KR20240045434A - Organic Light Emitting Display device having an emitting area and a transport area - Google Patents

Abstract

The present invention relates to an organic light emitting display device. More specifically, the light emitting area and the transmission area exist in common, and the difficulties in the process can be solved by patterning the electrode without using a shadow mask. This relates to an organic light emitting display device that can implement a full-screen display such as an image sensor or UDC.

Description

Organic light emitting display device having an emitting area and a transport area}

The present invention relates to an organic light emitting display device including a light-emitting area and a transmission area. More specifically, the light-emitting area and the transmission area exist in common, and the electrode can be patterned without using a shadow mask. It relates to an organic light emitting display device.

With the continued development of display technology, user demand for display devices is increasing. Terminal display devices are being developed in the direction of flexibility, full screen, and high integration. In the case of smartphone displays, in order to increase the screen size, a bezel size is reduced or a bezel-less under display is being developed. In this process, the physical buttons on the front of the smartphone disappear into the screen, and technologies such as UDC (Under Display Camera) or UPS (Under Panel Sensor) are being developed. UDC requires high light transmittance of the display for the camera to operate normally. Therefore, in the case of smartphones or electronic devices to which devices such as UDC are applied, it is necessary to secure high light transmittance. In Korean Patent No. 10-2324529, invented by the present applicant, this purpose can be achieved by forming a metal patterning layer. It is disclosed that it can be done. In addition, Korean Patent Publication No. 10-2022-0006001 discloses a metal patterning method using an organic thin film that selectively repels metal materials while forming an organic patterning layer by vacuum deposition.

In general, two major methods are used as electrode pattern methods. The first method is to pattern the electrode in the desired area using a shadow mask, or the second method is to create a pattern by irradiating a laser to the cathode. However, the electrode patterning method using a shadow mask causes bending during the high-temperature deposition process due to the typical material characteristics of a metal mask, which causes the mask shape and electrode pattern to be distorted. Accordingly, time and cost for maintaining the mask are inevitably required, making it not commercially suitable for mass production of devices.

In addition, the electrode patterning method using a laser causes the inconvenience of having to determine the type and intensity of the laser to prevent damage to the substrate by patterning the electrode due to the unique properties of the laser.

Therefore, in order to implement a full-screen display device such as an image sensor or UDC, it is necessary to implement a device that has both a light-emitting area and a transmission area, and development of optimal organic light-emitting display device technology that can also solve process difficulties is necessary. do.

In the present invention, in an organic light emitting display device, the light emitting area and the transmission area are common, and the difficulties in the process can be solved by patterning the electrode without using a shadow mask, and furthermore, the image sensor, UDC and The purpose is to provide an optimal organic light emitting display device that can implement the same full-screen display.

In one aspect, the present invention includes: a substrate;

An anode 100 disposed on the substrate;

a first portion 110 that is a light emitting area on the anode 100; and a second part 120, which is a transmission area, is present,

The first part 110 and the second part 120 include an organic material layer 111 formed in common,

The organic material layer 111 includes a hole transport layer 113 and an electron transport layer 115,

A cathode 118 exists on the organic material layer 111 of the first part 110,

A metal patterning layer 121 is present on the organic material layer 111 of the second part 120,

A third part 130, which is a common area, is included on the first part 110 and the second part 120,

The hole mobility of the hole transport layer 113 material is 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs, and the HOMO (Hightest Occupied Molecular) of the hole transport layer 113 material is Orbital) energy level is -5.5 eV to -5.0 eV,

The electron mobility of the electron transport layer 115 material is 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs, and the LUMO (Lowest Occupied Molecular) of the electron transport layer 115 material is Orbital) energy level is -3.5 eV to -2.8 eV,

The contact angle of the metal patterning layer 121 material is 100° to 180°,

The material of the third portion 130 provides an organic light emitting display device having a refractive index of 1.85 to 3.0.

In another aspect, the present invention provides an electronic device including the organic light emitting display device.

The organic light emitting display device according to the present invention has a light emitting area and a transmission area at the same time, can solve processing difficulties by patterning the electrode without using a shadow mask, and has high luminous efficiency and low driving voltage. This can be achieved and can be used to manufacture displays for UDC and UPS.

1 to 13 are exemplary diagrams of an organic light emitting display device according to the present invention.

When adding reference numerals to components in each drawing, it should be noted that identical components are given the same reference numerals as much as possible even if they are shown in different drawings. Additionally, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

When “comprises,” “has,” “consists of,” etc. mentioned in the specification are used, other parts may be added unless “only” is used. When a component is expressed in the singular, it can also include the plural, unless specifically stated otherwise.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

Additionally, when a component, such as a layer, membrane, region, plate, etc., is said to be "on" or "on" another component, it means not only that it is "directly above" the other component, but also that there is another component in between. It should be understood that it can also include cases. Conversely, when an element is said to be "right on top" of another part, it should be understood to mean that there is no other part in between.

As used in this specification and the appended claims, unless otherwise noted, the following terms have the following meanings.

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl), or iodine (I), unless otherwise specified.

As used in the present invention, the term "alkyl" or "alkyl group", unless otherwise specified, has a single bond of 1 to 60 carbon atoms, and includes straight chain alkyl group, branched chain alkyl group, cycloalkyl (cycloaliphatic) group, and alkyl-substituted cyclo. It refers to radicals of saturated aliphatic functional groups, including alkyl groups and cycloalkyl-substituted alkyl groups.

As used in the present invention, the terms "alkenyl group", "alkenyl group" or "alkynyl group", unless otherwise specified, each have a double or triple bond of 2 to 60 carbon atoms, and include a straight or branched chain group. , but is not limited to this.

The term “cycloalkyl” used in the present invention refers to alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.

As used in the present invention, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60, and is limited thereto, unless otherwise specified. That is not the case.

The term “aryloxyl group” or “aryloxy group” used in the present invention refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

The term “alkylthio group” used in this specification refers to an alkyl group to which a sulfur radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.

The term “arylthio group” used in this specification refers to an aryl group to which a sulfur radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, but is not limited thereto.

As used herein, the terms “aryl group” and “arylene group” each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or arylene group refers to an aromatic group of a single ring or multiple rings, and includes an aromatic ring formed by combining adjacent substituents or participating in a reaction. For example, the aryl group may be a phenyl group, biphenyl group, fluorene group, or spirofluorene group.

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 a radical substituted with an aryl group has the carbon number described in this specification. Additionally, when prefixes are named consecutively, it means that the substituents are listed in the order they are listed first. For example, an arylalkoxy group refers to an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group refers to a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group refers to an alkenyl group substituted with an arylcarbonyl group. And here, the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heterocyclic group", unless otherwise specified, contains one or more heteroatoms, has a carbon number of 2 to 60, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heterocyclic group. Contains an aromatic ring. It may also be formed by combining neighboring functional groups.

As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.

In addition, “heterocyclic group” refers to a single ring containing heteroatoms, ring aggregates, multiple fused ring systems, spiro compounds, etc. In addition, compounds containing heteroatom groups such as SO ₂ , P=O, etc., such as the compounds below, instead of carbon forming a ring, may also be included in the heterocyclic group.

The term "aliphatic ring" used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes single rings, ring aggregates, fused multiple ring systems, spiro compounds, etc., and has the number of carbon atoms unless otherwise specified. It means 3 to 60 rings, but is not limited thereto. For example, even when benzene, an aromatic ring, and cyclohexane, a non-aromatic ring, are fused, it is an aliphatic ring.

As used in the present invention, the terms "fluorenyl group", "fluorenylene group", and "fluorenetriyl group" refer to monovalent and 2-valent groups in which R, R' and R" are all hydrogen in the structures below, unless otherwise specified. It means a valent or trivalent functional group, and "substituted fluorenyl group", "substituted fluorenylene group" or "substituted fluorenetriyl group" means that at least one of the substituents R, R', and R" is other than hydrogen. It means a substituent, and includes cases where R and R' are bonded to each other to form a spiro compound with the carbon to which they are bonded. In this specification, fluorenyl group, fluorenylene group, and fluorenetriyl group may all be referred to as fluorene groups, regardless of valence.

In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., as examples of each symbol and its substituent, may be written as the 'name of the group reflecting the valence', but is written as the 'parent compound name'. You may. For example, in the case of 'phenanthrene', a type of aryl group, the name of the group may be written by distinguishing the valence, such as the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene', but the valence and Regardless, it can also be written as the parent compound name, ‘phenanthrene’. Similarly, in the case of pyrimidine, it can be written as 'pyrimidine' regardless of the valence, or it can be written as the 'name of the group' of the valence, such as pyrimidineyl group in the case of monovalent group, pyrimidineylene in the case of divalent group, etc. there is. Additionally, in this specification, when describing compound names or substituent names, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu. Orene can be described as dimethylfluorene, etc. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

Additionally, unless explicitly stated otherwise, the chemical formula used in the present invention is applied identically to the substituent definition by the index definition in the following chemical formula.

Here, if a is an integer of 0, the substituent R1 is absent, and if a is an integer of 1, one substituent ^R1 is bonded to any one of the carbons forming the benzene ring, and if a is an integer of 2 or 3, respectively. It is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is expressed as Omit it.

Additionally, unless otherwise specified in the specification, when expressing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. 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.

Additionally, unless otherwise specified in the specification, when a ring is expressed in the form of a 'number atom' such as a 5-member ring, a 6-member 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.

In addition, unless otherwise specified in the specification, the ring formed by combining adjacent groups is an aromatic ring group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and an aliphatic ring group of C ₃ to C ₆₀ .

At this time, unless otherwise specified in the specification, 'neighboring groups' refers to groups R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , Not only R ⁵ and R ⁶ but also R ⁷ and R ⁸ that share one carbon are included, and groups that are not immediately adjacent, such as between R ¹ and R ⁷ , between R ¹ and R ⁸ , or between R ⁴ and R ⁵ , etc. Substituents bonded to ring constituent elements (carbon, nitrogen, etc.) may also be included. In other words, if there are substituents on immediately adjacent ring elements such as carbon or nitrogen, they can become neighboring groups, but if no substituents are bonded to the immediately adjacent ring elements, they can be bonded to the next ring element. It can be a group adjacent to a substituent, and substituents bonded to carbons of the same ring can also be said to be neighboring groups.

In the formula below, when substituents bonded to the same carbon, such as R ⁷ and R ⁸ , combine to form a ring, a compound containing a spiro moiety may be formed.

In addition, in this specification, the expression 'neighboring groups can combine with each other to form a ring' is used in the same meaning as 'neighboring groups can selectively form a ring by combining with each other', and at least one pair This refers to a case where neighboring groups combine with each other to form a ring.

Hereinafter, an organic light emitting display device according to an embodiment of the present invention will be described in detail with reference to the accompanying FIGS. 1 to 13.

1 to 13 are diagrams schematically showing the configuration of an organic light emitting display device according to an embodiment of the present invention.

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), and a first portion (which is a light emitting area) on the anode 100. 110) and a second part 120 that is a transparent area, and a third part 130 that is a common area exists on the first part 110 and the second part 120. In addition, the first part 110 and the second part 120 include a common organic material layer 111, and the organic material layer 111 includes a hole transport layer 113 and an electron transport layer 115, A cathode 118 is formed on the organic material layer 111 of the first part 110, and a metal patterning layer 121 is formed on the organic material layer 111 of the second part 120.

1 to 11, the height of the first part 110 and the height of the second part 120 are shown to be the same, but their heights may be the same or different. In addition, FIGS. 1 to 11 are schematic drawings to explain the stacked structure of the organic light emitting display device, and the height, area, and formed positions of the first part 110 and the second part 120 are shown in these drawings. is not limited by

The anode 100 may be a transparent electrode. Typically, the material forming the transparent electrode is a transparent conducting oxide (TCO), such as indium tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO ₂ ), or indium zinc oxide (IZO), and combinations thereof. It may be selected, but is not limited thereto. Additionally, the anode 100 may be used as a multi-layer comprising two or more layers.

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 a light-emitting layer 114, and the light-emitting 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, a light emitting 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 consist of one or more layers. That is, it may be composed of a multi-layer hole transport layer 113 such as a first hole transport layer, a second hole transport layer, and a third hole transport layer, and the names of the multi-layer hole transport layers 113 may 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 called a light emitting auxiliary layer, a buffer layer, an electron blocking layer, an electron blocking layer, an exciton blocking layer, etc. In Figures 9, 11, 12, and 13, it is named the light emitting auxiliary layer 122. In addition, in Figure 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 to this. 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, and a third electron transport layer, and the names of the multilayer electron transport layers 115 may be different. For example, if the electron transport layer 115 is composed of two layers, the electron transport layer 115 adjacent to the light emitting layer 114 can be called an auxiliary layer, a buffer layer, A-ETL, a hole blocking layer, a hole blocking layer, etc. 9 to 13, it is named hole blocking layer 123. For example, the first part 110 is formed sequentially from the anode 100 to a hole injection layer 112/hole transport layer 113/light emission auxiliary layer 122/light emitting layer 114/hole blocking layer 123/electron. The transport layer 115/electron injection layer 116/cathode 118 may be laminated in that order, but is not limited thereto.

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

The emission color between the stacks may be different, and the material of each stack may be different. Additionally, 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 in a different color. When a plurality of light-emitting layers 114 are formed using a multi-layer stack structure, an organic light-emitting display device that emits white light can be manufactured by mixing the light emitted from each light-emitting layer 114, as well as light of various colors. An organic light emitting display device that emits light can also be manufactured.

The charge generation layer may be composed 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.

The hole injection layer 112 or the hole transport layer 113 may be made of any material commonly used as a hole injection/transport material, such as aromatic or heteroaromatic amine compounds and carbazole derivatives, but is not limited thereto. .

Additionally, the hole injection layer 112 may be composed of one or more compounds, and the compounds of the hole injection layer 112 and the compounds of the hole transport layer 113 may be the same or different.

The hole transport layer 113 preferably has a hole mobility of 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs. More preferably, it is 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-5 cm ² /Vs. The hole mobility of the hole transport layer 113 is a parameter that shows the degree to which hole injection/transport is performed well. In other words, the lower the hole mobility, the better hole injection/transport can be achieved. The hole mobility of the hole transport layer 113 can be measured and calculated using the SCLC (Space Charge Limited Current) calculation method, which will be described later.

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.

The hole transport layer 113 may be specifically selected from a compound represented by Formula 1 or Formula 2 below.

[Formula 1] [Formula 2]

In Formula 1 and Formula 2, each symbol may be defined as follows.

Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are each independently an alkyl group of C ₁ to C ₆₀ ; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₃ ~ C ₆₀ cycloalkyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; A C ₂ to C ₆₀ heteroaryl group containing at least one heteroatom selected from O, N, S, Si, and P; and a fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ;

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups. It may be an alkyl group.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C _25. , such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are heteroaryl groups, preferably C ₂ to C ₃₀ heteroaryl groups, more preferably C ₂ to C ₂₄ heteroaryl groups. It may be a heteroaryl group.

When Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are fused ring groups, they are preferably a fused ring of an aliphatic ring from C ₃ to C ₃₀ and an aromatic ring from C ₆ to C ₃₀ group, more preferably a fused ring group of a C ₃ to C ₂₄ aliphatic ring and a C ₆ to C ₂₄ aromatic ring.

L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C 30 arylene groups. It may be an arylene group of ₂₅ .

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to It may be a heterocyclic group of C ₂₄ .

When L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ are fused ring groups, preferably an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ It may be a fused ring group, more preferably a fused ring group of an aliphatic ring of C ₃ to C ₂₄ and an aromatic ring of C ₆ to C ₂₄ .

Here, the aryl group, heteroaryl 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 selected from deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ It refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.

Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1] [Formula 1-2] [Formula 1-3]

In Formulas 1-1 to 1-3, each symbol may be defined as follows.

Ar ² , Ar ³ , L ¹ , L ² and L ³ are the same as defined above,

Ar is the same as the definition of Ar ¹ above,

Ar' may be a C ₃ -C ₆₀ cycloalkyl group, preferably a C ₃ -C ₃₀ cycloalkyl group, and more preferably a C ₃ -C ₂₄ cycloalkyl group.

X ¹ and X ^{2 are} independently selected from the group consisting of a single bond, O, S, NR, CR'R" and SiR'R", except ^that

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R, R' and R" are each the same or different, and independently of each other hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group ; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si, and P; Fused ring group of C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxyl group; and C ₆ ~ C ₃₀ aryloxy group; a group consisting of is selected from, or R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R' and R" may form a ring by combining adjacent groups with each other,

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R, R' and R" are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups. It may be an aryl group such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R, R' and R" are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C It may be a heterocyclic group of ₂₄ .

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R, R' and R" are fused ring groups, preferably an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ It may be a fused ring group, more preferably a fused ring group of a C ₃ to C ₂₄ aliphatic ring and a C ₆ to C ₂₄ aromatic ring.

When R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R, R' and R" are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C 30 . It may be an alkyl group of ₂₄ .

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

Formula 1 may be represented by the following Formula 1-1-1 or Formula 1-1-2.

[Formula 1-1-1] [Formula 1-1-2]

{In Formula 1-1-1 and Formula 1-1-2, Ar ² , Ar ³ , L ¹ , L ² , L ³ , X ¹ , R ¹ , R ² , R', R", a and b is the same as defined above.}

Formula 1 may be represented by any one of the following Formulas 1-1-A to 1-1-C.

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

{In Formula 1-1-A to Formula 1-1-C,

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

R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same as the definition of R ¹ above, or adjacent groups may combine with each other to form a ring,

f and g are independently integers from 0 to 5, and h and i are independently integers from 0 to 4.}

Formula 1 may be represented by any one of the following Formulas 1-1-D to 1-1-F.

[Formula 1-1-D] [Formula 1-1-E]

[Formula 1-1-F]

{In Formula 1-1-D to Formula 1-1-F,

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

R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are the same as the definition of R ¹ above, or may combine with adjacent groups to form a ring,

j and k are independently integers from 0 to 5, and l and m are independently integers from 0 to 4.}

Ar' may be any one of the following formulas 1-3-1 to 1-3-5, but is not limited thereto.

[Formula 1-3-1] [Formula 1-3-2] [Formula 1-3-3]

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

{In Formula 1-3-1 to Formula 1-3-5,

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

z1 and z2 are independently integers from 0 to 10, z3 is an integer from 0 to 13,

* indicates the binding position.}

The formula 2 may be expressed as the following formula 2-1 or formula 2-2.

[Formula 2-1] [Formula 2-2]

{In Formula 2-1 and Formula 2-2,

Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , L ⁴ , L ⁵ , L ⁶ and L ⁷ are as defined above,

R ²¹ , R ²² and R ²³ are the same as the definition of R ¹ above, or adjacent groups may combine with each other to form a ring,

n is an integer from 1 to 3,

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

The formula 2 may be expressed as the following formula 2-1-1 or formula 2-1-2.

[Formula 2-1-1] [Formula 2-1-2]

{In Formula 2-1-1 and Formula 2-1-2,

Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , L ⁴ , L ⁵ , L ⁶ and L ⁷ are as defined above,

R ²⁴ , R ²⁵ , R ²⁶ and R ²⁷ are the same as the definition of R ¹ above, or adjacent groups may combine with each other to form a ring,

X is O, S, NR or CR'R",

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,

R, R' and R" are the same as defined above.}

Formula 2 may be represented by any one of the following Formulas 2-1-A to 2-1-H.

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

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

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

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

{In 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 the same as defined above.}

Formula 2 may be represented by any one of the following Formulas 2-1-I to 2-1-N.

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

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

{In Formula 2-1-I to Formula 2-1-N, Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , L ⁴ , L ⁵ , L ⁶ , L ⁷ , X, R ²⁶ , R ²⁷ , f ' and g' are the same as defined above.}

Formulas 1 and 2 may be represented by any one of the following compounds P1-1 to P1-90, but are not limited thereto.

The light emitting layer 114 may include a host and a dopant.

The host may be selected from any material commonly used as a host, such as aromatic or heteroaromatic amine compounds, azine compounds, condensed polycyclic aromatic compounds, carbazole compounds, etc., but is not limited thereto. Additionally, the host may consist of one or more compounds.

The dopant may be selected from any material commonly used as a dopant, such as a fluorescent compound, a phosphorescent compound, and a delayed fluorescent compound, for example, a condensed polycyclic aromatic compound, a condensed polycyclic aromatic amine compound, boron (B) It may be selected from compounds containing, carbazole compounds, organometallic complexes (organometallic compounds containing iridium (Ir), osmium (Os), ruthenium (Rh), platinum (Pt), etc.), but is not limited thereto. . Additionally, the dopant may consist of one or more compounds.

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

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.

Additionally, the electron injection layer 116 may include a metal or a compound containing a metal. In particular, materials with 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 their It may be formed of materials selected from the combination, but is not limited thereto.

The electron mobility of the electron transport layer 115 is preferably 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs. The electron mobility of the electron transport layer 115 is a parameter that shows the degree to which electron injection/transport is carried out well. In other words, the lower the electron mobility, the better electron injection/transport can be achieved. The electron mobility of the electron transport layer 115 can be measured and calculated using the SCLC (Space Charge Limited Current) calculation method, which will be described later.

The hole mobility of the hole transport layer 113 and/or the electron mobility of the electron transport layer 115 is based on the SCLC (Space Charge Limited Current) in the J-V Curve of the HOD (Hole Only Device)/EOD (Electron Only Device) device. It can be checked by calculating . SCLC is the point where the main emission begins and refers to the section in dynamic balance (space charge) where the charge is filled in the trap.

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

Equation 1 below is Child's Law, and Equation 2 below is about Poole-Frenkel Emission.

[Equation 1]

J=current density (A/Cm ² )

ε= Dielectric constant of organic matter (2.655×10 ^-13 As/Vcm)

d=thickness of thin film (cm)

V=applied voltage (V)

[Equation 2]

E= electric field (V/cm)

μ ₀ = Poole-frenkel mobility (cm ² /Vs)

β= Poole-frenkel constant

Combining Equation 1 and Equation 2 above gives Equation 3 below.

[Equation 3]

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

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 moved to the host of the light-emitting layer 114, which can contribute to increasing efficiency.

The electron transport layer 115 may be specifically selected from a compound represented by Formula 3 or Formula 4 below.

[Formula 3] [Formula 4]

In Formula 3 and Formula 4, each symbol may be defined as follows.

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

X ⁶ is O, S or NR ^a ,

Ar ¹⁰ , Ar ¹¹ , Ar ¹² and Ar ¹³ are the same as the definition of Ar ¹ above,

L ¹⁰ , L ¹¹ , L ¹² and L ¹³ are the same as the definition of L ¹ above,

R ¹⁰⁰ and R ^a are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or R ¹⁰⁰ may form a ring by combining adjacent groups,

When R ¹⁰⁰ and R ^a are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When R ¹⁰⁰ and R ^a are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups.

When R ¹⁰⁰ and R ^a are fused ring groups, preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably a C ₃ to C ₂₄ aliphatic ring It may be a fused ring group of an aromatic ring from C ₆ to C ₂₄ .

When R ¹⁰⁰ and R ^a are alkyl groups, they may be preferably C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

a100 is an integer from 0 to 4,

Here, the aryl group, heteroaryl 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 selected from deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ It refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.

Formula 3 may be represented by any one of the following Formulas 3-1 to 3-3.

[Formula 3-1] [Formula 3-2]

[Formula 3-3]

In Formulas 3-1 to 3-3, each symbol may be defined as follows.

X ³ , X ⁴ , X ⁵ , Ar ¹¹ , Ar ¹² , L ¹⁰ , L ¹¹ and L ¹² are as defined above,

X ⁷ and X ⁸ are the same as the definition of X ¹ above, except that both X ⁷ and X ⁸ are single bonds,

Ar" may be a C ₆ to C ₆₀ arylene group, preferably a C ₆ to C ₃₀ arylene group, and more preferably a C ₆ to C ₂₅ arylene group.

Ar ¹⁴ is the same as the definition of Ar ¹ above,

R ¹ ', R ² ', R ³ ', R ⁴ ' and R ⁵ ' are the same as the definition of R ¹⁰⁰ above, or adjacent groups may combine to form a ring,

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

a"≥1.}

Formula 3 may be represented by the following Formula 3-1-1 or Formula 3-1-2.

[Formula 3-1-1] [Formula 3-1-2]

In Formula 3-1-1 and Formula 3-1-2,

^{X 3 , X 4 , X 5 , ​ ​} It is the same as what was done.}

Formula 3 may be represented by any one of the following Formulas 3-1-A to 3-1-C.

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

[Formula 3-1-C]

{In Formula 3-1-A to Formula 3-1-C,

^{X 3 , X 4 , X 5 , ​ ​}

R ⁶ ', R ⁷ ', R ⁸ ' and R ⁹ ' are the same as the definition of R ¹⁰⁰ above, or adjacent groups may combine to form a ring,

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

Formula 3 may be represented by any one of the following Formulas 3-1-D to 3-1-F.

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

[Formula 3-1-F]

{In Formula 3-1-D to Formula 3-1-F,

^{X 3 , X 4 , X 5 , ​ ​}

R ¹⁰ ', R ¹¹ ', R ¹² ' and R ¹³ ' are the same as the definition of R ¹⁰⁰ above, or adjacent groups may combine to form a ring,

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

Formula 4 may be represented by any one of the following Formulas 4-1 to 4-5.

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

[Formula 4-4] [Formula 4-5]

{In Formula 4-1 to Formula 4-5,

X ⁶ , Ar ¹³ , L ¹³ , R ¹⁰⁰ and a100 are the same as defined above,

a100' is an integer from 0 to 3.}

Chemical Formula 4 may be expressed as Chemical Formula 4-6 below.

[Formula 4-6]

{In Formula 4-6 above,

X ⁶ , L ¹³ , R ¹⁰⁰ and a100 are the same as defined above,

R ¹⁰¹ is the same as the definition of R ¹⁰⁰ above, or may form a ring by combining with adjacent groups,

a101 is an integer from 0 to 9.}

Formulas 3 and 4 may be represented by any one of the following compounds P2-1 to P2-76, but are not limited thereto.

In the case of the first part 110, the cathode 118 is formed on the electron transport layer 115, and when the device is configured as above, the optimal conditions for constructing the organic electroluminescent device are obtained. In particular, as the hole mobility and electron mobility are lower, the transport capacity of holes and electrons increases, which has the effect of reducing the driving voltage, and the balance of holes and electrons in the hole transport layer 113 and the electron transport layer 115 is maintained at an appropriate value. If so, it becomes possible to manufacture highly efficient organic electroluminescent devices. Therefore, if the above conditions are satisfied, an optimal organic electroluminescent device with low driving voltage and high efficiency can be provided.

The cathode 118 is preferably made of one or more metal materials, and the metal materials include magnesium (Mg), silver (Ag), aluminum (Al), lithium (Li), calcium (Ca), and indium (In). and combinations thereof, and is preferably composed of a mixture of Mg and Ag, but is not limited thereto.

Additionally, the cathode 118 may be used as a multi-layer comprising two or more layers.

However, when the metal material is selected to form the cathode 118, it may be a reflective electrode and/or a transflective electrode. In the case of a reflective electrode and/or a transflective electrode, the transmittance is low, so the light required for UDC/UPS, etc. Since transmittance cannot be secured, there are limitations in implementing a transparent display. Therefore, it is necessary to form a region capable of having high light transmittance without forming the cathode 118. That is, an attempt was made to implement a transparent display so as to secure the light transmittance required for UDC/UPS, etc. by arranging the first part 110, which is the light-emitting area, and the second part 120, which is the transmissive area.

The metal patterning layer 121 is formed on the commonly formed organic material layer 111, and prevents the cathode 118 from being formed in the area where the metal patterning layer 121 is formed. That is, by disposing the metal patterning layer 121, only the portion or selective portion where the cathode 118 is to be formed can be formed. The organic material layer 111 commonly formed in the second part 120 includes a hole transport layer 113 and an electron transport layer 115, and a hole injection layer 112 is formed between the anode 100 and the hole transport layer 113. ) may further include, 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.

The organic material 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 Figures 1 and 3, the first part ( In 110), the remaining parts except for the cathode 118 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. Therefore, 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 material layer 111 of the second part 120 may be the same. Therefore, the second part 120 can prevent the formation of the cathode 118 by stacking the metal patterning layer 121 after stacking the commonly formed organic material layer 111 without stacking an additional separate 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 is composed of a hole transport layer 113 - an electron transport layer ( 115) - It may be composed of a metal patterning layer 121, and the first part 110 includes 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. If it is composed of a transport layer - a second light emitting layer - a second electron transport layer - an electron injection layer 116 - a cathode 118, the second part 120 is a hole injection layer 112 - a first hole transport layer - a first electron transport layer - It may be composed of a charge generation layer, a second hole transport layer, a second electron transport layer, an electron injection layer 116, and a metal patterning layer 121, but the configuration of the organic light emitting display device is not limited to the above example.

The metal patterning layer 121 is, for example, PBD (2-(4-biphenylyl)-5-phenyl-1,3,4-oxadiazole), PBD ₂ (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 a compound containing fluorine (F), preferably a compound containing fluorine. However, it is not limited to this.

The metal patterning layer 121 may be specifically selected from a compound represented by the following formula (A).

[Formula A]

[Formula A-1]

In Formula A and Formula A-1, each symbol may be defined as follows.

A ²⁰⁰ ring, B ²⁰⁰ ring and C ²⁰⁰ ring are each independently an aryl group of C ₆ to C ₆₀ ; or a C ₂ to C ₆₀ heteroaryl group containing at least one heteroatom selected from O, N, S, Si, and P;

When the A ²⁰⁰ ring, B ²⁰⁰ ring and C ²⁰⁰ ring are an aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₅ aryl group, such as phenyl, biphenyl, terphenyl, It may be naphthalene, etc.

When the A ²⁰⁰ ring, B ²⁰⁰ ring and C ²⁰⁰ ring are heteroaryl groups, they may be preferably C ₂ to C ₃₀ heteroaryl groups, more preferably C ₂ to C ₂₄ heteroaryl groups.

L ²⁰¹ is a single bond; NR ²⁰⁴ ; C R ²⁰⁴ R ²⁰⁵ ; or SiR ²⁰⁴ R ²⁰⁵ ;,

L ²⁰² is a single bond; C ₁ ~ C ₆₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; C ₂ ~ C ₂₀ alkynylene group; C ₁ ~ C ₃₀ alkoxylene group; C ₆ ~ C ₃₀ aryloxylene group; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ;

When L ²⁰² is an alkylene group, it is preferably a C ₁ to C ₃₀ alkylene group, and more preferably a C ₁ to C ₂₄ alkylene group.

When L ²⁰² is an arylene group, it is preferably a C ₆ to C ₃₀ arylene group, and more preferably a C ₆ to C ₂₅ arylene group.

When L ²⁰² is a heterocyclic group, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group.

When L ²⁰² is a fused ring group, it is preferably a fused ring group of an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ , more preferably a fused ring group of an aliphatic ring of C ₃ to C ₂₄ and an aromatic ring of C ₆ to C 30. It may be a fused ring group of the aromatic ring of C ₂₄ .

R ²⁰¹ , R ²⁰² and R ²⁰³ are each the same or different and, independently of each other, hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and a substituent represented by Formula A-1; selected from the group consisting of,

However, at least one of R ²⁰¹ , R ²⁰² and R ²⁰³ is fluorine or a substituent represented by the formula A-1,

When R ²⁰¹ , R ²⁰² and R ²⁰³ are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenyl, biphenyl, terphenyl, naphthalene, etc. You can.

When R ²⁰¹ , R ²⁰² and R ²⁰³ are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups.

When R ²⁰¹ , R ²⁰² and R ²⁰³ are fused ring groups, preferably a fused ring group of an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ , more preferably of a fused ring group of C ₃ to C ₂₄ It may be a fused ring group of an aliphatic ring and an aromatic ring of C ₆ to C ₂₄ .

When R ²⁰¹ , R ²⁰² and R ²⁰³ are an alkyl group, they may be preferably an alkyl group of C ₁ to C ₃₀ , and more preferably an alkyl group of C ₁ to C ₂₄ .

R ²⁰⁴ and R ²⁰⁵ are the same as the definition of R ^a above, or R ²⁰⁴ and R ²⁰⁵ may be combined with each other to form a ring,

n201 is an integer from 0 to 3, and a201, a202, a203 and a204 are independently integers from 1 to 10,

x is an integer from 1 to 50, y+z is 2x+1,

However, z is an integer greater than 1,

The x is preferably an integer of 1 to 20, more preferably an integer of 5 to 15, and even more preferably an integer of 5 to 12,

Here, the aryl group, heteroaryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, alkylene group, alkenyl Len group, alkynylene group, alkoxylene group and aryloxylene group each have deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ It refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.

The formula A may be represented by any one of the following formulas B to D.

[Formula B]

[Formula C]

[Formula D]

In the above formulas B to formula D, A ²⁰⁰ ring, B ²⁰⁰ ring, C ²⁰⁰ ring, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , a201, a202, a203 and n201 are the same as defined above. .}

The formula A may be represented by the formula E below.

[Formula E]

{In the formula E, A ²⁰⁰ ring, B ²⁰⁰ ring, C ²⁰⁰ ring, R ²⁰¹ , R ²⁰² , R ²⁰³ , a201, a202, a203, a204, n201, L ²⁰² , x, y and z are defined above. Same as bar.}

The formula A may be represented by the formula F below.

[Formula F]

{In the above formula F, B ²⁰⁰ ring, C ²⁰⁰ ring, R ²⁰² , R ²⁰³ , a202, a203, n201, x, y and z are the same as defined above.}

The formula A may be any one of the following compounds P3-1 to P3-106, but is not limited thereto.

The contact angle of the metal patterning layer 121 is preferably 100° to 180°, and more preferably 100° to 150°. Additionally, if the contact angle of the compound satisfies the above range, the compound may have high light transmittance.

In general, adhesion can be explained by the surface energy of a solid through the contact angle. In general, the larger the contact angle, the smaller the adhesion.

This can be confirmed through Young's Equation, Equation 4 below.

[Equation 4]

gLVcosθ=gSV-gSL

gSL: Interfacial tension between solid and liquid

gSV: Interfacial tension between solid surface and liquid vapor,

gLV: Interfacial tension between liquid and liquid vapor

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

[Equation 5]

Wa = gS + gLV - gSL = gS + gLV + (gLVcosθ = (gS - gSV) + gLV(1+cosθ)

gS in Equation 5 is the surface tension of the solid itself, and since gS and gSV can generally be considered equal at small and low surface energies, Equation 5 is organized as follows. (Young-Dupre equation)

[Equation 6]

Wa = gLV(1+cosθ)

As the contact angle approaches cosθ=-1 as it increases from 90° to 180°, the adhesiveness decreases. That is, due to the low surface energy, the adhesion of the metal (electrode) is reduced 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 entering the metal patterning layer 121, and ultimately, a very small amount of the cathode 118 is formed. It is formed or not formed.

At this time, light transmittance is used to determine whether the cathode 118 exists. The light transmittance of the metal patterning layer 121 is preferably 90% or more. The reason is that since the cathode 118 contains an electrically conductive metal, it attenuates and/or absorbs light, so when the light transmittance exceeds 90% in the visible light region of the electromagnetic spectrum, the cathode 118 is formed on the metal patterning layer 121. It can be considered to be substantially free of electrically conductive material.

As shown in FIG. 5, the second part 120 may further include a patterning auxiliary photosensitive layer 117. Preferably, the patterning auxiliary photosensitive layer 117 may be disposed below the metal patterning layer 121. The material currently applied to the metal patterning layer 121 has no photoluminescence properties or is very weak, so it may be difficult to measure its thickness using photoluminescence properties. If the thickness of the metal patterning layer 121 is too thick, agglomeration occurs and it is difficult to form a thin film with a uniform surface, so it is difficult to secure uniform light transmittance and problems arise when additionally forming a thin film such as the third part 130. do.

Therefore, in general, in order to easily measure the thickness of the metal patterning layer 121 using optical properties, a patterning auxiliary photosensitive layer 117 with excellent photoluminescence characteristics can be formed under the metal patterning layer 121. The patterning auxiliary photosensitive layer 117 may be formed of a photosensitive organic material that has a stronger photoluminescence intensity than the metal patterning layer 121 and exhibits optical properties that can be measured by optical methods. That is, after applying the patterning auxiliary photosensitive layer 117, the thickness of the metal patterning layer 121 can be measured using an ellipsometer.

The patterning auxiliary photosensitive layer 117 may include a compound containing at least one heterocycle. The heterocycle may preferably be a C ₂ to C ₆₀ heterocycle containing at least one hetero atom selected from O, N, S, Si and P, and more preferably a C ₂ to C ₃₀ heterocycle. More preferably, it may be a heterocycle of C ₂ to C ₂₄ , specifically oxazole, thiazole, benzooxazole, benzothiazole, pyridine, pyrimidine, pyrazine, triazine, quinoline, quinazoline, quinoxaline, Imidazole, triazole, benzoimidazole, benzotriazole, furan, thiophene, benzofuran, benzothiophene, indole, dibenzofuran, dibenzothiophene, carbazole, benzofuropyridine, benzothiophenopyridine , carboline, benzofuropyrimidine, benzothiophenopyrimidine, benzofuropyrazine, benzothiophenopyrazine, etc., but is not limited thereto.

Additionally, the thickness of the patterning auxiliary photosensitive layer 117 is preferably 5 nm or more.

By forming the third part 130, optical energy loss due to SPPs (Surface Plasmon Polaritons) at the cathode 118 can be reduced in the case of a top emission organic light emitting device, and bottom emission organic light emitting devices can be formed. In the case of a light emitting device, the third part 130 may 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, optical energy loss due to SPPs can be reduced when light emitted from the first part 110 passes through the third part 130. Therefore, it is preferable that the light transmittance of the third portion 130 in the visible light region is 70% or more, and more preferably 80% or more.

The refractive index of the material of the third part 130 is preferably 1.85 to 3.0. More preferably, it has a refractive index of 1.9 to 3.0, and more preferably, it has a refractive index of 1.9 to 2.5. In particular, it is preferred that the compound of the third portion 130 material has a refractive index of 2.1 or greater at a wavelength of 450 nm, a refractive index of 1.95 or greater at a wavelength of 530 nm, and a refractive index of 1.85 or greater at a wavelength of 620 nm. As the light emitted through the first part 110 passes through the third part 130, which has a relatively high refractive index, the wavelength of the light is amplified, thereby increasing luminous efficiency.

The third part 130 may have a single-layer or multi-layer structure. Additionally, the third portion 130 may be a single compound or a mixture of two or more compounds.

The material of the third part 130 may be specifically selected as a compound represented by the following formula G.

[Formula G]

In the above formula G, each symbol can be defined as follows.

X ³⁰¹ is O, S or NR ³⁰² ,

Y' is CR ³⁰⁰ or N,

L ³⁰² is NL ³⁰⁴ -Ar ³⁰² ,

L ³⁰¹ , L ³⁰³ and L ³⁰⁴ are the same as the definition of L ¹ above,

Ar ³⁰¹ and Ar ³⁰² are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ cycloalkyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -NAr ³⁰³ Ar ³⁰⁴ ;,

When Ar ³⁰¹ and Ar ³⁰² are an aryl group, they are preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When Ar ³⁰¹ and Ar ³⁰² are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups.

When Ar ³⁰¹ and Ar ³⁰² are a fused ring group, preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably a C ₃ to C ₂₄ aliphatic ring It may be a fused ring group of an aromatic ring from C ₆ to C ₂₄ .

Ar ³⁰³ and Ar ³⁰⁴ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,

When Ar ³⁰³ and Ar ³⁰⁴ are an aryl group, they may be preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When Ar ³⁰³ and Ar ³⁰⁴ are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups.

When Ar ³⁰³ and Ar ³⁰⁴ are a fused ring group, preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably a C ₃ to C ₂₄ aliphatic ring It may be a fused ring group of an aromatic ring from C ₆ to C ₂₄ .

R ³⁰⁰ , R ³⁰¹ and R ³⁰² are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₃ ~ C ₆₀ cycloalkyl group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or adjacent groups may be bonded to each other to form a ring,

When R ³⁰⁰ , R ³⁰¹ and R ³⁰² are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₂₅ , such as phenyl, biphenyl, terphenyl, naphthalene, etc. You can.

When R ³⁰⁰ , R ³⁰¹ and R ³⁰² are heterocyclic groups, they may be preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups.

When R ³⁰⁰ , R ³⁰¹ and R ³⁰² are a fused ring group, preferably a fused ring group of an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ , more preferably of a fused ring group of C ₃ to C ₂₄ It may be a fused ring group of an aliphatic ring and an aromatic ring of C ₆ to C ₂₄ .

When R ³⁰⁰ , R ³⁰¹ and R ³⁰² are an alkyl group, they may be preferably an alkyl group of C ₁ to C ₃₀ , and more preferably an alkyl group of C ₁ to C ₂₄ .

When R ³⁰⁰ , R ³⁰¹ and R ³⁰² are cycloalkyl groups, they may be C ₃ to C ₃₀ cycloalkyl groups, and more preferably C ₃ to C ₂₄ cycloalkyl groups.

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

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 each contain deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ It refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.

The formula G may be represented by the following formula H or formula I.

[Formula H] [Formula I]

{ ^In the ^{above formulas H and} formula ^{I ,}

The formula G may be represented by any one of the following formulas J to N.

[Formula J] [Formula K] [Formula L]

[Formula M] [Formula N]

{In Formula J to Formula N above,

X ³⁰¹ , L ³⁰¹ , L ³⁰³ , L ³⁰⁴ , AR ³⁰¹ , AR ³⁰² , R ³⁰⁰ , R ³⁰¹ and A301 are the same as defined above,

Ar ³⁰⁵ and Ar ³⁰⁶ are the same as the definition of Ar ³⁰³ above,

R ³⁰³ has the same definition as R ³⁰¹ ,

a303 is an integer from 0 to 8.}

The formula G may be represented by the formula O below.

[Formula O]

^{{ In the above formula O , ​}

L301 and L303 may be independently represented by any one of the following formulas L-1 to L-4.

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

{In Formula L-1 to Formula L-4,

R ³⁰⁴ , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁷ have the same definition as R ³⁰¹ ,

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

* indicates the binding position.}

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

In addition, it is preferable that the total light transmittance of the second part 120 and the third part 130 is 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 portion 130 and the metal patterning layer 121 is important, and an organic light emitting display with high light transmittance is required to improve the light emitting efficiency of the organic light emitting display device and implement UDC/UPS, etc. It is preferable that it is a device.

This organic layer 111 may be manufactured using various deposition methods. For example, the organic material layer 111 may be manufactured using a deposition method such as PVD or CVD, and may be manufactured using a solution process or solvent process rather than a deposition method, such as a spin coating process, nozzle printing process, inkjet printing process, or slot coating. It can be manufactured with fewer layers by methods such as a process, dip coating process, roll-to-roll process, doctor blading process, screen printing process, or heat transfer method.

Preferably, the organic material layer 111 may be formed by vacuum deposition. However, since the organic material layer 111 according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electric device according to an embodiment of the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

Additionally, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photoreceptors, organic transistors, monochromatic lighting devices, and quantum dot display devices.

Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit that controls the display device. At this time, 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 mobile phones, navigation devices, 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).

Hereinafter, the present invention will be described with reference to examples. The following examples are for illustrating the present invention, and the scope of the present invention is not limited by these examples.

[Synthesis method]

P1 compound synthesis method

1. P1-2 Synthesis Example

After dissolving 3-bromo-9,9-dimethyl-9H-fluorene (5.0 g, 18.3 mmol) in toluene (60 mL) in a round bottom flask, N-(4-(naphthalen-1-yl)phenyl)-[ 1,1'-biphenyl]-4-amine (6.8 g, 18.3 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 1.1 mmol), NaOt- Add Bu (3.5 g, 36.6 mmol) and proceed with the reaction at 60°C. When the reaction is completed, the extract is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the produced organic matter was recrystallized using a silicagel column to obtain 8 g of product. (yield 77%)

2. P1-24 synthesis example

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), Pd ₂ (dba) ₃ (0.5 g, 0.3 mmol), P(t-Bu) ₃ (0.4 mL, 1.1 mmol), NaOt-Bu (3.4 g, 35.9 mmol) were added and the P1-2 Using the synthetic method, 9.8 g of product was obtained. (yield 82%)

3. P1-28 Synthesis Example

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), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P(t-Bu) ₃ (0.27 mL, 0.7 mmol), NaOt-Bu (2.2 g, 22.6 mmol) were added and the P1-2 Using the synthetic method, 5.8 g of product was obtained. (yield 79%)

4. P1-35 synthesis example

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), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P(t-Bu) ₃ (0.27 mL, 0.7 mmol), NaOt-Bu (2.2 g, 22.6 mmol) were added and the P1-2 Using the synthetic method, 5.8 g of product was obtained. (yield 79%)

5. P1-37 synthesis example

9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl- in a round bottom flask. 9H-fluoren-2-amine (4.5 g, 12.6 mmol), Pd ₂ (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) was added and 7.6 g of product was obtained using the synthesis method of P1-2 above. (yield 89%)

6. P1-42 synthesis example

In a round bottom flask, 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), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 1.0 mmol), NaOt-Bu (3.3 g, 33.9 mmol) was added and 10 g of product was obtained using the synthesis method of P1-2 above. (yield 88%)

7. P1-51 synthesis example

N-([1,1'-biphenyl]-4-yl)-3'-bromo-N-phenyl-[1,1'-biphenyl]-4-amine (5.0 g, 10.5 mmol) in a round bottom flask, 4-(naphthalen-1-yl)-N-phenylaniline (3.1 g, 10.5 mmol), Pd ₂ (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) was added and 6 g of product was obtained using the synthesis method of P1-2 above. (yield 83%)

8. P1-57 synthesis example

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) in a round bottom flask. ), Pd ₂ (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 and the synthesis method of P1-2 was used. 6.4 g of product was obtained using . (yield 78%)

9. P1-79 Synthesis Example

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), Pd ₂ (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 P1. 8.6 g of product was obtained using the synthesis method of -2. (yield 86%)

Meanwhile, the FD-MS values of compounds P1-1 to P1-90 of the present invention prepared according to the above synthesis examples are shown in Table 1 below.

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

P2 compound synthesis method

1. P2-1 synthesis example

Dissolve dibenzo[b,d]furan-1-ylboronic acid (5.0 g, 23.6 mmol) in THF (59 mL) and water (20 mL) in a round bottom flask, then dissolve 2-([1,1'-biphenyl] -3-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.1 g, 23.6 mmol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 mmol), NaOH (1.8 g, 47.17 mmol) ) and proceed with the reaction at 85°C. When the reaction is completed, the extract is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the produced organic material was recrystallized using a silicagel column to obtain 9.8 g of product. (yield 87%)

2. P2-9 synthesis example

(4-(phenanthren-2-yl)phenyl)boronic acid (5.0 g, 16.8 mmol), 2-chloro-4-(9,9-diphenyl-9H-fluoren-4-yl)-6- in a round bottom flask. Add phenyl-1,3,5-triazine (8.5 g, 16.8 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), and NaOH (1.3 g, 33.5 mmol) and use the synthesis method of P2-1 above. 10.8 g of product was obtained. (yield 89%)

3. P2-21 synthesis example

(9,9-dimethyl-9H-xanthen-2-yl)boronic acid (5.0 g, 19.7 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro- in a round bottom flask. Add 6-phenyl-1,3,5-triazine (6.8 g, 19.7 mmol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol), and NaOH (1.6 g, 39.4 mmol) and synthesize P2-1. 8.1 g of product was obtained using . (yield 80%)

4. P2-34 synthesis example

In a round bottom flask, spiro[fluorene-9,9'-xanthen]-3'-ylboronic acid (5.0 g, 13.3 mmol), 2-chloro-4-(dibenzo[b,d]thiophen-4-yl-d ₇ )-6-phenyl-1,3,5-triazine (5.1 g, 13.3 mmol), Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and NaOH (1.1 g, 26.6 mmol) were added to the solution of P2-1 above. Using the synthetic method, 7.8 g of product was obtained. (yield 87%)

5. P2-39 synthesis example

(6-phenylnaphthalen-2-yl)boronic acid (5.0 g, 20.2 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1, Add 3,5-triazine (6.9 g, 20.2 mmol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol), and NaOH (1.6 g, 40.3 mmol) and obtain 9.4 g of product using the synthesis method of P2-1 above. got it (yield 91%)

6. P2-59 synthesis example

(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(PPh ₃ ) ₄ (0.4 g, 0.3 mmol), and NaOH (0.8 g, 21.1 mmol) were added, and 5.7 g of product was obtained using the synthesis method of P2-1 above. (yield 77%)

7. P2-60 synthesis example

4-chloro-1-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene (5.0 g, 12.2 mmol) and benzo[d]oxazol-2-ylboronic acid in a round bottom flask. (2.0 g, 12.2 mmol), Pd(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), and NaOH (1.0 g, 24.3 mmol) were added, and 4.8 g of product was obtained using the synthesis method of P2-1 above. (yield 80%)

8. P2-61 synthesis example

(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(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), and NaOH (1.1 g, 27.6 mmol) were added, and 7.2 g of product was obtained using the synthesis method of P2-1. (yield 89%)

Meanwhile, the FD-MS values of compounds P2-1 to P2-76 of the present invention prepared according to the above synthesis examples are shown in Table 2 below.

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

P3 compound synthesis method

1. P3-1 synthesis example

In a round bottom flask, bis(2',3',4',5',6'-pentafluoro-[1,1'-biphenyl]-4-yl)amine (3.0 g, 6.0 mmol) was mixed with Toluene (30 mL). After dissolving in 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), Pd ₂ (dba) ₃ (0.16 g, 0.18 mmol), P(t-Bu) ₃ (0.07 g, 0.36 mmol), NaOt-Bu (1.2 g, 12.0 mmol) and proceed with the reaction at 80°C. When the reaction is completed, the extract is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the produced organic matter was recrystallized using a silicagel column to obtain 3.3 g of product. (yield 74%)

2. P3-13 synthesis example

Bis(4-bromophenyl)diphenylsilane (3.0 g, 6.07 mmol), Cu (3.1 g, 48.6 mmol), and DMSO (12 mL) were added to a round bottom flask, dissolved at 70°C, and stirred for 30 minutes. Afterwards, perfluorohexyl iodide (6.0 g, 13.4 mmol) was slowly added dropwise over 1 hour and stirred at 120°C for 24 hours. When the reaction was completed, distilled water was added and the resulting solid was filtered under reduced pressure. Afterwards, the filtrate was extracted using ethyl acetate, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was separated using a silica gel column and recrystallized to obtain 4.4 g of product (yield: 75%).

3. P3-26 synthesis example

9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole) (3.0 g, 6.16 mmol), Cu (3.1 g, 49.2 mmol), Perfluorohexyl iodide (3.0 g, 6.77 mmol) and DMSO (12 mL) was obtained through the synthesis method of P3-13 above to obtain 3.2 g of product (yield: 72%).

4. P3-30 synthesis example

4-bromo-1,1':4',1''-terphenyl (3.0 g, 9.70 mmol), Cu (4.9 g, 77.6 mmol), Perfluorodecyl iodide (6.9 g, 10.7 mmol) and DMSO (19 mL) 5.1 g of product (yield: 70%) was obtained through the synthesis method of P3-13.

5. P3-37 synthesis example

After dissolving Sub5-37 (3.0 g, 3.64 mmol) in toluene (12 mL) in a round flask, Sub6-37 (1.9 g, 3.64 mmol), K ₂ CO ₃ (1.5 g, 10.9 mmol) and Pd(PPh ₃ ) ₄ (0.08 g, 0.07 mmol) was added and stirred at 120°C. When the reaction was completed, it was separated using a silica gel column and recrystallized to obtain 3.41 g of product (yield: 79%).

6. P3-45 synthesis example

4,4'-dibromo-1,1'-biphenyl (1.0 g, 3.21 mmol), Sub6-45 (5.9 g, 7.05 mmol), K ₂ CO ₃ (1.3 g, 9.62 mmol), Pd(PPh ₃ ) ₄ (0.07 g, 0.06 mmol) and Toluene (11 mL) were used to obtain 4.6 g of product (yield: 79%) through the synthesis method of P3-37.

7. P3-47 synthesis example

3,3'-dibromo-1,1'-biphenyl (1.0 g, 3.21 mmol), Sub6-47 (8.8 g, 7.05 mmol), K ₂ CO ₃ (1.3 g, 9.62 mmol), Pd(PPh ₃ ) ₄ (0.07 g, 0.06 mmol) and Toluene (11 mL) were used to obtain 5.3 g of product (yield: 70%) through the synthesis method of P3-37.

8. P3-56 synthesis example

9,10-dibromoanthracene (2.0 g, 6.99 mmol), Sub6-37 (8.0 g, 15.4 mmol), K ₂ CO ₃ (2.90 g, 21.0 mmol), Pd(PPh ₃ ) ₄ (0.16 g, 0.14 mmol), Toluene (23 mL) was obtained through the synthesis method of P3-37 above to obtain 4.8 g of product (yield: 75%).

Meanwhile, the FD-MS values of compounds P3-1 to P3-106 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P3-1 m/z=743.07(C ₃₆ H ₁₂ F ₁₅ N=743.48) P3-2 m/z=958.96(C ₃₆ F ₂₇ N=959.36) P3-3 m/z=555.12(C ₃₁ H ₁₇ F ₈ N=555.47) P3-4 m/z=703.14(C ₄₀ H ₁₉ F ₁₀ N=703.58) P3-5 m/z=517.09(C ₃₀ H ₁₆ F ₅ NS=517.52) P3-6 m/z=818.18(C ₄₈ H ₂₄ F ₁₀ N ₂ =818.72) P3-7 m/z=671.19(C ₄₀ H ₂₅ F ₈ N=671.63) P3-8 m/z=1199.03(C ₃₆ H ₁₂ F ₃₉ N=1199.44) P3-9 m/z=1040.15(C ₅₄ H ₂₂ F ₁₈ N ₂ =1040.76) P3-10 m/z=964.12(C ₄₈ H ₁₈ F ₁₈ N ₂ =964.66) P3-11 m/z=870.21(C ₅₂ H ₂₈ F ₁₀ N ₂ =870.79) P3-12 m/z=804.08(C ₄₂ H ₁₈ F ₁₀ N ₂ S ₂ =804.72) P3-13 m/z=972.08(C ₃₆ H ₁₈ F ₂₆ Si=972.58) P3-14 m/z=1124.14(C ₄₈ H ₂₆ F ₂₆ Si=1124.78) P3-15 m/z=1124.14(C ₄₈ H ₂₆ F ₂₆ Si=1124.78) P3-16 m/z=1124.14(C ₄₈ H ₂₆ F ₂₆ Si=1124.78) P3-17 m/z=1760.08(C ₆₀ H ₂₄ F ₅₂ Si=1760.85) P3-18 m/z=2162.05(C ₆₆ H ₂₂ F ₆₈ N ₂ Si=2162.89) P3-19 m/z=2260.09(C ₇₆ H ₂₈ F ₆₈ Si=2261.04) P3-20 m/z=2186.11(C ₇₆ H ₃₀ F ₆₄ Si=2187.06) P3-21 m/z=956.1(C ₃₇ H ₁₈ F ₂₆ =956.51) P3-22 m/z=866.22(C ₄₉ H ₃₁ F ₁₃ =866.77) P3-23 m/z=1056.13(C ₄₅ H ₂₂ F ₂₆ =1056.63) P3-24 m/z=1108.16(C ₄₉ H ₂₆ F ₂₆ =1108.71) P3-25 m/z=1044.11(C ₄₂ H ₁₈ F ₂₆ N ₂ =1044.58) P3-26 m/z=726.13(C ₃₆ H ₁₉ F ₁₃ N ₂ =726.54) P3-27 m/z=810.23(C ₄₂ H ₃₁ F ₁₃ N ₂ =810.7) P3-28 m/z=790.08(C ₃₆ H ₁₉ F ₁₃ N ₂ S ₂ =790.66) P3-29 m/z=548.08(C ₂₄ H ₁₃ F ₁₃ =548.35) P3-30 m/z=748.07(C ₂₈ H ₁₃ F ₂₁ =748.38) P3-31 m/z=1064.02(C ₃₄ H ₁₀ F ₃₄ =1064.4) P3-32 m/z=1190(C ₃₂ H ₈ F ₄₂ =1190.35) P3-33 m/z=753.1(C ₂₈ H ₈ D ₅ F ₂₁ =753.41) P3-34 m/z=564.08(C ₂₄ H ₁₃ F ₁₃ O=564.35) P3-35 m/z=978.18(C ₃₈ H ₂₈ F ₂₆ =978.6) P3-36 m/z=1002.03(C ₃₂ H ₁₀ F ₃₂ =1002.38) P3-37 m/z=1184.02(C ₃₆ H ₁₁ F ₃₉ =1184.42) P3-38 m/z=1820.07(C ₅₀ H ₇ D ₈ F ₆₃ =1820.62) P3-39 m/z=1266.03(C ₃₈ H ₁₂ F ₄₂ =1266.45) P3-40 m/z=1358.05(C ₄₄ H ₁₆ F ₄₂ O=1358.54) P3-41 m/z=1502(C ₄₂ H ₁₀ F ₅₂ =1502.46) P3-42 m/z=1634.09(C ₅₂ H ₂₂ F ₅₂ =1634.66) P3-43 m/z=1734.03(C ₅₈ H ₁₈ F ₅₂ S=1734.76) P3-44 m/z=1010.07(C ₃₇ H ₁₅ F ₂₉ =1010.48) P3-45 m/z=1578.03(C ₄₈ H ₁₄ F ₅₂ =1578.56) P3-46 m/z=1690.15(C ₅₆ H ₃₀ F ₅₂ =1690.77) P3-47 m/z=2377.98(C ₆₄ H ₁₄ F ₈₄ =2378.68) P3-48 m/z=2088.11(C ₇₂ H ₂₇ F ₆₃ =2088.91) P3-49 m/z=2088.11(C ₇₂ H ₂₇ F ₆₃ =2088.91) P3-50 m/z=3641.99(C ₁₀₂ H ₂₄ F ₁₂₆ =3643.11) P3-51 m/z=1806.12(C ₆₆ H ₂₆ F ₅₂ =1806.85) P3-52 m/z=916.07(C ₃₄ H ₁₄ F ₂₆ =916.44) P3-53 m/z=2427.99(C ₆₈ H ₁₆ F ₈₄ =2428.74) P3-54 m/z=916.07(C ₃₄ H ₁₄ F ₂₆ =916.44) P3-55 m/z=1552.01(C ₄₆ H ₁₂ F ₅₂ =1552.52) P3-56 m/z=966.08(C ₃₈ H ₁₆ F ₂₆ =966.5) P3-57 m/z=2458.04(C ₇₀ H ₂₂ F ₈₄ =2458.81) P3-58 m/z=942.08(C ₃₆ H ₁₆ F ₂₆ =942.48) P3-59 m/z=992.1(C ₄₀ H ₁₈ F ₂₆ =992.54) P3-60 m/z=943.08(C ₃₅ H ₁₅ F ₂₆ N=943.47) P3-61 m/z=992.1(C ₄₀ H ₁₈ F ₂₆ =992.54) P3-62 m/z=1242.1(C ₄₈ H ₂₀ F ₃₄ =1242.63) P3-63 m/z=943.08(C ₃₅ H ₁₅ F ₂₆ N=943.47) P3-64 m/z=1432.07(C ₅₀ H ₁₈ F ₄₂ O=1432.63) P3-65 m/z=1358.13(C ₅₁ H ₂₄ F ₃₈ =1358.69) P3-66 m/z=1136.12(C ₄₇ H ₂₁ F ₂₉ =1136.64) P3-67 m/z=1158.08(C ₄₆ H ₁₇ F ₃₁ =1158.59) P3-68 m/z=972.09(C ₃₇ H ₁₈ F ₂₆ O=972.51) P3-69 m/z=958.08(C ₃₆ H ₁₆ F ₂₆ O=958.48) P3-70 m/z=986.11(C ₃₈ H ₂₀ F ₂₆ O=986.54) P3-71 m/z=987.07(C ₃₆ H ₁₅ F ₂₆ NO ₂ =987.48) P3-72 m/z=998.15(C ₄₀ H ₂₄ F ₂₆ =998.59) P3-73 m/z=1024.16(C ₄₂ H ₂₆ F ₂₆ =1024.63) P3-74 m/z=1109.16(C ₄₈ H ₂₅ F ₂₆ N=1109.69) P3-75 m/z=970.08(C ₃₇ H ₁₆ F ₂₆ O=970.49) P3-76 m/z=1057.15(C ₄₁ H ₂₅ F ₂₆ NO ₂ =1057.61) P3-77 m/z=984.09(C ₃₈ H ₁₈ F ₂₆ O=984.52) P3-78 m/z=1014.1(C ₃₉ H ₂₀ F ₂₆ O ₂ =1014.55) P3-79 m/z=1082.08(C ₄₂ H ₂₀ F ₂₆ O ₂ S=1082.64) P3-80 m/z=1066.09(C ₄₂ H ₂₁ F ₂₆ OP=1066.56) P3-81 m/z=988.11(C ₄₃ H ₁₉ F ₂₃ O=988.59) P3-82 m/z=990.18(C ₄₆ H ₃₀ F ₂₀ Si=990.8) P3-83 m/z=878.22(C ₄₂ H ₃₂ F ₁₈ =878.69) P3-84 m/z=1242.15(C ₅₆ H ₂₉ F ₂₆ OP=1242.78) P3-85 m/z=1106.09(C ₄₀ H ₁₈ F ₃₂ =1106.53) P3-86 m/z=1206.08(C ₄₂ H ₁₈ F ₃₆ =1206.55) P3-87 m/z=1434.1(C ₄₈ H ₂₂ F ₄₄ =1434.63) P3-88 m/z=2034.06(C ₆₀ H ₂₂ F ₆₈ =2034.73) P3-89 m/z=1024.09(C ₃₈ H ₁₇ F ₂₉ =1024.51) P3-90 m/z=1274.07(C ₄₃ H ₁₇ F ₃₉ =1274.55) P3-91 m/z=1316.12(C ₄₆ H ₂₃ F ₃₉ =1316.63) P3-92 m/z=634.15(C ₃₂ H ₂₂ F ₁₂ =634.51) P3-93 m/z=834.14(C ₃₆ H ₂₂ F ₂₀ =834.54) P3-94 m/z=1434.1(C ₄₈ H ₂₂ F ₄₄ =1434.63) P3-95 m/z=970.11(C ₃₈ H ₂₀ F ₂₆ =970.54) P3-96 m/z=998.15(C ₄₀ H ₂₄ F ₂₆ =998.59) P3-97 m/z=1026.18(C ₄₂ H ₂₈ F ₂₆ =1026.64) P3-98 m/z=1054.21(C ₄₄ H ₃₂ F ₂₆ =1054.7) P3-99 m/z=1110.27(C ₄₈ H ₄₀ F ₂₆ =1110.81) P3-100 m/z=1054.21(C ₄₄ H ₃₂ F ₂₆ =1054.7) P3-101 m/z=516.13(C ₃₂ H ₁₈ F ₆ =516.49) P3-102 m/z=690.18(C ₄₆ H ₂₄ F ₆ =690.69) P3-103 m/z=572.16(C ₃₈ H ₂₁ F ₅ =572.58) P3-104 m/z=532.09(C ₂₉ H ₁₃ F ₉ =532.41) P3-105 m/z=456.15(C ₃₀ H ₂₀ F ₄ =456.48) P3-106 m/z=556.13(C ₃₄ H ₂₁ F ₅ S=556.59)

P4 compound synthesis method

1. P4-11 synthesis example

Dissolve 2-(4-bromophenyl)benzo[d]thiazole (5.0 g, 17.2 mmol) in toluene (57 mL) in a round bottom flask, then add bis(4-(naphthalen-1-yl)phenyl)amine (7.3 g) , 17.2 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 1.0 mmol), NaOt-Bu (3.3 g, 34.5 mmol) were added and reacted at 60°C. proceed. When the reaction is completed, the extract is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Afterwards, the produced organic material was recrystallized using a silicagel column to obtain 8.9 g of product. (yield 82%)

2. P4-13 synthesis example

In a round bottom flask, 2-(4-bromophenyl)benzo[d]oxazole (5.0 g, 18.2 mmol), dibenzo[b,d]thiophen-3-amine (1.8 g, 9.1 mmol), Pd ₂ (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, and 6.7 g of product was obtained using the synthesis method of P4-11 above. (yield 63%)

3. P4-14 synthesis example

2-(4-bromophenyl)benzo[d]thiazole (5.0 g, 17.2 mmol), 9,9'-spirobi[fluoren]-4-amine (2.9 g, 8.6 mmol), Pd ₂ (dba) in a round bottom flask. 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, and 8 g of product was obtained using the synthesis method of P4-11 above. got it (yield 62%)

4. P4-28 synthesis example

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 in a round bottom flask. -amine (6.9 g, 16.8 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 1.0 mmol), NaOt-Bu (3.2 g, 33.7 mmol) 7.3 g of product was obtained using the synthesis method of P4-11 above. (yield 69%)

5. P4-38 synthesis example

N-(4-(benzo[d]oxazol-2-yl)phenyl)-8-bromo-N-phenyldibenzo[b,d]thiophen-3-amine (5.0 g, 9.1 mmol), 4- in a round bottom flask. (benzo[d]oxazol-2-yl)-N-phenylaniline (2.6 g, 9.1 mmol), Pd ₂ (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, and 5.8 g of product was obtained using the synthesis method of P4-11 above. (yield 84%)

6. P4-53 synthesis example

(4-(benzo[d]oxazol-2-yl)phenyl)boronic acid (5.0 g, 20.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro in a round bottom flask. -6-phenyl-1,3,5-triazine (7.2 g, 20.9 mmol), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol), and NaOH (1.7 g, 41.8 mmol) were added and the synthesis of P4-11 was performed. 9.4 g of product was obtained using the method. (yield 89%)

7. P4-64 synthesis example

In a round bottom flask, 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(PPh ₃ ) ₄ (0.4 g, 0.4 mmol), and NaOH (1.0 g, 24.2 mmol) were added, and 7.9 g of product was obtained using the synthesis method of P4-53 above. (yield 84%)

8. P4-78 synthesis example

(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) in a round bottom flask. Add -fluoren-3-yl)anthracene (7.2 g, 15.9 mmol), Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), and NaOH (1.3 g, 31.8 mmol) using the synthesis method of P4-53 above. 8 g of product was obtained. (yield 79%)

9. P4-83 synthesis example

2-(4'-bromo-[1,1'-biphenyl]-4-yl)benzo[b]thiophene (5.0 g, 13.7 mmol), bis(4-(naphthalen-2-yl)phenyl) in a round bottom flask. )amine (5.8 g, 13.7 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), P(t-Bu) ₃ (0.3 mL, 0.8 mmol), NaOt-Bu (2.6 g, 27.4 mmol) and obtained 7.8 g of product using the synthesis method of P4-11 above. (yield 81%)

Meanwhile, the FD-MS values of compounds P4-1 to P4-92 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

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

[Example 1]

First, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1 was placed on the ITO layer (anode) formed on the glass substrate. ,4-diamine (hereinafter, 2-TNATA) film was vacuum deposited to form a 60 nm thick hole injection layer, and then the compound P1-51 represented by Formula 1 of the present invention was vacuum deposited on the hole injection layer to form a 60 nm thick hole injection layer. After forming the hole transport layer, 3-(4,6-Diphenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (hereinafter referred to as DPTPCz) as a host on the top of the hole transport layer As a doping material, tris(2-phenylpyridine)-iridium (hereinafter referred to as Ir(ppy) ₃ ) was doped at a weight ratio of 95:5 and a light emitting layer was deposited to a thickness of 30 nm. Next, the compound P2-48 represented by Formula 3 of the present invention was vacuum deposited to a thickness of 40 nm as an electron transport layer, and LiF, an alkali metal halide, 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. The first part 110, which is a light emitting area, was manufactured by depositing and using it as a cathode.

[Example 2] and [Example 3]

Compound P1-51 of the present invention was used as the hole transport layer material and Compound P2-48 of the present invention was used as the electron transport layer material, except that the compounds of the present invention shown in Table 5 below were used. Portion 110 was prepared.

[Comparative Example 1]

The first part was prepared in the same manner as in Example 1, except that Comparative Compound A was used as the hole transport layer material instead of Compound P1-51 of the present invention, and Comparative Compound B was used instead of Compound P2-48 of the present invention as the electron transport layer material. (110) was prepared.

[Comparative Compound A] [Comparative Compound B]

A forward bias direct current voltage was applied to the first part 110 of Examples 1 to 3 and Comparative Example 1 prepared in this way, and the electroluminescence (EL) characteristics were measured using PR-650 from Photoresearch. As a result of the measurement, the T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at a standard luminance of 5000 cd/m ² . Table 5 below shows the results of device fabrication and evaluation.

hole transport layer electron transport layer driving voltage
(V) electric current
(mA/ ^cm2 ) Luminance
(cd/ ^m2 ) 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 P1-51 P2-48 6.0 22.1 5000 22.6 92.7 Example 2 P1-57 P2-29 5.9 14.4 5000 34.7 95.3 Example 3 P1-3 P2-41 5.8 13.1 5000 38.1 100.1

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

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

Comparative compound A P1-51 Hole mobility 7.8ⅹ10 ^-3 cm ² /Vs 3.0ⅹ10 ^-4 cm ² /Vs HOMO 6.0 eV -5.5 eV

As can be seen in Table 6 above, P1-51 has a value of less than 1.0×10 ^-3 cm ² /Vs, and 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 the faster the hole mobility, the lower the driving voltage.

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

Comparative compound B P2-48 LUMO -2.6 eV -3.0 eV

As can be seen in Table 7 above, the LUMO value of comparative compound B is -2.6 eV, and the LUMO value of P2-48 is -3.0 eV. As can be seen in Tables 5 to 7, the injection characteristics of holes and electrons can be adjusted depending on the HOMO and LUMO values, and as the ratio of holes and electrons in the light emitting layer is similar, efficiency can also be increased. In other words, when the specific conditions of the hole transport layer and electron transport layer are met as described above, an optimal organic electroluminescent device can be manufactured.

[Example 4]

First, the organic material layer 111 of the present invention was vacuum-deposited to form a 60 nm thick organic material layer 111 on a glass substrate, and comparative compound B was vacuum-deposited on P1-7 to form a 40 nm thick layer. Afterwards, compound P3-13 of the present invention was vacuum deposited to a thickness of 10 nm on the organic material layer 111 to form a metal patterning layer. Next, Al was deposited as a cathode on the metal patterning layer. Then, in the third part, the compound P4-42 of the present invention was deposited to a thickness of 70 nm to prepare a sample required for measuring light transmittance.

[Example 5] to [Example 11]

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

[Comparative Example 2]

A light transmittance sample was produced in the same manner as Example 4, except that the metal patterning layer was not used.

[Comparative Example 3]

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

[Comparative Example 4]

A light transmittance sample was prepared in the same manner as in Example 4, except that Comparative Compound C was used instead of Compound P4-42 of the present invention as the third partial material.

[Comparative compound C]

The light transmittance of the light transmittance samples of Examples 4 to 11 and Comparative Examples 2 to 4 prepared in this way was measured in the visible light region at 550 nm using Perkinelmer's Lambda 365 UV/VIS Spectrometer measuring equipment, and the measurement results were is shown in Table 8 below.

Metal patterning layer Part 3 Transmittance T(%) Comparative Example 2 - P4-42 61.1% 100% Comparative Example 3 P1-7 P4-42 61.4% 100% Comparative Example 4 P3-13 Comparative compound C 66.2% 108% Example 4 P3-13 P4-42 73.8% 121% Example 5 P3-37 P4-42 74.8% 122% Example 6 P3-41 P4-42 74.4% 122% Example 7 P3-45 P4-42 74.5% 122% Example 8 P3-45 P4-13 75.3% 123% Example 9 P3-45 P4-15 75.5% 124% Example 10 P3-45 P4-21 75.8% 124% Example 11 P3-45 P4-38 76.3% 125%

As can be seen in Table 8, when Comparative Example 2, Comparative Example 3, and Examples of the present invention are compared, it can be confirmed that the light transmittance is high when the compound of the present invention is used as a metal patterning layer. This means that if there is no metal patterning layer or the adhesion to metal is high even if the metal patterning layer is present, the cathode (metal) is laminated before the third part is laminated. As a result, it can be seen that the transmittance is significantly lowered. And, comparing Comparative Example 4 and Examples of the present invention, it can be seen that when the compound of the present invention is used as the third part, high light transmittance is observed. In particular, it can be confirmed that high transmittance is shown when both the material of the metal patterning layer and the material of the third part are used as in the present invention.

The contact angles of Comparative Compound C and the metal patterning layer compound of the present invention are shown in Table 9 below.

contact angle Comparative compound C 83.2° P3-13 111.1° P3-41 103.6° P3-45 116.4°

Looking at Table 9 above, it can be seen that the contact angle of Comparative Compound C is 83.2°, whereas the metal patterning layer material of the present invention has a contact angle of 100° or more. Therefore, it is believed that high transmittance is shown when the contact angle of the metal patterning layer material is 100° or more. In other words, the higher the contact angle, the lower the adhesion to the metal, which can prevent metals from stacking. The refractive indices of comparative compound C and the third part compound P4-42 of the present invention are listed in Table 10 below.

Comparative compound C P4-42 refractive index 1.82 1.99

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 compound of the present invention is a material with a refractive index of 1.85 or more, and the refractive index of comparative compound C is 1.82. Therefore, when the metal patterning layer compound and the third partial compound of the present invention are used simultaneously, it can be confirmed that the total transmittance shows a high transmittance of more than 70%, and it can be considered very suitable when producing a display for UDC/UPS.

The above description is merely an illustrative description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting 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 in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100: anode 110: first part
111: Organic material layer 112: Hole injection layer
113: hole transport layer 114: light emitting layer
115: electron transport layer 116: electron injection layer
117: patterning auxiliary photosensitive layer 118: cathode
120: second part 121: metal patterning layer
122: Light-emitting auxiliary layer 123: Hole blocking layer
124: first light-emitting auxiliary layer 125: second light-emitting auxiliary layer
130: third part

Claims (23)

Board;
An anode 100 disposed on the substrate;
a first portion 110 that is a light emitting area on the anode 100; and a second part 120, which is a transmission area, is present,
The first part 110 and the second part 120 include an organic material layer 111 formed in common,
The organic material layer 111 includes a hole transport layer 113 and an electron transport layer 115,
A cathode 118 exists on the organic material layer 111 of the first part 110,
A metal patterning layer 121 is present on the organic material layer 111 of the second part 120,
A third part 130, which is a common area, is included on the first part 110 and the second part 120,
The hole mobility of the hole transport layer 113 material is 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs, and the HOMO (Hightest Occupied Molecular) of the hole transport layer 113 material is Orbital) energy level is -5.5 eV to -5.0 eV,
The electron mobility of the electron transport layer 115 material is 1.0×10 ^-8 cm ² /Vs to 1.0×10 ^-3 cm ² /Vs, and the LUMO (Lowest Occupied Molecular) of the electron transport layer 115 material is Orbital) energy level is -3.5 eV to -2.8 eV,
The contact angle of the metal patterning layer 121 material is 100° to 180°,
The organic light emitting display device, wherein the material of the third portion 130 has a refractive index of 1.85 to 3.0.
The organic light emitting display device of claim 1, wherein the second portion (120) further includes a patterning auxiliary photosensitive layer (117).
The organic light emitting display device of claim 1, wherein the hole transport layer 113 includes a compound represented by the following Chemical Formula 1 or Chemical Formula 2:
[Formula 1] [Formula 2]

{In Formula 1 and Formula 2 above,
Ar ¹ , Ar ² , Ar ³ , Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are each independently an alkyl group of C ₁ to C ₆₀ ; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₃ ~ C ₆₀ cycloalkyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; A C ₂ to C ₆₀ heteroaryl group containing at least one heteroatom selected from O, N, S, Si, and P; and a fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ;
L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , L ⁷ and L ⁸ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,
Here, the aryl group, heteroaryl 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 selected from deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ refers to a fused ring consisting of an aliphatic ring, an aromatic ring of C ₆ to C ₆₀ , a heterocycle of C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The organic light emitting display device of claim 1, wherein the electron transport layer 115 includes a compound represented by the following Chemical Formula 3 or Chemical Formula 4:
[Formula 3] [Formula 4]

{In Formula 3 and Formula 4 above,
X ³ , X ⁴ and X ⁵ are independently N or -CH, provided that at least one is N,
X ⁶ is O, S or NR ^a ,
Ar ¹⁰ , Ar ¹¹ , Ar ¹² and Ar ¹³ are the same as the definition of Ar ¹ in claim 3,
L ¹⁰ , L ¹¹ , L ¹² and L ¹³ are the same as the definition of L ¹ in claim 3 above,
R ¹⁰⁰ and R ^a are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or R ¹⁰⁰ may form a ring by combining adjacent groups,
a100 is an integer from 0 to 4,
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 each contain deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ refers to a fused ring consisting of an aliphatic ring, an aromatic ring from C ₆ to C ₆₀ , a heterocycle from C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The organic light emitting display device of claim 1, wherein the metal patterning layer 121 includes a compound represented by the following formula (A):
[Formula A]

[Formula A-1]

{In Formula A and Formula A-1 above,
A ²⁰⁰ ring, B ²⁰⁰ ring and C ²⁰⁰ ring are each independently an aryl group of C ₆ to C ₆₀ ; or a C ₂ to C ₆₀ heteroaryl group containing at least one heteroatom selected from O, N, S, Si, and P;
L ²⁰¹ is a single bond; NR ²⁰⁴ ; C R ²⁰⁴ R ²⁰⁵ ; or SiR ²⁰⁴ R ²⁰⁵ ;,
L ²⁰² is a single bond; C ₁ ~ C ₆₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; C ₂ ~ C ₂₀ alkynylene group; C ₁ ~ C ₃₀ alkoxylene group; C ₆ ~ C ₃₀ aryloxylene group; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ;
R ²⁰¹ , R ²⁰² and R ²⁰³ are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; And a substituent represented by the formula A-1; is selected from the group consisting of,
However, at least one of R ²⁰¹ , R ²⁰² and R ²⁰³ is fluorine or a substituent represented by Formula A-1,
R ²⁰⁴ and R ²⁰⁵ are the same as the definition of R ^a in claim 4, or R ²⁰⁴ and R ²⁰⁵ may be combined with each other to form a ring,
n201 is an integer from 0 to 3, and a201, a202, a203 and a204 are independently integers from 1 to 10,
x is an integer from 1 to 50, y+z is 2x+1,
However, z is an integer greater than 1,
Here, the aryl group, heteroaryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, alkylene group, alkenyl Len group, alkynylene group, alkoxylene group and aryloxylene group each have deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ refers to a fused ring consisting of an aliphatic ring, an aromatic ring from C ₆ to C ₆₀ , a heterocycle from C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The organic light emitting display device of claim 1, wherein the third portion 130 includes a compound represented by the following formula G:
[Formula G]

{In formula G above,
X ³⁰¹ is O, S or NR ³⁰² ,
Y' is CR ³⁰⁰ or N,
L ³⁰² is NL ³⁰⁴ -Ar ³⁰² ,
L ³⁰¹ , L ³⁰³ and L ³⁰⁴ are the same as the definition of L ¹ in claim 3 above,
Ar ³⁰¹ and Ar ³⁰² are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ cycloalkyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -NAr ³⁰³ Ar ³⁰⁴ ;,
Ar ³⁰³ and Ar ³⁰⁴ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,
R ³⁰⁰ , R ³⁰¹ and R ³⁰² are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₃ ~ C ₆₀ cycloalkyl group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or adjacent groups may be bonded to each other to form a ring,
a301 is an integer from 0 to 4, a302 is 0 or 1,
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 each contain deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ refers to a fused ring consisting of an aliphatic ring, an aromatic ring from C ₆ to C ₆₀ , a heterocycle from C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The organic light emitting display device of claim 1, wherein the metal patterning layer 121 material has a transmittance of 80% or more.
The organic light emitting display device of claim 1, wherein the material of the third portion (130) has a transmittance of 70% or more.
The organic light emitting display device according to claim 1, wherein the total light transmittance of the second portion 120 and the third portion 130 is 70% or more.
Board;
An anode 100 disposed on the substrate;
A first part 100 that is a light emitting area on the anode 100;
a second part 120 which is a transparent area formed outside the first part 110; and
In the organic light emitting display device including a third part (130) commonly formed on the first part (110) and the second part (120),
A metal patterning layer 121 is disposed on the surface of the second part 120 in contact with the third part 130,
The metal patterning layer 121 includes a compound represented by the following formula A; and the third portion 130 includes a compound represented by the following formula (G):
[Formula A]

[Formula A-1]

[Formula G]

{In Formula A, Formula A-1 and Formula G above,
A ²⁰⁰ ring, B ²⁰⁰ ring and C ²⁰⁰ ring are each independently an aryl group of C ₆ to C ₆₀ ; or a C ₂ to C ₆₀ heteroaryl group containing at least one heteroatom selected from O, N, S, Si, and P;
L ²⁰¹ is a single bond; NR ²⁰⁴ ; C R ²⁰⁴ R ²⁰⁵ ; or SiR ²⁰⁴ R ²⁰⁵ ;,
L ²⁰² is a single bond; C ₁ ~ C ₆₀ alkylene group; C ₂ ~ C ₂₀ alkenylene group; C ₂ ~ C ₂₀ alkynylene group; C ₁ ~ C ₃₀ alkoxylene group; C ₆ ~ C ₃₀ aryloxylene group; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ;
L ³⁰² is NL ³⁰⁴ -Ar ³⁰² ,
L ³⁰¹ , L ³⁰³ and L ³⁰⁴ are independently a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C ₂ ~ C ₆₀ heterocyclic group; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,
X ³⁰¹ is O, S or NR ³⁰² ,
Y' is CR ³⁰⁰ or N,
R ²⁰¹ , R ²⁰² and R ²⁰³ are each the same or different and, independently of each other, hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; And a substituent represented by the formula A-1; selected from the group consisting of,
However, at least one of R ²⁰¹ , R ²⁰² and R ²⁰³ is fluorine or a substituent represented by the formula A-1,
R ²⁰⁴ and R ²⁰⁵ are independently hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or R ²⁰⁴ and R ²⁰⁵ may be combined with each other to form a ring,
R ³⁰⁰ , R ³⁰¹ and R ³⁰² are each the same or different and, independently of each other, are hydrogen; heavy hydrogen; halogen; Aryl group of C ₆ to C ₆₀ ; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; C ₁ ~ C ₆₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₃ ~ C ₆₀ cycloalkyl group; C ₁ ~ C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; selected from the group consisting of,
n201 is an integer from 0 to 3, and a201, a202, a203 and a204 are independently integers from 1 to 10,
a301 is an integer from 0 to 4, a302 is 0 or 1,
x is an integer from 1 to 50, y+z is 2x+1,
However, z is an integer greater than 1,
Ar ³⁰¹ and Ar ³⁰² are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; C ₃ ~ C ₆₀ cycloalkyl group; A fused ring group of an aliphatic ring from C ₃ to C ₆₀ and an aromatic ring from C ₆ to C ₆₀ ; and -NAr ³⁰³ Ar ³⁰⁴ ;,
Ar ³⁰³ and Ar ³⁰⁴ are independently C ₆ to C ₆₀ aryl groups; fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one hetero atom among O, N, S, Si and P; and a fused ring group of an aliphatic ring of C ₃ to C ₆₀ and an aromatic ring of C ₆ to C ₆₀ ; selected from the group consisting of,
Here, the aryl group, heteroaryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, alkoxyl group, aryloxy group, alkylene group , alkenylene group, alkynylene group, alkoxylene group and aryloxylene group each have deuterium; halogen; Silane group; siloxane group; boron group; Germanium group; Cyano group; nitro group; C ₁ ~ C ₂₀ alkylthio group; C ₁ ~ C ₂₀ alkoxyl group; C ₆ ~ C ₂₀ aryloxy group; C ₁ ~ C ₂₀ alkyl group; C ₂ ~ C ₂₀ alkenyl group; C ₂ ~ C ₂₀ alkyne group; C ₆ ~ C ₂₀ aryl group; C ₆ ~ C ₂₀ aryl group substituted with deuterium; C ₆ ~ C ₂₀ aryl group substituted with halogen; fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group; C ₃ ~ C ₂₀ cycloalkyl group; C ₇ ~ C ₂₀ arylalkyl group; and C ₈ ~ C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' refers to a C ₃ ~ C ₆₀ refers to a fused ring consisting of an aliphatic ring, an aromatic ring from C ₆ to C ₆₀ , a heterocycle from C ₂ to C ₆₀ , or a combination thereof, and includes saturated or unsaturated rings.}
The organic light emitting display device of claim 10, wherein the second portion (120) further includes a patterning auxiliary photosensitive layer (117).
The organic light emitting display device of claim 10, wherein Formula A is represented by any one of Formulas B to Formulas D below:
[Formula B]

[Formula C]

[Formula D]

{In Formula B to Formula D above,
A ²⁰⁰ ring, B ²⁰⁰ ring, C ²⁰⁰ ring, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , a201, a202, a203 and n201 are as defined in claim 10 above.}
The organic light emitting display device of claim 10, wherein the formula G is represented by one of the following formulas J to N:
[Formula J] [Formula K] [Formula L]

[Formula M] [Formula N]

{In Formula J to Formula N above,
X ³⁰¹ , R ³⁰⁰ , R ³⁰¹ , A301, L ³⁰¹ , L ³⁰³ , L ³⁰⁴ , AR ³⁰¹ and AR ³⁰² are the same as defined in claim 10.
R ³⁰³ is the same as the definition of R ³⁰¹ in claim 10 above,
Ar ³⁰⁵ and Ar ³⁰⁶ are the same as the definition of Ar ³⁰³ in claim 10 above,
a303 is an integer from 0 to 8.}
The organic light emitting display device of claim 10, wherein the contact angle of Formula A is 100° to 180°.
The organic light emitting display device of claim 10, wherein the chemical formula G has a refractive index of 1.85 to 3.0.
The organic light emitting display device of claim 10, wherein the transmittance of Formula A is 80% or more.
The organic light emitting display device of claim 10, wherein the transmittance of Formula G is 70% or more.
The organic light emitting display device according to claim 10, wherein the total light transmittance of the second portion 120 and the third portion 130 is 70% or more.
The organic light emitting display device of claim 1, further comprising a light efficiency improvement layer formed on at least one side of the anode and the cathode opposite to the organic material layer.
The organic light emitting display device of claim 1, wherein the organic material layer includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on an anode.
The organic light emitting display device of claim 20, wherein the organic material layer further includes a charge generation layer formed between the two or more stacks.
A display device including the organic light emitting display device of claim 1; and a control unit that drives the display device.
The electronic device of claim 19, wherein the organic light emitting display device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic or white lighting device, and a display device.

Images