KR102377225B1 - organic light-emitting diode with high efficiency and long lifetime - Google Patents

Abstract

The present invention relates to a first electrode; a second electrode opposite the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode, wherein the light-emitting layer includes at least one condensed ring compound represented by [Formula A]; It also relates to an organic light-emitting device containing at least one heterocyclic compound represented by [Formula D], where [Formula A] and [Formula D] are the same as described in the detailed description of the invention.

Description

Organic light-emitting diode with high efficiency and long lifetime characteristics

The present invention relates to an organic light-emitting device having high efficiency and long lifespan characteristics, and more specifically, to an organic light-emitting device including a host material of a specific structure in a light-emitting layer within the organic light-emitting device.

Organic light emitting diode (OLED) is a display that uses the self-luminescence phenomenon, and has advantages such as a large viewing angle, being lightweight and compact compared to liquid crystal displays, and fast response speed, so it is full-color. ) Application to displays or lighting is expected.

In general, the organic light-emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials, and organic light-emitting devices using the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.

Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

The light-emitting materials can be classified into fluorescent materials derived from a singlet excited state of electrons and phosphorescent materials derived from a triplet excited state of electrons depending on the emission mechanism.

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and problems arise such as color purity being reduced or the efficiency of the device being reduced due to the emission attenuation effect. Therefore, color purity is increased and energy is reduced. A host-dopant system can be used as a light-emitting material to increase light-emitting efficiency through transition.

The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

As a prior art regarding the host compound among these light-emitting layers, Patent Publication No. 10-2011-0013220 (2011.02.09) discloses an organic compound in which an aromatic heterocycle is introduced into the skeleton of a 6-membered aromatic ring or a 6-membered heteroaromatic ring. This is described in Japanese Patent Application Laid-Open No. 2010-166070 (2010.7.29), which describes an organic compound in which an aryl or heteroaryl ring is bonded to a substituted or unsubstituted pyrimidine or quinazoline skeleton.

However, despite the prior art including the above prior literature, there is a continued need for the development of organic light emitting devices that exhibit improved efficiency and longer lifespan.

Public Patent Publication No. 10-2011-0013220 (2011.02.09)

Japanese Patent Laid-Open No. 2010-166070 (July 29, 2010)

Therefore, the technical problem to be achieved by the present invention is to provide a novel organic light emitting diode (OLED) with high efficiency and long lifespan characteristics by including a host of a specific structure in the light emitting layer of the organic light emitting device.

In order to achieve the above technical problems, the present invention includes: a first electrode; a second electrode opposite the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode, wherein the light-emitting layer includes at least one condensed ring compound represented by the following [Formula A]; Additionally, an organic light-emitting device comprising at least one heterocyclic compound represented by the following [Formula D] is provided.

[Formula A]

In [Formula A] above,

The substituents Ar1 and Ar2 are each the same or different, and are independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms, which can be combined with adjacent groups to form an aliphatic, aromatic, aliphatic hetero, or aromatic hetero condensed ring,

The linking groups L1 to L3 are each the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

The p, q and r are each integers from 0 to 3, but when each of them is 2 or more, each linking group L1 to L3 is the same or different from each other,

The substituent HAr1 is represented by any one of the following [Structural Formula 1] to [Structural Formula 3].

[Structural Formula 1] [Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],

Wherein X is any one selected from O, S and CR11R12,

The substituents R1 to R12 are the same or different, and are independently selected from hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms,

In Formula A, any one of the substituents R1 to R10 in Structural Formulas 1 to 3 represented by HAr1 is a single bond bonded to the linking group L1.

[Formula D]

In [Formula D] above,

The substituent HAr4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

n1 and n2 are each integers from 0 to 3, but when n1 and n2 are each 2 or more, HAr4 and L are the same as or different from each other,

)들은 서로 동일하거나 상이하며,The m1 is an integer from 1 to 4, but when m1 is 2 or more, the part containing HAr4 and L, respectively, in brackets [] (

) are the same or different from each other,

The Az is represented by any one of the following [Structural Formula 4] to [Structural Formula 10].

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In [Structural Formula 4] to [Structural Formula 10],

Wherein Z1 is N or CR21,

The Z2 is N or CR22,

Wherein Z3 is N or CR23,

The Z4 is N or CR24,

The Z5 is N or CR25,

The Z6 is N or CR26,

The Z7 is N or CR27,

The Z8 is N or CR28,

Wherein Z9 is N or CR29,

The Z10 is N or CR30,

The Z11 is N or CR31,

Y is any one selected from O, S, NR32 and CR33R34,

In structural formula 4, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 4 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,

In structural formula 5, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 5 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,

In the structural formula 6, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 6 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,

In structural formula 7, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 7 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,

In structural formula 8, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 8 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,

In structural formula 9, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 9 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,

In structural formula 10, at least one of Z1 to Z11 is N, and in order for the aromatic ring in structural formula 10 to have m1 bonds with the linking group L, m1 among R20 to R31 are each a single bond bonded to the linking group L,

The substituents R20 to R34 are the same or different, and are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms, and can be combined with adjacent groups to form an aliphatic, aromatic, aliphatic hetero, or aromatic hetero condensed ring.

The organic light emitting device according to the present invention can exhibit improved efficiency and longer lifespan compared to the organic light emitting device according to the prior art by using a host of a specific structure mixed in the light emitting layer.

1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimensions of the structures are enlarged or reduced from the actual size for clarity of the present invention, and known structures are omitted to reveal the characteristic structure, so it is not limited to the drawing. .

In explaining in detail the principles of a preferred embodiment of the present invention, if it is determined that a detailed description of a related known function or configuration may unnecessarily obscure the gist of the present invention, the detailed description will be omitted.

The present invention relates to a first electrode; a second electrode opposite the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode, wherein the light-emitting layer includes at least one condensed ring compound represented by the following [Formula A]; Additionally, an organic light-emitting device comprising at least one heterocyclic compound represented by the following [Formula D] is provided.

[Formula A]

In [Formula A] above,

The substituents Ar1 and Ar2 are each the same or different, and are independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms, which can be combined with adjacent groups to form an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring,

The linking groups L1 to L3 are each the same or different, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

The p, q and r are each integers from 0 to 3, but when each of them is 2 or more, each linking group L1 to L3 is the same or different from each other,

The substituent HAr1 is represented by any one of the following [Structural Formula 1] to [Structural Formula 3].

[Structural Formula 1] [Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],

Wherein X is any one selected from O, S and CR11R12,

The substituents R1 to R12 are the same or different, and are independently selected from hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms,

In Formula A, any one of the substituents R1 to R10 in Structural Formulas 1 to 3 represented by HAr1 is a single bond bonded to the linking group L1.

[Formula D]

In [Formula D] above,

The substituent HAr4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

n1 and n2 are each integers from 0 to 3, but when n1 and n2 are each 2 or more, HAr4 and L are the same as or different from each other,

)들은 서로 동일하거나 상이하며,The m1 is an integer from 1 to 4, but when m1 is 2 or more, the part containing HAr4 and L, respectively, in brackets [] (

) are the same or different from each other,

The Az is represented by any one of the following [Structural Formula 4] to [Structural Formula 10].

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In [Structural Formula 4] to [Structural Formula 10],

Wherein Z1 is N or CR21,

The Z2 is N or CR22,

Wherein Z3 is N or CR23,

The Z4 is N or CR24,

The Z5 is N or CR25,

The Z6 is N or CR26,

The Z7 is N or CR27,

The Z8 is N or CR28,

Wherein Z9 is N or CR29,

The Z10 is N or CR30,

The Z11 is N or CR31,

Y is any one selected from O, S, NR32 and CR33R34,

In structural formula 4, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 4 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,

In structural formula 5, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 5 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,

In the structural formula 6, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 6 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,

In structural formula 7, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 7 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,

In structural formula 8, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 8 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,

In structural formula 9, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 9 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,

In structural formula 10, at least one of Z1 to Z11 is N, and in order for the aromatic ring in structural formula 10 to have m1 bonds with the linking group L, m1 among R20 to R31 are each a single bond bonded to the linking group L,

The substituents R20 to R34 are the same or different, and are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted Any one selected from ringed heterocyclic groups having 5 to 30 carbon atoms, which can be combined with adjacent groups to form an aliphatic, aromatic, aliphatic hetero, or aromatic hetero condensed ring,

Here, 'substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula D] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, and 1 carbon atom. Halogenated alkyl group of 2 to 24 carbon atoms, alkenyl group of 2 to 24 carbon atoms, alkynyl group of 2 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, arylalkyl group of 7 to 24 carbon atoms, 2 to 2 carbon atoms Heteroaryl group of 24 or heteroarylalkyl group of 2 to 24 carbon atoms, alkoxy group of 1 to 24 carbon atoms, alkylamino group of 1 to 24 carbon atoms, arylamino group of 6 to 24 carbon atoms, heteroarylamino group of 1 to 24 carbon atoms, carbon number 1 It means being substituted with one or more substituents selected from the group consisting of an alkylsilyl group with 6 to 24 carbon atoms, an arylsilyl group with 6 to 24 carbon atoms, and an aryloxy group with 6 to 24 carbon atoms.

Meanwhile, considering the range of the alkyl group or aryl group in the “substituted or unsubstituted alkyl group having 1 to 24 carbon atoms” and “substituted or unsubstituted aryl group having 6 to 24 carbon atoms” in the present invention, the The range of the carbon number of the alkyl group having 1 to 24 carbon atoms and the aryl group having 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl portion or aryl portion when viewed as unsubstituted without considering the portion in which the substituent is substituted. will be. For example, a phenyl group substituted with a butyl group at the para position should be viewed as corresponding to an aryl group with 6 carbon atoms substituted with a butyl group with 4 carbon atoms.

Meanwhile, the aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen. When the aryl group has a substituent, it is fused with neighboring substituents to form an additional ring. can be formed.

Specific examples of the aryl group include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. are included, and at least one hydrogen atom of the aryl group is a deuterium atom or a halogen atom. , hydroxy group, nitro group, cyano group, silyl group, amino group (-NH ₂ , -NH(R), -N(R')(R''), R' and R" are independently of one another and have 1 to 10 carbon atoms. an alkyl group, in this case referred to as an “alkylamino group”), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group with 1 to 24 carbon atoms, halogenated alkyl group with 1 to 24 carbon atoms, 1 to 24 carbon atoms alkenyl group, alkynyl group of 1 to 24 carbon atoms, heteroalkyl group of 1 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, arylalkyl group of 6 to 24 carbon atoms, heteroaryl group of 2 to 24 carbon atoms or 2 to 24 carbon atoms of It may be substituted with a heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the compound of the present invention, has 2 carbon atoms and may contain 1 to 4 heteroatoms selected from N, O, P, Se, Te, Si, Ge or S in each ring of the aryl group. It refers to a heteroaromatic organic radical of 24 to 24, and the rings can be fused to form a ring. And one or more hydrogen atoms of the heteroaryl group may be replaced with the same substituent as that of the aryl group.

Additionally, in the present invention, the aromatic heterocycle means that one or more aromatic carbons in an aromatic hydrocarbon ring are substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more of the alkyl groups The hydrogen atom can be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., One or more hydrogen atoms of the alkoxy group may be replaced with the same substituent as that of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, and methylcyclobutylsilyl. , dimethylfurylsilyl, etc., and one or more hydrogen atoms of the silyl group may be replaced with the same substituent as that of the aryl group.

The present invention can provide an organic light emitting device with high efficiency and long lifespan by using the condensed ring compound represented by Formula A and the heterocyclic compound represented by Formula D in the light emitting layer of the organic light emitting device.

Here, to describe the characteristics of the condensed ring compound represented by Formula A in more detail, the condensed ring compound represented by Formula A has linking groups L1 to L3 bonded to nitrogen atoms, respectively, and the linking group L1 is one of the structural formulas 1 to 3. A 6-5-6-6 condensed ring in which a naphthalene ring is bonded to one side of the five-membered ring containing X and a benzene ring is bonded to the other side of the five-membered ring containing The structural feature is that the substituents Ar1 and Ar2 are bonded to the linking groups L2 and L3 to which the 6-5-6-6 condensed ring represented by any one of structural formula 3 is not bonded.

In addition, the heterocyclic compound represented by the formula D has as many linking groups L as m1 bonded to an aromatic heteroring containing at least one nitrogen, and each linking group L has 6 to 30 substituted or unsubstituted carbon atoms. It has the structural characteristic of being bonded to an aryl group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

Meanwhile, the linking groups L1 to L3 in the formula A are each the same or different, and are independently a single bond or any one selected from the following [Structural Formula 22] to [Structural Formula 30], and p, q, and r are each 1. Or it could be 2.

[Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25]

[Structural Formula 26] [Structural Formula 27] [Structural Formula 28] [Structural Formula 29]

[Structural Formula 30]

In Structural Formulas 22 to 30, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.

In addition, Az represented by [Structural Formula 4] to [Structural Formula 10] in Formula D may be any one selected from E1 to E24 below.

<E1> <E2> <E3> <E4> <E5>

<E6> <E7> <E8> <E9> <E10>

<E11> <E12> <E13> <E14> <E15>

<E16> <E17> <E18> <E19> <E20>

<E21> <E22> <E23> <E24>

In E1 to E24, X1 to It is a substituent selected from a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

Each m1 of X1 to X11 in E1 to E24 is a single bond bonded to the linking group L in Formula D.

Additionally, the linking group L in Formula D is a single bond or any one selected from [Structural Formula 22] to [Structural Formula 30] below, and n2 may be 1 or 2.

[Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25]

[Structural Formula 26] [Structural Formula 27] [Structural Formula 28] [Structural Formula 29]

[Structural Formula 30]

In Structural Formulas 22 to 30, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.

In addition, as an embodiment of the present invention, the substituents Ar1 and Ar2 in the [Formula A] are each the same or different, and are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. It may be any one selected from 3 to 30 heteroaryl groups.

Additionally, as an embodiment of the present invention, in the [Structural Formula 1] to [Structural Formula 3] in Formula A, one of the substituents R1 to R4 may be a single bond bonded to the linking group L1.

In addition, as an embodiment of the present invention, the substituents R20 to R31 in [Formula D] are each the same or different, and are independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. , a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

As an example, HAr4 in Formula D may be at least one substituent represented by any one of the following [Structural Formula 11] to [Structural Formula 13].

[Structural Formula 11]

[Structural Formula 12]

[Structural Formula 13]

In [Structural Formula 11] above,

The X12 is any one selected from O, S, NR49 and CR50R51,

Any one of the substituents R41 to R48 in Formula 11 is a single bond bonded to the linking group L in Formula D,

In [Structural Formula 12] above,

The X13 is any one selected from O, S, NR49 and CR50R51,

The X14 is any one selected from O, S, NR60 and CR61R62,

Any one of the substituents R45 to R48 and any one of the substituents R52 to R55 are each connected to each other as a single bond,

Among the substituents R41 to R48 in the structural formula 12, any one of the remaining seven substituents excluding the single bond connected to the condensed ring containing X14 is a single bond bonded to the linking group L in Formula D,

In [Structural Formula 13] above,

The X15 is any one selected from O, S, NR53, CR54R55, and

Y1 is any one selected from O, S, NR56, CR57R58,

Any one of the substituents R41 to R52 in Formula 13 is a single bond bonded to the linking group L in Formula D,

The two substituents adjacent to each other among R45 to R48 are single bonds connected to * of the structural formula Q1,

In [Structural Formulas 11] to [Structural Formulas 13], R41 to R62 are each the same or different, and are independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or Unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms group, substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted carbon atoms It is any one selected from aromatic hydrocarbon groups of 6 to 30 carbon atoms and substituted or unsubstituted heterocyclic groups of 5 to 30 carbon atoms.

Additionally, as an embodiment of the present invention, the substituent Ar1 or the substituent Ar2 in Formula A may be a substituent represented by the following structural formula 14.

[Structural Formula 14]

In [Structural Formula 14] above,

The X16 is any one selected from O, S and CR79R80,

R71 to R80 are the same or different, and are independently selected from hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or an unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms. Arylthio group, substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and substituted or unsubstituted It is any one selected from heterocyclic groups having 5 to 30 carbon atoms.

Any one of the substituents R71 to R78 in Formula 14 is a single bond bonded to the linking group L2 or L3 in Formula A.

Additionally, in the organic light emitting device according to the present invention, the condensed ring compound represented by Formula A may be any one selected from the group represented by Compound H1 to Compound H245 below, but is not limited thereto.

<Compound H1><Compound H2><Compound H3><Compound H4>

<Compound H5><Compound H6><Compound H7><Compound H8>

<Compound H9><Compound H10><Compound H11><Compound H12>

<Compound H13><Compound H14><Compound H15><Compound H16>

<Compound H17><Compound H18><Compound H19><Compound H20>

<Compound H21><Compound H22><Compound H23><Compound H24>

<Compound H25><Compound H26><Compound H27><Compound H28>

<Compound H29><Compound H30><Compound H31><Compound H32>

<Compound H33><Compound H34><Compound H35><Compound H36>

<Compound H37><Compound H38><Compound H39><Compound H40>

<Compound H41><Compound H42><Compound H43><Compound H44>

<Compound H45><Compound H46><Compound H47><Compound H48>

<Compound H49><Compound H50><Compound H51><Compound H52>

<Compound H53><Compound H54><Compound H55><Compound H56>

<Compound H57><Compound H58><Compound H59><Compound H60>

<Compound H61><Compound H62><Compound H63><Compound H64>

<Compound H65><Compound H66><Compound H67><Compound H68>

<Compound H69><Compound H70><Compound H71><Compound H72>

<Compound H73><Compound H74><Compound H75><Compound H76>

<Compound H77><Compound H78><Compound H79><Compound H80>

<Compound H81><Compound H82><Compound H83><Compound H84>

<Compound H85><Compound H86><Compound H87><Compound H88>

<Compound H89><Compound H90><Compound H91><Compound H92>

<Compound H93><Compound H94><Compound H95><Compound H96>

<Compound H97><Compound H98><Compound H99><Compound H100>

<Compound H101><Compound H102><Compound H103><Compound H104>

<Compound H105><Compound H106><Compound H107><Compound H108>

<Compound H109><Compound H110><Compound H111><Compound H112>

<Compound H113><Compound H114><Compound H115><Compound H116>

<Compound H117><Compound H118><Compound H119><Compound H120>

<Compound H121><Compound H122><Compound H123><Compound H124>

<Compound H125><Compound H126><Compound H127><Compound H128>

<Compound H129><Compound H130><Compound H131><Compound H132>

<Compound H133><Compound H134><Compound H135><Compound H136>

<Compound H137><Compound H138><Compound H139><Compound H140>

<Compound H141><Compound H142><Compound H143><Compound H144>

<Compound H145><Compound H146><Compound H147><Compound H148>

<Compound H146><Compound H147><Compound H148><Compound H149>

<Compound H150><Compound H151><Compound H152><Compound H153>

<Compound H154><Compound H155><Compound H156><Compound H157>

<Compound H158><Compound H159><Compound H160><Compound H161>

<Compound H162><Compound H163><Compound H164><Compound H165>

<Compound H166><Compound H167><Compound H168><Compound H169>

<Compound H170><Compound H171><Compound H172><Compound H173>

<Compound H174><Compound H175><Compound H176><Compound H177>

<Compound H178><Compound H179><Compound H180><Compound H181>

<Compound H182><Compound H183><Compound H184><Compound H185>

<Compound H186><Compound H187><Compound H188><Compound H189>

<Compound H190><Compound H191><Compound H192><Compound H193>

<Compound H194><Compound H195><Compound H196><Compound H197>

<Compound H198><Compound H199><Compound H200><Compound H201>

<Compound H202><Compound H203><Compound H204><Compound H205>

<Compound H206><Compound H207><Compound H208><Compound H209>

<Compound H210><Compound H211><Compound H212><Compound H213>

<Compound H214><Compound H215><Compound H216><Compound H217>

<Compound H218><Compound H219><Compound H220><Compound H221>

<Compound H222><Compound H223><Compound H224><Compound H225>

<Compound H226><Compound H227><Compound H228><Compound H229>

<Compound H230><Compound H231><Compound H232><Compound H233>

<Compound H234><Compound H235><Compound H236><Compound H237>

<Compound H238><Compound H239><Compound H240><Compound H241>

<Compound H242><Compound H243><Compound H244><Compound H245>

Additionally, in the organic light emitting device according to the present invention, the heterocyclic compound represented by Formula D may be any one selected from the group represented by Formula E1 to Formula E204 below, but is not limited thereto.

<Formula E1><Formula E2><Formula E3><Formula E4>

<Formula E5><Formula E6><Formula E7><Formula E8>

<Formula E9><Formula E10><Formula E11><Formula E12>

<Formula E13><Formula E14><Formula E15><Formula E16>

<Formula E17><Formula E18><Formula E19><Formula E20>

<Formula E21><Formula E22><Formula E23><Formula E24>

<Formula E25><Formula E26><Formula E27><Formula E28>

<Formula E29><Formula E30><Formula E31><Formula E32>

<Formula E33><Formula E34><Formula E35><Formula E36>

<Formula E37><Formula E38><Formula E39><Formula E40>

<Formula E41><Formula E42><Formula E43><Formula E44>

<Formula E45><Formula E46><Formula E47><Formula E48>

<Formula E49><Formula E50><Formula E51><Formula E52>

<Formula E53><Formula E54><Formula E55><Formula E56>

<Formula E57><Formula E58><Formula E59><Formula E60>

<Formula E61><Formula E62><Formula E63><Formula E64>

<Formula E65><Formula E66><Formula E67><Formula E68>

<Formula E69><Formula E70><Formula E71><Formula E72>

<Formula E73><Formula E74><Formula E75><Formula E76>

<Formula E77><Formula E78><Formula E79><Formula E80>

<Formula E81><Formula E82><Formula E83><Formula E84>

<Formula E85><Formula E86><Formula E87><Formula E88>

<Formula E89><Formula E90><Formula E91><Formula E92>

<Formula E93><Formula E94><Formula E95><Formula E96>

<Formula E97><Formula E98><Formula E99><Formula E100>

<Formula E101><Formula E102><Formula E103><Formula E104>

<Formula E105><Formula E106><Formula E107><Formula E108>

<Formula E109><Formula E110><Formula E111><Formula E112>

<Formula E113><Formula E114><Formula E115><Formula E116>

<Formula E117><Formula E118><Formula E119><Formula E120>

<Formula E121><Formula E122><Formula E123><Formula E124>

<Formula E125><Formula E126><Formula E127><Formula E128>

<Formula E129><Formula E130><Formula E131><Formula E132>

<Formula E133><Formula E134><Formula E135><Formula E136>

<Formula E137><Formula E138><Formula E139><Formula E140>

<Formula E141><Formula E142><Formula E143><Formula E144>

<Formula E145><Formula E146><Formula E147><Formula E148>

<Formula E149><Formula E150><Formula E151><Formula E152>

<Formula E153><Formula E154><Formula E155><Formula E156>

<Formula E157><Formula E158><Formula E159><Formula E160>

<Formula E161><Formula E162><Formula E163><Formula E164>

<Formula E165><Formula E166><Formula E167><Formula E168>

<Formula E169><Formula E170><Formula E171><Formula E172>

<Formula E173><Formula E174><Formula E175><Formula E176>

<Formula E177><Formula E178><Formula E179><Formula E180>

<Formula E181><Formula E182><Formula E183><Formula E164>

<Formula E185><Formula E186><Formula E187><Formula E188>

<Formula E189><Formula E190><Formula E191><Formula E192>

<Formula E193><Formula E194><Formula E195><Formula E196>

<Formula E197><Formula E198><Formula E199><Formula E200>

<Formula E201><Formula E202><Formula E203><Formula E204>

Meanwhile, in the present invention, when the substituent R4 in Structural Formulas 1 to 3 in Formula A is a single bond bonded to the linking group L1, the effect of long life can be further exhibited and efficiency can be improved.

Additionally, as a preferred embodiment of the present invention, the present invention includes a first electrode; a second electrode opposite the first electrode; And a light-emitting layer interposed between the first electrode and the second electrode; In the present invention, the condensed ring compound represented by [Formula A] and the heterocyclic compound represented by [Formula D] are each It can be used as a host in the light emitting layer.

Here, the condensed ring compound represented by [Formula A] and the heterocyclic compound represented by [Formula D] may be mixed at a weight ratio in the range of 1:9 to 9:1.

In addition, the organic light-emitting device according to the present invention may have a dopant added to the light-emitting layer, and in this case, the content of the dopant in the light-emitting layer is typically in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host. It may be selected, but is not limited to this.

In addition, examples of the dopant compound may be one or more compounds selected from compounds represented by the following general formulas (A-1) to (J-1), but are not limited thereto.

[General formula A-1]

The M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh and Re. , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, L ₁ , L ₂ and L ₃ may be the same as or different from each other as ligands and may each independently be one selected from the following structural formula D, but are not limited thereto.

In addition, “*” in the structural formula D below represents a site that coordinates with the metal ion M.

[Structural Formula D]

In the structural formula D, the R are different from or the same as each other and are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or an unsubstituted heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted alkene having 2 to 30 carbon atoms. Nyl group, substituted or unsubstituted alkylamino group with 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 1 to 30 carbon atoms, substituted or unsubstituted arylamino group with 6 to 30 carbon atoms, and substituted or unsubstituted 6 to 30 carbon atoms. It may be any one selected from 30 arylsilyl groups;

The R is each independently selected from an alkyl group with 1 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, an aryl group with 6 to 40 carbon atoms, a heteroaryl group with 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen. may be further substituted with one or more substituents;

In addition, R may be connected to each adjacent substituent with alkylene or alkenylene to form a cyclic ring and a monocyclic or polycyclic aromatic ring;

The L may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or fused ring.

As an example, the dopant represented by [Formula A-1] may be any one selected from the following compounds.

[General formula B-1]

In the general formula B-1,

M ^A1 represents the same metal ion as defined in general formula (A-1), and Y ^A11 , Y ^A14 , Y ^A15 , and Y ^A18 each independently represent a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, and L ^A11 , L ^A12 , L ^A13 , and L ^A14 are each a linking group as previously defined. , and Q ^A11 and Q ^A12 represent partial structures containing atoms bonded to M ^A1 .

An exemplary structure of the compound represented by the general formula B-1 is as follows, but is not limited thereto.

[General formula C-1]

In the general formula C-1,

M ^B1 represents the same metal ion as defined in General Formula A-1, Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, and Q ^B11 and Q ^B12 represent M It represents the partial structure containing the atom bonded to ^B1 .

An exemplary structure of the compound represented by the general formula C-1 is as follows, but is not limited thereto.

[General formula D-1]

In the general formula D-1,

M ^C1 represents the same metal ion as defined in General Formula A-1, and R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent that connects to each other to form a 5-ring ring, and a substituent that does not connect to each other. R ^C13 and R ^C14 each independently represent a hydrogen atom, a substituent connected to each other to form a 5-ring ring, and a substituent not connected to each other, and G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituted or unsubstituted group. It represents a carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

An exemplary structure of the compound represented by the general formula D-1 is as follows, but is not limited thereto.

[General formula E-1]

In the general formula E-1,

M ^D1 represents the same metal ion as defined in general formula (A-1), G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, J ^D11 , J ^D12 , J ^D13 and J ^D14 each independently represents an atom group necessary to form a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

An exemplary structure of the compound represented by the general formula E-1 is as follows, but is not limited thereto.

[General formula F-1]

In the general formula F-1,

M ^E1 represents the same metal ion as defined in General Formula A-1, and J ^E11 and J ^E12 each independently represent the atomic groups required to form a five-membered ring, G ^E11 , G ^E12 , and G ^E13. and G ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom or a substituted or unsubstituted carbon atom.

An exemplary structure of the compound represented by the general formula F-1 is as follows, but is not limited thereto.

[General formula G-1]

In the general formula G-1,

M ^F1 represents the same metal ion as defined in General Formula A-1,

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, R ^F11 and R ^F12 , R ^F12 and R ^F13 , R ^F13 and R ^F14 are connected to each other It can form a ring, and in this case, the ring formed by R ^F1 , R ^F12 , R ^F13 , and R ^F14 is a 5-membered ring. Additionally, Q ^F11 and Q ^F12 represent partial structures containing atoms bonded to M ^F1 .

An exemplary structure of the compound represented by the general formula G-1 is as follows, but is not limited thereto.

[General formula H-1] [General formula H-2] [General formula H-3]

In the general formula H-1,

R ¹¹ , R ¹² are substituents of alkyl, aryl or heteroaryl; In addition, a fused ring can be formed with substituents adjacent to each other, and q11 and q12 are integers from 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 are the same or different, respectively,

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, and more preferably an ortho metal (ortho metal) platinum complex. metal) It is a ligand that forms a white gold complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer from 0 to 3, preferably 0, and m ¹ is 1 or 2, preferably 2.

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the general formula H-1 a neutral complex.

In the general formula H-2, R ²¹ ,R ²² ,n ² ,m ² ,q ²² ,L ² are the same as R ¹¹ ,R ¹² ,n ¹ ,m ¹ ,q ¹² ,L ¹ respectively, and q ²¹ is an integer from 0 to 2, and 0 is preferable.

In the general formula H-3, R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , L ¹ respectively, and q ³¹ represents an integer from 0 to 8, and 0 to 2 is preferable, and 0 is more preferable.

Specific examples of compounds of the general formulas H-1 to H-3 are as follows, but are not limited thereto.

[General formula I-1]

In the general formula I-1,

Ring A, Ring B, Ring C, and Ring D represent nitrogen-containing heterocycles in which any two rings of rings A to D may have a substituent, and the remaining two rings represent an aryl ring or heteroaryl ring that may have a substituent. It represents a ring, and a condensed ring can be formed with ring A and ring B, ring A and ring C, and/or ring B and ring D. Any ^{two of} X ^{1 ,} Q ¹ , Q ² and Q ³ each independently represent a divalent atom (single) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Any two of Z ¹ , Z ² , Z ³ and Z ⁴ represent a coordination bond, and the other two represent a covalent bond, an oxygen atom, or a sulfur atom.

Specific examples of compounds of the general formula I-1 are as follows, but are not limited thereto.

[General formula J-1]

In the general formula J-1,

M represents the same metal ion as defined in General Formula A-1, Ar1 represents a substituted or unsubstituted ring structure, and in the two azomethine bonds (-C=N-) bonded to M, , the nitrogen atom (N) is each bonded to the M, and as a whole forms a tridentate ligand bonded to the M at the 3rd position.

Additionally, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a single-dentate ligand.

In the general formula J-1, M is preferably Pt. In addition, Ar1 is preferably selected from 5-membered rings, 6-membered rings, and condensed ring groups thereof.

Specific examples of compounds of the general formula J-1 are as follows, but are not limited thereto.

Additionally, the light emitting layer may further include various hosts and various dopant materials in addition to the host and dopant.

When the condensed ring compound represented by Formula A and the heterocyclic compound represented by Formula D in the present invention are used in the light emitting layer, the organic light emitting device can have improved efficiency and long lifespan characteristics.

In addition, the organic light emitting device according to the present invention may additionally include, in addition to the light emitting layer, at least one layer selected from among a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron transport layer, and an electron injection layer. You can.

Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described with reference to the drawings.

1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.

As shown in Figure 1, the organic light emitting device according to an embodiment of the present invention includes an anode 20, a hole transport layer 40, a light emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode ( 80) in sequential order, wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is provided between the anode and the light-emitting layer, and an electron transport layer is provided between the light-emitting layer and the cathode. Applies to organic light emitting devices.

In addition, the organic light emitting device according to an embodiment of the present invention includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron transport layer 60 and the cathode 80. An injection layer 70 may be included.

With reference to Figure 1, the organic light emitting device of the present invention and its manufacturing method will be examined as follows.

First, the positive electrode (anode) material is coated on the upper part of the substrate 10 to form the positive electrode 20. Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO), which are transparent and have excellent conductivity, are used as materials for the anode electrode.

The hole injection layer 30 is formed by vacuum heat deposition or spin coating of a hole injection layer material on the top of the anode 20 electrode. Next, the hole transport layer 40 is formed on the top of the hole injection layer 30 by vacuum thermal evaporation or spin coating of the hole transport layer material.

The hole injection layer material can be used without particular restrictions as long as it is commonly used in the industry, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ], etc. can be used, but the present invention is not necessarily limited thereto.

Additionally, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl -[1,1- Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used. However, the present invention is not necessarily limited thereto.

Subsequently, the light emitting layer 50 may be laminated on the hole transport layer 40 using a vacuum deposition method or a spin coating method.

Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.

Additionally, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.

Meanwhile, the electron transport layer 60 is deposited on the light emitting layer through a vacuum deposition method or a spin coating method, and then the electron injection layer 70 is formed, and the metal for forming the cathode is vacuum formed on the top of the electron injection layer 70. An organic light emitting device (OLED) is completed by forming a cathode 80 electrode through thermal evaporation.

Meanwhile, in the present invention, as the material for the electron transport layer, a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (cathode) can be used. Examples of known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10- olate: Bebq2), Compound 201, Compound 202, oxadiazole derivatives PBD, BMD, BND, etc. may be used, but are not limited thereto.

TAZ BAlq

<Compound 201> <Compound 202>

Additionally, the electron transport layer used in the present invention may be an organometallic compound represented by Chemical Formula F, used alone or in a mixture with the electron transport layer material.

[Formula F]

In the above [Formula F],

Y is a portion selected from C, N, O, and S that is directly bonded to the M to form a single bond, and a portion selected from C, N, O, and S that forms a coordination bond to the M. It is a ligand chelated by the single bond and coordination bond.

The M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom, and the OA is a monovalent ligand capable of single bonding or coordinating with the M,

O is oxygen,

A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms. Alkynyl group, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, and substituted or unsubstituted heteroatoms at least one selected from O, N, S and Si. Any one selected from heteroaryl groups having 2 to 50 carbon atoms,

When M is a metal selected from alkali metals, m = 1, n = 0,

When M is a metal selected from alkaline earth metals, m = 1, n = 1, or m = 2, n = 0,

When M is boron or aluminum, m = any one of 1 to 3, n is any one of 0 to 2 and satisfies m + n = 3;

'Substitution' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means being substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus, and boron.

In the present invention, Y may be the same or different, and may be independently selected from [Structural Formula C1] to [Structural Formula C39] below, but is not limited thereto.

[Structural Formula C1][Structural Formula C2][Structural Formula C3]

[Structural Formula C4][Structural Formula C5][Structural Formula C6]

[Structural Formula C7][Structural Formula C8][Structural Formula C9][Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14][Structural Formula C15][Structural Formula C16]

[Structural Formula C17][Structural Formula C18][Structural Formula C19][Structural Formula C20]

[Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[Structural Formula C24][Structural Formula C25][Structural Formula C26]

[Structural Formula C27][Structural Formula C28][Structural Formula C29][Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34][Structural Formula C35][Structural Formula C36]

[Structural Formula C37][Structural Formula C38][Structural Formula C39]

In the above [structural formula C1] to [structural formula C39],

R are the same or different from each other, and are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or An unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms. It may be selected from the group and connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

In addition, in the organic light emitting device of the present invention, an electron injection layer (EIL), which is a material that has the function of facilitating injection of electrons from the cathode, may be laminated on the electron transport layer, and the material is not particularly limited.

As the electron injection layer forming material, any material known as an electron injection layer forming material such as CsF, NaF, LiF, NaCl, Li ₂ O, BaO, etc. can be used. The deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are almost the same as those for forming the hole injection layer.

The thickness of the electron injection layer may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

In addition, in the present invention, the negative electrode includes lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( A cathode forming metal such as Mg-Ag) can be used, or a transmissive cathode using ITO or IZO can be used to obtain a top-emitting device.

Additionally, the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.

Additionally, in the present invention, one or more layers selected from each of the above layers may be formed by a single molecule deposition process or a solution process.

Here, the deposition process refers to a method of forming a thin film by evaporating the material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used to form each layer. It refers to a method of mixing a substance used as a material with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, and spin coating.

Additionally, the organic light emitting device in the present invention may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and a monochromatic or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

(Example)

Synthesis Example 1. Synthesis of Compound H1

Synthesis Example 1-(1): Synthesis of Intermediate 1-a

[Intermediate 1-a]

In a round bottom flask, 2-bromonaphthol (50g, 224mmol), bis(pinacolato)diborane (74g, 291mmol), tris(dibenzylideneacetone)palladium (8.2g, 11.2mmol), potassium acetate (63.9g) , 672 mmol), 500 ml of 1,4-dioxane was added under nitrogen conditions and refluxed. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 1-a]. (48.4g, 80%)

Synthesis Example 1-(2): Synthesis of Intermediate 1-b

[Intermediate 1-a] [Intermediate 1-b]

1-Bromo-3-fluoro-2-iodobenzene (48 g, 177 mmol), [Intermediate 1-a] (69.5 g, 231 mmol), (diphenylphosphine) palladium dichloride in a round bottom flask under nitrogen atmosphere. (2.4g, 3.5mmol), hydrazine monohydrate (0.3g, 5.3mmol), sodium tetraborate (53.6g, 266mmol), 500ml of 1,4-dioxane, and 400ml of water were added and refluxed for 24 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, the organic layer was concentrated, separated by column chromatography, and dried to obtain [Intermediate 1-b]. (36.6g, 65%)

Synthesis Example 1-(3): Synthesis of Intermediate 1-c

[Intermediate 1-b] [Intermediate 1-c]

[Intermediate 1-b] (34 g, 107 mmol), potassium carbonate (23.7 g, 171 mmol), and 350 ml of N-methyl-2-pyrrolidinone were added to a round bottom flask under a nitrogen atmosphere and refluxed at 150 degrees for 4 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated by column chromatography, and dried to obtain [Intermediate 1-c]. (28.3g, 89%)

Synthesis Example 1-(4): Synthesis of Compound H1

[Intermediate 1-c] [Compound H1]

In a round bottom flask, [Intermediate 1-c] (10g, 33.6mmol), bis(4-bipalyl)amine (11.8g, 37mmol), tris(dibenzylideneacetone)palladium (0.8g, 0.84mmol), 2, 2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.9g, 1.34mmol), sodium tertiary butoxide (8g, 84.1mmol), and 120ml of toluene were added under nitrogen conditions and incubated for 12 hours. It was refluxed. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Compound H1]. (11.7g, 65%)

MS (MALDI-TOF): m/z 537.21[M ⁺ ]

Synthesis Example 2. Synthesis of Compound H2

Synthesis Example 2-(1): Synthesis of Compound H2

[Intermediate 1-d] [Compound H2]

[Compound H2 ] was obtained. (9.6g, 49%)

MS (MALDI-TOF): m/z 577.24[M ⁺ ]

Synthesis Example 3. Synthesis of Compound H3

Synthesis Example 3-(1): Synthesis of Compound H3

[Intermediate 1-d] [Compound H3]

[Compound H3] was obtained by synthesis in the same manner except that bis(9,9'-dimethylfluorenyl)amine was used instead of bis(4-bipalyl)amine used in Synthesis Example 1-(4). (10.2g, 49%)

MS (MALDI-TOF): m/z 617.27[M ⁺ ]

Synthesis Example 4. Synthesis of Compound H10

Synthesis Example 4-(1): Synthesis of Intermediate 4-a

[Intermediate 4-a]

In a round bottom flask, 3-bromobiphenyl (30g, 128mmol), 2-amino-9,9'-dimethylfluorene (29.6g, 141mmol), tris(dibenzylideneacetone)palladium (2.9g, 3.21mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (3.2g, 5.14mmol), sodium tertiary butoxide (30.9g, 321mmol), and 300ml of toluene were added under nitrogen conditions and added at 12 It was refluxed for an hour. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 4-a]. (33g, 71%)

Synthesis Example 4-(2): Synthesis of Compound H10

[Intermediate 1-d] [Intermediate 4-a] [Compound H10]

[Compound H10] was obtained by synthesis in the same manner, except that [Intermediate 4-a] was used instead of the bis(4-bipalyl)amine used in Synthesis Example 1-(4). (8.2g, 42%)

MS (MALDI-TOF): m/z 577.24[M ⁺ ]

Synthesis Example 5. Synthesis of Compound H33

Synthesis Example 5-(1): Synthesis of Intermediate 5-a

[Formula 5-a]

In the same manner as the synthesis methods from Synthesis Examples 1-(1) to 1-(3), except that 3-bromo-2-naphthol was used instead of 2-bromonaphthol in Synthesis Example 1-(1). By synthesis, [Intermediate 5-a] was obtained (25g, 62%).

Synthesis Example 5-(2): Synthesis of Compound H33

[Intermediate 5-a] [Compound H33]

[Compound H33] was obtained by synthesis in the same manner, except that [Intermediate 5-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4). (15.7g, 87%)

MS (MALDI-TOF): m/z 537.21[M ⁺ ]

Synthesis Example 6. Synthesis of Compound H34

Synthesis Example 6-(1): Synthesis of Compound H34

[Intermediate 5-a] [Compound H34]

[Intermediate 5-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4), and instead of bis(4-biphenyl)amine, 2-(4-biphenylyl)amino-9.9'- [Compound H34] was obtained by synthesis in the same manner except that dimethylfluorene was used. (14.3g, 74%)

MS (MALDI-TOF): m/z 577.24[M ⁺ ]

Synthesis Example 7. Synthesis of Compound H35

Synthesis Example 7-(1): Synthesis of Compound H35

[Intermediate 5-a] [Compound H35]

[Intermediate 5-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4), and bis(9,9'-dimethylfluorenyl)amine was used instead of bis(4-bipalyl)amine. [Compound H35] was obtained by synthesizing in the same manner except. (12.8g, 62%)

MS (MALDI-TOF): m/z 617.27[M ⁺ ]

Synthesis Example 8. Synthesis of Compound H61

Synthesis Example 8-(1): Synthesis of Intermediate 8-a

[Intermediate 8-a]

In Synthesis Example 1-(1), 1-bromo-2-naphthol was used instead of 2-bromonaphthol, and in 1-(2), 4-bromo-3-fluoro-2-iodobenzene was used instead of 1-bromo-3-fluoro-2-iodobenzene. [Intermediate 8-a] was obtained by synthesizing in the same manner as in Synthesis Examples 1-(1) to 1-(3), except that bromo-1-fluoro-2-iodobenzene was used. . (22g, 83%)

Synthesis Example 8-(2): Synthesis of Compound H61

[Intermediate 8-a] [Compound H61]

[Compound H61] was obtained by synthesis in the same manner, except that [Intermediate 8-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4). (13.3g, 74%)

MS (MALDI-TOF): m/z 537.21[M ⁺ ]

Synthesis Example 9. Synthesis of Compound H63

Synthesis Example 9-(1): Synthesis of Compound H63

[Intermediate 8-a] [Compound H63]

[Intermediate 8-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4), and bis(9,9'-dimethylfluorenyl)amine was used instead of bis(4-bipalyl)amine. [Compound H63] was obtained by synthesizing in the same manner except that (10.3g, 50%).

MS (MALDI-TOF): m/z 617.27[M ⁺ ]

Synthesis Example 10. Synthesis of Formula E1

Synthesis Example 10-(1): Synthesis of Intermediate 10-a

[Intermediate 10-a]

Put 2-bromobenzophenanthrene (50g, 162mmol) in a round bottom flask, add 500ml of tetrahydrofuran under a nitrogen atmosphere, lower the temperature to -78℃, and then slowly add 1.6M n-butyllithium (112ml, 179mmol) dropwise. I give it to you. After 1 hour, trimethyl borate (20.3 ml, 195 mmol) was slowly added while maintaining low temperature, and the temperature was raised to room temperature and stirred. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to obtain [Intermediate 10-a]. (36.3g, 82%)

Synthesis Example 10-(2): Synthesis of Intermediate 10-b

[Intermediate 10-a] [Intermediate 10-b]

[Intermediate 10-a] (20 g, 73.5 mmol), 1-bromo-3-iodobenzene (24.9 g, 88.2 mmol), tetrakis(triphenylphosphine)palladium (1.7 g) in a round bottom flask under nitrogen atmosphere. , 1.4 mmol), potassium carbonate (20.3 g, 147 mmol), 200 ml of toluene, and 70 ml of water were added and refluxed for 24 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated by column chromatography, and dried to obtain [Intermediate 10-b]. (21.1g, 75%)

Synthesis Example 10-(3): Synthesis of Intermediate 10-c

[Intermediate 10-b] [Intermediate 10-c]

[Intermediate 10-c] was obtained by synthesis in the same manner, except that [Intermediate 10-b] was used instead of 2-bromonaphthol used in Synthesis Example 1-(1). (18.3 g, 77%)

Synthesis Example 10-(4): Synthesis of Formula E1

[Intermediate 10-c] [Formula E1]

2-Chloro-4,6-diphenyl-1,3,5-triazine (15 g, 56 mmol), [Intermediate 10-c] (24.1 g, 56 mmol), tetrakis(triphenyl) in a round bottom flask under nitrogen atmosphere. Phosphine) palladium (1.3 g, 1.1 mmol), potassium carbonate (15.5 g, 112 mmol), 150 ml of toluene, and 40 ml of water were added and refluxed for 24 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated by column chromatography, and dried to obtain [Formula E1]. (22.5g, 75%)

MS (MALDI-TOF): m/z 535.20[M ⁺ ]

Synthesis Example 11. Synthesis of Formula E4

Synthesis Example 11-(1): Synthesis of Intermediate 11-a

[Intermediate 11-a]

Except that dibenzofuran-2-boronic acid was used instead of [Intermediate 10-a] used in Synthesis Example 10-(2) and 4-iodophenylboronic acid was used instead of 1-bromo-3-iodobenzene. Then, it was synthesized in the same manner to obtain [Intermediate 11-a]. (35g, 46%)

Synthesis Example 11-(2): Synthesis of Formula E4

[Intermediate 11-a] [Formula E4]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 10-(4), 2-(3-bromophenyl)-4,6-diphenylpyrimidine was used. and synthesized in the same manner except that [Intermediate 11-a] was used instead of [Intermediate 10-c] to obtain [Formula E4]. (16.3g, 74%)

MS (MALDI-TOF): m/z 550.20[M ⁺ ]

Synthesis Example 12. Synthesis of Formula E15

Synthesis Example 12-(1): Synthesis of Intermediate 12-a

[Intermediate 12-a]

Dibenzothiophene-2-boronic acid was used instead of [Intermediate 10-a] used in Synthesis Example 10-(2), and (3-iodophenyl)boronic acid was used instead of 1-bromo-3-iodobenzene. [Intermediate 12-a] was obtained by synthesis in the same manner except that . (22 g, 57%)

Synthesis Example 12-(2): Synthesis of formula E15

[Intermediate 12-a] [Compound E15]

[Intermediate 12-a] was used instead of [Intermediate 10-c] used in Synthesis Example 10-(4), and 2-(3) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. -Bromophenyl)-4,6-diphenyl-1,3,5triazine was synthesized in the same manner to obtain [Formula E15]. (12 g, 71%)

MS (MALDI-TOF): m/z 567.18[M ⁺ ]

Synthesis Example 13. Synthesis of Formula E40

Synthesis Example 13-(1): Synthesis of Formula E40

[화학식 E40]

[Formula E40]

Phenyl boronic acid was used instead of [Intermediate 10-a] used in Synthesis Example 10-(2), and 2-(4-bromo-phenyl)-4-phenyl-quina was used instead of 1-bromo-3-iodobenzene. [Chemical formula E40] was obtained by synthesizing in the same manner except that zoline was used. (13 g, 66%)

MS (MALDI-TOF): m/z 358.15[M ⁺ ]

Synthesis Example 14. Synthesis of Formula E53

Synthesis Example 14-(1): Synthesis of Intermediate 14-a

[Intermediate 14-a]

In a 1L round bottom flask, 4-bromo-2-iodoaniline (30g, 100mmol), 4-chlorophenol (12.9g, 100mmol), copper iodide (1g, 5.0mmol), iron (III) acetylacetonate (1.1 g, 3.0 mmol), potassium carbonate (27.8 g, 201 mmol), and 400 ml of toluene were added under nitrogen conditions and refluxed for 12 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 14-a]. (20g, 67%)

Synthesis Example 14-(2): Synthesis of Intermediate 14-b

[Intermediate 14-a] [Intermediate 14-b]

[Intermediate 14-a] (20 g, 6.9 mmol) and p-toluenesulfonic acid (38.2 g, 200 mmol) were added to 500 ml of acetonitrile in a 1L beaker and stirred. After lowering the temperature to 0°C, sodium nitrite (9.2 g, 134 mmol) was dissolved in 30 ml of water and slowly added dropwise while the temperature was maintained. After 30 minutes, potassium iodide (27.8 g, 167 mmol) was dissolved in 70 ml of water and stirred at room temperature. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 14-b]. (19 g,69%)

Synthesis Example 14-(3): Synthesis of Intermediate 14-c

[Intermediate 14-b] [Intermediate 14-c]

[Intermediate 14-b] (19g, 46.4mmol), tetrakis(triphenylphosphine)palladium (1g, 0.9mmol), potassium acetate (5.5g, 55.6mmol), and 200ml of dimethylformaldehyde were added to a 500ml round bottom flask under nitrogen. It was added under normal conditions and refluxed for 12 hours. After completion of the reaction, the reactants were separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 14-c]. (10g, 77%)

Synthesis Example 14-(4): Synthesis of Intermediate 14-d

[Intermediate 14-c] [Intermediate 14-d]

[Intermediate 14-d] was obtained by synthesis in the same manner except that [Intermediate 13-c] was used instead of 2-bromobenzophenanthrene used in Synthesis Example 10-(1). (7.8 g, 89%)

Synthesis Example 14-(5): Synthesis of intermediate 14-e

[Intermediate 14-d] [Intermediate 14-e]

In Synthesis Example 1-(2), [Intermediate 14-d] was used instead of [Intermediate 1-a], and methyl-2-iodobenzoate was used instead of 1-bromo-3-fluoro-2-iodobenzene. [Intermediate 14-e] was obtained using the same method except that it was used. (9.3g, 87%)

Synthesis Example 14-(6): Synthesis of intermediate 14-f

[Intermediate 14-e] [Intermediate 14-f]

Add [Intermediate 14-e] (33.5 g, 99 mmol) to a round bottom flask containing 150 ml of tetrahydrofuran, lower the temperature to -10 degrees, and then slowly add 3M methylmagnesium bromide (85 ml, 254 mmol) dropwise. Afterwards, heat the temperature to 40 degrees and stir for 4 hours. Afterwards, lower the temperature to -10 degrees, slowly add 70ml of 2N salt ginseng dropwise, add 70ml of ammonium chloride aqueous solution, and raise the temperature to room temperature. After completion of the reaction, the reactant was washed with water, extracted with ethyl acetate, separated into layers, and the organic layer was concentrated under reduced pressure, separated on a column, and dried to obtain [Intermediate 14-f]. (26.5g, 79%)

Synthesis Example 14-(7): Synthesis of intermediate 14-g

[Intermediate 14-f] [Intermediate 14-g]

[Intermediate 14-f] (26 g, 77.2 mmol) and 70 ml of phosphoric acid were added to a round bottom flask under a nitrogen atmosphere and stirred at room temperature for 12 hours. After completion of the reaction, extraction was performed with ethyl acetate and water, the organic layer was concentrated, separated by column chromatography, and dried to obtain [Intermediate 14-g]. (18.5g, 75%)

Synthesis Example 14-(8): Synthesis of intermediate 14-h

[Intermediate 14-g] [Intermediate 14-h]

[Intermediate 14-h] was obtained by synthesis in the same manner, except that [Intermediate 14-g] was used instead of 2-bromonaphthol used in Synthesis Example 1-(2). (15.1g, 63%)

Synthesis Example 14-(9): Synthesis of Formula E53

[Intermediate 14-h] [Formula E53]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 10-(5), 2-chloranyl-4-(9,9-dimethylfluoren-2-yl) ) Quinazoline was used and [Formula E53] was obtained by synthesizing in the same manner except that [Intermediate 14-h] was used instead of [Intermediate 10-c]. (12.3g, 55%)

MS (MALDI-TOF): m/z 604.25[M ⁺ ]

Synthesis Example 15. Synthesis of Formula E54

Synthesis Example 15-(1): Synthesis of Intermediate 15-a

[Intermediate 15-a]

[Intermediate] was synthesized in the same manner as in Synthesis Examples 14-(1) to 14-(8), except that 3-monochlorophenol was used instead of 4-chlorophenol in Synthesis Example 14-(1). 15-a] was obtained. (6.9g, 63.8%)

Synthesis Example 15-(2): Synthesis of Formula E54

[Intermediate 15-a] [Formula E54]

[Formula E54] was obtained by synthesis in the same manner, except that [Intermediate 15-a] was used instead of [Intermediate 10-c] used in Synthesis Example 10-(5). (5.8g, 53.3%)

MS (MALDI-TOF): m/z 515.20[M ⁺ ]

Synthesis Example 16. Synthesis of Formula E100

Synthesis Example 16-(1): Synthesis of intermediate 16-a

[Intermediate 16-a]

Add 2-cyanophenol (24.5 g, 206 mmol), 2-bromoacetophenone (40.9 g, 206 mmol), potassium carbonate (85.3 g, 617 mmol), and 980 mL of acetone to a 2 L round bottom flask reactor and react at 60°C for 12 days. Stir for an hour. After completion of the reaction, the reaction solution is cooled to room temperature and filtered with acetone. The filtrate was concentrated and recrystallized with heptane to obtain [Intermediate 16-a]. (37g, 75%)

Synthesis Example 16-(2): Synthesis of Intermediate 16-b

[Intermediate 16-a] [Intermediate 16-b]

Add [Intermediate 16-a] (14 g, 58.5 mmol), urea (11.7 g, 195 mmol), and 70 mL of acetic acid to a 300 mL round bottom flask reactor and reflux and stir for 12 hours. After the reaction is completed, excess water is added to the reactant, allowed to precipitate, and then filtered. [Intermediate 16-b] was obtained by hot slurry with methanol and then filtered and dried. (9.3 g, 61%)

Synthesis Example 16-(3): Synthesis of intermediate 16-c

[Intermediate 16-b] [Intermediate 16-c]

Add [Intermediate 16-b] (9.3 g, 35.4 mmol) and 45 mL of phosphorus oxychloride to a 300 mL round bottom flask reactor and reflux and stir for 12 hours. After the reaction is completed, the reactant is slowly added to excess water at 0°C, the solid is precipitated, and then filtered. The solid was dissolved in dichlorobenzene, filtered under reduced pressure in a hot state, and recrystallized to obtain [Intermediate 16-c]. (7.0g, 70%)

Synthesis Example 16-(4): Synthesis of Formula E100

[Intermediate 16-c] [Formula E100]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 10-(5), [Intermediate 16-c] was used, and instead of [Intermediate 10-c], 4,4, [Formula E100] was synthesized in the same manner except that 5,5-titramethyl-2-(3-(phenanthren-9-yl)phenyl)-1,3,2,-dioxaborolene was used. got it (8.1g, 65%)

MS (MALDI-TOF): m/z 498.17[M ⁺ ]

Synthesis Example 17. Synthesis of Formula E124

Synthesis Example 17-(1): Synthesis of Intermediate 17-a

[Intermediate 17-a]

Add 4-dibenzofuranboronic acid (64 g, 302 mmol), bismuth (Ⅲ) nitrate pentahydrate (102.5 g, 211 mmol), and 640 ml of toluene to a dried 2 L reactor and reflux and stir for 6 hours. After lowering the temperature, if a solid is formed, it is removed by filtration with dichloromethane. The filtrate was concentrated and separated by column chromatography to obtain [Intermediate 17-a]. (48g, 75%)

Synthesis Example 17-(2): Synthesis of Intermediate 17-b

[Intermediate 17-a] [Intermediate 17-b]

Add potassium cyanide (15.8 g, 243 mmol), potassium hydroxide (24.7 g, 441 mmol), ethyl cyanoacetate (74.8 g, 661 mmol), and 380 ml of dimethylformamide to a dried 2 L round bottom flask reactor and stir. . [Intermediate 17-a] (47 g, 220 mmol) was dissolved in 90 ml of dimethylformamide and added dropwise at 20°C. Reflux and stir at 60°C for 12 hours. Add 250 ml of 5% sodium hydroxide and reflux and stir for 2 hours. After completion of the reaction, slowly add the reaction solution to 1500 mL of water, crystallize, and filter. The filtered solid was dissolved in tetrahydrofuran and separated by column chromatography to obtain [Intermediate 17-b]. (31g, 68%)

Synthesis Example 17-(3): Synthesis of intermediate 17-c

[Intermediate 17-b] [Intermediate 17-c]

[Intermediate 17-b] (11 g, 52.8 mmol) was added to a dried 500 ml round bottom flask reactor with 55 ml of tetrahydrofuran and stirred. 3 M phenylmagnesium bromide (37 ml, 101 mmol) and 33 ml of tetrahydrofuran were slowly added dropwise at 0°C and stirred under reflux for 2 hours. Add 6N hydrochloric acid dropwise at 0°C and stirred under reflux for 1 hour. Add 6 N sodium hydroxide at room temperature to adjust pH to 8 and extract with water and ethyl acetate. The organic layer was concentrated and recrystallized with dichloromethane and heptane to obtain [Intermediate 17-c]. (12.3g, 81%)

Synthesis Example 17-(4): Synthesis of intermediate 17-d

[Intermediate 17-c] [Intermediate 17-d]

[Intermediate 17-d] was obtained by synthesis in the same manner, except that [Intermediate 17-c] was used instead of [Intermediate 16-a] used in Synthesis Example 16-(2). (9.3g, 70%)

Synthesis Example 17-(5): Synthesis of intermediate 17-e

[Intermediate 17-d] [Intermediate 17-e]

[Intermediate 17-e] was obtained by synthesis in the same manner, except that [Intermediate 17-d] was used instead of [Intermediate 16-b] used in Synthesis Example 16-(3). (8.1g, 82%)

Synthesis Example 17-(6): Synthesis of intermediate 17-f

[Intermediate 17-f]

4 naphthalene-2-boronic acid was used instead of [Intermediate 10-a] used in Synthesis Example 10-(2), and 4-bromo-4-iodobiphenyl was used instead of 1-bromo-3-iodobenzene. [Intermediate 17-f] was obtained by synthesis in the same manner except that. (13 g, 66%)

Synthesis Example 17-(7): Synthesis of intermediate 17-g

[Intermediate 17-f] [Intermediate 17-g]

[Intermediate 17-g] was obtained by synthesis in the same manner, except that [Intermediate 17-f] was used instead of 2-bromobenzophenanthrene used in Synthesis Example 10-(1). (10.3 g, 72%)

Synthesis Example 17-(6): Synthesis of formula E124

[Intermediate 17-e] [Intermediate 17-g] [Formula E124]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 10-(5), [Intermediate 17-e] was used, and [Intermediate 17-e] was used instead of [Intermediate 10-c]. [Chemical formula E124] was obtained by synthesizing in the same manner except that [g] was used. (7.8g, 55%)

MS (MALDI-TOF): m/z 574.20[M ⁺ ]

Synthesis Example 18. Synthesis of Formula E138

Synthesis Example 18-(1): Synthesis of Intermediate 18-a

[Intermediate 18-a]

[Intermediate 18-a] was synthesized in the same manner except that 2-chloranylphenanthro(9,10-d)pyrimidine was used instead of 2-bromobenzophenanthrene used in Synthesis Example 10-(1). ] was obtained. (33g, 63.7%)

Synthesis Example 18-(2): Synthesis of Chemical Formula E138

[Intermediate 18-a] [Formula E138]

[Intermediate 18-a] was used instead of [Intermediate 10-a] used in Synthesis Example 10-(2), and 3-(3'-bromophenyl)pyridine was used instead of 1-bromo-3-iodobenzene. [Formula E138] was obtained by synthesizing in the same manner except that. (11 g, 76%)

MS (MALDI-TOF): m/z 383.14[M ⁺ ]

Example: Preparation of organic light emitting device

Examples 1 to 14

The ITO glass was patterned so that the light emitting area was 2 mm x 2 mm in size and then cleaned. After mounting the substrate in a vacuum chamber and setting the base pressure to 1x10 ^-6 torr, organic materials were applied on the ITO such as HATCN (50Å), NPD (1500Å), and compound H1 prepared according to the present invention as shown in Table 1 below. The weight ratio between H63 and formulas E1 to E138 was set to 5:5 (phosphorescent host) + red phosphorescent dopant (RD, 5%, 400Å), as an electron transport layer and an electron injection layer, as shown below. ET: Films were formed in the following order: Liq = 1:1 (300Å), Liq (10Å), and Al (1,000Å), and measurements were made at 0.4 mA.

<HATCN> <NPD> <RD>

<ET> <Liq>

Comparative Example 1

The organic light emitting diode device for Comparative Example 1 was the same as the device structures of Examples 1 to 14 except that BAlq, which is commonly used as a phosphorescent host material, was used instead of the compound (host) prepared by the invention. It was manufactured, and the structure of BAlq is as follows.

<BAlq>

Comparative Examples 2 to 19

Comparative Examples 2 to 19 used only one type of host when forming the light emitting layer, and co-deposited compounds H1 to H63 and RD at a weight ratio of 5 wt% (using only the first host), or used compounds of formulas E1 to E138 and RD An organic light-emitting device was manufactured using the same method as Examples 1 to 14, except that it was co-deposited at a weight ratio of 5 wt% (only the second host was used).

Evaluation example

For the organic electroluminescent devices manufactured according to Examples 1 to 14 and Comparative Examples 1 to 19, the voltage, current density, luminance, color coordinates, and lifespan were measured and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (3700 cd/m ² ) to 95%.

first host 2nd host content ratio
(wt/wt) driving voltage
(V) Luminous efficiency (cd/A) CIEx CIey T95 Comparative Example 1 Blaq One 6.2 14.7 0.665 0.334 40 Comparative example 2 Compound H1 One 4.5 5.5 0.667 0.333 5 Comparative example 3 Compound H2 One 4.8 4.5 0.665 0.335 10 Comparative example 4 Compound H3 One 4.8 3.8 0.666 0.334 10 Comparative Example 5 Compound H10 One 5.0 4.2 0.663 0.337 15 Comparative Example 6 Compound H33 One 4.6 4.1 0.665 0.335 5 Comparative example 7 Compound H34 One 4.7 5.0 0.667 0.333 5 Comparative example 8 Compound H35 One 4.8 3.9 0.665 0.335 10 Comparative Example 9 Compound H61 One 5.0 4.6 0.663 0.336 5 Comparative Example 10 Compound H63 One 4.9 4.5 0.666 0.334 10 Comparative Example 11 Formula E1 One 3.2 10.0 0.665 0.335 20 Comparative Example 12 Formula E4 One 3.1 10.3 0.665 0.335 25 Comparative Example 13 Formula E15 One 3.3 10.2 0.663 0.338 24 Comparative Example 14 Chemical formula E40 One 3.3 10.5 0.664 0.339 22 Comparative Example 15 Chemical formula E53 One 3.1 10.5 0.664 0.336 20 Comparative Example 16 Chemical formula E54 One 3.2 10.0 0.662 0.337 19 Comparative Example 17 Chemical formula E100 One 3.1 10.3 0.665 0.335 20 Comparative Example 18 Formula E124 One 3.4 10.0 0.666 0.333 23 Comparative Example 19 Formula E138 One 3.2 9.9 0.663 0.331 18 Example 1 Compound H1 Formula E1 5:5 4.0 25.2 0.667 0.333 230 Example 2 Compound H2 Formula E1 5:5 3.9 25.1 0.666 0.334 240 Example 3 Compound H3 Formula E4 5:5 3.8 21.3 0.667 0.333 200 Example 4 Compound H10 Formula E4 5:5 4.0 22.2 0.667 0.333 205 Example 5 Compound H33 Formula E15 5:5 4.1 21.9 0.665 0.335 200 Example 6 Compound H34 Chemical formula E40 5:5 4.0 21.5 0.655 0.335 220 Example 7 Compound H35 Chemical formula E53 5:5 3.7 22.8 0.667 0.333 230 Example 8 Compound H61 Chemical formula E54 5:5 3.9 20.3 0.667 0.333 160 Example 9 Compound H63 Chemical formula E100 5:5 4.2 19.8 0.663 0.337 150 Example 10 Compound H33 Chemical formula E100 5:5 3.9 22.9 0.666 0.335 170 Example 11 Compound H34 Formula E124 5:5 3.8 21.8 0.661 0.331 180 Example 12 Compound H35 Formula E124 5:5 3.8 22.7 0.665 0.338 175 Example 13 Compound H61 Chemical formula E138 5:5 4.1 21.1 0.659 0.337 147 Example 14 Compound H63 Formula E138 5:5 3.9 20.6 0.663 0.332 159

From Table 1, it can be seen that the organic light-emitting devices of Examples 1 to 14 have higher efficiency and longer lifespan characteristics than the organic light-emitting devices of Comparative Examples 1 to 19. In addition, it can be confirmed that among the above examples, Examples 1 to 7 and Examples 10 to 12 have more improved efficiency and longer life characteristics than other examples.

Claims (18)

first electrode;
a second electrode opposite the first electrode; and
Comprising a light-emitting layer interposed between the first electrode and the second electrode,
The light-emitting layer includes at least one type of condensed ring compound represented by the following [Chemical Formula A]; Additionally, an organic light-emitting device comprising at least one heterocyclic compound represented by the following [Chemical Formula D].
[Formula A]

In the above [Formula A],
The substituents Ar1 and Ar2 are each the same or different, and independently of each other, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted 6 to 30 carbon atoms. Any one selected from aromatic hydrocarbon groups, which can be combined with adjacent groups to form an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring,
The linking groups L1 to L3 are each the same or different, and are independently a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
The p, q and r are each integers from 0 to 3, but when each of them is 2 or more, each linking group L1 to L3 is the same or different from each other,
The substituent HAr1 is represented by any one of the following [Structural Formula 1] to [Structural Formula 3].
[Structural Formula 1] [Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],
Wherein X is any one selected from O, S and CR11R12,
The substituents R1 to R12 are the same or different, and are independently selected from hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or an unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms,
In Formula A, any one of the substituents R1 to R10 in Structural Formulas 1 to 3 represented by HAr1 is a single bond bonded to the linking group L1.

[Formula D]

In [Formula D] above,
The substituent HAr4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
The linking group L is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
n1 and n2 are each integers from 0 to 3, but when n1 and n2 are each 2 or more, HAr4 and L are the same or different from each other,
The m1 is an integer from 1 to 4, but when m1 is 2 or more, the part containing HAr4 and L, respectively, in brackets [] (

) are the same or different from each other,
The Az is represented by any one of the following [Structural Formula 4] to [Structural Formula 10].
[Structural Formula 4] [Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In [Structural Formula 4] to [Structural Formula 10],
Wherein Z1 is N or CR21,
The Z2 is N or CR22,
Wherein Z3 is N or CR23,
The Z4 is N or CR24,
The Z5 is N or CR25,
The Z6 is N or CR26,
The Z7 is N or CR27,
The Z8 is N or CR28,
Wherein Z9 is N or CR29,
The Z10 is N or CR30,
The Z11 is N or CR31,
Y is any one selected from O, S, NR32 and CR33R34,
In structural formula 4, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 4 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,
In structural formula 5, at least one of Z1 to Z5 is N, and in order for the aromatic ring in structural formula 5 to have m1 bonds with the linking group L, m1 among R20 to R25 are each a single bond bonded to the linking group L,
In the structural formula 6, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 6 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,
In structural formula 7, at least one of Z1 to Z8 is N, and in order for the aromatic ring in structural formula 7 to have m1 bonds with the linking group L, m1 among R21 to R28 are each a single bond bonded to the linking group L,
In structural formula 8, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 8 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,
In structural formula 9, at least one of Z1 to Z10 is N, and in order for the aromatic ring in structural formula 9 to have m1 bonds with the linking group L, m1 among R21 to R30 are each a single bond bonded to the linking group L,
In structural formula 10, at least one of Z1 to Z11 is N, and in order for the aromatic ring in structural formula 10 to have m1 bonds with the linking group L, m1 among R20 to R31 are each a single bond bonded to the linking group L,
The substituents R20 to R34 are the same or different, and are independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms. , a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, but each other Adjacent groups can be combined with each other to form a condensed ring of aliphatic, aromatic, aliphatic hetero, or aromatic hetero,
Here, 'substitution' in 'substituted or unsubstituted' in [Formula A] and [Formula D] means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 24 carbon atoms, carbon number. Halogenated alkyl group of 1 to 24 carbon atoms, aryl group of 6 to 24 carbon atoms, arylalkyl group of 7 to 24 carbon atoms, heteroaryl group of 2 to 24 carbon atoms or heteroarylalkyl group of 2 to 24 carbon atoms, alkylsilyl of 1 to 24 carbon atoms It means being substituted with one or more substituents selected from the group consisting of arylsilyl group and arylsilyl group having 6 to 24 carbon atoms. According to paragraph 1,
Az represented by [Structural Formula 4] to [Structural Formula 10] in Formula D is an organic light-emitting device, characterized in that each is selected from E1 to E24 below.

<E1><E2><E3><E4><E5>

<E6><E7><E8><E9><E10>

<E11><E12><E13><E14><E15>

<E16><E17><E18><E19><E20>

<E21><E22><E23><E24>
In E1 to E24, X1 to It is a substituent selected from cycloalkyl groups and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms,
Each m1 of X1 to X11 in E1 to E24 is a single bond bonded to the linking group L in Formula D. According to claim 1,
Linking groups L1 to L3 in Formula A are each the same or different, and are independently a single bond, or are represented by the following [Structural Formula 22], [Structural Formula 23], [Structural Formula 25], [Structural Formula 27], [Structural Formula 28], and [ Any one selected from [Structural Formula 30],
An organic light emitting device wherein p, q and r are each 1 or 2.
[Structural Formula 22] [Structural Formula 23] [Structural Formula 25]

[Structural Formula 27] [Structural Formula 28] [Structural Formula 30]

In Structural Formula 22, Structural Formula 23, Structural Formula 25, Structural Formula 27, Structural Formula 28, and Structural Formula 30, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring. According to paragraph 1,
The linking group L in the formula D is a single bond or any one selected from the following [Structural Formula 22], [Structural Formula 23], [Structural Formula 25], [Structural Formula 27], [Structural Formula 28], and [Structural Formula 30],
An organic light emitting device wherein n2 is 1 or 2.
[Structural Formula 22] [Structural Formula 23] [Structural Formula 25]

[Structural Formula 27] [Structural Formula 28] [Structural Formula 30]

In Structural Formula 22, Structural Formula 23, Structural Formula 25, Structural Formula 27, Structural Formula 28, and Structural Formula 30, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring. According to claim 1,
An organic light-emitting device, wherein the substituents Ar1 and Ar2 in Formula A are the same or different, and are independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. According to claim 1,
In the formula D, the substituents R20 to R31 are the same or different, and are independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or substituted or unsubstituted alkyl group having 3 to 30 carbon atoms. An organic light-emitting device, characterized in that it is selected from a cycloalkyl group and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. According to paragraph 1,
An organic light-emitting device characterized in that at least one HAr4 in Formula D is a substituent represented by any one of the following [Structural Formulas 11] to [Structural Formulas 13].
[Structural Formula 11]

[Structural Formula 12]

[Structural Formula 13]

In [Structural Formula 11] above,
The X12 is any one selected from O, S, NR49 and CR50R51,
Any one of the substituents R41 to R48 in Formula 11 is a single bond bonded to the linking group L in Formula D,
In [Structural Formula 12] above,
The X13 is any one selected from O, S, NR49 and CR50R51,
The X14 is any one selected from O, S, NR60 and CR61R62,
Any one of the substituents R45 to R48 and any one of the substituents R52 to R55 are each connected to each other as a single bond,
Among the substituents R41 to R48 in the structural formula 12, any one of the remaining seven substituents excluding the single bond connected to the condensed ring containing X14 is a single bond bonded to the linking group L in Formula D,
In [Structural Formula 13] above,
The X15 is any one selected from O, S, NR53, CR54R55, and
Y1 is any one selected from O, S, NR56, CR57R58,
Any one of the substituents R41 to R52 in Formula 13 is a single bond bonded to the linking group L in Formula D,
The two substituents adjacent to each other among R45 to R48 are single bonds connected to * of the structural formula Q1,
In [Structural Formula 11] to [Structural Formula 13],
R41 to R62 are the same or different, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, It is any one selected from a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms. According to claim 1,
An organic light emitting device, wherein the substituent Ar1 or Ar2 is a substituent represented by the following structural formula 14.
[Structural Formula 14]

In [Structural Formula 14] above,
The X16 is CR79R80,
R71 to R80 are the same or different, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, Any one selected from a substituted or unsubstituted alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms,
Any one of the substituents R71 to R78 in Formula 14 is a single bond bonded to the linking group L2 or L3 in Formula A. According to paragraph 1,
In the [Structural Formula 1] to [Structural Formula 3] in Formula A,
An organic light-emitting device, wherein one of the substituents R1 to R4 is a single bond bonded to the linking group L1. According to paragraph 1,
An organic light-emitting device, wherein the condensed ring compound represented by Formula A is any one selected from the group represented by Compound H1 to Compound H245 below.

<Compound H1><Compound H2><Compound H3><Compound H4>

<Compound H5><Compound H6><Compound H7><Compound H8>

<Compound H9><Compound H10><Compound H11><Compound H12>

<Compound H13><Compound H14><Compound H15><Compound H16>

<Compound H17><Compound H18><Compound H19><Compound H20>

<Compound H21><Compound H22><Compound H23><Compound H24>

<Compound H25><Compound H26><Compound H27><Compound H28>

<Compound H29><Compound H30><Compound H31><Compound H32>

<Compound H33><Compound H34><Compound H35><Compound H36>

<Compound H37><Compound H38><Compound H39><Compound H40>

<Compound H41><Compound H42><Compound H43><Compound H44>

<Compound H45><Compound H46><Compound H47><Compound H48>

<Compound H49><Compound H50><Compound H51><Compound H52>

<Compound H53><Compound H54><Compound H55><Compound H56>

<Compound H57><Compound H58><Compound H59><Compound H60>

<Compound H61><Compound H62><Compound H63><Compound H64>

<Compound H65><Compound H66><Compound H67><Compound H68>

<Compound H69><Compound H70><Compound H71><Compound H72>

<Compound H73><Compound H74><Compound H75><Compound H76>

<Compound H77><Compound H78><Compound H79><Compound H80>

<Compound H81><Compound H82><Compound H83><Compound H84>

<Compound H85><Compound H86><Compound H87><Compound H88>

<Compound H89><Compound H90><Compound H91><Compound H92>

<Compound H93><Compound H94><Compound H95><Compound H96>

<Compound H97><Compound H98><Compound H99><Compound H100>

<Compound H101><Compound H102><Compound H103><Compound H104>

<Compound H105><Compound H106><Compound H107><Compound H108>

<Compound H109><Compound H110><Compound H111><Compound H112>

<Compound H113><Compound H114><Compound H115><Compound H116>

<Compound H117><Compound H118><Compound H119><Compound H120>

<Compound H121><Compound H122><Compound H123><Compound H124>

<Compound H125><Compound H126><Compound H127><Compound H128>

<Compound H129><Compound H130><Compound H131><Compound H132>

<Compound H133><Compound H134><Compound H135><Compound H136>

<Compound H137><Compound H138><Compound H139><Compound H140>

<Compound H141><Compound H142><Compound H143><Compound H144>

<Compound H145><Compound H146><Compound H147><Compound H148>

<Compound H146><Compound H147><Compound H148><Compound H149>

<Compound H150><Compound H151><Compound H152><Compound H153>

<Compound H154><Compound H155><Compound H156><Compound H157>

<Compound H158><Compound H159><Compound H160><Compound H161>

<Compound H162><Compound H163><Compound H164><Compound H165>

<Compound H166><Compound H167><Compound H168><Compound H169>

<Compound H170><Compound H171><Compound H172><Compound H173>

<Compound H174><Compound H175><Compound H176><Compound H177>

<Compound H178><Compound H179><Compound H180><Compound H181>

<Compound H182><Compound H183><Compound H184><Compound H185>

<Compound H186><Compound H187><Compound H188><Compound H189>

<Compound H190><Compound H191><Compound H192><Compound H193>

<Compound H194><Compound H195><Compound H196><Compound H197>

<Compound H198><Compound H199><Compound H200><Compound H201>

<Compound H202><Compound H203><Compound H204><Compound H205>

<Compound H206><Compound H207><Compound H208><Compound H209>

<Compound H210><Compound H211><Compound H212><Compound H213>

<Compound H214><Compound H215><Compound H216><Compound H217>

<Compound H218><Compound H219><Compound H220><Compound H221>

<Compound H222><Compound H223><Compound H224><Compound H225>

<Compound H226><Compound H227><Compound H228><Compound H229>

<Compound H230><Compound H231><Compound H232><Compound H233>

<Compound H234><Compound H235><Compound H236><Compound H237>

<Compound H238><Compound H239><Compound H240><Compound H241>

<Compound H242><Compound H243><Compound H244><Compound H245> According to paragraph 1,
An organic light-emitting device, wherein the heterocyclic compound represented by Formula D is any one selected from the group represented by Formula E1 to Formula E204.

<Formula E1><Formula E2><Formula E3><Formula E4>

<Formula E5><Formula E6><Formula E7><Formula E8>

<Formula E9><Formula E10><Formula E11><Formula E12>

<Formula E13><Formula E14><Formula E15><Formula E16>

<Formula E17><Formula E18><Formula E19><Formula E20>

<Formula E21><Formula E22><Formula E23><Formula E24>

<Formula E25><Formula E26><Formula E27><Formula E28>

<Formula E29><Formula E30><Formula E31><Formula E32>

<Formula E33><Formula E34><Formula E35><Formula E36>

<Formula E37><Formula E38><Formula E39><Formula E40>

<Formula E41><Formula E42><Formula E43><Formula E44>

<Formula E45><Formula E46><Formula E47><Formula E48>

<Formula E49><Formula E50><Formula E51><Formula E52>

<Formula E53><Formula E54><Formula E55><Formula E56>

<Formula E57><Formula E58><Formula E59><Formula E60>

<Formula E61><Formula E62><Formula E63><Formula E64>

<Formula E65><Formula E66><Formula E67><Formula E68>

<Formula E69><Formula E70><Formula E71><Formula E72>

<Formula E73><Formula E74><Formula E75><Formula E76>

<Formula E77><Formula E78><Formula E79><Formula E80>

<Formula E81><Formula E82><Formula E83><Formula E84>

<Formula E85><Formula E86><Formula E87><Formula E88>

<Formula E89><Formula E90><Formula E91><Formula E92>

<Formula E93><Formula E94><Formula E95><Formula E96>

<Formula E97><Formula E98><Formula E99><Formula E100>

<Formula E101><Formula E102><Formula E103><Formula E104>

<Formula E105><Formula E106><Formula E107><Formula E108>

<Formula E109><Formula E110><Formula E111><Formula E112>

<Formula E113><Formula E114><Formula E115><Formula E116>

<Formula E117><Formula E118><Formula E119><Formula E120>

<Formula E121><Formula E122><Formula E123><Formula E124>

<Formula E125><Formula E126><Formula E127><Formula E128>

<Formula E129><Formula E130><Formula E131><Formula E132>

<Formula E133><Formula E134><Formula E135><Formula E136>

<Formula E137><Formula E138><Formula E139><Formula E140>

<Formula E141><Formula E142><Formula E143><Formula E144>

<Formula E145><Formula E146><Formula E147><Formula E148>

<Formula E149><Formula E150><Formula E151><Formula E152>

<Formula E153><Formula E154><Formula E155><Formula E156>

<Formula E157><Formula E158><Formula E159><Formula E160>

<Formula E161><Formula E162><Formula E163><Formula E164>

<Formula E165><Formula E166><Formula E167><Formula E168>

<Formula E169><Formula E170><Formula E171><Formula E172>

<Formula E173><Formula E174><Formula E175><Formula E176>

<Formula E177><Formula E178><Formula E179><Formula E180>

<Formula E181><Formula E182><Formula E183><Formula E164>

<Formula E185><Formula E186><Formula E187><Formula E188>

<Formula E189><Formula E190><Formula E191><Formula E192>

<Formula E193><Formula E194><Formula E195><Formula E196>

<Formula E197><Formula E198><Formula E199><Formula E200>

<Formula E201><Formula E202><Formula E203><Formula E204> According to claim 1,
An organic light-emitting device, wherein the condensed ring compound represented by [Formula A] and the heterocyclic compound represented by [Formula D] included in the light-emitting layer are each used as a host. According to clause 12,
An organic light-emitting device, characterized in that the condensed ring compound represented by [Formula A] and the heterocyclic compound represented by [Formula D] are mixed at a weight ratio in the range of 1:9 to 9:1. According to clause 12,
The organic light-emitting device is characterized in that a dopant is added to the light-emitting layer. According to clause 1,
The organic light-emitting device is characterized in that, in addition to the light-emitting layer, it additionally includes at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron transport layer, and an electron injection layer. Light emitting device. According to clause 15,
An organic light emitting device, wherein one or more layers selected from among the above layers are formed by a deposition process or a solution process. According to clause 1,
In Structural Formulas 1 to 3 in Formula A,
An organic light emitting device characterized in that the substituent R4 is a single bond bonded to the linking group L1. According to claim 1,
The organic light emitting device may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and, a monochromatic or white flexible lighting device.

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