KR20200062022A - Organometallic compound and organic light emitting device comprising the same - Google Patents

Abstract

Disclosed are an organic metal compound and an organic light emitting device. The organic light emitting device includes: a first electrode; a second electrode opposed to the first electrode; an organic layer disposed between the first electrode and the second electrode and including a light emitting layer; and at least one organometallic compound represented by chemical formula 1, wherein the chemical formula 1 is M(L_1)_n1(L_2 )_n2. Therefore, the organic light emitting device has a low driving voltage, high brightness, high efficiency and long lifespan.

Description

Organometallic compound and organic light emitting device comprising the same}

An organic metal compound and an organic light emitting device including the same.

Organic light emitting devices (organic light emitting device) is a self-emission type device, as compared to the conventional device, the viewing angle is wide and excellent in contrast, as well as a fast response time, brightness, driving voltage and response speed characteristics are excellent and multi-colorization It is possible.

In the organic light emitting device, a first electrode is disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. 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 emission layer region to generate excitons. As this exciton changes from the excited state to the ground state, light is generated.

It is to provide a novel organometallic compound and an organic light emitting device including the same.

According to one aspect, an organometallic compound represented by Formula 1 is provided:

<Formula 1>

M(L ₁ ) _n1 (L ₂ ) _n2

<Formula 2-1> <Formula 2-2>

<Formula 3>

In Formula 1,

M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti) ), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm);

In Formula 1, L ₁ is a ligand represented by Formula 2-1 or 2-2, n1 is 1, 2 or 3, and when n1 is 2 or more, 2 or more L ₁ are the same or different from each other,

In Formula 1, L ₂ is a ligand represented by Formula 3, n2 is 0, 1 or 2, and when n2 is 2 or more, 2 or more L ₂ is the same or different from each other,

In Formula 1, n1+n2 is 2 or 3,

In Formula 1, n1 L ₁ And n2 L ₂ Is optionally a single bond, a first linking group or a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ It can be connected to each other through a heterocyclic group,

The first connector is *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''-Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)- *''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₄ )=*', * ''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''' is selected,

In Formula 2-1, A ₁ is selected from a C ₅ -C ₆₀ carbocyclic group and a C ₁ -C ₆₀ heterocyclic group;

In Formula 2-1, X ₁ and X ₂ are each independently N or C(R ₃ );

In Formula 2-2, X ₁₁ and X ₁₂ are C(R ₁₅ ), X ₁₃ is N or C(R ₁₅ );

In Formula 3, T ₂₁ is *''-N(R ₂₄ )-*''', *''-B(R ₂₄ )-*''', *''-P(R ₂₄ )-*''',*''-C(R ₂₄ )(R ₂₅ )-*''', *''-Si(R ₂₄ )(R ₂₅ )-*''', *''-Ge(R ₂₄ ) (R ₂₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(= O)-*''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₂₄ )=* ', *''=C(R ₂₄ )-*''', *''-C(R ₂₄ )=C(R ₂₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''',

In Formulas 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , Hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group , Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted Or an unsubstituted monovalent non-aromatic condensed heterocyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ) , -P(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ) Is selected,

In Formula 2-1, b1 is selected from an integer of 1 to 6, and when b1 is 2 or more, 2 or more R ₁ are the same or different from each other,

In Formula 3, b21 to b23 are each independently selected from integers of 1 to 3, and when b21 is 2 or more, 2 or more R ₂₁ are the same or different from each other, and when b22 is 2 or more, 2 or more R ₂₂ is When same or different from each other, and b23 is 2 or more, 2 or more R ₂₃ are the same or different from each other,

In Formulas 2-1, 2-2 and 2-3, b1 R ₁ , R ₂ , R ₃ , R ₁₁ to R ₁₄ , R ₁₅ , b21 R ₂₁ , b22 R ₂₂ , b23 R ₂₃ , Two of R ₂₄ and R ₂₅ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. Can,

In Formula 3, a21 is selected from an integer of 1 to 3, and when a21 is 2 or more, two or more T ₂₁ are the same or different from each other,

In Chemical Formulas 2-1 and 2-2, * and *'are binding sites with M in Chemical Formula 1, and in Chemical Formulas 1 and 3, *'' and *''' are binding sites with neighboring atoms. ,

The substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, , Substituted C ₁ -C ₆₀ heteroaryloxy group, substituted C ₁ -C ₆₀ heteroarylthio group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group At least one substituent selected,

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

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

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

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

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

Is selected from

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

According to another aspect, the first electrode;

A second electrode opposed to the first electrode; And

It is disposed between the first electrode and the second electrode, an organic layer including a light emitting layer; includes,

An organic light emitting device including at least one organometallic compound represented by Chemical Formula 1 is provided.

The organic light emitting device including the organometallic compound may have a low driving voltage, high luminance, high efficiency, and long life.

1 to 4 are views schematically showing structures of organic light emitting devices according to one embodiment.

The organometallic compound is represented by Formula 1 below:

<Formula 1>

M(L ₁ ) _n1 (L ₂ ) _n2

In Formula 1, M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os) ), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).

According to one embodiment, the M may be selected from Pt, Ir, Pd, Cu, Ag and Au.

For example, the M may be Pt or Ir, but is not limited thereto.

<Formula 2-1> <Formula 2-2>

<Formula 3>

In Formula 1, L ₁ is a ligand represented by Formula 2-1 or 2-2, n1 is 1, 2 or 3, and when n1 is 2 or more, 2 or more L ₁ are the same or different from each other,

In Formula 1, L ₂ is a ligand represented by Formula 3, n2 is 0, 1 or 2, and when n2 is 2 or more, 2 or more L ₂ is the same or different from each other,

In Formula 1, n1+n2 is 2 or 3.

According to an embodiment, in Formula 1, n1+n2 is 2, M is Pt, or n1+n2 is 3, and M may be Ir.

For example, in Formula 1, n1 is 1, n2 is 1, n1 is 3, and n2 may be 0, but is not limited thereto.

The organometallic compound includes a 4 or 6 coordination ligand and a metal atom (M ₁ ), and the energy level (E _3MC ) of the ^triple metal centered state of the organometallic compound (E _3MC ) is ^It may be higher than the energy level of the _triple metal-to-ligand charge transfer state (E _3MLCT ).

For example, the organometallic compound satisfies E ₃ ≥ 5 kcal/mol, and E ₃ can be defined by Equation 1 below:

<Equation 1>

E ₃ =||E _MLCT | -|E _MC ||

According to one embodiment, the organometallic compound may satisfy E ₃ ≥ 5 kcal/mol. According to another embodiment, the organometallic compound may satisfy E ₃ ≥ 8 kcal/mol, for example E ₃ ≥ 19 kcal/mol, for example E ₃ ≥ 30 kcal/mol.

For example, the six-coordination ligand may have a hemicage or fullcage structure.

According to one embodiment, the organometallic compound may satisfy 5 kcal/mol ≤ E ₃ ≤ 50 kcal/mol, for example, 8 kcal/mol ≤ E ₃ ≤ 30 kcal/mol.

When the organometallic compound satisfies the range of E ₃ , the probability of transition of the organometallic compound from the ³ MCLT state to the ³ MC state, which is a non-emissive state is reduced, and thus the stability in the excited state is excellent, and the organometallic compound Efficiency and life of the organic light emitting device including may be increased.

In Formula 1, n1 L ₁ And n2 L ₂ Is optionally a single bond, a first linking group or a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ It can be connected to each other through a heterocyclic group,

The first connector is *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''-Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)- *''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₄ )=*', * ''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*'''.

According to an embodiment, n1 and n2 are 1, L ₁ is a group represented by Chemical Formula 2-1,

_One of b1 R ₁ and one of b23 R ₂₃ adjacent to each other may be connected through a single bond or a first connector.

For example, _one of b1 R ₂₃ adjacent to one of b1 R ₁ is connected through a first connector, and the first connector may be *''-O-*''', but is not limited thereto. It is not.

According to another embodiment, n1 is 3, L ₁ is a group represented by Chemical Formula 2-2,

X ₁₃ of the three L ₁ are all C (R ₁₅ ),

Three R ₁₄ of the three L ₁ are connected to each other through a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

Three R ₁₅ of the three L ₁ may be connected to each other through a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group.

In Formula 2-1, A ₁ is selected from a C ₅ -C ₆₀ carbocyclic group and a C ₁ -C ₆₀ heterocyclic group.

According to an embodiment, in Formula 2-1, A ₁ is,

Benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silol group, oxazole group, isoxazole group , Oxadiazole group, isoxadiazole group, oxatriazole group, isoxtriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatazole group, isothiatria Sol group, pyrazole group, imidazole group, triazole group, 1,2,4-triazole group, tetrazole group, azasilol group, diazasilol group, triazasilol group, cyclohexane group, and cyclohexene group;

Deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexyl Senyl group, phenyl group, biphenyl group, terphenyl group, pentaenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, Furanyl group, silolyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group, isoxazole group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group , Isoindoleyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, isoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quina Zolinyl group, benzoquinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group , Benzoisothiazolyl group, benzooxazolyl group, benzoisooxazolyl group, triazoleyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazoleyl group, dibenzofuranyl group, dibenzo Thiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosil Rollyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspyro-bifluorenyl group, azacarbazolyl group , Azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrroleyl group, indolopyrroleyl group, indenocarbazolyl group, indolocarbazoleyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)(Q ₃₁ )(Q ₃₂ ) and -P(=S)(Q ₃₁ )(Q ₃₂ ), substituted with at least one selected from benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole Group, silol group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxtriazol group, thiazole group, isothiazole group, thiadiazole group, isothia Diazol group, thiatazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, 1,2,4-triazole group, tetrazole group, azasilol group, diazasilol group, Triazasilol group, cyclohexane group, and cyclohexene group; Is selected from

Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ hetero arylthio group, a monovalent non-aromatic hydrocarbon ring substituted with at least one selected from the group consisting of condensed polycyclic group, heavy hydrogen, -F and a cyano group-condensed polycyclic aromatic group, a monovalent non- C ₁ -C ₆₀ alkyl group, deuterium, -F, and a C ₆ -C ₆₀ aryl group substituted with at least one selected from a cyano group, a biphenyl group and a terphenyl group.

For example, A ₁ is benzene substituted with at least one selected from a benzene group and deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group group; It may be selected from, but is not limited to.

In Formula 2-1, X ₁ and X ₂ are each independently N or C(R ₃ ); In Formula 2-2, X ₁₁ and X ₁₂ are C(R ₁₅ ), and X ₁₃ is N or C(R ₁₅ ).

According to one embodiment, in Formula 2-1, X ₁ to X ₂ are C(R ₃ ), and in Formula 2-2, X ₁₃ may be C(R ₁₅ ).

In Formula 3, T ₂₁ is *''-N(R ₂₄ )-*''', *''-B(R ₂₄ )-*''', *''-P(R ₂₄ )-*''',*''-C(R ₂₄ )(R ₂₅ )-*''', *''-Si(R ₂₄ )(R ₂₅ )-*''', *''-Ge(R ₂₄ ) (R ₂₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(= O)-*''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₂₄ )=* ', *''=C(R ₂₄ )-*''', *''-C(R ₂₄ )=C(R ₂₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*'''.

According to an embodiment, in Formula 3, T ₂₁ is *''-C(R ₂₄ )(R ₂₅ )-*''', and a21 may be 1 or 2.

In Formulas 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , Hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group , Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted Or an unsubstituted monovalent non-aromatic condensed heterocyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ) , -P(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ) Is selected,

In Formula 2-1, b1 is selected from an integer of 1 to 6, and when b1 is 2 or more, 2 or more R ₁ are the same or different from each other,

In Formula 3, b21 to b23 are each independently selected from integers of 1 to 3, and when b21 is 2 or more, 2 or more R ₂₁ are the same or different from each other, and when b22 is 2 or more, 2 or more R ₂₂ is When same or different from each other, and b23 is 2 or more, 2 or more R ₂₃ are the same or different from each other,

In Formulas 2-1, 2-2 and 2-3, b1 R ₁ , R ₂ , R ₃ , R ₁₁ to R ₁₄ , R ₁₅ , b21 R ₂₁ , b22 R ₂₂ , b23 R ₂₃ , Two of R ₂₄ and R ₂₅ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. Can be.

According to one embodiment, in Formula 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently of each other, hydrogen, deuterium, -F, -Cl , -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected from the group;

Cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, pyrrolyl group, indolyl group, isoindoleyl group, indazolyl group, quinolinyl group, isoquine A monolinyl group, a quinoxalinyl group, a quinazolinyl group, a sinolinyl group, and a triazinyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindole group, indazolyl group, quinolinyl group, isoquinolinyl group , Quinoxalinyl group, quinazolinyl group, sinolinyl group, and triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ ) Cyclo substituted with at least one selected from (Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ) Pentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazoleyl group, quinolinyl group, isoquinolinyl group, quinol group A salinyl group, a quinazolinyl group, a sinolinyl group, and a triazinyl group; And

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S (=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ );

Is selected from

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

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₂₀ aryl group, C ₁ -C ₂₀ hetero Aryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed polycyclic groups;

It can be selected from.

For example, in Formula 2-1, R ₂ is a C ₁ -C ₂₀ alkyl group, -N(Q ₁ )(Q ₂ ) and a phenyl group; And a C ₁ -C ₂₀ alkyl group substituted with a C ₁ -C ₂₀ alkyl group, a -N(Q ₁ )(Q ₂ ) and a phenyl group; Is selected from

The Q ₁ and Q ₂ may be a C ₁ -C ₂₀ alkyl group, but are not limited thereto.

For example, in Formula 2-2, R ₁₁ and R ₁₂ may be independently selected from hydrogen, -F, -Cl, cyano group, C ₁ -C ₂₀ alkyl group, and phenyl group, but are not limited thereto. no.

In Formula 3, a21 is selected from an integer of 1 to 3, and when a21 is 2 or more, two or more T ₂₁ are the same or different from each other.

In Formulas 2-1 and 2-2, * and *'are binding sites with M in Formula 1, and *'' and *''' in Formulas 1 and 3 are binding sites with neighboring atoms. .

According to one embodiment, the organometallic compound represented by Formula 1 may be a group represented by any one of the following Formulas 1-1 to 1-5:

In the above formula 1-1 to 1-5,

L ₁₁ to L ₁₅ are each independently a single bond, *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''- Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)-*''',*''-S(=O)-*''',*''-S(=O) ₂ -*''', *''-C( R ₄ )=*', *''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(= S)-*''' and *''-C≡C-*''',

c11 to c15 are each independently selected from integers of 1 to 3, when c11 is 2 or more, two or more L ₁₁ are the same or different from each other, and when c12 is 2 or more, two or more L ₁₂ are the same or different from each other , When c13 is 2 or more, 2 or more L ₁₃ are the same or different from each other, when c14 is 2 or more, 2 or more L ₁₄ are the same or different from each other, and when c15 is 2 or more, 2 or more L ₁₅ is the same or different from each other and,

로 표시된 그룹이고, Y₄는 N 또는 C(R₄₀)이고, *'', *''' 및 *''''는 이웃한 원자와의 결합 사이트이고, Ar ₁ and Ar ₂ are independently of each other, a substituted or unsubstituted trivalent C ₅ -C ₃₀ carbocyclic group, a substituted or unsubstituted trivalent C ₁ -C ₃₀ heterocyclic group, and

Group, Y ₄ is N or C(R ₄₀ ), *'', *''' and *'''' are bonding sites with neighboring atoms,

c11 and c12 are each independently selected from integers of 1 to 3, when c11 is 2 or more, two or more L ₁₁ are the same or different from each other, and when c12 is 2 or more, two or more L ₁₂ are the same or different from each other ,

R _1a to R _1c , R _3a to R _3b , R _15a to R _15b , R _21a to R _21c , R _22a to R _22c , R _23a to R _23b , R _24a to R _24b , R _25a to R _25b and R ₃₀ Each refers to the definitions of R ₁ , R ₃ , R ₁₅ , R ₂₁ to R ₂₅ in claim 1, and R ₂ , R ₄ , R ₅ and R ₁₁ to R ₁₃ are respectively R in claim 1 See definitions for ₂ , R ₄ , R ₅ and R ₁₁ to R ₁₃ .

For example, Ar ₁ and Ar ₂ may be each independently selected from the group represented by Formula 2A or 2B, but are not limited thereto:

<Formula 2A> <Formula 2B>

In the above formula 2A and 2B,

Y ₁ to Y ₄ are, independently of each other, N or C(R ₄₀ ), and *'', *''' and *'''' are binding sites with neighboring atoms.

According to one embodiment, the organometallic compound may be selected from the following compounds 1 to 14, but is not limited thereto:

.

.

The organometallic compound represented by Chemical Formula 1 must include a hydroxyl group (-OH group) and a nitrogen atom at a specific position among the ligands represented by Chemical Formula 2-2, and thus, between hydroxyl groups and nitrogen atoms of neighboring ligands. Stable blue phosphorescence can be exhibited by acquiring the attraction interaction energy due to hydrogen bonding.

In addition, the organometallic compound represented by Chemical Formula 1 has a structure in which a carbazole moiety and a pyridine moiety are necessarily linked through a linker (T ₂₁ ), such as the ligand represented by Chemical Formula 3, the ligand in the triplet It is possible to exert the effect of improving the life and efficiency of the device by a mechanism that greatly increases the energy required for rupture.

In addition, when the organometallic compound represented by Chemical Formula 1 optionally includes three ligands represented by Chemical Formula 2-2, the three ligands are represented by a group represented by Chemical Formula 2A or 2B (clipping linker). By having a structure that is connected to each other, it has a three-dimensional three-dimensional hemi-cage or full-cage 6-coordination ligand, and has excellent stability and durability of the compound even in an excited state.

In addition, since the clipping linker connects the carbocyclic or heterocyclic groups included in the ligand to each other, when the organometallic compound is applied to an organic light emitting device, triplet excitons are caused by ligand rupture. (triplet exciton) can be prevented from the phenomenon of transition to the non-emission state ³ MC state is excellent stability in the excited state and the life and efficiency of the organic light emitting device is excellent.

In addition, according to one embodiment, the organometallic compound represented by Formula 1 may satisfy the above-described range of E ₃ , and in this case, from the ³ MCLC state of the organometallic compound represented by Formula 1 to the ³ MC state, which is a non-emission state The transition probability of is reduced, the stability in the excited state is excellent, and the efficiency and lifetime of the organic light emitting device including the organometallic compound may be increased.

The organometallic compound may emit blue light. For example, the organometallic compound may emit blue light having a maximum emission wavelength of 440 nm or more and 490 nm or less (back emission CIE _x,y color coordinates X=0.13, Y=0.05 to 0.18), but is not limited thereto. It does not work. As a result, the organometallic compound represented by Chemical Formula 1 can be usefully used for manufacturing an organic light emitting device that emits blue light.

The method for synthesizing the organometallic compound represented by Chemical Formula 1 can be recognized by those skilled in the art with reference to Examples described later.

At least one of the organometallic compounds represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the organometallic compound may be included in the light emitting layer. The organometallic compound included in the light emitting layer may serve as a dopant. Alternatively, the organometallic compound represented by Chemical Formula 1 may be used as a capping layer material located outside the pair of electrodes of the organic light emitting device.

Therefore, the first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode and including an emission layer. An organic light emitting device including at least one organometallic compound represented by Chemical Formula 1 is provided.

In the present specification, "(organic layer) contains one or more organometallic compounds" means "(organic layer) one organometallic compound belonging to the category of Formula 1 or two different kinds belonging to the category of Formula 1". The above organometallic compound may be included."

For example, the organic layer may include only Compound 1 as the organometallic compound. At this time, the compound 1 may be present in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the organometallic compound. In this case, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light emitting layer), or in different layers (for example, the compound 1 is the light emitting layer) And compound 2 may be present in the electron transport region.

According to one embodiment,

The first electrode of the organic light emitting device is an anode,

The second electrode of the organic light emitting device is a cathode,

The organic layer further includes a hole transport region interposed between the first electrode and the emission layer and an electron transport region interposed between the emission layer and the second electrode,

The hole transport region includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer, or any combination thereof,

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

In the present specification, "organic layer" is a term that refers to a single and/or multiple layers interposed between the first electrode and the second electrode of the organic light emitting device. The material included in the “organic layer” layer is not limited to organic materials.

According to another embodiment, the light emitting layer includes an organometallic compound represented by Chemical Formula 1, the light emitting layer further includes a host, and the content of the host in the light emitting layer is greater than the content of the organometallic compound in the light emitting layer. Can be.

According to an embodiment, the hole transport region includes an electron blocking layer, and the organometallic compound is included in the electron blocking layer;

Alternatively, the electron transport region may include a hole blocking layer, and the organometallic compound may be included in the hole blocking layer.

According to one embodiment, the hole transport region may include a p-dopant having an LUMO energy level lower than -3.5 eV.

[Description of Fig. 1]

1 schematically illustrates a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150 and a second electrode 190.

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

[First electrode 110]

A substrate may be additionally disposed below the first electrode 110 or above the second electrode 190 of FIG. 1. As the substrate, a glass substrate or a plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance can be used.

The first electrode 110 may be formed, for example, by providing a material for the first electrode on the substrate using a deposition method or a sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In order to form the first electrode 110, which is a transmissive electrode, the material for the first electrode is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and any thereof It may be selected from a combination of, but is not limited thereto. Alternatively, in order to form the first electrode 110 which is a semi-transmissive electrode or a reflective electrode, the material for the first electrode is magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li) ), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but is not limited thereto.

The first electrode 110 may have a single layer structure, which is a single layer, or a multilayer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

[Organic layer 150]

The organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer.

The organic layer 150 includes a hole transport region interposed between the first electrode 110 and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode 190. region).

[Hole transport area in organic layer 150]

The hole transport region comprises: i) a single-layer structure composed of a single material, ii) a single-layer structure composed of a plurality of different materials, or iii) a multi-layer having a plurality of layers made of a plurality of different materials. It can have a structure.

The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, and an electron blocking layer (EBL).

For example, the hole transport region has a single layer structure made of a single layer made of a plurality of different materials, or a hole injection layer/hole transport layer, a hole injection layer/hole transport layer sequentially stacked from the first electrode 110 / It may have a multi-layer structure of a light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / a light emitting auxiliary layer or a hole injection layer / hole transport layer / electron blocking layer, but is not limited thereto.

The hole transport region is 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))), Pani/CSA (Polyaniline/ Camphor sulfonic acid (polyaniline/camphorsulfonic acid)), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate) (polyaniline/poly(4-styrenesulfonate))), compound represented by the following formula 201 and formula 202 below It may include at least one selected from compounds:

<Formula 201>

<Formula 202>

In Chemical Formulas 201 and 202,

L ₂₀₁ to L ₂₀₄ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted A substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

L ₂₀₅ is *-O-*', *-S-*', *-N(Q ₂₀₁ )-*', a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C _2- C ₂₀ alkenylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent A non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

xa1 to xa4 are each independently selected from integers of 0 to 3,

xa5 is selected from integers from 1 to 10,

R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocondensation Polycyclic groups.

For example, in the formula 202, R ₂₀₁ and R ₂₀₂ may be (optionally) connected to each other through a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R ₂₀₃ and R ₂₀₄ , optionally, It may be connected to each other through a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

According to one embodiment, in the formula 201 and 202,

L ₂₀₁ to L ₂₀₅ are independently of each other,

Phenylene group, pentalene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, inda selene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluore Nylene group, dibenzofluorenylene group, phenenylene group, phenanthrenylene group, anthracenyl group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenilen group, naphthacenylene group, picenylene group, phen Relenylene group, pentaphenylene group, hexasenylene group, pentasenylene group, rubisenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group , Benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group and pyridinylylene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Neil group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenenyl group , Phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pentacene group, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole Diphenyl substituted with at least one selected from diary, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) Ren group, pentalene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, inda selene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenyl Ren group, dibenzofluorenylene group, phenenylene group, phenanthrenylene group, anthracenyl group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenilen group, naphthacenylene group, picenylene group, perylene Nylene group, pentaphenylene group, hexasenylene group, pentasenylene group, rubisenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, Benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, and pyridinylylene group;

Is selected from

The Q ₃₁ to Q ₃₃ may be independently selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

According to another embodiment, xa1 to xa4 may be 0, 1, or 2 independently of each other.

According to another embodiment, xa5 may be 1, 2, 3 or 4.

According to another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are, independently of each other, a phenyl group, a biphenyl group, a terphenyl group, a pentaenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl group, an indenyl group, Acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, naphthacenyl group, pisenyl group, perillynyl group, pentaphenyl group, hexasenyl group, pentasenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazole Diary, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Neil group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenenyl group , Phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pentacene group, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole Diphenyl, a phenyl group substituted with at least one selected from dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) , Biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perenylenyl group, pentaphenyl group , Hexasenyl group, pentasenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindole group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group , Dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group;

Can be selected from

The description of Q ₃₁ to Q ₃₃ is referred to as described herein.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₃ in Formula 201 is independently of each other,

Fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, naphthyl group , Fluorenyl group, spiro-bifluorenyl group, carbazolyl group, di substituted with at least one selected from fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group Benzofuranyl group and dibenzothiophenyl group;

It may be selected from, but is not limited to.

According to another embodiment, in Formula 202, i) R ₂₀₁ and R ₂₀₂ may be connected to each other through a single bond, and/or ii) R ₂₀₃ and R ₂₀₄ may be connected to each other through a single bond.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₄ in Formula 202,

Carbazole group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, naphthyl group , A carbazolyl group substituted with at least one selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

It may be selected from, but is not limited to.

The compound represented by Chemical Formula 201 may be represented by Chemical Formula 201-1:

<Formula 201-1>

For example, the compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201-2, but is not limited thereto:

<Formula 201-2>

As another example, the compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201-2(1), but is not limited thereto:

<Formula 201-2(1)>

The compound represented by Chemical Formula 201 may be represented by Chemical Formula 201A:

<Formula 201A>

For example, the compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201A(1), but is not limited thereto:

<Formula 201A(1)>

As another example, the compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

According to an embodiment, the compound represented by Chemical Formula 202 may be represented by Chemical Formula 202-1:

<Formula 202-1>

According to another embodiment, the compound represented by Chemical Formula 202 may be represented by Chemical Formula 202-1(1):

<Formula 202-1(1)>

Meanwhile, the compound represented by Chemical Formula 202 may be represented by Chemical Formula 202A:

<Formula 202A>

According to another embodiment, the compound represented by Chemical Formula 202 may be represented by the following Chemical Formula 202A-1:

<Formula 202A-1>

Of the formulas 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A and 202A-1,

For descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ , see as described herein,

L ₂₀₅ is selected from a phenylene group and a fluorenylene group,

X ₂₁₁ is selected from O, S and N (R ₂₁₁ ),

X ₂₁₂ is selected from O, S and N (R ₂₁₂ ),

For description of R ₂₁₁ and R ₂₁₂ , refer to the description of R ₂₀₃ in the present specification,

R ₂₁₃ to R ₂₁₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ alkyl group substitution Phenyl group, -F-substituted phenyl group, pentaenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflu Orenyl group, dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group , Pentaphenyl group, hexasenyl group, pentasenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, di It can be selected from benzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group.

The hole transport region may include, but is not limited to, at least one compound selected from the following compounds HT1 to HT48:

The hole transport region may have a thickness of about 100 mm2 to about 10000 mm2, for example, about 100 mm2 to about 1000 mm2. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer has a thickness of about 100 mm 2 to about 9000 mm 2, for example, about 100 mm 2 to about 1000 mm 2, and the hole transport layer has a thickness of about 50 mm 2 To about 2000 mm 2, for example about 100 mm 2 to about 1500 mm 2. When the thickness of the hole transport region, the hole injection layer and the hole transport layer satisfies the above-described range, 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 the light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted from the light emitting layer, and the electron blocking layer is a layer that serves to prevent electron injection from the electron transport region to be. The light emitting auxiliary layer and the electron blocking layer may include materials as described above.

[p-dopant]

The hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described materials. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

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

According to one embodiment, the LUMO of the p-dopant may be lower than -3.5 eV.

The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.

For example, the p-dopant,

Quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane);

Metal oxides such as tungsten oxide and molybdenum oxide;

HAT-CN (1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile); And

A compound represented by the following Chemical Formula 221;

It may include at least one selected from, but is not limited to:

<HAT-CN> <F4-TCNQ>

<Formula 221>

In the above formula 221,

R ₂₂₁ to R ₂₂₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent Selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one of R ₂₂₁ to R ₂₂₃ is a cyano group, -F, -Cl, -Br, -I, -F-substituted C ₁ -C ₂₀ alkyl group, selected from a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted by a C ₁ -C ₂₀ alkyl group and is substituted by -Br -I -Cl is substituted by at least a Has one substituent.

[Emitting layer of organic layer 150]

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each subpixel. Alternatively, the light emitting layer has a structure in which two or more layers selected from a red light emitting layer, a green light emitting layer, and a blue light emitting layer are stacked by contact or separation, or two or more materials selected from a red light emitting material, a green light emitting material, and a blue light emitting material are layered. It has no mixed structure and can emit white light.

The emission layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant. In addition, the phosphorescent dopant may include an organometallic compound represented by Chemical Formula 1 in the present specification.

The content of the dopant in the light emitting layer may be generally selected from about 0.01 to about 15 parts by weight with respect to about 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100 mm 2 to about 1000 mm 2, for example, about 200 mm 2 to about 600 mm 2. When the thickness of the light emitting layer satisfies the above-described range, excellent light emission characteristics may be exhibited without substantially increasing the driving voltage.

[Host among emitting layers]

The host may include a compound represented by Formula 301 below.

<Formula 301>

[Ar ₃₀₁ ] _xb11 -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb21

In the above formula 301,

Ar ₃₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xb11 is 1, 2 or 3,

L ₃₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

xb1 is an integer selected from 0 to 5,

R ₃₀₁ is deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ Alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ), -N(Q ₃₀₁ )(Q ₃₀₂ ), -B(Q ₃₀₁ )(Q ₃₀₂ ), -C(=O)(Q ₃₀₁ ), -S(=O) ₂ (Q ₃₀₁ ) and -P(=O)(Q ₃₀₁ ) (Q ₃₀₂ ),

xb21 is an integer selected from 1 to 5,

Q ₃₀₁ to Q ₃₀₃ may be independently selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but are not limited thereto.

According to an embodiment, Ar ₃₀₁ in Formula 301 is

Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group , Chrysene group, naphthacene group, picene group, perylene group, pentafen group, indenoanthracene group, dibenzofuran group and dibenzothiophene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ),- A naphthalene group, a fluorene group, substituted with at least one selected from C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ), Spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene Group, pisene group, perylene group, pentafen group, indenoanthracene group, dibenzofuran group and dibenzothiophene group;

Is selected from

Q ₃₁ to Q ₃₃ may be independently selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but are not limited thereto.

When xb11 in Formula 301 is 2 or more, two or more Ar ₃₀₁ may be connected to each other through a single bond.

According to another embodiment, the compound represented by Chemical Formula 301 may be represented by the following Chemical Formula 301-1 or 301-2:

<Formula 301-1>

<Formula 301-2>

In the above formula 301-1 to 301-2

A ₃₀₁ to A ₃₀₄ are independently of each other, benzene, naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysene, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzoflu Orene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, Dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene,

X ₃₀₁ is O, S or N-[(L ₃₀₄ ) _xb4 -R ₃₀₄ ],

R ₃₁₁ to R ₃₁₄ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ),- B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ), ,

xb22 and xb23 are each independently 0, 1 or 2,

For descriptions of L ₃₀₁ , xb1, R ₃₀₁ and Q ₃₁ to Q ₃₃ , see as described herein,

The description of L ₃₀₂ to L ₃₀₄ is independent of each other, see the description of L ₃₀₁ above,

Description of xb2 to xb4 is independent of each other, refer to the description of xb1 above,

Descriptions of R ₃₀₂ to R ₃₀₄ are independent of each other, and refer to the description of R ₃₀₁ above.

For example, L ₃₀₁ to L ₃₀₄ in Formulas 301, 301-1, and 301-2 are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenenylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzo Puranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylylene group, imidazolylene group, pyrazolylene group , Thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl group Ren group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinylene group, acridinylene group, phenane Trolylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzooxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylylene group, imidazopyrimidine group Nylene group and azacarbazolylene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group , Isobenzooxazolyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ ) (Q ₃₂ ), substituted with at least one selected from phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenyl Ren group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenylene group, chrysylene group, perylenenylene group, pentaphenylene group, hexasenylene group, pentasenilene group, thiophenylene group, furanylene group, carba Zolylene group, indolylene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, Dibenzocarbazolylene group, dibenzosilolylene group, pyridinylylene group, imidazolylene group, pyrazolylene group, thiazoleylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiia Zolylene group, pyrazinylene group, pyrimidinylene group, pyridazinyl group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxali group Nylene group, quinazolinyl group, sinolinyl group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzooxazolylene group, iso Benzooxazolylene group, triazoleylene group, tetrazolylene group, imidazopyridinylylene group, imidazopyrimidinylene group and azacarbazolylene group;

Is selected from

The description of Q ₃₁ to Q ₃₃ may be referred to as described herein.

As another example, R ₃₀₁ to R ₃₀₄ in Formulas 301, 301-1, and 301-2 are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylene Neil group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentacene group, thiophenyl group, furanyl group, carbazole group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group , Isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group , Naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group, Isobenzooxazolyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group , Isobenzooxazolyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ ) (Q ₃₂ ), a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group , Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylene group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazole group, indolyl group , Isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosil Rollyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group, isoxazole group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, arc Ridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyridyl group A midinyl group and an azacarbazolyl group;

Is selected from

The description of Q ₃₁ to Q ₃₃ may be referred to as described herein.

As another example, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, Compound H55 below), a Mg complex, and a Zn complex.

The host is 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) and at least one selected from compounds H1 to H55 below, but is not limited thereto:

Alternatively, the host may include at least one of a silicon-containing compound (e.g., BCPDS used in the following examples) and a phosphine oxide-containing compound (e.g., POPCPA used in the following examples). Can be.

The host may include only one compound, or may include two or more different compounds from each other (for example, the host of the following example consists of BCPDS and POPCPA), and various modifications are possible.

[Phosphorescent dopant included in light emitting layer among organic layers 150]

The phosphorescent dopant may include an organometallic compound represented by Chemical Formula 1 in the present specification.

In addition, the phosphorescent dopant may include an organometallic complex represented by the following Chemical Formula 401:

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

In the above formulas 401 and 402,

M is iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) ) And Thulium (Tm),

L ₄₀₁ is selected from ligands represented by the formula 402, and xc1 is 1, 2 or 3, xc1 this case, 2 or more, two or more L ₄₀₁ are the same or different from each other,

L ₄₀₂ is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, 2 or more L ₄₀₂ are the same or different from each other,

X ₄₀₁ to X ₄₀₄ are, independently of each other, nitrogen or carbon,

X ₄₀₁ and X ₄₀₃ are connected through a single bond or a double bond, X ₄₀₂ and X ₄₀₄ are connected through a single bond or a double bond,

A ₄₀₁ and A ₄₀₂ are each independently a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

X ₄₀₅ 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=*', wherein Q ₄₁₁ and Q ₄₁₂ are , Hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group or naphthyl group,

X ₄₀₆ is a single bond, O or S,

R ₄₀₁ and R ₄₀₂ are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or Unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C _6- C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or Unsubstituted monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ ), wherein Q ₄₀₁ to Q ₄₀₃ are independent of each other As, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₁ -C ₂₀ heteroaryl group is selected from,

xc11 and xc12 are each independently selected from integers of 0 to 10,

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

According to an embodiment, A ₄₀₁ and A ₄₀₂ in Formula 402 are independently of each other, a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan ( furan) group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, quinoline group, iso Quinoline group, benzoquinoline group, quinoxaline group, quinazoline group, carbazole group, benzoimidazole group, benzofuran group, benzothiophene group, isobenzothiophene group, benzooxazole group, isobenzooxa It can be selected from sol group, triazole group, tetrazole group, oxadiazole group, triazine group, dibenzofuran group and dibenzothiophene group.

According to another embodiment, in Formula 402, i) X ₄₀₁ may be nitrogen, X ₄₀₂ may be carbon, or ii) X ₄₀₁ and X ₄₀₂ may both be nitrogen.

According to another embodiment, R ₄₀₁ and R ₄₀₂ in Formula 402 are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ Alkoxy groups;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, phenyl group, naphthyl group, cyclopentyl group, cyclohexyl group, ada A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected from a mantanyl group, a norbornanyl group, and a norbornenyl group;

Cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group Group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group A cyclopentyl group, cyclohexyl, substituted with at least one selected from a genyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group Practical group, adamantanyl group, norbornanyl group, norbornenyl group phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinyl group Nolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; And

-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 ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ );

Is selected from

The Q ₄₀₁ to Q ₄₀₃ may be independently selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, and naphthyl groups, but are not limited thereto.

According to yet another embodiment, if the above formula 401 xc1 is 2 or more of, two of the two or more L ₄₀₁ of A ₄₀₁ are either selectively connected to each other through a by (optionally), connected group X _407, 2 of A ₄₀₂ is optionally , Can be connected to each other through the linker X ₄₀₈ (see compounds PD1 to PD4 and PD7 below). X ₄₀₇ and X ₄₀₈ are each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q ₄₁₃ )-*', *-C(Q ₄₁₃ )(Q ₄₁₄ )-*' or *-C(Q ₄₁₃ )=C(Q ₄₁₄ )-*' (where Q ₄₁₃ and Q ₄₁₄ are independently of each other, hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group), but is not limited thereto.

L ₄₀₂ in Formula 401 may be any monovalent, divalent, or trivalent organic ligand. For example, L ₄₀₂ is halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g. picolinate), -C(=O), isonitrile, -CN and phosphorus It may be selected from materials (for example, phosphine (phosphine), phosphite), but is not limited thereto.

Alternatively, the phosphorescent dopant may be selected from, for example, the following compounds PD1 to PD25, but is not limited thereto:

[Fluorescent dopant in the light emitting layer]

The fluorescent dopant may include an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by the following Chemical Formula 501:

<Formula 501>

In the above formula 501,

Ar ₅₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

L ₅₀₁ to L ₅₀₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted A substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

xd1 to xd3 are each independently selected from integers of 0 to 3,

R ₅₀₁ and R ₅₀₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group Is selected,

xd4 may be selected from integers from 1 to 6.

According to one embodiment, Ar ₅₀₁ in the formula 501,

Naphthalene group, heptane group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenane group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group , Pyrene group, chrysene group, naphthacene group, pisene group, perylene group, pentafen group, indenoanthracene group and indenophenanthrene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , A naphthalene group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, phenylene substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group Group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, pisene group, perylene group, pentafen group, indenoanthracene group and indenophenane Tren group;

It can be selected from.

According to another embodiment, L ₅₀₁ to L ₅₀₃ in Formula 501 are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenenylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzo A furanylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylylene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Phenylene group, naphthylene group, fluorenylene group, spy, substituted with at least one selected from dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group Low-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenyl group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylene Nylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranyl Ren group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylylene group;

It can be selected from.

According to another embodiment, R ₅₀₁ and R ₅₀₂ in Formula 501 are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylene Neil group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentacene group, thiophenyl group, furanyl group, carbazole group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, tri Phenylenyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazole group, indolyl group, isoindolyl group, benzofuranyl group, benzothio Phenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group;

Is selected from

The Q ₃₁ to Q ₃₃ may be selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

According to another embodiment, xd4 in Formula 501 may be 2, but is not limited thereto.

For example, the fluorescent dopant can be selected from the following compounds FD1 to FD22:

Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto.

.

.

[The electron transport region in the organic layer 150]

The electron transport region includes i) a single layer structure composed of a single material, ii) a single layer structure composed of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials. Can have

The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may be an electron transport layer/electron injection layer, hole blocking layer/electron transport layer/electron injection layer, electron control layer/electron transport layer/electron injection layer, or buffer layer/electron transport layer/stacked sequentially from the light emitting layer/ It may have a structure such as an electron injection layer, but is not limited thereto.

The electron transport region (eg, a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing ring. .

The "π electron deficient nitrogen-containing ring" means a C ₁ -C ₆₀ heterocyclic group having at least one *-N=*' moiety as a ring-forming moiety.

For example, the "π electron deficient nitrogen-containing ring" is i) a 5-7 membered heteromonocyclic group having at least one *-N=*' moiety, or ii) at least one *- Two or more of the 5- to 7-membered heteromonocyclic groups having N=*' moieties are heteropolycyclic groups condensed with each other, or iii) 5-membered with at least one *-N=*' moiety It may be a heteropolycyclic group in which at least one of the 7 to 7 membered heteromonocyclic groups and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

Specific examples of the π electron-deficient nitrogen-containing ring include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine , Quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, sinoline, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, isobenzothiazole, benzo Oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, azacarbazole, and the like, but is not limited thereto.

For example, the electron transport region may include a compound represented by Chemical Formula 601 below.

<Formula 601>

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

In the above formula 601,

Ar ₆₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xe11 is 1, 2 or 3,

L ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

xe1 is an integer selected from 0 to 5,

R ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , Substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₆₀₁ ) (Q ₆₀₂ )(Q ₆₀₃ ), -C(=O)(Q ₆₀₁ ), -S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ ),

Q ₆₀₁ to Q ₆₀₃ are, independently of each other, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

xe21 is selected from the integers of 1-5.

According to an embodiment, at least one of the xe11 Ar ₆₀₁ and the xe21 R ₆₀₁ may include a π electron-deficient nitrogen-containing ring as described above.

According to one embodiment, the ring Ar ₆₀₁ in the formula 601,

Benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenane group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, Pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group , Thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, Phthazin group, naphthyridine group, quinoxaline group, quinazoline group, synolin group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group , Benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group ; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )( Q ₃₂ ), a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenane group, a phenanthrene group, anthracene group, Fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carba Sol group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline Group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, Benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, already Dazopyrimidine group and azacarbazole group;

Can be selected from

The Q ₃₁ to Q ₃₃ may be independently selected from C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.

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

According to another embodiment, Ar ₆₀₁ in Formula 601 may be an anthracene group.

According to another embodiment, the compound represented by 601 may be represented by the following Chemical Formula 601-1:

<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 X ₆₁₄ to X ₆₁₆ is N,

L ₆₁₁ to L ₆₁₃ independently of each other, refer to the description of L ₆₀₁ above,

xe611 to xe613 independently of each other, refer to the description of xe1 above,

R ₆₁₁ to R ₆₁₃ independently of each other, refer to the description of R ₆₀₁ above,

R ₆₁₄ to R ₆₁₆ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ It may be selected from -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group and naphthyl group.

According to an embodiment, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ in Formulas 601 and 601-1 are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenenylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzo Puranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylylene group, imidazolylene group, pyrazolylene group , Thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl group Ren group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinylene group, acridinylene group, phenane Trolylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzooxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylylene group, imidazopyrimidine group Nylene group and azacarbazolylene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group , Phenylene group, naphthylene group, fluorenylene group, substituted with at least one selected from isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, Spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylrenylene group, pyrenylene group, chrysenylene group, phen Relenylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofune group Lanylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazoleylene group, isothiazolylene group, oxazolyl group Ren group, isoxazole group, thiadiazole group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinyl group, benzoquinolinyl group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylylene group, sinolinylene group , Phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzooxazolylene group, isobenzooxazolylene group, triazoleylene group, tetrazolylene group , Imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group;

It may be selected from, but is not limited to.

According to another embodiment, in Formulas 601 and 601-1, xe1 and xe611 to xe613 may be 0, 1, or 2 independently of each other.

According to another embodiment, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ of Formulas 601 and 601-1 are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylene Neil group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentacene group, thiophenyl group, furanyl group, carbazole group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group , Isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group , Naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group, Isobenzooxazolyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazole group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group Group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, flu, substituted with at least one selected from isobenzooxazolyl group, triazoleyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylene group Neil group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Diazole group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group, isoxazole group, thiadiazolyl group, oxadia Solyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoqui Nolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group , Isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; And

-S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ );

Is selected from

For the description of Q ₆₀₁ and Q ₆₀₂ , refer to the descriptions herein.

The electron transport region may include, but is not limited to, at least one compound selected from the following compounds ET1 to ET36:

Alternatively, the electron transport region is BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , BAlq, TAZ ( It may include at least one compound selected from 3- (Biphenyl-4-yl) -5- (4- tert -butylphenyl) -4-phenyl-4 H -1,2,4-triazole) and NTAZ.

As another example, the electron transport region may be a phosphine oxide-containing compound or the like, but is not limited thereto. According to one embodiment, the phosphine oxide-containing compound may be used in the hole blocking layer in the electron transport region, but is not limited thereto.

The thickness of the buffer layer, hole blocking layer, or electron control layer may be, independently of each other, about 20 mm 2 to about 1000 mm 2, for example, about 30 mm 2 to about 300 mm 2. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer satisfies the above-described range, excellent hole blocking characteristics or electron control characteristics may be obtained without a substantial increase in driving voltage.

The thickness of the electron transport layer may be about 100 mm 2 to about 1000 mm 2, for example, about 150 mm 2 to about 500 mm 2. When the thickness of the electron transport layer satisfies the above-described range, it is possible to obtain a satisfactory electron transport property without substantially increasing the 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 above-described materials.

The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The metal ion of the alkali metal complex can be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the metal ions of the alkaline earth metal complexes are Be ions, Mg ions, Ca ions, Sr ions and Ba It can be selected from ions. 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, hydroxyphenyl Oxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline And cyclopentadiene, but is not limited thereto.

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

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

The electron injection layer comprises: i) a single layer structure made of a single material, ii) a single layer structure made of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers made of a plurality of different materials. Can have

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may be selected from Li, Na, K, Rb and Cs. According to one embodiment, the alkali metal may be Li, Na or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

The alkali metal compound, the alkaline earth metal compound and the rare earth metal compound may be selected from oxides and halides (eg, fluoride, chloride, bromide, iodide, etc.) of the alkali metal, the alkaline earth metal, and the rare earth metal. have.

The alkali metal compound may be selected from alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI. According to one embodiment, the alkali metal compound may be selected from LiF, Li ₂ O, NaF, LiI, NaI, CsI, KI, but is not limited thereto.

The alkaline earth metal compound may be selected from alkali earth metal compounds such as BaO, SrO, CaO, Ba _x Sr _{1 - x} O(0<x<1), Ba _x Ca _{1 -x} O(0<x<1), etc. have. According to one embodiment, the alkaline earth metal compound may be selected from BaO, SrO and CaO, but is not limited thereto.

The rare earth metal compound may be selected from YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , and TbF ₃ . According to one embodiment, the rare earth metal compound are _{YbF 3, ScF 3, TbF 3} , YbI 3, ScI 3, TbI 3 may be selected from, but is not limited to such.

The alkali metal complex, alkaline earth metal complex and rare earth metal complex include ions of alkali metal, alkaline earth metal and rare earth metal as described above, and are coordinated with metal ions of the alkali metal complex, alkaline earth metal complex and rare earth metal complex. Ligands, independently of each other, are hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxa Diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is not limited thereto. It is not.

The electron injection layer is composed of only the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof, as described above, or , It may further include the organic material. When the electron injection layer further includes an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any of these The combination may be uniformly or non-uniformly dispersed in the matrix made of the organic material.

The thickness of the electron injection layer may be about 1 mm 2 to about 100 mm 2, and about 3 mm 2 to about 90 mm 2. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[Second electrode 190]

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. At this time, as a material for the second electrode 190, a metal, alloy, electroconductive compound having a low work function, and combinations thereof (combination) can be used.

The second electrode 190 is lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) ), magnesium-silver (Mg-Ag), may include at least one selected from ITO and IZO, but is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single layer structure, which is a single layer, or a multilayer structure having a plurality of layers.

[Description of FIGS. 2 to 4]

Meanwhile, the organic light emitting device 20 of FIG. 2 has a structure in which the first capping layer 210, the first electrode 110, the organic layer 150, and the second electrode 190 are sequentially stacked, and the organic of FIG. The light emitting device 30 has a structure in which the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked, and the organic light emitting device 40 of FIG. The first capping layer 210, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked.

For descriptions of the first electrode 110, the organic layer 150, and the second electrode 190 in FIGS. 2 to 4, refer to the description of FIG. 1.

Light generated from the light emitting layer among the organic layers 150 of the organic light emitting devices 20 and 40 may be taken out through the first electrode 110 and the first capping layer 210 which are semi-transmissive electrodes or transmissive electrodes, Light generated from the light emitting layer among the organic layers 150 of the organic light emitting devices 30 and 40 may be taken out through the second electrode 190 and the second capping layer 220 which are semi-transmissive electrodes or transmissive electrodes.

The first capping layer 210 and the second capping layer 220 may serve to improve external luminous efficiency by the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may be independently of each other, an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one of the first capping layer 210 and the second capping layer 220, independently of each other, a carbocyclic compound, a heterocyclic compound, an amine-based compound, porphine derivatives, phthalocyanine derivative ( phthalocyanine derivatives), naphthalocyanine derivatives, alkali metal complexes and alkaline earth metal complexes. The carbocyclic compound, heterocyclic compound, and amine-based compound may be optionally substituted with a substituent including at least one element selected from O, N, S, Se, Si, F, Cl, Br and I. .

According to one embodiment, at least one of the first capping layer 210 and the second capping layer 220, independently of each other, may include an amine-based compound.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220, independently of each other, may include a compound represented by Formula 201 or a compound represented by Formula 202 have.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220, independently of each other, may include a compound selected from the compounds HT28 to HT33 and the following compounds CP1 to CP5 However, it is not limited thereto.

The organic light emitting device has been described above with reference to FIGS. 1 to 4, but is not limited thereto.

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

When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are respectively formed by a vacuum deposition method, deposition conditions are, for example, a deposition temperature of about 100 to about 500°C, about 10 It can be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed, within a vacuum degree of ^-8 to about 10 ^-3 torr and a deposition rate range of about 0.01 to about 100 kPa/sec.

When each layer included in the hole transport region, each light emitting layer and the electron transport region included in the hole transport region is formed by a spin coating method, the coating conditions are, for example, a coating speed of about 2000 rpm to about 5000 rpm and a coating speed of about 80 Within the heat treatment temperature range of ℃ to 200 ℃, may be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed.

[General definition of the substituent]

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

C ₂ -C ₆₀ alkenyl group used herein refers to a hydrocarbon group including one or more carbon double bonds at the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. Etc. are included. C ₂ -C ₆₀ alkenylene group used herein refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

C ₂ -C ₆₀ alkynyl group used herein refers to a hydrocarbon group containing at least one carbon triple bond at the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, propynyl group, and the like. Is included. C ₂ -C ₆₀ alkynylene group used herein refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

The C ₁ -C ₆₀ alkoxy group used herein 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 a methoxy group and an ethoxy group. , Isopropyloxy group, and the like.

C ₃ -C ₁₀ cycloalkyl group used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclo group. Heptyl groups and the like. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

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

C ₃ -C ₁₀ cycloalkenyl group as used herein refers to a monovalent monocyclic group having 3 to 10 carbon atoms, which means a group having at least one double bond in a ring, but no aromaticity, and specifics thereof Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. AC ₃ -C ₁₀ cycloalkenylene group used herein refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, and is a ring. Has at least one double bond in it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, and 2,3-dihydro And thiophenyl groups. AC ₁ -C ₁₀ heterocycloalkenylene group used herein refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

C ₆ -C ₆₀ aryl group used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and C ₆ -C ₆₀ arylene group having 6 to 60 carbocyclic aromatic systems having 6 to 60 carbon atoms. It means a divalent group having. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, and the like. 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.

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

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group).

In the present specification, 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-aromaticity. Means a monovalent group having (eg, having 8 to 60 carbon atoms). A specific example of the monovalent non-aromatic condensed polycyclic group includes a fluorenyl group and the like. In the present specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The monovalent non-aromatic condensed heteropolycyclic group of the present specification is at least one selected from N, O, Si, P, and S other than carbon as two or more rings condensed with each other and as ring-forming atoms. Means a monovalent group (eg, having 1 to 60 carbon atoms) containing a hetero atom and having the entire molecule non-aromatic. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group and the like. In the present specification, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The C ₄ -C ₆₀ carbocyclic group used herein refers to a monocyclic or polycyclic group having 4 to 60 carbon atoms including only carbon as a ring-forming atom. The C ₄ -C ₆₀ carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₄ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, it is the C ₄ -C according to the number attached to the substituent at the ₆₀ carbocyclic group, a C ₄ -C ₆₀ carbocyclic group during the various modifications can be made, such as in 3 or 4 is the group number of a group.

In the present specification, a C ₂ -C ₆₀ heterocyclic group has the same structure as the C ₄ -C ₆₀ carbocyclic group, and as a ring-forming atom, carbon (the number of carbon atoms may be 2 to 60), N , O, Si, P and S means a group including at least one hetero atom selected from.

In the present specification, the substituted C ₄ -C ₆₀ carbocyclic group, the substituted C ₂ -C ₆₀ heterocyclic group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkyl Ren group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted Divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed polycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, Substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted 1 At least one of the substituents of the non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C _2- C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

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

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

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

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

Is selected from

The Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, army Dino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C 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 C ₁ -C ₆₀ substituted with at least one selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, deuterium, -F and a cyano group, C ₆ -substituted with at least one selected from a deuterium, -F and a cyano group. C ₆₀ aryl group, biphenyl group and terphenyl group.

In the present specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "Bu ^t "means a tert-butyl group, and "OMe "Means a methoxy group.

In the present specification, "biphenyl group" means "phenyl group substituted with a phenyl group". The "biphenyl group" belongs to a "substituted phenyl group" in which the substituent is "C ₆ -C ₆₀ aryl group".

“Terphenyl group” in the present specification means “phenyl group substituted with a biphenyl group”. The "terphenyl group" belongs to a "substituted phenyl group" in which the substituent is "C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group".

*, *'and *" in the present specification mean a binding site with an adjacent atom in the chemical formula, unless otherwise defined.

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

[Synthesis example]

Synthesis Example 1: Synthesis of Compound 1

1) Synthesis of Intermediate Compound [1-A]

1-Bromo-2-nitrobenzene (1.0 eq), 4-methoxy phenylboronic acid (1.2 eq), K ₂ CO ₃ (2.0 eq), and 0.01 g of Pd(dppl) ₂ Cl ₂ catalyst are added to dissolve in DMSO solution After the preparation, the mixture was stirred at 130° C. for 6 hours until all the reactants were consumed. After the reaction mixture was cooled to room temperature, it was extracted three times with ethyl acetate and water to separate the organic layer from the mixture layer. The obtained organic layer was dried over magnesium sulfate, and concentrated to obtain an intermediate compound [1-A] (yield 78%) using column chromatography.

2) Synthesis of Intermediate Compound [1-B]

After the intermediate compound [1-A] (1.2 eq) was dissolved in dichloromethane (0.1 M), PPh ₃ (2.0 eq) was slowly added thereto while stirring at -78°C, followed by stirring for 2 hours. After the reaction mixture was cooled to room temperature, it was extracted three times with ethyl acetate and water, and the organic layer was separated from the mixture layer. After drying the obtained organic layer with magnesium sulfate, it was concentrated to obtain the intermediate compound [1-B] (yield 61%).

3) Synthesis of Intermediate Compound [1-C]

Intermediate compound [1-B] (1.5 eq) and methyl-2-bromoicotinate (1.1 eq) to Cuene (0.03 g), K ₂ CO ₃ (2.0 eq), and L-Proline (0.04 eq) toluene (0.1 M ), and stirred at 130° C. for 12 hours. After the reaction mixture was cooled to room temperature, the organic layer was dried over magnesium sulfate, and then concentrated to obtain an intermediate compound [1-C] (yield 59%) using column chromatography.

4) Synthesis of Intermediate Compound [1-D]

The intermediate compound [1-C] (1.3eq), Griniard reagent (1.3 eq) was dissolved in THF, and the mixture was stirred for 24 hours at room temperature until the reactants were completely consumed. Dichloromethane and water were extracted three times to obtain an organic layer. After drying the obtained organic layer with magnesium sulfate, it was concentrated to obtain an intermediate compound [1-D] (yield 45%) using column chromatography.

5) Synthesis of Intermediate Compound [1-E/1-F]

After dissolving the intermediate compound [1-D] (1.0 eq), di-p-tolyliodonium trifluoromethane sulfonate (1.5 eq) and CuOAc (0.1 eq) in toluene (0.1 M), the reactants are consumed for 10 hours at 100°C. Stir until The obtained intermediate compound [1-E] (1.0 eq) was subjected to a high temperature (500K), high pressure (10 atm) hydrogenation reaction under a Pd/C catalyst (0.02 g) to obtain intermediate compound [1-F] (yield 74%). Obtained.

6) Synthesis of intermediate compound and final compound [1-G/1-H/1]

Intermediate compound [1-F] (1.2 eq), 1-(3-boromo-phenyl)-1H-imidazole (1.0 eq), CuI (0.02 eq), tBuONa (2.0 eq), and L-Proline (0.04 eq) Was dissolved in toluene (0.1 M), and stirred at 160°C for 48 hours. After the obtained intermediate compound [1-G] was cooled to room temperature, it was extracted three times with CH ₂ Cl ₂ and water to obtain an organic layer. The obtained organic layer was dried over Na ₂ SO ₃ and concentrated to obtain an intermediate [1-H] ligand compound (yield 85%) using chromatography. The obtained intermediate [1-H] ligand compound (1.0 eq) was dissolved in dicholo(1,5-cyclootadienyl) plantinum (II) (1.05 eq), sodium acetate (3.0 eq) in THF (0.1 M), and then 120°C. It was stirred for 72 hours under a nitrogen atmosphere. After the reaction was cooled to room temperature, the solvent was removed under reduced pressure. The concentrated reaction was dissolved in dichloromethane, and the remaining precipitate was filtered through filtration. The filtrate was purified using column chromatography to obtain Compound 1 (20% yield).

MS cald. For C ₃₀ H ₂₂ N ₄ OPt (MS+1), m/z 649.6; observed 649.6

Synthesis Example 2: Synthesis of Compound 3

1) Synthesis of Intermediate Compound [3-A]

1-Bromo-3-chloro-2-nitrobenzene (1.0 eq), 4-methoxy phenylboronic acid (1.2 eq), K ₂ CO ₃ (2.0 eq), and 0.01 g of Pd(dppl) ₂ Cl ₂ catalyst After dissolving in the DMSO solution, stirring was continued at 130° C. for 6 hours until the reaction was completely consumed. After the reaction mixture was cooled to room temperature, it was extracted three times with ethyl acetate and water, and the organic layer was separated from the mixture layer. The obtained organic layer was dried over magnesium sulfate, and then concentrated to obtain an intermediate compound [3-A] (yield 75%) using column chromatography.

2) Synthesis of Intermediate Compound [3-B]

After the intermediate compound [3-A] (1.2 eq) was dissolved in dichloromethane (0.1 M), PPh ₃ (2.0 eq) was slowly added thereto while stirring at -78°C, followed by stirring for 2 hours. After the reaction mixture was cooled to room temperature, it was extracted three times with ethyl acetate and water, and the organic layer was separated from the mixture layer. The obtained organic layer was dried over magnesium sulfate, and then concentrated to obtain an intermediate compound [3-B] (yield 59%).

3) Synthesis of Intermediate Compound [3-C]

Intermediate compounds [3-B] (1.5 eq) and 2-bromo-3-vinylpyridine (1.1 eq) were added to Pd ₂ (dba) ₃ (0.03 g), PPh ₃ (2 eq), and t-BuONa (2.0 eq). After dissolving in Dioxane (0.1 M) together, the mixture was stirred at 130° C. for 12 hours. After the reaction mixture was cooled to room temperature, the organic layer was dried over magnesium sulfate, and concentrated to obtain an intermediate compound [3-C] (yield 51%) using column chromatography.

4) Synthesis of Intermediate Compound [3-D]

Intermediate compound [3-C] (1.3eq), Pd ₂ (dba) ₃ (0.03 g), DavePhos (1.3 eq), and t-BuONa (0.02 eq) were dissolved in Dioxane and the reactants were consumed at room temperature for 24 hours. Stirring was continued until possible. Dichloromethane and water were extracted three times to obtain an organic layer. After drying the obtained organic layer with magnesium sulfate, it was concentrated to obtain an intermediate compound [3-D] (yield 41%) using column chromatography.

5) Synthesis of Intermediate Compound [3-E/3-F]

After dissolving the intermediate compound [3-D] (1.0 eq), di-p-tolyliodonium trifluoromethane sulfonate (1.5 eq) and CuOAc (0.1 eq) in toluene (0.1 M), the reactants are consumed for 10 hours at 100°C. Stir until The obtained intermediate compound [3-E] (1.0 eq) was subjected to a high temperature (500K), high pressure (10 atm) hydrogenation reaction under a Pd/C catalyst (0.02 g) to obtain intermediate compound [3-F] (yield 42%). Obtained.

7) Synthesis of intermediate compound and final compound [3-G/3-H/3]

Intermediate compound [3-F] (1.2 eq), 1-(3-boromo-phenyl)-1H-imidazole (1.0 eq), CuI (0.02 eq), tBuONa (2.0 eq), and L-Proline (0.04 eq) Was dissolved in toluene (0.1 M), and stirred at 160°C for 48 hours. After the obtained intermediate compound [3-G] was cooled to room temperature, it was extracted three times with CH ₂ Cl ₂ and water to obtain an organic layer. The obtained organic layer was dried over Na ₂ SO ₃ , concentrated to obtain an intermediate [3-H] ligand compound (yield 80%) using chromatography. The obtained intermediate [3-H] ligand compound (1.0 eq) was dissolved in dicholo(1,5-cyclootadienyl) plantinum (II) (1.05 eq), sodium acetate (3.0 eq) in THF (0.1 M), and then 120°C. It was stirred for 72 hours under a nitrogen atmosphere. After the reaction was cooled to room temperature, the solvent was removed under reduced pressure. The concentrated reaction was dissolved in dichloromethane, and the remaining precipitate was filtered through filtration. The filtrate was purified using column chromatography to obtain compound 3 (yield 22%).

MS cald. For C ₂₉ H ₂₀ N ₄ OPt (MS+1), m/z 635.6; observed 635.6

Compounds 2, 4 and 5 were synthesized in addition to compounds 1 and 3 with reference to the methods disclosed in Synthesis Examples 1 and 2 above.

Evaluation Example 1: Quantum simulation analysis

The energy levels of the ³ MLCT states of Compounds 1 to 5 and Compounds A to C below as Comparative Compounds were evaluated using B3LYP functional, and in the case of Ir, the LANL2DZ basis set other C, H, N, and F atoms At the 6-311G(d,p) basis set level, the ground state energy and triplet energy, evaluated using the DFT method employing the structure-optimized Gaussian program, are calculated based on the ³ MC state energy level value, thereby From E ₃ is calculated according to Equation 1 as described above and is shown in Table 1.

compound T ₁ (eV) ³ MC (Kcal/mol) ³ MCLT E ₃ (kcal/mol) Compound 1 2.68 27.4 12.11 27.4 Compound 2 2.65 27.2 12.32 27.2 Compound 3 2.65 27.4 12.24 27.4 Compound 4 2.61 - 19.50 - Compound 5 2.79 31.0 24.08 31.0 Compound A 2.71 9.87 9.82 9.87 Compound B 2.14 22.45 15.32 6.08 Compound C 2.39 10.96 22.08 10.96

<Compound A> <Compound B>

<Compound C>

From Table 1, E ₃ the value of the compounds 1 to 5 were significantly higher than the value E ₃ of the compound A-C. Accordingly, the compounds 1 to 5 have excellent transition stability from the ³ MCLT state to the ³ MC state, which is a non-emission state, and have excellent stability in an excited state, and increase the efficiency and lifetime of the organic light emitting device including the organometallic compound. Can be.

Example 1

As a substrate and anode, Corning's 15 Ω/cm ² (1200 Å) ITO-formed glass substrate was cut into 50 mm x 50 mm x 0.7 mm size, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes, and then 30 minutes. While irradiated with ultraviolet rays, it was cleaned by exposure to ozone, and the glass substrate was installed in a vacuum deposition apparatus.

A vacuum injection layer of 2-TNATA was formed on the ITO anode formed on the organic substrate to form a hole injection layer having a thickness of 600 Å, and a hole transport layer having a thickness of 300 층 was formed by vacuum deposition of NPB on the hole injection layer.

Co-hosts BCPDS(bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane) and POPCPA((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl on the hole transport layer -phosphine oxide) (the weight ratio of BCPDS and POPCPA is 1:1) and the dopant compound 1 were co-deposited so that the weight ratio of the co-host and the dopant was 90:10 to form a 300 mm thick light emitting layer.

A hole blocking layer having a thickness of 50Å is formed by depositing diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) on the light emitting layer, and an electron transport layer having a thickness of 300Å is deposited by depositing Alq ₃ on the hole blocking layer. Then, after depositing LiF on the electron transport layer to form an electron injection layer having a thickness of 10 Å, Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3000 ,, thereby fabricating an organic light emitting device.

Examples 2 to 3 and Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 2 was used instead of Compound 1 as a dopant in the formation of the emission layer.

Evaluation Example 2

The driving voltage, current density, lifetime (LT ₉₅ ), emission efficiency, emission color, and maximum emission wavelength of the organic light emitting devices manufactured in Examples 1 to 3 and Comparative Example 1 were measured using Keithley SMU 236 and a luminance meter PR650, , The results are shown in Table 2.

Emitting layer
Medium dopant Driving voltage
(V) Current density
(㎃/㎠) Life Span (LT ₉₅ )
(hr) Emission color Emission wavelength (nm) Example 1 One 4.8 0.383 45 blue 464 Example 2 3 4.6 0.356 58 blue 468 Example 3 5 5.1 0.427 33 blue 445 Comparative Example 1 A 4.6 0.320 10 blue 467

Referring to Table 2, it can be seen that the organic light-emitting devices according to Examples 1 to 3 have significantly better current density and lifespan characteristics than the organic light-emitting devices according to Comparative Example 1.

10: organic light emitting device
110: first electrode
150: organic layer
190: second electrode
210: first capping layer
220: second capping layer

Claims (20)

A first electrode;
A second electrode opposed to the first electrode; And
It is disposed between the first electrode and the second electrode, an organic layer including a light emitting layer; includes,
An organic light emitting device comprising at least one organometallic compound represented by Formula 1 below:
<Formula 1>
M(L ₁ ) _n1 (L ₂ ) _n2
<Formula 2-1><Formula2-2>

<Formula 3>

In Formula 1,
M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti) ), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm);
In Formula 1, L ₁ is a ligand represented by Formula 2-1 or 2-2, n1 is 1, 2 or 3, and when n1 is 2 or more, 2 or more L ₁ are the same or different from each other,
In Formula 1, L ₂ is a ligand represented by Formula 3, n2 is 0, 1 or 2, and when n2 is 2 or more, 2 or more L ₂ is the same or different from each other,
In Formula 1, n1+n2 is 2 or 3,
In Formula 1, n1 L ₁ And n2 L ₂ Is optionally a single bond, a first linking group or a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ It can be connected to each other through a heterocyclic group,
The first connector is *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''-Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)- *''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₄ )=*', * ''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''' is selected,
In Formula 2-1, A ₁ is selected from a C ₅ -C ₆₀ carbocyclic group and a C ₁ -C ₆₀ heterocyclic group;
In Formula 2-1, X ₁ and X ₂ are each independently N or C(R ₃ );
In Formula 2-2, X ₁₁ and X ₁₂ are C(R ₁₅ ), X ₁₃ is N or C(R ₁₅ );
In Formula 3, T ₂₁ is *''-N(R ₂₄ )-*''', *''-B(R ₂₄ )-*''', *''-P(R ₂₄ )-*''',*''-C(R ₂₄ )(R ₂₅ )-*''', *''-Si(R ₂₄ )(R ₂₅ )-*''', *''-Ge(R ₂₄ ) (R ₂₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(= O)-*''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₂₄ )=* ', *''=C(R ₂₄ )-*''', *''-C(R ₂₄ )=C(R ₂₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''',
In Formulas 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , Hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group , Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted Or an unsubstituted monovalent non-aromatic condensed heterocyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ) , -P(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ) Is selected,
In Formula 2-1, b1 is selected from an integer of 1 to 6, and when b1 is 2 or more, 2 or more R ₁ are the same or different from each other,
In Formula 3, b21 to b23 are each independently selected from integers of 1 to 3, and when b21 is 2 or more, 2 or more R ₂₁ are the same or different from each other, and when b22 is 2 or more, 2 or more R ₂₂ is When same or different from each other, and b23 is 2 or more, 2 or more R ₂₃ are the same or different from each other,
In Formulas 2-1, 2-2 and 2-3, b1 R ₁ , R ₂ , R ₃ , R ₁₁ to R ₁₄ , R ₁₅ , b21 R ₂₁ , b22 R ₂₂ , b23 R ₂₃ , Two of R ₂₄ and R ₂₅ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. Can,
In Formula 3, a21 is selected from an integer of 1 to 3, and when a21 is 2 or more, two or more T ₂₁ are the same or different from each other,
In Chemical Formulas 2-1 and 2-2, * and *'are binding sites with M in Chemical Formula 1, and in Chemical Formulas 1 and 3, *'' and *''' are binding sites with neighboring atoms. ,
The substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C Import ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted C ₁ -C ₆₀ heteroaryl T , At least one substituent selected from the substituents of the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed polycyclic group,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ) and -P(=O)(Q ₁₁ )(Q ₁₂ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group substituted with at least one selected from;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- -Aromatic hetero-condensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) C ₃ -C ₁₀ cycloalkyl group substituted with at least one selected from (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₁ -C ₁₀ come heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl tea, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group; And
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );
Is selected from
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyan No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group , Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, deuterium, at least one selected from C ₁ -C ₆₀ alkyl group, deuterium, -F and cyano group substituted with at least one selected from -F and cyano groups It is selected from C ₆ -C ₆₀ aryl groups substituted with one, biphenyl groups, and terphenyl groups. According to claim 1,
The organometallic compound is 4-coordinated or six-coordinated ligand and the metal atom (M ₁₎ comprises, and the energy level (E _3MC) of ^3-MC state (triplet metal centered state) of the organometallic compound ³ of the organometallic compound to An organic light-emitting device having an energy level (E ₃ MLCT) of a triplet metal-to-ligand charge transfer state ( _MLCT ). According to claim 1,
The organometallic compound satisfies E ₃ ≥ 5 kcal/mol,
E ₃ is an organic light emitting device, as defined by the following equation 1:
<Equation 1>
E ₃ =||E _MLCT | -|E _MC || According to claim 1,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer includes the organometallic compound,
The organic layer further includes a hole transport region interposed between the first electrode and the emission layer and an electron transport region interposed between the emission layer and the second electrode,
The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, a buffer layer, a light emitting auxiliary layer, and an electron blocking layer,
The electron transport region, the organic light emitting device including at least one selected from a hole blocking layer, an electron transport layer and an electron injection layer. The method of claim 4,
The light emitting layer comprises the organic metal compound, an organic light emitting device. According to claim 1,
The organic light emitting device, wherein the light emitting layer emits blue light having a maximum emission wavelength of 440 nm to 490 nm. The method of claim 4,
The hole transport region comprises a p- dopant LUMO energy level is lower than -3.5eV, an organic light emitting device. An organometallic compound represented by Formula 1 below:
<Formula 1>
M(L ₁ ) _n1 (L ₂ ) _n2
<Formula 2-1><Formula2-2>

<Formula 3>

In Formula 1,
M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti) ), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm);
In Formula 1, L ₁ is a ligand represented by Formula 2-1 or 2-2, n1 is 1, 2 or 3, and when n1 is 2 or more, 2 or more L ₁ are the same or different from each other,
In Formula 1, L ₂ is a ligand represented by Formula 3, n2 is 0, 1 or 2, and when n2 is 2 or more, 2 or more L ₂ is the same or different from each other,
In Formula 1, n1+n2 is 2 or 3,
In Chemical Formula 1, n1 L ₁ and n2 L ₂ may be optionally connected to each other through a single bond or a first linking group,
The first connector is *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''-Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)- *''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₄ )=*', * ''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''' is selected,
In Formula 2-1, A ₁ is selected from a C ₅ -C ₆₀ carbocyclic group and a C ₁ -C ₆₀ heterocyclic group;
In Formula 2-1, X ₁ and X ₂ are each independently N or C(R ₃ );
In Formula 2-2, X ₁₁ and X ₁₂ are C(R ₁₅ ), X ₁₃ is N or C(R ₁₅ );
In Formula 3, T ₂₁ is *''-N(R ₂₄ )-*''', *''-B(R ₂₄ )-*''', *''-P(R ₂₄ )-*''',*''-C(R ₂₄ )(R ₂₅ )-*''', *''-Si(R ₂₄ )(R ₂₅ )-*''', *''-Ge(R ₂₄ ) (R ₂₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(= O)-*''', *''-S(=O)-*''', *''-S(=O) ₂ -*''', *''-C(R ₂₄ )=* ', *''=C(R ₂₄ )-*''', *''-C(R ₂₄ )=C(R ₂₅ )-*''', *''-C(=S)-*''' and *''-C≡C-*''',
In Formulas 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , Hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group , Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted Or an unsubstituted monovalent non-aromatic condensed heterocyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ) , -P(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ) Is selected,
In Formula 2-1, b1 is selected from an integer of 1 to 6, and when b1 is 2 or more, 2 or more R ₁ are the same or different from each other,
In Formula 3, b21 to b23 are each independently selected from integers of 1 to 3, and when b21 is 2 or more, 2 or more R ₂₁ are the same or different from each other, and when b22 is 2 or more, 2 or more R ₂₂ is When same or different from each other, and b23 is 2 or more, 2 or more R ₂₃ are the same or different from each other,
In Formulas 2-1, 2-2 and 2-3, b1 R ₁ , R ₂ , R ₃ , R ₁₁ to R ₁₄ , R ₁₅ , b21 R ₂₁ , b22 R ₂₂ , b23 R ₂₃ , Two of R ₂₄ and R ₂₅ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. Can,
In Formula 3, a21 is selected from an integer of 1 to 3, and when a21 is 2 or more, two or more T ₂₁ are the same or different from each other,
In Chemical Formulas 2-1 and 2-2, * and *'are binding sites with M in Chemical Formula 1, and in Chemical Formulas 1 and 3, *'' and *''' are binding sites with neighboring atoms. ,
The substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, , Substituted C ₁ -C ₆₀ heteroaryloxy group, substituted C ₁ -C ₆₀ heteroarylthio group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group At least one substituent selected,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ) and -P(=O)(Q ₁₁ )(Q ₁₂ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group substituted with at least one selected from;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- -Aromatic hetero-condensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) C ₃ -C ₁₀ cycloalkyl group substituted with at least one selected from (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₁ -C ₁₀ come heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl tea, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group; And
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );
Is selected from
Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyan No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group , Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, deuterium, at least one selected from C ₁ -C ₆₀ alkyl group, deuterium, -F and cyano group substituted with at least one selected from -F and cyano groups It is selected from C ₆ -C ₆₀ aryl groups substituted with one, biphenyl groups, and terphenyl groups. The method of claim 8,
In Chemical Formula 1, M is an organometallic compound selected from Pt, Ir, Pd, Cu, Ag and Au. The method of claim 8,
In Formula 1, n1 is 1, n2 is 1, n1 is 3, and n2 is 0, an organometallic compound. The method of claim 8,
In Formula 2-1, A ₁ is,
Benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silol group, oxazole group, isoxazole group , Oxadiazole group, isoxadiazole group, oxatriazole group, isoxtriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatazole group, isothiatria Sol group, pyrazole group, imidazole group, triazole group, 1,2,4-triazole group, tetrazole group, azasilol group, diazasilol group, triazasilol group, cyclohexane group, and cyclohexene group;
Deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexyl Senyl group, phenyl group, biphenyl group, terphenyl group, pentaenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, Furanyl group, silolyl group, imidazole group, pyrazole group, thiazole group, isothiazolyl group, oxazolyl group, isoxazole group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group , Isoindoleyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, isoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quina Zolinyl group, benzoquinazolinyl group, sinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group , Benzoisothiazolyl group, benzooxazolyl group, benzoisooxazolyl group, triazoleyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazoleyl group, dibenzofuranyl group, dibenzo Thiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosil Rollyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspyro-bifluorenyl group, azacarbazolyl group , Azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrroleyl group, indolopyrroleyl group, indenocarbazolyl group, indolocarbazoleyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)(Q ₃₁ )(Q ₃₂ ) and -P(=S)(Q ₃₁ )(Q ₃₂ ), substituted with at least one selected from benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole Group, silol group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxtriazol group, thiazole group, isothiazole group, thiadiazole group, isothia Diazol group, thiatazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, 1,2,4-triazole group, tetrazole group, azasilol group, diazasilol group, Triazasilol group, cyclohexane group, and cyclohexene group; Is selected from
Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ hetero arylthio group, a monovalent non-aromatic hydrocarbon ring substituted with at least one selected from the group consisting of condensed polycyclic group, heavy hydrogen, -F and a cyano group-condensed polycyclic aromatic group, a monovalent non- An organometallic compound selected from C ₆ -C ₆₀ aryl groups substituted with at least one selected from C ₁ -C ₆₀ alkyl groups, deuterium, -F and cyano groups, biphenyl groups and terphenyl groups. The method of claim 8,
In Formula 2-1, X ₁ to X ₂ are C(R ₃ ),
In Formula 2-2, X ₁₃ is C(R ₁₅ ), an organometallic compound. The method of claim 8,
In Formula 3, T ₂₁ is *''-C(R ₂₄ )(R ₂₅ )-*''', and a21 is 1 or 2, an organometallic compound. The method of claim 8,
In Formulas 2-1, 2-2 and 3, R ₁ to R ₅ , R ₁₁ to R ₁₅ and R ₂₁ to R ₂₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , Hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected from the group;
Cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, pyrrolyl group, indolyl group, isoindoleyl group, indazolyl group, quinolinyl group, isoquine A monolinyl group, a quinoxalinyl group, a quinazolinyl group, a sinolinyl group, and a triazinyl group; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , Cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindole group, indazolyl group, quinolinyl group, isoquinolinyl group , Quinoxalinyl group, quinazolinyl group, sinolinyl group, and triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ ) Cyclo substituted with at least one selected from (Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ) Pentyl group, cyclohexyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazoleyl group, quinolinyl group, isoquinolinyl group, quinol group A salinyl group, a quinazolinyl group, a sinolinyl group, and a triazinyl group; And
-Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S (=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ );
Is selected from
Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₂₀ aryl group, C ₁ -C ₂₀ hetero Aryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed polycyclic groups;
An organometallic compound selected from among. The method of claim 8,
In Formula 2-1, R ₂ is a C ₁ -C ₂₀ alkyl group, -N(Q ₁ )(Q ₂ ) and a phenyl group; And a C ₁ -C ₂₀ alkyl group substituted with a C ₁ -C ₂₀ alkyl group, a -N(Q ₁ )(Q ₂ ) and a phenyl group; Is selected from
The Q ₁ and Q ₂ are C ₁ -C ₂₀ alkyl groups, organometallic compounds. The method of claim 8,
In Formula 2-2, R ₁₁ and R ₁₂ are each independently selected from hydrogen, -F, -Cl, cyano group, C ₁ -C ₂₀ alkyl group, and phenyl group, an organometallic compound. The method of claim 8,
The n1 and n2 is 1, L ₁ is a group represented by the formula 2-1,
One of the b1 R ₁ and one of the adjacent b23 R ₂₃ is connected through a single bond or a first linking group, an organometallic compound. The method of claim 8,
N1 is 3, L ₁ is a group represented by Chemical Formula 2-2,
X ₁₃ of the three L ₁ are all C (R ₁₅ ),
Three R ₁₄ of the three L ₁ are connected to each other through a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
Of the three L ₁ , three R ₁₅ are linked to each other through a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group, an organometallic compound. The method of claim 8,
The organometallic compound is a group represented by any one of the following formulas 1-1 to 1-5, an organometallic compound:

In the above formula 1-1 to 1-5,
L ₁₁ to L ₁₅ are each independently a single bond, *''-N(R ₄ )-*''', *''-B(R ₄ )-*''', *''-P(R ₄ )-*''', *''-C(R ₄ )(R ₅ )-*''', *''-Si(R ₄ )(R ₅ )-*''', *''- Ge(R ₄ )(R ₅ )-*''', *''-S-*''', *''-Se-*''', *''-O-*''', *''-C(=O)-*''',*''-S(=O)-*''',*''-S(=O) ₂ -*''', *''-C( R ₄ )=*', *''=C(R ₄ )-*''', *''-C(R ₄ )=C(R ₅ )-*''', *''-C(= S)-*''' and *''-C≡C-*''',
c11 to c15 are each independently selected from integers of 1 to 3, when c11 is 2 or more, two or more L ₁₁ are the same or different from each other, and when c12 is 2 or more, two or more L ₁₂ are the same or different from each other , When c13 is 2 or more, 2 or more L ₁₃ are the same or different from each other, when c14 is 2 or more, 2 or more L ₁₄ are the same or different from each other, and when c15 is 2 or more, 2 or more L ₁₅ is the same or different from each other and,
Ar ₁ and Ar ₂ are independently of each other, a substituted or unsubstituted trivalent C ₅ -C ₃₀ carbocyclic group, a substituted or unsubstituted trivalent C ₁ -C ₃₀ heterocyclic group, and

Group, and *'', *''' and *'''' are bonding sites with neighboring atoms,
c11 and c12 are each independently selected from integers of 1 to 3, when c11 is 2 or more, two or more L ₁₁ are the same or different from each other, and when c12 is 2 or more, two or more L ₁₂ are the same or different from each other ,
R _1a to R _1c , R _3a to R _3b , R _15a to R _15b , R _21a to R _21c , R _22a to R _22c , R _23a to R _23b , R _24a to R _24b , R _25a to R _25b and R ₃₀ Each refers to the definitions of R ₁ , R ₃ , R ₁₅ , R ₂₁ to R ₂₅ in claim 1, and R ₂ , R ₄ , R ₅ and R ₁₁ to R ₁₃ are respectively R in claim 1 See definitions for ₂ , R ₄ , R ₅ and R ₁₁ to R ₁₃ . The method of claim 8,
The organometallic compound represented by Formula 1 is selected from Compounds 1 to 14 below:

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