KR20230134879A - Compound for organic optoelectronic device, organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display apparatus. Details of the chemical formula 1 are as defined in the specification. The present invention can implement long-lifespan organic optoelectronic devices. Another embodiment provides a display apparatus including the organic optoelectronic device.

Description

Compounds for organic optoelectronic devices, organic optoelectronic devices, and display devices {COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE}

It relates to compounds for organic optoelectronic devices, organic optoelectronic devices, and display devices.

An organic optoelectronic diode is a device that can mutually convert electrical energy and light energy.

Organic optoelectronic devices can be broadly divided into two types depending on their operating principles. One is a photoelectric device that generates electrical energy by separating exciton formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, and the other is a photoelectric device that generates electrical energy by supplying voltage or current to the electrode. It is a light emitting device that generates light energy from.

Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

Among these, organic light emitting diodes (OLEDs) have recently received great attention due to the increased demand for flat panel display devices. Organic light emitting devices are devices that convert electrical energy into light, and the performance of organic light emitting devices is greatly influenced by the organic materials located between electrodes.

One embodiment provides a compound for an organic optoelectronic device that can implement a long-life organic optoelectronic device.

Another embodiment provides an organic optoelectronic device containing the above compound.

Another embodiment provides a display device including the organic optoelectronic device.

According to one embodiment, a compound for an organic optoelectronic device represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

The interatomic distance indicated by A1 and A2 is 3.8 Å or more,

X is O or S,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

At least one of Ar ¹ , Ar ² and R ¹ to R ⁴ is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group,

n1 is one of the integers from 1 to 3,

n2 to n4 are each independently an integer of 1 to 4.

According to another embodiment, an organic optoelectronic device is provided, including an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer includes the compound for an organic optoelectronic device.

According to another embodiment, a display device including the organic optoelectronic device is provided.

Long-life organic optoelectronic devices can be implemented.

Figure 1 is a cross-sectional view showing an organic light-emitting device according to an embodiment.
Figure 2 is a graph showing the correlation between the distance between atoms in a molecule and the lifespan characteristics of an organic light-emitting device to which it is applied.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby, and the present invention is only defined by the scope of the claims to be described later.

In this specification, unless otherwise defined, “substitution” means that at least one hydrogen in the substituent or compound is deuterium, halogen group, hydroxyl group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group, cyano group, or a combination thereof.

In one example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. Additionally, in a specific example of the present invention, “substitution” means that at least one hydrogen in a substituent or compound is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. Additionally, in a specific example of the present invention, “substitution” means that at least one hydrogen in a substituent or compound is replaced with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means replacing at least one hydrogen in a substituent or compound with deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, or naphthyl group. It means that it has been done.

As used herein, unless otherwise defined, “hetero” means that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon. .

In this specification, “aryl group” is a general concept of a group having one or more hydrocarbon aromatic moieties. All elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated. A form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and two or more hydrocarbon aromatic moieties. It may include a non-aromatic fused ring to which they are directly or indirectly fused, such as a fluorenyl group.

Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings splitting adjacent pairs of carbon atoms) functional groups.

In this specification, “heterocyclic group” is a higher concept including heteroaryl group, and in ring compounds such as aryl group, cycloalkyl group, fused ring thereof, or combination thereof, N, O, instead of carbon (C) It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

As an example, “heteroaryl group” means that the aryl group contains at least one hetero atom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted Unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted It may be a cyclic furanyl group, or a combination thereof, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group includes a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, Substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted Substituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, Substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted Quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazine A substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene It may be a diary, or a combination thereof, but is not limited thereto.

As used herein, “hydrogen substitution (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

In this specification, the hole characteristic refers to the characteristic of forming a hole by donating electrons when an electric field is applied. It has conduction characteristics according to the HOMO level and injects holes formed at the anode into the light-emitting layer. It refers to a characteristic that facilitates the movement of holes formed in the anode and in the light emitting layer.

In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conduction properties along the LUMO level, such as injection of electrons formed at the cathode into the light-emitting layer, movement of electrons formed in the light-emitting layer to the cathode, and movement of electrons from the light-emitting layer. It refers to a characteristic that facilitates movement.

Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

A compound for an organic optoelectronic device according to one embodiment is represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1,

The interatomic distance indicated by A1 and A2 is 3.8 Å or more,

X is O or S,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

At least one of Ar ¹ , Ar ² and R ¹ to R ⁴ is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group,

n1 is one of the integers from 1 to 3,

n2 to n4 are each independently an integer of 1 to 4.

The compound represented by Formula 1 can reduce interatomic interference by sufficiently ensuring the distance between atoms, represented by A1 and A2, of 3.8 Å or more, thereby suppressing crystallization of molecules and improving the lifespan when manufacturing an organic light-emitting device. It can be.

In particular, the compound represented by Formula 1 has a bulky substituent on at least one of Ar ¹ and Ar ² or at least one of R ¹ to R ⁴ , such as a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 By introducing a C30 heterocyclic group, the molecular structure can be distorted and the distance between the atoms represented by A1 and A2 can be secured to 3.8 Å or more.

For example, the distance between atoms represented by A1 and A2 may be 3.8 Å to 4.3 Å.

As an example, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4.

[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4,

The definitions of A1, A2, X, Ar ¹ , Ar ² , R ¹ to R ⁸ , and n1 to n4 are as described above.

As a specific example, Formula 1-1 may be represented by any of the following Formulas 1-1A to 1-1E.

[Formula 1-1A] [Formula 1-1B]

[Formula 1-1C] [Formula 1-1D]

[Formula 1-1E]

In Formula 1-1A to Formula 1-1E,

The definitions of A1, A2, X, Ar ¹ , Ar ² , R ¹ to R ⁸ , and n1 to n4 are as described above.

As a specific example, Formula 1-2 may be represented by any one of Formulas 1-2A to 1-2F below.

[Formula 1-2A] [Formula 1-2B]

[Formula 1-2C] [Formula 1-2D]

[Formula 1-2E] [Formula 1-2F]

In Formulas ^1-2A to 1-2F, ^{the definitions} of A1, ^A2 ,

As a specific example, Formula 1-3 may be represented by any one of the following Formulas 1-3A to 1-3F.

[Formula 1-3A] [Formula 1-3B]

[Formula 1-3C] [Formula 1-3D]

[Formula 1-3E] [Formula 1-3F]

In Formulas 1-3A to 1-3F, ^{the definitions} of ^A1 , ^A2 ,

As a specific example, Formula 1-4 may be represented by any of the following Formulas 1-4A to 1-4F.

[Formula 1-4A] [Formula 1-4B]

[Formula 1-4C] [Formula 1-4D]

[Formula 1-4E] [Formula 1-4F]

In Formulas ^1-4A to 1-4F, ^the definitions of ^A1 , ^A2 ,

In one embodiment, Formula 1 may be represented by Formula 1-4A.

For example, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted anthracenyl group. group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. It can be.

As a specific example, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted Or it may be an unsubstituted dibenzothiophenyl group.

For example, R ¹ to R ⁸ are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group. It may be benzothiophene.

As a specific example, R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted anthracenyl group. Alternatively, it may be an unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, at least one of Ar ¹ , Ar ² and R ¹ to R ⁸ may be selected from the substituents listed in Group I below.

[Group Ⅰ]

In Group I above, * is the connection point.

In the most specific embodiment, the compound for an organic optoelectronic device represented by Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[Group 1]

In addition to the compounds for organic optoelectronic devices described above, one or more compounds may be further included.

For example, a dopant may be further included.

The dopant may for example be a phosphorescent dopant, for example a red, green or blue phosphorescent dopant, for example a red or green phosphorescent dopant.

A dopant is a substance that emits light when mixed in a small amount with a compound for an organic optoelectronic device. In general, a material such as a metal complex that emits light by multiple excitation that excites the triplet state or higher can be used. . The dopant may be, for example, an inorganic, organic, or organic/inorganic compound, and may be included in one or two or more types.

An example of a dopant is a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. and organometallic compounds containing. The phosphorescent dopant may be, for example, a compound represented by the following formula Z, but is not limited thereto.

[Formula Z]

L ⁵ MX ²

In the above formula Z, M is a metal, and L ⁵ and X ² are the same or different from each other and are ligands that form a complex with M.

The M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and ^the L ⁵ and It may be a dentate ligand.

Examples of the ligands represented by L ⁵ and X ² may be selected from the formulas listed in Group A below, but are not limited thereto.

[Group A]

In group A above,

R ³⁰⁰ to R ³⁰² are each independently hydrogen, deuterium, a C1 to C30 alkyl group with or without halogen substitution, a C6 to C30 aryl group with or without C1 to C30 alkyl substitution, or a halogen,

R ³⁰³ to R ³²⁴ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C1 to C30 alkoxy group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, or a substituted or unsubstituted C6 to C30 arylamino group, SF ₅ , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or It is a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

For example, it may include a dopant represented by Chemical Formula V below.

[Formula V]

In the above formula V,

R ¹⁰¹ to R ¹¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ,

R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group,

At least one of R ¹⁰¹ to R ¹¹⁶ is a functional group represented by the following formula V-1,

L ¹⁰⁰ is a bidentate ligand of a monovalent anion, which coordinates to iridium through a lone pair of electrons on carbon or a heteroatom,

n1 and n2 are independently any integer from 0 to 3, n1 + n2 is any integer from 1 to 3,

[Formula V-1]

In the above formula V-1,

R ¹³⁵ to R ¹³⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ,

* refers to the part connected to the carbon atom.

As an example, it may include a dopant represented by the following chemical formula Z-1.

[Formula Z-1]

In the above formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring;

R ^A , R ^B , R ^C , and R ^D each independently represent mono-substituted, di-substituted, tri-substituted, tetrasubstituted, or tetrasubstituted;

L ^B , L ^C , and L ^D are each directly bonded, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof. independently selected from the group consisting of;

When nA is 1, L ^E is a group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof is selected from; If nA is 0, L ^E does not exist;

R ^A , R ^B , R ^C , R ^D , R, and R' are each hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, and alkenyl group. , cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group. , and combinations thereof; Any adjacent R ^A , R ^B , R ^C , R ^D , R , and R' are optionally connected to form a ring; X ^B , X ^C , X ^D , and X ^E are each independently selected from the group consisting of carbon and nitrogen; Q ¹ , Q ² , Q ³ , and Q ⁴ each represent oxygen or a direct bond.

The dopant according to one embodiment may be a platinum complex, and may be represented, for example, by the following chemical formula VI.

[Formula Ⅵ]

In the above formula VI,

X ¹⁰⁰ is selected from O, S and NR ¹³¹ ,

R ¹¹⁷ to R ¹³¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR ¹³² R ¹³³ R ¹³⁴ ,

R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group,

At least one of R ¹¹⁷ to R ¹³¹ is -SiR ¹³² R ¹³³ R ¹³⁴ or a tert-butyl group.

Hereinafter, an organic optoelectronic device using the above-described compound for an organic optoelectronic device will be described.

The organic optoelectronic device is not particularly limited as long as it is a device that can mutually convert electrical energy and light energy, and examples include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photoreceptor drums.

Here, an organic light-emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 is a cross-sectional view showing an organic light-emitting device according to an embodiment.

Referring to FIG. 1, the organic light emitting device 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110. Includes.

The anode 120 may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of metal, metal oxide, and/or conductive polymer. The anode 120 is made of metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; Conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline may be included, but are limited thereto. That is not the case.

The cathode 110 may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of metal, metal oxide, and/or conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; Examples include, but are not limited to, multilayered materials such as LiF/Al, LiO ₂ /Al, LiF/Ca, and BaF ₂ /Ca.

The organic layer 105 may include the above-described compound for organic optoelectronic devices.

The organic layer 105 includes a light-emitting layer 130, and the light-emitting layer 130 may include the above-described compound for an organic optoelectronic device.

The composition for an organic optoelectronic device further comprising a dopant may be, for example, a red or green light-emitting composition.

The light emitting layer 130 may include, for example, the above-described compound for organic optoelectronic devices as a phosphorescent host.

The organic layer may further include a charge transport region in addition to the light emitting layer.

The charge transport region may be, for example, a hole transport region 140.

The hole transport region 140 can further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and is included in group B below. At least one of the listed compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[Group B]

In addition to the above-mentioned compounds, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds with similar structures may also be used in the hole transport region 140.

Additionally, the charge transport region may be, for example, an electron transport region 150.

The electron transport region 150 can further increase electron injection and/or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130, and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and is included in group C below. At least one of the listed compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[Group C]

One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

Another embodiment may be an organic light-emitting device including a light-emitting layer and a hole transport region as the organic layer.

Another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as the organic layer.

As shown in FIG. 1 , the organic light emitting device according to an embodiment of the present invention may include an organic layer 105 and a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130 .

Meanwhile, the organic light emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light emitting layer as the organic layer described above.

The organic light emitting device 100 forms an anode or a cathode on a substrate, forms an organic layer using a dry film deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forms a cathode or cathode on the organic layer. It can be manufactured by forming an anode.

The organic light emitting device described above can be applied to an organic light emitting display device.

The above-described implementation example will be described in more detail through examples below. However, the following examples are for illustrative purposes only and do not limit the scope of rights.

Hereinafter, starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H tech, or synthesized through known methods, unless otherwise specified.

(Manufacture of compounds for organic optoelectronic devices)

The compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

Synthesis Example 1: Synthesis of Compound 21

[Scheme 1]

Step 1: Synthesis of intermediate Int(1)

10 g (22 mmol) of 9-(4-2-chlorophenyl)dibenzo[b,d]thiophen-2-yl)-9H-carbazole was dissolved in 90 ml of xylene, then 6.57 g (1.2 equivalents) of bispinacolatodiborone, Pd. ₂ (dba) ₃ 0.59 g (0.03 equivalent), K(OAc) 6.35 g (3.0 equivalent), and P(Cy) ₃ 1.45 g (0.24 equivalent) were added, and then heated and refluxed and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 8.96 g (75.4% yield) of Int(1). got it

Step 2: Synthesis of Compound 21

Intermediate Int(1) 8.96g (16mmol) and 9-(4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine-2-yl)-9H- After dissolving 7.38 g (17 mmol) of carbazole in 60 ml of 1,4-dioxane and 30 ml of DI Water, 0.56 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 4.49 g (2.0 equivalent) of K ₂ CO ₃ were added and nitrogen atmosphere was added. Next, heat, reflux, and stir at 110°C. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 10.36 g (77.6% yield) of Compound 21 was obtained by recrystallization from xylene.

Synthesis Example 2: Synthesis of Compound 3

[Scheme 2]

8.5g (15mmol) of intermediate Int(1) and 5.79g (16mmol) of 2-chloro-4-(1-dibenzofuran-1-yl)-6-phenyl-1,3,5-triazine were mixed with 55ml of 1,4-dioxane. And after dissolving in 28ml of DI Water, 0.53g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 4.26g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 9.84 g (85.5% yield) of Compound 3 was obtained by recrystallization from xylene.

Synthesis Example 3: Synthesis of Compound 8

[Scheme 3]

8.8g (16mmol) of intermediate Int(1) and 7.25g (17mmol) of 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-2-Phenyl-9H-carbazole were added to 1, After dissolving in 53 ml of 4-dioxane and 26 ml of DI Water, 0.55 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 4.41 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed at 110°C under nitrogen atmosphere. . After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 9.72g (74.1% yield) of Compound 8 was obtained by recrystallization from xylene.

Synthesis Example 4: Synthesis of Compound 15

[Scheme 4]

Step 1: Synthesis of intermediate Int(2)

10 g (34 mmol) of 9-(4-(2-chlorophenyl)dibenzo[b,d]furan-2-yl)-9H-carbazole was dissolved in 135 ml of xylene, then 10.21 g (1.2 equivalents) of bispinacolatodiborone, 0.92 g (0.03 equivalent) of Pd ₂ (dba) ₃ , 9.87 g (3.0 equivalent) of K(OAc), and 2.26 g (0.24 equivalent) of P(Cy) ₃ were added, followed by heating and refluxing at 145°C under nitrogen atmosphere. . After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 35:15 to obtain 15.16 g (84.5% yield) of Int(2). got it

Step 2: Synthesis of Compound 15

10g (19mmol) of intermediate Int(2) and 7.02g (20mmol) of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine were mixed with 1,4 After dissolving in 65 ml of -dioxane and 33 ml of DI Water, 0.65 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 5.16 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. Compound 15 was obtained by recrystallizing 9.96g (73% yield) from xylene.

Synthesis Example 5: Synthesis of Compound 20

[Scheme 5]

9g (17mmol) of intermediate Int(2) and 7.67g (18mmol) of 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-4-phenyl-9H-carbazole were added to 1,4 After dissolving in 56 ml of -dioxane and 28 ml of DI Water, 0.58 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 4.66 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 10.13 g (74.5% yield) of compound 20 was obtained by recrystallization from xylene.

Synthesis Example 6: Synthesis of Compound 51

[Scheme 6]

Step 1: Synthesis of intermediate Pre-Int(3)

12 g (27 mmol) of 9-(4-(2-chloro-3-fluorophenyl)dibenzothiophen-2-yl)-9-carbazole and 4.93 g (29 mmol) of carbazole were mixed with N-methyl-2-p. It was dissolved in 120 ml of rolidone, 11.37 g (2.0 equivalents) of potassium phosphate (tripotassium phosphate) was added, and then heated, refluxed, and stirred at 200°C under a nitrogen atmosphere. After 18 hours, the reaction solution is cooled, concentrated, and stirred at 400 rpm for 30 minutes at room temperature with 300 ml of DI Water. The solid produced by stirring was collected by filtration and then recrystallized in xylene to obtain 11.6 g (71% yield) of Pre-Int(3).

Step 2: Synthesis of intermediate Int(3)

10 g (16 mmol) of Pre-Int (3) was dissolved in 120 ml of xylene, then 4.83 g (1.2 equivalents) of bispinacolatodiborone, 0.44 g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 4.67 g of K(OAc) ( 3.0 equivalent), and 1.07 g (0.24 equivalent) of P(Cy) ₃ were added, and then heated, refluxed, and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and extracted with dichloromethane and DI water. The extract was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 45:5 to obtain 8.43 g (74.2% yield) of Int(3). got it

Step 3: Synthesis of Compound 51

After dissolving 8g (17mmol) of intermediate Int(3) and 4.74g (18mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 60ml of 1,4-dioxane and 30ml of DI Water, Pd(PPh) ₃ ) Add 0.58 g (0.03 equivalent) of _{4 and} 4.66 g (2.0 equivalent) of K ₂ CO ₃ and heat, reflux, and stir at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 10.11 g (73% yield) of compound 51 was obtained by recrystallization from xylene.

Synthesis Example 7: Synthesis of Compound 67

[Scheme 7]

Step 1: Synthesis of intermediate Pre-Int(4)

12 g (28 mmol) of 9-(4-(2-chloro-4-fluorophenyl)dibenzothiophen-2-yl)-9-carbazole and 7.42 g (30 mmol) of 2-phenylcarbazole were mixed with N-methyl- Dissolve 2-pyrrolidone in 100 ml, add 11.76 g (2.0 equivalents) of potassium phosphate (tripotassium phosphate), and heat, reflux, and stir at 200°C under a nitrogen atmosphere. After 20 hours, the reaction solution is cooled, concentrated, and stirred at 500 rpm for 60 minutes at room temperature with 300 ml of DI Water. The solid produced by stirring was collected by filtration and then recrystallized in xylene to obtain 12.1 g (64% yield) of Pre-Int(4).

Step 2: Synthesis of intermediate Int(4)

10 g (16 mmol) of Pre-Int (4) was dissolved in 120 ml of xylene, then 4.83 g (1.2 equivalents) of bispinacolatodiborone, 0.44 g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 4.67 g of K(OAc) ( 3.0 equivalent), and 1.07 g (0.24 equivalent) of P(Cy) ₃ were added, and then heated, refluxed, and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 9.62 g (78.1% yield) of Int(4). got it

Step 3: Synthesis of Compound 67

After dissolving 9g (12mmol) of intermediate Int(4) and 3.26g (12mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 40ml of 1,4-dioxane and 20ml of DI Water, Pd(PPh) ₃ ) Add 0.4 g (0.03 equivalent) of ₄ and 3.2 g (2.0 equivalent) of K ₂ CO ₃ and heat, reflux, and stir at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 7.32g (71.6% yield) of compound 67 was obtained by recrystallization from xylene.

Synthesis Example 8: Synthesis of Compound 78

[Scheme 8]

Step 1: Synthesis of intermediate Pre-Int(5)

9-(4-(3-bromo-2-chlorophenyl)dibenzothiophen-2-yl)-9-carbazole 10g (19mmol) and dibenzofuranyl-3-boronic acid 4.13g (19mmol) After dissolving in 30ml of xylene, 30ml of tetrahydrofuran, and 30ml of DI Water, 0.64g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 5.13g (2.0 equivalent) of K ₂ CO ₃ were added and incubated at 130°C under nitrogen atmosphere. Heat to reflux and stir. After 18 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 7.34 g (63% yield) of Pre-Int (5) was obtained by recrystallization from xylene and column purification using a mixed solvent of hexane and dichloromethane in a volume ratio of 70:30.

Step 2: Synthesis of intermediate Int(5)

After dissolving 7g (11mmol) of Pre-Int (5) in 70ml of xylene, 3.38g (1.2 equivalents) of bispinacolatodiborone, 0.31g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 3.27 g (0.03 equivalents) of K(OAc) were added ( 3.0 equivalent), and 0.75 g (0.24 equivalent) of P(Cy) ₃ were added, and then heated, refluxed, and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 6.84 g (85.8% yield) of Int(5). got it

Step 3: Synthesis of Compound 78

After dissolving 6.5g (9mmol) of intermediate Int(5) and 2.55g (10mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 40ml of 1,4-dioxane and 20ml of DI Water, Pd ( 0.31 g (0.03 equivalent) of PPh ₃ ) ₄ and 2.5 g (2.0 equivalent) of K ₂ CO ₃ were added and heated, refluxed, and stirred at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 6.18g (83% yield) of compound 78 was obtained by recrystallization from xylene.

Synthesis Example 9: Synthesis of Compound 101

[Scheme 9]

Step 1: Synthesis of intermediate Pre-Int(6)

10 g (30 mmol) of [2-(9-carbazol-9-yl) dibenzothiophen-4-yl] boronic acid and 10.83 g (32 mmol) of 3-bromo-4-chloro terphenyl were mixed with 50 ml of xylene, After dissolving in 50 ml of tetrahydrofuran and 50 ml of DI Water, 1.04 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 8.29 g (2.0 equivalent) of K ₂ CO ₃ were added and heated, refluxed and stirred at 130°C under nitrogen atmosphere. do. After 18 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 13.18 g (71.8% yield) of Pre-Int (6) was obtained by recrystallization from xylene and column purification using a mixed solvent of hexane and dichloromethane in a volume ratio of 70:30.

Step 2: Synthesis of intermediate Int(6)

10 g (16 mmol) of Pre-Int (6) was dissolved in 100 ml of xylene, then 4.94 g (1.2 equivalents) of bispinacolatodiborone, 0.45 g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 4.77 g of K(OAc) ( 3.0 equivalent), and 1.09 g (0.24 equivalent) of P(Cy) ₃ were added, and then heated, refluxed, and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 8.84 g (77.5% yield) of Int(6). got it

Step 3: Synthesis of Compound 101

After dissolving 8.0g (11mmol) of intermediate Int(6) and 3.2g (12mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 80ml of 1,4-dioxane and 40ml of DI Water, Pd ( 0.39 g (0.03 equivalent) of PPh ₃ ) ₄ and 3.14 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed and stirred at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. Recrystallization from xylene yielded 7.11 g (77.3% yield) of Compound 101.

Synthesis Example 10: Synthesis of Compound 111

[Scheme 10]

Step 1: Synthesis of intermediate Pre-Int(7)

[2-(9-carbazol-9-yl)dibenzothiophen-4-yl]boronic acid 10g (30mmol) and 2-(3-bromo-4-chlorophenyl)phenanthrene 11.58g (32mmol) After dissolving in 50 ml of xylene, 50 ml of tetrahydrofuran, and 50 ml of DI Water, 1.04 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 8.29 g (2.0 equivalent) of K ₂ CO ₃ were added and incubated under nitrogen atmosphere for 130 minutes. Heat to reflux and stir at ℃. After 18 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 16.52 g (86.5% yield) of Pre-Int (7) was obtained by recrystallization from xylene and column purification using a mixed solvent of hexane and dichloromethane in a volume ratio of 60:40.

Step 2: Synthesis of intermediate Int(7)

10 g (16 mmol) of Pre-Int (7) was dissolved in 100 ml of xylene, then 4.75 g (1.2 equivalents) of bispinacolatodiborone, 0.43 g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 4.59 g of K(OAc) ( 3.0 equivalent), and 1.05 g (0.24 equivalent) of P(Cy) ₃ were added, and then heated, refluxed, and stirred at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 9.13 g (80.5% yield) of Int(7). got it

Step 3: Synthesis of Compound 111

After dissolving 9.0g (12mmol) of intermediate Int(7) and 3.48g (13mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine in 80ml of 1,4-dioxane and 40ml of DI Water, Pd ( 0.43 g (0.03 equivalent) of PPh ₃ ) ₄ and 3.42 g (2.0 equivalent) of K ₂ CO ₃ were added and heated, refluxed, and stirred at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 8.26 g (80.2% yield) of Compound 111 was obtained by recrystallization from xylene.

Comparative Synthesis Example 1: Synthesis of Compound R-1

[Scheme 11]

Step 1: Synthesis of Compound R-1

10 g (29 mmol) of 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 1-(3-dibenzothiophen-4-yl)phenyl)-carba After dissolving 11.8 g (31 mmol) of the sol in 100 ml of dimethylformamide, 20.52 g (2.0 equivalents) of cesium carbonate was added, and the mixture was heated, refluxed, and stirred at 150°C for 18 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 14.42 g (67.6% yield) of compound R-1 was obtained by recrystallization from xylene.

Comparative Synthesis Example 2: Synthesis of Compound R-2

[Scheme 12]

Step 1: Synthesis of Compound R-2

10 g (29 mmol) of 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 10.16 g of 4-(dibenzothiophen-1yl)-9-carbazole (29 mmol) was dissolved in 100 ml of dimethylformamide, then 12.35 g (2.0 equivalents) of potassium phosphate tribasic (potassium phosphate tribasic) was added, and the solution was heated, refluxed, and stirred at 150°C for 18 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 13.61 g (71.2% yield) of compound R-2 was obtained by recrystallization from xylene.

Comparative Synthesis Example 3: Synthesis of Compound R-3

[Scheme 13]

Step 1: Synthesis of Compound R-3

10 g (29 mmol) of 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 1-(4-(dibenzothiophen-4yl)phenyl)-9 - 12.38 g (29 mmol) of carbazole was dissolved in 100 ml of dimethylformamide, then 12.35 g (2.0 equivalents) of potassium phosphate tribasic (potassium phosphate tribasic) was added, and the mixture was heated, refluxed, and stirred at 150°C for 18 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 14.11 g (66.2% yield) of compound R-3 was obtained by recrystallization from xylene.

Comparative Synthesis Example 4: Synthesis of Compound R-4

[Scheme 14]

Step 1: Synthesis of Compound R-4

10 g (29 mmol) of 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 9.7 g of 4-(dibenzofuran-4-yl)-9-carbazole (29 mmol) was dissolved in 100 ml of dimethylformamide, then 10.66 g (2.0 equivalents) of potassium carbonate was added, and the mixture was heated, refluxed, and stirred at 150°C for 18 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 12.88 g (69.1% yield) of compound R-4 was obtained by recrystallization from xylene.

Comparative Synthesis Example 5: Synthesis of Compound R-5

[Scheme 15]

Step 1: Synthesis of Compound R-5

10 g (29 mmol) of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 9.7 g (29 mmol) of 3-(dibenzofuran-3-yl)-9-carbazole After dissolving in 100 ml of N-methyl-2-pyrrolidone, 12.35 g (2.0 equivalents) of potassium phosphate tribasic (potassium phosphate tribasic) was added, and the solution was heated, refluxed, and stirred at 220°C for 16 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 12.64 g (67.9% yield) of compound R-5 was obtained by recrystallization from xylene.

Comparative Synthesis Example 6: Synthesis of Compound R-6

[Scheme 16]

Step 1: Synthesis of Compound R-6

10 g (29 mmol) of 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 9.7 g (29 mmol) of 2-(dibenzofuran-3-yl)-9-carbazole After dissolving in 100 ml of N-methyl-2-pyrrolidone, 12.35 g (2.0 equivalents) of potassium phosphate tribasic (potassium phosphate tribasic) was added, and the solution was heated, refluxed, and stirred at 220°C for 16 hours under a nitrogen atmosphere. After adding water to the reaction solution at room temperature, filter it to obtain a solid and dry it under reduced pressure. 13.19 g (70.8% yield) of compound R-6 was obtained by recrystallization from xylene.

Comparative Synthesis Example 7: Synthesis of Compound R-7

[Scheme 17]

Step 1: Synthesis of intermediate Pre-Int(8)

10 g (30 mmol) of 3-(dibenzofuran-3-yl)-9-carbazole and 6.82 g (36 mmol) of 1-bromo-3-chlorobenzene were dissolved in 120 ml of xylene and then dissolved in sodium terrestrialtoxide NaO ( t-Bu) 4.31g (1.5 equivalent), trisdibenzelideneacetonedipalladium Pd ₂ (dba) ₃ 0.82g (0.03 equivalent), tertiary triphenylphosphine 50% toluene solution P(t-Bu) ₃ 50% Add 1.48ml (1.21g, 0.1 equivalent) of Toluene, heat to reflux and stir at 145°C under nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and washed with methanol and water to secure a solid and recrystallized with xylene-acetone to obtain 10.25 g (77.3% yield) of the intermediate Pre-Int(8).

Step 2: Synthesis of intermediate Int(8)

10 g (22 mmol) of Pre-Int (8) was dissolved in 100 ml of xylene, then 6.82 g (1.2 equivalents) of bispinacolatodiborone, 0.61 g (0.03 equivalents) of Pd ₂ (dba) ₃ , and 6.59 g (0.03 equivalents) of K(OAc) ( 3.0 equivalent), and 1.51 g (0.24 equivalent) of P(Cy) ₃ were added, followed by heating, refluxing, and stirring at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 70:30 to obtain 8.42 g (70.3% yield) of Int(8). got it

Step 3: Synthesis of Compound R-7

After dissolving 4g (15mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 8.4g (16mmol) of intermediate Int(8) in 100ml of 1,4-dioxane and 50ml of DI Water, Pd(PPh) ₃ ) Add 0.52 g (0.03 equivalent) of _{4 and} 4.13 g (2.0 equivalent) of K ₂ CO ₃ and heat, reflux, and stir at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. Recrystallization from xylene gave 6.85 g (71.6% yield) of compound R-7.

Comparative Synthesis Example 8: Synthesis of Compound R-8

[Scheme 18]

5.92 g (17 mmol) of 2-(biphenyl-4-yl)-4-phenyl-6-chloro-1,3,5-triazine and 10 g (18 mmol) of Int(1) were mixed with 100 ml of 1,4-dioxane and DI. After dissolving in 50 ml of water, 0.6 g (0.03 equivalent) of Pd(PPh ₃ ) ₄ and 4.77 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed at 110°C under nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. Recrystallized from xylene to obtain 7.86 g (62.2% yield) of compound R-8.

Comparative Synthesis Example 9: Synthesis of Compound R-9

[Scheme 19]

Step 1: Synthesis of intermediate Int(9)

10 g (22 mmol) of 9-(4-(2-chlorophenyl)dibenzofuran-2yl)-9-carbazole was dissolved in 100 ml of xylene, then 6.81 g (1.2 equivalents) of bispinacolatodiborone, Pd ₂ ( 0.61 g (0.03 equivalent) of dba) ₃ , 6.58 g (3.0 equivalent) of K(OAc), and 1.50 g (0.24 equivalent) of P(Cy) ₃ were added, followed by heating, refluxing and stirring at 145°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, concentrated, and the extract extracted with dichloromethane and DI water was column-purified with a mixed solvent of hexane and dichloromethane in a volume ratio of 60:40 to obtain 7.71 g (64.5% yield) of Int(9). got it

Step 2: Synthesis of Compound R-9

After dissolving 3.57g (13mmol) of 2,4-diphenyl-6-chloro-1,3,5-triazine and 7.5g (14mmol) of Int(9) in 100ml of 1,4-dioxane and 50ml of DI Water, Pd 0.46 g (0.03 equivalent) of (PPh ₃ ) ₄ and 3.69 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed and stirred at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. Recrystallization from xylene yielded 6.72 g (78.6% yield) of compound R-9.

Comparative Synthesis Example 10: Synthesis of Compound R-10

[Scheme 20]

After dissolving 4.18g (15mmol) of 2,4-diviphenyl-6-chloro-1,3,5-triazine and 8.6g (16mmol) of Int(9) in 130ml of 1,4-dioxane and 65ml of DI Water, Pd 0.51 g (0.03 equivalent) of (PPh ₃ ) ₄ and 3.87 g (2.0 equivalent) of K ₂ CO ₃ were added and heated and refluxed and stirred at 110°C under a nitrogen atmosphere. After 12 hours, the reaction solution is cooled, the water layer is removed, and the organic layer is dried under reduced pressure. 7.73 g (76.3% yield) of compound R-10 was obtained by recrystallization from xylene.

Evaluation 1: Interatomic distance measurement simulation

Draw the chemical structure with the Chemdraw 18.0 (PerkinElmer) chemical structure program, connect to the Supercom account (EODSSR), and save the log file created after energy level simulation (HOMO, LUMO, T1, S1 value calculation) with the Chemcraft (Ando Technology) program. was used to search for the optimized structure with the lowest molecular energy, select the atom and atoms of interest in the molecule, simulate the distance, obtain the value, and display it in Å units.

(Production of organic light-emitting devices)

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After washing with distilled water, the substrate was ultrasonic cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, and then transferred to a plasma cleaner. The substrate was cleaned using oxygen plasma for 10 minutes and then transferred to a vacuum evaporator. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å. Compound A was deposited to a thickness of 1350 Å on the top to form a hole transport layer. Compound B was deposited on the top of the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound 21 obtained in Synthesis Example 1 was used as a host on the top of the hole transport auxiliary layer, and PhGD was doped at 7 wt% as a dopant. A 400Å thick light emitting layer was formed by vacuum deposition. Next, Compound C was deposited on the top of the emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and Compound D and Liq were simultaneously vacuum deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light emitting device was manufactured by sequentially vacuum depositing 15Å of LiQ and 1200Å of Al on top of the electron transport layer to form a cathode.

ITO/Compound A (3% NDP-9 doping, 100Å)/ Compound A (1350Å)/ Compound B (350Å)/ EML [93 wt% of host (Compound 21): 7 wt% of PhGD] (400Å)/ Compound It was manufactured with the structure of C (50 Å)/Compound D:LiQ (300 Å)/LiQ (15 Å)/Al (1200 Å).

Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1 ''''-quinquephenyl]-3''''-yl)-1,3,5-triazine

Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[PhGD]

Examples 2 to 10, and Comparative Examples 1 to 10

The devices of Examples 2 to 10 and Comparative Examples 1 to 10 were manufactured in the same manner as Example 1, except that the host was changed as shown in Table 1 below.

Assessment 2: Lifespan Measurement

Using the Polaronics life measurement system for the manufactured organic light emitting device, the initial luminance (cd/m ² ) was 24,000 cd/m ² and the decrease in luminance over time was measured, and the luminance was found to be 93% of the initial luminance. The time point of decrease was measured as T93 lifespan.

Relative values based on the T93 lifespan of Example 8 are shown in Table 1 below.

In addition, the correlation between the distance between atoms in the molecule and the lifespan characteristics of the organic light-emitting device to which it is applied is shown in Figure 2.

host Longest distance between A1 and A2
(Å) LifespanT93
(%) Example 1 21 4.14 113 Example 2 3 3.92 108 Example 3 8 3.86 106 Example 4 15 3.83 103 Example 5 20 3.94 111 Example 6 51 4.03 106 Example 7 67 4.10 110 Example 8 78 3.98 100 Example 9 101 3.82 86 Example 10 111 3.84 93 Comparative Example 1 R-1 3.53 56 Comparative Example 2 R-2 3.28 38 Comparative Example 3 R-3 3.62 50 Comparative Example 4 R-4 3.24 23 Comparative Example 5 R-5 3.47 61 Comparative Example 6 R-6 3.58 48 Comparative Example 7 R-7 3.41 56 Comparative Example 8 R-8 3.32 12 Comparative Example 9 R-9 3.40 53 Comparative Example 10 R-10 3.38 52

Figure 2 is a graph showing the correlation between the distance between atoms in a molecule and the lifespan characteristics of an organic light-emitting device to which it is applied.

Referring to Table 1 and FIG. 2, the molecular structure of the compound according to the embodiment of the present invention maintains a twisted structure such that the distance between atoms is 3.8 Å or more, and accordingly, the organic light emission to which the compound or a composition containing the same is applied. It can be seen that the lifespan characteristics of the device are significantly improved compared to the organic light-emitting device according to the comparative example in which a compound with an interatomic distance in the molecule of less than 3.8 Å was applied.

Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention. will be.

100: Organic light emitting device
105: Organic layer
110: cathode
120: anode
130: light emitting layer
140: Hole transport area
150: Electron transport area

Claims (13)

Compound for organic optoelectronic devices represented by the following formula (1):
[Formula 1]

In Formula 1,
The interatomic distance indicated by A1 and A2 is 3.8 Å or more,
X is O or S,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
At least one of Ar ¹ , Ar ² and R ¹ to R ⁴ is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group,
n1 is one of the integers from 1 to 3,
n2 to n4 are each independently an integer of 1 to 4. According to paragraph 1,
A compound for an organic optoelectronic device wherein the distance between atoms represented by A1 and A2 is 3.8 Å to 4.3 Å. According to paragraph 1,
A compound for an organic optoelectronic device represented by any one of the following formulas 1-1 to 1-4:
[Formula 1-1] [Formula 1-2]

[Formula 1-3] [Formula 1-4]

In Formulas 1-1 to 1-4,
^{A1 , A2 ,} According to paragraph 3,
Formula 1-1 is a compound for an organic optoelectronic device represented by any one of the following Formulas 1-1A to 1-1E:
[Formula 1-1A] [Formula 1-1B]

[Formula 1-1C] [Formula 1-1D]

[Formula 1-1E]

In Formula 1-1A to Formula 1-1E,
^{A1 , A2 ,} According to paragraph 1,
Formula 1-2 is a compound for an organic optoelectronic device represented by any one of the following Formulas 1-2A to 1-2F:
[Formula 1-2A] [Formula 1-2B]

[Formula 1-2C] [Formula 1-2D]

[Formula 1-2E] [Formula 1-2F]

In Formula 1-2A to Formula 1-2F,
^{A1 , A2 ,} According to paragraph 1,
Formula 1-3 is a compound for an organic optoelectronic device represented by any one of the following Formulas 1-3A to 1-3F:
[Formula 1-3A] [Formula 1-3B]

[Formula 1-3C] [Formula 1-3D]

[Formula 1-3E] [Formula 1-3F]

In Formulas 1-3A to 1-3F,
^{A1 , A2 ,} According to paragraph 1,
The formula 1-4 is a compound for an organic optoelectronic device represented by any one of the following formulas 1-4A to 1-4F:
[Formula 1-4A] [Formula 1-4B]

[Formula 1-4C] [Formula 1-4D]

[Formula 1-4E] [Formula 1-4F]

In Formulas 1-4A to 1-4F,
^{A1 , A2 ,} According to paragraph 1,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, Compounds for organic optoelectronic devices. According to paragraph 1,
A compound for an organic optoelectronic device, wherein at least one of Ar ¹ , Ar ² and R ¹ to R ⁴ is selected from the substituents listed in Group I below:
[Group Ⅰ]

In Group I above, * is the connection point. According to paragraph 1,
A compound for an organic optoelectronic device selected from the compounds listed in Group 1 below:
[Group 1]

. Anode and cathode facing each other,
Comprising at least one organic layer located between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device according to any one of claims 1 to 10. According to clause 11,
The organic layer includes a light-emitting layer,
The light-emitting layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device. A display device comprising the organic optoelectronic device according to claim 11.