KR102509827B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage and lifetime of a device, an organic electric device using the same, and an electronic device thereof.

Description

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

The present invention relates to a delayed fluorescent material, an organic electric device using the delayed fluorescent material, and an electronic device thereof.

Research on improving the luminous efficiency of organic electric devices (organic EL devices) has been actively conducted until recently, and this has become a major issue in the development of organic electroluminescent devices.

In particular, organic electroluminescent devices using delayed fluorescent materials, which are evaluated as materials for third-generation organic electric devices following fluorescence and phosphorescent materials, have recently attracted attention.

Unlike phosphorescent materials, which convert singlet excitons into triplets and convert them into light, this material converts triplet excitons into singlets and converts them into light. Due to this process, it exhibits delayed fluorescence. Since this delayed fluorescent material can theoretically convert both singlet and triplet excitons into light, 100% internal quantum efficiency is possible, so it is expected to be a material that can overcome the limitations of lifespan and efficiency of blue phosphorescent materials. .

So far, organic electroluminescent devices using delayed fluorescent compounds containing metals such as Cu, Pt, In, Pd, Sn, and Zn have been reported in Patent Documents 1 to 4, and also combining acceptor compounds and donor compounds. Research reports on delayed fluorescence materials using Exciplex have recently been on the rise.

As delayed fluorescence materials using Exciplex, five-ring compound derivatives mainly including heterocycles, anthracene derivatives, biscarbazole derivatives, and fluorene derivatives have been reported in Patent Documents 5 to 8.

[Patent Document 1] JP2011-213643 (published)

[Patent Document 2] JP2013-095688 (published)

[Patent Document 3] JP2013-112608 (published)

[Patent Document 4] JP2013-120770 (published)

[Patent Document 5] JP2014-009352 (published)

[Patent Document 6] JP5565743 (registered)

[Patent Document 7] JP2013-265214 (published)

[Patent Document 8] JP2014-141571 (published)

In the present invention, a new delayed fluorescence material using Exciplex was developed, and a study was conducted to improve the luminous efficiency by applying it to an organic electric device.

An object of the present invention is to provide a compound, an organic electric element thereof, and an electronic device thereof, which achieve high luminous efficiency and low driving voltage and greatly improve the life of the element.

In one aspect, the present invention provides a compound represented by Formula 1 below.

In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by Formula 1 above.

By using the compound according to the present invention, it is possible to achieve high luminous efficiency and low driving voltage of the device, and greatly improve the lifespan of the device.

1 is an example of an organic electroluminescent device according to the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to components of each drawing, it should be noted that the same components have the same numerals as much as possible even if they are displayed on different drawings. In addition, 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.

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

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

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

As used herein, unless otherwise specified, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, and includes a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and the like. A radical of a saturated aliphatic functional group, including an alkyl group, a cycloalkyl-substituted alkyl group.

As used herein, the term "haloalkyl group" or "halogenalkyl group" refers to an alkyl group substituted with a halogen unless otherwise specified.

As used herein, the term "heteroalkyl group" means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.

As used herein, the term "alkenyl group" or "alkynyl group" has a double bond or triple bond of 2 to 60 carbon atoms, respectively, and includes straight or branched chain groups, unless otherwise specified, and is limited thereto. It is not.

As used herein, unless otherwise specified, the term "cycloalkyl" refers to an alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms, unless otherwise specified, and is limited thereto. It is not.

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" refers to an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 It has a carbon number of, but is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" 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 terms "aryl group" and "arylene group" used herein have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or an arylene group refers to a single-ring or multi-ring aromatic ring, and includes an aromatic ring formed by bonding or reacting with adjacent substituents. For example, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, a fluorene group, a spirofluorene group, or a spirobifluorene 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 carbon atoms described herein.

Also, when the prefixes are named consecutively, it means that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group. Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heteroalkyl" as used herein, unless otherwise specified, means an alkyl containing one or more heteroatoms. As used herein, the term "heteroaryl group" or "heteroarylene group" refers to an aryl group or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, and is limited thereto It does not, and includes at least one of a single ring and a multi-ring, and may be formed by combining adjacent functional groups.

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

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

In addition, the "heterocyclic group" may also include a ring containing SO ₂ instead of carbon forming the ring. For example, "heterocyclic group" includes the following compounds.

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

Unless otherwise specified, the term "ring" used herein refers to a fused ring composed of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, Contains saturated or unsaturated rings.

Other hetero compounds or heteroradicals other than the aforementioned hetero compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein is represented by -COR', where R' is hydrogen, an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 30 carbon atoms, or a carbon atom of 3 to 30 carbon atoms. A cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" as used herein is represented by -R-O-R', wherein R or R' are each independently hydrogen, an alkyl group of 1 to 20 carbon atoms, or a carbon atom of 6 to 30 carbon atoms. It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.

In addition, unless explicitly stated otherwise, “substituted” in the term “substituted or unsubstituted” as used herein means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkylamine group, C ₁ ~ C ₂₀ alkylthiophene group, C ₆ ~ C ₂₀ arylthiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, deuterium-substituted C ₆ ~ C ₂₀ aryl group, C ₈ ~ C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and C ₂ ~ C ₂₀ means substituted with one or more substituents selected from the group consisting of heterocyclic groups, but is not limited to these substituents.

In addition, unless explicitly stated otherwise, the chemical formula used in the present invention applies the same as the substituent definition by the exponent definition of the following formula.

Here, when a is an integer of 0, substituent R ¹ does not exist, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3 Each is combined as follows, wherein 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 indicating the hydrogen bonded to the carbon forming the benzene ring. is omitted.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) is provided with an organic material layer containing the compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), and the second electrode 180 may be a cathode (negative electrode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . At this time, other layers except for the light emitting layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like may be further included, and an electron transport layer 160 may serve as a hole blocking layer.

In addition, although not shown, the organic electric element according to the present invention may further include a protective layer or a capping layer formed on a surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.

The compound according to the present invention applied to the organic layer is a host or dopant of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, and the light emitting layer 150 or the light efficiency improvement layer. material can be used. Preferably, the compound of the present invention may be used as the light emitting layer 150 .

On the other hand, even in the same core, since the band gap, electrical properties, interface properties, etc. may vary depending on which substituent is attached to which position, the selection of the core and the combination of sub-substituents bonded thereto are also very important. It is important, and in particular, long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial property, etc.) is achieved.

Therefore, in the present invention, by forming a light emitting layer using the compound represented by Formula 1, the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interface properties, etc.) of the material are optimized to optimize the lifetime of the organic electric device. and efficiency can be improved at the same time.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer ( 160) and the electron injection layer 170, and then depositing a material that can be used as the cathode 180 thereon.

In addition, the organic material layer is formed by a solution process or a solvent process other than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, and a doctor blading process. It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric element according to the present invention may be a top emission type, a bottom emission type or a double side emission type depending on the material used.

WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent processability, and can be manufactured using the color filter technology of the existing LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting units are arranged in parallel on a mutually flat surface, and a stacking method in which R, G, and B light emitting layers are stacked up and down There is, and there is a color conversion material (CCM) method using electroluminescence by a blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using light from the electroluminescent layer. may also be applied to these WOLEDs.

In addition, the organic electric device according to the present invention may be one of an organic light emitting device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit controlling the display device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

A compound according to one aspect of the present invention is represented by Formula 1 below. This compound may be a delayed fluorescence compound.

In Formula 1, R ¹ to R ⁵ are each independently hydrogen, deuterium, halogen, nitro, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryloxy group, an amino group, Silyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, C ₂ ~ C ₆₀ heterocyclic group, carbonyl, ester, nitrile, sulfanyl , It is selected from the group consisting of sulfinyl, sulfonyl, phosphino, and fluorene groups, and at least one of R ¹ to R ⁵ may be A.

R ⁶ to R ¹³ are each independently hydrogen, deuterium, halogen, nitro, a C ₁ -C ₆₀ alkyl group (straight chain, branched chain), a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryloxy group , amino group, silyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, C ₂ ~ C ₆₀ heterocyclic group, carbonyl group, ester group, It is selected from the group consisting of a nitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a fluorene group, and any two adjacent R ⁶ to R ¹³ may combine with each other to form a ring, and condensate with carbazole. Fused carbazole can be excluded.

At least one of R ¹ to R ⁵ may be CN.

At least one of R ¹ to R ⁵ may be one of Formulas 2 to 6 below.

When two or more of R ¹ to R ⁵ are selected from Formulas 2 to 6, they may be different from each other.

In Chemical Formulas 2 to 6, X is O, S, CR ⁶ R ⁷ , Y ¹ to Y ⁴ are CR', N, and at least one may be N.

R′, R ¹⁴ to R ⁵¹ are each independently hydrogen, deuterium, halogen, nitro, a C ₁ -C ₆₀ alkyl group (straight chain, branched chain), a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ Aryloxy group, amino group, silyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, C ₂ ~ C ₆₀ heterocyclic group, carbonyl group, It may be selected from the group consisting of an ester group, a nitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a fluorene group. In this case, any two adjacent R ¹⁴ to R ⁵¹ may combine with each other to form a ring. For example, any two adjacent R ¹⁴ to R ⁴³ may combine with each other to form a ring. Hereinafter, examples in which adjacent groups in Chemical Formulas 2 to 6 combine with each other to form a ring will be described in detail.

L may be selected from the group consisting of a single bond, a C ₆ -C ₆₀ arylene group, a C ₂ -C ₆₀ heterocyclic group, and a fluorene group.

Each of the alkyl group, alkoxy group, aryloxy group, alkenyl group, aryl group, heteroaryl group, heterocyclic group, fluorenyl group, arylene group, heterocyclic group, fluorene group is deuterium, halogen, silane group, siloxane group , boron group, germanium group, cyano group, nitro group, -L'-N(R _c )(R _d ) (wherein L' is a single bond; C ₆ ~ C ₆₀ arylene group; fluorenylene group; C It is selected from the group consisting of ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fused ring group of aromatic ring; and C ₂ ~ C ₆₀ heterocyclic group; wherein R _c and R _d are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; and at least one heteroatom selected from O, N, S, Si and P A C ₂ ~ C ₆₀ heterocyclic group containing; selected from the group consisting of), C ₁ ~ C ₂₀ alkylthio group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₆ ~ C ₂₀ aryl group, deuterium-substituted C ₆ ~ C ₂₀ aryl group, fluorenyl group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ arylalkenyl group, carbonyl group, ether group, C ₂ ~ C ₂₀ alkoxylcarbonyl group, C ₆ ~ C ₃₀ aryloxy group, -O-Si(R ^x ) ₃ , and R ^x O-Si (R ^x ) ₂ - (wherein R ^x is hydrogen, a C ₆ ~ C ₂₀ aryl group, a C ₁ ~ C ₂₀ alkyl group, a C ₂ ~ C ₂₀ alkenyl group, a C ₈ ~ C ₂₀ arylalkenyl group, C ₇ ~ C ₂₀ arylalkoxyl group, or C ₂ ~ C ₂₀ alkoxylcarbonyl group) may be substituted with one or more substituents selected from the group consisting of.

Specifically, when two adjacent groups of R ⁶ to R ¹³ of A combine with each other to form a ring, A may be a delayed fluorescent compound represented by one of the following formulas, but is not limited thereto.

In Chemical Formulas A-1 to A-14, R ⁶ to R ¹³ and L may be the same as those defined in A above.

In addition, when two adjacent groups of R ¹⁴ to R ²¹ in Formula 2 combine with each other to form a ring, Formula 2 may be a delayed fluorescent compound of one of the following formulas, but is not limited thereto.

In Chemical Formulas 2-1 to 2-18, definitions of X and R ¹⁴ to R ²¹ are the same as defined in Chemical Formula 2, and Z ¹ to Z ²⁶ may be CR' or N.

In addition, when two adjacent groups of R ²² to R ²⁵ in Formula 3 are bonded to each other to form a ring, Formula 3 may be a delayed fluorescent compound of one of the following formulas, but is not limited thereto.

In Formulas 3-1 to 3-4, definitions of R ²² to R ²⁵ are the same as those defined in Formula 3, and definitions of Y ⁵ to Y ²⁰ may be the same as those defined in Y ¹ to Y ⁴ above. .

In addition, R ²⁶ to R ³¹ of Formula 4 When two groups adjacent to each other are bonded to each other to form a ring, Formula 4 may be a delayed fluorescent compound of one of the following formulas. It is not limited to this.

In Chemical Formulas 4-1 to 4-4, R ²⁶ to R ³¹ may be defined the same as those defined in Chemical Formula 4.

In addition, when two adjacent groups of R ³² to R ⁴³ in Formula 5 bond to each other to form a ring, Formula 5 may be a delayed fluorescence compound of one of the following formulas, but is not limited thereto.

In Chemical Formulas 5-1 to 5-4, R ³² to R ⁴³ may be defined the same as those defined in Chemical Formula 5.

Here, the aryl group may have 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms, and in the case of the heterocyclic group, carbon atoms 2 to 60, preferably 2 carbon atoms ~ 30, more preferably, it may be a heterocyclic ring having 2 to 20 carbon atoms, and in the case of the alkyl group, the number of carbon atoms is 1 to 50, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 20 carbon atoms It may be an alkyl group of 1 to 10.

Here, the single bond means a direct bond in the absence of L, and specific compounds 1-1 to 1-10, 1-15 to 1-18, and 1-21 to 1 that may be included in Formula 1 of the present invention -24, 1-26 to 1-35, 1-39, 1-42 to 1-47, 1-52 to 1-53, 1-55 to 1-56, 1-59 to 1-62, 1-65 , 1-68 to 1-71, 1-75 and the like describe compounds in which L is a single bond.

When the substituents are an aryl group or an arylene group, the aryl group or arylene group is independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a phenan. It may be a triylene group or the like.

More specifically, the compound represented by Formula 1 may be any one of the following compounds, but is not limited to the following compounds. That is, the compound represented by Formula 1 may be a delayed fluorescence compound that is any one of the compounds represented by Formulas 1-1 to 1-76 below.

As another embodiment, the present invention provides a compound for an organic electric device represented by Formula 1 above.

In another embodiment, the present invention provides an organic electric device containing the compound represented by Formula 1 above.

At this time, the organic electric element includes a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, wherein the organic material layer may include a compound represented by Chemical Formula 1, wherein the compound represented by Chemical Formula 1 is a hole injection layer and a hole transport layer of the organic material layer. , It may be contained in at least one layer of a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer. In particular, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

That is, the compound represented by Formula 1 may be used as a material for a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, or an electron injection layer. In particular, the compound represented by Formula 1 may be used as a material for the light emitting layer. Specifically, an organic electric device including one of the compounds represented by Formula 1 is provided in the organic layer, and more specifically, the An organic electric device including the compounds represented by the individual chemical formulas (1-1 to 1-76) in the organic material layer is provided.

In another embodiment, in at least one layer of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer of the organic material layer, the compound is contained alone, or the It provides an organic electric device characterized in that the compound is contained in a combination of two or more different types, or the compound is contained in a combination of two or more types with other compounds. In other words, each layer may contain a compound corresponding to Formula 1 alone, or may include a mixture of two or more types of compounds represented by Formula 1, and the compounds of claims 1 to 4 and compounds not applicable to the present invention. Mixtures with may be included. Here, the compound that does not correspond to the present invention may be a single compound or may be two or more types of compounds. In this case, when the above compounds are contained in a combination of two or more kinds of other compounds, the other compounds may be known compounds of each organic material layer or may be compounds to be developed in the future. In this case, the compound contained in the organic material layer may be composed of only the same type of compound, but may also be a mixture of two or more different types of compounds represented by Formula 1.

In another embodiment of the present invention, the present invention is a light efficiency improvement layer formed on at least one of one side opposite to the organic material layer among one side of the first electrode or one side opposite to the organic material layer among one side of the second electrode. It provides an organic electric element further comprising a.

Hereinafter, a synthesis example of the compound represented by Formula 1 and an example of manufacturing an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[ synthesis example ]

The final products represented by Chemical Formula 1 according to the present invention are synthesized by reacting Sub 1 and Sub 2 as shown in Schemes 1 to 3 below, but are not limited thereto.

Hereinafter, formulas 2 to 6 in R ¹ to R ⁵ are abbreviated as A', and the remaining R ¹ to R ⁵ are abbreviated as R'.

<Scheme 1> When L of A' is a single bond (Hal ¹ = F, Cl, Br, I)

(A' is one of Formulas 2 to 6, l, o, p = 1 to 3; n = 0 to 2; m = 1 to 4)

<Scheme 2> When L of A' is a single bond (Hal ¹ = F, Cl, Br, I)

<Scheme 3> When L in A' is not a single bond

I. Synthesis example of Sub 1

Sub 1 of Reaction Schemes 1 to 3 may be synthesized by the reaction pathways of Reaction Schemes 4 to 6 below, but is not limited thereto. In addition, Table 1 shows the FD-MS values of compounds belonging to Sub 1.

<Scheme 4> When L of A is a single bond (Hal ¹ = F, Cl, Br, I)

<Scheme 5> When L in A is a single bond

<Scheme 6> When L in A is not a single bond

Sub 1 of Reaction Schemes 1 to 3 describes specific synthesis examples synthesized by the reaction pathways of Reaction Schemes 4 to 6 below. In addition, Table 1 shows the FD-MS values of compounds belonging to Sub 1 synthesized by specific synthetic examples.

1. Synthesis of Sub 1-15

A mixture of 11H-benzo[a]carbazole (3.91g, 17.98mmol) and K2CO3 (2.48g, 17.98mmol) in DMSO (59mL) was stirred at room temperature for 1 hour. 4,5-difluorophthalonitrile (5.9g, 35.95mmol) was added to the reaction mixture and stirred for 2 hours, followed by stirring at 50 degrees for 15 hours. After cooling to room temperature, it was poured into H2O and filtered. After washing with H2O, the obtained solid was dissolved in dichloromethane and the organic layer was separated. It was dried over MgSO4, filtered through silica gel, and concentrated. Recrystallization from dichloromethane and methanol gave 4.16 g of product. (Yield: 64%)

2. Synthesis of Sub 1-14

9'-phenyl-9H,9'H-2,3'-bicarbazole (10.70g, 26.20mmol), K ₂ CO ₃ (4.71g, 34.06mmol), DMSO (43mL), 4,5-difluorophthalonitrile (4.3g , 26.20 mmol) was used to obtain 8.69 g of the product using the Sub 1-1 synthesis method. (Yield: 60%)

3. Synthesis of Sub 1-20

4,5-dibromophthalonitrile (8.1g, 28.33mmol), 11H-benzo[a]carbazole (6.16g, 28.33mmol), Pd ₂ (dba) ₃ (1.30g, 1.42mmol), P(t- After adding Bu) ₃ (0.57g, 2.83mmol), NaO t -Bu (4.08g, 42.49mmol), and toluene (297ml), the reaction was conducted at 100 °C. After the reaction was completed, extraction was performed with ether and water, the organic layer was dried with MgSO ₄ , concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 8.02 g of the product. (Yield: 67%)

4. Sub 1- 8 of synthesis

4,5-dibromophthalonitrile (6.2 g, 21.68 mmol) was added to a round bottom flask, and 9-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[ 1,1'-biphenyl]-4-yl)-9H-carbazole (9.66g, 21.68mmol), Pd(PPh ₃ ) ₄ (0.75g, 0.65mmol), K ₂ CO ₃ (8.99g, 65.05mmol), Add THF (95mL) and water (48mL). After that, it is heated to reflux at 80℃~90℃. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. After drying and concentrating the organic layer with MgSO ₄ , the resulting compound was recrystallized using a silica gel column to obtain 8.07 g of the product. (Yield: 71%)

5. Sub 1- 11 of synthesis

4,5-dibromophthalonitrile (6 g, 21.13 mmol) was added to a round bottom flask, and 9-(9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-9H-fluoren-2-yl)-9H-carbazole (10.26g, 21.13mmol), Pd(PPh ₃ ) ₄ (0.73g, 0.63mmol), K ₂ CO ₃ (8.76g, 63.4mmol), THF (93mL) and water (46mL). After that, it is heated to reflux at 80℃~90℃. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 8.23 g of the product. (Yield: 69%)

6.Sub One- 12 of synthesis

4,5-dibromophthalonitrile (5.9 g, 20.78 mmol) was added to a round bottom flask, and 9-(9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -yl)-9H-fluoren-2-yl)-9H-carbazole (9.88g, 20.78mmol), Pd(PPh ₃ ) ₄ (0.72g, 0.62mmol), K ₂ CO ₃ (8.62g, 62.34mmol), Add THF (91 mL) and water (46 mL). After that, it is heated to reflux at 80℃~90℃. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. After drying and concentrating the organic layer with MgSO ₄ , the resulting compound was recrystallized using a silica gel column to obtain 8.41 g of the product. (Yield: 73%)

Example of Sub 1

[Table 1]

II. Synthesis example of Sub 2

Sub 2 of Reaction Scheme 1 and Scheme 2 may be synthesized by the reaction pathway of Reaction Scheme 7 below, but is not limited thereto. In addition, Table 2 shows the FD-MS values of compounds belonging to Sub 2.

<Scheme 7> When L does not exist

(However, Hal2 is Br or Cl.)

(Ra is each R ₈ to R ₁₁ , Rb is each R ₁₂ to R ₁₅ , at least one of adjacent Ra and Rb necessarily forms a ring, and q and r are integers of 4.)

1. Synthesis of Sub 2-20

2-bromo-9,9-dimethyl-9H-fluorene (8g, 29.29mmol), 4-Aminobiphenyl (4.96g, 29.29mmol), Pd2(dba)3 (1.34g, 1.46mmol), P(t-Bu) 3 (0.59g, 2.93mmol), NaOt-Bu (4.22g, 43.93mmol), and toluene (307mL) were used to synthesize Sub 2-23 to obtain 6.78g of the product. (Yield: 64%)

2. Synthesis of Sub 2-31 (when L is not a single bond)

(1) Synthesis of Intermediate Sub 2-I-31

After dissolving the starting material 6-bromo-9H-pyrido[2,3-b]indole (7.5g, 30.35mmol) in THF (134ml), dibenzo[b,d]thiophen-2-ylboronic acid (6.92g, 30.35mmol), Pd(PPh3)4 (1.05g, 0.91mmol), K2CO3 (12.59g, 91.06mmol), and water (64ml) were added and stirred at 80°C. After the reaction was completed, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4, concentrated, and the resulting compound was recrystallized using a silica gel column to obtain 9.36 g of product (yield: 88%).

2) Synthesis of Intermediate Sub 2-II-31

After dissolving Sub 2-II-31 (7.0g, 19.98mmol) obtained in the above synthesis with nitrobenzene (100ml) in a round bottom flask, 1-bromo-3-iodobenzene (6.22g, 21.97mmol), Na2SO4 (2.84g, 19.98mmol), K2CO3 (2.76g, 19.98mmol), and Cu (0.38g, 5.99mmol) were added and stirred at 200°C. Upon completion of the reaction, nitrobenzene was removed by distillation and extracted with CH2Cl2 and water. After drying and concentrating the organic layer with MgSO4, the resulting compound was recrystallized using a silica gel column to obtain 7.88 g of the product (yield: 78%).

(3) Synthesis of Sub 2-31

After dissolving Sub 2-III-31 (7.88g, 15.59mmol) obtained in the above synthesis in DMF (98ml) in a round bottom flask, Bis(pinacolato)diboron (4.36g, 17.15mmol), Pd(dppf)Cl2 (0.34 g, 0.47mmol), KOAc (4.59g, 46.77mmol) were added and stirred at 90°C. Upon completion of the reaction, DMF was removed by distillation and extraction was performed with CH2Cl2 and water. After drying and concentrating the organic layer with MgSO4, the resulting compound was recrystallized using a silica gel column to obtain 6.29 g of the product (yield: 73%).

3. Synthesis of Sub 2-41

(1) Synthesis of Intermediate Sub 2-I-41

2,3,4,9-tetrahydro-1H-carbazole (5.29g, 30.89mmol), nitrobenzene (154ml), 3-bromo-7-iododibenzo[b,d]thiophene (13.22g, 33.98mmol), Na2SO4 (4.39 g, 30.89mmol), K2CO3 (4.27g, 30.89mmol), and Cu (0.59g, 9.27mmol) were used to obtain a product of 10.15g (yield: 76%) using the Sub 2-II-31 synthesis method.

(2) Synthesis of Sub 2-41

Sub 2-I-41 (10.15g, 23.48mmol), DMF (148ml), Bis(pinacolato)diboron (6.56g, 25.82mmol), Pd(dppf)Cl2 (0.52g, 0.7mmol), KOAc obtained from the above synthesis (6.91g, 70.42mmol) was obtained by using the Sub 2-31 synthesis method to obtain a product of 7.99g (yield: 71%).

4. Sub Synthesis of 2-42

(1) Synthesis of Intermediate Sub 2-I-42

1,1,2,2,3,3,4,4-octamethyl-2,3,4,9-tetrahydro-1H-carbazole (6.00g, 21.17mmol), nitrobenzene (106ml), 3-bromo-7- Iododibenzo[b,d]furan (8.68g, 23.29mmol), Na2SO4 (3.01g, 21.17mmol), K2CO3 (2.93g, 21.17mmol), Cu (0.40g, 6.35mmol) Sub 2-II-31 synthesis method 7.94 g (yield: 71%) of the product was obtained.

(2) Synthesis of Sub 2-42

Synthesis of Sub 2-I-42 (7.94g, 15.02mol), DMF (95ml), Bis(pinacolato)diboron (4.20g, 15.02mmol), Pd(dppf)Cl2 (0.33g, 0.45mmol), KOAc (4.42 g, 45.07 mol) was used to obtain 5.88 g (yield: 68%) of the product by using the Sub 2-31 synthesis method.

Example of Sub 2

[Table 2]

III. Example of Final Product Synthesis

1. Synthesis of compound 1-2

A mixture of Sub 1-2 (5.40g, 14.70mmol) and K2CO3 (2.64g, 19.11mmol) in DMSO (24mL) was stirred at room temperature for 1 hour. Sub 2-1 (2.93g, 14.70mmol) was added to the reaction mixture and stirred for 2 hours, followed by stirring at 50°C for 15 hours. After cooling to room temperature, it was poured into H2O and filtered. After washing with H2O, the obtained solid was dissolved in dichloromethane and the organic layer was separated. It was dried over MgSO4, filtered through silica gel, and concentrated. Recrystallization from dichloromethane and methanol gave 6.03 g of product. (Yield: 75%)

2. Synthesis of compounds 1-10

Sub 1-12 (6.74g, 10.45mmol), K2CO3 (1.88g, 13.59mmol), DMSO (17mL), Sub 2-1 (2.08g, 10.45mmol) were synthesized using the above 1-2 synthesis method to obtain a product of 6.03g got (Yield: 70%)

3. Synthesis of compounds 1-25

Put Sub 1-31 (4.90g, 8.94mmol) in a round bottom flask, Sub 2-29 (3.87g, 8.94mmol), Pd(PPh ₃ ) ₄ (0.31g, 0.27mmol), K ₂ CO ₃ (3.70 g, 26.80 mmol), THF (39 mL), and water (20 mL). After that, it is heated to reflux at 80℃~90℃. When the reaction is complete, distilled water is diluted at room temperature and extracted with methylene chloride and water. After drying and concentrating the organic layer with MgSO ₄ , the resulting compound was recrystallized using a silicagel column to obtain 6.10 g of the product. (Yield: 78%)

4. Synthesis of compounds 1-49

Sub 1-14 (6.50g, 14.5mmol), Sub 2-36 (4.63g, 14.5mmol), Pd(PPh ₃ ) ₄ (0.50g, 0.44mmol), K ₂ CO ₃ (6.01g, 43.5mmol), THF (64 mL) and water (32 mL) were used to obtain 6.10 g of product using the synthesis method of 1-25. (Yield: 75%)

5. Synthesis of compounds 1-52

Sub 1-16 (7.00g, 19.37mmol), Sub 2-9 (2.27g, 19.37mmol), Pd(PPh ₃ ) ₄ (0.67g, 0.58mmol), K ₂ CO ₃ (8.03g, 58.11mmol), THF (85mL) and water (43mL) were used to obtain 6.04g of the product according to the synthesis method of 1-25. (Yield: 68%)

6. Synthesis of compounds 1-58

Sub 1-29 (5.10g, 9.2mmol), Sub 2-41 (4.41g, 9.2mmol), Pd(PPh ₃ ) ₄ (0.32g, 0.28mmol), K ₂ CO ₃ (3.81g, 27.59mmol), THF (40mL) and water (20mL) were used to obtain 6.01 g of the product according to the synthesis method of 1-25. (Yield: 79%)

7. Synthesis of compounds 1-64

Sub 1-30 (5g, 9.29mmol), Sub 2-42 (5.35g, 9.29mmol), Pd(PPh ₃ ) ₄ (0.32g, 0.28mmol), K ₂ CO ₃ (3.85g, 27.86mmol), THF (41 mL) and water (20 mL) to obtain 6.07 g of product using the synthesis method of 1-25 above. (Yield: 72%)

8. Synthesis of compound 1-72

Sub 1-13 (4.5g, 10.04mmol), Sub 2-44 (5.50g, 10.04mmol), Pd(PPh ₃ ) ₄ (0.35g, 0.3mmol), K ₂ CO ₃ (4.16g, 30.11mmol), THF (44mL) and water (22mL) were used to obtain 6.10 g of product using the synthesis method of 1-25. (Yield: 77%)

[Table 4]

IV. Organic electric element manufacturing evaluation

[ Example 1] Fabrication and testing of organic light emitting devices ( delayed fluorescence )

An organic electroluminescent device was fabricated according to a conventional method using the compound obtained through synthesis as a dopant material for the light emitting layer. First, as a hole injection layer on the ITO layer (anode) formed on the glass substrate, N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino) A phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) as a hole transport compound was vacuum deposited on the film to a thickness of 20 nm to form a hole transport layer. was formed. 6% by weight of the inventive compound 1'-1 and 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (mCP) was co-deposited on top of the hole transport layer to form a thickness of 30 nm on the hole transport layer. of the light emitting layer was deposited. As a hole-blocking layer, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited to a thickness of 10 nm, and an electron transport layer was formed. A film of tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, followed by Al to a thickness of 150 nm, and Al/LiF was used as a cathode to manufacture an organic electroluminescent device.

[mCP]

[ comparative example One]

An organic light emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 was used instead of Compound 1'-1 of the present invention.

[ comparative example 2]

An organic light emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound 2 was used instead of Compound 1'-1 of the present invention.

[ Example 2] to [ Example 15]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compounds 1'-1 to 1'-36 of the present invention were used instead of Compound 1'-1 of the present invention.

A forward bias DC voltage was applied to the organic electroluminescent devices of Examples and Comparative Examples prepared as described above to measure electroluminescence (EL) characteristics with PR-650 of Photoresearch, and as a result of the measurement, at a standard luminance of 500 cd/m2 T90 life was measured through life measurement equipment manufactured by McScience. Table 5 below shows the device fabrication and evaluation results.

[Table 5]

As can be seen from the results of Table 5, the organic light emitting device using the material for the organic light emitting device of the present invention as a material for the light emitting layer can remarkably improve the luminous efficiency, driving voltage and lifetime.

In particular, Comparative Example 2 using Comparative Compound 2 containing two cyano groups and carbazole in the benzene ring showed higher results in terms of luminous efficiency than Comparative Compound 1, which is a general fluorescent dopant in which two amine groups are substituted in the anthracene core. , Compared to Comparative Example 2, the compound of the present invention including at least one carbazole core and at least one donor group such as Formulas 2 to 6, which is a heterocyclic group, has higher luminous efficiency and lower drive than Comparative Compounds 1 to 2 voltage and long life.

By including a donor group such as Formulas 2 to 6 in at least one carbazole core, the carbazole group, which is an electron donating substituent, is substituted with a specific molecule such as Formulas 2 to 6, and the donor unit and acceptor unit in one molecule It can be explained that it shows the result of high efficiency, long lifespan and low driving voltage because it is properly combined to form an exciplex.

In particular, looking at the device performance of the donor unit of the compound of the present invention, the aryl group connected to N is an open amine group (-N(Ar ₂ ) (Ar ₃ ) than in Formula 6, which has a form of a single bond or atom as a linking group, resulting in N In the case of chemical formulas 2 to 5, which make the structure of the aryl group flat (planar), the device performance in terms of driving voltage, efficiency, and lifetime was superior.

In Chemical Formulas 2 to 5, the compound having Chemical Formula 2 was superior to Chemical Formula 4 having an indole core in terms of efficiency and lifespan. A compound having S and O was excellent in terms of efficiency. In addition, Formula 5, which has a bulky core substituted with an alkyl group, was more efficient than the compound having Formula 2, and Formula 3, a carboline containing heteroatom N in the backbone core, was more efficient than Formula 5 in terms of efficiency and lifetime. Excellent device performance results were shown.

In the case of efficiency, it was confirmed that when a bulky substituent such as tert-buthyl is substituted with a secondary substituent, the efficiency is increased by minimizing the steric hindrance in which molecules stick together to facilitate the movement of exciton between the host and the dopant. (Example 2, 5, 8, 10, 16)

That is, even in the same core, it suggests that the energy level changes depending on the substituent and the characteristics of the device itself can be significantly different. In addition, in the evaluation results of the above-mentioned device fabrication, the device characteristics were described from the viewpoint of the light emitting layer, but the materials commonly used for the light emitting layer are organic electric devices such as the above-mentioned electron transport layer, electron injection layer, hole injection layer, hole transport layer, and light emitting auxiliary layer. It can be used alone or in combination with other materials. Therefore, for the reasons described above, the compound of the present invention may be used singly or in combination with other materials in other organic layers other than the light emitting layer, such as an electron transport layer, an electron injection layer, a hole injection layer, a hole transport layer, and a light emitting auxiliary layer.

The above description is merely illustrative 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 intended to explain, not limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed according to the following claims, and all technologies within the equivalent range should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer

Claims (13)

A delayed fluorescent compound represented by Formula 1 below:

In Formula 1,
R ¹ is CN;
R ² and R ⁵ are hydrogen;
one of R ³ and R ⁴ is A;

R ⁶ to R ¹³ are i) independently of each other hydrogen, deuterium, halogen, nitro, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryloxy group, amino group, silyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, C ₂ ~ C ₆₀ heterocyclic group, carbonyl group, ester group, nitrile group, sulfa It is selected from the group consisting of a yl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a fluorene group, or ii) any two adjacent R ⁶ to R ¹³ may combine with each other to form an aromatic hydrocarbon ring,
The other one of R ³ and R ⁴ is one of the following formulas 2 to 6,

In Formulas 2 to 6,
X is O, S or CR ⁶ R ⁷ ;
Y ¹ to Y ⁴ are CR' or N, and at least one is N;
R ⁶ and R ⁷ are each independently selected from the group consisting of hydrogen, heavy hydrogen, a C ₁ -C ₆₀ alkyl group, and a C ₆ -C ₆₀ aryl group, or R ⁶ and R ⁷ may combine with each other to form a ring, ,
R′, R ¹⁴ to R ⁵¹ are each independently selected from i) hydrogen, deuterium, halogen, nitro, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryloxy group, Amino group, silyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, C ₂ ~C ₆₀ heterocyclic group, carbonyl group, ester group, nitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, selected from the group consisting of a fluorene group, or ii) any two adjacent groups of R ¹⁴ to R ¹⁷ , any adjacent 2 groups of R ¹⁸ to R ²¹ two groups, any two adjacent groups of R ²² to R ²⁵ , any two adjacent groups of R ²⁸ to R ³¹ , any two adjacent groups of R ⁴⁴ to R ⁴⁷ , R ⁴⁸ to R Any two adjacent groups of ⁵¹ may be bonded to each other to form at least one ring,
L is selected from the group consisting of a single bond, a C ₆ -C ₆₀ arylene group, and a fluorene group;
Each of the alkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an aryl group, a heteroaryl group, a heterocyclic group, a fluorenyl group, an arylene group, and a fluorene group is deuterium, a halogen, a silane group, a siloxane group, a boron group, Germanium group, cyano group, nitro group, -L'-N(R _c )(R _d ) (Where L' is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorenylene group; C ₃ ~ C ₆₀ It is selected from the group consisting of an aliphatic ring and a C ₆ ~ C ₆₀ fused ring group of an aromatic ring; and a C ₂ ~ C ₆₀ heterocyclic group; wherein R _c and R _d are independently of each other C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; and C containing at least one heteroatom of O, N, S, Si and P ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of), C ₁ ~ C ₂₀ alkylthio group, C ₁ ~ C ₂₀ alkoxyl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl group, C ₆ ~ C ₂₀ aryl group, deuterium-substituted C ₆ ~ C ₂₀ aryl group, fluorenyl group, C ₂ ~ C ₂₀ heterocyclic group, C ₃ ~ C ₂₀ cycloalkyl group, C ₇ ~ C ₂₀ arylalkyl group, C ₈ ~ C ₂₀ arylalkenyl group, carbonyl group, ether group, C ₂ ~ C ₂₀ alkoxylcarbonyl group, C ₆ ~ C ₃₀ aryloxy group, -O-Si(R ^x ) ₃ , and R ^x O-Si (R ^x ) ₂ - (wherein R ^x is hydrogen, a C ₆ ~ C ₂₀ aryl group, a C ₁ ~ C ₂₀ alkyl group, a C ₂ ~ C ₂₀ alkenyl group, a C ₈ ~ C ₂₀ arylalkenyl group, A C ₇ ~ C ₂₀ arylalkoxyl group, or a C ₂ ~ C ₂₀ alkoxylcarbonyl group) may be substituted with one or more substituents selected from the group consisting of,
compound

,

,

,

are excluded from the present invention. According to claim 1,
Wherein A is a delayed fluorescent compound represented by one of the following formulas A-1 to A-14.

(In the formulas A-1 to A-14,
The R ⁶ to R ¹³ and L are the same as those defined in A) delete delete delete delete A delayed fluorescent compound that is any one of the compounds represented by Formula 1-2 to Formula 1-76:

. a first electrode;
a second electrode; and
In the organic electric device having at least one organic material layer including a light emitting layer between the first electrode and the second electrode,
An organic electric device characterized in that the light emitting layer contains the delayed fluorescent compound according to any one of claims 1, 2 and 7. According to claim 8,
The delayed fluorescent compound included in the light emitting layer is an organic electric device, characterized in that the same type or two or more heterogeneous compounds. According to claim 8,
The organic electric device further comprises a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer. According to claim 8,
The organic layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process. A display device comprising the organic electric element of claim 8; and
An electronic device comprising a controller for driving the display device. According to claim 12,
The electronic device according to claim 1 , wherein the organic electric element is one of an organic light emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white lighting.

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