KR20230164550A - Light emitting device, electronic device including the same and electronic apparatus including the same - Google Patents

Abstract

first electrode; a second electrode opposite the first electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer includes a light-emitting layer and an electron transport region, and the electron transport region is disposed between the light-emitting layer and the second electrode, The light emitting layer includes a first emitter, and the electron transport region provides a light emitting device including a heterocyclic compound, an electronic device including the light emitting device, and a consumer product including the light emitting device. For descriptions of the first emitter and heterocyclic compound, refer to what is described herein.

Description

Light emitting device, electronic device including the same, and electronic device including the same {Light emitting device, electronic device including the same and electronic apparatus including the same}

It relates to light-emitting devices, electronic devices including them, and electronic devices including them.

Among light-emitting devices, self-emissive devices (for example, organic light-emitting devices, etc.) 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.

The light-emitting device has a first electrode disposed on an upper portion of a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are sequentially disposed on the upper portion of the first electrode. It can have a structure. Holes injected from the first electrode move to the light-emitting layer via the hole transport region, and electrons injected from the second electrode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated as the exciton changes from the excited state to the ground state.

To provide a light emitting device with low driving voltage and high power efficiency, an electronic device including the same, and an electronic device including the same.

According to one aspect,

first electrode;

a second electrode opposite the first electrode; and

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

Including,

The intermediate layer includes a light emitting layer and an electron transport region,

The electron transport region is disposed between the light-emitting layer and the second electrode,

The light emitting layer includes a first emitter,

The first emitter emits first light having a first emission spectrum,

The first emitter includes platinum,

The triplet metal-to-ligand charge transfer state ( ^3MLCT ) of the first emitter is 7% or more,

The triplet metal-ligand charge transfer state was evaluated by performing quantum chemical calculations based on density functional theory (DFT),

The electron transport region includes a heterocyclic compound,

The heterocyclic compound is,

A first moiety comprising a group represented by one of the following formulas 8-1 to 8-4; and

a second moiety comprising a diazine group, a triazine group, or any combination thereof;

Including,

A light emitting device is provided wherein the first moiety and the second moiety are linked to each other through a single bond or a first linking group:

In formulas 8-1 to 8-4,

X ₈ is O, S, or Se,

* is a single bond bonded to the second moiety or a binding site with a first linking group bonded to the second moiety.

According to the other aspect,

first electrode;

a second electrode opposite the first electrode; and

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

Including,

The intermediate layer includes a light emitting layer and an electron transport region,

The electron transport region is disposed between the light-emitting layer and the second electrode,

The light emitting layer includes a first emitter,

The first emitter emits first light having a first emission spectrum,

The first emitter is an organometallic compound represented by the following formula (1),

The electron transport region includes a heterocyclic compound,

The heterocyclic compound is,

A first moiety comprising a group represented by one of the following formulas 8-1 to 8-4; and

a second moiety comprising a diazine group, a triazine group, or any combination thereof;

Including,

A light emitting device is provided wherein the first moiety and the second moiety are linked to each other through a single bond or a first linking group:

<Formula 1>

For a description of Formula 1, please refer to the description herein:

In formulas 8-1 to 8-4,

X ₈ is O, S, or Se,

* is a single bond bonded to the second moiety or a binding site with a first linking group bonded to the second moiety.

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

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

The light-emitting device has a low driving voltage and high power efficiency, and can be used to manufacture high-quality electronic devices and consumer goods.

Figure 1 is a diagram schematically showing the structure of a light-emitting device according to an embodiment.
2 and 3 are diagrams schematically showing the structure of a light-emitting device, which is one of the electronic devices according to an embodiment of the present invention.
Figures 4, 5, 6a, 6b, and 6c are diagrams schematically showing the structure of an electronic device according to an implementation example.

The light emitting device includes: a first electrode; a second electrode opposite the first electrode; and an intermediate layer disposed between the first electrode and the second electrode.

The intermediate layer may include a light emitting layer and an electron transport region.

The electron transport region may be disposed between the light emitting layer and the second electrode.

The light emitting layer may include a first emitter. The first emitter may emit first light having a first emission spectrum.

The peak emission wavelength (maximum emission wavelength, or maximum emission peak wavelength) of the first light may be 510 nm to 610 nm, or 511 nm to 604 nm.

The full width at half maximum (FWHM) of the first light may be 15 nm to 85 nm.

For example, the half width of the first light is 20 nm to 85 nm, 25 nm to 85 nm, 15 nm to 80 nm, 20 nm to 80 nm, 25 nm to 80 nm, 15 nm to 75 nm, 20 nm to 75 nm, 25 nm to 75 nm, 15 nm to 70 nm, 20 nm to 70 nm. , 25 nm to 70 nm, 15 nm to 65 nm, 20 nm to 65 nm, 25 nm to 65 nm, 15 nm to 60 nm, 20 nm to 60 nm, or 25 nm to 60 nm.

The emission peak wavelength (or maximum emission wavelength) and half width of the first light described in this specification may be evaluated from the emission spectrum of the film including the first emitter (for example, see Evaluation Example 2) . As used herein, the emission peak wavelength refers to the peak wavelength having the maximum emission intensity in the emission spectrum or electroluminescence spectrum.

The first light may be green light.

The first emitter may include platinum.

For example, the first emitter may be an organometallic compound including platinum. The first emitter may be neutral, may contain one platinum, and may not contain any other transition metal other than platinum.

The triplet metal-to-ligand charge transfer state ( ^3MLCT ) of the first emitter may be 7% or more.

For example, the triplet metal-ligand charge transfer state of the first emitter is 7% to 30%, 7% to 25%, 7% to 20%, 7% to 18%, 7% to 16%, 8%. % to 30%, 8% to 25%, 8% to 20%, 8% to 18%, 8% to 16%, 9% to 30%, 9% to 25%, 9% to 20%, 9% to 9% It may be 18%, or 9% to 16%.

The triplet metal-ligand charge transfer state may be evaluated (for example, see Evaluation Example 1 below) by performing quantum chemical calculations based on density functional theory (DFT).

According to another embodiment, the first emitter may further include, in addition to the platinum, a first ligand bound to the platinum.

According to another implementation, the first emitter may satisfy at least one of the following <Condition A> to <Condition C>:

<Condition A>

The first ligand is a tetradentate ligand,

There are three cyclometallated rings formed by chemical bonds between the platinum and the first ligand.

<Condition B>

Each of the carbon, nitrogen, and oxygen of the first ligand is chemically bonded to the platinum.

<Condition C>

The first ligand comprises an imidazole group, a benzimidazole group, a naphthoimidazole group, or any combination thereof.

According to another implementation, the first emitter may satisfy all of the <Condition A> to <Condition C>.

For a more detailed description of the first emitter, refer to what is described herein.

The electron transport region may include a heterocyclic compound.

The heterocyclic compound is,

A first moiety comprising a group represented by one of the following formulas 8-1 to 8-4; and

a second moiety comprising a diazine group (e.g., a pyrimidine group, a pyrazine group, a pyridazine group, etc.), a triazine group, or any combination thereof;

may include.

For a description of Chemical Formulas 8-1 to 8-4, refer to what is described later.

The first moiety and the second moiety may be linked to each other through a single bond or a first linking group. For a description of the first linking group, refer to the description of *-(Ar ₃ ) _x3 -*' in Chemical Formula 8, which will be described later.

In formulas 8-1 to 8-4,

X ₈ is O, S, or Se,

* is a single bond bonded to the second moiety or a binding site with a first linking group bonded to the second moiety.

For a more detailed description of the heterocyclic compounds, please refer to what is described herein.

The light-emitting device includes 1) a light-emitting layer including the first emitter and 2) an electron transport region including the heterocyclic compound, enabling efficient electron transport to the light-emitting layer, thereby reducing the number of electrons and holes in the light-emitting layer. Recombination balance can be increased. As a result, the light-emitting device can have a low driving voltage and high power efficiency, and high-quality electronic devices and devices can be manufactured using it.

According to one embodiment, CIEx among the color coordinates of light emitted from the light emitting device may be 0.20 to 0.80, or 0.23 to 0.70.

According to another embodiment, CIEy among the color coordinates of light emitted from the light emitting device may be 0.20 to 0.80, or 0.30 to 0.71.

According to another embodiment, the first emitter may include at least one deuterium.

According to another embodiment, the first emitter may include a deuterated C ₁ -C ₂₀ alkyl group, a deuterated C ₃ -C ₁₀ cycloalkyl group, or any combination thereof.

According to another embodiment, the HOMO energy level of the first emitter may be -5.50 eV to -4.70 eV or -5.20 eV to -4.84 eV.

According to another embodiment, the LUMO energy level of the first emitter may be -2.70 eV to -1.60 eV or -2.55 eV to -1.66 eV.

The HOMO and LUMO energy levels can be evaluated through cyclic voltammetry analysis (e.g., Evaluation Example 1) for the organometallic compound.

According to another aspect, the first emitter may be an organometallic compound represented by the following formula (1). For a detailed description of Formula 1, refer to what is described herein.

For example, the organometallic compound represented by Formula 1 may satisfy the triplet metal-ligand charge transfer state, first light condition, HOMO energy level, and/or LUMO energy level of the first emitter described herein.

In addition to the first emitter as described above, the light emitting layer may further include a host, an auxiliary dopant, a sensor, a delayed fluorescent material, or any combination thereof. Each of the host, auxiliary dopant, sensor, delayed fluorescent material, or any combination thereof may include at least one deuterium.

For example, the light emitting layer may include the first emitter and the host. The host is different from the first emitter, and the host may include an electron transport compound, a hole transport compound, a bipolar compound, or any combination thereof. The host may not contain metal. Each of the electron-transporting compounds, hole-transporting compounds and amphiphilic compounds is different from each other.

According to one embodiment, the light emitting layer includes the first emitter and a host, and the host may include an electron transport compound and a hole transport compound. The electron transporting compound and the hole transporting compound may form an exciplex.

For example, the electron transporting compound may include at least one π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group. For example, the electron transporting compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.

As another example, the hole transporting compound includes at _least one π electron-rich C ₃ -C ₆₀ cyclic group, a pyridine group, or _a combination thereof, Electron transporting groups (e.g., π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic groups excluding pyridine groups, cyano groups, sulfoxide groups, phosphine oxide groups, etc.) may not be included.

According to one embodiment, the following compounds may be excluded from the hole transport compounds.

According to one embodiment, the electron transport compound may include a compound represented by Formula 2-1 or a compound represented by Formula 2-2:

<Formula 2-1>

<Formula 2-2>

In formulas 2-1 and 2-2,

L ₅₁ to L ₅₃ are each independently a single bond, a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a , or a C ₁ -C ₆₀ substituted or unsubstituted with at least one R _10a It is a heterocyclic group,

b51 to b53 are independently one of the integers from 1 to 5,

A ₇ to A9 are each independently a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a (e.g., substituted or unsubstituted with at least one R _10a , benzene group, naphthalene group, etc.),

X ₅₄ is N or C(R ₅₄ ), X ₅₅ is N or C(R ₅₅ ), X ₅₆ is N or C(R ₅₆ ), and at least one of X ₅₄ to X ₅₆ is N,

X ₅₇ is O, S, N(R ₅₇ ), C(R _57a )(R _57b ) or Si(R _57a )(R _57b )

For descriptions of each of R ₅₁ to R ₅₇ , R _57a , R _57b and R _10a , refer to what is described herein.

According to another embodiment, the hole transporting compound is a compound represented by the following formula 3-1, a compound represented by the following formula 3-2, a compound represented by the following formula 3-3, a compound represented by the following formula 3-4, and a compound represented by the following formula 3 Compounds indicated by -5, or any combination thereof:

<Formula 3-1>

<Formula 3-2>

<Formula 3-3>

<Formula 3-4>

<Formula 3-5>

In Formulas 3-1 to 3-5,

Ring CY ₇₁ to ring CY ₇₄ are independently of each other, π electron-excessive C ₃ -C ₆₀ cyclic group (e.g., benzene group, naphthalene group, fluorene group, anthracene group, carbazole group, dibenzofuran group) , dibenzothiophene group, etc.) or pyridine group,

_{and _ _ _ _ _ _ _}

_{and _ _ _ _ _ _ _}

_{and _ _ _ _ _ _ _}

X ₈₅ is C or Si,

L ₈₁ to L ₈₅ are independently of each other, a single bond, *-C(Q ₄ )(Q ₅ )-*', *-Si(Q ₄ )(Q ₅ )-*', at least one R _10a substituted or an unsubstituted π electron-excessive C ₃ -C ₆₀ cyclic group (e.g., substituted or unsubstituted with at least one R _10a , benzene group, naphthalene group, fluorene group, anthracene group, carbazole group, dibenzofuran group, dibenzothiophene group, etc.) or a pyridine group substituted or unsubstituted with at least one R _10a , and the description of Q ₄ and Q ₅ refers to the description of Q ₁ in the present specification, respectively. ,

b81 to b85 are independently one of the integers from 1 to 5,

For a description of each of _{R 71} to R ₇₄ , R 81 to R ₈₅ , R _82a , R _82b , R _83a , R _83b , R _84a and R _84b , refer to what is described herein,

a71 to a74 are independently one of the integers from 0 to 20,

For a description of R _10a , refer to what is described herein.

For a description of Chemical Formulas 3-1 to 3-5, refer to what will be described later.

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

According to one embodiment, the electron transport region may include an electron transport layer, and the heterocyclic compound may be included in the electron transport layer. The electron transport layer may further include a metal-containing material in addition to the heterocyclic compound. For a description of the metal-containing material, reference may be made to what is described herein.

According to another embodiment, the electron transport layer containing the heterocyclic compound may be in direct contact with the light emitting layer.

According to another embodiment, the electron transport region includes a hole blocking layer and an electron transport layer, the hole blocking layer is disposed between the light emitting layer and the electron transport layer, and the hole blocking layer includes the heterocyclic compound. It is not included, and the heterocyclic compound may be included in the electron transport layer.

In this specification, “the middle layer (or electron transport region) includes a first emitter (or includes a heterocyclic compound)” means “the middle layer (or electron transport region) includes the first emitter.” One compound belonging to the category or two or more different compounds belonging to the category of the first emitter (or one compound belonging to the category of the heterocyclic compound or two compounds belonging to the category of the heterocyclic compound It can be interpreted as “may include more than one type of different compound).”

In this specification, “intermediate layer” is a term referring to all single and/or multiple layers disposed between the first electrode and the second electrode of the light emitting device.

According to another aspect, an electronic device including a light emitting device as described above is provided. The electronic device may further include a thin film transistor. For example, the electronic device further includes a thin film transistor including a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. Meanwhile, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For a more detailed description of the electronic device, please refer to what is described herein.

According to another aspect, an electronic device including a light emitting element as described above is provided. By employing a light-emitting device having a light-emitting layer including a first emitter and an electron transport region including a heterocyclic compound as described herein, the display quality, power consumption, durability, etc. of the electronic device can be improved.

For example, the consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal lights, head-up displays, fully or partially transparent displays, flexible displays, and rollables. (rollable displays, foldable displays, stretchable displays, laser printers, phones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, It may be one of a viewfinder, a micro display, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall containing multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.

Explanation of chemical formula

For example, the first emitter may be an organometallic compound represented by the following formula (1):

<Formula 1>

In Formula 1,

M is platinum (Pt),

X ₁ to X ₄ are each independently N or C,

T ₁₁ to T ₁₄ are independently of each other, a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R') (R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") or P(R')(R") ego,

When T ₁₁ is a chemical bond, X ₁ and M are directly bonded, when T _{12 is} a chemical bond, X ₂ and M are directly bonded, and when T ₁₃ is a chemical bond, Bonds directly, and when T ₁₄ is a chemical bond, X ₄ and M bond directly,

Two of the bonds between X ₁ or T ₁₁ and M, the bond between X ₂ or T ₁₂ and M, the bond between X ₃ or T ₁₃ and M, and the bond between X ₄ or T ₁₄ and M are coordinate bonds. , and the remaining two bonds are covalent bonds,

T ₁ is a single bond, double bond, *-N(R ₅ )-*', *-B(R ₅ )-*', *-P(R ₅ )-*', *-C(R _5a )( R _5b )-*', *-Si(R _5a )(R _5b )-*', *-Ge(R _5a )(R _5b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₅ )= *', *=C(R ₅ )-*', *-C(R _5a )=C(R _5b )-*', *-C(=S)-*' or *-C≡C-*' ego,

T ₂ is a single bond, double bond, *-N(R ₆ )-*', *-B(R ₆ )-*', *-P(R ₆ )-*', *-C(R _6a )( R _6b )-*', *-Si(R _6a )(R _6b )-*', *-Ge(R _6a )(R _6b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₆ )= *', *=C(R ₆ )-*', *-C(R _6a )=C(R _6b )-*', *-C(=S)-*' or *-C≡C-*' ego,

T ₃ is a single bond, double bond, *-N(R ₇ )-*’, *-B(R ₇ )-*’, *-P(R ₇ )-*’, *-C(R _7a )( R _7b )-*', *-Si(R _7a )(R _7b )-*', *-Ge(R _7a )(R _7b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₇ )= *', *=C(R ₇ )-*', *-C(R _7a )=C(R _7b )-*', *-C(=S)-*' or *-C≡C-*' ego,

Ring CY ₁ , ring CY ₃ and ring CY ₄ are, independently of each other, a C ₃ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

X ₂₁ is N or C(R ₂₁ ), X ₂₂ is N or C(R ₂₂ ), X ₂₃ is N or C(R ₂₃ ),

X ₂₄ is O, S, N(R ₂₄ ) or C(R _24a )(R _24b ),

R ₁ , R ₂₁ to R ₂₄ , R _24a , R _24b , R ₃ to R 7, R _5a , R _5b , R _6a , R _6b , R _7a , _{R 7b ,} R', and R" are independently of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₆₀ alkyl group substituted or unsubstituted with at least one R _10a , with at least one R _10a Substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group substituted or unsubstituted with at least one R _10a , C ₁ -C ₆₀ alkoxy group substituted or unsubstituted with at least one R _10a , C ₃ -C _{60 carbocyclic} group unsubstituted or substituted with at least one R _10a , C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R 10a , substituted with at least one R _10a or an unsubstituted C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group unsubstituted or substituted with at least one R _10a , a C ₇ -C ₆₀ aryl substituted or unsubstituted with at least one R _10a Alkyl group, C ₂ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ), or -P( =O)(Q ₁ )(Q ₂ ),

a1, a3 and a4 are independently one of the integers from 0 to 20,

* and *' are bonding sites with neighboring atoms, respectively,

i) 2 groups of a1 R ₁ , ii) 2 groups of R ₂₁ to R ₂₃ , iii) 2 groups of a3 R ₃ , iv) 2 groups of a4 R ₄ , v) R _5a and R _5b , vi) R _6a and R _6b , and vii) two groups of R _7a and R _7b are each optionally bonded to each other through a single bond, double bond or first linking group, forming at least one R It may form a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with _10a or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,

The R _10a is,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₁₁ )( Q ₁₂ ), or substituted or unsubstituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro 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 carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group , C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₂₁ )(Q ₂₂ ), or any combination thereof, substituted or unsubstituted, C ₃ - C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, or C ₂ -C ₆₀ hetero Arylalkyl group; or

-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 ), or -P(=O)(Q ₃₁ )(Q ₃₂ );

ego,

Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; or C ₁ -C 60 alkyl group, _{C 2} substituted or unsubstituted with deuterium, -F, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, biphenyl group, or any combination thereof. -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group, or C ₁ -C ₆₀ heterocyclic group;

According to one embodiment, in Formula 1,

i) X ₁ and X ₃ are C and X ₂ and X ₄ are N, or

ii) X ₁ and X ₄ are C and X ₂ and X ₃ are N, or

iii) X ₁ , X ₂ and X ₃ may be C, and X ₄ may be N.

According to another embodiment, in Formula 1,

T ₁₁ is O or S,

Each of T ₁₂ to T ₁₄ may be a chemical bond.

According to another embodiment, in Formula 1,

T ₁₁ is O or S,

Each of T ₁₂ to T ₁₄ is a chemical bond,

i) each of the bonds between T ₁₁ and M and _the bond between X ₃ and M is a _covalent bond and each of the bonds between X ₂ and M and the bond between Each of the bonds between M and the bond between X ₄ and M may be a covalent bond, and each of the bonds between X ₂ and M and the bond between X ₃ and M may be a coordinate bond.

According to another embodiment, each of T ₁ to T ₃ in Formula 1 may be a single bond.

According to another embodiment, ring CY ₁ in Formula 1 may be a benzene group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilol group.

According to another embodiment, in Formula 1, X ₂₁ may be C(R ₂₁ ), X ₂₂ may be C(R ₂₂ ), and X ₂₃ may be C(R ₂₃ ).

According to another embodiment, in Formula 1, X ₂₄ may be N(R ₂₄ ).

According to another embodiment, ring CY ₃ in Formula 1 is a benzene group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilol group, a pyridine group, and a pyrimidine group. group, pyrazine group, pyridazine group, quinoline group, isoquinoline group, quinoxaline group, azadibenzofuran group, azadibenzothiophene group, azacarbazole group, azafluorene group or azadibenzosilol group. there is.

According to another embodiment, ring CY ₄ in Formula 1 is a benzene group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilol group, a pyridine group, and a pyrimidine group. group, pyrazine group, pyridazine group, quinoline group, isoquinoline group, quinoxaline group, azadibenzofuran group, azadibenzothiophene group, azacarbazole group, azafluorene group, azadibenzosilol group, imi It may be a dazole group, a benzimidazole group, or a naphthoimidazole group.

According to another embodiment, ring CY ₄ in Formula 1 may not be an imidazole group or a benzimidazole group.

According to another embodiment, in Formula 1, R ₁ , R _{21 to R 24 ,} R _24a , R _24b , R ₃ to R ₇ , R _5a , R _5b , R _6a , R _6b , R _7a , R _7b , R', and R" are independent of each other,

Hydrogen, deuterium, -F or cyano group;

C ₁ -C ₂₀ alkyl group or C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted with deuterium, -F, cyano group, or any combination thereof; or

Deuterium, -F, cyano group, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group. , biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C ₁ -C ₂₀ alkyl) biphenyl group, or any combination of substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, dibenzofuranyl group, or di Benzothiophenyl group (or, thienyl group);

It can be.

In Formula 1, a1, a3 and a4 each represent the number of R ₁ , R ₃ and R ₄ and, for example, may be independently 0, 1, 2, 3, 4, 5 or 6. .

_{According to another embodiment , _ _} It may be a C ₃ -C ₆₀ carbocyclic group, or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a .

According to another embodiment, at least one of R ₁ , R ₃ and R ₄ is a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , or substituted with at least one R _10a Or it may be an unsubstituted C ₁ -C ₆₀ heterocyclic group.

로 표시된 그룹은 하기 화학식 CY1(1) 내지 CY1(16) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 1,

The group represented by may be a group represented by one of the formulas CY1(1) to CY1(16):

Among the formulas CY1(1) to CY1(16),

For a description of X ₁ , refer to what is described herein,

The description of each of R ₁₁ to R ₁₄ is the same as the description of R ₁ in the present specification, except that each of R ₁₁ to R ₁₄ is not hydrogen,

* is the binding site with T ₁₁ in Formula 1,

*' is the binding site with T ₁ in Chemical Formula 1.

로 표시된 그룹은 하기 화학식 CY3(1) 내지 CY3(12) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 1,

The group represented by may be a group represented by one of the formulas CY3(1) to CY3(12):

Among the formulas CY3(1) to CY3(12),

For a description of X ₃ , refer to what is described herein,

X ₃₉ is O, S, N(R ₃₉ ), C(R _39a )(R _39b ) or Si(R _39a )(R _39b )

The description of each of R ₃₁ to R ₃₃ , R ₃₉ , R _39a and R _39b is the same as the description for R ₃ in the specification, but each of R ₃₁ to R ₃₃ is not hydrogen,

* is the binding site with T ₁₃ in Formula 1,

*' is the binding site with T ₃ in Formula 1,

*" is the binding site with T ₂ in Chemical Formula 1.

로 표시된 그룹은 하기 화학식 CY4(1) 내지 CY4(27) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 1,

The group represented by may be a group represented by one of the formulas CY4(1) to CY4(27):

Among the formulas CY4(1) to CY4(27),

For a description of X ₄ , refer to what is described herein,

_{and _ _ _ _ _}

The description of each of R ₄₁ to R ₄₄ , R ₄₉ , R _49a and R _49b is the same as the description of R ₄ in the specification, but each of R ₄₁ to R ₄₄ is not hydrogen,

* is the binding site with T ₁₄ in Formula 1,

*' is the binding site with T ₃ in Chemical Formula 1.

로 표시된 그룹은 하기 화학식 CY4(1) 내지 CY4(23) 중 하나로 표시된 그룹일 수 있다.According to another embodiment, in Formula 1,

The group represented by may be a group represented by one of the following formulas CY4(1) to CY4(23).

According to another embodiment _, R ₁ , R 21 to R ₂₄ , R _24a , R _24b , R ₃ to R ₇ , R _5a , R _5b , R 6a , R _6b , R _7a , _{R 7b ,} R’, and R" may include at least one deuterium.

According to another embodiment _, R ₁ , R 21 to R ₂₄ , R _24a , R _24b , R ₃ to R ₇ , R _5a , R _5b , R 6a , R _6b , R _7a , _{R 7b ,} R’, and R" may be a deuterated C ₁ -C ₂₀ alkyl group or a deuterated C ₃ -C ₁₀ cycloalkyl group.

Meanwhile, the heterocyclic compound may be a compound represented by the following formula (8):

<Formula 8>

In the above formula 8,

X ₁₄ is N or C(Z ₄ ), X ₁₅ is N or C(Z ₅ ), X ₁₆ is N or C(Z ₆ ),

2 or more of X ₁₄ to X ₁₆ are N,

Ar ₁ to Ar ₃ are each independently a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a , or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R _10a Click group,

x1 to x3 are independently one of the integers from 0 to 10,

i) When x1 is 0, *-(Ar ₁ ) _x1 -*' becomes a single bond, ii) When x2 is 0, *-(Ar ₂ ) _x2 -*' becomes a single bond, iii) When x3 is 0, *-(Ar ₃ ) _x3 -*' becomes a single bond, * and *' are each a bonding site with a neighboring atom,

Ar ₁₃ is a group represented by one of the following formulas 8-1 to 8-4,

Z ₁ to Z ₆ are each independently C ₁ -substituted or unsubstituted with hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R _10a C ₆₀ alkyl group, C _{2 -C 60 alkenyl} group substituted or unsubstituted with at least one R 10a, C ₂ -C ₆₀ alkynyl group substituted or unsubstituted with at least one R _10a , substituted with at least one R _10a or Unsubstituted C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a Click group, C ₆ -C ₆₀ aryloxy group, unsubstituted or substituted with at least one R _10a , C ₆ -C ₆₀ arylthio group, unsubstituted or substituted with at least one R _10a , substituted with at least one R _10a or an unsubstituted C ₇ -C ₆₀ arylalkyl group, a C ₂ -C ₆₀ heteroarylalkyl group unsubstituted or substituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ) or -P(=O)(Q ₁ )(Q ₂ ),

y1 to y3 are independently one of the integers from 0 to 5,

The R _10a is the same as the description for R _10a in Formula 1:

In formulas 8-1 to 8-4,

X ₈ is O, S, or Se,

* is a binding site with Ar ₃ in Chemical Formula 8.

According to one embodiment, Ar ₁ to Ar ₃ in Formula 8 are independently of each other substituted or unsubstituted with at least one R _10a , a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a dibenzofuran group, It may be a dibenzothiophene group, a carbazole group, a fluorene group, or a pyridine group.

In Formula 8, each of x1 to x3 represents the number of Ar ₁ to Ar ₃ . When x1 is 2 or more, 2 or more Ar ₁ may be the same or different from each other, when x2 is 2 or more, 2 or more Ar ₂ may be the same or different from each other, and when x3 is 2 or more, 2 or more Ar ₃ may be the same as each other. It may be the same or different. For example, in Formula 8, x1 and x2 are independently integers of 1 to 10, and x3 may be 0, 1, or 2.

According to one embodiment, at least one of x1 and x2 in Formula 8 may be 2 or more (eg, 2, 3, 4, or 5).

According to another embodiment, in Formula 8, x1 and x2 are independently of each other, one of the integers of 1 to 10, x3 is 0, 1, or 2, and Ar ₁ to Ar ₃ are independently of each other, at least one R It may be substituted or unsubstituted with _10a , a benzene group, naphthalene group, phenanthrene group, anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, or pyridine group.

According to another embodiment, in Formula 8, at least one of x1 Ar ₁ , at least one of x2 Ar ₂ , or any combination thereof is independently substituted or unsubstituted with at least one R _10a , It may be a benzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a pyridine group.

According to another embodiment, in Formula 8, at least one of x1 Ar ₁ , at least one of x2 Ar ₂ , or any combination thereof is independently substituted or unsubstituted with at least one R _10a , It may be a benzofuran group, a dibenzothiophene group, or a carbazole group.

Ar ₁₃ in Formula 8 is a group represented by one of Formulas 8-1 to 8-4, and Z ₃ , which is not hydrogen, may be substituted at any position of Ar ₁₃ .

According to another embodiment, in Formula 8, Z ₁ to Z ₆ are independently of each other,

Hydrogen, deuterium, -F or cyano group;

C ₁ -C ₂₀ alkyl group or C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted with deuterium, -F, cyano group, or any combination thereof;

Deuterium, -F, cyano group, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group. , biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C ₁ -C ₂₀ alkyl) biphenyl group, or any combination of substituted or unsubstituted phenyl group, biphenyl group, naphthyl group, dibenzofuranyl group, or di Benzothiophenyl group (or, thienyl group); or

-Si(Q ₁ )(Q ₂ )(Q ₃ );

It can be. Here, the description of each of Q ₁ to Q ₃ refers to what is described herein.

According to another embodiment, at least one of Z ₁ to Z ₆ may include at least one deuterium.

According to another embodiment, at least one of Z ₁ to Z ₆ may be a deuterated C ₁ -C ₂₀ alkyl group or a deuterated C ₃ -C ₁₀ cycloalkyl group.

In Formula 8, each of y1 to y3 represents the number of Z ₁ to Z ₃ and may be, for example, one of the integers from 0 to 5. For example, y1 to y3 may independently be 0, 1, or 2.

As used herein, “biphenyl group” refers to a monovalent substituent having a structure in which two benzene groups are linked to each other through a single bond.

In this specification, examples of C ₃ -C ₁₀ cycloalkyl groups may include cyclopentyl group, cyclohexyl group, cycloheptyl group, adamantanyl group, and norbornanyl group.

As used herein, “deuteration” includes both fully deuteration and partially deuteration.

As used herein, “fluorination” includes both completely fluoride and partially fluoride.

In Formulas 2-1 and 2-2, b51 to b53 represent the number of L ₅₁ to L ₅₃ , respectively, and may be one of the integers from 1 to 5. When b51 is 2 or more, two or more L ₅₁ 's are the same as or different from each other, when b52 is 2 or more, two or more L ₅₂ 's are the same as or different from each other, and when b53 is 2 or more, two or more L ₅₃ 's are the same as each other. Or it may be different. For example, b51 to b53 may be independently 1 or 2.

In Formulas 2-1 and 2-2, L ₅₁ to L ₅₃ are independently of each other,

single bond; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidi Nyl group, triazinyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, dimethyldibenzosilolyl group , diphenyldibenzosilolyl group, -O(Q ₃₁ ), -S(Q ₃₁ ), -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B (Q ₃₁ )(Q ₃₂ ), -P(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)( Q ₃₁ ) (Q ₃₂ ), or any combination thereof, substituted or unsubstituted, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group , furan group, thiophene group, silol group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzosilol group, di Benzosilol group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilol group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group , quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, iso Thiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, dibenzoxacillin group, dibenzothiacillin group, dibenzodihydroazacillin group, dibenzodihydrodicillin group, dibenzodihydrociline group, dibenzodioxine group, dibenzooxathiin group, dibenzoxazine group, Dibenzopyran group, dibenzodithiine group, dibenzothiazine group, dibenzothiopyran group, dibenzocyclohexadiene group, dibenzodihydropyridine group, dibenzodihydropyrazine group, indolocarbazole group, indolodibenzofuran group, or indolodibenzothiophene group;

ego,

Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, It may be a pyrazinyl group or a triazinyl group.

In Formulas 2-1 and 2-2, _{X 54} is N or C(R ₅₄ ), X ₅₅ is N or C(R ₅₅ ), X ₅₆ is N or C(R ₅₆ ), and At least one of ₅₆ may be N. For a description of R ₅₄ to R ₅₆ , refer to what is described in the present specification. For example, two or three of X ₅₄ to X ₅₆ may be N.

In the present specification, R ₅₁ to R ₅₇ , R _57a , R _57b , R ₇₁ to R ₇₄ , R ₈₁ to R _{85, R 82a, R 82b , R 83a} , R _83b , R _84a and R _84b are each independently hydrogen , deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted with at least one R _10a A substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted with R _10a , a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, at least one R , substituted or unsubstituted with R _10a Substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted with _10a , C ₃ -C ₆₀ carbocyclic group, substituted or unsubstituted with at least one R _10a , substituted or unsubstituted with at least one R _10a Ringed C ₁ -C ₆₀ heterocyclic group, C ₆ -C 60 aryloxy group unsubstituted or substituted _with at least one R _10a , C ₆ -C ₆₀ arylthi substituted or unsubstituted with at least one R _10a group, C ₇ -C ₆₀ arylalkyl group substituted or unsubstituted with at least one R _10a , C ₂ -C ₆₀ heteroarylalkyl group substituted or unsubstituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)( It may be Q ₁ ), -S(=O) ₂ (Q ₁ ), or -P(=O)(Q ₁ )(Q ₂ ). For descriptions of Q ₁ to Q ₃ , refer to what is described in the present specification.

For example, i) in Formula 1, R ₁ , R _{21 to R 24 ,} R _24a , R _24b , R ₃ to R 7 , R _5a , R _5b , R _6a , R _6b , _{R 7a ,} R _7b , R ', and R" ii) R ₅₁ to R 57 , R _57a , R _57b , R ₇₁ to R ₇₄ , R ₈₁ to R ₈₅ , R _82a in Formulas 2-1, 2-2 and 3-1 _to 3-5 , R _82b , R _83a , R _83b , R _84a and R _84b and iii) R _10a are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, C ₁ -C ₁₀ Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexyl. C ₁ -C 20 alkyl group or C ₁ -C ₂₀ alkoxy group substituted with cenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, pyridinyl group, _pyrimidinyl group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group ), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C ₁ -C ₁₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazolyl group Zinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinoli Nyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzothiazolyl group, benzoisoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -O (Q ₃₁ ), -S (Q ₃₁ ), -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -P(Q ₃₁ )(Q ₃₂ ), Substituted or unsubstituted with -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)(Q ₃₁ )(Q ₃₂ ), or any combination thereof, Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl group, biphenyl group, C ₁ -C ₁₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thio Phenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group , indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, Benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzooxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group , benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azafluorenyl group, azadibenzosilol The group denoted by diary or formula 91; or

-C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ) or -P(=O)(Q ₁ )(Q ₂ );

ego,

Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH 2 CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH _{2 CDH 2} , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

n-propyl, substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, or any combination thereof group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyrite Dinyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, or triazinyl group;

It can be:

<Formula 91>

In Formula 91 above,

Ring CY ₉₁ and ring CY ₉₂ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group unsubstituted or substituted with at least one R _10a or a C ₁ -C ₃₀ heterocyclic group unsubstituted or substituted with at least one R _10a It is a cyclic group,

_{and _ _ _ _ _ _}

For descriptions of R ₉₁ , R _91a and R _91b , refer to the descriptions of R ₈₂ , R _82a and R _82b in this specification, respectively,

For a description of R _10a , refer to what is described herein,

* is a bonding site with a neighboring atom.

For example, in Formula 91 above,

Ring CY ₉₁ and ring CY ₉₂ are, independently of each other, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, substituted or unsubstituted with at least one R _10a ,

R ₉₁ , R _91a and R _91b are independently of each other,

hydrogen or C ₁ -C ₁₀ alkyl group; or

Substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, biphenyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, or any combination thereof, phenyl group, pyridine Dinyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, or triazinyl group;

It can be.

According to another embodiment, i) in Formula 1, R ₁ , R ₂₁ to R ₂₄ , R _24a , R _24b , R ₃ to R ₇ , R _5a , R _5b , R _{6a , R 6b ,} R _7a , R _7b , R', and R", ii) R ₅₁ to R 57, R _57a , R _57b , R ₇₁ to R ₇₄ , and R ₈₁ in Formulas _2-1 , 2-2, and 3-1 to 3-5 R ₈₅ , R _82a , R _82b , R _83a , R _83b , R _84a and R _84b , and iii) R _10a are independently of each other hydrogen, deuterium, -F, cyano group, nitro group, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by one of the following formulas 9-1 to 9-19, one of the following formulas 10-1 to 10-246 The group shown, -C(Q ₁ )(Q ₂ )(Q ₃ ), -Si(Q ₁ )(Q ₂ )(Q ₃ ), or -P(=O)(Q ₁ )(Q ₂ ) (only , the description of Q ₁ to Q ₃ refers to what is described herein) (provided that R _10a is not hydrogen):

In Formulas 9-1 to 9-19 and 10-1 to 10-246, * is a bonding site with an adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.

In Formulas 3-1 to 3-5, a71 to a74 each represent the number of R ₇₁ to R ₇₄ and may independently be an integer of 0 to 20. When a71 is 2 or more, 2 or more R ₇₁ 's may be the same as or different from each other, and when a72 is 2 or more, 2 or more R ₇₂ 's may be the same or different from each other. When a73 is 2 or more, 2 or more R ₇₃ 's may be the same as or different from each other. It may be the same or different, and when a74 is 2 or more, 2 or more R ₇₄ may be the same or different from each other. The a71 to a74 may be independently integers from 0 to 8.

In Formula 1, i) 2 groups among a1 R ₁ , ii) 2 groups among R ₂₁ to R ₂₃ , iii) 2 groups among a3 R ₃ , iv) 2 groups among a4 R ₄ , v) R _5a and R _5b , vi) R _6a and R _6b , and vii) R _7a and R _7b are each optionally bonded to each other through a single bond, double bond, or first linking group. , it may form _a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R 10a.

Meanwhile, in Formulas 3-1 to 3-5, L ₈₁ to L ₈₅ are independently of each other,

single bond;

*-C(Q ₄ )(Q ₅ )-*' or *-Si(Q ₄ )(Q ₅ )-*'; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidi Nyl group, triazinyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, dimethyldibenzosilolyl group , diphenyldibenzosilolyl group, -O(Q ₃₁ ), -S(Q ₃₁ ), -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B (Q ₃₁ )(Q ₃₂ ), -P(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)( Q ₃₁ ) (Q ₃₂ ), or any combination thereof, substituted or unsubstituted, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group , furan group, thiophene group, silol group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzosilol group, di Benzosilol group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilol group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group , quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, iso thiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzooxazole group, benzothiazole group, benzoxadiazole group or benzothiadiazole group;

ego,

Q ₄ , Q ₅ , Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, pyridinyl group, pyrimidinyl group , it may be a pyridazinyl group, a pyrazinyl group, or a triazinyl group.

로 표시된 그룹은 하기 화학식 CY71-1(1) 내지 CY71-1(8) 중 하나로 표시된 그룹이고, 및/또는 As another example, in Formulas 3-1 and 3-2,

The group represented by is a group represented by one of the following formulas CY71-1(1) to CY71-1(8), and/or

로 표시된 그룹은 하기 화학식 CY71-2(1) 내지 CY71-2(8) 중 하나로 표시된 그룹이고, 및/또는 Of formulas 3-1 and 3-3

The group represented by is a group represented by one of the following formulas CY71-2(1) to CY71-2(8), and/or

로 표시된 그룹은 하기 화학식 CY71-3(1) 내지 CY71-3(32) 중 하나로 표시된 그룹이고, 및/또는 Of formulas 3-2 and 3-4

The group represented by is a group represented by one of the following formulas CY71-3(1) to CY71-3(32), and/or

로 표시된 그룹은 하기 화학식 CY71-4(1) 내지 CY71-4(32) 중 하나로 표시된 그룹이고, 및/또는 In formulas 3-3 to 3-5,

The group represented by is a group represented by one of the following formulas CY71-4(1) to CY71-4(32), and/or

로 표시된 그룹은 하기 화학식 CY71-5(1) 내지 CY71-5(8) 중 하나로 표시된 그룹일 수 있다:In Formula 3-5 above,

The group represented by may be a group represented by one of the following formulas CY71-5(1) to CY71-5(8):

The formula CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4 (32) and CY71-5 (1) to CY71-5 (8),

_{For descriptions of X 81} to

_{and _ _ _ _ _ _}

_{and _ _ _ _ _ _}

In the formulas CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32), X ₈₆ and X ₈₇ are not a single bond at the same time,

_{and _ _ _ _ _ _}

_{and _ _ _ _ _ _}

In the formulas CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to _CY71-5 ( ₈ ), At the same time, it is not a single bond,

For descriptions of R ₈₆ to R ₈₉ , R _86a , R _86b , R _87a , R _87b , R _88a , R _88b , R _89a and R _89b , respectively, refer to the description of R ₈₁ in this specification.

Compound Specific Examples

According to one embodiment, the first emitter or the organometallic compound represented by Formula 1 may be one of the following compounds PD01 to PD08:

According to another embodiment, the heterocyclic compound may be one of the following compounds ET-1 to ET-6:

[Description of Figure 1]

Figure 1 schematically shows a cross-sectional view of a light-emitting device 10 according to an embodiment of the present invention. The light emitting device 10 includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

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

[First electrode (110)]

A substrate may be additionally disposed below the first electrode 110 or above the second electrode 150 in FIG. 1 . As the substrate, a glass substrate or a plastic substrate can be used. Alternatively, the substrate may be a flexible substrate, for example, polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate ( It may include a plastic with excellent heat resistance and durability, such as PAR (polyarylate), polyetherimide, or any combination thereof.

The first electrode 110 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. When the first electrode 110 is an anode, a high work function material that facilitates hole injection can be used as the first electrode material.

The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 110, which is a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or a material for the first electrode is used. Any combination can be used. Alternatively, in order to form the first electrode 110, which is a transflective electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), or aluminum-lithium (Al-Li) may be used as the first electrode material. ), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.

The first electrode 110 may have a single-layer structure (consist of a single layer) or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.

[Middle layer (130)]

An intermediate layer 130 is disposed on the first electrode 110. The intermediate layer 130 includes a light emitting layer.

The intermediate layer 130 includes a hole transport region disposed between the first electrode 110 and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode 150. region) may be further included.

In addition to various organic materials, the intermediate layer 130 may further include metal-containing compounds such as organometallic compounds and inorganic materials such as quantum dots.

Meanwhile, the intermediate layer 130 includes i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) between two adjacent emitting units. It may include a charge generation layer disposed in. When the intermediate layer 130 includes the light emitting unit and the charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.

[Hole transport area in middle layer 130]

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

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

For example, the hole transport region is a hole injection layer/hole transport layer, a hole injection layer/hole transport layer/light-emitting auxiliary layer, a hole injection layer/light-emitting auxiliary layer, and a hole transport layer/light-emitting layer, which are sequentially stacked from the first electrode 110. It may have a multi-layer structure of an auxiliary layer or a hole injection layer/hole transport layer/electron blocking layer.

The hole transport region may include a compound represented by Formula 201 below, a compound represented by Formula 202 below, or any combination thereof:

<Formula 201>

<Formula 202>

In formulas 201 and 202,

L ₂₀₁ to L ₂₀₄ are each independently a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a Click group,

L ₂₀₅ is *-O-*', *-S-*', *-N(Q ₂₀₁ )-*', at least one C ₁ -C ₂₀ alkylene group substituted or unsubstituted with at least one R _10a C ₂ -C ₂₀ alkenylene group substituted or unsubstituted with R _10a , C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a , or unsubstituted or substituted with at least one R _10a is a C ₁ -C ₆₀ heterocyclic group,

xa1 to xa4 are independently one of the integers from 0 to 5,

xa5 is one of the integers from 1 to 10,

R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a , or a C ₁ -C substituted or unsubstituted with at least one R _{10a 60} heterocyclic groups,

R ₂₀₁ and R ₂₀₂ are optionally a single bond, a C ₁ -C ₅ alkylene group substituted or unsubstituted with at least one R _10a , or a C ₂ -C substituted or unsubstituted with at least one R _{10a 5} may be linked to each other through an alkenylene group to form a C ₈ -C ₆₀ polycyclic group (e.g., carbazole group, etc.) substituted or unsubstituted with at least one R _10a (e.g., the following compounds HT16, etc.),

R ₂₀₃ and R ₂₀₄ are optionally a single bond, a C ₁ -C 5 alkylene group substituted or unsubstituted with at least one R _10a , or a C ₂ -C ₅ unsubstituted or substituted with at least _one R _10a may be linked to each other through an alkenylene group to form a C ₈ -C ₆₀ polycyclic group substituted or unsubstituted with at least one R _10a ,

na1 may be one of the integers from 1 to 4.

For example, each of Formulas 201 and 202 may include at least one of the groups represented by the following Formulas CY201 to CY217:

In the above formulas CY201 to CY217, the description of R _10b and R _10c each refers to the description of R _10a in the specification, and rings CY ₂₀₁ to CY ₂₀₄ are each independently a C ₃ -C ₂₀ carbocyclic group. or a C ₁ -C ₂₀ heterocyclic group, and at least one hydrogen in the formulas CY201 to CY217 may be substituted or unsubstituted with R _10a as described herein.

According to one embodiment, rings CY ₂₀₁ to CY ₂₀₄ in the formula CY201 to CY217 may independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

According to another embodiment, each of Formulas 201 and 202 may include at least one of the groups represented by Formulas CY201 to CY203.

According to yet another embodiment, Formula 201 may include at least one of the groups represented by Formulas CY201 to CY203 and at least one of the groups represented by Formulas CY204 to CY217, respectively.

According to another embodiment, in Formula 201, xa1 is 1, R ₂₀₁ is a group represented by one of the formulas CY201 to CY203, xa2 is 0, and R ₂₀₂ may be a group represented by one of the formulas CY204 to CY207. .

According to another embodiment, each of Formulas 201 and 202 may not include the group represented by Formulas CY201 to CY203.

According to yet another embodiment, each of the formulas 201 and 202 does not include the group represented by the formulas CY201 to CY203, and may include at least one of the groups represented by the formulas CY204 to CY217.

As another example, each of Formulas 201 and 202 may not include the group represented by Formulas CY201 to CY217.

For example, the hole transport region is one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB , TAPC, HMTPD, TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline/ Dodecylbenzenesulfonic acid (polyaniline/dodecylbenzenesulfonic acid)), PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) nate))), Pani/CSA (Polyaniline/Camphor sulfonic acid), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate)), or any of them. May include combinations of:

The thickness of the hole transport region may be about 50Å to about 10000Å, for example, about 100Å to about 4000Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer is about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is The thickness may be from about 50 Å to about 2000 Å, for example from about 100 Å to about 1500 Å. When the thickness of the hole transport region, hole injection layer, and hole transport layer satisfies the above-mentioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

The light emitting auxiliary layer is a layer that serves to increase light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light emitting layer, and the electron blocking layer prevents electron leakage from the light emitting layer to the hole transport region. It is a layer that plays a role. Materials that can be included in the hole transport region described above can be included in the light emitting auxiliary layer and the electron blocking layer.

[p-dopant]

In addition to the materials described above, the hole transport region may include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed (eg, in the form of a single layer consisting of the charge-generating material) within the hole transport region.

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

For example, the LUMO energy level of the p-dopant may be -3.5 eV or less.

According to one embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, an element EL1 and an element EL2-containing compound, or any combination thereof.

Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.

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

<Formula 221>

In Formula 221,

R ₂₂₁ to R ₂₂₃ are each independently a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a It's a group,

At least one of R ₂₂₁ to R ₂₂₃ is independently a cyano group; -F; -Cl; -Br; -I; a C ₁ -C ₂₀ alkyl group substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof; Or it may be a C ₃ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group substituted with any combination thereof.

Among the element EL1 and element EL2-containing compounds, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a non-metal, a metalloid, or a combination thereof.

Examples of the metal include alkali metals (eg, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); Alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); 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), etc.); metals after transfer (eg, zinc (Zn), indium (In), tin (Sn), etc.); Lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), and terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); It may include etc.

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

Examples of the non-metal may include oxygen (O), halogen (eg, F, Cl, Br, I, etc.).

For example, the element EL1 and element EL2-containing compounds include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g. , metalloid fluoride, metalloid chloride, metalloid bromide, metalloid iodide, etc.), metal telluride, or any combination thereof.

Examples of the metal oxide include tungsten oxide (e.g., WO, W ₂ O ₃ , WO ₂ , WO ₃ , W ₂ O ₅ , etc.), vanadium oxide (e.g., VO, V ₂ O ₃ , VO ₂ , V ₂ O ₅ , etc.), molybdenum oxide (MoO, Mo ₂ O ₃ , MoO ₂ , MoO ₃ , Mo ₂ O ₅ , etc.), rhenium oxide (for example, ReO ₃ etc.), etc.

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 halides include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc. It can be included.

Examples of the alkaline earth metal halides include BeF ₂ , MgF ₂ , CaF ₂ , SrF ₂ , BaF ₂ , BeCl ₂ , MgCl ₂ , CaCl ₂ , SrCl ₂ , BaCl ₂ , BeBr ₂ , MgBr ₂ , CaBr ₂ , SrBr ₂ , BaBr ₂ , BeI ₂ , MgI ₂ , CaI ₂ , SrI ₂ , BaI _2, etc.

Examples of the transition metal halides include titanium halides (e.g., TiF ₄ , TiCl ₄ , TiBr ₄ , TiI _{4 ,} etc.), zirconium halides (e.g., ZrF ₄ , ZrCl ₄ , ZrBr ₄ , ZrI ₄ etc.), hafnium halides (e.g. HfF ₄ , HfCl ₄ , HfBr ₄ , HfI ₄ etc.), vanadium halides (e.g. VF ₃ , VCl ₃ , VBr ₃ , VI ₃ etc.), niobium halides (e.g., NbF ₃ , NbCl ₃ , NbBr ₃ , NbI _{3 ,} etc.), tantalum halides (e.g., TaF ₃ , TaCl ₃ , TaBr ₃ , TaI _{3 ,} etc.), chromium halides (e.g., CrF ₃ , CrCl ₃ , CrBr ₃ , CrI _3, etc.), molybdenum halides (e.g., MoF ₃ , MoCl ₃ , MoBr ₃ , MoI _3, etc.), tungsten halides (e.g., WF ₃ , WCl ₃ , WBr) ₃ , WI _3, etc.), manganese halides (e.g., MnF ₂ , MnCl ₂ , MnBr ₂ , MnI _2, etc.), technetium halides (e.g., TcF ₂ , TcCl ₂ , TcBr ₂ , TcI ₂ , etc.) , rhenium halides (e.g., ReF ₂ , ReCl ₂ , ReBr ₂ , ReI _{2 ,} etc.), iron halides (e.g., FeF ₂ , FeCl ₂ , FeBr ₂ , FeI _{2 ,} etc.), ruthenium halides (e.g. For example, RuF ₂ , RuCl ₂ , RuBr ₂ , RuI _2, etc.), osmium halides (for example, OsF ₂ , OsCl ₂ , OsBr ₂ , OsI _2, etc.), cobalt halides (for example, CoF ₂ , CoCl ₂ , CoBr ₂ , CoI _{2 ,} etc.), rhodium halides (e.g. RhF ₂ , RhCl ₂ , RhBr 2 , RhI ₂ , etc.), iridium halides (e.g. IrF ₂ , IrCl ₂ , IrBr _{2 ,} etc.) IrI _2, etc.), nickel halides (e.g., NiF ₂ , NiCl ₂ , NiBr ₂ , NiI _2, etc.), palladium halides (e.g., PdF ₂ , PdCl ₂ , PdBr ₂ , PdI _2, etc.), platinum Halides (e.g., PtF ₂ , PtCl ₂ , PtBr ₂ , PtI _{2 ,} etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl , AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

Examples of metal halides after the transfer include zinc halides (e.g. ZnF ₂ , ZnCl ₂ , ZnBr ₂ , ZnI ₂ etc.), indium halides (e.g. InI ₃ etc.), tin halides (e.g. For example, SnI _2, etc.), etc. may be included.

Examples of the lanthanide metal halide include YbF, YbF ₂ , YbF ₃ , SmF ₃ , YbCl, YbCl ₂ , YbCl ₃ SmCl ₃ , YbBr, YbBr ₂ , YbBr ₃ , SmBr ₃ , YbI, YbI ₂ , YbI ₃ , It may include SmI ₃ , etc.

Examples of the metalloid halide may include antimony halide (eg, SbCl ₅ , etc.).

Examples of the metal telluride include alkali metal telluride (e.g., Li ₂ Te, Na ₂ Te, K ₂ Te, Rb ₂ Te, Cs ₂ Te, etc.), alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g. TiTe ₂ , ZrTe ₂ , HfTe ₂ , V ₂ Te ₃ , Nb ₂ Te ₃ , Ta ₂ Te ₃ , Cr ₂ Te ₃ , Mo ₂ Te ₃ , W ₂ Te ₃ , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu ₂ Te, CuTe, Ag ₂ Te, AgTe, Au ₂ Te, etc.), After transfer metal telluride (e.g. ZnTe, etc.), lanthanide metal telluride (e.g. LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.) may be included.

[Emitting layer in the middle layer (130)]

When the light-emitting device 10 is a full-color light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and/or a blue light-emitting layer for each subpixel. Alternatively, the light-emitting layer may have a structure in which two or more layers of a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked in contact or spaced apart, or two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material are mixed without layer distinction. It has a structured structure and can emit white light.

According to one embodiment, the light emitting layer may further include a host, an auxiliary dopant, a sensor, a delayed fluorescent material, or any combination thereof in addition to the first emitter as described herein.

When the light emitting layer further includes a host in addition to the first emitter, the content of the first emitter may be about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.

The thickness of the light emitting layer may be about 100Å to about 1000Å, for example, about 200Å to about 600Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[host]

The host in the emitting layer is an electron transport compound described herein (for example, see the compound represented by Formula 2-1 or 2-2), a hole transport compound (for example, a compound represented by Formula 3-1 to 3-5) (refer to the compound indicated as one), or a combination thereof.

As another example, the host may include an alkaline earth metal complex, a post-transfer metal complex, or any combination thereof. For example, the host may include a Be complex (eg, compound H55 below), an Mg complex, a Zn complex, or any combination thereof.

As another example, the host is one of the following compounds H1 to H130, ADN (9,10-Di(2-naphthyl)anthracene), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene ), TBADN (9,10-di(2-naphthyl)-2-t-butyl-anthracene), CBP (4,4′-bis(N-carbazolyl)-1,1′-biphenyl), mCP (1, 3-di-9-carbazolylbenzene), TCP (1,3,5-tri(carbazol-9-yl)benzene), or any combination thereof:

Alternatively, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.

The host may be modified in various ways, such as containing only one type of compound or containing two or more different types of compounds.

[Phosphorescent dopant]

The light emitting layer is a phosphorescent dopant and may include a first emitter as described herein.

Alternatively, the light emitting layer may further include an organometallic compound represented by the following formula 401 in addition to the first emitter as described herein:

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

Among the formulas 401 and 402,

M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), and terbium. (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

L ₄₀₁ is a ligand represented by the above formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, 2 or more L ₄₀₁ are the same or different from each other,

L ₄₀₂ is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and when xc2 is 2 or more, 2 or more L ₄₀₂ are the same or different from each other,

X ₄₀₁ and X ₄₀₂ are independently of each other nitrogen or carbon,

Ring A ₄₀₁ and Ring A ₄₀₂ are, independently of each other, a C ₃ -C ₆₀ carbocyclic group, or a C ₁ -C ₆₀ heterocyclic group,

T ₄₀₁ is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q ₄₁₁ )-*', *-C(Q ₄₁₁ )( Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=C(Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=*' or *=C(Q ₄₁₁ )=*',

_{X 403 and _ _ _} )(Q ₄₁₄ ) or Si(Q ₄₁₃ )(Q ₄₁₄ ),

For the description of Q ₄₁₁ to Q ₄₁₄ , refer to the description of Q ₁ in the specification, respectively,

R ₄₀₁ and R ₄₀₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -substituted or unsubstituted with at least one R _10a C ₂₀ alkyl group, C _{1 -C 20 alkoxy} group substituted or unsubstituted with at least one R _10a , C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R 10a, with at least one R _10a Substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group, -Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), -C(=O)(Q ₄₀₁ ), -S(=O) ₂ (Q ₄₀₁ ), or -P(=O)(Q ₄₀₁ )(Q ₄₀₂ ),

For the description of Q ₄₀₁ to Q ₄₀₃ , refer to the description of Q ₁ in the specification, respectively,

xc11 and xc12 are independently one of the integers from 0 to 10,

* and *' in Formula 402 are each binding sites with M in Formula 401.

For example, in Formula 402, i) X ₄₀₁ may be nitrogen and X ₄₀₂ may be carbon, or ii) both X ₄₀₁ and X ₄₀₂ may be nitrogen.

As another example, when xc1 in Formula 402 is 2 or more, two rings A ₄₀₁ among 2 or more L ₄₀₁ are optionally connected to each other through a linking group T ₄₀₂ , or two rings A ₄₀₂ are optionally connected to each other, They can be connected to each other through the linking group T ₄₀₃ (see compounds PD1 to PD4 and PD7 below). For descriptions of T ₄₀₂ and T ₄₀₃ , refer to the description of T ₄₀₁ in this specification.

In Formula 401, L ₄₀₂ may be any organic ligand. For example, L ₄₀₂ is a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), -C (=O), an isonitrile group. , -CN group, phosphorus group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.

[Fluorescent dopant]

The light emitting layer may further include a fluorescent dopant in addition to the first emitter as described herein.

The fluorescent dopant may include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.

For example, the fluorescent dopant may include a compound represented by the following formula 501:

<Formula 501>

In formula 501,

Ar ₅₀₁ , L ₅₀₁ to L ₅₀₃ , R ₅₀₁ and R ₅₀₂ are each independently a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , or substituted or unsubstituted with at least one R _10a It is a circular C ₁ -C ₆₀ heterocyclic group,

xd1 to xd3 are independently 0, 1, 2, or 3,

xd4 can be 1, 2, 3, 4, 5, or 6.

For example, Ar ₅₀₁ in Formula 501 may include a condensed ring group in which three or more monocyclic groups are condensed with each other (eg, an anthracene group, chrysene group, pyrene group, etc.).

As another example, in Formula 501, xd4 may be 2.

For example, the fluorescent dopant may include one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

[Delayed fluorescent material]

The light emitting layer may further include a delayed fluorescent material.

The delayed fluorescent material herein may be selected from any compound capable of emitting delayed fluorescence by a delayed fluorescence emission mechanism.

The delayed fluorescent material included in the light-emitting layer may function as a host or dopant, depending on the type of other material included in the light-emitting layer.

According to one embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be 0 eV or more and 0.5 eV or less. The difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the range described above, thereby changing the delayed fluorescent material from the triplet state to the singlet state. Reverse energy transfer (up-conversion) is effectively achieved, and the luminous efficiency of the light-emitting device 10 can be improved.

For example, the delayed fluorescent material may _include : i) at _least one electron donor (e.g., a π electron-rich C ₃ -C ₆₀ cyclic group such as a carbazole group) group), etc.) and at least one electron acceptor (e.g., sulfoxide group, cyano group, π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group (π electron-deficient nitrogen-containing C ₁ - ii) materials containing a C _{8 -C 60} polycyclic group containing two or more cyclic groups condensed while sharing boron (B); and ii) materials containing a C ₈ -C ₆₀ polycyclic group.

Examples of the delayed fluorescent material may include at least one of the following compounds DF1 to DF14:

[Electron transport area in middle layer 130]

The electron transport region is i) a single layer structure consisting of a single material, ii) a single layer structure consisting of a plurality of different materials, or iii) a plurality of structures. It may have a multi-layer structure including a plurality of layers containing 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 any combination thereof.

For example, the electron transport region may be an electron transport layer/electron injection layer, a hole blocking layer/electron transport layer/electron injection layer, an electron control layer/electron transport layer/electron injection layer, or a buffer layer/electron transport layer/ It may have a structure such as an electron injection layer.

The electron transport region may include a heterocyclic compound (e.g., a compound represented by Formula 8 above) as described herein.

For example, the electron transport region may have a structure in which an electron transport layer and an electron injection layer are sequentially stacked, and the heterocyclic compound described herein may be included in the electron transport layer.

As another example, the electron transport region may have a structure in which a hole blocking layer, an electron transport layer, and an electron injection layer are sequentially stacked, and the heterocyclic compound described herein may be included in the electron transport layer.

The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer of the electron transport region) contains at least one π electron-deficient compound in addition to the heterocyclic compound as described herein. It may include _{a metal-free compound containing a π electron-deficient nitrogen-containing C 1 -C 60 cyclic group .}

For example, the electron transport region may further include a compound represented by Formula 601 below, in addition to the heterocyclic compounds described herein.

<Formula 601>

[Ar ₆₀₁ ] _xe11 -[(L ₆₀₁ ) _xe1 -R ₆₀₁ ] _xe21

In the above formula 601,

Ar ₆₀₁ , and L ₆₀₁ are each independently a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a It is a cyclic group,

xe11 is 1, 2, or 3,

xe1 is 0, 1, 2, 3, 4, or 5,

R ₆₀₁ is a C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least _one R 10a, -Si(Q ₆₀₁ )(Q ₆₀₂ )(Q ₆₀₃ ), -C(=O)(Q ₆₀₁ ), -S(=O) ₂ (Q ₆₀₁ ), or -P(=O)(Q ₆₀₁ )(Q ₆₀₂ ) ,

For the description of Q ₆₀₁ to Q ₆₀₃ , respectively, refer to the description of Q ₁ in this specification,

xe21 is 1, 2, 3, 4, or 5,

At least one of Ar ₆₀₁ , L ₆₀₁ and R ₆₀₁ may independently be a π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group substituted or unsubstituted with at least one R _10a .

For example, when xe11 in Formula 601 is 2 or more, 2 or more Ar ₆₀₁ may be connected to each other through a single bond.

As another example, Ar ₆₀₁ in Formula 601 may be a substituted or unsubstituted anthracene group.

As another example, the electron transport region may further include a compound represented by the following formula 601-1, in addition to the heterocyclic compounds described herein:

<Formula 601-1>

In the above formula 601-1,

X ₆₁₄ is N or C(R ₆₁₄ ), X ₆₁₅ is N _or C ₍ R ₆₁₅ ), X ₆₁₆ is N or C(R ₆₁₆ ), and at least one of

For descriptions of L ₆₁₁ to L ₆₁₃ , refer to the description of L ₆₀₁ above, respectively.

For descriptions of xe611 to xe613, refer to the description of xe1 above, respectively.

For descriptions of R ₆₁₁ to R ₆₁₃ , refer to the description of R ₆₀₁ above, respectively.

R ₆₁₄ to R ₆₁₆ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , a C _{3 -C 60 carbocyclic} group substituted or unsubstituted with at least one R _10a , or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R 10a.

For example, in Formulas 601 and 601-1, xe1 and xe611 to xe613 may be independently 0, 1, or 2.

According to one embodiment, the electron transport region is, in addition to the heterocyclic compounds described herein, one of the following compounds ET1 to ET46, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline) , Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , BAlq, TAZ, NTAZ, or any combination thereof:

The thickness of the electron transport region may be about 100Å to about 5000Å, for example, about 160Å to about 4000Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer is independently from each other, about 20 Å to about 1000 Å, For example, it may be about 30Å to about 300Å, and the thickness of the electron transport layer may be about 100Å to about 1000Å, for example, about 150Å to about 500Å. When the thickness of the buffer layer, hole blocking layer, electron control layer, electron transport layer, and/or electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.

The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkaline metal complex may be a Li ion, Na ion, K ion, Rb ion, or Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, Mg ion, Ca ion, Sr ion, or Ba ion. You can. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, and hydroxyphenyl. Oxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclo Pentadiene, or any combination thereof.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1(LiQ) or ET-D2:

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

The electron injection layer has i) a single layer structure consisting of a single material (consist of), ii) a single layer structure (consist of) a single layer containing a plurality of different materials, or iii) a plurality of layers. It may have a multilayer structure having a plurality of layers containing different materials.

The electron injection layer is 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 complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof. It can be included.

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

The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound are oxides, halides (e.g., fluoride, chloride, bromide, iodide, etc.), telluride, or any combination thereof.

The alkali metal-containing compound is an alkali metal oxide such as Li ₂ O, Cs ₂ O, K ₂ O, an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI, or the like. It may include any combination thereof. The alkaline earth metal-containing compounds include BaO, SrO, CaO, Ba _x Sr _1-x O (x is a real number satisfying 0<x<1), Ba _x Ca _1-x O (x is 0<x< It may include alkaline earth metal compounds such as (a real number that satisfies 1). The rare earth metal-containing compound is YbF ₃ , ScF ₃ , Sc ₂ O ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , TbF ₃ , YbI ₃ , ScI ₃ , TbI ₃ , or any combination thereof. It can be included. Alternatively, the rare earth metal-containing compound may include the lanthanide metal telluride. Examples of the lanthanide metal telluride include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La ₂ Te ₃ , Ce ₂ Te ₃ , Pr ₂ Te ₃ , Nd ₂ Te ₃ , Pm ₂ Te ₃ , Sm ₂ Te ₃ , Eu ₂ Te ₃ , Gd ₂ Te ₃ , Tb ₂ Te 3 , Dy ₂ Te ₃ , Ho _{2 Te 3 ,} Er ₂ Te ₃ , It may include Tm ₂ Te ₃ , Yb ₂ Te ₃ , Lu ₂ Te ₃ , etc.

The alkali metal complex, alkaline earth metal complex and rare earth metal complex include i) one of the metal ions of the alkali metal, alkaline earth metal and rare earth metal as described above and ii) a ligand bound to the metal ion, for example, hydroxy Quinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, It may include hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

The electron injection layer is an alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or thereof as described above. It may consist of any combination, or may further include an organic substance (for example, a compound represented by Chemical Formula 601).

According to one embodiment, the electron injection layer i) consists of 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). alkali metal halides); and b) alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, or a LiF:Yb co-deposited layer.

When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal The complex, or any combination thereof, may be uniformly or non-uniformly dispersed in the matrix containing the organic material.

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

[Second electrode (150)]

The second electrode 150 is disposed on the middle layer 130 as described above. The second electrode 150 may be a cathode, which is an electron injection electrode. In this case, the material for the second electrode 150 is a metal, alloy, electrically conductive compound, or any of the materials having a low work function. A combination of can be used.

The second electrode 150 includes lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In). ), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any 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 having a plurality of layers.

[Capping layer]

A first capping layer may be disposed outside the first electrode 110, and/or a second capping layer may be disposed outside the second electrode 150. Specifically, the light emitting device 10 has a structure in which a first capping layer, a first electrode 110, an intermediate layer 130, and a second electrode 150 are sequentially stacked, the first electrode 110, the intermediate layer 130 , a structure in which the second electrode 150 and the second capping layer are sequentially stacked, or a structure in which the first capping layer, the first electrode 110, the middle layer 130, the second electrode 150, and the second capping layer are sequentially stacked. It can have a structure.

The light generated in the light-emitting layer of the intermediate layer 130 of the light-emitting device 10 may pass through the first electrode 110, which is a transflective electrode or a transmissive electrode, and the first capping layer, and be extracted to the outside of the light-emitting device 10. Light generated in the light-emitting layer of the middle layer 130 may pass through the second electrode 150 and the second capping layer, which are semi-transmissive or transmissive electrodes, and be taken out to the outside.

The first capping layer and the second capping layer may serve to improve external light emission efficiency based on the principle of constructive interference. As a result, the light extraction efficiency of the light-emitting device 10 can be increased, and the light-emitting efficiency of the light-emitting device 10 can be improved.

Each of the first capping layer and the second capping layer may include a material having a refractive index (at 589 nm) of 1.6 or more.

The first capping layer and the second capping layer may independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

At least one of the first capping layer and the second capping layer is, independently of each other, a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, porphine derivatives, phthalocyanine derivatives, It may include naphthalocyanine derivatives, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compounds, heterocyclic compounds and amine group-containing compounds may optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. You can. According to one embodiment, at least one of the first capping layer and the second capping layer may independently include an amine group-containing compound.

For example, at least one of the first capping layer and the second capping layer may independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

According to another embodiment, at least one of the first capping layer and the second capping layer is, independently of each other, one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any compound thereof. May include:

[Electronic Device]

The light emitting device may be included in various electronic devices. For example, an electronic device including the light-emitting device may be a light-emitting device, an authentication device, or the like.

The electronic device (eg, light-emitting device) may further include, in addition to the light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or color conversion layer may be disposed in at least one direction of travel of light emitted from the light emitting device. For example, the light emitted from the light emitting device may be blue light, green light, or white light. For a description of the light emitting device, refer to the above description. According to one embodiment, the color conversion layer may include quantum dots.

The electronic device may include a first substrate. The first substrate includes a plurality of subpixel areas, the color filter includes a plurality of color filter areas corresponding to each of the plurality of subpixel areas, and the color conversion layer is located in each of the plurality of subpixel areas. It may include a plurality of corresponding color conversion areas.

A pixel defining layer is disposed between the plurality of subpixel areas to define each subpixel area.

The color filter may further include a plurality of color filter regions and a light-shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions. It may further include.

The plurality of color filter areas (or the plurality of color conversion areas) include: a first area emitting first color light; a second region emitting second color light; and/or a third region emitting third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. For example, 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. For example, the plurality of color filter regions (or plurality of color conversion regions) may include quantum dots. Specifically, 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. For a description of quantum dots, refer to what is described herein. The first area, the second area, and/or the third area may each further include a scatterer.

For example, the light emitting device emits first light, the first region absorbs the first light and emits 1-1 color light, and the second region absorbs the first light, Light of the 2-1st color may be emitted, and the third region may absorb the first light to emit light of the 3-1st color. At this time, the 1-1 color light, the 2-1 color light, and the 3-1 color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 color light may be blue light.

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

The thin film transistor may further include a gate electrode, a gate insulating film, etc.

The active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, etc.

The electronic device may further include a sealing portion that seals the light emitting device. The sealing part may be disposed between the color filter and/or color conversion layer and the light emitting device. The sealing part allows light from the light emitting device to be extracted to the outside, while simultaneously blocking external air and moisture from penetrating into the light emitting device. The sealing unit may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulating layer including one or more organic layers and/or inorganic layers. When the sealing part is a thin film encapsulation layer, the electronic device can be flexible.

In addition to the color filter and/or color conversion layer, various functional layers may be additionally disposed on the sealing portion depending on the purpose of the electronic device. Examples of the functional layer may include a touch screen layer, a polarizing layer, and the like. The touch screen layer may be a resistive 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 that authenticates an individual using biometric information (eg, fingertips, eyes, etc.).

The authentication device may further include a means for collecting biometric information in addition to the light emitting device described above.

The electronic devices include various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game machines, and medical devices (e.g., electronic thermometers, blood pressure monitors). , blood sugar meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasonic diagnostic devices, endoscope display devices), fish finders, various measuring devices, instruments (e.g., instruments for vehicles, aircraft, and ships), projectors, etc. It can be applied.

[Electronics]

The light emitting device may be included in various electronic devices.

For example, electronic devices including the above light-emitting elements include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal lights, head-up displays, fully or partially transparent displays, Flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, phones, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, One of a digital camera, camcorder, viewfinder, micro display, 3D display, virtual or augmented reality display, vehicle, video wall including multiple displays tiled together, theater or stadium screen, phototherapy device, and signage. It can be.

Since the light-emitting device has excellent luminous efficiency and long lifespan, the electronic device including the light-emitting device can have characteristics such as high brightness, high resolution, and low power consumption.

[Explanation of Figures 2 and 3]

Figure 2 is a cross-sectional view of a light emitting device, which is one of the electronic devices according to an embodiment of the present invention.

The light emitting device of FIG. 2 includes a substrate 100, a thin film transistor (TFT), a light emitting element, and an encapsulation unit 300 that seals the light emitting element.

The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 prevents impurities from penetrating through the substrate 100 and may serve to provide a flat surface on the upper part of the substrate 100.

A thin film transistor (TFT) may be disposed on the buffer layer 210. The thin film transistor (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 includes a source region, a drain region, and a channel region.

A gate insulating film 230 may be disposed on top of the active layer 220 to insulate the active layer 220 and the gate electrode 240, and a 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. The interlayer insulating film 250 is disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate them.

A source electrode 260 and a 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 the source and drain regions of the active layer 220, and the source electrode 260 may be in contact with the exposed source and drain regions of the active layer 220. ) and a drain electrode 270 may be disposed.

Such a thin film transistor (TFT) can be electrically connected to a light-emitting device to drive the light-emitting device, and is covered and protected 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 intermediate layer 130, and a second electrode 150.

The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a predetermined area without covering the entire drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed drain electrode 270.

A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining film 290 exposes a predetermined area of the first electrode 110, and an intermediate layer 130 may be formed in the exposed area. The pixel defining layer 290 may be a polyimide or polyacrylic organic layer. Although not shown in FIG. 2 , some or more of the middle layer 130 may extend to the upper part of the pixel defining layer 290 and be disposed in the form of a common layer.

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

An encapsulation portion 300 may be disposed on the second capping layer 170. The encapsulation portion 300 may be disposed on the light emitting device to protect the light emitting device from moisture or oxygen. The encapsulation portion 300 is an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof, polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, Polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) ) or an organic layer including any combination thereof, or a combination of an inorganic layer and an organic layer.

Figure 3 is a cross-sectional view of a light-emitting device, which is one of electronic devices according to another embodiment of the present invention.

The light emitting device of FIG. 3 is the same as the light emitting device of FIG. 2 except that a light blocking pattern 500 and a functional area 400 are additionally disposed on the encapsulation portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. According to one embodiment, the light-emitting device included in the light-emitting device of FIG. 3 may be a tandem light-emitting device.

[Description of Figure 4]

FIG. 4 is a perspective view schematically showing an electronic device 1 including a light-emitting device according to an embodiment of the present invention. The electronic device 1 is a device that displays moving images or still images, such as a mobile phone, a smart phone, a tablet personal computer, a mobile communication terminal, an electronic notebook, an e-book, or a PMP. It may be a variety of products or a part of them, such as a portable multimedia player (portable multimedia player) or a navigation device, a portable electronic device (Ultra Mobile PC (UMPC)), a television, a laptop, a monitor, a billboard, or the Internet of Things (IOT). Additionally, the electronic device 1 may be or be part of a wearable device such as a smart watch, a watch phone, a glasses-type display, or a head mounted display (HMD). Of course, the present invention is not limited to this. For example, the electronic device 1 includes a dashboard of a car, a center information display (CID) placed on the center fascia or dashboard of a car, and a room mirror display that replaces the side mirror of a car. display), entertainment for the rear seats of a car or a display placed on the back of the front seat, a head-up display (HUD) installed in the front of the car or projected on the front window glass, a holographic augmented reality head-up display (Computer Generated) It may be a Hologram Augmented Reality Head Up Display (CGH AR HUD). Figure 4 shows a case where the electronic device 1 is a smart phone for convenience of explanation.

The electronic device 1 may include a display area (DA) and a non-display area (NDA) outside the display area (DA). A display device can implement an image through an array of a plurality of pixels arranged two-dimensionally in the display area (DA).

The non-display area (NDA) is an area that does not display images and may entirely surround the display area (DA). Drivers for providing electrical signals or power to display elements arranged in the display area (DA) may be placed in the non-display area (NDA). A pad, which is an area where electronic devices or printed circuit boards can be electrically connected, may be placed in the non-display area (NDA).

The electronic device 1 may have different lengths in the x-axis direction and lengths in the y-axis direction. For example, as shown in FIG. 4, the length in the x-axis direction may be shorter than the length in the y-axis direction. For another example, the length in the x-axis direction and the length in the y-axis direction may be the same. For another example, the length in the x-axis direction may be longer than the length in the y-axis direction.

[Description of Figures 5 and 6a to 6c]

FIG. 5 is a diagram schematically showing the exterior of a vehicle 1000 as an electronic device including a light-emitting device according to an embodiment of the present invention. 6A to 6C are diagrams schematically showing the interior of a vehicle 1000 according to various implementation examples of the present invention.

Referring to FIGS. 5, 6A, 6B, and 6C, the vehicle 1000 may refer to various devices that move a vehicle such as a human, object, or animal from a source to a destination. The vehicle 1000 may include a vehicle traveling on a road or track, a ship moving on the sea or a river, and an airplane flying in the sky using the action of air.

The vehicle 1000 can travel on a road or track. The vehicle 1000 may move in a predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three- or four-wheeled vehicle, construction equipment, a two-wheeled vehicle, a motor vehicle, a bicycle, and a train running on a track.

The vehicle 1000 may include a body having an interior and an exterior, and a chassis on which mechanical devices necessary for driving are installed in the remaining parts excluding the body. The exterior of the car body may include fillers provided at the boundaries between the front panel, bonnet, roof panel, rear panel, trunk, and doors. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a running device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front, rear, left and right wheels, etc.

The vehicle 1000 includes a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger dashboard 1600, and a display device 2. It can be included.

The side window glass 1100 and the front window glass 1200 may be partitioned by a filler disposed between the side window glass 1100 and the front window glass 1200.

The side window glass 1100 may be installed on the side of the vehicle 1000. In one embodiment, the side window glass 1100 may be installed on the door of the vehicle 1000. There may be a plurality of side window glasses 1100 and they may face each other. In one embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one embodiment, the first side window glass 1110 may be disposed adjacent to the cluster 1400. The second side window glass 1120 may be placed adjacent to the passenger seat dashboard 1600.

In one embodiment, the side window glasses 1100 may be spaced apart from each other in the x-direction or -x-direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or -x direction. In other words, the virtual straight line L connecting the side window glasses 1100 may extend in the x direction or -x direction. For example, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x direction or -x direction.

The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.

The side mirror 1300 may provide a view of the rear of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one implementation, a plurality of side mirrors 1300 may be provided. One of the plurality of side mirrors 1300 may be disposed outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 may be disposed outside the second side window glass 1120.

Cluster 1400 may be located in front of the steering wheel. The cluster 1400 includes a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge turn indicator light, a high beam indicator light, a warning light, a seat belt warning light, an odometer, an odometer, an automatic shift selection lever indicator light, a door open warning light, an engine oil warning light, and /Or a low fuel warning light may be placed.

The center fascia 1500 may include a control panel with a plurality of buttons for controlling an audio device, an air conditioning device, and a seat heater. The center fascia 1500 may be placed on one side of the cluster 1400.

The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 interposed therebetween. In one embodiment, the cluster 1400 may be arranged to correspond to the driver's seat (not shown), and the passenger seat dashboard 1600 may be placed to correspond to the passenger seat (not shown). In one implementation, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.

In one embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be placed inside the vehicle 1000. In one embodiment, the display device 2 may be disposed between side window glasses 1100 facing each other. The display device 2 may be disposed on at least one of the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.

The display device 2 may include an organic light emitting display, an inorganic light emitting display, a quantum dot display, etc. Hereinafter, the present invention will be described. As the display device 2 according to one embodiment, an organic light emitting display device including a light emitting element according to the present invention will be described as an example. However, various types of display devices as described above may be used in embodiments of the present invention.

Referring to FIG. 6A , the display device 2 may be placed on the center fascia 1500. In one implementation, the display device 2 can display navigation information. In one implementation, the display device 2 can display audio, video, or information about vehicle settings.

Referring to FIG. 6B, the display device 2 may be disposed in a cluster 1400. In this case, the cluster 1400 can display driving information, etc. through the display device 2. That is, the cluster 1400 can be implemented digitally. The digital cluster 1400 can display vehicle information and driving information as images. For example, tachometer needles and gauges and various warning light icons can be displayed by digital signals.

Referring to FIG. 6C, the display device 2 may be placed on the passenger seat dashboard 1600. The display device 2 may be embedded in the passenger seat dashboard 1600 or may be located on the passenger seat dashboard 1600. In one implementation, the display device 2 disposed on the passenger seat dashboard 1600 may display an image related to the information displayed on the cluster 1400 and/or the information displayed on the center fascia 1500. In another implementation, the display device 2 disposed on the passenger dashboard 1600 may display information different from the information displayed on the cluster 1400 and/or the information displayed on the center fascia 1500.

[Manufacturing method]

Each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region are, respectively, vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, and laser method. It can be formed in a predetermined area using various methods such as thermal transfer (Laser Induced Thermal Imaging, LITI).

When forming each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., about 10 A vacuum degree of ^-8 to about 10 ^-3 torr and a deposition rate of about 0.01 to about 100 Å/sec may be selected in consideration of the materials to be included in the layer to be formed and the structure of the layer to be formed.

[Definition of Terms]

As used herein, a C ₃ -C ₆₀ carbocyclic group refers to a cyclic group with 3 to 60 carbon atoms consisting only of carbon as a ring-forming atom, and a C ₁ -C ₆₀ heterocyclic group refers to a cyclic group containing, in addition to carbon, ring-forming atoms. It refers to a cyclic group with 1 to 60 carbon atoms that further contains a hetero atom as an atom. Each of the C ₃ -C ₆₀ carbocyclic group and C ₁ -C ₆₀ heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C ₁ -C ₆₀ heterocyclic group may be 3 to 61.

As used herein, cyclic groups include both the C ₃ -C ₆₀ carbocyclic group and the C ₁ -C ₆₀ heterocyclic group.

As used herein, _the π electron-rich C ₃ -C ₆₀ cyclic group is a ring-forming moiety and is a cyclic group having 3 to 60 _carbon atoms excluding *-N=*'. refers to a group, and the π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group is _a ring-forming _moiety containing *-N=*'. It refers to a heterocyclic group having 1 to 60 carbon atoms.

for example,

The C ₃ -C ₆₀ carbocyclic group is i) group T1 or ii) a condensed ring group in which two or more groups T1 are condensed with each other (e.g., cyclopentadiene group, adamantane group, norbornane group, Benzene group, pentalene group, naphthalene group, azulene group, indacene group, acenaphthylene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, perylene group, pentaphene group, hepthalene group, naphthacene group, picene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, indene group, fluorene group, spiro -bifluorene group, benzofluorene group, indenophenanthrene group, or indenoanthracene group),

The C ₁ -C ₆₀ heterocyclic group is i) a group T2, ii) a condensed ring group in which two or more groups T2 are condensed with each other, or iii) a condensed ring group in which one or more groups T2 and one or more groups T1 are condensed with each other (e.g. For example, pyrrole group, thiophene group, furan group, indole group, benzoindole group, naphthoindole group, isoindole group, benzoisoindole group, naphthoisoindole group, benzosilol group, benzothiophene group, benzoyl group. Furan group, carbazole group, dibenzosilol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzo Silolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilol group, benzofurodibenzofuran group, benzofurodibenzothiophene group , benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyra Sol group, benzimidazole group, benzoxazole group, benzoisoxazole group, benzothiazole group, benzoisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, Isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, Dazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzothiophene group , azadibenzofuran group, etc.),

The π electron-excess C ₃ -C ₆₀ cyclic group is i) group T1, ii) a condensed ring group in which two or more groups T1 are condensed with each other, iii) group T3, iv) a condensed ring in which two or more groups T3 are condensed with each other. group or v) a condensed ring group in which one or more groups T3 and one or more groups T1 are condensed with each other (e.g., the C ₃ -C ₆₀ carbocyclic group, 1H-pyrrole group, silole group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzoindole group, naphthoindole group, isoindole group, benzoisoindole group, naphthoisoindole group, benzosilol group, benzoti ophene group, benzofuran group, carbazole group, dibenzosilol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarba Sol group, benzosilolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilol group, benzofurodibenzofuran group, benzofurodi benzothiophene group, benzothienodibenzothiophene group, etc.),

The π electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group is i) group T4, ii) a condensed ring group in which two or more groups T4 are condensed with each other, iii) one or more groups T4 and one or more groups T1 are condensed with each other. a condensed ring group, iv) a condensed ring group in which one or more groups T4 and one or more groups T3 are condensed with each other, or v) a condensed ring group in which one or more groups T4, one or more groups T1 and one or more groups T3 are condensed with each other (e.g. For example, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group. , benzooxazole group, benzoisoxazole group, benzothiazole group, benzoisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group. , benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyridine group. Limidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzothiophene group, azadibenzofuran group, etc. ) can be,

The group T1 is a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, and a cyclohexadiene group. , cycloheptene group, adamantane group, norbornane (or, bicyclo[2.2.1]heptane) group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group, or benzene It's a group,

The group T2 is a furan group, thiophene group, 1H-pyrrole group, silole group, borole group, 2H-pyrrole group, 3H-pyrrole group, imidazole group, pyrazole group, triazole group, tetrazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, azacylol group, azabolol group, pyridine group, pyrimidine group, pyrazine group, Pyridazine group, triazine group, tetrazine group, pyrrolidine group, imidazolidine group, dihydropyrrole group, piperidine group, tetrahydropyridine group, dihydropyridine group, hexahydropyrimidine group, tetra A hydropyrimidine group, a dihydropyrimidine group, a piperazine group, a petrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,

The group T3 is a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group,

The group T4 is 2H-pyrrole group, 3H-pyrrole group, imidazole group, pyrazole group, triazole group, tetrazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group. , isothiazole group, thiadiazole group, azacylol group, azaborole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group or tetrazine group.

As used herein, a cyclic group, a C ₃ -C ₆₀ carbocyclic group, a C ₁ -C ₆₀ heterocyclic group, a π electron-excessive C ₃ -C ₆₀ cyclic group, or a π electron-deficient nitrogen-containing C ₁ - The term C ₆₀ cyclic group refers to a group condensed to any cyclic group, a monovalent group, or a multivalent group (e.g., a divalent group, a trivalent group, 4 group, etc.). For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by those skilled in the art, depending on the structure of the chemical formula containing the “benzene group”.

For example, examples of monovalent C ₃ -C ₆₀ carbocyclic groups and monovalent C ₁ -C ₆₀ heterocyclic groups include 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, and monovalent non-aromatic hetero It may include a condensed polycyclic group, and examples of the divalent C ₃ -C ₆₀ carbocyclic group and monovalent C ₁ -C ₆₀ heterocyclic group include C ₃ -C ₁₀ cycloalkylene group, C ₁ -C ₁₀ Heterocycloalkylene group, C ₃ -C ₁₀ cycloalkenylene group, C ₁ -C ₁₀ heterocycloalkenylene group, C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups.

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 thereof include methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -iso Pentyl group, n -hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n -heptyl group, isoheptyl group, sec -heptyl group, tert -heptyl group, n -octyl group, isooctyl group, sec -octyl group, tert -octyl group, n -nonyl group, isononyl group, sec -nonyl group, tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group, tert -decyl 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 monovalent hydrocarbon group containing one or more carbon-carbon double bonds in the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group and propenyl group. , butenyl group, etc. 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 monovalent hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group and propynyl group. etc. are 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 cyclic group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclohepyl group. Tyl group, cyclooctyl group, adamantanyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]phen These include bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. 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, a C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent cyclic group having 1 to 10 carbon atoms that further contains at least one hetero atom as a ring-forming atom in addition to a carbon atom, and specific examples thereof include 1, Includes 2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), tetrahydrofuranyl group, tetrahydrothiophenyl group, 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 cyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring, but does not have aromaticity. Specific examples thereof 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, a C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent cyclic group having 1 to 10 carbon atoms, which further contains at least one hetero atom as a ring-forming atom in addition to a carbon atom, and has at least one double bond in the ring. have 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, pentalenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, and fluoranthenyl group. , triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, Includes hepthalenyl group, naphthacenyl group, picenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl 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, C ₁ -C ₆₀ heteroaryl group refers to a monovalent group that further contains at least one hetero atom as a ring-forming atom in addition to a carbon atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms, and C ₁ -C ₆₀ heteroarylene group refers to a divalent group that, in addition to carbon atoms, further contains at least one hetero atom as a ring-forming atom and has a heterocyclic aromatic system of 1 to 60 carbon atoms. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, benzoquinolinyl group, isoquinolinyl group, and benzoyl group. Includes isoquinolinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cynolinyl group, phenanthrolinyl group, phthalazinyl group, naphthyridinyl 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, 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 indenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, indenophenanthrenyl group, indenoanthracenyl group, etc. 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 has two or more rings condensed with each other, further contains at least one hetero atom in addition to a carbon atom as a ring-forming atom, and the entire molecule is It refers to a monovalent group having non-aromatic properties (e.g., having 1 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl group, thiophenyl group, furanyl group, indolyl group, benzoindolyl group, naphthoindolyl group, isoindoleyl group, benzoisoindolyl group, naphthoisoindolyl group. , benzosilolyl group, benzothiophenyl group, benzofuranyl group, carbazolyl group, dibenzosilolyl group, dibenzothiophenyl group, dibenzofuranyl group, azacarbazolyl group, azafluorenyl group, azadibenzosilolyl group, azadi Benzothiophenyl group, azadibenzofuranyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, thiazolyl group Diazolyl group, benzopyrazolyl group, benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazo Triazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazolyl group, indolocarbazolyl group, benzofurocarbazolyl group, benzothienocarbazolyl group, benzosilolocarbazolyl group, Benzoindolocarbazolyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilolyl group, benzofurodibenzofuranyl group, benzofurodibenzothiophenyl group, benzothienodibenzothiophenyl group , etc. are included. 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 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, C ₇ -C ₆₀ arylalkyl group refers to -A ₁₀₄ A ₁₀₅ (where A ₁₀₄ is a C ₁ -C ₅₄ alkylene group and A ₁₀₅ is a C ₆ -C ₅₉ aryl group), and as used herein, C ₂ -C ₆₀ heteroarylalkyl group refers to -A ₁₀₆ A ₁₀₇ (where A ₁₀₆ is a C ₁ -C ₅₉ alkylene group and A ₁₀₇ is a C ₁ -C ₅₉ heteroaryl group).

In this specification, “R _10a ” means,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₁₁ )( Q ₁₂ ), or substituted or unsubstituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro 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 carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group , C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₂₁ )(Q ₂₂ ), or any combination thereof, substituted or unsubstituted, C ₃ - C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, or C ₂ -C ₆₀ hetero Arylalkyl group; or

-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 ), or -P(=O)(Q ₃₁ )(Q ₃₂ );

It can be.

In this specification, Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; or C ₁ -C 60 alkyl group, _{C 2} substituted or unsubstituted with deuterium, -F, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, biphenyl group, or any combination thereof. It may be a -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₆₀ carbocyclic group, or a C ₁ -C ₆₀ heterocyclic group.

In this specification, a hetero atom means any atom other than a carbon atom. Examples of such heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

In this specification, third-row transition metals include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), and platinum (Pt). ) and gold (Au).

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 *', unless otherwise defined, mean a binding site with a neighboring atom in the corresponding chemical formula or moiety.

Below, a light-emitting device according to an embodiment of the present invention will be described in more detail through examples.

[Example]

Evaluation example 1

HOMO energy level (eV), LUMO energy level (eV), bandgap (eV), and ³ MLCT ( %) was evaluated and the results are shown in Table 2.

How to Evaluate HOMO Energy Levels Cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NPF ₆ / solvent: DMF (dimethylforamide) / electrode: using a 3-electrode system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)) After obtaining the potential (V)-current (A) graph of each compound, calculate the HOMO energy level of each compound from the oxidation onset of the graph. How to Evaluate LUMO Energy Levels Cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NPF ₆ / solvent: DMF (dimethylforamide) / electrode: using a 3-electrode system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)) After obtaining the potential (V)-current (A) graph of each compound, calculate the LUMO energy level of each compound from the reduction onset of the graph. Band gap evaluation method Calculate the absolute value of the difference between HOMO energy level and LUMO energy level Method for evaluating triplet metal-to-ligand charge transfer state ( ³ MLCT) during total intramolecular charge transfer For each compound, quantum chemical calculations are performed using Gaussian 09, a quantum chemical calculation program manufactured by Gaussian, USA (B3LYP is used for ground state structure optimization, and 6-311G (d,p) is used as a function).

HOMO
energy level
(eV) LUMO
energy level
(eV) band gap
(eV) ³ MLCTs
(%) PD01 -4.98 -2.48 2.50 15.33 PD02 -5.20 -2.55 2.65 11.01 PD03 -4.98 -1.66 3.32 9.96 PD04 -4.84 -2.39 2.45 14.57 PD06 -4.85 -2.33 2.52 12.74 PD08 -4.98 -2.14 2.84 10.31 B01 -5.05 -1.98 3.07 5.91 B02 -5.06 -1.89 3.17 -2.11 B03 -4.95 -1.90 3.06 0.29

From Table 2, it can be seen that ^{the 3} MLCT of compounds PD01, PD02, PD03, PD04, PD06 and PD08 is more than 9%.

Evaluation example 2

After mixing PMMA and compound PD01 (4 wt% compared to PMMA) in CH ₂ Cl ₂ solution, the resulting product was coated on a quartz substrate using a spin coater, heat treated in an oven at 80°C, and then cooled at room temperature. Film PD01 with a thickness of 40 nm was manufactured by cooling. Then, using the same method as the production method of film PD01, except that instead of compound PD01, compounds PD02, PD03, PD04, PD06, PD08, B01, B02, and B03 were used, respectively, films PD02 and PD03 were produced. , PD04, PD06, PD08, B01, B02 and B03 were prepared.

The emission spectra of each of the films PD01, PD02, PD03, PD04, PD06, PD08, B01, B02 and B03 were measured using Hamamatsu's Quantaurus-QY Absolute PL quantum yield spectrometer (xenon light source, monochromator). , was equipped with a photonic multichannel analyzer, and an integrating sphere, and was measured using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During measurement, the excitation wavelength was measured by scanning at 10 nm intervals from 320 nm to 380 nm. Among these, the spectrum measured at an excitation wavelength of 340 nm was taken, and from this, the maximum emission wavelength (emission peak wavelength) and half width of the compound included in each film were determined. (FWHM) was obtained and summarized in Table 3 below.

Film No. Compounds contained in the film
(4 wt% in PMMA) Maximum emission wavelength (nm) Luminance half width (nm) PD01 PD01 522 32 PD02 PD02 556 25 PD03 PD03 511 26 PD04 PD04 516 53 PD06 PD06 534 60 PD08 PD08 604 41 B01 B01 496 90 B02 B02 524 55 B03 B03 522 31

Evaluation example 3

The HOMO energy level and LUMO energy level of compounds ET-1 to ET-6 and PET-1 to PET-4 were evaluated according to the method in Table 1, and the results are shown in Table 4.

Meanwhile, the hole mobility and electron mobility of compounds ET-1 to ET-6 and PET-1 to PET-4, respectively, are expressed as "Hole mobility of N,N'-bis(naphtanlen-1-yl)-N,N In the Space-charge-limited current (SCLC) method described in '-bis(phenyl)benzidine investigated by using space-charge-limited currents, 'Appl. Phys. Lett. 90, 203512 (2007)" was evaluated and the results are shown in Table 4.

HOMO
Energy level (eV) LUMO
Energy level (eV) Band gap (eV) Hole mobility (cm ² /Vs) Electron mobility (cm ² /Vs) ET-1 -6.01 -2.67 3.33 2.44 x 10 ^-4 1.16 x 10 ^-3 ET-2 -5.98 -2.69 3.29 2.70 x 10 ^-4 8.16 x 10 ^-4 ET-3 -5.94 -2.79 3.16 1.40 x 10 ^-4 3.45 x 10 ^-4 ET-4 -5.82 -2.67 3.15 1.90 x 10 ^-4 1.56 x 10 ^-4 ET-5 -5.86 -2.68 3.19 8.88 x 10 ^-5 3.71 x 10 ^-4 ET-6 -6.07 -2.81 3.26 2.40 x 10 ^-5 2.41 x 10 ^-4 PET-1 -5.35 -2.50 2.85 1.31 x 10 ^-3 1.07 x 10 ^-3 PET-2 -6.10 -2.57 3.52 5.34 x 10 ^-4 1.00 x 10 ^-3 PET-3 -5.93 -2.57 3.37 3.32 x 10 ^-4 5.88 x 10 ^-4 PET-4 -5.95 -2.13 3.82 1.97 x 10 ^-4 2.40 x 10 ^-3 PET-5 -5.62 -2.28 3.34 4.48 x 10 ^-5 5.91 x 10 ^-5 PET-6 -5.73 -2.23 3.50 2.73 x 10 ^-6 1.49 x 10 ^-4

Example 1

A glass substrate (made by Corning) with 15 Ω/cm ² (1200 Å) ITO as an anode was cut into 50 mm x 50 mm x 0.7 mm and ultrasonic cleaned for 5 minutes each using isopropyl alcohol and pure water. It was irradiated with ultraviolet rays for 30 minutes, cleaned by exposure to ozone, and installed in a vacuum evaporation device.

HT3 was vacuum deposited on the anode to form a hole transport layer with a thickness of 600 Å, and HT40 was vacuum deposited on the hole transport layer to form a light emitting auxiliary layer with a thickness of 250 Å.

Compound H125, Compound H126, and Compound PD01 (first emitter) were vacuum deposited on the light emitting auxiliary layer at a weight ratio of 45:45:10 to form a light emitting layer with a thickness of 300 Å.

Compound ET37 was vacuum deposited on the emitting layer to form a hole blocking layer with a thickness of 50 Å, and ET-1 and LiQ were vacuum deposited at a weight ratio of 5:5 on the hole blocking layer to form an electron transport layer with a thickness of 310 Å. Next, Yb was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of 15 Å, and then Ag and Mg were vacuum deposited to form a cathode with a thickness of 100 Å, thereby manufacturing an organic light emitting device.

Other Examples and Comparative Examples

Examples and comparisons shown in Tables 5 to 10 using the same method as Example 1, except that the compounds shown in Tables 5 to 10 were used instead of PD01 in the light emitting layer and/or ET-1 in the electron transport layer. An example organic light emitting device was manufactured.

Evaluation example 4

Driving voltage (V), maximum power efficiency (cd/W), and color coordinate (CIE and CIE y) were measured using Keithley MU 236 and luminance meter PR650, and the results are shown in Tables 5 to 10, respectively.

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 1 PD01 ET-1 2.9 24.09 0.43 0.57 Example 2 PD01 ET-2 2.95 23.68 0.43 0.57 Example 3 PD01 ET-3 2.75 25.38 0.43 0.57 Example 4 PD01 ET-4 2.95 23.67 0.43 0.57 Example 5 PD01 ET-5 2.9 24.09 0.43 0.57 Example 6 PD01 ET-6 2.8 24.94 0.43 0.57 Comparative Example 1 PD01 PET-1 3.5 19.89 0.43 0.57 Comparative Example 2 PD01 PET-2 3.3 21.15 0.43 0.57 Comparative Example 3 PD01 PET-3 3.3 21.17 0.43 0.57 Comparative Example 4 PD01 PET-4 3.3 21.17 0.43 0.57 Comparative Example 5 PD01 PET-5 3.3 21.05 0.43 0.57 Comparative Example 6 PD01 PET-6 3.3 21.14 0.43 0.57 Comparative Example 37 B01 ET-1 2.9 15.35 0.42 0.56 Comparative Example 38 B01 ET-2 2.95 15.09 0.42 0.56 Comparative Example 39 B01 ET-3 2.75 16.17 0.42 0.56 Comparative Example 40 B01 ET-4 2.95 15.08 0.42 0.56 Comparative Example 41 B01 ET-5 2.9 15.35 0.42 0.56 Comparative Example 42 B01 ET-6 2.8 15.89 0.42 0.56 Comparative Example 43 B02 ET-1 2.9 11.18 0.32 0.66 Comparative Example 44 B02 ET-2 2.95 10.99 0.32 0.66 Comparative Example 45 B02 ET-3 2.75 11.77 0.32 0.66 Comparative Example 46 B02 ET-4 2.95 10.98 0.32 0.66 Comparative Example 47 B02 ET-5 2.9 11.18 0.32 0.66 Comparative Example 48 B02 ET-6 2.8 11.57 0.32 0.66 Comparative Example 49 B03 ET-1 2.9 14.09 0.32 0.66 Comparative Example 50 B03 ET-2 2.95 13.86 0.32 0.66 Comparative Example 51 B03 ET-3 2.75 14.85 0.32 0.66 Comparative Example 52 B03 ET-4 2.95 13.85 0.32 0.66 Comparative Example 53 B03 ET-5 2.9 14.09 0.32 0.66 Comparative Example 54 B03 ET-6 2.8 14.59 0.32 0.66 Comparative Example 55 B01 PET-1 3.5 12.68 0.42 0.56 Comparative Example 56 B01 PET-2 3.3 13.48 0.42 0.56 Comparative Example 57 B01 PET-3 3.3 13.49 0.42 0.56 Comparative Example 58 B01 PET-4 3.3 13.49 0.42 0.56 Comparative Example 59 B01 PET-5 3.3 13.41 0.42 0.56 Comparative Example 60 B01 PET-6 3.3 13.47 0.42 0.56 Comparative Example 61 B02 PET-1 3.5 9.23 0.32 0.66 Comparative Example 62 B02 PET-2 3.3 9.81 0.32 0.66 Comparative Example 63 B02 PET-3 3.3 9.82 0.32 0.66 Comparative Example 64 B02 PET-4 3.3 9.82 0.32 0.66 Comparative Example 65 B02 PET-5 3.3 9.77 0.32 0.66 Comparative Example 66 B02 PET-6 3.3 9.81 0.32 0.66 Comparative Example 67 B03 PET-1 3.5 11.64 0.32 0.66 Comparative Example 68 B03 PET-2 3.3 12.37 0.32 0.66 Comparative Example 69 B03 PET-3 3.3 12.39 0.32 0.66 Comparative Example 70 B03 PET-4 3.3 12.39 0.32 0.66 Comparative Example 71 B03 PET-5 3.3 12.31 0.32 0.66 Comparative Example 72 B03 PET-6 3.3 12.37 0.32 0.66

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 7 PD02 ET-1 2.9 23.23 0.47 0.53 Example 8 PD02 ET-2 2.95 22.84 0.47 0.53 Example 9 PD02 ET-3 2.75 24.47 0.47 0.53 Example 10 PD02 ET-4 2.95 22.83 0.47 0.53 Example 11 PD02 ET-5 2.9 23.23 0.47 0.53 Example 12 PD02 ET-6 2.8 24.05 0.47 0.53 Comparative Example 7 PD02 PET-1 3.5 19.18 0.47 0.53 Comparative Example 8 PD02 PET-2 3.3 20.40 0.47 0.53 Comparative Example 9 PD02 PET-3 3.3 20.42 0.47 0.53 Comparative Example 10 PD02 PET-4 3.3 20.42 0.47 0.53 Comparative Example 11 PD02 PET-5 3.3 20.3 0.47 0.53 Comparative Example 12 PD02 PET-6 3.3 20.39 0.47 0.53

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 13 PD03 ET-1 2.9 22.69 0.23 0.71 Example 14 PD03 ET-2 2.95 22.3 0.23 0.71 Example 15 PD03 ET-3 2.75 23.9 0.23 0.71 Example 16 PD03 ET-4 2.95 22.29 0.23 0.71 Example 17 PD03 ET-5 2.9 22.68 0.23 0.71 Example 18 PD03 ET-6 2.8 23.49 0.23 0.71 Comparative Example 13 PD03 PET-1 3.5 18.73 0.23 0.71 Comparative Example 14 PD03 PET-2 3.3 19.92 0.23 0.71 Comparative Example 15 PD03 PET-3 3.3 19.94 0.23 0.71 Comparative Example 16 PD03 PET-4 3.3 19.94 0.23 0.71 Comparative Example 17 PD03 PET-5 3.3 19.82 0.23 0.71 Comparative Example 18 PD03 PET-6 3.3 19.91 0.23 0.71

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 19 PD04 ET-1 2.9 24.02 0.42 0.57 Example 20 PD04 ET-2 2.95 23.61 0.42 0.57 Example 21 PD04 ET-3 2.75 25.3 0.42 0.57 Example 22 PD04 ET-4 2.95 23.6 0.42 0.57 Example 23 PD04 ET-5 2.9 24.02 0.42 0.57 Example 24 PD04 ET-6 2.8 24.87 0.42 0.57 Comparative Example 19 PD04 PET-1 3.5 19.84 0.42 0.57 Comparative Example 20 PD04 PET-2 3.3 21.09 0.42 0.57 Comparative Example 21 PD04 PET-3 3.3 21.11 0.42 0.57 Comparative Example 22 PD04 PET-4 3.3 21.11 0.42 0.57 Comparative Example 23 PD04 PET-5 3.3 20.99 0.42 0.57 Comparative Example 24 PD04 PET-6 3.3 21.08 0.42 0.57

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 25 PD06 ET-1 2.9 23.75 0.48 0.52 Example 26 PD06 ET-2 2.95 23.35 0.48 0.52 Example 27 PD06 ET-3 2.75 25.02 0.48 0.52 Example 28 PD06 ET-4 2.95 23.34 0.48 0.52 Example 29 PD06 ET-5 2.9 23.75 0.48 0.52 Example 30 PD06 ET-6 2.8 24.59 0.48 0.52 Comparative Example 25 PD06 PET-1 3.5 19.61 0.48 0.52 Comparative Example 26 PD06 PET-2 3.3 20.85 0.48 0.52 Comparative Example 27 PD06 PET-3 3.3 20.87 0.48 0.52 Comparative Example 28 PD06 PET-4 3.3 20.87 0.48 0.52 Comparative Example 29 PD06 PET-5 3.3 20.75 0.48 0.52 Comparative Example 30 PD06 PET-6 3.3 20.84 0.48 0.52

1st
emitter electron transport layer material driving voltage
(V)
at 1000 cd/ ^m2 Maximum power efficiency (cd/W) CIE x CIE y Example 31 PD08 ET-1 2.9 22.9 0.70 0.30 Example 32 PD08 ET-2 2.95 22.51 0.70 0.30 Example 33 PD08 ET-3 2.75 24.12 0.70 0.30 Example 34 PD08 ET-4 2.95 22.5 0.70 0.30 Example 35 PD08 ET-5 2.9 22.89 0.70 0.30 Example 36 PD08 ET-6 2.8 23.7 0.70 0.30 Comparative Example 31 PD08 PET-1 3.5 18.91 0.70 0.30 Comparative Example 32 PD08 PET-2 3.3 20.10 0.70 0.30 Comparative Example 33 PD08 PET-3 3.3 20.12 0.70 0.30 Comparative Example 34 PD08 PET-4 3.3 20.12 0.70 0.30 Comparative Example 35 PD08 PET-5 3.3 20 0.70 0.30 Comparative Example 36 PD08 PET-6 3.3 20.09 0.70 0.30

From Tables 5 to 10, it can be seen that the light emitting device manufactured in the Example has improved driving voltage and maximum power efficiency compared to the light emitting device manufactured in the Comparative Example.

10: Organic light emitting device
110: first electrode
130: middle layer
150: second electrode

Claims (20)

first electrode;
a second electrode opposite the first electrode; and
an intermediate layer disposed between the first electrode and the second electrode;
Including,
The intermediate layer includes a light emitting layer and an electron transport region,
The electron transport region is disposed between the light-emitting layer and the second electrode,
The light emitting layer includes a first emitter,
The first emitter emits first light having a first emission spectrum,
The first emitter includes platinum,
The triplet metal-to-ligand charge transfer state ( ^3MLCT ) of the first emitter is 7% or more,
The triplet metal-ligand charge transfer state was evaluated by performing quantum chemical calculations based on density functional theory (DFT),
The electron transport region includes a heterocyclic compound,
The heterocyclic compound is,
A first moiety comprising a group represented by one of the following formulas 8-1 to 8-4; and
a second moiety comprising a diazine group, a triazine group, or any combination thereof;
Including,
A light emitting device in which the first moiety and the second moiety are bound to each other through a single bond or a first linking group:

In formulas 8-1 to 8-4,
X ₈ is O, S, or Se,
* is a single bond bonded to the second moiety or a binding site with a first linking group bonded to the second moiety. According to paragraph 1,
A light emitting device wherein the peak emission wavelength of the first light is 510 nm to 610 nm. According to paragraph 1,
A light emitting device wherein the half width of the first light is 15 nm to 85 nm. According to paragraph 1,
The first emitter further includes a first ligand bound to the platinum,
The first emitter is a light emitting device that satisfies at least one of the following <Condition A> to <Condition C>:
<Condition A>
The first ligand is a tetradentate ligand,
There are three cyclometallated rings formed by chemical bonds between the platinum and the first ligand.
<Condition B>
Each of the carbon, nitrogen, and oxygen of the first ligand is chemically bonded to the platinum.
<Condition C>
The first ligand comprises an imidazole group, a benzimidazole group, a naphthoimidazole group, or any combination thereof. According to paragraph 1,
A light emitting device wherein the first emitter is an organometallic compound represented by the following formula (1):
<Formula 1>

In Formula 1,
M is platinum (Pt),
X ₁ to X ₄ are each independently N or C,
T ₁₁ to T ₁₄ are independently of each other, a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R') (R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") or P(R')(R") ego,
When T ₁₁ is a chemical bond, X ₁ and M are directly bonded, when T _{12 is} a chemical bond, X ₂ and M are directly bonded, and when T ₁₃ is a chemical bond, Bonds directly, and when T ₁₄ is a chemical bond, X ₄ and M bond directly,
Two of the bonds between X ₁ or T ₁₁ and M, the bond between X ₂ or T ₁₂ and M, the bond between X ₃ or T ₁₃ and M, and the bond between X ₄ or T ₁₄ and M are coordinate bonds. , and the remaining two bonds are covalent bonds,
T ₁ is a single bond, double bond, *-N(R ₅ )-*', *-B(R ₅ )-*', *-P(R ₅ )-*', *-C(R _5a )( R _5b )-*', *-Si(R _5a )(R _5b )-*', *-Ge(R _5a )(R _5b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₅ )= *', *=C(R ₅ )-*', *-C(R _5a )=C(R _5b )-*', *-C(=S)-*' or *-C≡C-*' ego,
T ₂ is a single bond, double bond, *-N(R ₆ )-*', *-B(R ₆ )-*', *-P(R ₆ )-*', *-C(R _6a )( R _6b )-*', *-Si(R _6a )(R _6b )-*', *-Ge(R _6a )(R _6b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₆ )= *', *=C(R ₆ )-*', *-C(R _6a )=C(R _6b )-*', *-C(=S)-*' or *-C≡C-*' ego,
T ₃ is a single bond, double bond, *-N(R ₇ )-*’, *-B(R ₇ )-*’, *-P(R ₇ )-*’, *-C(R _7a )( R _7b )-*', *-Si(R _7a )(R _7b )-*', *-Ge(R _7a )(R _7b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₇ )= *', *=C(R ₇ )-*', *-C(R _7a )=C(R _7b )-*', *-C(=S)-*' or *-C≡C-*' ego,
Ring CY ₁ , ring CY ₃ and ring CY ₄ are, independently of each other, a C ₃ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,
X ₂₁ is N or C(R ₂₁ ), X ₂₂ is N or C(R ₂₂ ), X ₂₃ is N or C(R ₂₃ ),
X ₂₄ is O, S, N(R ₂₄ ) or C(R _24a )(R _24b ),
R ₁ , R ₂₁ to R ₂₄ , R _24a , R _24b , R ₃ to R 7, R _5a , R _5b , R _6a , R _6b , R _7a , _{R 7b ,} R', and R" are independently of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₆₀ alkyl group substituted or unsubstituted with at least one R _10a , with at least one R _10a Substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group substituted or unsubstituted with at least one R _10a , C ₁ -C ₆₀ alkoxy group substituted or unsubstituted with at least one R _10a , C ₃ -C _{60 carbocyclic} group unsubstituted or substituted with at least one R _10a , C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R 10a , substituted with at least one R _10a or an unsubstituted C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group unsubstituted or substituted with at least one R _10a , a C ₇ -C ₆₀ aryl substituted or unsubstituted with at least one R _10a Alkyl group, C ₂ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ), or -P( =O)(Q ₁ )(Q ₂ ),
a1, a3 and a4 are independently one of the integers from 0 to 20,
* and *' are bonding sites with neighboring atoms, respectively,
i) 2 groups of a1 R ₁ , ii) 2 groups of R ₂₁ to R ₂₃ , iii) 2 groups of a3 R ₃ , iv) 2 groups of a4 R ₄ , v) R _5a and R _5b , vi) R _6a and R _6b , and vii) two groups of R _7a and R _7b are each optionally bonded to each other through a single bond, double bond or first linking group, forming at least one R It may form a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with _10a or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,
The R _10a is,
Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₁₁ )( Q ₁₂ ), or substituted or unsubstituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro 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 carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group , C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₂₁ )(Q ₂₂ ), or any combination thereof, substituted or unsubstituted, C ₃ - C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, or C ₂ -C ₆₀ hetero Arylalkyl group; or
-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 ), or -P(=O)(Q ₃₁ )(Q ₃₂ );
ego,
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; or C ₁ -C 60 alkyl group, _{C 2} substituted or unsubstituted with deuterium, -F, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, biphenyl group, or any combination thereof. -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group, or C ₁ -C ₆₀ heterocyclic group; According to clause 5,
X ₁ and X ₃ are each C,
A light emitting element where X ₂ and X ₄ are each N. According to clause 6,
T ₁₁ is O or S,
A light emitting device wherein each of T ₁₂ to T ₁₄ is a chemical bond. According to paragraph 1,
The electron transport region includes an electron transport layer,
A light emitting device wherein the heterocyclic compound is included in the electron transport layer. According to clause 8,
A light-emitting device wherein the electron transport layer is in direct contact with the light-emitting layer. According to paragraph 1,
The electron transport region includes a hole blocking layer and an electron transport layer,
The hole blocking layer is disposed between the light emitting layer and the electron transport layer,
The hole blocking layer does not contain the heterocyclic compound,
A light emitting device wherein the heterocyclic compound is included in the electron transport layer. According to paragraph 1,
A light emitting device wherein the heterocyclic compound is a compound represented by the following formula (8):
<Formula 8>

In the above formula 8,
X ₁₄ is N or C(Z ₄ ), X ₁₅ is N or C(Z ₅ ), X ₁₆ is N or C(Z ₆ ),
2 or more of X ₁₄ to X ₁₆ are N,
Ar ₁ to Ar ₃ are each independently a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _10a , or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R _10a Click group,
x1 to x3 are independently one of the integers from 0 to 10,
i) When x1 is 0, *-(Ar ₁ ) _x1 -*' becomes a single bond, ii) When x2 is 0, *-(Ar ₂ ) _x2 -*' becomes a single bond, iii) When x3 is 0, *-(Ar ₃ ) _x3 -*' becomes a single bond, * and *' are each a bonding site with a neighboring atom,
Ar ₁₃ is a group represented by one of the following formulas 8-1 to 8-4,
Z ₁ to Z ₆ are each independently C ₁ -substituted or unsubstituted with hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R _10a C ₆₀ alkyl group, C _{2 -C 60 alkenyl} group substituted or unsubstituted with at least one R 10a, C ₂ -C ₆₀ alkynyl group substituted or unsubstituted with at least one R _10a , substituted with at least one R _10a or Unsubstituted C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _10a , C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _10a Click group, C ₆ -C ₆₀ aryloxy group, unsubstituted or substituted with at least one R _10a , C ₆ -C ₆₀ arylthio group, unsubstituted or substituted with at least one R _10a , substituted with at least one R _10a or an unsubstituted C ₇ -C ₆₀ arylalkyl group, a C ₂ -C ₆₀ heteroarylalkyl group unsubstituted or substituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ) or -P(=O)(Q ₁ )(Q ₂ ),
y1 to y3 are independently one of the integers from 0 to 5,
The R _10a is,
Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₁₁ )( Q ₁₂ ), or substituted or unsubstituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro 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 carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group , C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₂₁ )(Q ₂₂ ), or any combination thereof, substituted or unsubstituted, C ₃ - C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, or C ₂ -C ₆₀ hetero Arylalkyl group; or
-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 ), or -P(=O)(Q ₃₁ )(Q ₃₂ );
ego,
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; or C ₁ -C 60 alkyl group, _{C 2} substituted or unsubstituted with deuterium, -F, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, biphenyl group, or any combination thereof. -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group or C ₁ -C ₆₀ heterocyclic group;
It can be:

In formulas 8-1 to 8-4,
X ₈ is O, S, or Se,
* is a binding site with Ar ₃ in Chemical Formula 8. According to clause 11,
A light emitting device wherein at least one of x1 and x2 is 2 or more. According to clause 11,
x1 and x2 are independently one of the integers from 1 to 10,
x3 is 0, 1, or 2,
Ar ₁ to Ar ₃ are each independently substituted or unsubstituted with at least one R _10a , a benzene group, a naphthalene group, a phenanthrene group, anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, A light-emitting device comprising a fluorene group or a pyridine group. first electrode;
a second electrode opposite the first electrode; and
an intermediate layer disposed between the first electrode and the second electrode;
Including,
The intermediate layer includes a light emitting layer and an electron transport region,
The electron transport region is disposed between the light-emitting layer and the second electrode,
The light emitting layer includes a first emitter,
The first emitter emits first light having a first emission spectrum,
The first emitter is an organometallic compound represented by the following formula (1),
The electron transport region includes a heterocyclic compound,
The heterocyclic compound is,
A first moiety comprising a group represented by one of the following formulas 8-1 to 8-4; and
a second moiety comprising a diazine group, a triazine group, or any combination thereof;
Including,
A light emitting device in which the first moiety and the second moiety are bound to each other through a single bond or a first linking group:
<Formula 1>

In Formula 1,
M is platinum (Pt),
X ₁ to X ₄ are each independently N or C,
T ₁₁ to T ₁₄ are independently of each other, a chemical bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R') (R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R") or P(R')(R") ego,
When T ₁₁ is a chemical bond, X ₁ and M are directly bonded, _when T ₁₂ is a chemical bond, X ₂ and M are directly bonded, and when T ₁₃ is a chemical bond, Bonds directly, and when T ₁₄ is a chemical bond, X ₄ and M bond directly,
Two of the bonds between X ₁ or T ₁₁ and M, the bond between X ₂ or T ₁₂ and M, the bond between X ₃ or T ₁₃ and M, and the bond between X ₄ or T ₁₄ and M are coordinate bonds. , and the remaining two bonds are covalent bonds,
T ₁ is a single bond, double bond, *-N(R ₅ )-*', *-B(R ₅ )-*', *-P(R ₅ )-*', *-C(R _5a )( R _5b )-*', *-Si(R _5a )(R _5b )-*', *-Ge(R _5a )(R _5b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₅ )= *', *=C(R ₅ )-*', *-C(R _5a )=C(R _5b )-*', *-C(=S)-*' or *-C≡C-*' ego,
T ₂ is a single bond, double bond, *-N(R ₆ )-*', *-B(R ₆ )-*', *-P(R ₆ )-*', *-C(R _6a )( R _6b )-*', *-Si(R _6a )(R _6b )-*', *-Ge(R _6a )(R _6b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₆ )= *', *=C(R ₆ )-*', *-C(R _6a )=C(R _6b )-*', *-C(=S)-*' or *-C≡C-*' ego,
T ₃ is a single bond, double bond, *-N(R ₇ )-*’, *-B(R ₇ )-*’, *-P(R ₇ )-*’, *-C(R _7a )( R _7b )-*', *-Si(R _7a )(R _7b )-*', *-Ge(R _7a )(R _7b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₇ )= *', *=C(R ₇ )-*', *-C(R _7a )=C(R _7b )-*', *-C(=S)-*' or *-C≡C-*' ego,
Ring CY ₁ , ring CY ₃ and ring CY ₄ are, independently of each other, a C ₃ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,
X ₂₁ is N or C(R ₂₁ ), X ₂₂ is N or C(R ₂₂ ), X ₂₃ is N or C(R ₂₃ ), and X ₂₄ is O, S, N(R ₂₄ ) or C (R _24a )(R _24b ),
R ₁ , R ₂₁ to R ₂₄ , R _24a , R _24b , R ₃ to R 7, R _5a , R _5b , R _6a , R _6b , R _7a , _{R 7b ,} R', and R" are independently of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₁ -C ₆₀ alkyl group substituted or unsubstituted with at least one R _10a , with at least one R _10a Substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group substituted or unsubstituted with at least one R _10a , C ₁ -C ₆₀ alkoxy group substituted or unsubstituted with at least one R _10a , C ₃ -C _{60 carbocyclic} group unsubstituted or substituted with at least one R _10a , C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R 10a , substituted with at least one R _10a or an unsubstituted C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group unsubstituted or substituted with at least one R _10a , a C ₇ -C ₆₀ aryl substituted or unsubstituted with at least one R _10a Alkyl group, C ₂ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted with at least one R _10a , -C(Q ₁ )(Q ₂ )(Q ₃ ), -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 ), or -P( =O)(Q ₁ )(Q ₂ ),
a1, a3 and a4 are independently one of the integers from 0 to 20,
* and *' are bonding sites with neighboring atoms, respectively,
i) 2 groups of a1 R ₁ , ii) 2 groups of R ₂₁ to R ₂₃ , iii) 2 groups of a3 R ₃ , iv) 2 groups of a4 R ₄ , v) R _5a and R _5b , vi) R _6a and R _6b , and vii) two groups of R _7a and R _7b are each optionally bonded to each other through a single bond, double bond or first linking group, forming at least one R It may form a C ₃ -C ₆₀ carbocyclic group substituted or unsubstituted with _10a or a C ₁ -C ₆₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,
The R _10a is,
Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₁₁ )( Q ₁₂ ), or substituted or unsubstituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro 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 carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group , C ₂ -C ₆₀ heteroarylalkyl 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 ), -P(=O)(Q ₂₁ )(Q ₂₂ ), or any combination thereof, substituted or unsubstituted, C ₃ - C ₆₀ carbocyclic group, C ₁ -C ₆₀ heterocyclic group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₇ -C ₆₀ arylalkyl group, or C ₂ -C ₆₀ hetero Arylalkyl group; or
-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 ), or -P(=O)(Q ₃₁ )(Q ₃₂ );
ego,
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; or C ₁ -C 60 alkyl group, _{C 2} substituted or unsubstituted with deuterium, -F, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, biphenyl group, or any combination thereof. -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ carbocyclic group or C ₁ -C ₆₀ heterocyclic group; may be:

In formulas 8-1 to 8-4,
X ₈ is O, S, or Se,
* is a single bond bonded to the second moiety or a binding site with a first linking group bonded to the second moiety. According to clause 14,
X ₁ and X ₃ are each C,
A light emitting element where X ₂ and X ₄ are each N. According to clause 14,
T ₁₁ is O or S,
A light emitting device wherein each of T ₁₂ to T ₁₄ is a chemical bond. An electronic device comprising the light emitting device of any one of claims 1 to 16. According to clause 17,
An electronic device further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. An electronic device comprising the light emitting device of any one of claims 1 to 16. According to clause 19,
Flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal lights, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable ( foldable displays, stretchable displays, laser printers, phones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays. , an electronic device that is one of a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.

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