Organometallic compound, light-emitting device, and electronic apparatus including light-emitting device

文档序号：400948 发布日期：2021-12-17 浏览：21次中文

阅读说明：本技术 有机金属化合物、发光装置和包括发光装置的电子设备 (Organometallic compound, light-emitting device, and electronic apparatus including light-emitting device ) 是由韩定勋高秀秉金性范申秀珍安恩秀李在晟于 2021-05-28 设计创作，主要内容包括：提供了由式1表示的有机金属化合物：[式1]M(L-(1))-(n1)(L-(2))-(n2)[式2][式2A]*-(T-(4))-(a4)-(R-(4))-(b4)式1中的L-(1)为由式2表示的配体,式2中的Z-(4)由式2A表示,并且对式1、2和2A的完全描述在说明书中描述。也提供了包括有机金属化合物的发光装置和包括发光装置的电子设备。(An organometallic compound represented by formula 1 is provided: [ formula 1]M(L 1 ) n1 (L 2 ) n2 [ formula 2]] [ formula 2A)]*‑(T 4 ) a4 ‑(R 4 ) b4 L in formula 1 1 Is a ligand represented by formula 2, Z in formula 2 4 Is represented by formula 2A, and a complete description of formulae 1,2, and 2A is described in the specification. Also provided are a light-emitting device including the organometallic compound and an electronic apparatus including the light-emitting device.)

1. An organometallic compound represented by formula 1:

[ formula 1]

M(L₁)_n1(L₂)_n2

[ formula 2]

[ formula 2A ]

*-(T₄)_a4-(R₄)_b4

Wherein in formulas 1,2 and 2A,

m is a transition metal, and M is a transition metal,

L₁is a ligand represented by the formula 2,

L₂is an organic ligand and is a non-organic ligand,

n1 is 1,2 or 3, and when n1 is 2 or greater, two or more of L₁Are the same as or different from each other,

n2 is 0, 1,2,3 or 4, and when n2 is 2 or greater, two or more of L₂Are the same as or different from each other,

the sum of n1 and n2 is 2,3,4 or 5,

each of × 'and ×' in formula 2 indicates a binding site to M,

ring A₁Is C₄-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group,

Z₄is represented by the formula 2A, wherein,

the symbol x in formula 2A indicates a binding site to an adjacent atom,

G₁is nitrogen or carbon, and can be used as the catalyst,

T₁to T₄Each independently a single bond, represented by-C (R)_10b)(R_10c) A radical, unsubstituted or substituted by at least one R_10aSubstituted C₄-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

a1 to a4 are each independently an integer selected from 1 to 10,

b1 to b4 are each independently an integer selected from 1 to 20,

d4 is an integer selected from 0 to 20,

R₁to R₄、R_10bAnd R_10cEach independently of the others being hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkenyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkynyl, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkoxy, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic ringRadicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic radical, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Aryloxy, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Arylthio, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₁)(Q₂)、-B(Q₁)(Q₂)、-C(＝O)(Q₁)、-S(＝O)₂(Q₁) or-P (═ O) (Q)₁)(Q₂) And is and

R_10acomprises the following steps:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

each unsubstituted or substituted by C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl or C₁-C₆₀Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C₃-C₆₀Carbocyclic group, C₁-C₆₀Heterocyclic group, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio, -Si (Q)₁₁)(Q₁₂)(Q₁₃)、-N(Q₁₁)(Q₁₂)、-B(Q₁₁)(Q₁₂)、-C(＝O)(Q₁₁)、-S(＝O)₂(Q₁₁)、-P(＝O)(Q₁₁)(Q₁₂) Or a combination thereof;

each unsubstituted or substituted by C₃-C₆₀Carbocyclic group, C₁-C₆₀Heterocyclic group, C₆-C₆₀Aryloxy radical or C₆-C₆₀Arylthio groups: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₆₀Carbocyclic group, C₁-C₆₀Heterocyclic group, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio, -Si (Q)₂₁)(Q₂₂)(Q₂₃)、-N(Q₂₁)(Q₂₂)、-B(Q₂₁)(Q₂₂)、-C(＝O)(Q₂₁)、-S(＝O)₂(Q₂₁)、-P(＝O)(Q₂₁)(Q₂₂) Or a combination thereof; or

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁) or-P (═ O) (Q)₃₁)(Q₃₂)，

Wherein Q₁To Q₃、Q₁₁To Q₁₃、Q₂₁To Q₂₃And Q₃₁To Q₃₃Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c₁-C₆₀An alkyl group; c₂-C₆₀An alkenyl group; c₂-C₆₀An alkynyl group; c₁-C₆₀An alkoxy group; or each unsubstituted or by deuterium, -F, cyano, C₁-C₆₀Alkyl radical, C₁-C₆₀C substituted with alkoxy, phenyl, biphenyl or combinations thereof₃-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group.

2. The organometallic compound according to claim 1, wherein

Ring A₁Represented by one of formulae 2-1 to 2-19:

wherein in formulae 2-1 to 2-19,

X₁is O, S, Se or N (R)_1a)，

Ring A₁₁Selected from the group consisting of phenyl, naphthyl, indenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl and pyrazolopyridyl,

R_1aand R in the combined formulae 2 and 2A_10bAre the same as described, andand is

Each indicates a binding site to an adjacent atom.

3. The organometallic compound of claim 1 wherein T₁To T₄Each independently selected from:

a single bond;

by-C (R)_10b)(R_10c) A group represented by; and

each unsubstituted or substituted by at least one R_10aSubstituted phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, dibenzothiophene 5, 5-dioxide, pyridyl, pyrimidinyl, triazinyl, pyrazolyl, triazolyl, and oxadiazolyl.

4. The organometallic compound of claim 1 wherein L₂Is a ligand represented by one of formulae 4-1 to 4-4:

wherein in formulae 4-1 to 4-4,

Y₁₁is O, N, N (R)₁₃)、P(R₁₃)(R₁₄) Or As (R)₁₃)(R₁₄)，

Y₁₂Is O, N, N (R)₁₅)、P(R₁₅)(R₁₆) Or As (R)₁₅)(R₁₆)，

T₁₁Selected from single bond, double bond, — C (R)₁₁)(R₁₂)-*'、*-C(R₁₁)＝C(R₁₂)-*'、*＝C(R₁₁)-*'、*-C(R₁₁)＝*'、*＝C(R₁₁)-C(R₁₂)＝C(R₁₃)-*'、*-C(R₁₁)＝C(R₁₂)-C(R₁₃) (ii) and (R)₁₁)-*'，

Y₁₃To Y₁₆Each independently being C or N,

Y₁₇is C, N (R)₁₇) Or P (R)₁₇)，

Ring A₁₁And ring A₁₂Each independently selected from C₄-C₆₀Carbocyclic group and C₁-C₆₀A heterocyclic group,

R₁₁to R₁₇Each with R in combination formulas 2 and 2A_10bThe same as that described above is true for the description,

c11 and c12 are each independently an integer selected from 1 to 10, and

each indicates a binding site to M in formula 1.

5. The organometallic compound of claim 1 wherein the organometallic compound is selected from compounds 1 to 100:

6. a light emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an interlayer disposed between the first electrode and the second electrode and including an emission layer; and

at least one organometallic compound according to any one of claims 1 to 5.

7. The light emitting device of claim 6, wherein

The light emitting device further includes a capping layer disposed on the second electrode, and

the capping layer has a refractive index greater than or equal to 1.6.

8. The light-emitting device of claim 7, wherein the capping layer comprises a compound represented by formula 201, a compound represented by formula 202, or a combination thereof:

[ formula 201]

[ formula 202]

Wherein in the formulae 201 and 202,

L₂₀₁to L₂₀₄Each independently being unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

L₂₀₅is-O-, 'S-,' N (Q)₂₀₁) -, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₂₀Alkylene, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₂₀Alkenylene, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

xa1 through xa4 are each independently an integer selected from 0 through 5,

xa5 is an integer selected from 1 to 10,

R₂₀₁to R₂₀₄And Q₂₀₁Each independently being unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

R₂₀₁and R₂₀₂Optionally via a single bond, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₅Alkylene being unsubstituted or substituted by at least one R_10aSubstituted C₂-C₅Alkenylene radicals being linked to one another to form radicals which are unsubstituted or substituted by at least one R_10aSubstituted C₈-C₆₀A polycyclic group which is a cyclic group,

R₂₀₃and R₂₀₄Optionally via a single bond, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₅Alkylene being unsubstituted or substituted by at least one R_10aSubstituted C₂-C₅Alkenylene radicals being linked to one another to form radicals which are unsubstituted or substituted by at least one R_10aSubstituted C₈-C₆₀A polycyclic group which is a cyclic group,

R_10ais the same as described in connection with formulas 2 and 2A, and

each indicates a binding site to an adjacent atom.

9. The light-emitting device of claim 6, wherein the emissive layer emits blue or blue-green light having a maximum light emission wavelength in a range of 400nm to 500 nm.

10. An electronic device comprising the light-emitting device according to any one of claims 6 to 9.

Technical Field

Embodiments relate to an organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device.

Background

The light emitting device is a self-emission device which has a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of luminance, driving voltage, and response speed, compared to conventional devices, and produces a full color image.

In the light emitting device, a first electrode is positioned on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes supplied from the first electrode may move to the emission layer through the hole transport region, and electrons supplied from the second electrode may move to the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.

Disclosure of Invention

Embodiments include an organometallic compound having excellent color purity and long life, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device.

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

According to an aspect, an organometallic compound represented by formula 1 is provided.

[ formula 1]

M(L₁)_n1(L₂)_n2

[ formula 2]

[ formula 2A ]

*-(T₄)_a4-(R₄)_b4

In the formulae 1,2 and 2A,

m may be a transition metal, and M may be a transition metal,

L₁may be a ligand represented by formula 2,

L₂can be an organic ligand and can be a metal complex,

n1 can be 1,2 or 3, and when n1 is 2 or greater, two or more L s₁Are the same as or different from each other,

n2 can be 0, 1,2,3 or 4, and when n2 is 2 or greater, two or more L s₂Are the same as or different from each other,

the sum of n1 and n2 may be 2,3,4 or 5,

each of × 'and ×' in formula 2 indicates a binding site to M in formula 1,

ring A₁Can be C₄-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group,

Z₄can be represented by the formula 2A, and,

the symbol x in formula 2A indicates a binding site to an adjacent atom,

G₁can be nitrogen (N) or carbon (C),

T₁to T₄May each independently be a single bond, represented by-C (R)_10b)(R_10c) A radical, unsubstituted or substituted by at least one R_10aSubstituted C₄-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

a1 to a4 may each independently be an integer selected from 1 to 10,

b1 to b4 may each independently be an integer selected from 1 to 20,

d4 can be an integer selected from 0 to 20,

R₁to R₄、R_10bAnd R_10cCan each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkenyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkynyl, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkoxy, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic radical, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Aryloxy, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Arylthio, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₁)(Q₂)、-B(Q₁)(Q₂)、-C(＝O)(Q₁)、-S(＝O)₂(Q₁) or-P (═ O) (Q)₁)(Q₂) And is and

R_10a(may be)

deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro,

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁) or-P (═ O) (Q)₃₁)(Q₃₂)，

According to another aspect, there is provided a light emitting device, which may include a first electrode, a second electrode facing the first electrode, an organic layer disposed between the first electrode and the second electrode and including an emission layer, and at least one organometallic compound as described above.

In an embodiment, the first electrode may be an anode, the second electrode may be a cathode, the emissive layer may include at least one organometallic compound, and the interlayer may further include a hole transport region disposed between the first electrode and the emissive layer and an electron transport region disposed between the emissive layer and the second electrode.

In an embodiment, the light emitting device may further include a capping layer disposed on the second electrode, and the capping layer may have a refractive index greater than or equal to about 1.6.

In an embodiment, the emissive layer may emit blue or blue-green light having a maximum emission wavelength in a range of about 400nm to about 500 nm.

According to another aspect, an electronic device including a light emitting apparatus is provided.

In an embodiment, the electronic device may further include a thin film transistor, the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the light emitting apparatus may be electrically connected to at least one of the source electrode and the drain electrode of the thin film transistor.

In embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.

Drawings

The above and other aspects, features and advantages of embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings in which

Fig. 1 to 3 are each a schematic cross-sectional view of a structure of a light-emitting device according to an embodiment.

Detailed Description

Reference will now be made in detail to the embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the embodiments may have different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by referring to the drawings to explain the described aspects.

In the description, it will be understood that when an element (region, layer or portion, etc.) is referred to as being "on," "connected to" or "coupled to" another element, it can be directly on, connected or coupled to the other element or an intermediate third element may be disposed therebetween.

As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. For example, "a and/or B" may be understood to mean "A, B, or a and B". The terms "and" or "may be used in a connected or disconnected sense, and may be understood to be equivalent to" and/or ".

The term "at least one" is intended to include the meaning of "at least one selected from …" for its meaning and purpose of explanation. For example, "at least one of a and B" can be understood to mean "A, B, or a and B". The term "at least one" when preceding a list of elements modifies the entire list of elements without modifying individual elements in the list.

It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. For example, a first element could be termed a second element, and, similarly, a second element could be termed a first element, without departing from the scope of embodiments of the inventive concept. Terms in the singular may include the plural unless the context clearly dictates otherwise.

The terms "below," "lower," "above," and "upper," etc. are used to describe the relationship of the configurations shown in the figures. These terms are used as relative terms and are described with reference to the directions indicated in the drawings.

It will be understood that the terms "comprises," "comprising," "includes," "including," "has," "having," "has," "contains" and/or "containing" are intended to specify the presence of stated features, integers, steps, operations, elements, components, or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or groups thereof.

The term "about" or "approximately" as used herein includes a stated value and is intended to be within an acceptable deviation of the stated value as determined by one of ordinary skill in the art taking into account the measurement in question and the error associated with the measurement of the stated quantity (i.e., the limitations of the measurement system). For example, "about" may mean within one or more standard deviations, or within 20%, 10%, or 5% of a stated value.

Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure 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 relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

The organometallic compound is represented by formula 1:

[ formula 1]

M(L₁)_n1(L₂)_n2

[ formula 2]

[ formula 2A ]

*-(T₄)_a4-(R₄)_b4。

M in formula 1 may be a transition metal.

In embodiments, M may be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), and osmium (Os).

In formula 1, L₁May be a ligand represented by formula 2.

In formula 1, L₂May be an organic ligand.

In formula 1, n1 may be 1,2 or 3, and when n1 is 2 or greater, two or more L s₁May be the same as or different from each other.

In formula 1, n2 can be 0, 1,2,3, or 4, and when n2 is 2 or greater, two or more L s₂May be the same as or different from each other.

The sum of n1 and n2 in formula 1 can be 2,3,4, or 5.

Each of ×, and ×' in formula 2 indicates a binding site to M in formula 1.

In formula 2, ring A₁Can be C₄-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group.

In an embodiment, ring a in formula 2₁May be phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, cyclopentadienyl, 1,2,3, 4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoborole, benzophosphole, indenyl, benzosilacyclopentadienyl, benzogermaneocyclopentadienyl, benzothienyl, benzoselenophenyl, benzofuranyl, carbazolyl, dibenzoborole, dibenzophosphole, fluorenyl, dibenzosilacyclopentadienyl, dibenzogermaneocyclopentadienyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuranyl, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5, 5-dioxide, azaindolyl, azabenzoborole, Azabenzophosphodienyl, azaindenyl, azabenzosilacyclopentadienyl, azabenzogerstrodienyl, azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azabenzoboranopentadienyl, azabenzophosphodienyl, azafluorenyl, azabenzosilacyclopentadienyl, azabenzogermanepentadienyl, azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azabenzothiophenyl 5-oxideA group, aza-9H-fluoren-9-onyl, aza-dibenzothiophene 5, 5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl, or 5,6,7, 8-tetrahydroquinolinyl.

In an embodiment, ring a in formula 2₁May be represented by one of formulae 2-1 to 2-19:

in formulae 2-1 to 2-19,

X₁can be O, S, Se or N (R)_1a)，

Ring A₁₁Can be selected from phenyl, naphthyl, indenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl and pyrazolopyridyl,

R_1acan be combined with R_10bAre the same as described, and

each indicates a binding site to an adjacent atom.

In an embodiment, the compound represented by formula 2The moiety represented may be represented by one of formulas 5-1 to 5-13:

in formulae 5-1 to 5-13,

Z₄₁to Z₄₃And Z₄₅Can be combined with Z₄Are the same as described, and

each indicates a binding site to an adjacent atom.

In formula 2, Z₄Can be represented by formula 2A, and

the x in formula 2A indicates a binding site to an adjacent atom.

G in formula 2₁Can be nitrogen (N) or carbon (C).

T in formula 2₁To T₄May each independently be a single bond, represented by-C (R)_10b)(R_10c) A radical, unsubstituted or substituted by at least one R_10aSubstituted C₄-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group.

In an embodiment, T₁To T₄May each be independently selected from:

a single bond; by-C (R)_10b)(R_10c) A group represented by; and each unsubstituted or substituted by at least one R_10aSubstituted phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, dibenzothiophene 5, 5-dioxide, pyridyl, pyrimidinyl, triazinyl, pyrazolyl, triazolyl, and oxadiazolyl.

In an embodiment, T₁To T₄May each be independently selected from:

a single bond; by-C (R)_10b)(R_10c) A group represented by formula 2- (1) to 2- (50):

in formulae 2- (1) to 2- (50),

X₂can be O, S, Se or N (R)_2a)，

Y₁Can be N or C (R)_1b)，

Y₂Can be N or C (R)_2b)，

Y₃Can be N or C (R)_3b)，

Y₄Can be N or C (R)_4b)，

Y₅Can be N or C (R)_5b)，

Y₆Can be N or C (R)_6b)，

d13 can be an integer selected from 0 to 3,

d14 can be an integer selected from 0 to 4,

d16 can be an integer selected from 0 to 6, and

d17 can be an integer selected from 0 to 7.

R_10a、R_10bAnd R_10cIs the same as that described in the specification, and

R_2aand R_1bTo R_6bWith the binding of R_10bThe same is described, wherein each of and indicates a binding site to an adjacent atom.

In formulae 2 and 2A, a1 to a4 may each independently be an integer selected from 1 to 10.

In formulas 2 and 2A, b1 to b4 may each independently be an integer selected from 1 to 20.

In formula 2, d4 may be an integer selected from 0 to 20.

In formulae 2 and 2A, R₁To R₄、R_10bAnd R_10cCan each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkenyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkynyl, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkoxy, unsubstituted or substituted by at least oneR is_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic radical, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Aryloxy, unsubstituted or substituted by at least one R_10aSubstituted C₆-C₆₀Arylthio, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₁)(Q₂)、-B(Q₁)(Q₂)、-C(＝O)(Q₁)、-S(＝O)₂(Q₁) or-P (═ O) (Q)₁)(Q₂)。

In an embodiment, R₁To R₄、R_10bAnd R_10cMay each independently be:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

each unsubstituted or substituted by C₁-C₂₀Alkyl radical, C₂-C₂₀Alkenyl radical, C₂-C₂₀Alkynyl or C₁-C₂₀Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -Si (Q)₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁)、-P(＝O)(Q₃₁)(Q₃₂) Or a combination thereof;

cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, substituted or unsubstituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, thienyl, and the like,Isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂Hydroxy, cyano, nitro, C₁-C₂₀Alkyl radical, C₂-C₂₀Alkenyl radical, C₂-C₂₀Alkynyl, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, Dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q)₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁)、-P(＝O)(Q₃₁)(Q₃₂) Or a combination thereof; or

-B(Q₁)(Q₂)、-P(Q₁)(Q₂) or-C (═ O) (Q)₁)。

R_10aCan be as follows:

deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁) or-P (═ O) (Q)₃₁)(Q₃₂) And is and

Q₁to Q₃、Q₁₁To Q₁₃、Q₂₁To Q₂₃And Q₃₁To Q₃₃May each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c₁-C₆₀An alkyl group; c₂-C₆₀An alkenyl group; c₂-C₆₀An alkynyl group; c₁-C₆₀An alkoxy group; or each unsubstituted or by deuterium, -F, cyano, C₁-C₆₀Alkyl radical, C₁-C₆₀Alkoxy, phenyl, biphenyl, or combinations thereof substituted for C₃-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group.

In an embodiment, in formulas 2 and 2A, - (T)₁)_a1-(R₁)_b1、*-(T₂)_a2-(R₂)_b2、*-(T₃)_a3-(R₃)_b3Or: - (T)₄)_a4-(R₄)_b4May be represented by any one of formulas 3-1 to 3-77:

in formulae 3-1 to 3-77,

X₁₂can be O, S, Se or N (R)_12a)，

R₄₀To R₄₈Can be combined with R₁The same as that described above is true for the description,

R₄₁to R₄₈It may be other than hydrogen and it may be,

d14 can be an integer selected from 1 to 4,

d22 can be an integer selected from 1 to 2,

d23 can be an integer selected from 1 to 3,

d24 can be an integer selected from 1 to 4,

d27 can be an integer selected from 1 to 7,

R_10a、R_10band R_10cAs is the case with the description in the specification,

R_12awith the binding of R_10bAre the same as described, and

indicates the binding sites to adjacent atoms.

In an embodiment, R in formula 2₂And R₃At least one of conditions 1 to 3 may be satisfied:

condition 1

R₂Is unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group or-N (Q)_1a)(Q_2a)。

Condition 2

R₃Is unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group or-N (Q)_1b)(Q_2b)。

Condition 3

R₂Is unsubstituted or substituted by at least one R_10aSubstituted byC₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group or-N (Q)_1a)(Q_2a) (ii) a And is

Q_1a、Q_2a、Q_1bAnd Q_2bAnd combined with Q₁Are the same as described, and

R_10aas described in the specification.

In an embodiment, in formula 1, L₂May be a bidentate ligand and the sum of n1 and n2 may be 2 or 3.

In an embodiment, in formula 1, L₂May be a non-carbene ligand.

In an embodiment, in formula 1, n2 may be 1 or greater.

In an embodiment, in formula 1, L₂May be a ligand represented by one of formulae 4-1 to 4-4:

in formulae 4-1 to 4-4,

Y₁₁can be O, N, N (R)₁₃)、P(R₁₃)(R₁₄) Or As (R)₁₃)(R₁₄)，

Y₁₂Can be O, N, N (R)₁₅)、P(R₁₅)(R₁₆) Or As (R)₁₅)(R₁₆)，

T₁₁Can be selected from single bond, double bond, and-C (R)₁₁)(R₁₂)-*'、*-C(R₁₁)＝C(R₁₂)-*'、*＝C(R₁₁)-*'、*-C(R₁₁)＝*'、*＝C(R₁₁)-C(R₁₂)＝C(R₁₃)-*'、*-C(R₁₁)＝C(R₁₂)-C(R₁₃) (ii) and (R)₁₁)-*'，

Y₁₃To Y₁₆May each independently be C or N,

Y₁₇can be C, N (R)₁₇) Or P (R)₁₇)，

Ring A₁₁And ring A₁₂Can be independently selected from C₄-C₆₀Carbocyclic group and C₁-C₆₀A heterocyclic group,

R₁₁to R₁₇With the binding of R_10bThe same as that described above is true for the description,

c11 and c12 may each independently be an integer selected from 1 to 10, and

each indicates a binding site to M in formula 1.

In an embodiment, R₁₁To R₁₇May each independently be:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

each unsubstituted or substituted by C₁-C₂₀Alkyl radical, C₂-C₂₀Alkenyl radical, C₂-C₂₀Alkynyl or C₁-C₂₀Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂，-C(CH₃)₃，-C(CH₃)₂H，-C(CH₃)H₂Hydroxy, cyano, nitro, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -Si (Q)₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁)、-P(＝O)(Q₃₁)(Q₃₂) Or combinations thereof；

Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, each unsubstituted or substituted, Triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl group: deuterium, -F, -Cl, -Br, -I, -CD₃、-CD₂H、-CDH₂、-CF₃、-CF₂H、-CFH₂，-C(CH₃)₃，-C(CH₃)₂H，-C(CH₃)H₂Hydroxy, cyano, nitro, C₁-C₂₀Alkyl radical, C₂-C₂₀Alkenyl radical, C₂-C₂₀Alkynyl, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, and triazolylA radical, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si (Q)₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁)、-P(＝O)(Q₃₁)(Q₃₂) Or a combination thereof; or

-B(Q₁)(Q₂)、-P(Q₁)(Q₂) or-C (═ O) (Q)₁)。

In an embodiment, L in formula 1₂Can be represented by the formula 4-2, and

in formula 4-2, Y₁₁Can be O, Y₁₂May be O, and

T₁₁can be-C (R)₁₁)＝C(R₁₂)-C(R₁₃) Or ═ C (R)₁₁)-C(R₁₂)＝C(R₁₃)-*'。

In an embodiment, the organometallic compound may be selected from compounds 1 to 100, but embodiments of the disclosure are not limited thereto:

the organometallic compound represented by formula 1 may emit blue light or blue-green light.

The organometallic compound represented by formula 1 may emit light having a maximum light emission wavelength in a range of about 400nm to about 500 nm.

The organometallic compound represented by formula 1 has a structure including a carbene ligand having a diboron skeleton represented by formula 2.

Since formula 2 has a diboron skeleton, the durability during driving can be high. The efficiency and lifetime characteristics of the organic electroluminescent light-emitting device can be improved by combining an organometallic compound with a phosphorescent light-emitting material and a delayed fluorescent light-emitting material.

The ligand represented by formula 2 is linked to the central metal in the form of carbene, resulting in high luminous efficiency, high color purity and improved material stability.

Accordingly, an electronic device, such as a light-emitting device, including the organometallic compound represented by formula 1 may have a low driving voltage, a high maximum quantum efficiency, a high efficiency, and a long lifetime.

The method of synthesizing the organometallic compound represented by formula 1 can be recognized by those of ordinary skill in the art by referring to the synthetic examples and/or examples provided below.

At least one organometallic compound represented by formula 1 may be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, a light emitting device is provided, which may include a first electrode; a second electrode facing the first electrode; an interlayer disposed between the first electrode and the second electrode and including an emission layer; and at least one organometallic compound represented by formula 1.

In an embodiment, the light emitting device may further include at least one of a first capping layer disposed outside the first electrode and a second capping layer disposed outside the second electrode, and the organometallic compound represented by formula 1 may be included in at least one of the first capping layer and the second capping layer. The more detailed description of the first capping layer and the second capping layer is the same as that in the specification.

In an embodiment, a light emitting device may include:

a first capping layer disposed outside the first electrode and including an organometallic compound represented by formula 1;

a second capping layer disposed outside the second electrode and including an organometallic compound represented by formula 1; or

A first capping layer and a second capping layer.

In an embodiment of the present invention, the substrate is,

the first electrode of the light emitting device may be an anode,

the second electrode of the light emitting device may be a cathode,

the interlayer 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 can include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking 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.

In an embodiment, the organometallic compound may be included between a pair of electrodes of a light-emitting device. Thus, the organometallic compound may be included in an interlayer of the light emitting device, for example, an emissive layer of the interlayer.

In an embodiment, the emissive layer may include a host and a dopant,

the host and the dopant are different from each other,

the amount of the host is greater than the amount of the dopant, and

the organometallic compound may be included in the dopant.

In an embodiment, the emissive layer may include a dopant and a host, and

the host may include at least one organometallic compound represented by formula 1.

In embodiments, the organometallic compound may emit blue or blue-green light having a maximum light emission wavelength in a range of about 400nm to about 500 nm.

In an embodiment, the light emitting device may further include a second capping layer disposed on the second electrode.

In an embodiment, the second capping layer may have a refractive index greater than or equal to about 1.6.

In an embodiment, the second capping layer may include a compound represented by formula 201 or formula 202:

[ formula 201]

[ formula 202]

In the equations 201 and 202, the first and second equations,

L₂₀₁to L₂₀₄May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

L₂₀₅can be selected from-O-, -S-, -N (Q)₂₀₁) -, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₂₀Alkylene, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₂₀Alkenylene, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

xa1 through xa4 may each independently be an integer selected from 0 through 5,

xa5 can be an integer selected from 1 to 10,

R₂₀₁to R₂₀₄And Q₂₀₁May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic ringsThe radical(s) is (are),

R_10amay be the same as described in connection with formulae 2 and 2A, wherein each indicates a binding site to an adjacent atom.

In an embodiment, the emission layer may emit light having a maximum emission wavelength in a range of about 400nm to about 500 nm.

In an embodiment, the emissive layer may emit blue or blue-green light.

As used herein, the expression "(interlayer and/or capping layer) includes an organometallic compound" may include the case where "(interlayer and/or capping layer) includes one kind of the same organometallic compound represented by formula 1" and the case where "(interlayer and/or capping layer) includes two or more different organometallic compounds represented by formula 1".

In embodiments, the interlayer and/or capping layer may comprise an organometallic compound and may comprise only compound 1. In this regard, compound 1 may be present in the emissive layer of a light emitting device. In an embodiment, the interlayer may include compound 1 and compound 2 as organometallic compounds. In this regard, compound 1 and compound 2 can be present in the same layer (e.g., compound 1 and compound 2 can both be present in the emissive layer) or in different layers (e.g., compound 1 can be present in the emissive layer and compound 2 can be present in the electron transport region).

The term "interlayer" as used herein refers to a single layer and/or all layers between the first and second electrodes of a light emitting device.

According to another aspect, an electronic device including a light emitting apparatus is provided. The electronic device may further include a thin film transistor. In an embodiment, the electronic device may further include a thin film transistor including a source electrode and a drain electrode, and the first electrode of the light emitting apparatus may be electrically connected to at least one of the source electrode and the drain electrode of the thin film transistor. The electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof. The more detailed description of the electronic device is the same as that described in the specification.

[ description of FIG. 1]

Fig. 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.

Hereinafter, the structure of the light emitting device 10 and the method of manufacturing the light emitting device 10 according to the embodiment will be described with reference to fig. 1.

[ first electrode 110]

In fig. 1, a substrate may be additionally disposed below the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. The substrate may be a flexible substrate. In embodiments, the substrate may include a plastic having superior heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyaromatic ester (PAR), polyetherimide, or a combination thereof.

The first electrode 110 may be formed by, for example, depositing or spraying a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that can easily inject holes may be used as a material for forming the first electrode 110.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO)) Tin oxide (SnO)₂) Zinc oxide (ZnO), or a combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or a combination thereof may be used as a material for forming the first electrode 110.

The first electrode 110 may have a single layer structure composed of a single layer or a multi-layer structure including a plurality of layers. In an embodiment, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO.

[ interlayer 130]

The interlayer 130 is disposed on the first electrode 110. The interlayer 130 includes an emission layer.

The interlayer 130 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 150.

The interlayer 130 may further include a metal-containing compound such as an organometallic compound and an inorganic material such as quantum dots, etc., in addition to various organic materials.

In an embodiment, the interlayer 130 may include i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two emission units. When the interlayer 130 includes an emission unit and a charge generation layer, the light emitting device 10 may be a tandem light emitting device.

[ hole transport region in interlayer 130]

The hole transport region may have: i) a single layer structure consisting of a single layer consisting of a single material, ii) a single layer structure consisting of a single layer consisting of a different material, or iii) a multi-layer structure comprising layers comprising different materials.

The hole transport region may include a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission auxiliary layer, an Electron Blocking Layer (EBL), or a combination thereof.

For example, the hole transport region may have a multi-layer structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein in each structure, the layers are sequentially stacked from the first electrode 110.

The hole transport region may include a compound represented by formula 201, a compound represented by formula 202, or a combination thereof, wherein formulae 201 and 202 are the same as described above.

In an embodiment, formulae 201 and 202 may each include at least one group represented by formulae CY201 through CY 217:

with respect to formulae CY201 to CY217, R_10bAnd R_10cCan be combined with R_10aAs described, ring CY₂₀₁To ring CY₂₀₄May each independently be C₃-C₂₀Carbocyclic group or C₁-C₂₀A heterocyclic group, and at least one hydrogen in formulae CY201 to CY217 may be unsubstituted or substituted with at least one R as described herein_10aAnd (4) substitution.

In an embodiment, ring CY in formulas CY201 through CY217₂₀₁To ring CY₂₀₄May each independently be phenyl, naphthyl, phenanthryl or anthracyl.

In an embodiment, formulae 201 and 202 can each include at least one group represented by formulae CY201 through CY 203.

In embodiments, formula 201 may include at least one group represented by formulae CY201 through CY203 and at least one group represented by formulae CY204 through CY 217.

In an embodiment, in formula 201, xa1 is 1, R₂₀₁Is a group represented by one of the formulae CY201 to CY203, xa2 is 0, R₂₀₂Is a group represented by one of formulae CY204 to CY 207.

In an embodiment, each of formulae 201 and 202 may not include a group represented by one of formulae CY201 to CY 203.

In an embodiment, each of formulas 201 and 202 may not include a group represented by one of formulas CY201 to CY203 and may include at least one group represented by formulas CY204 to CY 217.

In an embodiment, each of formulas 201 and 202 may not include a group represented by one of formulas CY201 through CY 217.

For example, the hole transport region may comprise one of the compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β -NPB, TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), or a combination thereof:

the hole transport region may have a thickness of aboutTo aboutWithin the range of (1). For example, the hole transport region can have a thickness of aboutTo aboutWithin the range of (1). When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the hole transport region may have a thickness of aboutTo aboutAnd the thickness of the hole transport layer may be aboutTo aboutWithin the range of (1). For example, the hole injection layer may be about thickTo about Within the range of (1). For example, the hole transport layer may have a thickness of aboutTo aboutWithin the range of (1). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

The emission auxiliary layer may increase light emission efficiency by compensating a light resonance distance according to a wavelength of light emitted from the emission layer, and the electron blocking layer may block a flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer may include materials as described above.

[ P-dopant ]

In addition to these materials, the hole transport region may further include a charge generation material for improving the conductive property. The charge generating material can be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer of charge generating material).

The charge generating material may be, for example, a p-dopant.

In embodiments, the Lowest Unoccupied Molecular Orbital (LUMO) energy level of the p-dopant may be less than or equal to about-3.5 eV.

In embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound containing the element EL1 and the element EL2, or a combination thereof.

Examples of quinone derivatives may include TCNQ and F4-TCNQ.

Examples of the cyano group-containing compound may include HAT-CN and a compound represented by the following formula 221.

[ formula 221]

In the formula 221, the first and second groups,

R₂₂₁to R₂₂₃May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group, and

R₂₂₁to R₂₂₃May each independently be C each substituted by₃-C₆₀Carbocyclic group or C₁-C₆₀Heterocyclic group: a cyano group; -F; -Cl; -Br; -I; c substituted by cyano, -F, -Cl, -Br, -I or combinations thereof₁-C₂₀An alkyl group; or a combination thereof.

With respect to the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a nonmetal, a metalloid, or a combination thereof.

Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or the like); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), or the like); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), or the like); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), or the like); and lanthanoid metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), or the like).

Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).

Examples of the nonmetal may include oxygen (O) and halogen (e.g., F, Cl, Br, I, etc.).

In embodiments, examples of the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, or a metal iodide), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or a combination thereof.

Examples of the metal oxide may include tungsten oxide (e.g., WO, W)₂O₃、WO₂、WO₃Or W₂O₅) Vanadium oxide (e.g., VO, V)₂O₃、VO₂Or V₂O₅) Molybdenum oxide (MoO, Mo)₂O₃、MoO₂、MoO₃Or Mo₂O₅) And rhenium oxide (e.g., ReO)₃)。

Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

Examples of alkaline earth metal halides may include BeF₂、MgF₂、CaF₂、SrF₂、BaF₂、BeCl₂、MgCl₂、CaCl₂、SrCl₂、BaCl₂、BeBr₂、MgBr₂、CaBr₂、SrBr₂、BaBr₂、BeI₂、MgI₂、CaI₂、SrI₂And BaI₂。

Examples of the transition metal halide may include titanium halide (e.g., TiF)₄、TiCl₄、TiBr₄Or TiI₄) Zirconium halide (e.g., ZrF)₄、ZrCl₄、ZrBr₄Or ZrI₄) Hafnium halides (e.g., HfF)₄、HfCl₄、HfBr₄Or HfI₄) Vanadium halides (e.g. VF)₃、VCl₃、VBr₃Or VI₃) Niobium halides (e.g., NbF)₃、NbCl₃、NbBr₃Or NbI₃) Tantalum halides (e.g., TaF)₃、TaCl₃、TaBr₃Or TaI₃) Chromium halides (e.g., CrF)₃、CrCl₃、CrBr₃Or CrI₃) Molybdenum halides (e.g., MoF)₃、MoCl₃、MoBr₃Or MoI₃) Tungsten halides (e.g., WF)₃、WCl₃、WBr₃Or WI₃) Manganese halides (e.g., MnF)₂、MnCl₂、MnBr₂Or MnI₂) Technetium halides (e.g., TcF)₂、TcCl₂、TcBr₂Or TcI₂) Rhenium halides (e.g., ReF)₂、ReCl₂、ReBr₂Or ReI₂) Iron halides (e.g., FeF)₂、FeCl₂、FeBr₂Or FeI₂) Ruthenium halide (e.g., RuF)₂、RuCl₂、RuBr₂Or RuI₂) Osmium halides (e.g., OsF)₂、OsCl₂、OsBr₂Or OsI₂) Cobalt halide (e.g., CoF)₂、CoCl₂、CoBr₂Or CoI₂) Rhodium halides (e.g. RhF)₂、RhCl₂、RhBr₂Or RhI₂) Iridium halides (e.g., IrF)₂、IrCl₂、IrBr₂Or IrI₂) Nickel halide (e.g., NiF)₂、NiCl₂、NiBr₂Or NiI₂) Palladium halides (e.g., PdF)₂、PdCl₂、PdBr₂Or Pdi₂) Platinum halides (e.g., PtF)₂、PtCl₂、PtBr₂Or PtI₂) Copper halides (e.g., CuF, CuCl, CuBr, or CuI), silver halides (e.g., AgF, AgCl, AgBr, or AgI), and gold halides (e.g., AuF, AuCl, AuBr, or AuI).

Examples of the late transition metal halide may include zinc halide (e.g., ZnF)₂、ZnCl₂、ZnBr₂Or ZnI₂) Indium halides (e.g., InI)₃) And tin halides (e.g., SnI)₂)。

Examples of lanthanide metal halides can include YbF, YbF₂、YbF₃、SmF₃、YbCl、YbCl₂、YbCl₃、SmCl₃、YbBr、YbBr₂、YbBr₃、SmBr₃、YbI、YbI₂、YbI₃And SmI₃。

Examples of the metalloid halide may include antimony halide (e.g., SbCl)₅)。

Examples of the metal telluride may include alkali metal telluride (e.g., Li)₂Te、Na₂Te、K₂Te、Rb₂Te or Cs₂Te), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, or BaTe), transition metal tellurides (e.g., TiTe)₂、ZrTe₂、HfTe₂、V₂Te₃、Nb₂Te₃、Ta₂Te₃、Cr₂Te₃、Mo₂Te₃、W₂Te₃、MnTe、TcTe、ReTe、FeTe、RuTe、OsTe、CoTe、RhTe、IrTe、NiTe、PdTe、PtTe、Cu₂Te、CuTe、Ag₂Te, AgTe or Au₂Te), LaTe transition metal tellurides (e.g., or ZnTe), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, or LuTe).

[ emitting layer in interlayer 130]

When the light emitting device 10 is a full color light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer according to sub-pixels. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or are separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials of a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

The emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or a combination thereof.

The dopant may include an organometallic compound represented by formula 1.

The amount of the dopant in the emission layer may range from about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.

In an embodiment, the emissive layer may comprise quantum dots.

The emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or dopant in the emission layer.

The thickness of the emissive layer may be aboutTo aboutWithin the range of (1). For example, the thickness of the emissive layer may be aboutTo aboutWithin the range of (1). When the thickness of the emission layer is within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[ Main body ]

The host may include a compound represented by formula 301 below:

[ formula 301]

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21

In the formula 301, the process is carried out,

Ar₃₀₁and L₃₀₁May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

xb11 can be 1,2 or 3,

xb1 can be an integer selected from 0 to 5,

R₃₀₁can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkenyl, unsubstituted or substituted by at least one R_10aSubstituted C₂-C₆₀Alkynyl, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Alkoxy, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic radical, -Si (Q)₃₀₁)(Q₃₀₂)(Q₃₀₃)、-N(Q₃₀₁)(Q₃₀₂)、-B(Q₃₀₁)(Q₃₀₂)、-C(＝O)(Q₃₀₁)、-S(＝O)₂(Q₃₀₁) or-P (═ O)(Q₃₀₁)(Q₃₀₂)，

xb21 can be an integer selected from 1 to 5, and

Q₃₀₁to Q₃₀₃In combination with description Q₁The same is described.

In an embodiment, when xb11 in formula 301 is 2 or more, two or more Ar' s₃₀₁May be connected to each other via a single bond.

In an embodiment, the subject may include a compound represented by formula 301-1, a compound represented by formula 301-2, or a combination thereof:

[ formula 301-1]

[ formula 301-2]

In the formulae 301-1 and 301-2,

ring A₃₀₁To ring A₃₀₄May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

X₃₀₁can be O, S, N- [ (L)₃₀₄)_xb4-R₃₀₄]、C(R₃₀₄)(R₃₀₅) Or Si (R)₃₀₄)(R₃₀₅)，

xb22 and xb23 can each independently be 0, 1 or 2,

L₃₀₁xb1 and R₃₀₁As is the case with the description in the specification,

L₃₀₂to L₃₀₄Each independently with a binding L₃₀₁The same as that described above is true for the description,

xb 2-xb 4 can each independently be the same as described in connection with xb1, and

R₃₀₂to R₃₀₅And R₃₁₁To R₃₁₄With the binding of R₃₀₁The same is described.

In an embodiment, the body may include an alkaline earth metal composite. In embodiments, the host can Be a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or a combination thereof.

In embodiments, the host may include one of compounds H1-H124, 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 9, 10-bis (2-naphthyl) -2-tert-butyl-anthracene (TBADN), 4 '-bis (N-carbazolyl) -1, 1' -biphenyl (CBP), 1, 3-bis-9-carbazolylbenzene (mCP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), or a combination thereof, although embodiments of the disclosure are not limited thereto:

[ delayed fluorescent Material ]

The emission layer may include a delayed fluorescence material.

The delayed fluorescence material as used herein may be selected from any compound capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

Depending on the type of other materials included in the emission layer, the delayed fluorescence material included in the emission layer may be used as a host or a dopant.

In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be in a range of about 0eV to about 0.5 eV. When the difference between the triplet level (eV) of the delayed fluorescent material and the singlet level (eV) of the delayed fluorescent material satisfies the above range, the up-conversion of the triplet state to the singlet state of the delayed fluorescent material can be effectively occurred, and thus, the light emitting efficiency of the light emitting device 10 can be improved.

In embodiments, the delayed fluorescent material may comprise i) at least one electron donor (e.g., pi electron rich C)₃-C₆₀Cyclic groups such as carbazolyl) and at least one electron acceptor (e.g., sulfoxide, cyano, or C containing a pi-electron depleted nitrogen₁-C₆₀Cyclic group) ii) comprises C₈-C₆₀Materials of polycyclic radicals, in C₈-C₆₀Two or more cyclic groups in the polycyclic group share boron (B) and are fused to each other.

The delayed fluorescence material may comprise at least one of compounds DF1 to DF 9:

[ Quantum dots ]

The emissive layer may comprise quantum dots.

As used herein, quantum dots refer to crystals of semiconductor compounds and may include any material capable of emitting light of various emission wavelengths depending on the crystal size.

The diameter of the quantum dots can be, for example, in the range of about 1nm to about 10 nm.

Quantum dots can be synthesized by wet chemical processes, metal organic chemical vapor deposition processes, molecular beam epitaxy processes, or processes similar to these.

The wet chemical process refers to a method in which a solvent and a precursor material are mixed and then a quantum dot particle crystal is grown. When the crystal grows, the organic solvent serves as a dispersing agent that coordinates naturally on the surface of the quantum dot crystal and controls the growth of the crystal. Accordingly, the quantum dot particle growth may be controlled by using processes such as a Metal Organic Chemical Vapor Deposition (MOCVD) process and a Molecular Beam Epitaxy (MBE) process, which are easily performed at low cost compared to a vapor deposition process.

The quantum dots may include group III-VI semiconductor compounds, group II-VI semiconductor compounds, group III-V semiconductor compounds, group I-III-VI semiconductor compounds, group IV elements or compounds, or combinations thereof.

Examples of the group II-VI semiconductor compound may include: binary compounds such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSeTe; or a combination thereof.

Examples of the group III-V semiconductor compound may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, gainp, GaInNAs, gainsb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, inalnpas, inalnpsb, or GaAlNP; or a combination thereof. The group III-V semiconductor compound may further include a group II element. Examples of the group III-V semiconductor compound further including a group II element may include InZnP, InGaZnP, or InAlZnP.

Examples of the group III-VI semiconductor compounds may include: binary compounds, e.g. GaS, GaSe, Ga₂Se₃、GaTe、InS、In₂S₃、InSe、In₂Se₃Or InTe; ternary compounds, e.g. InGaS₃Or InGaSe₃(ii) a Or a combination thereof.

Examples of the group I-III-VI semiconductor compounds may include: ternary compounds, e.g. AgInS, AgInS₂、CuInS、CuInS₂、CuGaO₂、AgGaO₂Or AgAlO₂(ii) a Or a combination thereof.

Examples of the group IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, or SnPbSTe; or a combination thereof.

In embodiments, the group IV element or compound may include: single element compounds such as Si or Ge; binary compounds such as SiC or SiGe; or a combination thereof.

Each element included in the multi-element compound such as binary compounds, ternary compounds, and quaternary compounds may be present in the particles in a uniform concentration or a non-uniform concentration.

The quantum dot may have a single structure or a double structure of a core shell in which each element is included in the corresponding quantum dot in a uniform concentration. For example, the material included in the core may be different from the material included in the shell.

The shell of the quantum dot may serve as a protective layer for maintaining semiconductor properties by preventing chemical degradation of the core, and/or may serve as a charging layer for imparting electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases towards the center.

Examples of shells for quantum dots are metal or non-metal oxides, semiconductor compounds, or combinations thereof. Examples of metal or nonmetal oxides may include: binary compounds, e.g. SiO₂、Al₂O₃、TiO₂、ZnO、MnO、Mn₂O₃、Mn₃O₄、CuO、FeO、Fe₂O₃、Fe₃O₄、CoO、Co₃O₄Or NiO; ternary compounds, e.g. MgAl₂O₄、CoFe₂O₄、NiFe₂O₄Or CoMn₂O₄(ii) a Or a combination thereof. Examples of the semiconductor compound may include group III-VI semiconductor compounds, group II-VI semiconductor compounds, group III-V semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or combinations thereof, as described herein. In an embodiment, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or a combination thereof.

The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dots may be less than or equal to about 45 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots may be less than or equal to about 40 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dots may be less than or equal to about 30 nm. When the FWHM of the emission wavelength spectrum of the quantum dot is within this range, color purity or color reproduction can be improved. Light emitted through these quantum dots is illuminated in all directions. Therefore, a wide viewing angle can be increased.

The quantum dots can be spherical, pyramidal, multi-armed, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanosheet particles.

By adjusting the size of the quantum dots, the energy band gap can also be adjusted, thereby obtaining light of various wavelengths in the quantum dot emission layer. Therefore, by using quantum dots of different sizes, light emitting devices emitting light of various wavelengths can be realized. In detail, the size of the quantum dots may be selected to emit red, green and/or blue light. The size of the quantum dots may be adjusted so that light of various colors is combined to emit white light.

[ Electron transport region in interlayer 130]

The electron transport region may have: i) a single layer structure consisting of a single layer consisting of a single material, ii) a single layer structure consisting of a single layer consisting of a different material, or iii) a multi-layer structure comprising layers comprising different materials.

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

In embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein for each structure, the constituent layers are sequentially stacked from the emission layer.

The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) can include a metal-free compound comprising at least one C containing pi-electron depleted nitrogen₁-C₆₀A cyclic group.

In embodiments, the electron transport region may comprise a compound represented by formula 601 below:

[ formula 601]

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21

In the formula 601, the first and second groups,

Ar₆₀₁and L₆₀₁May each independently be unsubstituted or substituted with at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals or unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group,

xe11 may be 1,2 or 3,

xe1 may be 0, 1,2,3,4, or 5,

R₆₀₁may be unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic radicals, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀Heterocyclic radical, -Si (Q)₆₀₁)(Q₆₀₂)(Q₆₀₃)、-C(＝O)(Q₆₀₁)、-S(＝O)₂(Q₆₀₁) or-P (═ O) (Q)₆₀₁)(Q₆₀₂)，

Q₆₀₁To Q₆₀₃And combined with Q₁The same as that described above is true for the description,

xe21 can be 1,2,3,4, or 5, and

Ar₆₀₁、L₆₀₁and R₆₀₁May each independently be unsubstituted or substituted by at least one R_10aSubstituted C containing pi-electron depleted nitrogen₁-C₆₀A cyclic group.

In an embodiment, when xe11 in formula 601 is 2 or greater, two or more Ar s₆₀₁May be connected to each other via a single bond.

In an embodiment, Ar in formula 601₆₀₁Can be a substituted or unsubstituted anthracenyl group.

In an embodiment, the electron transport region may comprise a compound represented by formula 601-1:

[ formula 601-1]

In the formula 601-1, the reaction mixture,

X₆₁₄can be N or C (R)₆₁₄)，X₆₁₅Can be N or C (R)₆₁₅)，X₆₁₆Can be N or C (R)₆₁₆) And X₆₁₄To X₆₁₆At least one of which may be N,

L₆₁₁to L₆₁₃Can be incorporated by reference₆₀₁The description is given for the sake of understanding,

xe611 through xe613 may be understood by reference to the description in connection with xe1,

R₆₁₁to R₆₁₃Can be combined by reference with R₆₀₁Is understood by the description of (A), an

R₆₁₄To R₆₁₆Can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, unsubstituted or substituted by at least one R_10aSubstituted C₃-C₆₀Carbocyclic group, unsubstituted or substituted by at least one R_10aSubstituted C₁-C₆₀A heterocyclic group.

In embodiments, xe1 and xe 611-xe 613 in formulas 601 and 601-1 can each independently be 0, 1, or 2.

The electron transport region may comprise one of the compounds ET1 to ET45, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), Alq₃BAlq, TAZ, NTAZ, or a combination thereof:

the electron transport region may have a thickness of aboutTo aboutWithin the range of (1). For example, the electron transport region can have a thickness of aboutTo aboutWithin the range of (1). When the electron transport region comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or a combination thereof, the buffer layer, the hole blocking layer, or the electron control layer can each independently have a thickness of aboutTo aboutAnd the thickness of the electron transport layer may be aboutTo about Within the range of (1). For example, the buffer layer, hole blocking layer, or electron control layer can each independently have a thickness of aboutTo aboutWithin the range of (1). For example, the electron transport layer may have a thickness of aboutTo aboutWithin the range of (1). When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, and/or the electron transport layer are within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.

The metal-containing material can include an alkali metal composite, an alkaline earth metal composite, or a combination thereof. The metal ion of the alkali metal complex may Be a Li ion, a Na ion, a K ion, an Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex may Be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligands coordinated to the metal ion of the alkali metal complex or alkaline earth metal complex may each independently be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthredine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

In an embodiment, the metal-containing material may include a Li composite. Li complexes may include, for example, the compounds ET-D1(LiQ) or ET-D2:

the electron transport region may include an electron injection layer facilitating injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

The electron injection layer may have: i) a single layer structure consisting of a single layer consisting of a single material, ii) a single layer structure consisting of a single layer consisting of a different material, or iii) a multi-layer structure comprising layers comprising different materials.

The electron injection layer can include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal composite, an alkaline earth metal composite, a rare earth metal composite, or combinations thereof.

The alkali metal may include Li, Na, K, Rb, Cs, or combinations thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or combinations thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or combinations thereof.

The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound can be oxides and halides (e.g., fluorides, chlorides, bromides, or iodides), tellurides, or combinations thereof, of alkali metals, alkaline earth metals, and rare earth metals.

The alkali metal-containing compound may be an alkali metal oxide such as Li₂O、Cs₂O or K₂O, an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or a combination thereof. The alkaline earth metal-containing compound may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba_xSr_1-xO (x is 0<x<Real number of 1 condition) or Ba_xCa_1-xO (x is 0<x<1 real number of condition). The rare earth metal-containing compound may include YbF₃、ScF₃、Sc₂O₃、Y₂O₃、Ce₂O₃、GdF₃、TbF₃、YbI₃、ScI₃、TbI₃Or a combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La, or the like₂Te₃、Ce₂Te₃、Pr₂Te₃、Nd₂Te₃、Pm₂Te₃、Sm₂Te₃、Eu₂Te₃、Gd₂Te₃、Tb₂Te₃、Dy₂Te₃、Ho₂Te₃、Er₂Te₃、Tm₂Te₃、Yb₂Te₃And Lu₂Te₃。

The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may include i) one of metal ions of alkali metals, alkaline earth metals, and rare earth metals, and ii) as a ligand to be connected to the metal ions, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenylpyridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal composite, an alkaline earth metal composite, a rare earth metal composite, or a combination thereof, or may further include an organic material (e.g., a compound represented by formula 601).

In an embodiment, the electron injection layer may consist of: i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or a combination thereof. In an embodiment, the electron injection layer may be a KI: Yb codeposit layer or an RbI: Yb codeposit layer.

When the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkali earth metal-containing compound, rare earth metal-containing compound, alkali metal composite, alkaline earth metal composite, rare earth metal composite, or a combination thereof may be uniformly or non-uniformly dispersed in the matrix comprising the organic material.

The electron injection layer may have a thickness of aboutTo aboutWithin the range of (1). For example, the electron injection layer may be about thickTo aboutWithin the range of (1). When the thickness of the electron injection layer is within the above range, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

[ second electrode 150]

The second electrode 150 may be disposed on the interlayer 130 having such a structure. The second electrode 150 may be a cathode that is an electron injection electrode, and as a material for forming the second electrode 150, metals, alloys, conductive compounds, or a combination thereof, each having a low work function, may be used.

The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 150 may have a single layer structure or a multi-layer structure including two or more layers.

[ capping layer ]

The first capping layer may be disposed outside the first electrode 110, and/or the second capping layer may be disposed outside the second electrode 150. The light emitting device 10 may have a structure in which a first capping layer, a first electrode 110, an interlayer 130, and a second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.

Light generated in the emission layer of the interlayer 130 of the light emitting device 10 may be emitted outward through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, and light generated in the emission layer of the interlayer 130 of the light emitting device 10 may be emitted outward through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.

According to the principle of constructive interference, the first capping layer and the second capping layer may increase external light emitting efficiency. Therefore, the light emission efficiency of the light emitting device 10 increases, so that the light emission efficiency of the light emitting device 10 can be improved.

Each of the first capping layer and the second capping layer may comprise a material having a refractive index (at 589 nm) greater than or equal to about 1.6.

The first capping layer and the second capping layer may each independently be an organic capping layer comprising an organic material, an inorganic capping layer comprising an inorganic material, or a composite capping layer comprising an organic material and an inorganic material.

At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compounds, heterocyclic compounds, and amine group-containing compounds can be optionally substituted with substituents comprising O, N, S, Se, Si, F, Cl, Br, I, or combinations thereof. In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.

In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by formula 201, a compound represented by formula 202, or a combination thereof.

In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of the compounds HT28 through HT33, one of the compounds CP1 through CP6, β -NPB, or a combination thereof:

[ electronic apparatus ]

The light emitting device may be included in various electronic apparatuses. In an embodiment, the electronic device including the light emitting apparatus may be a light emitting device or an authentication device, or the like.

In addition to the light emitting device, the electronic apparatus (e.g., light emitting apparatus) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be disposed in at least one traveling direction of light emitted from the light emitting device. In embodiments, the light emitted from the light emitting device may be blue light or white light. The light emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dots can be, for example, quantum dots as described herein.

An electronic device may include a first substrate. The first substrate includes sub-pixels, the color filters include color filter regions respectively corresponding to the sub-pixels, and the color conversion layer may include color conversion regions respectively corresponding to the sub-pixels.

The pixel defining layer may be between the sub-pixels to define each sub-pixel.

The color filter may further include color filter regions and light blocking patterns between the color filter regions, and the color conversion layer may further include color conversion regions and light blocking patterns between the color conversion regions.

The color filter region (or the color conversion region) may include a first region emitting a first color light, a second region emitting a second color light, and/or a third region emitting a third color light, and the first color light, the second color light, and/or the third color light may have maximum emission wavelengths different from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. In detail, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as described in this specification. The first region, the second region and/or the third region may further comprise a scatterer.

In an embodiment, the light emitting device may emit first light, the first region may absorb the first light to emit first color light, the second region may absorb the first light to emit second first color light, and the third region may absorb the first light to emit third first color light. In this regard, the first, second, and third first color lights may have different maximum emission wavelengths from each other. In detail, the first light may be blue light, the first color light may be red light, the second first color light may be green light, and the third first color light may be blue light.

In addition to the light emitting device as described above, the electronic apparatus may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein at least one of the source electrode and the drain electrode may be electrically connected to any one of a first electrode and a second electrode of the light emitting device.

The thin film transistor may further include a gate electrode, a gate insulating film, or the like.

The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

The electronic apparatus may further include a sealing portion for sealing the light emitting device. The sealing portion may be between the color filter and/or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be extracted to the outside while preventing ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing part may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

On the sealing portion, various functional layers may be further provided in addition to the color filter and/or the color conversion layer according to the use of the electronic device. The functional layers may include a touch screen layer, a polarizing layer, and the like. The touch screen layer can be a pressure-sensitive touch screen layer, a capacitive touch screen layer or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device for authenticating an individual by using biometric information of a biometric body (e.g., a fingertip, a pupil, or the like).

The authentication apparatus may further include a biometric information collector in addition to the light emitting device.

The electronic apparatus is applicable to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game machines, medical tools (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measurement tools, meters (e.g., meters for vehicles, aircraft, and ships), projectors, and the like.

[ description of FIGS. 2 and 3 ]

Fig. 2 is a schematic cross-sectional view of a light emitting device according to an embodiment.

The light emitting apparatus of fig. 2 includes a substrate 100, a Thin Film Transistor (TFT), a light emitting device, and a package portion 300 sealing the light emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating through the substrate 100 and may provide a flat surface on the substrate 100.

The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.

An interlayer insulating film 250 may be disposed on the gate electrode 240. An interlayer insulating film 250 is disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose source and drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed portions of the source and drain regions of the active layer 220.

The TFT may be electrically connected to a light emitting device to drive the light emitting device, and covered by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light emitting device is provided on the passivation layer 280. The light emitting device includes a first electrode 110, an interlayer 130, and a second electrode 150.

The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a region of the drain electrode 270, and the first electrode 110 may be connected to the exposed region of the drain electrode 270.

A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in fig. 2, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and thus may be provided in the form of a common layer.

The second electrode 150 may be disposed on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. A capping layer 170 may be formed to cover the second electrode 150.

The encapsulation part 300 may be disposed on the capping layer 170. The encapsulation portion 300 may be disposed on the light emitting device and may protect the light emitting device from moisture or oxygen. The encapsulation part 300 may include: inorganic film comprising silicon nitride (SiN)_x) Silicon oxide (SiO)_x) Indium tin oxide, indium zinc oxide, or combinations thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinylsulfonate, polyoxymethylene, polyaromatic ester, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate or polyacrylic acid), epoxy-based resins (e.g., Aliphatic Glycidyl Ether (AGE)), or a combination thereof; or a combination of inorganic and organic films.

Fig. 3 is a schematic cross-sectional view showing a light emitting apparatus according to an embodiment of the present disclosure.

The light emitting apparatus of fig. 3 is the same as the light emitting apparatus of fig. 2 except that the light blocking pattern 500 and the functional region 400 are disposed on the encapsulation portion 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. In an embodiment, the light emitting devices included in the light emitting apparatus of fig. 3 may be series light emitting devices.

[ production method ]

The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region may be formed in the region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, langmuir-blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, a deposition temperature of about 100 ℃ to about 500 ℃, about 10 ℃ may be possible by considering the materials contained in the layer to be formed and the structure of the layer to be formed^-8Is supported to about 10^-3Vacuum degree of tray and its combinationTo aboutIs deposited at a deposition rate of (3).

[ definition of terms ]

The term "C" as used herein₃-C₆₀Carbocyclic group "means a cyclic group consisting of carbon only and having 3 to 60 carbon atoms, preferably C₄-C₆₀A carbocyclic group, and the term "C" as used herein₁-C₆₀The heterocyclic group "means a cyclic group having 1 to 60 carbon atoms and further including a heteroatom in addition to carbon. C₃-C₆₀Carbocyclic group and C₁-C₆₀The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. In an embodiment, C₁-C₆₀The number of ring-forming atoms of the heterocyclic group may be 3 to 61.

The term "cyclic group" as used herein includes C₃-C₆₀Carbocyclic group and C₁-C₆₀A heterocyclic group.

The term "pi electron rich C" as used herein₃-C₆₀The cyclic group "refers to a cyclic group having 3 to 60 carbon atoms and not including-N ═ N' as a ring-forming moiety, and the term" C containing pi-electron depleted nitrogen as used herein₁-C₆₀The cyclic group "means a heterocyclic group having 1 to 60 carbon atoms and including-N ═ N' as a ring-forming moiety.

For example,

C₃-C₆₀the carbocyclic group may be i) a group T1 or ii) a fused ring group in which two or more groups T1 are fused to each other (e.g. cyclopentadienyl, adamantyl, norbornyl, phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthrenyl, perylenyl, pentylphenyl, heptenophenyl, tetracenyl, picenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, indenyl, perillyl, azulenyl, phenanthrenyl, anthrenyl, etc,Fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl or indenonanthryl),

C₁-C₆₀the heterocyclic group can be i) a group T2, ii) a fused ring group in which two or more groups T2 are fused to each other, or iii) a fused ring group in which at least one group T2 and at least one group T1 are fused to each other (e.g., pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilacyclopentadienyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilacyclopentadienyl, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilacarbazolyl, benzindolocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilacyclopentadienyl, benzofurodibenzofuryl, benzonaphthobenzofuranyl, and dibenzofuryl, Benzofurodibenzothienyl, benzothiophenyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalyl, benzoquinoxalyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azabicycloheptanyl, azadibenzothienyl or azadibenzofuranyl),

c rich in pi electrons₃-C₆₀The cyclic group may be i) a group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) a group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (for example,C₃-C₆₀carbocyclic groups, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilacyclopentadienyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilacyclopentadienyl, dibenzothienyl, dibenzofuryl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilacarbazolyl, benzindoloncarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthobenzothienyl, benzonaphthosilaheterocyclic cyclopentadienyl, benzofurodibenzofuryl, benzofurodibenzothienyl or benzothienodibenzothienyl),

c containing pi-electron depleted nitrogen₁-C₆₀The cyclic group may be i) a group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1, and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzisoquinolyl, quinoxalinyl, Benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilacyclopentadienyl, azadibenzothienyl or azadibenzofuranyl),

the group T1 may be a cyclopropane, cyclobutenyl, cyclopentanyl, cyclohexane, cycloheptanyl, cyclooctanyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or, bicyclo [2.2.1] heptanyl), norbornenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.2] octyl or phenyl group,

the group T2 may be furyl, thienyl, 1H-pyrrolyl, silacyclopentadienyl, borapentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilacyclopentadienyl, azaboroheterocyclopentadienyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl,

the group T3 may be furyl, thienyl, 1H-pyrrolyl, silacyclopentadienyl or boracyclopentadienyl, and

the group T4 may be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilacyclopentadienyl, azaborole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

The terms "cyclic group", "C" as used herein₃-C₆₀Carbocyclic group "," C₁-C₆₀Heterocyclic radical "," pi-electron rich C₃-C₆₀Cyclic group "or" C containing pi-electron depleted nitrogen₁-C₆₀The cyclic group "refers to a group condensed with a cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, or the like) according to the structure of the formula described with the corresponding term. In embodiments, "phenyl" may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of the formula including "phenyl".

In an embodiment, monovalent C₃-C₆₀Carbocyclic group and monovalent C₁-C₆₀Examples of heterocyclic groups may include C₃-C₁₀Cycloalkyl radical, C₁-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group and a monovalent non-aromatic fused heteropolycyclic group, and a divalent C₃-C₆₀Carbocyclic group and divalent C₁-C₆₀Examples of heterocyclic groups may include C₃-C₁₀Cycloalkylene radical, C₁-C₁₀Heterocycloalkylene, C₃-C₁₀Cycloalkenylene group, C₁-C₁₀Heterocyclylene radical, C₆-C₆₀Arylene radical, C₁-C₆₀Heteroarylene, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

The term "C" as used herein₁-C₆₀The alkyl group "means a straight or branched chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 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, sec-decyl, and tert-decyl. The term "C" as used herein₁-C₆₀Alkylene "means with C₁-C₆₀The alkyl groups being divalent radicals of the same structure, preferably C₁-C₂₀Alkylene or C₁-C₅An alkylene group.

The term "C" as used herein₂-C₆₀Alkenyl "is as indicated at C₂-C₆₀The monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term "C" as used herein₂-C₆₀Alkenylene refers to the group with C₂-C₆₀The alkenyl groups being divalent radicals of the same structure, preferably C₂-C₂₀Alkenylene or C₂-C₅An alkenylene group.

The term "C" as used herein₂-C₆₀Alkynyl "means at C₂-C₆₀The monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term "C" as used herein₂-C₆₀Alkynylene "means with C₂-C₆₀Alkynyl groups have divalent radicals of the same structure.

The term "C" as used herein₁-C₆₀Alkoxy "means a group consisting of-OA₁₀₁(wherein A is₁₀₁Is C₁-C₆₀Alkyl), and examples thereof include methoxy, ethoxy, and isopropoxy.

The term "C" as used herein₃-C₁₀Cycloalkyl "refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [2.2.1] alkyl)]Heptyl), bicyclo [1.1.1]Pentyl, bicyclo [2.1.1]Hexyl and bicyclo [2.2.2]And (4) octyl. The term "C" as used herein₃-C₁₀Cycloalkylene "means a compound with C₃-C₁₀Cycloalkyl groups have divalent radicals of the same structure.

The term "C" as used herein₁-C₁₀The heterocycloalkyl group "means a monovalent cyclic group further including at least one hetero atom as a ring-forming atom in addition to carbon atoms and having 1 to 10 carbon atoms, and examples thereof include a1, 2,3, 4-oxatriazolyl group, a tetrahydrofuranyl group, and a tetrahydrothienyl group. The term "C" as used herein₁-C₁₀Heterocycloalkylene "means a group with C₁-C₁₀Heterocycloalkyl groups have divalent radicals of the same structure.

The term "C" as used herein₃-C₁₀The cycloalkenyl group "means a monovalent cyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in its ring and no aromaticity, and examples thereof include cyclopentenyl group, cyclohexenyl group and cycloheptenyl group. The term "C" as used herein₃-C₁₀Cycloalkenyl is taken to mean radicals with C₃-C₁₀Cycloalkenyl groups are divalent radicals of the same structure.

The term "C" as used herein₁-C₁₀Heterocycloalkenyl "refers to a monovalent cyclic group having at least one heteroatom as a ring-forming atom in addition to carbon atoms, 1 to 10 carbon atoms, and having at least one double bond in its cyclic structure. C₁-C₁₀Examples of heterocycloalkenyl groups include 4, 5-dihydro-1, 2,3, 4-oxatriazolyl, 2, 3-dihydrofuranyl, and 2, 3-dihydrothienyl. The term "C" as used herein₁-C₁₀Heterocycloalkenylene "means a group with C₁-C₁₀Heterocycloalkenyl groups have divalent radicals of the same structure.

The term "C" as used herein₆-C₆₀Aryl "refers to a monovalent group having a carbocyclic aromatic system containing from 6 to 60 carbon atoms, and as used herein the term" C₆-C₆₀Arylene "refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. C₆-C₆₀Examples of the aryl group include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthryl, anthracyl, fluoranthenyl, triphenylenyl, pyrenyl, 1, 2-benzophenanthryl, perylenyl, pentylenenyl, heptenophenyl, tetracenyl, picenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, and oval-phenyl groups. When C is present₆-C₆₀Aryl and C₆-C₆₀When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

The term "C" as used herein₁-C₆₀Heteroaryl "refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom as a ring-forming atom in addition to carbon atoms and having from 1 to 60 carbon atoms. The term "C" as used herein₁-C₆₀Heteroarylene "means a divalent group having a heterocyclic aromatic system having at least one hetero atom as a ring-forming atom in addition to carbon atoms and having 1 to 60 carbon atoms. C₁-C₆₀Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, tripyrimidinylOxazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalyl, benzoquinoxalyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. When C is present₁-C₆₀Heteroaryl and C₁-C₆₀When the heteroarylenes each include two or more rings, the two or more rings may be fused to each other.

The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and having no aromaticity in its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups include indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthrenyl, and indenonanthrenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having at least one heteroatom other than carbon atoms as a ring-forming atom, and having no aromaticity (e.g., having 1 to 60 carbon atoms) in its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilacyclopentadienyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilacyclopentadienyl, dibenzothienyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azabicycloheptacyclopentadienyl, azabenzothienyl, azabenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, oxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, and the like, Imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indonocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilacyclopentacarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilacyclopentadienyl, benzofurodibenzofuranyl, benzofurodibenzothienyl, and benzothienodibenzothienyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

The term "C" as used herein₆-C₆₀Aryloxy means-OA₁₀₂(wherein A is₁₀₂Is C₆-C₆₀Aryl), and the term "C" as used herein₆-C₆₀Arylthio "means-SA₁₀₃(wherein A is₁₀₃Is C₆-C₆₀Aryl).

The term "R" as used herein_10a"can be:

deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

-Si(Q₃₁)(Q₃₂)(Q₃₃)、-N(Q₃₁)(Q₃₂)、-B(Q₃₁)(Q₃₂)、-C(＝O)(Q₃₁)、-S(＝O)₂(Q₃₁) or-P (═ O) (Q)₃₁)(Q₃₂)。

Q as used herein₁To Q₃、Q₁₁To Q₁₃、Q₂₁To Q₂₃And Q₃₁To Q₃₃May each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c₁-C₆₀An alkyl group; c₂-C₆₀An alkenyl group; c₂-C₆₀An alkynyl group; c₁-C₆₀An alkoxy group; or each unsubstituted or by deuterium, -F, cyano, C₁-C₆₀Alkyl radical, C₁-C₆₀C substituted with alkoxy, phenyl, biphenyl or combinations thereof₃-C₆₀Carbocyclic group or C₁-C₆₀A heterocyclic group.

The term "heteroatom" as used herein refers to any atom that is not a carbon atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, and combinations thereof.

The term "Ph" as used herein refers to phenyl, the term "Me" as used herein refers to methyl, the term "Et" as used herein refers to ethyl, the term "tert-Bu" or "Bu" as used herein refers to ethyl^t"refers to a tert-butyl group, and the term" OMe "as used herein refers to methoxy.

The term "biphenyl" as used herein refers to a "phenyl group substituted with a phenyl group". In other words, "biphenyl" is a compound having C₆-C₆₀Aryl as a substituent.

The term "terphenyl" as used herein refers to a "phenyl group substituted with a biphenyl group". For example, "terphenyl" is a compound having a structure represented by formula C₆-C₆₀Aryl substituted C₆-C₆₀Aryl as a substituent.

Unless otherwise defined, each of, 'and' as used herein refers to a binding site to an adjacent atom in the respective formula.

Hereinafter, a compound according to an embodiment and a light-emitting device according to an embodiment will be described in detail with reference to synthesis examples and examples. The phrase "replacing A with B" as used in describing the synthetic examples means replacing A with an equivalent molar equivalent of B.

[ examples ]

Synthesis example 1: synthesis of Compound 1

Synthesis of intermediate [1-A ]

10.0g (107.4mmol) of aniline, 7.4g (50.0mmol) of triethyl orthoformate and 150mg (2.5mmol) of glacial acetic acid are stirred at 160 ℃ for 12 h. After completion of the reaction, the reaction resultant was cooled to room temperature, 50mL of 10% aqueous sodium carbonate solution was added thereto, and subjected to an extraction process by using ether. The extracted organic layer was dried by using sodium sulfate, and the solvent was removed therefrom, whereby 4.7g (24mmol) of intermediate [1-A ] was obtained.

Synthesis of intermediate [1-B ]

4.7g (24mmol) of intermediate [1-A ] were added to the reaction vessel and suspended in 50mL of tetrahydrofuran. To this was added 12mL (24mmol) of n-butyllithium (2.0M in hexane) at room temperature, and stirred at room temperature for 2 hours. Thereafter, 2.9g (26.4mmol) of TMS-Cl was slowly added thereto and stirred at room temperature for 12 hours. After the reaction is completed, the solvent is removed therefrom, and it is subjected to an extraction process by using hexane. The extracted organic layer was dried over sodium sulfate, and the solvent was removed therefrom, whereby 5.7g (21.1mmol) of intermediate [1-B ] was obtained.

Synthesis of intermediate [1-C ]

5.7g (21.1mmol) of intermediate [1-B ] and 4.0g (22.0mmol) of bis (dimethylamino) dichlorodiborane were suspended in 70mL of dichloromethane and stirred at room temperature for 1 hour. Thereafter, 5.0g (21.1mmol) of trimethylsilyl trifluoromethanesulfonate was added thereto, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was removed therefrom to obtain 8.7g (19.2mmol) of intermediate [1-C ].

Synthesis of Compound 1

8.7g (19.2mmol) of intermediate [1-C ]]And 2.2g (9.6mmol) of silver (I) oxide were suspended in 500mL of dioxane and stirred at room temperature for 24 hours. Thereafter, 5.7g (19.2mmol) of1,5-Cyclooctadieneplatinum dichloride, the temperature was raised and the mixture was stirred at 120 ℃ for 24 hours. Thereafter, the solvent was completely removed therefrom, 15.4g (153.6mmol) of 2, 4-pentanedione and 17.2g (153.6mmol) of potassium tert-butoxide were added thereto, suspended in 500mL of DMF, and stirred at room temperature for 24 hours. Thereafter, the temperature was raised to 100 ℃, and the mixture was stirred for 24 hours. After the completion of the reaction, the reaction resultant was cooled at room temperature, 500mL of distilled water was added thereto, and subjected to an extraction process by using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue from which the solvent had been removed was separated by using column chromatography, thereby obtaining 480mg (0.8mmol) of compound 1.

Synthesis example 2: synthesis of Compound 4

470mg (0.7mmol) of Compound 4 was obtained in the same manner as in Synthesis example 1, except that N1, N1-dimethylbenzene-1, 4-diamine was used in place of aniline.

Synthesis example 3: synthesis of Compound 6

610mg (0.9mmol) of Compound 6 was obtained in the same manner as in Synthesis example 1, except that 2,2,6, 6-tetramethylheptane-3, 5-dione was used in place of 2, 4-pentanedione.

Synthesis example 4: synthesis of Compound 11

430mg (0.7mmol) of Compound 11 was obtained in the same manner as in Synthesis example 1, except that ((CD) was used₃)₂NBCl)₂In place of bis (dimethylamino) dichlorodiborane (Me)₂NBCl)₂。

Synthesis example 5: synthesis of Compound 16

630mg (1.0mmol) of compound 16 was obtained in the same manner as in Synthesis example 1, except that methylaniline was used instead of aniline.

Synthesis example 6: synthesis of Compound 33

450mg (0.6mmol) of compound 33 was obtained in the same manner as in Synthesis example 1, except that 4- (pyridin-4-yl) aniline was used in place of aniline.

By passing¹The synthesized compounds were identified by H NMR and MS/FAB, and the results are shown in Table 1 below. The synthesis of compounds other than those shown in table 1 can be readily identified by those skilled in the art by reference to the synthetic routes and starting materials described above.

[ Table 1]

Example 1

As an anode, 15. omega./cm obtained from Corning Corp² The ITO glass substrate was cut into a size of 50mm × 50mm × 0.7mm, cleaned by ultrasonic treatment using isopropyl alcohol and pure water for 5 minutes, respectively, and by irradiating ultraviolet rays and exposing them to ozone for 30 minutes. The resulting glass substrate was loaded on a vacuum deposition apparatus.

Reacting 4,4' -tri [ 2-naphthyl (phenyl) amino]Triphenylamine (2-TNATA) was vacuum deposited on an ITO anode formed on a glass substrate to a thickness ofAnd 4,4' -bis [ N- (1-naphthyl) -N-phenylaminobiphenyl](NPB) vacuum-depositing on the hole-injecting layer to a thickness ofThe hole transport layer of (1).

A mixed host in which bis (4- (9H-carbazol-9-yl) phenyl) diphenylsilane (BCPDS) and 4- (1- (4- (diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-Phosphine Oxide (POPCPA) were mixed in a weight ratio of 1:1 and dopant compound 1 were co-deposited in a weight ratio of 90:10 on the hole transport layer to form a layer having a thickness of 90:10The emission layer of (1).

Subsequently, TSPO1 is deposited on the emissive layer to form a thickness ofThe hole-blocking layer of (a) is,and reacting Alq₃Is deposited on the hole blocking layer to a thickness ofThe electron transport layer of (1).

Depositing LiF on the electron transport layer to a thickness ofVacuum depositing Al on the electron injection layer to form a thickness ofAnd HT28 is vacuum deposited on the cathode to a thickness of Thereby completing the fabrication of the light emitting device.

Examples 2 to 6 and comparative examples 1 and 2

Light-emitting devices were manufactured in the same manner as in example 1, except that in forming the emission layers, compounds shown in table 2 were each used in place of compound 1.

Evaluation example 1

In order to evaluate the characteristics of the light emitting devices manufactured in examples 1 to 6 and comparative examples 1 and 2, the voltage at 50mA/cm was measured²The driving voltage, luminance, and luminous efficiency of the light emitting devices manufactured in examples 1 to 6 and comparative examples 1 and 2 at the current density of (a). The driving voltage of the light emitting device was measured by using a source meter (Keithley Instruments, 2400 series). Table 2 below shows the evaluation results of the characteristics of the light emitting device.

[ Table 2]

It is confirmed from table 2 that the light emitting devices of examples 1 to 6 have excellent driving voltage, excellent luminance, and excellent light emitting efficiency, compared to the light emitting devices of comparative examples 1 and 2.

The organometallic compound can be used for manufacturing a light-emitting device having excellent color purity and long life, and the light-emitting device can be used for manufacturing a high-quality electronic apparatus having excellent color purity and long life.

It is to be understood that the embodiments described herein are to be considered merely as illustrative and not for purposes of limitation. Descriptions of features or aspects in each embodiment should generally be considered as available for other similar features or aspects in other embodiments. Although the embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope defined by the appended claims.

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Organometallic compound, light-emitting device, and electronic apparatus including light-emitting device

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