KR102344798B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides an organic electric device comprising a compound represented by Formula 1, 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 device do. By including the compound represented by Chemical Formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, and luminous efficiency and lifespan 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.

A material used as an organic layer in an organic electric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function. In addition, the light emitting material can be classified into a high molecular type and a low molecular type according to the molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to the light emission mechanism. have. In addition, the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color according to the emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength shifts to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is decreased due to the emission attenuation effect. A host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through the The principle is that when a small amount of a dopant having a smaller energy band gap than that of the host forming the emission layer is mixed in the emission layer, excitons generated in the emission layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is a large-area display, and the size thereof is increasing, so that power consumption greater than the power consumption required for the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and the problem of efficiency and lifespan must also 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 T ₁ value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time. .

Therefore, it is necessary to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer, and in particular, it is necessary to develop a host material for the light emitting layer.

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 is an exemplary view of an organic electroluminescent device according to 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 includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.

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, the heterocyclic ring used in the present invention may include a compound including a heteroatom group such as _{SO 2 , P=O, etc., such as the following compound instead of carbon forming a ring.}

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to It includes the case of forming a compound as a spy together.

The term "spiro compound" used in the present invention has a 'spiro union', and the spiro linkage means a connection formed by sharing only one atom in 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.

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, pyrimidinylene in the case of divalent. have.

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 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; C ₃ ~ C ₆₀ An aliphatic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} And it may be selected from the group consisting of combinations thereof.

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

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.

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 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 an embodiment of the present invention includes a first electrode 120 , a second electrode 180 , and a first electrode 120 formed on a substrate 110 , and An organic material layer including the compound according to the present invention is included between the second electrodes 180 . 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 include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , an electron injection layer 170 , etc. sequentially stacked on the first electrode 120 . . At this time, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, etc., and the electron transport layer 160, etc. It may also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or on a surface of both surfaces of the second electrode that does not contact the organic material layer.

The compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), a host or dopant of the emission layer 150, or a material of the light efficiency improving layer. Preferably, the compound according to Formula 1 of the present invention may be used as a host of the light emitting layer.

On the other hand, even with the same and similar 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 sub-substituents coupled thereto In particular, 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, long lifespan and high efficiency can be achieved at the same time.

Therefore, in the present invention, by using the compound represented by Formula 1 as a host for the light emitting layer, the energy level and T ₁ value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, 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 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 120, and the hole injection layer 130 thereon. , after forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon. have. In addition, an auxiliary light emitting layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150 , and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160 .

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.

Y ₁ to Y ₄ are each independently N or CL ₁ -Ar ₁ , _{at least two of Y 1} to Y ₄ are N, a plurality of L ₁ are the same or different from each other, and a plurality of Ar ₁ are the same or different from each other. do. Accordingly, the hexagonal _{ring including Y 1} to Y ₄ may be a derivative such as pyrimidine, pyrazine, pyridazine, or triazine.

X ₁ is NL ₂ -Ar ₂ , O or S.

X ₂ and X ₃ are each independently a single bond, NL ₃ -Ar ₃ , O or S, _{except when both X 2} and X ₃ are single bonds, and a plurality of L ₃ are the same or different from each other, and a plurality of Ar ₃ are the same as or different from each other. n and m are each an integer of 0 or 1, and n+m is an integer of 1 or more. That is, at least one of n and m is 1.

The L _{One To} L _{3 Are} each independently a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; may be selected from the group consisting of.

When L ₁ to L ₃ is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₁₈ arylene group, such as phenyl, biphenyl, terphenyl, or the like.

The Ar _{1 To} Ar _{3 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; C ₃ ~ C ₆₀ An aliphatic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} and -L′-N(R _a )(R _b ).

When Ar ₁ to Ar ₃ is an aryl group, preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, and triphenylene.

When Ar ₁ is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₈ heterocyclic group, such as pyridine, pyrimidine, triazine, quinazoline, quinoline, carba Sol, phenylcarbazole, benzocarbazole, dibenzocarbazole, dibenzothiophene, benzothienopyridine, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, indolocarbazole, indenocarbazole , benzothienocarbazole, benzofurocarbazole, indenofluorene, fluorenobenzofuran, fluorenobenzothiophene, dibenzothienobenzofuran, and the like.

R ₁ are each independently 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 ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ Aryloxy group; and -L′-N(R _a )(R _b ) may be selected from the group consisting of, and adjacent groups may be bonded to each other to form a ring.

a is an integer of 0 to 4, and when a is an integer of 2 or more, a plurality of R ₁ are the same as or different from each other.

When R ₁ is an aryl group, it may be preferably a C ₆ ~ C ₃₀ aryl group, more preferably a C ₆ ~ C ₁₈ aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, or the like.

The L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And it may be selected from the group consisting of combinations thereof.

The R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ An aliphatic group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And it may be selected from the group consisting of combinations thereof.

The L ₁ to L ₃ , Ar ₁ to Ar ₃ , R ₁ , L′, R _a and R _b are each deuterium; halogen; a silane group 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 Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; _{a C 6} -C ₂₀ aryl group substituted with deuterium; 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; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ An aryl alkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

Preferably, Chemical Formula 1 may be represented by one of the following Chemical Formulas I-1 to I-6.

<Formula I-1> <Formula I-2> <Formula I-3>

<Formula I-4> <Formula I-5> <Formula I-6>

In Formulas I-1 to I-6, X ₁ to X ₃ , R ₁ , a, Ar ₁ , and L ₁ are the same as defined in Formula 1.

Preferably, Ar ₁ may be represented by Formula A or Formula B below.

<Formula A> <Formula B>

In Formulas A and B, each symbol may be defined as follows.

X ₄ is NL ₅ -Ar ₅ , O, S or C(R ₂ )(R ₃ ).

A ring and B ring are each independently C ₆ ~ C ₃₀ aromatic hydrocarbon; Or O, N, S, Si, P is a C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom. Preferably, ring A and ring B are each independently C ₆ ~ C ₂₄ aromatic hydrocarbon; Or O, N, S, Si, P is a C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom.

In this case, ring A and ring B may be further substituted with ^{one or more R a , respectively.} Here, R ^a is hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} cyano group; nitro group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl 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; And C ₃ -C ₂₀ An aliphatic ring group; may be selected from the group consisting of.

The L ₅ is a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; C ₃ ~ C ₂₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; may be selected from the group consisting of.

The Ar ₅ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ).

The R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} cyano group; nitro group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl 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; and a C ₃ -C ₂₀ aliphatic ring group; selected from the group consisting of, and R ₂ and R ₃ may be bonded to each other to form a ring.

L', R _a and R _b are the same as defined in Formula 1.

Preferably, in Formulas A and B, ring A and ring B may be selected from the group consisting of the following Formulas B-1 to B-16.

(B-1) (B-2) (B-3) (B-4) (B-5) (B-6)

(B-7) (B-8) (B-9) (B-10) (B-11)

(B-12) (B-13) (B-14) (B-15) (B-16)

In Formulas B-1 to B-16, * represents a condensed position. That is, * represents a position condensed with a 5-membered ring including _{X 4 or a 5-membered ring including N.}

V is independently of each other C(R ^a ) or N, and X ₅ is NL ₆ -Ar ₆ , O, S or C(R ₄ )(R ₅ ).

Wherein R ^a is as defined in Formulas A and B above.

The L ₆ is a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; C ₃ ~ C ₂₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; may be selected from the group consisting of.

The Ar ₆ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic group; and -L′-N(R _a )(R _b ).

The R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C _{20 aryl group;} cyano group; nitro group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl 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; and a C ₃ -C ₂₀ aliphatic ring group; may be selected from the group consisting of, and R ₄ and R ₅ may be bonded to each other to form a ring.

L', R _a and R _b are the same as defined in Formula 1.

Preferably, Ar ₁ may be selected from the group consisting of the following Chemical Formulas 1-1 to 1-9.

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

<Formula 1-4> <Formula 1-5> <Formula 1-6>

<Formula 1-7> <Formula 1-8> <Formula 1-9>

In Formulas 1-1 to 1-9, each symbol may be defined as follows. * indicates a position bonding with _{L 1 .}

X ₆ is N, N-(L ₇ -Ar ₇ ), O or S, provided that in Formulas 1-7 and 1-8, X ₆ is N-(L ₇ -Ar ₇ ), O or S.

X ₇ and X ₈ are each independently a single bond, N, N-(L ₈ -Ar ₈ ), O or S, with the proviso that X ₇ and X _{8 in Formulas 1-6 and 1-9 are independently of each other a single bond} a bond, N-(L ₈ -Ar ₈ ), O or S, a plurality of L ₈ are the same or different from each other, a plurality of Ar ₈ are the same or different from each other, and X ₇ and X ₈ are both single bonds , o and p are integers of 0 or 1, and at least one of o and p is an integer of 1.

R ₆ to R ₈ are hydrogen; heavy hydrogen; halogen; a silane group 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 Alkoxy group; C ₆ -C ₂₀ Arylalkoxy 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; And C ₃ -C ₂₀ An aliphatic ring group; may be selected from the group consisting of.

b, c and f are each an integer of 0-4, d and e are each an integer of 0-6, and when each of these is an integer of 2 or more, each of R ^{6 ,} each of R ^{7 , and} each of R ⁸ are the same as or different from each other.

The L ₇ and L ₈ are each independently a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; C ₃ ~ C ₂₀ An aliphatic group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; may be selected from the group consisting of.

The Ar ₇ and Ar ₈ are each independently a C ₆ ~ C ₂₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ An aliphatic group; C ₃ ~ C ₂₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{20 aromatic ring;} and -L′-N(R _a )(R _b ). Here, L', R _a and R _b 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, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is one type represented by Formula 1 A single compound or two or more types of compounds are included.

The organic 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 is included in the light emitting layer.

Synthesis example

The compound represented by Formula 1 according to the present invention (final products) may be synthesized by reacting Sub 1 and Sub 2 or Sub 1 and Sub 3 as shown in Scheme 1 below, but is not limited thereto. Scheme 1 below represents a case in which one of Y ₁ to Y ₄ in Formula 1 is C-(L ₁ -Ar ₁ ), wherein Ar ₁ is Formula A or Formula B.

<Scheme 1>

In Scheme 1, _{two of Y 1} to Y ₄ are N, and one of the _{other is C combined with L 1} -Sub 2 or L ₁ -Sub 3, and the other is N or C-(L ₁ -Ar ₁ ), and _{two of Y 5} to Y ₈ are N, and one of the other is _{C bonded to L 1} -Cl, the other is N or C-(L ₁ -Ar ₁ ), and the rest of the symbols are chemical formulas. 1, as defined in Formulas A and B.

I. Sub 1 Synthesis example

Sub 1 of Scheme 1 may be synthesized by the reaction routes of Schemes 2 to 4, but is not limited thereto.

1. Synthesis of Sub 1-A

<Scheme 2>

Synthesis of Sub 1-A-3

Sub 1-A-1, Sub 1-A-2, K ₂ CO ₃ (3 equivalents) and Pd(PPh ₃ ) ₄ (0.05 equivalents) were dissolved in anhydrous THF and a small amount of water, and then at 80° C. for 12 hours. refluxed. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by silica gel column to obtain Sub 1-A-3.

Synthesis of Sub 1-A-4

Sub 1-A-3 and triphenylphosphine (2.5 equivalents) were dissolved in o- dichlorobenzene, and refluxed for 24 hours. When the reaction is completed, the solvent is removed by distillation under reduced pressure. Thereafter, impurities were removed from the concentrate by silica gel column and recrystallization to obtain Sub 1-A-4.

Synthesis of Sub 1-A

Sub 1-A-4 to Sub 1-A-5, Pd ₂ (dba) ₃ (0.05 eq.), P (t-Bu) ₃ (0.1 equiv), NaO t -Bu (3 eq.), After the addition of toluene, refluxed at 100 ℃ stirred for 24 hours. Upon completion of the reaction, extraction is performed with ether and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, impurities were removed from the concentrate by silica gel column and recrystallization to obtain Sub 1-A.

1) Sub 1-43 Synthesis example

(1) Synthesis of Sub 1-43-A

(2,4-dichlorofuro[3,2-d]pyrimidin-7-yl)boronic acid (15 g, 64.43 mmol) in 1-bromo-2-nitrobenzene (15.62 g, 77.32 mmol), K ₂ CO ₃ (26.71 g, 193.29 mmol), Pd(PPh ₃ ) ₄ (3.72 g, 3.22 mmol), THF (300 ml) and water (150 ml) were added, followed by the same method as the synthesis method of Sub 1-A-3 Proceeded to obtain Sub 1-43-A (14.78 g, 74%).

(2) Sub 1-43-B synthesis

After adding triphenylphosphine (29.6 g, 112.87 mmol) and o- dichlorobenzene (280 ml) to Sub 1-43-A (14 g, 45.15 mmol), proceed in the same manner as in the synthesis method of Sub 1-A-4 to Sub 1-43-B (5.65 g, 45%) was obtained.

(3) Sub 1-43-C synthesis

Sub 1-43-B (5 g, 17.98 mmol) in bromobenzene (3.25 g, 20.68 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.9 mmol), P(t-Bu) ₃ (0.4 g, 1.8 mmol) ), NaO t -Bu (5.18 g, 53.94 mmol), and toluene (200 ml) were added, and then proceeded in the same manner as in the synthesis of Sub 1-A to obtain Sub 1-43-C (4.2 g, 66%). got it

(4) Sub 1-43 synthesis

Sub 1-43-C (4 g, 11.29 mmol) in phenylboronic acid (1.65 g, 13.55 mmol), K ₂ CO ₃ (4.68 g, 33.88 mmol), Pd(PPh ₃ ) ₄ (0.65 g, 0.56 mmol), THF (80 ml) and water (40 ml) were added, and then proceeded in the same manner as in the synthesis of Sub 1-A-3 to obtain Sub 1-43 (3.17 g, 71%). got it

2. Synthesis of Sub 1-B

<Scheme 3>

Synthesis of Sub 1-B-3

Sub 1-B-1, Sub 1-B-2, Pd(PPh ₃ ) ₄ (0.03 equiv.) and K ₂ CO ₃ (1.5 equiv.) were dissolved in anhydrous THF and EtOH, H ₂ O was added, and 12 at 90 ° C. time reflux. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by silica gel column to obtain the desired Sub 1-B-3.

Synthesis of Sub 1-B

3-nitropyridine (0.05 equiv), BzOOtBu (tert-butyl peroxybenzoate) (2 equiv), C ₆ F ₆ (hexafluorobenzene), DMI (N,N) to Sub 1-B-3 and Pd(OAc) _{2 (0.05 equiv.)} '-dimethylimidazolidinone) was added and refluxed at 90°C for 3 hours. Upon completion of the reaction, the solvent was removed by vacuum distillation, and impurities were removed from the concentrated product by silica gel column and recrystallization to obtain Sub 1-B.

2) Sub 1-23 Synthesis Example

(1) Sub 1-23-A synthesis

6-bromo-2,4-dichloro-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine (20 g, 58.31 mmol) in (2-hydroxyphenyl)boronic acid (9.65 g, 69.97 mmol), K ₂ After adding CO ₃ (12.09 g, 87.46 mmol), THF (400 ml), EtOH (100 ml), and H ₂ O (100 ml), proceed in the same manner as in the synthesis of Sub 1-B-3 to Sub 1 -23-A (8.1 g, 39%) was obtained.

(2) Sub 1-23-B synthesis

Sub 1-23-A (8 g, 22.46 mmol) in Pd(OAc) ₂ (0.25 g, 1.12 mmol), 3-nitropyridine (0.14 g, 1.12 mmol), BzOOtBu (tert-butyl peroxybenzoate) (8.72 g, 44.92) mmol), C ₆ F ₆ (hexafluorobenzene) (200 ml), and DMI (N,N'-dimethylimidazolidinone) (130 ml) were added, and then proceeded in the same manner as in the synthesis method of Sub 1-B, followed by Sub 1-23- B (3.05 g, 44%) was obtained.

(3) Sub 1-23 synthesis

Sub 1-23-B (3 g, 8.47 mmol) in phenylboronic acid (1.24 g, 10.16 mmol), K ₂ CO ₃ (3.51 g, 25.41 mmol), Pd(PPh ₃ ) ₄ (0.49 g, 0.42 mmol), THF (60 ml) and water (30 ml) were added, and then proceeded in the same manner as in the synthesis of Sub 1-A-3 to obtain Sub 1-43 (2.55 g, 76%). got it

3) Synthesis of Sub 1-C

<Scheme 4>

Synthesis of Sub 1-C-3

Sub 1-C-1 to Sub 1-C-2, Pd ₂ (dba) ₃ (0.05 equivalent), DPEPhos (Oxydi-2,1-phenylene)bis(diphenylphosphine) (0.15 equivalent), t-BuONa (1.1 equivalent) ), add toluene and reflux at 60°C for 2 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was separated using a silica gel filter to obtain Sub 1-C-3.

Synthesis of Sub 1-C

After adding Pd(OAc) ₂ (0.05 equiv), P(t-Bu) ₃ (0.1 equiv), K ₂ CO ₃ (3 equiv), and DMA to Sub 1-C-3 and stirring and refluxing, when the reaction is complete The temperature of the reactant is cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} and concentrated, and impurities were removed by silica gel column and recrystallization to obtain Sub 1-C.

3. Sub 1-17 Synthesis Example

(1) Synthesis of Sub 1-17-A

6,7-dibromo-2,3-dichlorofuro[2,3-b]pyrazine (30 g, 86.51 mmol) in benzenethiol (11.4 g, 103.81 mmol), Pd ₂ (dba) ₃ (4 g, 4.33 mmol), After adding DPEPhos (Oxydi-2,1-phenylene)bis(diphenylphosphine) (7 g, 12.98 mmol), t-BuONa (9.1 g, 95.16 mmol), and toluene, the same method as for the synthesis of Sub 1-C-3 to obtain Sub 1-17-A (20.1 g, 62%).

(2) Sub 1-17-B synthesis

Sub 1-17-A (19 g, 50.53 mmol) in Pd(OAc) ₂ (0.6 g, 2.53 mmol), P(t-Bu) ₃ (1 g, 5.1 mmol), K ₂ CO ₃ (21 g, 151.59 mmol) and DMA were added, and the same method was followed for the synthesis of Sub 1-C to obtain Sub 1-17-B (5.4 g, 0.36%).

(3) Sub 1-17 Synthesis

Sub 1-17-B (4 g, 13.55 mmol) in phenylboronic acid (1.98 g, 16.26 mmol), K ₂ CO ₃ (5.62 g, 40.66 mmol), Pd(PPh ₃ ) ₄ (0.78 g, 0.68 mmol), THF (80 ml) and water (40 ml) were added, and then proceeded in the same manner as in the synthesis of Sub 1-A-3 to obtain Sub 1-17 (3.24 g, 71%). got it

Compounds belonging to Sub 1 are as follows, but are not limited thereto, and FD-MS values of these compounds are shown in Table 1.

[Table 1]

II. Sub 2's Synthesis example

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.

<Scheme 5>

1. Sub 2-15 Synthesis Example

(1) Sub 2-15a synthesis

2-bromo-9-phenyl-9H-carbazole (50 g, 155.18 mmol), bis(pinacolato)diboron (51.23 g, 201.73 mmol), KOAc (45.69 g, 465.54 mmol), PdCl ₂ (dppf) (5.68 g, 7.76 mmol) was dissolved in DMF (1L) solvent, and then refluxed at 120° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and wiped with 1N HCl. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was _{recrystallized using CH 2} Cl ₂ and methanol solvent to obtain a product (36.09 g, 81%).

(2) Synthesis of Sub 2-15b

Sub 1-15a (30 g, 104.48 mmol), 1-bromo-2-nitrobenzene (27.44 g, 135.83 mmol), K ₂ CO ₃ (43.32 g, 313.45 mmol), Pd(PPh ₃ ) ₄ (6.04 g, 5.22) mmol) was placed in a round-bottom flask, dissolved in THF (600 mL) and water (300 mL), and then refluxed at 80° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by silica gel column to obtain a product (26.27 g, 69%).

(3) Sub 2-15 synthesis

Sub 1-15b (10 g, 27.44 mmol) and triphenylphosphine (17.99 g, 68.61 mmol) were dissolved in o- dichlorobenzene (200 mL), and refluxed at 180° C. for 24 hours. When the reaction was completed, the solvent was removed by vacuum distillation, and impurities were separated from the concentrated product by silica gel column and recrystallization to obtain the desired product (6.39 g, 70%).

2. Sub 2-30 Synthesis Example

(1) Sub 2-30a synthesis

5-bromobenzo[b]naphtha[1,2-d]thiophene (50 g, 159.64 mmol) in bis(pinacolato)diboron (52.7 g, 207.53 mmol), KOAc (47 g, 478.91 mmol), PdCl ₂ (dppf) (5.84 g, 7.98 mmol) was added, followed by the same procedure as for the synthesis of Sub 2-15a to obtain a product (35.52 g, 80%).

(2) Sub 2-30b synthesis

1-bromo-2-nitrobenzene (27.44 g, 135.83 mmol) in Sub 2-30a (30 g, 104.48 mmol), K ₂ CO ₃ (43.32 g, 313.45 mmol), Pd(PPh ₃ ) ₄ (6.04 g, 5.22) mmol), THF (600mL), and water (300mL) were added, and the same procedure as in Sub 2-15b was followed to obtain a product (27.11 g, 73%).

(3) Sub 2-30 Synthesis

After addition of triphenylphosphine (18.45 g, 70.34 mmol) and o- dichlorobenzene (200 mL) to Sub 2-30b (10 g, 28.14 mmol), proceed in the same manner as in the synthesis of Sub 2-15 above, the product (6.27 g, 67%) was obtained.

Compounds belonging to Sub 2 are the same as the following compounds, but are not limited thereto, and Table 2 shows FD-MS values of these compounds.

[Table 2]

III. Sub 3's Synthesis example

Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 6 below, but is not limited thereto.

<Scheme 6>

1. Sub 3-50 Synthesis Example

(1) Synthesis of Sub 3-50a

2-bromodibenzo[b,d]thiophen-3-ol (25 g, 89.56 mmol), (2-chloro-6-fluorophenyl)boronic acid (20.3 g, 116.42 mmol), K ₂ CO ₃ (37.13 g, 268.67 mmol) ), Pd(PPh ₃ ) ₄ (5.17 g, 4.48 mmol) was placed in a round-bottom flask, dissolved in THF (500 mL) and water (250 mL), and refluxed at 80° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by silica gel column to obtain a product (16.2 g, 55%).

(2) Sub 3-50b synthesis

Sub 3-50a (20 g, 60.83 mmol) and K ₂ CO ₃ (21.02 g, 152.07 mmol) were placed in a round-bottom flask, NMP was added, and refluxed at 110°C. When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and separated by silica gel column to obtain a product (11.46 g, 61%).

(3) Sub 3-50 synthesis

Sub 3-50b (10 g, 32.39 mmol), bis(pinacolato)diboron (10.69 g, 42.1 mmol), KOAc (9.54 g, 97.16 mmol), PdCl ₂ (dppf) (1.18 g, 1.62 mmol) in DMF (250) mL), and then refluxed at 120° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and wiped with 1N HCl. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was _{recrystallized from CH 2} Cl ₂ and methanol solvent to obtain a product (7.93 g, 77%).

(1) Sub 3-53a synthesis

(9-chlorodibenzo[b,d]thiophen-2-yl)boronic acid (30 g, 114.28 mmol), 1-bromo-2-nitrobenzene (30 g, 148.57 mmol), K ₂ CO ₃ (47.38 g, 342.84 mmol), Pd(PPh ₃ ) ₄ (6.6 g, 5.71 mmol) was placed in a round-bottom flask, dissolved in THF (600 mL) and water (300 mL), and then at 80°C for 12 hours. refluxed while When the reaction was completed, the temperature of the reactant was cooled to room temperature _{, extracted with CH 2} Cl ₂ , and washed with water. The organic layer _{was dried over MgSO 4} , concentrated and separated by silica gel column to obtain a product (27.57 g, 71%).

(2) Sub 3-53b synthesis

Sub 3-53a (20 g, 58.86 mmol) and triphenylphosphine (38.60 g, 147.15 mmol) were dissolved in o- dichlorobenzene (400 mL), and refluxed at 200 °C for 24 hours. Upon completion of the reaction, the solvent was removed by vacuum distillation, and impurities were separated from the concentrated product by silica gel column and recrystallization to obtain a product (11.23 g, 62%).

(3) Sub 3-53c synthesis

After dissolving Sub 3-53b (10 g, 32.49 mmol) in toluene, bromobenzene (5.87 g, 37.36 mmol), Pd ₂ (dba) ₃ (1.49 g, 1.62 mmol), P(t-Bu) ₃ (0.66 g) , 3.25 mmol), NaO t -Bu (9.37 g, 97.47 mmol), and toluene were added, and the mixture was stirred and refluxed at 100° C. for 24 hours. Upon completion of the reaction, extraction was performed with ether and water, and the organic layer _{was dried over MgSO 4} and concentrated, and impurities were separated by silica gel column and recrystallization to obtain a product (9.73 g, 78%).

(4) Sub 3-53 synthesis

Sub 3-53c (9 g, 23.44 mmol), bis(pinacolato)diboron (7.74 g, 30.48 mmol), KOAc (6.9 g, 70.33 mmol), PdCl ₂ (dppf) (0.86 g, 1.17 mmol) was mixed with DMF (180 mL), and then proceeded in the same manner as in the synthesis of Sub 3-50 to obtain a product (7.84 g, 85%).

Compounds belonging to Sub 3 are the same as the following compounds, but are not limited thereto, and FD-MS values of these compounds are shown in Table 3 below.

[Table 3]

Ⅲ. of the final compound Synthesis example

Synthesis of 1-23

Sub 1-35 (5 g, 14.85 mmol) to Sub 2-30 (5.52 g, 17.07 mmol), NaO t -Bu (4.28 g, 44.54 mmol), Pd ₂ (dba) ₃ (0.68 g, 0.74 mmol), After adding P(t-Bu) ₃ (0.3 g, 1.48 mmol) and toluene (200 mL), The mixture was stirred and refluxed at 100°C for 24 hours. When the reaction is complete, extraction is performed with ether and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the concentrate was separated from impurities by silica gel column and recrystallization to obtain 6.57 g (yield: 71%) of the product.

Synthesis of 1-76

Sub 1-12 ( 4 g, 9.71 mmol) to Sub 2-32 (3.43 g, 11.17 mmol), NaO t -Bu (2.8 g, 29.13 mmol), Pd ₂ (dba) ₃ (0.44 g, 0.49 mmol), After adding P(t-Bu) ₃ (0.2 g, 0.97 mmol) and toluene (160 mL), In the same manner as in the synthesis method of 1-23, 5.11 g of a product (yield: 77%) was obtained.

Synthesis of 1-87

Sub 1-34 (3 g, 9.35 mmol) to Sub 2-13 (2.88 g, 10.76 mmol), NaO t -Bu (2.7 g, 28.06 mmol), Pd ₂ (dba) ₃ (0.43 g, 0.47 mmol), After adding P(t-Bu) ₃ (0.2 g, 0.94 mmol) and toluene (120 mL), In the same manner as in the experimental method of 1-23, 3.51 g of the final compound (yield: 68%) was obtained.

Synthesis of 1-107

Sub 1-26 (5 g, 14.85 mmol) to Sub 3-51 (6.72 g, 17.82 mmol), Pd(PPh ₃ ) ₄ (0.86 g, 0.74 mmol), K ₂ CO ₃ (6.16 g, 44.54 mmol), THF (100 ml), EtOH (30 ml), H ₂ O (30 ml) were added and refluxed at 90° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and washed with water. The organic layer _{was dried over MgSO 4} , concentrated, and then impurities were removed using a silica gel column to obtain 6.96 g (74%) of the product.

FD-MS values of compounds 1-1 to 1-134 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[ Example One] Red organic electroluminescent device (host)

^{N 1} -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on the ITO layer (anode) formed on the glass substrate After vacuum deposition of -1,4-diamine to a thickness of 60 nm to form a hole injection layer, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl on the hole injection layer was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Thereafter, compound 1-1 of the present invention as a host material and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate as a dopant material on the hole transport layer were doped with a dopant such that the weight ratio was 95:5, and the thickness was 30 nm. of the light emitting layer was deposited.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and on the hole blocking layer Et tris(8-quinolinol)aluminum was deposited to a thickness of 40 nm to form an electron transport layer.

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

[ Example 2] to [ Example 26]

An organic electroluminescent device was always prepared in the same manner as in Example 1, except that the compound of the present invention shown in Table 5 was used instead of Compound 1-1 as the host material of the light emitting layer.

[ comparative example 1] to [ comparative example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following Comparative Compounds A to D was used instead of Compound 1-1 of the present invention as a host material for the light emitting layer.

<Comparative compound A> <Comparative compound B> <Comparative compound C> <Comparative compound D>

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 26 and Comparative Examples 1 to 4 prepared in this way, the electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, and 2500 cd/m ^{2 The} lifetime of T95 was measured using a lifetime measuring device manufactured by McScience at the reference luminance. The measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results in Table 5, the organic electroluminescent device using the material for an organic light emitting device of the present invention as a phosphorescent host of the light emitting layer has significantly improved efficiency and lifespan compared to Comparative Compounds A to D, and lowered the driving voltage.

Comparative compound B in which pyrrolopyrimidine is condensed with benzofuran, comparative compound C in which pyrrolopyridine is condensed with indole, or pyrrolopyridine condensed with benzothiophene rather than Comparative Compound A (CBP), which is generally used as a host material The device results of Comparative Compound D were excellent, and when the compounds of the present invention were used, the device results were better than those of Comparative Compounds B to D. Therefore, depending on the number of amines (the number of nitrogen contained in the outer hexagonal ring), the type of substituents bonded to the outer ring including N, the number of substituents bonded to the outer ring including N and the bonding position, the driving voltage and efficiency of the device and life expectancy.

When the comparative compound C or D was used as a host, the driving voltage was lower and the efficiency was improved compared to the case where the comparative compound B was used.

And when the compound of the present invention and comparative compounds C and D are compared, the energy level (energy level) of the compound according to the number of N in the hexagonal ring including N among the 4-ring core, the bonding position of the substituents substituted thereto, the number of substituents, etc. level) is changed, and therefore, it is judged that the band gap of the compound of the present invention is easier for hole and electron movement than the comparative compound, and thus the luminous efficiency is increased.

That is, Y ₁ ~ Y in formula 1 and ₄₂ N of the dog, the dog remaining 2 CL ₁ -Ar ₁ in the device characteristics were improved as compared with the case of using the comparative compounds when using the compounds of the present invention to a host, in particular Ar ₁ In the case of Chemical Formula A, it has an energy level that is easy for hole movement and has an effect of lowering the driving voltage, and in the case of Chemical Formula B, it has an appropriate T ₁ value and a deep HOMO value at the same time to increase the charge balance in the light emitting layer It appears that the luminous efficiency is maximized.

The data measured using the DFT method (B3LYP/6-31g(D)) of the Gaussian program for each type of compound are shown in Table 6 below.

<B Type> <C Type> <D Type>

Type B is when H bonded to the carbon of the hexagonal ring (pyridine ring) including N is not substituted with another substituent, and type C is when one heterocycle (carbazole) is bonded to the carbon of the pyrimidine ring , D type is a compound of the present invention in which an aryl type (phenyl) and a heterocyclic ring (carbazole) are bonded to each carbon of the pyrimidine ring. That is, the B-type and C-type have different numbers and types of substituents substituted on the pyrimidine moiety compared to the D-type compound of the present invention. Due to the difference in the presence or absence and number of such substituent bonds, the physical properties of each compound are different as shown in Table 6 below.

[Table 6]

Referring to Table 6, since the LUMO value of type D is the smallest (deep), it is most likely to be most advantageous for electron transport. Also, compared to types B and C, the D type of the present invention has a narrow band gap and a small ( deep) T ₁ value, which is advantageous for realizing high efficiency and lifespan. This can be confirmed through the device data results in Table 5 above.

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 skilled in the art to which the present invention pertains. Accordingly, the embodiments disclosed in the present specification are intended to illustrate rather than 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 technologies 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 (12)

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

In Formula 1,
Y ₁ to Y ₄ are each independently N or C-(L ₁ -Ar ₁ ), _{two of Y 1} to Y ₄ are N, a plurality of L ₁ are the same or different, and a plurality of Ar ₁ are each same or different,
X ₁ is N-(L ₂ -Ar ₂ ), O or S,
n and m are each an integer of 0 or 1,
when n is 1, X ₂ is N-(L ₃ -Ar ₃ ), O or S, and X ₃ is a single bond,
When m is 1, X ₃ is N-(L ₃ -Ar ₃ ), O or S, X ₂ is a single bond,
R ₁ are each independently hydrogen; heavy hydrogen; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; And C _{1 To} C _{50 It} is selected from the group consisting of an alkyl group, a is 0 or 1,
L ₁ is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
L ₂ and L ₃ are a single bond,
Ar _{1 To} Ar _{3 Are} each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{60 It} is selected from the group consisting of a heterocyclic group,
The Ar ₁ is deuterium; halogen; cyano group; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; _{a C 6} -C ₂₀ aryl group substituted with deuterium; fluorenyl group; And it may be substituted with one or more substituents selected from the group consisting of _{a C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P. The method of claim 1,
Formula 1 is a compound characterized in that it is represented by one of the following Formulas I-1 to I-6:
<Formula I-1><FormulaI-2><FormulaI-3>

<Formula I-4><FormulaI-5><FormulaI-6>

In Formulas I-1 to I-6, X ₁ to X ₃ , R ₁ , a, Ar ₁ , and L ₁ are the same as defined in claim 1. The method of claim 1,
Wherein Ar ₁ Is a compound characterized in that represented by the following formula A or formula B:
<Formula A><FormulaB>

In the above formulas A and B,
X ₄ is NL ₅ -Ar ₅ , O, S or C(R ₂ )(R ₃ ),
A ring and B ring are each independently C ₆ ~ C ₃₀ aromatic hydrocarbon; Or O, N, S, Si, P is a C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom, the A ring and the B ring may be further substituted with ^{one or more R a} , each the same as or different from each other,
The L ₅ is a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group,
The Ar ₅ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group,
The R ₂ , R ₃ and R ^a are each independently hydrogen; heavy hydrogen; halogen; cyano group; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; And O, N, S, Si and P is selected from the _{group consisting of a C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of, R ₂ and R ₃ are bonded to each other to form a ring can do. 4. The method of claim 3,
The A ring and the B ring is a compound, characterized in that selected from the group consisting of Formulas B-1 to B-16:
(B-1) (B-2) (B-3) (B-4) (B-5) (B-6)

(B-7) (B-8) (B-9) (B-10) (B-11)

(B-12) (B-13) (B-14) (B-15) (B-16)

In Formulas B-1 to B-16, * represents a condensed position,
V is independently of each other C(R ^a ) or N,
X ₅ is NL ₆ -Ar ₆ , O, S or C(R ₄ )(R ₅ ),
The R ^a , R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; cyano group; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; And O, N, S, Si and P is selected from the _{group consisting of a C 2} -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of, R ₄ and R ₅ are bonded to each other to form a ring can do,
The L ₆ is a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; And O, N, S, Si and P containing at least one heteroatom ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group,
The Ar ₆ is a C ₆ ~ C ₂₀ aryl group; fluorenyl group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group. The method of claim 1,
Wherein Ar ₁ is a compound, characterized in that selected from the group consisting of Formulas 1-1 to 1-9:
<Formula 1-1><Formula1-2><Formula1-3>

<Formula 1-4><Formula1-5><Formula1-6>

<Formula 1-7><Formula1-8><Formula1-9>

In Formulas 1-1 to 1-9, * represents a position bonding with _{L 1 ,}
X ₆ is N, N-(L ₇ -Ar ₇ ), O or S, with the proviso that X ₆ in Formulas 1-7 and 1-8 is N-(L ₇ -Ar ₇ ), O or S,
X ₇ and X ₈ are each independently a single bond, N, N-(L ₈ -Ar ₈ ), O or S, with the proviso that X ₇ and X _{8 in Formulas 1-6 and 1-9 are independently of each other a single bond} a bond, N-(L ₈ -Ar ₈ ), O or S, a plurality of L ₈ are the same or different from each other, a plurality of Ar ₈ are the same or different from each other, and X ₇ and X ₈ are both single bonds Except for, o and p are integers of 0 or 1, and at least one of o and p is an integer of 1,
R ₆ to R ₈ are each independently hydrogen; heavy hydrogen; halogen; cyano group; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ Aryl group; fluorenyl group; And it is selected from the group consisting of _{a C 2} -C ₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P,
b, c and f are each an integer of 0-4, d and e are each an integer of 0-6, and when each of these is an integer of 2 or more, each of R ^{6 ,} each of R ^{7 , and} each of R ⁸ are the same as or different from each other,
The L ₇ and L ₈ are each independently a single bond; C ₆ ~ C ₂₀ Arylene group; fluorenylene group; And O, N, S, Si and P, including at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group,
The Ar ₇ and Ar ₈ are each independently a C ₆ ~ C ₂₀ aryl group; fluorenyl group; And O, N, S, Si and P containing at least one heteroatom C ₂ ~ C _{20 It} is selected from the group consisting of a heterocyclic group. 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. 8. The method of claim 7,
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. 9. The method of claim 8,
The compound is an organic electric device, characterized in that contained in the light emitting layer. 8. The method of claim 7,
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 7; and
An electronic device comprising a; a control unit for driving the display device. 12. The method of claim 11,
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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