KR20210153439A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; and an electronic device including the organic electric element. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered, and luminous efficiency and lifespan of the organic electric element can be improved.

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.

Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, 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.

In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer should exist between the hole transport layer and the light emitting layer, and different light emitting auxiliary layers according to each light emitting layer (R, G, B). development is required.

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

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

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 embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan of the device can be greatly improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of the present invention.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise specified in the present specification, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

As used herein, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and as used in the present invention, the fluorenyl group or The fluorenylene group includes cases in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.

"Substituted fluorenyl group", "substituted fluorenylene group" means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, and the like may all be referred to as a fluorene group.

As used herein, the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like. _{In addition, a compound including a heteroatom group such as SO 2} , P=O, etc., such as the following compound instead of carbon forming a ring, may also be included in the heterocyclic group.

The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a single ring type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.

In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine' or as the 'name of the group' of the valence, such as a pyrimidinyl group in the case of monovalent or pyrimidinylene in the case of divalent. have.

In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless there is an explicit explanation, the formula used in the present invention applies 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 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring. It can be omitted and the chemical formula or compound can be described. In addition, 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, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same as or different from each other.

In addition, unless otherwise specified in the present specification, when representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.

In addition, unless otherwise specified in the present specification, when a ring is expressed in the form of a 'numeric atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.

In addition, unless otherwise stated in the present specification, the ring formed by bonding adjacent groups to each other is a C ₆ ~ C ₆₀ aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ An aliphatic ring group; may be selected from the group consisting of. For example, when adjacent groups are bonded to each other to form an aromatic ring, the aromatic ring may be benzene, naphthalene, phenanthrene, or the like.

At this time, unless otherwise explained in the present specification, 'neighboring groups' refers to each other when describing the following chemical formula as an example, R ₁ and R _{2 each other} , R ₂ and R _{3 each other} , R ₃ and R _{4 each other} , It includes _{not only R 5} and R ₆ , but also R ₇ and R ₈ that share one carbon, R ₁ and R ₇ , R ₁ and R _{8 ,} or R ₄ and R _{5 that} are not immediately adjacent Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included. That is, if there is a substituent on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.

In the following formula, _{when substituents bonded to the same carbon as R 7} and R ₈ combine with each other to form a ring, a compound including a spiro moiety may be formed.

,

,

In addition, in the present specification, the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.

Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .

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 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 elements from other elements, and the essence, order, or order of the elements 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 also be “connected,” “coupled,” or “connected.”

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

1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). ) and an organic material layer formed between the second electrode 170 .

The first electrode 110 may be an anode (anode), the second electrode 170 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 include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 . Specifically, the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .

Preferably, the light efficiency improving layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 that is not in contact with the organic material layer, and when the light efficiency improving layer 180 is formed Light efficiency of the organic electric device may be improved.

For example, the light efficiency improving layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the light efficiency improving layer 180 is formed to form the second electrode 170 . ) can reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.

A buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .

2, the organic electric device 200 according to another embodiment of the present invention is a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode. can be

Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .

In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .

Referring to FIG. 3 , in the organic electric device 300 according to another embodiment of the present invention, there are two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.

Specifically, in the organic electric device according to an embodiment of the present invention, a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , and a second electrode 170 and the light efficiency improving layer 180 may be included.

The first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 . . As described above, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.

A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 . The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 . The charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and to smoothly distribute charges.

The first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.

In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .

When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3, an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.

The compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer 210, a light emitting auxiliary layer 220, an electron transport layer (150, 350) , 450), the electron injection layer 160, the light emitting layers 140, 340, 440, or the light efficiency improving layer 180 may be used as a material, preferably, the light emitting auxiliary layer 220 and / or the light efficiency improving layer 180 ) can be used as a material for

A study on the selection of a core and a combination of sub-substituents bonded thereto because the band gap, electrical properties, and interfacial properties, etc. may vary depending on which position and which substituent is bonded even for the same and similar core _{In particular, long lifespan and high efficiency can be achieved at the same time when the energy level and T 1} value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.

Therefore, in the present invention, by using the compound represented by Chemical Formula 1 as a material for the light emitting auxiliary layer 220 and/or the light efficiency improving layer 180 , the energy level and T ₁ value between each organic material layer, and the intrinsic properties of the material (mobility) , interface characteristics, etc.) can be optimized to simultaneously improve the lifespan and efficiency of the organic electric device.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have. In addition, an auxiliary light emitting layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.

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 an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on a material used.

In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.

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).

<Formula 1>

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

X is O, S or N(-L ¹ -Ar ¹ ).

L is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

Ar is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; And C ₆ ~ C ₆₀ Aromatic ring and C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring group.

n is an integer of 2 or 3, when n is 2 or 3, each of a plurality of L is the same as or different from each other, and a plurality of Y ₁ to a plurality of Y ₁₆ are the same as or different from each other, respectively.

Y ₁ to Y ₁₆ are each independently N or C(R ¹ ).

wherein R ¹ is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and C ₃ ~ C _{60 aliphatic ring group;} C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); and adjacent groups may combine with each other to form a ring, with the proviso that when n is 2, two sets of Y ₁ -Y _{In 16} , when n is 3, in the three sets of Y ₁ -Y ₁₆ , at least one pair of neighboring R ^{1 in} each set bonds to each other to form a ring.

Therefore, when n is 2, since two spiro moieties in which the condensed ring containing X and the fluorene form are fused are substituted for the nitrogen of the amino group, at least one pair of neighboring R ¹ for each spiro moiety is bonded to each other. A substituent is bonded to, and when n is 3, three substituents are substituted at the nitrogen of the amino group by a fused spiro substituent.

A ring formed by bonding adjacent R ^{1 to} each other is a C ₆ ~ C ₆₀ aromatic ring; fluorene; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ Heterocycle; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring. For example, when adjacent groups are bonded to each other to form an aromatic ring, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₀ , C ₆ ~ C ₁₆ , C ₆ ~ C ₁₄ , C ₆ ~ C ₁₀ , C _{6 ,} etc. An aromatic ring may be formed, and specifically, an aromatic ring such as benzene, naphthalene, or phenanthrene may be formed.

The Ar ¹ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b );

The L ¹ and L' are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group.

When at least one of Ar, Ar ¹ , R ¹ , R _a , and R _b is an aryl group, the aryl group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~ It _{may be an aryl group such as C 10} , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, or the like.

The L, L ¹ And when at least one of L' is an arylene group, the arylene group, for example, C ₆ ~ C ₃₀ , C ₆ ~ C ₂₉ , C ₆ ~ C ₂₈ , C ₆ ~ C ₂₇ , C ₆ ~ C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , It _{may be an arylene group such as C 12} , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, and the like.

The Ar, Ar ¹ , R ¹ , R _a , R _b , L, L ¹ And when at least one of L' is a heterocyclic group, the heterocycle is, for example, C ₂ ~ C ₃₀ , C ₂ ~ C ₂₉ , C ₂ ~ C ₂₈ , C ₂ ~ C ₂₇ , C ₂ ~ C ₂₆ , C ₂ ~C ₂₅ , C ₂ ~C ₂₄ , C ₂ ~C ₂₃ , C ₂ ~C ₂₂ , C ₂ ~C ₂₁ , C ₂ ~C ₂₀ , C ₂ ~C ₁₉ , C ₂ ~C ₁₈ , C ₂ ~C ₁₇ , C ₂ ~C ₁₆ , C ₂ ~C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , C ₁₁ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ , C ₂₃ , C ₂₄ , C ₂₅ , C ₂₆ , C ₂₇ , C ₂₈ , _{may be a heterocyclic group such as C 29} , and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene , indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline , benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, phenanthrobenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenan Trobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, Benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, ben Zosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl- 9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], and the like.

At least one of Ar, Ar ¹ , R ¹ , R _a , R _b is a fluorenyl group, or L, L ¹ And when at least one of L' is a fluorenylene group, the fluorenyl group or the fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9' - as a by-fluorene, spy spy [benzo [b] fluorene -11,9'- fluorene], benzo [b] fluorene, diphenyl-11,11- -11 H-benzo [b] fluorene, 9- (naphthalen-2-yl) phenyl--9 H - may be a fluorene.

When at least one of Ar, Ar ¹ , R ¹ , R _a , and R _b is an aliphatic cyclic group, the aliphatic cyclic group is, for example, C ₆ to C ₃₀ , C ₆ to C ₂₉ , C ₆ to C ₂₈ , C ₆ to C ₂₇ , C ₆ ~C ₂₆ , C ₆ ~C ₂₅ , C ₆ ~C ₂₄ , C ₆ ~C ₂₃ , C ₆ ~C ₂₂ , C ₆ ~C ₂₁ , C ₆ ~C ₂₀ , C ₆ ~C ₁₉ , C ₆ ~C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ to C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ may be an aliphatic group.

When ^{at least one of Ar 1} and R ¹ is an alkyl group, the alkylyl group is, for example, C ₁ ~C ₂₀ , C ₁ ~C ₁₀ , C ₁ ~C ₄ , C ₁ , C ₂ , C ₃ , C _{4 ,} etc. It may be an alkylyl group of

When R ¹ is an alkenyl group, the alkenyl group may be, for example, an alkenyl group such as C ₂ to C ₂₀ , C ₂ to C ₁₀ , C ₂ to C ₄ , C ₂ , C ₃ , C ₄ .

The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ An arylthio 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; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ) may be substituted with one or more substituents selected from the group consisting of. Here, L', R _a and R _b are as defined above.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an aryl group, the aryl group is, for example, C ₆ ~ C ₂₀ , C ₆ ~ C ₁₉ , C ₆ ~ C ₁₈ , C ₆ ~ C ₁₇ , C ₆ ~ C ₁₆ , C ₆ ~ C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , It may be an aryl group such as _{C 17} or C _{18 .}

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a heterocyclic group, the heterocyclic group is, for example, C ₂ ~ C ₂₀ , C ₂ ~ C ₁₉ , C ₂ ~ C ₁₈ , C ₂ ~ C ₁₇ , C ₂ ~ C ₁₆ , C ₂ ~ C ₁₅ , C ₂ ~C ₁₄ , C ₂ ~C ₁₃ , C ₂ ~C ₁₂ , C ₂ ~C ₁₁ , C ₂ ~C ₁₀ , C ₂ ~C ₉ , C ₂ ~C ₈ , C ₂ ~C ₇ , C ₂ ~C ₆ , C ₂ ~C ₅ , C ₂ ~C ₄ , C ₂ ~C ₃ , C ₂ , C ₃ , C ₄ , C ₅ , C ₆ , C ₇ , C ₈ , C ₉ , C ₁₀ , It may be a heterocyclic group such as _{C 11} , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C _{20 .}

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with -L'-N(R _a )(R _b ), L' is, for example, C ₆ -C ₂₀ , C ₆ -C ₁₉ , C ₆ -C ₁₈ , C ₆ -C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , It may be an arylene group such as _{C 13} , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C _{18 , and R a} and R _b are, for example, C ₆ -C ₂₀ , C ₆ -C ₁₉ , C ₆ -C ₁₈ , C ₆ ~C ₁₇ , C ₆ ~C ₁₆ , C ₆ ~C ₁₅ , C ₆ ~C ₁₄ , C ₆ ~C ₁₃ , C ₆ ~C ₁₂ , C ₆ ~C ₁₁ , C ₆ ~C ₁₀ , C ₆ , C ₁₀ , C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ may be an aryl group.

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkenyl group, the alkenyl group may be, for example, an alkenyl group such as C ₂ to C ₂₀ , C ₂ to C ₁₀ , C ₂ to C ₄ , C ₂ , C ₃ , C ₄ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkoxyl group, the alkoxyl group may be, for example, an alkoxyl group such as C ₁ -C ₂₀ , C ₁ -C ₁₀ , C ₁ -C ₄ .

Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene , spiro [benzo [ b ] fluorene-11,9'-fluorene], benzo [ b ] fluorene, 11,11-diphenyl-11 H -benzo [ b ] fluorene, 9- (naphthalene-2) - it may be a fluorene-yl) -9 H 9-phenyl.

Formula 1 may be represented by Formula 2 or Formula 3 below.

<Formula 2>

<Formula 3>

In Formulas 2 and 3, X, Y ₁ to Y ₁₆ , L and Ar are as defined in Formula 1.

In addition, Chemical Formula 1 may be represented by Chemical Formula 4 below.

<Formula 4>

In Formula 4, X, L and Ar are as defined in Formula 1, a to d are each an integer of 0 to 2, at least one of a and b is an integer of 1 or more, and at least one of c and d is An integer greater than or equal to 1.

Formula 4 may be represented by Formula 5 or Formula 6 below.

<Formula 5>

<Formula 6>

In Formulas 5 and 6, X, L, Ar, and a to d are as defined in Formula 4.

In addition, Chemical Formula 1 may be represented by one of Chemical Formulas 7 to 10 below.

<Formula 7> <Formula 8>

<Formula 9> <Formula 10>

In Formulas 7 to 10, X, L and Ar are as defined in Formula 1.

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

.

.

In another aspect of the present invention, the present invention provides an organic electric device including an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.

In another aspect of the present invention, the present invention provides an organic electric device comprising an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improving layer. In this case, the light efficiency improving layer is formed on one side not in contact with the organic material layer among both surfaces of the anode or the cathode, and the organic material layer or the light efficiency improving layer includes the compound represented by Formula 1 above.

The organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound may be included in the light emission auxiliary layer.

The organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generating layer formed between the two or more stacks.

In another aspect of the present invention, there is provided an electronic device including a display device including the organic electric device represented by Formula 1, and a control unit for driving the display device.

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

[ Synthesis Example 1 ]

The compound represented by Formula 1 according to the present invention may be synthesized as shown in Scheme 1 below, but is not limited thereto.

In Chemical Formula 1 of the present invention, when n=3, Ar is the same as the synthesis route when n=2, except that it has a structure of Sub 2 below.

<Scheme 1> (Hal is I, Br or Cl)

Synthesis example of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

1. of Sub 1-7 Synthesis example

Synthesis of Sub 1-7-a

THF (401 ml) was added to 1-bromo-2-phenoxybenzene (30 g, 120.4 mmol), and 2.5M n-BuLi (7.7 ml, 120.4 mmol) was slowly added at -78°C and stirred at -78°C for 1 hour. do. 3-chloro-11H-benzo[b]fluoren-11-one (31.8 g, 120.4 mmol) dissolved in THF was added at -78°C and slowly raised to room temperature. When the reaction is complete, _{quenching is performed using NH 4} Cl and the solvent is removed. Then, acetic acid (AcOH) (280 ml) and HCl (60 ml) were added and stirred at 80° C. for 5 hours. When the reaction was completed, the temperature was cooled to room temperature, filtered, extracted with methyl chloride, and then washed with water. Thereafter, the organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated by a silica gel column to obtain a product Sub 1-7-a43.4 g (86.4%).

Synthesis of Sub 1-7

After dissolving Sub 1-7-a (43.4 g, 104.1 mmol) in toluene (1067 ml), Sub 1-7-b (43.4 g, 109.3 mmol), Pd ₂ (dba) ₃ (0.03 equivalent), P(t) -Bu) ₃ (0.06 equiv) and NaOt-Bu (3 equiv) were added and stirred at 100°C. Upon completion of the reaction _{, the mixture was extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 1-767.8 g (yield: 84.3%) of the product.

2. Sub 1-16 Synthesis example

Sub 1-16-a (28 g, 67.2 mmol) to Sub 1-16-b (28 g, 70.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO t After -Bu (3 equivalents) and Toluene (688ml) were added, the same method as the Sub 1-7 synthesis method was followed to obtain 42.9 g of a product (yield: 82.1%).

3. Sub 1-20 of Synthesis example

Sub 1-20-a (25 g, 50.1 mmol) to Sub 1-20-b (20.9 g, 52.6 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO After the addition of t- Bu (3 equivalents) and Toluene (513ml), the same method as in the Sub 1-7 synthesis method was followed to obtain 34.1 g of a product (yield: 79.1%).

4. of Sub 1-34 Synthesis example

Sub 1-34-a (27 g, 62.4 mmol) to Sub 1-34-b (26 g, 65.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (639ml) were added, followed by the same method as the Sub 1-7 synthesis method to obtain 41.4 g (yield: 83.6%) of the product.

5.Sub 1-41's Synthesis example

Sub 1-41-a (19 g, 38.5 mmol) to Sub 1-41-b (16.7 g, 40.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO After adding t- Bu (3 equivalents) and Toluene (395ml), the same method as in the Sub 1-7 synthesis method was followed to obtain 23.4 g (yield: 69.8%) of the product.

6.Sub 1-61's Synthesis example

Sub 1-61-a (21 g, 41.3 mmol) to Sub 1-61-b (17.9 g, 43.3 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO After the addition of t- Bu (3 equivalents) and Toluene (423ml), the same method as for the synthesis of Sub 1-7 was performed to obtain 26.9 g of a product (yield: 73.7%).

The compound belonging to Sub 1 may be a compound as follows, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 1 below.

[Table 1]

Exemplary compounds of Sub 2

The compound belonging to Sub 2 of Scheme 1 may be a compound as follows, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds are shown in Table 2 below.

[Table 2]

of the final compound Synthesis example

1. Synthesis of P-6

Sub 1-6 (27 g, 34.7 mmol) to Sub 2-1 (4.1 g, 36.4 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu ( 3 equivalents) and Toluene (356ml) were added and stirred at 100°C. Upon completion of the reaction _{, the mixture was extracted with CH 2} Cl ₂ and water, and the organic layer was dried over _{MgSO 4 and concentrated.} Then, the concentrate was passed through a silica gel column and recrystallized to obtain 23.7 g of a product (yield: 80%).

2. Synthesis of P-23

Sub 1-63 (23 g, 29.8 mmol) to Sub 2-2 (5.9 g, 31.2 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu ( 3 equivalents) and toluene (305 ml) were added, and the same method as in the synthesis of P-6 was followed to obtain 23.5 g (yield: 84.8%) of the product.

3. Synthesis of P-32

Sub 1-2 (25 g, 32.1 mmol) to Sub 2-11 (6.8 g, 33.7 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO t- Bu ( 3 equivalents) and Toluene (329ml) were added, and then, the same method as in the synthesis of P-6 was followed to obtain 23 g (yield: 75.9%) of the product.

4. Synthesis of P-39

Sub 1-27 (23 g, 28.4 mmol) to Sub 2-16 (8.3 g, 29.8 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu ( 3 equivalents) and toluene (291 ml) were added, and the same method was followed for the synthesis of P-6 to obtain 21.6 g (yield: 72.3%) of the product.

5. Synthesis of P-53

Sub 1-37 (19 g, 22.3 mmol) to Sub 2-22 (3.7 g, 22.6 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu ( 3 equivalents) and Toluene (228ml) were added, and the same method was followed for the synthesis of P-6 to obtain 19.8 g (yield: 78.1%) of the product.

6. Synthesis of P-60

Sub 1-42 (20 g, 21.5 mmol) to Sub 2-4 (3.7 g, 22.6 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t- Bu) ₃ (0.06 equiv), NaO t- Bu ( 3 equivalents) and Toluene (221ml) were added, and the same method as in the synthesis of P-6 was followed to obtain 17.6 g (yield: 77.6%) of the product.

7. Synthesis of P-82

Sub 1-7 (22 g, 28.3 mmol) to Sub 2-51 (12.4 g, 29.7 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu ( 3 equivalents) and Toluene (290 ml) were added, and the same method was followed for the synthesis of P-6 to obtain 25 g of a product (yield: 76.3%).

8. Synthesis of P-97

Sub 1-61 (19 g, 21.4 mmol) to Sub 2-62 (11 g, 22.5 mmol), Pd ₂ (dba) ₃ (0.03 equiv) P( t -Bu) ₃ (0.06 equiv), NaO t -Bu (3 equivalent) and toluene (220 ml) were added, and the same method as in the synthesis of P-6 was followed to obtain 21.1 g of a product (yield: 73.4%).

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

[Table 3]

Manufacturing and evaluation of organic electric devices

[ Example 1 ] Green organic electroluminescent device ( light emitting layer )

4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a 60 nm-thick hole injection layer Then, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was After vacuum deposition to form a hole transport layer having a thickness of 60 nm, the compound P-3 of the present invention was vacuum deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.

Next, on the light emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as "CBP") as a host material and tris(2-phenylpyridine)-iridium (hereinafter, "Ir(ppy) ₃ ) was used, but the host and dopant were doped with a dopant in a weight ratio of 95:5 to form a light emitting layer with a thickness of 30 nm on the hole transport layer.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as 'BAlq') was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter _{abbreviated as Alq 3} ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.

Then, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 24]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-3 of the present invention as a light emitting auxiliary layer material.

[ comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light-emitting auxiliary layer was not formed.

[ comparative example 2] to [ comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following Comparative Compounds 1 to 3 were used instead of the compound P-3 of the present invention as the light emitting auxiliary layer material.

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 24 and Comparative Examples 1 to 4 of the present invention, the electroluminescence (EL) characteristics were obtained with PR-650 of Photoresearch. It was measured, and the T95 lifespan was measured using the life measuring equipment of McScience at 5000cd ^{/m 2 standard luminance.} The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, when the compound of the present invention is used as a material for the light-emitting auxiliary layer, the light-emitting auxiliary layer is not formed (Comparative Example 1), Comparative Compound 1 (Comparative Example 2), Comparative Compound 2 (Comparative Example) 3) or Comparative Compound 3 (Comparative Example 4) can lower the driving voltage of the organic light emitting device compared to the case of using the light emitting auxiliary layer material, and the luminous efficiency and lifespan are significantly improved.

In Comparative Examples 2 to 4, compared to Comparative Example 1, it can be seen that the device characteristics are improved when the light emitting auxiliary layer is formed, as the device characteristics are improved. In addition, compared to Comparative Examples 2 to 4, when the compound according to Formula 1 of the present invention was used as a material for the light emitting auxiliary layer, device characteristics were remarkably improved.

In the compound of the present invention (when X=O), in two or three sets of Y1-Y16, at least one pair of neighboring R1 in each set bonds with each other to form a ring, for example, benzofluorene or dibenzoflu A spiro compound (hereinafter referred to as a fused spiro substituent) in which a fluorene moiety and a xanthene moiety are fused to one more benzene ring, such as orene, is a form in which two or three are bonded to the nitrogen of the amino group.

On the other hand, Comparative Compounds 1 to 3 are fused-type spiro compounds in that at least one spiro compound (hereinafter referred to as a simple spiro substituent) in which a simple fluorene moiety and a xante moiety are fused to the nitrogen of the amino group is substituted. It is different from the present invention in which only a substituent is substituted.

In the case of Comparative Compounds 2 and 3, compared to Comparative Compound 1, it is seen that the device characteristics are improved, and when at least one of the simple spiro substituents is substituted with an amino group, the device characteristics are excellent, It can be seen that when three of the substituents are substituted with two, the characteristics of the device are excellent.

When a compound in which at least two fusion spiro substituents are substituted with nitrogen of an amino group, like the compound of the present invention, is used as a light emitting auxiliary layer material, it is considered that the device has the best characteristics, so at least two fusion spiro substituents are substituted with amino groups In this case, it is expected to have more suitable physical properties (HOMO, UMO, T1, etc.) as a light-emitting auxiliary layer material, particularly a green light-emitting auxiliary layer material. As a result, it seems that the driving voltage, efficiency, and lifespan of the device are improved by acting as a major factor in device performance improvement (charge balance between holes and electrons, electron mobility and charge mobility, etc.) in the device deposition process.

In addition, looking at the device results of Examples 1 to 24 of the present invention, it can be seen that the device results vary depending on the substitution position of the fusion spiro substituent bonded to the N of the amino group. That is, in the fused ring moiety (xanthene moiety, thioxanthene moiety, acridine moiety) containing X rather than a structure connected to the nitrogen of the amino group in the fluorene moiety of the fused spiro substituent, it is linked to the nitrogen of the amino group. When the compound of the structure used as the light emitting auxiliary layer material was used, the device characteristics were excellent. This means that when a substituent is substituted with a fused spiro on the nitrogen of the amino group, it is connected to the nitrogen of the amino group in the condensed ring moiety (xanthene moiety, thioxanthene moiety, acridine moiety) including X. It suggests that it has more suitable physical properties for use as a material.

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

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (14)

A compound represented by the following formula (1):
<Formula 1>

In Formula 1,
X is O, S or N(-L ¹ -Ar ¹ ),
L is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
Ar is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; And C ₆ ~ C ₆₀ Aromatic ring and C ₃ ~ C _{60 It} is selected from the group consisting of a fused ring group of an aliphatic ring group,
n is an integer of 2 or 3, when n is 2 or 3, each of a plurality of L is the same as or different from each other, and a plurality of Y ₁ to a plurality of Y ₁₆ are each the same as or different from each other,
Y ₁ to Y ₁₆ are each independently N or C(R ¹ ),
wherein R ¹ is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₆ ~ C ₆₀ A fused ring group of an aromatic ring and C ₃ ~ C _{60 aliphatic ring group;} C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L'-N(R _a )(R _b ); and adjacent groups may combine with each other to form a ring, with the proviso that when n is 2, two sets of Y ₁ -Y _{In 16} , when n is 3, in three sets of Y ₁ -Y ₁₆ , at least one pair of neighboring R ^{1 in} each set binds to each other to form a ring,
The Ar ¹ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ An aliphatic group; C ₁ ~ C ₃₀ Alkyl group; C ₂ ~ C ₃₀ Alkenyl group; C ₂ ~ C ₃₀ Alkynyl group; C ₁ ~ C ₃₀ An alkoxyl group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b );
The L ¹ and L' are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic cyclic group,
The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, and a ring formed by bonding adjacent groups to each other deuterium, respectively; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} siloxane group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₆ -C ₂₀ Aryloxy group; C ₆ -C ₂₀ Arylthio 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; fluorenyl group; _{C 2} -C ₂₀ A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ) may be substituted with one or more substituents selected from the group consisting of. The method of claim 1,
Formula 1 is a compound represented by Formula 2 or Formula 3 below:
<Formula 2>

<Formula 3>

In Formulas 2 and 3, X, Y ₁ to Y ₁₆ , L and Ar are as defined in claim 1. The method of claim 1,
Formula 1 is a compound, characterized in that represented by the following formula 4:
<Formula 4>

In Formula 4, X, L and Ar are as defined in claim 1, a to d are each an integer of 0 to 2, at least one of a and b is an integer of 1 or more, and at least one of c and d is an integer greater than or equal to 1. 4. The method of claim 3,
Formula 4 is a compound, characterized in that represented by Formula 5 or Formula 6:
<Formula 5>

<Formula 6>

In Formulas 5 and 6, X, L, Ar, and a to d are as defined in claim 3. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas 7 to 10:
<Formula 7><Formula8>

<Formula 9><Formula10>

In Formulas 7 to 10, X, L and Ar are as defined in claim 1. The method of claim 1,
The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:

. An organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is an organic electric device comprising a compound represented by the formula (1) of claim 1. In the organic electric device comprising a first electrode, a second electrode, and an organic material layer and a light efficiency improving layer formed between the first electrode and the second electrode,
The light efficiency improving layer is formed on one surface of both surfaces of the first electrode and the second electrode that is not in contact with the organic material layer,
The organic material layer or the light efficiency improving layer is an organic electric device comprising a compound represented by the formula (1) of claim 1. 9. The method according to claim 7 or 8,
The organic material layer is an organic electric device comprising at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. 10. The method of claim 9,
The compound is an organic electric device, characterized in that included in the light emitting auxiliary layer. 9. The method according to claim 7 or 8,
The organic material layer comprises at least two stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode. 12. The method of claim 11,
The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks. A display device comprising the organic electric device of claim 7 or 8; and
An electronic device comprising a; a control unit for driving the display device. 14. The method of claim 13,
The organic electric device is an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, an electronic device, characterized in that selected from the group consisting of a single color lighting device and a quantum dot display device.

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