran and connected to the other side via a linker having 4-dibenzothiophene exhibit significantly different improved results compared to comparative compounds A through D. It is suggested that the energy levels (HOMO, LUMO, T1, etc.) of compounds can vary significantly depending on the type or position of substituents, and that differences in the physical properties of compounds can serve as key factors in improving device performance (e.g., energy balance) during device deposition, leading to different device outcomes.

[0345] Table 8 shows that when the compounds represented by formula (12) and formula (1) are mixed, they significantly outperform other comparative combinations. This result also supports the explanation for the single-body case, and when combined with the compound of formula (12), the driving voltage and efficiency can be improved by approximately 24% and the lifetime by approximately 63% compared to the single-body case. When the two bodies are premixed, the aging rate is crucial for deposition at a given rate, and the compounds of the present invention exhibit better aging rates than other materials, and in particular, Ar… 1 Ar 3 and R 3 At least one of them is C6-C 24 Compounds with aryl groups showed the best results in aging tests.

[0346] Table 9 shows examples of using a mixture of compounds of formula (1) and formula (12) as the emitter layer host and using a compound represented by formula (18) in the emitter auxiliary layer, and shows that the efficiency is improved by about 60% and the lifetime is improved by about 20% compared to Table 8. Here, compared to the results in Table 7, using the compound represented by formula (18) as the hole transport compound also produces slight improvements in driving voltage, efficiency and lifetime.

[0347] That is, the compounds of the present invention show improved results even when used as a single entity compared with known compounds, but significant results are obtained when used in combination with compounds represented by formula (12), or when compounds represented by formula (18) are used in emission auxiliary layers or hole transport layers.

[0348] Example 5) Fabrication and Evaluation of Blue Organic Light Emitting Diode

[0349] First, on the ITO layer (anode) formed on the glass substrate, N... 1 -(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1 1,4-Phenylenyl-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with a thickness of 60 nm. Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) was vacuum deposited on this layer to a thickness of 60 nm to form a hole transport layer. Then, the compound of the present invention, as the emission assist layer material, was vacuum deposited to a thickness of 20 nm to form an emission assist layer. After forming the emission assist layer, 9,10-bis(naphthyl-2-yl)anthracene as the host and BD-052X (Idemitsu Kosan) as the dopant were used on the emission assist layer in a 96:4 ratio, thereby depositing an emission layer with a thickness of 30 nm on the emission assist layer. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0350] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2 The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0351] [Comparative Examples 35 to 37]

[0352] OLEDs were prepared in the same manner as in Comparative Example 5, but without using an emission auxiliary layer and with comparative compound F, comparative compound G, and compounds 2-81 of the present invention used as hole transport layer materials.

[0353] [Comparative Example 38]

[0354] OLEDs were prepared in the same manner as in Comparative Example 5, but without using an emission-assisted layer.

[0355] [Comparative Examples 39 to 40]

[0356] OLEDs were prepared in the same manner as in Comparative Example 5, but comparative compound F or comparative compound G was used as the emission auxiliary layer material.

[0357]

[0358] [Table 11]

[0359]

[0360] Example 6) Fabrication and Evaluation of Green Organic Light Emitting Diodes

[0361] First, on the ITO layer (anode) formed on the glass substrate, N... 1 -(naphthyl-2-yl)-N 4 N 4 -bis(4-(naphth-2-yl(phenyl)amino)phenyl)-N 1 1,4-phenylphenyl-1,4-diamine (hereinafter abbreviated as 2-TNATA) was vacuum deposited to form a hole injection layer with a thickness of 60 nm. Then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) as a hole transport compound was vacuum deposited to a thickness of 60 nm to form a hole transport layer. Then, the compound of the present invention represented by formula (30) as the emission assist layer material was vacuum deposited to a thickness of 20 nm to form an emission assist layer. After the emission assist layer was formed, 4,4-bis(9H-carbazole-9-yl)-1,1'-biphenyl as the host and Ir(ppy)3[tris(2-phenylpyridine)-iridium] as the dopant was used on the emission assist layer in a ratio of 95:5, thereby depositing an emission layer with a thickness of 30 nm. An OLED was fabricated by vacuum-depositing (1,1'-biphenyl)-4-hydroxyaluminum (2-methyl-8-quinoline hydroxyaluminum, hereinafter abbreviated as BAlq) to a thickness of 10 nm as a hole-blocking layer and tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) to a thickness of 40 nm. Subsequently, an 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.

[0362] A forward bias DC voltage was applied to the OLEDs manufactured through the examples and comparative examples, and electroluminescence (EL) was measured using a PR-650 from Photoresearch Co., and lifetime measurement was performed using a lifetime measurement instrument manufactured by McScience Inc. at 5000 cd / m². 2The reference luminance measurement T95 lifetime is shown in the table below. The manufacturing and evaluation results of the device are presented.

[0363] [Comparative Examples 41 to 42]

[0364] OLEDs were prepared in the same manner as in Comparative Example 5, but comparative compound F or comparative compound G was used as the emission auxiliary layer material.

[0365] [Table 12]

[0366]

[0367]

[0368] As can be seen from the results in Tables 11 and 12, when OLEDs are manufactured using the material of the present invention for organic electroluminescent devices as the emission auxiliary layer material, the driving voltage of the organic electroluminescent device can be reduced and the luminous efficiency and lifetime can be significantly improved compared with the comparative examples that do not use the material for the emission auxiliary layer or use comparative compound F or comparative compound G.

[0369] Table 11 shows the production results of the blue organic light-emitting device. It can be confirmed that excellent results were obtained when the compounds of the present invention were used as emission auxiliary layers. The results of Comparative Examples 39 or 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 superior to 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 this difference in physical properties is a major factor in improving device performance (e.g., energy balance) during device deposition, thus resulting in different device outcomes.

[0370] Table 12 shows the production results of the green organic light-emitting device. When the compounds of the present invention are used as the emission auxiliary layer, the results are significantly better than those of the comparative compounds. This is also due to the influence of specific substituents such as DBT, DBF, Cz, and fluorene, and specifically, the green auxiliary layer is significantly superior to the blue auxiliary layer. Furthermore, in the case of the blue auxiliary layer, the compounds substituted with DBT and DBF exhibit the best properties, but the results for the green auxiliary layer show that the fluorene-substituted compounds have the best results. This indicates that even with the same emission auxiliary layer compound, the properties required depending on the color of the emission layer differ, thus yielding results that cannot be deduced by those skilled in the art.

[0371] Although exemplary embodiments of the invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the invention as disclosed in the appended claims. Therefore, the embodiments disclosed herein are intended to illustrate the scope of the inventive concept, and the scope of the invention is not limited by the embodiments. The scope of the invention should be interpreted based on the appended claims, and should be construed as including all inventive concepts within the scope equivalent to the claims.

Claims

1. A compound represented by formula (1) Formula (1) wherein, In formula (1), 1) Ar 1 , Ar 2 , and Ar 3 each independently is a C6-C 24 aryl group, 2) 1 and e are an integer of 0 to 4, d and m are an integer of 0 to 4, a and b are an integer of 0 to 3, n is 1, c is an integer of 0 to 4, 3) R 1 , R 2 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen; deuterium; halogen; and C1-C 50 alkyl groups; R 3 is selected from the group consisting of hydrogen; deuterium; halogen; phenyl groups; biphenyl groups; fluorenyl groups; and C1-C 50 alkyl groups; or multiple R 1 , multiple R 2 , multiple R 3 , multiple R 4 , and multiple R 5 may combine with each other to form a benzene ring, wherein the aryl group, fluorenyl group, and alkyl group can be substituted with one or more substituents selected from the group consisting of deuterium; halogen; and C1-C4alkyl group. 20 alkyl group.

2. The compound according to claim 1, wherein the compound represented by formula (1) is any one of the following formulae (2), (5) and (6) <Formula (2)> <Formula (5)> <Formula (6)> In formulae (2), (5) and (6), 3. The compound according to claim 1, wherein formula (1) is any one of the following formulae (8) and (10) Ar 1 , Ar 2 , Ar 3 , 1, m, a, b, c, d, e, R 1 , R 2 , R 3 , R 4 and R 5 are the same as defined in claim 1. <Formula (8)> <Formula (10)> In formulae (8) and (10), 4. The compound according to claim 1, wherein the compound represented by formula (1) is formula (11) Ar 1 , Ar 2 , Ar 3 , 1, m, a, b, d, e, R 1 , R 2 , R 4 and R 5 are the same as defined in claim 1. <Formula (11)> In formula (11), 5. The compound according to claim 1, wherein the compound represented by formula (1) is any one of the following compounds Ar 1 , Ar 2 , Ar 3 , 1, m, n, a, b, c, d, e, R 1 , R 2 , R 3 , R 4 and R 5 are the same as defined in claim 1. a first electrode; 。 6. An organic electronic element, comprising: a second electrode; and an organic material layer provided between the first electrode and the second electrode and containing the compound according to any one of claims 1 to 5.

7. The organic electronic element according to claim 6, 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.

8. The organic electronic element according to claim 7, wherein the compound is contained in the emission layer.

9. The organic electronic element according to claim 8, wherein a compound represented by formula (12) is further contained in the emission layer <Formula (12)> In formula (12), 10. The organic electronic element according to claim 9, wherein formula (12) is any one of the following formulae (13) to (16) 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, wherein R is hydrogen; or C1-C 50 alkyl groups, 2) L 2 is a single bond; 3) W is NAr 5 O, S or CR'R"; R' and R" are each independently selected from the group consisting of C1-C 50 alkyl groups; C6-C 60 aryl groups; C3-C 60 heterocyclic groups; and R' and R" can be combined with each other to form a spiro ring; 4) Ar 4 and Ar 5 each independently is selected from a C6-C 30 aryl group. Formula (13) Formula (14) Formula (15) Formula (16) In formulae (13) to (16), 11. The organic electronic element according to claim 8, wherein a compound represented by formula (17) is further contained in the emission layer 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 in claim 9. <Formula (17)> In formula (17), 4) y is an integer of 0 to 3, z is an integer of 0 to 4. 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 are the same as defined in claim 9, 1) L 1 is a single bond, 2) Y is O, S or NAr 5 , 3) R a and R b each independently is selected from the group consisting of hydrogen; deuterium; halogen; and C1-C 50 alkyl groups, 12. The organic electronic element according to claim 9 or 11, wherein the compound represented by formula (12) or (17) is any one of the following compounds 13. A display device comprising the organic electronic element according to claim 6; and a control means for driving the display device. 。 14. The display device according to claim 13, wherein the organic electronic element is at least one of elements of an OLED, an organic solar cell, an organic photoconductor and an organic transistor. ​ 15. The display device according to claim 13, wherein the organic electronic element is an element for monochromatic or white illumination.

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