KR102294677B1 - 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 lifespan of the device, an organic electric device using the same, and an electronic device thereof.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof

The present invention relates to a novel delayed fluorescence material, an organic electroluminescent device using the delayed fluorescence material, and an electronic device thereof.

Research to increase the luminous efficiency of organic electroluminescent devices (organic EL devices) has been actively conducted until recently, which has become a major issue in the development of organic electroluminescent devices.

In particular, recently, after fluorescent and phosphorescent materials, organic electroluminescent devices using delayed fluorescence materials, which are evaluated as materials for third-generation organic electronic devices, are attracting attention.

Unlike phosphorescent materials that convert singlet excitons into triplets and convert to light, this material converts triplet excitons into singlets and converts them into light, and because of this process, it exhibits delayed fluorescence. This delayed fluorescent material can theoretically convert both singlet and triplet excitons into light, so 100% internal quantum efficiency is possible. .

So far, organic electroluminescent devices using delayed fluorescence compounds containing metals such as Cu, Pt, In, Pd, Sn, Zn, etc. have been reported in Patent Documents 1 to 4 below, and a combination of an acceptor compound and a donor compound. Research reports on delayed fluorescence materials using Exciplex are increasing in recent years.

As a delayed fluorescence material using Exciplex, a 5-cyclic compound derivative containing a heterocyclic ring, an anthracene derivative, a biscarbazole derivative, a fluorene derivative, etc. 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)

By developing a new delayed fluorescence material using Exciplex and applying it to an organic electroluminescent device, it was studied as a task to improve luminous efficiency.

In one aspect, the present invention provides a compound represented by the following formula.

(Ring A and Ring B include a carbocyclic or heterocyclic aromatic ring, and are the same as or different from each other)

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

By using the compound according to the present invention, high luminous efficiency and low driving voltage of the device can be achieved, and the lifespan of the device can be greatly improved.

1 is an exemplary view 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 the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though they are indicated 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 thereof will be omitted.

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the components from other components, and the essence, order, or order of the components are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should 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” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond having 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term “haloalkyl group” or “halogenalkyl group” refers to an alkyl group substituted with 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.

The term "alkenyl group" or "alkynyl group" used in the present invention, unless otherwise specified, has a double or triple bond of 2 to 60 carbon atoms, respectively, and includes a straight or branched chain group, and is limited thereto it is not

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms unless otherwise specified, 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. it is not

As used herein, the term "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and unless otherwise specified, 2 to 60 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 in the present invention 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 means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an 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 the radical substituted with an aryl group has the number of carbon atoms described herein.

Also, when prefixes are named consecutively, it is meant 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 and wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heteroalkyl" refers to an alkyl containing one or more heteroatoms, unless otherwise specified. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl group or arylene group having 2 to 60 carbon atoms each containing one or more heteroatoms, unless otherwise specified, No, it includes at least one of a single ring and a multiple ring, and may be formed by combining adjacent functional groups.

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, 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. aromatic rings. It may 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 include a ring including _{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 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" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a combination thereof, saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.

Unless otherwise specified, the term "carbonyl" used in the present invention is represented by -COR', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. of 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" used in the present invention is represented by -RO-R', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 6 to 30 carbon atoms. An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

In addition, unless explicitly stated otherwise, in the term "substituted or unsubstituted" used in the present invention, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, but is not limited to these substituents.}

In addition, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponential definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3 Each is bonded 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 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 device 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 . ), an organic layer containing the compound according to the present invention is provided. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), 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 . In this case, the remaining layers except for the emission layer 150 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151 , a buffer layer 141 , and the like, and the electron transport layer 160 and the like may serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material 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, the light emitting layer 150, or the light efficiency improvement layer. material could be used. Preferably, the compound of the present invention may be used as the light emitting layer 150 .

On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, so the selection of the core and the combination of the sub-substituents coupled thereto are also very In particular, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

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 characteristics, etc.) of the material are optimized, and the lifespan of the organic electric device. and efficiency can be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) 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, the electron transport layer ( 160) and an organic material layer including the electron injection layer 170 may be formed, and then a material that can be used as the cathode 180 is deposited thereon.

In addition, the organic layer is a solution process or a solvent process rather 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, Dr. Blay 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 material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

The organic electric device according to the present invention may be a top emission type, a back 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 in processability, and can be manufactured using the color filter technology of the existing LCD. Various structures for a white organic light emitting diode mainly used as a backlight device have been proposed and patented. Typically, the R (Red), G (Green), and B (Blue) light emitting units are arranged in parallel in a planar manner (side-by-side), and the R, G, and B light emitting layers are stacked up and down in a stacking method. There is a color conversion material (CCM) method using electroluminescence by the blue (B) organic light emitting layer and photo-luminescence of an inorganic phosphor using the light therefrom, and the present invention could also be applied to such WOLEDs.

In addition, the organic electric device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and a single color or white lighting device.

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 for controlling the display device. In this case, 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 control, a navigation system, a game machine, various TVs, and various computers.

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

The compound according to one aspect of the present invention is represented by the following formula (1). The present compound may be a delayed fluorescence compound.

<Formula 1>

In Formula 1,

R ¹ and R ² are each independently hydrogen; heavy hydrogen; C ₁ -C ₆₀ Alkyl group; C ₆ -C ₆₀ Aryl group; It may be selected from the group consisting of a cyano group, wherein ^{at least one of R 1} and R ² is a cyano group.

Ring A and Ring B may include a carbocyclic or heterocyclic aromatic ring, and may be the same as or different from each other.

Each of the aryl group, alkyl group, cyano group, carbocyclic aromatic ring, and heterocyclic aromatic ring is deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, -L'-N ( R _a ) (R _b ) (wherein L 'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorenylene group; C ₃ ~ C ₆₀ Aliphatic ring and C ₆ ~ C ₆₀ A fused ring of an aromatic ring and a C ₂ ~ C ₆₀ heterocyclic group; selected from the group consisting of, wherein R _a and R _b are each independently C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ aliphatic A fused ring group of a ring and a C ₆ ~ C _{60 aromatic ring; and a C 2} ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; selected from the group consisting of) , C ₁ ~ C ₂₀ coming of the alkylthio, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C ₂₀ of the of 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, C ₆ ~ C ₂₀ aryl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₈ ~ C ₂₀ arylalkenyl group, It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkoxyl group, or C ₂ ~ C _{20 alkoxylcarbonyl group).}

Here, in the case of the aryl group, it may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 30 carbon atoms,

In the case of the heterocyclic group, it may be a heterocyclic ring having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms,

In the case of the alkyl group, the alkyl group may have 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms.

Specifically, Ring A and Ring B of Formula 1 may be represented by one of the following Formulas.

<Formula 2> <Formula 3> <Formula 4>

<Formula 5> <Formula 6>

In Formulas 2 to 6,

X is O, S, CR ³ R ⁴ or a single bond.

Here, the single bond refers to direct bonding in the absence of X, and formulas 1'-1 to 1'-35, 1'-39 to 1'-41, 2' that may be included in Formula 1 of the present invention -25 et al. describe compounds wherein X is a single bond.

Y ¹ to Y ⁴ are each independently CR′ or N, at least one is N, and when a plurality of R′ is present, a plurality of R′ may be the same as or different from each other.

The R ³ and R ⁴ are each independently hydrogen; heavy hydrogen; C ₁ -C ₆₀ Alkyl group; C ₆ -C ₆₀ An aryl group; may be selected from the group consisting of.

In addition, R ³ and R ⁴ may be bonded to each other to form at least one ring. In this case, R ³ , R ⁴ that does not form a ring may be defined the same as defined above.

R ⁵ to R ⁴² and R' are each independently hydrogen; heavy hydrogen; halogen; nitro; C ₁ -C ₆₀ Alkyl group (straight chain, branched chain); C ₁ -C ₆₀ Alkoxy group; C ₆ -C ₆₀ Aryloxy; amino group; silyl group; C ₂ -C ₆₀ alkenyl group; C ₆ -C ₆₀ Aryl group; C ₂ -C ₆₀ A heteroaryl group; carbonyl group; ester group; nitrile group; sulfanyl group; sulfinyl group; sulfonyl group; phosphino group; It may be selected from the group consisting of; fluorenyl group.

In addition, ^{any two adjacent groups of R 5} to R ¹² , any two adjacent groups of R ¹³ to R ¹⁶ , any two adjacent groups of R ¹⁷ to R ²⁴ , or any of R ²⁷ to R ³⁰ Any two adjacent groups, any two adjacent groups of R ³⁹ to R ⁴² , and any two adjacent groups of a plurality of R′ may each be bonded to each other to form at least one ring. ^{At this time, R 5} to which do not form a ring R ⁴² and R' may be defined as defined above.

L is a C ₆ -C ₆₀ arylene group; C ₂ -C ₆₀ A heterocyclic group; It may be selected from the group consisting of; a fluorenylene group.

For example, when R ¹ to R ⁴² , R′ and L are an aryl group or an arylene group, R ¹ to R ⁴² , R′ and L are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, or It may be a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a phenanthrylene group.

Specifically, when ^{two adjacent groups of R 5} to R ¹² of Formula 2 combine with each other to form a ring, Formula 2 may be represented by one of the following Formulas, but is not limited thereto.

<Formula 2-1> <Formula 2-2> <Formula 2-3> <Formula 2-4>

<Formula 2-5> <Formula 2-6> <Formula 2-7> <Formula 2-8>

<Formula 2-9> <Formula 2-10> <Formula 2-11> <Formula 2-12>

<Formula 2-13> <Formula 2-14> <Formula 2-15> <Formula 2-16>

<Formula 2-17> <Formula 2-18>

In Formulas 2-1 to 2-18,

X, R ⁵ to R ¹² and L are the same as X, R ⁵ to R ¹² and L defined in Formulas 2 to 6 above.

Z ¹ to Z ²⁶ are each independently CR′ or N, R′ is the same as R′ as defined in Formulas 2 to 6, and when a plurality of R′ is present, a plurality of R′ is the same as or different from each other do.

Specifically, when ^{two adjacent groups of R 13} to R ¹⁶ of Formula 3 combine with each other to form a ring, Formula 3 may be represented by one of the following Formulas, but is not limited thereto.

<Formula 3-1> <Formula 3-2> <Formula 3-3> <Formula 3-4>

In Formulas 3-1 to 3-4,

R ¹³ to R ¹⁶ and L are the same as R ¹³ to R ¹⁶ and L defined in Formulas 2 to 6 above.

Y ⁵ to Y ²⁰ are the same ^{as Y 1} to Y ⁴ defined in Formulas 2 to 6 above.

Specifically, when ^{two adjacent groups of R 27} to R ³⁰ of Formula 5 combine with each other to form a ring, Formula 5 may be represented by one of the following Formulas, but is not limited thereto.

<Formula 5-1> <Formula 5-2> <Formula 5-3> <Formula 5-4>

In Formulas 5-1 to 5-4,

R ²⁵ to R ³⁰ and L are the same as R ²⁵ to R ³⁰ and L defined in Formulas 2 to 6 above.

Specifically, when ^{two adjacent groups of R 39} to R ⁴² in Formula 6 combine with each other to form a ring, Formula 6 may be represented by one of the following Formulas, but is not limited thereto.

<Formula 6-1> <Formula 6-2> <Formula 6-3> <Formula 6-4>

In Formulas 6-1 to 6-4,

R ³¹ to R ⁴² and L are the same as R ³¹ to R ⁴² and L defined in Formulas 2 to 6 above.

More specifically, the compound represented by Formula 1 may be any one of the following compounds, but is not limited thereto.

In another embodiment, the present invention provides a compound for an organic electric device represented by the formula (1).

In another embodiment, the present invention provides an organic electric device containing the compound represented by the formula (1).

At this time, the organic electric device includes a first electrode; a second electrode; and an organic material layer positioned between the first electrode and the second electrode, and the organic material layer may include a compound represented by Formula 1, wherein the compound represented by 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 of the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer. In particular, the compound represented by Formula 1 may be included in the emission layer.

That is, the compound represented by Formula 1 may be used as a material of the hole injection layer, the hole transport layer, the light emission auxiliary layer, the light emitting layer, the electron transport layer or the 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 material layer, and more specifically, the The individual formulas (1'-1 to 1'-42, 2'-1 to 2'-28, 3'-1 to 3'-29, 4'-1 to 4'-30 and 5'-1 in the organic layer) To 5'-24) provides an organic electric device comprising a compound represented.

In another embodiment, in at least one of the hole injection layer, the hole transport layer, the light emission 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 It provides an organic electric device characterized in that the compound is contained in a combination of two or more different compounds, or the compound is contained in a combination of two or more other compounds. In other words, each layer may contain a compound corresponding to Formula 1 alone, a mixture of two or more compounds of Formula 1 may be included, and the compound of claims 1 to 7 and a compound not corresponding to the present invention mixtures may be included. Here, the compound not falling under the present invention may be a single compound or may be two or more types of compounds. In this case, when the compound is contained in a combination of two or more other compounds, the other compound may be a known compound of each organic layer, or a compound to be developed in the future. In this case, the compound contained in the organic material layer may consist only of the same type of compound, or may be a mixture in which two or more heterogeneous compounds represented by Formula 1 are mixed.

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

Hereinafter, a synthesis example of the compound represented by Formula 1 and a manufacturing example of 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 compound (final products) represented by Formula 1 according to the present invention is represented by the following <Scheme 1> and <Scheme 2>, but is not limited thereto.

<Scheme 1> L-W and L-W' are A ring or B ring

<Scheme 2> L-W and L-W' are A ring or B ring

I. Sub 1 of Synthesis example

Sub 1 of Scheme 1 may be synthesized by the reaction routes of <Scheme 3> and <Scheme 4>, but is not limited thereto. In addition, Table 1 shows the FD-MS values of the compounds belonging to Sub 1.

<Scheme 3> Hal=F, Br, Cl, I, and L-W is A ring or B ring

<Scheme 4> Hal=F, Br, Cl, I, and L-W and L-W' are ring A or ring B

One. Sub 1-1 Synthesis

<Scheme 5>

In a round flask, put 9H-carbazole (9.2g, 55mmol) and t-BuOK (6.5 g, 57.75mmol), and add bis(4-fluorophenyl)methanone (6.0 g, 27.50mmol) to the mixture dissolved in DMF (84 mL) at 65℃. ) and stirred overnight. After cooling to room temperature, adding water, filtering, and washing with water. The obtained solid _{was dissolved in CH 2} Cl ₂ , the organic layer and the aqueous layer were separated, and MgSO ₄ was added to the organic layer and dried. The mixture was filtered and the resulting filtrate was concentrated. The obtained solid _{was recrystallized from CH 2} Cl ₂ and methanol to obtain 7.89 g (yield: 56%) of the product.

2. Sub 1-5 Synthesis

<Scheme 6>

intermediate Sub 1-I-5 synthesis

In a round flask, 9H-carbazole (5.98g, 35.79mmol), t-BuOK (4.42g, 39.37mmol), DMF (109mL), bis(4-fluorophenyl)methanone (7.81g, 35.79mmol) was added to the above Sub 1-1 Using the synthetic method, 7.71 g (yield: 42%) of the product was obtained.

Sub 1-5 Synthesis

In a round flask, 9-phenyl-9H,9'H-3,3'-bicarbazole (8.61g, 21.07mmol), t-BuOK (4.97g, 44.25mmol), DMF (64mL), Sub 1-I-5 ( 7.7 g, 21.07 mmol) was obtained by using the Sub 1-1 synthesis method to obtain 8.1 g (yield: 51%) of the product.

3. Sub 1-36 Synthesis

<Scheme 7>

intermediate Sub 1-I-36 synthesis

N-([1,1'-biphenyl]-4-yl)naphthalen-1-amine (17.33g, 58.66mmol), t-BuOK (7.24g, 64.53mmol), DMF (179 mL), bis in a round flask 12.16g (yield: 42%) of (4-fluorophenyl)methanone (12.8g, 58.66mmol) was obtained by using the Sub 1-1 synthesis method.

Sub 1-36 Synthesis

9,9-dimethyl-9,10-dihydroacridine (5.09g, 24.31mmol) in a round flask,

t-BuOK (3g, 26.74mmol), DMF (74mL), Sub 1-I-36 (12g, 24.31mmol) was obtained by using the above Sub 1-1 synthesis method to obtain 8.13g (yield: 49%) of the product.

4. Sub 1-52 Synthesis

<Scheme 8>

In a round flask, 5H-pyrido[4,3-b]indole (8.7g, 51.71mmol), t-BuOK (6.09g, 54.30mmol), DMF (79mL), bis(8-fluorodibenzo[b,d]furan- 3-yl)methanone (10.3g, 25.86mmol) was synthesized using the Sub 1-1 synthesis method to obtain 8.08g (yield: 45%) of the product.

5. Sub 1-55 Synthesis

<Scheme 9>

6-(quinazolin-2-yl)-9H-pyrido[2,3-b]indole (15.22g, 51.36mmol), t-BuOK (6.05g, 53.93mmol), DMF (78mL), bis( 4-fluorophenyl)methanone (5.6g, 25.68mmol) was obtained by using the Sub 1-1 synthesis method to obtain 8.12g (yield: 41%) of the product.

6. Sub 1-68 Synthesis

<Scheme 10>

Intermediate Sub 1-I-68 Synthesis

9H-pyrido[2,3-b]indole (6.63g, 39.41mmol), t-BuOK (4.86g, 43.35mmol), DMF (120mL), bis(4-fluorophenyl)methanone (8.6g, 39.41) in a round flask mmol) was obtained by using the above Sub 1-1 synthesis method to obtain 5.63 g (yield: 39%) of the product.

Sub 1-68 Synthesis

1,1,2,2,3,3,4,4-octamethyl-2,3,4,9-tetrahydro-1H-carbazole (8.43g, 29.75mmol), t-BuOK (3.67g, 32.72) in a round flask mmol), DMF (91 mL), and Sub 1-I-68 (10.9 g, 29.75 mmol) were obtained by using the above Sub 1-1 synthesis method to obtain 8.06 g (yield: 43%) of the product.

7. Sub 1-74 Synthesis

<Scheme 11>

N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (12.47g, 34.49mmol), t-BuOK (4.06g, 36.21mmol) in a round flask ), DMF (52mL), and bis(4-fluorophenyl)methanone (3.76g, 17.24mmol) were obtained using the Sub 1-1 synthesis method to obtain 8.08g (yield: 43%) of the product.

8. Sub 1-119 Synthesis

<Scheme 12>

In a round flask, 1H-indole (7.07g, 60.39mmol), t-BuOK (7.11g, 63.41mmol), DMF (92mL), (7-fluoro-9,9-dimethyl-9H-fluoren-2-yl)( 8.05 g (yield: 42%) of 7-fluorodibenzo[b,d]thiophen-3-yl)methanone (13.3g, 30.19mmol) was obtained by using the Sub 1-1 synthesis method.

9. Sub 1-128 Synthesis

<Scheme 13>

2,3,4,9-tetrahydro-1H-carbazole (8.50g, 49.64mmol), t-BuOK (5.85g, 52.12mmol), DMF (76mL), bis(6-fluoronaphthalen-2-yl) in a round flask 8.01 g (yield: 52%) of methanone (7.9 g, 24.82 mmol) was obtained by using the Sub 1-1 synthesis method.

10. Sub 1-136 Synthesis

<Scheme 14>

intermediate Sub 1-I-136 synthesis

1,1,2,2,3,3,4,4-octamethyl-2,3,4,9-tetrahydro-1H-carbazole (10.11g, 35.68mmol), t-BuOK (4.4g, 39.25) in a round flask mmol), DMF (109 mL), (4'-fluoro-[1,1'-biphenyl]-4-yl)(4-fluorophenyl)methanone (10.5g, 35.68mmol) was synthesized by the above Sub 1-1 synthesis method. was used to obtain 7.96 g (yield: 40%) of the product.

Sub 1-136 Synthesis

6-([1,1':3',1''-terphenyl]-5'-yl)-2,3,4,9-tetrahydro-1H-carbazole (6.73 g, 16.85 mmol), t -BuOK (2.08g, 18.54mmol), DMF (51mL), Sub 1-I-136 (9.4g, 16.85mmol) was obtained by using the above Sub 1-1 synthesis method to obtain 8.06g (yield: 51%) of the product. .

Sub 1 example

[Table 1]

II. Final Product Synthesis example

1. Synthesis of 1'-1

<Scheme 15>

THF (5mL) and diethyl (cyanomethyl)phosphonate (2.3g, 13.27mmol) were placed in a round-bottom flask, and a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 13.27 mL, 13.27 mmol) was slowly added at 0°C. . After stirring for 40 minutes, the solution was slowly added to a solution of Sub 1 (4 g, 7.8 mmol) in THF (12 mL). After stirring overnight, it was poured into water and extracted with t-BuOMe. The aqueous layer _{was extracted with CH 2} Cl ₂ , and the organic layer was dried _{over MgSO 4 .} The mixture was filtered and the resulting filtrate was concentrated. The obtained solid _{was recrystallized from CH 2} Cl ₂ and methanol to obtain 6.75 g (yield: 95%) of the product.

2. Synthesis of 1'-2

<Scheme 16>

Sub 1 (6g, 11.71mmol) and malononitrile (7.7g, 117.05mmol) were added to a round-bottom flask, dissolved in pyridine (110mL), and stirred at 90°C overnight. The reaction mixture was concentrated under reduced pressure _{, dissolved in CH 2} Cl ₂ , and extracted by adding water. After extraction, the organic layer and the aqueous layer were separated, and MgSO ₄ was added to the organic layer and dried. After drying, the mixture was filtered through silica gel and the filtrate was concentrated. The obtained solid _{was recrystallized from CH 2} Cl ₂ and methanol to obtain 5.91 g (yield: 90%) of the product.

3. Synthesis of 1'-6

<Scheme 17>

Sub 1-5 (6.6g, 8.75mmol), malononitrile (5.8g, 87.55mmol), and pyridine (81.8mL) in a round-bottom flask, 5.97g (yield: 85%) using the 1'-2 synthesis method got

4. Synthesis of 1'-37

<Scheme 18>

Sub 1-36 (6.9g, 10.10mmol), malononitrile (6.68g, 101.05mmol), and pyridine (91mL) in a round-bottom flask, using the above 1'-2 synthesis method, 6.06g (yield: 82%) of the product got it

5. Synthesis of 1'-42

<Scheme 19>

Sub 1-41 (7g, 11.75mmol), malononitrile (7.76g, 117.51mmol), and pyridine (105mL) in a round-bottom flask were used for the above 1'-2 synthesis method to obtain 6.05g (yield: 80%) of the product. .

6. Synthesis of 2'-12

<Scheme 20>

Sub 1-52 (7.2g, 10.38mmol), malononitrile (6.9g, 103.79mmol), and pyridine (97mL) in a round-bottom flask, using the above 1'-2 synthesis method, 6.01g (yield: 78%) of the product got it

7. Synthesis of 2'-15

<Scheme 21>

THF (5mL), diethyl (cyanomethyl)phosphonate (1.6g, 8.82mmol), lithium bis(trimethylsilyl)amide (1.0 M in THF, 8.82mL, 8.82mmol) solution was added to a round-bottom flask, and THF (12 mL) ) of Sub 1-55 (4g, 5.19mmol) was obtained by using the above 1'-1 synthesis method to obtain 6.23g (yield: 89%) of the product.

8. Synthesis of 2'-28

<Scheme 22>

Sub 1-68 (7.0g, 11.11mmol), malononitrile (7.34g, 111.14mmol), and pyridine (100mL) in a round-bottom flask, 6.10g (yield: 81%) of the product using the 1'-2 synthesis method got it

9. Synthesis of 3'-6

<Scheme 23>

THF (5mL), diethyl (cyanomethyl)phosphonate (1.3g, 7.55mmol), lithium bis(trimethylsilyl)amide (1.0 M in THF, 7.55mL, 7.55mmol) solution was added to a round-bottom flask, and THF (12 mL) ) of Sub 1-74 (4g, 4.44mmol) was obtained by using the above 1'-1 synthesis method to obtain 5.85g (yield: 84%) of the product.

10. Synthesis of 3'-29

<Scheme 24>

Sub 1-97 (6.3g, 9.77mmol), malononitrile (6.5g, 97.7mmol), and pyridine (91mL) in a round-bottom flask, 5.96g (yield: 88%) of the product using the 1'-2 synthesis method got it

11. Synthesis of 4'-22

<Scheme 25>

Sub 1-119 (7.2g, 11.34mmol), malononitrile (7.5g, 113.42mmol), and pyridine (106mL) in a round-bottom flask, 5.96g (yield: 77%) of the product using the 1'-2 synthesis method got it

12. Synthesis of 5'-3

<Scheme 26>

It was made by adding a solution of THF (5mL), diethyl (cyanomethyl)phosphonate (1.9g, 10.95mmol), lithium bis(trimethylsilyl)amide (1.0 M in THF, 10.95mL, 10.95mmol) to a round-bottom flask, and THF (12 mL) ) of Sub 1-128 (4g, 6.44mmol) was obtained by using the above 1'-1 synthesis method to obtain 6.14g (yield: 87%) of the product.

13. Synthesis of 5'-24

<Scheme 27>

Sub 1-136 (7.5g, 8mmol), malononitrile (5.3g, 80.02mmol), and pyridine (75mL) in a round-bottom flask were used for the above 1'-2 synthesis method to obtain 5.83g (yield: 74%) of the product. .

Meanwhile, the FD-MS values of the compounds 1'-1 to 5'-24 of the present invention prepared according to the above synthesis examples are shown in Table 2 below.

[Table 2]

Manufacturing evaluation of organic electric devices

[ Example 1] Manufacturing and testing of organic electroluminescent devices ( delayed fluorescence )

An organic electroluminescent device was manufactured according to a conventional method by using the compound obtained through synthesis as a dopant material for the emission layer. ^{First, N 1} -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino) as a hole injection layer on the ITO layer (anode) formed on the glass substrate. A phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form 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. 30 nm thick on the hole transport layer by vacuum-depositing 6 wt% of the invention compound 1'-1 and 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (mCP) on the hole transport layer of the light emitting layer was deposited. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, and an electron transport layer Tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm, and the Al/LiF was used as a cathode to manufacture an organic electroluminescent device.

[mCP]

[Example 2] to [Example 38]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that compounds 1'-2 to 5'-13 of the present invention described in Table 3 were used instead of compound 1'-1 of the present invention.

[ comparative example ]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound 1 was used instead of the compound 1'-1 of the present invention.

<Comparative compound 1>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples and Comparative Examples prepared as described above, electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, and as a result of the measurement, 500cd/m ² standard luminance T90 lifespan was measured using a life measuring device manufactured by McScience. Table 3 below shows the device fabrication and evaluation results.

[Table 3]

As can be seen from the results of Table 3, the organic light emitting device using the material for the organic light emitting device of the present invention as the light emitting layer material can significantly improve luminous efficiency, driving voltage and lifespan.

In other words, compared to Comparative Compound 1, which is a general fluorescent dopant in which two amine groups are substituted in the anthracene core, two donor units are connected in a cis type centering on a pi bond, and an invention compound containing at least one cyano group as an acceptor unit It can be seen that this low driving voltage, high efficiency, and long life are exhibited. In particular, the compound in which one cyano group and one hydrogen were substituted showed a blue shift pattern compared to the compound containing two cyano groups.

In addition, in the case of efficiency, as a bulky substituent such as tert-butyl is substituted with a secondary substituent of the compound of the present invention, the steric hindrance of molecules coagulating with each other is minimized to facilitate the movement of excitons between the host and the dopant, thereby increasing the efficiency. is judged to be

The Thermally Activated Delayed Fluorescence (TADF) material of the present invention, which can solve the problem of external quantum efficiency of conventional fluorescent materials like Comparative Compound 1, is an appropriate combination of an electron donor unit and an electron acceptor unit in a molecule. Because it forms an exciplex, it can be explained that it shows the result of high efficiency, long life and low driving voltage.

That is, this suggests that even with the same core, the energy level is changed depending on the substituent and the characteristics of the device itself can be significantly changed. In addition, although the device characteristics were described in terms of the light emitting layer in the evaluation results of the above-described device fabrication, materials typically used as the light emitting layer are organic electric devices such as the aforementioned electron transport layer, electron injection layer, hole injection layer, hole transport layer and light emitting auxiliary layer. It can be used alone or mixed with other materials as an organic layer of Therefore, for the above reasons, the compound of the present invention may be used singly or mixed with other materials in other organic layers other than the light emitting layer, for example, an electron transport layer, an electron injection layer, a hole injection layer, a hole transport layer and a light emission auxiliary layer.

The above description is merely illustrative of the present invention, and various modifications will be possible without departing from the essential characteristics of the present invention by those of ordinary skill in the art to which the present invention pertains. Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to 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 by the following claims, and all descriptions within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100: organic electric device 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
180: second electrode

Claims (13)

A delayed fluorescence compound represented by the following formula.
<Formula 1>

[In Formula 1,
R ¹ and R ² are each independently hydrogen; heavy hydrogen; C ₁ -C ₆₀ Alkyl group; C ₆ -C ₆₀ Aryl group; cyano group; selected from the group consisting of, at least one of ^{R 1} and R ^{2 is a cyano group,}
Ring A and ring B are represented by one of the following formulas,
<Formula 2><Formula3><Formula4>

<Formula 5><Formula6>

In Formulas 2 to 6,
X is O, S, CR ³ R ⁴ or a single bond,
Y ¹ to Y ⁴ are each independently CR' or N, at least one is N, and when a plurality of R' exist, a plurality of R' are the same or different from each other,
The R ³ and R ⁴ are i) independently of each other hydrogen; heavy hydrogen; C ₁ -C ₆₀ Alkyl group; C ₆ -C ₆₀ Aryl group; or selected from the group consisting of, or ii) R ³ and R ⁴ may be bonded to each other to form at least one ring (provided that R ³ and R ^{4 do not form a ring)} is the same as defined in i) above),
R ⁵ to R ⁴² and R' are i) independently of each other hydrogen; heavy hydrogen; halogen; nitro; C ₁ -C ₆₀ Alkyl group (straight chain, branched chain); C ₁ -C ₆₀ Alkoxy group; C ₆ -C ₆₀ Aryloxy; amino group; silyl group; C ₂ -C ₆₀ alkenyl group; C ₆ -C ₆₀ Aryl group; C ₂ -C ₆₀ A heteroaryl group; carbonyl group; ester group; nitrile group; sulfanyl group; sulfinyl group; sulfonyl group; phosphino group; fluorenyl group; or ii) ^{any two adjacent groups of R 5} to R ¹² , any two adjacent groups of R ¹³ to R ¹⁶ , and any of R ¹⁷ to R ²⁴ two adjacent groups, any two adjacent groups of R ²⁷ to R ³⁰ , any two adjacent groups of R ³⁹ to R ⁴² , and any two adjacent groups of a plurality of R' are bonded to each other, It can form at least one ring (provided that R ⁵ to which do not form a ring R ⁴² and R' are the same as defined in i) above),
L is a C ₆ -C ₆₀ arylene group; C ₂ -C ₆₀ A heterocyclic group; It is selected from the group consisting of; fluorenylene group;
Each of the aryl group, alkyl group, and cyano group is deuterium, halogen, silane group, siloxane group, boron group, germanium group, cyano group, nitro group, -L'-N(R _a )(R _b ) (wherein L' is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorenylene group; C ₃ ~ C ₆₀ An aliphatic ring and C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; And C ₂ ~ C ₆₀ Heterocyclic group ; is selected from the group consisting of, wherein R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; a fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ fusion of an aromatic ring _{A cyclic group; and a C 2} ~ C ₆₀ heterocyclic group comprising at least one heteroatom of O, N, S, Si and P; selected from the group consisting of); C ₁ ~ C ₂₀ coming of the alkylthio, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ alkynyl, C ₆ ~ C ₂₀ of the of 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, C ₆ ~ C ₂₀ aryl group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₈ ~ C ₂₀ arylalkenyl group, It may be substituted with one or more substituents selected from the group consisting of C ₇ ~ C ₂₀ arylalkoxyl group, or C ₂ ~ C _{20 alkoxylcarbonyl group).]} delete The method of claim 1,
When two adjacent groups of R ⁵ to R ¹² of Formula 2 combine with each other to form a ring, Formula 2 is a delayed fluorescence compound, characterized in that it is represented by the following Formula.
<Formula 2-1><Formula2-2><Formula2-3><Formula2-4>

<Formula 2-5><Formula2-6><Formula2-7><Formula2-8>

<Formula 2-9><Formula2-10><Formula2-11><Formula2-12>

<Formula 2-13><Formula2-14><Formula2-15><Formula2-16>

<Formula 2-17><Formula2-18>

[In Formulas 2-1 to 2-18,
wherein X, R ⁵ to R ¹² and L is the same as defined in Formulas 2 to 6,
Z ¹ to Z ²⁶ are each independently CR′ or N, R′ is the same as defined in Formulas 2 to 6, and when a plurality of R′ is present, a plurality of R′ are the same or different from each other.] The method of claim 1,
Two adjacent groups of R ¹³ to R ¹⁶ in Formula 3 are bonded to each other, When a ring is formed, Chemical Formula 3 is a delayed fluorescence compound, characterized in that it is represented by the following Chemical Formula.
<Formula 3-1><Formula3-2><Formula3-3><Formula3-4>

(In Formulas 3-1 to 3-4,
wherein R ¹³ to R ¹⁶ and L is the same as defined in Formulas 2 to 6, and Y ⁵ to Y ²⁰ are the same as ^{Y 1} to Y ⁴ defined in Formulas 2 to 6) The method of claim 1,
When two adjacent groups of R ²⁷ to R ³⁰ of Formula 5 combine with each other to form a ring, Formula 5 is a delayed fluorescence compound, characterized in that it is represented by the following Formula.
<Formula 5-1><Formula5-2><Formula5-3><Formula5-4>

(In Formulas 5-1 to 5-4,
wherein R ²⁵ to R ³⁰ and L are the same as defined in Formulas 2 to 6) The method of claim 1,
When two adjacent groups of R ³⁹ to R ⁴² of Formula 6 combine with each other to form a ring, Formula 6 is a delayed fluorescence compound, characterized in that it is represented by the following Formula.
<Formula 6-1><Formula6-2><Formula6-3><Formula6-4>

(In Formulas 6-1 to 6-4,
wherein R ³¹ to R ⁴² and L are the same as defined in Formulas 2 to 6) The method of claim 1,
Delayed fluorescence compound, characterized in that one of the following compounds.

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,
The light emitting layer is an organic electric device, characterized in that it contains the delayed fluorescence compound according to any one of claims 1 and 3 to 7. 9. The method of claim 8,
The delayed fluorescence compound contained in the light emitting layer is an organic electric device, characterized in that used in a mixture of two or more heterogeneous compounds represented by the formula (1). 9. The method of claim 8,
The organic electric device further comprising a light efficiency improving layer formed on at least one surface opposite to the organic material layer of one surface of the first electrode and the second electrode. 9. The method of claim 8,
The organic material layer is an organic electric device, characterized in that 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 device of claim 8; and
An electronic device comprising a; a control unit for driving the display device. 13. The method of claim 12,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an electronic device, characterized in that one of a single color or white lighting device.

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