KR102595917B1 - Heterocyclic compound and electronic apparatus comprising the same - Google Patents

Abstract

Heterocyclic compounds and electronic devices containing them are disclosed.

Description

Heterocyclic compounds and electronic devices containing them {HETEROCYCLIC COMPOUND AND ELECTRONIC APPARATUS COMPRISING THE SAME}

It relates to heterocyclic compounds and electronic devices containing them.

An electronic device including an organic light emitting device includes an organic light emitting device including a hole injection electrode, an electron injection electrode, and an organic light emitting layer formed between them. Organic light emitting devices are self-emitting devices, and compared to conventional devices, they not only have a wide viewing angle and excellent contrast, but also have a fast response time and excellent brightness, driving voltage, and response speed characteristics. For example, in an organic light emitting display device, which is a type of electronic device including an organic light emitting device, an exciton generated by combining holes injected from a hole injection electrode and electrons injected from an electron injection electrode in an organic light emitting layer is in an excited state ( It is a self-luminous display device that generates light by falling from an excited state to a ground state.

Organic light emitting display devices, which are self-emitting display devices, do not require a separate light source, so they can be driven at low voltage and can be configured in a lightweight and thin form. They have excellent viewing angle, contrast, response speed, etc., so they can be used as MP3 players. The scope of application is expanding from personal portable devices such as mobile phones and mobile phones to televisions.

Meanwhile, as outdoor use of information devices such as electronic devices including organic light-emitting devices increases, the time that electronic devices including organic light-emitting devices are exposed to sunlight is gradually increasing. Additionally, in the process of manufacturing organic light emitting devices, there are many cases where irradiation of ultraviolet rays is required. In this way, if external ultraviolet rays freely penetrate into the interior of the organic light-emitting device, the light-emitting layer containing organic materials may be seriously damaged.

Electronic devices such as organic light-emitting displays may suffer serious damage, especially to the light-emitting layer and insulating film containing organic materials, if ultraviolet rays enter from the outside of the device or enter the device during the manufacturing process and penetrate into the inside of the device. .

The present invention is intended to solve various problems including the problems described above, and aims to provide an electronic device that can reduce the amount of ultraviolet rays transmitted into the electronic device. However, these tasks are illustrative and do not limit the scope of the present invention.

According to one aspect,

Heterocyclic compounds are provided, represented by Formula 1:

<Formula 1>

In Formula 1,

L ₁ is a (m1+m2) C ₂ -C ₂₀ organic group connecting A ₁ and A ₂ ,

A ₁ is a UV-absorbing group,

A ₂ is a radical-scavenging group,

m1 is an integer from 1 to 3,

m2 is an integer from 1 to 3.

According to another aspect, a substrate; an organic light emitting device on the substrate; and a thin film encapsulation part that seals the organic light emitting device, wherein the thin film encapsulation part includes the heterocyclic compound.

Electronic devices containing the heterocyclic compound can have a long lifespan by preventing damage to the light-emitting layer and insulating film containing organic materials by ultraviolet rays.

1 and 2 are cross-sectional views schematically showing an organic light emitting display device as an example of an electronic device according to an embodiment of the present invention.
Figure 3 shows the transmittance according to exposure time of the thin film encapsulation portion of the electronic device of Example 1 and the electronic device of Comparative Examples 1 and 2, which are electronic devices according to an embodiment.

Since the present invention can be modified in various ways and can have various embodiments, specific embodiments will be illustrated in the drawings and described in detail in the detailed description. The effects and features of the present invention and methods for achieving them will become clear by referring to the embodiments described in detail below along with the drawings. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various forms.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. When describing with reference to the drawings, identical or corresponding components will be assigned the same reference numerals and redundant description thereof will be omitted. .

In the following embodiments, when various components such as layers, films, regions, and plates are said to be “on” other components, this does not only mean that they are “directly on” the other components, but also when other components are interposed between them. Also includes cases where Additionally, for convenience of explanation, the sizes of components may be exaggerated or reduced in the drawings. For example, the size and thickness of each component shown in the drawings are shown arbitrarily for convenience of explanation, so the present invention is not necessarily limited to what is shown.

In the following embodiments, terms such as first and second are used only for the purpose of distinguishing one component from another component.

In the following embodiments, the x-axis, y-axis, and z-axis are not limited to the three axes in the Cartesian coordinate system, but can be interpreted in a broad sense including these. For example, the x-axis, y-axis, and z-axis may be orthogonal to each other, but may also refer to different directions that are not orthogonal to each other.

[Heterocyclic compounds]

The heterocyclic compound is represented by the following formula (1):

<Formula 1>

In Formula 1, L ₁ is a C ₂ -C ₂₀ organic group with a valence of (m1+m2) connecting A ₁ and A ₂ .

According to one embodiment, L ₁ may be a group represented by Formula 2 below:

<Formula 2>

X _{1 and} ego,

L ₁₁ is a C ₂ -C ₁₂ alkylene group, a C ₂ -C ₁₂ alkenylene group, and a C ₂ -C ₁₂ alkynylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , C ₃ -C ₂₀ Cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, N(Q ₃₁ )(Q ₃₂ ) and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), a C ₂ -C ₁₂ alkylene group, a C ₂ -C ₁₂ alkenylene group, and a C ₂ -C ₁₂ alkynylene group substituted with at least one substituent selected from;

is selected from,

n1 and n2 are independently integers of 1 to 3,

Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group selected from the group, biphenyl group and terphenyl group,

* and *' are binding sites with neighboring atoms.

In this specification, -NHC(=O)NH- represents the following structure:

In the above structure, * and *' are each bonding sites with neighboring atoms.

According to one embodiment, L ₁ may be a group represented by any one of the following formulas 2-1 to 2-5:

<Formula 2-1>

<Formula 2-2>

<Formula 2-3>

<Formula 2-4>

<Formula 2-5>

In formulas 2-1 to 2-5,

For a description of L ₁₁ , refer to the description provided herein,

* and *' are binding sites with neighboring atoms.

According to one embodiment, L ₁₁ is ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene ( nonylene group, decanylene group, undecylene group and dodecylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group. ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decanylene group, undecylene group and dodecylene group, substituted with at least one substituent selected from among;

can be selected from among.

In Formula 1, A ₁ is a UV-absorbing group.

According to one embodiment, A ₁ is a hydroxy benzophenone-containing group, a benzoquinone-containing group, an anthraquinone-containing group, a xanthone-containing group, benzotriazine. (benzotriazine)-containing group, benzotriazinone-containing group, benzotriazole-containing group, benzoate-containing group, cyanoacrylate-containing group, triazine ( It may include one or more selected from a triazine-containing group, an oxanilide-containing group, a salicylate-containing group, and a pyrene-containing group.

The benzophenone-containing group is, for example, 2-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octylbenzophenone , 4-dodecyloxy-2-hydroxybenzophenone, 4-benzyloxy-2-hydroxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2,2'-dihydroxy -4,4'-dimethoxybenzophenone, etc. may be included.

The benzoquinone-containing group may include, for example, 2-hydroxybenzoquinone.

The anthraquinone-containing group may include, for example, 1-hydroxyanthraquinone, 1,5-hydroxyanthraquinone, 1,8-hydroxyanthraquinone, etc.

The benzotriazole-containing group is, for example, 2-(2-hydroxyphenyl)benzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy- 3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)benzotriazole, 2-(3- t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2 It may include -(3,5-di-t-acyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, etc.

The benzoate-containing group includes, for example, phenyl 2-hydroxybenzoate, 2,4-di-t-butylphenyl-3',5'-di-t-butyl-4-hydroxybenzoate, etc. It can be included.

The triazine-containing group is, for example, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenol, 2-(4,6-diphenyl-1,3, 5-triazin-2-yl)-5-(hexyl)oxy-phenol, 2-[4-[(2-hydroxy-3-dodecyloxypropyl)oxy]-2-hydroxyphenyl]-4, It may include 6-bis(2,4-dimethylphenyl)-1,3,5-triazine, etc.

The salicylate-containing group may include, for example, phenyl salicylate, 4-t-butylphenyl salicylate, etc.

According to one embodiment, A ₁ may be a group represented by any one of the following formulas 3-1 to 3-3:

<Formula 3-1>

<Formula 3-2>

<Formula 3-3>

In formulas 3-1 to 3-3,

CY ₁ and CY ₂ are independently selected from a benzene group, a naphthalene group, an anthracene group, a pyrene group and a phenanthrene group,

R ₁ and R ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or Unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed Polycyclic group, Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ), or

R ₁ and R ₂ are optionally connected to each other to form a -(Y ₁ ) _k1 - linking group,

Y ₁ is -O-, -S-, or -C(=O)-,

k1 is an integer from 1 to 3,

One of Y ₂ and Y ₃ is N, and the other is a single bond, double bond, or -C(=O)-,

R ₁₀ , R ₂₀ , R ₃₀ and R ₄₀ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, Hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ - C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloc Group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted 1 is a non-aromatic heterocondensed polycyclic group, Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O )(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

a10 is an integer from 1 to 7,

a20 is an integer from 1 to 3,

a30 and a40 are independently integers of 1 to 4,

At least one R ₁₀ , at least one R ₂₀ and at least one R ₃₀ are hydroxyl groups,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₆₀ cycloalkoxy group , substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ - C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substitution At least one of the substituents of the monovalent non-aromatic condensed heteropolycyclic group is,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalke Nyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent ratio -aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), substituted with at least one selected from C ₃ - C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from,

Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group , C ₆ -C ₆₀ aryl group substituted with a C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group, terphenyl group, C ₁ -C ₆₀ heteroaryl group, C ₁ - C ₁ -C ₆₀ heteroaryl group substituted with C ₆₀ alkyl group, C ₁ -C ₆₀ heteroaryl group substituted with C ₆ -C ₆₀ aryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group selected from the group, biphenyl group and terphenyl group,

* is a bonding site with a neighboring atom.

According to one embodiment, in Formulas 3-1 to 3-3, R ₁ and R ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group , C ₁ -C ₂₀ alkoxy group, C ₃ -C ₂₀ cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluore. Nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, furanyl group, benzofuranyl group, dibenzofuranyl group, C ₁ -C 20 alkyl group and C 1 -C ₂₀ substituted with at least one of thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and _{triazinyl group} . Alkoxy group;

is selected from, or

R ₁ and R ₂ are connected to each other to form a -(Y ₁ ) _k1 - linking group,

-(Y ₁ ) _k1 - may be -O-, -S-, or -C(=O)-.

For example, R ₁ and R ₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydra is selected from a zono group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group,

R ₁ and R ₂ are connected to each other to form a -(Y ₁ ) _k1 - linking group,

-(Y ₁ ) _k1 - may be -O-, -S-, or -C(=O)-.

According to one embodiment, in Formulas 3-1 to 3-3, R ₁₀ , R ₂₀ , R ₃₀ and R ₄₀ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydrogen roxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group , C ₁ -C ₂₀ alkoxy group, C ₃ -C ₂₀ cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluore. Nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, furanyl group, benzofuranyl group, dibenzofuranyl group, C ₁ -C 20 alkyl group and C 1 -C ₂₀ substituted with at least one of thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and _{triazinyl group} . Alkoxy group;

can be selected from among.

For example, R ₁₀ , R ₂₀ , R ₃₀ and R ₄₀ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group. , hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group , C ₁ -C ₂₀ alkoxy group, C ₃ -C ₂₀ cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluore. Nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, furanyl group, benzofuranyl group, dibenzofuranyl group, C ₁ -C 20 alkyl group and C 1 -C ₂₀ substituted with at least one of thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and _{triazinyl group} . Alkoxy group;

can be selected from among.

According to one embodiment, A ₁ may be a group represented by any one of the following formulas 4-1 to 4-30:

In formulas 4-1 to 4-30,

For a description of R ₃ , R ₄ , R ₁₁ to R ₁₈ , refer to the description of R ₁₀ above,

a16 is 1, 2, 3 or 4,

b16 is 1 or 2,

b17 is 1, 2, 3, or 4,

c15 is 1 or 2,

c16 is 1, 2 or 3,

c17 is 1 or 2,

For a description of R ₂₁ to R ₂₃ , refer to the description of R ₂₀ above,

For a description of R ₃₁ to R ₃₅ , refer to the description of R ₃₀ above,

For a description of R ₄₁ to R ₄₄ , refer to the description of R ₄₀ above,

At least one of R ₁₁ to R ₁₈ , at least one of R ₂₁ to R ₂₃ and at least one of R ₃₁ to R ₃₅ are hydroxyl groups,

* is a bonding site with a neighboring atom.

According to one embodiment, in Formulas 4-1 to 4-26, at least one of R ₁₁ , R ₁₅ and R ₁₈ may be a hydroxyl group. For example, R ₁₁ may be a hydroxyl group, but the present invention is not limited thereto.

According to another embodiment, R ₂₁ in Formula 4-27 may be a hydroxyl group.

According to another embodiment, at least one of R ₃₁ and R ₃₅ in Formulas 4-28 to 4-30 may be a hydroxyl group. For example, R ₃₁ may be a hydroxyl group, but is not limited thereto.

According to one embodiment, A ₁ may be a group represented by the following formula 5-1 or 5-2:

In formulas 5-1 and 5-2,

For descriptions of R ₁₄ , R ₁₅ and R ₁₆ , refer to the description of R ₁₀ above,

* is a bonding site with a neighboring atom.

In Formula 1, A ₂ is a radical-scavenging group.

According to one embodiment, the A ₂ may include at least one selected from a phenol-containing group, a hindered amine-containing compound, and a phenylenediamine-containing group.

The phenol-containing compounds include butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), tert-Butylhydroquinone (TBHQ), and propyl gallate ( It may be propyl gallate (PG), catechol (1,2-benzenediol), 1,2-naphthalenediol (1,2-naphthalenediol), etc.

The hindered amine-containing compound is bis-(2,2,6,6-tetramethyl-4-piperidyl)seba

Cate, bis-(N-methyl-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis-(1,2,2,6,6-pentamethyl-4-piperidyl) ) Sebacate, 1,2,2,6,6-pentamethyl-4-piperidyl-tridecyl-1,2,3,4-butanetetracarboxylate, tetrakis-(2,2,6, 6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, and tetrakis-(N-methyl-2,2,6,6-tetramethyl-4-piperi) It may be dil)-1,2,3,4-butane tetracarboxylate, etc.

The phenylenediamine-containing compound may be o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, etc., or may contain deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group. , nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₂₀ alkoxy group, o-phenylenediamine, m -It may be phenylenediamine, p-phenylenediamine, etc.

According to one embodiment, A ₂ may be a group represented by any one of the following formulas 6-1 to 6-3:

<Formula 6-1>

<Formula 6-2>

<Formula 6-3>

In formulas 6-1 to 6-3,

Ar ₁ is a benzene ring or a naphthalene ring,

R ₅₀ , R ₆₀ , R ₆₁ and R ₇₀ to R ₇₄ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydra Zino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted Ringed monovalent non-aromatic heterocondensed polycyclic group, Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C (=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

a50 is an integer from 1 to 6,

a60 is an integer from 1 to 4,

a70 is an integer from 1 to 3,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₆₀ cycloalkoxy group , substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ - C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substitution At least one of the substituents of the monovalent non-aromatic condensed heteropolycyclic group is,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalke Nyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent ratio -aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), substituted with at least one selected from C ₃ - C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from,

Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group , C ₆ -C ₆₀ aryl group substituted with a C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group, terphenyl group, C ₁ -C ₆₀ heteroaryl group, C ₁ - C ₁ -C ₆₀ heteroaryl group substituted with C ₆₀ alkyl group, C ₁ -C ₆₀ heteroaryl group substituted with C ₆ -C ₆₀ aryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group selected from the group, biphenyl group and terphenyl group,

* is a bonding site with a neighboring atom.

According to one embodiment, R ₅₀ , R ₆₀ , R ₆₁ and R ₇₀ to R ₇₄ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group , C ₁ -C ₂₀ alkoxy group, C ₃ -C ₂₀ cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluore. Nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, furanyl group, benzofuranyl group, dibenzofuranyl group, C ₁ -C 20 alkyl group and C 1 -C ₂₀ substituted with at least one of thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and _{triazinyl group} . Alkoxy group;

can be selected from among.

According to one embodiment, R ₅₀ , R ₆₀ , R ₆₁ and R ₇₀ to R ₇₄ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group , C ₁ -C ₂₀ alkoxy group, C ₃ -C ₂₀ cycloalkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluore. Nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, furanyl group, benzofuranyl group, dibenzofuranyl group, C ₁ -C 20 alkyl group and C 1 -C ₂₀ substituted with at least one of thiophenyl group, benzothiophenyl group, dibenzothiophenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and _{triazinyl group} . Alkoxy group;

can be selected from among.

According to one embodiment, A ₂ may be a group represented by any one of the following formulas 7-1 to 7-3:

In formulas 7-1 to 7-3,

For descriptions of R ₅₁ , R ₅₂ and R ₅₃ , refer to the description of R ₅₀ above,

For descriptions of R ₆₁ to R ₆₆ , refer to the description of R ₆₀ above,

For a description of R ₇₁ to R ₇₄ , refer to the description of R ₇₁ to R ₇₄ above,

For descriptions of R ₇₅ and R ₇₆ , refer to the description of R ₇₀ above,

* is a bonding site with a neighboring atom.

According to one embodiment, A ₂ may be a group selected from the following formulas 8-1 to 8-12:

In formulas 8-1 to 8-12,

For descriptions of R ₆₁ , R ₇₅ and R ₇₆ , refer to the descriptions of R ₆₁ , R ₇₅ and R ₇₆ above,

* is a bonding site with a neighboring atom.

In Formula 1, m1 is an integer from 1 to 3, and m2 is an integer from 1 to 3.

According to one embodiment, in Formula 1, m1 may be 1 and m2 may be 1.

According to one embodiment, the heterocyclic compound may be selected from the following compounds 1 to 14:

Among the compounds 1 to 14,

R ₈₁ to R ₈₃ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group.

According to one embodiment, a composition for forming a thin film encapsulation unit may include the heterocyclic compound.

The composition for forming the thin film encapsulation unit includes the heterocyclic compound and may further include a solvent.

The solvent is, for example, di(meth)acrylate (containing at least one selected from C ₁₀ -C ₂₀ alkyl group, C ₁₀ -C ₂₀ alkyl group, C ₁₀ -C ₂₀ alkenyl group and C ₁₀ -C ₂₀ alkynyl group) It may include di(meth)acrylate), di(meth)acryl-terminated silicon, and diepoxy-terminated silicon. In addition, the solvent may further include mono(meth)acrylate, monoepoxy, etc. as a diluent.

For another example, the solvent may have a visible light transmittance of 70% or more.

The solvent may have a viscosity of 5 to 10000 cP.

The composition for forming the thin film encapsulation may further include a photoinitiator or a thermal initiator. The photoinitiator or thermal initiator known in the art may be used without particular limitation. According to one embodiment, the composition for forming the thin film encapsulation part may include two or more types of heterocyclic compounds.

For example, the thin film encapsulation unit includes a first heterocyclic compound represented by Formula 1 and a second heterocyclic compound represented by Formula 1, and the wavelength range of light absorbed by the first heterocyclic compound is The wavelength of light absorbed by the second heterocyclic compound may be different.

According to one embodiment, when the composition for forming the thin film encapsulation includes two or more of the heterocyclic compounds, the thin film encapsulation formed using the composition for forming the thin film encapsulation has a wavelength range of 380 nm to 400 nm. The average transmittance may be 10% or less, and the average transmittance in the wavelength range of 400 nm to 430 nm may be 60% or more.

According to one embodiment, a monomer for forming the matrix resin, a photopolymerization initiator, a solvent, etc. may be further included.

For example, the composition for forming the thin film encapsulation part may further include a monomer for forming a matrix resin. The monomer for forming the matrix resin is one or more of acrylic resin, methacrylic resin, isoprene-based resin, vinyl-based resin, epoxy-based resin, urethane-based resin, cellulose-based resin, perylene-based resin, imide-based resin, and silicone-based resin. It may be a monomer for

According to one embodiment, the monomer for forming the matrix resin may be a (meth)acrylic monomer.

For another example, the composition for forming the thin film encapsulation part may further include a photopolymerization initiator. The photopolymerization initiator may be one known in the art without particular limitation, and for example, one capable of curing at a wavelength of 360 to 420 nm may be used.

According to one embodiment, the composition for forming the thin film encapsulation part may further include two or more types of photopolymerization initiators. For example, among the two or more types of photopolymerization initiators, one type is capable of curing in the UV region (for example, a wavelength of 360 to 420 nm), and the other type is capable of curing in the visible light region (for example, a wavelength of 400 to 770 nm) It may be possible to cure at a wavelength of . According to another example, all of the two or more types of photopolymerization initiators may be capable of curing in the UV region, or all of the two or more types of photopolymerization initiators may be capable of curing in the visible light region.

According to one embodiment, the composition for forming the thin film encapsulation part may further include a monomer for forming a matrix resin and a photopolymerization initiator.

The monomer for forming the matrix resin can form the matrix resin included in the thin film encapsulation portion through photopolymerization. For example, the monomer for forming the matrix resin can be photopolymerized using a photopolymerization initiator to form the matrix resin included in the thin film encapsulation part. For a description of the photopolymerization initiator, refer to what is described herein.

[Electronic Device]

According to another aspect of the present invention,

Board;

an organic light emitting device on the substrate; and

It includes a thin film encapsulation part that seals the organic light emitting device,

An electronic device is provided wherein the thin film encapsulation part includes the heterocyclic compound.

For example, the electronic device may include a substrate; an organic light emitting device included within a pixel crystal region on the substrate; and a thin film encapsulation part that seals the organic light emitting device, wherein the thin film encapsulation part includes the heterocyclic compound.

Hereinafter, among electronic devices containing the heterocyclic compound in the thin film encapsulation portion, an organic light emitting display device will be described as an example. However, embodiments of the present invention are not limited to organic light emitting display devices.

1 is a schematic cross-sectional view of an organic light emitting display device according to an embodiment of the present invention.

Referring to FIG. 1 , an organic light emitting display device 10 according to an embodiment of the present invention includes a substrate 100, an organic light emitting element 200, and a thin film encapsulation unit 300.

The substrate 100 may be a substrate commonly used in an organic light emitting display device, and may be an inorganic or organic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

For example, the substrate may be an inorganic substrate made of transparent glass containing SiO ₂ as a main component, but is not limited thereto.

For another example, the substrate may be an organic substrate with insulating properties. Organic materials having the above insulating properties include, for example, polyethersulphone (PES), polyacrylate (PAR), polyetherimide (PEI), polyethylene naphthalate (PEN), and polyethylene. Polyethyeleneterepthalate (PET), polyphenylene sulfide (PPS), polyallylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), and cellulose acetate propionate. (cellulose acetate propionate: CAP), but is not limited thereto.

An organic light emitting device 200 is disposed on the substrate 100. The organic light emitting device 200 may include a first electrode, an intermediate layer including a light emitting layer, and a second electrode.

The first electrode may be formed, for example, by providing a first electrode material on the top of the substrate using a deposition method or sputtering method. When the first electrode is an anode, the material for the first electrode may be selected from materials with a high work function to facilitate hole injection.

The first electrode may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode, which is a transmissive electrode, the material for the first electrode is selected from among indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and any combination thereof. It may be selected, but is not limited to this. Alternatively, to form a first electrode that is a transflective electrode or a reflective electrode, the material for the first electrode may be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), or calcium. (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but is not limited thereto.

The first electrode may have a single-layer structure or a multi-layer structure having a plurality of layers. For example, the first electrode may have a three-layer structure of ITO/Ag/ITO, but is not limited to this.

An intermediate layer including a light-emitting layer may be disposed on top of the first electrode.

The intermediate layer may further include a hole transport region between the first electrode and the light-emitting layer and an electron transport region between the light-emitting layer and the second electrode. It is not limited.

A second electrode is disposed on the upper part of the intermediate layer. The second electrode may be a cathode, which is an electron injection electrode. In this case, the material for the second electrode may be a metal, alloy, electrically conductive compound, or a combination thereof having a low work function. there is.

The second electrode is lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium -It may include at least one selected from (Mg-Ag), ITO, and IZO, but is not limited thereto. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode may have a single-layer structure or a multi-layer structure having a plurality of layers.

A thin film encapsulation part 300 is disposed on the organic light emitting device 200.

The thin film encapsulation unit 300 includes the heterocyclic compound. For a description of the heterocyclic compounds, refer to what is described herein.

According to one embodiment, the thin film encapsulation part 300 may include two or more types of heterocyclic compounds.

For example, the thin film encapsulation unit includes a first heterocyclic compound represented by Formula 1 and a second heterocyclic compound represented by Formula 1, and the wavelength range of light absorbed by the first heterocyclic compound is The wavelength of light absorbed by the second heterocyclic compound may be different.

According to one embodiment, when the thin film encapsulation part includes two or more of the heterocyclic compounds, the average transmittance is 10% or less in the wavelength range of 380 nm to 400 nm, and the average transmittance is 10% or less in the wavelength range of 400 nm to 430 nm. The average transmittance may be 60% or more.

The heterocyclic compound can absorb ultraviolet rays and prevent the ultraviolet rays from penetrating into the organic light emitting device 200. Accordingly, the organic light emitting display device 10 including the heterocyclic compound in the thin film encapsulation portion 300 can prevent the light emitting layer and insulating film containing organic materials from being damaged by ultraviolet rays.

According to one embodiment, the thin film encapsulation part 300 further includes a matrix resin, and the heterocyclic compound may be dispersed in the matrix resin. At this time, the heterocyclic compound may be simply dispersed in the matrix resin. Alternatively, the heterocyclic compound may be cross-linked with the matrix resin. For example, the heterocyclic compound may include the polymerizable functional group, and the heterocyclic compound may be cross-linked with the matrix resin.

According to one embodiment, the thin film encapsulation part 300 may further include a photopolymerization initiator. For a description of the photopolymerization initiator, refer to the contents described in this specification.

According to one embodiment, the thin film encapsulation part 300 may further include metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride.

For example, the thin film encapsulation part 300 may be formed of MgF ₂ , LiF, AlF ₃ , NaF, silicon oxide, silicon nitride, silicon oxynitride, aluminum oxide, aluminum nitride, aluminum oxynitride, titanium oxide, titanium nitride, and tantalum oxide. , tantalum nitride, hafnium oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, tin oxide, tin nitride, and magnesium oxide, but is not limited thereto.

According to one embodiment, the thin film encapsulation part 300 includes at least one organic layer, the at least one organic layer includes a first organic layer, and the heterocyclic compound is included in the first organic layer. You can.

According to one embodiment, the thin film encapsulation part (e.g., first organic layer) containing the heterocyclic compound is 10% or less (10% or less) with respect to light having a wavelength of 400 nm to 410 nm (e.g., 405 nm). For example, it may have a transmittance of 8% or less.

According to another embodiment, the thin film encapsulation part (e.g., first organic layer) containing the heterocyclic compound has a transmittance of 80% or more (e.g., 90% or more) for light with a wavelength of 430 nm or more. and may have a transmittance of 10% or less for light with a wavelength of 405 nm or less.

According to one embodiment, the first organic layer may have a transmittance change of less than 5% in the wavelength range of 400 nm to 410 nm when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ² . .

According to another embodiment, the first organic layer may have a transmittance change of less than 3% in the wavelength range of 400 nm to 405 nm when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ² . .

According to another embodiment, the first organic layer has a transmittance change of less than 1% in the wavelength range of 400 nm to 405 nm when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ² . You can.

According to another embodiment, the first organic layer has a wavelength range of 380 nm to 410 nm and a wavelength range of 400 nm to 410 nm when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ^2. The change in transmittance may be less than 5%.

According to another embodiment, the first organic layer has a wavelength range of 380 nm to 410 nm, and when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ² , the first organic layer has a wavelength range of 400 nm to 405 nm. The change in transmittance over the wavelength range may be less than 3%.

According to another embodiment, the first organic layer has a wavelength range of 380 nm to 410 nm and a wavelength range of 400 nm to 405 nm when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ^2. The change in transmittance may be less than 1%.

The change in transmittance in the wavelength range can be measured, for example, by exposing the first organic layer to an LED lamp that emits light with a wavelength range of 380 nm to 410 nm and a maximum emission wavelength of 405 nm.

According to one embodiment, the thickness of the first organic layer may be 10 nm to 20 μm, for example, 10 nm to 10 μm.

According to one embodiment, the content of the heterocyclic compound may be 3 to 10 parts by weight per 100 parts by weight of the first organic layer. By controlling the content of the heterocyclic compound in the first organic layer, the maximum absorption wavelength of the first organic layer can be finely adjusted and the UV absorption spectrum can be controlled.

For example, the at least one organic layer may be made of the heterocyclic compound.

For another example, the at least one organic layer may further include the matrix resin in addition to the heterocyclic compound, and the heterocyclic compound may be dispersed in the matrix resin. At this time, the heterocyclic compound may be simply dispersed in the matrix resin, or the heterocyclic compound may be cross-linked with the matrix resin.

According to one embodiment, the first organic layer further includes a matrix resin,

The matrix resin may include one or more of acrylic resin, methacrylic resin, isoprene-based resin, vinyl-based resin, epoxy-based resin, urethane-based resin, cellulose-based resin, perylene-based resin, imide-based resin, and silicone-based resin.

For another example, the at least one organic layer may further include a photopolymerization initiator in addition to the heterocyclic compound. For a description of the photopolymerization initiator, refer to what is described herein.

For another example, the at least one organic layer may further include the matrix resin and the photopolymerization initiator in addition to the heterocyclic compound.

The at least one organic layer is formed using various methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). , can be formed in a predetermined area. The number and thickness of the organic layers may be appropriately selected in consideration of productivity or device characteristics.

According to one embodiment, the thin film encapsulation part may further include at least one inorganic layer, and the at least one inorganic layer may include a first inorganic layer.

According to one embodiment, the inorganic layer may include metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride.

For example, the inorganic film may be MgF ₂ , LiF, AlF ₃ , NaF, silicon oxide, silicon nitride, silicon oxynitride, aluminum oxide, aluminum nitride, aluminum oxynitride, titanium oxide, titanium nitride, tantalum oxide, tantalum nitride, hafnium. It may include, but is not limited to, at least one of oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, tin oxide, tin nitride, and magnesium oxide.

The at least one inorganic film is applied to a predetermined area using various methods such as chemical vapor deposition (CVD), plasma chemical vapor deposition (PECVD), sputtering, atomic layer deposition (ALD), thermal evaporation, etc. can be formed. The number and thickness of the inorganic films may be appropriately selected in consideration of productivity or device characteristics.

According to one embodiment, the at least one organic layer includes a first organic layer, the at least one inorganic layer includes a first inorganic layer, and the first organic layer is connected to the organic light emitting device 200 and the first inorganic layer. There may be something in between. For example, the at least one organic layer includes a first organic layer, the at least one inorganic layer includes a first inorganic layer, and the first organic layer and the second inorganic layer are sequential from the organic light emitting device 200. It may be stacked as is. Here, saying that they are sequentially stacked does not exclude that another film is interposed between the organic light-emitting device 200 and the first organic film, and/or between the first organic film and the first inorganic film. It must be understood.

According to another embodiment, the at least one organic layer includes a first organic layer, the at least one inorganic layer includes a first inorganic layer, and the first inorganic layer is connected to the organic light emitting device 200 and the first organic layer. There may be something in between. For example, the at least one organic layer includes a first organic layer, the at least one inorganic layer includes a first inorganic layer, and the first inorganic layer and the first organic layer are sequential from the organic light emitting device 200. It may be stacked as is.

According to another embodiment, the at least one organic layer includes a first organic layer, the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the first inorganic layer is emitted from the organic light emitting device 200. A film, the first organic film, and the second inorganic film may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, the at least one inorganic layer includes a first inorganic layer, and the first organic layer is emitted from the organic light emitting device 200. The film, the first inorganic film, and the second organic film may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the organic light emitting device 200 The first inorganic layer, the first organic layer, the second inorganic layer, and the second organic layer may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the organic light emitting device 200 The first organic layer, the first inorganic layer, the second organic layer, and the second inorganic layer may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the organic light emitting device 200 The first inorganic layer, the second inorganic layer, the first organic layer, and the second organic layer may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the organic light emitting device 200 The first organic layer, the second organic layer, the first inorganic layer, and the second inorganic layer may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer and a second organic layer, and the at least one inorganic layer includes a first inorganic layer, a second inorganic layer, and a third inorganic layer, and the organic layer In the light emitting device 200, the first inorganic layer, the first organic layer, the second inorganic layer, the second organic layer, and the third inorganic layer may be sequentially stacked.

According to another embodiment, the at least one organic layer includes a first organic layer, a second organic layer, and a third organic layer, and the at least one inorganic layer includes a first inorganic layer and a second inorganic layer, and the organic layer includes a first organic layer and a third organic layer. From the light emitting device 200, the first organic film, the first inorganic film, the second organic film, the second inorganic film, and the third organic film may be sequentially stacked, but are not limited to this, and the organic film and the inorganic film are not limited thereto. Not only the number, but also the stacking order of the inorganic and organic films can be appropriately modified depending on the design.

The organic light emitting display device 10 may include a plurality of organic light emitting devices 200. Therefore, according to one embodiment, it includes a substrate, an organic light-emitting portion including a plurality of organic light-emitting devices 200 on the substrate, and a thin film encapsulation portion 300 for sealing the organic light-emitting portion on the organic light-emitting portion, wherein the thin film The encapsulation part 300 is provided with an organic light emitting display device 10 containing a heterocyclic compound. For a description of the heterocyclic compounds, see the description herein.

When the organic light emitting display device 10 includes a plurality of organic light emitting devices 200, each of the plurality of organic light emitting devices has a pixel crystal region, and may emit light in different sections according to wavelength bands.

For example, the thin film encapsulation unit 300 may include the heterocyclic compound and may further include a matrix resin in addition to the heterocyclic compound. For a description of the matrix resin, refer to what is described herein.

For another example, the thin film encapsulation part 300 may further include metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride in addition to the heterocyclic compound. .

For another example, the thin film encapsulation unit 300 may include at least one organic layer and at least one inorganic layer, and the at least one organic layer may include the UV absorber. For descriptions of the at least one organic layer and the at least one inorganic layer, refer to what is described herein.

According to another aspect of the present invention, forming an organic light emitting device on a substrate; and

It includes forming a thin film encapsulation portion that seals the organic light emitting device on the substrate,

The step of forming the thin film encapsulation includes providing and curing a composition for forming the thin film encapsulation to cover the organic light emitting device,

A method of manufacturing an electronic device is provided, wherein the composition for forming the thin film encapsulation includes the heterocyclic compound.

For descriptions of the thin film encapsulation part, the heterocyclic compound, and the composition for forming the thin film encapsulation part, refer to what is described in the present specification. When manufacturing an electronic device according to the above manufacturing method, damage that may occur when the organic light emitting device is continuously exposed to UV light is prevented by blocking external UV light from reaching the organic light emitting device, The durability of organic light emitting devices and electronic devices including them can be improved.

Figure 2 is a cross-sectional view schematically showing an organic light emitting display device as an example of an electronic device according to an embodiment of the present invention.

Referring to Figure 2, first, a backplane is formed. Here, the backplane refers to at least the substrate 100, a plurality of first electrodes 210R, 210G, and 210B formed on the substrate 100, and a central portion of each of the plurality of first electrodes 210R, 210G, and 210B. It can be understood that it includes a pixel definition film 180 formed to expose at least a portion including. At this time, the pixel definition film 180 may have a shape that protrudes (in the +z direction) beyond the plurality of first electrodes 210R, 210G, and 210B when the substrate 100 is centered.

The plurality of first electrodes 210R, 210G, and 210B can be understood as pixel electrodes. Among the pixel electrodes, the pixel electrode 210B can be understood as a first pixel electrode, the pixel electrode 210R can be understood as a second pixel electrode, and the pixel electrode 210G can be understood as a third pixel electrode. This is because the intermediate layers formed on the first to third pixel electrodes may be different. Hereinafter, for convenience, the terms pixel electrode 210R, pixel electrode 210G, and pixel electrode 210B will be used instead of the first pixel electrode, second pixel electrode, and third pixel electrode. For a description of the pixel electrode, refer to the description of the first electrode.

The pixel definition film 180 has an opening corresponding to each subpixel, that is, an opening that exposes the central portion of each of the pixel electrodes 210R, 210G, and 210B or the entire pixel electrodes 210R, 210G, and 210B, thereby forming a pixel It can play a role in defining . In addition, the pixel definition film 180 increases the distance between the ends of the pixel electrodes 210R, 210G, and 210B and the second electrode (not shown) on the top of the pixel electrodes 210R, 210G, and 210B. It can serve to prevent arcs, etc. from occurring at the ends of (210R, 210G, 210B).

Of course, the backplane may further include various other components as needed. For example, as shown in FIG. 2, a thin film transistor (TFT) or a capacitor (Cap) may be formed on the substrate 100. And a buffer layer 110 formed to prevent impurities from penetrating into the semiconductor layer of the thin film transistor (TFT), a gate insulating film 130 to insulate the semiconductor layer and the gate electrode of the thin film transistor (TFT), It may be provided with an interlayer insulating film 150 for insulating the source/drain electrodes and gate electrodes, a planarization film 170 that covers the thin film transistor (TFT) and has a substantially flat top surface, or other components.

After forming the backplane in this way, intermediate layers 220R, 220G, and 220B are formed. The middle layers 220R, 220G, and 220B may have a multi-layer structure including a light-emitting layer. In this case, unlike what is shown, some of the middle layers 220R, 220G, and 220B are approximately on the entire surface of the substrate 100. It may be a corresponding common layer, and other partial layers may be patterned layers patterned to correspond to the pixel electrodes 210R, 210G, and 210B.

After forming the middle layers 220R, 220G, and 220B, the second electrode 230 is formed on the middle layers 220R, 220G, and 220B.

After forming the second electrode 230, the organic light emitting elements 200 including the pixel electrodes 210R, 210G, 210B, intermediate layers 220R, 220G, 220B, and the second electrode 230 are exposed to the outside. A thin film encapsulation portion 300 is formed to protect from impurities such as oxygen or moisture.

The thin film encapsulation part 300 may extend to cover not only the top surface but also the side surface of the organic light emitting device 200 and may be formed to contact a portion of the substrate 100 . This can effectively prevent external oxygen and moisture from penetrating into the organic light emitting device 200.

The thin film encapsulation unit 300 includes a UV absorber represented by Formula 1 above.

[General definition of substituent]

As used herein, C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl group, ethyl group, propyl group, isobutyl group, and sec-butyl group. group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, etc. As used herein, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

As used herein, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, and butenyl group. etc. are included. As used herein, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

As used herein, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, propynyl group, etc. Included. As used herein, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group and ethoxy group. , isopropyloxy group, etc.

As used herein, C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclo Heptyl group, etc. are included. As used herein, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom. , Specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, etc. As used herein, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, C ₃ -C ₁₀ cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring but does not have aromaticity, and its specific details Examples include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, etc. As used herein, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, forming a ring. It has at least one double bond within it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, 2,3-dihydro Thiophenyl group, etc. are included. As used herein, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

As used herein, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It means a divalent group with . Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, etc. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be condensed with each other.

As used herein, the C ₁ -C ₆₀ heteroaryl group is a monovalent group containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms. means, and the C ₁ -C ₆₀ heteroarylene group is 2 which contains at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms. means group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, etc. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be condensed with each other.

As used herein, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group refers to -SA ₁₀₃ (where A 102 is the C 6 -C 60 aryl group). , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group).

As used herein, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring forming atom, and the entire molecule is non-aromatic. It means a monovalent group having (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclic group (non-aromatic condensed heteropolycyclic group) has two or more rings condensed with each other, and at least one selected from N, O, Si, P and S in addition to carbon as a ring forming atom. It refers to a monovalent group (for example, having 1 to 60 carbon atoms) that contains a heteroatom and the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

As used herein, the C ₅ -C ₆₀ carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms containing only carbon as a ring-forming atom. The C ₅ -C ₆₀ carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₅ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents connected to the C ₅ -C ₆₀ carbocyclic group, various modifications are possible, such as the C ₅ -C ₆₀ carbocyclic group being a trivalent group or a tetravalent group.

As used herein, the C ₁ -C ₆₀ heterocyclic group has the same structure as the C ₅ -C ₆₀ carbocyclic group, but as ring-forming atoms, in addition to carbon (carbon number may be 1 to 60), N , refers to a group containing at least one hetero atom selected from O, Si, P and S.

As used herein, the substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkyl Len group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted Divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, Substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₆₀ cycloalkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cyclo Alkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C At least one of _{the 1} -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituent of the substituted monovalent non-aromatic condensed heteropolycyclic group,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ - C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalke Nyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent ratio -aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), substituted with at least one selected from C ₃ - C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from,

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amine Dino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group , C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ It may be selected from a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

In this specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “ter-Bu” or “Bu ^t ” refers to a tert-butyl group, and “OMe " means a methoxy group.

As used herein, “biphenyl group” means “a phenyl group substituted with a phenyl group.” The “biphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group”.

As used herein, “terphenyl group” means “a phenyl group substituted with a biphenyl group.” The “terphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group.”

In this specification, * and *' refer to bonding sites with neighboring atoms in the corresponding chemical formula, unless otherwise defined.

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present invention will be described in more detail through examples. In the following synthesis example, in the expression "B was used instead of A," the molar equivalent of A and the molar equivalent of B are the same.

[Synthesis example]

Synthesis example 1: Synthesis of compound 14

The solvents and reagents used in the synthesis were commercially available, and those not specified were used as purchased. ¹ H-NMR analysis was performed using a 400 MHz NMR spectrometer at 25°C, and DMSO-d ₆ was used as a solvent. Chemical shift is expressed in δ units (Parts per million (ppm)) based on δ _H 2.50 of CHD ₂ (CD ₃ )SO.

3-(3-(2H-Benzo[d][1,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl)propanoic acid (2 mmol), 4-hydroxy- 1,2,2,6,6-pentamethylpiperidine (4-Hydroxy-1,2,2,6,6-pentamethylpiperidine) 2.4 mmol, N,N-diisopropylethylamine ) 4 mmol, 1-hydroxybenzotriazole (HOBt, anhydrous) 2.88 mmol, and diisopropylcarbodiimide (Diisopropylcarbodiimide) 2.88 mmol were added to 50 mL of dried dimethylchloride solvent and reacted with stirring at room temperature. After completion of the reaction, water and ethyl acetate were added to the product to extract the organic layer, which was washed three times with a saturated aqueous sodium chloride solution. Only the extracted organic layer was collected, moisture was removed using magnesium sulfate, and then dried. Afterwards, the product was purified/separated by flash column chromatography (Ethylacetate: n-Hexane = 9:1), and the solvent was removed through vacuum drying to obtain Compound 14 as a white solid (final yield 78%). .

¹ H-NMR (400MHz, DMSO-d ₆ ) δppm 11.25 (br. S, 1H), 8.00~8.20 (m, 2H), 7.95 (d, J=2.1Hz, 1H), 7.50~7.67 (m, 2H) ), 7.28 (d, J=2.1 Hz, 1H), 5.8 (m, 1H), 2.87 (t, J=7.5 Hz, 2H), 2.56 (t, J=7.5 Hz, 2H), 2.35 (s, 3H) ), 1.80-1.96 (m, 4H), 1.45 (s, 9H), 1.27 (s, 12H).

[Example]

Example One

Using the composition for forming a thin film encapsulation containing Compound 14 synthesized in Synthesis Example 1, an electronic device including a thin film encapsulation for sealing an organic light emitting device on a substrate was formed.

Comparative example One

A thin film encapsulation portion for sealing the organic light emitting device on the substrate was formed in the same manner as in Example 1, except that Compound A below was used instead of Compound 14.

Comparative example 2

A thin film encapsulation portion for sealing the organic light-emitting device on the substrate was formed in the same manner as in Example 1, except that a 1:1 equivalent mixture of Compound A and Compound B below was used instead of Compound 14.

Evaluation example One

The initial transmittance (T ₁ ) of the thin film encapsulation portion of the electronic device manufactured in Example 1 and Comparative Examples 1 and 2 and the transmittance after exposure to an exposure dose of 52000 Wh/m ² with LED lighting having a maximum emission wavelength of 405 nm (“after exposure Transmittance (T ₂ )") was measured respectively, and the results are shown in FIG. 3.

In addition, with respect to the initial transmittance (T ₁ ) and the transmittance after exposure (T ₂ ) of the thin film encapsulation portion of the electronic device manufactured in Example 1 and Comparative Examples 1 and 2, the transmittance change (ΔT) as expressed in Equation 1 below %) was calculated and shown in Table 1.

<Equation 1>

Transmittance change (ΔT%) = Transmittance after exposure (T ₂ ) - Initial transmittance (T ₁ )

Transmittance change based on 405nm
(ΔT%@405nm) Example 1 0.15% Comparative Example 1 3.50% Comparative Example 2 4.50%

Referring to FIG. 3 and Table 1, the electronic device according to one embodiment, unlike the electronic devices of Comparative Examples 1 and 2, shows little change in the initial transmittance of the thin film encapsulation portion and the transmittance after exposure (transmittance change of 0.15%). It was confirmed that photocuring resistance was excellent.

Therefore, the organic light emitting display device including the heterocyclic compound in the encapsulation portion according to one embodiment can prevent the light emitting layer and the insulating film including the organic material from being damaged by ultraviolet rays and short-wavelength visible light.

10: Organic light emitting device
100: substrate
200: Organic light emitting device
300: Encapsulation part

Claims (20)

Heterocyclic compounds, represented by Formula 1:
<Formula 1>

In Formula 1,
L ₁ is a group represented by the following formula 2-1,
<Formula 2-1>

L ₁₁ is a C ₂ -C ₁₂ alkylene group,
* and *' are binding sites with neighboring atoms,
A ₁ is a UV-absorbing group,
A ₂ is a radical-scavenging group,
m1 is an integer from 1 to 3,
m2 is an integer from 1 to 3,
A ₁ is a group represented by the following formula 4-29,

In Formula 4-29,
R ₃₁ and R ₃₃ to R ₃₅ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group , substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy Group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non- Aromatic heterocondensed polycyclic group, Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q 2 ), -B(Q ₁ )( _{Q 2 )} , -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),
R ₄₁ to R ₄₄ are each hydrogen,
* is a binding site with a neighboring atom,
The A ₂ is a group represented by the following formula 6-2,
<Formula 6-2>

In Formula 6-2,
R ₆₀ and R ₆₁ are independently hydrogen or methyl groups,
a60 is an integer from 1 to 4,
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₆₀ cycloalkoxy group , substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ - C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substitution At least one of the substituents of the monovalent non-aromatic condensed heteropolycyclic group is,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ). C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group and C ₃ -C ₆₀ cycloalkoxy group substituted with at least one selected from among;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalke Nyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent ratio -aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), substituted with at least one selected from C ₃ - C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );
is selected from,
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ cycloalkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group , C ₆ -C ₆₀ aryl group substituted with a C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group, terphenyl group, C ₁ -C ₆₀ heteroaryl group, C ₁ - C ₁ -C ₆₀ heteroaryl group substituted with C ₆₀ alkyl group, C ₁ -C ₆₀ heteroaryl group substituted with C ₆ -C ₆₀ aryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group selected from the group, biphenyl group and terphenyl group,
* is a bonding site with a neighboring atom. delete delete delete delete delete delete delete According to paragraph 1,
The A ₂ is a heterocyclic compound represented by the following formula 7-2:

In Formula 7-2,
For a description of R ₆₁ to R ₆₆ , refer to the description of R ₆₀ in paragraph 1,
* is a bonding site with a neighboring atom. Compound 14, a heterocyclic compound:
. A composition for forming a thin film encapsulation portion, comprising the heterocyclic compound of any one of claims 1, 9, and 10. According to clause 11,
A composition for forming a thin film encapsulation further comprising a monomer for forming a matrix resin and a photopolymerization initiator. Board;
an organic light emitting device on the substrate; and
It includes a thin film encapsulation part that seals the organic light emitting device,
The thin film encapsulation part is an electronic device comprising the heterocyclic compound of any one of claims 1, 9, and 10. According to clause 13,
The thin film encapsulation part includes at least one organic film,
The at least one organic layer includes a first organic layer,
An electronic device wherein the heterocyclic compound is included in the first organic layer. According to clause 14,
The first organic layer further includes a matrix resin,
The matrix resin is an electronic device including one or more of acrylic resin, methacrylic resin, isoprene-based resin, vinyl-based resin, epoxy-based resin, urethane-based resin, cellulose-based resin, perylene-based resin, imide-based resin, and silicone-based resin. According to clause 14,
The electronic device wherein the content of the heterocyclic compound is 3 to 10 parts by weight per 100 parts by weight of the first organic layer. According to clause 14,
The first organic film has a transmittance of 80% or more for light with a wavelength of 430 nm or more,
An electronic device having a transmittance of 10% or less for light with a wavelength of 405 nm or less. According to clause 14,
The first organic film is an electronic device in which a change in transmittance in the wavelength range of 400 nm to 410 nm is less than 5% when exposed to light with a maximum emission wavelength of 405 nm at an exposure dose of 52000 Wh/m ² . According to clause 14,
An electronic device wherein the first organic layer has a thickness of 10 nm to 20 ㎛. According to clause 14,
The thin film encapsulation part further includes at least one inorganic film,
Wherein the at least one inorganic layer includes one or more selected from metal, metal halide, metal nitride, metal oxide, metal oxynitride, silicon nitride, silicon oxide, and silicon oxynitride.