KR20190131468A - Amine-based compound and organic light-emitting device comprising the same - Google Patents

Abstract

Disclosed is an amine compound having a predetermined chemical formula. The present invention is to provide the amine compound and an organic light emitting device comprising the same. The organic light emitting device comprising the amine compound can have a low driving voltage, high efficiency, long lifespan, and high maximum quantum efficiency.

Description

Amine compound and organic light emitting device including the same {AMINE-BASED COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME}

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

The organic light emitting device is a self-luminous device, and has a wider viewing angle and superior contrast, faster response time, excellent luminance, drive voltage and response speed, and more multi-colored devices than conventional devices. It is possible.

In the organic light emitting diode, a first electrode is disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. It can have a structure. Holes injected from the first electrode move to the light emitting layer via the hole transport region, and electrons injected from the second electrode move to the light emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.

It is to provide an amine compound and an organic light emitting device including the same.

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

<Formula 1>

<Formula 2>

In Formulas 1 and 2,

Ar ₁ , Ar ₂ , L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₆₀ heterocyclic group,

a1 and a2 are each independently selected from an integer of 0 to 5, when a1 is 2 or more, two or more L ₁ are the same or different from each other, and when a2 is 2 or more, two or more L ₂ are the same or different, and

When a1 is 0, *-(L ₁ ) _a1- * 'is a single bond; when a2 is 0, *-(L ₂ ) _a2- *' is a single bond,

R ₁ to R ₁₀ are independently of each other, a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino Groups, hydrazono groups, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkynyl groups, substituted or unsubstituted C _1- C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or Unsubstituted C ₂ -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, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or unsubstituted monovalent non- Hyangjok condensed polycyclic heterocyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -B (Q 1) (Q 2), -C (= O) (Q 1), -P (= O) ( Q ₁ ) (Q ₂ ), -P (= S) (Q ₁ ) (Q ₂ ), -S (= O) (Q ₁ ) (Q ₂ ) and -S (= O) ₂ (Q ₁ ) ( Q ₂ )

One of R ₁ to R ₁₀ is a group represented by the formula (2),

R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution 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 an unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted 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, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -B (Q ₁ ) (Q ₂ ), -C (= O) (Q ₁ ), -P (= O) (Q ₁ ) (Q ₂ ), -P ( = S) (Q ₁ ) (Q ₂ ), -S (= O) (Q ₁ ) (Q ₂ ) and -S (= O) ₂ (Q ₁ ) (Q ₂ ),

b1 and b2 are each independently selected from an integer of 1 to 10, when b1 is 2 or more, two or more R ₁₁ are the same or different from each other, and when b2 is 2 or more, two or more R ₁₂ are the same or different, and

The substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₂ -C ₆₀ 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, At least one substituent selected from a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted monovalent non-aromatic condensed polycyclic group and a 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 ), -B (Q ₁₁ ) (Q ₁₂ ), -C (= 0) (Q ₁₁ ), -S (= 0) ₂ (Q ₁₁ ) and -P (= 0) (Q ₁₁ ) (Q ₁₂ ) substituted with at least one selected from C ₁ -C _{A 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;

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 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, 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 heterocondensed polycyclic group, -Si (Q ₂₁ ) (Q ₂₂ ) (Q ₂₃ ), -B (Q ₂₁ ) (Q ₂₂ ), -C (= O) (Q ₂₁ ), -S (= O) C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cyclo substituted with at least one selected from ₂ (Q ₂₁ ) and -P (= 0) (Q ₂₁ ) (Q ₂₂ ) alkenyl group, a 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, 1 Non-aromatic condensed polycyclic he And one is a non-aromatic heterocyclic group, fused polycyclic; And

-Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), -B (Q ₃₁ ) (Q ₃₂ ), -C (= O) (Q ₃₁ ), -S (= O) ₂ (Q ₃₁ ), and- P (= 0) (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, and 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, biphenyl group and terphenyl group,

* Is a bonding site with a neighboring atom.

According to another aspect, the first electrode; A second electrode opposite the first electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one kind of the amine compound.

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

1 to 4 schematically illustrate structures of organic light emitting diodes according to example embodiments.

As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in detail in the written description. Effects and features of the present invention, and methods of achieving them will be apparent with reference to the embodiments described below in detail in conjunction with the drawings. However, the present invention is not limited to the embodiments disclosed below, but may be implemented in various forms.

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

In the following embodiments, the singular forms "a", "an" and "the" include plural forms unless the context clearly indicates otherwise.

In the following embodiments, the terms including or having have meant that there is a feature or component described in the specification and does not preclude the possibility of adding one or more other features or components.

In the following embodiments, when a part of a film, an area, a component, etc. is said to be on or on another part, as well as being directly above another part, other films, areas, components, etc. are interposed therebetween. It also includes cases where there is.

In the drawings, components may be exaggerated or reduced in size for convenience of description. For example, the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of description, and thus the present invention is not necessarily limited to the illustrated.

The amine compound is represented by the following Formula 1:

<Formula 1>

<Formula 2>

In Formulas 1 and 2, Ar ₁ , Ar ₂ , L ₁ and L ₂ are each independently a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₆₀ heterocy. It can be selected from click groups.

In one embodiment, Ar ₁ , Ar ₂ , L ₁ and L ₂ are each independently a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₃₀ heterocy. It can be selected from click groups.

In another embodiment, Ar ₁ , Ar ₂ , L ₁ and L ₂ are independently of each other, a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptylene group, an indacene group, acenaphthalene Group, fluorene group, spiro-fluorene group, benzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthrene group, triphenylene group, pyrene group, chrysene group, naphthacene group , Pysene group, perylene group, pentafen group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group, indazole Group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cynoline group, carbazole group, phenanthridine group, acridine group , Nantroline group, phenazine group, benzoxazole group, benzoimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, iso Oxazole group, oxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, benzoxazole group, dibenzofuran group, dibenzothiophene group, benzocarbazole group and dibenzocarbazole group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Benzene group, pentalene group, indene group substituted with at least one selected from alkoxy group, C ₆ -C ₂₀ aryl group, C ₂ -C ₂₀ heteroaryl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) , Naphthalene group, azulene group, heptalene group, indacene group, acenaphthalene group, fluorene group, spiro-fluorene group, benzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthrene Group, triphenylene group, pyrene group, chrysene group, naphthacene group, pysene group, perylene group, pentaphene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group , Pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinol Group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cynoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, Phenazine group, benzoxazole group, benzoimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxa Sol groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, benzoxazole groups, dibenzofuran groups, dibenzothiophene groups, benzocarbazole groups and dibenzocarbazole groups;

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

In one embodiment, L ₁ and L ₂ may be independently selected from the group represented by Formulas 3-1 to 3-46, but is not limited thereto.

In Formulas 3-1 to 3-46,

Y ₁ is O, S, C (Z ₃ ) (Z ₄ ), N (Z ₅ ) or Si (Z ₆ ) (Z ₇ ),

Z ₁ to Z ₇ 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, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolin Nyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl and- Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ),

d2 is selected from an integer of 0 to 2, when d2 is 2 or more, two or more Z ₁ are the same as or different from each other,

d3 is selected from an integer of 0 to 3, when d3 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,

d4 is selected from an integer of 0 to 4, when d4 is 2 or more, two or more Z ₁ are the same as or different from each other,

d5 is selected from an integer of 0 to 5, when d5 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,

d6 is selected from an integer of 0 to 6, when d6 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,

d8 is selected from an integer of 0 to 8, and when d8 is 2 or more, two or more Z ₁ are the same as or different from each other,

* And * 'are binding sites with neighboring atoms.

In Formula 2, a1 and a2 may be each independently selected from an integer of 0 to 5. a1 represents the number of L _{1. When} a1 is 2 or more, two or more L ₁ may be the same or different. The description of a2 may be understood with reference to the description of a1.

When a1 is 0, *-(L ₁ ) _a1- * 'is a single bond, and when a2 is 0, *-(L ₂ ) _a2- *' is a single bond.

In one embodiment, a1 and a2 may be 0 or 1 independently of each other, but are not limited thereto.

In one embodiment, Ar ₁ and Ar ₂ are independently of each other, a benzene group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C A benzene group substituted with at least one selected from a ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a C ₂ -C ₂₀ heteroaryl group, and —Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ); It may be selected from, but is not limited thereto.

In another embodiment, Ar ₁ and Ar ₂ may be independently selected from the group represented by Formulas 5-1 to 5-80, but are not limited thereto.

In Formulas 5-1 to 5-80,

Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or Si (Z ₃₆ ) (Z ₃₇ ),

Z ₃₁ to Z ₃₇ 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, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene- benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanyl group Trolnyl group, phenazinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ),

e2 is selected from an integer of 0 to 2, when e2 is 2 or more, two or more Z ₃₂ are the same as or different from each other,

e3 is selected from an integer of 0 to 3, when e3 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,

e4 is selected from an integer of 0 to 4, when e4 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,

e5 is selected from an integer of 0 to 5, when e5 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,

e6 is selected from an integer of 0 to 6, when e6 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,

e7 is selected from an integer of 0 to 7, when e7 is 2 or more, two or more Z ₃₁ are the same as or different from each other,

e9 is selected from an integer of 0 to 9, when e9 is 2 or more, two or more Z ₃₁ are the same as or different from each other,

* Is a bonding site with a neighboring atom.

R ₁ to R ₁₀ in Formula 1 are each independently a group represented by Formula 2, 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 ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalke Nyl group, substituted or unsubstituted C ₂ -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, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or Substituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -B (Q 1) (Q 2), -C (= O) (Q 1), - P (= O) (Q ₁ ) (Q ₂ ), -P (= S) (Q ₁ ) (Q ₂ ), -S (= O) (Q ₁ ) (Q ₂ ) and -S (= O) ₂ (Q ₁ ) (Q ₂ ),

One of R ₁ to R ₁₀ is a group represented by the formula (2),

R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution 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 an unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted 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, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -B (Q ₁ ) (Q ₂ ), -C (= O) (Q ₁ ), -P (= O) (Q ₁ ) (Q ₂ ), -P ( = S) (Q ₁ ) (Q ₂ ), -S (= 0) (Q ₁ ) (Q ₂ ) and -S (= 0) ₂ (Q ₁ ) (Q ₂ ).

In one embodiment, R ₁ to R ₁₀ are independently of each other, a group represented by Formula 2, 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 ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ),

R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution Or an unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic ring Groups and substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), but is not limited thereto.

In another embodiment, R ₁ to R ₁₀ are each independently a group represented by Formula 2, 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, the group represented by the formula 5-1 to 5-80 and -Si (Q ₁ ) (Q ₂ ) ( Q ₃ )

R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution Or an unsubstituted C ₁ -C ₆₀ alkyl group, a group represented by Formulas 5-1 to 5-80, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), but is not limited thereto. .

In another embodiment, R ₁₁ and R ₁₂ may be independently selected from the group represented by the following Chemical Formulas 6-1 to 6-34, but are not limited thereto.

In Chemical Formulas 6-1 to 6-34,

Ph is a phenyl group,

* Is a bonding site with a neighboring atom.

In Formula 2, b1 and b2 may be independently selected from integers of 1 to 10. b1 represents the number of R _{11. When} b1 is 2 or more, two or more R ₁₁ may be identical to or different from each other. The description of b2 may be understood with reference to the description of b1 above.

In one embodiment, the amine compound represented by Formula 1 may be represented by any one of the following Formula 1-1 to 1-6, but is not limited thereto:

<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

In Formulas 1-1 to 1-6, Ar ₁ , Ar ₂ , L ₁ , L ₂ , a1, a2, R ₁ to R ₁₂ , b1 and b2 are the same as described in the description of Formula 1 above.

In one embodiment, in Formulas 1-1 to 1-6, R ₁ to R ₁₀ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group , Nitro, amidino, hydrazino, hydrazono, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, ter-butyl, pentyl, iso -May be selected from amyl, hexyl, phenyl and biphenyl groups, but is not limited thereto.

In another embodiment,

i) when the amine compound represented by Chemical Formula 1 is represented by Chemical Formula 1-1, R ₂ to R ₁₀ are hydrogen;

ii) When the amine compound represented by Chemical Formula 1 is represented by Chemical Formula 1-2, R ₈ and R ₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a methyl group, An ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, phenyl group and biphenyl group are selected from R ₁ , R ₃ to R ₇ and R ₁₀ are hydrogen;

iii) when the amine compound represented by Chemical Formula 1 is represented by Chemical Formula 1-3, R ₁ , R _2, and R ₄ to R ₁₀ are hydrogen;

iv) when the amine compound represented by Chemical Formula 1 is represented by Chemical Formula 1-4, R ₁ to R ₃ and R ₅ to R ₁₀ are hydrogen;

iv) when the amine compound represented by Chemical Formula 1 is represented by Chemical Formula 1-5, R ₁ to R ₇ and R ₉ to R ₁₀ are hydrogen; or

v) When the amine compound represented by Formula 1 is represented by Formula 1-6, R ₂ is hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, propyl group, isopropyl Group, n-butyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, phenyl group and biphenyl group, selected from R ₁ , R ₃ to R ₈ and R ₁₀ may be hydrogen, but is not limited thereto.

In some embodiments, in Formulas 1-1 to 1-6, Ar ₁ and Ar ₂ may be each independently selected from a benzene group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C A benzene group substituted with at least one selected from a ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a C ₂ -C ₂₀ heteroaryl group, and —Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ); It may be selected from, but is not limited thereto.

In some embodiments, in Formulas 1-1 to 1-6, R ₁₁ and R ₁₂ may be selected independently from each other, but are not limited thereto.

In another embodiment, in Formulas 1-1 to 1-6, R ₁₁ and R ₁₂ may be each independently selected from Formulas 6-1 to 6-34, but are not limited thereto.

In another embodiment, in Formulas 1-1 to 1-6,

R ₁₁ and R ₁₂ are each independently selected from Chemical Formulas 6-1 to 6-34,

Ar ₁ and Ar ₂ may be each independently selected from a benzene group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C A benzene group substituted with at least one selected from a ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a C ₂ -C ₂₀ heteroaryl group, and —Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ); It may be selected from, but is not limited thereto.

In one embodiment, the substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₂ -C ₆₀ 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 cycloalke group, a substituted C ₁ -C ₁₀ heteroaryl 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 At least one substituent selected from a -C ₆₀ heteroaryl group, a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted monovalent non-aromatic condensed polycyclic group and a 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 ), -B (Q ₁₁ ) (Q ₁₂ ), -C (= 0) (Q ₁₁ ), -S (= 0) ₂ (Q ₁₁ ) and -P (= 0) (Q ₁₁ ) (Q ₁₂ ) substituted with at least one selected from C ₁ -C _{A 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;

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 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, 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 heterocondensed polycyclic group, -Si (Q ₂₁ ) (Q ₂₂ ) (Q ₂₃ ), -B (Q ₂₁ ) (Q ₂₂ ), -C (= O) (Q ₂₁ ), -S (= O) C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cyclo substituted with at least one selected from ₂ (Q ₂₁ ) and -P (= 0) (Q ₂₁ ) (Q ₂₂ ) alkenyl group, a 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, 1 Non-aromatic condensed polycyclic he And one is a non-aromatic heterocyclic group, fused polycyclic; And

-Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), -B (Q ₃₁ ) (Q ₃₂ ), -C (= O) (Q ₃₁ ), -S (= O) ₂ (Q ₃₁ ), and- P (= 0) (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, and 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, biphenyl group and terphenyl group,

* Is a bonding site with a neighboring atom.

In one embodiment, the amine compound represented by Formula 1 may be selected from the following compounds 1 to 144, but is not limited thereto.

In the amine compound represented by Formula 1, benzene is further condensed at a specific position of fluorene, and satisfies a structure including a substituent having a cyclic structure at a specific position of fluorene, thereby hopping holes by orbital delocalization ( facilitate hole hopping). Therefore, since the amine compound has a high charge mobility, the organic light emitting device including the amine compound can be driven at low power.

In addition, the amine-based compound includes a single amine group in a molecule, and thus has a lower highest Occupied Molecular Orbital energy level than a compound including two or more amine groups, thereby optimizing energy levels for hole transport. Has Therefore, an electronic device employing the amine compound, for example, an organic light emitting device, may have a low driving voltage, high efficiency and long life.

The synthesis method of the amine compound represented by Chemical Formula 1 may be recognized by those skilled in the art with reference to the following examples.

At least one of the amine compounds represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the amine compound may be included in at least one of a hole transport region, an electron transport region, and a light emitting layer. Alternatively, the amine 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.

Thus, the first electrode; A second electrode opposed to the first electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one amine compound represented by Chemical Formula 1.

In the present specification, "(organic layer) includes one or more amine compounds" means "(organic layer) is one amine compound belonging to the category of Formula 1 or two different kinds belonging to the category of Formula 1 It may include the above amine-based compound ".

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

According to one embodiment, the first electrode is an anode, the second electrode is a cathode, the organic layer is a hole transport region disposed between the first electrode and the light emitting layer and disposed between the light emitting layer and the second electrode. Further comprising an electron transport region, wherein 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, and the electron transport region includes a hole blocking layer and an electron transport layer. , An electron injection layer or any combination thereof.

In one embodiment, the hole transport region may include the amine compound.

In another embodiment, the hole transport region may include a hole transport layer, and the hole transport layer may include the amine compound.

In one embodiment, the light emitting layer may include the amine compound.

In one embodiment, the hole transport region may include a p-dopant, and the LUMO of the p-dopant may be -3.5 eV or less.

In one embodiment, the light emitting layer may include at least one of a styryl-based compound, an anthracene-based compound, a pyrene-based compound and a spiro-bifluorene-based compound.

In one embodiment, the light emitting layer is a first color light emitting-emitting layer,

Between the first electrode and the second electrode, i) at least one second color light-emitting layer is further included, or ii) at least one second color light-emitting layer and at least one third color light-emitting layer This is additionally included,

The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same or different from each other,

The mixed color light in which the first color light and the second color light are mixed with each other or the mixed color light in which the first color light, the second color light and the third color light are mixed with each other may be emitted.

As used herein, the term "organic layer" refers to a single and / or a plurality of all layers interposed between the first electrode and the second electrode of the organic light emitting element. The material included in the layer of the "organic layer" is not limited to the organic material.

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting diode 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 diode 10 according to the exemplary embodiment of the present invention will be described with reference to FIG. 1.

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

The first electrode 110 may be formed by, for example, providing a material for the first electrode on the substrate by 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 transflective 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, the first electrode material may be magnesium (Mg), silver (Ag), aluminum (Al), or aluminum-lithium (Al-Li) to form the first electrode 110 that is a transflective electrode or a reflective electrode. ), 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 as 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.

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) may be further included.

The hole transport region may comprise i) a single layer structure consisting of a single material, ii) a single layer structure consisting of a plurality of different materials, or iii) a multilayer structure having a plurality of layers consisting of a plurality of different materials. It may 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 composed of a single layer composed of a plurality of different materials, or a hole injection layer / hole transport layer, a hole injection layer / hole transport layer, which are sequentially stacked from the first electrode 110. It may have a multilayer structure of / light emitting auxiliary layer, hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer or a hole injection layer / hole transport layer / electron blocking layer, but is not limited thereto.

The hole transport region may include an amine compound represented by Chemical Formula 1.

In addition, the hole transport region, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-in addition to the amine compound represented by the formula (1) 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-styrene Sulfonates))), Pani / CSA (Polyaniline / Camphor sulfonic acid), PANI / PSS (Polyaniline / Poly (4-styrenesulfonate) (polyaniline / poly (4-styrenesulfonate)), It may include at least one selected from a compound represented by 201 and a compound represented by the formula (202):

<Formula 201>

<Formula 202>

In 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 heterocondensed 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 heterocondensed polycyclic group,

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

xa5 is selected from an integer of 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 heterocondensate It may be selected from polycyclic groups.

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

According to one embodiment, in Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are each independently of the other,

Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalylene group, indasenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorene Neylene group, dibenzo fluorenylene group, penalenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, pisenylene group, phenylene group Reillyenylene group, pentaphenylene group, hexasenylene group, pentaxenylene group, rubisenylene group, coronylene group, ovalenylene group, thiophenylene group, furanylene group, carbazoleylene group, indolylene group, isoindoleylene group A benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group and a pyridinylene 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 Neyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group , Phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perrylenyl group, pentaphenyl group, hexasenyl group, pentaxenyl group, Rubisenyl group, coronyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzo Furanyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) ) And -N (Q ₃₁ ) (Q ₃₂ ) substituted with at least one selected from phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indasenylene group, acenaphthyl Ethylene group, fluorenylene group, spiro-nonfluorenylene group, benzofluorenylene group, dibenzofluorenylene group, penalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenyl Len, pyrenylene, chrysenylene, naphthacelene, pisenylene, peryleneylene, pentaphenylene, hexasenylene, pentanesene, rubisenylene, coronylene, ovalenylene and thio Phenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzofuranyl Group, benzo thiophenyl group, a dibenzo-furanyl group, a dibenzo thiophenyl group, a benzo carbazolyl group, a dibenzo-carbazolyl group, a dibenzo room rolil group and a pyridinyl group;

Is selected from

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

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

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

According to yet another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indaseyl group, Acenaphthyl group, fluorenyl group, spiro-nonfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pentansenyl group, rubisenyl group, coronyl 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 Neyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group , Phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perrylenyl group, pentaphenyl group, hexasenyl group, pentaxenyl group, Rubisenyl group, coronyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzo Furanyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) Phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indaseyl group, ace substituted with at least one selected from-) and -N (Q ₃₁ ) (Q ₃₂ ) Naphthyl group, fluorenyl group, spiro-nonfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyre Neyl group, chrysenyl group, naphthacenyl group, pisenyl group, peryleneyl group, pentaphenyl group, hexasenyl group, pentansenyl group, rubisenyl group, coronyl group, ovalenyl group, thiophenyl group, furanyl group, carbazoleyl group , Indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl Groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups and pyridinyl groups;

Can be selected from

For a description of the above Q ₃₁ to Q ₃₃ refer to what is described herein.

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

Fluorenyl group, spiro-nonfluorenyl 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 , A fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, di, substituted with at least one selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group Benzofuranyl group and dibenzothiophenyl group;

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

According to another embodiment, i) R ₂₀₁ and R ₂₀₂ in Formula 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 yet another embodiment, at least one of R ₂₀₁ to R ₂₀₄ in Formula 202,

Carbazolyl groups; 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 thereto.

The compound represented by Formula 201 may be represented by the following Formula 201A:

<Formula 201A>

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

<Formula 201A-1>

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

<Formula 202A>

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

<Formula 202A-1>

In Formulas 201A, 201A (1), 201A-1, 202A, and 202A-1,

For descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ , refer to what is described herein.

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

R ₂₁₃ to R ₂₁₇ are each independently of the other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ Substituted-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 Phenyl group, phenyl group substituted by -F, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indasenyl group, acenaphthyl group, fluorenyl group, spiro-nonfluorenyl group, benzoflu Orenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perenyl group , Pentaphenyl group, hexasenyl group, pentasenyl group, rubisenyl group, coronyl group, ovalenyl group, thiophenyl group, furanyl group, To be selected from a basolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridinyl group Can be.

The hole transport region may include at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto.

The hole transport region may have a thickness of about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa. 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 kPa to about 9000 kPa, for example, about 100 kPa to about 1000 kPa, and the thickness of the hole transport layer is about 50 kPa. To about 2000 kPa, for example, about 100 kPa to about 1500 kPa. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

The emission auxiliary layer is a layer that serves to increase optical emission efficiency by compensating an optical resonance distance according to the wavelength of light emitted from the emission layer, and the electron blocking layer is a layer that prevents electron injection from an electron transport region. to be. The emission auxiliary layer and the electron blocking layer may include the above materials.

In addition to the materials described above, the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or heterogeneously 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 -3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.

For example, the p-dopant,

Quinone derivatives such as TCNQ (Tetracyanoquinodimethane) 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 Formula 221;

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

<HAT-CN> <F4-TCNQ>

<Formula 221>

In 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 A non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic 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.

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 may have 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 in contact or spaced apart, or two or more materials selected from among a red light emitting material, a green light emitting material, and a blue light emitting material may be layered. It can have a mixed structure without emitting white light.

The light emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

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

The light emitting layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 200 kPa to about 600 kPa. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.

The host may include a compound represented by the following Formula 301.

<Formula 301>

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

In 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 heterocondensed polycyclic group,

xb1 is selected from an integer of 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, Groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, -Si (Q ₃₀₁ ) (Q ₃₀₂ ) (Q ₃₀₃ ), -N (Q ₃₀₁ ) (Q ₃₀₂ ), Choose from -B (Q ₃₀₁ ) (Q ₃₀₂ ), -C (= O) (Q ₃₀₁ ), -S (= O) ₂ (Q ₃₀₁ ) and -P (= O) (Q ₃₀₁ ) (Q ₃₀₂ ) Become,

xb21 is selected from an integer of 1 to 5,

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

According to one embodiment, Ar ₃₀₁ in Formula 301 is

Naphthalene group, fluorene group, spiro-nonfluorene 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, pentaphene 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 ),- Naphthalene group, fluorene group, substituted with at least one selected from C (= 0) (Q ₃₁ ), -S (= 0) ₂ (Q ₃₁ ) and -P (= 0) (Q ₃₁ ) (Q ₃₂ ), Spiro-nonfluorene group, benzofluorene group, dibenzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene Groups, pisene groups, perylene groups, pentafen groups, indenoanthracene groups, dibenzofuran groups and dibenzothiophene groups;

Is selected from

Q ₃₁ to Q ₃₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, 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 Formula 301 may be represented by the following Formula 301-1 or 301-2:

<Formula 301-1>

<Formula 301-2>

In Formulas 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 each independently of the 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 ),- Is selected from 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 refer to what is described herein,

For the description of L ₃₀₂ to L ₃₀₄ , independently of one another, refer to the description of L ₃₀₁ above,

For descriptions of Xb2 to xb4 independently of each other, refer to the description of xb1,

For the description of R ₃₀₂ to R ₃₀₄ , independently of one another, refer to the description for R ₃₀₁ .

For example, L ₃₀₁ to L ₃₀₄ in Formulas 301, 301-1, and 301-2 may be each independently

Phenylene group, naphthylene group, fluorenylene group, spiro-nonfluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, peryleneylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazoleylene group, indolylene group, isoindoleylene group, benzo Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group, dibenzosilol ylene group, pyridinylene group, imidazole ylene group, pyrazol ylene group , Thiazole ylene group, isothiazole ylene group, oxazole ylene group, isoxazole ylene group, thiadiazole ylene group, oxadiazole ylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Len group, isoquinolinyl group, ben Quinolinyl group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinyl group, cynolinylene group, phenantridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzo Imidazolylene group, isobenzothiazoleylene group, benzoxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group, and azacarbazoylene 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, peryllenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyrida Genyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenantridinyl group, acridinyl group , Phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group , Azacarbazolyl, -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), -N (Q ₃₁ ) (Q ₃₂ ), -B (Q ₃₁ ) (Q ₃₂ ), -C (= O) ( Q ₃₁ ), phenylene group, naphthylene group, fluorenylene group, spy substituted with at least one selected from -S (= O) ₂ (Q ₃₁ ) and -P (= O) (Q ₃₁ ) (Q ₃₂ ) Low-non-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylene Nilene group, penta Neylene group, hexasenylene group, pentaxenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzo Thiophenylene group, benzocarbazole ylene group, dibenzocarbazole ylene group, dibenzosilol ylene group, pyridinylene group, imidazole ylene group, pyrazol ylene group, thiazole ylene group, isothiazo ylene group, oxazol ylene group, isoxazolyl Ylene group, thiadiazole ylene group, oxadiazole ylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl Len group, naphthyridinylene group, quinoxalinylene group, quinazolinyl group, cynolinylene group, phenantridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiane Solylene group, benzoxazolylene group, two Sobenzooxazolylene group, triazolylene group, tetrazoleylene group, imidazopyridinylene group, imidazopyrimidinylene group, and azacarbazole ylene group;

Is selected from

Reference to 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 may be each independently,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle Neyl group, pyrenyl group, chrysenyl group, perylenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , Isoxazolyl 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, Cynolinyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl , 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, peryllenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyrida Genyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenantridinyl group, acridinyl group , Phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group , Azacarbazolyl, -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), -N (Q ₃₁ ) (Q ₃₂ ), -B (Q ₃₁ ) (Q ₃₂ ), -C (= O) ( Q ₃₁ ), phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorine substituted with at least one selected from -S (= O) ₂ (Q ₃₁ ) and -P (= O) (Q ₃₁ ) (Q ₃₂ ) Nyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perrylenyl group , Pentaphenyl group, Sasenyl group, pentaxenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo Carbazolyl, dibenzosilolyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl and pyrazinyl Group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, Phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl and imidazopi Ridinyl, imidazopyrimidinyl and azaka Sol group;

Is selected from

Reference to Q ₃₁ to Q ₃₃ may be referred to as described herein.

As another example, the host may comprise an alkaline earth metal complex. For example, the host can be selected from Be complexes (eg, the following compound H55), Mg complexes and Zn complexes.

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 the following compounds H1 to H55, but are not limited thereto:

The phosphorescent dopant may include an organometallic complex represented by Formula 401:

<Formula 401>

M (L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

In 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 Formula 402, xc1 is 1, 2 or 3, when xc1 is 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, when xc2 is 2 or more, two or more L ₄₀₂ are the same or different from each other,

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

X ₄₀₁ and X ₄₀₃ are connected via 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, independently from each other, 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 = *', and 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 each independently of the other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution 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 heterocondensed polycyclic 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 each independently of the other 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,

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

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

According to one embodiment, A ₄₀₁ and A ₄₀₂ in Formula 402 may be each independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, and 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, benzoxazole group, isobenzooxa It may be selected from sol group, triazole group, tetrazole group, oxadiazole group, triazine group, dibenzofuran group and dibenzothiophene group.

According to another embodiment, i) X ₄₀₁ in Formula 402 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 may be 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 and C ₁ -C ₂₀ An alkoxy group;

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, adada 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, norbornanyl group and norbornenyl group;

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

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, cyclohexyl, adamantanyl, norbornanyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyrida Cyclopentyl group, cyclohexene substituted with at least one selected from the group consisting of a genyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group Real 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, qui Nolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl Groups, dibenzofuranyl groups and dibenzothiophenyl groups; 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

Q ₄₀₁ to Q ₄₀₃ may be independently selected from C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, biphenyl group and naphthyl group, 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 , X ₄₀₈ , which is a linking group, may be linked to each other (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 )-*' wherein 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.

In Formula 401, L ₄₀₂ may be any monovalent, divalent, or trivalent organic ligand. For example, L ₄₀₂ is halogen, diketone (eg acetylacetonate), carboxylic acid (eg picolinate), -C (= 0), isonitrile, -CN and phosphorus (For example, phosphine, phosphite) may be selected from, 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.

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

The fluorescent dopant may include a compound represented by Formula 501 below:

<Formula 501>

In 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 heterocondensed polycyclic group,

xd1 to xd3 are each independently selected from an integer 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 polycyclic group Selected,

xd4 may be selected from an integer of 1 to 6.

According to one embodiment, Ar ₅₀₁ in Formula 501 is

Naphthalene group, heptalene group, fluorene group, spiro-nonfluorene group, benzofluorene group, dibenzofluorene group, penalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group , Pyrene group, chrysene group, naphthacene group, pisene group, perylene group, pentaphene 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 Naphthalene group, heptalene group, fluorene group, spiro-nonfluorene group, benzofluorene group, dibenzofluorene group, phenylene, substituted with at least one selected from phenyl group, biphenyl group, terphenyl group and naphthyl group Group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, pisene group, perylene group, pentaphene group, indenoanthracene group and indenophenane Tren group;

Can be selected from.

According to another embodiment, L ₅₀₁ to L ₅₀₃ in Formula 501 may be each independently,

Phenylene group, naphthylene group, fluorenylene group, spiro-nonfluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, peryleneylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazoleylene group, indolylene group, isoindoleylene group, benzo Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group, dibenzosilol ylene group, pyridinylene 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, peryllenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , A 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 Rho-nonfluorenylene group, benzofluorenylene group, dibenzofluorenylene group, Phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, peryleneylene group, pentaphenylene group, hexasenylene group, pentansenylene group, thiophenylene group, furanyl Benzene group, carbazoleylene group, indolylene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazoleylene group, dibenzocarbazoleylene group, dibenzo Silolylene group and pyridinylene group;

Can be selected from.

According to another embodiment, R ₅₀₁ and R ₅₀₂ in Formula 501 may be each independently

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle Neyl group, pyrenyl group, chrysenyl group, perylenyl 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 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, peryllenyl group, pentaphenyl group, hexasenyl group, pentasenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group , Dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl and at least one selected from -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluore Nilyl group, dibenzo fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pentacenyl group, thio Phenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and Pyridinyl group;

Is selected from

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

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

For example, the fluorescent dopant may 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 may comprise 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 made of a plurality of different materials. It 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 include an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / It may have a structure such as an electron injection layer, but is not limited thereto.

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

The "π electron deficient nitrogen 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 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) a 5-membered member having at least one * -N = *' moiety It may be a heteropolycyclic group in which at least one of the 7 to 7 membered heteromonocyclic group and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

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

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

<Formula 601>

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

In 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 heterocondensed polycyclic group,

xe1 is selected from an integer of 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 polycyclic 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 each independently 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 an integer of 1-5.

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

According to one embodiment, the ring Ar ₆₀₁ in Formula ₆₀₁ may be

Benzene group, naphthalene group, fluorene group, spiro-nonfluorene group, benzofluorene group, dibenzofluorene group, penalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, Pyrene group, chrysene group, naphthacene group, pisene group, perylene group, pentaphene 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, Phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cynoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzoti Azole group, benzoxazole group, isobenzooxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azakaba Sol groups; 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 ) ( Benzene group, naphthalene group, fluorene group, spiro-nonfluorene group, benzofluorene group, dibenzofluorene group, phenylene group, phenanthrene group, anthracene group, substituted with at least one selected from Q ₃₂ ), Fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, pysene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, kava Sol group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyri Chopped group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cynoline group, phenanthridine group, acridine Groups, phenanthroline groups, phenazine groups, benzoimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzooxazole groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, Thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups and azacarbazole groups;

Can be selected from

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

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 Formula 601-1:

<Formula 601-1>

In 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 ), at least one of X ₆₁₄ to X ₆₁₆ is N,

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

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

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

R ₆₁₄ to R ₆₁₆ are each independently 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 one embodiment, in Formulas 601 and 601-1, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ may be each independently,

Phenylene group, naphthylene group, fluorenylene group, spiro-nonfluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, peryleneylene group, pentaphenylene group, hexasenylene group, pentasenylene group, thiophenylene group, furanylene group, carbazoleylene group, indolylene group, isoindoleylene group, benzo Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazole ylene group, dibenzo carbazole ylene group, dibenzosilol ylene group, pyridinylene group, imidazole ylene group, pyrazol ylene group , Thiazole ylene group, isothiazole ylene group, oxazole ylene group, isoxazole ylene group, thiadiazole ylene group, oxadiazole ylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Len group, isoquinolinyl group, ben Quinolinyl group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinyl group, cynolinylene group, phenantridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzo Imidazolylene group, isobenzothiazoleylene group, benzoxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group, and azacarbazoylene 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, peryllenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyrida Genyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenantridinyl group, acridinyl group , Phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group And a phenylene group, a naphthylene group, a fluorenylene group, a spiro-nonfluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group substituted with at least one selected from an azacarbazolyl group. , Anthracenylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, peryleneylene group, pentaphenylene group, hexasenylene group, pentansenylene group, thiophenylene group, furanylene group, carbazolyl Rengi, Indole Benzene group, isoindoleylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazoleylene group, dibenzocarbazoleylene group, dibenzosilolylene group, pyridinylene group, Imidazole ylene group, pyrazol ylene group, thiazole ylene group, isothiazole ylene group, oxazole ylene group, isoxazole ylene group, thiadiazole ylene group, oxadiazole ylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group , Triazinylene group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cynolinylene group, phenantridinyl Ethylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazole ylene group, isobenzothiazole ylene group, benzoxazole ylene group, isobenzooxazole ylene group, triazole ylene group, tetrazole ylene group, imidazopi Lidinylene group, imida Pyrimidinyl group and a carbazolyl group aza;

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

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

According to another embodiment, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ in Formulas 601 and 601-1 may be each independently,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle Neyl group, pyrenyl group, chrysenyl group, perylenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , Isoxazolyl 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, Cynolinyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl , 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, peryllenyl 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, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyrida Genyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenantridinyl group, acridinyl group , Phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group And a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, substituted with at least one selected from azacarbazolyl group, Anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, peryleneyl, pentaphenyl, hexasenyl, pentanesyl, thiophenyl, furanyl, carbazolyl, indolyl, Isoindol Diary, Zofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, Isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzo Quinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothia Solyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and azacarbazolyl group; And

-S (= 0) ₂ ( _Q601 ) and -P (= 0) ( _Q601 ) ( _Q602 );

Is selected from

For a description of Q ₆₀₁ and Q ₆₀₂ refer to what is described herein.

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

Alternatively, the electron transport region may include 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.

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

The electron transport layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 150 kPa to about 500 kPa. When the thickness of the electron transporting layer satisfies the aforementioned range, a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.

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

The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The metal ions of the alkali metal complex may be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, and Ba. It can be selected from ions. Ligands coordinated to the metal ions of the alkali metal complex and alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Oxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclo It may be selected from pentadienes, 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 may comprise 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 made of a plurality of different materials. It 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, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromide, iodide, etc.) of the alkali metals, the alkaline earth metals and the rare earth metals. have.

The alkali metal compound may be selected from alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O and the like and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI and the like. 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 alkaline 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), and the like. 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 may be selected from YbF ₃ , ScF ₃ , TbF ₃ , YbI ₃ , ScI ₃ , TbI ₃ , but is not limited thereto.

The alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes contain ions of alkali metals, alkaline earth metals and rare earth metals as described above, and are coordinated with the metal ions of the alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes. The ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadia Sol, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is not limited thereto. .

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. It may further include the organic material. When the electron injection layer further includes an organic material, 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 heterogeneously dispersed in the matrix of the organics.

The electron injection layer may have a thickness of about 1 kPa to about 100 kPa and about 3 kPa to about 90 kPa. When the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage.

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, wherein the material for the second electrode 190 is a metal, an alloy, an electrically conductive compound having a low work function, and a combination 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), ITO and IZO may include at least one selected from, but is not limited thereto. The second electrode 190 may be a transmissive electrode, a transflective electrode, or a reflective electrode.

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

Meanwhile, the organic light emitting diode 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 light emitting diode 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 stacked in this order.

2 to 4, the description of the first electrode 110, the organic layer 150, and the second electrode 190 will be described with reference to FIG. 1.

Light generated in the light emitting layer of the organic layers 150 of the organic light emitting diodes 20 and 40 may be extracted to the outside through the first electrode 110 and the first capping layer 210 which are semi-transmissive electrodes or transmissive electrodes, Light generated in the light emitting layer among the organic layers 150 of the organic light emitting diodes 30 and 40 may be extracted to the outside 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 light emitting 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, carbocyclic compound, heterocyclic compound, amine compound, porphine derivatives (porphine derivatives), phthalocyanine derivative ( phthalocyanine derivatives), naphthalocyanine derivatives (naphthalocyanine derivatives), an alkali metal complex and an alkaline earth metal complex. The carbocyclic compound, heterocyclic compound, and amine 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 an embodiment, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine compound.

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

As mentioned above, the organic light emitting diode has been described with reference to FIGS.

Each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region may be vacuum deposited, spin coated, cast, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser. It may be formed in a predetermined region using a variety of methods, such as laser induced thermal imaging (LITI).

In the case of forming each layer included in the hole transport region, each of the light emitting layer and each layer included in the electron transport region by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 ° C., about 10 It 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 within a vacuum degree of ^-8 to about 10 ^-3 torr and a deposition rate range of about 0.01 to about 100 Pa / sec.

In the case of forming each layer included in the hole transport region, each of the light emitting layer, and each layer included in the electron transport region by spin coating, the coating conditions are, for example, a coating speed of about 2000 rpm to about 5000 rpm and about 80 Within the range of the heat treatment temperature of ℃ to 200 ℃, it 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.

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

As used herein, a C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group including at least one carbon double bond in 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. As used herein, a C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

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

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having a chemical formula of —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.

In the present specification, a C ₃ -C ₁₀ cycloalkyl group means 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 Heptyl group and the like. As used herein, a C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, a C ₁ -C ₁₀ heterocycloalkyl group means 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. As used herein, a C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, a C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one double bond in a ring, but having no aromaticity, and examples thereof Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. As used herein, a C ₃ -C ₁₀ cycloalkenylene group 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, Have 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 Thiophenyl groups and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

As used herein, a C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It means a divalent group having a. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, 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.

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. Wherein the C ₁ -C ₆₀ heteroarylene group comprises 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, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an 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 represents the C ₆ -C ₆₀ aryl group.

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

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

As used herein, a C ₅ -C ₆₀ carbocyclic group means a monocyclic or polycyclic group having 5 to 60 carbon atoms including only carbon as a ring-forming atom. The C ₅ -C ₆₀ carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₅ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, it is the C ₅ -C according to the number attached to the substituent at the ₆₀ carbocyclic group, a C ₅ -C ₆₀ carbocyclic group during the various modifications can be made, such as in 3 or 4 is the group number of a group.

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

As used herein, the substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkyl Ethylene 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 Has non-aromatic condensation Group and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused 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 ) 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 substituted with at least one selected from among;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed 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, 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 heterocondensed polycyclic group, -Si (Q ₂₁ ) (Q ₂₂ ) (Q ₂₃ ), -N (Q ₂₁ ) (Q ₂₂ ), -B (Q ₂₁ ) (Q ₂₂ ), -C (= O) A 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 groups and monovalent non-aromatic heterocondensed polycyclic groups; And

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

Is selected from

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, or AMI. 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 It may be selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group and a 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 "non-group", the substituent belongs to the "C ₆ -C ₆₀ aryl group" of "substituted phenyl group".

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

In the present specification, * and * 'means a binding site with a neighboring 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 examples, the molar equivalent of A and the molar equivalent of B are the same in the expression "B was used instead of A".

Synthesis Example

Synthesis Example 1 Synthesis of Compound 2

(1) Synthesis of Intermediate 2-3

Methyl 5-bromo-2-iodobenzoate (2-1) (10 g) and naphthalene-1-boronic acid (2-2) (5 g) were diluted in tetrahydrofuran (100 ml) and water (25 ml). Pd (PPh ₃ ) ₄ (1 g) and K ₂ CO ₃ (12 g) were added dropwise. The reaction solution was stirred at reflux for 6 hours at 65 ° C. After the temperature was lowered to room temperature, tetrahydrofuran was removed under reduced pressure, and extracted three times with ethyl acetate. The residue obtained by drying under anhydrous magnesium sulfate and then filtered under reduced pressure was purified by column chromatography, to obtain intermediate 2-3 (8.3 g, yield 83%).

C18H13BrO2 M + 1: 341.01

(2) Synthesis of Intermediate 2-4

Intermediate 2-3 (8.3 g) was diluted in tetrahydrofuran (120 ml) and then slowly dropwise added PhMgBr (1 M, 60 ml) dropwise at 0 degrees. After slowly raising the temperature to room temperature, the mixture was stirred for 16 hours. The reaction was terminated with an aqueous saturated ammonium chloride solution at 0 ° C., extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, and the residue obtained by filtration under reduced pressure was purified by column chromatography to obtain intermediate 2-4 (7.7 g, yield 68). %) Was obtained.

C29H21BrO M + 1: 465.08

(3) Synthesis of Intermediate 2-5

After diluting intermediate 2-4 (7.7 g) in dichloromethane (80 ml), methanesulfonyl acid (0.5 ml) was added thereto, followed by stirring for 3 hours. After the reaction was terminated with triethylamine (1 ml), the residue obtained by filtration under reduced pressure was purified by column chromatography to obtain Intermediate 2-5 (7.0 g, 95% yield).

C29H19Br M + 1: 447.07

(4) Synthesis of Compound 2

Intermediates 2-5 (3g) and N-phenyl- [1,1'-biphenyl] -4-amine (3g), Pd ₂ (dba) ₃ (0.34g), PtBu ₃ (0.1ml) and KOtBu (3.6g ) Was dissolved in toluene (60ml) and stirred at 85 ° C for 2 hours. The reaction solution was cooled to room temperature, terminated with water, and extracted three times with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure, and then purified by silica gel column chromatography to obtain a compound 2 (3.7 g, yield 90%).

C47H33N M + 1: 612.26

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.72-7.50 (m, 6H), 7.48-7.38 (m, 5H), 7.25-6.94 (m, 16H), 6.77 (td, 1H), 6.55 (dt, 1H), 6.09 (m, 1H), 6.05 (m, 2H), 6.00 (dd, 1H)

Synthesis Example 2 Synthesis of Compound 10

Except for using N-phenyl- [1,1'-biphenyl] -2-amine (3 g) instead of N-phenyl- [1,1'-biphenyl] -4-amine, Compound 10 (3.2 g, yield 78%) was obtained.

C47H33N M + 1: 612.26

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.72-7.50 (m, 6H), 7.48-7.43 (m, 4H), 7.32 (dt, 1H), 7.25-6.94 (m, 16H), 6.77 (td, 1H), 6.55 (dt, 1H), 6.09 (m, 1H), 6.05 (m, 2H), 6.00 (dd, 1H)

Synthesis Example 3 Synthesis of Compound 11

Compounds using the same method as in the synthesis of compound 2, except that N-phenyldibenzo [b, d] furan-1-amine (3g) is used instead of N-phenyl- [1,1'-biphenyl] -4-amine 11 (3.4 g, yield 81%) was obtained.

C47H31NO M + 1: 626.24

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.79 (m, 1H), 7.72-7.60 (m, 5H), 7.49-7.44 (m, 2H), 7.33-7.25 (m, 4H), 7.22-7.16 ( m, 4H), 7.15-6.99 (m, 9H), 6.67 (dd, 1H), 6.61 (dt, 1H), 6.63 (dd, 1H), 6.26 (m, 3H)

Synthesis Example 4 Synthesis of Compound 16

9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (16-1) (3g) was used instead of N-phenyl- [1,1'-biphenyl] -4-amine, and Intermediate 2-5 Instead of using the intermediate 16-2 (3g) to obtain a compound 16 (3.0g, 69% yield) using the same method as the synthesis of Compound 2.

C50H37N M + 1: 651.29

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.81 (dd, 1H), 7.75 (dd, 1H), 7.62 (s, 1H), 7.55-7.52 (m, 2H), 7.47-7.41 (m, 2H) , 7.36-7. 25 (m, 2H), 7.23-6.93 (m, 16H), 6.82 (td, 1H), 6.65-6.60 (m, 2H), 6.36 (d, 1H), 6.11 (m, 2H), 1.61 (s , 6H)

Synthesis Example 5 Synthesis of Compound 21

N-([1,1'-biphenyl] -4-yl) naphthalen-2-amine (3g) is used instead of N-phenyl- [1,1'-biphenyl] -4-amine, and instead of intermediate 2-5 Compound 21 (2.7 g, yield 60%) was obtained using the same method as the synthesis of compound 2, except using Intermediate 16-2 (3 g).

C51H35N M + 1: 662.28

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.81-7.75 (m, 2H), 7.70 (m, 1H), 7.66-7.60 (m, 3H), 7.59-7.34 (m, 13H), 7.28-7.05 ( m, 12H)., 6.99 (dt, 1H), 6.84-6.74 (m, 4H)

Synthesis Example 6 Synthesis of Compound 34

(1) Synthesis of Intermediate 34-2

Intermediate 34-2 (8 g) using the same method as the synthesis of Intermediate 2-3, except that (4-fluoronaphthalen-1-yl) boronic acid (34-1) (5 g) was used instead of naphthalene-1-boronic acid. , Yield 85%) was obtained.

C18H12BrFO2 M + 1: 359.00

(2) Synthesis of Intermediate 34-3

Intermediate 34-3 (8 g, yield 74%) was obtained by the same method as the synthesis of intermediate 2-4, except that intermediate 34-2 (8 g) was used instead of intermediate 2-3.

C29H20BrFO M + 1: 483.07

(3) Synthesis of Intermediate 34-4

Intermediate 34-4 (6.5 g, yield 84%) was obtained by the same method as the synthesis of intermediate 2-5, except that intermediate 34-3 (8 g) was used instead of intermediate 2-4.

C29H18BrF M + 1: 465.06

(4) Synthesis of Compound 34

Compound 34 (3.4 g, yield 84%) was obtained by the same method as the synthesis of compound 10, except that intermediate 34-4 (3 g) was used instead of intermediate 2-5.

C47H32FN M + 1: 630.25

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.76-7.70 (m, 2H), 7.62-7.53 (m, 3H), 7.50-7.44 (m, 3H), 7.37-7.30 (m, 5H), 7.25- 6.95 (m, 13H), 6.77 (dd, 1H), 6.65 (dt, 1H), 6.18 (d, 1H), 6.06 (m, 3H)

Synthesis Example 7 Synthesis of Compound 38

(1) Synthesis of Intermediate 38-3

Except for using (4-bromonaphthalen-1-yl) boronic acid (38-2) (10 g) instead of naphthalene-1-boronic acid, the intermediate 38-3 ( 12 g, yield 80%) was obtained.

C18H12BrFO2 M + 1: 359.00

(2) Synthesis of Intermediate 38-4

Intermediate 38-4 (14 g, yield 87%) was obtained using the same method as the synthesis of intermediate 2-4, except that intermediate 38-3 (12 g) was used instead of intermediate 2-3.

C29H20BrFO M + 1: 483.07

(3) Synthesis of Intermediate 38-5

Intermediate 38-5 (8 g, yield 59%) was obtained by the same method as the synthesis of intermediate 2-5, except that intermediate 38-4 (14 g) was used instead of intermediate 2-4.

C29H18BrF M + 1: 465.06

(4) Synthesis of Compound 38

Compound 38 (3.1 g, yield 60%) was obtained by the same method as the synthesis of compound 2, except that intermediate 38-5 (3 g) was used instead of intermediate 2-5.

C47H32FN M + 1: 630.25

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.77 (m, 1H), 7.65-7.60 (m, 2H), 7.55-7.28 (m, 11H), 7.22-6.94 (m, 12H), 6.78 (m, 2H), 6.65 (dt, 1H), 6.43 (dd, 1H), 6.12 (m, 2H)

Synthesis Example 8: Synthesis of Compound 54

(1) Synthesis of Intermediate 54-1

Dilute 1-bromo-4-methylbenzene (5 g) in THF and lower the temperature to -78 ° C. N-BuLi (12.3 mL, 2.5 M in hexane) was slowly added dropwise while maintaining the temperature. After 1 hour, intermediate 2-3 (5 g) diluted in THF was slowly added dropwise to the reaction vessel. After slowly raising the temperature to room temperature, the reaction was terminated with a saturated ammonium chloride solution and extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography to obtain an intermediate 54-1 (4.8 g, yield 66%).

C31H25BrO M + 1: 493.11

(2) Synthesis of Intermediate 54-2

Intermediate 54-2 (3.6 g, yield 75%) was obtained using the same method as the synthesis of intermediate 2-5, except using intermediate 54-1 (4.8 g).

C31H23Br M + 1: 475.10

(3) Synthesis of Compound 54

N-phenyldibenzo [b, d] furan-2-amine (3 g) was used instead of N-phenyl- [1,1'-biphenyl] -4-amine, and intermediate 54-2 (3.5 g) was used instead of intermediate 2-5. Compound 54 (3.8 g, yield 79%) was obtained by the same method as the synthesis of compound 2, except that 1) was used.

C49H35NO M + 1: 654.27

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.84 (m, 1H), 7.74-7.65 (m, 4H), 7.63 (m, 1H), 7.55-7.46 (m, 4H), 7.44 (m, 1H, 7.32 (dt, 1H), 7.13-6.98 (m, 7H), 6.95 (dd, 1H), 6.86 (m, 4H), 6.67 (dt, 1H), 6.42 (d, 1H), 6.30 (m, 3H) , 2.34 (s, 3H), 2.32 (s, 3H)

Synthesis Example 9 Synthesis of Compound 64

(1) Synthesis of Intermediate 64-1

Intermediate 64-1 (6.6 g, yield 90%) was obtained by the same method as the synthesis of intermediate 2-4, except that 1-bromo-4-fluorobenzene (5.5 g) was used.

C29H19BrF2O M + 1: 501.06

(2) Synthesis of Intermediate 64-2

Intermediate 64-2 (5.3 g, 83%) was obtained using the same method as the synthesis of Intermediate 2-5, except that Intermediate 64-1 (6.6 g) was used instead of Intermediate 2-4.

C29H17BrF2 M + 1: 484.05

(3) Synthesis of Compound 64

Use 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (3 g) instead of N-phenyl- [1,1'-biphenyl] -4-amine and substitute 64-64 as intermediate 2-5 Using the same method as the synthesis of compound 2, except that (3g) was used, compound 64 (3.4 g, yield 80%) was obtained.

C50H35F2N M + 1: 688.27

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.78 (td, 1H), 7.72-7.64 (m, 3H), 7.63 (m, 1H), 7.58 (d, 1H), 7.50 (d, 1H), 7.36 -7.27 (m, 2H), 7.14-7.00 (m, 9H), 6.72 (dd, 1H), 6.66 (td, 1H), 6.51-6.46 (m, 4H), 6.42 (dd, 1H), 6.33 ( dd, 2H), 6.22 (m, 2H), 1.62 (s, 6H)

Synthesis Example 10 Synthesis of Compound 81

Compound 81 (3.7 g, yield 74%) was obtained by the same method as the synthesis of compound 21, except that intermediate 81-1 (3 g) was used instead of intermediate 16-2.

C51H35N M + 1: 662.28

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.78-7.62 (m, 7H), 7.57-7.32 (m, 11H), 7.31 (dt, 1H), 7.18-7.01 (m, 8H), 6.96 (t, 1H), 6.78-6.75 (m, 4H), 6.41 (m, 2H), 5.71 (dd, 1H)

Synthesis Example 11 Synthesis of Compound 95

Compound 95 (2.5 g, yield 86%) was obtained using the same method as the synthesis of compound 11, except that intermediate 95-1 (2.5 g) was used instead of intermediate 2-5.

C47H31NO M + 1: 626.24

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.79-7.66 (m, 5H), 7.49-7.44 (m, 2H), 7.36-7.27 (m, 4H), 7.21-7.19 (m, 4H), 7.14- 7.01 (m, 10H), 6.69-6.60 (m, 2H), 6.39 (dd, 1H), 6.34 (m, 2H), 6.05 (d, 1H)

Synthesis Example 12 Synthesis of Compound 98

Synthesis of Compound 2 except using N-phenyl- [1,1'-biphenyl] -4-amine (2.5 g) and using Intermediate 98-1 (2.5 g) instead of Intermediate 2-5 (3 g) Compound 98 (2.9 g, yield 85%) was obtained using the same method as the method above.

C47H33N M + 1: 612.26

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.92 (d, 1H), 7.67-7.58 (m, 4H), 7.54-7.30 (m, 7H), 7.26-7.01 (m, 13H), 6.94 (dd, 1H), 6.83 (m, 2H), 6.65 (dt, 1H), 6.57 (dd, 1H), 6.22 (m, 2H), 5.58 (t, 1H)

Synthesis Example 13: Synthesis of Compound 112

(1) Synthesis of Intermediate 112-2

Use methyl 2-bromobenzoate (112-1) (8.4 g) instead of methyl 5-bromo-2-iodobenzoate and (5-bromonaphthalen-1-yl) boronic acid (10 g) instead of naphthalene-1-boronic acid Compound 112-2 (8.8 g, yield 68%) was obtained by the same method as the synthesis of Intermediate 2-3, except for using.

C18H13BrO2: M + 1 341.01

(2) Synthesis of Intermediate 112-3

Intermediate 112-3 (8.5 g, yield 71%) was obtained by the same method as the synthesis of Intermediate 2-4, except that Intermediate 112-2 (8.8 g) was used instead of Intermediate 2-3.

C29H21BrO: M + 1 465.08

(3) Synthesis of Intermediate 112-4

Intermediate 112-4 (6.6 g, 81% yield) was obtained by the same method as the synthesis of Intermediate 2-5, except that Intermediate 112-3 (8.5 g) was used instead of Intermediate 2-4.

C29H19Br: M + 1 447.07

(4) Synthesis of Compound 112

Compound 112 (3.1 g, yield 71%) was obtained by the same method as the synthesis of compound 16, except that Intermediate 112-4 (2.8 g) was used instead of Intermediate 16-2.

C50H37N: M + 1 652.29

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.81 (td, 1H), 7.76 (td, 1H), 7.63 (d, 1H), 7.55 (td, 1H), 7.51 (dd, 1H), 7.45 (dt , 1H), 7.36-7.25 (m, 2H), 7.22-7.01 (m, 15H), 6.86 (td, 1H), 6.81 (d, 1H), 6.65-6.59 (m, 2H), 6.37 (dd, 1H) ), 6.31 (m, 1H), 6.12-6.08 (m, 2H), 1.61 (s, 6H)

Synthesis Example 14 Synthesis of Compound 124

Compound 124 (2.7 g, yield 75%) was obtained using the same method as the synthesis of compound 16, except that Intermediate 124-1 (2.6 g) was used instead of Intermediate 16-2.

C56H41N: M + 1 728.32

¹ H NMR (500 MHz, CDCl ₃ ) δ = 8.15 (d, 1H), 8.07-8.03 (m, 2H), 7.78 (d, 1H), 7.70 (d, 1H), 7.60-7.55 (m, 2H) , 7.51-7.43 (m, 2H), 7.41-7.28 (m, 4H), 7.25-7.18 (m, 4H), 7.13-7.02 (m, 10H), 6.88 (d, 1H), 6.72-6.70 (m , 2H), 6.42 (m, 2H), 6.29 (d, 1H), 6.22 (m, 2H), 1.62 (s, 6H)

Synthesis Example 15 Synthesis of Compound 136

Compound 136 (2.3 g, yield 69%) was obtained using the same method as the synthesis of compound 16, except that Intermediate 136-1 (2.3 g) was used instead of Intermediate 16-2.

C50H36FN: M + 1 670.28

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.78 (td, 1H), 7.74 (dd, 1H), 7.58-7.52 (m, 2H), 7.48-7.40 (m, 2H), 7.36-7.28 (m, 1H), 7.25-7.20 (m, 4H), 7.18- 7.05 (m, 11H), 6.96 (d, 1H), 6.72 (dd, 1H), 6.66 (t, 1H), 6.42-6.39 (m, 2H ), 6.29 (d, 1H), 6.22 (m, 2H), 1.62 (s, 6H)

EXAMPLE

Comparative Example 1 :

The anode was cut into corning 15Ω / cm ² (1200Å) ITO glass substrates of 50mm x 50mm x 0.7mm size, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes, and then irradiated with ultraviolet light for 30 minutes. The glass substrate was installed in a vacuum deposition apparatus by washing with exposure to ozone.

2-TNATA, a known material as a hole injection layer, was vacuum deposited on the substrate to form a thickness of 600 Å, followed by 4,4'-bis [N- (1-naphthyl) as a hole transporting compound. ) -N-phenylamino] biphenyl (hereinafter referred to as NPB) was vacuum deposited to a thickness of 300 GPa to form a hole transport layer.

4,4'-bis [2- (4-, a known compound as 9,10-di (naphthalen-2-yl) anthracene (hereinafter referred to as DNA) and a blue fluorescent dopant as a known blue fluorescent host on the hole transport layer. (N, N-diphenylamino) phenyl) vinyl] biphenyl (hereinafter referred to as DPAVBi) was co-deposited at a weight ratio of 98: 2 to form a light emitting layer having a thickness of 300 GPa.

Subsequently, Alq ₃ was deposited on the emission layer with an electron transport layer at a thickness of 300 GPa, LiF, which is a halogenated alkali metal, was deposited on the electron transport layer, at an electron injection layer, at a thickness of 10 GPa, and Al was deposited at 3000 mA (cathode electrode). An organic EL device was manufactured by vacuum evaporation to a thickness to form a LiF / Al electrode.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound A was used instead of NPB to form the hole transport layer.

<Compound A>

Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound B was used instead of NPB to form the hole transport layer.

<Compound B>

Comparative Example 4

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound C was used instead of NPB to form the hole transport layer.

<Compound C>

Comparative Example 5

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound D was used instead of NPB to form the hole transport layer.

<Compound D>

Comparative Example 6

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound E was used instead of NPB to form the hole transport layer.

<Compound E>

Comparative Example 7

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound F was used instead of NPB to form the hole transport layer.

<Compound F>

Comparative Example 8

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound G was used instead of NPB to form the hole transport layer.

<Compound G>

Example 1

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 2 was used instead of NPB to form the hole transport layer.

Example 2

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 10 was used instead of NPB to form the hole transport layer.

Example 3

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 11 was used instead of NPB to form the hole transport layer.

Example 4

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 16 was used instead of NPB to form the hole transport layer.

Example 5

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 21 was used instead of NPB to form the hole transport layer.

Example 6

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 34 was used instead of NPB to form the hole transport layer.

Example 7

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 38 was used instead of NPB to form the hole transport layer.

Example 8

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 54 was used instead of NPB in forming the HTL.

Example 9

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 64 was used instead of NPB when forming the HTL.

Example 10

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 81 was used instead of NPB to form the hole transport layer.

Example 11

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 95 was used instead of NPB to form the hole transport layer.

Example 12

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 98 was used instead of NPB when forming the hole transport layer.

Example 13

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 112 was used instead of NPB in forming the HTL.

Example 14

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 124 was used instead of NPB to form the hole transport layer.

Example 15

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Compound 136 was used instead of NPB when forming the hole transport layer.

The Comparative Examples 1 to 8 and Examples 1 device performance at a current density of 50 mA / cm ² with respect to the organic light emitting device manufactured in to 15 (driving voltage, luminance efficiency) and half of a current density of 100 mA / cm ² The lifetime was measured using the following method and the results are shown in Table 1.

Luminance: Powered on a current-voltmeter (Kethley SMU 236) and measured using luminance meter PR650.

Efficiency: Powered from a current-voltmeter (Kethley SMU 236) and measured using luminance meter PR650.

On the other hand, the half life is the time (hr) taken for the luminance to reach 50% when the initial luminance (at 100 mA / cm ² ) is 100%.

Hole transport material Driving voltage
(V) Current density
(mA / cm ² ) Luminance
(cd / ㎡) efficiency
(cd / A) Luminous color Half-life
(hr @ 100 mA / cm ² ) Comparative Example 1 NPB 7.01 50 2645 5.29 blue 258 Comparative Example 2 Compound A 6.31 50 2775 5.55 blue 283 Comparative Example 3 Compound B 6.21 50 2810 5.62 blue 299 Comparative Example 4 Compound C 6.11 50 2755 5.51 blue 305 Comparative Example 5 Compound d 6.42 50 2775 5.55 blue 220 Comparative Example 6 Compound E 6.89 50 2330 4.66 blue 210 Comparative Example 7 Compound F 6.60 50 2615 5.23 blue 243 Comparative Example 8 Compound G 6.76 50 2310 4.62 blue 200 Example 1 Compound 2 4.89 50 3410 6.82 blue 412 Example 2 Compound 10 4.87 50 3435 6.87 blue 406 Example 3 Compound 11 4.64 50 3385 6.77 blue 419 Example 4 Compound 16 4.56 50 3460 6.92 blue 423 Example 5 Compound 21 4.67 50 3475 6.95 blue 410 Example 6 Compound 34 4.72 50 3440 6.88 blue 408 Example 7 Compound 38 4.79 50 3280 6.56 blue 420 Example 8 Compound 54 4.81 50 3360 6.72 blue 392 Example 9 Compound 64 4.92 50 3440 6.88 blue 381 Example 10 Compound 81 4.99 50 3460 6.92 blue 399 Example 11 Compound 95 4.87 50 3265 6.53 blue 378 Example 12 Compound 98 4.83 50 3265 6.53 blue 388 Example 13 Compound 112 4.89 50 3235 6.47 blue 391 Example 14 Compound 124 4.82 50 3280 6.56 blue 368 Example 15 Compound 136 4.87 50 3115 6.23 blue 368

From Table 1, as a result of using the compound according to the embodiment of the present invention as a hole transporting material in the organic electroluminescent device, all of the examples using the compound of the present invention organic light-emitting of Comparative Example 1 using a known material NPB Compared to the device, the driving voltage was improved and the efficiency was improved, and the IVL characteristics were excellent. In addition, it can be seen that the driving voltage is improved and the efficiency and the half life are excellent, as compared with Comparative Examples 2 to 8 using the compounds A to G.

Although the present invention has been described with reference to the synthesis examples and examples, this is merely exemplary, and those skilled in the art to which the present invention pertains various modifications and equivalent other embodiments. Will understand. Therefore, the true technical protection scope of the present invention will be defined by the technical spirit of the appended claims.

10, 20, 30, 40: organic light emitting element
110: first electrode
150: organic layer
190: second electrode
210: first capping layer
220: second capping layer

Claims (18)

An amine compound represented by any one of the following Chemical Formulas 1-1 and 1-3 to 1-6:
<Formula 1-1>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 2>

In Formulas 1-1 and 1-3 to 1-6 and Formula 2,
Ar ₁ , Ar ₂ , L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₆₀ heterocyclic group,
a1 and a2 are each independently selected from an integer of 0 to 5, when a1 is 2 or more, two or more L ₁ are the same or different from each other, and when a2 is 2 or more, two or more L ₂ are the same or different, and
When a1 is 0, *-(L ₁ ) _a1- * 'is a single bond; when a2 is 0, *-(L ₂ ) _a2- *' is a single bond,
R ₁ to R ₁₀ are independently of each other, a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino Groups, hydrazono groups, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkynyl groups, substituted or unsubstituted C _1- C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or Unsubstituted C ₂ -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, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or unsubstituted monovalent non- Hyangjok condensed polycyclic heterocyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -B (Q 1) (Q 2), -C (= O) (Q 1), -P (= O) ( Q ₁ ) (Q ₂ ), -P (= S) (Q ₁ ) (Q ₂ ), -S (= O) (Q ₁ ) (Q ₂ ) and -S (= O) ₂ (Q ₁ ) ( Q ₂ )
R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution 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 an unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted 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, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -B (Q ₁ ) (Q ₂ ), -C (= O) (Q ₁ ), -P (= O) (Q ₁ ) (Q ₂ ), -P ( = S) (Q ₁ ) (Q ₂ ), -S (= O) (Q ₁ ) (Q ₂ ) and -S (= O) ₂ (Q ₁ ) (Q ₂ ),
b1 and b2 are each independently selected from an integer of 1 to 10, when b1 is 2 or more, two or more R ₁₁ are the same or different from each other, and when b2 is 2 or more, two or more R ₁₂ are the same or different, and
The substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₂ -C ₆₀ 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, At least one substituent selected from a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted monovalent non-aromatic condensed polycyclic group and a 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 ), -B (Q ₁₁ ) (Q ₁₂ ), -C (= 0) (Q ₁₁ ), -S (= 0) ₂ (Q ₁₁ ) and -P (= 0) (Q ₁₁ ) (Q ₁₂ ) substituted with at least one selected from C ₁ -C _{A 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;
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 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, 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 heterocondensed polycyclic group, -Si (Q ₂₁ ) (Q ₂₂ ) (Q ₂₃ ), -B (Q ₂₁ ) (Q ₂₂ ), -C (= O) (Q ₂₁ ), -S (= O) C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cyclo substituted with at least one selected from ₂ (Q ₂₁ ) and -P (= 0) (Q ₂₁ ) (Q ₂₂ ) alkenyl group, a 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, 1 Non-aromatic condensed polycyclic he And one is a non-aromatic heterocyclic group, fused polycyclic; And
-Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), -B (Q ₃₁ ) (Q ₃₂ ), -C (= O) (Q ₃₁ ), -S (= O) ₂ (Q ₃₁ ), and- P (= 0) (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, and 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, biphenyl group and terphenyl group,
* And * 'are binding sites with neighboring atoms. The method of claim 1,
Ar ₁ , Ar ₂ , L ₁ and L ₂ are independently of each other,
Benzene group, pentalene group, indene group, naphthalene group, azulene group, heptalene group, indaene group, acenaphthalene group, fluorene group, spiro-fluorene group, benzofluorene group, phenylene group, phenane Tren Group, Anthracene Group, Fluoranthrene Group, Triphenylene Group, Pyrene Group, Chrysene Group, Naphthacene Group, Pysene Group, Perylene Group, Pentafen Group, Hexane Group, Pyrrole Group, Imidazole Group, Pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine Group, quinoxaline group, quinazoline group, cynoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoxazole group, benzoimidazole group, Furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxazole group, triazole group, tetrazole group, oxadiazole Groups, triazine groups, benzoxazole groups, dibenzofuran groups, dibenzothiophene groups, benzocarbazole groups and dibenzocarbazole groups; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Benzene group, pentalene group, indene group substituted with at least one selected from alkoxy group, C ₆ -C ₂₀ aryl group, C ₂ -C ₂₀ heteroaryl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) , Naphthalene group, azulene group, heptalene group, indacene group, acenaphthalene group, fluorene group, spiro-fluorene group, benzofluorene group, phenylene group, phenanthrene group, anthracene group, fluoranthrene Group, triphenylene group, pyrene group, chrysene group, naphthacene group, pysene group, perylene group, pentaphene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group , Pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinol Group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cynoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, Phenazine group, benzoxazole group, benzoimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxa Sol groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, benzoxazole groups, dibenzofuran groups, dibenzothiophene groups, benzocarbazole groups and dibenzocarbazole groups;
An amine compound selected from among. The method of claim 1,
Ar ₁ and Ar ₂ may be each independently selected from a benzene group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C A benzene group substituted with at least one selected from a ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a C ₂ -C ₂₀ heteroaryl group, and —Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ); An amine compound selected from among. The method of claim 1,
The L ₁ and L ₂ are independently from each other, an amine compound selected from the group represented by the following formulas 3-1 to 3-46:

In Formulas 3-1 to 3-46,
Y ₁ is O, S, C (Z ₃ ) (Z ₄ ), N (Z ₅ ) or Si (Z ₆ ) (Z ₇ ),
Z ₁ to Z ₇ 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, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolin Nyl, naphthyridinyl, quinoxalinyl, quinazolinyl, carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl and- Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ),
d2 is selected from an integer of 0 to 2, when d2 is 2 or more, two or more Z ₁ are the same as or different from each other,
d3 is selected from an integer of 0 to 3, when d3 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,
d4 is selected from an integer of 0 to 4, when d4 is 2 or more, two or more Z ₁ are the same as or different from each other,
d5 is selected from an integer of 0 to 5, when d5 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,
d6 is selected from an integer of 0 to 6, when d6 is 2 or more, two or more Z ₁ and Z ₂ are the same as or different from each other,
d8 is selected from an integer of 0 to 8, and when d8 is 2 or more, two or more Z ₁ are the same as or different from each other,
* And * 'are binding sites with neighboring atoms. The method of claim 1,
Wherein a1 and a2 are each independently 0 or 1, an amine compound. The method of claim 1,
R ₁ to R ₁₀ are independently of each other, a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydra Gino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl 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 polycyclic group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ),
R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution Or an unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic ring An amine compound selected from the group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ). The method of claim 1,
R ₁ to R ₁₀ are independently of each other, a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydra A geno group, a hydrazono group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a group represented by the following formulas 5-1 to 5-80 and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ); ,
R ₁₁ and R ₁₂ independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substitution Or an amine compound selected from an unsubstituted C ₁ -C ₆₀ alkyl group, a group represented by the following Formulas 5-1 to 5-80 and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ):

In Formulas 5-1 to 5-80,
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or Si (Z ₃₆ ) (Z ₃₇ ),
Z ₃₁ to Z ₃₇ 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, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene- benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, penalenyl group, phenanthrenyl group, anthracenyl group, fluoranthhenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanyl group Trolnyl group, phenazinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ),
e2 is selected from an integer of 0 to 2, when e2 is 2 or more, two or more Z ₃₂ are the same as or different from each other,
e3 is selected from an integer of 0 to 3, when e3 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,
e4 is selected from an integer of 0 to 4, when e4 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,
e5 is selected from an integer of 0 to 5, when e5 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,
e6 is selected from an integer of 0 to 6, when e6 is 2 or more, two or more Z ₃₁ and Z ₃₂ are the same as or different from each other,
e7 is selected from an integer of 0 to 7, when e7 is 2 or more, two or more Z ₃₁ are the same as or different from each other,
e9 is selected from an integer of 0 to 9, when e9 is 2 or more, two or more Z ₃₁ are the same as or different from each other,
* Is a bonding site with a neighboring atom. The method of claim 1,
R ₁₁ and R ₁₂ are each independently selected from the group represented by the following Chemical Formulas 6-1 to 6-34, an amine compound:

In Chemical Formulas 6-1 to 6-34,
Ph is a phenyl group,
* Is a bonding site with a neighboring atom. The method of claim 1,
R ₁ to R ₁₀ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, or methyl group , Amine compound selected from ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, phenyl group and biphenyl group . The method of claim 1,
An amine compound selected from the following compounds 13 to 24, 37 to 48 and 73 to 120:

. A first electrode;
A second electrode opposite the first electrode; And
And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer.
The organic light-emitting device in which the said organic layer contains 1 or more types of the amine compound of any one of Claims 1-10. The method of claim 11,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer further includes a hole transport region disposed between the first electrode and the light emitting layer, and an electron transport region disposed between the light emitting layer and the second electrode,
The hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof,
And the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The method of claim 12,
And the hole transport region comprises the amine compound. The method of claim 12,
And the hole transport layer comprises a hole transport layer, and the hole transport layer comprises the amine compound. The method of claim 11,
The light emitting layer includes the amine compound, an organic light emitting device. The method of claim 12,
The hole transport region comprises a p-dopant,
The LUMO of the p-dopant is -3.5 eV or less, and an organic light emitting device. The method of claim 11,
The organic light emitting device of claim 1, wherein the light emitting layer comprises at least one of a styryl compound, an anthracene compound, a pyrene compound, and a spiro-bifluorene compound. The method of claim 11,
The light emitting layer is a first color light emitting-emitting layer,
Between the first electrode and the second electrode, i) at least one second color light-emitting layer is further included, or ii) at least one second color light-emitting layer and at least one third color light-emitting layer This is additionally included,
The maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same or different from each other,
And a mixed color light in which the first color light and the second color light are mixed with each other or mixed color light in which the first color light, the second color light and the third color light are mixed with each other.

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