Organic electronic element and electronic device thereof

Abstract

The present invention relates to an organic light emitting display device and, more specifically, to an organic light emitting display device in which a light emitting area and a transmitting area coexist, and which can solve process difficulty by patterning an electrode without using a shadow mask, and can implement a full-screen display such as a UDC and an image sensor, and furthermore, can respond to concerns about human health and the environment.

Description

Organic electronic components and electronic devices thereof

[0001] The present invention relates to an organic light-emitting display device including a light-emitting region and a transmission region that do not use a perfluorinated compound.

[0002] With the continuous advancement of display technology, user demand for display devices is increasing. Terminal display devices are being developed toward flexibility, full screens, and high integration. For smartphone displays, bezels are being reduced to increase screen size, and bezel-less under-displays are being developed. This process is also leading to the development of technologies such as the Under Display Camera (UDC) or Under Panel Sensor (UPS), where physical buttons on the front of the smartphone disappear into the screen. For UDC cameras to function properly, the display must have high light transmittance. Therefore, smartphones and electronic devices incorporating devices such as UDCs require high light transmittance. Korean Patent No. 10-2324529, an invention by the present applicant, discloses that this goal can be achieved by forming a metal patterning layer. In addition, Korean Patent Publication No. 10-2022-0006001 discloses a metal patterning method using an organic thin film that forms an organic patterning layer by vacuum deposition and selectively repels metal materials.

[0003] Two main electrode patterning methods are commonly used. The first is to pattern electrodes in the desired area using a shadow mask, and the second is to create a pattern by irradiating the cathode with a laser. However, electrode patterning using a shadow mask is problematic because the typical material properties of metal masks cause warping during the high-temperature deposition process, distorting the mask shape and electrode pattern. Consequently, mask maintenance inevitably requires time and costs, making it unsuitable for mass production of devices.

[0004] In addition, the method of patterning electrodes using a laser causes the inconvenience of having to determine the type and intensity of the laser so that the substrate is not damaged in the way the electrodes are patterned due to the inherent properties of the laser.

[0005] Therefore, in order to implement full-screen display devices such as image sensors and UDCs, it is essential to implement a device in which both a light-emitting area and a transparent area exist simultaneously, and it is also necessary to develop optimal organic light-emitting display technology that can resolve process difficulties.

[0006] Meanwhile, perfluorinated compounds (PFCs) possess excellent water and oil repellency, as well as heat resistance and friction reduction. These chemicals are widely used in adhesives, coatings, and plastics. They are also highly versatile as metal patterning layers. However, they are easily bioaccumulative, persistent in nature, long-lasting, and highly toxic. Consequently, concerns about their potential impact on human health and the environment are prompting legislation in several countries to restrict their use.

[0007] The present invention aims to provide an optimal organic light-emitting display device in which a light-emitting area and a transparent area exist in common, electrodes are patterned without using a shadow mask to resolve process difficulties, and a full-screen display such as an image sensor or UDC can be implemented, and furthermore, concerns about human health and the environment can be addressed.

[0008] The present invention comprises a substrate; an anode (100) disposed on the substrate; a first portion (110) which is a light-emitting region; and a second portion (120) which is a transmission region on the anode (100);

[0009] The first part (110) and the second part (120) include an organic layer (111) formed in common;

[0010] The above organic layer (111) includes a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115).

[0011] A cathode (118) exists on the organic layer (111) of the first part (110).

[0012] A metal patterning layer (121) exists on the organic layer (111) of the second part (120).

[0013] The above metal patterning layer (121) provides an organic electric element that does not contain a perfluorinated compound.

[0014] In addition, in another aspect, the present invention provides an electronic device including the organic electric element.

[0015] The organic light-emitting display device according to the present invention has a light-emitting area and a transmissive area simultaneously, and can solve process difficulties by patterning electrodes without using a shadow mask, and can achieve high light-emitting efficiency and low driving voltage, so that it can be used in the manufacture of displays for UDC and UPS, and furthermore, can respond to concerns about human health and the environment.

[0016] Figures 1 to 13 are exemplary diagrams of an organic light-emitting display device according to the present invention.

[0017] 100: positive pole 110: first part

[0018] 111: Organic layer 112: Hole injection layer

[0019] 113: Hole transport layer 114: Light emitting layer

[0020] 115: Electron transport layer 116: Electron injection layer

[0021] 117: Patterning auxiliary photosensitive layer 118: Cathode

[0022] 120: Part 2 121: Metal patterning layer

[0023] 122: Light-emitting auxiliary layer 123: Hole-blocking layer

[0024] 124: First light-emitting auxiliary layer 125: Second light-emitting auxiliary layer

[0025] 130: Part 3

[0026] When assigning reference numerals to components in each drawing, it should be noted that identical components are assigned the same numerals whenever possible, even if they appear on different drawings. Furthermore, when describing the present invention, if a detailed description of a related known configuration or function is deemed likely to obscure the gist of the present invention, such detailed description will be omitted.

[0027] In the specification, where "includes," "has," and "consists of" are used, other parts may be added, unless "only" is used. When a component is expressed in the singular, it may include cases where it includes the plural, unless otherwise explicitly stated.

[0028] Additionally, terms such as first, second, A, B, (a), (b), etc. may be used to describe components of the present invention. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0029] Furthermore, when a component such as a layer, membrane, region, or plate is said to be "on" or "over" another component, it should be understood that this includes not only the case where it is "directly on" the other component, but also the case where there are other components in between. Conversely, when a component is said to be "directly on" another part, it should be understood that there are no other components in between.

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

[0031] The term “halo” or “halogen” as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

[0032] The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0033] The term "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise stated, includes a straight-chain or branched chain group having a double bond or triple bond of 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms or 2 to 12 carbon atoms, but is not limited thereto.

[0034] The term "cycloalkyl" or "cycloalkyl" as used in the present invention means, unless otherwise stated, an alkyl forming a ring having 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 25 carbon atoms, 3 to 18 carbon atoms or 3 to 12 carbon atoms, but is not limited thereto.

[0035] The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms.

[0036] The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise specified, has, but is not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.

[0037] The term "alkylthio group" as used herein means an alkyl group having a sulfur radical attached thereto, and unless otherwise stated, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms.

[0038] The term "arylthio group" as used herein means an aryl group having a sulfur radical attached thereto, and unless otherwise stated, has, but is not limited to, 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 25 carbon atoms, 1 to 18 carbon atoms, or 1 to 12 carbon atoms.

[0039] The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, have, but are not limited to, 6 to 60 carbon atoms, 6 to 30 carbon atoms, 6 to 25 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms, respectively. In the present invention, the aryl group or arylene group refers to a single ring or multi-ring aromatic group, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0040] The prefix "aryl" or "ar" refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the aryl-substituted radical has the number of carbon atoms described herein.

[0041] Also, when prefixes are named consecutively, it means that the substituents are listed in the order they were first written. For example, in the case of arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of arylcarbonylalkenyl group, it means an alkenyl group substituted with an arylcarbonyl group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

[0042] The term "heterocyclic group" used in the present invention, unless otherwise stated, includes one or more heteroatoms, has 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 25 carbon atoms, 2 to 18 carbon atoms, or 2 to 12 carbon atoms, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heteroaromatic ring. It may also be formed by bonding adjacent functional groups.

[0043] The term “heteroatom” as used herein refers to N, O, S, P or Si unless otherwise stated.

[0044] Additionally, “heterocyclic group” refers to a single ring, ring aggregate, fused multiple ring system, spiro compound, etc. containing a heteroatom. In addition, compounds containing a heteroatom group such as SO2, P=O, etc. instead of carbon forming a ring, such as the compounds below, may also be included in the heterocyclic group.

[0045]

[0046] The term "aliphatic ring" used in the present invention means a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, means a ring having 3 to 60 carbon atoms, a ring having 3 to 30 carbon atoms, a ring having 3 to 25 carbon atoms, a ring having 3 to 18 carbon atoms, or a ring having 3 to 12 carbon atoms, but is not limited thereto. For example, even when an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, are fused, it is considered an aliphatic ring.

[0047] The term "fluorenyl group", "fluorenylene group" or "fluorenetriyl group" used in the present invention, unless otherwise stated, means a monovalent, divalent or trivalent functional group in which R, R' and R" in the structure below are all hydrogen, and a "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" means that at least one of the substituents R, R' and R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded. In the present specification, regardless of valence, a fluorenyl group, a fluorenylene group and a fluorenetriyl group may all be referred to as a fluorene group.

[0048]

[0049] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', but may also be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, but it may also be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent. In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing the compound name or substituent name. For example, pyrido[4,3-d]pyrimidine can be written as pyridopyrimidine, benzofuro[2,3-d]pyrimidine can be written as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene can be written as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline can be written as benzoquinoxaline.

[0050] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0051]

[0052] Here, if a is an integer of 0, the substituent R 1 is absent, and if a is an integer of 1, there is one substituent R 1 is bonded to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it is bonded as follows, in which case R 1may be the same or different, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0053]

[0054] Additionally, unless otherwise stated herein, when indicating a condensed ring, the number in the expression "number-condensed ring" indicates the number of condensed rings. For example, a form in which three rings are condensed together, such as anthracene, phenanthrene, and benzoquinazoline, can be expressed as a 3-condensed ring.

[0055] Additionally, unless otherwise stated herein, when a ring is expressed in the form of a 'number-atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' represents the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.

[0056] In addition, unless otherwise stated in this specification, the rings formed by bonding adjacent groups to each other are C6~C 60 Aromatic ring group; Fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 may be selected from the group consisting of aliphatic ring groups;

[0057] At this time, unless otherwise stated in this specification, 'neighboring groups' means, as explained with the following chemical formula as an example, R 1 and R 2 Kiri, R 2 Wow R 3 Kiri, R 3 and R 4 Kiri, R 5 Wow R 6 Not only that, but R shares one carbon 7 and R 8Kirido is included, and R 1 and R 7 Kiri, R 1 and R 8 Kiri or R 4 Wow R 5 Substituents bonded to non-adjacent ring constituents (such as carbon or nitrogen) may also be included. That is, if there is a substituent on an adjacent ring constituent such as carbon or nitrogen, they can be adjacent groups, but if no substituent is bonded to the ring constituent at the adjacent position, the substituent bonded to the next ring constituent can be a neighboring group, and substituents bonded to the same ring constituent carbon can also be considered neighboring groups.

[0058] In the chemical formula below, R 7 and R 8 When substituents bonded to the same carbon combine with each other to form a ring, a compound containing a spiro moiety can be formed.

[0059]

[0060] Additionally, in this specification, the expression 'adjacent groups can combine with each other to form a ring' is used with the same meaning as 'adjacent groups combine with each other to selectively form a ring', and means a case where at least one pair of adjacent groups combine with each other to form a ring.

[0061] In addition, the term "perfluorinated compound" used in this specification refers to a perfluorinated (-C) compound in which hydrogen in the basic skeleton of a hydrocarbon is replaced with fluorine. n F 2n+1 ) refers to a compound in which an alkyl group is substituted, and for example, it refers to a compound in which a fully fluorinated carbon backbone is substituted by a functional group such as carboxylate, sulfonate, or phosphonate. However, sp 2Compounds in which F, CF2 or CF3 substituents are directly substituted on sp carbon are not included in perfluorinated compounds.

[0062] Additionally, the term "sp carbon" as used herein refers to carbon in which one s orbital and one p orbital are hybridized and are bonded to two atoms (including a triple bond).

[0063] Also, the term "sp" used in this specification 2 Carbon" is a hybridized carbon with one s orbital and two p orbitals, and is bonded to three atoms (including double bonds).

[0064] Also, the term "sp" used in this specification 3 Carbon" is a hybridized carbon with one s orbital and three p orbitals, and is bonded to four atoms (all single bonds).

[0065]

[0066] Hereinafter, an organic electric device according to an embodiment of the present invention will be described in detail with reference to the attached FIGS. 1 to 13.

[0067] FIGS. 1 to 13 are drawings schematically illustrating the configuration of an organic light-emitting display device according to one embodiment of the present invention.

[0068] Referring to FIGS. 1 to 13, an organic light-emitting display device according to an embodiment of the present invention sequentially includes an anode (100) on a substrate (not shown), a first portion (110) as a light-emitting area, and a second portion (120) as a transmissive area on the anode (100), and a third portion (130) as a common area on the first portion (110) and the second portion (120). In addition, the first part (110) and the second part (120) include an organic layer (111) that is formed in common, and the organic layer (111) includes a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115). A cathode (118) is formed on the organic layer (111) of the first part (110), and a metal patterning layer (121) is formed on the organic layer (111) of the second part (120).

[0069] In FIGS. 1 to 11, the height of the first portion (110) and the height of the second portion (120) are illustrated as being the same, but their heights may be the same or different. In addition, FIGS. 1 to 11 are schematic drawings for explaining the laminated structure of an organic light-emitting display device, and the height, area, formation position, etc. of the first portion (110) and the second portion (120) are not limited by these drawings.

[0070] The anode (100) may be a transparent electrode. Typically, a material forming the transparent electrode may be selected from transparent conductive oxides (TCOs), such as indium tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO2), or indium zinc oxide (IZO), and combinations thereof, but is not limited thereto. In addition, the anode (100) may be used as a multilayer including two or more layers.

[0071] The first part (110) includes a hole transport layer (113) and an electron transport layer (115). Preferably, as can be seen in FIGS. 2 to 13, the first part (110) further includes an emission layer (114), and the emission layer (114) is disposed between the hole transport layer (113) and the electron transport layer (115). In other words, the first part (110) may include a hole transport layer (113), an emission layer (114), an electron transport layer (115), and a cathode (118). In addition, as can be seen in FIGS. 6, 9, 10, 11, 12, and 13, a hole injection layer (112) may be further included between the anode (100) and the hole transport layer (113), and the hole transport layer (113) may be composed of one or more layers. That is, it can be composed of a multi-layer hole transport layer (113) such as a first hole transport layer, a second hole transport layer, a third hole transport layer, etc., and the names of the multi-layer hole transport layers (113) can be different. For example, when the hole transport layer (113) is composed of two layers, the hole transport layer (113) adjacent to the light-emitting layer (114) can be named as a light-emitting auxiliary layer, a buffer layer, an electron blocking layer, an electron blocking layer, an exciton blocking layer, etc. In FIGS. 9, 11, 12, and 13, it is named as a light-emitting auxiliary layer (122). In addition, in FIG. 11, it can be seen that it is composed of a first light-emitting auxiliary layer (124) and a second light-emitting auxiliary layer (125). However, it is not limited thereto. In addition, an electron injection layer (116) may be further included between the electron transport layer (115) and the cathode (118), and the electron transport layer (115) may be composed of one or more layers. That is, it may be composed of multiple electron transport layers (115) such as a first electron transport layer, a second electron transport layer, a third electron transport layer, etc., and the names of the multiple electron transport layers (115) may be different. For example, when the electron transport layer (115) is composed of two layers, the electron transport layer (115) adjacent to the light-emitting layer (114) may be named as an auxiliary layer, a buffer layer, an A-ETL, a hole-blocking layer, a hole-blocking layer, etc. In FIGS. 9 to 13, it is named as a hole-blocking layer (123).For example, the first part (110) may be sequentially laminated in the order of a hole injection layer (112) / hole transport layer (113) / light-emitting auxiliary layer (122) / light-emitting layer (114) / hole blocking layer (123) / electron transport layer (115) / electron injection layer (116) / cathode (118) on the anode (100), but is not limited thereto.

[0072] As shown in FIGS. 7 and 8, the first portion (110) may be formed in a form in which two or more stacks (ST) including a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115) are formed. Two or more sets (n≥2) of stacks of multilayer organic layers (111) may be formed between the anode (100) and the cathode (118), and a charge generation layer (CGL; not shown) may be formed between the stacks of organic layers (111). In other words, when n is 2, a hole transport layer (113) may be stacked again on the electron transport layer (115), and a charge generation layer (CGL) may be included between the electron transport layer (115) and the hole transport layer (113). For example, it may sequentially include an anode (100), a first stack (first hole transport layer-first light-emitting layer-first electron transport layer), a charge generation layer (CGL), a second stack (second hole transport layer-second light-emitting layer-second electron transport layer), and a cathode (118). The charge generation layer (CGL) may be arranged between stacks, and serves to increase current efficiency and smoothly distribute charges.

[0073] The emission colors between the stacks may be different, and the materials of each stack may be different. In addition, electrons and holes are supplied from the CGL, the anode (100), and the cathode (118) to enable each light-emitting layer (114) to emit light. That is, each light-emitting layer (114) may emit light with a different color. When a plurality of light-emitting layers (114) are formed by a multilayer stack structure, an organic light-emitting display device that emits white light by the mixing effect of the light emitted from each light-emitting layer (114) can be manufactured, and an organic light-emitting display device that emits light of various colors can also be manufactured.

[0074] The above charge generation layer may be formed of an n-doped layer and / or a p-doped layer for injecting electrons and holes, and may be selected from, for example, n and p conductive dopants, but is not limited thereto.

[0075] The above hole injection layer (112) or hole transport layer (113) may be composed of any material commonly used as a hole injection / transport material, such as an aromatic or heteroaromatic amine compound and a carbazole derivative, but is not limited thereto.

[0076] Additionally, the hole injection layer (112) may be composed of one or more compounds, and the compound of the hole injection layer (112) and the compound of the hole transport layer (113) may be the same or different.

[0077] The hole mobility of the above hole transport layer (113) is 1.0×10 -8 cm 2 / Vs to 1.0×10 -3 cm 2 / Vs is preferable. More preferably 1.0×10 -8 cm 2 / Vs to 1.0×10 -5 cm 2 / Vs is preferable. The hole mobility of the hole transport layer (113) is a parameter that can show the degree to which hole injection / transport is performed well. In other words, the lower the hole mobility, the better the hole injection / transport can be performed. The hole mobility of the hole transport layer (113) can be measured and calculated using the SCLC (Space Charge Limited Current) calculation method described below.

[0078] In addition, it is preferable that the HOMO (Highest Occupied Molecular Orbital) energy level of the hole transport layer (113) is -5.5 eV to -5.0 eV. When the HOMO energy level of the hole transport layer (113) satisfies the above range, holes can be smoothly moved to the host of the light-emitting layer (114), which can contribute to increasing efficiency.

[0079]

[0080] The above hole transport layer (113) can be specifically selected as a compound represented by the following chemical formula 1 or chemical formula 2.

[0081] [Chemical Formula 1] [Chemical Formula 2]

[0082]

[0083] In the above chemical formulas 1 and 2, each symbol can be defined as follows.

[0084] Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heteroaryl group of; C3~C 60 Aliphatic ring and C6~C 60Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; C6~C 30 Aryloxy group of; and C3~C 60 is selected from the group consisting of cycloalkyl groups;

[0085] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0086] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is a heteroaryl group, preferably C2~C 30 Heteroaryl group of, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heteroaryl group.

[0087] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0088] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0089] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0090] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0091] The above Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7If it is a cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0092] L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0093] Above L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 If it is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc.

[0094] Above L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0095] Above L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 and L 8 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

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

[0097] Here, the aryl group, arylene group, heteroaryl group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20Aryl group of; C6~C substituted with halogen 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0098]

[0099] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-1 to 1-3.

[0100] [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3]

[0101]

[0102] In the above chemical formulas 1-1 to 1-3, each symbol can be defined as follows.

[0103] Ar 2 , Ar 3 , L 1 , L 2 and L 3 is the same as defined in the above chemical formula 1,

[0104] Ar is the above Ar 1 is identical to the definition of

[0105] Ar' is C3~C 60 is a cycloalkyl group, preferably C3~C 30Cycloalkyl group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0106] X 1 and X 2 is independently selected from the group consisting of single bonds, O, S, NR, C(R')(R") and Si(R')(R"), with the proviso that X 1 and X 2 Except for the case where all are single bonds,

[0107] R 1 , R 2 , R 3 , R 4 , R 5 , R, R' and R" are each the same or different from each other and independently hydrogen; deuterium; halogen; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; and C3~C 20 is selected from the group consisting of an aliphatic ring; or a plurality of adjacent R 1 R's or multiple R's 2 R's or multiple R's 3 R's or multiple R's 4 R's or multiple R's 5 They can combine with each other to form a ring, or R' and R" can combine with each other to form a spiro ring,

[0108] a, c, d and e are independently integers from 0 to 4, and b is an integer from 0 to 3.

[0109]

[0110] The above chemical formula 1 can be represented by the following chemical formula 1-1-1 or chemical formula 1-1-2.

[0111] [Chemical Formula 1-1-1] [Chemical Formula 1-1-2]

[0112]

[0113] {In the above chemical formulas 1-1-1 and 1-1-2, Ar 2 , Ar 3 , L 1 , L 2 , L 3 , X 1 , R 1 , R 2 , R', R", a and b are as defined above.}

[0114]

[0115] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-1-A to 1-1-C.

[0116] [Chemical Formula 1-1-A] [Chemical Formula 1-1-B] [Chemical Formula 1-1-C]

[0117]

[0118] {In the above chemical formulas 1-1-A to 1-1-C,

[0119] Ar 2 , Ar 3 , L 1 , L 2 , L 3 , R 1 , R 2 , a and b are as defined above,

[0120] R 6 , R 7 , R 8 and R 9 is the above R 1is the same as the definition of , or adjacent groups can combine with each other to form a ring,

[0121] f and g are independently integers from 0 to 5, and h and i are independently integers from 0 to 4.

[0122]

[0123] The above chemical formula 1 can be represented by any one of the following chemical formulas 1-1-D to 1-1-F.

[0124] [Chemical Formula 1-1-D] [Chemical Formula 1-1-E]

[0125]

[0126] [Chemical Formula 1-1-F]

[0127]

[0128] {In the above chemical formulas 1-1-D to 1-1-F,

[0129] Ar 2 , Ar 3 , L 1 , L 2 , L 3 , X 1 , R 1 , R 2 , a and b are as defined above,

[0130] R 10 , R 11 , R 12 and R 13 Silver is the above R 1 is identical to the definition of , or can form a ring by combining adjacent groups,

[0131] j and k are each independently an integer from 0 to 5, and l and m are each independently an integer from 0 to 4.

[0132]

[0133] The above Ar' may be any one of the following chemical formulas 1-3-1 to 1-3-5, but is not limited thereto.

[0134] [Chemical Formula 1-3-1] [Chemical Formula 1-3-2] [Chemical Formula 1-3-3]

[0135]

[0136] [Chemical Formula 1-3-4] [Chemical Formula 1-3-5]

[0137]

[0138] {In the above chemical formulas 1-3-1 to 1-3-5,

[0139] Z is the above R 1 is the same as the definition of , or adjacent groups can combine with each other to form a ring,

[0140] z1 and z2 are integers from 0 to 11, independently of each other, and z3 is an integer from 0 to 15,

[0141] * indicates the position of joining.}

[0142]

[0143] The above chemical formula 2 can be represented by the following chemical formula 2-1 or chemical formula 2-2.

[0144] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0145]

[0146] {In the above chemical formula 2-1 and chemical formula 2-2,

[0147] Ar 4 , Ar 5 , Ar 6 , Ar 7 , L 4 , L 5 , L 6 and L 7 is the same as defined in the above chemical formula 2,

[0148] R 21 , R 22 and R 23 Silver is the above R 1 is the same as the definition of , or adjacent groups can combine with each other to form a ring,

[0149] n is an integer from 1 to 3,

[0150] a' is an integer from 0 to 4, and b' and c' are independently integers from 0 to 3.

[0151]

[0152] The above chemical formula 2 can be represented by the following chemical formula 2-1-1 or chemical formula 2-1-2.

[0153] [Chemical Formula 2-1-1] [Chemical Formula 2-1-2]

[0154]

[0155] {In the above chemical formulas 2-1-1 and 2-1-2,

[0156] Ar 4 , Ar 5 , Ar 6 , Ar 7 , L 4 , L 5 , L 6 and L 7 is the same as defined in the above chemical formula 2,

[0157] R 24 , R 25 , R 26 and R 27 Silver is the above R 1 is the same as the definition of , or adjacent groups can combine with each other to form a ring,

[0158] X is O, S, NR or C(R')(R"),

[0159] d' and e' are independently integers from 0 to 3, f' is an integer from 0 to 4, g' is an integer from 0 to 2,

[0160] The above R, R' and R" are as defined above.

[0161]

[0162] The above chemical formula 2 can be represented by any one of the following chemical formulas 2-1-A to 2-1-H.

[0163] [Chemical Formula 2-1-A] [Chemical Formula 2-1-B]

[0164]

[0165] [Chemical Formula 2-1-C] [Chemical Formula 2-1-D]

[0166]

[0167] [Chemical Formula 2-1-E] [Chemical Formula 2-1-F]

[0168]

[0169] [Chemical Formula 2-1-G] [Chemical Formula 2-1-H]

[0170]

[0171] {In the above chemical formulas 2-1-A to 2-1-H, Ar 4 , Ar 5 , Ar 6 , Ar 7 , L 4 , L 5 , L 6 , L 7 , X, R 24 , R 25 , d' and e' are as defined above.}

[0172]

[0173] The above chemical formula 2 can be represented by any one of the following chemical formulas 2-1-I to 2-1-N.

[0174] [Chemical Formula 2-1-I] [Chemical Formula 2-1-J] [Chemical Formula 2-1-K]

[0175]

[0176] [Chemical Formula 2-1-L] [Chemical Formula 2-1-M] [Chemical Formula 2-1-N]

[0177]

[0178] {In the above chemical formulas 2-1-I to 2-1-N, Ar 4 , Ar 5 , Ar6 , Ar 7 , L 4 , L 5 , L 6 , L 7 , X, R 26 , R 27 , f' and g' are as defined above.}

[0179]

[0180] The above chemical formulas 1 and 2 may be represented by any one of the compounds P1-1 to P1-90 below, but are not limited thereto.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] The above light-emitting layer (114) may include a host and a dopant.

[0206] The host may be selected from any material commonly used as a host, such as, but not limited to, an aromatic or heteroaromatic amine compound, an azine compound, a condensed polycyclic aromatic compound, a carbazole compound, and the like. In addition, the host may be composed of one or more compounds.

[0207] The above dopant may be selected from any material commonly used as a dopant, such as a fluorescent luminescent compound, a phosphorescent luminescent compound, and a delayed fluorescent luminescent compound, and may be selected from, for example, a condensed polycyclic aromatic compound, a condensed polycyclic aromatic amine compound, a compound containing boron (B), a carbazole compound, an organometallic complex (an organometallic compound containing iridium (Ir), osmium (Os), ruthenium (Rh), platinum (Pt), etc.), but is not limited thereto. In addition, the dopant may be composed of one or more compounds.

[0208] The electron injection layer (116) or electron transport layer (115) may be formed of a material selected from any material commonly used as an electron injection / transport material, such as a heteroaromatic compound such as an azine derivative, a carbazole derivative, a phenanthroline derivative, an imidazole derivative, a benzimidazole derivative, and a benzoxazole derivative, or a metal complex such as an aluminum (Al) complex and a zinc (Zn) complex, but is not limited thereto.

[0209] Additionally, the electron injection layer (116) may be composed of one or more compounds, and the compound of the electron injection layer (116) and the compound of the electron transport layer (115) may be the same or different.

[0210] In addition, the electron injection layer (116) may include a metal or a compound including a metal. In particular, it may be formed of a material selected from among materials having high electrical conductivity, such as silver (Ag), magnesium (Mg), aluminum (Al), ytterbium (Yb), copper (Cu), zinc (Zn), cadmium (Cd), gold (Au), nickel (Ni), cobalt (Co), iron (Fe), molybdenum (Mo), niobium (Nb), palladium (Pd), platinum (Pt), lithium (Li), sodium (Na), potassium (Ca), and combinations thereof, but is not limited thereto.

[0211] The electron mobility of the above electron transport layer (115) is 1.0×10 -8 cm 2 / Vs to 1.0×10 -3 cm 2 / Vs is preferable. The electron mobility of the electron transport layer (115) is a parameter that can be used to determine the degree to which electron injection / transport is performed well. In other words, the lower the electron mobility, the better the electron injection / transport can be performed. The electron mobility of the electron transport layer (115) can be measured and calculated using the SCLC (Space Charge Limited Current) calculation method described below.

[0212] The hole mobility of the above hole transport layer (113) and / or the electron mobility of the electron transport layer (115) can be calculated and confirmed based on the SCLC (Space Charge Limited Current) in the JV Curve of the HOD (Hole Only Device) / EOD (Electron Only Device) device. SCLC refers to the section where the main emission starts and is in a dynamic equilibrium (Space Charge) state where charges are filled in the trap.

[0213] At this time, the hole / electron mobility (μ) can be calculated using Child's Law and the Poole-Frenkel Emission equation.

[0214] Equation 1 below is Child's Law, and Equation 2 below is the equation for Poole-Frenkel Emission.

[0215]

[0216] J = current density (A / Cm) 2 )

[0217] ε = dielectric constant of organic matter (2.655×10 -13 As / Vcm)

[0218] d = thickness of the film (cm)

[0219] V = applied voltage (V)

[0220]

[0221] E = electric field (V / cm)

[0222] μ0 = Poole-frenkel mobility (cm 2 / Vs)

[0223] β= Poole-frenkel constant

[0224]

[0225] Combining the above equations 1 and 2, we obtain equation 3 below.

[0226]

[0227] At this time, β and μ0 are different depending on the material and device configuration of the device, so they can be calculated by referring to the JV Curve. Therefore, by introducing the calculated β and μ0 into Equation 2, the hole / electron mobility (μ) can be calculated. At this time, the hole / electron mobility range for the SCLC section can be calculated, or the hole / electron mobility (μ0) in the zero field (i.e., when E is 0) can be calculated to calculate the hole mobility for the material. In this specification, the hole / electron mobility of a compound means the hole mobility in the zero field.

[0228] It is preferable that the LUMO (Lowest Occupied Molecular Orbital) energy level of the electron transport layer (115) is -3.5 eV to -2.8 eV. When the LUMO energy level of the electron injection layer (116) satisfies the above range, electrons can be smoothly transferred to the host of the light-emitting layer (114), which can contribute to increasing efficiency.

[0229]

[0230] The above electron transport layer (115) can be specifically selected as a compound represented by the following chemical formula 3 or chemical formula 4.

[0231] [Chemical Formula 3] [Chemical Formula 4]

[0232]

[0233] In the above chemical formulas 3 and 4, each symbol can be defined as follows.

[0234] X 3 , X 4 and X 5 are independently N or -CH, provided that at least one is N,

[0235] X 6 is O, S or NR a and,

[0236] Ar 10 , Ar 11 , Ar12 and Ar 13 Silver is the above Ar 1 is identical to the definition of

[0237] L 10 , L 11 , L 12 and L 13 Silver is the above L 1 is identical to the definition of

[0238] R 100 and R a are each the same or different, and independently of each other, hydrogen; deuterium; halogen; cyano group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group of R; or 100 The neighboring elements can combine with each other to form rings,

[0239] The above R 100 and R a In this case, it is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0240] The above R 100 and R a In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0241] The above R 100 and R a In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0242] The above R 100 and R a In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0243] The above R 100 and R a In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0244] The above R 100 and R a In the case of this aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0245] a100 is an integer from 0 to 4,

[0246] Here, the aryl group, arylene group, heteroaryl group, heterocyclic group, fluorenyl group, fluorenylene group, cycloalkyl group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C6~C substituted with halogen 20 Aryl group of; C6~C substituted with cyano group 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0247]

[0248] The above chemical formula 3 can be represented by any one of the following chemical formulas 3-1 to 3-3.

[0249] [Chemical Formula 3-1] [Chemical Formula 3-2]

[0250]

[0251] [Chemical Formula 3-3]

[0252]

[0253] In the above chemical formulas 3-1 to 3-3, each symbol can be defined as follows.

[0254] X 3 , X 4 , X 5 , Ar 11 , Ar 12 , L 10 , L 11 and L 12 is the same as defined above,

[0255] X 7 and X 8 is the above X 1 Same as the definition of , except that X 7 and X 8 Except for the case where all are single bonds,

[0256] Ar" is C6~C 60 is an arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc.

[0257] Ar 14 is the above Ar 1 is identical to the definition of

[0258] R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ' are each the same or different from each other, and independently represent hydrogen; deuterium; halogen; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C20 Alkoxyl group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 20 Heterocyclic group of; and C3~C 20 selected from the group consisting of aliphatic ring groups; or adjacent multiple R 1 'R' or 'R's' 2 'R' or 'R's' 3 'R' or 'R's' 4 'R' or 'R's' 5 'They can combine with each other to form rings,

[0259] a', c', d' and e' are independently integers from 0 to 4, b' is an integer from 0 to 3,

[0260] a"≥1.}

[0261]

[0262] The above chemical formula 3 can be represented by the following chemical formula 3-1-1 or chemical formula 3-1-2.

[0263] [Chemical Formula 3-1-1] [Chemical Formula 3-1-2]

[0264]

[0265] In the above chemical formulas 3-1-1 and 3-1-2,

[0266] X 3 , X 4 , X 5 , X 7 , Ar 11 , Ar 12 , L 10 , L 11 , L 12 , R', R", R 1 ', R 2 ', a' and b' are as defined above.

[0267]

[0268] The above chemical formula 3 can be represented by any one of the following chemical formulas 3-1-A to 3-1-C.

[0269] [Chemical Formula 3-1-A] [Chemical Formula 3-1-B]

[0270]

[0271] [Chemical Formula 3-1-C]

[0272]

[0273] {In the above chemical formulas 3-1-A to 3-1-C,

[0274] X 3 , X 4 , X 5 , X 7 , Ar 11 , Ar 12 , L 10 , L 11 , L 12 , R 1 ', R 2 ', a' and b' are as defined above,

[0275] R 6 ', R 7 ', R 8 ' and R 9 ' is the above R 1 ' is the same as the definition of, or adjacent groups can be combined to form a ring,

[0276] f' and g' are independently integers from 0 to 5, and h' and i' are independently integers from 0 to 4.

[0277]

[0278] The above chemical formula 3 can be represented by any one of the following chemical formulas 3-1-D to 3-1-F.

[0279] [Chemical Formula 3-1-D] [Chemical Formula 3-1-E]

[0280]

[0281] [Chemical Formula 3-1-F]

[0282]

[0283] {In the above chemical formulas 3-1-D to 3-1-F,

[0284] X 3 , X 4 , X 5 , X 7 , Ar 11 , Ar 12 , L 10 , L 11 , L 12 , R 1 ', R 2 ', a' and b' are as defined above,

[0285] R 10 ', R 11 ', R 12 ' and R 13 ' is the above R 1 ' is the same as the definition of, or adjacent groups can be combined to form a ring,

[0286] j' and k' are independently integers from 0 to 5, and l' and m' are independently integers from 0 to 4.

[0287]

[0288] The above chemical formula 4 can be represented by any one of the following chemical formulas 4-1 to 4-5.

[0289] [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3]

[0290]

[0291] [Chemical Formula 4-4] [Chemical Formula 4-5]

[0292]

[0293] {In the above chemical formulas 4-1 to 4-5,

[0294] X 6 , Ar 13 , L 13 , R 100and a100 are as defined above,

[0295] a100' is an integer from 0 to 3.

[0296]

[0297] The above chemical formula 4 can be represented by the following chemical formula 4-6.

[0298] [Chemical Formula 4-6]

[0299]

[0300] {In the above chemical formula 4-6,

[0301] X 6 , L 13 , R 100 and a100 are as defined above,

[0302] R 101 Silver is the above R 1 ' is the same as the definition of, or adjacent groups can be combined to form a ring,

[0303] a101 is an integer from 0 to 9.}

[0304]

[0305] The above chemical formulas 3 and 4 may be represented by any one of the compounds P2-1 to P2-76 below, but are not limited thereto.

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] In the case of the first part (110), a cathode (118) is formed on the electron transport layer (115). When the device is configured as described above, the optimal conditions for configuring an organic electroluminescent device are achieved. In particular, as the hole mobility and electron mobility decrease, the transport capacity of holes and electrons increases, resulting in a decrease in the driving voltage. In addition, when the balance of holes and electrons in the hole transport layer (113) and the electron transport layer (115) has an appropriate value, a highly efficient organic electroluminescent device can be manufactured. Therefore, when the above conditions are satisfied, an optimal organic electroluminescent device with a low driving voltage and high efficiency can be provided.

[0327] The above cathode (118) is preferably composed of one or more metal materials, and the metal materials may be selected from magnesium (Mg), silver (Ag), aluminum (Al), lithium (Li), calcium (Ca), indium (In), and combinations thereof, and is preferably composed of a mixture of Mg and Ag, but is not limited thereto.

[0328] Additionally, the cathode (118) may be used as a multi-layer including two or more layers.

[0329] However, when the above metal material is selected to form the cathode (118), it may be a reflective electrode and / or a semi-transparent electrode. In the case of a reflective electrode and / or a semi-transparent electrode, the transmittance is low, so the light transmittance required for UDC / UPS, etc. cannot be secured, which limits the implementation of a transparent display. Therefore, it is necessary to form a region capable of having high light transmittance without forming the cathode (118). That is, the first part (110), which is the light-emitting region, and the second part (120), which is the transmissive region, were arranged to implement a transparent display so as to secure the light transmittance required for UDC / UPS, etc.

[0330] The above metal patterning layer (121) is formed on the organic layer (111) that is formed in common, and suppresses the formation of the cathode (118) in the portion where the metal patterning layer (121) is formed. That is, by arranging the metal patterning layer (121), the cathode (118) can be formed only in the portion where it is desired to be formed or in a selective portion. The organic layer (111) that is formed in common in the second portion (120) includes a hole transport layer (113) and an electron transport layer (115), and may further include a hole injection layer (112) between the anode (100) and the hole transport layer (113), and the hole transport layer (113) may be composed of one or more layers. In addition, an electron injection layer (116) may be further included between the electron transport layer (115) and the metal patterning layer (121), and the electron transport layer (115) may be composed of one or more layers.

[0331] The organic layer (111) commonly formed in the second part (120) may include a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115), and as shown in FIGS. 1 and 3, the remaining portion except for the cathode (118) in the first part (110) may be the same, or, in the case of the light-emitting layer (114) of the first part (110), a shadow mask must be used to implement R / G / B pixels, so as shown in FIGS. 4 and 7, the remaining layers except for the light-emitting layer (114) and the cathode (118) of the first part (110) and the organic layer (111) of the second part (120) may be the same. Accordingly, the second part (120) can suppress the formation of the cathode (118) by laminating a metal patterning layer (121) after laminating a commonly formed organic layer (111) without laminating a separate additional layer. For example, if the first part (110) is composed of a hole transport layer (113) - a light-emitting layer (114) - an electron transport layer (115) - a cathode (118), the second part (120) can be composed of a hole transport layer (113) - an electron transport layer (115) - a metal patterning layer (121), and if the first part (110) is composed of a hole injection layer (112) - a first hole transport layer - a first light-emitting layer - a first electron transport layer - a charge generation layer - a second hole transport layer - a second light-emitting layer - a second electron transport layer - an electron injection layer (116) - a cathode (118), the second part (120) can be composed of a hole injection layer (112) - a first hole transport layer - a first electron transport layer - a charge generation layer - a It may be composed of a second hole transport layer, a second electron transport layer, an electron injection layer (116), and a metal patterning layer (121), but the composition of the organic light-emitting display device is not limited by the above example.

[0332] The metal patterning layer 121 is, for example, PBD (2-(4-biphenylyl)-5-phenyl-1,3,4-oxadiazole), PBD2 (2-([1,1'-biphenyl]-4-yl)-5-phenyl-1,3,4-oxadiazole), mCP (1,3-Bis(N-carbazolyl)benzene), TAZ (3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-124-triazole), β'-Bis(naphthalen-2-yl)-N,N'-bis(phenyl)-benzidine), NTAZ (4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBUP-TAZ (3,5-bis(4-(tert-butyl)phenyl)-4-phenyl-4H-1,2,4-triazole), BND (2,5-(binaphth-1-yl)-1,3,4-oxadiazole), TBADN (2-tert-Butyl-9,10-di(naphth-2-yl)anthracene), CBP (4,4'-Bis(carbazol-9-yl)biphenyl), BAlq (Bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium), m-BPC (9-([1,1'-biphenyl]-3-yl)-9H-carbazole), Ir(ppy)3(tris(2-phenylpyridine)iridium(III)) and compounds containing fluorine (F), and preferably, it may be a compound containing fluorine, but does not include a perfluorinated compound.

[0333] The perfluorinated compound may be a perfluorinated sulfonate (PFSA) or a perfluoroalkyl acid (PFAA), and the perfluorinated alkynic acid includes a perfluoroalkyl carboxylic acid (PFCA).

[0334] For example, the perfluorinated compounds include, but are not limited to, perfluorooctane sulfonate (PFOS), perfluorobutane sulfonate (PFBS), perfluorohexane sulfonate (PFHxS), perfluorooctanoic acid (PFOA), perfluorohexanoic acid (PFHxA), perfluoroundecanoic acid (PFUnDA), perfluoroheptanoic acid (PFHpA), perfluorododecanoic acid (PFDnDA), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA).

[0335] Also, the molecular formula of the perfluorinated compound is C6HF 11 O2, C7HF 13 O2, C8HF 15 O2, C9HF 17 O2, C 10 HF 19 O2, C 11 HF 21 O2, C 12 HF 23 O2, C4HF9SO2, C6HF 13 SO2, C8HF 17 It can be expressed as SO2, etc., but is not limited to this.

[0336] In the present invention, monofluorinated compounds; or aromatic or alkene compounds containing at least one carbon substituted with F, CF2 or CF3 at a hydrogen position and containing a carbon not substituted with fluorine at a hydrogen position; are not included in perfluorinated compounds.

[0337]

[0338] The above metal patterning layer (121) can be specifically selected as a compound represented by the following chemical formula A.

[0339] [Chemical Formula A]

[0340]

[0341] In the above chemical formula A, each symbol can be defined as follows.

[0342] A 200 Hwan, B 200 Hwan and C 200 The rings are independently C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heteroaryl group;

[0343] A above 200 Hwan, B 200 Hwan and C 200 If the ring is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0344] A above 200 Hwan, B 200 Hwan and C 200 If the ring is a heteroaryl group, preferably C2~C 30 Heteroaryl group of, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heteroaryl group.

[0345] L 201 is a single bond; NR 204 ; C(R 204 )(R 205 ); or Si(R 204 )(R 205 ); and,

[0346] R 201 , R 202and R 203 are each the same or different and independently represent hydrogen; deuterium; halogen; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; C6~C 30 Aryloxy group of; CF3; CF2H; C4H4F3; C3H2F3; C3F5; SF5; N(R 401 )(R 402 ); and Si(R 401 )(R 402 )(R 403 ); is selected from the group consisting of,

[0347] But, R 201 , R 202 and R 203 At least one of them is selected from the group consisting of fluorine (F); CF3; CF2H; C4H4F3; C3H2F3; C3F5; and SF5;

[0348] The above R 201 , R 202 and R 203 In this case, it is preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0349] The above R 201 , R 202 and R 203 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0350] The above R 201 , R 202 and R 203 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0351] The above R 201 , R 202 and R 203 In this case, it is preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0352] The above R 201 , R 202 and R 203 In the case of this alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0353] The above R 201 , R 202 and R 203In the case of this aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0354] R 204 and R 205 are independently hydrogen; deuterium; halogen; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group of R, or 204 Wow R 205 can combine with each other to form rings,

[0355] The above R 204 and R 205 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0356] The above R 204 and R 205 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0357] The above R 204 and R 205 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0358] The above R 204 and R 205 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0359] The above R 204 and R 205 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0360] The above R 204 and R 205 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0361] R 401, R 402 and R 403 are independently C6~C 20 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 20 is a heterocyclic group;

[0362] n201 is an integer from 0 to 3, a201, a202 and a203 are independently integers from 1 to 10,

[0363] Here, the aryl group, arylene group, heteroaryl group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C1~C substituted with halogen 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C6~C substituted with halogen 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0364]

[0365] The above chemical formula A can be represented by any one of the following chemical formulas B to D.

[0366] [Chemical Formula B]

[0367]

[0368] [Chemical Formula C]

[0369]

[0370] [Chemical Formula D]

[0371]

[0372] In the above chemical formulas B to D, A 200 Hwan, B 200 Hwan, C 200 Hwan, R 201 , R 202 , R 203 , R 204 , R 205 , a201, a202, a203 and n201 are the same as defined in the above chemical formula A.

[0373]

[0374] The above chemical formula A may be any one of the following compounds P3-1 to P3-23, but is not limited thereto.

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382] The contact angle of the above metal patterning layer (121) is preferably 100° to 180°, more preferably 100° to 150°. In addition, when the contact angle of the compound satisfies the above range, it may be a compound with high light transmittance.

[0383] In general, adhesion can be explained by the solid surface energy through the contact angle, and generally, the larger the contact angle, the lower the adhesion.

[0384] This can be confirmed through Young's Equation 4 below.

[0385]

[0386] In the above equation 4, each symbol is as follows.

[0387] gSL: interfacial tension between solid and liquid

[0388] gSV: interfacial tension between solid surface and liquid vapor

[0389] gLV: interfacial tension between liquid and liquid vapor

[0390]

[0391] The equation for work of adhesion (Wa) presented by Dupre in Equation 4 above is expressed as follows.

[0392]

[0393] In the above equation 5, gS is the surface tension of the solid itself, and since gS and gSV can generally be considered equal at small low surface energies, the above equation 5 is summarized as follows. (Young-Dupre equation)

[0394]

[0395] As the contact angle increases from 90° to 180° and approaches cosθ = -1, the adhesion decreases. That is, the adhesion of the metal (electrode) decreases due to the low surface energy, and the bonding of the cathode (118) is suppressed. In other words, when the metal patterning layer (121) is coated, the formation of the cathode (118) on the metal patterning layer (121) is suppressed depending on the structure of the compound included in the metal patterning layer (121), and ultimately, the cathode (118) is formed in a very small amount or not formed at all.

[0396] At this time, the light transmittance is used to determine the presence or absence of the cathode (118). The light transmittance of the metal patterning layer (121) is preferably 90% or more. This is because the cathode (118) contains an electrically conductive metal, which attenuates and / or absorbs light. Therefore, if the light transmittance exceeds 90% in the visible light region of the electromagnetic spectrum, it can be considered that the metal patterning layer (121) does not substantially contain an electrically conductive material.

[0397] The second portion (120) may further include a patterning auxiliary photosensitive layer (117). Preferably, the patterning auxiliary photosensitive layer (117) may be arranged under the metal patterning layer (121). Since the material currently applied to the metal patterning layer (121) has no or very weak photoluminescence characteristics, it may be difficult to measure its thickness using the photoluminescence characteristics. If the thickness of the metal patterning layer (121) is too thick, a coagulation phenomenon occurs, making it difficult to form a thin film with a uniform surface, making it difficult to secure uniform light transmittance, and causing problems when additionally forming a thin film such as the third portion (130).

[0398] Therefore, in order to easily measure the thickness of the metal patterning layer (121) using optical characteristics, a patterning auxiliary photosensitive layer (117) having excellent photoluminescence characteristics can be formed under the metal patterning layer (121). The patterning auxiliary photosensitive layer (117) can be formed of a photosensitive organic material having a stronger photoluminescence intensity than the metal patterning layer (121) and optical characteristics that can be measured by an optical method. That is, after applying the patterning auxiliary photosensitive layer (117), the thickness of the metal patterning layer (121) can be measured using an ellipsometer.

[0399] The patterning auxiliary photosensitive layer (117) may include a compound containing at least one heterocycle. The heterocycle is preferably C2~C containing at least one heteroatom among O, N, S, Si, and P. 60 It may be a heterocyclic ring, more preferably C2~C 30 Heterocyclic ring, more preferably CC2~C 24 It may be a heterocyclic ring of, and specifically, it may be oxazole, thiazole, benzoxazole, benzothiazole, pyridine, pyrimidine, pyrazine, triazine, quinoline, quinazoline, quinoxaline, imidazole, triazole, benzimidazole, benzotriazole, furan, thiophene, benzofuran, benzothiophene, indole, dibenzofuran, dibenzothiophene, carbazole, benzofuropyridine, benzothiophenopyridine, carboline, benzofuropyrimidine, benzothiophenopyrimidine, benzofuropyrazine, and benzothiophenopyrazine, but is not limited thereto.

[0400] Additionally, it is preferable that the thickness of the patterning auxiliary photosensitive layer (117) be 5 nm or more.

[0401] By forming the third part (130), in the case of a top emission organic light emitting device, the optical energy loss due to SPPs (Surface Plasmon Polaritons) at the cathode can be reduced, and in the case of a bottom emission organic light emitting device, the third part (130) can serve as a buffer for the first part (110) and the second part (120). In particular, when the light transmittance of the material of the third part (130) is high, the optical energy loss due to SPPs can be reduced when light emitted from the first part (110) passes through the third part (130) and is emitted. Therefore, it is preferable that the light transmittance of the third part (130) in the visible light region is 70% or more, and more preferably 80% or more.

[0402] The refractive index of the material of the third part (130) is preferably 1.85 to 3.0. More preferably, it is 1.9 to 3.0, and even more preferably, it is 1.9 to 2.5. In particular, it is preferable that the compound of the material of the third part (130) has a refractive index of 2.1 or more at a wavelength of 450 nm, a refractive index of 1.95 or more at a wavelength of 530 nm, and a refractive index of 1.85 or more at a wavelength of 620 nm. When light emitted through the first part (110) passes through the third part (130) having a relatively high refractive index, the wavelength of the light is amplified, so that the luminous efficiency can be increased.

[0403] The third portion (130) may have a single-layer or multi-layer structure. In addition, the third portion (130) may be a single compound or a mixture of two or more compounds.

[0404] The material of the third part (130) may be specifically selected as a compound represented by the following chemical formula G.

[0405] [Chemical formula G]

[0406]

[0407] In the above chemical formula G, each symbol can be defined as follows.

[0408] X 301 is O, S or NR 302 and,

[0409] Y' is CR 300 or N,

[0410] L 302 is NL 304 -Ar 302 and,

[0411] L 301 , L 303 and L 304 are independently of each other and are single bonds; C6~C 60 Arylene group; Fluorenylene group; C2~C 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0412] Above L 301 , L 303 and L 304 In the case of this arylene group, preferably C6~C 30 Arylene group, more preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an arylene group, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc.

[0413] Above L 301 , L 303 and L 304 In this case, it is preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0414] Above L 301 , L 303 and L 304 In this case, the fusion ring is preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0415] Ar 301 and Ar 302 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Cycloalkyl group of; C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring; and -NAr 303 Ar 304 ; is selected from the group consisting of,

[0416] The above Ar 301 and Ar 302 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0417] The above Ar301 and Ar 302 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0418] The above Ar 301 and Ar 302 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0419] Ar 303 and Ar 304 are independently C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 A fused ring group of an aromatic ring is selected from the group consisting of;

[0420] The above Ar 303 and Ar 304 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0421] The above Ar 303 and Ar 304 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0422] The above Ar 303 and Ar 304 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0423] R 300 , R 301 and R 302 are each the same or different and independently represent hydrogen; deuterium; halogen; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C3~C60 Cycloalkyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy groups; or adjacent groups can be combined with each other to form a ring,

[0424] The above R 300 , R 301 and R 302 If it is an aryl group, preferably C6~C 30 Aryl group of, more preferably C6~C 25 , C6~C 18 or C6~C 12 The aryl group may be, for example, phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

[0425] The above R 300 , R 301 and R 302 If it is a heterocyclic group, preferably C2~C 30 A heterocyclic group, more preferably C2~C 25 , C2~C 18 or C2~C 12 It may be a heterocyclic group, and examples thereof include pyrazine, thiophene, pyridine, pyrimidine, quinoline, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, quinoxaline, benzoquinazoline, carbazole, dibenzoquinazoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, etc.

[0426] The above R 300 , R 301 and R 302 If it is a fusion ring, preferably C3~C 30 Aliphatic ring and C6~C 30 A fused ring group of an aromatic ring, more preferably C3~C 25 Aliphatic ring and C6~C 25 It may be a fused ring group of an aromatic ring.

[0427] The above R 300 , R 301 and R 302 If it is an alkyl group, preferably C1~C 30 It may be an alkyl group of, more preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkyl group, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a pentyl group, etc.

[0428] The above R 300 , R 301 and R 302 If it is a cycloalkyl group, preferably C3~C 30 Cycloalkyl group, more preferably C3~C 25 , C3~C 18 or C3~C 12 It may be a cycloalkyl group, and specifically, it may be cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0429] The above R 300 , R 301 and R 302 If it is an alkoxyl group, preferably C1~C 25 , C1~C 18 or C1~C 12 It may be an alkoxyl group.

[0430] The above R 300 , R 301 and R 302 If it is an aryloxy group, preferably C6~C 25 , C6~C 18 or C6~C 12 It may be an aryloxy group.

[0431] a301 is an integer from 0 to 4, a302 is 0 or 1,

[0432] Here, the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C6~C substituted with halogen 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 It refers to a fused ring composed of a heterocycle or a combination thereof, and includes a saturated or unsaturated ring.

[0433]

[0434] The above chemical formula G can be represented by the following chemical formula H or chemical formula I.

[0435] [Chemical Formula H] [Chemical Formula I]

[0436]

[0437] {In the above chemical formula H and chemical formula I, X 301 , L 301, L 302 , L 303 , Ar 301 , R 300 , R 301 , a301 and a302 are the same as defined in the above chemical formula G.

[0438]

[0439] The above chemical formula G can be represented by any one of the following chemical formulas J to N.

[0440] [Chemical Formula J] [Chemical Formula K] [Chemical Formula L]

[0441]

[0442] [Chemical Formula M] [Chemical Formula N]

[0443]

[0444] {In the above chemical formulas J to N,

[0445] X 301 , L 301 , L 303 , L 304 , Ar 301 , Ar 302 , R 300 , R 301 and a301 are as defined above,

[0446] Ar 305 and Ar 306 Silver is the above Ar 303 is identical to the definition of

[0447] R 303 Silver R 301 is identical to the definition of

[0448] a303 is an integer from 0 to 8.

[0449]

[0450] The above chemical formula G can be represented by the following chemical formula O.

[0451] [chemical formula O]

[0452]

[0453] {In the above chemical formula O, X 301 , L 301 , L 303 , L 304 , Ar 302 , Ar 303 , Ar 304 , R 301 and a301 are the same as defined in the above chemical formula G.

[0454]

[0455] Above L 301 or L 303 can be independently represented by any one of the following chemical formulas L-1 to L-4.

[0456] [Chemical Formula L-1] [Chemical Formula L-2] [Chemical Formula L-3] [Chemical Formula L-4]

[0457]

[0458] {In the above chemical formulas L-1 to L-4,

[0459] R 304 , R 305 , R 306 and R 307 Silver R 301 is identical to the definition of

[0460] X 302 is O, S, NR or C(R')(R"),

[0461] R, R' and R" are as defined above,

[0462] a304 and a309 are each independently an integer from 0 to 4, a306 and a307 are each independently an integer from 0 to 3, a308 is an integer from 0 to 2, a305 is an integer from 0 to 6,

[0463] * indicates the position where it is combined.}

[0464]

[0465] The above chemical formula G may be any one of the following compounds P4-1 to P4-92, but is not limited thereto.

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490] In addition, it is preferable that the overall light transmittance of the second part (120) and the third part (130) be 70% or more. That is, as described above, it must have the light transmittance required for UDC / UPS, etc., and in particular, the second part (120) and the third part (130) have a great influence on the light transmittance. Therefore, high light transmittance of the third part (130) and the metal patterning layer (121) is important, and it is preferable that the organic light emitting display device have high light transmittance in order to implement UDC / UPS, etc. while increasing the luminous efficiency of the organic light emitting display device.

[0491] These organic layers may be manufactured using various deposition methods. For example, the organic layers may be manufactured using deposition methods such as PVD or CVD, and may be manufactured in fewer layers using solution or solvent processes other than deposition methods, such as spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer.

[0492] Preferably, the organic layer may be formed by vacuum deposition. However, since the organic layer according to the present invention may be formed by various methods, the scope of the present invention is not limited by the formation method.

[0493] An organic electric device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0494] In addition, the organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0495] Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as cell phones, navigation systems, game consoles, various TVs, and various computers. Preferably, the display device includes a transparent display, and the electronic device may include an Under Display Camera (UDC) or an Under Panel Sensor (UPS).

[0496]

[0497] Hereinafter, the present invention will be described with reference to examples. The following examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[0498]

[0499] [Synthesis method]

[0500] P1 compound synthesis method

[0501] 1. P1-2 Synthesis Example

[0502]

[0503] 3-Bromo-9,9-dimethyl-9H-fluorene (5.0 g, 18.3 mmol) was dissolved in toluene (60 mL) in a round-bottomed flask, and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (6.8 g, 18.3 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), P(t-Bu)3 (0.4 mL, 1.1 mmol), and NaOt-Bu (3.5 g, 36.6 mmol) were added and the reaction was carried out at 60°C. Upon completion of the reaction, the organic layer was extracted with CH2Cl2 and water, dried over MgSO4, and concentrated. The resulting organic material was then purified by silica gel column chromatography and recrystallization to obtain 8 g of the product (yield 77%).

[0504]

[0505] 2. P1-24 Synthesis Example

[0506]

[0507] 2-chloro-7-phenyldibenzo[b,d]furan (5.0 g, 17.9 mmol), N-(4-fluorophenyl)-9,9'-spirobi[fluoren]-4-amine (7.6 g, 17.9 mmol), Pd2(dba)3 (0.5 g, 0.3 mmol), P(t-Bu)3 (0.4 mL, 1.1 mmol), and NaOt-Bu (3.4 g, 35.9 mmol) were added to a round-bottom flask, and 9.8 g of the product was obtained using the synthetic method of P1-2 above. (Yield 82%)

[0508]

[0509] 3. P1-28 Synthesis Example

[0510]

[0511] 2-bromo-9,9-diphenyl-9H-xanthene (5.0 g, 12.1 mmol), N-phenylphenanthren-2-amine (3.3 g, 12.1 mmol), Pd2(dba)3 (0.3 g, 0.4 mmol), P(t-Bu)3 (0.3 mL, 0.7 mmol), and NaOt-Bu (2.3 g, 24.2 mmol) were added to a round-bottomed flask, and 6.2 g of the product was obtained using the synthetic method of P1-2 above. (Yield 85%)

[0512]

[0513] 4. P1-35 Synthesis Example

[0514]

[0515] 3-(4-chlorophenyl)spiro[fluorene-9,9'-xanthene] (5.0 g, 11.3 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (2.8 g, 11.3 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol), P(t-Bu)3 (0.27 mL, 0.7 mmol), and NaOt-Bu (2.2 g, 22.6 mmol) were added to a round-bottom flask, and 5.8 g of the product was obtained using the synthetic method of P1-2 above. (Yield 79%)

[0516]

[0517] 5. P1-37 Synthesis Example

[0518]

[0519] 9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (4.5 g, 12.6 mmol), Pd2(dba)3 (0.3 g, 0.4 mmol), P(t-Bu)3 (0.3 mL, 0.8 mmol), NaOt-Bu (2.4 g, 25.2 mmol) were added to a round-bottom flask, and 7.6 g of the product was obtained using the synthetic method of P1-2 above. (Yield 89%)

[0520]

[0521] 6. P1-42 Synthesis Example

[0522]

[0523] 3-(4-chlorophenyl)dibenzo[b,d]thiophene (5.0 g, 17.0 mmol), N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (7 g, 17.0 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), P(t-Bu)3 (0.4 mL, 1.0 mmol), and NaOt-Bu (3.3 g, 33.9 mmol) were added to a round-bottom flask, and 10 g of the product was obtained using the synthetic method of P1-2 above. (Yield 88%)

[0524]

[0525] 7. P1-51 Synthesis Example

[0526]

[0527] N-([1,1'-biphenyl]-4-yl)-3'-bromo-N-phenyl-[1,1'-biphenyl]-4-amine (5.0 g, 10.5 mmol), 4-(naphthalen-1-yl)-N-phenylaniline (3.1 g, 10.5 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol), P(t-Bu)3 (0.3 mL, 0.6 mmol), NaOt-Bu (2.0 g, 21.0 mmol) were added to a round-bottom flask, and 6 g of the product was obtained using the synthetic method of P1-2 above. (Yield 83%)

[0528]

[0529] 8. P1-57 Synthesis Example

[0530]

[0531] 8-chloro-N,N-diphenyldibenzo[b,d]furan-1-amine (5.0 g, 13.5 mmol), N-phenyldibenzo[b,d]thiophen-3-amine (3.7 g, 13.5 mmol), Pd2(dba)3 (0.4 g, 0.4 mmol), P(t-Bu)3 (0.3 mL, 0.8 mmol), and NaOt-Bu (2.6 g, 27.0 mmol) were added to a round-bottom flask, and 6.4 g of the product was obtained using the synthetic method of P1-2 above. (Yield 78%)

[0532]

[0533] 9. P1-79 Synthesis Example

[0534]

[0535] 3-chloro-N,N-diphenyldibenzo[b,d]thiophen-1-amine (5.0 g, 13.0 mmol), N-phenylspiro[fluorene-9,9'-xanthen]-2'-amine (5.5 g, 13.0 mmol), Pd2(dba)3 (0.4 g, 0.4 mmol), P(t-Bu)3 (0.3 mL, 0.8 mmol), and NaOt-Bu (2.5 g, 25.9 mmol) were added to a round-bottom flask, and 8.6 g of the product was obtained using the synthetic method of P1-2 above. (Yield 86%)

[0536]

[0537] Meanwhile, the FD-MS values ​​of compounds P1-1 to P1-90 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 1 below.

[0538] Compound FD-MS Compound FD-MSP1-1 m / z = 437.21 (C 33 H 27 N=437.59)P1-2m / z=563.26(C 43 H 33 N=563.74)P1-3m / z=639.29(C 49 H 37N=639.84)P1-4m / z=653.27(C 49 H 35 NO=653.83)P1-5m / z=543.2(C 39 H 29 NS=543.73)P1-6m / z=653.27(C 49 H 35 NO=653.83)P1-7m / z=678.3(C 51 H 38 N2=678.88)P1-8m / z=643.29(C 48 H 37 NO=643.83)P1-9m / z=639.29(C 49 H 37 N=639.84)P1-10m / z=589.37(C 44 H 47 N=589.87)P1-11m / z=637.28(C 49 H 35 N=637.83)P1-12m / z=693.34(C 53 H 43 N=693.93)P1-13m / z=791.28(C 59 H 37 NO2=791.95)P1-14m / z=687.29(C 53 H 37 N=687.89)P1-15m / z=731.36(C 56 H 45 N=731.98)P1-16m / z=763.32(C 59 H 41 N=763.98)P1-17m / z=801.34(C 59 H 47 NS=802.09)P1-18m / z=782.37(C 59 H 46 N2=783.03)P1-19m / z=700.37(C 53 H 20 D 15 N=700.96)P1-20m / z=889.35(C 67 H 43 N3=890.1)P1-21m / z=609.25(C 47 H 31 N=609.77)P1-22m / z=659.26(C51 H 33 N=659.83)P1-23m / z=649.24(C 49 H 31 NO=649.79)P1-24m / z=667.23(C 49 H 30 FNO=667.78)P1-25m / z=517.2(C 37 H 27 NO2=517.63)P1-26m / z=590.28(C 42 H 30 D5NS=590.84)P1-27m / z=692.32(C 52 H 40 N2=692.91)P1-28m / z=601.24(C 45 H 31 NO=601.75)P1-29m / z=733.24(C 53 H 35 NOS=733.93)P1-30m / z=728.32(C 55 H 40 N2=728.94)P1-31m / z=631.29(C 47 H 37 NO=631.82)P1-32m / z=757.24(C 55 H 35 NOS=757.95)P1-33m / z=717.25(C 53 H 35 NS=717.93)P1-34m / z=574.24(C 43 H 30 N2=574.73)P1-35m / z=651.26(C 49 H 33 NO=651.81)P1-36m / z=777.3(C 59 H 39 NO=777.97)P1-37m / z=677.31(C 52 H 39 N=677.89)P1-38m / z=734.33(C 55 H 30 D7NO=734.95)P1-39m / z=681.21(C 49 H 31 NOS=681.85)P1-40m / z=561.21(C 42 H 27NO=561.68)P1-41m / z=607.16(C 42 H 25 NO2S=607.73)P1-42m / z=668.23(C 48 H 32 N2S=668.86)P1-43m / z=611.22(C 46 H 29 NO=611.74)P1-44m / z=609.3(C 45 H 39 NO=609.81)P1-45m / z=644.32(C 48 H 40 N2=644.86)P1-46m / z=611.23(C 43 H 33 NOS=611.8)P1-47m / z=733.37(C 56 H 47 N=734)P1-48m / z=549.34(C 41 H 43 N=549.8)P1-49m / z=723.3(C 53 H 41 NS=723.98)P1-50m / z=564.26(C 42 H 32 N2=564.73)P1-51m / z=690.3(C 52 H 38 N2=690.89)P1-52m / z=714.3(C 54 H 38 N2=714.91)P1-53m / z=618.3(C 46 H 38 N2=618.82)P1-54m / z=654.27(C 48 H 34 N2O=654.81)P1-55m / z=594.3(C 44 H 38 N2=594.8)P1-56m / z=644.23(C 46 H 32 N2S=644.84)P1-57m / z=608.19(C 42 H 28 N2OS=608.76)P1-58m / z=700.2(C 48 H 32 N2S2=700.92)P1-59m / z=734.24(C52 H 34 N2OS=734.92)P1-60m / z=694.3(C 51 H 38 N2O=694.88)P1-61m / z=684.22(C 48 H 32 N2OS=684.86)P1-62m / z=772.25(C 55 H 36 N2OS=772.97)P1-63m / z=784.31(C 57 H 40 N2O2=784.96)P1-64m / z=634.3(C 46 H 38 N2O=634.82)P1-65m / z=769.35(C 57 H 43 N3=769.99)P1-66m / z=760.25(C 54 H 36 N2OS=760.96)P1-67m / z=758.28(C 55 H 38 N2S=758.98)P1-68m / z=642.23(C 46 H 30 N2O2=642.76)P1-69m / z=698.2(C 48 H 30 N2O2S=698.84)P1-70m / z=677.28(C 50 H 35 N3=677.85)P1-71m / z=800.29(C 57 H 40 N2OS=801.02)P1-72m / z=748.35(C 55 H 44 N2O=748.97)P1-73m / z=774.27(C 55 H 38 N2OS=774.98)P1-74m / z=742.3(C 52 H 42 N2OS=742.98)P1-75m / z=862.25(C 61 H 38 N2S2=863.11)P1-76m / z=720.26(C 52 H 36 N2S=720.93)P1-77m / z=684.22(C48 H 32 N2OS=684.86)P1-78m / z=583.27(C 42 H 25 D5N2O=583.75)P1-79m / z=772.25(C 55 H 36 N2OS=772.97)P1-80m / z=778.25(C 54 H 35 FN2OS=778.95)P1-81m / z=810.36(C 60 H 46 N2O=811.04)P1-82m / z=748.22(C 52 H 32 N2O2S=748.9)P1-83m / z=895.36(C 66 H 45 N3O=896.11)P1-84m / z=654.27(C 48 H 34 N2O=654.81)P1-85m / z=726.31(C 52 H 42 N2S=726.98)P1-86m / z=719.33(C 51 H 29 D9N2S=719.99)P1-87m / z=788.21(C 54 H 32 N2O3S=788.92)P1-88m / z=758.28(C 55 H 38 N2S=758.98)P1-89m / z=577.37(C 43 H 47 N=577.86)P1-90m / z=613.37(C 40 H 47 N=613.89)

[0539] P2 compound compound

[0540] 1. P2-1 synthesis

[0541]

[0542] In a round-bottomed flask, dibenzo[b,d]furan-1-ylboronic acid (5.0 g, 23.6 mmol) was dissolved in THF (59 mL) and water (20 mL), and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.1 g, 23.6 mmol), Pd(PPh3)4 (0.8 g, 0.7 mmol), and NaOH (1.8 g, 47.17 mmol) were added, and the reaction was carried out at 85°C. Upon completion of the reaction, the organic layer was extracted with CH2Cl2 and water, dried over MgSO4, and concentrated. The resulting organic material was then purified by silica gel column chromatography and recrystallization to obtain 9.8 g of the product (yield 87%).

[0543]

[0544] 2. P2-9 Synthesis Example

[0545]

[0546] In a round-bottom flask, (4-(phenanthren-2-yl)phenyl)boronic acid (5.0 g, 16.8 mmol), 2-chloro-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine (8.5 g, 16.8 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and NaOH (1.3 g, 33.5 mmol) were added, and 10.8 g of the product was obtained using the synthetic method of P2-1 above. (Yield 89%)

[0547]

[0548] 3. P2-21 Synthesis Example

[0549]

[0550] In a round-bottom flask, (9,9-dimethyl-9H-xanthen-2-yl)boronic acid (5.0 g, 19.7 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.8 g, 19.7 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), and NaOH (1.6 g, 39.4 mmol) were added, and 8.1 g of the product was obtained using the synthetic method of P2-1 above. (Yield 80%)

[0551]

[0552] 4. P2-34 Synthesis Example

[0553]

[0554] In a round-bottomed flask, spiro[fluorene-9,9'-xanthen]-3'-ylboronic acid (5.0 g, 13.3 mmol), 2-chloro-4-(dibenzo[b,d]thiophen-4-yl-d7)-6-phenyl-1,3,5-triazine (5.1 g, 13.3 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), and NaOH (1.1 g, 26.6 mmol) were added, and 7.8 g of the product was obtained using the synthetic method of P2-1 above. (Yield 87%)

[0555]

[0556] 5. P2-39 Synthesis Example

[0557]

[0558] In a round-bottom flask, (6-phenylnaphthalen-2-yl)boronic acid (5.0 g, 20.2 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.2 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), and NaOH (1.6 g, 40.3 mmol) were added, and 9.4 g of the product was obtained using the synthetic method of P2-1 above. (Yield 91%)

[0559]

[0560] 6. P2-59 Synthesis Example

[0561]

[0562] In a round-bottomed flask, (9,10-di(naphthalen-2-yl)anthracen-2-yl)boronic acid (5.0 g, 10.5 mmol), 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole (3.7 g, 10.5 mmol), Pd(PPh3)4 (0.4 g, 0.3 mmol), and NaOH (0.8 g, 21.1 mmol) were added, and 5.7 g of the product was obtained using the synthetic method of P2-1 above. (Yield 77%)

[0563]

[0564] 7. P2-60 Synthesis Example

[0565]

[0566] 4-chloro-1-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene (5.0 g, 12.2 mmol), benzo[d]oxazol-2-ylboronic acid (2.0 g, 12.2 mmol), Pd(PPh3)4 (0.4 g, 0.4 mmol), and NaOH (1.0 g, 24.3 mmol) were added to a round-bottomed flask, and 4.8 g of the product was obtained using the synthetic method of P2-1 above. (Yield 80%)

[0567]

[0568] 8. P2-61 Synthesis Example

[0569]

[0570] In a round-bottom flask, (3-(9-phenyl-9H-fluoren-9-yl)phenyl)boronic acid (5.0 g, 13.8 mmol), 7-chloro-1,2-diphenyl-1H-benzo[d]imidazole (4.2 g, 13.8 mmol), Pd(PPh3)4 (0.5 g, 0.4 mmol), and NaOH (1.1 g, 27.6 mmol) were added, and 7.2 g of the product was obtained using the synthetic method of P2-1 above. (Yield 89%)

[0571]

[0572] Meanwhile, the FD-MS values ​​of compounds P2-1 to P2-76 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 2 below.

[0573] Compound FD-MS Compound FD-MSP2-1 m / z = 475.17 (C 33 H 21 N3O=475.55)P2-2m / z=576.2(C 40 H 24 N4O=576.66)P2-3m / z=730.24(C 53 H 34 N2S=730.93)P2-4m / z=682.18(C 46 H 26N4OS=682.8)P2-5m / z=577.25(C 42 H 31 N3=577.73)P2-6m / z=628.26(C 45 H 32 N4=628.78)P2-7m / z=628.26(C 45 H 32 N4=628.78)P2-8m / z=576.22(C 42 H 28 N2O=576.7)P2-9m / z=725.28(C 54 H 35 N3=725.9)P2-10m / z=719.27(C 52 H 34 FN3=719.86)P2-11m / z=716.26(C 51 H 32 N4O=716.84)P2-12m / z=832.27(C 59 H 36 N4S=833.03)P2-13m / z=729.26(C 52 H 35 N3Si=729.96)P2-14m / z=697.25(C 52 H 31 N3=697.84)P2-15m / z=829.35(C 62 H 43 N3=830.05)P2-16m / z=715.26(C 52 H 33 N3O=715.86)P2-17m / z=750.25(C 52 H 26 D5N3OS=750.93)P2-18m / z=728.26(C 52 H 32 N4O=728.86)P2-19m / z=681.2(C 46 H 27 N5S=681.82)P2-20m / z=745.16(C 46 H 24 F5N3S=745.77)P2-21m / z=517.22(C 36 H 27 N3O=517.63)P2-22m / z=658.24(C 47 H 34N2S=658.86)P2-23m / z=615.27(C 45 H 33 N3=615.78)P2-24m / z=730.27(C 52 H 34 N4O=730.87)P2-25m / z=682.24(C 47 H 30 N4O2=682.78)P2-26m / z=748.23(C 51 H 32 N4OS=748.9)P2-27m / z=867.34(C 63 H 41 N5=868.06)P2-28m / z=766.31(C 56 H 38 N4=766.95)P2-29m / z=740.26(C 53 H 32 N4O=740.87)P2-30m / z=762.27(C 57 H 34 N2O=762.91)P2-31m / z=704.26(C 50 H 32 N4O=704.83)P2-32m / z=741.25(C 52 H 31 N5O=741.85)P2-33m / z=689.22(C 48 H 27 N5O=689.78)P2-34m / z=676.23(C 46 H 20 D7N3OS=676.84)P2-35m / z=739.27(C 53 H 33 N5=739.88)P2-36m / z=714.28(C 52 H 34 N4=714.87)P2-37m / z=702.28(C 51 H 34 N4=702.86)P2-38m / z=854.34(C 63 H 42 N4=855.06)P2-39m / z=511.2(C 37 H 25 N3=511.63)P2-40m / z=551.14(C 33 H 18F5N3=551.52)P2-41m / z=410.15(C 28 H 18 N4=410.48)P2-42m / z=670.31(C 48 H 38 N4=670.86)P2-43m / z=536.2(C 38 H 24 N4=536.64)P2-44m / z=565.2(C 37 H 23 N7=565.64)P2-45m / z=594.28(C 42 H 34 N4=594.76)P2-46m / z=638.25(C 46 H 30 N4=638.77)P2-47m / z=537.2(C 37 H 23 N5=537.63)P2-48m / z=537.22(C 39 H 27 N3=537.67)P2-49m / z=436.16(C 31 H 20 N2O=436.51)P2-50m / z=583.29(C 43 H 17 D 11 N2=583.78)P2-51m / z=663.27(C 49 H 33 N3=663.82)P2-52m / z=727.26(C 53 H 33 N3O=727.87)P2-53m / z=701.25(C 51 H 31 N3O=701.83)P2-54m / z=505.25(C 36 H 31 N3=505.67)P2-55m / z=537.18(C 38 H 23 N3O=537.62)P2-56m / z=639.23(C 46 H 29 N3O=639.76)P2-57m / z=674.27(C 51 H 34 N2=674.85)P2-58m / z=653.19(C 46 H 27N3S=653.8)P2-59m / z=698.27(C 53 H 34 N2=698.87)P2-60m / z=493.15(C 34 H 23 NOS=493.62)P2-61m / z=586.24(C 44 H 30 N2=586.74)P2-62m / z=641.27(C 48 H 35 NO=641.81)P2-63m / z=528.13(C 36 H 20 N2OS=528.63)P2-64m / z=627.23(C 45 H 29 N3O=627.75)P2-65m / z=605.19(C 42 H 27 N3S=605.76)P2-66m / z=666.21(C 48 H 30 N2S=666.84)P2-67m / z=600.22(C 44 H 28 N2O=600.72)P2-68m / z=542.16(C 36 H 22 N4S=542.66)P2-69m / z=614.27(C 46 H 34 N2=614.79)P2-70m / z=674.27(C 51 H 34 N2=674.85)P2-71m / z=549.18(C 39 H 23 N3O=549.63)P2-72m / z=454.11(C 30 H 18 N2OS=454.55)P2-73m / z=662.27(C 50 H 34 N2=662.84)P2-74m / z=628.2(C 45 H 28 N2S=628.79)P2-75m / z=525.18(C 37 H 23 N3O=525.61)P2-76m / z=605.19(C 42 H 27 N3S=605.76)

[0574] P3 compound synthesis method

[0575] 1. P3-1 Synthesis Example

[0576]

[0577] In a round-bottomed flask, dissolve bis(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)amine (3.0 g, 6.0 mmol) in toluene (30 mL), add 4,4,5,5-tetramethyl-2-(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane (2.2 g, 6.0 mmol), Pd2(dba)3 (0.16 g, 0.18 mmol), P(t-Bu)3 (0.07 g, 0.36 mmol), and NaOt-Bu (1.2 g, 12.0 mmol), and react at 80°C. After the reaction is complete, extract with CH2Cl2 and water, dry the organic layer with MgSO4, and concentrate. Afterwards, the generated organic material was purified through a silica gel column and recrystallized to obtain 3.3 g of the product (yield 74%).

[0578]

[0579] 2. P3-14 Synthesis Example

[0580]

[0581] 4,4'-dibromo-1,1'-biphenyl (1.0 g, 3.21 mmol), Sub6-13 (2.4 g, 7.05 mmol), K2CO3 (1.3 g, 9.62 mmol), Pd(PPh3)4 (0.07 g, 0.06 mmol), and toluene (11 mL) were synthesized using the above P3-1 method to obtain 1.26 g of the product (yield: 68%).

[0582]

[0583] Meanwhile, the FD-MS values ​​of compounds P3-1 to P3-23 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 3 below.

[0584] Compound FD-MS Compound FD-MSP3-1 m / z = 743.07 (C 36 H 12 F 15 N=743.48)P3-2m / z=958.96(C 36 F 27 N=959.36)P3-3m / z=555.12(C 31 H 17 F8N=555.47)P3-4m / z=703.14(C 40 H 19 F 10 N=703.58)P3-5m / z=517.09(C 30 H 16 F5NS=517.52)P3-6m / z=818.18(C 48 H 24 F 10 N2=818.72)P3-7m / z=671.19(C 40 H 25 F8N=671.63)P3-8m / z=1199.03(C 36 H 12 F 39 N=1199.44)P3-9m / z=1040.15(C 54 H 22 F 18 N2=1040.76)P3-10m / z=964.12(C 48 H 18 F 18 N2=964.66)P3-11m / z=870.21(C 52 H 28 F 10 N2=870.79)P3-12m / z=804.08(C 42 H 18 F 10 N2S2=804.72)P3-13m / z=628.11(C 32 H 16 F 12 =628.46)P3-14m / z=578.09(C 28 H 14 F 12=578.40)P3-15m / z=486.05(C 24 H8F 10 =486.31)P3-16m / z=986.01(C 34 H8F 30 =986.39)P3-17m / z=718.10(C 30 H 16 F 18 =718.43)P3-18m / z=682.15(C 36 H 22 F 12 =682.55)P3-19m / z=826.08(C 36 H 14 F 20 =826.48)P3-20m / z=1032.10(C 44 H 20 F 24 Si=1032.69)P3-21m / z=1410.07(C 54 H 22 F 36 Si2=1410.88)P3-22m / z=1168.18(C 57 H 28 F 24 =1168.81)P3-23m / z=1984.03(C 69 H 16 F 60 =1984.79)

[0585] P4 화합물 합성법

[0586] 1. P4-11 합성예

[0587]

[0588] 2-(4-bromophenyl)benzo[d]thiazole (5.0 g, 17.2 mmol) was dissolved in toluene (57 mL) in a round-bottomed flask, and bis(4-(naphthalen-1-yl)phenyl)amine (7.3 g, 17.2 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), P(t-Bu)3 (0.4 mL, 1.0 mmol), and NaOt-Bu (3.3 g, 34.5 mmol) were added, and the reaction was carried out at 60°C. Upon completion of the reaction, the organic layer was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The resulting organic material was then purified by silica gel column chromatography and recrystallization to obtain 8.9 g of the product (yield 82%).

[0589]

[0590] 2. P4-13 Synthesis Example

[0591]

[0592] 2-(4-bromophenyl)benzo[d]oxazole (5.0 g, 18.2 mmol), dibenzo[b,d]thiophen-3-amine (1.8 g, 9.1 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol), P(t-Bu)3 (0.2 mL, 0.5 mmol), and NaOt-Bu (1.8 g, 18.2 mmol) were added to a round-bottomed flask, and 6.7 g of the product was obtained using the synthetic method of P4-11 above. (Yield 63%)

[0593]

[0594] 3. P4-14 Synthesis Example

[0595]

[0596] 2-(4-bromophenyl)benzo[d]thiazole (5.0 g, 17.2 mmol), 9,9'-spirobi[fluoren]-4-amine (2.9 g, 8.6 mmol), Pd2(dba)3 (0.2 g, 0.3 mmol), P(t-Bu)3 (0.2 mL, 0.5 mmol), and NaOt-Bu (1.7 g, 17.2 mmol) were added to a round-bottomed flask, and 8 g of the product was obtained using the synthetic method of P4-11 above. (Yield 62%)

[0597]

[0598] 4. P4-28 Synthesis Example

[0599]

[0600] 9-bromonaphtho[1,2-b]benzofuran (5.0 g, 16.8 mmol), N-(2-(benzo[d]thiazol-2-yl)phenyl)dibenzo[b,d]thiophen-2-amine (6.9 g, 16.8 mmol), Pd2(dba)3 (0.5 g, 0.5 mmol), P(t-Bu)3 (0.4 mL, 1.0 mmol), and NaOt-Bu (3.2 g, 33.7 mmol) were added to a round-bottomed flask, and 7.3 g of the product was obtained using the synthetic method of P4-11 above. (Yield 69%)

[0601]

[0602] 5. P4-38 Synthesis Example

[0603]

[0604] N-(4-(benzo[d]oxazol-2-yl)phenyl)-8-bromo-N-phenyldibenzo[b,d]thiophen-3-amine (5.0 g, 9.1 mmol), 4-(benzo[d]oxazol-2-yl)-N-phenylaniline (2.6 g, 9.1 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol), P(t-Bu)3 (0.2 mL, 0.5 mmol), NaOt-Bu (1.8 g, 18.3 mmol) were added to a round-bottom flask, and 5.8 g of the product was obtained using the synthetic method of P4-11 above. (Yield 84%)

[0605]

[0606] 6. P4-53 Synthesis Example

[0607]

[0608] In a round-bottom flask, (4-(benzo[d]oxazol-2-yl)phenyl)boronic acid (5.0 g, 20.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.2 g, 20.9 mmol), Pd(PPh3)4 (0.7 g, 0.6 mmol), and NaOH (1.7 g, 41.8 mmol) were added, and 9.4 g of the product was obtained using the synthetic method of P2-1 above. (Yield 89%)

[0609]

[0610] 7. P4-64 Synthesis Example

[0611]

[0612] 2-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)benzo[d]thiazole (5.0 g, 12.1 mmol), 2-chloro-4-phenyl-6-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,5-triazine (6.3 g, 12.1 mmol), Pd(PPh3)4 (0.4 g, 0.4 mmol), NaOH (1.0 g, 24.2 mmol) were added to a round-bottom flask, and 7.9 g of the product was obtained using the synthetic method of P2-1 above. (Yield 84%)

[0613]

[0614] 8. P4-78 Synthesis Example

[0615]

[0616] In a round-bottom flask, (3-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid (5.0 g, 15.9 mmol), 9-bromo-10-(9,9-dimethyl-9H-fluoren-3-yl)anthracene (7.2 g, 15.9 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and NaOH (1.3 g, 31.8 mmol) were added, and 8 g of the product was obtained using the synthetic method of P2-1 above. (Yield 79%)

[0617]

[0618] 9. P4-83 Synthesis Example

[0619]

[0620] 2-(4'-bromo-[1,1'-biphenyl]-4-yl)benzo[b]thiophene (5.0 g, 13.7 mmol), bis(4-(naphthalen-2-yl)phenyl)amine (5.8 g, 13.7 mmol), Pd2(dba)3 (0.4 g, 0.4 mmol), P(t-Bu)3 (0.3 mL, 0.8 mmol), and NaOt-Bu (2.6 g, 27.4 mmol) were added to a round-bottomed flask, and 7.8 g of the product was obtained using the synthetic method of P2-1 above. (Yield 81%)

[0621]

[0622] Meanwhile, the FD-MS values ​​of compounds P4-1 to P4-92 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 4 below.

[0623] Compound FD-MS Compound FD-MSP4-1 m / z = 286.11 (C 19 H 14 N2O=286.33)P4-2m / z=454.15(C 31 H 22 N2S=454.59)P4-3m / z=403.13(C 26 H 17 N3O2=403.44)P4-4m / z=495.14(C 32 H 21 N3OS=495.6)P4-5m / z=509.12(C 32 H 19 N3O2S=509.58)P4-6m / z=657.19(C 45 H 27 N3OS=657.79)P4-7m / z=554.18(C 39 H 26 N2S=554.71)P4-8m / z=554.18(C 39 H 26 N2S=554.71)P4-9m / z=362.14(C 25 H 18 N2O=362.43)P4-10m / z=589.25(C 43 H 31 N3=589.74)P4-11m / z=630.21(C45 H 30 N2S=630.81)P4-12m / z=605.21(C 42 H 27 N3O2=605.7)P4-13m / z=585.15(C 38 H 23 N3O2S=585.68)P4-14m / z=749.2(C 51 H 31 N3S2=749.95)P4-15m / z=661.18(C 44 H 27 N3O2S=661.78)P4-16m / z=511.12(C 32 H 21 N3S2=511.66)P4-17m / z=651.14(C 42 H 25 N3OS2=651.8)P4-18m / z=372.2(C 25 H8D 10 N2O=372.49)P4-19m / z=561.13(C 36 H 23 N3S2=561.72)P4-20m / z=587.15(C 38 H 25 N3S2=587.76)P4-21m / z=635.17(C 42 H 25 N3O2S=635.74)P4-22m / z=644.12(C 39 H 24 N4S3=644.83)P4-23m / z=784.25(C 56 H 36 N2OS=784.98)P4-24m / z=665.19(C 44 H 28 FN3OS=665.79)P4-25m / z=648.31(C 47 H 40 N2O=648.85)P4-26m / z=721.22(C 50 H 31 N3OS=721.88)P4-27m / z=736.23(C 50 H 32 N4OS=736.89)P4-28m / z=624.13(C 41 H 24N2OS2=624.78)P4-29m / z=579.23(C 41 H 29 N3O=579.7)P4-30m / z=730.31(C 53 H 38 N4=730.92)P4-31m / z=737.29(C 52 H 39 N3S=737.97)P4-32m / z=604.23(C 42 H 28 N4O=604.71)P4-33m / z=813.24(C 56 H 35 N3O2S=813.98)P4-34m / z=875.3(C 62 H 41 N3OS=876.09)P4-35m / z=692.17(C 44 H 28 N4OS2=692.86)P4-36m / z=635.2(C 43 H 29 N3OS=635.79)P4-37m / z=768.2(C 50 H 32 N4OS2=768.95)P4-38m / z=752.22(C 50 H 32 N4O2S=752.89)P4-39m / z=665.16(C 43 H 27 N3OS2=665.83)P4-40m / z=760.27(C 53 H 36 N4S=760.96)P4-41m / z=661.26(C 46 H 35 N3S=661.87)P4-42m / z=752.22(C 50 H 32 N4O2S=752.89)P4-43m / z=724.23(C 49 H 32 N4OS=724.88)P4-44m / z=751.32(C 53 H 41 N3O2=751.93)P4-45m / z=725.21(C 49 H 31 N3O2S=725.87)P4-46m / z=751.21(C 51 H33 N3S2=751.97)P4-47m / z=635.2(C 43 H 29 N3OS=635.79)P4-48m / z=745.27(C 53 H 35 N3O2=745.88)P4-49m / z=752.22(C 50 H 32 N4O2S=752.89)P4-50m / z=815.22(C 55 H 33 N3O3S=815.95)P4-51m / z=893.29(C 62 H 43 N3S2=894.17)P4-52m / z=803.24(C 55 H 37 N3S2=804.04)P4-53m / z=502.18(C 34 H 22 N4O=502.58)P4-54m / z=666.24(C 47 H 30 N4O=666.78)P4-55m / z=622.18(C 41 H 26 N4OS=622.75)P4-56m / z=560.15(C 36 H 21 FN4S=560.65)P4-57m / z=607.18(C 40 H 25 N5S=607.74)P4-58m / z=733.23(C 50 H 31 N5S=733.89)P4-59m / z=685.19(C 45 H 27 N5OS=685.81)P4-60m / z=482.21(C 32 H 26 N4O=482.59)P4-61m / z=602.21(C 42 H 26 N4O=602.7)P4-62m / z=608.17(C 40 H 24 N4OS=608.72)P4-63m / z=503.17(C 33 H 21 N5O=503.57)P4-64m / z=772.23(C 53 H32 N4OS=772.93)P4-65m / z=648.2(C 43 H 28 N4OS=648.78)P4-66m / z=648.2(C 43 H 28 N4OS=648.78)P4-67m / z=568.17(C 38 H 24 N4S=568.7)P4-68m / z=568.17(C 38 H 24 N4S=568.7)P4-69m / z=549.21(C 41 H 27 NO=549.67)P4-70m / z=437.12(C 31 H 19 NS=437.56)P4-71m / z=528.17(C 37 H 24 N2S=528.67)P4-72m / z=710.27(C 54 H 34 N2=710.88)P4-73m / z=447.16(C 33 H 21 NO=447.54)P4-74m / z=553.15(C 39 H 23 NOS=553.68)P4-75m / z=615.2(C 45 H 29 NS=615.79)P4-76m / z=573.21(C 43 H 27 NO=573.7)P4-77m / z=598.24(C 45 H 30 N2=598.75)P4-78m / z=638.27(C 48 H 34 N2=638.81)P4-79m / z=629.18(C 45 H 27 NOS=629.78)P4-80m / z=670.17(C 46 H 26 N2O2S=670.79)P4-81m / z=285.12(C 20 H 15 NO=285.35)P4-82m / z=513.21(C 38 H 27NO=513.64)P4-83m / z=705.25(C 52 H 35 NS=705.92)P4-84m / z=635.17(C 44 H 29 NS2=635.84)P4-85m / z=641.13(C 42 H 27 NS3=641.87)P4-86m / z=569.27(C 42 H 35 NO=569.75)P4-87m / z=619.2(C 44 H 29 NOS=619.78)P4-88m / z=705.25(C 52 H 35 NS=705.92)P4-89m / z=501.18(C 35 H 23 N3O=501.59)P4-90m / z=531.14(C 35 H 21 N3OS=531.63)P4-91m / z=769.26(C 55 H 35 N3S=769.97)P4-92m / z=593.19(C 41 H 27 N3S=593.75)

[0624] Meanwhile, although the exemplary synthetic examples of the present invention represented by Chemical Formulas 1 to 4, Chemical Formula A and Chemical Formula G have been described above, these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504) and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and it will be easily understood by those skilled in the art that the above reaction proceeds even if other substituents defined in Chemical Formulas 1 to 4, Chemical Formula A and Chemical Formula G are combined in addition to the substituents specified in the specific synthetic examples.

[0625]

[0626] [Component Data]

[0627] [Example 1]

[0628] First, a N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (hereinafter, 2-TNATA) film was vacuum-deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer with a thickness of 60 nm, and then a compound P1-51 represented by the chemical formula 1 of the present invention was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 60 nm, and then a light-emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping DPTPCz [3-(4,6-Diphenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole] as a host and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] as a dopant material at a weight ratio of 95:5. Next, the compound P2-48 represented by the chemical formula 3 of the present invention was vacuum-deposited to a thickness of 40 nm as an electron transport layer, LiF, a halogenated alkali metal, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing the first part, which is a light-emitting region.

[0629]

[0630] [Example 2] and [Example 3]

[0631] A first part was prepared in the same manner as in Example 1, except that the compounds of the present invention described in Table 5 below were used instead of the compound P1-51 of the present invention as a hole transport layer material and the compound P2-48 of the present invention as an electron transport layer material.

[0632]

[0633] [Comparative Example 1]

[0634] A first part was prepared in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P1-51 of the present invention as a hole transport layer material, and the following comparative compound B was used instead of the compound P2-48 of the present invention as an electron transport layer material.

[0635] [Comparative Compound A] [Comparative Compound B]

[0636]

[0637]

[0638] The electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch by applying a forward bias DC voltage to the first part of the example and comparative example manufactured in this way, and the measurement result was 5000 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. Table 5 below shows the results of the device fabrication and evaluation.

[0639] This measuring device can evaluate the performance of new materials compared to reference compounds under identical conditions, regardless of possible daily variations in deposition rate, vacuum quality, or other parameters. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner demonstrate statistical significance.

[0640] Hole transport layer Electron transport layer Driving voltage (V) Current (mA / cm) 2 ) Luminance (cd / m 2 ) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound A Comparative Compound B 6.6 27.5 5000 18.2 84.2 Example 1 P1-5 1 P2-4 86.0 22.1 5000 22.6 9 2.7 Example 2 P1-5 7 P2-2 95.9 14.4 5000 34.7 9 5.3 Example 3 P1-3 P2-4 15.8 13.1 5000 38.1 100.1

[0641] Looking at Table 5 above, it can be confirmed that the device performance is greatly improved when the compound of the present invention is used as a hole transport layer and an electron transport layer.

[0642] The hole mobility and HOMO values ​​of the comparative compounds A and P1-51 are shown in Table 6 below.

[0643] Comparative compound AP1-51 hole mobility 7.8×10 -3 cm 2 / Vs3.0×10 -4 cm 2 / VsHOMO6.0 eV-5.5 eV

[0644] As can be seen in Table 6 above, P1-51 is 1.0×10 -3 cm 2 / Vs or less, and the HOMO also has a value of -5.5 eV. In the case of hole mobility, the lower the value, the faster the hole movement speed, and there is a phenomenon in which the driving voltage decreases as the hole mobility increases.

[0645] Additionally, the LUMO values ​​of the comparative compounds B and P2-48 are shown in Table 7 below.

[0646] Comparative compound BP2-48LUMO-2.6 eV-3.0 eV

[0647] As can be seen in Table 7 above, the LUMO value of comparative compound B has a value of -2.6 eV, and the LUMO value of P2-48 has a value of -3.0 eV. As can be seen in Tables 5 to 7 above, the injection characteristics of holes and electrons can be controlled according to the HOMO and LUMO values, and the more similar the ratio of holes and electrons in the light-emitting layer, the higher the efficiency can be. That is, when the hole transport layer and electron transport layer of specific conditions are satisfied as described above, an optimal organic electroluminescence device can be manufactured.

[0648]

[0649] [Example 4]

[0650] First, P1-7 was vacuum-deposited as an organic layer on a glass substrate to form a 60 nm thickness, and comparative compound B was vacuum-deposited on P1-7 to form a 40 nm thickness. Then, compound P3-13 of the present invention was vacuum-deposited on the organic layer to form a 10 nm thickness, thereby forming a metal patterning layer. Subsequently, Al was deposited as a cathode on the metal patterning layer. Thereafter, compound P4-42 of the present invention was deposited as a third part to a 70 nm thickness, thereby producing a sample necessary for measuring light transmittance.

[0651]

[0652] [Example 5] to [Example 8]

[0653] A light transmittance sample was prepared in the same manner as in Example 4, except that the compound of the present invention described in Table 8 below was used instead of the compound P3-13 of the present invention as the metal patterning layer material.

[0654]

[0655] [Comparative Example 2]

[0656] A light transmittance sample was produced in the same manner as in Example 4, except that no metal patterning layer was used.

[0657]

[0658] [Comparative Example 3]

[0659] A light transmittance sample was produced in the same manner as in Example 4, except that P1-7 was used instead of the compound P3-13 of the present invention as the metal patterning layer material.

[0660]

[0661] [Comparative Example 4]

[0662] A light transmittance sample was prepared in the same manner as in Example 4, except that the comparative compound C below was used instead of the compound P4-42 of the present invention as the third part material.

[0663] [Comparative Compound C]

[0664]

[0665]

[0666] The light transmittance of the examples and comparative examples manufactured in this manner was measured at 550 nm in the visible light range using a Lambda 365 UV / VIS Spectrometer measuring device from Perkinelmer, and the results of the measurement are shown in Table 8 below.

[0667] Metal patterning layer 3 Partial transmittance T(%) Comparative example 2-P4-4 261.1% 100% Comparative example 3P1-7P4-4 261.4% 100% Comparative example 4P3-13 Comparative compound C 6 8.4% 112% Example 4P3-13P4-4 275.3% 125% Example 5P3-16P4-4 276.1% 127% Example 6P3-18P4-4 278.4% 124% Example 7P3-19P4-4 277.5% 126% Example 8P3-20P4-13 76.9% 125%

[0668] As can be seen in Table 8, when comparing Comparative Examples 2 to 3 and the Examples of the present invention, it can be confirmed that when the compound of the present invention is used as a metal patterning layer, the light transmittance is high. This can be seen that when there is no metal patterning layer or when the metal patterning layer is present but has high adhesion to the metal, the cathode (metal) is laminated before the third part is laminated, resulting in a significantly lower transmittance.

[0669] And, when comparing Comparative Example 4 and the examples of the present invention, it can be confirmed that when the compound of the present invention is used as the third part, high light transmittance is exhibited. In particular, when both materials with high transmittance are used as the material of the metal patterning layer and the material of the third part, as in the present invention, it can be confirmed that high transmittance is exhibited.

[0670]

[0671] The contact angles of comparative compound C and the metal patterning layer compound P3-13 of the present invention are shown in Table 9 below.

[0672] Contact angle comparison compound C83.2°P3-13106.1°

[0673] Looking at Table 9 above, it can be confirmed that while the contact angle of Comparative Compound C is 83.2°, the metal patterning layer material of the present invention has a contact angle of 100° or more. Therefore, it is believed that when the contact angle of the metal patterning layer material is 100° or more, it exhibits high transmittance. In other words, the higher the contact angle, the less adhesion to the metal, which can prevent the metal from being laminated.

[0674] The refractive indices of comparative compound C and the third part compound P4-42 of the present invention are shown in Table 10 below.

[0675] Comparative compound CP4-42 refractive index 1.82 1.99

[0676] As can be seen in Table 10 above, when the compound of the present invention is used as the third part, it can be confirmed that the refractive index of the compound of the present invention is 1.85 or higher, and the refractive index of the comparative compound C is 1.82. Therefore, when the metal patterning layer compound of the present invention and the third part compound are used simultaneously, it can be confirmed that the overall transmittance shows a high transmittance of 70% or higher, and it can be seen that it is very suitable when manufacturing a display for UDC / UPS.

[0677] Additionally, since it does not contain perfluorinated compounds, it can provide an optimal organic light-emitting display device that can address concerns about human health and the environment.

[0678]

[0679] The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are intended to illustrate, not limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all techniques within a scope equivalent thereto should be interpreted as being included within the scope of the present invention.

[0680] According to the present invention, an organic device having excellent device characteristics such as high brightness, high luminescence, and long lifespan can be manufactured, and thus has industrial applicability.

Claims

1. Substrate; An anode (100) disposed on the above substrate; On the above anode (100), there are a first part (110) which is a light-emitting area; and a second part (120) which is a transmission area; The first part (110) and the second part (120) include an organic layer (111) formed in common; The above organic layer (111) includes a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115). A cathode (118) exists on the organic layer (111) of the first part (110). A metal patterning layer (121) exists on the organic layer (111) of the second part (120). An organic electric element characterized in that the above metal patterning layer (121) does not contain a perfluorinated compound.

2. An organic electric device according to claim 1, characterized in that the perfluorinated compound is perfluorinated sulfonate (PFSA) or perfluoroalkyl acid (PFAA).

3. An organic electric device according to claim 1, characterized in that the perfluorinated compound is perfluorooctane sulfonate (PFOS), perfluorobutane sulfonate (PFBS), or perfluorohexane sulfonate (PFHxS).

4. An organic electric device according to claim 1, wherein the perfluorinated compound is perfluorooctanoic acid (PFOA), perfluorohexanoic acid (PFHxA), perfluoroundecanoic acid (PFUnDA), perfluoroheptanoic acid (PFHpA), perfluorododecanoic acid (PFDnDA), perfluorononanoic acid (PFNA), or perfluorodecanoic acid (PFDA).

5. In the first paragraph, the metal patterning layer (121) is characterized in that it includes a monofluorinated compound; or an aromatic or alkene compound including at least one carbon substituted with F, CF2 or CF3 at a hydrogen position and a carbon not substituted with fluorine at a hydrogen position; 6. In the first paragraph, the metal patterning layer (121) is characterized in that it includes a compound represented by the following chemical formula A. [Chemical Formula A] {In the above chemical formula A, {In the above chemical formula A and chemical formula A-1, A 200 Hwan, B 200 Hwan and C 200 The rings are independently C6~C 60 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 60 is a heteroaryl group; L 201 is a single bond; NR 204 ; CR 204 R 205 ; or SiR 204 R 205 ;and, R 201 , R 202 and R 203 are each the same or different and independently represent hydrogen; deuterium; halogen; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; C6~C 30 Aryloxy group of; CF3; CF2H; C4H4F3; C3H2F3; C3F5; SF5; N(R 401 )(R 402 ); and Si(R 401 )(R 402 )(R 403 ); is selected from the group consisting of, However, R 201 , R 202 and R 203 At least one of them is selected from the group consisting of fluorine (F); CF3; CF2H; C4H4F3; C3H2F3; C3F5; and SF5; R 204 and R 205 are independently hydrogen; deuterium; halogen; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1~C 60 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 30 Alkoxyl group of; and C6~C 30 is selected from the group consisting of aryloxy group of R, or 204 Wow R 205 can combine with each other to form rings, R 401 , R 402 and R 403 are independently C6~C 20 Aryl group of; or C2~C containing at least one heteroatom among O, N, S, Si and P 20 is a heterocyclic group; and n201 is an integer from 0 to 3, a201, a202 and a203 are independently integers from 1 to 10, Here, the aryl group, arylene group, heteroaryl group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group and aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C1~C 20 Alkylthio group of; C1~C 20 Alkoxyl group of; C1~C 20 Alkyl group of; C1~C substituted with halogen 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkyne group of; C6~C 20 Aryl group of; C6~C substituted with deuterium 20 Aryl group of; C6~C substituted with halogen 20 Aryl group of; Fluorenyl group; C2~C 20 Heterocyclic group of; C3~C 20 Aliphatic ring group; C7~C 20 Arylalkyl group of; C8~C 20 Aryl alkenyl group of; and C7~C 20 It may be further substituted with one or more substituents selected from the group consisting of alkylaryl groups; and further, the hydrogen of these substituents may be further substituted with one or more deuteriums, and further, these substituents may be combined with each other to form a ring, wherein the 'ring' means C3~C 60 Aliphatic ring or C6~C 60 Aromatic ring or C2~C 60 A fused ring composed of a heterocycle or a combination thereof, including a saturated or unsaturated ring.

7. An organic electric element characterized in that the transmittance of the metal patterning layer (121) material in the first paragraph is 80% or more.

8. An organic electric device according to claim 1, further comprising a light efficiency improvement layer formed on at least one surface of the anode (100) and the cathode (118) opposite to the organic layer.

9. In the first paragraph, an organic electric device characterized in that the organic material layer includes two or more stacks including a hole transport layer (113), a light-emitting layer (114), and an electron transport layer (115) sequentially formed on an anode (100).

10. An organic electric device according to claim 9, characterized in that the organic layer further includes a charge generation layer formed between the two or more stacks.

11. An electronic device comprising a display device including the organic electric element of paragraph 1; and a control unit for driving the display device.

12. In the 11th paragraph, the organic light-emitting display device is an electronic device characterized in that it is at least one of an organic electroluminescent element, an organic solar cell, an organic photoconductor, an organic transistor, a monochrome or white lighting element, and a display element.

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