CN117479566A

CN117479566A - Composition, light emitting device including the same, and electronic device including the light emitting device

Info

Publication number: CN117479566A
Application number: CN202310943274.3A
Authority: CN
Inventors: 洪英基; 郭丞燕; 金圣玟; 李晟熏; 石原慎吾; 李龙柱; 崔炳基; 黄圭荣
Original assignee: Samsung Electronics Co Ltd
Current assignee: Samsung Electronics Co Ltd
Priority date: 2022-07-29
Filing date: 2023-07-28
Publication date: 2024-01-30

Abstract

Disclosed are compositions, light emitting devices including the same, and electronic devices including the light emitting devices. The composition includes m1 dopants; and m2 hosts, wherein m1 and m2 are each an integer of 1 or more, when m1 is 2 or more, the two or more dopants are different from each other, when m2 is 2 or more, the two or more hosts are different from each other, and the composition has coordinates of an improved image represented by (X, Y) as defined herein.

Description

Composition, light emitting device including the same, and electronic device including the light emitting device

Cross reference to related applications

The present application claims priority and rights, and ownership rights and attributes derived therefrom, of korean patent application No.10-2022-0095044, filed at the korean intellectual property office at the date of 2022, 7, and 29, and korean patent application No.10-2023-0097229, filed at the date of 2023, 7, and 26, the contents of which are incorporated herein by reference in their entirety.

Technical Field

The present subject matter relates to compositions, light emitting devices including the same, and electronic devices including the light emitting devices.

Background

Among the light emitting devices, an Organic Light Emitting Device (OLED) is a self-emission device having improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full color images.

For example, a typical OLED may include an anode, a cathode, and an organic layer between the anode and the cathode, where the organic layer includes an emissive layer. The hole transport region may be located between the anode and the emissive layer, and the electron transport region may be located between the emissive layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and electrons may then recombine in the emissive layer to generate excitons. The excitons may transition from an excited state to a ground state, thereby generating light.

Disclosure of Invention

Provided are a composition capable of improving the turn-off (off) time of a light emitting device and a light emitting device whose turn-off time is improved by using the composition. An electronic device comprising the light emitting device is also provided.

Additional aspects will be set forth in part in the detailed description which follows, and in part will be obvious from the description, or may be learned by practice of the presented embodiments.

According to one aspect, a composition includes m1 dopants and m2 hosts, wherein

m1 and m2 are each an integer of 1 or more,

when m1 is 2 or more, two or more kinds of dopants are different from each other,

When m2 is 2 or more, two or more kinds of main bodies are different from each other, and

the composition has coordinates of an improved image represented by:

(X,Y)

wherein the method comprises the steps of

X isAnd->The sum, and calculated as debye,

y is { HOMO (H) _min )-HOMO(D _min )}×{1-W(H _{LUMO_max} ) Calculated, and in electron volts (eV),

the coordinates of the improved image exist within a quadrilateral having four vertices at (1.112,0.119), (1.720,0.119), (1.530,0.160), and (1.112,0.180),

x is a variable from 1 to m1,

y is a variable from 1 to m2,

DM (Dx) is the dipole moment of the x-th dopant and is calculated as Debye,

DM (Hy) is the dipole moment of the y-th host, and is calculated as Debye,

dm (Dx) and Dm (Hy) are each calculated based on density functional theory,

w (Dx) is the weight fraction of the x-th dopant relative to the total weight of the m1 dopants and the m2 host, and

w (Hy) is the weight fraction of the y-th host relative to the total weight of the m1 dopants and the m2 hosts,

HOMO(H _min ) Is the minimum of the absolute values of the highest occupied molecular orbital levels of the m2 hosts, and is calculated in eV,

HOMO(D _min ) Is the minimum of the absolute values of the highest occupied molecular orbital levels of the m1 dopants, and is calculated in eV,

W(H _{LUMO_max} ) A weight fraction of the host having a maximum value among absolute values of lowest unoccupied molecular orbital energy levels of the m2 host relative to a total weight of the m1 dopants and the m2 host, and

The highest occupied molecular orbital energy level and the lowest unoccupied molecular orbital energy level are each negative values measured using differential pulse voltammetry using ferrocene as a reference material.

According to another aspect, a light emitting device includes

The first electrode is arranged to be electrically connected to the first electrode,

a second electrode opposite to the first electrode, and

an intermediate layer disposed between the first electrode and the second electrode,

wherein the intermediate layer comprises an emissive layer, and

wherein the emissive layer comprises the composition.

For example, the intermediate layer of the light emitting device may include

M light emitting units each including at least one emission layer, and

m-1 charge generation layers arranged between two adjacent light emitting units of the m light emitting units, wherein

m is an integer of 2 or more, and

the emission layer of at least one light emitting unit among the m light emitting units may include the composition.

In one or more embodiments, the light emitting device may further include a substrate including red, green, and blue sub-pixels,

the first electrode is patterned for each of the red sub-pixel, the green sub-pixel, and the blue sub-pixel,

The emission layers may include a red emission layer corresponding to the red sub-pixel, a green emission layer corresponding to the green sub-pixel, and a blue emission layer corresponding to the blue sub-pixel, and

the green emissive layer comprises a composition as described herein.

According to another aspect, an electronic device includes the light emitting device.

Drawings

These and/or other aspects will be apparent from and more readily appreciated from the following description of the embodiments taken in conjunction with the following considerations:

fig. 1 is a schematic diagram of a light emitting device 10 according to one or more embodiments; and

fig. 2 is a graph of Y-coordinates versus X-coordinates and shows a contour plot of off-time based on (X, Y) coordinates and off-time values for each of OLEDs 1 to 24 as described herein.

Detailed Description

Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the exemplary embodiments may have different forms and should not be construed as limited to the detailed description set forth herein. Accordingly, exemplary embodiments are described in further detail below only by reference to the accompanying drawings to illustrate some aspects and features. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. The expression "at least one of the elements" for example, modifies the entire list of elements when before or after the list of elements without modifying individual elements of the list.

The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term "or" means "and/or". It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

It will be understood that, although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present embodiment.

Exemplary embodiments are described herein with reference to cross-sectional illustrations that are schematic illustrations of idealized embodiments. In this way, deviations from the shape of the figures as a result of, for example, manufacturing techniques and/or tolerances, will be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, an area illustrated or described as flat may typically have rough and/or nonlinear features. Moreover, the sharp corners illustrated may be rounded. Accordingly, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the claims.

It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the present disclosure and relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

As used herein, "about" or "approximately" includes the stated values and is meant to be within an acceptable range of deviation from the particular values as determined by one of ordinary skill in the art in view of the measurements in question and the errors associated with the measurement of the particular quantities (i.e., limitations of the measurement system). For example, "about" may mean that the deviation from the stated value is within one or more standard deviations, or within + -10% or 5%.

A composition according to one aspect includes m1 dopants and m2 hosts.

In the composition, the total weight of the m2 hosts may be greater than the total weight of the m1 dopants. In other words, the total amount of the m1 dopants in the composition may be greater than the total amount of the m2 hosts in the composition, based on the total weight of the composition.

m1 and m2 are each an integer of 1 or more. For example, m1 and m2 may each independently be an integer of 1 to 5, or an integer of 1 to 3.

When m1 is 2 or more, two or more dopants are different from each other. That is, the composition may include one type of dopant, or may include two or more types of dopants different from each other.

When m2 is 2 or more, two or more kinds of bodies are different from each other. That is, the composition may include one type of body, or may include two or more types of bodies different from each other.

In one or more embodiments, m1 and m2 may each be independently 1 or 2. For example, m1 may be 1 and m2 may be 2.

The composition has coordinates (IM coordinates) of an improved image represented by:

(X,Y)。

x isAnd->And Y is calculated as Debye and Y is calculated by { HOMO (H _min )-HOMO(D _min )}×{1-W(H _{LUMO_max} ) Calculated, and in electron volts (eV). Coordinates of the modified image defined by (X, Y) exist within (including on the boundaries of) quadrilaterals having four vertices at (1.112,0.119), (1.720,0.119), (1.530,0.160), and (1.112,0.180).

At the position ofWherein x is a variable from 1 to m 1.

At the position ofWherein y is a variable from 1 to m 2.

DM (Dx) is the dipole moment of the x-th dopant and is in debye, and DM (Hy) is the dipole moment of the y-th host and is in debye.

DM (Dx) and DM (Hy) are each calculated based on Density Functional Theory (DFT). The DFT-based calculation method may be performed using various programs (e.g., gaussian 16 (Gaussian 16) programs, etc.).

In one or more embodiments, when the dopant is an organometallic compound, the dopant molecular structure may be optimized by using a B3LYP/LanL2DZ function for the metal in the dopant and a B3LYP/6-31G (D, P) function for the organic ligand in the dopant, and then a Density Functional Theory (DFT) calculation may be performed using a Gaussian 16 program to calculate the dipole moment of the dopant (see, e.g., table 1).

In one or more embodiments, each molecular structure may be optimized for the host using a B3LYP/6-31G (D, P) function, and then a Density Functional Theory (DFT) calculation using a Gaussian 16 program may be performed to calculate the dipole moment of the host (see, e.g., table 1).

W (Dx) is the weight fraction of the x-th dopant relative to the total weight of the m1 dopants and the m2 hosts. For example, W (Dx) may be calculated from the weight of the xth dopant/the total weight of the m1 dopants and the m2 hosts.

W (Hy) is the weight fraction of the y-th host relative to the total weight of the m1 dopants and the m2 hosts. For example, W (Hy) may be calculated by the weight of the y-th host/the total weight of the m1 dopants and the m2 hosts.

The sum of "W (D1) +W (D2) + … +W (Dx-1) +W (Dx)" and "W (H1) +W (H2) + … +W (Hy-1) +W (Hy)" in the emission layer may be 1.

In one or more embodiments, "W (D1) +W (D2) + … +W (Dx-1) +W (Dx)" may be from about 0.03 to about 0.20, from about 0.05 to about 0.18, from about 0.05 to about 0.10, or from about 0.07 to about 0.15.

In one or more embodiments, "W (H1) +w (H2) + … +w (Hy-1) +w (Hy)" may be about 0.80 to about 0.97, about 0.82 to about 0.95, about 0.90 to about 0.95, or about 0.85 to about 0.93.

For example, when m1 is 1 and m2 is 2 in the composition,

the dopant includes only the first dopant,

the body includes a first body and a second body different from each other,

is DM (D1). W (D1), i.e., "dipole moment of the first dopant x weight fraction of the first dopant", and

is DM (H1). W (H1) +DM (H2). W (H2), i.e., "(dipole moment of first body x weight of first body)Fraction) + (dipole moment of the second body x weight fraction of the second body). "

In one or more embodiments, when m1 and m2 in the emissive layer are each 2,

the dopants include a first dopant and a second dopant that are different from each other,

the body includes a first body and a second body different from each other,

is DM (D1). W (D1) +DM (D2). W (D2), i.e., "(dipole moment of first dopant x weight fraction of first dopant) + (dipole moment of second dopant x weight fraction of second dopant)", and

is DM (h1) +w (h1) +dm (h2) +w (H2), i.e., "(dipole moment of the first body×weight fraction of the first body) + (dipole moment of the second body×weight fraction of the second body). "

The first host may be a hole transporting compound and the second host may be an electron transporting compound. Each of the hole transporting compound and the electron transporting compound may be understood by reference to the description provided herein.

In one or more embodiments, the first host may be a hole transporting compound, the second host may be an electron transporting compound, and the weight fraction W (H1) of the first host and the weight fraction W (H2) of the second host may be W (H1) > W (H2).

In one or more embodiments, the first host may be a hole transporting compound, the second host may be an electron transporting compound, and W (H1) may be about 0.5 to about 0.7, for example about 0.503 to about 0.697, about 0.503 to about 0.651, or about 0.558 to about 0.651.

In one or more embodiments, the first host may be a hole transporting compound, the second host may be an electron transporting compound, and W (H2) may be about 0.2 to about 0.45, for example about 0.225 to about 0.427, or about 0.233 to about 0.427.

In one or more embodiments, the dipole moment of at least one of the m1 dopants (e.g., each of the m1 dopants) in the composition can be about 6 debye or less, such as about 1.5 debye to about 6 debye, or about 1.5 debye to about 5 debye, or about 1.5 debye to about 4 debye.

At the same time, HOMO (H _min ) Is the smallest value among the absolute values of the highest occupied molecular orbital levels of the m2 hosts, and is calculated as eV, HOMO (D _min ) Is the smallest value among the absolute values of the highest occupied molecular orbital levels of the m1 dopants and is calculated in eV, and W (H _{LUMO_max} ) A weight fraction of the host having a maximum value among absolute values of Lowest Unoccupied Molecular Orbital (LUMO) energy levels of the m2 hosts, relative to a total weight of the m1 dopants and the m2 hosts.

The HOMO level and the LUMO level are each negative values measured using differential pulse voltammetry using ferrocene as a reference material. For example, the HOMO energy level and the LUMO energy level may each be measured according to the methods described in table 1.

In one or more embodiments, the composition may have coordinates of an improved image represented by (X, Y) satisfying the following condition: x is about 1.112 to about 1.534 and Y is about 0.119 to about 0.160, or X is about 1.112 to about 1.534 and Y is about 0.119 to about 0.151.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) in the composition can emit green light.

In one or more embodiments, the maximum emission wavelength (peak emission wavelength) in the emission spectrum of at least one of the m1 dopants (e.g., each of the m1 dopants) in the composition can be from about 500 nanometers (nm) to about 580nm, such as from about 510nm to about 540nm.

When the composition has coordinates of an improved image represented by (X, Y) existing within a quadrangle having 4 vertices at (1.112,0.119), (1.720,0.119), (1.530,0.160), and (1.112,0.180), the off time of a light emitting device using the composition can be reduced. Therefore, it is possible to substantially prevent afterimages (residual images) from occurring after turning off or stopping current for a light emitting device using the composition. In addition, the turn-on time of a light emitting device using the composition can be reduced. Accordingly, a color dragging (hysteresis) phenomenon after applying a current to a light emitting device using the composition can be substantially prevented.

For example, when at least one of the m1 dopants (e.g., each of the m1 dopants) included in the composition emits green light, a light emitting device using the composition may emit green light while its off-time is simultaneously reduced. In addition, the on time is also reduced.

Accordingly, by using a light emitting device using the composition, a high quality electronic device (e.g., a display device) can be manufactured.

At least one of the m1 dopants (e.g., each of the m1 dopants) may be an organometallic compound containing a transition metal, and each of the m2 hosts may be a compound that may not include a transition metal. In other words, each of the m2 hosts may be an organic compound.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) is an iridium-containing organometallic compound, and the iridium-containing organometallic compound may contain a first ligand, a second ligand, and a third ligand, wherein each of the first ligand, the second ligand, and the third ligand is bound to iridium, and each of the first ligand, the second ligand, and the third ligand may be a bidentate ligand that is bonded to iridium via C and N.

For example, the number of the cells to be processed,

the first ligand, the second ligand, and the third ligand may be the same as each other, or

The first ligand and the second ligand may be the same as each other, and the second ligand and the third ligand may be different from each other, or

The first ligand and the second ligand may be different from each other, and the second ligand and the third ligand may be the same as each other, or

The first ligand, the second ligand, and the third ligand may be different from one another.

In one or more embodiments, the first ligand, the second ligand, and the third ligand may be identical to one another.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) is an iridium-containing organometallic compound, and the iridium-containing organometallic compound may include at least one of the following: deuterium, fluoro groups, si, ge, or combinations thereof. For example, the iridium-containing organometallic compound may include at least one of: deuterium, fluoro group, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, -Si (Q) ₃ )(Q ₄ )(Q ₅ )、-Ge(Q ₃ )(Q ₄ )(Q ₅ ) Or a combination thereof, wherein Q ₃ -Q ₅ Can each independently be C ₁ -C ₂₀ Alkyl or phenyl.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) may be an iridium-containing organometallic compound, and the iridium-containing organometallic compound may include at least one of: a naphtho-benzosilol group, a naphtho-benzogermano-cyclopentadienyl group phenanthrobenzofuran group, phenanthrobenzothien group a naphtho-benzosilole group, a naphtho-benzogermano-cyclopentadienyl group, a phenanthro-benzofuran group, a phenanthro-benzothiophene group, a naphtho-benzofuranyl group, a phenanthro-benzofuranyl group phenanthrobenzselenophene group, phenanthrobenzopyrrole group, phenanthrobenzgermanium heterocyclopentadiene group, azadibenzofuran group an azadibenzoselenophene group, an azadibenzosilole group, an azadibenzogermacrene group, an azanaphthacene benzofurane group, an azanaphthacene phenoselenophene group, an azanaphthacenesilole group, an azanaphthacene germacrene group, an azaphenanthrobenzbenzofurane group, an azaphenanthrobenzselenophene group, an azaphenanthrobenzsilole group, an azaphenanthrobenzgermeneamine group, or a combination thereof.

For example, the iridium-containing organometallic compound may include at least one of: dibenzofuran groups, dibenzothiophene groups, naphthobenzofuran groups, naphthobenzothiophene groups, phenanthrobenzfuran groups, phenanthrobenzothiophene groups, azadibenzofuran groups, azadibenzothiophene groups, azanaphthobenzofuran groups, azanaphthobenzothiophene groups, azaphenanthrobenzothiophene groups, or combinations thereof, each of which may be attached to iridium via a C.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) may be an iridium-containing organometallic compound, and the iridium-containing organometallic compound may include at least one of: benzimidazole groups, each of which may be attached to iridium via N, benzoAn azole group, a benzothiazole group naphthoimidazole group, naphtho->An azole group, a naphthothiazole group, a phenanthroimidazole group, a phenanthroi ∈ ->An azole group, a phenanthrothiazole group, a pyridoimidazole group, a pyrido +.>An azole group, a pyridothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, or a combination thereof.

For example, the iridium-containing organometallic compound may include at least one of: a benzimidazole group, a naphthazole group, a phenanthroimidazole group, or a combination thereof, each of which may be attached to iridium via N.

In one or more embodiments, at least one of the m1 dopants (e.g., each of the m1 dopants) may be an iridium-containing organometallic compound, and the iridium-containing organometallic compound may include a ring a connected to iridium via N ₃ And ring a linked to iridium via C ₄ Wherein ring A ₃ And ring A ₄ Connected to each other by single bonds, ring A ₃ Can be a benzimidazole group, a benzoAn azole group, a benzothiazole group naphthoimidazole group, naphtho->An azole group, a naphthothiazole group, a phenanthroimidazole group, a phenanthroi ∈ ->An azole group, a phenanthrothiazole group, a pyridoimidazole group, a pyrido +.>An azole group, a pyridothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, or an isoquinoline group, and ring A ₄ May be a dibenzofuran group, dibenzothiophene group, naphthobenzofuran group, naphthobenzothiophene group, phenanthrobenzfuran group, phenanthrobenzothene group, azadibenzofuran group, azadibenzothiophene group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azaphenanthrobenzfuran group, or azaphenanthrobenzothene group.

In one or more embodiments, the host having the maximum value among absolute values of LUMO levels of the m2 hosts may include a triazine group.

The compositions as described herein may be used in emissive layers of electronic devices, such as light emitting devices. Thus, according to another aspect, there is provided a light emitting device comprising: a first electrode; a second electrode opposite to the first electrode; and an intermediate layer located between the first electrode and the second electrode, wherein the intermediate layer comprises an emissive layer, and wherein the emissive layer comprises a composition described herein.

In one or more embodiments, the emission layer may emit green light.

For example, the maximum emission wavelength of the electroluminescent spectrum of light emitted from the emissive layer may be from about 500nm to about 580nm, such as from about 510nm to about 540nm.

In one or more embodiments, the light emitting device comprising a composition as described herein may have an off time of about 100 microseconds (μs) or less, or about 10 μs to about 100 μs, about 30 μs to about 95 μs, about 50 μs to about 90 μs, about 55 μs to about 85 μs, about 60 μs to about 80 μs, or about 64 μs to about 80 μs.

In one or more embodiments, the light emitting device comprising the composition as described herein may have an on time of about 300 μs or less, about 50 μs to about 300 μs, about 100 μs to about 270 μs, about 150 μs to about 260 μs, or about 180 μs to about 256 μs.

In the case of a light emitting device having off-time and on-time of these ranges, a phenomenon in which an afterimage is formed after a current is cut off and a color dragging phenomenon after a current is applied can be substantially prevented.

The term "off-time" as used herein refers to the time required for the luminance of a light emitting device to reach 10% of the maximum luminance after stopping the current applied to the light emitting device.

The term "on-time" as used herein refers to the time required for the luminance of a light emitting device to reach 90% of the maximum luminance after a current is applied to the light emitting device.

In one or more embodiments, the intermediate layer of the light emitting device may further include a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

The term "intermediate layer" as used herein refers to a single layer or multiple layers arranged between a first electrode and a second electrode of a light emitting device. The "intermediate layer" may include not only organic compounds but also organometallic complexes comprising metals.

In one or more embodiments, the intermediate layer may include

M light emitting units each including at least one emission layer, and

m-1 charge generation layers disposed between two adjacent light emitting units of the m light emitting units,

m is an integer of 2 or more, and

the emissive layer included in at least one light emitting unit of the m light emitting units comprises a composition described herein. That is, the light emitting device may have a serial structure in which a plurality of light emitting cells are vertically stacked between a first electrode and a second electrode. For example, m may be 2, 3, 4, 5, 6, 7, 8, 9, or 10. In one or more embodiments, m can be 2, 3, 4, 5, or 6.

The light emitted from the m light emitting units may be the same or different from each other.

In one or more embodiments, the light emitted from each of the m light emitting units may be green light.

In one or more embodiments, the light emitted from at least one of the m light emitting units may be green light, and the light emitted from at least one of the remaining light emitting units may be blue light.

In one or more embodiments, the light emitting device may further include a substrate including a red sub-pixel, a green sub-pixel, and a blue sub-pixel, the first electrode may be patterned for each of the red sub-pixel, the green sub-pixel, and the blue sub-pixel, and the emission layer may include a red emission layer corresponding to the red sub-pixel, a green emission layer corresponding to the green sub-pixel, and a blue emission layer corresponding to the blue sub-pixel, wherein the green emission layer may contain a composition described herein. That is, the light emitting device may be a full color light emitting device.

In one or more embodiments, the region of the green sub-pixel of the intermediate layer of the light emitting device may include:

m light emitting units each of which may include at least one emission layer; and

m-1 charge generation layers which can be arranged between two adjacent light emitting units of the m light emitting units, wherein

m is an integer of 2 or more, and

the emission layer included in at least one of the m light emitting units may be a green emission layer, and the green emission layer may include a composition as described herein.

In one or more embodiments, the |R of the light emitting device _{Shut off} -G _{Shut off} I and B _{Shut off} -G _{Shut off} At least one of the (e.g., |r) _{Shut off} -G _{Shut off} I and B _{Shut off} -G _{Shut off} All of i) may be about 100 mus or less. In this regard, R _{Shut off} G for a time required for the luminance of red light emitted from the red emission layer to reach 10% of the maximum luminance of the red light after stopping (cutting off) the current to the light emitting device _{Shut off} For a time required for the luminance of green light emitted from the green emission layer to reach 10% of the maximum luminance of the green light after stopping (cutting off) the current for the light emitting device, and B _{Shut off} A time required for the luminance of blue light emitted from the blue emission layer to reach 10% of the maximum luminance of the blue light after stopping (cutting off) a current for the light emitting device. Thus, what isThe difference between the off-time of the red light and the off-time of the green light and/or the difference between the off-time of the blue light and the off-time of the green light in the light emitting device may be significantly reduced so that any afterimage (e.g., green afterimage) that may be generated after the current is cut off or stopped for the light emitting device may be substantially prevented.

In one or more embodiments, the |R of the light emitting device _{Opening the valve} -G _{Opening the valve} I and B _{Opening the valve} -G _{Opening the valve} At least one of the (e.g., |r) _{Opening the valve} -G _{Opening the valve} I and B _{Opening the valve} -G _{Opening the valve} All of i) may be about 150 μs or less, for example about 100 μs or less. In this regard, R _{Opening the valve} G for a time required for the luminance of red light emitted from the red emission layer to reach 90% of the maximum luminance of the red light after applying a current to the light emitting device _{Opening the valve} For a time required for the luminance of green light emitted from the green emission layer to reach 90% of the maximum luminance of the green light after applying a current to the light emitting device, and B _{Opening the valve} A time required for the luminance of blue light emitted from the blue emission layer to reach 90% of the maximum luminance of the blue light after applying a current to the light emitting device. Accordingly, a difference between an on-time of red light and an on-time of green light and/or a difference between an on-time of blue light and an on-time of green light in the light emitting device may be significantly reduced, so that a color dragging phenomenon after a current is applied to the light emitting device may be substantially prevented.

While not intending to be limited by a particular theory, in general, the on-time and off-time of green light in a full-color light emitting device are relatively large compared to the on-time and off-time of red light and blue light. Therefore, since the brightness of red light and blue light increases more rapidly than the brightness of green light after applying a current to the full-color light emitting device, instead of directly changing from a black screen to a white screen over time (for example, within several seconds) after applying a current, a black screen, a purple screen, and a white screen may be sequentially visualized, that is, a purple dragging phenomenon may occur. Also, since the luminance of red light and blue light is reduced more rapidly than that of green light after current is cut off for the full-color light emitting device, instead of being changed from a white screen directly to a black screen over time (for example, within several seconds) after current is cut off, a white screen, a green screen, and a black screen may be sequentially visualized, that is, a green afterimage may be formed. In this regard, since green light has high visibility to the human eye, control of the on-time and off-time of the green light may have a direct effect on improving the overall image quality of the light emitting device.

This problem can be solved by using a composition as described herein with coordinates of an improved image represented by (X, Y): the (X, Y) exists within a quadrilateral having four vertices at (1.112,0.119), (1.720,0.119), (1.530,0.160), and (1.112,0.180).

While not intending to be limited by any particular theory, in general, the off time for the emission of red and blue light may be approximately about 100 μs. Thus, in the case of a full color light emitting device having a green emissive layer comprising a composition as described herein, the off-time of the green light may be substantially similar to the off-time of each of the red light and the blue light. Accordingly, an afterimage such as a green afterimage after current is cut off or stopped for the full-color light emitting device can be substantially prevented.

In addition, while not intending to be limited by a particular theory, in general, the on-time for the emission of red and blue light may be approximately from about 140 μs to about 200 μs. Thus, in the case of a full color light emitting device having a green emissive layer comprising a composition as described herein, the on-time of the green light may be substantially similar to the on-time of each of the red and blue light. Accordingly, a color dragging phenomenon, such as a purple dragging phenomenon, after a current is applied to the full-color light emitting device can be substantially prevented.

Accordingly, a full-color light emitting device using the composition described herein can provide high quality images without afterimage and color dragging phenomena even under various brightness and driving conditions (e.g., low brightness, and high scan rate driving conditions such as 120 hz).

In one or more embodiments, the iridium-containing organometallic compound as described herein may be an organometallic compound represented by formula 2:

2, 2

M ₂ (L ₁₁ ) _n11 (L ₁₂ ) _n12 (L ₁₃ ) _n13 。

M in formula 2 ₂ Iridium (Ir) may be used.

In formula 2, L ₁₁ Can be a ligand represented by formula 2-1, L ₁₂ Can be a ligand represented by formula 2-2, and L ₁₃ May be a ligand represented by formula 2-1 or 2-2:

wherein formulae 2-1 and 2-2 are as described herein. Each of formulas 2-1 and 2-2 represents M in formula 2 ₂ Is a binding site for a polypeptide.

In formula 2, L ₁₁ And L ₁₂ May be different from each other.

In formula 2, n11 to n13 each represent L ₁₁ Number of (3) to L ₁₃ And may each independently be 0, 1, 2, or 3, where n11+n12+n13 may be 3.

In one or more embodiments, in formula 2, n11 may be 1, 2, or 3, and n12 and n13 may each independently be 0, 1, or 2.

In one or more embodiments, in formula 2, n12 may be 1, 2, or 3, and n11 and n13 may each independently be 0, 1, or 2.

In one or more embodiments, n11 may be 1, n12 may be 2, and n13 may be 0.

In one or more embodiments, n11 may be 2, n12 may be 1, and n13 may be 0.

In one or more embodiments, n11 can be 3, and n12 and n13 can each be 0.

In one or more embodiments, n12 can be 3, and n11 and n13 can each be 0.

The organometallic compound represented by formula 2 may be a heteroleptic complex or a homoleptic complex.

In one or more embodiments, the organometallic compound represented by formula 2 may be a homoleptic complex. That is, the three ligands in the organometallic compound represented by formula 2 may be identical to each other.

Y in the formulae 2-1 and 2-2 ₁ -Y ₄ And each independently may be C or N.

In one or more embodiments, in formulas 2-1 and 2-2, Y ₁ And Y ₃ Each may be N, and Y ₂ And Y ₄ Each may be C.

Ring A in formulae 2-1 and 2-2 ₁ Ring A ₄ Can each independently be C ₅ -C ₃₀ Carbocyclic group or C ₁ -C ₃₀ A heterocyclic group.

For example, ring A in formulas 2-1 and 2-2 ₁ Ring A ₄ May each independently be i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring,

Wherein the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group silol groups, borole groups, phosphole groups, germanium heterocyclopentadiene groups, selenophene groups,An azole group,Diazole groups, (-)>Triazole groups, thiazole groups, thiadiazole groups, thiatriazole groups, pyrazole groups, imidazole groups, triazole groups, tetrazole groups,Or an azasilol group, and +.>

The second ring may be an adamantyl group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

In one or more embodiments, ring A in formulas 2-1 and 2-2 ₁ Ring A ₄ Can be independently cyclopentane group, cyclohexane group, cyclohexene group, phenyl group, naphthalene group, anthracene group, phenanthrene group, benzo [9,10 ]]A phenanthrene group, a pyrene group,A group, 1,2,3, 4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, silole group, borole group, phosphole group, germanium heterocyclopentadiene group, selenophene group, indene group, indole group, benzofuran group, benzothiophene group, benzoborole group, benzophospholopentadiene group, benzogermanium heterocyclopentadiene group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilole group, dibenzoborole group, dibenzophosphole group, dibenzogermanium heterocyclopentadiene group, dibenzoselenophene group, benzofluorene group, benzocarbazole group, benzogermanium heterocyclopentadiene group, benzoimidazole group, benzothiophene group, dibenzothiophene group a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzoxazole group, a naphthobenzoborolane group, a naphthobenzophospholane group, a naphthobenzogermanium heterocyclopenadiene group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a naphthogermanium heterocyclopenadiene group, a naphthoselenophene group, a dibenzofluorene group, a dinaphthofuran group, a naphthothiophene group, a naphthobenzoxazole group, a naphthogermanium group, a naphthoselenophene group, a naphthobenzoxepin group, a dibenzocarbazole group, a naphthobenzoxepin group, a naphthobenzoxalon group, a naphthoxazole group, a naphthobenzoxalone group, a naphtho-and a naphtho-benzoxalon group a dinaphthophor group, a dinaphthopelemene group, an indenophene group, an indolophene group, a phenanthrobenzofuran group, phenanthrobenzothien group, phenanthrobenzothiolo group, phenanthrobenzoboropentadienyl group, phenanthrobenzopyrrole diene group, phenanthrobenzopyrrole group, Phenanthrene-benzogermanium-heterocyclopenadiene group, phenanthrene-benzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5, 5-dioxide group, azaindene group, azaindole group, and process for preparing the same an azabenzofuran group, an azabenzothiophene group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermane cyclopentadiene group azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanium heterocyclopentadiene group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group an azanaphthacene benzofuranyl group, an azanaphthacene benzosilol group, an azanaphthacene benzoborole group, an azanaphthacene benzophosphole group, an azanaphthacene benzogermanium cyclopentadiene group, an azanaphthacene benzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group an azadinaphthozole group, an azadinaphthoborole group, an azadinaphthophor group, an azadinaphtho-phosphine group, an azadinaphthogermanium heterocyclopentadine group, an azadinaphthoselenophene group an azaindeno phenanthrene group, an azaindolo phenanthrene group, an azaphenanthro benzofurane group, an azaphenanthro acene benzothiophene group, an azaphenanthro acene silole group, an azaphenanthro acene borole group, an azaphenanthro, azaphenanthrene acenaphthophosphorus heterocyclopentadiene group, azaphenanthrene acenaphthogermanium heterocyclopentadiene group, azaphenanthrene acenaphthoselenophene group, azadibenzothiophene 5-oxide group, aza 9H-fluorene-9-one group, azadibenzothiophene 5, 5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyridine group, Pyrazole group, imidazole group, triazole group, < ->An azole group, iso->An azole group, a thiazole group, an isothiazole group,/-thiazole group>Diazole groups, thiadiazole groups, azasilole groups, azaborole groups, azaphosphole groups, azagermanium cyclopentadiene groups, azaselenophene groups, benzopyrrole groups, benzopyrazole groups, benzimidazole groups, benzo->Azole groups, benziso->An azole group, a benzothiazole group, a benzisothiazole group, and a benzoDiazole group, benzothiadiazole group, pyridopyrrole group, pyridopyrazole group, pyridoimidazole group, and pyridoAzole group, pyrido-iso->An azole group, a pyridothiazole group, a pyridoisothiazole group, pyrido +.>Diazole group, pyridothiadiazole group, pyrimidopyrrole group, pyrimidopyrazole group, pyrimidoimidazole group, pyrimido +.>Azole group, pyrimidoiso->An azole group, a pyrimidothiazole group, a pyrimidoisothiazole group, a pyrimido +.>Diazole group, pyrimidothiadiazole group, naphtopyrrole group, naphtopyrazole group, naphtoimidazole group, naphto +.>Azole groups, naphtho-iso- >An azole group, a naphthothiazole group, a naphthoisothiazole group, and naphtho +.>Diazole group, naphthacenediazole group, phenanthropyrrole group, phenanthropyrazole group, phenanthroimidazole +.>Azole group, phenanthroi->An azole group, a phenanthrothiazole group, a phenanthroisothiazole group, and a phenanthro +.>An diazole group, a phenanthrothiadiazole group, a 5,6,7, 8-tetrahydroisoquinoline group, a 5,6,7, 8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a phenyl group having a cyclohexane group fused thereto, a phenyl group having a norbornane group fused thereto, a pyridine group having a cyclohexane group fused thereto, or a pyridine group having a norbornane group fused thereto.

In formulae 2-1 and 2-2, ring A ₁ And ring A ₃ May be the same or different from each other.

In one or more embodiments, ring a ₁ Contains Y ₁ Monocyclic group of (C), ring A ₂ Contains Y ₂ And ring A ₄ Contains Y ₄ Can each independently be a 6 membered ring.

In one or more embodiments, ring a ₃ Contains Y ₃ The monocyclic group of (2) may be a 6 membered ring.

In one or more embodiments, ring a ₃ Contains Y ₃ The monocyclic group of (2) may be a 5-membered ring.

In one or more embodiments, ring a ₁ Contains Y ₁ The monocyclic group of (2) may be a 6-membered ring, and ring A ₃ Contains Y ₃ The monocyclic group of (2) may be a 5-membered ring.

In one or more embodiments, in formulas 2-1 and 2-2, ring A ₁ And ring A ₃ May each independently be i) a group A, ii) a polycyclic ring group in which two or more groups A are fused to each other, or iii) a polycyclic ring group in which at least one group A and at least one group B are fused to each other,

wherein the group A may comprise a pyridine group, pyrimidine group, pyridazine group, pyrazine group, or triazine group, and

the group B may include a cyclohexane group, cyclohexene group, norbornane group, phenyl group, furan group, thiophene group, selenophene group, pyrrole group, cyclopentadiene group, or silole group.

In one or more embodiments, in formula 2-2, ring A ₃ May be i) a group C, ii) a polycyclic ring group in which two or more groups C are fused to each other, or iii) a polycyclic ring group in which at least one group C and at least one group D are fused to each other,

wherein the group C may comprise a pyrrole group, a pyrazole group, an imidazole group, a triazole group,An azole group, iso- >An azole group, a thiazole group, or an isothiazole group, and

the group D may include a cyclohexane group, a cyclohexene group, a norbornane group, a phenyl group, a furan group, a thiophene group, a selenophene group, a cyclopentadiene group, a silole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group.

In one or more embodiments, ring A in formula 2-1 ₁ The method comprises the following steps:

a pyridine group, pyrimidine group, pyridazine group, or pyrazine group; or (b)

Each with at least one of a fused pyridine group, pyrimidine group, pyridazine group, or pyrazine group, as follows: a cyclohexane group, a norbornane group, a phenyl group, or a combination thereof.

In one or more embodiments, ring A in formula 2-2 ₃ The method comprises the following steps:

a pyridine group, pyrimidine group, pyridazine group, or pyrazine group;

a pyridine group, pyrimidine group, pyridazine group, or pyrazine group each fused to a cyclohexane group, norbornane group, phenyl group, or a combination thereof; or (b)

Imidazole groups, benzimidazole groups, naphthazole groups, phenanthroimidazole groups, pyridoimidazole groups,Azole groups, benzo->Azole group, naphtho->Azole group, phenanthro- >Azole group, pyrido->An azole group, a thiazole group, a benzothiazole group, a naphthothiazole group, a phenanthrothiazole group, or a pyridothiazole group.

In one or more embodiments, ring A in formulas 2-1 and 2-2 ₂ And ring A ₄ May be different from each other.

In one or more embodiments, in formulas 2-1 and 2-2, ring A ₂ And ring A ₄ May each independently be i) a group E, ii) a polycyclic ring group in which two or more groups E are fused to each other, or iii) a polycyclic ring group in which at least one group E and at least one group F are fused to each other,

wherein the group E may comprise a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and

the group F may include furan groups, thiophene groups, selenophene groups, pyrrole groups, cyclopentadiene groups, silole groups, pyrazole groups, imidazole groups,An azole group, a thiazole group, and i->An azole group, or an isothiazole group.

In one or more embodiments, in formula 2-1, ring A ₂ May be a polycyclic ring group in which two or more groups E and at least one group F are fused to each other.

In one or more embodiments, in formula 2-2, ring A ₄ May be a polycyclic ring group in which two or more groups E and at least one group F are fused to each other.

In one or more embodiments, ring A in formula 2-1 ₂ The method comprises the following steps:

a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, or a dibenzosilole group; or (b)

Each with at least one fused phenyl group, naphthalene group, phenanthrene group, dibenzofuran group, dibenzothiophene group, dibenzoselenophene group, carbazole group, fluorene group, or dibenzosilol group as follows: a cyclohexane group, a norbornane group, a phenyl group, or a combination thereof.

In one or more embodiments, ring A in formula 2-2 ₄ The method comprises the following steps:

a phenyl group, a naphthalene group, a phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a dibenzoselenophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzoselenophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group; or (b)

Each with at least one fused phenyl group, naphthalene group, phenanthrene group, dibenzofuran group, dibenzothiophene group, dibenzoselenophene group, carbazole group, fluorene group, dibenzosilole group, azadibenzofuran group, azadibenzothiophene group, azadibenzoselenophene group, azacarbazole group, azafluorene group, or azadibenzosilole group: phenyl group, pyridyl group, pyrimidine group, pyridazine group, pyrazine group, cyclohexane group, norbornane group, furan group thiophene group, selenophene group, pyrrole group, cyclopentadiene group, silole group, pyrazole group, imidazole group, An azole group, a thiazole group, and i->An azole group, an isothiazole group, or a combination thereof.

In one or more embodiments, ring A in formula 2-2 ₄ Can be dibenzofuran group, dibenzothiophene group, dibenzoselenophene group a dibenzosilol group, a dibenzogermanium heterocyclopentadiene group,A naphthabenzofuranyl group, a naphthabenzothiophenyl group, a naphthabenzoselenophenyl group, a naphthabenzosilol group, a naphthabenzobenzothiophenyl group, a naphthabenzoguanyl group, a phenanthrobenzbenzothiophene group, a phenanthrobenzselenophene group, a phenanthrobenzthianthrene group, a phenanthrobenzgermanium heterocyclopentadienyl group, an azadibenzofuranyl group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzosilole group, an azadibenzogermylene group, an azanaphthacene group, an azanaphthabenzobenzothiophene group, an azanaphthacene benzothiophene group, an azanaphthacene benzoguanene group, an azaphenanthrobenzbenzothiophene group, an azabenzophenocene group, an azaphenanthrobenzselenophene group, an azabenzophenole group, or an azabenzophenodiene group.

W in formulas 2-1 and 2-2 ₁ -W ₄ Can each independently be a single bond, unsubstituted or substituted with at least one R _10a Substituted C ₁ -C ₂₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₅ -C ₃₀ Carbocyclic groups, either unsubstituted or substituted with at least one R _10a Substituted C ₁ -C ₃₀ A heterocyclic group.

For example, W in formulas 2-1 and 2-2 ₁ -W ₄ Each independently can be:

a single bond; or (b)

Each unsubstituted or substituted by at least one R _10a Substituted cyclopentenyl groups, cyclohexane groups, cyclohexene groups, phenyl groups, naphthalene groups, anthracene groups, phenanthrene groups, benzo [9,10 ]]A phenanthrene group, a pyrene group,Groups, cyclopentadienyl groups, 1,2,3, 4-tetrahydronaphthyl groups, thienyl groups, furyl groups, indolyl groups, benzoborolan groups, benzophospholan groups, indenyl groups, benzothiophenyl groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenophene groups, benzofuran groups, carbazolyl groupsGroup, dibenzoborolane group, dibenzophospholane group, fluorene group, dibenzosilol group, dibenzogermanium cyclopentalane group, dibenzothiophene group dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-ketone group, dibenzothiophene 5, 5-dioxide group dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group 9H-fluoren-9-one group, dibenzothiophene 5, 5-dioxide group azadibenzoborole groups, azadibenzophosphole groups, azafluorene groups, azadibenzosilole groups, azadibenzogermanium heterocyclopentadene groups an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, a catalyst comprising at least one of an azadibenzothiophene and an azadibenzothiophene aza-9H-fluoren-9-one group, aza-dibenzothiophene 5, 5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group >An azole group, iso->An azole group, a thiazole group, an isothiazole group,/-thiazole group>Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo +.>An azole group, a benzothiazole group, a benzo +.>An diazole group, a benzothiadiazole group, a 5,6,7, 8-tetrahydroisoquinoline group, a 5,6,7, 8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

In one or more embodiments, W in formulas 2-1 and 2-2 ₁ -W ₄ Each independently can be:

a single bond; or (b)

Each unsubstituted or substituted by at least one R _10a A substituted phenyl group, a naphthalene group, a pyridine group, a fluorene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group.

a single bond; or (b)

C each unsubstituted or substituted by at least one of ₁ -C ₂₀ An alkylene group, a phenyl group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, C ₃ -C ₁₀ Cycloalkyl, deuterated C ₃ -C ₁₀ Cycloalkyl, fluoro C ₃ -C ₁₀ Cycloalkyl, (C) ₁ -C ₂₀ Alkyl) C ₃ -C ₁₀ Cycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, naphthyl, pyridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, or a combination thereof.

Z in the formulae 2-1 and 2-2 ₁ -Z ₄ Can be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF, each independently ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ Alkyl, substituted or unsubstituted C ₂ -C ₆₀ Alkenyl, substituted or unsubstituted C ₂ -C ₆₀ Alkynyl, substituted or unsubstituted C ₁ -C ₆₀ Alkoxy, substituted or unsubstituted C ₁ -C ₆₀ Alkylthio, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkyl, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ Aryl, substituted or unsubstituted C ₇ -C ₆₀ Alkylaryl, substituted or unsubstituted C ₇ -C ₆₀ Arylalkyl, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy, substituted or unsubstituted C ₆ -C ₆₀ Arylthio, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl, substituted or unsubstituted C ₂ -C ₆₀ Alkyl heteroaryl, substituted or unsubstituted C ₂ -C ₆₀ Heteroarylalkyl, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryloxy, substituted or unsubstituted C ₁ -C ₆₀ Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N (Q) ₁ )(Q ₂ )、-Si(Q ₃ )(Q ₄ )(Q ₅ )、-Ge(Q ₃ )(Q ₄ )(Q ₅ )、-B(Q ₆ )(Q ₇ )、-P(＝O)(Q ₈ )(Q ₉ ) or-P (Q) ₈ )(Q ₉ )。Q ₁ -Q ₉ Each as described herein.

For example, Z in formulas 2-1 and 2-2 ₁ -Z ₄ Each independently can be:

hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ Alkyl, C ₂ -C ₂₀ Alkenyl, C ₁ -C ₂₀ Alkoxy, or C ₁ -C ₂₀ Alkylthio;

c each substituted by at least one of ₁ -C ₂₀ Alkyl, C ₂ -C ₂₀ Alkenyl, C ₁ -C ₂₀ Alkoxy, or C ₁ -C ₂₀ Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF ₅ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [ 2.2.1)]Heptyl), norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1]Amyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.2]Octyl group, (C) ₁ -C ₂₀ Alkyl) cyclopentyl, (C ₁ -C ₂₀ Alkyl) cyclohexyl, (C ₁ -C ₂₀ Alkyl) cycloheptyl, (C) ₁ -C ₂₀ Alkyl) cyclooctyl, (C ₁ -C ₂₀ Alkyl) adamantyl, (C ₁ -C ₂₀ Alkyl) norbornyl, (C ₁ -C ₂₀ Alkyl) norbornenyl, (C) ₁ -C ₂₀ Alkyl) cyclopentenyl, (C ₁ -C ₂₀ Alkyl) cyclohexenyl, (C ₁ -C ₂₀ Alkyl) cycloheptenyl, (C ₁ -C ₂₀ Alkyl) bicyclo [1.1.1]Amyl, (C) ₁ -C ₂₀ Alkyl) bicyclo [2.1.1]Hexyl, (C) ₁ -C ₂₀ Alkyl) bicyclo [2.2.2]Octyl, phenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [ 1.1.1.1, each unsubstituted or substituted with at least one of]Amyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.2]Octyl, phenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and,Radix et rhizoma PyriPyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl,/-thiazolyl>Azolyl, iso->Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzo- >Azolyl, benziso->Oxazolyl, triazolyl, tetrazolyl, < >>Diazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothienyl: deuterium, -F, -Cl, -Br, -I, -SF ₅ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, C ₁ -C ₂₀ Alkoxy, C ₁ -C ₂₀ Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1 ]]Amyl, bicyclo [2.1.1]Hexyl, bicyclo [2 ].2.2]Octyl group, (C) ₁ -C ₂₀ Alkyl) cyclopentyl, (C ₁ -C ₂₀ Alkyl) cyclohexyl, (C ₁ -C ₂₀ Alkyl) cycloheptyl, (C) ₁ -C ₂₀ Alkyl) cyclooctyl, (C ₁ -C ₂₀ Alkyl) adamantyl, (C ₁ -C ₂₀ Alkyl) norbornyl, (C ₁ -C ₂₀ Alkyl) norbornenyl, (C) ₁ -C ₂₀ Alkyl) cyclopentenyl, (C ₁ -C ₂₀ Alkyl) cyclohexenyl, (C ₁ -C ₂₀ Alkyl) cycloheptenyl, (C ₁ -C ₂₀ Alkyl) bicyclo [1.1.1]Amyl, (C) ₁ -C ₂₀ Alkyl) bicyclo [2.1.1 ]Hexyl, (C) ₁ -C ₂₀ Alkyl) bicyclo [2.2.2]Octyl, phenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, deuterated phenyl, fluorinated phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,>a group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>Azolyl, iso->Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzo->Azolyl, benziso->Oxazolyl, triazolyl, tetrazolyl, < >>Diazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or a combination thereof; or (b)

-N(Q ₁ )(Q ₂ )、-Si(Q ₃ )(Q ₄ )(Q ₅ )、-Ge(Q ₃ )(Q ₄ )(Q ₅ )、-B(Q ₆ )(Q ₇ )、-P(＝O)(Q ₈ )(Q ₉ ) or-P (Q) ₈ )(Q ₉ )，

Wherein Q is ₁ -Q ₉ Each independently can be:

deuterium, -F, -CH ₃ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CH ₂ CH ₃ 、-CH ₂ CD ₃ 、-CH ₂ CD ₂ H、-CH ₂ CDH ₂ 、-CHDCH ₃ 、-CHDCD ₂ H、-CHDCDH ₂ 、-CHDCD ₃ 、-CD ₂ CD ₃ 、-CD ₂ CD ₂ H、-CD ₂ CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、-CH ₂ CF ₃ 、-CH ₂ CF ₂ H、-CH ₂ CFH ₂ 、-CHFCH ₃ 、-CHFCF ₂ H、-CHFCFH ₂ 、-CHFCF ₃ 、-CF ₂ CF ₃ 、-CF ₂ CF ₂ H. or-CF ₂ CFH ₂ The method comprises the steps of carrying out a first treatment on the surface of the Or (b)

N-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-butyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl each of which is unsubstituted or substituted with at least one of: deuterium, -F, C ₁ -C ₁₀ Alkyl, phenyl, or a combination thereof.

In one or more embodiments, Z in formulas 2-1 and 2-2 ₁ -Z ₄ Each independently can be:

hydrogen, deuterium, -F, or cyano;

c which is unsubstituted or substituted by at least one of ₁ -C ₂₀ Alkyl: deuterium, -F, cyano, C ₃ -C ₁₀ Cycloalkyl, deuterated C ₃ -C ₁₀ Cycloalkyl, fluoro C ₃ -C ₁₀ Cycloalkyl, (C) ₁ -C ₂₀ Alkyl) C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, deuterated C ₁ -C ₁₀ Heterocycloalkyl, fluoro C ₁ -C ₁₀ Heterocycloalkyl, (C) ₁ -C ₂₀ Alkyl) C ₁ -C ₁₀ Heterocycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C) ₁ -C ₂₀ Alkyl) dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, fluorodibenzothienyl, (C) ₁ -C ₂₀ Alkyl) dibenzothienyl, or a combination thereof;

c each unsubstituted or substituted by at least one of ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, phenyl, biphenyl, naphthyl, pyridyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothienyl: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, C ₁ -C ₂₀ Alkoxy, C ₁ -C ₂₀ Alkylthio, deuterated C ₁ -C ₂₀ Alkoxy, fluoro C ₁ -C ₂₀ Alkoxy, C ₃ -C ₁₀ Cycloalkyl, deuterated C ₃ -C ₁₀ Cycloalkyl, fluoro C ₃ -C ₁₀ Cycloalkyl, (C) ₁ -C ₂₀ Alkyl) C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, deuterated C ₁ -C ₁₀ Heterocycloalkyl, fluoro C ₁ -C ₁₀ Heterocycloalkyl, (C) ₁ -C ₂₀ Alkyl) C ₁ -C ₁₀ Heterocycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C) ₁ -C ₂₀ Alkyl) dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, fluorodibenzothienyl, (C) ₁ -C ₂₀ Alkyl) dibenzothienyl, or a combination thereof; or (b)

-Si(Q ₃ )(Q ₄ )(Q ₅ ) or-Ge (Q) ₃ )(Q ₄ )(Q ₅ )。

In one or more embodiments, in formula 2-1, e1 and d1 may each be other than 0, and a plurality of Z ₁ At least one of (2) may be deuterated C ₁ -C ₂₀ Alkyl, -Si (Q) ₃ )(Q ₄ )(Q ₅ ) or-Ge (Q) ₃ )(Q ₄ )(Q ₅ )。Q ₃ -Q ₅ As described herein.

For example, Q ₃ -Q ₅ Each independently can be:

c which is unsubstituted or substituted by at least one of ₁ -C ₆₀ Alkyl: deuterium, C ₁ -C ₆₀ Alkyl, C ₆ -C ₆₀ Aryl, or a combination thereof; or (b)

C which is unsubstituted or substituted by at least one of ₆ -C ₆₀ Aryl: deuterium, C ₁ -C ₆₀ Alkyl, C ₆ -C ₆₀ Aryl, or a combination thereof.

In one or more embodiments, Q ₃ -Q ₅ Each independently can be:

-CH ₃ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CH ₂ CH ₃ 、-CH ₂ CD ₃ 、-CH ₂ CD ₂ H、-CH ₂ CDH ₂ 、-CHDCH ₃ 、-CHDCD ₂ H、-CHDCDH ₂ 、-CHDCD ₃ 、-CD ₂ CD ₃ 、-CD ₂ CD ₂ H. or-CD ₂ CDH ₂ The method comprises the steps of carrying out a first treatment on the surface of the Or (b)

N-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-butyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl each of which is unsubstituted or substituted with at least one of: deuterium, C ₁ -C ₁₀ Alkyl, phenyl, or a combination thereof.

In one or more embodiments, Q ₃ -Q ₅ May be identical to each other.

In one or more embodiments, Q ₃ -Q ₅ May be different from each other.

In one or more embodiments, the organometallic compound represented by formula 2 may satisfy at least one of the conditions (1) to (9):

condition (1)

E1 and d1 in formula 2-1 are each other than 0, and

at least one Z ₁ Including deuterium;

condition (2)

E2 and d2 in formula 2-1 are each other than 0, and

at least one Z ₂ Including deuterium;

condition (3)

E3 and d3 in formula 2-2 are each other than 0, and

at least one Z ₃ Including deuterium;

condition (4)

E4 and d4 in formula 2-2 are each other than 0, and

at least one Z ₄ Including deuterium;

condition (5)

E1 and d1 in formula 2-1 are each other than 0, and

at least one Z ₁ Comprising a fluorine group;

condition (6)

E2 and d2 in formula 2-1 are each other than 0, and

at least one Z ₂ Comprising a fluorine group;

condition (7)

E3 and d3 in formula 2-2 are each other than 0, and

at least one Z ₃ Comprising a fluorine group;

condition (8)

E4 and d4 in formula 2-2 are each other than 0, and

at least one Z ₄ Comprising a fluorine group;

condition (9)

N11 and n13 in formula 2 are each 0,

n12 in the formula 2 is 3,

three L in formula 2 ₁₂ Are identical to each other in that,

y in formula 2-2 ₃ Is the nitrogen, and is the nitrogen content of the alloy,

y in formula 2-2 ₄ Is a carbon source, which is a carbon source,

ring A in formula 2-2 ₃ Is a benzimidazole group, benzoAn azole group, a benzothiazole group naphthoimidazole group, naphtho->An azole group, a naphthothiazole group, a phenanthroimidazole group, a phenanthroi ∈ ->An azole group, a phenanthrothiazole group, a pyridoimidazole group, a pyrido +.>An azole group, or a pyridothiazole group, and

ring A in formula 2-2 ₄ Is dibenzofuran group, dibenzothiophene group, dibenzoselenophene group, dibenzosilole group, dibenzogermanium heterocyclopenadiene group, naphthobenzofuran group, naphthobenzothiophene group, naphthoselenophene group, naphthobenzophenone group, naphthogermanium heterocyclopenadiene group, phenanthrobenzfuran group, phenanthrobenzthiophene group, phenanthrobenzselenophene group, phenanthrobenzsilole group, phenanthrobenzene group, phenanthrobenzgermanium heterocyclopenadiene group, azadibenzofuran group A group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzothiophene group, an azadibenzogermacrene group, an azanaphthacene benzofuran group, an azanaphthacene thiophene group, an azanaphthacene selenophene group, an azanaphthacene silole group, an azanaphthacene heterocyclopentadiene group, an azaphenanthrobenzbenzofuran group, an azaphenanthrobenzthiophene group, an azaphenanthrobenzselenophene group, an azaphenanthrobenzzole group, or an azanaphthacene heterocyclopenadiene group.

In one or more embodiments, Z in formulas 2-1 and 2-2 ₁ -Z ₄ Can be hydrogen, deuterium, -F, -CH ₃ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₂ -C ₁₀ Alkenyl, C ₁ -C ₁₀ Alkoxy, C ₁ -C ₁₀ Alkylthio, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by-F, a group represented by one of formulas 9-201 to 9-227 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulas 9-201 to 9-227 in which at least one hydrogen is replaced by-F, a group represented by one of formulas 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulas 10-1 to 10-129 in which at least one hydrogen is replaced by-F, a group represented by one of formulas 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium, a group represented by one of formulas 10-201 to 10-350 in which at least one hydrogen is replaced by-F, a group represented by one of formulas 10-10 to 10-350 in which at least one of hydrogen is replaced by-F is represented by-Q (Si, a group represented by one of formulas-10 to-10-350) ₃ )(Q ₄ )(Q ₅ ) or-Ge (Q) ₃ )(Q ₄ )(Q ₅ ) Wherein Q is ₃ -Q ₅ Each as described herein.

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In formulas 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350, the expression "Ph" represents a binding site to an adjacent atom, the expression "TMS" represents a trimethylsilyl group, and the expression "TMG" represents a trimethylgermyl group.

The "group represented by one of the formulae 9-1 to 9-39 in which at least one hydrogen is replaced with deuterium" and the "group represented by one of the formulae 9-201 to 9-227 in which at least one hydrogen is replaced with deuterium" may each be, for example, a group represented by one of the formulae 9-501 to 9-514 and 9-601 to 9-636:

"the group represented by one of the formulae 9-1 to 9-39 in which at least one hydrogen is replaced with-F" and "the group represented by one of the formulae 9-201 to 9-227 in which at least one hydrogen is replaced with-F" may each be, for example, a group represented by one of the formulae 9-701 to 9-710:

"the group represented by one of the formulae 10-1 to 10-129 in which at least one hydrogen is replaced with deuterium" and "the group represented by one of the formulae 10-201 to 10-350 in which at least one hydrogen is replaced with deuterium" may be, for example, a group represented by one of the formulae 10-501 to 10-553:

/>

"the group represented by one of the formulae 10-1 to 10-129 in which at least one hydrogen is replaced by-F" and "the group represented by one of the formulae 10-201 to 10-350 in which at least one hydrogen is replaced by-F" may be, for example, a group represented by one of the formulae 10-601 to 10-617:

E1-e4 and d1-d4 in the formulae 2-1 and 2-2 each independently represent Z ₁ -Z ₄ By- [ W ] ₁ -(Z ₁ ) _e1 ]A group represented by: - [ W ] ₂ -(Z ₂ ) _e2 ]A group represented by: - [ W ] ₃ -(Z ₃ ) _e3 ]A group represented by, and represented by: - [ W ] ₄ -(Z ₄ ) _e4 ]The number of groups represented, and may each independently be an integer from 0 to 20. When e1 is 2 or more, two or more Z ₁ May be the same as or different from each other, when e2 is 2 or more, two or more Z ₂ May be the same as or different from each other, when e3 is 2 or more, two or more Z ₃ Can be mutually connected withIdentical or different, when e4 is 2 or more, two or more Z ₄ May be the same or different from each other, and when d1 is 2 or more, two or more are represented by the formula- [ W ₁ -(Z ₁ ) _e1 ]The radicals represented may be identical or different from one another, two or more radicals represented by the formula- [ W when d2 is 2 or more ₂ -(Z ₂ ) _e2 ]The radicals represented may be identical or different from one another, two or more are represented by the formula- [ W when d3 is 2 or more ₃ -(Z ₃ ) _e3 ]The radicals represented may be identical or different from one another and, when d4 is 2 or more, two or more are represented by the formula- [ W ₄ -(Z ₄ ) _e4 ]The radicals represented may be identical or different from one another. For example, e1-e4 and d1-d4 in formulas 2-1 and 2-2 may each independently be 0, 1, 2, or 3.

Meanwhile, in one or more embodiments, the iridium-containing organometallic compound may not be tris [ 2-phenylpyridine ] iridium.

In one or more embodiments, in formula 2-1, the following may be excluded: wherein Y is ₁ Is N, ring A ₁ Is a pyridine group, Y ₂ C, ring A ₂ Is a phenyl group, and d1 and d2 are each 0.

In formulas 2-1 and 2-2, at least one of the following groups may be independently and optionally bonded to each other to form a group that is unsubstituted or substituted with at least one R _10a Substituted C ₅ -C ₃₀ Carbocyclic groups, either unsubstituted or substituted with at least one R _10a Substituted C ₁ -C ₃₀ Heterocyclic group: i) Multiple Z ₁ Ii) a plurality of Z ₂ Iii) a plurality of Z ₃ Iv) a plurality of Z ₄ And v) Z ₁ -Z ₄ Is a single-phase alternating current power supply.

R _10a Can be as described herein with respect to Z ₁ Described.

The symbols x and x' as used herein each represent a binding site to an adjacent atom unless otherwise stated.

In some embodiments of the present invention, in some embodiments,

y in formula 2-1 ₁ It may be that it is N,and

in formula 2-1The group represented may be a group represented by one of formulas A1-1 to A1-3:

wherein, in the formulae A1-1 to A1-3,

Z ₁₁ -Z ₁₄ can each be as for Z ₁ As described in the description of the present invention,

R _10a can be obtained by reference to R provided herein _10a It will be understood that by way of a description of the (c),

a14 may be an integer from 0 to 4,

a18 may be an integer from 0 to 8,

* ' represents M in formula 2 ₂ Binding sites of (C), and

* "means and ring A ₂ Is a binding site for a polypeptide.

For example, Z in formulae A1-1 to A1-3 ₁₁ 、Z ₁₂ And Z ₁₄ At least one of (e.g., Z ₁₄ ) The method comprises the following steps:

c which is unsubstituted or substituted by at least one of ₁ -C ₂₀ Alkyl: deuterium, -F, phenyl, or a combination thereof;

-Si(Q ₃ )(Q ₄ )(Q ₅ ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)

-Ge(Q ₃ )(Q ₄ )(Q ₅ )。

In one or more embodiments of the present invention,

y in formula 2-2 ₃ Can be N, and

formula 2-2 is represented byThe group represented may be a group represented by one of the formulae NR1 to NR 48: />

/>

Wherein, in the formulae NR1 to NR48,

Y ₃₉ can be O, S, se, N- [ W ₃ -(Z ₃ ) _e3 ]、C(Z _39a )(Z _39b ) Or Si (Z) _39a )(Z _39b )，

W ₃ 、Z ₃ And e3 may each be as described herein, and Z _39a And Z _39b Can each be as for Z ₃ As described in the description of the present invention,

* ' represents M in formula 2 ₂ Binding sites of (C), and

* "means and ring A ₄ Is a binding site for a polypeptide.

In one or more embodiments of the present invention,

in the formulae 2-1 and 2-2, Y ₂ And Y ₄ Each may be C, and

in formula 2-1The radicals represented and the radicals represented by +.2-2>The groups represented may each independently be a group represented by one of formulas CR1 to CR 29:

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wherein, in the formulas CR1 to CR29,

Y ₄₉ can be O, S, se, N- [ W ₂ -(Z ₂ ) _e2 ]、N-[W ₄ -(Z ₄ ) _e4 ]、C(Z _29a )(Z _29b )、C(Z _49a )(Z _49b )、Si(Z _29a )(Z _29b ) Or Si (Z) _49a )(Z _49b )，

W ₂ 、W ₄ 、Z ₂ 、Z ₄ Each of e2, and e4 may be as described herein, Z _29a And Z _29b Can each be as for Z ₂ Described, and Z _49a And Z _49b Can each be as for Z ₄ As described in the description of the present invention,

Y ₂₁ -Y ₂₄ each of which may independently be N or C,

Ring A ₄₀ Can be C ₅ -C ₃₀ Carbocyclic group or C ₁ -C ₃₀ Heterocyclic groups (e.g., phenyl groups, naphthyl groups, phenanthrene groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, benzoisoquinoline groups, quinoxaline groups, benzoquinoxaline groups, quinazoline groups, or benzoquinazoline groups),

* M in the expression and formula 2 ₂ Binding sites of (C), and

* "means and ring A ₁ Or ring A ₃ Is a binding site for a polypeptide.

In one or more embodiments of the present invention,

from among formulae CR24 to CR29The group represented may be a group represented by one of formulas CR (1) to CR (13): />

Wherein, in the formulas CR (1) to CR (13),

Y ₄₉ as may be described herein, and

Y ₃₁ -Y ₃₄ and Y ₄₁ -Y ₄₈ And each independently may be C or N.

In one or more embodiments, the iridium-containing organometallic compound may include at least one deuterium.

In one or more embodiments, the iridium-containing organometallic compound may be an organometallic compound represented by formula 2 satisfying all of the following i) -v):

i) n11 and n13 are each 0,

ii) n12 is 3, and three L ₁₂ Are identical to each other in that,

iii) In formula 2-2, Y ₃ Is N, and Y ₄ In the form of C, the catalyst is a catalyst,

iv) the formula 2-2The group represented may be a group represented by one of the formulae NR29 to NR48, and +. >

v) the formula 2-2The group represented by one of the formulae CR24 to CR29 is a group represented by one of the formulae CR24 to CR29, and Y in the formulae CR24 to CR29 ₄₉ Can be O, S, se, or Si (Z) _49a )(Z _49b )。

For example, the iridium-containing organometallic compound may be at least one of the compounds of groups 1-1 to 1-7:

group 1-1

/>

Group 1-2

/>

Groups 1-3

/>

Groups 1-4

/>

Groups 1-5

/>

Groups 1-6

/>

Groups 1-7

As used herein, "Ome" is methoxy, "TMS" is trimethylsilyl, and "TMG" is trimethylgermyl.

Meanwhile, the m2 hosts in the emission layer may each include a hole transport compound, an electron transport compound, a bipolar compound, or a combination thereof. Each of the m2 hosts may not include a transition metal.

For example, m2 may be 2, and the host may include a hole transport compound and an electron transport compound, and the hole transport compound and the electron transport compound may be different from each other.

In one or more embodiments, the hole transport compound may include at least one pi-electron rich C ₃ -C ₆₀ Cyclic groups, and may not include electron transport groups. Examples of the electron transporting group include a cyano group, a fluorine group, a cyclic group containing nitrogen deficient in pi electrons, a phosphine oxide group, a sulfoxide group, and the like.

The term "cyclic group containing pi electron deficient nitrogen" as used herein refers to C having at least one x-n= x' moiety as the cyclic moiety ₁ -C ₆₀ A heterocyclic group. Non-limiting examples of the pi electron deficient nitrogen containing cyclic group may include triazine groups, imidazole groups, and the like.

The term "pi-electron rich C" as used herein ₃ -C ₆₀ The cyclic group "may be C excluding the x-n= moiety as the cyclic moiety ₃ -C ₆₀ A cyclic group. Said pi-electron rich C ₃ -C ₆₀ Non-limiting examples of cyclic groups may include phenyl groups, naphthyl groups, benzo [9,10]Phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indolodibenzofuran groups, indolodibenzothiophene groups, indolocarbazole groups, naphthobenzofuran groups, naphthobenzothiophene groups, benzocarbazole groups, phenanthrobenzofuran groups, phenanthrobenzothiene groups, naphthocarbazole groups, dinaphthofuran groups, dinaphthothiophene groups, dibenzocarbazole groups, and the like.

For example, the hole transport compound may include two or more carbazole groups.

In one or more embodiments, the electron transport compound may be a compound including at least one electron transport group. The electron transport group may be cyano, fluoro, C containing pi electron deficient nitrogen ₁ -C ₆₀ A cyclic group, a phosphine oxide group, a sulfoxide group, or a combination thereof. In one or more embodiments, the electron transport compound may include a triazine group.

For example, the electron transport compound may includeAt least one electron transporting group (e.g., triazine group, etc.) and at least one pi-electron rich C ₃ -C ₆₀ Cyclic groups (e.g. phenyl groups, naphthyl groups, benzo [9, 10)]Phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indolobidibenzofuran groups, indolobibenzothiophene groups, indolocarbazole groups, naphthobenzofuran groups, naphthobenzothiophene groups, benzocarbazole groups, phenanthrobenzofuran groups, phenanthrobenzothiene groups, naphthocarbazole groups, dinaphthofuran groups, dinaphthothiophene groups, dibenzocarbazole groups, and the like, or combinations thereof).

In one or more embodiments, the hole transport compound may be a compound represented by formula 6, but embodiments are not limited thereto:

6. The method is to

Wherein, in the formula 6,

L ₆₁ and L ₆₂ Can each independently be pi-electron rich C unsubstituted or substituted by at least one of ₃ -C ₆₀ Cyclic group (e.g., phenyl group): deuterium, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof,

e61 and e62 may each independently be integers from 1 to 6,

R ₆₁ -R ₆₄ each independently can be:

hydrogen, deuterium, C ₁ -C ₂₀ Alkyl, or deuterated C ₁ -C ₂₀ An alkyl group;

pi-electron rich C unsubstituted or substituted by at least one of ₃ -C ₆₀ Cyclic group (e.g., phenyl group): deuterium, C ₁ -C ₂₀ Alkyl groupDeuterated C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof; or (b)

-Si(Q ₃ )(Q ₄ )(Q ₅ )。

a63 and a64 may each independently be an integer of 0 to 7.

Q ₃ -Q ₅ And Q ₃₃ -Q ₃₅ Each as described herein.

In one or more embodiments, the hole transport compound may be a compound represented by one of formulas 6-1, 6-2, or 6-3, but the embodiment is not limited thereto:

6-1

6-2

6-3

Wherein, in the formulae 6-1 to 6-3, L ₆₁ 、L ₆₂ 、R ₆₁ -R ₆₄ E61, e62, a63, and a64, respectively, are as described herein.

In one or more embodiments, the hole transport compound may be one of the compounds H-HT1 to H-HT4, but the embodiment is not limited thereto:

in one or more embodiments, the electron transport compound may be a compound represented by formula 7:

7. The method of the invention

Wherein, in the formula 7,

X ₇₄ can be C (R) ₇₄ ) Or N, X ₇₅ Can be C (R) ₇₅ ) Or N, X ₇₆ Can be C (R) ₇₆ ) Or N, and X ₇₄ -X ₇₆ Can be N, at least one of which is,

L ₇₁ -L ₇₃ can each independently be C which is unsubstituted or substituted by at least one of ₅ -C ₃₀ Carbocyclic group or C ₁ -C ₃₀ Heterocyclic group: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof,

e71-e73 may each independently be an integer from 1 to 10,

R ₇₁ -R ₇₆ each independently can be:

hydrogen, deuterium, -F, or cyano;

c which is unsubstituted or substituted by at least one of ₁ -C ₂₀ Alkyl: deuterium, -F, cyano, or a combination thereof;

c each unsubstituted or substituted by at least one of ₅ -C ₃₀ Carbocyclic group or C ₁ -C ₃₀ Heterocyclic group: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, and fluorineSubstituted biphenylyl (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof; or (b)

-Si(Q ₃ )(Q ₄ )(Q ₅ )。

Q ₃ -Q ₅ And Q ₃₃ -Q ₃₅ Each as described herein.

In one or more embodiments, X in formula 7 ₇₄ -X ₇₆ Each may be N.

In one or more embodiments, L in formula 7 ₇₁ -L ₇₃ Can each independently be a phenyl group, a naphthyl group, a benzo [9,10 ] each unsubstituted or substituted with at least one of]Phenanthrene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, indolodibenzofuran groups, indolodibenzothiophene groups, indolocarbazole groups, naphthobenzofuran groups, naphthobenzothiophene groups, benzocarbazole groups, phenanthrobenzofuran groups, phenanthrobenzothiene groups, naphthocarbazole groups, dinaphthofuran groups, dinaphthothiophene groups, or dibenzocarbazole groups: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof.

In one or more embodiments, in formula 7, e 71L ₇₁ E 72L ₇₂ E 73L ₇₃ Each independently a dibenzofuran group, dibenzothiophene group, carbazole group, indolodibenzofuran group, each unsubstituted or substituted with at least one of indolobenzothioyl group, indolocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, benzocarbazole group, phenanthrobenzofuran group, phenanthrobenzothioyl group, naphthobenzothiophene group, and naphthobenzothiophene group, A naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof.

In one or more embodiments, in formula 7, e 71L ₇₁ E 72L ₇₂ E 73L ₇₃ Comprises a carbazole group, an indolocarbazole group, a benzocarbazole group, a naphtocarbazole group, or a dibenzocarbazole group, wherein the nitrogen atom of the pyrrole group in the carbazole group, indolocarbazole group, benzocarbazole group, naphtocarbazole group, or dibenzocarbazole group may be attached to a moiety comprising X in formula 7 ₇₄ -X ₇₆ Is a 6-membered ring having a single bond or adjacent L therebetween ₇₁ 、L ₇₂ And/or L ₇₃ 。

In one or more embodiments, e71-e73 in formula 7 each independently represent L ₇₁ -L ₇₃ And may each independently be, for example, 1, 2, 3, 4, or 5.

In one or more embodiments, R in formula 7 ₇₁ -R ₇₆ Each independently can be:

Hydrogen, deuterium, -F, or cyano;

phenyl, naphthyl, benzo [9,10 ] each of which is unsubstituted or substituted by at least one of]Phenanthrene group, dibenzofuran group, dibenzothiophene group, carbazole group, indolodibenzothiophene group, indolocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, and benzocarbazole groupA phenanthrobenzofuran group, a phenanthrobenzothiene group, a naphthazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group: deuterium, -F, cyano, C ₁ -C ₂₀ Alkyl, deuterated C ₁ -C ₂₀ Alkyl, fluoro C ₁ -C ₂₀ Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C) ₁ -C ₂₀ Alkyl) phenyl, biphenyl, deuterated biphenyl, fluorinated biphenyl, (C) ₁ -C ₂₀ Alkyl) biphenyl, -Si (Q) ₃₃ )(Q ₃₄ )(Q ₃₅ ) Or a combination thereof; or (b)

-Si(Q ₃ )(Q ₄ )(Q ₅ )。

In one or more embodiments, the electron transport compound may be one of the compounds H-ET1 to H-ET5, but the embodiment is not limited thereto:

according to another aspect, the light emitting device may be included in an electronic apparatus. Accordingly, an electronic apparatus including the light emitting device is also provided. The electronic device may include, for example, a display, a lighting device, a sensor, etc., but embodiments are not limited thereto.

Description of FIG. 1

Fig. 1 schematically illustrates a cross-sectional view of an organic light-emitting device 10, the organic light-emitting device 10 being a light-emitting device according to one or more embodiments. Hereinafter, the structure and manufacturing method of the organic light emitting device 10 according to one or more embodiments will be described in further detail with respect to fig. 1.

The organic light emitting device 10 of fig. 1 includes a first electrode 11, a second electrode 19, and an intermediate layer 15 between the first electrode 11 and the second electrode 19. The intermediate layer 15 may include a hole transport region, an emission layer, and an electron transport region.

A substrate may be additionally provided under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in an organic light emitting device, such as a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance.

The first electrode 11 may be manufactured by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode. The material used to form the first electrode 11 may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) ₂ ) Or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO.

The hole transport region may be located between the first electrode 11 and the emission layer.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, the respective layers are sequentially stacked in the stated order from the first electrode 11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using various methods such as a vacuum deposition method, spin coating, casting, langmuir-blodgett (LB) method, inkjet printing, or the like.

When the hole injection layer is formed by vacuum deposition, deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, deposition stripesThe article may comprise a deposition temperature of about 100 ℃ to about 500 ℃ and a deposition temperature of about 10 ^-8 Tray to about 10 ^-3 Vacuum pressure of about 0.01 angstrom/second-about->Is used for the deposition rate of (a).

When the hole injection layer is formed by spin coating, coating conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed in the range of about 2,000 revolutions per minute (rpm) to about 5,000rpm and a heat treatment temperature of about 80 ℃ to about 200 ℃ for removing the solvent after coating.

The conditions for forming the hole transport layer and the electron blocking layer may be the same as or similar to the conditions for forming the hole injection layer.

The hole transport region may include at least one of: 4,4',4 "-tris (3-methylphenylphenylamino) triphenylamine (m-MTDATA), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), 4',4 "-tris { N- (2-naphthyl) -N-phenylamino } -triphenylamine (2-TNATA), N, N ' -bis (1-naphthyl) -N, N ' -diphenyl benzidine (NPB), beta-NPB, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4' -cyclohexylidene bis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4' -bis [ N, N ' - (3-tolyl) amino ] -3,3' -dimethylbiphenyl (HMTPD), 4' -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-sulfostyrene) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-sulfostyrene) (PANI/PSS), and, the compound represented by formula 201, the compound represented by formula 202, or a combination thereof, but the embodiment is not limited thereto:

201, a method for manufacturing a semiconductor device

202, respectively

In formula 201, ar ₁₀₁ And Ar is a group ₁₀₂ Can each independently be phenylene, pentalene, indenylene, naphthylene, azulenylene, heptylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo [9,10 ] ene, each unsubstituted or substituted with at least one of]Phenanthryl, pyrenyl, and pyrenylA group, a tetracene group, a picene group, a perylene group, or a pentacene group: deuterium, -F, -Cl, -Br, -I, -SF ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ Alkyl, C ₂ -C ₆₀ Alkenyl, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy, C ₁ -C ₆₀ Alkylthio, C ₃ -C ₁₀ Cycloalkyl, C ₃ -C ₁₀ Cycloalkenyl, C ₁ -C ₁₀ Heterocycloalkyl, C ₁ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ Aryl, C ₇ -C ₆₀ Alkylaryl, C ₇ -C ₆₀ Arylalkyl, C ₆ -C ₆₀ Aryloxy, C ₆ -C ₆₀ Arylthio, C ₁ -C ₆₀ Heteroaryl, C ₂ -C ₆₀ Alkyl heteroaryl, C ₂ -C ₆₀ Heteroarylalkyl, C ₁ -C ₆₀ Heteroaryloxy, C ₁ -C ₆₀ Heteroarylthio, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, or combinations thereof.

Xa and xb in formula 201 may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0.

R in formulas 201 and 202 ₁₀₁ -R ₁₀₈ 、R ₁₁₁ -R ₁₁₉ And R is ₁₂₁ -R ₁₂₄ Each independently can be:

hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ Hydroxy, cyano, nitro, amino, C ₁ -C ₁₀ Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C ₁ -C ₁₀ Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.), or C ₁ -C ₁₀ Alkylthio;

c each unsubstituted or substituted by at least one of ₁ -C ₁₀ Alkyl, C ₁ -C ₁₀ Alkoxy, C ₁ -C ₁₀ Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF ₅ A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof; or (b)

Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each unsubstituted or substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ Alkyl, C ₁ -C ₁₀ Alkoxy, C ₁ -C ₁₀ Alkylthio, or a combination thereof.

In formula 201, R ₁₀₉ May be phenyl, naphthyl, anthracenyl, or pyridinyl, each of which is unsubstituted or substituted with at least one of: deuterium, -F, -Cl, -Br 、-I、-SF ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ Alkyl, C ₁ -C ₂₀ Alkoxy, C ₁ -C ₁₀ Alkylthio, phenyl, naphthyl, anthracenyl, pyridinyl, or a combination thereof.

In one embodiment, the compound represented by formula 201 may be represented by formula 201A, but the embodiment is not limited thereto:

201A

R in formula 201A ₁₀₁ 、R ₁₁₁ 、R ₁₁₂ And R ₁₀₉ Each as described herein.

For example, the hole transport region 120 may include at least one of the compounds HT1 to HT20, or a combination thereof, but the embodiment is not limited thereto:

/>

the hole transport region may have a thickness of about-about->For example about->-aboutWhen the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof, the hole injection layer may have a thickness of about +.>-about->For example about->-about->And the thickness of the hole transport layer may be about +.>-about->For example about->-about->When the thicknesses of the hole injection layer and the hole transport layer of the hole transport region satisfy these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

In addition to these materials, the hole transport region may further include a charge generating material to improve conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group containing compound, or a combination thereof. For example, the p-dopant may include at least one of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ), 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ), 1,3,4,5,7, 8-hexafluorotetracyanonaphthaquinone dimethane (F6-TCNNQ), and the like; metal oxides such as tungsten oxide, molybdenum oxide, and the like; cyano group-containing compounds such as compound HT-D1 and the like; or a combination thereof, but the embodiments are not limited thereto:

the hole transport region may include a buffer layer.

In addition, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may include a material, a host material, or a combination thereof, which may be used in the hole transport region as described above. For example, when the hole transport region includes an electron blocking layer, H-HT2 or the like may be used as a material for the electron blocking layer.

The emission layer may be formed on the hole transport region by using, for example, a vacuum deposition method, a spin coating method, a casting method, an LB method, and/or an inkjet printing method. When the emission layer is formed by vacuum deposition or spin coating, deposition or coating conditions may be similar to those applied when forming the hole injection layer, although deposition or coating conditions may vary depending on materials used to form the emission layer.

The emissive layer may comprise a composition as described herein.

The thickness of the emissive layer may be about-about->For example about->-about->About-about->About->-about->Or about->-about->When the thickness of the emission layer is within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

An electron transport region may be located on the emissive layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure, or an electron transport layer/electron injection layer structure. The electron transport layer may have a multi-layer structure or a single-layer structure including two or more different materials.

The conditions for forming the hole blocking layer, the electron transporting layer, and the electron injecting layer constituting the electron transporting region can be understood by referring to the conditions for forming the hole injecting layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of: 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), or a combination thereof, but the embodiments are not limited thereto:

in one or more embodiments, the hole blocking layer may include any host material, a material for an electron transport layer, a material for an electron injection layer, or a combination thereof, which will be described later.

The hole blocking layer may have a thickness of about-about->For example about->-about->Within a range of (2). When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.

The electron transport layer may include at least one of: 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 1,3, 5-tris (1-phenyl-1H-benzo [ d ] ]2-imidazolyl) benzene (TPBi), tris (8-hydroxy-quinoline) aluminum (Alq) ₃ ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 3- (4-biphenyl) -4-phenyl-5-tert-butylphenyl-1, 2, 4-Triazole (TAZ), 4- (naphthalen-1-yl) -3, 5-diphenyl-4H-1, 2, 4-triazole (NTAZ), or combinations thereof, although the embodiments are not limited theretoThis is:

in one or more embodiments, the electron transport layer may include one of the compounds ET1 to ET25, or a combination thereof, but embodiments are not limited thereto:

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the electron transport layer may have a thickness of about-about->For example about->-about->Within a range of (2). When the thickness of the electron transport layer is within the above range, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

The electron transport layer may include a metal-containing material in addition to the materials as described herein.

The metal-containing material may include a Li complex. The Li complex may include, for example, a compound ET-D1 or ET-D2, but the embodiment is not limited thereto:

the electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 into it.

The electron injection layer may include at least one of: liF, naCl, csF, li ₂ O, baO, yb, compound ET-D1, compound ET-D2, or combinations thereof, but embodiments are not limited thereto:

the electron injection layer may have a thickness of about-about->And e.g. about->-about->When the thickness of the electron injection layer is within the above range, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage. />

The second electrode 19 may be located above the electron transport region. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, the material used to form the second electrode 19 may be Li, mg, al, ag, al-Li, ca, mg-In, mg-Ag, or the like. In one or more embodiments, in order to manufacture a top emission type light emitting device, a transparent or semitransparent electrode formed using ITO or IZO may be used as the second electrode 19.

Description of the terms

The term "C" as used herein ₁ -C ₆₀ Alkyl "refers to a straight or branched saturated aliphatic having 1 to 60 carbon atomsA hydrocarbon monovalent group, and the term "C" as used herein ₁ -C ₆₀ Alkylene "means having a radical corresponding to C ₁ -C ₆₀ Divalent groups of the same structure as the alkyl group.

C ₁ -C ₆₀ Alkyl, C ₁ -C ₂₀ Alkyl, and/or C ₁ -C ₁₀ Non-limiting examples of alkyl groups can include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-butyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, and the like, each of which is unsubstituted or substituted with at least one of: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-butyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, zhong Guiji, tert-decyl, or a combination thereof. For example, formulas 9-33 are branched C ₆ Alkyl groups, for example, tert-butyl groups substituted with two methyl groups.

The term "C" as used herein ₁ -C ₆₀ Alkoxy "means a radical derived from-OA ₁₀₁ (wherein A ₁₀₁ Is C ₁ -C ₆₀ Alkyl), and non-limiting examples thereof may include methoxy, ethoxy, propoxy, butoxy, pentoxy, and the like.

The term "C" as used herein ₁ -C ₆₀ Alkylthio "means a radical derived from-SA ₁₀₁ (wherein A ₁₀₁ Is C ₁ -C ₆₀ Alkyl) a monovalent group represented by an alkyl group.

The term "C" as used herein ₂ -C ₆₀ Alkenyl "means by at C ₂ -C ₆₀ Of alkyl groupsHydrocarbon groups formed by substitution of at least one carbon-carbon double bond at the middle or at the end, and non-limiting examples thereof may include ethenyl, propenyl, butenyl, and the like. The term "C" as used herein ₂ -C ₆₀ Alkenylene "means having a radical corresponding to C ₂ -C ₆₀ Alkenyl groups are divalent radicals of the same structure.

The term "C" as used herein ₂ -C ₆₀ Alkynyl "means by at C ₂ -C ₆₀ The alkyl group is substituted with at least one carbon-carbon triple bond at the middle or end thereof, and non-limiting examples thereof may include ethynyl, propynyl, and the like. The term "C" as used herein ₂ -C ₆₀ Alkynylene "means having a radical different from C ₂ -C ₆₀ Alkynyl groups are divalent radicals of the same structure.

The term "C" as used herein ₃ -C ₁₀ Cycloalkyl "refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and C ₃ -C ₁₀ Cycloalkylene radicals having the meaning as defined in claim C ₃ -C ₁₀ Cycloalkyl groups are divalent radicals of the same structure.

C ₃ -C ₁₀ Non-limiting examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [ 2.2.1)]Heptyl), bicyclo [1.1.1]Amyl, bicyclo [2.1.1]Hexyl, bicyclo [2.2.2]Octyl, and the like.

The term "C" as used herein ₁ -C ₁₀ Heterocyclyl "refers to a monovalent saturated cyclic group comprising at least one heteroatom selected from N, O, P, si, S, se, ge, and B as ring-forming atom and 1-10 carbon atoms as ring-forming atoms, and the term" C "as used herein ₁ -C ₁₀ Heterocyclylene "means having a radical corresponding to C ₁ -C ₁₀ Divalent groups of the same structure as the heterocycloalkyl group.

C ₁ -C ₁₀ Non-limiting examples of heterocycloalkyl groups can include silacyclopentyl, silahexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothienyl, and the like.

As used herein to makeThe term "C" is used ₃ -C ₁₀ Cycloalkenyl "refers to a monovalent cyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. The term "C" as used herein ₃ -C ₁₀ Cycloalkenylene "means having a radical corresponding to C ₃ -C ₁₀ Divalent groups of the same structure as cycloalkenyl groups.

The term "C" as used herein ₁ -C ₁₀ Heterocycloalkenyl "refers to a monovalent cyclic group having in its ring at least one heteroatom selected from N, O, P, si, S, se, ge, and B as a ring-forming atom, 1-10 carbon atoms as ring-forming atoms, and at least one double bond. C (C) ₁ -C ₁₀ Non-limiting examples of heterocycloalkenyl groups can include 2, 3-dihydrofuryl, 2, 3-dihydrothienyl, and the like. The term "C" as used herein ₁ -C ₁₀ Heterocycloalkenylene "means having a structural formula corresponding to C ₁ -C ₁₀ Divalent groups of the same structure as the heterocycloalkenyl group.

The term "C" as used herein ₆ -C ₆₀ Aryl "refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term" C "as used herein ₆ -C ₆₀ Arylene "refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. C (C) ₆ -C ₆₀ Non-limiting examples of aryl groups may include phenyl, naphthyl, anthracyl, phenanthryl, pyrenyl,A base, etc. When C ₆ -C ₆₀ Aryl and C ₆ -C ₆₀ Where arylene groups each include two or more rings, the rings may be fused to each other.

The term "C" as used herein ₇ -C ₆₀ Alkylaryl "means an alkylaryl group interrupted by at least one C ₁ -C ₅₄ Alkyl substituted C ₆ -C ₅₉ Aryl groups. The term "C" as used herein ₇ -C ₆₀ Arylalkyl "means substituted with at least one C ₆ -C ₅₉ Aryl substituted C ₁ -C ₅₄ An alkyl group.

The term "C" as used herein ₁ -C ₆₀ Heteroaryl "refers to a monovalent group comprising a cyclic aromatic system as follows: the cyclic aromatic system has at least one heteroatom selected from N, O, P, si, S, se, ge, and B as a ring forming atom and has from 1 to 60 carbon atoms as ring forming atoms, and the term "C" as used herein ₁ -C ₆₀ Heteroarylene "refers to a divalent group comprising a cyclic aromatic system as follows: the cyclic aromatic system has at least one heteroatom selected from N, O, P, si, S, se, ge, and B as a ring forming atom and has 1 to 60 carbon atoms as ring forming atoms. C (C) ₁ -C ₆₀ Non-limiting examples of heteroaryl groups can include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like. When C ₁ -C ₆₀ Heteroaryl and C ₁ -C ₆₀ When each heteroarylene includes two or more rings, the rings may be fused to each other.

The term "C" as used herein ₂ -C ₆₀ Alkyl heteroaryl "means substituted with at least one C ₁ -C ₅₉ Alkyl substituted C ₁ -C ₅₉ Heteroaryl groups. The term "C" as used herein ₂ -C ₆₀ Heteroarylalkyl "means a radical containing at least one C ₁ -C ₅₉ Heteroaryl substituted C ₁ -C ₅₉ An alkyl group.

The term "C" as used herein ₆ -C ₆₀ Aryloxy "represents-OA ₁₀₂ (wherein A ₁₀₂ Represent C ₆ -C ₆₀ Aryl), C ₆ -C ₆₀ Arylthio representation-SA ₁₀₃ (wherein A ₁₀₃ Represent C ₆ -C ₆₀ Aryl), and C ₁ -C ₆₀ Alkylthio represents-SA ₁₀₄ (wherein A ₁₀₄ Represent C ₁ -C ₆₀ Alkyl).

The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having from about 8 to about 60 carbon atoms) as follows: it has two or more rings condensed with each other, has only carbon atoms as ring-forming atoms, and has no aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups can include fluorenyl and the like. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic groups described above.

The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having from about 1 to about 60 carbon atoms) as follows: it has two or more rings condensed with each other, has at least one hetero atom selected from N, O, P, si, S, se, ge, and B as a ring-forming atom in addition to a carbon atom, and has no aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups can include carbazolyl groups and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic groups described above.

The term "C" as used herein ₅ -C ₃₀ A carbocyclic group "refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. C (C) ₅ -C ₃₀ The carbocyclic group may be a monocyclic group or a polycyclic group. As used herein "(unsubstituted or substituted with at least one R) _10a Substituted) C ₅ -C ₃₀ Non-limiting examples of carbocyclic groups "are each unsubstituted or substituted with at least one R _10a Substituted adamantyl groups, norbornene groups, bicyclo [1.1.1]Pentanyl groups, bicyclo [2.1.1]Hexane radical, bicyclo [2.2.1]Heptane (norbornane) groups, bicyclo [2.2.2]Octyl groups, cyclopentane groups, cyclohexane groups, cyclohexene groups, phenyl groups, naphthalene groups, anthracene groups, phenanthrene groups, benzo [9,10 ]]A phenanthrene group, a pyrene group,A group, a 1,2,3, 4-tetrahydronaphthalene group, a cyclopentadiene group, a fluorene group, and the like.

The term as used herein“C ₁ -C ₃₀ A heterocyclic group "refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, si, S, se, ge, and B as a ring-forming atom in addition to 1 to 30 carbon atoms as a ring-forming atom. C (C) ₁ -C ₃₀ The heterocyclic group may be a monocyclic group or a polycyclic group. "(unsubstituted or substituted by at least one R _10a Substituted) C ₁ -C ₃₀ The heterocyclic groups "may be, for example, each unsubstituted or substituted with at least one R _10a Substituted thiophene groups, furan groups, pyrrole groups, silole groups, borole groups, phosphole groups, selenophene groups, germanium phosphole groups, benzothiophene groups, benzofuran groups, indole groups, benzothiophene groups, benzoborole groups, benzophosphole groups, benzoselenophene groups, benzogermanium cyclopentene groups, dibenzothiophene groups, dibenzofuran groups, carbazole groups, dibenzothiazyl groups, dibenzothiamine groups, dibenzofuran groups, carbazole groups, dibenzothiazole groups, dibenzoborole groups, dibenzophosphole groups, dibenzoselenophene groups, dibenzogermanium cyclopentadiene groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-ketone groups, dibenzothiophene 5, 5-dioxide groups, azabenzothiophene groups, azabenzofuran groups, azaindole groups, azaindene groups, azabenzothizole groups, azabenzoborole groups, azabenzophosphole groups, azabenzoselenophene groups, azabenzogermanopyrrole groups, azabenzopentalene groups, azabenzoselenophene groups, azapentalene groups, azabenzogermane groups, azabenzopentalene groups, azabenzoselenophene groups, azabenzopentalene groups, azabenzoselenophene derivatives, and azabenzopenthese groups, and azabenzoguanthese groups may be substituted by an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilol group, an azadibenzoborole group, an azacyclopentadiene group Azadibenzophosphole groups, azadibenzoselenophene groups, azadibenzogermanium heterocyclopentenene groups, azadibenzothiophene 5-oxide groups, aza-9H-fluoren-9-one groups, azadibenzothiophene 5, 5-dioxide groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, An azole group, iso->An azole group, a thiazole group, an isothiazole group,/-thiazole group>Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo +.>An azole group, a benzothiazole group, a benzo +.>Diazole groups, benzothiadiazole groups, 5,6,7, 8-tetrahydroisoquinoline groups, 5,6,7, 8-tetrahydroquinoline groups, and the like.

"C" as used herein ₅ -C ₃₀ Carbocycle groups "and" C ₁ -C ₃₀ Examples of heterocyclic groups "include i) a first ring, ii) a second ring, iii) a fused ring system in which two or more first rings are fused to each other, iv) a fused ring system in which two or more second rings are fused to each other, or v) a fused ring system in which at least one first ring is fused to at least one second ring,

wherein the first ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group silol groups, borole groups, phosphole groups, germanium heterocyclopentadiene groups, selenophene groups,An azole group,Diazole groups, (-)>Triazole group, thiazole groupA group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, or azasilole group, and

The term "fluoro C ₁ -C ₆₀ Alkyl (or fluoro C) ₁ -C ₂₀ Alkyl, etc) "," fluoro C ₃ -C ₁₀ Cycloalkyl "," fluoro C ₁ -C ₁₀ Heterocyclyl ", and" fluorophenyl "each represent C, each substituted with at least one fluoro group (-F) ₁ -C ₆₀ Alkyl (or C) ₁ -C ₂₀ Alkyl, etc.), C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, and phenyl. For example, the term "fluoro C ₁ Alkyl (i.e., fluoromethyl) "includes-CF ₃ 、-CF ₂ H. and-CFH ₂ . "fluoro C ₁ -C ₆₀ Alkyl (or fluoro C) ₁ -C ₂₀ Alkyl, etc) "," fluoro C ₃ -C ₁₀ Cycloalkyl "," fluoro C ₁ -C ₁₀ Heterocycloalkyl ", or" fluorophenyl "may be i) fully fluorinated C ₁ -C ₆₀ Alkyl (or fully fluorinated C) ₁ -C ₂₀ Alkyl, etc.), fully fluorinated C ₃ -C ₁₀ Cycloalkyl, fully fluorinated C ₁ -C ₁₀ Heterocycloalkyl, or fully fluorinated phenyl, wherein, in each group, all of the hydrogens included therein are replaced with fluorine groups, or ii) partially fluorinated C ₁ -C ₆₀ Alkyl (or partially fluorinated C) ₁ -C ₂₀ Alkyl, etc.), partially fluorinated C ₃ -C ₁₀ Cycloalkyl, partially fluorinated C ₁ -C ₁₀ Heterocycloalkyl, or partially fluorinated phenyl, wherein, in each group, the hydrogen included therein is not entirely replaced by a fluorine group.

The term "deuterated C ₁ -C ₆₀ Alkyl (or deuterated C ₁ -C ₂₀ Alkyl, etc) "," deuterated C ₃ -C ₁₀ Cycloalkyl "," deuterated C ₁ -C ₁₀ Heterocycloalkyl ", and" deuterated phenyl "each represent C, each substituted with at least one deuterium ₁ -C ₆₀ Alkyl (or C) ₁ -C ₂₀ Alkyl, etc.), C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, and phenyl. For example, "deuterated C ₁ Alkyl (i.e., deuterated methyl) "may include-CD ₃ 、-CD ₂ H. and-CDH ₂ And "deuterated C ₃ -C ₁₀ Examples of cycloalkyl "are, for example, formulas 10-501, etc. "deuterated C ₁ -C ₆₀ Alkyl (or deuterated C ₁ -C ₂₀ Alkyl, etc) "," deuterated C ₃ -C ₁₀ Cycloalkyl "," deuterated C ₁ -C ₁₀ Heterocycloalkyl ", or" deuterated phenyl "may be i) fully deuterated C ₁ -C ₆₀ Alkyl (or fully deuterated C ₁ -C ₂₀ Alkyl, etc.), fully deuterated C ₃ -C ₁₀ Cycloalkyl, fully deuterated C ₁ -C ₁₀ Heterocycloalkyl, or fully deuterated phenyl wherein, in each group, all hydrogen included therein is replaced by deuterium, or ii) partially deuterated C ₁ -C ₆₀ Alkyl (or partially deuterated C ₁ -C ₂₀ Alkyl, etc.), partially deuterated C ₃ -C ₁₀ Cycloalkyl, partially deuterated C ₁ -C ₁₀ Heterocycloalkyl, or partially deuterated phenyl, wherein, in each group, the hydrogen included therein is not entirely replaced by deuterium.

The term "(C) as used herein ₁ -C ₂₀ Alkyl) 'X' group "means a group containing at least one C ₁ -C ₂₀ An alkyl substituted 'X' group. For example, the term "(C) as used herein ₁ -C ₂₀ Alkyl) C ₃ -C ₁₀ Cycloalkyl "means substituted with at least one C ₁ -C ₂₀ Alkyl substituted C ₃ -C ₁₀ Cycloalkyl, and the term "(C) as used herein ₁ -C ₂₀ Alkyl) phenyl "means substituted with at least one C ₁ -C ₂₀ An alkyl-substituted phenyl group. (C) ₁ Examples of the alkyl) phenyl group may include tolyl and the like.

As used herein, the terms azabenzboryl group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermanium heterocyclopenyl group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzothiophene group, azadibenzogermanium heterocyclopentadiene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group and azadibenzothiophene 5, 5-dioxide groups "refer to heterocyclic groups having the same backbone as" indole groups, benzoborole groups, benzophospholane groups, indene groups, benzothiophene groups, benzosilole groups, benzogermanopyranene groups, benzothiophene groups, benzoselenophene groups, benzofuran groups, carbazole groups, dibenzoborole groups, dibenzophospholane groups, fluorene groups, dibenzosilole groups, dibenzogermanopyranene groups, dibenzothiophene groups, dibenzoselenophene groups, dibenzofuran groups, dibenzothiophene 5-oxide groups, 9H-fluoren-9-one groups, and dibenzothiophene 5, 5-dioxide groups, "respectively, wherein at least one carbon selected from the ring-forming carbons is replaced by nitrogen in each group.

Substituted C ₅ -C ₃₀ Carbocycle group, substituted C ₁ -C ₃₀ Heterocyclic groups, substituted C ₁ -C ₆₀ Alkyl, substituted C ₂ -C ₆₀ Alkenyl, substituted C ₂ -C ₆₀ Alkynyl, substituted C ₁ -C ₆₀ Alkoxy, substituted C ₁ -C ₆₀ Alkylthio, substituted C ₃ -C ₁₀ Cycloalkyl, substituted C ₁ -C ₁₀ Heterocycloalkyl, substituted C ₃ -C ₁₀ Cycloalkenyl, substituted C ₁ -C ₁₀ Heterocycloalkenyl, substituted C ₆ -C ₆₀ Aryl, substituted C ₇ -C ₆₀ Alkylaryl, substituted C ₇ -C ₆₀ Arylalkyl, substituted C ₆ -C ₆₀ Aryloxy, substituted C ₆ -C ₆₀ Arylthio, substituted C ₁ -C ₆₀ Heteroaryl, substituted C ₂ -C ₆₀ Alkyl heteroaryl, substituted C ₂ -C ₆₀ Heteroarylalkyl, substituted C ₁ -C ₆₀ Heteroaryloxy, substituted C ₁ -C ₆₀ The at least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:

deuterium, -F, -Cl, -Br, -I, -SF ₅ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ Alkyl, C ₂ -C ₆₀ Alkenyl, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy, or C ₁ -C ₆₀ Alkylthio;

c each substituted by at least one of ₁ -C ₆₀ Alkyl, C ₂ -C ₆₀ Alkenyl, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy, or C ₁ -C ₆₀ Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF ₅ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, C ₃ -C ₁₀ Cycloalkenyl, C ₁ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ Aryl, C ₇ -C ₆₀ Alkylaryl, C ₆ -C ₆₀ Aryloxy, C ₆ -C ₆₀ Arylthio, C ₁ -C ₆₀ Heteroaryl, C ₂ -C ₆₀ Alkyl groupHeteroaryl, C ₁ -C ₆₀ Heteroaryloxy, C ₁ -C ₆₀ Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N (Q) ₁₁ )(Q ₁₂ )、-Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ )、-Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ )、-B(Q ₁₆ )(Q ₁₇ )、-P(＝O)(Q ₁₈ )(Q ₁₉ )、-P(Q ₁₈ )(Q ₁₉ ) Or a combination thereof;

c each unsubstituted or substituted by at least one of ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, C ₃ -C ₁₀ Cycloalkenyl, C ₁ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ Aryl, C ₇ -C ₆₀ Alkylaryl, C ₆ -C ₆₀ Aryloxy, C ₆ -C ₆₀ Arylthio, C ₁ -C ₆₀ Heteroaryl, C ₂ -C ₆₀ Alkyl heteroaryl, C ₁ -C ₆₀ Heteroaryloxy, C ₁ -C ₆₀ Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF ₅ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ Alkyl, C ₂ -C ₆₀ Alkenyl, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy, C ₁ -C ₆₀ Alkylthio, C ₃ -C ₁₀ Cycloalkyl, C ₁ -C ₁₀ Heterocycloalkyl, C ₃ -C ₁₀ Cycloalkenyl, C ₁ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ Aryl, C ₇ -C ₆₀ Alkylaryl, C ₇ -C ₆₀ Arylalkyl, C ₆ -C ₆₀ Aryloxy, C ₆ -C ₆₀ Arylthio, C ₁ -C ₆₀ Heteroaryl, C ₂ -C ₆₀ Alkyl groupHeteroaryl, C ₂ -C ₆₀ Heteroarylalkyl, C ₁ -C ₆₀ Heteroaryloxy, C ₁ -C ₆₀ Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N (Q) ₂₁ )(Q ₂₂ )、-Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ )、-Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ )、-B(Q ₂₆ )(Q ₂₇ )、-P(＝O)(Q ₂₈ )(Q ₂₉ )、-P(Q ₂₈ )(Q ₂₉ ) Or a combination thereof;

-N(Q ₃₁ )(Q ₃₂ )、-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ )、-Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ )、-B(Q ₃₆ )(Q ₃₇ )、-P(＝O)(Q ₃₈ )(Q ₃₉ ) or-P (Q) ₃₈ )(Q ₃₉ ) The method comprises the steps of carrying out a first treatment on the surface of the Or (b)

A combination thereof.

In the present specification, Q ₁ -Q ₉ 、Q ₁₁ -Q ₁₉ 、Q ₂₁ -Q ₂₉ And Q ₃₁ -Q ₃₉ Can be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF, each independently ₅ Hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ Alkyl, substituted or unsubstituted C ₂ -C ₆₀ Alkenyl, substituted or unsubstituted C ₂ -C ₆₀ Alkynyl, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkyl, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkyl, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkenyl, substituted or unsubstituted C ₆ -C ₆₀ Aryl, substituted or unsubstituted C ₇ -C ₆₀ Alkylaryl, substituted or unsubstituted C ₇ -C ₆₀ Arylalkyl, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy, substituted or unsubstituted C ₆ -C ₆₀ Arylthio, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl, substituted or unsubstitutedSubstituted C ₂ -C ₆₀ Alkyl heteroaryl, substituted or unsubstituted C ₂ -C ₆₀ Heteroarylalkyl, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryloxy, substituted or unsubstituted C ₁ -C ₆₀ Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

For example, Q as described herein ₁ -Q ₉ 、Q ₁₁ -Q ₁₉ 、Q ₂₁ -Q ₂₉ And Q ₃₁ -Q ₃₉ Each independently can be:

Hereinafter, the light emitting device according to the exemplary embodiment is described in further detail with reference to examples. However, the exemplary embodiments are not limited thereto.

Examples

Synthesis example 1 (Compound D6)

Synthesis of Compound 6-1

50 milliliters (mL) of Tetrahydrofuran (THF) and 20mL of Deionized (DI) water were combined with compound 6-1 (1) (5.00 grams (g), 14.00 millimoles (mmol)), compound6-1 (2) (3.56 g,16.80 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh) ₃ ) ₄ ) (0.81 g,0.70 mmol), and K ₂ CO ₃ (5.80 g,42.0 mmol) and then stirred and heated at reflux for 18 hours. After allowing the temperature to drop to room temperature, the organic layer was extracted with dichloromethane, separated and dried over anhydrous magnesium sulfate (MgSO ₄ ) Dried and then filtered to obtain the product. The solvent was removed under reduced pressure and the obtained residue was purified by column chromatography (ethyl acetate (EA): hexane=1:6, weight/weight) to obtain compound 6-1 (4.3 g,68% yield). The synthesis process was repeated to obtain a sufficient amount of compound 6-1 for use in the next reaction.

Synthesis of Compound 6-2

Compound 6-1 (7.0 g,15.81 mmol) and iridium chloride trihydrate (2.68 g,7.60 mmol) were mixed with 50mL of 2-ethoxyethanol and 20mL of DI water, and then the resulting mixture was stirred and heated under reflux for 24 hours. Then, the temperature was allowed to drop to room temperature. The resulting solid was isolated by filtration, thoroughly washed in the stated order using DI water, methanol, and hexane, and the obtained solid was dried in a vacuum oven to obtain compound 6-2 (6.35 g,75% yield).

Synthesis of Compound 6-3

Compound 6-2 (5.8 g,2.60 mmol) was mixed with 90mL of Methylene Chloride (MC), and silver triflate (AgOTf) (1.4 g,5.46 mmol) dissolved in 30mL of methanol was added thereto. After that, the reaction mixture was stirred at room temperature for 18 hours in a state where light was blocked with aluminum foil, then the resulting solid was removed by filtration through celite, and the solvent was removed from the filtrate under reduced pressure to obtain a solid (compound 6-3). The solid obtained was used in the next reaction without additional purification.

Synthesis of Compound D6

Compound 6-3 (6.45 g,5.0 mmol) and compound 6-1 (2.22 g,5.0 mmol) were mixed with 80mL of 2-ethoxyethanol and 80mL of N, N-dimethylformamide, and then the reaction mixture was stirred and heated at 120 ℃ under reflux for 24 hours. Then, the temperature was allowed to drop to room temperature. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EA/hexane, 1:8 w/w) to obtain compound D6 (5.3 g,70% yield). Compound D6 was characterized by high resolution mass spectrometry (HRMS (MALDI)) using matrix-assisted laser desorption ionization.

HRMS (MALDI): for C ₉₃ H ₈₁ IrN ₆ O ₃ Is calculated by the following steps: m/z:1523.6033, found: 1523.4889.

synthesis example 2 (Compound D7)

Synthesis of Compound 7-1

Compound 7-1 (4.05 g,62.5% yield) was obtained in a similar manner to that used for synthesizing compound 6-1 of synthesis example 1, except that: compound 7-1 (2) (5.24 g,16.80 mmol) was used instead of compound 6-1 (2).

Synthesis of Compound D7

Compound 7-1 (1.96 g,4.24 mmol) and bis (1, 5-cyclooctadiene) iridium tetrafluoroborate (I) (Ir (COD) ₂ BF ₄ ) (0.6 g,1.21 mmol) was dissolved in 20mL of 2-ethoxyethanol and stirred at 160℃for 24 hoursUndergo a reaction, after which the temperature is allowed to cool to room temperature. The solid thus obtained was dried by filtration, and then purified by column chromatography (EA: hexane, 1:7 weight/weight) to obtain compound D7 (0.85 g,45% yield).

HRMS (MALDI): for C ₉₃ H ₇₈ F ₃ IrN ₆ O ₃ Is calculated by the following steps: m/z:1576.5717, found: 1576.9442.

evaluation example 1

For the host and dopant included in compositions 1 to 24 shown in tables 2 and 3, dipole Moment (DM), HOMO level, and LUMO level were evaluated according to the methods described in table 1, and based on the evaluation results, values X and Y were calculated for each composition. The results are shown in tables 2 and 3.

Each of the compositions 1 to 24 includes one type of dopant (first dopant) and two types of host (first host and second host), and these compositions correspond to the compositions in this specification in which m1 is 1 and m2 is 2. The amounts of the first dopant, the first host, and the second host included in each composition satisfy the weight fractions of W (D1), W (H1), and W (H2) shown in table 2.

TABLE 1

TABLE 2

¹ : DM (H1) =dipole moment of first body

² : DM (H2) =dipole moment of the second body

³ : DM (D1) =dipole moment of first dopant

⁴ : w (H1) =weight fraction of the first body relative to the total weight of the first body, the second body, and the first dopant, by "each ofCalculation of (weight of first host/total weight of first host, second host, and first dopant) in composition

⁵ : w (H2) =weight fraction of the second body relative to the total weight of the first body, second body, and first dopant, calculated by "weight of the second body/total weight of the first body, second body, and first dopant" in each composition

⁶ : w (D1) =weight fraction of the first dopant relative to the total weight of the first host, second host, and first dopant, calculated by "weight of the first dopant/total weight of the first host, second host, and first dopant" in each composition

⁷ : the value x= "DM (h1) ·w (h1) +dm (h2) ·w (H2) +dm (D1) ·w (D1)".

/>

TABLE 3 Table 3

⁸ : HOMO (H1) =homo energy level of first host ⁹ : HOMO (H2) =homo level of second host ¹⁰ : HOMO (D1) =homo level of first dopant ¹¹ : LUMO (H1) =lumo energy level of first host ¹² : LUMO (H2) =lumo level of the second host

¹³ ：Y＝“{HOMO(H1)-HOMO(D1)}×{1-W(H2)}”

From table 3, it is confirmed that in each composition, i) the absolute value of the HOMO level of the first host is smaller than the absolute value of the HOMO level of the second host, and ii) the absolute value of the LUMO level of the second host is larger than the absolute value of the LUMO level of the first host.

Fabrication of OLED 1

Deposit thereon ITO/Ag/ITO (as anode)Is cut into a size of 50 millimeters (mm) ×50mm×0.5mm, sonicated with isopropyl alcohol and DI water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes each. The resulting glass substrate is then loaded onto a vacuum deposition apparatus.

The compounds HT3 and F6-TCNNQ were co-deposited on the anode by vacuum in a weight ratio of 98:2 to form a polymer having a molecular weight of 98:2And vacuum depositing a compound HT3 on the hole injection layer to form a layer having +.>A hole transport layer of a thickness of (a). Then, a compound H-HT2 is deposited on the hole transport layer to form a film having +. >Electron blocking layer of a thickness of (a).

Then, the first host, the second host, and the first dopant included in composition 1 of table 2 were co-deposited on the electron blocking layer to form a polymer film having a structure ofIs a layer of a thickness of the emissive layer. The weight ratios of the first host, second host, and first dopant in the emissive layer were adjusted to satisfy W (H1), W (H2), and W (D1) described in table 2 as weight fractions of the first host, second host, and first dopant in composition 1.

Then, the compounds ET3 and ET-D1 were co-deposited on the emissive layer in a 50:50 volume ratio to form a polymer havingAnd vacuum depositing LiF on the electron transport layer to form an electron injection layer having a thickness of 1 nm. Co-depositing Mg and Ag on the electron injection layer in a weight ratio of 90:10 to form a film having +.>And thus completing the fabrication of the organic light emitting device.

Fabrication of OLED 2 to OLED 24

The OLEDs 2 to 24 are manufactured in a similar manner as for the manufacture of the OLED 1, except for the following: in forming the emission layer, the thicknesses of the first host, the second host, and the first dopant included in each of the compositions 2 to 24 of table 2 and the emission layer of each of the OLEDs 2 to 24 of table 4 are used instead of the thicknesses of the first host, the second host, and the first dopant included in the composition 1 of table 2 and the emission layer of the OLED 1 of table 4, and the weight fractions of the first host, the second host, and the first dopant in each of the compositions shown in table 2 are applied.

Evaluation example 2

Then, keithley 6221 equipment was used at 1mA/cm ² The OLED 1 was driven while applying a pulse current under conditions of 50Hz, and 5% duty cycle (i.e., one pulse is 1,000 μs) to evaluate the luminance of the OLED 1 over time. As a result, a plot of time (μs) versus relative brightness (arbitrary units) of OLED 1 was obtained.

From the time (μs) -relative luminance (arbitrary unit) graph of OLED 1, i) the on time, which is the time required for the luminance to reach 90% of the maximum luminance after the current was applied, and ii) the off time, which is the time required for the luminance to reach 10% of the maximum luminance after the current was cut off, were each evaluated, and the results thereof are shown in table 4.

The on-time and off-time of each of OLED 2 to OLED 24 were evaluated. The results are shown in Table 4. From the electroluminescence spectra of the OLEDs 1 to 24, the respective maximum emission wavelengths (emission peak wavelengths) of the OLEDs 1 to 24 were evaluated. The results are shown in Table 4.

Fig. 2 shows a contour diagram of the turn-off times of the OLEDs 1 to 24, respectively, based on (X, Y) coordinates and turn-off time data.

TABLE 4 Table 4

An organic light emitting device using a composition having (X, Y) coordinates (i.e., coordinates of an improved image) belonging to the region a in fig. 2 may have an off-time of, for example, 100 μs or less. For example, as confirmed from table 4, the (X, Y) coordinates of the OLEDs 6 to 13 in table 4 belong to the region a in fig. 2, and the OLEDs 6 to 13 have an off time of 100 μs or less. In addition, as demonstrated in table 4, OLEDs 6 to 13 have an on time of 256 μs or less.

While not intending to be limited by any particular theory, in general, the off time for the emission of red and blue light may be about 100 μs. Thus, in the case of a full-color light emitting device having a green emission layer comprising a composition as described in the present specification, the off-time of green light may be very close to the off-time of each of red light and blue light. Accordingly, an afterimage such as a green afterimage after current is cut off for the full-color light emitting device can be substantially prevented.

Although not intending to be limited by a particular theory, it is generally at 1mA/cm ² The on-time for the emission of red and blue light at a current density of about 140 mus to about 200 mus. Thus, in the case of a full color light emitting device having a green emissive layer comprising a composition as described herein, the on-time of green light can be very close to that of red and blueThe respective on times of the colored lights. Accordingly, a color dragging phenomenon, such as a purple dragging phenomenon, after a current is applied to the full-color light emitting device can be substantially prevented.

Light emitting devices using the compositions as described herein have improved off-times and, therefore, can provide high quality electronics.

It should be understood that the exemplary embodiments described herein should be considered in descriptive sense only and not for purposes of limitation. The descriptions of features or aspects in various exemplary embodiments should typically be considered as available for other similar features or aspects in other exemplary embodiments.

Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims

1. A composition comprising:

m1 dopants; and

m2 kinds of main bodies, namely, a plurality of main bodies,

wherein:

m1 and m2 are each an integer of 1 or more,

the composition has coordinates of an improved image represented by:

(X,Y)

wherein the method comprises the steps of

X isAnd->The sum, and calculated as debye,

y is { HOMO (H) _min )-HOMO(D _min )}×{1-W(H _{LUMO_max} ) Calculated, and measured in electronic volts,

x is a variable from 1 to m1,

y is a variable from 1 to m2,

DM (Dx) is the dipole moment of the x-th dopant and is calculated as Debye,

DM (Hy) is the dipole moment of the y-th host, and is calculated as Debye,

dm (Dx) and Dm (Hy) are each calculated based on density functional theory,

HOMO(H _min ) Is the minimum value among the absolute values of the highest occupied molecular orbital energy levels of the m2 hosts, and is calculated in electron volts,

HOMO(D _min ) Is the minimum of the absolute values of the highest occupied molecular orbital energy levels of the m1 dopants, and is calculated in electron volts,

2. The composition of claim 1, wherein

m1 and m2 are each independently 1 or 2.

3. The composition of claim 1, wherein

The dipole moment of at least one of the m1 dopants is 6 debye or less.

4. The composition of claim 1, wherein

The coordinates of the improved image satisfy the following conditions: x is more than or equal to 1.112 and less than or equal to 1.534, and Y is more than or equal to 0.119 and less than or equal to 0.160.

5. The composition of claim 1, wherein

Each of the m1 dopants emits green light.

6. The composition of claim 1, wherein

The maximum emission wavelength of the emission spectrum of each of the m1 dopants is 500 nm to 580 nm.

7. The composition of claim 1, wherein

At least one of the m1 dopants is an organometallic compound containing a transition metal, and

each of the m2 hosts does not include a transition metal.

8. The composition of claim 1, wherein

At least one of the m1 dopants is an iridium-containing organometallic compound, and

the iridium-containing organometallic compound includes a first ligand, a second ligand, and a third ligand, wherein each of the first ligand, the second ligand, and the third ligand is bound to iridium, and

the first ligand, the second ligand, and the third ligand are each bidentate ligands that bind to iridium via C and N.

9. The composition of claim 8, wherein

The first ligand, the second ligand, and the third ligand are the same as each other, or

The first ligand and the second ligand are the same as each other, and the second ligand and the third ligand are different from each other, or

The first ligand and the second ligand are different from each other, and the second ligand and the third ligand are the same as each other, or

The first ligand, the second ligand, and the third ligand are different from each other.

10. The composition of claim 1, wherein

the iridium-containing organometallic compound includes dibenzofuran groups, dibenzothiophene groups, dibenzoselenophene groups, dibenzosilole groups, dibenzogermanium heterocyclopenadiene groups, naphthobenzofuran groups, naphthobenzothiophene groups, naphthoselenophene groups, naphthobenzophenosilole groups, naphthogermacrene groups, phenanthrobenzbenzofuran groups, phenanthrobenzbenzothiophene groups, phenanthrobenzselenophene groups, phenanthrobenzopyrrole groups, phenanthrobenzenepentadiene groups, azadibenzofuran groups, iridium-containing organometallic compounds, and iridium-containing organometallic compounds an azadibenzoselenophene group, an azadibenzosilole group, an azadibenzogermacrene group, an azanaphthacene benzofurane group, an azanaphthacene phenoselenophene group, an azanaphthacenesilole group, an azanaphthacene germacrene group, an azaphenanthrobenzbenzofurane group, an azaphenanthrobenzselenophene group, an azaphenanthrobenzsilole group, an azaphenanthrobenzgermeneamine group, or a combination thereof.

11. The composition of claim 1, wherein

the iridium-containing organometallic compound includes benzimidazole groups, benzoates each of which is linked to iridium via NAn azole group, a benzothiazole group naphthoimidazole group, naphtho->An azole group, a naphthothiazole group, a phenanthroimidazole group, a phenanthroi ∈ ->An azole group, a phenanthrothiazole group, a pyridoimidazole group, a pyrido +.>An azole group, a pyridothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, or a combination thereof.

12. The composition of claim 1, wherein

The host having the largest value among the absolute values of the lowest unoccupied molecular orbital levels of the m2 hosts includes a triazine group.

13. A light emitting device, comprising:

a first electrode;

a second electrode opposite to the first electrode; and

wherein the intermediate layer comprises an emissive layer, and

wherein the emissive layer comprises the composition of any one of claims 1-12.

14. The light emitting device of claim 13, wherein

The emission layer emits green light.

15. The light emitting device of claim 13, wherein

The maximum emission wavelength of the electroluminescent spectrum of light emitted from the emission layer is 500 nm to 580 nm.

16. The light emitting device of claim 13, wherein

The off-time is 100 microseconds or less,

wherein the off-time is a time required for the luminance of the light emitting device to reach 10% of the maximum luminance of the light emitting device after stopping the current for the light emitting device.

17. The light emitting device of claim 13, wherein

The intermediate layer includes:

m light emitting units each including at least one emission layer; and

m is an integer of 2 or more, and

the emissive layer of at least one of the m light emitting units comprises the composition.

18. The light emitting device of claim 13, further comprising:

a substrate including red, green, and blue sub-pixels,

wherein the first electrode is patterned for each of the red sub-pixel, the green sub-pixel, and the blue sub-pixel,

The emission layer includes a red emission layer corresponding to the red sub-pixel, a green emission layer corresponding to the green sub-pixel, and a blue emission layer corresponding to the blue sub-pixel, and

the green emissive layer comprising the composition of any one of claims 1-12.

19. The light emitting device of claim 18, wherein

|R _{Shut off} -G _{Shut off} I and B _{Shut off} -G _{Shut off} At least one of the is 100 microseconds or less,

R _{shut off} In order to be a time required for the luminance of the red light emitted from the red emission layer to reach 10% of the maximum luminance of the red light after stopping the current for the light emitting device,

G _{shut off} For a time required for the luminance of green light emitted from the green emission layer to reach 10% of the maximum luminance of the green light after stopping the current for the light emitting device, and

B _{shut off} A time required for the luminance of blue light emitted from the blue emission layer to reach 10% of the maximum luminance of the blue light after stopping the current for the light emitting device.

20. An electronic device comprising the light emitting device according to any one of claims 13-19.